Organic EL device

Abstract
In an organic EL device comprising organic layers between a pair of electrodes participating in at least a light emitting function, at least one organic layer contains an organic compound selected from naphthacene, tetraaryldiamine, anthracene and quinoxaline derivatives as a host material and an organic compound having a specific skeleton, typically diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative as a dopant. The device is capable of light emission to a satisfactory luminance, especially in a long wavelength region, and with a chromatic purity sufficient for use in full color displays, and had a sufficient durability to sustain such improved light emission performance over a long time.
Description


BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention


[0002] This invention relates to an organic electroluminescent (EL) device, and more particularly, to a compound for use in a device of the type wherein an electric field is applied across a thin film of an organic compound to emit light.


[0003] 2. Background Art


[0004] Organic electroluminescent (EL) devices include a thin film containing a luminescent organic compound interleaved between an electron injecting electrode and a hole injecting electrode. Electrons and holes are injected into the thin film where they are recombined to create excitons. Light is emitted by utilizing luminescence (phosphorescence or fluorescence) upon deactivation of excitons.


[0005] The organic EL devices are characterized by plane light emission at a high luminance of about 100 to 10,000 cd/m2 with a voltage of about 10 volts and light emission in a spectrum from blue to red color by a simple choice of the type of fluorescent material.


[0006] Doping is one technique for producing light emission of any desired color from organic EL devices. It was reported in Jpn. J. Appl. Phys., 10, 527 (1971) to change emission color from blue to green by doping anthracene crystals with a minor level of tetracene. With respect to organic thin film EL devices having a multilayer structure, it was reported in JP-A 63-264692 to incorporate in a host material having a light emitting function a minor amount of a fluorescent dye capable of emitting light different from that of the host material in response to light emission from the host material as a dopant to form a light emitting layer, thereby changing the color of light emission from green to orange or red.


[0007] With respect to long wavelength light emission of yellow to red, known light emitting materials or dopant materials include laser dyes capable of red oscillation (EPO 281381), compounds capable of exciplex emission (JP-A 2-255788), perylene compounds (JP-A 3-791), coumarin compounds (JP-A 3-792), dicyanomethylene compounds (JP-A 3-162481), thioxanthene compounds (JP-A 3-177486), mixtures of a conjugated polymer and an electron transporting compound (JP-A 6-73374), squalirium compounds (JP-A 6-93257), oxadiazole compounds (JP-A 6-136359), oxynate derivatives (JP-A 6-145146), and pyrene compounds (JP-A 6-240246).


[0008] It is reported in J. Am. Chem. Soc., 118, 2374-2379, 1996, that benzofluoranthene derivatives have a very high fluorescent quantum yield. JP-A 10-330295 and JP-A 11-233261 disclose organic EL devices having a light emitting layer in which a variety of host materials are doped with dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivatives derived from benzofluoranthene.


[0009] Other light emitting materials disclosed heretofore include condensed polycyclic aromatic compounds (JP-A 5-32966 and 5-214334). Also dopant materials proposed heretofore include various condensed polycyclic aromatic compounds (JP-A 5-258859).


[0010] However, when these materials are used as the dopant, EL devices often fail to allow dopant molecules to exert their own fluorescence due to the interaction between dopants or between the dopant and the host.


[0011] Therefore, with respect to organic EL devices of the type in which a host material is doped with a fluorescent dye, a choice of host material is an important and difficult task in order for the device to produce high efficiency light emission. Currently available organic EL devices fail to reach a practically acceptable level of emission efficiency although fluorescent dyes having a high fluorescent quantum yield are used as the dopant.


[0012] When organic EL devices are fabricated using the doping technique, the energy transfer from host molecules in the excited state to the dopant is not 100%, and often not only the dopant, but also the host material emit light. Especially in the case of red light emitting devices, the chromatic purity is often exacerbated by faint light emission of the host material since the host material emits light in a wavelength region of higher visibility than the dopant. Further improvements in properties pertaining to the luminous lifetime and durability are needed, with the target placed on practical application.



SUMMARY OF THE INVENTION

[0013] An object of the invention is to provide an organic EL device capable of light emission to a satisfactory luminance, especially in a long wavelength region, and with a chromatic purity sufficient for use in full color displays, and having a sufficient durability to sustain such improved light emission performance over a long time.


[0014] The above and other objects are achieved by the invention which is defined below.


[0015] [1] An organic EL device comprising one or more organic layers between a pair of electrodes participating in at least a light emitting function,


[0016] at least one of the organic layers containing at least one of organic compounds having basic skeletons of the following formulas (I) to (IV) and at least one organic compound having a skeleton of the following formula (V) at the same time:
1


[0017]  wherein Q1 to Q8 are independently hydrogen or substituted or unsubstituted alkyl, aryl, amino, heterocyclic or alkenyl radicals,
2


[0018]  wherein R1, R2, R3 and R4 are independently aryl, fluorene, carbazolyl, alkyl, alkoxy, aryloxy, amino or halogen radicals, at least one of R1, R2, R3 and R4 is aryl, r1, r2, r3 and r4 each are 0 or an integer of 1 to 5, with the proviso that r1, r2, r3 and r4 are not 0 at the same time, R5 and R6 are independently alkyl, alkoxy, amino, aryl or halogen radicals and may be the same or different, r5 and r6 each are 0 or an integer of 1 to 4,
3


[0019]  wherein A101 is a monophenylanthryl or diphenylanthryl radical and may be the same or different, L is hydrogen, a single bond or an n-valent linkage, and n is an integer of 1 to 4,


Qn-L101  (IV)


[0020]  wherein Q is a pyrazinyl radical having fused thereto a six-membered aromatic ring containing 0 to 2 nitrogen atoms and may be the same or different, n is 2 or 3, and L101 is a single bond or n-valent radical,
4


[0021]  wherein X1 to X10, L1 and L2 are independently hydrogen, halogen atoms, straight, branched or cyclic alkyl radicals which may have substituents, straight, branched or cyclic alkoxy radicals which may have substituents, straight, branched or cyclic alkylthio radicals which may have substituents, straight, branched or cyclic alkenyl radicals which may have substituents, straight, branched or cyclic alkenyloxy radicals which may have substituents, straight, branched or cyclic alkenylthio radicals which may have substituents, substituted or unsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxy radicals, substituted or unsubstituted aralkylthio radicals, substituted or unsubstituted aryl radicals, substituted or unsubstituted aryloxy radicals, substituted or unsubstituted arylthio radicals, substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR1 radicals (wherein R1 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical or a substituted or unsubstituted aryl radical), —COR2 radicals (wherein R2 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical or an amino radical), or —OCOR3 radicals (wherein R3 is a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), or at least two adjoining radicals selected from X1 to X10, L1 and L2 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached, or L1 and L2 each may be a single bond. n is 1 or 2.


[0022] [2] The organic EL device of [1] wherein the at least one of the organic layers contains a host material and a dopant,


[0023] said host material comprises at least one compound selected from the organic compounds having basic skeletons of the formulas (I) to (IV) and


[0024] said dopant comprises at least one compound selected from the organic compounds having a skeleton of the formula (V).


[0025] [3] The organic EL device of [1] or [2] wherein in formula (V), at least two adjoining radicals selected from X1 to X10, L1 and L2 bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached.


[0026] [4] The organic EL device of any one of [1] to [3] wherein the compound of formula (V) is a compound of the following formula (VI):
5


[0027] wherein X1 to X6, X9, X10, X11 to X16, X19 and X20 are independently hydrogen, halogen atoms, straight, branched or cyclic alkyl radicals which may have substituents, straight, branched or cyclic alkoxy radicals which may have substituents, straight, branched or cyclic alkylthio radicals which may have substituents, straight, branched or cyclic alkenyl radicals which may have substituents, straight, branched or cyclic alkenyloxy radicals which may have substituents, straight, branched or cyclic alkenylthio radicals which may have substituents, substituted or unsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxy radicals, substituted or unsubstituted aralkylthio radicals, substituted or unsubstituted aryl radicals, substituted or unsubstituted aryloxy radicals, substituted or unsubstituted arylthio radicals, substituted or unsubstituted arylalkenyl radicals, substituted or unsubstituted alkenylaryl radicals, substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR1 radicals (wherein R1 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical or a substituted or unsubstituted aryl radical), —COR2 radicals (wherein R2 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical or an amino radical), or —OCOR3 radicals (wherein R3 is a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), or at least two adjoining radicals selected from X1 to X20 may bond together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached.


[0028] [5] The organic EL device of [4] wherein the compound of formula (VI) is a compound of the following formula (VI′):
6


[0029] wherein X1 to X44 are as defined for X1 to X20 in formula (VI).


[0030] [6] The organic EL device of [4] or [5] wherein X1 to X20 in formula (VI) and X1 to X44 in formula (VI′) are independently substituted or unsubstituted aryl, alkyl, alkenyl, alkoxy or aryloxy radicals.


[0031] [7] The organic EL device of any one of [4] to [6] wherein at least one of X1 to X20 in formula (VI) and X1 to X44 in formula (VI′) is an ortho-substituted phenyl radical. [8] The organic EL device of any one of [4] to [7] wherein in formula (VI) or (VI′), either one or both of X1 and X4 and/or either one or both of X11 and X14 are ortho-substituted phenyl radicals.


[0032] [9] The organic EL device of any one of [1] to [8] wherein said at least one of the organic layers contains at least one organic compound having a basic skeleton of the formula (I).


[0033] [10] The organic EL device of any one of [1] to [9] wherein said at least one of the organic layers contains at least one organic compound having a basic skeleton of the formula (I) and at least one organic compound having a basic skeleton of the formula (II) at the same time.


[0034] [11] The organic EL device of any one of [4] to [10] wherein at least one of the organic compounds has a vibration structure in both an excitation spectrum and a fluorescence spectrum.


[0035] [12] The organic EL device of any one of [4] to [11] wherein at least one of the organic compounds has a Stokes shift of up to 0.1 eV.


[0036] [13] The organic EL device of any one of [4] to [12] wherein the host material in a light emitting layer has a greater electron affinity than an electron transporting layer and/or a hole transporting layer.


[0037] [14] The organic EL device of any one of [1] to [13] wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least two of Q1 to Q8 are substituted or unsubstituted aryl radicals.


[0038] [15] The organic EL device of [14] wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least six of Q1 to Q8 are substituted or unsubstituted aryl radicals.


[0039] [16] The organic EL device of [14] or [15] wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least two of Q1, Q2, Q3 and Q4 are substituted or unsubstituted aryl radicals.


[0040] [17] The organic EL device of any one of [14] to [16] wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least four of Q1, Q2, Q3 and Q4 are substituted or unsubstituted aryl radicals.


[0041] [18] The organic EL device of any one of [14] to [17] wherein at least two of the aryl radicals represented by Q1, Q2, Q3 and Q4 have aryl radicals substituted thereon.


[0042] [19] The organic EL device of any one of [2] to [18] wherein the at least one of the organic layers contains 80 to 99.9% by weight of the host material.


[0043] [20] An organic EL device wherein at least one of organic layers contains at least one organic compound having a basic skeleton of the formula (I) as set forth in [16] and at least one organic compound having a basic skeleton of the formula (IV′).


[0044] [21] The organic EL device of any one of [1] to [20], further comprising at least one hole injecting and transporting layer.


[0045] [22] The organic EL device of any one of [1] to [21], further comprising at least one electron injecting and transporting layer.


[0046] [23] An organic EL device comprising one or more organic layers between a pair of electrodes participating in at least a light emitting function, wherein the one or more organic layers contain organic compounds, at least one of which has a vibration structure in both an excitation spectrum and a fluorescence spectrum.


[0047] [24] An organic EL device comprising one or more organic layers between a pair of electrodes participating in at least a light emitting function, wherein the one or more organic layers contain organic compounds, at least one of which has a Stokes shift of up to 0.1 eV.


[0048] [25] The organic EL device of [24] wherein a host material in a light emitting layer has a greater electron affinity than an electron transporting layer and/or a hole transporting layer.







BRIEF DESCRIPTION OF THE DRAWINGS

[0049]
FIG. 1 is a schematic cross-sectional view showing the basic construction of an organic EL device according to the invention.


[0050]
FIG. 2 is a diagram showing the excitation and fluorescence spectra of the host material and dopant used in Example.


[0051]
FIG. 3 is a diagram showing the excitation and fluorescence spectra of the host material and dopant used in Comparative Example.







DESCRIPTION OF THE PREFERRED EMBODIMENT

[0052] According to the invention, an organic EL device having a high luminous efficiency and a long lifetime is obtained by combining an organic compound of formula (V) or (VI) with at least one of organic compounds of formulas (I) to (IV), especially by combining an organic compound of formula (V) or (VI) as a dopant with an organic compound of formula (I) as a host material. First the organic compounds useful as the host material are described in detail.


[0053] Host Materials


[0054] Naphthacene Compounds


[0055] One class of organic compounds useful as the host material according to the invention have a basic skeleton of the following formula (I).


[0056] In the device of the invention, the use of the naphthacene derivative, preferably as the host material, helps induce strong light emission from the dopant.


[0057] Naphthacene derivatives belong to a class of preferable organic compounds, especially effective as the host material, among others. For example, the fluorescence intensity of a film of a naphthacene derivative of host material in example 1 doped with 1 wt % of a dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative of dopant material in Example 1, as measured on photoexcitation, is about 2 times the fluorescence intensities of films of other organic compounds (e.g., Alq3) as the host.


[0058] The reason why such intense fluorescence is produced is presumably that the combination of a naphthacene derivative with the above dopant is an ideal combination that avoids interaction such as formation of an exciplex, and bipolar interaction between the respective molecules maintains a high intensity of fluorescence.


[0059] In the event of a red dopant, since the energy gap of a naphthacene derivative is relatively approximate to that of the dopant, an energy transfer phenomenon due to emission resorption takes place as well as energy transfer by electron exchange. This accounts for a high fluorescence intensity as well.


[0060] The combination with the above host material minimizes the concentration quenching of the dopant, which also accounts for a high fluorescence intensity.


[0061] In an exemplary organic EL device which was fabricated using the above doped film as a light emitting layer, a luminance of at least 600 cd/m2 at maximum was obtained at a current density of 10 mA/cm2 and a drive voltage as low as about 6 V. When operated at a current density of about 600 mA/cm2, the device consistently produced a luminance of greater than about 20,000 cd/m2. As compared with other organic compounds (e.g., Alq3) serving as the host, this provides a luminous efficiency greater by a factor of about 4 when assessed in terms of current efficiency, and because of possible driving at a lower voltage, a luminous efficiency greater by a factor of about 5 when assessed in terms of power efficiency. In the event of doping with a red dopant as in the above example, entailing the high efficiency of energy transfer from the host to the dopant, the device is characterized by a high chromatic purity in that only the dopant produces light emission, with little light emission from the host being observable.


[0062] It is believed that such a very high luminous efficiency exerted when organic EL devices are fabricated is due to the effects of an improved recombination probability of carriers in the light emitting layer and a singlet excitation state that the dopant forms as a result of energy transfer from the triplet excitation state of naphthacene, as well as the above-mentioned mechanism of providing a high fluorescence intensity.


[0063] As opposed to conventional organic EL devices whose drive voltage is increased by carrier trapping of the dopant, the inventive organic EL device using the above-mentioned light emitting layer has a very low drive voltage, because the order of carrier trapping of the dopant is low and high efficiency light emission is accomplished by the above-mentioned mechanism. Another accomplished by the above-mentioned mechanism. Another probable reason is the ease of injection of carriers into the light emitting layer.


[0064] Since the naphthacene derivative is very stable and highly durable against carrier injection, the device fabricated using the above host-dopant combination has a very long lifetime. For example, an organic EL device having a light emitting layer of a compound of formula (VII′) doped with 1 wt % of a dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative of dopant material in Example 1 is highly durable as demonstrated by its ability to sustain a luminance of at least 2,400 cd/m2 over a period of 1,000 hours or longer, with an attenuation of less than about 1%, when driven at 50 mA/cm2.


[0065] In organic EL devices as mentioned above, the dopant concentration ensuring a chromatic purity and maximum efficiency is about 1% by weight although dopant concentrations of about 2 or 3% by weight lead to devices which are practically acceptable albeit a drop of less than about 10%.
7


[0066] In formula (I), Q1 to Q4 are independently selected from among hydrogen and substituted or unsubstituted alkyl, aryl, amino, heterocyclic and alkenyl radicals. Preferred are aryl, amino, heterocyclic and alkenyl radicals. It is also desirable that Q2 and Q3 are these preferred radicals and Q1 and Q4 are hydrogen.


[0067] The aryl radicals represented by Q1 to Q4 may be monocyclic or polycyclic, inclusive of fused rings and a collection of rings. Those aryl radicals having 6 to 30 carbon atoms in total are preferred and they may have substituents. Preferred examples of the aryl radical include phenyl, o-, m- and p-tolyl, pyrenyl, perylenyl, coronenyl, 1- and 2-naphthyl, anthryl, o-, m- and p-biphenylyl, terphenyl and phenanthryl.


[0068] The amino radicals represented by Q1 to Q4 may be selected from among alkylamino, arylamino, aralkylamino and analogous radicals. They preferably have aliphatic radicals having 1 to 6 carbon atoms in total and/or aromatic carbocyclic radicals having 1 to 4 rings. Illustrative examples include dimethylamino, diethylamino, dibutylamino, diphenylamino, ditolylamino, bisdiphenylylamino, and bisnaphthylamino radicals.


[0069] The heterocyclic radicals represented by Q1 to Q4 include 5- or 6-membered ring aromatic heterocyclic radicals containing O, N or S as a hetero atom, and fused polycyclic aromatic heterocyclic radicals having 2 to 20 carbon atoms. Examples of the aromatic heterocyclic radicals and fused polycyclic aromatic heterocyclic radicals include thienyl, furyl, pyrolyl, pyridyl, quinolyl, and quinoxalyl radicals.


[0070] The alkenyl radicals represented by Q1 to Q4 are preferably those having a phenyl group as at least one substituent, such as 1- and 2-phenylalkenyl, 1,2- and 2,2-diphenylalkenyl, and 1,2,2-triphenylalkenyl although unsubstituted alkenyl radicals are acceptable.


[0071] When Q1 to Q4 are substituted radicals, at least two of the substituents are preferably aryl, amino, heterocyclic, alkenyl or aryloxy groups. These aryl, amino, heterocyclic and alkenyl groups are as illustrated above for Q1 to Q4. The aryloxy groups to substitute on Q1 to Q4 are preferably those of aryl groups having 6 to 18 carbon atoms in total, for example, o-, m- and p-phenoxy. At least two of these substituents may form a fused ring. Also, these substituents may be further substituted ones, in which preferred substituents are as described above.


[0072] When Q1 to Q4 have substituents, it is preferred that at least two of the substituents have the above-described substituents. The position of substitution is not particularly limited and may be a meta, para or ortho position. Q1 and Q4, and Q2 and Q3 in the respective pairs are preferably identical although they may be different.


[0073] Q5 to Q8 are independently selected from among hydrogen and substituted or unsubstituted alkyl, aryl, amino, heterocyclic and alkenyl radicals.


[0074] The alkyl radicals represented by Q5 to Q8 are preferably those of 1 to 6 carbon atoms, which may be straight or branched. Preferred examples of the alkyl radical include methyl, ethyl, n- and i-propyl, n-, i-, sec- and tert-butyl, n-, i-, neo- and tert-pentyl.


[0075] The aryl, amino and alkenyl radicals represented by Q5 to Q8 are as illustrated above for Q1 to Q4. Q5 and Q6, and Q7 and Q8 in the respective pairs are preferably identical although they may be different.


[0076] It is preferred that rubrene of formula (I) wherein all Q1 to Q4 are phenyl and all Q5 to Q8 are hydrogen be excluded.


[0077] The naphthacene derivative contained in the light emitting layer should preferably have a basic skeleton of the following formula (VII).
8


[0078] In formula (VII), Q11 to Q13, Q21 to Q23, Q31 to Q33 and Q41 to Q43 are hydrogen, aryl, amino, heterocyclic, aryloxy or alkenyl radicals. Preferably the Q's in at least one of these sets are radicals having substituents selected from among aryl, amino, heterocyclic and aryloxy groups. Two or more of these Q's may form a fused ring.


[0079] Preferred examples of the aryl, amino, heterocyclic and aryloxy radicals are as exemplified above for Q1 to Q4. Preferably Q11 to Q13 and Q41 to Q43, and Q21 to Q23 and Q31 to Q33 in the respective paired sets are identical although they may be different.


[0080] The amino groups substituting on Q11 to Q13, Q21 to Q23, Q31 to Q33 and Q41 to Q43 may be selected from among alkylamino, arylamino, aralkylamino and analogous groups. They preferably have aliphatic groups having 1 to 6 carbon atoms in total and/or aromatic carbocyclic groups having 1 to 4 rings. Illustrative examples include dimethylamino, diethylamino, dibutylamino, diphenylamino, ditolylamino, and bisbiphenylylamino groups.


[0081] Examples of the fused ring include indene, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, quinoxaline, phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine, benzothiazole, benzothiophene, benzofuran, acridone, benzimidazole, coumarin, and flavone.


[0082] Of the naphthacene derivatives used herein, those of the following formula (VII′) are preferred because devices are given a longer lifetime.
9


[0083] In formula (VII′), Q51 to Q55 and Q21 to Q25 are the same as Q11 in formula (VII).


[0084] Illustrative examples of the preferred naphthacene derivatives used herein are given below as IB-1 to IB-189. The substituents Q1 to Q8 are denoted as Q10 to Q80.
1TABLE 1SUBSTITUENTCompoundNo.Q10Q20Q30Q40Q50Q60Q70Q80IB-110111213HHHHIB-214151617HHHHIB-318192021HHHHIB-422232425HHHHIB-526272829HHHHIB-630313233HHHHIB-734353637HHHHIB-838394041HHHH


[0085]

2





TABLE 2










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-9 


42







43







44







45





H
H
H
H





IB-10


46







47







48







49





H
H
H
H





IB-11


50







51







52







53





H
H
H
H





IB-12


54







55







56







57





H
H
H
H





IB-13


58







59







60







61





H
H
H
H





IB-14


62







63







64







65





H
H
H
H





IB-15


66







67







68







69





H
H
H
H





IB-16


70







71







72







73





H
H
H
H










[0086]

3





TABLE 3










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-17


74







75







76







77





H
H
H
H





IB-18


78







79







80







81





H
H
H
H





IB-19


82







83







84







85





H
H
H
H





IB-20


86







87







88







89





H
H
H
H





IB-21


90







91







92







93





H
H
H
H





IB-22


94







95







96







97





H
H
H
H





IB-23


98







99







100







101





H
H
H
H





IB-24


102







103







104







105





H
H
H
H










[0087]

4





TABLE 4










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-25


106







107







108







109





H
H
H
H





IB-26


110







111







112







113





H
H
H
H





IB-27


114







115







116







117





H
H
H
H





IB-28


118







119







120







121





H
H
H
H





IB-29


122







123







124







125





H
H
H
H





IB-30


126







127







128







129





H
H
H
H





IB-31


130







131







132







133





H
H
H
H





IB-32


134







135







136







137





H
H
H
H










[0088]

5





TABLE 5










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-33


138







139







140







141





H
H
H
H





IB-34


142







143







144







145





H
H
H
H





IB-35


146







147







148







149





H
H
H
H





IB-36


150







151







152







153





H
H
H
H





IB-37


154







155







156







157





H
H
H
H





IB-38


158







159







160







161





H
H
H
H





IB-39


162







163







164







165





H
H
H
H





IB-40


166







167







168







169





H
H
H
H










[0089]

6





TABLE 6










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-41


170







171







172







173





H
H
H
H





IB-42


174







175







176







177





H
H
H
H





IB-43


178







179







180







181





H
H
H
H





IB-44


182







183







184







185





H
H
H
H





IB-45


186







187







188







189





H
H
H
H





IB-46


190







191







192







193





H
H
H
H





IB-47


194







195







196







197





H
H
H
H










[0090]

7





TABLE 7










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-48


198







199







200







201





H
H
H
H





IB-49


202







203







204







205





H
H
H
H





IB-50


206







207







208







209





H
H
H
H





IB-51


210







211







212







213





H
H
H
H





IB-52


214







215







216







217





H
H
H
H





IB-53


218







219







220







221





H
H
H
H





IB-54


222







223







224







225





H
H
H
H





IB-55


226







227







228







229





H
H
H
H










[0091]

8





TABLE 8










SUBSTITUENT


























Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-56


230







231







232







233





H
H
H
H





IB-57


234







235







236







237





H
H
H
H





IB-58


238







239







240







241





H
H
H
H





IB-59


242







243







244







245





H
H
H
H





IB-60


246







247







248







249





H
H
H
H





IB-61


250







251







252







253





H
H
H
H





IB-62


254







255







256







257





H
H
H
H










[0092]

9





TABLE 9










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-63


258







259







260







261





H
H
H
H





IB-64


262







263







264







265





H
H
H
H





IB-65


266







267







268







269





H
H
H
H





IB-66


270







271







272







273





H
H
H
H





IB-67


274







275







276







277





H
H
H
H





IB-68


278







279







280







281





H
H
H
H





IB-69


282







283







284







285





H
H
H
H










[0093]

10





TABLE 10










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-70


286







287







288







289





H
H
H
H





IB-71


290







291







292







293





H
H
H
H





IB-72


294







295







296







297





H
H
H
H





IB-73


298







299







300







301





H
H
H
H





IB-74


302







303







304







305





H
H
H
H





IB-75


306







307







308







309





H
H
H
H





IB-76


310







311







312







313





H
H
H
H





IB-77


314







315







316







317





H
H
H
H










[0094]

11





TABLE 11










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80





























IB-78


318







319







320







321





H
H
H
H





IB-79


322







323







324







325





H
H
H
H





IB-80


326







327







328







329





H
H
H
H





IB-81


330







331







332







333





H
H
H
H





IB-82


334







335







336







337





H
H
H
H





IB-83


338







339







340







341





H
H
H
H





IB-84


342







343







344







345





H
H
H
H





IB-85


346







347







348







349





H
H
H
H










[0095]

12





TABLE 12










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-86


350







351







352







353





H
H
H
H





IB-87


354







355







356







357





H
H
H
H





IB-88


358







359







360







361





H
H
H
H





IB-89


362







363







364







365





H
H
H
H





IB-90


366







367







368







369





H
H
H
H





IB-91


370







371







372







373





H
H
H
H





IB-92


374







375







376







377





H
H
H
H





IB-93


378







379







380







381





H
H
H
H










[0096]

13





TABLE 13










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-94


382







383







384







385





H
H
H
H





IB-95


386







387







388







389





H
H
H
H





IB-96


390







391







392







393





H
H
H
H





IB-97


394







395







396







397





H
H
H
H





IB-98


398







399







400







401





H
H
H
H





IB-99


402







403







404







405





H
H
H
H





IB-100


406







407







408







409





H
H
H
H










[0097]

14





TABLE 14










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-101


410







411







412







413





H
H
H
H





IB-102


414







415







416







417





H
H
H
H





IB-103


418







419







420







421





H
H
H
H





IB-104


422







423







424







425





H
H
H
H





IB-105


426







427







428







429





H
H
H
H





IB-106


430







431







432







433





H
H
H
H





IB-107


434







435







436







437





H
H
H
H





IB-108


438







439







440







441





H
H
H
H










[0098]

15





TABLE 15










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-109


442







443







444







445





H
H
H
H





IB-110


446







447







448







449





H
H
H
H





IB-111


450







451







452







453





H
H
H
H





IB-112


454







455







456







457





H
H
H
H





IB-113


458







459







460







461





H
H
H
H





IB-114


462







463







464







465





H
H
H
H





IB-115


466







467







468







469





H
H
H
H





IB-116


470







471







472







473





H
H
H
H










[0099]

16





TABLE 16










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-117


474







475







476







477





H
H
H
H





IB-118


478







479







480







481





H
H
H
H





IB-119


482







483







484







485





H
H
H
H





IB-120


486







487







488







489





H
H
H
H





IB-121


490







491







492







493





H
H
H
H





IB-122


494







495







496







497





H
H
H
H





IB-123


498







499







500







501





H
H
H
H





IB-124


502







503







504







505





H
H
H
H










[0100]

17





TABLE 17










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-125


506







507







508







509





H
H
H
H





IB-126


510







511







512







513





H
H
H
H





IB-127


514







515







516







517





H
H
H
H





IB-128


518







519







520







521





H
H
H
H





IB-129


522







523







524







525





H
H
H
H





IB-130


526







527







528







529





H
H
H
H





IB-131


530







531







532







533





H
H
H
H





IB-132


534







535







536







537





H
H
H
H










[0101]

18





TABLE 18










SUBSTITUENT


























Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-133


538







539







540







541





H
H
H
H





IB-134


542







543







544







545





H
H
H
H





IB-135


546







547







548







549





H
H
H
H





IB-136


550







551







552







553





H
H
H
H





IB-137


554







555







556







557





H
H
H
H





IB-138


558







559







560







561





H
H
H
H





IB-139


562







563







564







565





H
H
H
H





IB-140


566







567







568







569





H
H
H
H





IB-141


570







571







572







573





H
H
H
H










[0102]

19





TABLE 19















574










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-142


575







576







577







578







579







580





H
H





IB-143


581







582







583







584





CH3
CH3
H
H





IB-144


585







586







587







588







589







590







591







592










IB-145


593







594







595







596







597







598





H
H





IB-146


599







600







601







602







603







604





H
H





IB-147


605







606







607







608







609







610





H
H





IB-148


611







612







613







614





CH3
CH3
CH3
CH3





IB-149


615







616







617







618







619







620





CH3
CH3





IB-150


621







622







623







624







625







626







627







628










IB-151


629







630







631







632







633







634







635







636










IB-152


637







638







639







640







641







642







643







644















[0103]

20





TABLE 20















645










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-153


646







647







648







649





H
H
H
H





IB-154


650







651







652







653







654







655





H
H





IB-155


656







657







658







659





CH3
CH3
H
H





IB-156


660







661







662







663







664







665







666







667










IB-157


668







669







670







671







672







673





H
H





IB-158


674







675







676







677







678







679





H
H





IB-159


680







681







682







683







684







685





H
H





IB-160


686







687







688







689





CH3
CH3
CH3
CH3





IB-161


690







691







692







693







694







695





CH3
CH3










[0104]

21





TABLE 21















696










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-162


697







698







699







700





CH3
CH3
H
H





IB-163


701







702







703







704





CH3
CH3
H
H





IB-164
CH3


705







706





CH3
H
H
H
H





IB-165
CH3


707







708





CH3
H
H
H
H





IB-166
CH3


709







710





CH3
H
H
H
H





IB-167
CH3


711







712





CH3
H
H
H
H





IB-168
H


713







714





H
CH3
CH3
H
H





IB 169
H


715







716





H
CH3
CH3
H
H





IB-170
H


717







718





H
CH3
CH3
H
H










[0105]

22





TABLE 22















719










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-171
H


720







721





H
CH3
CH3
H
H





IB-172
H


722







723





H
CH3
CH3
CH3
CH3





IB-173
H


724







725





H
CH3
CH3
CH3
CH3





IB-174
H


726







727





H
CH3
CH3
CH3
CH3





IB-175
H


728







729





H
CH3
CH3
CH3
CH3










[0106]

23





TABLE 23










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-176


730







731







732







733





CH3
CH3
H
H





IB-177


734







735







736







737





CH3
CH3
H
H





IB-178
CH3


738







739





CH3
H
H
H
H





IB-179
CH3


740







741





CH3
H
H
H
H





IB-180
CH3


742







743





CH3
H
H
H
H





IB-181
CH3


744







745





CH3
H
H
H
H










[0107]

24





TABLE 24










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IB-182
H


746







747





H
CH3
CH3
H
H





IB-183
H


748







749





H
CH3
CH3
H
H





IB-184
H


750







751





H
CH3
CH3
H
H





IB-185
H


752







753





H
CH3
CH3
H
H





IB-186
H


754







755





H
CH3
CH3
CH3
CH3





IB-187
H


756







757





H
CH3
CH3
CH3
CH3





IB-188
H


758







759





H
CH3
CH3
CH3
CH3





IB-189
H


760







761





H
CH3
CH3
CH3
CH3










[0108] Other illustrative examples of the preferred naphthacene derivatives used herein are given below as IIB-1 to IIB-32 and IIIB-1 to IIIB-36. The substituents Q1 to Q8 are denoted as Q10 to Q80.
25TABLE 25SUBSTITUENTCom-poundNo.Q10Q20Q30Q40Q50Q60Q70Q80IIB-1762763764765HHHHIIB-2766767768769HHHHIIB-3770771772773HHHHIIB-4774775776777HHHHIIB-5778779780781HHHHIIB-6782783784785HHHHIIB-7786787788789HHHHIIB-8790791792793HHHH


[0109]

26





TABLE 26










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IIB-9


794







795







796







797





H
H
H
H





IIB-10


798







799







800







801





H
H
H
H





IIB-11


802







803







804







805





H
H
H
H





IIB-12


806







807







808







809





H
H
H
H





IIB-13


810







811







812







813





H
H
H
H





IIB-14


814







815







816







817





H
H
H
H





IIB-15


818







819







820







821





H
H
H
H










[0110]

27





TABLE 27










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IIB-16


822







823







824







825





H
H
H
H





IIB-17


826







827







828







829





H
H
H
H





IIB-18


830







831







832







833





H
H
H
H





IIB-19


834







835







836







837





H
H
H
H





IIB-20


838







839







840







841





H
H
H
H





IIB-21


842







843







844







845





H
H
H
H










[0111]

28





TABLE 28










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IIB-22


846







847







848







849





H
H
H
H





IIB-23


850







851







852







853





H
H
H
H





IIB-24


854







855







856







857





H
H
H
H





IIB-25


858







859







860







861





H
H
H
H





IIB-26


862







863







864







865





H
H
H
H










[0112]

29





TABLE 29










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IIB-27


866







867







868







869





H
H
H
H





IIB-28


870







871







872







873





H
H
H
H





IIB-29


874







875







876







877





H
H
H
H





IIB-30


878







879







880







881





H
H
H
H





IIB-31


882







883







884







885





H
H
H
H





IIB-32


886







887







888







889





H
H
H
H










[0113]

30





TABLE 30










SUBSTITUENT















Com-










pound


No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IIIB-1


890







891







892







893





H
H
H
H





IIIB-2


894







895







896







897





H
H
H
H





IIIB-3


898







899







900







901





H
H
H
H





IIIB-4


902







903







904







905





H
H
H
H





IIIB-5


906







907







908







909





H
H
H
H





IIIB-6


910







911







912







913





H
H
H
H










[0114]

31





TABLE 31










SUBSTITUENT










Compound No.
Q10
Q20
Q30





IIIB-7 


914







915







916










IIIB-8 


917







918







919










IIIB-9 


920







921







922










IIIB-10


923







924







925










IIIB-11


926







927







928










IIIB-12


929







930







931

















SUBSTITUENT














Compound No.
Q40
Q50
Q60
Q70
Q80







IIIB-7 


932





H
H
H
H







IIIB-8 


933





H
H
H
H







IIIB-9 


934





H
H
H
H







IIIB-10


935





H
H
H
H







IIIB-11


936





H
H
H
H







IIIB-12


937





H
H
H
H











[0115]

32





TABLE 32










SUBSTITUENT










Compound No.
Q10
Q20
Q30





IIIB-13


938







939







940










IIIB-14


941







942







943










IIIB-15


944







945







946










IIIB-16


947







948







949










IIIB-17


950







951







952










IIIB-18


953







954







955

















SUBSTITUENT














Compound No.
Q40
Q50
Q60
Q70
Q80







IIIB-13


956





H
H
H
H







IIIB-14


957





H
H
H
H







IIIB-15


958





H
H
H
H







IIIB-16


959





H
H
H
H







IIIB-17


960





H
H
H
H







IIIB-18


961





H
H
H
H











[0116]

33





TABLE 33










SUBSTITUENT











Compound No.
Q10
Q20
Q30
Q40





IIIB-19


962







963







964







965










IIIB-20


966







967







968







969










IIIB-21


970







971







972







973










IIIB-22


974







975







976







977










IIIB-23


978







979







980







981










IIIB-24


982







983







984







985

















SUBSTITUENT













Compound No.
Q50
Q60
Q70
Q80







IIIB-19
H
H
H
H



IIIB-20
H
H
H
H



IIIB-21
H
H
H
H



IIIB-22
H
H
H
H



IIIB-23
H
H
H
H



IIIB-24
H
H
H
H











[0117]

34





TABLE 34










SUBSTITUENT











Compound No.
Q10
Q20
Q30
Q40





IIIB-25


986







987







988







989










IIIB-26


990







991







992







993










IIIB-27


994







995







996







997










IIIB-28


998







999







1000







1001










IIIB-29


1002







1003







1004







1005










IIIB-30


1006







1007







1008







1009

















SUBSTITUENT













Compound No.
Q50
Q60
Q70
Q80







IIIB-25
H
H
H
H



IIIB-26
H
H
H
H



IIIB-27
H
H
H
H



IIIB-28
H
H
H
H



IIIB-29
H
H
H
H



IIIB-30
H H
H
H











[0118]

35





TABLE 35










SUBSTITUENT










Compound No.
Q10
Q20
Q30





IIIB-31


1010







1011







1012










IIIB-32


1013







1014







1015










IIIB-33


1016







1017







1018










IIIB-34


1019







1020







1021










IIIB-35


1022







1023







1024










IIIB-36


1025







1026







1027

















SUBSTITUENTS














Compound No.
Q40
Q50
Q60
Q70
Q80







IIIB-31


1028





H
H
H
H







IIIB-32


1029





H
H
H
H







IIIB-33


1030





H
H
H
H







IIIB-34


1031





H
H
H
H







IIIB-35


1032





H
H
H
H







IIIB-36


1033





H
H
H
H











[0119] Further illustrative examples of the preferred naphthacene derivatives used herein are given below as IVB-1 to IVB-206 and VB-1 to VB-142. The substituents Q1 to Q8 are denoted as Q10 to Q80.
36TABLE 36SUBSTITUENTCompound No.Q10Q20Q30IVB-1 103410351036IVB-2 103710381039IVB-3 104010411042IVB-4 104310441045IVB-5 104610471048IVB-6 104910501051IVB-7 105210531054IVB-8 105510561057IVB-9 105810591060IVB-10106110621063IVB-11106410651066SUBSTITUENTCompound No.Q40Q50Q60Q70Q80IVB-1 1067CH3CH3HHIVB-2 1068CH3CH3HHIVB-3 1069CH3CH3HHIVB-4 1070CH3CH3HHIVB-5 1071CH3CH3HHIVB-6 1072CH3CH3CH3CH3IVB-7 1073CH3CH3CH3CH3IVB-8 1074CH3CH3CH3CH3IVB-9 1075CH3CH3CH3CH3IVB-101076CH3CH3CH3CH3IVB-111077CH3CH3CH3CH3


[0120]

37





TABLE 37










SUBSTITUENT













Compound No.
Q10
Q20
Q30
Q40
Q50
Q60





IVB-12


1078







1079







1080







1081





CH3
CH3





IVB-13


1082







1083







1084







1085





CH3
CH3





IVB-14


1086







1087







1088







1089





CH3
CH3





IVB-15


1090







1091







1092







1093





CH3
CH3





IVB-16


1094







1095







1096







1097







1098







1099










IVB-17


1100







1101







1102







1103







1104







1105










IVB-18


1106







1107







1108







1109







1110







1111










IVB-19


1112







1113







1114







1115







1116







1117

















SUBSTITUENT











Compound No.
Q70
Q80







IVB-12
CH3
CH3



IVB-13
CH3
CH3



IVB-14
CH3
CH3



IVB-15
CH3
CH3







IVB-16


1118







1119












IVB-17


1120







1121












IVB-18


1122







1123












IVB-19


1124







1125
















[0121]

38





TABLE 38










SUBSTITUENT












Compound No.
Q10
Q20
Q30
Q40
Q50





IVB-20


1126







1127







1128







1129







1130










IVB-21


1131







1132







1133







1134







1135










IVB-22


1136







1137







1138







1139







1140










IVB-23


1141







1142







1143







1144







1145










IVB-24


1146







1147







1148







1149







1150










IVB-25


1151







1152







1153







1154







1155










IVB-26


1156







1157







1158







1159







1160










IVB-27


1161







1162







1163







1164







1165










IVB-28


1166







1167







1168







1169







1170










IVB-29


1171







1172







1173







1174







1175










IVB-30


1176







1177







1178







1179







1180










IVB-31


1181







1182







1183







1184







1185










IVB-32


1186







1187







1188







1189







1190















SUBSTITUENT










Compound No.
Q60
Q70
Q80





IVB-20


1191







1192







1193










IVB-21


1194







1195







1196










IVB-22


1197







1198







1199










IVB-23


1200







1201







1202










IVB-24


1203







1204







1205










IVB-25


1206







1207







1208










IVB-26


1209







1210







1211










IVB-27


1212







1213







1214










IVB-28


1215







1216







1217










IVB-29


1218







1219







1220










IVB-30


1221







1222







1223










IVB-31


1224







1225







1226










IVB-32


1227







1228







1229















[0122]

39





TABLE 39










SUBSTITUENT










Compound No.
Q10
Q20
Q30





IVB-33


1230







1231







1232










IVB-34


1233







1234







1235










IVB-35


1236







1237







1238










IVB-36


1239







1240







1241










IVB-37


1242







1243







1244










IVB-38


1245







1246







1247










IVB-39


1248







1249







1250










IVB-40


1251







1252







1253










IVB-41


1254







1255







1256










IVB-42


1257







1258







1259










IVB-43


1260







1261







1262










IVB-44


1263







1264







1265










IVB-45


1266







1267







1268















SUBSTITUENT














Compound No.
Q40
Q50
Q60
Q70
Q80







IVB-33


1269







1270







1271







1272







1273












IVB-34


1274







1275







1276







1277







1278












IVB-35


1279







1280







1281







1282







1283












IVB-36


1284







1285







1286







1287







1288












IVB-37


1289







1290







1291







1292







1293












IVB-38


1294







1295







1296







1297







1298












IVB-39


1299







1300







1301







1302







1303












IVB-40


1304







1305







1306





H
H







IVB-41


1307







1308







1309





H
H







IVB-42


1310







1311







1312





H
H







IVB-43


1313







1314







1315





H
H







IVB-44


1316







1317







1318





H
H







IVB-45


1319







1320







1321





H
H











[0123]

40





TABLE 40










SUBSTITUENT










Compound No.
Q10
Q20
Q30





IVB-46


1322







1323







1324










IVB-47


1325







1326







1327










IVB-48


1328







1329







1330










IVB-48


1331







1332







1333










IVB-49


1334







1335







1336










IVB-50


1337







1338







1339










IVB-51


1340







1341







1342










IVB-52


1343







1344







1345










IVB-53


1346







1347







1348










IVB-54


1349







1350







1351










IVB-55


1352







1353







1354










IVB-56


1355







1356







1357










IVB-57


1358







1359







1360










IVB-58


1361







1362







1363















SUBSTITUENTS










Compound No.
Q40
Q50
Q60





IVB-46


1364







1365







1366










IVB-47


1367







1368







1369










IVB-48


1370







1371







1372










IVB-49


1373







1374







1375










IVB-50


1376







1377







1378










IVB-51


1379







1380







1381










IVB-52


1382





CH3
CH3





IVB-53


1383





CH3
CH3





IVB-54


1384





CH3
CH3





IVB-55


1385





CH3
CH3





IVB-56


1386





CH3
CH3





IVB-57


1387





CH3
CH3





IVB-58


1388





CH3
CH3












SUBSTITUENT











Compound No.
Q70
Q80







IVB-46
H
H



IVB-47
H
H



IVB-48
H
H



IVB-49
H
H



IVB-50
H
H



IVB-51
H
H



IVB-52
H
H



IVB-53
H
H



IVB-54
H
H



IVB-55
H
H



IVB-56
H
H



IVB-57
H
H



IVB-58
H
H











[0124]

41





TABLE 41










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-59


1389







1390







1391







1392





CH3
CH3
H
H





IVB-60


1393







1394







1395







1396





CH3
CH3
H
H





IVB-61


1397







1398







1399







1400





CH3
CH3
H
H





IVB-62


1401







1402







1403







1404





CH3
CH3
H
H





IVB-63


1405







1406







1407







1408





CH3
CH3
H
H





IVB-64


1409







1410







1411







1412





CH3
CH3
H
H





IVB-65


1413







1414







1415







1416





CH3
CH3
H
H





IVB-66


1417







1418







1419







1420





CH3
CH3
H
H





IVB-67


1421







1422







1423







1424





CH3
CH3
H
H





IVB-68


1425







1426







1427







1428





CH3
CH3
H
H





IVB-69


1429







1430







1431







1432





CH3
CH3
H
H










[0125]

42





TABLE 42










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-70


1433







1434







1435







1436





CH3
CH3
H
H





IVB-71


1437







1438







1439







1440





CH3
CH3
H
H





IVB-72


1441







1442







1443







1444





CH3
CH3
H
H





IVB-73


1445







1446







1447







1448





CH3
CH3
H
H





IVB-74


1449







1450







1451







1452





CH3
CH3
H
H





IVB-75


1453







1454







1455







1456





CH3
CH3
H
H





IVB-76


1457







1458







1459







1460





CH3
CH3
H
H





IVB-77


1461







1462







1463







1464





CH3
CH3
H
H





IVB-78


1465







1466







1467







1468





CH3
CH3
H
H





IVB-79


1469







1470







1471







1472





CH3
CH3
H
H










[0126]

43





TABLE 42










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-80


1473







1474







1475







1476





CH3
CH3
H
H





IVB-81


1477







1478







1479







1480





CH3
CH3
H
H





IVB-82


1481







1482







1483







1484





CH3
CH3
H
H





IVB-83


1485







1486







1487







1488





CH3
CH3
H
H





IVB-84


1489







1490







1491







1492





CH3
CH3
CH3
CH3





IVB-85


1493







1494







1495







1496





CH3
CH3
CH3
CH3





IVB-86


1497







1498







1499







1500





CH3
CH3
CH3
CH3





IVB-87


1501







1502







1503







1504





CH3
CH3
CH3
CH3










[0127]

44





TABLE 44










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-88


1505







1506







1507







1508





CH3
CH3
CH3
CH3





IVB-89


1509







1510







1511







1512





CH3
CH3
CH3
CH3





IVB-90


1513







1514







1515







1516





CH3
CH3
CH3
CH3





IVB-91


1517







1518







1519







1520





CH3
CH3
CH3
CH3





IVB-92


1521







1522







1523







1524





CH3
CH3
CH3
CH3





IVB-93


1525







1526







1527







1528





CH3
CH3
CH3
CH3





IVB-94


1529







1530







1531







1532





CH3
CH3
CH3
CH3





IVB-95


1533







1534







1535







1536





CH3
CH3
CH3
CH3





IVB-96


1537







1538







1539







1540





CH3
CH3
CH3
CH3





IVB-97


1541







1542







1543







1544





CH3
CH3
CH3
CH3





IVB-98


1545







1546







1547







1548





CH3
CH3
CH3
CH3










[0128]

45





TABLE 45










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-99 


1549







1550







1551







1552





CH3
CH3
CH3
CH3





IVB-100


1553







1554







1555







1556





CH3
CH3
CH3
CH3





IVB-101


1557







1558







1559







1560





CH3
CH3
CH3
CH3





IVB-102


1561







1562







1563







1564





CH3
CH3
CH3
CH3





IVB-103


1565







1566







1567







1568





CH3
CH3
CH3
CH3





IVB-104


1569







1570







1571







1572





CH3
CH3
CH3
CH3





IVB-105


1573







1574







1575







1576





CH3
CH3
CH3
CH3





IVB-106


1577







1578







1579







1580





CH3
CH3
CH3
CH3





IVB-107


1581







1582







1583







1584





CH3
CH3
CH3
CH3





IVB-108


1585







1586







1587







1588





CH3
CH3
CH3
CH3










[0129]

46





TABLE 46










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-109


1589







1590







1591







1592





CH3
CH3
CH3
CH3





IVB-110


1593







1594







1595







1596





CH3
CH3
CH3
CH3





IVB-111


1597







1598







1599







1600





CH3
CH3
CH3
CH3





IVB-112


1601







1602







1603







1604





CH3
CH3
CH3
CH3





IVB-113


1605







1606







1607







1608





CH3
CH3
CH3
CH3





IVB-114


1609







1610







1611







1612







1613







1614







1615







1616










IVB-115


1617







1618







1619







1620







1621







1622







1623







1624










IVB-116


1625







1626







1627







1628







1629







1630







1631







1632















[0130]

47





TABLE 47










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-117


1633







1634







1635







1636







1637







1638







1639







1640










IVB-118


1641







1642







1643







1644







1645







1646







1647







1648










IVB-119


1649







1650







1651







1652







1653







1654







1655







1656










IVB-120


1657







1658







1659







1660







1661







1662







1663







1664










IVB-121


1665







1666







1667







1668







1669







1670







1671







1672










IVB-122


1673







1674







1675







1676







1677







1678







1679







1680










IVB-123


1681







1682







1683







1684







1685







1686







1687







1688










IVB-124


1689







1690







1691







1692







1693







1694







1695







1696










IVB-125


1697







1698







1699







1700







1701







1702







1703







1704















[0131]

48





TABLE 48










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-126


1705







1706







1707







1708







1709







1710







1711







1712










IVB-127


1713







1714







1715







1716







1717







1718







1719







1720










IVB-128


1721







1722







1723







1724







1725







1726







1727







1728










IVB-129


1729







1730







1731







1732







1733







1734







1735







1736










IVB-130


1737







1738







1739







1740







1741







1742







1743







1744










IVB-131


1745







1746







1747







1748







1749







1750







1751







1752










IVB-132


1753







1754







1755







1756







1757







1758







1759







1760










IVB-133


1761







1762







1763







1764







1765







1766







1767







1768










IVB-134


1769







1770







1771







1772







1773







1774







1775







1776















[0132]

49





TABLE 49










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-135


1777







1778







1779







1780







1781







1782







1783







1784










IVB-136


1785







1786







1787







1788







1789







1790







1791







1792










IVB-137


1793







1794







1795







1796







1797







1798







1799







1800










IVB-138


1801







1802







1803







1804







1805







1806







1807







1808










IVB-139


1809







1810







1811







1812







1813







1814







1815







1816










IVB-140


1817







1818







1819







1820







1821







1822







1823







1824










IVB-141


1825







1826







1827







1828







1829







1830







1831







1832















[0133]

50





TABLE 50










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-142


1833







1834







1835







1836







1837







1838







1839







1840










IVB-143


1841







1842







1843







1844







1845







1846







1847







1848










IVB-144


1849







1850







1851







1852







1853







1854





H
H





IVB-145


1855







1856







1857







1858







1859







1860





H
H





IVB-146


1861







1862







1863







1864







1865







1866





H
H





IVB-147


1867







1868







1869







1870







1871







1872





H
H





IVB-148


1873







1874







1875







1876







1877







1878





H
H





IVB-149


1879







1880







1881







1882







1883







1884





H
H





IVB-150


1885







1886







1887







1888







1889







1890





H
H










[0134]

51





TABLE 51










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-151


1891







1892







1893







1894







1895







1896





H
H





IVB-152


1897







1898







1899







1900







1901







1902





H
H





IVB-153


1903







1904







1905







1906







1907







1908





H
H





IVB-154


1909







1910







1911







1912







1913







1914





H
H





IVB-155


1915







1916







1917







1918







1919







1920





H
H





IVB-156


1921







1922







1923







1924







1925







1926





H
H





IVB-157


1927







1928







1929







1930







1931







1932





H
H





IVB-158


1933







1934







1935







1936







1937







1938





H
H





IVB-159


1939







1940







1941







1942







1943







1944





H
H





IVB-160


1945







1946







1947







1948







1949







1950





H
H





IVB-161


1951







1952







1953







1954







1955







1956





H
H










[0135]

52





TABLE 52










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-162


1957







1958







1959







1960







1961







1962





H
H





IVB-163


1963







1964







1965







1966







1967







1968





H
H





IVB-164


1969







1970







1971







1972







1973







1974





H
H





IVB-165


1975







1976







1977







1978







1979







1980





H
H





IVB-166


1981







1982







1983







1984







1985







1986





H
H





IVB-167


1987







1988







1989







1990







1991







1992





H
H





IVB-168


1993







1994







1995







1996







1997







1998





H
H





IVB-169


1999







2000







2001







2002







2003







2004





H
H










[0136]

53





TABLE 53










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-170


2005







2006







2007







2008







2009







2010





H
H





IVB-171


2011







2012







2013







2014







2015







2016





H
H





IVB-172


2017







2018







2019







2020







2021







2022





H
H





IVB-173


2023







2024







2025







2026







2027







2028





H
H





IVB-174


2029







2030







2031







2032







2033







2034





H
H





IVB-175


2035







2036







2037







2038







2039







2040





H
H










[0137]

54





TABLE 54










SUBSTITUTENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-176


2041







2042







2043







2044







2045







2046





H
H





IVB-177


2047







2048







2049







2050







2051







2052





H
H





IVB-178


2053







2054







2055







2056







2057







2058





H
H





IVB-179


2059







2060







2061







2062







2063







2064





H
H





IVB-180


2065







2066







2067







2068







2069







2070





H
H





IVB-181


2071







2072







2073







2074







2075







2076





H
H





IVB-182


2077







2078







2079







2080







2081







2082





H
H





IVB-183


2083







2084







2085







2086







2087







2088





H
H





IVB-184


2089







2090







2091







2092







2093







2094





H
H





IVB-185


2095







2096







2097







2098







2099







2100





H
H










[0138]

55





TABLE 55










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-186


2101







2102







2103







2104







2105







2106





H
H





IVB-187


2107







2108







2109







2110







2111







2112





H
H





IVB-188


2113







2114







2115







2116







2117







2118





H
H





IVB-189


2119







2120







2121







2122







2123







2124





H
H





IVB-190


2125







2126







2127







2128







2129







2130







2131







2132










IVB-191


2133







2134







2135







2136







2137







2138







2139







2140










IVB-192


2141







2142







2143







2144







2145







2146







2147







2148










IVB-193


2149







2150







2151







2152







2153







2154







2155







2156










IVB-194


2157







2158







2159







2160







2161







2162







2163







2164















[0139]

56





TABLE 56










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















IVB-195


2165







2166







2167







2168







2169







2170







2171







2172










IVB-196


2173







2174







2175







2176







2177







2178







2179







2180










IVB-197


2181







2182







2183







2184







2185







2186







2187







2188










IVB-198


2189







2190







2191







2192







2193







2194







2195







2196










IVB-199


2197







2198







2199







2200







2201







2202







2203







2204










IVB-200


2205







2206







2207







2208







2209







2210







2211







2212










IVB-201


2213







2214







2215







2216







2217







2218







2219







2220










IVB-202


2221







2222







2223







2224







2225







2226







2227







2228










IVB-203


2229







2230







2231







2232







2233







2234







2235







2236















[0140]

57





TABLE 57










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q70
Q70
Q80
















IVB-204


2237







2238







2239







2240







2241







2242







2243







2244










IVB-205


2245







2246







2247







2248







2249







2250







2251







2252










IVB-206


2253







2254







2255







2256







2257







2258







2259







2260















[0141]

58





TABLE 58










SUBSTITUENT


























Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-1
H


2261







2262





H
H
H
H
H





VB-2
H


2263







2264





H
H
H
H
H





VB-3
H


2265







2266





H
H
H
H
H





VB-4
H


2267







2268





H
H
H
H
H





VB-5
H


2269







2270





H
H
H
H
H





VB-6
H


2271







2272





H
H
H
H
H





VB-7
H


2273







2274





H
H
H
H
H





VB-8
H


2275







2276





H
H
H
H
H





VB-9
H


2277







2278





H
H
H
H
H





VB-10
H


2279







2280





H
H
H
H
H





VB-11
H


2281







2282





H
H
H
H
H





VB-12
H


2283







2284





H
H
H
H
H





VB-13
H


2285







2286





H
H
H
H
H





VB-14
H


2287







2288





H
H
H
H
H










[0142]

59





TABLE 59










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-15
H


2289







2290





H
H
H
H
H





VB-16
H


2291







2292





H
H
H
H
H





VB-17
H


2293







2294





H
H
H
H
H





VB-18
H


2295







2296





H
H
H
H
H





VB-19
H


2297







2298





H
H
H
H
H





VB-20
H


2299







2300





H
H
H
H
H





VB-21
H


2301







2302





H
H
H
H
H





VB-22
H


2303







2304





H
H
H
H
H





VB-23
H


2305







2306





H
H
H
H
H





VB-24
H


2307







2308





H
H
H
H
H





VB-25
H


2309







2310





H
H
H
H
H





VB-26
H


2311







2312





H
H
H
H
H










[0143]

60





TABLE 60










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-27
H


2313







2314





H
H
H
H
H





VB-28
H


2315







2316





H
H
H
H
H





VB-29
H


2317







2318





H
H
H
H
H





VB-30
H


2319







2320





H
H
H
H
H





VB-31
H


2321







2322





H
H
H
H
H





VB-32
H


2323







2324





H
H
H
H
H





VB-33
H


2325







2326





H
H
H
H
H





VB-34
H


2327







2328





H
H
H
H
H





VB-35
H


2329







2330





H
H
H
H
H





VB-36
H


2331







2332





H
H
H
H
H





VB-37
H


2333







2334





H
H
H
H
H





VB-38
H


2335







2336





H
H
H
H
H





VB-39
H


2337







2338





H
H
H
H
H










[0144]

61





TABLE 61










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-40
H


2339







2340





H
H
H
H
H





VB-41
H


2341







2342





H
H
H
H
H





VB-42
H


2343







2344





H
H
H
H
H





VB-43
H


2345







2346





H
H
H
H
H





VB-44
H


2347







2348





H
H
H
H
H





VB-45
H


2349







2350





H
H
H
H
H





VB-46
H


2351







2352





H
H
H
H
H





VB-47
H


2353







2354





H
H
H
H
H





VB-48
H


2355







2356





H
H
H
H
H





VB-49
H


2357







2358





H
H
H
H
H





VB-50
H


2359







2360





H
H
H
H
H





VB-51
H


2361







2362





H
H
H
H
H










[0145]

62





TABLE 62










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-52
H


2363







2364





H
H
H
H
H





VB-53
H


2365







2366





H
H
H
H
H





VB-54
H


2367







2368





H
H
H
H
H





VB-55
H


2369







2370





H
H
H
H
H





VB-56
H


2371







2372





H
H
H
H
H





VB-57
H


2373







2374





H
H
H
H
H





VB-58
H


2375







2376





H
H
H
H
H





VB-59
H


2377







2378





H
H
H
H
H





VB-60
H


2379







2380





H
H
H
H
H










[0146]

63





TABLE 63










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-61
H


2381







2382





H
H
H
H
H





VB-62
H


2383







2384





H
H
H
H
H





VB-63
H


2385







2386





H
H
H
H
H





VB-64
H


2387







2388





H
H
H
H
H





VB-65
H


2389







2390





H
H
H
H
H





VB-66
H


2391







2392





H
H
H
H
H





VB-67
H


2393







2394





H
H
H
H
H





VB-68
H


2395







2396





H
H
H
H
H





VB-69
H


2397







2398





H
H
H
H
H





VB-70
H


2399







2400





H
H
H
H
H










[0147]

64





TABLE 64










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-71
H


2401







2402





H
Ph
Ph
Ph
Ph





VB-72
H


2403







2404





H
Ph
Ph
Ph
Ph





VB-73
H


2405







2406





H
Ph
Ph
Ph
Ph





VB-74
H


2407







2408





H
Ph
Ph
Ph
Ph





VB-75
H


2409







2410





H
Ph
Ph
Ph
Ph





VB-76
H


2411







2412





H
Ph
Ph
Ph
Ph





VB-77
H


2413







2414





H
Ph
Ph
Ph
Ph





VB-78
H


2415







2416





H
Ph
Ph
Ph
Ph





VB-79
H


2417







2418





H
Ph
Ph
Ph
Ph





VB-80
H


2419







2420





H
Ph
Ph
Ph
Ph





VB-81
H


2421







2422





H
Ph
Ph
Ph
Ph





VB-82
H


2423







2424





H
Ph
Ph
Ph
Ph





VB-83
H


2425







2426





H
Ph
Ph
Ph
Ph





VB-84
H


2427







2428





H
Ph
Ph
Ph
Ph










[0148]

65





TABLE 65










SUBSTITUENT















Compound No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-85
H


2429







2430





H
Ph
Ph
Ph
Ph





VB-86
H


2431







2432





H
Ph
Ph
Ph
Ph





VB-87
H


2433







2434





H
Ph
Ph
Ph
Ph





VB-88
H


2435







2436





H
Ph
Ph
Ph
Ph





VB-89
H


2437







2438





H
Ph
Ph
Ph
Ph





VB-90
H


2439







2440





H
Ph
Ph
Ph
Ph





VB-91
H


2441







2442





H
Ph
Ph
Ph
Ph





VB-92



2443







2444





H
Ph
Ph
Ph
Ph





VB-93
H


2445







2446





H
Ph
Ph
Ph
Ph





VB-94
H


2447







2448





H
Ph
Ph
Ph
Ph





VB-95
H


2449







2450





H
Ph
Ph
Ph
Ph





VB-96
H


2451







2452





H
Ph
Ph
Ph
Ph










[0149]

66





TABLE 66










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-97 
H


2453







2454





H
Ph
Ph
Ph
Ph





VB-98 
H


2455







2456





H
Ph
Ph
Ph
Ph





VB-99 
H


2457







2458





H
Ph
Ph
Ph
Ph





VB-100
H


2459







2460





H
Ph
Ph
Ph
Ph





VB-101
H


2461







2462





H
Ph
Ph
Ph
Ph





VB-102
H


2463







2464





H
Ph
Ph
Ph
Ph





VB-103
H


2465







2466





H
Ph
Ph
Ph
Ph





VB-104
H


2467







2468





H
Ph
Ph
Ph
Ph





VB-105
H


2469







2470





H
Ph
Ph
Ph
Ph





VB-106
H


2471







2472





H
Ph
Ph
Ph
Ph










[0150]

67





TABLE 67










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-107
H


2473







2474





H
Ph
Ph
H
H





VB-108
H


2475







2476





H
Ph
Ph
H
H





VB-109
H


2477







2478





H
Ph
Ph
H
H





VB-110
H


2479







2480





H
Ph
Ph
H
H





VB-111
H


2481







2482





H
Ph
Ph
H
H





VB-112
H


2483







2484





H
Ph
Ph
H
H





VB-113
H


2485







2486





H
Ph
Ph
H
H





VB-114
H


2487







2488





H
Ph
Ph
H
H





VB-115
H


2489







2490





H
Ph
Ph
H
H





VB-116
H


2491







2492





H
Ph
Ph
H
H





VB-117
H


2493







2494





H
Ph
Ph
H
H





VB-118
H


2495







2496





H
Ph
Ph
H
H





VB-119
H


2497







2498





H
Ph
Ph
H
H





VB-120
H


2499







2500





H
Ph
Ph
H
H










[0151]

68





TABLE 68










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-121
H


2501







2502





H
Ph
Ph
H
H





VB-122
H


2503







2504





H
Ph
Ph
H
H





VB-123
H


2505







2506





H
Ph
Ph
H
H





VB-124
H


2507







2508





H
Ph
Ph
H
H





VB-125
H


2509







2510





H
Ph
Ph
H
H





VB-126
H


2511







2512





H
Ph
Ph
H
H





VB-127
H


2513







2514





H
Ph
Ph
H
H





VB-128
H


2515







2516





H
Ph
Ph
H
H





VB-129
H


2517







2518





H
Ph
Ph
H
H





VB-130
H


2519







2520





H
Ph
Ph
H
H





VB-131
H


2521







2522





H
Ph
Ph
H
H





VB-132
H


2523







2524





H
Ph
Ph
H
H










[0152]

69





TABLE 69










SUBSTITUENT















Compound










No.
Q10
Q20
Q30
Q40
Q50
Q60
Q70
Q80
















VB-133
H


2525







2526





H
Ph
Ph
H
H





VB-134
H


2527







2528





H
Ph
Ph
H
H





VB-135
H


2529







2530





H
Ph
Ph
H
H





VB-136
H


2531







2532





H
Ph
Ph
H
H





VB-137
H


2533







2534





H
Ph
Ph
H
H





VB-138
H


2535







2536





H
Ph
Ph
H
H





VB-139
H


2537







2538





H
Ph
Ph
H
H





VB-140
H


2539







2540





H
Ph
Ph
H
H





VB-141
H


2541







2542





H
Ph
Ph
H
H





VB-142
H


2543







2544





H
Ph
Ph
H
H










[0153] The naphthacene derivatives used herein can be synthesized, for example, using diphenyltetracene quinone and analogues. A typical synthesis scheme is shown below.
2545


[0154] The naphthacene derivatives are used as the host material in combination with dopants.


[0155] Tetraaryldiamine Compounds


[0156] Another class of organic compounds useful as the host material according to the invention are tetraaryldiamine derivatives of the following formula (II).


[0157] In the device of the invention, the use of the tetraaryldiamine derivative, preferably as the host material, helps induce strong light emission from the dopant while controlling the interaction with the dopant.


[0158] In an exemplary organic EL device which was fabricated using a tetraaryldiamine derivative doped with a dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative, a luminance of at least 300 cd/m2 at maximum was obtained at a current density of 10 mA/cm2 and a drive voltage as low as about 6.5 V. When operated at a current density of about 500 mA/cm2, the device consistently produced a luminance of greater than about 15,000 cd/m2. When operated at a current density of about 50 mA/cm2, the device marked a very long lifetime as demonstrated by a half-life time of more than 300 hours at an initial luminance of at least 2400 cd/cm2. Since the tetraaryldiamine derivative has hole transporting ability, a mixture thereof with another of the above-mentioned host materials enables to control carrier balance, resulting in a device with a high efficiency and long lifetime.


[0159] In organic EL devices as mentioned above, the dopant concentration ensuring a chromatic purity and maximum efficiency is about 1% by weight although dopant concentrations of about 2 or 3% by weight lead to devices which are practically acceptable albeit a drop of less than about 10%.
2546


[0160] In formula (II), R1 to R4 are independently aryl, fluorene, carbazolyl, alkyl, alkoxy, aryloxy, amino or halogen radicals, at least one of R1 to R4 is aryl, and r1 to r4 each are 0 or an integer of 1 to 5, with the proviso that r1 to r4 are not 0 at the same time, that is, r1+r2+r3+r4 is an integer of at least 1. R5 and R6 are independently alkyl, alkoxy, amino or halogen radicals and may be the same or different, and r5 and r6 each are 0 or an integer of 1 to 4.


[0161] The aryl radicals represented by R1 to R4 may be monocyclic or polycyclic, inclusive of fused rings and a collection of rings. Those aryl radicals having 6 to 20 carbon atoms in total are preferred. They may have substituents, examples of which are alkyl, alkoxy, aryl, aryloxy, amino and halogen groups. Preferred examples of the aryl radical represented by R1 to R4 include phenyl, o-, m- and p-tolyl, pyrenyl, naphthyl, anthryl, biphenylyl, phenylanthryl and tolylanthryl. Of these, phenyl is most preferred. Preferably the aryl radical, especially phenyl is bonded at the 3- or 4-position.


[0162] The alkyl radicals represented by R1 to R4 may be straight or branched alkyl radicals, preferably of 1 to 10 carbon atoms. They may have substituents, examples of which are as illustrated for the aryl radicals. Preferred examples of the alkyl radical represented by R1 to R4 include methyl, ethyl, n- and i-propyl, n-, i-, sec- and tert-butyl.


[0163] The alkoxy radicals represented by R1 to R4 are preferably those having an alkyl moiety of 1 to 6 carbon atoms, for example, methoxy, ethoxy, and t-butoxy. The alkoxy radicals may have substituents.


[0164] Examples of the aryloxy radicals represented by R1 to R4 include phenoxy, 4-methylphenoxy, and 4-(t-butyl)phenoxy.


[0165] The amino radicals represented by R1 to R4 may be substituted or unsubstituted, with the substituted amino radicals being preferred. Illustrative examples include dimethylamino, diethylamino, diphenylamino, phenyltolylamino and bis(biphenyl)amino radicals.


[0166] Examples of the halogen atom represented by R1 to R4 are chlorine and bromine.


[0167] At least one of R1 to R4 is an aryl radical, and preferably at least two, more preferably at least three of R1 to R4 are aryl radicals. It is then preferred that at least two, more preferably at least three of r1 to r4 are integers of at least 1. Especially at least two, even more preferably at least three of r1 to r4 are equal to 1.


[0168] In formula (II), the alkyl, alkoxy, amino and halogen radicals represented by R5 and R6 are the same as illustrated for R1 to R4.


[0169] It is preferred that both r5 and r6 be 0, that is, the biphenylene radical connecting two arylamino radicals be an unsubstituted one.


[0170] When r1 to r4 are integers of at least 2, the R1 groups, R2 groups, R3 groups and R4 groups may be identical or different, respectively. When r5 and r6 are integers of at least 2, the R5 groups and R6 groups may be identical or different, respectively.


[0171] Of the compounds of formula (II), those compounds of the following formulas (II-1) and (II-2) are preferred.
2547


[0172] In formulas (II-1) and (II-2), R7 to R10 are independently alkyl, alkoxy, aryl, aryloxy, amino radicals or halogen atoms, and may be the same or different. Illustrative examples are the same as described for R1 to R4 in formula (II). Letters r7 to r10 are each 0 or an integer of 1 to 4. It is preferred that r7 to r10 be 0 in both formulas (II-1) and (II-2).


[0173] R11 to R14 are independently alkyl, alkoxy, aryl, aryloxy, amino radicals or halogen atoms, and may be the same or different. Illustrative examples are the same as described for R1 to R4 in formula (II). Letters r11 to r14 are each 0 or an integer of 1 to 5.


[0174] R5, R6, r5 and r6 in formulas (II-1) and (II-2) are as defined in formula (II). It is preferred that r5 and r6 be 0.


[0175] In formulas (II-1) and (II-2), when each of r7 to r10 is an integer of at least 2, the R7 groups, R8 groups, R9 groups and R10 groups may be the same or different, respectively; and when each of r11 to r14 is an integer of at least 2, the R11 groups, R12 groups, R13 groups and R14 groups may be the same or different, respectively.


[0176] Of the compounds of formula (II), those compounds of the following formula (II-3) are also preferred.
2548


[0177] R5, R6, r5 and r6 in formula (II-3) are as defined in formula (II). It is preferred that r5 and r6 be 0.


[0178] Ar1 and Ar2 each are an aryl radical and may be the same or different. Illustrative examples of the aryl radical are as described for R1 to R4 in formula (II). Phenyl and biphenyl radicals are preferred among others.


[0179] R15 and R16 are independently alkyl, alkoxy, aryl, aryloxy, amino radicals or halogen atoms, and may be the same or different. Illustrative examples are the same as described for R1 to R4 in formula (II). Letters r15 and r16 are each 0 or an integer of 1 to 4. It is preferred that r15 and r16 be 0.


[0180] R17 and R18 are independently alkyl, alkoxy, aryloxy, amino radicals or halogen atoms, and may be the same or different. Illustrative examples are the same as described for R1 to R4 in formula (II). Letters r17 and r18 are each 0 or an integer of 1 to 5. It is preferred that r17 and r18 be 0.


[0181] In formula (II-3), when each of r15 and r16 is an integer of at least 2, the R15 groups and R16 groups may be the same or different, respectively; and when each of r17 and r18 is an integer of at least 2, the R17 groups and R18 groups may be the same or different, respectively.


[0182] Illustrative, non-limiting, examples of the compound of formula (II) are given below. It is noted that general formulas are followed by lists of R's to show illustrative examples by combinations of R's and optionally Ar's. As to a set of R's, when all R's in that set are hydrogen, H is assigned to that set. When a substituent is present as any of R's in a set, only the substituent is designated in the set, indicating that the remainders are hydrogen. Ar1 and Ar2 are individually shown.
702549Com-poundNo.R1˜R4R5˜R9R10˜R13R14˜R18R19˜R22R23˜R27R28˜R31R32˜R36R37˜R44I-1HHHHHHHHHI-2HR6 = CH3HR17═CH3HR26 = CH3HR35 = CH3HI-3HR7 = CH3HR16 = CH3HR25 = CH3HR34 = CH3HI-4HR7 = t-C4H9HR16 = t-C4H9HR25 = t-C4H9HR34 = t-C4H9HI-5HR7 = OCH3HR16 = OCH3HR25 = OCH3HR34 = OCH3HI-6HR7 = PhHR16 = PhHR25 = PhHR34 = PhHI-7H2550H2551H2552H2553HI-8HR7 = OPhHR16 = OPhHR25 = OPhHR34 = OPhHI-9HR7 = N(C2H5)2HR16 = N(C2H5)2HR25 = N(C2H5)2HR34 = N(C2H5)2HI-10HR7 = N(Ph)2HR16 = N(Ph)2HR25 = N(Ph)2HR34 = N(Ph)2HI-11HR7 = ClHR16 = ClHR25 = ClHR34 = ClHI-12R2 = CH3HR11 = CH3HR20 = CH3HR29 = CH3HHI-13HR6 = PhHR17 = PhHR26 = PhHR35 = PhHI-14HR7 = PhHR16 = PhHHHHHI-15HR6 = PhHR17 = PhHHHHHI-16R2 = OCH3HR11 = OCH3HR20 = OCH3HR29 = OCH3HHI-17R2 = PhHR11 = PhHR20 = PhHR29 = PhHHI-18R2 = OPhHR11 = OPhHR20 = OPhHR29 = OPhHHI-19R2 = N(C2H5)2HR11 = N(C2H5)2HR20 = N(C2H5)2HR29 = N(C2H5)2HHI-20R2 = ClHR11 = ClHR20 = ClHR29 = ClHHI-21HHHHHHHHR37 = R42 = CH3I-22HHHHHHHHR37 = R42 = OCH3I-23HHHHHHHHR37 = R42 = N(C2H5)2I-24HHHHHHHHR37 = R42 = ClI-25HHHHHHHHR40 = R43 = CH3I-26R2 = PhR7 = PhR11 = PhR16 = PhR20 = PhR25 = PhR29 = PhR34 = PhHI-27R2 = N(Ph)2HR11 = PhHR20 = PhHR29 = PhHHI-28HR6 = CH3HR16 = CH3HR26 = CH3HR34 = CH3HI-29HR6 = R8 = CH3HHHR24 = R26 = CH3HHH


[0183]

71
















2554
























Com-











pound


No.
R51˜R54
R55˜R59
R60˜R63
R64˜R68
R69˜R72
R73˜R77
R78˜R81
R82˜R86
R87˜R94

















II-1
H
H
H
H
H
H
H
H
H


II-2
H
R56 = CH3
H
R67 = CH3
H
R74 = CH3
H
R85 = CH3
H


II-3
H
R57 = CH3
H
R66 = CH3
H
R75 = CH3
H
R84 = CH3
H


II-4
H
R57 = t-C4H9
H
R66 = t-C4H9
H
R75 = t-C4H9
H
R84 = t-C4H9
H


II-5
H
R57 = OCH3
H
R66 = OCH3
H
R75 = OCH3
H
R84 = OCH3
H


II-6
H
R57 = Ph
H
R66 = Ph
H
R75 = Ph
H
R84 = Ph
H





II-7
H


2555





H


2556





H


2557





H


2558





H





II-8
H
R57 = OPh
H
R66 = OPh
H
R75 = OPh
H
R84 = OPh
H


II-9
H
R57 = N(C2H5)2
H
R66 = N(C2H5)2
H
R75 = N(C2H5)2
H
R84 = N(C2H5)2
H


II-10
H
R57 = N(Ph)2
H
R66 = N(Ph)2
H
R75 = N(Ph)2
H
R84 = N(Ph)2
H


II-11
H
R57 = Cl
H
R66 = Cl
H
R75 = Cl
H
R84 = Cl
H


II-12
R52 = CH3
H
R62 = CH3
H
R72 = CH3
H
R79 = CH3
H
H


II-13
R52 = OCH3
H
R62 = OCH3
H
R72 = OCH3
H
R79 = OCH3
H
H


II-14
R52 = Ph
H
R62 = Ph
H
R72 = Ph
H
R79 = Ph
H
H


II-15
R52 = OPh
H
R62 = OPh
H
R72 = OPh
H
R79 = OPh
H
H


II-16
R52 = N(C2H5)2
H
R62 = N(C2H5)2
H
R72 = N(C2H5)2
H
R79 = N(C2H5)2
H
H


II-17
R52 = Cl
H
R62 = Cl
H
R72 = Cl
H
R79 = Cl
H
H


II-18
H
H
H
H
H
H
H
H
R87 = R92 = CH3


II-19
H
H
H
H
H
H
H
H
R87 = R92 = OCH3


II-20
H
H
H
H
H
H
H
H
R87 = R92 = N(C2H5)2


II-21
H
H
H
H
H
H
H
H
R87 = R92 = Cl


II-22
H
H
H
H
H
H
H
H
R90 = R92 = CH3


II-23
H
R57 = CH3
H
R67 = CH3
H
R75 = CH3
H
R85 = CH3
H


II-24
H
R56 = R58 = CH3
H
H
H
R74 = R76 = CH3
H
H
H










[0184]

72
















2559






















Com-









pound


No.
Ar1
Ar2
R101˜R104
R105˜R108
R109˜R113
R114˜R118
R119˜R126















III-1
Ph
Ph
H
H
H
H
H


III-2
Ph
Ph
H
H
R110 = CH3
R115 = CH3
H


III-3
Ph
Ph
H
H
R111 = CH3
R116 = CH3
H


III-4
Ph
Ph
H
H
R111 = t-C4H9
R116 = t-C4H9
H


III-5
Ph
Ph
H
H
R111 = OCH3
R116 = OCH3
H


III-6
Ph
Ph
H
H
R111 = Ph
R116 = Ph
H





III-7
Ph
Ph
H
H


2560







2561





H





III-8
Ph
Ph
H
H
R111 = OPh
R116 = OPh
H


III-9
Ph
Ph
H
H
R111 = N(C2H5)2
R116 = N(C2H5)2
H


III-10
Ph
Ph
H
H
R111 = N(Ph)2
R116 = N(Ph)2
H


III-11
Ph
Ph
H
H
R111 = Cl
R116 = Cl
H


III-12
Ph
Ph
R102 = CH3
R106 = CH3
H
H
H


III-13
Ph
Ph
H
H
R111 = CH3
R115 = CH3
H


III-14
Ph
Ph
H
H
R111 = OCH3
R115 = OCH3
H


III-15
Ph
Ph
R102 = OCH3
R106 = OCH3
H
H
H


III-16
Ph
Ph
R102 = Ph
R106 = Ph
H
H
H


III-17
Ph
Ph
R102 = OPh
R106 = OPh
H
H
H


III-18
Ph
Ph
R102 = N(C2H5)2
R106 = N(C2H5)2
H
H
H


III-19
Ph
Ph
R102 = Cl
R106 = Cl
H
H
H


III-20
Ph
Ph
H
H
H
H
R119 = R124 = CH3


III-21
Ph
Ph
H
H
H
H
R119 = R124 = OCH3


III-22
Ph
Ph
H
H
H
H
R119 = R124 = N(C2H5)2


III-23
Ph
Ph
H
H
H
H
R119 = R124 = Cl





III-24


2562







2563





H
H
H
H
H





III-25


2564







2565





H
H
H
H
H





III-26


2566







2567





H
H
H
H
H





III-27
Ph


2568





H
H
H
H
H





III-28


2569







2570





H
H
H
H
H










[0185]

73


















IV-1


2571










IV-2


2572










IV-3


2573










IV-4


2574










IV-5


2575










V-1


2576










V-2


2577










V-3


2578










V-4


2579










V-5


2580










VI-1


2581










VI-2


2582










VI-3


2583










VI-4


2584













2585













2586




















R3 = R23
R4 = R24
R13 = R33
R14 = R44














Ph
H
H
H



H
Ph
H
H



Ph
H
Ph
H



H
Ph
H
Ph



CH3
H
H
H



H
CH3
H
H



CH3
H
CH3
H



H
CH3
H
CH3











[0186] The above-described host compounds can be synthesized by the method described in Jean Piccard, Herr. Chim. Acta., 7, 789 (1924), Jean Piccard, J. Am. Chem. Soc., 48, 2878 (1926), etc. or similar methods. More particularly, Ullmann reaction is effected by heating in the presence of copper a combination of a di(biphenyl)amine compound with a diiodobiphenyl compound or a combination of a N,N′-diphenylbenzidine compound with a iodobiphenyl compound, selected in accordance with the end compound.


[0187] The host compounds can be identified by mass analysis, infrared (IR) absorption spectroscopy or nuclear magnetic resonance spectroscopy (1H-NMR).


[0188] These compounds have a molecular weight of about 640 to about 800, a high melting point of about 190 to about 300° C., and a high glass transition temperature of about 80 to about 150° C. On conventional vacuum evaporation, they form satisfactory smooth films which are transparent and remain amorphous even above room temperature. The films maintain the stable amorphous state over a long period of time. Accordingly, thin films can be formed from the compounds alone without a need for binder resins.


[0189] Anthracene Compounds


[0190] A further class of organic compounds useful as the host material according to the invention are phenylanthracene derivatives of the following formula (III).


[0191] In the device of the invention, the use of the anthracene derivative of formula (III), preferably as the host material, helps induce strong light emission from the dopant while controlling the interaction with the dopant. Since the anthracene derivatives are fully heat resistant and durable, organic EL devices with a longer lifetime are obtainable.


[0192] In an exemplary organic EL device which was fabricated using an anthracene derivative doped with a dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative, a luminance of at least 250 cd/m2 was obtained at a current density of 10 mA/cm2 and a drive voltage as low as about 6.5 V. When operated at a current density of about 600 mA/cm2, the device consistently produced a luminance of greater than about 13,000 cd/m2. When operated at a current density of about 50 mA/cm2, the device marked a very long lifetime as demonstrated by a half-life time of more than 300 hours at an initial luminance of at least 2400 cd/cm2.


[0193] In organic EL devices as mentioned above, the dopant concentration ensuring a chromatic purity and maximum efficiency is about 1% by weight although dopant concentrations of about 2 or 3% by weight lead to devices which are practically acceptable albeit a drop of less than about 10%.
2587


[0194] Herein A101 is a monophenylanthryl or diphenylanthryl radical and may be the same or different, L is hydrogen, a single bond or a divalent linkage, and n is an integer of 1 or 2.


[0195] Of the compounds of formula (III), those compounds of the following formulas (III-1) and (III-2) are preferred.
2588


[0196] Evaporated films of these compounds remain in a stable amorphous state, that is, have sufficient physical properties to produce consistent uniform light emission. The films remain stable over one year in the ambient atmosphere without crystallization.


[0197] Referring to formula (III), A101 is a monophenylanthryl or diphenylanthryl radical and may be the same or different, and n is an integer of 1 or 2. The monophenylanthryl or diphenylanthryl radical represented by A101 may be substituted or unsubstituted. Exemplary substituents are alkyl, aryl, alkoxy, aryloxy and amino groups. These substituents may further have substituents thereon and will be described later. The position of a substituent on the monophenylanthryl or diphenylanthryl radical is not critical although the preferred substitution position is on the phenyl group bonded to the anthracene ring rather than the anthracene ring.


[0198] Preferably the phenyl group is bonded to the anthracene ring at the 9- and 10-positions.


[0199] In formula (III), L is hydrogen, a single bond or a divalent linkage. The divalent linkage represented by L is preferably an arylene radical which may be separated by an alkylene or analogous group. The arylene radical will be described later.


[0200] Of the phenylanthracene derivatives of formula (III), those of formulas (III-1) and (III-2) are preferred. Formula (III-1) is described in detail.


[0201] In formula (III-1), M1 and M2 each are alkyl, cycloalkyl, aryl, alkoxy, aryloxy, amino or heterocyclic radicals.


[0202] The alkyl radicals represented by M1 and M2 may be substituted or unsubstituted, straight or branched alkyl radicals, preferably of 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms. Unsubstituted alkyl radicals of 1 to 4 carbon atoms are preferred, such as, for example, methyl, ethyl, n- and i-propyl, and n-, i-, sec- and tert-butyl.


[0203] Exemplary of the cycloalkyl radicals represented by M1 and M2 are cyclohexyl and cyclopentyl.


[0204] The aryl radicals represented by M1 and M2 are preferably those aryl radicals having 6 to 20 carbon atoms which may have substituents such as phenyl and tolyl. Preferred examples of the aryl radical include phenyl, o-, m- and p-tolyl, pyrenyl, naphthyl, anthryl, biphenyl, phenylanthryl and tolylanthryl.


[0205] The alkenyl radicals represented by M1 and M2 are preferably those having 6 to 50 carbon atoms in total, which may be substituted or unsubstituted, with the substituted ones being preferred. Such substituents are aryl groups such as phenyl. Exemplary alkenyl radicals are triphenylvinyl, tritolylvinyl and tribiphenylvinyl.


[0206] The alkoxy radicals represented by M1 and M2 are preferably those having an alkyl moiety of 1 to 6 carbon atoms, for example, methoxy and ethoxy. The alkoxy radicals may have substituents.


[0207] Exemplary of the aryloxy radicals represented by M1 and M2 is phenoxy.


[0208] The amino radicals represented by M1 and M2 may be substituted or unsubstituted, with the substituted amino radicals being preferred. Such substituents are alkyl groups such as methyl and ethyl and aryl groups such as phenyl. Illustrative examples of the amino radical include diethylamino, diphenylamino and di(m-tolyl)amino radicals.


[0209] The heterocyclic radicals represented by M1 and M2 include bipyridyl, pyrimidyl, quinolyl, pyridyl, thienyl, furyl and oxadiazoyl radicals and may have substituents such as methyl and phenyl.


[0210] In formula (III-1), q1 and q2 each are 0 or an integer of 1 to 5, especially 0 or 1. When q1 and q2 each are an integer of 1 to 5, especially 1 or 2, M1 and M2 each are preferably alkyl, aryl, alkenyl, alkoxy, aryloxy or amino radicals.


[0211] In formula (III-1), M1 and M2 may be the same or different. Where a plurality of M1 or M2 are included, the M1 groups or M2 groups may be the same or different. Alternatively, the M1 groups or M2 groups bond together to form a ring such as a benzene ring. The ring formation is also a preferred embodiment.


[0212] In formula (III-1), L1 is hydrogen, a single bond or an arylene radical. The arylene radicals represented by L1 are preferably unsubstituted ones, for example, ordinary arylene radicals such as phenylene, biphenylene and anthrylene as well as two or more arylene radicals which are directly bonded. L1 is preferably a single bond, p-phenylene or 4,4′-biphenylene.


[0213] The arylene radical represented by L1 may consist of two or more arylene radicals which are connected by an alkylene radical, —O—, —S— or —NR— wherein R is an alkyl or aryl radical. Exemplary alkyl radicals are methyl and ethyl, and an exemplary aryl radical is phenyl. R is preferably an aryl radical, such as phenyl. Alternatively, R is A101 or a phenyl radical having A101 substituted thereon. The alkylene radicals are preferably methylene and ethylene.


[0214] Illustrative examples of the arylene radical are given below.
2589


[0215] Next referring to formula (III-2), M3 and M4 are the same as M1 and M2 in formula (III-1), q3 and q4 are the same as q1 and q2 in formula (III-1), and L2 is the same as L1 in formula (III-1). Preferred examples of these radicals are also the same.


[0216] In formula (III-2), M3 and M4 may be the same or different. Where a plurality of M3 or M4 are included, the M3 groups or M4 groups may be the same or different. Alternatively, the M3 groups or M4 groups bond together to form a ring such as a benzene ring. The ring formation is also a preferred embodiment.


[0217] Illustrative, non-limiting, examples of the compounds of formulas (III-1) and (III-2) are given below. It is noted that general formulas are followed by lists of M's to show illustrative examples by combinations of M11 to M15 and M21 to M25 or combinations of M31 to M35 and M41 to M45.
742590Compound No.M11M12M13M14M15M21M22M23M24M25I-1 HHHHHHHHHHI-2 CH3HHHHCH3HHHHI-3 t-C4H9HHHHt-C4H9HHHHI-4 OCH3HHHHOCH3HHHHI-5 OPhHHHHOPhHHHHI-6 N(C2H5)2HHHHN(C2H5)2HHHHI-7 N(Ph)2HHHHN(Ph)2HHHHI-8 PhHHHHPhHHHHI-9 2591HHHH2592HHHHI-10HCH3HHHHCH3HHHI-11HCH3HCH3HHCH3HCH3HI-12HHCH3HHHHCH3HHI-13HCH3HHCH3HCH3HHCH3I-14t-C4H9HHHHHHHHHI-152593HHHH2594HHHHI-16HPhHHHHPhHHHI-17HHPhHHHHPhHHI-182595HHHH2596HHHHI-19n-C4H9HHHHn-C4H9HHHHI-202597HHHH2598HHHHI-21HH2599HHHH2600HHI-222601HHHH2602HHHHI-23HH2603HHHH2604HHI-24HHPhHPhHHPhHPhI-25HHPhPhHHHPhPhH


[0218]

75
















2605

























Compound No.
M11
M12
M13
M14
M15
M21
M22
M23
M24
M25





II-1 
H
H
H
H
H
H
H
H
H
H


II-2 
CH3
H
H
H
H
CH3
H
H
H
H


II-3 
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H


II-4 
OCH3
H
H
H
H
OCH3
H
H
H
H


II-5 
OPh
H
H
H
H
OPh
H
H
H
H


II-6 
N(C2H5)2
H
H
H
H
N(C2H5)2
H
H
H
H


II-7 
N(Ph)2
H
H
H
H
N(Ph)2
H
H
H
H


II-8 
Ph
H
H
H
H
Ph
H
H
H
H





II-9 


2606





H
H
H
H


2607





H
H
H
H


II-10
H
CH3
H
H
H
H
CH3
H
H
H


II-11
H
H
CH3
H
H
H
CH3
CH3
H
H


II-12
H
H
CH3
CH3
H
H
H
CH3
CH3
H


II-13
H
H
CH3
H
CH3
H
CH3
CH3
H
CH3


II-14
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3


II-15
t-C4H9
H
H
H
H
H
H
H
H
H





II-16


2608





H
H
H
H


2609





H
H
H
H





II-17
H
Ph
H
H
H
H
Ph
H
H
H


II-18
H
H
Ph
H
H
H
H
Ph
H
H





II-19
H
H


2610





H
H
H
H


2611





H
H





II-20


2612





H
H
H
H


2613





H
H
H
H





II-21


2614





H
H
H
H


2615





H
H
H
H





II-22
H
H


2616





H
H
H
H


2617





H
H





II-23
H
H
Ph
H
Ph
H
H
Ph
H
Ph


II-24
H
H
Ph
Ph
H
H
H
Ph
Ph
H










[0219]

76
















2618

























Compound No.
M11
M12
M13
M14
M15
M21
M22
M23
M24
M25





III-1 
H
H
H
H
H
H
H
H
H
H


III-2 
CH3
H
H
H
H
CH3
H
H
H
H


III-3 
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H


III-4 
OCH3
H
H
H
H
OCH3
H
H
H
H


III-5 
OPh
H
H
H
H
OPh
H
H
H
H


III-6 
N(C2H5)2
H
H
H
H
N(C2H5)2
H
H
H
H


III-7 
N(Ph)2
H
H
H
H
N(Ph)2
H
H
H
H


III-8 
Ph
H
H
H
H
Ph
H
H
H
H





III-9 


2619





H
H
H
H


2620





H
H
H
H





III-10
H
CH3
H
H
H
H
CH3
H
H
H


III-11
H
H
CH3
H
H
H
H
CH3
H
H


III-12
H
H
CH3
CH3
H
H
H
CH3
CH3
H


III-13
H
H
CH3
H
CH3
H
H
CH3
H
CH3


III-14
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3


III-15
H
Ph
H
H
H
H
Ph
H
H
H


III-16
H
H
Ph
H
H
H
H
Ph
H
H





III-17


2621





H
H
H
H


2622





H
H
H
H





III-18
t-C4H9
H
H
H
H
H
H
H
H
H





III-19


2623





H
H
H
H


2624





H
H
H
H





III-20


2625





H
H
H
H


2626





H
H
H
H





III-21


2627





H
H
H
H


2628





H
H
H
H





III-22


2629





H
H
H
H


2630





H
H
H
H





III-23


2631





H
H
H
H


2632





H
H
H
H





III-24
H
H


2633





H
H
H
H


2634





H
H





III-25


2635





H
H
H
H


2636





H
H
H
H





III-26
H
H


2637





H
H
H
H


2638





H
H





III-27
H
H
Ph
H
Ph
H
H
Ph
H
Ph


III-28
H
H
Ph
Ph
H
H
H
Ph
Ph
H










[0220]

77
















2639

























Compound No.
M11
M12
M13
M14
M15
M21
M22
M23
M24
M25





IV-1 
H
H
H
H
H
H
H
H
H
H


IV-2 
CH3
H
H
H
H
CH3
H
H
H
H


IV-3 
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H


IV-4 
OCH3
H
H
H
H
OCH3
H
H
H
H


IV-5 
OPh
H
H
H
H
OPh
H
H
H
H


IV-6 
N(C2H5)2
H
H
H
H
N(C2H5)2
H
H
H
H


IV-7 
N(Ph)2
H
H
H
H
N(Ph)2
H
H
H
H


IV-8 
Ph
H
H
H
H
Ph
H
H
H
H





IV-9 


2640





H
H
H
H


2641





H
H
H
H





IV-10
H
CH3
H
H
H
H
CH3
H
H
H


IV-11
H
H
CH3
H
H
H
H
CH3
H
H


IV-12
H
H
CH3
CH3
H
H
H
CH3
CH3
H


IV-13
H
H
CH3
H
CH3
H
H
CH3
H
CH3


IV-14
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3


IV-15
H
H
H
H
H
H
H
H
H
H


IV-16
H
H
Ph
H
H
H
H
Ph
H
H





IV-17


2642





H
H
H
H


2643





H
H
H
H


IV-18
t-C4H9
H
H
H
H
H
H
H
H
H





IV-19


2644





H
H
H
H


2645





H
H
H
H





IV-20


2646





H
H
H
H


2647





H
H
H
H





IV-21


2648





H
H
H
H


2649





H
H
H
H





IV-22
H
H


2650





H
H
H
H


2651





H
H





IV-23


2652





H
H
H
H


2653





H
H
H
H





IV-24
H
H


2654





H
H
H
H


2655





H
H





IV-25
H
H
Ph
H
Ph
H
H
Ph
H
Ph


IV-26
H
H
Ph
Ph
H
H
H
Ph
Ph
H










[0221]

78
















2656

























Compound No.
M31
M32
M33
M34
M35
M41
M42
M43
M44
M45





V-1 
H
H
H
H
H
H
H
H
H
H


V-2 
CH3
H
H
H
H
CH3
H
H
H
H


V-3 
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H


V-4 
OCH3
H
H
H
H
OCH3
H
H
H
H


V-5 
OPh
H
H
H
H
OPh
H
H
H
H


V-6 
N(C2H5)2
H
H
H
H
N(C2H5)2
H
H
H
H


V-7 
N(Ph)2
H
H
H
H
N(Ph)2
H
H
H
H


V-8 
Ph
H
H
H
H
Ph
H
H
H
H





V-9 


2657





H
H
H
H


2658





H
H
H
H





V-10
H
CH3
H
H
H
H
CH3
H
H
H


V-11
H
H
CH3
H
H
H
H
CH3
H
H


V-12
H
H
CH3
CH3
H
H
H
CH3
CH3
H


V-13
H
H
CH3
H
CH3
H
H
CH3
H
CH3


V-14
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3


V-15
H
Ph
H
H
H
H
Ph
H
H
H


V-16
H
H
Ph
H
H
H
H
Ph
H
H





V-17


2659





H
H
H
H


2660





H
H
H
H





V-18
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H





V-19


2661





H
H
H
H


2662





H
H
H
H





V-20


2663





H
H
H
H


2664





H
H
H
H





V-21


2665





H
H
H
H


2666





H
H
H
H





V-22


2667





H
H
H
H


2668





H
H
H
H





V-23


2669





H
H
H
H


2670





H
H
H
H





V-24


2671





H
H
H
H


2672





H
H
H
H





V-25
H
H


2673





H
H
H
H


2674





H
H





V-26


2675





H
H
H
H


2676





H
H
H
H





V-27
H
H


2677





H
H
H
H


2678





H
H





V-28
H
H
Ph
H
Ph
H
H
Ph
H
Ph


V-29
H
H
Ph
Ph
H
H
H
Ph
Ph
H










[0222]

79
















2679

























Compound No.
M31
M32
M33
M34
M35
M41
M42
M43
M44
M45





VI-1 
H
H
H
H
H
H
H
H
H
H


VI-2 
CH3
H
H
H
H
CH3
H
H
H
H


VI-3 
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H


VI-4 
OCH3
H
H
H
H
OCH3
H
H
H
H


VI-5 
OPh
H
H
H
H
OPh
H
H
H
H


VI-6 
N(C2H5)2
H
H
H
H
N(C2H5)2
H
H
H
H


VI-7 
N(Ph)2
H
H
H
H
N(Ph)2
H
H
H
H


VI-8 
Ph
H
H
H
H
Ph
H
H
H
H





VI-9 


2680





H
H
H
H


2681





H
H
H
H





VI-10
H
CH3
H
H
H
H
CH3
H
H
H


VI-11
H
H
CH3
H
H
H
H
CH3
H
H


VI-12
H
H
CH3
CH3
H
H
H
CH3
CH3
H


VI-13
H
H
CH3
H
CH3
H
H
CH3
H
CH3


VI-14
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3


VI-15
H
Ph
H
H
H
H
Ph
H
H
H


VI-16
H
H
Ph
H
H
H
H
Ph
H
H





VI-17


2682





H
H
H
H


2683





H
H
H
H





VI-18
t-C4H9
H
H
H
H
H
H
H
H
H





VI-19


2684





H
H
H
H


2685





H
H
H
H





VI-20


2686





H
H
H
H


2687





H
H
H
H





VI-21


2688





H
H
H
H
H
H
H
H
H





VI-22


2689





H
H
H
H
CH3
H
H
H
H





VI-23


2690





H
H
H
H


2691





H
H
H
H





VI-24


2692





H
H
H
H


2693





H
H
H
H





VI-25
H
H
Ph
H
Ph
H
H
Ph
H
Ph


VI-26
H
H
Ph
Ph
H
H
H
Ph
Ph
H





VI-27
H
H


2694





H
H
H
H


2695





H
H





VI-28
H
H


2696





H
H
H
H


2697





H
H










[0223]

80
















2698

























Compound No.
M31
M32
M33
M34
M35
M41
M42
M43
M44
M45





VII-1 
H
H
H
H
H
H
H
H
H
H


VII-2 
CH3
H
H
H
H
CH3
H
H
H
H


VII-3 
t-C4H9
H
H
H
H
t-C4H9
H
H
H
H


VII-4 
OCH3
H
H
H
H
OCH3
H
H
H
H


VII-5 
OPh
H
H
H
H
OPh
H
H
H
H


VII-6 
N(C2H5)2
H
H
H
H
N(C2H5)2
H
H
H
H


VII-7 
N(Ph)2
H
H
H
H
N(Ph)2
H
H
H
H


VII-8 
Ph
H
H
H
H
Ph
H
H
H
H





VII-9 


2699





H
H
H
H


2700





H
H
H
H





VII-10
H
H
CH3
CH3
H
H
H
CH3
CH3
H


VII-11
H
H
CH3
H
CH3
H
H
CH3
H
CH3


VII-12
H
CH3
H
H
H
H
CH3
H
H
H


VII-13
H
H
CH3
H
H
H
H
CH3
H
H


VII-14
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3


VII-15
H
H
Ph
H
Ph
H
H
Ph
H
Ph


VII-16
H
H
Ph
Ph
H
H
H
Ph
Ph
H





VII-17
H
H


2701





H
H
H
H


2702





H
H





VII-18
H
H


2703





H
H
H
H


2704





H
H





VII-19
H
Ph
H
H
H
H
Ph
H
H
H


VII-20
H
H
Ph
H
H
H
H
Ph
H
H





VII-21


2705





H
H
H
H


2706





H
H
H
H





VII-22
t-C4H9
H
H
H
H
H
H
H
H
H





VII-23


2707





H
H
H
H


2708





H
H
H
H





VII-24


2709





H
H
H
H


2710





H
H
H
H





VII-25


2711





H
H
H
H


2712





H
H
H
H





VII-26


2713





H
H
H
H


2714





H
H
H
H





VII-27


2715





H
H
H
H


2716





H
H
H
H





VII-28
n-C4H9
H
H
H
H
n-C4H9
H
H
H
H


VII-29
H
H
OCH3
H
H
H
H
OCH3
H
H















VII-30
H
R32 and R33
H
H
H
R32 and R33
H
H




form a fused



form a fused




benzene ring.



benzene ring.






























VII-31


2717





H
H
H
H


2718





H
H
H
H





VII-32


2719





H
H
H
H


2720





H
H
H
H





VII-33
H
H


2721





H
H
H
H


2722





H
H





VII-34


2723





H
H
H
H


2724





H
H
H
H





VII-35
H
H


2725





H
H
H
H


2726





H
H





VII-36
H
H
Ph
H
Ph
H
H
Ph
H
Ph


VII-37
H
H
Ph
Ph
H
H
H
Ph
Ph
H










[0224]

81
















2727




















Compound







No.
M11═M21
M12═M22
M13═M23
M14═M24
M15═M25





VIII′-1
H
H
H
H
H


VIII′-2
CH3
H
H
H
H


VIII′-3
H
CH3
H
H
H


VIII′-4
H
H
CH3
H
H


VIII′-5
Ph
H
CH3
CH3
H


VIII′-6
H
Ph
H
H
H


VIII′-7
H
H
Ph
H
H


VIII′-8
H
H
Ph
Ph
H


VIII′-9
H
H
Ph
H
Ph





VIII′-10
H
H


2728





H
H





VIII′-11


2729





H
H
H
H





VIII′-12
H
H


2730





H
H





VIII′-13


2731





H
H
H
H





VIII′-14
N(Ph)2
H
H
H
H


VIII′-15
N(C2H5)2
H
H
H
H


VIII′-16
OCH3
H
H
H
H


VIII′-17
Oph
H
H
H
H





VIII′-18


2732





H
H
H
H





VIII′-19


2733





H
H
H
H










[0225]

2734






[0226] The phenylanthracene derivatives used herein can be prepared by coupling a halogenated diphenylanthracene compound with Ni(cod)2 wherein cod represents 1,5-cyclooctadiene, or cross-coupling a Grignard reagent of a dihalogenated aryl with a nickel complex such as NiCl2(dppe) or NiCl2(dppp) wherein dppe represents diphenylphosphinoethane and dppp represents diphenylphosphinopropane. Alternatively, the phenylanthracene derivatives are prepared by a cross-coupling process involving reacting anthraquinone, benzoquinone, phenylanthrone or bianthrone with a Grignard reagent of aryl or a lithiated aryl followed by reduction.


[0227] These compounds can be identified by elemental analysis, mass analysis, IR spectroscopy, 1H and 13C NMR, etc.


[0228] In general, the phenylanthracene derivatives have a molecular weight of about 400 to about 2,000, preferably about 400 to about 1,000, a high melting point of about 200 to about 500° C., and a high glass transition temperature (Tg) of about 80 to about 250° C., preferably about 100 to 250° C., more preferably about 130 to 250° C., especially about 150 to 250° C. By conventional vacuum deposition or the like, they form a transparent, smooth film of quality which maintains a stable amorphous state even above room temperature and over a long period of time.


[0229] Since the phenylanthracene derivatives are relatively neutral compounds, better results are obtained on use of them in a light emitting layer. A freedom of design of the recombination/light emitting region is available by controlling the film thickness in consideration of the carrier mobility and carrier density (which is dependent on ionization potential and electron affinity) of the light emitting layer, hole injecting and transporting layer, and electron injecting and transporting layer to be combined. This enables free design of luminous color, control of the luminance and spectrum of light emission by the interference of the electrodes, and control of the space distribution of light emission.


[0230] Quinoxaline Compounds


[0231] A still further class of organic compounds useful as the host material according to the invention are quinoxaline compounds of the following formula (IV).


Qn-L101  (IV)


[0232] Herein Q is a pyrazinyl radical having fused thereto a six-membered aromatic ring containing 0 to 2 nitrogen atoms and may be the same or different, and n is 2 or 3. Two or three Q radicals may be the same or different. The six-membered aromatic rings forming part of Q are preferably benzene, pyridine, pyrimidine and pyridazine rings. Such a six-membered aromatic ring may be fused to the pyrazine ring at any positions although it is preferred that carbon atoms be present and nitrogen atoms be absent at the fusion positions. It is therefore preferred that fusion be on the side between the 2 and 3-positions or 5 and 6-positions on the pyrazine ring, and on the side between the 2 and 3-positions (or 5 and 6-positions) or the side between the 3 and 4-positions (or 4 and 5-positions) on the pyridine ring, on the side between the 4 and 5-positions (or 5 and 6-positions) on the pyrimidine ring, and on the side between the 3 and 4-positions (or 5 and 6-positions) or the side between the 5 and 4-positions on the pyridazine ring.


[0233] L101 is a single bond or n-valent radical, i.e., di- or trivalent radical. Preferred divalent radicals are arenediyl radicals, such as phenylene, biphenyldiyl, naphthalenediyl, anthracenediyl and pyrenediyl. Preferred trivalent radicals are arenetriyl radicals (e.g., benzenetriyl), nitrogen atoms, and triarylaminetriyl radicals (e.g., triphenylaminetriyl).


[0234] The radicals represented by Q and L101 may further have substituents. Such substituents may be ones containing Q therein. The total number of Q radicals per molecule should preferably be 2 to 10, more preferably 2 to 4. Two or more Q radicals included in one molecule may be the same or different although they are often the same for the sake of easy synthesis.


[0235] Of the quinoxaline compounds of formula (IV), those of formula (VIII) are preferred.
2735


[0236] In formula (VIII), Z is a group of atoms necessary to form a benzene, pyridine, pyrimidine or pyridazine ring with the two carbon atoms of the pyrazine ring.


[0237] The ring completed by Z may further have a substituent(s) or a fused ring. The preferred positions of fusion of the ring completed by Z to the pyrazine ring are the same as described above in conjunction with formula (IV).


[0238] A is a monovalent substituent attached to the pyrazine ring, and k is 0, 1 or 2. Preferred examples of the substituents on the ring completed by Z and the substituents represented by A are the same as A13 etc. in formulas (VIII-a) to (VIII-m) to be described later and will be described later.


[0239] The letter n is 2 or 3. When n is 2, L101 is a single bond, phenylene, biphenyldiyl or naphthalenediyl radical. When n is 3, L101 is a benzenetriyl radical, nitrogen atom or triphenylaminetriyl radical. These radicals will be described later in conjunction with formulas (VIII-a) to (VIII-m).


[0240] The rings completed by Z may be the same or different although they are preferably the same as described in conjunction with formula (IV).


[0241] The fused pyrazine ring having the ring completed by Z may be bonded, at any position, to L101.


[0242] Of the quinoxaline compounds of formula (VIII), those of formulas (VIII-a) to (VIII-m) are preferred.
2736


[0243] First described are those compounds wherein L101 in formula (VIII) is a divalent radical L111 or single bond, as represented by formulas (VIII-a) to (VIII-f) and (VIII-m).


[0244] In formulas (VIII-a) to (VIII-f) and (VIII-m), L111 is a phenylene, biphenyldiyl or naphthalenediyl radical. The phenylene radical represented by L111 may be an o-, m- or p-phenylene radical, with the p-phenylene being especially preferred. The preferred biphenyldiyl radical represented by L111 is 4,4′-biphenyl-1,1′-diyl. The preferred naphthalenediyl radical represented by L111 is 1,5-naphthalenediyl. These divalent radicals are preferably unsubstituted although they may have substituents such as alkyl and aryl groups.


[0245] A13, A15 to A18, A23, A25 to A28 in formula (VIII-a), A13, A16 to A18, A23, A26 to A28 in formula (VIII-b), A13, A15, A17, A18, A23, A25, A27 and A28 in formula (VIII-c), A13, A16, A18, A23, A26 and A28 in formula (VIII-d), A13, A17, A18, A23, A27 and A28 in formula (VIII-e), A13, A15, A18, A23, A25 and A28 in formula (VIII-f), A12, A13, A15, A17, A18, A22, A23, A25, A27 and A28 in formula (VIII-m) each independently stand for hydrogen, halogen atoms, hydroxyl, carboxy, nitro, cyano, alkyl, aryl, alkoxy, aryloxy, amino, alkylthio, arylthio and heterocyclic radicals. In each formula, these radicals may be the same or different.


[0246] Examples of the halogen atoms represented by A13 etc. include fluorine and chlorine atoms.


[0247] The alkyl radicals represented by A13 etc. are preferably those of 1 to 6 carbon atoms in total, which may be straight or branched. The alkyl radicals are preferably unsubstituted ones although they may have substituents such as halogen atoms (e.g., F and Cl). Illustrative examples of the alkyl radicals include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl and hexyl.


[0248] The aryl radicals represented by A13 etc. are preferably those of 6 to 30 carbon atoms in total, which may be monocyclic or polycyclic (fused ring or ring collection) or have substituents. Such substituents are halogen atoms (e.g., F and Cl), alkyl groups (e.g., methyl) and heterocyclic groups. The heterocyclic groups as the substituent are preferably the same as the fused pyrazinyl radical bonded to L111 in formula (VIII-a), such as quinoxalinyl. Illustrative examples of the aryl radicals represented by A13, etc. include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, and 4-biphenylyl radicals, which may have substituted thereon a fused pyradinyl group such as quinoxalinyl.


[0249] The alkoxy radicals represented by A13, etc. are preferably those of alkyls of 1 to 6 carbon atoms in total. The alkoxy radicals are preferably unsubstituted ones although they may have substituents. Illustrative examples of the alkoxy radicals include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and t-butoxy.


[0250] Exemplary of the aryloxy radicals represented by A13, etc. is phenoxy.


[0251] The amino radicals represented by A13, etc. may have substituents such as alkyl and aryl groups. Exemplary amino radicals are amino, methylamino, dimethylamino, phenylamino and diphenylamino.


[0252] Examples of the alkylthio radical represented by A13, etc. include methylthio and ethylthio.


[0253] Exemplary of the arylthio radical represented by A13, etc. is phenylthio.


[0254] Examples of the heterocyclic radicals represented by A13, etc. include furyl, thienyl, pyrrole, pyridyl, and quinolyl as well as the same as the fused pyradinyl radical bonded to L111 in formula (VIII-a) such as quinoxalinyl.


[0255] Two adjoining ones among A15 to A18 and A25 to A28 in formula (VIII-a), two adjoining ones among A16 to A18 and A26 to A28 in formula (VIII-b), a pair of A17 and A18 or a pair of A27 and A28 in formula (VIII-c), a pair of A17 and A18 or a pair of A27 and A28 in formula (VIII-e), and a pair of A12 and A13, a pair of A17 and A18, a pair of A22 and A23 or a pair of A27 and A28 in formula (VIII-m) may bond together to form a ring. The ring formed herein is preferably a benzene ring. Two or more benzene rings thus formed may be fused together, or the benzene ring thus formed may further have a ring fused thereto.


[0256] In preferred embodiments, A13 and A23 in formulas (VIII-a) to (VIII-f) and A12, A13, A22 and A23 in formula (VIII-m) are aryl radicals; A15 to A18 and A25 to A28 in formula (VIII-a) are hydrogen, alkyl or alkoxy radicals or two adjoining ones thereof bond together to form a benzene ring; and A16 to A18 and A26 to A28 in formula (VIII-b), A15, A17, A18, A25, A27 and A28 in formula (VIII-c), A16, A18, A26 and A28 in formula (VIII-d), A17, A18, A27 and A28 in formula (VIII-e), A15, A18, A25 and A28 in formula (VIII-f), and A15, A17, A18, A25, A27 and A28 in formula (VIII-m) are hydrogen.


[0257] Described next are those compounds wherein L101 in formula (VIII) is a trivalent radical L112, as represented by formulas (VIII-g) to (VIII-l).


[0258] In formulas (VIII-g) to (VIII-l), L112 is a benzenetriyl radical, nitrogen atom or triphenylaminetriyl radical. The preferred benzenetriyl radical represented by L112 is 1,3,5-benzenetriyl. The preferred triphenylaminetriyl radical represented by L112 is 4,4′,4″-triphenyl-1,1′,1″-triyl. These trivalent radicals are preferably unsubstituted although they may have substituents such as alkyl and aryl groups.


[0259] A13, A15 to A18, A23, A25 to A28, A33, A35 to A38 in formula (VIII-g), A13, A16 to A18, A23, A26 to A28, A33, A36 to A38 in formula (VIII-h), A13, A15, A17, A18, A23, A25, A27, A28, A33, A35, A37 and A38 in formula (VIII-i), A13, A16, A18, A23, A26, A28, A33, A36 and A38 in formula (VIII-j), A13, A17, A18, A23, A27, A28, A33, A37 and A38 in formula (VIII-k), A13, A15, A18, A23, A25 A28, A33, A35 and A38 in formula (VIII-l) each independently stand for hydrogen, halogen atoms, hydroxyl, carboxy, nitro, cyano, alkyl, aryl, alkoxy, aryloxy, amino, alkylthio, arylthio and heterocyclic radicals. In each formula, these radicals may be the same or different. Illustrative examples of these radicals are the same as described above in conjunction with formulas (VIII-a) to (VIII-f).


[0260] Two adjoining ones among A15 to A18, A25 to A28 and A35 to A38 in formula (VIII-g), two adjoining ones among A16 to A18, A26 to A28 and A36 to A38 in formula (VIII-h), a pair of A17 and A18 or a pair of A27 and A28, or a pair of A37 and A38 in formula (VIII-i), and a pair of A17 and A18, a pair of A27 and A28 or a pair of A37 and A38 in formula (VIII-k) may bond together to form a ring. Illustrative examples of the ring are the same as described above in conjunction with formulas (VIII-a) to (VIII-f). A13, A23 and A33 in formulas (VIII-a) to (VIII-l) are preferably hydrogen and aryl radicals such as phenyl.


[0261] In preferred embodiments, A15 to A18, A25 to A28 and A35 to A38 in formula (VIII-g) are hydrogen, or two adjoining ones among them bond together to form a ring; A16 to A18, A26 to A28, and A36 to A38 in formula (VIII-h), A15, A17, A18, A25, A27, A28, A35, A37 and A38 in formula (VIII-i), A16, A18, A26, A28, A36 and A38 in formula (VIII-j), A17, A18, A27, A28, A37 and A38 in formula (VIII-k), A15, A18, A25 A28, A35 and A38 in formula (VIII-l) are hydrogen.


[0262] Illustrative, non-limiting, examples of the quinoxaline compounds of formula (IV) are given below. They are shown by combinations of L111, L112, and A's in formulas (VIII-a) to (VIII-m). When A13 and A23 are different, they are individually shown. The expressions of formulas (VIII-a) to (VIII-m) are typical examples and to be construed to encompass corresponding structural isomers because an actual product as synthesized is a mixture of structural isomers due to the synthesis route.
82Formula (VIII)Compound No.L111A13═A23A15═A15A16═A26A17═A27A18═A28VIII-a-12737—PhHHHHVIII-a-22738—PhHHCH3HVIII-a-32739—PhHCH3CH3HVIII-a-42740—PhHHC2H5HVIII-a-52741—PhHHn-C3H7HVIII-a-62742—PhHHn-C4H9HVIII-a-72743—PhHHt-C4H9HVIII-a-82744—PhHH—OCH3HVIII-a-92745—PhHHA17 and A18 form a benzene ring. A27 A28 form a benzene ringVIII-a-102746—PhHA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.HVIII-a-112747—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ringA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-a-122748—PhHA16 and A18, and A17 and A18 form benzene rings, respectively, which are fused to form a phenalene ring as a whole. (The same applies to A26 to A28.)VIII-a-132749—PhA15 and A16, A16 and A17, and A17 and A18 form benzene rings, respectively, which form a phenanthrene ring as a whole. (The same applies to A25 to A28.)VIII-a-142750—PhHH—PhHVIII-a-152751—PhH—Ph—PhHVIII-a-162752—Ph—PhHH—PhVIII-a-172753—PhHH1-naphthylHVIII-a-182754—PhHH2-naphthylHVIII-a-192755—PhHH4-biphenylylHVIII-a-202756—PhHH3-biphenylylHVIII-a-212757—PhHH2-biphenylylHVIII-a-222758—PhH4-biphenylyl4-biphenylylHVIII-a-232759—PhHHClHVIII-a-242760—PhHH—OHHVIII-a-252761—PhHH—NO2HVIII-a-262762—PhHH—CNHVIII-a-272763—PhHH—OPhHVIII-a-282764—PhHH—SCH3HVIII-a-292765—PhHH—SPhHVIII-a-302766—PhHHHHVIII-a-312767—PhHHCH3HVIII-a-322768—PhHCH3CH3HVIII-a-332769—PhCH3HHCH3VIII-a-342770—PhHHC2H5HVIII-a-352771—PhHHn-C3H7HVIII-a-362772—PhHHn-C4H9HVIII-a-372773—PhHHt-C4H9HVIII-a-382774—PhHH—OCH3HVIII-a-392775—PhHHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-a-402776—PhHA16 and A17 form a benzene ring. A26 and A27 form a benzene ringHVIII-a-412777—PhA15 and A16 form a benzene ring. A25 and A26 form a benzen ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-a-422778—PhHA16 and A18 +L, and A17 and A18 form benzene rings, respectively, which are fused to form a phenalene ring as a whole. (The same applies to A26 to A28 .)VIII-a-432779—PhA15 and A16 +L, A16 and A17 , and A17 and A18 form benzene rings, respectively, which form a phenanthrene ring as a whole. (The same applies to A25 to A28 .)VIII-a-442780—PhHH—PhHVIII-a-452781—PhH—Ph—PhHVIII-a-462782—Ph—PhHH—PhVIII-a-472783—PhHH1-naphthylHVIII-a-482784—PhHH2-naphthylHVIII-a-492785—PhHH4-biphenylylHVIII-a-502786—PhHH3-biphenylylHVIII-a-512787—PhHH2-biphenylylHVIII-a-522788—PhHHClHVIII-a-532789—PhHH—OHHVIII-a-542790—PhHH—NO2HVIII-a-552791—PhHH—CNHVIII-a-562792—PhHH—OPhHVIII-a-572793—PhHH—SCH3HVIII-a-582794—PhHH—SPhHVIII-a-592795—PhHHHHVIII-a-602796—PhHHCH3HVIII-a-612797—PhHCH3CH3HVIII-a-622798—PhCH3HHCH3VIII-a-632799—PhCH3CH3CH3HVIII-a-642800—PhCH3CH3CH3CH3VIII-a-652801—PhHHC2H5HVIII-a-662802—PhHHn-C3H7HVIII-a-672803—PhHHn-C4H9HVIII-a-682804—PhHHt-C4H9HVIII-a-692805—PhHH—OCH3HVIII-a-702806—PhHHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-a-712807—PhHA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.HVIII-a-722808—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ringVIII-a-732809—PhHA16 and A18 +L, and A17 and A16 form benzene rings, respectively, which are fused to form a phenalene ring as a whole. (The same applies to A26 to A26 .)VIII-a-742810—PhA15 and A16 +L, A16 and A17 , and A17 and A18 form benzene rings, respectively, which form a phenanthrene ring as a whole. (The same applies to A25 to A28 .)VIII-a-752811—PhHH—PhHVIII-a-762812—PhH—Ph—PhHVIII-a-772813—Ph—PhHH—PhVIII-a-782814—PhHH1-naphthylHVIII-a-792815—PhHH2-naphthylHVIII-a-802816—PhHH4-biphenylylHVIII-a-812817—PhHH3-biphenylylHVIII-a-822818—PhHH2-biphenylylHVIII-a-832819—PhHHClHVIII-a-842820—PhHH—OHHVIII-a-852821—PhHH—NO2HVIII-a-862822—PhHH—CNHVIII-a-872823—PhHH—OPhHVIII-a-882824—PhHH—SCH3HVIII-a-892825—PhHH—SPhHVIII-a-9028262827HHHHVIII-a-9128282829
A23 = —Ph
A15 and A16 form a benzene ring. A25 and A26 form a benzen ring.HH
VIII-a-9228302831A15 and A16 form a benzene ring. A25 and A26 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring.A23 = —PhVIII-a-9328322833HHHHA23 = —PhVIII-a-9428342835A15 and A16 form a benzene ring. A25 and A26 form a benzene ring.HHA23 = —PhVIII-a-9528362837A15 and A16 form a benzene ring. A25 and A26 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring.A23 = —PhVIII-a-962838—PhHH—NPh2HVIII-a-972839—PhHH—COOHHVIII-a-982840—PhHH2-pyridylHVIII-a-992841—PhHH—NPh2HVIII-a-1002842—PhHH—COOHHVIII-a-1012843—PhHH2-pyridylHVIII-a-1022844—PhHH—NPh2HVIII-a-1032845—PhHH—COOHHVIII-a-1042846—PhHH2-pyridylHFormula (VIII)Compound No.L111A13 ═A23A16═A26 A17═A27A18═A28VIII-b-12847—PhHHHVIII-b-22848—PhHHHVIII-b-32849—PhHHHVIII-b-428502851HHHA23 = —PhVIII-b-528522853HHHA23 = —PhVIII-b-62854—PhHHCH3VIII-b-72855—PhHCH3HVIII-b-82856—PhCH3HHVIII-b-92857—PhHC2H5HVIII-b-102858—PhHn-C3H7HVIII-b-112859—PhHn-C4H9HVIII-b-122860—PhHt-C4H9HVIII-b-132861—PhH—OCH3HVIII-b-142862—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.HVIII-b-15 2863—PhHA17 and A18 form a benzene ring. Ahd 27 and A28 form a benzene ring.VIII-b-162864—PhHPhHVIII-b-172865—PhPhPhHVIII-b-182866—PhH1-naphthylHVIII-b-192867—Ph1-naphthyl1-naphthylHVIII-b-202868—PhH2-naphthylHVIII-b-212869—Ph2-naphthyl2-naphthylHVIII-b-222870—PhH4-biphenylylHVIII-b-232871—Ph4-biphenylyl4-biphenylylHVIII-b-242872—PhH3-biphenylylHVIII-b-252873—Ph3-biphenylyl3-biphenylylHVIII-b-262874—PhH2-biphenylylHVIII-b-272875—Ph2-biphenylyl2-biphenylylHVIII-b-282876—PhHClHVIII-b-292877—PhH—OHHVIII-b-302878—PhH—NO2HVIII-b-312879—PhH—CNHVIII-b-322880—PhH—OPhHVIII-b-332881—PhH—SCH3HVIII-b-342882—PhH—SPhHVIII-b-352883—PhH—NPh2HVIII-b-362884—PhH—COOHHVIII-b-372885—PhH2-pyridylHVIII-b-382886—PhHHCH3VIII-b-392887—PhHCH3HVIII-b-402888—PhCH3HHVIII-b-412889—PhHC2H5HVIII-b-422890—PhHn-C3H7HVIII-b-432891—PhHn-C4H9HVIII-b-442892—PhHt-C4H9HVIII-b-452893—PhH—OCH3HVIII-b-462894—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.HVIII-b-47 2895—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-b-482896—PhHPhHVIII-b-492897—PhPhPhHVIII-b-502898—PhH1-naphthylHVIII-b-512899—Ph1-naphthyl1-naphthylHVIII-b-522900—PhH2-naphthylHVIII-b-532901—Ph2-naphthyl2-naphthylHVIII-b-542902—PhH4-biphenylylHVIII-b-552903—Ph4-biphenylyl4-biphenylylHVIII-b-562904—PhH3-biphenylylHVIII-b-572905—Ph3-biphenylyl3-biphenylylHVIII-b-582906—PhH2-biphenylylHVIII-b-592907—Ph2-biphenylyl2-biphenylylHVIII-b-602908—PhHClHVIII-b-612909—PhH—OHHVIII-b-622910—PhH—NO2HVIII-b-632911—PhH—CNHVIII-b-642912—PhH—OPhHVIII-b-652913—PhH—SCH3HVIII-b-662914—PhH—SPhHVIII-b-672915—PhH—NPh2HVIII-b-682916—PhH—COOHHVIII-b-692917—PhH2-pyridylHVIII-b-702918—PhHHCH3VIII-b-712919—PhHCH3HVIII-b-722920—PhCH3HHVIII-b-732921—PhHC2H5HVIII-b-742922—PhHn-C3H7HVIII-b-752923—PhHn-C4H9HVIII-b-762924—PhHHt-C4H9VIII-b-772925—PhHt-C4H9HVIII-b-782926—PhH—OCH3HVIII-b-79 2927—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.HVIII-b-802928—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-b-812929—PhH—PhHVIII-b-822930—PhPhPhHVIII-b-832931—PhH1-naphthylHVIII-b-842932—Ph1-naphthyl1-naphthylHVIII-b-852933—PhH2-naphthylHVIII-b-862934—Ph2-naphthyl2-naphthylHVIII-b-872935—PhH4-biphenylylHVIII-b-882936—Ph4-biphenylyl4-biphenylylHVIII-b-892937—PhH3-biphenylylHVIII-b-902938—Ph3-biphenylyl3-biphenylylHVIII-b-912939—PhH2-biphenylylHVIII-b-922940—Ph2-biphenylyl2-biphenylylHVIII-b-932941—PhHClHVIII-b-942942—PhH—OHHVIII-b-952943—PhH—NO2HVIII-b-962944—PhH—CNHVIII-b-972945—PhH—OPhHVIII-b-982946—PhH—SCH3HVIII-b-992947—PhH—SPhHVIII-b-1002948—PhH—NPh2HVIII-b-1012949—PhH—COOHHVIII-b-1022950—PhH2-pyridylHFormula (VIII)Compound No.L111A13═A23A15═A25A17═A27A18═A28VIII-c-12951—PhHHHVIII-c-22952—PhHHHVIII-c-32953—PhHHHVIII-c-429542955HHHA23 = —PhVIII-c-529562957HHHA23 = —PhVIII-c-62958—PhHHCH3VIII-c-72959—PhHCH3HVIII-c-82960—PhCH3HHVIII-c-92961—PhHC2H5HVIII-c-102962—PhHn-C3H7HVIII-c-112963—PhHn-C4H9HVIII-c-122964—PhHt-C4H9HVIII-c-132965—PhH—OCH3HVIII-c-142966—PhHA17 and A18 form a benzene ring. A27 and A28 form a beozene ring.VIII-c-152967—PhHH—PhVIII-c-162968—PhH—PhHVIII-c-172969—Ph—PhHHVIII-c-182970—PhH1-naphthylHVIII-c-192971—PhH2-naphthylHVIII-c-202972—PhH4-biphenylylHVIII-c-212973—PhH3-biphenylylHVIII-c-222974—PhH2-biphenylylHVIII-c-232975—PhHClHVIII-c-242976—PhH—OHHVIII-c-252977—PhH—NO2HVIII-c-262978—PhH—CNHVIII-c-272979—PhH—OPhHVIII-c-282980—PhH—SCH3HVIII-c-292981—PhH—SPhHVIII-c-302982—PhH—NPh2HVIII-c-312983—PhH—COOHHVIII-c-322984—PhH2-pyridylHVIII-c-332985—PhHHCH3VIII-c-342986—PhHCH3HVIII-c-352987—PhCH3HHVIII-c-362988—PhHC2H5HVIII-c-372989—PhHn-C3H7HVIII-c-382990—PhHn-C4H9HVIII-c-392991—PhHt-C4H9HVIII-c-402992—Ph—OCH3HHVIII-c-41 2993—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-c-422994—PhHH—PhVIII-c-432995—PhH—PhHVIII-c-442996—Ph—PhHHVIII-c-452997—PhH1-naphthylHVIII-c-462998—PhH2-naphthylHVIII-c-472999—PhH4-biphenylylHVIII-c-483000—PhH3-biphenylylHVIII-c-493001—PhH2-biphenylylHVIII-c-503002—PhHClHVIII-c-513003—PhH—OHHVIII-c-523004—PhH—NO2HVIII-c-533005—PhH—CNHVIII-c-543006—PhH—OPhHVIII-c-553007—PhH—SCH3HVIII-c-563008—PhH—SPhHVIII-c-573009—PhH—NPh2HVIII-c-583010—PhH—COOHHVIII-c-593011—PhH2-pyridylHVIII-c-603012—PhHHCH3VIII-c-613013—PhHCH3HVIII-c-623014—PhCH3HHVIII-c-633015—PhHC2H5HVIII-c-643016—PhHn-C3H7HVIII-c-653017—PhHn-C4H9HVIII-c-663018—PhHt-C4H9HVIII-c-673019—PhH—OCH3HVIII-c-68 3020—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-c-693021—PhHH—PhVIII-c-703022—PhH—PhHVIII-c-713023—Ph—PhHHVIII-c-723024—PhH1-naphthylHVIII-c-733025—PhH2-naphthylHVIII-c-743026—PhH4-biphenylylHVIII-c-753027—PhH2-biphenylylHVIII-c-763028—PhHClHVIII-c-773029—PhH—OHHVIII-c-783030—PhH—NO2HVIII-c-793031—PhH—CNHVIII-c-803032—PhH—OPhHVIII-c-813033—PhH—SCH3HVIII-c-823034—PhH—SPhHVIII-c-833035—PhH—NPh2HVIII-c-843036—PhH—COOHHVIII-c-853037—PhH2-pyridylHFormula (VIII)Compound No.L111A13 ═A23A16═A26 A18═A28VIII-d-13038—PhHHVIII-d-23039—PhHHVIII-d-33040—PhHHVIII-d-430413042HHA23 = —PhVIII-d-530433044HHA23 = —PhVIII-d-63045—PhHCH3VIII-d-73046—PhCH3HVIII-d-83047—PhCH3CH3VIII-d-93048—PhC2H5HVIII-d-103049—Phn-C3H7HVIII-d-113050—Phn-C4H9HVIII-d-123051—Pht-C4H9HVIII-d-133052—Ph—OCH3HVIII-d-143053—PhH—PhVIII-d-153054—Ph—PhHVIII-d-163055—Ph1-naphthylHVIII-d-173056—Ph2-naphthylHVIII-d-183057—Ph4-biphenylylHVIII-d-193058—Ph3-biphenylylHVIII-d-203059—Ph2-biphenylylHVIII-d-213060—PhClHVIII-d-223061—Ph—OHHVIII-d-233062—Ph—NO2HVIII-d-243063—Ph—CNHVIII-d-253064—Ph—OPhHVIII-d-263065—Ph—SCH3HVIII-d-273066—Ph—SPhHVIII-d-283067—Ph—NH2HVIII-d-293068—Ph—NH—PhHVIII-d-303069—Ph—NPh2HVIII-d-313070—Ph—COOHHVIII-d-323071—Ph2-pyridylHVIII-d-333072—PhHCH3VIII-d-343073—PhCH3HVIII-d-353074—PhCH3CH3VIII-d-363075—PhC2H5HVIII-d-373076—Phn-C3H7HVIII-d-383077—Phn-C4H9HVIII-d-393078—Pht-C4H9HVIII-d-403079—Ph—OCH3HVIII-d-413080—PhH—PhVIII-d-423081—Ph—PhHVIII-d-433082—Ph1-naphthylHVIII-d-443083—Ph4-biphenylylHVIII-d-453084—Ph3-biphenylylHVIII-d-463085—Ph2-biphenylylHVIII-d-473086—PhClHVIII-d-483087—Ph—OHHVIII-d-493088—PhNO2HVIII-d-503089—Ph—CNHVIII-d-513090—Ph—OPhHVIII-d-523091—Ph—SCH3HVIII-d-533092—Ph—SPhHVIII-d-543093—Ph—NPh2HVIII-d-553094—Ph—COOHHVIII-d-563095—Ph2-pyridylHVIII-d-573096—PhHCH3VIII-d-583097—PhCH3HVIII-d-593098—PhCH3CH3VIII-d-603099—PhHC2H5VIII-d-613100—PhC2H5HVIII-d-623101—Phn-C3H7HVIII-d-633102—Phn-C4H9HVIII-d-643103—Pht-C4H9HVIII-d-653104—PhH—OCH3VIII-d-663105—Ph—OCH3HVIII-d-673106—Ph—OCH3—OCH3VIII-d-683107—PhH—PhVIII-d-693108—Ph—PhHVIII-d-703109—PhH1-naphthylVIII-d-713110—Ph1-naphthylHVIII-d-723111—Ph2-naphthylHVIII-d-733112—PhH4-biphenylylVIII-d-743113—Ph4-biphenylylHVIII-d-753114—Ph3-biphenylylHVIII-d-763115—Ph2-biphenylylHVIII-d-773116—PhClHVIII-d-783117—Ph—OHHVIII-d-793118—Ph—NO2HVIII-d-803119—Ph—CNHVIII-d-813120—Ph—OPhHVIII-d-823121—Ph—SCH3HVIII-d-833122—Ph—SPhHVIII-d-843123—Ph—NPh2HVIII-d-853124—Ph—COOHHVIII-d-863125—Ph2-pyridylHFormula (VIII)Compound No.L111A13═A23A17═A27A18═A28VIII-e-13126—PhHHVIII-e-23127—PhHHVIII-e-33128—PhHHVIII-e-43129—PhHCH3VIII-e-53130—PhCH3HVIII-e-63131—PhCH3CH3VIII-e-73132—PhC2H5HVIII-e-83133—Phn-C3H7HVIII-e-93134—Phn-C3H7n-C3H7VIII-e-103135—Phn-C4H9HVIII-e-113136—Pht-C4H9HVIII-e-123137—Ph—OCH3HVIII-e-133138—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-e-143139—PhH—PhVIII-e-153140—Ph—PhHVIII-e-163141—Ph—Ph—PhVIII-e-173142—Ph1-naphthylHVIII-e-183143—Ph2-naphthylHVIII-e-193144—Ph4-biphenylylHVIII-e-203145—Ph3-biphenylylHVIII-e-213146—Ph2-biphenylylHVIII-e-223147—PhClHVIII-e-233148—Ph—OHHVIII-e-243149—Ph—NO2HVIII-e-253150—Ph—CNHVIII-e-263151—Ph—OPhHVIII-e-273152—Ph—SCH3HVIII-e-283153—Ph—SPhHVIII-e-293154—Ph—NPh2HVIII-e-303155—Ph—COOHHVIII-e-313156—Ph2-pyridylHVIII-e-323157—PhHCH3VIII-e-333158—PhCH3HVIII-e-343159—PhCH3CH3VIII-e-353160—PhC2H5HVIII-e-363161—Phn-C3H7HVIII-e-373162—Phn-C3H7n-C3H7VIII-e-383163—Phn-C4H9HVIII-e-393164—Pht-C4H9HVIII-e-403165—PhH—OCH3VIII-e-413166—Ph—OCH3HVIII-e-423167—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-e-433168—PhH—PhVIII-e-443169—Ph—PhHVIII-e-453170—Ph—Ph—PhVIII-e-463171—Ph1-naphthylHVIII-e-473172—Ph2-naphthylHVIII-e-483173—PhH4-biphenylylVIII-e-493174—Ph4-biphenylyl4-biphenylylVIII-e-503175—Ph3-biphenylylHVIII-e-513176—Ph2-biphenylylHVIII-e-523177—PhClHVIII-e-533178—Ph—OHHVIII-e-543179—Ph—NO2HVIII-e-553180—Ph—CNHVIII-e-563181—Ph—OPhHVIII-e-573182—Ph—SCH3HVIII-e-583183—Ph—SPhHVIII-e-593184—Ph—NPh2HVIII-e-603185—Ph—COOHHVIII-e-613186—Ph2-pyridylHVIII-e-623187—PhHCH3VIII-e-633188—PhCH3HVIII-e-643189—PhCH3CH3VIII-e-653190—PhC2H5HVIII-e-663191—Phn-C3H7HVIII-e-673192—Phn-C3H7n-C3H7VIII-e-683193—Phn-C4H9HVIII-e-693194—Pht-C4H9HVIII-e-703195—Pht-C4H9t-C4H9VIII-e-713196—Ph—OCH3HVIII-e-723197—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.VIII-e-733198—PhH—PhVIII-e-743199—Ph—PhHVIII-e-753200—Ph—Ph—PhVIII-e-763201—Ph1-naphthylHVIII-e-773202—Ph2-naphthylHVIII-e-783203—Ph3-biphenylylHVIII-e-793204—Ph2-biphenylylHVIII-e-803205—PhClHVIII-e-813206—Ph—OHHVIII-e-823207—Ph—NO2HVIII-e-833208—Ph—CNHVIII-e-843209—Ph—OPhHVIII-e-853210—Ph—SCH3HVIII-e-863211—Ph—SPhHVIII-e-873212—Ph—NPh2HVIII-e-883213—Ph—COOHHVIII-e-893214—Ph2-pyridylHFormula (VIII)Compound No.L111 A13═A23A15═A25 A18═A28VIII-f-13215—PhHHVIII-f-23216—PhHHVIII-f-33217—PhHHVIII-f-43218—PhHCH3VIII-f-53219—PhCH3HVIII-f-63220—PhCH3CH3VIII-f-73221—PhC2H5HVIII-f-83222—Phn-C3H7HVIII-f-93223—Phn-C4H9HVIII-f-103224—Pht-C4H9HVIII-f-113225—Ph—OCH3HVIII-f-123226—PhH—PhVIII-f-133227—Ph—PhHVIII-f-143228—Ph—Ph—PhVIII-f-153229—PhH1-naphthylVIII-f-163230—Ph1-naphthylHVIII-f-173231—Ph2-naphthylHVIII-f-183232—Ph4-biphenylylHVIII-f-193233—Ph3-biphenylylHVIII-f-203234—Ph2-biphenylylHVIII-f-213235—PhClHVIII-f-223236—Ph—OHHVIII-f-233237—Ph—NO2HVIII-f-243238—Ph—CNHVIII-f-253239—Ph—OPhHVIII-f-263240—Ph—SCH3HVIII-f-273241—Ph—SPhHVIII-f-283242—Ph—NPh2HVIII-f-293243—Ph—COOHHVIII-f-303244—Ph2-pyridylHVIII-f-313245—PhHCH3VIII-f-323246—PhCH3HVIII-f-333247—PhCH3CH3VIII-f-343248—PhC2H5HVIII-f-353249—Phn-C3H7HVIII-f-363250—Phn-C4H9HVIII-f-373251—Pht-C4H9HVIII-f-383252—Ph—OCH3HVIII-f-393253—PhH—PhVIII-f-403254—Ph—PhHVIII-f-413255—Ph—Ph—PhVIII-f-423256—Ph1-naphthylHVIII-f-433257—Ph2-naphthylHVIII-f-443258—Ph4-biphenylylHVIII-f-453259—Ph3-biphenylylHVIII-f-463260—Ph2-biphenylylHVIII-f-473261—PhClHVIII-f-483262—PhOHHVIII-f-493263—Ph—NO2HVIII-f-503264—Ph—CNHVIII-f-513265—Ph—OPhHVIII-f-523266—Ph—SCH3HVIII-f-533267—Ph—SPhHVIII-f-543268—Ph—NPh2HVIII-f-553269—Ph—COOHHVIII-f-563270—Ph2-pyridylHVIII-f-573271—PhHCH3VIII-f-583272—PhCH3HVIII-f-593273—PhCH3CH3VIII-f-603274—PhC2H5HVIII-f-613275—Phn-C3H7HVIII-f-623276—Phn-C4H9HVIII-f-633277—Pht-C4H9HVIII-f-643278—Ph—OCH3HVIII-f-653279—PhH—PhVIII-f-663280—Ph—PhHVIII-f-673281—Ph—Ph—PhVIII-f-683282—Ph1-naphthylHVIII-f-693283—Ph2-naphthylHVIII-f-703284—Ph4-biphenylylHVIII-f-713285—Ph3-biphenylylHVIII-f-723286—Ph2-biphenylylHVIII-f-733287—PhClHVIII-f-743288—Ph—OHHVIII-f-753289—Ph—NO2HVIII-f-763290—Ph—CNHVIII-f-773291—Ph—OPhHVIII-f-783292—Ph—SCH3HVIII-f-793293—Ph—SPhHVIII-f-803294—Ph—NPh2HVIII-f-813295—Ph—COOHHVIII-f-823296—Ph2-pyridylHFormula (VIII)A13═A23A15═A25A16═A26A17═A27A18═A28Compound No.L112 ═A33═A35═A36═A37 A38VIII-g-13297HHHHHVIII-g-23298HA15 and A18 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-g-33299HA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HHVIII-g-43300—PhHHHHVIII-g-53301—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-g-63302—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HHVIII-g-73303HHHHHVIII-g-83304HA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-g-93305HA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HHVIII-g-10 3306—PhHHHHVIII-g-113307—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-g-123308—PhA15 and A15 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HHVIII-g-133309HHHHHVIII-g-14 3310HA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HHVIII-g-153311HA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-g-163312—PhHHHHVIII-g-173313—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.A17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-g-183314—PhA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HHVIII-g-193315—PhHH—PhHVIII-g-203316—Ph—PhHHHVIII-g-213317—PhH—PhHHVIII-g-223318—PhHHH—PhVIII-g-233319—PhHHClHVIII-g-243320—PhHH—OHHVIII-g-253321—PhHH—NO2HVIII-g-263322—PhHH—CNHVIII-g-273323—PhHH—OPhHVIII-g-283324—PhHH—SCH3HVIII-g-293325—PhHH—SPhHVIII-g-303326—PhHH—NPhHVIII-g-313327—PhHHCH3HVIII-g-323328—PhHH—OCH3HVIII-g-333329—PhHH—COOHHVIII-g-343330—PhHH2-pyridylHVIII-g-353331—PhHH—PhHVIII-g-363332—Ph—PhHHHVIII-g-373333—PhH—PhHHVIII-g-383334—PhHHH—PhVIII-g-393335—PhHHClHVIII-g-403336—PhHH—OHHVIII-g-413337—PhHH—NO2HVIII-g-423338—PhHH—CNHVIII-g-433339—PhHH—OPhHVIII-g-443340—PhHHSCH3HVIII-g-453341—PhHH—SPhHVIII-g-463342—PhHH—NPhHVIII-g-473343—PhHHCH3HVIII-g-483344—PhHH—OCH3HVIII-g-493345—PhHH—COOHHVIII-g-503346—PhHH2-pyridylHVIII-g-513347—PhHH—PhHVIII-g-523348—Ph—PhHHHVIII-g-533349—PhH—PhHHVIII-g-543350—PhHHH—PhVIII-g-553351—PhHHClHVIII-g-563352—PhHH—OHHVIII-g-573353—PhHH—NO2HVIII-g-583354—PhHH—CNHVIII-g-593355—PhHH—OPhHVIII-g-603356—PhHH—SCH3HVIII-g-613357—PhHH—SPhHVIII-g-623358—PhHH—NPhHVIII-g-633359—PhHHCH3HVIII-g-643360—PhHH—OCH3HVIII-g-653361—PhHH—COOHHVIII-g-663362—PhHH2-pyridylHFormula (VIII)A13═A23A16═A26A17═A27A18═A28Compound No.L112 ═A33═A36═A37═A38VIII-h-13363HHHHVIII-h-23364—PhHHHVIII-h-33365HHHHVIII-h-43366—PhHHHVIII-h-53367HHHHVIII-h-63368—PhHHHVIII-h-73369HA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.HVIII-h-83370—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.HVIII-h-93371HHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-h-103372—PhHA17 and A18 form a benzene ring. A37 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-h-113373—Ph—PhHHVIII-h-123374—PhH—PhHVIII-h-133375—PhHH—PhVIII-h-143376—PhHClHVIII-h-153377—PhH—OHHVIII-h-163378—PhH—NO2HVIII-h-173379—PhH—CNHVIII-h-183380—PhH—OPhHVIII-h-193381—PhH—SCH3HVIII-h-203382—PhH—SPhHVIII-h-213383—PhH—NPh2HVIII-h-223384—PhHCH3HVIII-h-233385—PhH—OCH3HVIII-h-243386—PhH—COOHHVIII-h-253387—PhH2-pyridylHVIII-h-263388HA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.HVIII-h-273389—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.HVIII-h-283390HHA17 and A16 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-h-293391—PhHA17 and A16 form a benzene ring. A27 and A28 form a benzene ring. A37 and A36 form a benzene ring.VIII-h-303392—Ph—PhHHVIII-h-313393—PhH—PhHVIII-h-323394—PhHH—PhVIII-h-333395—PhHClHVIII-h-343396—PhH—OHHVIII-h-353397—PhH—NO2HVIII-h-363398—PhH—CNHVIII-h-373399—PhH—OPhHVIII-h-383400—PhH—SCH3HVIII-h-393401—PhH—SPhHVIII-h-403402—PhH—NPh2HVIII-h-413403—PhHCH3HVIII-h-423404—PhH—OCH3HVIII-h-433405—PhH—COOHHVIII-h-443406—PhH2-pyridylHVIII-h-453407HA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.HVIII-h-463408—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.HVIII-h-473409HHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-h-483410—PhHA17 and A18 form a henzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-h-493411—Ph—PhHHVIII-h-503412—PhH—PhHVIII-h-513413—PhHH—PhVIII-h-523414—PhHClHVIII-h-533415—PhH—OHHVIII-h-543416—PhH—NO2HVIII-h-553417—PhH—CNHVIII-h-563418—PhH—OPhHVIII-h-573419—PhH—SCH3HVIII-h-583420—PhH—SPhHVIII-h-593421—PhH—NPh2HVIII-h-603422—PhHCH3HVIII-h-613423—PhH—OCH3HVIII-h-623424—PhH—COOHHVIII-h-633425—PhH2-pyridylHVIII-i-13426HHHHVIII-i-23427—PhHHHVIII-i-33428HHHHVIII-i-43429HHHHVIII-i-53430—PhHHHVIII-i-63431HHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-i-73432—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-i-83433HHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-i-93434HHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-i-103435—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-i-113436—Ph—PhHHVIII-i-123437—PhH—PhHVIII-i-133438—PhHH—PhVIII-i-143439—PhHClHVIII-i-153440—PhH—OHHVIII-i-163441—PhH—NO2HVIII-i-173442—PhH—CNHVIII-i-183443—PhH—OPhHVIII-i-193444—PhH—SCH3HVIII-i-203445—PhH—SPhHVIII-i-213446—PhH—N—Ph2HVIII-i-223447—PhHCH3HVIII-i-233448—PhH—OCH3HVIII-i-243449—PhH—COOHHVIII-i-253450—PhH2-pyridylHVIII-i-263451—Ph—PhHHVIII-i-273452—PhH—PhHVIII-i-283453—PhHH—PhVIII-i-293454—PhHClHVIII-i-303455—PhH—OHHVIII-i-313456—PhH—NO2HVIII-i-323457—PhH—CNHVIII-i-333458—PhH—OPhHVIII-i-343459—PhH—SCH3HVIII-i-353460—PhH—SPhHVIII-i-363461—PhH—N—Ph2HVIII-i-373462—PhHCH3HVIII-i-383463—PhH—OCH3HVIII-i-393464—PhH—COOHHVIII-i-403465—PhH2-pyridylHVIII-i-413466—Ph—PhHHVIII-i-423467—PhH—PhHVIII-i-433468—PhHH—PhVIII-i-443469—PhHClHVIII-i-453470—PhH—OHHVIII-i-463471—PhH—NO2HVIII-i-473472—PhH—CNHVIII-i-483473—PhH—OPhHVIII-i-493474—PhH—SCH3HVIII-i-503475—PhH—SPhHVIII-i-513476—PhH—N—Ph2HVIII-i-523477—PhHCH3HVIII-i-533478—PhH—OCH3HVIII-i-543479—PhH—COOHHVIII-i-553480—PhH2-pyridylHFormula (VIII)Compound No.L112A13 ═A23═A33A16 ═A26═A36A18 ═A28═A38VIII-j-13481HHHVIII-j-23482—PhHHVIII-j-33483HHHVIII-j-43484HHHVIII-j-53485—PhHHVIII-j-63486—Ph—PhHVIII-j-73487—PhH—PhVIII-j-83488—PhClHVIII-j-93489—Ph—OHHVIII-j-103490—Ph—NO2HVIII-j-113491—Ph—CNHVIII-j-123492—Ph—OPhHVIII-j-133493—Ph—SCH3HVIII-j-143494—Ph—SPhHVIII-j-153495—Ph—N—Ph2HVIII-j-163496—PhCH3HVIII-j-173497—Ph—OCH3HVIII-j-183498—Ph—COOHHVIII-j-193499—Ph2-pyridylHVIII-j-203500—Ph—PhHVIII-j-213501—PhH—PhVIII-j-223502—PhClHVIII-j-233503—Ph—OHHVIII-j-243504—Ph—NO2HVIII-j-253505—Ph—CNHVIII-j-263506—Ph—OPhHVIII-j-273507—Ph—SCH3HVIII-j-283508—Ph—SPhHVIII-j-293509—Ph—N—Ph2HVIII-j-303510—PhCH3HVIII-j-313511—Ph—OCH3HVIII-j-323512—Ph—COOHHVIII-j-333513—Ph2-pyridylHVIII-j-343514—Ph—PhHVIII-j-353515—PhH—PhVIII-j-363516—PhClHVIII-j-373517—Ph—OHHVIII-j-383518—Ph—NO2HVIII-j-393519—Ph—CNHVIII-j-403520—Ph—OPhHVIII-j-413521—Ph—SCH3HVIII-j-423522—Ph—SPhHVIII-j-433523—Ph—N—Ph2HVIII-j-443524—PhCH3HVIII-j-453525—Ph—OCH3HVIII-j-463526—Ph—COOHHVIII-j-473527—Ph2-pyridylHFormula (VIII)Compound No.L112A13 ═A23═A33A17 ═A27═A37A18 ═A28═A38VIII-k-13528HHHVIII-k-23529—PhHHVIII-k-33530HHhVIII-k-43531—PhHHVIII-k-53532HHHVIII-k-63533—PhHHVIII-k-73534HA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-k-83535—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-k-93536HA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-k-103537—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-k-113538HA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-k-123539—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring. A37 and A38 form a benzene ring.VIII-k-133540—Ph—PhHVIII-k-143541—PhH—PhVIII-k-153542—PhClHVIII-k-163543—Ph—OHHVIII-k-173544—Ph—NO2HVIII-k-183545—Ph—CNHVIII-k-193546—Ph—OPhHVIII-k-203547—Ph—SCH3HVIII-k-213548—Ph—SPhHVIII-k-223549—Ph—N—Ph2HVIII-k-233550—PhCH3HVIII-k-243551—Ph—OCH3HVIII-k-253552—Ph—COOHHVIII-k-263553—Ph2-pyridylHVIII-k-273554—Ph—PhHVIII-k-283555—PhH—PhVIII-k-293556—PhClHVIII-k-303557—Ph—OHHVIII-k-313558—Ph—NO2HVIII-k-323559—Ph—CNHVIII-k-333560—Ph—OPhHVIII-k-343561—Ph—SCH3HVIII-k-353562—Ph—SPhHVIII-k-363563—Ph—N—Ph2HVIII-k-373564—PhCH3HVIII-k-383565—Ph—OCH3HVIII-k-393566—Ph—COOHHVIII-k-403567—Ph2-pyridylHVIII-k-413568—Ph—PhHVIII-k-423569—PhH—PhVIII-k-433570—PhClHVIII-k-443571—Ph—OHHVIII-k-453572—Ph—NO2HVIII-k-463573—Ph—CNHVIII-k-473574—Ph—OPhHVIII-k-483575—Ph—SCH3HVIII-k-493576—Ph—SPhHVIII-k-503577—Ph—N—Ph2HVIII-k-513578—PhCH3HVIII-k-523579—Ph—OCH3HVIII-k-533580—Ph—COOHHVIII-k-543581—Ph2-pyridylHFormula (VIII)Compound No.L112A13 ═A23═A33A15 ═A25═A35A18 ═A28═A38VIII-l-13582HHHVIII-l-23583—PhHHVIII-l-33584HHHVIII-l-43585—PhHHVIII-l-53586HHHVIII-l-63587—Ph—PhHVIII-l-73588—PhH—PhVIII-l-83589—PhClHVIII-l-93590—Ph—OHHVIII-l-103591—Ph—NO2HVIII-l-113592—Ph—CNHVIII-l-123593—Ph—OPhHVIIl-l-133594—Ph—SCH3HVIII-l-143595—Ph—SPhHVIII-l-153596—Ph—N—Ph2HVIII-l-163597—PhCH3HVIII-l-173598—Ph—OCH3HVIII-l-183599—Ph—COOHHVIII-l-193600—Ph2-pyridylHVIII-l-203601—Ph—PhHVIII-l-213602—PhH—PhVIII-l-223603—PhClHVIII-l-233604—Ph—OHHVIII-l-243605—Ph—NO2HVIII-l-253606—Ph—CNHVIII-l-263607—Ph—OPhHVIII-l-273608—Ph—SCH3HVIII-l-283609—Ph—SPhHVIII-l-293610—Ph—N—Ph2HVIII-l-303611—PhCH3HVIII-l-313612—Ph—OCH3HVIII-l-323613—Ph—COOHHVIII-l-333614—Ph2-pyridylHVIII-l-343615—Ph—PhHVIII-l-353616—PhH—PhVIII-l-363617—PhClHVIII-l-373618—Ph—OHHVIII-l-383619—Ph—NO2HVIII-l-393620—Ph—CNHVIII-l-403621—Ph—OPhHVIII-l-413622—Ph—SCH3HVIII-l-423623—Ph—SPhHVIII-l-433624—Ph—N—Ph2HVIII-l-443625—PhCH3HVIII-l-453626—Ph—OCH3HVIII-l-463627—Ph—COOHHVIII-l-473628—Ph2-pyridylHFormula (VIII)Compound No.L111A12═A22A13═A23A15═A25A17═A27A18═A28VIII-m-1single bondHHHHHVIII-m-2single bondHHCH3HHVIII-m-3single bondHHHCH3HVIII-m-4single bondHHHHCH3VIII-m-5single bondHHHn-C2H5HVIII-m-6single bondHHHn-C3H7HVIII-m-7single bondHHHn-C4H9HVIII-m-8single bondHHHt-C4H9HVIII-m-9single bondHHPhHHVIII-m-10single bondHHHPhHVIII-m-11single bondHHHHPhVIII-m-12single bondHHH1-naphthylHVIII-m-13single bondHHH2-naphthylHVIII-m-14single bondHHH4-biphenylylHVIII-m-15single bondHHH3-biphenylylHVIII-m-16single bondHHH2-biphenylylHVIII-m-17single bondHHH2-biphenylylHVIII-m-18single bondPhPhHHHVIII-m-19single bondPhPhCH3HHVIII-m-20single bondPhPhHCH3HVIII-m-21single bondPhPhHHCH3VIII-m-22single bondPhPhHn- C2H5HVIII-m-23single bondPhPhHn-C3H7HVIII-m-24single bondPhPhHn-C4H9HVIII-m-25single bondPhPhHt-C4H9HVIII-m-26single bondPhPhPhHHVIII-m-27single bondPhPhHPhHVIII-m-28single bondPhPhHHPhVIII-m-29single bondPhPhH1-naphthylHVIII-m-30single bondPhPhH2-naphthylHVIII-m-31single bondPhPhH4-biphenylylHVIII-m-32single bondPhPhH3-biphenylylHVIII-m-33single bondPhPhH2-biphenylylHVIII-m-34single bond36293630HHHVIII-m-35single bond36313632CH3HHVIII-m-36single bond36333634HCH3HVIII-m-37single bond36353636HHCH3VIII-m-38single bond36373638Hn-C2H5HVIII-m-39single bond36393640Hn-C3H7HVIII-m-40single bond36413642Hn-C4H9HVIII-m-41single bond36433644Ht-C4H9HVIII-m-42single bond36453646—PhHHVIII-m-43single bond36473648H—PhHVIII-m-44single bond36493650HHPhVIII-m-45single bond36513652H1-naphthylHVIII-m-46single bond36533654H2-naphthylHVIII-m-47single bond36553656H4-biphenylylHVIII-m-48single bond36573658H3-biphenylylHVIII-m-49single bond36593660H2-biphenylylHVIII-m-503661HHHHHVIII-m-513662HHCH3HHVIII-m-523663HHHCH3HVIII-m-533664HHHHCH3VIII-m-543665HHHn-C2H5HVIII-m-553666HHHn-C3H7HVIII-m-563667HHHn-C4H9HVIII-m-573668HHHt-C4H9HVIII-m-583669HHPhHHVIII-m-593670HHHPhHVIII-m-603671HHHHPhVIII-m-613672HHH1-naphthylHVIII-m-623673HHH2-naphthylHVIII-m-633674HHH4-biphenylylHVIII-m-643675HHH3-biphenylylHVIII-m-653676HHH2-biphenylylHVIII-m-663677HHH2-biphenylylHVIII-m-673678PhPhHHHVIII-m-683679PhPhCH3HHVIII-m-693680PhPhHCH3HVIII-m-703681PhPhHHCH3VIII-m-713682PhPhHn-C2H5HVIII-m-723683PhPhHn-C3H7HVIII-m-733684PhPhHn-C4H9HVIII-m-743685PhPhHt-C4H9HVIII-m-753686PhPhPhHHVIII-m-763687PhPhHPhHVIII-m-773688PhPhHHPhVIII-m-783689PhPhH1-naphthylHVIII-m-793690PhPhH2-naphthylHVIII-m-803691PhPhH4-biphenylylHVIII-m-813692PhPhH3-biphenylylHVIII-m-823693PhPhH2-biphenylylHVIII-m-83369436953696HHHVIII-m-84369736983699CH3HHVIII-m-85370037013702HCH3HVIII-m-86370337043705HHCH3VIII-m-87370637073708Hn-C2H5HVIII-m-88370937103711Hn-C3H7HVIII-m-89371237133714Hn-C4H9HVIII-m-90371537163717Ht-C4H9HVIII-m-91371837193720PhHHVIII-m-92372137223723HPhHVIII-m-93372437253726HHPhVIII-m-94372737283729H1-naphthylHVIII-m-95373037313732H2-naphthylHVIII-m-96373337343735H4-biphenylylHVIII-m-97373637373738H3-biphenylylHVIII-m-98373937403741H2-biphenylylHVIII-m-993742HHHHHVIII-m-1003743HHCH3HHVIII-m-1013744HHHCH3HVIII-m-1023745HHHHCH3VIII-m-1033746HHHn-C2H5HVIII-m-1043747HHHn-C3H7HVIII-m-1053748HHHn-C4H9HVIII-m-1063749HHHt-C4H9HVIII-m-1073750HHPhHHVIII-m-1083751HHHPhHVIII-m-1093752HHHHPhVIII-m-1103753HHH1-naphthylHVIII-m-1113754HHH2-naplithylHVIII-m-1123755HHH4-biphenylylHVIII-m-1133756HHH3-biphenylylHVIII-m-1143757HHH2-biphenylylHVIII-m-1153758HHH2-biphenylylHVIII-m-1163759PhPhHHHVIII-m-1173760PhPhCH3HHVIII-m-1183761PhPhHCH3HVIII-m-1193762PhPhHHCH3VIII-m-1203763PhPhHn-C2H5HVIII-m-1213764PhPhHn-C3H7HVIII-m-1223765PhPhHn-C4H9HVIII-m-1233766PhPhHt-C4H9HVIII-m-1243767PhPhPhHHVIII-m-1253768PhPhHPhHVIII-m-1263769PhPhHHPhVIII-m-1273770PhPhH1-naphthylHVIII-m-1283771PhPhH2-naphthylHVIII-m-1293772PhPhH4-biphenylylHVIII-m-1303773PhPhH3-biphenylylHVIII-m-1313774PhPhH2-biphenylylHVIII-m-132377537763777HHHVIII-m-133377837793780CH3HHVIII-m-134378137823783HCH3HVIII-m-135378437853786HHCH3VIII-m-136378737883789Hn-C2H5HVIII-m-137379037913792Hn-C3H7HVIII-m-138379337943795Hn-C4H9HVIII-m-139379637973798Ht-C4H9HVIII-m-140379938003801PhHHVIII-m-141380238033804HPhHVIII-m-142380538063807HHPhVIII-m-143380838093810H1-naphthylHVIII-m-144381138123813H2-naphthylHVIII-m-145381438153816H4-biphenylylHVIII-m-146381738183819H3-biphenylylHVIII-m-147382038213822H3-biphenylylH


[0263] These quinoxaline compounds are obtained by (i) a process involving condensing diaminobenzene or derivatives thereof, diaminopyridine or derivatives thereof, diaminopyrimidine or derivatives thereof, diaminopyridazine or derivatives thereof with a halogenated diketone compound, followed by coupling using a nickel complex of 1,5-cyclooctadiene or the like, (ii) condensing diaminobenzene or derivatives thereof, diaminopyridine or derivatives thereof, diaminopyrimidine or derivatives thereof, diaminopyridazine or derivatives thereof with a bisdiketone compound, (iii) condensing a bisdiamine compound with a diketone compound, or (iv) converting a starting compound into an organometallic reagent of tin or the like, followed by cross-coupling.


[0264] These compounds can be identified by elemental analysis, mass analysis, IR spectroscopy, 1H and 13C NMR, etc.


[0265] In general, the quinoxaline compounds have a molecular weight of about 500 to about 2,000, a melting point of about 250 to about 500° C., and a glass transition temperature (Tg) of about 90 to about 200° C. By conventional vacuum deposition or the like, they form a transparent, smooth film of quality which maintains a stable amorphous state even above room temperature and over a long period of time.


[0266] The term “host material” used herein means a material which participates in light emission, but does not emit light by itself or emits light at a very low luminance. Specifically, an appropriate difference in luminance between the host and the dopant is such that the maximum luminance of the host is equal to or less than 10%, especially equal to or less than 2% of the maximum luminance of the dopant.


[0267] Dopants


[0268] A class of organic compounds useful as the dopant according to the invention are compounds of the following formula (V).
3823


[0269] Herein X1 to X10, L1 and L2 are independently hydrogen, halogen atoms, straight, branched or cyclic alkyl radicals which may have substituents, straight, branched or cyclic alkoxy radicals which may have substituents, straight, branched or cyclic alkylthio radicals which may have substituents, straight, branched or cyclic alkenyl radicals which may have substituents, straight, branched or cyclic alkenyloxy radicals which may have substituents, straight, branched or cyclic alkenylthio radicals which may have substituents, substituted or unsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxy radicals, substituted or unsubstituted aralkylthio radicals, substituted or unsubstituted aryl radicals, substituted or unsubstituted aryloxy radicals, substituted or unsubstituted arylthio radicals, substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR1 radicals (wherein R1 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical or a substituted or unsubstituted aryl radical), —COR2 radicals (wherein R2 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical or an amino radical), or —OCOR3 radicals (wherein R3 is a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), or at least two adjoining groups selected from X1 to X10, L1 and L2 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached, or L1 and L2 each may be a single bond.


[0270] Preferably, at least two adjoining groups selected from X1 to X10, L1 and L2 bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached. L1 and L2 each may be a single bond. n is 1 or 2.


[0271] Of the compounds of formula (V), preferred are diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivatives, having a skeleton of the following formula (VI).
3824


[0272] In formula (VI), X1 to X6, X9 to X10, X11 to X16, X19 and X20 are independently hydrogen, halogen atoms, straight, branched or cyclic alkyl radicals which may have substituents, straight, branched or cyclic alkoxy radicals which may have substituents, straight, branched or cyclic alkylthio radicals which may have substituents, straight, branched or cyclic alkenyl radicals which may have substituents, straight, branched or cyclic alkenyloxy radicals which may have substituents, straight, branched or cyclic alkenylthio radicals which may have substituents, substituted or unsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxy radicals, substituted or unsubstituted aralkylthio radicals, substituted or unsubstituted aryl radicals, substituted or unsubstituted aryloxy radicals, substituted or unsubstituted arylthio radicals, substituted or unsubstituted arylalkenyl radicals, substituted or unsubstituted alkenylaryl radicals, substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR1 radicals (wherein R1 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical or a substituted or unsubstituted aryl radical), —COR2 radicals (wherein R2 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical or an amino radical), or —OCOR3 radicals (wherein R3 is a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), or at least two adjoining groups selected from X1 to X20 may bond together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached.


[0273] The term “aryl radicals” is used herein to encompass carbocyclic aromatic radicals such as phenyl and naphthyl and heterocyclic aromatic radicals such as furyl, thienyl and pyridyl.


[0274] The straight, branched or cyclic alkyl radicals, straight, branched or cyclic alkoxy radicals, straight, branched or cyclic alkylthio radicals, straight, branched or cyclic alkenyl radicals, straight, branched or cyclic alkenyloxy radicals, and straight, branched or cyclic alkenylthio radicals, represented by X1 to X20 in formulas (V) and (VI), may have a substituent or substituents, for example, halogen atoms, aryl groups of 4 to 20 carbon atoms, alkoxy groups of 1 to 20 carbon atoms, alkoxyalkoxy groups of 2 to 20 carbon atoms, alkenyloxy groups of 2 to 20 carbon atoms, aralkyloxy groups of 4 to 20 carbon atoms, aralkyloxyalkoxy groups of 5 to 20 carbon atoms, aryloxy groups of 3 to 20 carbon atoms, aryloxyalkoxy groups of 4 to 20 carbon atoms, arylalkenyl groups of 5 to 20 carbon atoms, aralkylalkenyl groups of 6 to 20 carbon atoms, alkylthio groups of 1 to 20 carbon atoms, alkoxyalkylthio groups of 2 to 20 carbon atoms, alkylthioalkylthio groups of 2 to 20 carbon atoms, alkenylthio groups of 2 to 20 carbon atoms, aralkylthio groups of 4 to 20 carbon atoms, aralkyloxyalkylthio groups of 5 to 20 carbon atoms, aralkylthioalkylthio groups of 5 to 20 carbon atoms, arylthio groups of 3 to 20 carbon atoms, aryloxyalkylthio groups of 4 to 20 carbon atoms, arylthioalkylthio groups of 4 to 20 carbon atoms, and heteroatom-containing cyclic alkyl groups of 4 to 20 carbon atoms. The aryl groups included in these substituents may be further substituted with halogen atoms, alkyl groups of 1 to 10 carbon atoms, alkoxy groups of 1 to 10 carbon atoms, aryl groups of 3 to 10 carbon atoms, and aralkyl groups of 4 to 10 carbon atoms, among others.


[0275] The aralkyl radicals, aralkyloxy radicals, aralkylthio radicals, aryl radicals, aryloxy radicals and arylthio radicals, represented by X1 to X20 in formulas (V) and (VI), may have a substituent or substituents, for example, alkyl groups of 1 to 20 carbon atoms, alkenyl groups of 2 to 20 carbon atoms, aralkyl groups of 4 to 20 carbon atoms, aryl groups of 3 to 20 carbon atoms, alkoxy groups of 1 to 20 carbon atoms, alkoxyalkyl groups of 2 to 20 carbon atoms, alkoxyalkyloxy groups of 2 to 20 carbon atoms, alkenyloxy groups of 2 to 20 carbon atoms, alkenyloxyalkyl groups of 3 to 20 carbon atoms, alkenyloxyalkyloxy groups of 3 to 20 carbon atoms, aralkyloxy groups of 4 to 20 carbon atoms, aralkyloxyalkyl groups of 5 to 20 carbon atoms, aralkyloxyalkyloxy groups of 5 to 20 carbon atoms, aryloxy groups of 3 to 20 carbon atoms, aryloxyalkyl groups of 4 to 20 carbon atoms, aryloxyalkyloxy groups of 4 to 20 carbon atoms, alkylcarbonyl groups of 2 to 20 carbon atoms, alkenylcarbonyl groups of 3 to 20 carbon atoms, aralkylcarbonyl groups of 5 to 20 carbon atoms, arylcarbonyl groups of 4 to 20 carbon atoms, alkoxycarbonyl groups of 2 to 20 carbon atoms, alkenyloxycarbonyl groups of 3 to 20 carbon atoms, aralkyloxycarbonyl groups of 5 to 20 carbon atoms, aryloxycarbonyl groups of 4 to 20 carbon atoms, alkylcarbonyloxy groups of 2 to 20 carbon atoms, alkenylcarbonyloxy groups of 3 to 20 carbon atoms, aralkylcarbonyloxy groups of 5 to 20 carbon atoms, arylcarbonyloxy groups of 4 to 20 carbon atoms, alkylthio groups of 1 to 20 carbon atoms, aralkylthio groups of 4 to 20 carbon atoms, arylthio groups of 3 to 20 carbon atoms, nitro, cyano, formyl, halogen atoms, halogenated alkyl, hydroxyl, amino, N-mono-substituted amino groups of 1 to 20 carbon atoms, and N,N-di-substituted amino groups of 2 to 40 carbon atoms. The aryl groups included in these substituents may be further substituted with halogen atoms, alkyl groups of 1 to 10 carbon atoms, alkoxy groups of 1 to 10 carbon atoms, aryl groups of 6 to 10 carbon atoms, and aralkyl groups of 7 to 10 carbon atoms, among others.


[0276] The amino radicals represented by X1 to X20 in formulas (V) and (VI) may have a substituent or substituents, for example, be mono- or di-substituted with alkyl groups of 1 to 20 carbon atoms, aralkyl groups of 4 to 20 carbon atoms, and aryl groups of 3 to 20 carbon atoms.


[0277] The alkyl, alkenyl, aralkyl and aryl radicals represented by R1, R2 and R3 in formulas (V) and (VI) may have a substituent or substituents, as exemplified for X1 to X20.


[0278] In a preferred embodiment, X5, X6, X9, X10, X15, X16, X19 and X20 are hydrogen, and X1 to X4 and X11 to X14 are independently hydrogen, halogen atoms, straight, branched or cyclic alkyl radicals of 1 to 24 carbon atoms in total which may have substituents, straight, branched or cyclic alkoxy radicals of 1 to 24 carbon atoms in total which may have substituents, straight, branched or cyclic alkenyl, alkenylaryl and arylalkenyl radicals of 2 to 24 carbon atoms in total which may have substituents, substituted or unsubstituted aralkyl groups of 7 to 24 carbon atoms in total, substituted or unsubstituted aryl radicals of 6 to 24 carbon atoms in total, cyano radicals, heterocyclic radicals, hydroxyl radicals, —COOR1, —COR2 or —OCOR3 radicals wherein R1, R2 and R3 are as defined above.


[0279] Two adjoining groups selected from X1 to X20 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached.


[0280] The organic EL device of the invention is characterized by the inclusion of at least one fluoranthene derivative or diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative. The use of a diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative in a light emitting layer as a luminescent component, for example, enables to produce an organic EL device having improved luminance and durability over similar EL devices of the prior art. The use of the specific derivative in combination with another luminescent component to form a light emitting layer enables to produce an organic EL device capable of emitting white light and having improved luminance and durability.


[0281] Illustrative, non-limiting, examples of the compounds of formulas (V) and (VI) according to the invention are given below. Ph designates phenyl.
83+TC,51/ 3825“A and B form a fused ring” in3826means3827Com-poundNo.X1X2X3X6X7X8A-1HHHHHHA-2HHHHHHA-3HHHHHHA-4HHHHHHA-5HHHHHHA-6HHHHHHA-7HHHHHHA-8HHHHHHA-9HHHHHHA-10HHHHHHA-11PhHHHHPhA-123828HHHH3829A-13CH3HHHHCH3A-14HPhHHPhHA-15H3830HH3831HA-16HCH3HHCH3HA-17X1 and X2 form a fused ring.HHHHA-18X1 and X2 form a fused ring.HHHHA-19X1 and X2 form a fused ring.HHHHA-20X1 and X2 form a fused ring.HHHHA-21X1 and X2 form a fused ring.HHHHA-22X1 and X2 form a fused ring.HHHHA-23X1 and X2 form a fused ring.HHHHA-24X1 and X2 form a fused ring.HHHHA-25X1 and X2 form a fused ring.HHHHA-26X1 and X2 form a fused ring.HHHHA-27X1 and X2 form a fused ring.HHHPhA-28X1 and X2 form a fused ring.HHH3832A-29X1 and X2 form a fused ring.HHHCH3A-30X1 and X2 form a fused ring.HHPhHA-31X1 and X2 form a fused ring.HH3833HA-32X1 and X2 form a fused ring.HHCH3HA-33HHHHHHA-34HHHHHHA-35HHHHHHA-36HHHHHHA-37HHHHHHA-38HHHHHHA-39HHHHHHA-40HHHHHHA-41HHHHHHA-42HHHHHHA-43PhHHHHPhA-443834HHHH3835A-45CH3HHHHCH3A-46HPhHHPhHA-47H3836HH3837HA-48CH3HHCH3HA-49HHHHHHA-50PhHHHHPhA-513838HHHH3839A-52CH3HHHHCH3A-53HPhHHPhHA-54H3840HH3841HA-55HCH3HHCH3HA-56X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-57X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-58X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-59X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-60X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-61X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-62X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-63X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-64X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-65X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.A-66X1 and X2 form a fused ring.HHX1 and X2 form a fused ring.Com-poundNo.X11X12X13X14A-1HHHHA-2PhHHPhA-33842HH3843A-43844HH3845A-53846HH3847A-6CH3HHCH3A-73848HH3849A-8PhPhPhPhA-9Ph38503851PhA-10PhCH3CH3PhA-11PhHHPhA-12PhHHPhA-13PhHHPhA-14PhHHPhA-15PhHHPhA-16PhHHPhA-17HHHHA-18PhHHPhA-193852HH3853A-203854HH3855A-213856HH3857A-22CH3HHCH3A-233858HH3859A-24PhPhPhPhA-25Ph38603861PhA-26PhCH3CH3PhA-27PhHHPhA-28PhHHPhA-29PhHHPhA-30PhHHPhA-31PhHHPhA-32PhHHPhA-33HHX13 and X14 form a fused ring.A-34PhHX13 and X14 form a fused ring.A-353862HX13 and X14 form a fused ring.A-363863HX13 and X14 form a fused ring.A-373864HX13 and X14 form a fused ring.A-38CH3HX13 and X14 form a fused ring.A-393865HX13 and X14 form a fused ring.A-40PhPhX13 and X14 form a fused ring.A-41Ph3866X13 and X14 form a fused ring.A-42PhCH3X13 and X14 form a fused ring.A-43PhHX13 and X14 form a fused ring.A-44PhHX13 and X14 form a fused ring.A-45PhHX13 and X14 form a fused ring.A-46PhHX13 and X14 form a fused ring.A-47PhHX13 and X14 form a fused ring.A-48PhHX13 and X14 form a fused ring.A-49X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-50X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-51X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-52X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-53X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-54X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-55X13 and X14 form a fused ring.X13 and X14 form a fused ring.A-56HHHHA-57PhHHPhA-583867HH3868A-593869HH3870A-603871HH3872A-61CH3HHCH3A-623873HH3874A-63PhPhPhPhA-64Ph38753876PhA-65PhCH3CH3PhA-66PhHHPh


[0282]

84


























3877





“A and B form a fused ring in


3878





means


3879






















Compound No.
X1
X2
X3
X6
X7
X8
X11





B-1
H
H
H
H
H
H
H


B-2
H
H
H
H
H
H
Ph





B-3
H
H
H
H
H
H


3880










B-4
H
H
H
H
H
H


3881










B-5
H
H
H
H
H
H


3882










B-6
H
H
H
H
H
H
CH3





B-7
H
H
H
H
H
H


3883










B-8


3884





H
H
H
H


3885





Ph





B-9
CH3
H
H
H
H
CH3
Ph


B-10
H
Ph
H
H
Ph
H
Ph





B-11
H


3886





H
H


3887





H
Ph





B-12
H
CH3
H
H
CH3
H
Ph













B-13
H
H
H
H
X7 and X8 form a fused ring.
H


B-14
H
H
H
H
X7 and X8 form a fused ring.
Ph





B-15
H
H
H
H
X7 and X8 form a fused ring.


3888










B-16
H
H
H
H
X7 and X8 form a fused ring.


3889










B-17
H
H
H
H
X7 and X8 form a fused ring.


3890










B-18
H
H
H
H
X7 and X8 form a fused ring.
CH3





B-19
H
H
H
H
X7 and X8 form a fused ring.


3891










B-20
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-21
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-22
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-23
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-24
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-25
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-26
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-27
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-28
H
H
H
H
X7 and X8 form a fused ring.
Ph


B-29
Ph
H
H
H
X7 and X8 form a fused ring.
Ph





B-30


3892





H
H
H
X7 and X8 form a fused ring.
Ph





B-31
CH3
H
H
H
X7 and X8 form a fused ring.
Ph














B-32
H
H
H
H
H
H
H


B-33
H
H
H
H
H
H
Ph





B-34
H
H
H
H
H
H


3893










B-35
H
H
H
H
H
H


3894










B-36
H
H
H
H
H
H


3895










B-37
H
H
H
H
H
H
CH3





B-38
H
H
H
H
H
H


3896










B-39
H
H
H
H
H
H
Ph


B-40
H
H
H
H
H
H
Ph


B-41
H
H
H
H
H
H
Ph


B-42
H
H
H
H
H
H
Ph


B-43
H
H
H
H
H
H
Ph


B-44
H
H
H
H
H
H
Ph


B-45
H
H
H
H
H
H
Ph


B-46
H
H
H
H
H
H
Ph


B-47
H
H
H
H
H
H
Ph


B-48
Ph
H
H
H
H
Ph
Ph





B-49


3897





H
H
H
H


3898





Ph





B-50
CH3
H
H
H
H
CH3
Ph


B-51
H
Ph
H
H
Ph
H
Ph





B-52
H


3899





H
H


3900





H
Ph





B-53
H
CH3
H
H
CH3
H
Ph


B-54
H
H
H
H
H
H
H


B-55
H
H
H
H
H
H
Ph





B-56
H
H
H
H
H
H


3901










B-57
H
H
H
H
H
H


3902










B-58
H
H
H
H
H
H


3903










B-59
H
H
H
H
H
H
CH3





B-60
H
H
H
H
H
H


3904










B-61
H
H
H
H
H
H
Ph


B-62
H
H
H
H
H
H
Ph


B-63
H
H
H
H
H
H
Ph


B-64
H
H
H
H
H
H
Ph


B-65
H
H
H
H
H
H
Ph


B-66
H
H
H
H
H
H
Ph


B-67
H
H
H
H
H
H
Ph


B-68
H
H
H
H
H
H
Ph


B-69
H
H
H
H
H
H
Ph


B-70
Ph
H
H
H
H
Ph
Ph





B-71


3905





H
H
H
H


3906





Ph





B-72
CH3
H
H
H
H
CH3
Ph


B-73
H
Ph
H
H
Ph
H
Ph





B-74
H


3907





H
H


3908





H
Ph





B-75
H
CH3
H
H
CH3
H
Ph












B-76
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
H


B-77
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph





B-78
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.


3909










B-79
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.


3910










B-80
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.


3911










B-81
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
CH3





B-82
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.


3912










B-83
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-84
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-85
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-86
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-87
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-88
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-89
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-90
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph


B-91
X1 and X2 form a fused ring.
H
H
X7 and X8 form a fused ring.
Ph

















Compound No.
X14
X15
X16
X17
X18
















B-1
H
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



B-2
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.







B-3


3913





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.







B-4


3914





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.







B-5


3915





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.







B-6
CH3
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.







B-7


3916





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.







B-8
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



B-9
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



B-10
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



B-11
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



B-12
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.














B-13
H
H
H
H
H



B-14
Ph
H
H
H
H







B-15


3917





H
H
H
H







B-16


3918





H
H
H
H







B-17


3919





H
H
H
H







B-18
CH3
H
H
H
H







B-19


3920





H
H
H
H







B-20
Ph
Ph
H
H
Ph







B-21
Ph


3921





H
H


3922












B-22
Ph


3923





H
H


3924












B-23
Ph


3925





H
H


3926












B-24
Ph
CH3
H
H
CH3







B-25
Ph


3927





H
H


3928












B-26
Ph
H
Ph
Ph
H







B-27
Ph
H


3929







3930





H







B-28
Ph
H
CH3
CH3
H



B-29
Ph
H
H
H
H



B-30
Ph
H
H
H
H



B-31
Ph
H
H
H
H













B-32
H
X15 and X16 form a fused ring.
H
H



B-33
Ph
X15 and X16 form a fused ring.
H
H







B-34


3931





X15 and X16 form a fused ring.
H
H







B-35


3932





X15 and X16 form a fused ring.
H
H







B-36


3933





X15 and X16 form a fused ring.
H
H







B-37
CH3
X15 and X16 form a fused ring.
H
H







B-38


3934





X15 and X16 form a fused ring.
H
H







B-39
Ph
X15 and X16 form a fused ring.
H
Ph







B-40
Ph
X15 and X16 form a fused ring.
H


3935












B-41
Ph
X15 and X16 form a fused ring.
H


3936












B-42
Ph
X15 and X16 form a fused ring.
H


3937












B-43
Ph
X15 and X16 form a fused ring.
H
CH3







B-44
Ph
X15 and X16 form a fused ring.
H


3938












B-45
Ph
X15 and X16 form a fused ring.
Ph
H







B-46
Ph
X15 and X16 form a fused ring.


3939





H







B-47
Ph
X15 and X16 form a fused ring.
CH3
H



B-48
Ph
X15 and X16 form a fused ring.
H
H



B-49
Ph
X15 and X16 form a fused ring.
H
H



B-50
Ph
X15 and X16 form a fused ring.
H
H



B-51
Ph
X15 and X16 form a fused ring.
H
H



B-52
Ph
X15 and X16 form a fused ring.
H
H



B-53
Ph
X15 and X16 form a fused ring.
H
H














B-54
H
H
H
H
H



B-55
Ph
H
H
H
H







B-56


3940





H
H
H
H







B-57


3941





H
H
H
H







B-58


3942





H
H
H
H







B-59
CH3
H
H
H
H







B-60


3943





H
H
H
H







B-61
Ph
Ph
H
H
Ph







B-62
Ph


3944





H
H


3945












B-63
Ph


3946





H
H


3947












B-64
Ph


3948





H
H


3949












B-65
Ph
CH3
H
H
CH3







B-66
Ph


3950





H
H


3951












B-67
Ph
H
Ph
Ph
H







B-68
Ph
H


3952







3953





H







B-69
Ph
H
CH3
CH3
H



B-70
Ph
H
H
H
H



B-71
Ph
H
H
H
H



B-72
Ph
H
H
H
H



B-73
Ph
H
H
H
H



B-74
Ph
H
H
H
H



B-75
Ph
H
H
H
H



B-76
H
H
H
H
H



B-77
Ph
H
H
H
H







B-78


3954





H
H
H
H







B-79


3955





H
H
H
H







B-80


3956





H
H
H
H







B-81
CH3
H
H
H
H







B-82


3957





H
H
H
H







B-83
Ph
Ph
H
H
Ph







B-84
Ph


3958





H
H


3959












B-85
Ph


3960





H
H


3961












B-86
Ph


3962





H
H


3963












B-87
Ph
CH3
H
H
CH3







B-88
Ph


3964





H
H


3965












B-89
Ph
H
Ph
Ph
H







B-90
Ph
H


3966







3967





H







B-91
Ph
H
CH3
CH3
H
























3968





“C, A and B form a fused ring” in


3969





means


3970























Compound No.
X1
X2
X8
X3
X6
X7
X11
X14
















B-92
X1, X2 and X8 form a fused ring.
H
H
H
H
H


B-93
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph





B-94
X1, X2 and X8 form a fused ring.
H
H
H


3971







3972










B-95
X1, X2 and X8 form a fused ring.
H
H
H


3973







3974










B-96
X1, X2 and X8 form a fused ring.
H
H
H


3975







3976










B-97
X1, X2 and X8 form a fused ring.
H
H
H
CH3
CH3





B-98
X1, X2 and X8 form a fused ring.
H
H
H


3977







3978










B-99
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-100
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-101
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-102
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-103
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-104
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-105
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-106
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-107
X1, X2 and X8 form a fused ring.
H
H
H
Ph
Ph


B-108
X1, X2 and X8 form a fused ring.
H
H
Ph
Ph
Ph





B-109
X1, X2 and X8 form a fused ring.
H
H


3979





Ph
Ph





B-110
X1, X2 and X8 form a fused ring.
H
H
CH3
Ph
Ph
















Compound No.
X15
X16
X17
X18







B-92
H
H
H
H



B-93
H
H
H
H



B-94
H
H
H
H



B-95
H
H
H
H



B-96
H
H
H
H



B-97
H
H
H
H



B-98
H
H
H
H



B-99
Ph
H
H
Ph







B-100


3980





H
H


3981












B-101


3982





H
H


3983












B-102


3984





H
H


3985












B-103
CH3
H
H
CH3







B-104


3986





H
H


3987












B-105
H
Ph
Ph
H







B-106
H


3988







3989





H







B-107
H
CH3
CH3
H



B-108
H
H
H
H



B-109
H
H
H
H



B-110
H
H
H
H











[0283]

85


























3990





“A and B form a fused ring in


3991





means


3992





















Com-








pound








No.
X1
X2
X3
X6
X7
X8





C-1
H
H
H
H
H
H


C-2
H
H
H
H
H
H


C-3
H
H
H
H
H
H


C-4
H
H
H
H
H
H


C-5
H
H
H
H
H
H


C-6
H
H
H
H
H
H


C-7
H
H
H
H
H
H


C-8
H
H
H
H
H
H


C-9
H
H
H
H
H
H


C-10
H
H
H
H
H
H


C-11
Ph
H
H
H
H
Ph





C-12


3993





H
H
H
H


3994










C-13
CH3
H
H
H
H
CH3


C-14
H
Ph
H
H
Ph
H





C-15
H


3995





H
H


3996





H





C-16
H
CH3
H
H
CH3
H
















Com-







pound







No.
X11
X14
P1
P2







C-1
H
H
H
H



C-2
Ph
Ph
H
H







C-3


3997







3998





H
H







C-4


3999







4000





H
H







C-5


4001







4002





H
H







C-6
CH3
CH3
H
H







C-7


4003







4004





H
H







C-8
Ph
Ph
Ph
Ph







C-9
Ph
Ph


4005







4006








C-10
Ph
Ph
CH3
CH3



C-11
Ph
Ph
H
H



C-12
Ph
Ph
H
H



C-13
Ph
Ph
H
H



C-14
Ph
Ph
H
H



C-15
Ph
Ph
H
H



C-16
Ph
Ph
H
H











[0284]

86


























4007





“A and B form a fused ring” in


4008





means


4009

























Compound No.
X1
X2
X3
X4
X5
X6
X7
X8
X11
X14





D-1
H
H
H
H
H
H
H
H
H
H


D-2
H
H
H
H
H
H
H
H
Ph
Ph





D-3
H
H
H
H
H
H
H
H


4010







4011










D-4
H
H
H
H
H
H
H
H


4012







4013










D-5
H
H
H
H
H
H
H
H
CH3
CH3





D-6
H
H
H
H
H
H
H
H


4014







4015










D-7
H
H
H
H
H
H
H
H


4016







4017










D-8
H
H
H
H
H
H
H
H
Ph
Ph


D-9
H
H
H
H
H
H
H
H
Ph
Ph


D-10
H
H
H
H
H
H
H
H
Ph
Ph


D-11
H
H
H
H
H
H
H
H
Ph
Ph


D-12
H
H
H
H
H
H
H
H
Ph
Ph


D-13
H
H
H
H
H
H
H
H
Ph
Ph


D-14
Ph
H
H
H
H
H
H
Ph
Ph
Ph





D-15


4018





H
H
H
H
H
H


4019





Ph
Ph





D-16
CH3
H
H
H
H
H
H
CH3
Ph
Ph
















D-17
H
H
H
H
X5 and X6 form a fused ring.
H
H
H
H


D-18
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph





D-19
H
H
H
H
X5 and X6 form a fused ring.
H
H


4020







4021










D-20
H
H
H
H
X5 and X6 form a fused ring.
H
H


4022







4023










D-21
H
H
H
H
X5 and X6 form a fused ring.
H
H
CH3
CH3





D-22
H
H
H
H
X5 and X6 form a fused ring.
H
H


4024







4025










D-23
H
H
H
H
X5 and X6 form a fused ring.
H
H


4026







4027










D-24
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph


D-25
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph


D-26
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph


D-27
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph


D-28
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph


D-29
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph
Ph


D-30
Ph
H
H
H
X5 and X6 form a fused ring.
H
Ph
Ph
Ph





D-31


4028





H
H
H
X5 and X6 form a fused ring.
H


4029





Ph
Ph





D-32
CH3
H
H
H
X5 and X6 form a fused ring.
H
CH3
Ph
Ph
















Compound No.
X15
X16
X17
X18







D-1
H
H
H
H



D-2
H
H
H
H



D-3
H
H
H
H



D-4
H
H
H
H



D-5
H
H
H
H



D-6
H
H
H
H



D-7
H
H
H
H



D-8
Ph
H
H
Ph







D-9


4030





H
H


4031












D-10
CH3
H
H
CH3



D-11
H
Ph
Ph
H







D-12
H


4032







4033





H







D-13
H
CH3
CH3
H



D-14
H
H
H
H



D-15
H
H
H
H



D-16
H
H
H
H



D-17
H
H
H
H



D-18
H
H
H
H



D-19
H
H
H
H



D-20
H
H
H
H



D-21
H
H
H
H



D-22
H
H
H
H



D-23
H
H
H
H



D-24
Ph
H
H
Ph







D-25


4034





H
H


4035












D-26
CH3
H
H
CH3



D-27
H
Ph
Ph
H







D-28
H


4036







4037





H







D-29
H
CH3
CH3
H



D-30
H
H
H
H



D-31
H
H
H
H



D-32
H
H
H
H
























4038





“A and B form a fused ring” in


4039





means


4040
























Compound No.
X1
X2
X3
X4
X5
X6
X7
X8
X11





D-33
H
H
H
H
H
H
H
H
H


D-34
H
H
H
H
H
H
H
H
Ph





D-35
H
H
H
H
H
H
H
H


4041










D-36
H
H
H
H
H
H
H
H


4042










D-37
H
H
H
H
H
H
H
H
CH3





D-38
H
H
H
H
H
H
H
H


4043










D-39
H
H
H
H
H
H
H
H


4044










D-40
H
H
H
H
H
H
H
H
Ph


D-41
H
H
H
H
H
H
H
H
Ph


D-42
H
H
H
H
H
H
H
H
Ph


D-43
Ph
H
H
H
H
H
H
Ph
Ph





D-44


4045





H
H
H
H
H
H


4046





Ph





D-45
CH3
H
H
H
H
H
H
CH3
Ph















D-46
H
H
H
H
X5 and X6 form a fused ring.
H
H
H


D-47
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph





D-48
H
H
H
H
X5 and X6 form a fused ring.
H
H


4047










D-49
H
H
H
H
X5 and X6 form a fused ring.
H
H


4048










D-50
H
H
H
H
X5 and X6 form a fused ring.
H
H
CH3





D-51
H
H
H
H
X5 and X6 form a fused ring.
H
H


4049










D-52
H
H
H
H
X5 and X6 form a fused ring.
H
H


4050










D-53
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph


D-54
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph


D-55
H
H
H
H
X5 and X6 form a fused ring.
H
H
Ph


D-56
Ph
H
H
H
X5 and X6 form a fused ring.
H
Ph
Ph





D-57


4051





H
H
H
X5 and X6 form a fused ring.
H


4052





Ph





D-58
CH3
H
H
H
X5 and X6 form a fused ring.
H
CH3
Ph















D-59
H
X2 and X3 form a fused ring.
H
H
H
H
H
H


D-60
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph





D-61
H
X2 and X3 form a fused ring.
H
H
H
H
H


4053










D-62
H
X2 and X3 form a fused ring.
H
H
H
H
H


4054










D-63
H
X2 and X3 form a fused ring.
H
H
H
H
H
CH3





D-64
H
X2 and X3 form a fused ring.
H
H
H
H
H


4055










D-65
H
X2 and X3 form a fused ring.
H
H
H
H
H


4056










D-66
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph


D-67
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph


D-68
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph


D-69
Ph
X2 and X3 form a fused ring.
H
H
H
H
Ph
Ph





D-70


4057





X2 and X3 form a fused ring.
H
H
H
H


4058





Ph





D-71
CH3
X2 and X3 form a fused ring.
H
H
H
H
CH3
Ph















Compound No.
X14
X15
X16







D-33
H
H
H



D-34
Ph
H
H







D-35


4059





H
H







D-36


4060





H
H







D-37
CH3
H
H







D-38


4061





H
H







D-39


4062





H
H







D-40
Ph
Ph
Ph







D-41
Ph


4063







4064












D-42
Ph
CH3
CH3



D-43
Ph
H
H



D-44
Ph
H
H



D-45
Ph
H
H



D-46
H
H
H



D-47
Ph
H
H







D-48


4065





H
H







D-49


4066





H
H







D-50
CH3
H
H







D-51


4067





H
H







D-52


4068





H
H







D-53
Ph
Ph
Ph







D-54
Ph


4069







4070












D-55
Ph
CH3
CH3



D-56
Ph
H
H



D-57
Ph
H
H



D-58
Ph
H
H



D-59
H
H
H



D-60
Ph
H
H







D-61


4071





H
H







D-62


4072





H
H







D-63
CH3
H
H







D-64


4073





H
H







D-65


4074





H
H







D-66
Ph
Ph
Ph







D-67
Ph


4075







4076












D-68
Ph
CH3
CH3



D-69
Ph
H
H



D-70
Ph
H
H



D-71
Ph
H
H
























4077





“A and B form a fused ring” in


4078





means


4079

























Compound No.
X1
X2
X3
X4
X5
X6
X7
X8
X11
X14



















D-72
H
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


D-73
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph





D-74
H
X2 and X3 form a fused ring.
H
H
H
H
H


4080







4081










D-75
H
X2 and X3 form a fused ring.
H
H
H
H
H


4082







4083










D-76
H
X2 and X3 form a fused ring.
H
H
H
H
H
CH3
CH3





D-77
H
X2 and X3 form a fused ring.
H
H
H
H
H


4084







4085










D-78
H
X2 and X3 form a fused ring.
H
H
H
H
H


4086







4087










D-79
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph


D-80
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph


D-81
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph


D-82
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph


D-83
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph


D-84
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph


D-85
Ph
X2 and X3 form a fused ring.
H
H
H
H
Ph
Ph
Ph





D-86


4088





X2 and X3 form a fused ring.
H
H
H
H


4089





Ph
Ph





D-87
CH3
X2 and X3 form a fused ring.
H
H
H
H
CH3
Ph
Ph


D-88
H
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


D-89
H
X2 and X3 form a fused ring.
H
H
H
H
H
Ph
Ph





D-90
H
X2 and X3 form a fused ring.
H
H
H
H
H


4090







4091










D-91
H
X2 and X3 form a fused ring.
H
H
H
H
H


4092







4093










D-92
H
X2 and X3 form a fused ring.
H
H
H
H
H
CH3
CH3





D-93
H
X2 and X3 form a fused ring.
H
H
H
H
H


4094







4095










D-94
H
X2 and X3 form a fused ring.
H
H
H
H
H


4096







4097










D-95
Ph
X2 and X3 form a fused ring.
H
H
H
H
Ph
Ph
Ph





D-96


4098





X2 and X3 form a fused ring.
H
H
H
H


4099





Ph
Ph





D-97
CH3
X2 and X3 form a fused ring.
H
H
H
H
CH3
Ph
Ph
















Compound No.
X15
X16
X17
X18







D-72
H
H
H
H



D-73
H
H
H
H



D-74
H
H
H
H



D-75
H
H
H
H



D-76
H
H
H
H



D-77
H
H
H
H



D-78
H
H
H
H



D-79
Ph
H
H
Ph







D-80


4100





H
H


4101












D-81
CH3
H
H
CH3



D-82
H
Ph
Ph
H







D-83
H


4102







4103





H







D-84
H
CH3
CH3
H



D-85
H
H
H
H



D-86
H
H
H
H



D-87
H
H
H
H











D-88
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-89
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-90
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-91
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-92
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-93
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-94
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-95
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-96
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



D-97
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.











[0285]

87


























4104





“A and B form a fused ring” in


4105





means


4106























Com-










pound










No.
X2
X3
X6
X7
X11 = 21
X12 = X22
X13 = X23
X14 = X24





E-1
H
H
H
H
H
H
H
H


E-2
H
H
H
H
Ph
H
H
Ph





E-3
H
H
H
H


4107





H
H


4108










E-4
H
H
H
H


4109





H
H


4110










E-5
H
H
H
H


4111





H
H


4112










E-6
H
H
H
H
CH3
H
H
CH3





E-7
H
H
H
H


4113





H
H


4114










E-8
H
H
H
H
Ph
Ph
Ph
Ph





E-9
H
H
H
H
Ph


4115







4116





Ph





E-10
H
H
H
H
Ph
CH3
CH3
Ph


E-11
Ph
H
Ph
H
Ph
H
H
Ph





E-12


4117





H


4118





H
Ph
H
H
Ph





E-13
CH3
H
CH3
H
Ph
H
H
Ph




















Compound No.
X2
X3
X6
X7
X11 = 21
X12 = X22
X13
X14
X23
X24

















E-14
H
H
H
H
H
H
X13 and X14, X23 and X24 form fused rings.


E-15
H
H
H
H
Ph
H
X13 and X14, X23 and X24 form fused rings.





E-16
H
H
H
H


4119





H
X13 and X14, X23 and X24 form fused rings.





E-17
H
H
H
H


4120





H
X13 and X14, X23 and X24 form fused rings.





E-18
H
H
H
H


4121





H
X13 and X14, X23 and X24 form fused rings.





E-19
H
H
H
H
CH3
H
X13 and X14, X23 and X24 form fused rings.





E-20
H
H
H
H


4122





H
X13 and X14, X23 and X24 form fused rings.





E-21
H
H
H
H
Ph
Ph
X13 and X14, X23 and X24 form fused rings.





E-22
H
H
H
H
Ph


4123





X13 and X14, X23 and X24 form fused rings.





E-23
H
H
H
H
Ph
CH3
X13 and X14, X23 and X24 form fused rings.


E-24
Ph
H
H
Ph
Ph
H
X13 and X14, X23 and X24 form fused rings.





E-25


4124





H
H


4125





Ph
H
X13 and X14, X23 and X24 form fused rings.





E-26
CH3
H
H
CH3
Ph
H
X13 and X14, X23 and X24 form fused rings.


















Compound No.
X2
X3
X6
X7
X11 = X21
X12 = X22
X13 = X23
X14 = X24
















E-27
H
H
H
H
X11 and X12, X21 and X22 form fused rings.
X13 and X14, X23 and X24 form fused rings.


E-28
Ph
H
Ph
H
X11 and X12, X21 and X22 form fused rings.
X13 and X14, X23 and X24 form fused rings.





E-29


4126





H


4127





H
X11 and X12, X21 and X22 form fused rings.
X13 and X14, X23 and X24 form fused rings.





E-30
CH3
H
CH3
H
X11 and X12, X21 and X22 form fused rings.
X13 and X14, X23 and X24 form fused rings.
















Compound No.
X2
X3
X6
X7
X11 = 21
X12 = X22





E-31
H
H
H
H
H
H


E-32
H
H
H
H
Ph
H





E-33
H
H
H
H


4128





H





E-34
H
H
H
H


4129





H





E-35
H
H
H
H


4130





H





E-36
H
H
H
H
CH3
H





E-37
H
H
H
H


4131





H





E-38
H
H
H
H
Ph
Ph





E-39
H
H
H
H
Ph


4132










E-40
H
H
H
H
Ph
CH3


E-41
Ph
H
Ph
H
Ph
H





E-42


4133





H


4134





H
Ph
H





E-43
CH3
H
CH3
H
Ph
H
















Compound No.
X13
X14
X23
X24
















E-31
X13 and X14 form a fused ring.
H
H



E-32
X13 and X14 form a fused ring.
H
Ph







E-33
X13 and X14 form a fused ring.
H


4135












E-34
X13 and X14 form a fused ring.
H


4136












E-35
X13 and X14 form a fused ring.
H


4137












E-36
X13 and X14 form a fused ring.
H
CH3







E-37
X13 and X14 form a fused ring.
H


4138












E-38
X13 and X14 form a fused ring.
Ph
Ph







E-39
X13 and X14 form a fused ring.


4139





Ph







E-40
X13 and X14 form a fused ring.
CH3
Ph



E-41
X13 and X14 form a fused ring.
H
Ph



E-42
X13 and X14 form a fused ring.
H
Ph



E-43
X13 and X14 form a fused ring.
H
Ph

















Compound No.
X2
X3
X6
X7
X11       X12
X13       X14





E-44
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-45
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-46
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-47
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-48
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-49
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-50
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-51
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-52
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-53
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-54
Ph
H
Ph
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.





E-55


4140





H


4141





H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.





E-56
CH3
H
CH3
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.
















Compound No.
X21
X22
X23
X24







E-44
H
H
H
H



E-45
Ph
H
H
Ph







E-46


4142





H
H


4143












E-47


4144





H
H


4145












E-48


4146





H
H


4147












E-49
CH3
H
H
CH3







E-50


4148





H
H


4149












E-51
Ph
Ph
Ph
Ph







E-52
Ph


4150







4151





Ph







E-53
Ph
CH3
CH3
Ph



E-54
Ph
H
H
Ph



E-55
Ph
H
H
Ph



E-56
Ph
H
H
Ph

















Compound No.
X2
X3
X6
X7
X11 = 21
X12





E-57
H
H
H
H
H
H


E-58
H
H
H
H
Ph
H





E-59
H
H
H
H


4152





H





E-60
H
H
H
H


4153





H





E-61
H
H
H
H


4154





H





E-62
H
H
H
H
CH3
H





E-63
H
H
H
H


4155





H





E-64
H
H
H
H
Ph
Ph





E-65
H
H
H
H
Ph


4156










E-66
H
H
H
H
Ph
CH3


E-67
Ph
H
Ph
H
Ph
H





E-68


4157





H


4158





H
Ph
H





E-69
CH3
H
CH3
H
Ph
H

















Compound No.
X13
X14
X22
X23
X24
















E-57
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
H



E-58
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph







E-59
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4159












E-60
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4160












E-61
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4161












E-62
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
CH3







E-63
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4162












E-64
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-65
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-66
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-67
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-68
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-69
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph

















Compound No.
X2
X3
X6
X7
X11 = 24
X12 = X23





E-70
H
H
H
H
H
H


E-71
H
H
H
H
Ph
H





E-72
H
H
H
H


4163





H





E-73
H
H
H
H


4164





H





E-74
H
H
H
H


4165





H





E-75
H
H
H
H
CH3
H





E-76
H
H
H
H


4166





H





E-77
H
H
H
H
Ph
Ph





E-78
H
H
H
H
Ph


4167










E-79
H
H
H
H
Ph
CH3


E-80
Ph
H
Ph
H
Ph
H





E-81


4168





H


4169





H
Ph
H





E-82
CH3
H
CH3
H
Ph
H
















Compound No.
X13
X14
X21
X22















E-70
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-71
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-72
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-73
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-74
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-75
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-76
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-77
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-78
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-79
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-80
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-81
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



E-82
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.



















Compound No.
X2
X3
X6
X7
 X11
X12
 X13
X14
















E-83
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-84
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-85
H
H
H
H
X11 and X12 form a fuaed ring.
X13 and X14 form a fused ring.


E-86
H
H
H
H
X11 and X12 form a fuaed ring.
X13 and X14 form a fused ring.


E-87
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-88
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-89
H
H
H
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.


E-90
Ph
H
Ph
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.





E-91


4170





H


4171





H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.





E-92
CH3
H
CH3
H
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.
















Compound No.
X21
X22
X23
X24
















E-83
H
X22 and X23 form a fused ring.
H



E-84
Ph
X22 and X23 form a fused ring.
Ph







E-85


4172





X22 and X23 form a fused ring.


4173












E-86


4174





X22 and X23 form a fused ring.


4175












E-87


4176





X22 and X23 form a fused ring.


4177












E-88
CH3
X22 and X23 form a fused ring.
CH3







E-89


4178





X22 and X23 form a fused ring.


4179












E-90
Ph
X22 and X23 form a fused ring.
Ph



E-91
Ph
X22 and X23 form a fused ring.
Ph



E-92
Ph
X22 and X23 form a fused ring.
Ph



















Compound No.
 X2
X3
X6
X7
X11
X12
X13
X14
















E-93
X2 and X3 form a fused ring.
H
H
H
H
X13 and X14 form a fused ring.


E-94
X2 and X3 form a fused ring.
H
H
Ph
H
X13 and X14 form a fused ring.





E-95
X2 and X3 form a fused ring.
H
H


4180





H
X13 and X14 form a fused ring.





E-96
X2 and X3 form a fused ring.
H
H


4181





H
X13 and X14 form a fused ring.





E-97
X2 and X3 form a fused ring.
H
H


4182





H
X13 and X14 form a fused ring.





E-98
X2 and X3 form a fused ring.
H
H
CH3
H
X13 and X14 form a fused ring.





E-99
X2 and X3 form a fused ring.
H
H


4183





H
X13 and X14 form a fused ring.





E-100
X2 and X3 form a fused ring.
H
H
Ph
Ph
X13 and X14 form a fused ring.





E-101
X2 and X3 form a fused ring.
H
H
Ph


4184





X13 and X14 form a fused ring.





E-102
X2 and X3 form a fused ring.
H
H
Ph
CH3
X13 and X14 form a fused ring.


E-103
X2 and X3 form a fused ring.
Ph
H
Ph
H
X13 and X14 form a fused ring.





E-104
X2 and X3 form a fused ring.


4185





H
Ph
H
X13 and X14 form a fused ring.





E-105
X2 and X3 form a fused ring.
CH3
H
Ph
H
X13 and X14 form a fused ring.
















Compound No.
X21
X22
X23
X24
















E-93
X21 and X22 form a fused ring.
H
H



E-94
X21 and X22 form a fused ring.
H
Ph







E-95
X21 and X22 form a fused ring.
H


4186












E-96
X21 and X22 form a fused ring.
H


4187












E-97
X21 and X22 form a fused ring.
H


4188












E-98
X21 and X22 form a fused ring.
H
CH3







E-99
X21 and X22 form a fused ring.
H


4189












E-100
X21 and X22 form a fused ring.
Ph
Ph







E-101
X21 and X22 form a fused ring.


4190





Ph







E-102
X21 and X22 form a fused ring.
CH3
Ph



E-103
X21 and X22 form a fused ring.
H
Ph



E-104
X21 and X22 form a fused ring.
H
Ph



E-105
X21 and X22 form a fused ring.
H
Ph



















Com-










pound










No.
X2
X3
X6
X7
X11 = 21
X12 = X22
X13 = X23
X14 = X24

















E-106
X2 and X3 form a fused ring.
H
H
H
H
H
H


E-107
X2 and X3 form a fused ring.
H
H
Ph
H
H
Ph





E-108
X2 and X3 form a fused ring.
H
H


4191





H
H


4192










E-109
X2 and X3 form a fused ring.
H
H


4193





H
H


4194










E-110
X2 and X3 form a fused ring.
H
H


4195





H
H


4196










E-111
X2 and X3 form a fused ring.
H
H
CH3
H
H
CH3





E-112
X2 and X3 form a fused ring.
H
H


4197





H
H


4198










E-113
X2 and X3 form a fused ring.
H
H
Ph
Ph
Ph
Ph





E-114
X2 and X3 form a fused ring.
H
H
Ph


4199







4200





Ph





E-115
X2 and X3 form a fused ring.
H
H
Ph
CH3
CH3
Ph


E-116
X2 and X3 form a fused ring.
Ph
H
Ph
H
H
Ph





E-117
X2 and X3 form a fused ring.


4201





H
Ph
H
H
Ph





E-118
X2 and X3 form a fused ring.
CH3
H
Ph
H
H
Ph















Compound No.
X2      X3
X6
X7
X11 = 21
X12





E-119
X2 and X3 form a fused ring.
H
H
H
H


E-120
X2 and X3 form a fused ring.
H
H
Ph
H





E-121
X2 and X3 form a fused ring.
H
H


4202





H





E-122
X2 and X3 form a fused ring.
H
H


4203





H





E-123
X2 and X3 form a fused ring.
H
H


4204





H





E-124
X2 and X3 form a fused ring.
H
H
CH3
H





E-125
X2 and X3 form a fused ring.
H
H


4205





H





E-126
X2 and X3 form a fused ring.
H
H
Ph
Ph





E-127
X2 and X3 form a fused ring.
H
H
Ph


4206










E-128
X2 and X3 form a fused ring.
H
H
Ph
CH3


E-129
X2 and X3 form a fused ring.
Ph
H
Ph
H





E-130
X2 and X3 form a fused ring.


4207





H
Ph
H





E-131
X2 and X3 form a fused ring.
CH3
H
Ph
H
















Compound No.
X13
X22
X23
X14 = X24
















E-119
H
X22 and X23 form a fused ring.
H



E-120
H
X22 and X23 form a fused ring.
Ph







E-121
H
X22 and X23 form a fused ring.


4208












E-122
H
X22 and X23 form a fused ring.


4209












E-123
H
X22 and X23 form a fused ring.


4210












E-124
H
X22 and X23 form a fused ring.
CH3







E-125
H
X22 and X23 form a fused ring.


4211












E-126
Ph
X22 and X23 form a fused ring.
Ph







E-127


4212





X22 and X23 form a fused ring.
Ph







E-128
CH3
X22 and X23 form a fused ring.
Ph



E-129
H
X22 and X23 form a fused ring.
Ph



E-130
H
X22 and X23 form a fused ring.
Ph



E-131
H
X22 and X23 form a fused ring.
Ph



















Compound No.
X2
X3
X6
X7
X11 = 21
X12 = X22
X13 = X23
X14 = X24
















E-132
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H


E-133
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H
H
Ph





E-134
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4213





H
H


4214










E-135
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4215





H
H


4216










E-136
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4217





H
H


4218










E-137
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H
H
CH3





E-138
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4219





H
H


4220










E-139
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
Ph
Ph





E-140
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph


4221







4222





Ph





E-141
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
CH3
CH3
Ph














Compound No.
X2       X3
X6       X7
X11 = 21
X12





E-142
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H


E-143
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H





E-144
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4223





H





E-145
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4224





H





E-146
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4225





H





E-147
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H





E-148
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4226





H





E-149
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph





E-150
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph


4227










E-151
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
CH3
















Compound No.
X13
X22
X23
X14 = X24
















E-142
H
X22 and X23 form a fused ring.
H



E-143
H
X22 and X23 form a fused ring.
Ph







E-144
H
X22 and X23 form a fused ring.


4228












E-145
H
X22 and X23 form a fused ring.


4229












E-146
H
X22 and X23 form a fused ring.


4230












E-147
H
X22 and X23 form a fused ring.
CH3







E-148
H
X22 and X23 form a fused ring.


4231












E-149
Ph
X22 and X23 form a fused ring.
Ph







E-150


4232





X22 and X23 form a fused ring.
Ph







E-151
CH3
X22 and X23 form a fused ring.
Ph















Compound No.
X2       X3
X6       X7
X11 = 21
X12 = 22





E-152
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H


E-153
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H





E-154
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4233





H





E-155
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4234





H





E-156
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4235





H





E-157
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H





E-158
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4236





H





E-159
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph





E-160
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph


4237










E-161
X2 and X3 forms fused ring.
X6 and X7 form a fused ring.
Ph
CH3
















Compound No.
X13
X14
X23
X24
















E-152
X13 and X14 form a fused ring.
H
H



E-153
X13 and X14 form a fused ring.
H
Ph







E-154
X13 and X14 form a fused ring.
H


4238












E-155
X13 and X14 form a fused ring.
H


4239












E-156
X13 and X14 form a fused ring.
H


4240












E-157
X13 and X14 form a fused ring.
H
CH3







E-158
X13 and X14 form a fused ring.
H


4241












E-159
X13 and X14 form a fused ring.
Ph
Ph







E-160
X13 and X14 form a fused ring.


4242





Ph







E-161
X13 and X14 form a fused ring.
CH3
Ph





















Compound No.
X2
X3
X6
X7
X11 = 21
X12 = X22
X13
X14
X23
X24
















E-162
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.


E-163
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-164
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4243





H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-165
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4244





H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-166
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4245





H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-167
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-168
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4246





H
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-169
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-170
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph


4247





X13 and X14 form a fused ring.
X23 and X24 form a fused ring.





E-171
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
CH3
X13 and X14 form a fused ring.
X23 and X24 form a fused ring.
















Compound No.
X2       X3
X6       X7
X11
X12
X13
X14















E-172
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
X13 and X14 form a fused ring.


E-173
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H
X13 and X14 form a fused ring.





E-174
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4248





H
X13 and X14 form a fused ring.





E-175
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4249





H
X13 and X14 form a fused ring.





E-176
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4250





H
X13 and X14 form a fused ring.





E-177
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H
X13 and X14 form a fused ring.





E-178
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4251





H
X13 and X14 form a fused ring.





E-179
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
X13 and X14 form a fused ring.





E-180
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph


4252





X13 and X14 form a fused ring.





E-181
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
CH3
X13 and X14 form a fused ring.
















Compound No.
X21
X22
X23
X24
















E-172
X21 and X22 form a fused ring.
H
H



E-173
X21 and X22 form a fused ring.
H
Ph







E-174
X21 and X22 form a fused ring.
H


4253












E-175
X21 and X22 form a fused ring.
H


4254












E-176
X21 and X22 form a fused ring.
H


4255












E-177
X21 and X22 form a fused ring.
H
CH3







E-178
X21 and X22 form a fused ring.
H


4256












E-179
X21 and X22 form a fused ring.
Ph
Ph







E-180
X21 and X22 form a fused ring.


4257





Ph







E-181
X21 and X22 form a fused ring.
CH3
Ph















Compound No.
X2       X3
X6       X7
X11 = 21
X12





E-182
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H


E-183
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H





E-184
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4258





H





E-185
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4259





H





E-186
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4260





H





E-187
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H





E-188
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4261





H





E-189
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph





E-190
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph


4262










E-191
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
CH3

















Compound No.
X13
X14
X22
X23
X24
















E-182
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
H



E-183
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph







E-184
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4263












E-185
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4264












E-186
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4265












E-187
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
CH3







E-188
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.


4266












E-189
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-190
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph



E-191
X13 and X14 form a fused ring.
X22 and X23 form a fused ring.
Ph











[0286]

88


























4267





“A and B form a fused ring” in


4268





means


4269






















Compound No.
X2
X3
X6
X7
X11 = X21
X14 = X24
X15 = X25





F-1
H
H
H
H
H
H
H


F-2
H
H
H
H
Ph
Ph
H





F-3
H
H
H
H


4270







4271





H





F-4
H
H
H
H


4272







4273





H





F-5
H
H
H
H


4274







4275





H





F-6
H
H
H
H
CH3
CH3
H





F-7
H
H
H
H


4276







4277





H





F-8
H
H
H
H
Ph
Ph
Ph





F-9
H
H
H
H
Ph
Ph


4278










F-10
H
H
H
H
Ph
Ph
CH3


F-11
H
H
H
H
Ph
Ph
H


F-12
H
H
H
H
Ph
Ph
H


F-13
H
H
H
H
Ph
Ph
H













F-14
X2 and X3 form a fused ring.
H
H
H
H
H


F-15
X2 and X3 form a fused ring.
H
H
Ph
Ph
H





F-16
X2 and X3 form a fused ring.
H
H


4279







4280





H





F-17
X2 and X3 form a fused ring.
H
H


4281







4282





H





F-18
X2 and X3 form a fused ring.
H
H


4283







4284





H





F-19
X2 and X3 form a fused ring.
H
H
CH3
CH3
H





F-20
X2 and X3 form a fused ring.
H
H


4285







4286





H





F-21
X2 and X3 form a fused ring.
H
H
Ph
Ph
Ph





F-22
X2 and X3 form a fused ring.
H
H
Ph
Ph


4287










F-23
X2 and X3 form a fused ring.
H
H
Ph
Ph
CH3


F-24
X2 and X3 form a fused ring.
H
H
Ph
Ph
H


F-25
X2 and X3 form a fused ring.
H
H
Ph
Ph
H


F-26
X2 and X4 form a fused ring.
H
H
Ph
Ph
H















Compound No.
X16 = X26
X17 = X27
X18 = X28







F-1
H
H
H



F-2
H
H
H



F-3
H
H
H



F-4
H
H
H



F-5
H
H
H



F-6
H
H
H



F-7
H
H
H



F-8
H
H
Ph







F-9
H
H


4288












F-10
H
H
CH3



F-11
Ph
Ph
H







F-12


4289







4290





H







F-13
CH3
CH3
H



F-14
H
H
H



F-15
H
H
H



F-16
H
H
H



F-17
H
H
H



F-18
H
H
H



F-19
H
H
H



F-20
H
H
H



F-21
H
H
Ph







F-22
H
H


4291












F-23
H
H
CH3



F-24
Ph
Ph
H







F-25


4292







4293





H







F-26
CH3
CH3
H



















Compound No.
X2
X3
X6
X7
X11 = X21
X14 = X24
X15 = X25
X16       X17





F-27
H
H
H
H
H
H
H
X16 and X17 form a fused ring.


F-28
H
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.





F-29
H
H
H
H


4294







4295





H
X16 and X17 form a fused ring.





F-30
H
H
H
H


4296







4297





H
X16 and X17 form a fused ring.





F-31
H
H
H
H


4298







4299





H
X16 and X17 form a fused ring.





F-32
H
H
H
H
CH3
CH3
H
X16 and X17 form a fused ring.





F-33
H
H
H
H


4300







4301





H
X16 and X17 form a fused ring.





F-34
H
H
H
H
Ph
Ph
Ph
X16 and X17 form a fused ring.





F-35
H
H
H
H
Ph
Ph


4302





X16 and X17 form a fused ring.





F-36
H
H
H
H
Ph
Ph
CH3
X16 and X17 form a fused ring.


F-37
H
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.


F-38
H
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.


F-39
H
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.















Compound No.
X18 = X28
X26
X27







F-27
H
H
H



F-28
H
H
H



F-29
H
H
H



F-30
H
H
H



F-31
H
H
H



F-32
H
H
H



F-33
H
H
H



F-34
Ph
H
H







F-35


4303





H
H







F-36
CH3
H
H



F-37
H
H
Ph







F-38
H
H


4304












F-39
H
H
CH3



















Compound No.
X2
X3
X6
X7
X11 = X21
X14 = X24
X15 = X25
X16       X17





F-40
H
H
H
H
H
H
H
X16 and X17 form a fused ring.


F-41
H
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.





F-42
H
H
H
H


4305







4306





H
X16 and X17 form a fused ring.





F-43
H
H
H
H


4307







4308





H
X16 and X17 form a fused ring.





F-44
H
H
H
H


4309







4310





H
X16 and X17 form a fused ring.





F-45
H
H
H
H
CH3
CH3
H
X16 and X17 form a fused ring.





F-46
H
H
H
H


4311







4312





H
X16 and X17 form a fused ring.





F-47
H
H
H
H
Ph
Ph
Ph
X16 and X17 form a fused ring.





F-48
H
H
H
H
Ph
Ph


4313





X16 and X17 form a fused ring.





F-49
H
H
H
H
Ph
Ph
CH3
X16 and X17 form a fused ring.














Compound No.
X18 = X28
X26       X27







F-40
H
X26 and X27 form a fused ring.



F-41
H
X26 and X27 form a fused ring.



F-42
H
X26 and X27 form a fused ring.



F-43
H
X26 and X27 form a fused ring.



F-44
H
X26 and X27 form a fused ring.



F-45
H
X26 and X27 form a fused ring.



F-46
H
X26 and X27 form a fused ring.



F-47
Ph
X26 and X27 form a fused ring.







F-48


4314





X26 and X27 form a fused ring.







F-49
CH3
X26 and X27 form a fused ring.
















Compound No.
X2       X3
X6       X7
X11 = X21
X14 = X24
X15 = X25





F-50
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H


F-51
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
H





F-52
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4315







4316





H





F-53
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4317







4318





H





F-54
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4319







4320





H





F-55
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
CH3
H





F-56
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4321







4322





H





F-57
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
Ph





F-58
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph


4323










F-59
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
CH3


F-60
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
H


F-61
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
H


F-62
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
H















Compound No.
X16 = X26
X17 = X27
X18 = X28







F-50
H
H
H



F-51
H
H
H



F-52
H
H
H



F-53
H
H
H



F-54
H
H
H



F-55
H
H
H



F-56
H
H
H



F-57
H
H
Ph







F-58
H
H


4324












F-59
H
H
CH3



F-60
Ph
Ph
H







F-61


4325







4326





H







F-62
CH3
CH3
H




















Compound No.
X2
X3
X6
X7
X11 = X21
X15
X16
X14 = X24
X25
















F-63
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
X15 and X16 form a fused ring.
H
H


F-64
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph
H





F-65
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4327





X15 and X16 form a fused ring.


4328





H





F-66
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4329





X15 and X16 form a fused ring.


4330





H





F-67
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4331





X15 and X16 form a fused ring.


4332





H





F-68
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
X15 and X16 form a fused ring.
CH3
H





F-69
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4333





X15 and X16 form a fused ring.


4334





H





F-70
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph
Ph





F-71
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph


4335










F-72
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph
CH3


F-73
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph
H


F-74
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph
H


F-75
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
Ph
H















Compound No.
X26
X17 = X27
X18 = X28







F-63
H
H
H



F-64
H
H
H



F-65
H
H
H



F-66
H
H
H



F-67
H
H
H



F-68
H
H
H



F-69
H
H
H



F-70
H
H
Ph







F-71
H
H


4336












F-72
H
H
CH3



F-73
Ph
Ph
H







F-74


4337







4338





H







F-75
CH3
CH3
H





















Compound No.
X2
X3
X6
X7
X11 = X21
X15
X16
X17
X18
X14 = X24
















F-76
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
H


F-77
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph





F-78
X2 and X3 form a fused ring.
X6 and X7 form a fused ring


4339





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.


4340










F-79
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4341





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.


4342










F-80
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4343





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.


4344










F-81
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
CH3





F-82
X2 and X3 form a fused ring.
X6 and X7 form a fused ring


4345





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.


4346










F-83
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph


F-84
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph


F-85
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph


F-86
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph


F-87
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph


F-88
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
Ph
















Compound No.
X25
X26
X27
X28







F-76
H
H
H
H



F-77
H
H
H
H



F-78
H
H
H
H



F-79
H
H
H
H



F-80
H
H
H
H



F-81
H
H
H
H



F-82
H
H
H
H



F-83
Ph
H
H
Ph







F-84


4347





H
H


4348












F-85
CH3
H
H
CH3



F-86
H
Ph
Ph
H







F-87
H


4349







4350





H







F-88
H
CH3
CH3
H




















Compound No.
X2
X3
X6
X7
X11 = X21
X15
X16
X17
X18
















F-89
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
X15 and X16 form a fused ring.
H
H


F-90
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
H
H





F-91
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4351





X15 and X16 form a fused ring.
H
H





F-92
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4352





X15 and X16 form a fused ring.
H
H





F-93
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4353





X15 and X16 form a fused ring.
H
H





F-94
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
X15 and X16 form a fused ring.
H
H





F-95
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4354





X15 and X16 form a fused ring.
H
H





F-96
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
H
H





F-97
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.


4355





H





F-98
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
CH3
H


F-99
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
H
Ph





F-100
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
H


4356










F-101
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
X15 and X16 form a fused ring.
H
CH3

















Compound No.
X14 = X24
X25
X26
X27
X28

















F-89
H
X25 and X26 form a fused ring.
H
H



F-90
Ph
X25 and X26 form a fused ring.
H
H







F-91


4357





X25 and X26 form a fused ring.
H
H







F-92


4358





X25 and X26 form a fused ring.
H
H







F-93


4359





X25 and X26 form a fused ring.
H
H







F-94
CH3
X25 and X26 form a fused ring.
H
H







F-95


4360





X25 and X26 form a fused ring.
H
H







F-96
Ph
X25 and X26 form a fused ring.
H
Ph







F-97
Ph
X25 and X26 form a fused ring.
H


4361












F-98
Ph
X25 and X26 form a fused ring.
H
CH3



F-99
Ph
X25 and X26 form a fused ring.
Ph
H







F-100
Ph
X25 and X26 form a fused ring.


4362





H







F-101
Ph
X25 and X26 form a fused ring.
CH3
H
















Compound No.
X2       X3
X6       X7
X11 = X21
X14 = X24
X15 = X25





F-102
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H


F-103
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
H





F-104
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4363







4364





H





F-105
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4365







4366





H





F-106
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4367







4368





H





F-107
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
CH3
H





F-108
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4369







4370





H





F-109
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
Ph





F-110
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph


4371










F-111
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
Ph
CH3















Compound No.
X16 = X26
X17 = X27
X18 = X28















F-102
X16 and X17, X26 and X27 form fused rings.
H



F-103
X16 and X17, X26 and X27 form fused rings.
H







F-104
X16 and X17, X26 and X27 form fused rings.
H







F-105
X16 and X17, X26 and X27 form fused rings.
H







F-106
X16 and X17, X26 and X27 form fused rings.
H







F-107
X16 and X17, X26 and X27 form fused rings.
H







F-108
X16 and X17, X26 and X27 form fused rings.
H







F-109
X16 and X17, X26 and X27 form fused rings.
Ph







F-110
X16 and X17, X26 and X27 form fused rings.


4372












F-111
X16 and X17, X26 and X27 form fused rings.
CH3
























4373





“A and B form a fused ring” in


4374





means


4375

























Com-












pound






X-
X-




No.
X2
X3
X6
X7
X32
X33
36
37
X11
X12





F-112
H
H
H
H
H
H
H
H
H
H


F-113
H
H
H
H
H
H
H
H
Ph
H





F-114
H
H
H
H
H
H
H
H


4376





H





F-115
H
H
H
H
H
H
H
H


4377





H





F-116
H
H
H
H
H
H
H
H


4378





H





F-117
H
H
H
H
H
H
H
H
CH3
H





F-118
H
H
H
H
H
H
H
H


4379





H





F-119
Ph
H
H
H
Ph
H
H
H
Ph
H





F-120


4380





H
H
H


4381





H
H
H
Ph
H





F-121
CH3
H
H
H
CH3
H
H
H
Ph
H


F-122
H
Ph
H
H
H
Ph
H
H
Ph
H





F-123
H


4382





H
H
H


4383





H
H
Ph
H





F-124
H
CH3
H
H
H
CH3
H
H
Ph
H


F-125
H
H
H
H
H
H
H
H
Ph
Ph





F-126
H
H
H
H
H
H
H
H
Ph


4384










F-127
H
H
H
H
H
H
H
H
Ph
CH3


















Com-









pound









No.
X13
X14
X21
X22
X23
X24







F-112
H
H
H
H
H
H



F-113
H
Ph
Ph
H
H
Ph







F-114
H


4385







4386





H
H


4387












F-115
H


4388







4389





H
H


4390












F-116
H


4391







4392





H
H


4393












F-117
H
CH3
CH3
H
H
CH3







F-118
H


4394







4395





H
H


4396












F-119
H
Ph
Ph
H
H
Ph



F-120
H
Ph
Ph
H
H
Ph



F-121
H
Ph
Ph
H
H
Ph



F-122
H
Ph
Ph
H
H
Ph



F-123
H
Ph
Ph
H
H
Ph



F-124
H
Ph
Ph
H
H
Ph



F-125
Ph
Ph
Ph
Ph
Ph
Ph







F-126


4397





Ph
Ph


4398







4399





Ph







F-127
CH3
Ph
Ph
CH3
CH3
Ph




















Compound No.
X2
X3
X6
X7
X32
X33
X36
X37
X11





F-128
H
H
H
H
H
H
H
H
H


F-129
H
H
H
H
H
H
H
H
Ph





F-130
H
H
H
H
H
H
H
H


4400










F-131
H
H
H
H
H
H
H
H


4401










F-132
H
H
H
H
H
H
H
H


4402










F-133
H
H
H
H
H
H
H
H
CH3





F-134
H
H
H
H
H
H
H
H


4403










F-135
Ph
H
H
H
Ph
H
H
H
Ph





F-136


4404





H
H
H


4405





H
H
H
Ph





F-137
CH3
H
H
H
CH3
H
H
H
Ph


F-138
H
Ph
H
H
H
Ph
H
H
Ph





F-139
H


4406





H
H
H


4407





H
H
Ph





F-140
H
CH3
H
H
H
CH3
H
H
Ph


F-141
H
H
H
H
H
H
H
H
Ph


F-142
H
H
H
H
H
H
H
H
Ph


F-143
H
H
H
H
H
H
H
H
Ph

















Compound No.
X12
X13
X14
X21
X22
X23
X24
















F-128
X12 and X13 form a fused ring.
H
H
H
H
H


F-129
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph





F-130
X12 and X13 form a fused ring.


4408







4409





H
H


4410










F-131
X12 and X13 form a fused ring.


4411







4412





H
H


4413










F-132
X12 and X13 form a fused ring.


4414







4415





H
H


4416










F-133
X12 and X13 form a fused ring.
CH3
CH3
H
H
CH3





F-134
X12 and X13 form a fused ring.


4417







4418





H
H


4419










F-135
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph


F-136
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph


F-137
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph


F-138
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph


F-139
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph


F-140
X12 and X13 form a fused ring.
Ph
Ph
H
H
Ph


F-141
X12 and X13 form a fused ring.
Ph
Ph
Ph
Ph
Ph





F-142
X12 and X13 form a fused ring.
Ph
Ph


4420







4421





Ph





F-143
X12 and X13 form a fused ring.
Ph
Ph
CH3
CH3
Ph



















Compound No.
X2
X3
X6
X7
X32
X33
X36
X37
X11





F-144
H
H
H
H
H
H
H
H
H


F-145
H
H
H
H
H
H
H
H
Ph





F-146
H
H
H
H
H
H
H
H


4422










F-147
H
H
H
H
H
H
H
H


4423










F-148
H
H
H
H
H
H
H
H


4424










F-149
H
H
H
H
H
H
H
H
CH3





F-150
H
H
H
H
H
H
H
H


4425










F-151
Ph
H
H
H
Ph
H
H
H
Ph





F-152


4426





H
H
H


4427





H
H
H
Ph





F-153
CH3
H
H
H
CH3
H
H
H
Ph


F-154
H
Ph
H
H
H
Ph
H
H
Ph





F-155
H


4428





H
H
H


4429





H
H
Ph





F-156
H
CH3
H
H
H
CH3
H
H
Ph


F-157
H
H
H
H
H
H
H
H
Ph


F-158
H
H
H
H
H
H
H
H
Ph


F-159
H
H
H
H
H
H
H
H
Ph



















Compound No.
X12
X13
X14
X21
X22
X23
X24


















F-144
H
H
H
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-145
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-146
H
H


4430





X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-147
H
H


4431





X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-148
H
H


4432





X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-149
H
H
CH3
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-150
H
H


4433





X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-151
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-152
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-153
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-154
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-155
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-156
H
H
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-157
Ph
Ph
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-158


4434







4435





Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.







F-159
CH3
CH3
Ph
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.




















Compound No.
X2
X3
X6
X7
X32
X33
X36
X37
X11       X12





F-160
H
H
H
H
H
H
H
H
X11 and X12 form a fused ring.


F-161
Ph
H
H
H
Ph
H
H
H
X11 and X12 form a fused ring.





F-162


4436





H
H
H


4437





H
H
H
X11 and X12 form a fused ring.





F-163
CH3
H
H
H
CH3
H
H
H
X11 and X12 form a fused ring.


F-164
H
Ph
H
H
H
Ph
H
H
X11 and X12 form a fused ring.





F-165
H


4438





H
H
H


4439





H
H
X11 and X12 form a fused ring.





F-166
H
CH3
H
H
H
CH3
H
H
X11 and X12 form a fused ring.


















Compound No.
X13
X14
X21
X22
X23
X24
















F-160
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-161
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-162
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-163
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-164
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-165
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.



F-166
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
X23 and X24 form a fused ring.




















Compound No.
X2
X3
X6
X7
X32
X33
X36
X37
X11





F-167
H
H
H
H
H
H
H
H
H


F-168
H
H
H
H
H
H
H
H
Ph





F-169
H
H
H
H
H
H
H
H


4440










F-170
H
H
H
H
H
H
H
H


4441










F-171
H
H
H
H
H
H
H
H


4442










F-172
H
H
H
H
H
H
H
H
CH3





F-173
H
H
H
H
H
H
H
H


4443










F-174
Ph
H
H
H
Ph
H
H
H
Ph





F-175


4444





H
H
H


4445





H
H
H
Ph





F-176
CH3
H
H
H
CH3
H
H
H
Ph


F-177
H
Ph
H
H
H
Ph
H
H
Ph





F-178
H


4446





H
H
H


4447





H
H
Ph





F-179
H
CH3
H
H
H
CH3
H
H
Ph


F-180
H
H
H
H
H
H
H
H
Ph


F-181
H
H
H
H
H
H
H
H
Ph


F-182
H
H
H
H
H
H
H
H
Ph



















Compound No.
X12
X13
X14
X21
X22
X23
X24


















F-167
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
H



F-168
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph







F-169
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H


4448












F-170
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H


4449












F-171
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H


4450












F-172
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
CH3







F-173
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H


4451












F-174
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph



F-175
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph



F-176
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph



F-177
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph



F-178
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph



F-179
H
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
H
Ph



F-180
Ph
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
Ph
Ph







F-181


4452





X13 and X14 form a fused ring.
X21 and X22 form a fused ring.


4453





Ph







F-182
CH3
X13 and X14 form a fused ring.
X21 and X22 form a fused ring.
CH3
Ph




















Compound No.
X2
X3
X6
X7
X32
X33
X36
X37
X11





F-183
H
H
H
H
H
H
H
H
H


F-184
H
H
H
H
H
H
H
H
Ph





F-185
H
H
H
H
H
H
H
H


4454










F-186
H
H
H
H
H
H
H
H


4455










F-187
H
H
H
H
H
H
H
H


4456










F-188
H
H
H
H
H
H
H
H
CH3





F-189
H
H
H
H
H
H
H
H


4457










F-190
Ph
H
H
H
Ph
H
H
H
Ph





F-191


4458





H
H
H


4459





H
H
H
Ph





F-192
CH3
H
H
H
CH3
H
H
H
Ph


F-193
H
Ph
H
H
H
Ph
H
H
Ph





F-194
H


4460





H
H
H


4461





H
H
Ph





F-195
H
CH3
H
H
H
CH3
H
H
Ph


F-196
H
H
H
H
H
H
H
H
Ph


F-197
H
H
H
H
H
H
H
H
Ph


F-198
H
H
H
H
H
H
H
H
Ph



















Compound No.
X12
X13
X14
X21
X22
X23
X24



















F-183
H
X13 and X14 form a fused ring.
H
H
H
H














F-184
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.







F-185
H
X13 and X14 form a fused ring.


4462





H
X23 and X24 form a fused ring.







F-186
H
X13 and X14 form a fused ring.


4463





H
X23 and X24 form a fused ring.







F-187
H
X13 and X14 form a fused ring.


4464





H
X23 and X24 form a fused ring.







F-188
H
X13 and X14 form a fused ring.
CH3
H
X23 and X24 form a fused ring.







F-189
H
X13 and X14 form a fused ring.


4465





H
X23 and X24 form a fused ring.







F-190
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.



F-191
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.



F-192
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.



F-193
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.



F-194
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.



F-195
H
X13 and X14 form a fused ring.
Ph
H
X23 and X24 form a fused ring.



F-196
Ph
X13 and X14 form a fused ring.
Ph
Ph
X23 and X24 form a fused ring.







F-197


4466





X13 and X14 form a fused ring.
Ph


4467





X23 and X24 form a fused ring.







F-198
CH3
X13 and X14 form a fused ring.
Ph
CH3
X23 and X24 form a fused ring.











[0287]

89


























4468





“A and B form a fused ring” in


4469





means


4470






















Compound No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X11
X14
X15





G-1
H
H
H
H
H
H
H


G-2
H
H
H
H
Ph
Ph
H





G-3
H
H
H
H


4471







4472





H





G-4
H
H
H
H


4473







4474





H





G-5
H
H
H
H


4475







4476





H





G-6
H
H
H
H
CH3
CH3
H





G-7
H
H
H
H


4477







4478





H





G-8
H
H
H
H
Ph
Ph
Ph





G-9
H
H
H
H
Ph
Ph


4479










G-10
H
H
H
H
Ph
Ph
CH3


G-11
H
H
H
H
Ph
Ph
H


G-12
H
H
H
H
Ph
Ph
H


G-13
H
H
H
H
Ph
Ph
H


G-14
Ph
H
H
H
Ph
Ph
H





G-15


4480





H
H
H
Ph
Ph
H





G-16
CH3
H
H
H
Ph
Ph
H















Compound No.
X16
X17
X18
X21
X24





G-1
H
H
H
H
H


G-2
H
H
H
Ph
Ph





G-3
H
H
H


4481







4482










G-4
H
H
H


4483







4484










G-5
H
H
H


4485







4486










G-6
H
H
H
CH3
CH3





G-7
H
H
H


4487







4488










G-8
H
H
Ph
Ph
Ph





G-9
H
H


4489





Ph
Ph





G-10
H
H
CH3
Ph
Ph


G-11
Ph
Ph
H
Ph
Ph





G-12


4490







4491





H
Ph
Ph





G-13
CH3
CH3
H
Ph
Ph


G-14
H
H
H
Ph
Ph


G-15
H
H
H
Ph
Ph


G-16
H
H
H
Ph
Ph
















Compound No.
X25
X26
X27
X28







G-1
H
H
H
H



G-2
H
H
H
H



G-3
H
H
H
H



G-4
H
H
H
H



G-5
H
H
H
H



G-6
H
H
H
H



G-7
H
H
H
H



G-8
Ph
H
H
Ph







G-9


4492





H
H


4493












G-10
CH3
H
H
CH3



G-11
H
Ph
Ph
H







G-12
H


4494







4495





H







G-13
H
CH3
CH3
H



G-14
H
H
H
H



G-15
H
H
H
H



G-16
H
H
H
H




















Compound











No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X11
X14
X15
X16
X17


















G-17
H
H
H
H
H
H
H
X16 and X17 form a fused ring.


G-18
H
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.





G-19
H
H
H
H


4496







4497





H
X16 and X17 form a fused ring.





G-20
H
H
H
H


4498







4499





H
X16 and X17 form a fused ring.





G-21
H
H
H
H


4500







4501





H
X16 and X17 form a fused ring.





G-22
H
H
H
H
CH3
CH3
H
X16 and X17 form a fused ring.





G-23
H
H
H
H


4502







4503





H
X16 and X17 form a fused ring.





G-24
H
H
H
H
Ph
Ph
Ph
X16 and X17 form a fused ring.





G-25
H
H
H
H
Ph
Ph


4504





X16 and X17 form a fused ring.





G-26
H
H
H
H
Ph
Ph
CH3
X16 and X17 form a fused ring.


G-27
Ph
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.





G-28


4505





H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.





G-29
CH3
H
H
H
Ph
Ph
H
X16 and X17 form a fused ring.



















Compound










No.
X18
X21
X24
X25
X26
X27
X28



















G-17
H
H
H
H
X26 and X27 form a fused ring
H



G-18
H
Ph
Ph
H
X26 and X27 form a fused ring
H







G-19
H


4506







4507





H
X26 and X27 form a fused ring
H







G-20
H


4508







4509





H
X26 and X27 form a fused ring
H







G-21
H


4510







4511





H
X26 and X27 form a fused ring
H







G-22
H
CH3
CH3
H
X26 and X27 form a fused ring
H







G-23
H


4512







4513





H
X26 and X27 form a fused ring
H







G-24
Ph
Ph
Ph
Ph
X26 and X27 form a fused ring
H







G-25


4514





Ph
Ph


4515





X26 and X27 form a fused ring
H







G-26
CH3
Ph
Ph
CH3
X26 and X27 form a fused ring
H



G-27
H
Ph
Ph
H
X26 and X27 form a fused ring
H



G-28
H
Ph
Ph
H
X26 and X27 form a fused ring
H



G-29
H
Ph
Ph
H
X26 and X27 form a fused ring
H


















Compound No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X11
X14
X15





G-30
H
H
H
H
H
H
H


G-31
H
H
H
H
Ph
Ph
H





G-32
H
H
H
H


4516







4517





H





G-33
H
H
H
H


4518







4519





H





G-34
H
H
H
H


4520







4521





H





G-35
H
H
H
H
CH3
CH3
H





G-36
H
H
H
H


4522







4523





H





G-37
H
H
H
H
Ph
Ph
Ph





G-38
H
H
H
H
Ph
Ph


4524










G-39
H
H
H
H
Ph
Ph
CH3


G-40
H
H
H
H
Ph
Ph
H


G-41
H
H
H
H
Ph
Ph
H


G-42
H
H
H
H
Ph
Ph
H


G-43
Ph
H
H
H
Ph
Ph
H





G-44


4525





H
H
H
Ph
Ph
H





G-45
CH3
H
H
H
Ph
Ph
H















Compound No.
X16       X17
X18
X21
X24
X25





G-30
X16 and X17 form a fused ring.
H
H
H
H


G-31
X16 and X17 form a fused ring.
H
Ph
Ph
H





G-32
X16 and X17 form a fused ring.
H


4526







4527





H





G-33
X16 and X17 form a fused ring.
H


4528







4529





H





G-34
X16 and X17 form a fused ring.
H


4530







4531





H





G-35
X16 and X17 form a fused ring.
H
CH3
CH3
H





G-36
X16 and X17 form a fused ring.
H


4532







4533





H





G-37
X16 and X17 form a fused ring.
Ph
Ph
Ph
Ph





G-38
X16 and X17 form a fused ring.


4534





Ph
Ph


4535










G-39
X16 and X17 form a fused ring.
CH3
Ph
Ph
CH3


G-40
X16 and X17 form a fused ring.
H
Ph
Ph
H


G-41
X16 and X17 form a fused ring.
H
Ph
Ph
H


G-42
X16 and X17 form a fused ring.
H
Ph
Ph
H


G-43
X16 and X17 form a fused ring.
H
Ph
Ph
H


G-44
X16 and X17 form a fused ring.
H
Ph
Ph
H


G-45
X16 and X17 form a fused ring.
H
Ph
Ph
H















Compound No.
X26
X27
X28







G-30
H
H
H



G-31
H
H
H



G-32
H
H
H



G-33
H
H
H



G-34
H
H
H



G-35
H
H
H



G-36
H
H
H



G-37
H
H
Ph







G-38
H
H


4536












G-39
H
H
CH3



G-40
Ph
Ph
H







G-41


4537







4538





H







G-42
CH3
CH3
H



G-43
H
H
H



G-44
H
H
H



G-45
H
H
H




















Compound











No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X11
X14
X15
X16
X17


















G-46
H
H
H
H
H
H
X15 and X16 form a fused ring.
H


G-47
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
H





G-48
H
H
H
H


4539







4540





X15 and X16 form a fused ring.
H





G-49
H
H
H
H


4541







4542





X15 and X16 form a fused ring.
H





G-50
H
H
H
H


4543







4544





X15 and X16 form a fused ring.
H





G-51
H
H
H
H
CH3
CH3
X15 and X16 form a fused ring.
H





G-52
H
H
H
H


4545







4546





X15 and X16 form a fused ring.
H





G-53
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
H


G-54
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
H


G-55
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
H


G-56
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
Ph





G-57
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.


4547










G-58
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
CH3


G-59
Ph
H
H
H
Ph
Ph
X15 and X16 form a fused ring.






G-60


4548





H
H
H
Ph
Ph
X15 and X16 form a fused ring.






G-61
CH3
H
H
H
Ph
Ph
X15 and X16 form a fused ring.



















Compound










No.
X18
X21
X24
X25
X26
X27
X28



















G-46
H
H
H
H
H
X27 and X28 form a fused ring.



G-47
H
Ph
Ph
H
H
X27 and X28 form a fused ring.







G-48
H


4549







4550





H
H
X27 and X28 form a fused ring.







G-49
H


4551







4552





H
H
X27 and X28 form a fused ring.







G-50
H


4553







4554





H
H
X27 and X28 form a fused ring.







G-51
H
CH3
CH3
H
H
X27 and X28 form a fused ring.







G-52
H


4555







4556





H
H
X27 and X28 form a fused ring.







G-53
Ph
Ph
Ph
Ph
H
X27 and X28 form a fused ring.







G-54


4557





Ph
Ph


4558





H
X27 and X28 form a fused ring.







G-55
CH3
Ph
Ph
CH3
H
X27 and X28 form a fused ring.



G-56
H
Ph
Ph
H
Ph
X27 and X28 form a fused ring.







G-57
H
Ph
Ph
H


4559





X27 and X28 form a fused ring.







G-58
H
Ph
Ph
H
CH3
X27 and X28 form a fused ring.



G-59
H
Ph
Ph
H
H
X27 and X28 form a fused ring.



G-60
H
Ph
Ph
H
H
X27 and X28 form a fused ring.



G-61
H
Ph
Ph
H
H
X27 and X28 form a fused ring.





















Compound












No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X11
X14
X15
X16
X17
X18


















G-62
H
H
H
H
H
H
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.


G-63
H
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-64
H
H
H
H


4560







4561





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-65
H
H
H
H


4562







4563





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-66
H
H
H
H


4564







4565





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-67
H
H
H
H
CH3
CH3
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-68
H
H
H
H


4566







4567





X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-69
Ph
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-70


4568





H
H
H
Ph
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.





G-71
CH3
H
H
H
Ph
Ph
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.


















Compound









No.
X21
X24
X25
X26
X27
X28

















G-62
H
H
X25 and X26 form a fused ring.
X27 and X28 form a fused ring.



G-63
Ph
Ph
X25 and X26 form a fused ring.
X27 and X28 form a fused ring.







G-64


4569







4570





X25 and X26 form a fused ring.
X27 and X28 form a fused ring.







G-65


4571







4572





X25 and X26 form a fused ring.
X27 and X28 form a fused ring.







G-66


4573







4574





X25 and X26 form a fused ring.
X27 and X28 form a fused ring.







G-67
CH3
CH3
X25 and X26 form a fused ring.
X27 and X28 form a fused ring.







G-68


4575







4576





X25 and X26 form a fused ring.
X27 and X28 form a fused ring.







G-69
Ph
Ph
X25 and X26 form a fused ring.
X27 and X28 form a fused ring.



G-70
Ph
Ph
X25 and X26 form a fused ring.
X27 and X28 form a fused ring.



G-71
Ph
Ph
X25 and X26 form a fused ring.
X27 and X28 form a fused ring.




















Compound No.
X2       X3
X6
X7
X32
X33
X36
X37
X11 = X21
X14 = X24





G-72
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
H


G-73
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph





G-74
X2 and X3 form a fused ring.
H
H
H
H
H
H


4577







4578










G-75
X2 and X3 form a fused ring.
H
H
H
H
H
H


4579







4580










G-76
X2 and X3 form a fused ring.
H
H
H
H
H
H


4581







4582










G-77
X2 and X3 form a fused ring.
H
H
H
H
H
H
CH3
CH3





G-78
X2 and X3 form a fused ring.
H
H
H
H
H
H


4583







4584










G-79
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph


G-80
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph


G-81
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph


G-82
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph


G-83
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph


G-84
X2 and X3 form a fused ring.
H
H
H
H
H
H
Ph
Ph


G-85
X2 and X3 form a fused ring.
H
H
Ph
H
H
H
Ph
Ph





G-86
X2 and X3 form a fused ring.
H
H


4585





H
H
H
Ph
Ph





G-87
X2 and X3 form a fused ring.
H
H
CH3
H
H
H
Ph
Ph
















Compound No.
X15 = X25
X16 = X26
X17 = X27
X18 = X28







G-72
H
H
H
H



G-73
H
H
H
H



G-74
H
H
H
H



G-75
H
H
H
H



G-76
H
H
H
H



G-77
H
H
H
H



G-78
H
H
H
H



G-79
Ph
H
H
Ph







G-80


4586





H
H


4587












G-81
CH3
H
H
CH3



G-82
H
Ph
Ph
H







G-83
H


4588







4589





H







G-84
H
CH3
CH3
H



G-85
H


H



G-86
H


H



G-87
H


H



















Compound No.
X2       X3
X6
X7
X32       X33
X36
X37
X11 = X21
X14 = X24





G-88
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
H


G-89
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph





G-90
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H


4590







4591










G-91
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H


4592







4593










G-92
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H


4594







4595










G-93
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
CH3
CH3





G-94
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H


4596







4597










G-95
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph


G-96
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph


G-97
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph


G-98
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph


G-99
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph


G-100
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
Ph
Ph
















Compound No.
X15 = X25
X16 = X26
X17 = X27
X18 = X28







G-88
H
H
H
H



G-89
H
H
H
H



G-90
H
H
H
H



G-91
H
H
H
H



G-92
H
H
H
H



G-93
H
H
H
H



G-94
H
H
H
H



G-95
Ph
H
H
Ph







G-96


4598





H
H


4599












G-97
CH3
H
H
CH3



G-98
H
Ph
Ph
H







G-99
H


4600







4601





H







G-100
H
CH3
CH3
H











[0288]

90


























4602





“A and B form a fused ring” in


4603





means


4604

























Compound No.
X2
X3
X6
X7
X32       X33
X36
X37
X34 = X35
X11
X14





H-1
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
H
H


H-2
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph





H-3
H
H
H
H
X2 and X3 form a fused ring.
H
H
H


4605







4606










H-4
H
H
H
H
X2 and X3 form a fused ring.
H
H
H


4607







4608










H-5
H
H
H
H
X2 and X3 form a fused ring.
H
H
H


4609







4610










H-6
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
CH3
CH3





H-7
H
H
H
H
X2 and X3 form a fused ring.
H
H
H


4611







4612










H-8
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph


H-9
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph


H-10
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph


H-11
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph


H-12
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph


H-13
H
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph


H-14
Ph
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph





H-15


4613





H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph





H-16
CH3
H
H
H
X2 and X3 form a fused ring.
H
H
H
Ph
Ph
















Compound No.
X15
X16
X17
X18







H-1
H
H
H
H



H-2
H
H
H
H



H-3
H
H
H
H



H-4
H
H
H
H



H-5
H
H
H
H



H-6
H
H
H
H



H-7
H
H
H
H



H-8
Ph
H
H
Ph







H-9


4614





H
H


4615












H-10
CH3
H
H
CH3



H-11
H
Ph
Ph
H







H-12
H


4616







4617





H







H-13
H
CH3
CH3
H



H-14
H
H
H
H



H-15
H
H
H
H



H-16
H
H
H
H



















Compound No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X34 = X35
X11
X14
X15





H-17
H
H
H
H
H
H
H
H


H-18
H
H
H
H
H
Ph
Ph
H





H-19
H
H
H
H
H


4618







4619





H





H-20
H
H
H
H
H


4620







4621





H





H-21
H
H
H
H
H


4622







4623





H





H-22
H
H
H
H
H
CH3
CH3
H





H-23
H
H
H
H
H


4624







4625





H





H-24
H
H
H
H
H
Ph
Ph
Ph





H-25
H
H
H
H
H
Ph
Ph


4626










H-26
H
H
H
H
H
Ph
Ph
CH3


H-27
H
H
H
H
H
Ph
Ph
H


H-28
H
H
H
H
H
Ph
Ph
H


H-29
H
H
H
H
H
Ph
Ph
H


H-30
Ph
H
H
H
H
Ph
Ph
H





H-31


4627





H
H
H
H
Ph
Ph
H





H-32
CH3
H
H
H
H
Ph
Ph
H















Compound No.
X16
X17
X18







H-17
H
H
H



H-18
H
H
H



H-19
H
H
H



H-20
H
H
H



H-21
H
H
H



H-22
H
H
H



H-23
H
H
H



H-24
H
H
Ph







H-25
H
H


4628












H-26
H
H
CH3



H-27
Ph
Ph
H







H-28


4629







4630





H







H-29
CH3
CH3
H



H-30
H
H
H



H-31
H
H
H



H-32
H
H
H


















Compound No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X34 = X35
X11
X14





H-33
H
H
H
H

H
H


H-34
H
H
H
H

Ph
Ph





H-35
H
H
H
H



4631







4632










H-36
H
H
H
H



4633







4634










H-37
H
H
H
H



4635







4636










H-38
H
H
H
H

CH3
CH3





H-39
H
H
H
H
H


4637







4638










H-40
H
H
H
H
H
Ph
Ph


H-41
H
H
H
H
H
Ph
Ph


H-42
H
H
H
H
H
Ph
Ph


H-43
H
H
H
H
H
Ph
Ph


H-44
H
H
H
H
H
Ph
Ph


H-45
H
H
H
H
H
Ph
Ph


H-46
Ph
H
H
H
H
Ph
Ph





H-47


4639





H
H
H
H
Ph
Ph





H-48
CH3
H
H
H
H
Ph
Ph
















Compound No.
X15
X16
X17
X18
















H-33
X15 and X16 form a fused ring.
H
H



H-34
X15 and X16 form a fused ring.
H
H



H-35
X15 and X16 form a fused ring.
H
H



H-36
X15 and X16 form a fused ring.
H
H



H-37
X15 and X16 form a fused ring.
H
H



H-38
X15 and X16 form a fused ring.
H
H



H-39
X15 and X16 form a fused ring.
H
H



H-40
X15 and X16 form a fused ring.
H
Ph







H-41
X15 and X16 form a fused ring.
H


4640












H-42
X15 and X16 form a fused ring.
H
CH3



H-43
X15 and X16 form a fused ring.
Ph
H







H-44
X15 and X16 form a fused ring.


4641





H







H-45
X15 and X16 form a fused ring.
CH3
H



H-46
X15 and X16 form a fused ring.

H



H-47
X15 and X16 form a fused ring.

H



H-48
X15 and X16 form a fused ring.

H


















Compound No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X34 = X35
X11
X14





H-49
H
H
H
H
H
H
H


H-50
H
H
H
H
H
Ph
Ph





H-51
H
H
H
H
H


4642







4643










H-52
H
H
H
H
H


4644







4645










H-53
H
H
H
H
H


4646







4647










H-54
H
H
H
H
H
CH3
CH3





H-55
H
H
H
H
H


4648







4649










H-56
H
H
H
H
H
Ph
Ph


H-57
H
H
H
H
H
Ph
Ph


H-58
H
H
H
H
H
Ph
Ph


H-59
H
H
H
H
H
Ph
Ph


H-60
H
H
H
H
H
Ph
Ph


H-61
H
H
H
H
H
Ph
Ph


H-62
Ph
H
H
H
H
Ph
Ph





H-63


4650





H
H
H
H
Ph
Ph





H-64
CH3
H
H
H
H
Ph
Ph
















Compound No.
X15
X16
X17
X18
















H-49
H
X16 and X17 form a fused ring.
H



H-50
H
X16 and X17 form a fused ring.
H



H-51
H
X16 and X17 form a fused ring.
H



H-52
H
X16 and X17 form a fused ring.
H



H-53
H
X16 and X17 form a fused ring.
H



H-54
H
X16 and X17 form a fused ring.
H



H-55
H
X16 and X17 form a fused ring.
H



H-56
Ph
X16 and X17 form a fused ring.
Ph







H-57


4651





X16 and X17 form a fused ring.


4652












H-58
CH3
X16 and X17 form a fused ring.
CH3



H-59
H
X16 and X17 form a fused ring.
H



H-60
H
X16 and X17 form a fused ring.
H



H-61
H
X16 and X17 form a fused ring.
H



H-62
H
X16 and X17 form a fused ring.
H



H-63
H
X16 and X17 form a fused ring.
H



H-64
H
X16 and X17 form a fused ring.
H


















Compound No.
X2 = X32
X3 = X33
X6 = X36
X7 = X37
X34 = X35
X11
X14





H-65
H
H
H
H
H
H
H


H-66
H
H
H
H
H
Ph
Ph





H-67
H
H
H
H
H


4653







4654










H-68
H
H
H
H
H


4655







4656










H-69
H
H
H
H
H


4657







4658










H-70
H
H
H
H
H
CH3
CH3





H-71
H
H
H
H
H


4659







4660










H-72
Ph
H
H
H
H
Ph
Ph





H-73


4661





H
H
H
H
Ph
Ph





H-74
CH3
H
H
H
H
Ph
Ph














Compound No.
X15       X16
X17       X18







H-65
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-66
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-67
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-68
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-69
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-70
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-71
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-72
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-73
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.



H-74
X15 and X16 form a fused ring.
X17 and X18 form a fused ring.
























4662





“A and B form a fused ring” in


4663





means


4664
























Compound No.
X2       X3
X6
X7
X32       X33
X36
X37
X34 = X35
X11
X14





H-75
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
H
H


H-76
X2 and X4 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph





H-77
X2 and X5 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4665







4666










H-78
X2 and X6 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4667







4668










H-79
X2 and X7 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4669







4670










H-80
X2 and X8 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
CH3
CH3





H-81
X2 and X9 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4671







4672










H-82
X2 and X10 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph


H-83
X2 and X11 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph


H-84
X2 and X12 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph


H-85
X2 and X13 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph


H-86
X2 and X14 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph


H-87
X2 and X15 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph
Ph
















Compound No.
X15
X16
X17
X18







H-75
H
H
H
H



H-76
H
H
H
H



H-77
H
H
H
H



H-78
H
H
H
H



H-79
H
H
H
H



H-80
H
H
H
H



H-81
H
H
H
H



H-82
Ph
H
H
Ph







H-83


4673





H
H


4674












H-84
CH3
H
H
CH3



H-85
H
Ph
Ph
H







H-86
H


4675







4676





H







H-87
H
CH3
CH3
H
























4677





“A and B form a fused ring” in


4678





means


4679

























Compound No.
X2       X3
X6
X7
X32
X33
X36
X37
X34 = X35
X11
X14





H-88
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
H
H


H-89
X2 and X4 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph





H-90
X2 and X5 form a fused ring.
H
H
H
H
H
H
H


4680







4681










H-91
X2 and X6 form a fused ring.
H
H
H
H
H
H
H


4682







4683










H-92
X2 and X7 form a fused ring.
H
H
H
H
H
H
H


4684







4685










H-93
X2 and X8 form a fused ring.
H
H
H
H
H
H
H
CH3
CH3





H-94
X2 and X9 form a fused ring.
H
H
H
H
H
H
H


4686







4687










H-95
X2 and X10 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph


H-96
X2 and X11 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph


H-97
X2 and X12 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph


H-98
X2 and X13 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph


H-99
X2 and X14 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph


H-100
X2 and X15 form a fused ring.
H
H
H
H
H
H
H
Ph
Ph


H-101
X2 and X16 form a fused ring.
H
H
Ph
H
H
H
H
Ph
Ph





H-102
X2 and X17 form a fused ring.
H
H


4688





H
H
H
H
Ph
Ph





H-103
X2 and X18 form a fused ring.
H
H
CH3
H
H
H
H
Ph
Ph
















Compound No.
X15
X16
X17
X18







H-88
H
H
H
H



H-89
H
H
H
H



H-90
H
H
H
H



H-91
H
H
H
H



H-92
H
H
H
H



H-93
H
H
H
H



H-94
H
H
H
H



H-95
Ph
H
H
Ph







H-96


4689





H
H


4690












H-97
CH3
H
H
CH3



H-98
H
Ph
Ph
H







H-99
H


4691







4692





H







H-100
H
CH3
CH3
H



H-101
H
H
H
H



H-102
H
H
H
H



H-103
H
H
H
H











[0289]

91


























4693





“A and B form a fused ring” in


4694





means


4695
























Compound No.
X2
X3
X6
X7
X32
X33
X34 = X35
X36
X37





I-1
H
H
H
H
H
H
H
H
H


I-2
H
H
H
H
H
H
H
H
H


I-3
H
H
H
H
H
H
H
H
H


I-4
H
H
H
H
H
H
H
H
H


I-5
H
H
H
H
H
H
H
H
H


I-6
H
H
H
H
H
H
H
H
H


I-7
H
H
H
H
H
H
H
H
H


I-8
Ph
H
H
H
Ph
H
H
H
H





I-9


4696





H
H
H


4697





H
H
H
H





I-10
CH3
H
H
H
CH3
H
H
H
H


I-11
H
Ph
H
H
H
Ph
H
H
H





I-12
H


4698





H
H
H


4699





H
H
H





I-13
H
CH3
H
H
H
CH3
H
H
H


I-14
H
H
H
H
H
H
H
H
H


I-15
H
H
H
H
H
H
H
H
H


I-16
H
H
H
H
H
H
H
H
H


I-17
H
H
H
H
H
H
H
H
H


I-18
H
H
H
H
H
H
H
H
H


I-19
H
H
H
H
H
H
H
H
H


I-20
H
H
H
H
H
H
H
H
H


I-21
H
H
H
H
H
H
H
H
H


I-22
H
H
H
H
H
H
H
H
H


I-23
H
H
H
H
H
H
H
H
H


I-24
Ph
H
H
H
Ph
H
H
H
H





I-25


4700





H
H
H


4701





H
H
H
H





I-26
CH3
H
H
H
CH3
H
H
H
H


I-27
H
Ph
H
H
H
Ph
H
H
H





I-28
H


4702





H
H
H


4703





H
H
H





I-29
H
CH3
H
H
H
CH3
H
H
H


I-30
H
H
H
H
H
H
H
H
H


I-31
H
H
H
H
H
H
H
H
H


I-32
H
H
H
H
H
H
H
H
H
















Compound No.
X11
X12
X13
X14







I-1
H
H
H
H



I-2
Ph
H
H
Ph







I-3


4704





H
H


4705












I-4


4706





H
H


4707












I-5


4708





H
H


4709












I-6
CH3
H
H
CH3







I-7


4710





H
H


4711












I-8
Ph
H
H
Ph



I-9
Ph
H
H
Ph



I-10
Ph
H
H
Ph



I-11
Ph
H
H
Ph



I-12
Ph
H
H
Ph



I-13
Ph
H
H
Ph



I-14
Ph
Ph
Ph
Ph







I-15
Ph


4712







4713





Ph







I-16
Ph
CH3
CH3
Ph












I-17
H
H
X13 and X14 form a fused ring.



I-18
Ph
H
X13 and X14 form a fused ring.







I-19


4714





H
X13 and X14 form a fused ring.







I-20


4715





H
X13 and X14 form a fused ring.







I-21


4716





H
X13 and X14 form a fused ring.







I-22
CH3
H
X13 and X14 form a fused ring.







I-23


4717





H
X13 and X14 form a fused ring.







I-24
Ph
H
X13 and X14 form a fused ring.



I-25
Ph
H
X13 and X14 form a fused ring.



I-26
Ph
H
X13 and X14 form a fused ring.



I-27
Ph
H
X13 and X14 form a fused ring.



I-28
Ph
H
X13 and X14 form a fused ring.



I-29
Ph
H
X13 and X14 form a fused ring.



I-30
Ph
Ph
X13 and X14 form a fused ring.







I-31
Ph


4718





X13 and X14 form a fused ring.







I-32
Ph
CH3
X13 and X14 form a fused ring.



















Compound No.
X2
X3
X6
X7
X32
X33
X36
X37





I-33
H
H
H
H
H
H
H
H


I-34
Ph
H
H
H
Ph
H
H
H





I-35


4719





H
H
H


4720





H
H
H





I-36
CH3
H
H
H
CH3
H
H
H


I-37
H
Ph
H
H
H
Ph
H
H





I-38
H


4721





H
H
H


4722





H
H





I-39
H
CH3
H
H
H
CH3
H
H














Compound No.
X11       X12
X13       X14







I-33
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.



I-34
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.



I-35
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.



I-36
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.



I-37
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.



I-38
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.



I-39
X11 and X12 form a fused ring.
X13 and X14 form a fused ring.




















Compound No.
X2       X3
X6
X7
X32
X33
X34 = X35
X36
X37
X11





I-40
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
H


I-41
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
Ph





I-42
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


4723










I-43
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


4724










I-44
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


4725










I-45
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
CH3





I-46
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


4726










I-47
X2 and X3 form a fused ring.
H
H
Ph
H
H
H
H
Ph





I-48
X2 and X3 form a fused ring.
H
H


4727





H
H
H
H
Ph





I-49
X2 and X3 form a fused ring.
H
H
CH3
H
H
H
H
Ph


I-50
X2 and X3 form a fused ring.
H
H
H
Ph
H
H
H
Ph





I-51
X2 and X3 form a fused ring.
H
H
H


4728





H
H
H
Ph





I-52
X2 and X3 form a fused ring.
H
H
H
CH3
H
H
H
Ph


I-53
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
Ph


I-54
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
Ph


I-55
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
Ph















Compound No.
X12
X13
X14







I-40
H
H
H



I-41
H
H
Ph







I-42
H
H


4729












I-43
H
H


4730












I-44
H
H


4731












I-45
H
H
CH3







I-46
H
H


4732












I-47
H
H
Ph



I-48
H
H
Ph



I-49
H
H
Ph



I-50
H
H
Ph



I-51
H
H
Ph



I-52
H
H
Ph



I-53
Ph
Ph
Ph







I-54


4733







4734





Ph







I-55
CH3
CH3
Ph




















Compound No.
X2
X3
X6
X7
X32       X33
X34 = X35
X36
X37
X11





I-56
H
H
H
H
X32 and X33 form a fused ring.
H
H
H
H


I-57
H
H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph





I-58
H
H
H
H
X32 and X33 form a fused ring.
H
H
H


4735










I-59
H
H
H
H
X32 and X33 form a fused ring.
H
H
H


4736










I-60
H
H
H
H
X32 and X33 form a fused ring.
H
H
H


4737










I-61
H
H
H
H
X32 and X33 form a fused ring.
H
H
H
CH3





I-62
H
H
H
H
X32 and X33 form a fused ring.
H
H
H


4738










I-63
Ph
H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph





I-64


4739





H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph





I-65
CH3
H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph


I-66
H
H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph


I-67
H
H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph


I-68
H
H
H
H
X32 and X33 form a fused ring.
H
H
H
Ph















Compound No.
X12
X13
X14







I-56
H
H
H



I-57
H
H
Ph







I-58
H
H


4740












I-59
H
H


4741












I-60
H
H


4742












I-61
H
H
CH3







I-62
H
H


4743












I-63
H
H
Ph



I-64
H
H
Ph



I-65
H
H
Ph



I-66
Ph
Ph
Ph







I-67


4744







4745





Ph







I-68
CH3
CH3
Ph



















Compound No.
X2       X3
X6
X7
X32       X33
X34 = X35
X36
X37
X11





I-69
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
H


I-70
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph





I-71
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4746










I-72
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4747










I-73
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4748










I-74
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
CH3





I-75
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


4749










I-76
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph


I-77
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph


I-78
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H
Ph















Compound No.
X12
X13
X14







I-69
H
H
H



I-70
H
H
Ph







I-71
H
H


4750












I-72
H
H


4751












I-73
H
H


4752












I-74
H
H
CH3







I-75
H
H


4753












I-76
Ph
Ph
Ph







I-77


4754







4755





Ph







I-78
CH3
CH3
Ph



















Compound No.
X2      X3
X6
X7
X32
X33
X34 = X35
X36
X37





I-79
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-80
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-81
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-82
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-83
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-84
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-85
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-86
X2 and X3 form a fused ring.
H
H
Ph
H
H
H
H





I-87
X2 and X3 form a fused ring.
H
H


4756





H
H
H
H





I-88
X2 and X3 form a fused ring.
H
H
CH3
H
H
H
H


I-89
X2 and X3 form a fused ring.
H
H
H
Ph
H
H
H





I-90
X2 and X3 form a fused ring.
H
H
H


4757





H
H
H





I-91
X2 and X3 form a fused ring.
H
H
H
CH3
H
H
H


I-92
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-93
X2 and X3 form a fused ring.
H
H
H
H
H
H
H


I-94
X2 and X3 form a fused ring.
H
H
H
H
H
H
H
















Compound No.
X11
X12
X13
X14
















I-79
H
H
X13 and X14 form a fused ring.



I-80
Ph
H
X13 and X14 form a fused ring.







I-81


4758





H
X13 and X14 form a fused ring.







I-82


4759





H
X13 and X14 form a fused ring.







I-83


4760





H
X13 and X14 form a fused ring.







I-84
CH3
H
X13 and X14 form a fused ring.







I-85


4761





H
X13 and X14 form a fused ring.







I-86
Ph
H
X13 and X14 form a fused ring.



I-87
Ph
H
X13 and X14 form a fused ring.



I-88
Ph
H
X13 and X14 form a fused ring.



I-89
Ph
H
X13 and X14 form a fused ring.



I-90
Ph
H
X13 and X14 form a fused ring.



I-91
Ph
H
X13 and X14 form a fused ring.



I-92
Ph
Ph
X13 and X14 form a fused ring.







I-93
Ph


4762





X13 and X14 form a fused ring.







I-94
Ph
CH3
X13 and X14 form a fused ring.





























4763





“A and B form a fused ring” in


4764







4765





means


4766























Compound No.
X2       X3
X6
X7
X32       X33
X34 = X35
X36
X37





I-95
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-96
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-97
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-98
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-99
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-100
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-101
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-102
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-103
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H


I-104
X2 and X3 form a fused ring.
H
H
X32 and X33 form a fused ring.
H
H
H















Compound No.
X11       X12
X13
X14







I-95
X11 and X12 form a fused ring.

H



I-96
X11 and X12 form a fused ring.

Ph







I-97
X11 and X12 form a fused ring.



4767












I-98
X11 and X12 form a fused ring.



4768












I-99
X11 and X12 form a fused ring.



4769












I-100
X11 and X12 form a fused ring.

CH3







I-101
X11 and X12 form a fused ring.



4770












I-102
X11 and X12 form a fused ring.
Ph
Ph







I-103
X11 and X12 form a fused ring.


4771





Ph







I-104
X11 and X12 form a fused ring.
CH4
Ph
























4772





“A and B form a fused ring” in


4773





means


4774























Compound No.
X2
X3
X6
X7
X32       X33
X34 = X35
X36       X37
X11





I-105
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
H


I-106
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
Ph





I-107
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.


4775










I-108
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.


4776










I-109
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.


4777










I-110
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
CH3





I-111
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.


4778










I-112
H
Ph
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
Ph





I-113
H


4779





H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
Ph





I-114
H
CH3
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
Ph


I-115
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
Ph


I-116
H
H
H
H
X32 and X33 form a fused ring.
H
X36 and X37 form a fused ring.
Ph


I-117
H
H
H
H
X32 and X33 forms fused ring.
H
X36 and X37 form a fused ring.
Ph















Compound No.
X12
X13
X14







I-105
H
H
H



I-106
H
H
Ph







I-107
H
H


4780












I-108
H
H


4781












I-109
H
H


4782












I-110
H
H
CH3







I-111
H
H


4783












I-112
H
H
Ph







I-113
H
H
Ph







I-114
H
H
Ph



I-115
Ph
Ph
Ph







I-116


4784







4785





Ph







I-117
CH3
CH3
Ph


















Compound No.
X2       X3
X6       X7
X32
X33
X34 = X35
X36
X37





I-118
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-119
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-120
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-121
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-122
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-123
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-124
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-125
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
Ph
H
H
H
H





I-126
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.


4786





H
H
H
H





I-127
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
CH3
H
H
H
H


I-128
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
Ph
H
H
H





I-129
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H


4787





H
H
H





I-130
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
CH3
H
H
H


I-131
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-132
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H


I-133
X2 and X3 form a fused ring.
X6 and X7 form a fused ring.
H
H
H
H
H
















Compound No.
X11
X12
X13
X14







I-118
H
H
H
H



I-119
Ph
H
H
Ph







I-120


4788





H
H


4789












I-121


4790





H
H


4791












I-122


4792





H
H


4793












I-123
CH3
H
H
CH3







I-124


4794





H
H


4795












I-125
Ph
H
H
Ph



I-126
Ph
H
H
Ph



I-127
Ph
H
H
Ph



I-128
Ph
H
H
Ph



I-129
Ph
H
H
Ph



I-130
Ph
H
H
Ph



I-131
Ph
Ph
Ph
Ph







I-132
Ph


4796







4797





Ph







I-133
Ph
CH3
CH3
Ph











[0290]

92






















4798







4799








J-1
J-2


















4800







4801







J-3
J-4







4802







4803







J-5
J-6

















4804







4805







J-7
J-8



















4806







4807







4808







J-9
J-10
J-11







4809







4810








J-12
J-13








4811







4812







4813







J-14
J-15
J-16







4814







4815







4816







J-17
J-18
J-19







4817







4818







4819







J-20
J-21
J-22

















4820







4821







J-23
J-24



















4822







4823







4824







J-25
J-26
J-27

















4825







4826







J-28
J-29







4827







4828







J-30
J-31



















4829







4830







4831







J-32
J-33
J-34







4832







4833







4834







J-35
J-36
J-37

















4835







4836







J-38
J-39







4837







4838







J-40
J-41







4839







4840







J-42
J-43







4841







4842







J-44
J-45















4843







J-46










[0291] The above dopants, for example, the compounds of formula (VI) can be produced, for example, by the method described in J. Amer. Chem. Soc., 118, 2374 (1996). Specifically, as shown by the following scheme, the end compound can be produced by reacting a compound of formula (2) with a compound of formula (3) in the presence of aluminum chloride/sodium chloride, cobalt fluoride or thallium trifluoroacetate.
4844


[0292] It is noted that the fluoranthene derivatives of formulas (V), (2) and (3), can be produced, for example, by the method described in J. Amer. Chem. Soc., 118, 2374 (1996). Specifically, as shown by the following scheme, the end compound can be produced by reacting a compound of formula (4) with a compound of formula (5).
4845


[0293] Once the skeleton of formula (VI) is formed, exchange of substituents is effected by a conventional method, obtaining a compound having the desired substituent(s).


[0294] The compounds of formula (VI) are preferably compounds, dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivatives in the following formula (VI′).
4846


[0295] In formula (VI′), X1 to X44 are as defined for X1 to X20 in formula (VI).


[0296] Preferably, X1 to X20 in formula (VI) and X1 to X44 in formula (VI′) are independently selected from among substituted or unsubstituted aryl, alkyl, alkenyl, alkoxy and aryloxy radicals.


[0297] Further preferably, at least one of X1 to X20 in formula (VI) and X1 to X44 in formula (VI′) is an ortho-substituted phenyl radical. Even more preferably, in formula (VI) or (VI′), either one or both of X1 and X4 and/or either one or both of X11 and X14 are ortho-substituted phenyl radicals. The introduction of a substituent at the ortho-position holds down the propensity for the compound to decompose upon sublimation purification and improves fluorescence.


[0298] The use of the ortho-substituted compound is effective for increasing the fluorescent luminance and holding down the concentration quenching of the EL device, thereby spreading the margin of the EL dopant and improving the freedom of design.


[0299] The introduction of an ortho-substituted phenyl group has several advantages. The ortho-substituted phenyl group introduced makes it possible to control the association of the perylene skeleton by virtue of its steric hindrance, to improve the solubility in solvents and to purify the compound to a high purity. For the same reason, sublimation purification becomes possible at a lower temperature and entails little decomposition. This is also advantageous in obtaining a high purity material. Using such a pure material, an organic EL device having a high emission efficiency is obtainable because the deactivation of excitons by impurities is minimized. Another reason accounting for the high efficiency is that the association between similar or distinct molecules in the light emitting layer is suppressed whereby concentration quenching is restrained.


[0300] Preferred examples of the compound of formula (VI′) are given below.
4847


[0301] The diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative should preferably have a vibration structure in both an excitation spectrum and a fluorescence spectrum. The presence of such a vibration structure is ascertainable by the appearance of two or more peaks in each of the spectra.


[0302] More preferably, a host material obtained by doping the indenoperylene derivative has such a vibration structure.


[0303] The possession of a vibration structure leads to the manufacture of an organic EL device having improved temperature characteristics.


[0304] It is believed that a drop of EL luminous efficiency by temperature is due to thermal relaxation entailing a change of conformation in the excited state. Once a change of conformation in the excited state occurs, the overlap of molecular orbital function between the ground state and the excited state changes so that the fluorescence spectrum does not become a mirror image of the absorption spectrum. The fluorescence spectrum of a compound which can take a plurality of conformations in the excited state is the total of various vibration structures and thus becomes a broad spectrum apparently free of a vibration structure.


[0305] Accordingly, an organic compound which exhibits a vibration structure in the fluorescence spectrum and specifically, a compound whose vibration structure is a mirror image of the absorption spectrum experiences a minimal change of conformation in the excited state and therefore, when used as a luminescent material in an organic EL device, enables to produce a device having improved temperature characteristics as demonstrated by a minimal drop of EL luminous efficiency by temperature during driving.


[0306] For the same reason as above, the organic compound should preferably have a Stokes shift of up to 0.1 eV, especially up to 0.05 eV. The lower limit of Stokes shift is not critical although it is usually about 0.01 eV.


[0307] Another factor that governs the temperature characteristics of an organic EL device is the thermal excitation of carriers from the trap level. Especially in a doped light emitting layer, the dopant creates a trap level. Upon a temperature change, the hopping probability of carriers by thermal excitation changes. This sometimes results in changes of the carrier balance in the light emitting layer, leading to temperature dependent characteristics with a high efficiency. In contrast, the device of the invention has a minimized thermal change of the trapping of the light emitting layer, that is, minimized temperature dependence with a high efficiency.


[0308] In a preferred embodiment, the host material, especially at least one of the organic compounds of formulas (I) to (IV), in a light emitting layer has a greater electron affinity than an electron transporting layer and/or a hole transporting layer. If the host material in a light emitting layer has a greater electron affinity than an electron transporting layer and/or a hole transporting layer, the injection efficiency of electrons into the light emitting layer increases and electrons are blocked at the hole transporting layer interface, leading to an improvement in luminous efficiency and hence, device lifetime.


[0309] Others


[0310] The light emitting layer containing the host material and the dopant according to the invention has functions of injecting holes and electrons, transporting them, and recombining holes and electrons to create excitons. The use of relatively electronically neutral compounds in the light emitting layer in addition to the compounds of the invention enables easy and well-balanced injection and transportation of electrons and holes.


[0311] The host material may be used alone or in admixture of two or more. When a mixture of two or more host materials is used, the mix ratio is not critical. In a preferred embodiment, the light emitting layer contains 80 to 99.9%, more preferably 90 to 99.9%, even more preferably 95.0 to 99.5% by weight of the host material.


[0312] The thickness of the light emitting layer preferably ranges from the thickness corresponding to a single molecule layer to less than the thickness of an organic compound layer, for example, preferably from 1 to 85 nm, more preferably 5 to 60 nm, most preferably 5 to 50 nm.


[0313] Preferably the mix layer is formed by a co-deposition process of evaporating the compounds from distinct sources. If both the compounds have equal or very close vapor pressure or evaporation temperature, they may be pre-mixed in a common evaporation boat, from which they are evaporated together. The mix layer is preferably a uniform mixture of both the compounds although the compounds can be present in island form. The light emitting layer is generally formed to a predetermined thickness by evaporating an organic fluorescent material or coating a dispersion thereof in a resin binder.


[0314] One exemplary construction of the organic EL light emitting device fabricated using the inventive compounds has on a substrate, a hole injecting electrode, a hole injecting and transporting layer, a light emitting and electron injecting and transporting layer, and an electron injecting electrode in the described order. If desired, a protective electrode, an auxiliary electrode and a sealing layer are provided on the electron injecting electrode.


[0315] The organic EL device of the invention is not limited to the above exemplary construction and may have various other constructions. In another exemplary construction, the light emitting layer is provided singly and an electron injecting and transporting layer is interposed between the light emitting layer and the electron injecting electrode. Also, the light emitting layer may be mixed with the hole injecting and transporting layer, if desired.


[0316] The thicknesses of the light emitting layer, hole injecting and transporting layer, and electron injecting and transporting layer are not critical and vary with a particular formation technique. Usually a single layer is about 5 to 500 nm thick, especially about 10 to 300 nm thick.


[0317] The thicknesses of the hole injecting and transporting layer and electron injecting and transporting layer are equal to or range from {fraction (1/10)} to 10 times the thickness of the light emitting layer although they depend on the design of a recombination/light emitting region. When the electron or hole injecting and transporting layer is divided into an injecting layer and a transporting layer, preferably the injecting layer is at least 1 nm thick and the transporting layer is at least 1 nm thick. The upper limit of thickness is generally about 500 nm for the injecting layer and about 500 nm for the transporting layer. The same applies when two injecting and transporting layers are provided.


[0318] The hole injecting and transporting layer has functions of facilitating injection of holes from the hole injecting electrode, transporting them stably, and blocking electrons. The electron injecting and transporting layer has functions of facilitating injection of electrons from the electron injecting electrode, transporting them stably, and blocking holes. These layers are effective for increasing the number of holes and electrons injected into the light emitting layer and confining holes and electrons therein for optimizing the recombination region to improve light emission efficiency.


[0319] In the hole injecting and transporting layer, there may be used various organic compounds as described, for example, in JP-A 63-295695, 2-191694, 3-792, 5-234681, 5-239455, 5-299174, 7-126225, 7-126226, and 8-100172, and EPO 650955A1. Exemplary are tetraarylbenzidine compounds (triaryldiamines or triphenyldiamines: TPD), aromatic tertiary amines, hydrazone derivatives, carbazole derivatives, triazole derivatives, imidazole derivatives, oxadiazole derivatives having an amino group, and polythiophenes. Two or more of these compounds may be used, and on such combined use, they may be formed as separate layers or mixed.


[0320] Where the hole injecting and transporting layer is formed separately as a hole injecting layer and a hole transporting layer, two or more compounds are selected in a proper combination from the compounds commonly used in hole injecting and transporting layers. In this regard, it is preferred to laminate layers in such an order that a layer of a compound having a lower ionization potential may be disposed adjacent the hole injecting electrode (ITO). It is also preferred to use a compound having good thin film forming ability at the hole injecting electrode surface. The order of lamination also applies where a plurality of hole injecting and transporting layers are provided. Such an order of lamination is effective for lowering the drive voltage and preventing current leakage and the development and growth of dark spots. Since evaporation is utilized in the manufacture of devices, films as thin as about 1 to 10 nm can be formed uniform and pinhole-free, which restrains any change in color tone of light emission and a drop of efficiency by re-absorption even if a compound having a low ionization potential and absorption in the visible range is used in the hole injecting layer. Like the light emitting layer, the hole injecting and transporting layer may be formed by evaporating the above-mentioned compounds.


[0321] In the electron injecting and transporting layer, there may be used quinoline derivatives including organic metal complexes having 8-quinolinol or a derivative thereof as a ligand such as tris(8-quinolinolato)aluminum (Alq3), oxadiazole derivatives, perylene derivatives, pyridine derivatives, pyrimidine derivatives, quinoxaline derivatives, diphenylquinone derivatives, and nitro-substituted fluorene derivatives. The electron injecting and transporting layer can also serve as the light emitting layer. Like the light emitting layer, the electron injecting and transporting layer may be formed by evaporation or the like.


[0322] Where the electron injecting and transporting layer is formed separately as an electron injecting layer and an electron transporting layer, two or more compounds are selected in a proper combination from the compounds commonly used in electron injecting and transporting layers. In this regard, it is preferred to stack layers in such an order that a layer of a compound having a greater electron affinity may be disposed adjacent the electron injecting electrode. The order of stacking also applies where a plurality of electron injecting and transporting layers are provided.


[0323] In forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer, vacuum evaporation is preferably used because homogeneous thin films are available. By utilizing vacuum evaporation, there is obtained a homogeneous thin film which is amorphous or has a crystal grain size of less than 0.1 μm. If the grain size is more than 0.1 μm, uneven light emission would take place and the drive voltage of the device must be increased with a substantial drop of hole injection efficiency.


[0324] The conditions for vacuum evaporation are not critical although a vacuum of 10−4 Pa or lower and a deposition rate of about 0.01 to 1 nm/sec are preferred. It is preferred to successively form layers in vacuum because the successive formation in vacuum can avoid adsorption of impurities on the interface between the layers, thus ensuring better performance. Also, the drive voltage of a device can be reduced and the development and growth of dark spots be restrained.


[0325] In the embodiment wherein the respective layers are formed by vacuum evaporation, where it is desired for a single layer to contain two or more compounds, preferably boats having the compounds received therein are individually temperature controlled to achieve co-deposition.


[0326] The electron injecting electrode is preferably made of metals, alloys or intermetallic compounds having a work function of up to 4 eV. With a work function of more than 4 eV, the electron injecting efficiency lowers and consequently, the light emission efficiency lowers. Examples of the metal having a work function of up to 4 eV of which the electron injecting electrode film is constructed include alkali metals such as Li, Na and K, alkaline earth metals such as Mg, Ca, Sr and Ba, rare earth metals such as La and Ce, and Al, In, Ag, Sn, Zn, and Zr. Examples of the film-forming alloy having a work function of up to 4 eV include Ag—Mg (Ag: 0.1 to 50 at %), Al—Li (Li: 0.01 to 12 at %), In—Mg (Mg: 50 to 80 at %), and Al—Ca (Ca: 0.01 to 20 at %). These materials may be present alone or in combination of two or more. Where two or more materials are combined, their mixing ratio is arbitrary. It is also acceptable that an oxide or halide of an alkali metal, alkaline earth metal or rare earth metal is thinly deposited and a supporting electrode (auxiliary electrode or wiring electrode) of aluminum etc. is used.


[0327] The electron injecting electrode may be formed by evaporation or sputtering.


[0328] The electron injecting electrode may have at least a sufficient thickness to effect electron injection, for example, a thickness of at least 0.1 nm. Although the upper limit is not critical, the electrode thickness is typically about 0.1 to about 500 nm.


[0329] The hole injecting electrode is preferably formed of such a material to such a thickness that the electrode may have a transmittance of at least 80% of emitted light. Illustratively, oxide transparent conductive thin films are preferred. For example, materials based on tin-doped indium oxide (ITO), zinc-doped indium oxide (IZO), indium oxide (In2O3), tin oxide (SnO2) or zinc oxide (ZnO) are preferable. These oxides may deviate somewhat from their stoichiometry. An appropriate proportion of SnO2 mixed with In2O3 is about 1 to 20% by weight, more preferably about 5 to 12% by weight. An appropriate proportion of ZnO2 mixed with In2O3 is about 12 to 32% by weight.


[0330] The hole injecting electrode should preferably have a light transmittance of at least 80%, especially at least 90% in the light emission band, typically from 350 to 800 nm, and especially at each light emission. Since the emitted light is generally taken out through the hole injecting electrode, with a lower transmittance, the light emitted by the light emitting layer would be attenuated through the electrode, failing to provide a luminance necessary as a light emitting device. It is noted that only the side from which the emitted light exits has a transmittance of at least 80%.


[0331] The hole injecting electrode has at least a sufficient thickness to effect hole injection, preferably a thickness of 50 to 500 nm, especially 50 to 300 nm. Although the upper limit of the electrode thickness is not critical, a too thick electrode would have the risk of separation. Too thin an electrode would have problems with respect to film strength during fabrication, hole transporting ability, and resistance value.


[0332] In depositing the hole injecting electrode, a sputtering process is preferred. The sputtering process may be a high-frequency sputtering process using an RF power supply although a dc sputtering process is preferably used when the ease of control of physical properties of the hole injecting electrode being deposited and the flatness of the deposited film are taken into account.


[0333] A protective film may be formed if necessary. The protective film may be formed using an inorganic material such as SiOx or an organic material such as Teflon. The protective film may be either transparent or opaque and have a thickness of about 50 to 1,200 nm. Apart from the reactive sputtering process mentioned above, the protective film may also be formed by an ordinary sputtering or evaporation process.


[0334] Further, a sealing layer is provided on the device in order to prevent the organic layers and electrodes from oxidation. In order to prevent the ingress of moisture, the sealing layer is formed by attaching a sealing plate such as a glass plate to the substrate with an adhesive resin layer such as a commercially available low moisture absorption photo-curable adhesive, epoxy base adhesive, silicone base adhesive, or crosslinking ethylene-vinyl acetate copolymer adhesive sheet. Metal plates and plastic plates may also be used instead of the glass plate.


[0335] Transparent or translucent materials such as glass, quartz and resins are used as the substrate when the emitted light exits from the substrate side. The substrate may be provided with a color filter film, a fluorescent material-containing color conversion film or a dielectric reflecting film for controlling the color of light emission. In the case of the inversely stacked layer structure, the substrate may be either transparent or opaque. For the opaque substrate, ceramic and other materials may be used.


[0336] The color filter film used herein may be a color filter as used in liquid crystal displays and the like. The properties of a color filter may be adjusted in accordance with the light emission of the organic EL device so as to optimize the extraction efficiency and chromatic purity.


[0337] It is also preferred to use a color filter capable of cutting external light of short wavelength which is otherwise absorbed by the EL device materials and fluorescence conversion layer, because the light resistance and display contrast of the device are improved.


[0338] An optical thin film such as a dielectric multilayer film may be used instead of the color filter.


[0339] Referring to FIG. 1, there is illustrated one exemplary construction of the organic EL device fabricated according to the invention. The organic EL device is shown in FIG. 1 as having on a substrate 1, a hole injecting electrode (or anode) 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron injecting and transporting layer 6, an electron injecting electrode (or cathode) 7, and optionally, a protective electrode 8 in the described order. The organic EL device of the invention is not limited to the illustrated construction, and various other constructions are possible depending on the desired device function. For example, the order of lamination may be inverse to the above-described order. The hole injecting 3, the hole transporting layer 4 and the electron injecting and transporting layer 6 may be omitted or either one of them may be a common layer to the light emitting layer 5.


[0340] The organic EL device of the invention is generally of the dc or pulse drive type while it can be of the ac drive type. The applied voltage is generally about 2 to 30 volts.



EXAMPLE

[0341] Examples of the present invention are given below together with Comparative Examples for further illustrating the invention.



Example 1

[0342] On a glass substrate, a transparent ITO electrode thin film was deposited to a thickness of 100 nm by RF sputtering and patterned. The glass substrate having the transparent ITO electrode was subjected to ultrasonic washing with neutral detergent, acetone, and ethanol, pulled up from boiling ethanol, and dried. The transparent electrode surface was further cleaned with UV/ozone. Thereafter, the substrate was secured by a holder in a vacuum evaporation chamber, which was evacuated to a vacuum of 1×10−5 Pa or lower.


[0343] With the vacuum kept, N,N′-diphenyl-N,N′-bis[N-(4-methylphenyl)-N-phenyl-(4-aminophenyl)]-1,1′-biphenyl-4,4′-diamine was evaporated at a deposition rate of 0.1 nm/sec. to a thickness of 50 nm, forming a hole injecting layer.


[0344] Then, N,N,N′,N′-tetrakis(m-biphenyl)-1,1′-biphenyl-4,4′-diamine (TPD) was evaporated at a deposition rate of 0.1 nm/sec to a thickness of 20 nm, forming a hole transporting layer.


[0345] With the vacuum kept, the host material and dopant of the following structural formulas were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer.
4848


[0346] Next, with the vacuum kept, tris(8-quinolinolato)aluminum was evaporated at a deposition rate of 0.1 nm/sec to a thickness of 20 nm, forming an electron transporting layer.


[0347] With the vacuum kept, LiF was evaporated at a deposition rate of 0.01 nm/sec to a thickness of 0.3 nm, forming an electron injecting electrode. Finally, aluminum was evaporated to a thickness of 150 nm to form a protective electrode, completing an organic EL device.


[0348] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 614 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.9 volts. The current efficiency was 6.1 cd/A, the power efficiency was 3.3 lm/W, the chromaticity coordinates (x, y) were (0.65, 0.35), and the maximum luminance was 19,600 cd/m2. When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 3,200 cd/m2 and a luminance half-life period of more than 600 hours.



Example 2

[0349] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4849


[0350] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 504 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.9 volts. The current efficiency was 5.0 cd/A, the power efficiency was 2.7 lm/W, the chromaticity coordinates (x, y) were (0.64, 0.36), and the maximum luminance was 11,500 cd/m2. When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,170 cd/m2 and a luminance half-life period of more than 1,500 hours.



Example 3

[0351] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4850


[0352] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 449 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.9 volts. The current efficiency was 4.5 cd/A, the power efficiency was 2.4 lm/W, the chromaticity coordinates (x, y) were (0.66, 0.34), and the maximum luminance was 17,200 cd/m2. When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,440 cd/m2 and a luminance half-life period of more than 1,500 hours.



Example 4

[0353] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4851


[0354] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 441 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.9 volts. The current efficiency was 4.4 cd/A, the power efficiency was 2.3 lm/W, the chromaticity coordinates (x, y) were (0.65, 0.34), and the maximum luminance was 35,200 cd/m2. When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,400 cd/m2 and a luminance attenuation of up to 10% after 1,000 hours and up to 15% after 4,500 hours.


[0355] The host material and dopant used in this device were assessed for excitation and fluorescence spectra, from which a Stokes shift was computed. The host material and dopant had a Stokes shift of 0.06 eV and 0.03 eV, respectively. FIG. 2 shows excitation and fluorescence spectra of the host material and dopant. It is seen from these spectral curves that both the host material and dopant have vibration structures.


[0356] The temperature characteristics of the device were examined to find the following luminance change on 10 mA/cm2 constant current driving in various temperature ranges:


[0357] −40° C. to 20° C.: ≦10%


[0358] 20° C. to 60° C.: ≦3%


[0359] −40° C. to 60° C.: ≦13%.


[0360] After 500 hours of continuous driving at 85° C., the device exhibited a luminance change of up to 10% and a drive voltage change of less than 2 V.



Example 5

[0361] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4852


[0362] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 296 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6.7 volts. The current efficiency was 3.0 cd/A, the power efficiency was 1.4 lm/W, the chromaticity coordinates (x, y) were (0.60, 0.38), and the maximum luminance was 16,500 cd/m2. When the device was continuously driven by conducting a constant current of 79 mA/cm2, it exhibited an initial luminance of at least 2,400 cd/m2 and a luminance half-life period of more than 300 hours.



Example 6

[0363] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4853


[0364] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 267 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6.6 volts. The current efficiency was 2.7 cd/A, the power efficiency was 1.3 lm/W, the chromaticity coordinates (x, y) were (0.55, 0.37), and the maximum luminance was 12,860 cd/m2. When the device was continuously driven by conducting a constant current of 97 mA/cm2, it exhibited an initial luminance of at least 2,400 cd/m2 and a luminance half-life period of more than 300 hours.



Example 7

[0365] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4854


[0366] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 260 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6.7 volts. The current efficiency was 2.6 cd/A, the power efficiency was 1.2 lm/W, the chromaticity coordinates (x, y) were (0.64, 0.36), and the maximum luminance was 8,780 cd/m2. When the device was continuously driven by conducting a constant current of 95 mA/cm2, it exhibited an initial luminance of at least 2,400 cd/m2 and a luminance half-life period of more than 300 hours.



Example 8

[0367] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to a mixture of the following compounds in a weight ratio of 9:1 (the former compound is the same as used in Example 4).
4855


[0368] The host material (mixture) and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer.


[0369] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 494 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.9 volts. The current efficiency was 4.9 cd/A, the power efficiency was 2.6 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.34). When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,640 cd/m2 and a luminance attenuation of up to 10% after 2,000 hours.



Example 9

[0370] An organic EL device was prepared as in Example 8 except that the weight ratio of the host compounds in the light emitting layer was changed to 7.5:2.5.


[0371] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 510 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6 volts. The current efficiency was 5.1 cd/A, the power efficiency was 2.8 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.34). When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,330 cd/m2 and a luminance attenuation of up to 10% after 2,000 hours.



Example 10

[0372] An organic EL device was prepared as in Example 8 except that the weight ratio of the host compounds in the light emitting layer was changed to 5:5.


[0373] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 534 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.9 volts. The current efficiency was 5.3 cd/A, the power efficiency was 2.8 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.35). When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,391 cd/m2 and a luminance attenuation of up to 10% after 2,000 hours.



Example 11

[0374] An organic EL device was prepared as in Example 1 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4856


[0375] The host material and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer. The dopant material had to be heated at 460° C. or higher for purification by sublimation.


[0376] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 505 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.7 volts. The current efficiency was 5.1 cd/A, the power efficiency was 2.8 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.35). When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,330 cd/m2 and a luminance attenuation of up to 30% after 1,700 hours.



Example 12

[0377] An organic EL device was prepared as in Example 1 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4857


[0378] The host material and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer.


[0379] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 438 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6 volts. The current efficiency was 4.4 cd/A, the power efficiency was 2.3 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.35). When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 2,650 cd/m2 and a luminance attenuation of up to 10% after 2,300 hours.



Example 13

[0380] An organic EL device was prepared as in Example 1 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4858


[0381] The host material and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer.


[0382] The host material and dopant used in this device were assessed for excitation and fluorescence spectra, from which a Stokes shift was computed. The host material had a Stokes shift of 0.24 eV. It is seen from the spectral curves that both the host material and dopant have vibration structures.


[0383] The temperature characteristics of the device were examined to find the following luminance change in various temperature ranges:


[0384] −40° C. to 20° C.: ≦−4%


[0385] 20° C. to 60° C.: ≦−3%


[0386] −40° C. to 60° C.: ≦−7%.



Example 14

[0387] An organic EL device was prepared as in Example 1 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4859


[0388] The host material and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer. It is noted that the dopant material could be purified by sublimation at a temperature below 360° C.


[0389] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 660 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 5.6 volts. The current efficiency was 6.6 cd/A, the power efficiency was 3.7 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.35). The maximum luminance was 55,000 cd/m2. When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 3,530 cd/m2 and a luminance attenuation of up to 10% after 500 hours.



Example 15

[0390] An organic EL device was prepared as in Example 1 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4860


[0391] The host material and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer. It is noted that the dopant material could be purified by sublimation at a temperature below 360° C.


[0392] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 764 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6 volts. The current efficiency was 7.6 cd/A, the power efficiency was 4.0 lm/W, and the chromaticity coordinates (x, y) were (0.65, 0.35). The maximum luminance was 24,500 cd/m2. When the device was continuously driven by conducting a constant current of 50 mA/cm2, it exhibited an initial luminance of at least 4,200 cd/m2 and a luminance attenuation of up to 10% after 500 hours.



Comparative Example 1

[0393] An organic EL device was prepared as in Example 1 except that the host material in the light emitting layer was changed to the following compound.
4861


[0394] A DC voltage was applied across the organic EL device. Initially, the device was found to produce light emission to a luminance of 160 cd/m2 when operated at a current density of 10 mA/cm2 and a drive voltage of 6.9 volts. The current efficiency was 1.6 cd/A, the power efficiency was 0.7 lm/W, the chromaticity coordinates (x, y) were (0.61, 0.37), and the maximum luminance was 9,570 cd/m2. When the device was continuously driven by conducting a constant current of 145 mA/cm2, it exhibited an initial luminance of at least 2,400 cd/m2 and a luminance half-life period of less than 300 hours.



Comparative Example 2

[0395] An organic EL device was prepared as in Example 4 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4862


[0396] The host material and the dopant were evaporated in a weight ratio of 97:3 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer.


[0397] The host material and dopant used in this device were assessed for excitation and fluorescence spectra, from which a Stokes shift was computed. The host material and dopant had a Stokes shift of 0.2 eV and 0.31 eV, respectively. FIG. 3 shows excitation and fluorescence spectra of the host material and dopant. It is seen from the spectral curves that the dopant does not have a vibration structure in the excitation spectrum, and the host material does not have a vibration structure in the fluorescence spectrum.


[0398] The temperature characteristics of the device were examined to find the following luminance change on 10 mA/cm2 constant current driving in various temperature ranges:


[0399] −40° C. to 20° C.: ≧−12%


[0400] 20° C. to 60° C.: ≧−9%


[0401] −40° C. to 60° C.: ≧−21%.



Comparative Example 3

[0402] An organic EL device was prepared as in Example 4 except that the host material and the dopant in the light emitting layer were changed to the following compounds.
4863


[0403] The host material and the dopant were evaporated in a weight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm, forming a light emitting layer.


[0404] The host material and dopant used in this device were assessed for excitation and fluorescence spectra, from which a Stokes shift was computed. The host material and dopant had a Stokes shift of 0.2 eV and 0.31 eV, respectively. It is seen from the spectral curves that neither the host material nor the dopant has a vibration structure.


[0405] The temperature characteristics of the device were examined to find the following luminance change in various temperature ranges:


[0406] −40° C. to 20° C.: ≧31%


[0407] 20° C. to 60° C.: ≧18%


[0408] −40° C. to 60° C.: ≧49%.


[0409] There has been described an organic EL device which emits light to a satisfactory luminance, especially in a long wavelength region, is operated at a constant voltage, and has a sufficient durability to maintain satisfactory light emission performance over a long period of time, experience a minimal voltage rise during continuous operation, and undergo a minimal degradation on driving at elevated temperature. Especially when a red light emitting device is fabricated, it has a high chromatic purity because the host produces little light emission. Over a wide temperature region, the device produces a consistent luminance with minimal changes of efficiency. The device can produce linear luminance characteristics in proportion to current flow over a wide current region covering from the low current region for use in TFT driving to the high current region for use in simple matrix driving and thus provide a satisfactory tone display.


[0410] Although some preferred embodiments have been described, many modifications and variations may be made thereto in light of the above teachings. It is therefore to be understood that the invention may be practiced otherwise than as specifically described without departing from the scope of the appended claims.


[0411] This application is based on Japanese patent applications JP 2000-121724, filed Apr. 21, 2000, and JP 2001-121664, filed Apr. 19, 2001, the entire contents of each of which are hereby incorporated by reference, the same as if set forth at length.


Claims
  • 1. An organic EL device comprising one or more organic layers between a pair of electrodes participating in at least a light emitting function, at least one of the organic layers containing at least one of organic compounds having basic skeletons of the following formulas (I) to (IV) and at least one organic compound having a skeleton of the following formula (V) at the same time: 4864 wherein Q1 to Q8 are independently hydrogen or substituted or unsubstituted alkyl, aryl, amino, heterocyclic or alkenyl radicals, 4865 wherein R1, R2, R3 and R4 are independently aryl, fluorene, carbazolyl, alkyl, alkoxy, aryloxy, amino or halogen radicals, at least one of R1, R2, R3 and R4 is aryl, r1, r2, r3 and r4 each are 0 or an integer of 1 to 5, with the proviso that r1, r2, r3 and r4 are not 0 at the same time, R5 and R6 are independently alkyl, alkoxy, amino, aryl or halogen radicals and may be the same or different, r5 and r6 each are 0 or an integer of 1 to 4, 4866 wherein A101 is a monophenylanthryl or diphenylanthryl radical and may be the same or different, L is hydrogen, a single bond or an n-valent linkage, and n is an integer of 1 to 4, Qn-L101  (IV)  wherein Q is a pyrazinyl radical having fused thereto a six-membered aromatic ring containing 0 to 2 nitrogen atoms and may be the same or different, n is 2 or 3, and L101 is a single bond or n-valent radical, 4867 wherein X1 to X10, L1 and L2 are independently hydrogen, halogen atoms, straight, branched or cyclic alkyl radicals which may have substituents, straight, branched or cyclic alkoxy radicals which may have substituents, straight, branched or cyclic alkylthio radicals which may have substituents, straight, branched or cyclic alkenyl radicals which may have substituents, straight, branched or cyclic alkenyloxy radicals which may have substituents, straight, branched or cyclic alkenylthio radicals which may have substituents, substituted or unsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxy radicals, substituted or unsubstituted aralkylthio radicals, substituted or unsubstituted aryl radicals, substituted or unsubstituted aryloxy radicals, substituted or unsubstituted arylthio radicals, substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR1 radicals (wherein R1 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical or a substituted or unsubstituted aryl radical), —COR2 radicals (wherein R2 is hydrogen, a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical or an amino radical), or —OCOR3 radicals (wherein R3 is a substituted or unsubstituted straight, branched or cyclic alkyl radical, a substituted or unsubstituted straight, branched or cyclic alkenyl radical, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), or at least two adjoining radicals selected from X1 to X10, L1 and L2 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached, or L1 and L2 each may be a single bond. n is 1 or 2.
  • 2. The organic EL device of claim 1 wherein the at least one of the organic layers contains a host material and a dopant, said host material comprises at least one compound selected from the organic compounds having basic skeletons of the formulas (I) to (IV) and said dopant comprises at least one compound selected from the organic compounds having a skeleton of the formula (V).
  • 3. The organic EL device of claim 1 or 2 wherein in formula (V), at least two adjoining radicals selected from X1 to X10, L1 and L2 bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms to which they are attached.
  • 4. The organic EL device of any one of claims 1 to 3 wherein the compound of formula (V) is a compound of the following formula (VI):
  • 5. The organic EL device of claim 4 wherein the compound of formula (VI) is a compound of the following formula (VI′):
  • 6. The organic EL device of claim 4 or 5 wherein X1 to X20 in formula (VI) and X1 to X44 in formula (VI′) are independently substituted or unsubstituted aryl, alkyl, alkenyl, alkoxy or aryloxy radicals.
  • 7. The organic EL device of any one of claims 4 to 6 wherein at least one of X1 to X20 in formula (VI) and X1 to X44 in formula (VI′) is an ortho-substituted phenyl radical.
  • 8. The organic EL device of any one of claims 4 to 7 wherein in formula (VI) or (VI′), either one or both of X1 and X4 and/or either one or both of X11 and X14 are ortho-substituted phenyl radicals.
  • 9. The organic EL device of any one of claims 1 to 8 wherein said at least one of the organic layers contains at least one organic compound having a basic skeleton of the formula (I).
  • 10. The organic EL device of any one of claims 1 to 9 wherein said at least one of the organic layers contains at least one organic compound having a basic skeleton of the formula (I) and at least one organic compound having a basic skeleton of the formula (II) at the same time.
  • 11. The organic EL device of any one of claims 4 to 10 wherein at least one of the organic compounds has a vibration structure in both an excitation spectrum and a fluorescence spectrum.
  • 12. The organic EL device of any one of claims 4 to 11 wherein at least one of the organic compounds has a Stokes shift of up to 0.1 eV.
  • 13. The organic EL device of any one of claims 4 to 12 wherein the host material in a light emitting layer has a greater electron affinity than an electron transporting layer and/or a hole transporting layer.
  • 14. The organic EL device of any one of claims 1 to 13 wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least two of Q1 to Q8 are substituted or unsubstituted aryl radicals.
  • 15. The organic EL device of claim 14 wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least six of Q1 to Q8 are substituted or unsubstituted aryl radicals.
  • 16. The organic EL device of claim 14 or 15 wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least two of Q1, Q2, Q3 and Q4 are substituted or unsubstituted aryl radicals.
  • 17. The organic EL device of any one of claims 14 to 16 wherein the organic compound having a basic skeleton of the formula (I) is one wherein at least four of Q1, Q2, Q3 and Q4 are substituted or unsubstituted aryl radicals.
  • 18. The organic EL device of any one of claims 14 to 17 wherein at least two of the aryl radicals represented by Q1, Q2, Q3 and Q4 have aryl radicals substituted thereon.
  • 19. The organic EL device of any one of claims 2 to 18 wherein the at least one of the organic layers contains 80 to 99.9% by weight of the host material.
  • 20. An organic EL device wherein at least one of organic layers contains at least one organic compound having a basic skeleton of the formula (I) as set forth in claim 16 and at least one organic compound having a basic skeleton of the formula (IV′).
  • 21. The organic EL device of any one of claims 1 to 20, further comprising at least one hole injecting and transporting layer.
  • 22. The organic EL device of any one of claims 1 to 21, further comprising at least one electron injecting and transporting layer.
  • 23. An organic EL device comprising one or more organic layers between a pair of electrodes participating in at least a light emitting function, wherein the one or more organic layers contain organic compounds, at least one of which has a vibration structure in both an excitation spectrum and a fluorescence spectrum.
  • 24. An organic EL device comprising one or more organic layers between a pair of electrodes participating in at least a light emitting function, wherein the one or more organic layers contain organic compounds, at least one of which has a Stokes shift of up to 0.1 eV.
  • 25. The organic EL device of claim 24 wherein a host material in a light emitting layer has a greater electron affinity than an electron transporting layer and/or a hole transporting layer.
Priority Claims (2)
Number Date Country Kind
2000-121724 Apr 2000 JP
2001-121664 Apr 2001 JP