Information
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Patent Application
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20030027016
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Publication Number
20030027016
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Date Filed
April 20, 200123 years ago
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Date Published
February 06, 200322 years ago
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Inventors
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Original Assignees
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CPC
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US Classifications
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International Classifications
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 1
|
|
SUBSTITUENT
Compound
No.Q10Q20Q30Q40Q50Q60Q70Q80
|
|
IB-110111213HHHH
|
IB-214151617HHHH
|
IB-318192021HHHH
|
IB-422232425HHHH
|
IB-526272829HHHH
|
IB-630313233HHHH
|
IB-734353637HHHH
|
IB-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 25
|
|
SUBSTITUENT
Com-
pound
No.Q10Q20Q30Q40Q50Q60Q70Q80
|
|
IIB-1762763764765HHHH
|
IIB-2766767768769HHHH
|
IIB-3770771772773HHHH
|
IIB-4774775776777HHHH
|
IIB-5778779780781HHHH
|
IIB-6782783784785HHHH
|
IIB-7786787788789HHHH
|
IIB-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 36
|
|
SUBSTITUENT
Compound No.Q10Q20Q30
|
IVB-1 103410351036
|
IVB-2 103710381039
|
IVB-3 104010411042
|
IVB-4 104310441045
|
IVB-5 104610471048
|
IVB-6 104910501051
|
IVB-7 105210531054
|
IVB-8 105510561057
|
IVB-9 105810591060
|
IVB-10106110621063
|
IVB-11106410651066
|
SUBSTITUENT
Compound No.Q40Q50Q60Q70Q80
|
IVB-1 1067CH3CH3HH
|
IVB-2 1068CH3CH3HH
|
IVB-3 1069CH3CH3HH
|
IVB-4 1070CH3CH3HH
|
IVB-5 1071CH3CH3HH
|
IVB-6 1072CH3CH3CH3CH3
|
IVB-7 1073CH3CH3CH3CH3
|
IVB-8 1074CH3CH3CH3CH3
|
IVB-9 1075CH3CH3CH3CH3
|
IVB-101076CH3CH3CH3CH3
|
IVB-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.
70|
|
|
2549
|
Com-
pound
No.R1˜R4R5˜R9R10˜R13R14˜R18R19˜R22R23˜R27R28˜R31R32˜R36R37˜R44
|
|
I-1HHHHHHHHH
I-2HR6 = CH3HR17═CH3HR26 = CH3HR35 = CH3H
I-3HR7 = CH3HR16 = CH3HR25 = CH3HR34 = CH3H
I-4HR7 = t-C4H9HR16 = t-C4H9HR25 = t-C4H9HR34 = t-C4H9H
I-5HR7 = OCH3HR16 = OCH3HR25 = OCH3HR34 = OCH3H
I-6HR7 = PhHR16 = PhHR25 = PhHR34 = PhH
|
I-7H2550H2551H2552H2553H
|
I-8HR7 = OPhHR16 = OPhHR25 = OPhHR34 = OPhH
I-9HR7 = N(C2H5)2HR16 = N(C2H5)2HR25 = N(C2H5)2HR34 = N(C2H5)2H
I-10HR7 = N(Ph)2HR16 = N(Ph)2HR25 = N(Ph)2HR34 = N(Ph)2H
I-11HR7 = ClHR16 = ClHR25 = ClHR34 = ClH
I-12R2 = CH3HR11 = CH3HR20 = CH3HR29 = CH3HH
I-13HR6 = PhHR17 = PhHR26 = PhHR35 = PhH
I-14HR7 = PhHR16 = PhHHHHH
I-15HR6 = PhHR17 = PhHHHHH
I-16R2 = OCH3HR11 = OCH3HR20 = OCH3HR29 = OCH3HH
I-17R2 = PhHR11 = PhHR20 = PhHR29 = PhHH
I-18R2 = OPhHR11 = OPhHR20 = OPhHR29 = OPhHH
I-19R2 = N(C2H5)2HR11 = N(C2H5)2HR20 = N(C2H5)2HR29 = N(C2H5)2HH
I-20R2 = ClHR11 = ClHR20 = ClHR29 = ClHH
I-21HHHHHHHHR37 = R42 = CH3
I-22HHHHHHHHR37 = R42 = OCH3
I-23HHHHHHHHR37 = R42 = N(C2H5)2
I-24HHHHHHHHR37 = R42 = Cl
I-25HHHHHHHHR40 = R43 = CH3
I-26R2 = PhR7 = PhR11 = PhR16 = PhR20 = PhR25 = PhR29 = PhR34 = PhH
I-27R2 = N(Ph)2HR11 = PhHR20 = PhHR29 = PhHH
I-28HR6 = CH3HR16 = CH3HR26 = CH3HR34 = CH3H
I-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.
74|
|
|
2590
|
Compound No.M11M12M13M14M15M21M22M23M24M25
|
I-1 HHHHHHHHHH
I-2 CH3HHHHCH3HHHH
I-3 t-C4H9HHHHt-C4H9HHHH
I-4 OCH3HHHHOCH3HHHH
I-5 OPhHHHHOPhHHHH
I-6 N(C2H5)2HHHHN(C2H5)2HHHH
I-7 N(Ph)2HHHHN(Ph)2HHHH
I-8 PhHHHHPhHHHH
|
I-9 2591HHHH2592HHHH
|
I-10HCH3HHHHCH3HHH
I-11HCH3HCH3HHCH3HCH3H
I-12HHCH3HHHHCH3HH
I-13HCH3HHCH3HCH3HHCH3
I-14t-C4H9HHHHHHHHH
|
I-152593HHHH2594HHHH
|
I-16HPhHHHHPhHHH
I-17HHPhHHHHPhHH
|
I-182595HHHH2596HHHH
|
I-19n-C4H9HHHHn-C4H9HHHH
|
I-202597HHHH2598HHHH
|
I-21HH2599HHHH2600HH
|
I-222601HHHH2602HHHH
|
I-23HH2603HHHH2604HH
|
I-24HHPhHPhHHPhHPh
I-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.
82|
|
Formula (VIII)
Compound No.L111A13═A23A15═A15A16═A26A17═A27A18═A28
|
|
VIII-a-12737—PhHHHH
|
VIII-a-22738—PhHHCH3H
|
VIII-a-32739—PhHCH3CH3H
|
VIII-a-42740—PhHHC2H5H
|
VIII-a-52741—PhHHn-C3H7H
|
VIII-a-62742—PhHHn-C4H9H
|
VIII-a-72743—PhHHt-C4H9H
|
VIII-a-82744—PhHH—OCH3H
|
|
VIII-a-92745—PhHHA17 and A18 form a benzene ring. A27 A28 form a benzene ring
|
|
VIII-a-102746—PhHA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.H
|
|
VIII-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—PhH
|
VIII-a-152751—PhH—Ph—PhH
|
VIII-a-162752—Ph—PhHH—Ph
|
VIII-a-172753—PhHH1-naphthylH
|
VIII-a-182754—PhHH2-naphthylH
|
VIII-a-192755—PhHH4-biphenylylH
|
VIII-a-202756—PhHH3-biphenylylH
|
VIII-a-212757—PhHH2-biphenylylH
|
VIII-a-222758—PhH4-biphenylyl4-biphenylylH
|
VIII-a-232759—PhHHClH
|
VIII-a-242760—PhHH—OHH
|
VIII-a-252761—PhHH—NO2H
|
VIII-a-262762—PhHH—CNH
|
VIII-a-272763—PhHH—OPhH
|
VIII-a-282764—PhHH—SCH3H
|
VIII-a-292765—PhHH—SPhH
|
VIII-a-302766—PhHHHH
|
VIII-a-312767—PhHHCH3H
|
VIII-a-322768—PhHCH3CH3H
|
VIII-a-332769—PhCH3HHCH3
|
VIII-a-342770—PhHHC2H5H
|
VIII-a-352771—PhHHn-C3H7H
|
VIII-a-362772—PhHHn-C4H9H
|
VIII-a-372773—PhHHt-C4H9H
|
VIII-a-382774—PhHH—OCH3H
|
|
VIII-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 ringH
|
|
VIII-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—PhH
|
VIII-a-452781—PhH—Ph—PhH
|
VIII-a-462782—Ph—PhHH—Ph
|
VIII-a-472783—PhHH1-naphthylH
|
VIII-a-482784—PhHH2-naphthylH
|
VIII-a-492785—PhHH4-biphenylylH
|
VIII-a-502786—PhHH3-biphenylylH
|
VIII-a-512787—PhHH2-biphenylylH
|
VIII-a-522788—PhHHClH
|
VIII-a-532789—PhHH—OHH
|
VIII-a-542790—PhHH—NO2H
|
VIII-a-552791—PhHH—CNH
|
VIII-a-562792—PhHH—OPhH
|
VIII-a-572793—PhHH—SCH3H
|
VIII-a-582794—PhHH—SPhH
|
VIII-a-592795—PhHHHH
|
VIII-a-602796—PhHHCH3H
|
VIII-a-612797—PhHCH3CH3H
|
VIII-a-622798—PhCH3HHCH3
|
VIII-a-632799—PhCH3CH3CH3H
|
VIII-a-642800—PhCH3CH3CH3CH3
|
VIII-a-652801—PhHHC2H5H
|
VIII-a-662802—PhHHn-C3H7H
|
VIII-a-672803—PhHHn-C4H9H
|
VIII-a-682804—PhHHt-C4H9H
|
VIII-a-692805—PhHH—OCH3H
|
|
VIII-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.H
|
|
VIII-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 ring
|
|
VIII-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—PhH
|
VIII-a-762812—PhH—Ph—PhH
|
VIII-a-772813—Ph—PhHH—Ph
|
VIII-a-782814—PhHH1-naphthylH
|
VIII-a-792815—PhHH2-naphthylH
|
VIII-a-802816—PhHH4-biphenylylH
|
VIII-a-812817—PhHH3-biphenylylH
|
VIII-a-822818—PhHH2-biphenylylH
|
VIII-a-832819—PhHHClH
|
VIII-a-842820—PhHH—OHH
|
VIII-a-852821—PhHH—NO2H
|
VIII-a-862822—PhHH—CNH
|
VIII-a-872823—PhHH—OPhH
|
VIII-a-882824—PhHH—SCH3H
|
VIII-a-892825—PhHH—SPhH
|
VIII-a-9028262827HHHH
|
|
VIII-a-9128282829
A23 = —PhA15 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 = —Ph
|
|
VIII-a-9328322833HHHH
|
A23 = —Ph
|
|
VIII-a-9428342835A15 and A16 form a benzene ring. A25 and A26 form a benzene ring.HH
|
A23 = —Ph
|
|
VIII-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 = —Ph
|
|
VIII-a-962838—PhHH—NPh2H
|
VIII-a-972839—PhHH—COOHH
|
VIII-a-982840—PhHH2-pyridylH
|
VIII-a-992841—PhHH—NPh2H
|
VIII-a-1002842—PhHH—COOHH
|
VIII-a-1012843—PhHH2-pyridylH
|
VIII-a-1022844—PhHH—NPh2H
|
VIII-a-1032845—PhHH—COOHH
|
VIII-a-1042846—PhHH2-pyridylH
|
Formula (VIII)
Compound No.L111A13 ═A23A16═A26 A17═A27A18═A28
|
|
VIII-b-12847—PhHHH
|
VIII-b-22848—PhHHH
|
VIII-b-32849—PhHHH
|
VIII-b-428502851HHH
|
A23 = —Ph
|
VIII-b-528522853HHH
|
A23 = —Ph
|
VIII-b-62854—PhHHCH3
|
VIII-b-72855—PhHCH3H
|
VIII-b-82856—PhCH3HH
|
VIII-b-92857—PhHC2H5H
|
VIII-b-102858—PhHn-C3H7H
|
VIII-b-112859—PhHn-C4H9H
|
VIII-b-122860—PhHt-C4H9H
|
VIII-b-132861—PhH—OCH3H
|
|
VIII-b-142862—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.H
|
|
VIII-b-15 2863—PhHA17 and A18 form a benzene ring. Ahd 27 and A28 form a benzene ring.
|
|
VIII-b-162864—PhHPhH
|
VIII-b-172865—PhPhPhH
|
VIII-b-182866—PhH1-naphthylH
|
VIII-b-192867—Ph1-naphthyl1-naphthylH
|
VIII-b-202868—PhH2-naphthylH
|
VIII-b-212869—Ph2-naphthyl2-naphthylH
|
VIII-b-222870—PhH4-biphenylylH
|
VIII-b-232871—Ph4-biphenylyl4-biphenylylH
|
VIII-b-242872—PhH3-biphenylylH
|
VIII-b-252873—Ph3-biphenylyl3-biphenylylH
|
VIII-b-262874—PhH2-biphenylylH
|
VIII-b-272875—Ph2-biphenylyl2-biphenylylH
|
VIII-b-282876—PhHClH
|
VIII-b-292877—PhH—OHH
|
VIII-b-302878—PhH—NO2H
|
VIII-b-312879—PhH—CNH
|
VIII-b-322880—PhH—OPhH
|
VIII-b-332881—PhH—SCH3H
|
VIII-b-342882—PhH—SPhH
|
VIII-b-352883—PhH—NPh2H
|
VIII-b-362884—PhH—COOHH
|
VIII-b-372885—PhH2-pyridylH
|
VIII-b-382886—PhHHCH3
|
VIII-b-392887—PhHCH3H
|
VIII-b-402888—PhCH3HH
|
VIII-b-412889—PhHC2H5H
|
VIII-b-422890—PhHn-C3H7H
|
VIII-b-432891—PhHn-C4H9H
|
VIII-b-442892—PhHt-C4H9H
|
VIII-b-452893—PhH—OCH3H
|
|
VIII-b-462894—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.H
|
|
VIII-b-47 2895—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-b-482896—PhHPhH
|
VIII-b-492897—PhPhPhH
|
VIII-b-502898—PhH1-naphthylH
|
VIII-b-512899—Ph1-naphthyl1-naphthylH
|
VIII-b-522900—PhH2-naphthylH
|
VIII-b-532901—Ph2-naphthyl2-naphthylH
|
VIII-b-542902—PhH4-biphenylylH
|
VIII-b-552903—Ph4-biphenylyl4-biphenylylH
|
VIII-b-562904—PhH3-biphenylylH
|
VIII-b-572905—Ph3-biphenylyl3-biphenylylH
|
VIII-b-582906—PhH2-biphenylylH
|
VIII-b-592907—Ph2-biphenylyl2-biphenylylH
|
VIII-b-602908—PhHClH
|
VIII-b-612909—PhH—OHH
|
VIII-b-622910—PhH—NO2H
|
VIII-b-632911—PhH—CNH
|
VIII-b-642912—PhH—OPhH
|
VIII-b-652913—PhH—SCH3H
|
VIII-b-662914—PhH—SPhH
|
VIII-b-672915—PhH—NPh2H
|
VIII-b-682916—PhH—COOHH
|
VIII-b-692917—PhH2-pyridylH
|
VIII-b-702918—PhHHCH3
|
VIII-b-712919—PhHCH3H
|
VIII-b-722920—PhCH3HH
|
VIII-b-732921—PhHC2H5H
|
VIII-b-742922—PhHn-C3H7H
|
VIII-b-752923—PhHn-C4H9H
|
VIII-b-762924—PhHHt-C4H9
|
VIII-b-772925—PhHt-C4H9H
|
VIII-b-782926—PhH—OCH3H
|
|
VIII-b-79 2927—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring.H
|
|
VIII-b-802928—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-b-812929—PhH—PhH
|
VIII-b-822930—PhPhPhH
|
VIII-b-832931—PhH1-naphthylH
|
VIII-b-842932—Ph1-naphthyl1-naphthylH
|
VIII-b-852933—PhH2-naphthylH
|
VIII-b-862934—Ph2-naphthyl2-naphthylH
|
VIII-b-872935—PhH4-biphenylylH
|
VIII-b-882936—Ph4-biphenylyl4-biphenylylH
|
VIII-b-892937—PhH3-biphenylylH
|
VIII-b-902938—Ph3-biphenylyl3-biphenylylH
|
VIII-b-912939—PhH2-biphenylylH
|
VIII-b-922940—Ph2-biphenylyl2-biphenylylH
|
VIII-b-932941—PhHClH
|
VIII-b-942942—PhH—OHH
|
VIII-b-952943—PhH—NO2H
|
VIII-b-962944—PhH—CNH
|
VIII-b-972945—PhH—OPhH
|
VIII-b-982946—PhH—SCH3H
|
VIII-b-992947—PhH—SPhH
|
VIII-b-1002948—PhH—NPh2H
|
VIII-b-1012949—PhH—COOHH
|
VIII-b-1022950—PhH2-pyridylH
|
|
Formula (VIII)
Compound No.L111A13═A23A15═A25A17═A27A18═A28
|
|
VIII-c-12951—PhHHH
|
VIII-c-22952—PhHHH
|
VIII-c-32953—PhHHH
|
VIII-c-429542955HHH
|
A23 = —Ph
|
VIII-c-529562957HHH
|
A23 = —Ph
|
VIII-c-62958—PhHHCH3
|
VIII-c-72959—PhHCH3H
|
VIII-c-82960—PhCH3HH
|
VIII-c-92961—PhHC2H5H
|
VIII-c-102962—PhHn-C3H7H
|
VIII-c-112963—PhHn-C4H9H
|
VIII-c-122964—PhHt-C4H9H
|
VIII-c-132965—PhH—OCH3H
|
|
VIII-c-142966—PhHA17 and A18 form a benzene ring. A27 and A28 form a beozene ring.
|
|
VIII-c-152967—PhHH—Ph
|
VIII-c-162968—PhH—PhH
|
VIII-c-172969—Ph—PhHH
|
VIII-c-182970—PhH1-naphthylH
|
VIII-c-192971—PhH2-naphthylH
|
VIII-c-202972—PhH4-biphenylylH
|
VIII-c-212973—PhH3-biphenylylH
|
VIII-c-222974—PhH2-biphenylylH
|
VIII-c-232975—PhHClH
|
VIII-c-242976—PhH—OHH
|
VIII-c-252977—PhH—NO2H
|
VIII-c-262978—PhH—CNH
|
VIII-c-272979—PhH—OPhH
|
VIII-c-282980—PhH—SCH3H
|
VIII-c-292981—PhH—SPhH
|
VIII-c-302982—PhH—NPh2H
|
VIII-c-312983—PhH—COOHH
|
VIII-c-322984—PhH2-pyridylH
|
VIII-c-332985—PhHHCH3
|
VIII-c-342986—PhHCH3H
|
VIII-c-352987—PhCH3HH
|
VIII-c-362988—PhHC2H5H
|
VIII-c-372989—PhHn-C3H7H
|
VIII-c-382990—PhHn-C4H9H
|
VIII-c-392991—PhHt-C4H9H
|
VIII-c-402992—Ph—OCH3HH
|
|
VIII-c-41 2993—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-c-422994—PhHH—Ph
|
VIII-c-432995—PhH—PhH
|
VIII-c-442996—Ph—PhHH
|
VIII-c-452997—PhH1-naphthylH
|
VIII-c-462998—PhH2-naphthylH
|
VIII-c-472999—PhH4-biphenylylH
|
VIII-c-483000—PhH3-biphenylylH
|
VIII-c-493001—PhH2-biphenylylH
|
VIII-c-503002—PhHClH
|
VIII-c-513003—PhH—OHH
|
VIII-c-523004—PhH—NO2H
|
VIII-c-533005—PhH—CNH
|
VIII-c-543006—PhH—OPhH
|
VIII-c-553007—PhH—SCH3H
|
VIII-c-563008—PhH—SPhH
|
VIII-c-573009—PhH—NPh2H
|
VIII-c-583010—PhH—COOHH
|
VIII-c-593011—PhH2-pyridylH
|
VIII-c-603012—PhHHCH3
|
VIII-c-613013—PhHCH3H
|
VIII-c-623014—PhCH3HH
|
VIII-c-633015—PhHC2H5H
|
VIII-c-643016—PhHn-C3H7H
|
VIII-c-653017—PhHn-C4H9H
|
VIII-c-663018—PhHt-C4H9H
|
VIII-c-673019—PhH—OCH3H
|
|
VIII-c-68 3020—PhHA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-c-693021—PhHH—Ph
|
VIII-c-703022—PhH—PhH
|
VIII-c-713023—Ph—PhHH
|
VIII-c-723024—PhH1-naphthylH
|
VIII-c-733025—PhH2-naphthylH
|
VIII-c-743026—PhH4-biphenylylH
|
VIII-c-753027—PhH2-biphenylylH
|
VIII-c-763028—PhHClH
|
VIII-c-773029—PhH—OHH
|
VIII-c-783030—PhH—NO2H
|
VIII-c-793031—PhH—CNH
|
VIII-c-803032—PhH—OPhH
|
VIII-c-813033—PhH—SCH3H
|
VIII-c-823034—PhH—SPhH
|
VIII-c-833035—PhH—NPh2H
|
VIII-c-843036—PhH—COOHH
|
VIII-c-853037—PhH2-pyridylH
|
|
Formula (VIII)
Compound No.L111A13 ═A23A16═A26 A18═A28
|
|
VIII-d-13038—PhHH
|
VIII-d-23039—PhHH
|
VIII-d-33040—PhHH
|
VIII-d-430413042HH
|
A23 = —Ph
|
VIII-d-530433044HH
|
A23 = —Ph
|
VIII-d-63045—PhHCH3
|
VIII-d-73046—PhCH3H
|
VIII-d-83047—PhCH3CH3
|
VIII-d-93048—PhC2H5H
|
VIII-d-103049—Phn-C3H7H
|
VIII-d-113050—Phn-C4H9H
|
VIII-d-123051—Pht-C4H9H
|
VIII-d-133052—Ph—OCH3H
|
VIII-d-143053—PhH—Ph
|
VIII-d-153054—Ph—PhH
|
VIII-d-163055—Ph1-naphthylH
|
VIII-d-173056—Ph2-naphthylH
|
VIII-d-183057—Ph4-biphenylylH
|
VIII-d-193058—Ph3-biphenylylH
|
VIII-d-203059—Ph2-biphenylylH
|
VIII-d-213060—PhClH
|
VIII-d-223061—Ph—OHH
|
VIII-d-233062—Ph—NO2H
|
VIII-d-243063—Ph—CNH
|
VIII-d-253064—Ph—OPhH
|
VIII-d-263065—Ph—SCH3H
|
VIII-d-273066—Ph—SPhH
|
VIII-d-283067—Ph—NH2H
|
VIII-d-293068—Ph—NH—PhH
|
VIII-d-303069—Ph—NPh2H
|
VIII-d-313070—Ph—COOHH
|
VIII-d-323071—Ph2-pyridylH
|
VIII-d-333072—PhHCH3
|
VIII-d-343073—PhCH3H
|
VIII-d-353074—PhCH3CH3
|
VIII-d-363075—PhC2H5H
|
VIII-d-373076—Phn-C3H7H
|
VIII-d-383077—Phn-C4H9H
|
VIII-d-393078—Pht-C4H9H
|
VIII-d-403079—Ph—OCH3H
|
VIII-d-413080—PhH—Ph
|
VIII-d-423081—Ph—PhH
|
VIII-d-433082—Ph1-naphthylH
|
VIII-d-443083—Ph4-biphenylylH
|
VIII-d-453084—Ph3-biphenylylH
|
VIII-d-463085—Ph2-biphenylylH
|
VIII-d-473086—PhClH
|
VIII-d-483087—Ph—OHH
|
VIII-d-493088—PhNO2H
|
VIII-d-503089—Ph—CNH
|
VIII-d-513090—Ph—OPhH
|
VIII-d-523091—Ph—SCH3H
|
VIII-d-533092—Ph—SPhH
|
VIII-d-543093—Ph—NPh2H
|
VIII-d-553094—Ph—COOHH
|
VIII-d-563095—Ph2-pyridylH
|
VIII-d-573096—PhHCH3
|
VIII-d-583097—PhCH3H
|
VIII-d-593098—PhCH3CH3
|
VIII-d-603099—PhHC2H5
|
VIII-d-613100—PhC2H5H
|
VIII-d-623101—Phn-C3H7H
|
VIII-d-633102—Phn-C4H9H
|
VIII-d-643103—Pht-C4H9H
|
VIII-d-653104—PhH—OCH3
|
VIII-d-663105—Ph—OCH3H
|
VIII-d-673106—Ph—OCH3—OCH3
|
VIII-d-683107—PhH—Ph
|
VIII-d-693108—Ph—PhH
|
VIII-d-703109—PhH1-naphthyl
|
VIII-d-713110—Ph1-naphthylH
|
VIII-d-723111—Ph2-naphthylH
|
VIII-d-733112—PhH4-biphenylyl
|
VIII-d-743113—Ph4-biphenylylH
|
VIII-d-753114—Ph3-biphenylylH
|
VIII-d-763115—Ph2-biphenylylH
|
VIII-d-773116—PhClH
|
VIII-d-783117—Ph—OHH
|
VIII-d-793118—Ph—NO2H
|
VIII-d-803119—Ph—CNH
|
VIII-d-813120—Ph—OPhH
|
VIII-d-823121—Ph—SCH3H
|
VIII-d-833122—Ph—SPhH
|
VIII-d-843123—Ph—NPh2H
|
VIII-d-853124—Ph—COOHH
|
VIII-d-863125—Ph2-pyridylH
|
Formula (VIII)
Compound No.L111A13═A23A17═A27A18═A28
|
|
VIII-e-13126—PhHH
|
VIII-e-23127—PhHH
|
VIII-e-33128—PhHH
|
VIII-e-43129—PhHCH3
|
VIII-e-53130—PhCH3H
|
VIII-e-63131—PhCH3CH3
|
VIII-e-73132—PhC2H5H
|
VIII-e-83133—Phn-C3H7H
|
VIII-e-93134—Phn-C3H7n-C3H7
|
VIII-e-103135—Phn-C4H9H
|
VIII-e-113136—Pht-C4H9H
|
VIII-e-123137—Ph—OCH3H
|
|
VIII-e-133138—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-e-143139—PhH—Ph
|
VIII-e-153140—Ph—PhH
|
VIII-e-163141—Ph—Ph—Ph
|
VIII-e-173142—Ph1-naphthylH
|
VIII-e-183143—Ph2-naphthylH
|
VIII-e-193144—Ph4-biphenylylH
|
VIII-e-203145—Ph3-biphenylylH
|
VIII-e-213146—Ph2-biphenylylH
|
VIII-e-223147—PhClH
|
VIII-e-233148—Ph—OHH
|
VIII-e-243149—Ph—NO2H
|
VIII-e-253150—Ph—CNH
|
VIII-e-263151—Ph—OPhH
|
VIII-e-273152—Ph—SCH3H
|
VIII-e-283153—Ph—SPhH
|
VIII-e-293154—Ph—NPh2H
|
VIII-e-303155—Ph—COOHH
|
VIII-e-313156—Ph2-pyridylH
|
VIII-e-323157—PhHCH3
|
VIII-e-333158—PhCH3H
|
VIII-e-343159—PhCH3CH3
|
VIII-e-353160—PhC2H5H
|
VIII-e-363161—Phn-C3H7H
|
VIII-e-373162—Phn-C3H7n-C3H7
|
VIII-e-383163—Phn-C4H9H
|
VIII-e-393164—Pht-C4H9H
|
VIII-e-403165—PhH—OCH3
|
VIII-e-413166—Ph—OCH3H
|
|
VIII-e-423167—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-e-433168—PhH—Ph
|
VIII-e-443169—Ph—PhH
|
VIII-e-453170—Ph—Ph—Ph
|
VIII-e-463171—Ph1-naphthylH
|
VIII-e-473172—Ph2-naphthylH
|
VIII-e-483173—PhH4-biphenylyl
|
VIII-e-493174—Ph4-biphenylyl4-biphenylyl
|
VIII-e-503175—Ph3-biphenylylH
|
VIII-e-513176—Ph2-biphenylylH
|
VIII-e-523177—PhClH
|
VIII-e-533178—Ph—OHH
|
VIII-e-543179—Ph—NO2H
|
VIII-e-553180—Ph—CNH
|
VIII-e-563181—Ph—OPhH
|
VIII-e-573182—Ph—SCH3H
|
VIII-e-583183—Ph—SPhH
|
VIII-e-593184—Ph—NPh2H
|
VIII-e-603185—Ph—COOHH
|
VIII-e-613186—Ph2-pyridylH
|
VIII-e-623187—PhHCH3
|
VIII-e-633188—PhCH3H
|
VIII-e-643189—PhCH3CH3
|
VIII-e-653190—PhC2H5H
|
VIII-e-663191—Phn-C3H7H
|
VIII-e-673192—Phn-C3H7n-C3H7
|
VIII-e-683193—Phn-C4H9H
|
VIII-e-693194—Pht-C4H9H
|
VIII-e-703195—Pht-C4H9t-C4H9
|
VIII-e-713196—Ph—OCH3H
|
|
VIII-e-723197—PhA17 and A18 form a benzene ring. A27 and A28 form a benzene ring.
|
|
VIII-e-733198—PhH—Ph
|
VIII-e-743199—Ph—PhH
|
VIII-e-753200—Ph—Ph—Ph
|
VIII-e-763201—Ph1-naphthylH
|
VIII-e-773202—Ph2-naphthylH
|
VIII-e-783203—Ph3-biphenylylH
|
VIII-e-793204—Ph2-biphenylylH
|
VIII-e-803205—PhClH
|
VIII-e-813206—Ph—OHH
|
VIII-e-823207—Ph—NO2H
|
VIII-e-833208—Ph—CNH
|
VIII-e-843209—Ph—OPhH
|
VIII-e-853210—Ph—SCH3H
|
VIII-e-863211—Ph—SPhH
|
VIII-e-873212—Ph—NPh2H
|
VIII-e-883213—Ph—COOHH
|
VIII-e-893214—Ph2-pyridylH
|
Formula (VIII)
Compound No.L111 A13═A23A15═A25 A18═A28
|
|
VIII-f-13215—PhHH
|
VIII-f-23216—PhHH
|
VIII-f-33217—PhHH
|
VIII-f-43218—PhHCH3
|
VIII-f-53219—PhCH3H
|
VIII-f-63220—PhCH3CH3
|
VIII-f-73221—PhC2H5H
|
VIII-f-83222—Phn-C3H7H
|
VIII-f-93223—Phn-C4H9H
|
VIII-f-103224—Pht-C4H9H
|
VIII-f-113225—Ph—OCH3H
|
VIII-f-123226—PhH—Ph
|
VIII-f-133227—Ph—PhH
|
VIII-f-143228—Ph—Ph—Ph
|
VIII-f-153229—PhH1-naphthyl
|
VIII-f-163230—Ph1-naphthylH
|
VIII-f-173231—Ph2-naphthylH
|
VIII-f-183232—Ph4-biphenylylH
|
VIII-f-193233—Ph3-biphenylylH
|
VIII-f-203234—Ph2-biphenylylH
|
VIII-f-213235—PhClH
|
VIII-f-223236—Ph—OHH
|
VIII-f-233237—Ph—NO2H
|
VIII-f-243238—Ph—CNH
|
VIII-f-253239—Ph—OPhH
|
VIII-f-263240—Ph—SCH3H
|
VIII-f-273241—Ph—SPhH
|
VIII-f-283242—Ph—NPh2H
|
VIII-f-293243—Ph—COOHH
|
VIII-f-303244—Ph2-pyridylH
|
VIII-f-313245—PhHCH3
|
VIII-f-323246—PhCH3H
|
VIII-f-333247—PhCH3CH3
|
VIII-f-343248—PhC2H5H
|
VIII-f-353249—Phn-C3H7H
|
VIII-f-363250—Phn-C4H9H
|
VIII-f-373251—Pht-C4H9H
|
VIII-f-383252—Ph—OCH3H
|
VIII-f-393253—PhH—Ph
|
VIII-f-403254—Ph—PhH
|
VIII-f-413255—Ph—Ph—Ph
|
VIII-f-423256—Ph1-naphthylH
|
VIII-f-433257—Ph2-naphthylH
|
VIII-f-443258—Ph4-biphenylylH
|
VIII-f-453259—Ph3-biphenylylH
|
VIII-f-463260—Ph2-biphenylylH
|
VIII-f-473261—PhClH
|
VIII-f-483262—PhOHH
|
VIII-f-493263—Ph—NO2H
|
VIII-f-503264—Ph—CNH
|
VIII-f-513265—Ph—OPhH
|
VIII-f-523266—Ph—SCH3H
|
VIII-f-533267—Ph—SPhH
|
VIII-f-543268—Ph—NPh2H
|
VIII-f-553269—Ph—COOHH
|
VIII-f-563270—Ph2-pyridylH
|
VIII-f-573271—PhHCH3
|
VIII-f-583272—PhCH3H
|
VIII-f-593273—PhCH3CH3
|
VIII-f-603274—PhC2H5H
|
VIII-f-613275—Phn-C3H7H
|
VIII-f-623276—Phn-C4H9H
|
VIII-f-633277—Pht-C4H9H
|
VIII-f-643278—Ph—OCH3H
|
VIII-f-653279—PhH—Ph
|
VIII-f-663280—Ph—PhH
|
VIII-f-673281—Ph—Ph—Ph
|
VIII-f-683282—Ph1-naphthylH
|
VIII-f-693283—Ph2-naphthylH
|
VIII-f-703284—Ph4-biphenylylH
|
VIII-f-713285—Ph3-biphenylylH
|
VIII-f-723286—Ph2-biphenylylH
|
VIII-f-733287—PhClH
|
VIII-f-743288—Ph—OHH
|
VIII-f-753289—Ph—NO2H
|
VIII-f-763290—Ph—CNH
|
VIII-f-773291—Ph—OPhH
|
VIII-f-783292—Ph—SCH3H
|
VIII-f-793293—Ph—SPhH
|
VIII-f-803294—Ph—NPh2H
|
VIII-f-813295—Ph—COOHH
|
VIII-f-823296—Ph2-pyridylH
|
Formula (VIII)A13═A23A15═A25A16═A26A17═A27A18═A28
Compound No.L112 ═A33═A35═A36═A37 A38
|
|
VIII-g-13297HHHHH
|
|
VIII-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.HH
|
|
VIII-g-43300—PhHHHH
|
|
VIII-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.HH
|
|
VIII-g-73303HHHHH
|
|
VIII-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.HH
|
|
VIII-g-10 3306—PhHHHH
|
|
VIII-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.HH
|
|
VIII-g-133309HHHHH
|
|
VIII-g-14 3310HA15 and A16 form a benzene ring. A25 and A26 form a benzene ring. A35 and A36 form a benzene ring.HH
|
|
VIII-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—PhHHHH
|
|
VIII-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.HH
|
|
VIII-g-193315—PhHH—PhH
|
VIII-g-203316—Ph—PhHHH
|
VIII-g-213317—PhH—PhHH
|
VIII-g-223318—PhHHH—Ph
|
VIII-g-233319—PhHHClH
|
VIII-g-243320—PhHH—OHH
|
VIII-g-253321—PhHH—NO2H
|
VIII-g-263322—PhHH—CNH
|
VIII-g-273323—PhHH—OPhH
|
VIII-g-283324—PhHH—SCH3H
|
VIII-g-293325—PhHH—SPhH
|
VIII-g-303326—PhHH—NPhH
|
VIII-g-313327—PhHHCH3H
|
VIII-g-323328—PhHH—OCH3H
|
VIII-g-333329—PhHH—COOHH
|
VIII-g-343330—PhHH2-pyridylH
|
VIII-g-353331—PhHH—PhH
|
VIII-g-363332—Ph—PhHHH
|
VIII-g-373333—PhH—PhHH
|
VIII-g-383334—PhHHH—Ph
|
VIII-g-393335—PhHHClH
|
VIII-g-403336—PhHH—OHH
|
VIII-g-413337—PhHH—NO2H
|
VIII-g-423338—PhHH—CNH
|
VIII-g-433339—PhHH—OPhH
|
VIII-g-443340—PhHHSCH3H
|
VIII-g-453341—PhHH—SPhH
|
VIII-g-463342—PhHH—NPhH
|
VIII-g-473343—PhHHCH3H
|
VIII-g-483344—PhHH—OCH3H
|
VIII-g-493345—PhHH—COOHH
|
VIII-g-503346—PhHH2-pyridylH
|
VIII-g-513347—PhHH—PhH
|
VIII-g-523348—Ph—PhHHH
|
VIII-g-533349—PhH—PhHH
|
VIII-g-543350—PhHHH—Ph
|
VIII-g-553351—PhHHClH
|
VIII-g-563352—PhHH—OHH
|
VIII-g-573353—PhHH—NO2H
|
VIII-g-583354—PhHH—CNH
|
VIII-g-593355—PhHH—OPhH
|
VIII-g-603356—PhHH—SCH3H
|
VIII-g-613357—PhHH—SPhH
|
VIII-g-623358—PhHH—NPhH
|
VIII-g-633359—PhHHCH3H
|
VIII-g-643360—PhHH—OCH3H
|
VIII-g-653361—PhHH—COOHH
|
VIII-g-663362—PhHH2-pyridylH
|
Formula (VIII)A13═A23A16═A26A17═A27A18═A28
Compound No.L112 ═A33═A36═A37═A38
|
|
VIII-h-13363HHHH
|
VIII-h-23364—PhHHH
|
VIII-h-33365HHHH
|
VIII-h-43366—PhHHH
|
VIII-h-53367HHHH
|
VIII-h-63368—PhHHH
|
|
VIII-h-73369HA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.H
|
VIII-h-83370—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.H
|
|
VIII-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—PhHH
|
VIII-h-123374—PhH—PhH
|
VIII-h-133375—PhHH—Ph
|
VIII-h-143376—PhHClH
|
VIII-h-153377—PhH—OHH
|
VIII-h-163378—PhH—NO2H
|
VIII-h-173379—PhH—CNH
|
VIII-h-183380—PhH—OPhH
|
VIII-h-193381—PhH—SCH3H
|
VIII-h-203382—PhH—SPhH
|
VIII-h-213383—PhH—NPh2H
|
VIII-h-223384—PhHCH3H
|
VIII-h-233385—PhH—OCH3H
|
VIII-h-243386—PhH—COOHH
|
VIII-h-253387—PhH2-pyridylH
|
|
VIII-h-263388HA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.H
|
VIII-h-273389—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.H
|
|
VIII-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—PhHH
|
VIII-h-313393—PhH—PhH
|
VIII-h-323394—PhHH—Ph
|
VIII-h-333395—PhHClH
|
VIII-h-343396—PhH—OHH
|
VIII-h-353397—PhH—NO2H
|
VIII-h-363398—PhH—CNH
|
VIII-h-373399—PhH—OPhH
|
VIII-h-383400—PhH—SCH3H
|
VIII-h-393401—PhH—SPhH
|
VIII-h-403402—PhH—NPh2H
|
VIII-h-413403—PhHCH3H
|
VIII-h-423404—PhH—OCH3H
|
VIII-h-433405—PhH—COOHH
|
VIII-h-443406—PhH2-pyridylH
|
|
VIII-h-453407HA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.H
|
VIII-h-463408—PhA16 and A17 form a benzene ring. A26 and A27 form a benzene ring. A36 and A37 form a benzene ring.H
|
|
VIII-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—PhHH
|
VIII-h-503412—PhH—PhH
|
VIII-h-513413—PhHH—Ph
|
VIII-h-523414—PhHClH
|
VIII-h-533415—PhH—OHH
|
VIII-h-543416—PhH—NO2H
|
VIII-h-553417—PhH—CNH
|
VIII-h-563418—PhH—OPhH
|
VIII-h-573419—PhH—SCH3H
|
VIII-h-583420—PhH—SPhH
|
VIII-h-593421—PhH—NPh2H
|
VIII-h-603422—PhHCH3H
|
VIII-h-613423—PhH—OCH3H
|
VIII-h-623424—PhH—COOHH
|
VIII-h-633425—PhH2-pyridylH
|
VIII-i-13426HHHH
|
VIII-i-23427—PhHHH
|
VIII-i-33428HHHH
|
VIII-i-43429HHHH
|
VIII-i-53430—PhHHH
|
|
VIII-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—PhHH
|
VIII-i-123437—PhH—PhH
|
VIII-i-133438—PhHH—Ph
|
VIII-i-143439—PhHClH
|
VIII-i-153440—PhH—OHH
|
VIII-i-163441—PhH—NO2H
|
VIII-i-173442—PhH—CNH
|
VIII-i-183443—PhH—OPhH
|
VIII-i-193444—PhH—SCH3H
|
VIII-i-203445—PhH—SPhH
|
VIII-i-213446—PhH—N—Ph2H
|
VIII-i-223447—PhHCH3H
|
VIII-i-233448—PhH—OCH3H
|
VIII-i-243449—PhH—COOHH
|
VIII-i-253450—PhH2-pyridylH
|
VIII-i-263451—Ph—PhHH
|
VIII-i-273452—PhH—PhH
|
VIII-i-283453—PhHH—Ph
|
VIII-i-293454—PhHClH
|
VIII-i-303455—PhH—OHH
|
VIII-i-313456—PhH—NO2H
|
VIII-i-323457—PhH—CNH
|
VIII-i-333458—PhH—OPhH
|
VIII-i-343459—PhH—SCH3H
|
VIII-i-353460—PhH—SPhH
|
VIII-i-363461—PhH—N—Ph2H
|
VIII-i-373462—PhHCH3H
|
VIII-i-383463—PhH—OCH3H
|
VIII-i-393464—PhH—COOHH
|
VIII-i-403465—PhH2-pyridylH
|
VIII-i-413466—Ph—PhHH
|
VIII-i-423467—PhH—PhH
|
VIII-i-433468—PhHH—Ph
|
VIII-i-443469—PhHClH
|
VIII-i-453470—PhH—OHH
|
VIII-i-463471—PhH—NO2H
|
VIII-i-473472—PhH—CNH
|
VIII-i-483473—PhH—OPhH
|
VIII-i-493474—PhH—SCH3H
|
VIII-i-503475—PhH—SPhH
|
VIII-i-513476—PhH—N—Ph2H
|
VIII-i-523477—PhHCH3H
|
VIII-i-533478—PhH—OCH3H
|
VIII-i-543479—PhH—COOHH
|
VIII-i-553480—PhH2-pyridylH
|
Formula (VIII)
Compound No.L112A13 ═A23═A33A16 ═A26═A36A18 ═A28═A38
|
|
VIII-j-13481HHH
|
VIII-j-23482—PhHH
|
VIII-j-33483HHH
|
VIII-j-43484HHH
|
VIII-j-53485—PhHH
|
VIII-j-63486—Ph—PhH
|
VIII-j-73487—PhH—Ph
|
VIII-j-83488—PhClH
|
VIII-j-93489—Ph—OHH
|
VIII-j-103490—Ph—NO2H
|
VIII-j-113491—Ph—CNH
|
VIII-j-123492—Ph—OPhH
|
VIII-j-133493—Ph—SCH3H
|
VIII-j-143494—Ph—SPhH
|
VIII-j-153495—Ph—N—Ph2H
|
VIII-j-163496—PhCH3H
|
VIII-j-173497—Ph—OCH3H
|
VIII-j-183498—Ph—COOHH
|
VIII-j-193499—Ph2-pyridylH
|
VIII-j-203500—Ph—PhH
|
VIII-j-213501—PhH—Ph
|
VIII-j-223502—PhClH
|
VIII-j-233503—Ph—OHH
|
VIII-j-243504—Ph—NO2H
|
VIII-j-253505—Ph—CNH
|
VIII-j-263506—Ph—OPhH
|
VIII-j-273507—Ph—SCH3H
|
VIII-j-283508—Ph—SPhH
|
VIII-j-293509—Ph—N—Ph2H
|
VIII-j-303510—PhCH3H
|
VIII-j-313511—Ph—OCH3H
|
VIII-j-323512—Ph—COOHH
|
VIII-j-333513—Ph2-pyridylH
|
VIII-j-343514—Ph—PhH
|
VIII-j-353515—PhH—Ph
|
VIII-j-363516—PhClH
|
VIII-j-373517—Ph—OHH
|
VIII-j-383518—Ph—NO2H
|
VIII-j-393519—Ph—CNH
|
VIII-j-403520—Ph—OPhH
|
VIII-j-413521—Ph—SCH3H
|
VIII-j-423522—Ph—SPhH
|
VIII-j-433523—Ph—N—Ph2H
|
VIII-j-443524—PhCH3H
|
VIII-j-453525—Ph—OCH3H
|
VIII-j-463526—Ph—COOHH
|
VIII-j-473527—Ph2-pyridylH
|
Formula (VIII)
Compound No.L112A13 ═A23═A33A17 ═A27═A37A18 ═A28═A38
|
|
VIII-k-13528HHH
|
VIII-k-23529—PhHH
|
VIII-k-33530HHh
|
VIII-k-43531—PhHH
|
VIII-k-53532HHH
|
VIII-k-63533—PhHH
|
|
VIII-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—PhH
|
VIII-k-143541—PhH—Ph
|
VIII-k-153542—PhClH
|
VIII-k-163543—Ph—OHH
|
VIII-k-173544—Ph—NO2H
|
VIII-k-183545—Ph—CNH
|
VIII-k-193546—Ph—OPhH
|
VIII-k-203547—Ph—SCH3H
|
VIII-k-213548—Ph—SPhH
|
VIII-k-223549—Ph—N—Ph2H
|
VIII-k-233550—PhCH3H
|
VIII-k-243551—Ph—OCH3H
|
VIII-k-253552—Ph—COOHH
|
VIII-k-263553—Ph2-pyridylH
|
VIII-k-273554—Ph—PhH
|
VIII-k-283555—PhH—Ph
|
VIII-k-293556—PhClH
|
VIII-k-303557—Ph—OHH
|
VIII-k-313558—Ph—NO2H
|
VIII-k-323559—Ph—CNH
|
VIII-k-333560—Ph—OPhH
|
VIII-k-343561—Ph—SCH3H
|
VIII-k-353562—Ph—SPhH
|
VIII-k-363563—Ph—N—Ph2H
|
VIII-k-373564—PhCH3H
|
VIII-k-383565—Ph—OCH3H
|
VIII-k-393566—Ph—COOHH
|
VIII-k-403567—Ph2-pyridylH
|
VIII-k-413568—Ph—PhH
|
VIII-k-423569—PhH—Ph
|
VIII-k-433570—PhClH
|
VIII-k-443571—Ph—OHH
|
VIII-k-453572—Ph—NO2H
|
VIII-k-463573—Ph—CNH
|
VIII-k-473574—Ph—OPhH
|
VIII-k-483575—Ph—SCH3H
|
VIII-k-493576—Ph—SPhH
|
VIII-k-503577—Ph—N—Ph2H
|
VIII-k-513578—PhCH3H
|
VIII-k-523579—Ph—OCH3H
|
VIII-k-533580—Ph—COOHH
|
VIII-k-543581—Ph2-pyridylH
|
Formula (VIII)
Compound No.L112A13 ═A23═A33A15 ═A25═A35A18 ═A28═A38
|
|
VIII-l-13582HHH
|
VIII-l-23583—PhHH
|
VIII-l-33584HHH
|
VIII-l-43585—PhHH
|
VIII-l-53586HHH
|
VIII-l-63587—Ph—PhH
|
VIII-l-73588—PhH—Ph
|
VIII-l-83589—PhClH
|
VIII-l-93590—Ph—OHH
|
VIII-l-103591—Ph—NO2H
|
VIII-l-113592—Ph—CNH
|
VIII-l-123593—Ph—OPhH
|
VIIl-l-133594—Ph—SCH3H
|
VIII-l-143595—Ph—SPhH
|
VIII-l-153596—Ph—N—Ph2H
|
VIII-l-163597—PhCH3H
|
VIII-l-173598—Ph—OCH3H
|
VIII-l-183599—Ph—COOHH
|
VIII-l-193600—Ph2-pyridylH
|
VIII-l-203601—Ph—PhH
|
VIII-l-213602—PhH—Ph
|
VIII-l-223603—PhClH
|
VIII-l-233604—Ph—OHH
|
VIII-l-243605—Ph—NO2H
|
VIII-l-253606—Ph—CNH
|
VIII-l-263607—Ph—OPhH
|
VIII-l-273608—Ph—SCH3H
|
VIII-l-283609—Ph—SPhH
|
VIII-l-293610—Ph—N—Ph2H
|
VIII-l-303611—PhCH3H
|
VIII-l-313612—Ph—OCH3H
|
VIII-l-323613—Ph—COOHH
|
VIII-l-333614—Ph2-pyridylH
|
VIII-l-343615—Ph—PhH
|
VIII-l-353616—PhH—Ph
|
VIII-l-363617—PhClH
|
VIII-l-373618—Ph—OHH
|
VIII-l-383619—Ph—NO2H
|
VIII-l-393620—Ph—CNH
|
VIII-l-403621—Ph—OPhH
|
VIII-l-413622—Ph—SCH3H
|
VIII-l-423623—Ph—SPhH
|
VIII-l-433624—Ph—N—Ph2H
|
VIII-l-443625—PhCH3H
|
VIII-l-453626—Ph—OCH3H
|
VIII-l-463627—Ph—COOHH
|
VIII-l-473628—Ph2-pyridylH
|
Formula (VIII)
Compound No.L111A12═A22A13═A23A15═A25A17═A27A18═A28
|
|
VIII-m-1single bondHHHHH
VIII-m-2single bondHHCH3HH
VIII-m-3single bondHHHCH3H
VIII-m-4single bondHHHHCH3
VIII-m-5single bondHHHn-C2H5H
VIII-m-6single bondHHHn-C3H7H
VIII-m-7single bondHHHn-C4H9H
VIII-m-8single bondHHHt-C4H9H
VIII-m-9single bondHHPhHH
VIII-m-10single bondHHHPhH
VIII-m-11single bondHHHHPh
VIII-m-12single bondHHH1-naphthylH
VIII-m-13single bondHHH2-naphthylH
VIII-m-14single bondHHH4-biphenylylH
VIII-m-15single bondHHH3-biphenylylH
VIII-m-16single bondHHH2-biphenylylH
VIII-m-17single bondHHH2-biphenylylH
VIII-m-18single bondPhPhHHH
VIII-m-19single bondPhPhCH3HH
VIII-m-20single bondPhPhHCH3H
VIII-m-21single bondPhPhHHCH3
VIII-m-22single bondPhPhHn- C2H5H
VIII-m-23single bondPhPhHn-C3H7H
VIII-m-24single bondPhPhHn-C4H9H
VIII-m-25single bondPhPhHt-C4H9H
VIII-m-26single bondPhPhPhHH
VIII-m-27single bondPhPhHPhH
VIII-m-28single bondPhPhHHPh
VIII-m-29single bondPhPhH1-naphthylH
VIII-m-30single bondPhPhH2-naphthylH
VIII-m-31single bondPhPhH4-biphenylylH
VIII-m-32single bondPhPhH3-biphenylylH
VIII-m-33single bondPhPhH2-biphenylylH
|
VIII-m-34single bond36293630HHH
|
VIII-m-35single bond36313632CH3HH
|
VIII-m-36single bond36333634HCH3H
|
VIII-m-37single bond36353636HHCH3
|
VIII-m-38single bond36373638Hn-C2H5H
|
VIII-m-39single bond36393640Hn-C3H7H
|
VIII-m-40single bond36413642Hn-C4H9H
|
VIII-m-41single bond36433644Ht-C4H9H
|
VIII-m-42single bond36453646—PhHH
|
VIII-m-43single bond36473648H—PhH
|
VIII-m-44single bond36493650HHPh
|
VIII-m-45single bond36513652H1-naphthylH
|
VIII-m-46single bond36533654H2-naphthylH
|
VIII-m-47single bond36553656H4-biphenylylH
|
VIII-m-48single bond36573658H3-biphenylylH
|
VIII-m-49single bond36593660H2-biphenylylH
|
VIII-m-503661HHHHH
|
VIII-m-513662HHCH3HH
|
VIII-m-523663HHHCH3H
|
VIII-m-533664HHHHCH3
|
VIII-m-543665HHHn-C2H5H
|
VIII-m-553666HHHn-C3H7H
|
VIII-m-563667HHHn-C4H9H
|
VIII-m-573668HHHt-C4H9H
|
VIII-m-583669HHPhHH
|
VIII-m-593670HHHPhH
|
VIII-m-603671HHHHPh
|
VIII-m-613672HHH1-naphthylH
|
VIII-m-623673HHH2-naphthylH
|
VIII-m-633674HHH4-biphenylylH
|
VIII-m-643675HHH3-biphenylylH
|
VIII-m-653676HHH2-biphenylylH
|
VIII-m-663677HHH2-biphenylylH
|
VIII-m-673678PhPhHHH
|
VIII-m-683679PhPhCH3HH
|
VIII-m-693680PhPhHCH3H
|
VIII-m-703681PhPhHHCH3
|
VIII-m-713682PhPhHn-C2H5H
|
VIII-m-723683PhPhHn-C3H7H
|
VIII-m-733684PhPhHn-C4H9H
|
VIII-m-743685PhPhHt-C4H9H
|
VIII-m-753686PhPhPhHH
|
VIII-m-763687PhPhHPhH
|
VIII-m-773688PhPhHHPh
|
VIII-m-783689PhPhH1-naphthylH
|
VIII-m-793690PhPhH2-naphthylH
|
VIII-m-803691PhPhH4-biphenylylH
|
VIII-m-813692PhPhH3-biphenylylH
|
VIII-m-823693PhPhH2-biphenylylH
|
VIII-m-83369436953696HHH
|
VIII-m-84369736983699CH3HH
|
VIII-m-85370037013702HCH3H
|
VIII-m-86370337043705HHCH3
|
VIII-m-87370637073708Hn-C2H5H
|
VIII-m-88370937103711Hn-C3H7H
|
VIII-m-89371237133714Hn-C4H9H
|
VIII-m-90371537163717Ht-C4H9H
|
VIII-m-91371837193720PhHH
|
VIII-m-92372137223723HPhH
|
VIII-m-93372437253726HHPh
|
VIII-m-94372737283729H1-naphthylH
|
VIII-m-95373037313732H2-naphthylH
|
VIII-m-96373337343735H4-biphenylylH
|
VIII-m-97373637373738H3-biphenylylH
|
VIII-m-98373937403741H2-biphenylylH
|
VIII-m-993742HHHHH
|
VIII-m-1003743HHCH3HH
|
VIII-m-1013744HHHCH3H
|
VIII-m-1023745HHHHCH3
|
VIII-m-1033746HHHn-C2H5H
|
VIII-m-1043747HHHn-C3H7H
|
VIII-m-1053748HHHn-C4H9H
|
VIII-m-1063749HHHt-C4H9H
|
VIII-m-1073750HHPhHH
|
VIII-m-1083751HHHPhH
|
VIII-m-1093752HHHHPh
|
VIII-m-1103753HHH1-naphthylH
|
VIII-m-1113754HHH2-naplithylH
|
VIII-m-1123755HHH4-biphenylylH
|
VIII-m-1133756HHH3-biphenylylH
|
VIII-m-1143757HHH2-biphenylylH
|
VIII-m-1153758HHH2-biphenylylH
|
VIII-m-1163759PhPhHHH
|
VIII-m-1173760PhPhCH3HH
|
VIII-m-1183761PhPhHCH3H
|
VIII-m-1193762PhPhHHCH3
|
VIII-m-1203763PhPhHn-C2H5H
|
VIII-m-1213764PhPhHn-C3H7H
|
VIII-m-1223765PhPhHn-C4H9H
|
VIII-m-1233766PhPhHt-C4H9H
|
VIII-m-1243767PhPhPhHH
|
VIII-m-1253768PhPhHPhH
|
VIII-m-1263769PhPhHHPh
|
VIII-m-1273770PhPhH1-naphthylH
|
VIII-m-1283771PhPhH2-naphthylH
|
VIII-m-1293772PhPhH4-biphenylylH
|
VIII-m-1303773PhPhH3-biphenylylH
|
VIII-m-1313774PhPhH2-biphenylylH
|
VIII-m-132377537763777HHH
|
VIII-m-133377837793780CH3HH
|
VIII-m-134378137823783HCH3H
|
VIII-m-135378437853786HHCH3
|
VIII-m-136378737883789Hn-C2H5H
|
VIII-m-137379037913792Hn-C3H7H
|
VIII-m-138379337943795Hn-C4H9H
|
VIII-m-139379637973798Ht-C4H9H
|
VIII-m-140379938003801PhHH
|
VIII-m-141380238033804HPhH
|
VIII-m-142380538063807HHPh
|
VIII-m-143380838093810H1-naphthylH
|
VIII-m-144381138123813H2-naphthylH
|
VIII-m-145381438153816H4-biphenylylH
|
VIII-m-146381738183819H3-biphenylylH
|
VIII-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” in3826means3827
|
Com-
pound
No.X1X2X3X6X7X8
|
A-1HHHHHH
A-2HHHHHH
A-3HHHHHH
A-4HHHHHH
A-5HHHHHH
A-6HHHHHH
A-7HHHHHH
A-8HHHHHH
A-9HHHHHH
A-10HHHHHH
A-11PhHHHHPh
|
A-123828HHHH3829
|
A-13CH3HHHHCH3
A-14HPhHHPhH
|
A-15H3830HH3831H
|
A-16HCH3HHCH3H
A-17X1 and X2 form a fused ring.HHHH
A-18X1 and X2 form a fused ring.HHHH
A-19X1 and X2 form a fused ring.HHHH
A-20X1 and X2 form a fused ring.HHHH
A-21X1 and X2 form a fused ring.HHHH
A-22X1 and X2 form a fused ring.HHHH
A-23X1 and X2 form a fused ring.HHHH
A-24X1 and X2 form a fused ring.HHHH
A-25X1 and X2 form a fused ring.HHHH
A-26X1 and X2 form a fused ring.HHHH
A-27X1 and X2 form a fused ring.HHHPh
|
A-28X1 and X2 form a fused ring.HHH3832
|
A-29X1 and X2 form a fused ring.HHHCH3
A-30X1 and X2 form a fused ring.HHPhH
|
A-31X1 and X2 form a fused ring.HH3833H
|
A-32X1 and X2 form a fused ring.HHCH3H
A-33HHHHHH
A-34HHHHHH
A-35HHHHHH
A-36HHHHHH
A-37HHHHHH
A-38HHHHHH
A-39HHHHHH
A-40HHHHHH
A-41HHHHHH
A-42HHHHHH
A-43PhHHHHPh
|
A-443834HHHH3835
|
A-45CH3HHHHCH3
A-46HPhHHPhH
|
A-47H3836HH3837H
|
A-48CH3HHCH3H
A-49HHHHHH
A-50PhHHHHPh
|
A-513838HHHH3839
|
A-52CH3HHHHCH3
A-53HPhHHPhH
|
A-54H3840HH3841H
|
A-55HCH3HHCH3H
A-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-
pound
No.X11X12X13X14
|
A-1HHHH
A-2PhHHPh
|
A-33842HH3843
|
A-43844HH3845
|
A-53846HH3847
|
A-6CH3HHCH3
|
A-73848HH3849
|
A-8PhPhPhPh
|
A-9Ph38503851Ph
|
A-10PhCH3CH3Ph
A-11PhHHPh
A-12PhHHPh
A-13PhHHPh
A-14PhHHPh
A-15PhHHPh
A-16PhHHPh
A-17HHHH
A-18PhHHPh
|
A-193852HH3853
|
A-203854HH3855
|
A-213856HH3857
|
A-22CH3HHCH3
|
A-233858HH3859
|
A-24PhPhPhPh
|
A-25Ph38603861Ph
|
A-26PhCH3CH3Ph
A-27PhHHPh
A-28PhHHPh
A-29PhHHPh
A-30PhHHPh
A-31PhHHPh
A-32PhHHPh
A-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-56HHHH
A-57PhHHPh
|
A-583867HH3868
|
A-593869HH3870
|
A-603871HH3872
|
A-61CH3HHCH3
|
A-623873HH3874
|
A-63PhPhPhPh
|
A-64Ph38753876Ph
|
A-65PhCH3CH3Ph
A-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 |
|