Organic electroluminescent element

Abstract
An organic electroluminescent element having at least one pair of electrodes including an anode and a cathode, at least one of which having light transmissive, and at least one organic compound layer disposed between the electrodes, wherein the at least one organic compound layer contains at least one kind of non-conjugated polymer having terminal groups, and at least one of terminal groups of the non-conjugated polymer contains a fluorescent substance emitting fluorescence in a solid state.
Description


BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention


[0002] The present invention relates to an element which emits light by converting electric energy into light, and more particularly to an organic electroluminescent element which can be suitably used in the fields of display elements, back lights of liquid crystals, illumination light sources, exposing apparatus for electrophotography, labels, sign boards and the like.


[0003] 2. Description of the Related Art


[0004] Since an electroluminescent element is a spontaneously emitting wholly solid element, has high visibility, and withstands impacts, wide application thereof is expected. Currently, an electroluminescent element using an inorganic fluorescent substance is popular and is used widely. Since such an electroluminescent element requires alternating current voltage in a range of 200 V or greater and 50 to 1000 Hz for driving, it has a problem in that a running cost thereof is high and luminance is insufficient. On the other hand, study of an electroluminescent element using an organic compound first started using a single crystal of anthracene or the like, but a film thickness of the element is as great as 1 mm, and the element requires a driving voltage of 100 V or greater. For that reason, as reported in Thin Solid Films, 94, 171(1982), thinning by a deposition method has been tried.


[0005] Light emission by these electroluminescent elements is a phenomenon in which electrons are injected from one electrode and holes are injected from another electrode, whereby, a light emitting material in an electroluminescent element is excited to a high energy level, and an excited light emitting substance releases, as light, extra energy produced when returned to a ground state. However, in these electroluminescent elements, a driving voltage is still as high as 30 V, densities of electron carriers and hole carriers present in a film are low, and a probability of production of photons by recombination of carriers is low. Therefore, sufficient luminance cannot be obtained, and these electroluminescent elements have not been put to practical use.


[0006] However, in 1997, Tang et al. reported in Appl. Phys. Lett., 51, 913(1987) and Japanese Patent Application Laid-Open (JP-A) No. 59-194393 that a high luminance of 1000 cd/m2 or larger can be obtained under a low driving voltage of around 10 V by an organic electroluminescent element. This organic electroluminescent element is a function separated-type organic electroluminescent element in which a hole transporting organic low-molecular compound, and a fluorescent organic low-molecular compound having electron transporting ability are successively deposited in order, as an extremely thin film, on a transparent substrate by a vacuum deposition method. Since this study by Tang et al., organic luminescence elements have been actively studied and developed.


[0007] These multilayer electroluminescent elements have a structure in which an organic light emitting substance and a charge transporting organic compound (charge transporting material) are deposited on an electrode, and the light emission by these elements is caused by recombination of holes and electrons, which are generated in both materials and move in the charge transporting material.


[0008] In this case, as the organic light emitting substance, organic dyes emitting fluorescene such as a 8-quinlinol aluminium complex and a coumarin compound are used. In addition, examples of the charge transporting material include diamino compounds such as N,N-di(m-tolyl) N,N′-diphenylbenzidine and 1,1-bis[N,N-di(p-tolyl)aminophenyl]cyclohexane, a 4-(N,N-diphenyl)aminobenzaldehyde-N,N-diphenylhydrazone compound and the like.


[0009] Organic electroluminescent elements using these organic compounds have high light emitting properties, but they have problems with respect to heat stability upon light emission and the storage stability. A thickness of a layer formed of an organic compound in an electroluminescent element is very thin, being as thin as several tens to several hundred of nanometers. Therefore, a voltage applied per unit thickness of a layer composed of this organic compound becomes very high, and the element is driven at a high current density of a few mA/cm2. Therefore, a large amount of Joule heat is generated from this layer. For this reason, a hole transporting low-molecular compound and a fluorescent organic low-molecular compound which are formed into an amorphous film are gradually crystallized as a temperature thereof is elevated and, finally, those compounds are melted, thereby causing a reduction in luminance and dielectric breakdown in many cases. Therefore, there is a problem in that a lifetime of the organic electroluminescent element is reduced. It is considered that the low heat stability of this organic electroluminescent element is derived from a low glass transition temperature of a material used in an organic electroluminescent element. That is, low-molecular compounds used as such a material have a low melting point and have high symmetry.


[0010] Thus, in order to solve the problem regarding heat stability, an organic electroluminescent element using N,N-di(1-naphthyl)N,N′-diphenylbenzidine with an α-naphthyl group introduced therein, as a material which has an improved glass transition temperature and can obtain a stable amorphous state, has been reported in Technical Study Report of the Electronic Information Communication Society, OME95-54(1995) and, for the same purpose, an organic electroluminescent element using a star burst amine has been reported in Proceedings of the 40th Applied Physics Related Associated Seminar 30a-SZK-14(1993). However, when these materials are used alone, since there is an energy barrier derived from ionization potential of a hole transporting material, hole injectability from an anode or hole injectability into a light emitting layer can not be satisfied. Further, in a 2-layered type element in which a hole transporting layer and a light emitting layer are deposited, a mutual diffusion phenomenon is caused. In addition, it is required that a material used in an organic electroluminescent element has heat stability with respect to heat treatment during a step of preparing an organic electroluminescent element, such as deposition, baking, annealing, wiring, sealing and the like, and with respect to change over time due to long term use of the organic electroluminescent element. For this reason, it is desired that a glass transition temperature of a material used in an organic electroluminescent element is even higher.


[0011] On the other hand, an electroluminescent element using a high-molecular material in place of a low-molecular compound has also been studied and developed. For example, in Nature, 357,577(1992) and JP-A No. 10-92576, there has been proposed an element using an electrically conductive polymer such as poly(p-phenylenevinylene) or the like. In addition, in Proceedings of the 42nd Polymer Discussion Meeting 20J21(1993), there has been proposed an element using a polymer in which triphenylamine is introduced on a side chain of polyphosphazene. Further, in Proceedings of the 38th Applied Physics Related Associated Seminar 31p-GI-2(1991), there has been proposed an element using a material in which an electron transporting material and a fluorescent dye are mixed into hole transporting polyvinylcarbazole.


[0012] These high-molecular materials have a comparatively higher glass transition points than that of a low-molecular compound. However, since poly(p-phenylenevinylene) is subjected to heat treatment after spin coating with a soluble precursor, defects are easily generated in a conjugated polymer on a main chain and light emitting properties are remarkably reduced. In addition, phosphazene has a high ionization potential, and thus, charge injecting properties are reduced. Further, polyvinylcarbazole has a high glass transition point, but has a problem due to traps. In addition, when a low-molecular compound is mixed into polyvinylcarbazole, the low-molecular compound acts as a plasticizer. For this reason, an organic electroluminescent element using these high-molecular materials has not yet caught up with the multilayer-type electroluminescent element using an organic low-molecular compound, in luminance, light emitting efficiency and the like.


[0013] In addition, a method of preparing an organic electroluminescent element is desirably a coating method in view of simplification of preparation, processibility, enlargement, cost and the like and, additionally, Proceedings of the 50th Applied Physics Society Seminar, 29p-ZP-5(1989) and Proceeding of the 51th Applied Physics Society Seminar, 28a-PB-7(1990) report that an organic electroluminescent element can also be prepared by a casting method. However, since a charge transporting material has deteriorated solubility in or compatibility with a solvent or a resin, the charge transporting material is easily crystallized and, thus, the above preparation methods lead to defects in preparation and properties of an organic electroluminescent element.



SUMMARY OF THE INVENTION

[0014] An object of the present invention is to solve the various problems of the prior art as described above.


[0015] That is, an object of the invention is to provide an organic electroluminescent element which has high light emitting intensity, has high light emitting efficiency, has a long element life and is easily prepared, using a non-conjugated polymer having a light emitting function which is excellent in the heat stability during light emission, storage stability, and solubility in and compatibility with a solvent and a resin.


[0016] In order to attain the above object, the present inventors intensively studied a non-conjugated polymer having light emitting properties. As a result, the present inventors have found that a non-conjugated polymer having a fluorescent substance emitting fluorescence in a solid state on at least one terminal group has charge injecting properties, charge mobility, thin film forming ability and light emitting properties which are suitable for the organic electroluminescent element, which resulted in completion of the invention.


[0017] That is, a first aspect of the invention provides an electroluminescent element comprising at least one pair of electrodes comprising an anode and a cathode, at least one of which having light transmissive, and at least one organic compound layer disposed between the electrodes, wherein the at least one organic compound layer contains at least one kind of non-conjugated polymer having terminal groups, and at least one terminal group of the non-conjugated polymer contains a fluorescent substance emitting fluorescence in a solid state.


[0018] A second aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein the non-conjugated polymer may be selected from the group consisting of polyester, polyether and polyurethane.


[0019] A third aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein the non-conjugated polymer may be hole transporting polymer.


[0020] A fourth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein the non-conjugated polymer may comprises a repetition unit containing at least one partial structure selected from the group consisting of the following general formulas (I-1) and (I-2),
1


[0021] wherein, in the general formulas (I-1) and (I-2), Ar represents a group selected from the group consisting of a substituted or unsubstituted monovalent benzene ring, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having an aromatic ring number of 2 to 10, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having an aromatic ring number of 2 to 10, and a substituted or unsubstituted monovalent aromatic heterocyclic ring; X represents a group selected from the group consisting of a substituted or unsubstituted divalent benzene ring, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having an aromatic ring number of 2 to 10, a substituted or unsubstituted divalent condensed aromatic hydrocarbon having an aromatic ring number of 2 to 10, and a substituted or unsubstituted divalent aromatic heterocyclic ring; T represents a group selected from the group consisting of a divalent straight hydrocarbon group having a carbon number of 1 to 6 and a divalent branched hydrocarbon group having a carbon number of 2 to 10; and k, i and j each independently represent an integer selected from 0 to 1.


[0022] A fifth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein the at least one organic compound layer may comprise 2 or more layers including at least a light emitting layer, and the light emitting layer may contain at least one kind of the non-conjugated polymer.


[0023] A sixth aspect of the invention provides an organic electroluminescent element according to the fifth aspect, wherein the at least one organic compound layer may have a construction selected from the group consisting of a construction comprising the light emitting layer and an electron transporting layer, a construction comprising the light emitting layer and an electron injecting layer, and a construction comprising the light emitting layer, an electron transporting layer and an electron injecting layer.


[0024] A seventh aspect of the invention provides an organic electroluminescent element according to the fifth aspect, wherein the at least one organic compound layer may have a construction selected from the group consisting of a construction comprising the light emitting layer and a hole transporting layer, a construction comprising the light emitting layer and a hole injecting layer, and a construction comprising the light emitting layer, a hole transporting layer and a hole injecting layer.


[0025] An eighth aspect of the invention provides an organic electroluminescent element according to the fifth aspect, wherein the at least one organic compound layer may have a construction selected from the group consisting of a construction comprising the light emitting layer, a hole transporting layer and an electron transporting layer, a construction comprising the light emitting layer, a hole transporting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole transporting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole injecting layer and an electron transporting layer, a construction comprising the light emitting layer, a hole injecting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole injecting layer, an electron transporting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole transporting layer, a hole injecting layer and an electron transporting layer, a construction comprising the light emitting layer, a hole transporting layer, a hole injecting layer and an electron injecting layer, and a construction comprising the light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer and an electron injecting layer.


[0026] A ninth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein the at least one organic compound layer may be composed only of a light emitting layer having a charge transporting function, and the light emitting layer having the charge transporting function may contain one or more kinds of non-conjugated polymers.


[0027] A tenth aspect of the invention provides an organic selectroluminescent element according to the fourth aspect, wherein the non-conjugated polymer may be a polyester selected from the group consisting of the following general formulas (II-1) and (II-2),
2


[0028] wherein, in the general formulas (II-1) and (II-2), Al represents at least one structure selected from the group consisting of general formulas (I-1) and (I-2), Y1 represents a divalent alcohol residue, Z1 represents a divalent carboxylic acid residue, m represents an integer from 1 to 5, and p represents an integer selected from the range of 5 to 5,000.


[0029] An eleventh aspect of the invention provides an organic electroluminescent element according to the fourth aspect, wherein the non-conjugated polymer may be a polyether represented by the following general formula (III-1),
3


[0030] wherein, in the general formula (III-1), A1 represents at least one structure selected from the group consisting of general formulas (I-1) and (I-2), and p represents an integer from 5 to 5,000.


[0031] A twelfth aspect of the invention provides an organic electroluminescent element according to the fourth aspect, wherein the non-conjugated polymer may be a polyurethane selected from the group consisting of the general formulas (IV-1) and (IV-2),
4


[0032] wherein, in the general formulas (IV-1) and (IV-2), A1 represents at least one structure selected from the group consisting of general formulas (I-1) and (I-2), T represents a group selected from the group consisting of a divalent straight hydrocarbon group having a carbon number of 1 to 6, and a divalent branched hydrocarbon group having a carbon number of 2 to 10; Y2 and Z2 each independently represents a group selected from the group consisting of divalent diisocyanate, alcohol and amine residue; m represents an integer from 1 to 5; and p represents an integer from 5 to 5,000.


[0033] A thirteenth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein the fluorescent substance may be an organic fluorescent substance.


[0034] A fourteenth aspect of the invention provides an organic electroluminescent element according to the thirteenth aspect, wherein the organic fluorescent substance may be selected from the group consisting of a compound including an aromatic hydrocarbon having an aromatic ring number of 2 or more, and a chelating metal complex.


[0035] A fifteenth aspect of the invention provides an organic electroluminescent element according to the fourteenth aspect, wherein the compound including an aromatic hydrocarbon having an aromatic ring number of 2 or more may be an organic fluorescent substance selected from the group consisting of a polyacene derivative compound, a styrylamine compound, a quinacridone derivative compound, a rubulen derivative compound, a coumarin derivative compound, and a pyran derivative compound.


[0036] A sixteenth aspect of the invention provides an organic electroluminescent element according to the fifteenth aspect, wherein the polyacene derivative compound may be selected from the group consisting of a naphthalene derivative, an anthracene derivative, a tetracene derivative, a perylene derivative, and a pyrne derivative.


[0037] A seventeenth aspect of the invention provides an organic electroluminescent element according to the fourteenth aspect, wherein the chelating metal complex may contain a metal selected from the group consisting of Al, Zn, Be, Mg, Eu, Ga, Pt and Ir.


[0038] An eighteenth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein a maximum peak wavelength of a fluorescent spectrum of the fluorescent substance may be in the a visible light region.


[0039] A nineteenth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein both terminal groups of the non-conjugated polymer may contain a fluorescent substance emitting fluorescence in a solid state.


[0040] A twentieth aspect of the invention provides an organic electroluminescent element according to the first aspect, wherein emission colors of fluorescent substances emitting fluorescence in a solid state and respectively contained in the terminal groups may be different from each other.







BRIEF DESCRIPTION OF THE DRAWINGS

[0041]
FIG. 1 is a schematic view showing one example of a layer construction of the organic electroluminescent element of the present invention.


[0042]
FIG. 2 is a schematic view showing another example of a layer construction of the organic electroluminescent element of the invention.


[0043]
FIG. 3 is a schematic view showing another example of a layer construction of the organic electroluminescent element of the invention.


[0044]
FIG. 4 is a schematic view showing another example of a layer construction of the organic electroluminescent element of the invention.







DETAILED DESCRIPTION OF THE INVENTION

[0045] The organic electroluminescent element of the present invention is an electroluminescent element, which comprises at least one pair of electrodes comprising an anode and a cathode, at least one of which having light transmissive, and at least one organic compound layer disposed between the electrodes, wherein the at least one organic compound layer contains at least one kind of non-conjugated polymer having terminal groups, and at least one of terminal groups of the non-conjugated polymer contains a fluorescent substance emitting fluorescence in a solid state.


[0046] In the invention, the “non-conjugated polymer” is a polymer having a repetition structure containing at least one σ bond on a main chain of the polymer, and is not particularly limited as long as at least one of terminal ends of the main chain has a fluorescent substance emitting fluorescence in a solid state (hereinafter, referred to as “fluorescent substance”).


[0047] In a non-conjugated molecule such as a molecule in which a plurality of light emitting compounds such as a fluorescent substance and the like continuously link together, an emitting intensity of the light emitting compound contained in the molecule is remarkably reduced as compared with a light emitting compound unlinked with any compound in some cases. In view of this point, it is preferable that the emitting compound is dispersed in a molecule. Since the non-conjugated polymer used in the invention has at least one non-connected fluorescent substance at terminal ends of a chain of the molecule, the aforementioned reduction in light emitting efficiency can be prevented and, as a result, sufficient light emitting intensity can be obtained.


[0048] Alternatively, a fluorescent substance may be added to any position other than terminal ends of a molecular chain of a polymer. However, when a non-conjugated polymer dose not have a fluorescent substance at terminal ends of the molecular chain, functional groups at terminal ends of the molecular chain may has an adverse effect on light emission of a fluorescent substance added to a part other than the terminal ends in some cases. In addition, when a charge moves on a molecular chain, functional groups at the terminal ends may suppress mobility of the charge in some cases.


[0049] However, since the non-conjugated polymer used in the invention has a fluorescent substance in place of at least one of functional groups at terminal ends of a molecular chain, it can sufficiently exert the light emitting properties of a non-connected fluorescent substance. In addition, when a charge moves on a molecular chain, mobility of the charge may be improved. Further, replacement of a functional group at a terminal end with a fluorescent substance is easy in synthesis of a non-conjugated polymer.


[0050] Further, the non-conjugated polymer used in the invention may have a fluorescent substance on both terminal ends. In this case, an emission color of the non-conjugated polymer can be easily adjusted to a desired color by choosing from combinations of fluorescent substances having different emission colors from each other. Such a non-conjugated polymer can be easily synthesized by copolymerization reaction.


[0051] Since the aforementioned non-conjugated polymer can be synthesized by selecting a structure of a part other than a fluorescent substance and adjusting a molecular weight, it is easy to obtain desired properties (e.g. heat stability, solubility in and compatibility with solvent and resin). For this reason, a non-conjugated polymer having excellent heat stability and film forming ability can be easily obtained.


[0052] As explained above, the non-conjugated polymer used in the invention has a high light emitting intensity, has high light emitting efficiency, has excellent charge moving properties, and is excellent in heat stability, and a film of the polymer can be easily made. Therefore, since in the organic electroluminescent element of the invention, the at least one organic compound layer contains the aforementioned non-conjugated polymer, light emitting intensity is high, the light emitting efficiency is high, a life of the element is long, and it is easy to make the element.


[0053] Examples of a fundamental structure of such a non-conjugated polymer include polymers comprising polyester, polyether, polyurethane, polyimide, polyamide, polyetherketone, polycarbonate, polysulfide, polyethersulfide, a silicon-containing polymer, and a germanium-containing polymer, or copolymers thereof. Among these, it is preferable that a fundamental structure of the non-conjugated polymer is any of polyester, polyether and polyurethane, in view of ease of synthesizing, heat stability, solubility in and the compatibility with a solvent and a resin, and the like.


[0054] In addition, the non-conjugated polymer may have a molecular chain on which a charge can move. In this case, it is preferable that the non-conjugated polymer is a hole transporting polymer.


[0055] It is preferable that the non-conjugated polymer as explained above comprises a repetition unit containing at least one partial structure selected from the group consisting of the following general formulas (I-1) and (I-2).


[0056] Since such a non-conjugated polymer is excellent in the heat stability during light emission, and solubility in and compatibility with a solvent and a resin, it is easy to prepare an organic electroluminescent element and, further, as an organic electroluminescent element, reliability of the light emitting property and a element life can be improved.
5


[0057] Wherein, in the general formulas (I-1) and (I-2), Ar represents a group selected from the group consisting of a substituted or unsubstituted monovalent benzene ring, a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having an aromatic ring number of 2 to 10, a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having an aromatic ring number of 2 to 10, and a substituted or unsubstituted monovalent aromatic heterocyclic ring; X represents a group selected from the group consisting of a substituted or unsubstituted divalent benzene ring, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having an aromatic ring number of 2 to 10, a substituted or unsubstituted divalent condensed aromatic hydrocarbon having an aromatic ring number of 2 to 10, and a substituted or unsubstituted divalent aromatic heterocyclic ring; T represents a group selected from the group consisting of a divalent straight hydrocarbon group having a carbon number of 1 to 6, and a divalent branched hydrocarbon group having a carbon number of 2 to 10; and k, i and j each independently represent an integer selected from 0 to 1.


[0058] In addition, the polynuclear aromatic hydrocarbon and the condensed aromatic hydrocarbon specifically are compounds defined below in the invention.


[0059] That is, the “polynuclear hydrocarbon” represents hydrocarbon containing 2 or more aromatic rings composed of carbon and hydrogen, in which aromatic rings are connected by a carbon-carbon bond. Examples thereof include biphenyl and terphenyl. In addition, the “condensed aromatic hydrocarbon” represents hydrocarbon containing 2 or more aromatic rings composed of carbon and hydrogen, in which aromatic rings share one pair of carbon atoms. Examples thereof include naphthalene, anthracene, phenanthrene and fluorene.


[0060] In addition, as a heterocyclic ring, heterocyclic rings having the number of atoms (Nr) constituting the ring skeleton of 5 and/or 6 are preferably used. In addition, atoms (hetero atom) other than carbon atoms constituting the ring skeleton are not particularly limited, but for example, a sulfur atom, a nitrogen atom, an oxygen atom and the like are preferably used. In addition, the ring skeleton may contain two or more kinds of and/or two or more hetero atoms. In particular, as a heterocyclic ring having a 5-membered ring structure, thiophene, pyrrole and furan, or heterocyclic rings in which 3- and 4-positional carbon atoms are replaced with nitrogen atoms are preferably used. In addition, as a heterocyclic ring having a 6-membered ring structure, pyridine is preferably used.


[0061] Examples of a substituent of the benzene ring, the polynuclear aromatic hydrocarbon or the condensed aromatic hydrocarbon include a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a substituted amino group, a halogen atom and the like. As the alkyl group, alkyl groups having a carbon number of 1 to 10 are preferable, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group and the like. As the alkoxy group, alkoxy groups having a carbon number of 1 to 10 are preferable, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group and the like. As the aryl group, aryl groups having a carbon number of 6 to 20 are preferable, and examples thereof include a phenyl group, a toluyl group and the like. As the aralkyl group, aralkyl groups having a carbon number of 7 to 20, and examples thereof include a benzyl group, a phenethyl group and the like. Examples of the substituent of the substituted amino group include an alkyl grouop, an aryl group, an aralkyl group and the like, and specific examples are as described above.


[0062] X represents a substituted or unsubstituted divalent benzene ring, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having an aromatic ring number of 2 to 10, a substituted or unsubstituted divalent condensed aromatic hydrocarbon having an aromatic ring number of 2 to 10, or a substituted or unsubstituted divalent aromatic heterocyclic ring, and examples thereof include a group selected from the following formulas (1) to (13).
67


[0063] In the formulas (1) to (13), R1 to R14 represent a hydrogen atom, an alkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, a substituted or unsubstituted phenyl group, a substituted or unsubstituted aralkyl group, or a halogen atom, a means 0 or 1, and b means an integer of 0 to 10. In addition, V represents a group selected from the following formulas (14) to (34).
89


[0064] In formulas (14) to (34), R15 represents a hydrogen atom, an alkyl group or a cyano group, R16 to R17 represent a hydrogen atom, an alkyl group having a carbon number of 1 to 10, an alkoxyl group having a carbon number of 1 to 10, a substituted or unsubstituted phenyl group, a substituted or unsubstituted aralkyl group, or a halogen atom, and c means an integer of 0 to 10.


[0065] In addition, T represents a divalent straight hydrocarbon group having a carbon number of 1 to 6, or a divalent branched hydrocarbon group having a carbon number of 2 to 10, and is preferably selected from a divalent straight hydrocarbon group having a carbon number of 2 to 6, and a divalent branched hydrocarbon group having a carbon number of 3 to 7. Specific structures are shown below.
1011


[0066] In addition, specific examples of the structure represented by the general formulas (I-1) are shown in Table 1 to Table 49, and specific examples of the structure represented by the general formula (I-2) are shown in Table 50 to Table 88. In Table 1 to Table 88, the number described in the “Bonding Point.” column shows that carbon in a benzene ring with this number added thereto is a bonding position, in the general formulas (I-1) and (I-2).
1TABLE 1BondingStructurekXArPointijT101213300201415411—CH2CH2301617301—CH2CH24018194012050212240123602425401—CH2CH2702627401—CH2CH2


[0067]

2












TABLE 2












Bonding





Structure
k
X
Ar
Point
i
j
T
































8
0


28







29





4
0
1
—CH2





9
0


30







31





4
0
1
—CH2CH2





10
0


32







33





4
1
0






11
0


34







35





4
0
1
—CH2





12
0


36







37





4
0
1
—CH2CH2





13
0


38







39





4
0
1
—CH2





14
0


40







41





4
0
1
—CH2CH2










[0068]

3












TABLE 3












Bonding





Structure
k
X
Ar
Point
i
j
T

















15
0


42







43





4
0
1


44










16
0


45







46





4
0
1
—CH2





17
0


47







48





4
0
1
—CH2CH2





18
0


49







50





4
0
1
—CH2CH2





19
0


51







52





4
0
1
—CH2CH2










[0069]

4












TABLE 4












Bonding





Structure
k
X
Ar
Point
i
j
T

















20
0


53







54





4
0
1
—CH2CH2





21
0


55







56





3
0
1
—CH2CH2





22
0


57







58





4
0
1
—CH2CH2





23
0


59







60





4
0
1


61










24
0


62







63





4
0
1
—CH2CH2





25
0


64







65





4
0
1
—CH2CH2





26
0


66







67





4
0
1
—CH2










[0070]

5












TABLE 5












Bonding





Structure
k
X
Ar
Point
i
j
T

















27
0


68







69





4
0
0






28
0


70







71





4
1
0






29
0


72







73





4
0
1
—CH2CH2





30
0


74







75





4
1
0






31
0


76







77





4
0
0






32
0


78







79





4
0
0






33
0


80







81





4
0
0











[0071]

6












TABLE 6












Bonding





Structure
k
X
Ar
Point
i
j
T

















34
0


82







83





4
0
0






35
0


84







85





4
0
0






36
0


86







87





3
1
1
—CH2CH2





37
0


88







89





4
1
1
—CH2





38
0


90







91





4
1
1
—CH2CH2





39
0


92







93





4
1
1
—CH2





40
0


94







95





4
1
1
—CH2










[0072]

7












TABLE 7












Bonding





Structure
k
X
Ar
Point
i
j
T

















41
1


96







97





4
0
1
—CH2CH2





42
1


98







99





4
0
1
—CH2CH2





43
1


100







101





4
0
1
—CH2CH2





44
1


102







103





4
0
1
—CH2CH2





45
1


104







105





4
0
1
—CH2CH2





46
1


106







107





4
0
1
—CH2CH2










[0073]

8












TABLE 8












Bonding





Structure
k
X
Ar
Point
i
j
T

















47
1


108







109





4
0
1
—CH2





48
1


110







111





4
0
1


112










49
1


113







114





4
0
1


115










50
1


116







117





4
0
1
—CH2CH2





51
1


118







119





4
0
1
—CH2CH2





52
1


120







121





4
0
1
—CH2CH2










[0074]

9












TABLE 9












Bonding





Structure
k
X
Ar
Point
i
j
T

















53
1


122







123





4
0
1
—CH2CH2





54
1


124







125





2
0
1
—CH2CH2





55
1


126







127





3
0
1
—CH2CH2





56
1


128







129





4
0
1
—CH2





57
1


130







131





4
0
1
—CH2CH2





58
1


132







133





4
0
1
—(CH2)4










[0075]

10












TABLE 10












Bond-





Struc-



ing


ture
k
X
Ar
Point
i
j
T

















59
1


134







135





4
0
1


136










60
1


137







138





4
0
1
—CH2CH2





61
1


139







140





4
0
1
—CH2CH2





62
1


141







142





3
0
1
—CH2CH2





63
1


143







144





4
0
1
—CH2CH2





64
1


145







146





4
0
1


147










65
1


148







149





3
0
1
—CH2CH2










[0076]

11












TABLE 11












Bonding





Structure
k
X
Ar
Point
i
j
T
































66
1


150







151





4
0
1
—CH2CH2





67
1


152







153





4
0
1
—(CH2)3





68
1


154







155





4
0
1
—CH2CH2





69
1


156







157





4
0
1


158










70
1


159







160





4
0
1
—CH2CH2





71
1


161







162





4
0
1
—CH2CH2





72
1


163







164





4
0
1
—CH2CH2










[0077]

12












TABLE 12












Bond-









ing


Structure
k
X
Ar
Point
i
j
T

















73
1


165







166





3
0
1
—CH2





74
1


167







168





3
0
1
—CH2CH2





75
1


169







170





4
0
0






76
1


171







172





4
0
0






77
1


173







174





4
0
0






78
1


175







176





4
0
0











[0078]

13












TABLE 13












Bonding





Structure
k
X
Ar
Point
i
j
T
































79
1


177







178





4
0
1






80
1


179







180





4
0
1
—CH2





81
1


181







182





4
0
1
—CH2





82
1


183







184





4
0
1
—CH2





83
1


185







186





4
0
1
—CH2





84
1


187







188





4
0
1
—CH2





85
1


189







190





4
0
1
—CH2CH2










[0079]

14












TABLE 14












Bonding





Structure
k
X
Ar
Point
i
j
T
































86
1


191







192





4
0
1
—CH2CH2





87
1


193







194





4
0
1
—CH2CH2





88
1


195







196





4
0
1
—CH2CH2





89
1


197







198





4
0
1
—CH2CH2





90
1


199







200





4
0
1
—CH2CH2





91
1


201







202





4
0
1
—CH2CH2










[0080]

15












TABLE 15












Bonding





Structure
k
X
Ar
Point
i
j
T
































92
1


203







204





4
0
1
—CH2CH2





93
1


205







206





4
0
1
—CH2CH2





94
1


207







208





4
0
1
—CH2CH2





95
1


209







210





4
0
1
—CH2CH2





96
1


211







212





4
0
1
—(CH2)4





97
1


213







214





4
0
1


215















[0081]

16












TABLE 16












Bonding





Structure
k
X
Ar
Point
i
j
T
































98
1


216







217





4
0
1
—CH2CH2





99
1


218







219





4
0
1
—CH2CH2





100
1


220







221





4
0
1
−CH2





101
1


222







223





4
0
1
—CH2CH2





102
1


224







225





4
0
1
—CH2CH2





103
1


226







227





4
0
1
—CH2CH2





104
1


228







229





4
0
1
—CH2CH2










[0082]

17












TABLE 17












Bonding





Structure
k
X
Ar
Point
i
j
T
































105
1


230







231





4
0
1
—CH2CH2





106
1


232







233





4
0
1


234










107
1


235







236





4
0
1
—CH2CH2





108
1


237







238





4
0
1
—CH2





109
1


239







240





4
0
1
—CH2CH2





110
1


241







242





4
0
0






111
1


243







244





4
0
0











[0083]

18












TABLE 18












Bonding





Structure
k
X
Ar
Point
i
j
T
































112
1


245







246





4
0
0






113
1


247







248





4
0
0






114
1


249







250





4
0
0






115
1


251







252





4
0
1
—CH2





116
1


253







254





4
0
1
—CH2





117
1


255







256





4
0
1
—CH2





118
1


257







258





4
0
1
—CH2










[0084]

19












TABLE 19












Bonding





Structure
k
X
Ar
Point
i
j
T
































119
1


259







260





4
0
1
—CH2





120
1


261







262





4
0
1
—CH2CH2





121
1


263







264





4
0
1
—CH2





122
1


265







266





4
0
1
—CH2CH2





123
1


267







268





4
0
1
—CH2CH2





124
1


269







270





4
0
1


271










125
1


272







273





4
0
0











[0085]

20












TABLE 20












Bonding





Structure
k
X
Ar
Point
i
j
T
































126
1


274







275





4
0
1
—CH2





127
1


276







277





4
0
1
—CH2CH2





128
1


278







279





4
0
1
—CH2CH2





129
1


280







281





4
0
1
—CH2CH2





130
1


282







283





4
0
1
—CH2CH2





131
1


284







285





4
0
1
—CH2CH2





132
1


286







287





4
0
1
—CH2CH2










[0086]

21












TABLE 21












Bonding





Structure
k
X
Ar
Point
i
j
T

















133
1


288







289





4
0
1
—CH2CH2





134
1


290







291





4
0
1
—CH2CH2





135
1


292







293





4
0
1
—CH2CH2





136
1


294







295





4
0
1
—CH2CH2





137
1


296







297





4
0
1
—CH2CH2





138
1


298







299





4
0
1
—(CH2)4










[0087]

22












TABLE 22












Bonding





Structure
k
X
Ar
Point
i
j
T

















139
1


300







301





4
0
1


302










140
1


303







304





4
0
1
—CH2CH2





141
1


305







306





4
0
0






142
1


307







308





4
0
1
—CH2





143
1


309







310





3
0
0






144
1


311







312





4
0
0






145
1


313







314





4
0
1
—CH2CH2










[0088]

23












TABLE 23












Bond-









ing


Structure
k
X
Ar
Point
i
j
T

















146
1


315







316





4
1
0






147
1


317







318





4
0
1
—CH2





148
1


319







320





4
0
1


321










149
1


322







323





4
0
1
—CH2CH2





150
1


324







325





4
0
1
—CH2CH2





151
1


326







327





4
0
1
—CH2CH2










[0089]

24












TABLE 24












Bonding





Structure
k
X
Ar
Point
i
j
T

















152
1


328







329





4
0
1
—CH2CH2





153
1


330







331





4
0
1
—CH2CH2





154
1


332







333





4
0
1
—CH2CH2





155
1


334







335





4
0
1
—CH2CH2





156
1


336







337





4
0
1
—CH2CH2





157
1


338







339





4
0
1
—CH2CH2










[0090]

25












TABLE 25












Bonding





Structure
k
X
Ar
Point
i
j
T

















158
1


340







341





4
0
1
—CH2CH2





159
1


342







343





4
0
1
—CH2CH2





160
1


344







345





4
0
1
—CH2CH2





161
1


346







347





4
0
1
—CH2CH2





162
1


348







349





4
0
1
—CH2CH2





163
1


350







351





4
0
1
—CH2CH2










[0091]

26












TABLE 26












Bonding





Structure
k
X
Ar
Point
i
j
T

















164
1


352







353





4
0
1
—CH2CH2





165
1


354







355





4
0
1
—CH2CH2





166
1


356







357





4
0
1
—CH2CH2





167
1


358







359





4
0
1
—CH2CH2





168
1


360







361





4
0
1
—CH2CH2





169
1


362







363





4
0
1
—CH2CH2










[0092]

27












TABLE 27












Bonding





Structure
k
X
Ar
Point
i
j
T

















170
1


364







365





4
0
1
—CH2CH2





171
1


366







367





4
0
0






172
1


368







369





4
0
1
—CH2





173
1


370







371





4
0
0






174
1


372







373





4
1
0






175
1


374







375





4
0
1
—CH2CH2





176
1


376







377





4
0
1
—CH2CH2










[0093]

28








TABLE 28










Structure
k
X
Ar





177
1


378







379










178
1


380







381










179
1


382







383










180
1


384







385










181
1


386







387










182
1


388







389






















Bond-






Structure
Point
i
j
T







177
4
0
1
—CH2CH2



178
4
0
1
—CH2CH2



179
4
0
1
—CH2CH2



180
4
0
1
—CH2CH2



181
4
0
1
—CH2CH2



182
4
0
1
—CH2CH2











[0094]

29












TABLE 29












Bond-





Struc-



ing


ture
k
X
Ar
Point
i
j
T

















183
1


390







391





4
0
1
—CH2CH2





184
1


392







393





4
0
1
—CH2CH2





185
1


394







395





4
0
1
—CH2





186
1


396







397





4
0
1
—CH2CH2





187
1


398







399





4
0
1
—CH2CH2





188
1


400







401





4
0
1
—CH2CH2





189
1


402







403





4
0
0











[0095]

30








TABLE 30










Structure
k
X
Ar





190
1


404







405










191
1


406







407










192
1


408







409










193
1


410







411










194
1


412







413










195
1


414







415










196
1


416







417






















Bonding






Structure
Point
i
j
T







190
4
0
1
—CH2



191
4
0
1
—CH2



192
4
0
1
—CHCH2



193
4
0
1


418












194
4
0
1
—CH2CH2



195
4
0
1
—CH2CH2



196
4
0
1
—CH2CH2











[0096]

31












TABLE 31












Bonding





Structure
k
X
Ar
Point
i
j
T
































197
1


419







420





4
0
1
—CH2CH2





198
1


421







422





4
0
1
—CH2CH2





199
1


423







424





4
0
1
—CH2CH2





200
1


425







426





4
0
1
—CH2CH2





201
1


427







428





4
0
1
—CH2CH2





202
1


429







430





4
0
1
—(CH2)3










[0097]

32












TABLE 32












Bonding





Structure
k
X
Ar
Point
i
j
T
































203
1


431







432





4
0
1
—CH2CH2





204
1


433







434





4
0
1
—CH2CH2





205
1


435







436





4
0
0






206
1


437







438





4
0
1
—CH2





207
1


439







440





4
0
1
—CH2CH2





208
1


441







442





4
0
1
—CH2CH2





209
1


443







444





4
0
1
—CH2CH2










[0098]

33












TABLE 33












Bonding





Structure
k
X
Ar
Point
i
j
T
































210
1


445







446





4
0
1
—CH2CH2





211
1


447







448





4
0
1
—CH2CH2





212
1


449







450





4
0
1
—CH2CH2





213
1


451







452





4
0
1
—CH2CH2





214
1


453







454





4
0
1
—CH2CH2





215
1


455







456





4
0
1
—CH2CH2










[0099]

34












TABLE 34












Bonding





Structure
k
X
Ar
Point
i
j
T
































216
1


457







458





4
0
1
—CH2CH2





217
1


459







460





4
0
1
—CH2CH2





218
1


461







462





4
0
0






219
1


463







464





4
0
1
—CH2





220
1


465







466





4
0
1
—CH2





221
1


467







468





4
0
1
—CH2





222
1


469







470





4
0
0











[0100]

35












TABLE 35












Bonding





Structure
k
X
Ar
Point
i
j
T
































223
1


471







472





4
0
1
—(CH2)3





224
1


473







474





4
0
1
—CH2CH2





225
1


475







476





4
0
1
—CH2CH2





226
1


477







478





4
0
1
—CH2CH2





227
1


479







480





4
0
1
—CH2CH2





228
1


481







482





4
0
1
—CH2










[0101]

36












TABLE 36












Bonding





Structure
k
X
Ar
Point
i
j
T
































229
1


483







484





4
0
1
—(CH2)3





230
1


485







486





4
0
0






231
1


487







488





4
0
1
—CH2





232
1


489







490





4
0
1
—CH2CH2





233
1


491







492





4
0
1
—CH2





234
1


493







494





4
0
1
—CH2





235
1


495







496





4
0
1
—CH2










[0102]

37












TABLE 37












Bonding





Structure
k
X
Ar
Point
i
j
T

















236
1


497







498





4
0
1
—CH2CH2





237
1


499







500





4
0
1
—CH2





238
1


501







502





4
0
1
—CH2CH2





239
1


503







504





4
0
1
—CH2CH2





240
1


505







506





4
0
1
—CH2CH2





241
1


507







508





4
0
1
—CH2










[0103]

38












TABLE 38












Bonding





Structure
k
X
Ar
Point
i
j
T
































242
1


509







510





4
0
1
—(CH2)3





243
1


511







512





4
0
1
—CH2CH2





244
1


513







514





4
0
1
—CH2





245
1


515







516





4
0
1
—CH2





246
1


517







518





4
0
1
—CH2





247
1


519







520





4
0
1
—CH2CH2










[0104]

39












TABLE 39












Bonding





Structure
k
X
Ar
Point
i
j
T
































248
1


521







522





4
0
1
—CH2





249
1


523







524





4
0
1
—CH2





250
1


525







526





4
0
1
—CH2





251
1


527







528





4
0
1
—CH2CH2





252
1


529







530





4
0
1
—CH2










[0105]

40












TABLE 40












Bonding





Structure
k
X
Ar
Point
i
j
T
































253
1


531







532





4
0
1
—CH2





254
1


533







534





4
0
1
—CH2





255
1


535







536





4
0
1
—CH2CH2





256
1


537







538





4
1
1
—CH2





257
1


539







540





4
0
1
—CH2





258
1


541







542





4
0
1
—CH2CH2










[0106]

41












TABLE 41












Bonding





Structure
k
X
Ar
Point
i
j
T
































259
1


543







544





4
0
1
—CH2





260
1


545







546





4
0
1
—CH2CH2





261
1


547







548





4
0
1
—(CH2)3





262
1


549







550





4
0
1
—CH2CH2





263
1


551







552





4
0
1
—CH2CH2










[0107]

42












TABLE 42












Bonding





Structure
k
X
Ar
Point
i
j
T
































264
1


553







554





4
0
1
—CH2





265
1


555







556





4
0
1
—CH2CH2





266
1


557







558





4
0
1
—CH2





267
1


559







560





4
0
1
—CH2CH2





268
1


561







562





4
0
1
—CH2










[0108]

43












TABLE 43












Bonding





Structure
k
X
Ar
Point
i
j
T
































269
1


563







564





4
0
1
—CH2CH2





270
1


565







566





4
0
1
—CH2CH2





271
1


567







568





4
0
1
—CH2CH2





272
1


569







570





4
0
1
—CH2CH2





273
1


571







572





4
0
1
—CH2CH2










[0109]

44












TABLE 44












Bonding





Structure
k
X
Ar
Point
i
j
T

















274
1


573







574





4
0
1
—CH2CH2





275
1


575







576





4
0
1
—CH2CH2





276
1


577







578





4
0
1
—CH2





277
1


579







580





4
0
1
—CH2





278
1


581







582





4
0
1
—CH2CH2










[0110]

45












TABLE 45












Bonding





Structure
k
X
Ar
Point
i
j
T

















279
1


583







584





4
0
1
—CH2





280
1


585







586





4
0
1
—CH2CH2





281
1


587







588





4
0
1
—CH2CH2





282
1


589







590





4
0
1
—CH2CH2





283
1


591







592





4
0
1
—CH2CH2





284
1


593







594





4
0
1
—CH2CH2










[0111]

46












TABLE 46












Bonding





Structure
k
X
Ar
Point
i
j
T

















285
1


595







596





4
0
1
—CH2CH2





286
1


597







598





4
0
1
—CH2CH2





287
1


599







600





4
0
1
—CH2CH2





288
1


601







602





4
0
1
—CH2CH2





289
1


603







604





4
0
1
—CH2










[0112]

47












TABLE 47












Bonding





Structure
k
X
Ar
Point
i
j
T

















290
1


605







606





4
0
1
—(CH2)3





291
1


607







608





4
0
1
—CH2CH2





292
1


609







610





4
0
1
—CH2CH2





293
1


611







612





4
0
1
—CH2CH2





294
1


613







614





4
0
1
—CH2










[0113]

48












TABLE 48












Bonding





Structure
k
X
Ar
Point
i
j
T

















295
1


615







616





4
0
1
—CH2





296
1


617







618





4
0
1
—CH2





297
1


619







620





4
0
1
—CH2CH2





298
1


621







622





4
0
1
—CH2CH2





299
1


623







624





4
0
1
—CH2










[0114]

49












TABLE 49












Bonding





Structure
k
X
Ar
Point
i
j
T
































300
1


625







626





4
0
1
—(CH2)3





301
1


627







628





4
0
1
—CH2CH2





302
1


629







630





4
0
1
—CH2CH2










[0115]

50












TABLE 50












Bonding





Structure
k
X
Ar
Point
i
j
T

















303
0


631







632





4, 4′
0
0






304
0


633







634





4, 4′
1
1
—CH2CH2





305
0


635







636





4, 4′
0
1
—CH2CH2





306
0


637







638





4, 4′
0
1


639










307
0


640







641





4, 4′
0
1
—CH2CH2





308
0


642







643





4, 4′
0
1


644










309
0


645







646





4, 4′
0
1
—CH2CH2





310
0


647







648





4, 4′
0
1
—CH2










[0116]

51












TABLE 51












Bonding





Structure
k
X
Ar
Point
i
j
T

















311
0


649







650





4, 4′
0
1
—CH2CH2





312
0


651







652





4, 4′
0
1
—CH2CH2





313
0


653







654





4, 4′
0
1
—CH2





315
0


655







656





4, 4′
0
1


657










316
0


658







659





4, 4′
0
1
—CH2





317
0


660







661





4, 4′
0
1
—CH2CH2










[0117]

52












TABLE 52












Bonding





Structure
k
X
Ar
Point
i
j
T

















318
0


662







663





4, 4′
0
1
—CH2CH2





319
0


664







665





4, 4′
0
1
—CH2CH2





320
0


666







667





4, 4′
0
1
—CH2CH2





321
0


668







669





4, 4′
0
1
—CH2CH2





322
0


670







671





4, 4′
0
1


672










323
0


673







674





4, 4′
0
1
—CH2CH2





324
0


675







676





4, 4′
0
1
—CH2CH2










[0118]

53












TABLE 53












Bonding





Structure
k
X
Ar
Point
i
j
T

















325
0


677







678





4, 4′
0
1
—CH2





326
0


679







680





4, 4′
0
0






327
0


681







682





4, 4′
1
0






328
0


683







684





4, 4′
0
1
—CH2CH2





329
0


685







686





4, 4′
1
0
—(CH2)4





330
0


687







688





4, 4′
0
0






331
0


689







690





4, 4′
0
0






332
0


691







692





4, 4′
0
0











[0119]

54












TABLE 54












Bonding





Structure
k
X
Ar
Point
i
j
T

















333
0


693







694





4, 4′
0
0






334
0


695







696





4, 4′
0
0
—CH2CH2





335
0


697







698





4, 4′
0
0
—CH2





336
0


699







700





4, 4′
0
0
—CH2CH2





337
0


701







702





4, 4′
0
0
—CH2





338
0


703







704





4, 4′
1
1
—CH2





339
1


705







706





4, 4′
1
1
—CH2CH2





340
1


707







708





4, 4′
1
1
—CH2CH2










[0120]

55












TABLE 55












Bonding





Structure
k
X
Ar
Point
i
j
T

















341
1


709







710





4, 4′
0
1
—CH2CH2





342
1


711







712





4, 4′
0
1
—CH2CH2





343
1


713







714





4, 4′
0
1
—CH2CH2





344
1


715







716





4, 4′
0
1
—CH2CH2





345
1


717







718





4, 4′
0
1
—CH2





346
1


719







720





4, 4′
0
1


721










347
1


722







723





4, 4′
0
1


724















[0121]

56












TABLE 56












Bonding





Structure
k
X
Ar
Point
i
j
T

















348
1


725







726





4, 4′
0
1
—CH2CH2





349
1


727







728





4, 4′
0
1
—CH2CH2





350
1


729







730





4, 4′
0
1
—CH2CH2





351
1


731







732





4, 4′
0
1
—CH2CH2





352
1


733







734





4, 4′
0
1
—CH2CH2





353
1


735







736





4, 4′
0
1
—(CH2)4





354
1


737







738





4, 4′
0
1


739















[0122]

57












TABLE 44








Struct-



Bonding





ure
k
X
Ar
Point
i
j
T

















355
1


740







741





4, 4′
0
1
—CH2CH2





356
1


742







743





4, 4′
0
1
—CH2CH2





357
1


744







745





4, 4′
0
1
—CH2CH2





358
1


746







747





4, 4′
0
1


748










359
1


749







750





4, 4′
0
1
—CH2CH2





360
1


751







752





4, 4′
0
1
—(CH2)3





361
1


753







754





4, 4′
0
1


755















[0123]

58












TABLE 58












Bonding





Structure
k
X
Ar
Point
i
j
T

















363
1


756







757





4, 4′
0
1


758










364
1


759







760





4, 4′
0
1
—CH2CH2





365
1


761







762





4, 4′
0
1
—CH2CH2





366
1


763







764





4, 4′
0
0






367
1


765







766





4, 4′
0
1
—CH2CH2





368
1


767







768





4, 4′
0
1
—CH2CH2





369
1


769







770





4, 4′
0
1
—CH2CH2










[0124]

59












TABLE 59












Bonding





Structure
k
X
Ar
Point
i
j
T

















370
1


771







772





4, 4′
0
0






371
1


773







774





4, 4′
0
1
—CH2





372
1


775







776





4, 4′
0
1
—CH2





373
1


777







778





4, 4′
0
1
—CH2





374
1


779







780





4, 4′
0
1
—CH2





375
1


781







782





4, 4′
0
1
—CH2





376
1


783







784





4, 4′
0
1
—CH2CH2





377
1


785







786





4, 4′
0
1
—CH2CH2










[0125]

60












TABLE 60












Bonding





Structure
k
X
Ar
Point
i
j
T

















378
1


787







788





4, 4′
1
1
—CH2CH2





379
1


789







790





4, 4′
0
1
—CH2CH2





380
1


791







792





4, 4′
0
1
—CH2CH2





381
1


793







794





4, 4′
0
1
—CH2CH2





382
1


795







796





4, 4′
0
1
—CH2CH2





383
1


797







798





4, 4′
0
1
—CH2CH2





384
1


799







800





4, 4′
0
1
—CH2CH2










[0126]

61












TABLE 61












Bond-





Struct-



ing


ure
k
X
Ar
Point
i
j
T

















385
1


801







802





4, 4′
0
1
—CH2CH2





386
1


803







804





4, 4′
0
1
—CH2CH2





387
1


805







806





4, 4′
0
1
—(CH2)4





388
1


807







808





4, 4′
0
1


809










389
1


810







811





4, 4′
0
1
—CH2CH2





390
1


812







813





4, 4′
0
1
—CH2





391
1


814







815





4, 4′
0
1
—CH2CH2





392
1


816







817





4, 4′
0
1
—CH2CH2










[0127]

62








TABLE 62










Structure
k
X
Ar





393
1


818







819










394
1


820







821










395
1


822







823










396
1


824







825










307
1


826







827










398
1


828







829










399
1


830







831










400
1


832







833






















Bonding






Structure
Point
i
j
T







393
4,4′
0
1
—CH2CH2



394
4,4′
0
1
—CH2CH2



395
4,4′
0
1


834












396
4,4′
0
1
—CH2CH2



397
4,4′
0
1
—CH2



398
4,4′
0
1
—CH2CH2



399
4,4′
0
1
—CH2CH2



400
4,4′
0
1
—CH2CH2











[0128]

63








TABLE 63










Structure
k
X
Ar





401
1


835







836










402
1


837







838










403
1


839







840










404
1


841







842










405
1


843







844










406
1


845







846










407
1


847







848










408
1


849







850






















Bonding






Structure
Point
i
j
T







401
4,4′
0
1
—CH2CH2



402
4,4′
0
1
—CH2CH2



403
4,4′
0
1
—CH2CH2



404
4,4′
0
1
—CH2



405
4,4′
0
1
—CH2



406
4,4′
0
1
—CH2



407
4,4′
0
1
—CH2



408
4,4′
0
1
—CH2











[0129]

64












TABLE 64












Bonding





Structure
k
X
Ar
Point
i
j
T

















409
1


851







852





4,4′
0
1
—CH2CH2





410
1


853







854





4,4′
0
1
—CH2





411
1


855







856





4,4′
1
1
—CH2CH2





412
1


857







858





4,4′
0
1
—CH2CH2





413
1


859







860





4,4′
0
1


861










414
1


862







863





4,4′
0
0






415
1


864







865





4,4′
0
1
—CH2





416
1


866







867





4,4′
0
1
—CH2CH2










[0130]

65












TABLE 65












Bonding





Structure
k
X
Ar
Point
i
j
T

















417
1


868







869





4,4′
0
1
—CH2CH2





418
1


870







871





4,4′
0
1
—CH2CH2





419
1


872







873





4,4′
0
1
—CH2CH2





420
1


874







875





4,4′
0
1
—CH2CH2





421
1


876







877





4,4′
0
1
—CH2CH2





422
1


878







879





4,4′
0
1
—CH2CH2





423
1


880







881





4,4′
0
1
—CH2CH2










[0131]

66












TABLE 66












Bonding





Structure
k
X
Ar
Point
i
j
T

















424
1


882







883





4,4′
0
1
—CH2CH2





425
1


884







885





4,4′
0
1
—CH2CH2





426
1


886







887





4,4′
0
1
—CH2CH2





427
1


888







889





4,4′
0
1
—CH2CH2





428
1


890







891





4,4′
0
1


892










429
1


893







894





4,4′
0
1
—CH2CH2





430
1


895







896





4,4′
0
1
—CH2





431
1


897







898





4,4′
0
1
—CH2CH2










[0132]

67












TABLE 67








Struc-



Bonding





ture
k
X
Ar
Point
i
j
T

















432
1


899







900





4,4′
0
0






433
1


901







902





4,4′
0
1
—CH2CH2





434


903







904





4,4′
1
0






435
1


905







906





4,4′
0
1
—CH2





436
1


907







908





4,4′
0
1


909










437
1


910







911





4,4′
0
1
—CH2CH2





438
1


912







913





4,4′
0
1
—CH2CH2





439
1


914







915





4,4′
0
1
—CH2CH2










[0133]

68












TABLE 68












Bonding





Structure
k
X
Ar
Point
i
j
T

















440
1


916







917





4,4′
0
1
—CH2CH2





441
1


918







919





4,4′
0
1
—CH2CH2





442
1


920







921





4,4′
0
1
—CH2CH2





443
1


922







923





4,4′
0
1
—CH2CH2





444
1


924







925





4.4′
0
1
—CH2CH2





445
1


926







927





4,4′
0
1
—CH2CH2





446
1


928







929





4,4′
0
1
—CH2CH2










[0134]

69












TABLE 69












Bonding





Structure
k
X
Ar
Point
i
j
T

















447
1


930







931





4,4′
0
1
—CH2CH2





448
1


932







933





4,4′
0
1
—CH2CH2





449
1


934







935





4,4′
0
1
—CH2CH2





450
1


936







937





4,4′
0
1
—CH2CH2





451
1


938







939





4,4′
0
1
—CH2CH2





452
1


940







941





4,4′
0
1
—(CH2)3





453
1


942







943





4,4′
0
1
—CH2CH2










[0135]

70








TABLE 70










Structure
k
X
Ar





454
1


944







945










455
1


946







947










456
1


948







949










457
1


950







951










458
1


952







953










459
1


954







955










460
1


956







957






















Bonding






Structure
Point
i
j
T







454
4,4′
0
1
—CH2CH2







455
4,4′
0
1
—CH2CH2







456
4,4′
0
1
—CH2CH2







457
4,4′
0
1
—CH2CH2







458
4,4′
0
1
—CH2CH2







459
4,4′
0
1
—CH2







460
4,4′
0
1
—CH2











[0136]

71








TABLE 71










Structure
k
X
Ar





461
1


958







959










462
1


960







961










463
1


962







963










464
1


964







965










465
1


966







967










466
1


968







969










467
1


970







971






















Bonding






Structure
Point
i
j
T







461
4,4′
1
0








462
4,4′
0
1
—CH2CH2







463
4,4′
0
1
—CH2CH2







464
4,4′
0
1
—CH2CH2







465
4,4′
0
1
—CH2CH2







466
4,4′
0
1
—CH2CH2







467
4,4′
0
1
—CH2CH2











[0137]

72












TABLE 72












Bonding





Structure
k
X
Ar
Point
i
j
T

















468
1


972







973





4, 41
0
1
—CH2CH2





469
1


974







975





4, 41
0
1
—CH2CH2





470
1


976







977





4, 41
0
1
—CH2CH2





471
1


978







979





4, 41
0
1
—CH2





472
1


980







981





4, 41
0
1
—CH2CH2





473
1


982







983





4, 41
0
1
—CH2CH2





474
1


984







985





4, 41
0
1
—CH2CH2





475
1


986







987





4, 41
0
0











[0138]

73












TABLE 73












Bonding





Structure
k
X
Ar
Point
i
j
T

















476
1


988







989





4, 4′
0
1
—CH2





477
1


990







991





4, 4′
0
1
—CH2





478
1


992







993





4, 4′
0
1
—CH2CH2





479
1


994







995





4, 4′
0
1


996










480
1


997







998





4, 4′
0
1
—CH2CH2





481
1


999







1000





4, 4′
0
1
—CH2CH2





482
1


1001







1002





4, 4′
0
1
—CH2CH2





483
1


1003







1004





4, 4′
0
1
—CH2CH2










[0139]

74












TABLE 74












Bonding





Structure
k
X
Ar
Point
i
j
T

















484
1


1005







1006





4, 4′
0
1
—CH2





485
1


1007







1008





4, 4′
0
1
—CH2





486
1


1009







1010





4, 4′
0
1
—CH2





487
1


1011







1012





4, 4′
0
1
—CH2





488
1


1013







1014





4, 4′
0
1
—(CH2)3





489
1


1015







1016





4, 4′
0
1
—CH2





490
1


1017







1018





4, 4′
0
1
—CH2










[0140]

75












TABLE 75












Bonding





Structure
k
X
Ar
Point
i
j
T

















491
1


1019







1020





4, 4′
0
0






492
1


1021







1022





4, 4′
0
1
—CH2





493
1


1023







1024





4, 4′
0
1
—CH2CH2





494
1


1025







1026





4, 4′
0
1
—CH2CH2





495
1


1027







1028





4, 4′
0
1
—CH2CH2





496
1


1029







1030





4, 4′
0
1
—CH2CH2





497
1


1031







1032





4, 4′
0
1
—CH2CH2










[0141]

76












TABLE 76












Bonding





Structure
k
X
Ar
Point
i
j
T

















498
1


1033







1034





4, 4′
0
1
—CH2CH2





499
1


1035







1036





4, 4′
0
1
—CH2CH2





500
1


1037







1038





4, 4′
0
1
—CH2CH2





501
1


1039







1040





4, 4′
0
1
—CH2CH2





502
1


1041







1042





4, 4′
0
1
—CH2CH2





503
1


1043







1044





4, 4′
0
1
—CH2CH2





504
1


1045







1046





4, 4′
0
0






505
1


1047







1048





4, 4′
0
1
—CH2










[0142]

77












TABLE 77












Bonding





Structure
k
X
Ar
Point
i
j
T

















506
1


1049







1050





4, 4′
0
1
—CH2





507
1


1051







1052





4, 4′
0
1
—CH2





508
1


1053







1054





4, 4′
0
0






509
1


1055







1056





4, 4′
0
1
—(CH2)3





510
1


1057







1058





4, 4′
0
1
—CH2CH2





511
1


1059







1060





4, 4′
0
1
—CH2CH2





512
1


1061







1062





4, 4′
0
1
—(CH2)3










[0143]

78












TABLE 78












Bonding





Structure
k
X
Ar
Point
i
j
T

















513
1


1063







1064





4, 4′
0
1
—CH2CH2





514
1


1065







1066





4, 4′
0
1
—CH2





515
1


1067







1068





4, 4′
0
1
—(CH2)3





516
1


1069







1070





4, 4′
0
0






517
1


1071







1072





4, 4′
0
1
—CH2





518
1


1073







1074





4, 4′
0
1
—CH2CH2





519
1


1075







1076





4, 4′
0
1
—CH2CH2





520
1


1077







1078





4, 4′
0
1
—CH2CH2










[0144]

79












TABLE 79












Bonding





Structure
k
X
Ar
Point
i
j
T

















521
1


1079







1080





4, 4′
0
1
—(CH2)3





522
1


1081







1082





4, 4′
0
1
—CH2





523
1


1083







1084





4, 4′
0
1
—CH2CH2





524
1


1085







1086





4, 4′
0
1
—CH2CH2





525
1


1087







1088





4, 4′
0
1
—CH2CH2





526
1


1089







1090





4, 4′
0
1
—CH2





527
1


1091







1092





4, 4′
0
1
—(CH2)3










[0145]

80












TABLE 80












Bonding





Structure
k
X
Ar
Point
i
j
T

















528
1


1093







1094





4, 4′
0
1
—CH2CH2





529
1


1095







1096





4, 4′
0
1
—CH2





530
1


1097







1098





4, 4′
0
1
—CH2





531
1


1099







1100





4, 4′
0
1
—CH2





532
1


1101







1102





4, 4′
0
1
—CH2CH2





533
1


1103







1104





4, 4′
0
1
—CH2CH2





534
1


1105







1106





4, 4′
0
1
—CH2










[0146]

81












TABLE 81












Bonding





Structure
k
X
Ar
Point
i
j
T

















535
1


1107







1108





4, 4′
0
1
—CH2CH2





536
1


1109







1110





4, 4′
0
1
—CH2





537
1


1111







1112





4, 4′
0
1
—CH2





538
1


1113







1114





4, 4′
0
1
—CH2





539
1


1115







1116





4, 4′
0
1
—CH2CH2





540
1


1117







1118





4, 4′
0
1
—CH2





541
1


1119







1120





4, 4′
0
1
—CH2










[0147]

82












TABLE 82








Structure
k
X
Ar
Bonding Point
i
j
T

















542
1


1121







1122





4,4′
0
1
—CH2CH2





543
1


1123







1124





4,4′
0
1
—CH2





544
1


1125







1126





4,4′
0
1
—CH2CH2





545
1


1127







1128





4,4′
0
1
—(CH2)3





546
1


1129







1130





4,4′
0
1
—CH2CH2





547
1


1131







1132





4,4′
0
1
—CH2CH2





548
1


1133







1134





4,4′
0
1
—CH2










[0148]

83












TABLE 83








Structure
k
X
Ar
Bonding Point
i
j
T

















549
1


1135







1136





4,4′
0
1
—CH2CH2





550
1


1137







1138





4,4′
0
1
—CH2





551
1


1139







1140





4,4′
0
1
—CH2CH2





552
1


1141







1142





4,4′
0
1
—CH2





553
1


1143







1144





4,4′
0
1
—CH2CH2





554
1


1145







1146





4,4′
0
1
—CH2CH2










[0149]

84












TABLE 84












Bond-





Struc-



ing





ture
k
X
Ar
Point
i
j
T

















555
1


1147







1148





4,4′
0
1
—CH2CH2





556
1


1149







1150





4,4′
0
1
—CH2CH2





557
1


1151







1152





4,4′
0
1
—CH2CH2





558
1


1153







1154





4,4′
0
1
—CH2CH2





559
1


1155







1156





4,4′
0
1
—CH2





560
1


1157







1158





4,4′
0
1
—CH2










[0150]

85












TABLE 85












Bond-





Struc-



ing





ture
k
X
Ar
Point
i
j
T

















561
1


1159







1160





4,4′
0
1
—CH2CH2





562
1


1161







1162





4,4′
0
1
—CH2





563
1


1163







1164





4,4′
0
1
—CH2CH2





564
1


1165







1166





4,4′
0
1
—CH2CH2





565
1


1167







1168





4,4′
0
1
—CH2CH2





566
1


1169







1170





4,4′
0
1
—CH2CH2





567
1


1171







1172





4,4′
0
1
—(CH2)3










[0151]

86












TABLE 86








Structure
k
X
Ar
Bonding Point
i
j
T

















568
1


1173







1174





4,4′
0
1
—CH2CH2





569
1


1175







1176





4,4′
0
1
—CH2CH2





570
1


1177







1178





4,4′
0
1
—CH2CH2





571
1


1179







1180





4,4′
0
1
—CH2CH2





572
1


1181







1182





4,4′
0
1
—CH2





573
1


1183







1184





4,4′
0
1
—(CH2)3










[0152]

87












TABLE 87












Bond-





Struc-



ing





ture
k
X
Ar
Point
i
j
T

















574
1


1185







1186





4,4′
0
1
—CH2CH2





575
1


1187







1188





4,4′
0
1
—CH2CH2





576
1


1189







1190





4,4′
0
1
—(CH2)3





577
1


1191







1192





4,4′
0
1
—CH2





578
1


1193







1194





4,4′
0
1
—(CH2)3





579
1


1195







1196





4,4′
0
1
—CH2










[0153]

88












TABLE 88








Structure
k
X
Ar
Bonding Point
i
j
T

















580
1


1197







1198





4,4′
0
1
—CH2CH2





581
1


1199







1200





4,4′
0
1
—CH2CH2





582
1


1201







1202





4,4′
0
1
—CH2





583
1


1203







1204





4,4′
0
1
—(CH2)3





584
1


1205







1206





4,4′
0
1
—CH2CH2










[0154] A non-conjugated polymer comprising a repetition unit at least one partial structure selected from the group consisting of the general formulas (I-1) and (I-2) is not particularly limited, but a polyester represented by the following formula (II-1) or (II-2), a polyether represented by the following general formula (III-1), and a polyurethane represented by the following general formula (IV-1) or (IV-2) are suitable.
1207


[0155] In the general formulas (II-1) and (II-2), A1 represents at least one selected from the structures represented by the above general formulas (I-1) and (I-2), Y1 represents a divalent alcohol residue, Z1 represents a divalent carboxylic acid residue, m represents an integer of 1 to 5, and p represents selected from a range of 5 to 5,000.


[0156] In the general formula (III-1), A1 represents at least one selected from the structures represented by the above general formulas (I-1) and (I-2), and p represents an integer from 5 to 5,000.


[0157] In addition, in the general formulas (IV-1) and (IV-2), A1 represents at least one selected from the structures represented by the above general formulas (I-1) and (I-2), T represents a divalent straight hydrocarbon group having a carbon number of 1 to 6, or a divalent branched hydrocarbon group having a carbon number of 2 to 10, Y2 and Z2 represent divalent diisocyanate, alcohol or amine residue, m represents an integer from 1 to 5, and p represents an integer from 5 to 5,000.


[0158] The structure represented by A1 in the general formulas (II-1), (II-2), (III-1), (IV-1) and (IV-4) represents at least one selected from the structures represented by the general formulas (I-1) and (I-2), and two or more structures may be used, if necessary.


[0159] In addition, in the non-conjugated polymer used in the invention as explained above, at least one of terminal groups has a fluorescent substance emitting fluorescence in a solid state. Such a fluorescent substance may be an inorganic fluorescent substance or an organic fluorescent substance, an organic fluorescent substance is preferable in view of a magnitude of light emitting quantum efficiency and diversity of a material, and an organic fluorescent substance which has a further high quantum efficiency, is chemically stable, and has heat resistance is more preferable.


[0160] Examples of such a organic fluorescent substance include a compound having a substituted or unsubstituted monovalent benzene ring or a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having an aromatic ring number of 2 to 10, a compound having a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having an aromatic ring number of 2 to 10, and a compound having a substituted or unsubstituted monovalent aromatic heterocyclic ring.


[0161] More specifically, examples thereof include polyacene derivative compounds such as a naphthalene derivative, an anthracene derivative, a tetracene derivative, a perylene derivative, a pyrene derivative and the like, a styrylamine compound, a quinacridone derivative compound, a rubulene derivative compound, a coumarin derivative compound and a pyran derivative compound


[0162] In addition, since chelating metal complexes containing a metal such as Al, Zn, Be, Mg, Eu, Ga, Pt, Ir and the like have high fluorescent quantum efficiency, are chemically stable and have heat resistance, they can be suitably used as a fluorescent substance.


[0163] In addition, it is preferable that a maximum peak wavelength of fluorescent spectrum of a fluorescent substance is in the visible light region (380 nm to 700 nm). When a maximum peak wavelength is outside a range of the visible light region, sufficient light emitting intensity is not obtained in some cases.


[0164] Examples of such a fluorescent substance are shown in Tables 89 to 95, but the fluorescent substance used in the invention is not limited to them.
89TABLE 89StructureFluorscent material585120858612095871210588121158912125901213591121459212155931216594121759512185961219


[0165]

90






TABLE 90








Structure
Fluorscent











597


1220










598


1221










599


1222










600


1223










601


1224










602


1225










603


1226










604


1227










605


1228










606


1229










607


1230










608


1231















[0166]

91






TABLE 91








Structure
Fluorscent material











609


1232










610


1233










611


1234










612


1235










613


1236










614


1237










615


1238










616


1239










617


1240










618


1241















[0167]

92






TABLE 92








Structure
Fluorscent material











619


1242










620


1243










621


1244










622


1245










623


1246










624


1247










625


1248










626


1249










627


1250










628


1251















[0168]

93






TABLE 93








Structure
Fluorscent material











629


1252










630


1253










631


1254










632


1255










633


1256










634


1257










635


1258










636


1259










637


1260










638


1261















[0169]

94






TABLE 94








Structure
Fluorscent material











639


1262










640


1263










641


1264










642


1265










643


1266










644


1267










645


1268










646


1269










647


1270










648


1271










649


1272










650


1273















[0170]

95






TABLE 95








Structure
Fluorscent material











651


1274










652


1275










653


1276










654


1277










655


1278










656


1279










657


1280










658


1281










659


1282










660


1283















[0171] A weight average molecular weight Mw of the non-conjugated polymer used in the invention is not particularly limited, but when the non-conjugated polymer comprises a repetition unit containing at least one partial structure selected from the group consisting of the general formulas (I-1) and (I-2), it is preferable that the weight average molecular weigh Mw is in the range of 5000 to 300000.


[0172] Below, as a non-conjugated polymer, examples of polyester represented by the general formula (I-1) or (II-2) are shown in Tables 96 to 101, examples of polyether represented by the general formula (III-1) are shown in Tables 102 to 103, and examples of polyurethane represented by the general formula (IV-1) or (IV-2) are shown in Tables 104 to 107, but the polyester, the polyether and the polyurethane used in the invention are not limited to these examples.


[0173] Herein, the number in “A1” column of the “monomer” in Tables 96 to 107 corresponds to a compound having the number described in “structure” column in Tables 1 to 88 (specific examples of the above general formulas (I-1) and (I-2)). In addition, “m” means “m” shown in the general formulas (I-1) and (I-2). Hereinafter, an example (compound) with each number added thereto in Tables 96 to 107 is described as an example compound and, for example, an example with number 15 added thereto describes an exemplified compound (15).


[0174] In addition, in Table 96 to Table 101, example compounds, a partial structure of which is described only in “Y1” column, among “Y1” and “Z1” columns, mean polyester represented by the general formula (II-1). In addition, example compounds, a partial structure of which is described in both “Y1” and “Z1” columns, mean polyester represented by the general formula (II-2).


[0175] In addition, in Table 104 to Table 107, example compounds, a partial structure of which is described only in “Y2” column, among “Y2” and “Z2” columns, mean polyurethane represented by the general formula (IV-1). In addition, example compounds, a partial structure of which is described only in “Z2” column, among “Y2” and “Z2” columns, mean polyurethane represented by the general formula (IV-2).
96TABLE 96MononerFluorscentCompoundA1RatioY1Z1materialmp (1)2—CH2CH2585112 (2)5—CH2CH2585150 (3)9—CH2CH2585158 (4)9—CH2CH21284585162 (5)9—CH2CH21285585195 (6)9—CH2CH21286585248 (7)131287587135 (8)131288—(CH2)4587131 (9)191289587125(10)19—CH2CH2587125(11)41—CH2CH2589125(12)42—CH2CH2589147(13)42—CH2CH21290590275(14)39—CH2CH2—(CH2)4590189


[0176]

97










TABLE 97













Monomer

Fluorscent















Compound
A1
Ratio
Y1
Z1
material
m
p





(15)
46

—CH2CH2

594
1
59





(16)
46

—CH2CH2


1291





594
2
44





(17)
49



1292






594
1
78





(18)
53



1293






594
1
74





(19)
80



1294







1295





600
1
67





(20)
80

—CH2CH2

603
1
55





(21)
80

—CH2CH2


1296





609
1
87





(22)
85



1297






609
1
48





(23)
87



1298






609
1
36





(24)
87



1299







1300





609
1
66





(25)
88

—CH2CH2

616
1
48


(26)
92

—CH2CH2

616
1
44










[0177]

98










TABLE 98













Mononer

Fluorscent















Compound
A1
Ratio
Y1
Z1
material
m
p















(27)
127

—CH2CH2


1301





616
1
85





(28)
127



1302






616
1
66





(29)
127



1303






616
1
78





(30)
127



1304







1305





616
1
14





(31)
137

—CH2CH2

626
1
74





(32)
156

—CH2CH2


1306





629
1
74





(33)
160

—CH2CH2

633
1
56


(34)
173

—CH2CH2

618
1
63


(35)
175

—CH2CH2

618
1
78


(36)
178

—CH2CH2

618
1
75


(37)
181

—CH2CH2

618
1
25


(38)
182

—CH2CH2

618
1
65


(39)
183

—CH2CH2

618
1
45


(40)
191

—CH2CH2

630
1
42


(41)
193

—CH2CH2

630
1
85










[0178]

99










TABLE 99













Monomer

Fluorsoent















Compound
A1
Ratio
Y1
Z1
material
m
p





(42)
233

—CH2CH2

630
1
45


(43)
234

—CH2CH2

630
1
54





(44)
238

—CH2CH2


1307





616
1
86





(45)
243

—(CH2)4
—(CH2)4
616
1
65





(46)
243



1308






616
1
23





(47)
243

—CH2CH2

606
1
78





(48)
243

—CH2CH2


1309





587
1
92





(49)
248



1310






597
1
79





(50)
249

—CH2CH2

597
1
86


(51)
251

—CH2CH2

604
1
58





(52)
251



1311






639
1
98





(53)
255



1312






639
1
36





(54)
262

—CH2CH2

639
1
59





(55)
267

—CH2CH2


1313





645
1
48










[0179]

100










TABLE 100













Monomer

Fluorscent















Compound
A1
Ratio
Y1
Z1
material
m
p















(56)
305



1314






655
1
18





(57)
307



1315






655
1
47





(58)
305



1316







1317





655
1
22





(59)
267

—CH2CH2

655
1
45





(60)
336

—CH2CH2


1318





656
1
56





(61)
336



1319






656
1
44





(62)
336



1320






656
1
47





(63)
352



1321







1322





656
1
35





(64)
352



1323






656
1
38





(65)
376



1324






656
1
75










[0180]

101










TABLE 101













Monomer

Fluorscent















Compound
A1
Ratio
Y1
Z1
material
m
p















(66)
376



1325






659
1
53





(67)
379

—CH2CH2

659
1
45





(68)
379

—CH2CH2


1326





658
1
55





(69)
 7/92
1/1
—CH2CH2

658
1
63


(70)
 7/92
1/1
—CH2CH2

658
2
80





(71)
 7/92
1/1


1327







1328





658
1
45





(72)
 7/92
1/1
—CH2CH2

658
1
43


(73)
 7/127
1/1
—CH2CH2

618
1
60


(74)
 7/127
1/1
—CH2CH2

613
2
26


(75)
 7/175
1/1
—CH2CH2

613
1
24


(76)
7/92/17
1/1/1
—CH2CH2

618
1
75


(77)
173/220
1/1
—CH2CH2

613
1
63





(78)
 7/311
1/1
—CH2CH2


1329





613
1
70





(79)
 7/311
1/2
—CH2CH2

618
1
42


(80)
311/338
2/1
—CH2CH2

613
1
38










[0181]

102









TABLE 102













Monomer
Fluorscent















Compound
A1
Ratio
material
m
p


















 (81)
3

585
1
23



 (82)
5

587
2
43



 (83)
6

587
1
45



 (84)
7

587
1
70



 (85)
12

587
2
45



 (86)
12

587
1
65



 (87)
19

587
1
35



 (88)
20

587
0
31



 (89)
22

587
1
45



 (90)
41

587
1
68



 (91)
43

587
1
74



 (92)
44

587
1
35



 (93)
47

600
2
36



 (94)
49

600
1
62



 (95)
53

600
2
33



 (96)
56

600
1
65



 (97)
88

600
1
61



 (98)
90

606
1
39



 (99)
92

606
1
25



(100)
93

606
1
45



(101)
127

606
1
35



(102)
145

606
1
61



(103)
175

606
1
43



(104)
176

606
1
58



(105)
178

616
1
68



(106)
179

616
1
65



(107)
181

616
1
35



(108)
188

616
1
34



(109)
221

616
1
37



(110)
243

616
1
62



(111)
245

616
1
36



(112)
247

616
1
46



(113)
249

616
1
38



(114)
262

616
1
98



(115)
265

616
1
38











[0182]

103









TABLE 103













Monomer
Fluorscent















Compound
A1
Ratio
material
m
p







(116)
267

616
1
68



(117)
273

618
1
78



(118)
277

618
1
88



(119)
297

618
1
65



(120)
304

618
1
93



(121)
305

618
1
75



(122)
307

618
1
67



(123)
311

618
1
37



(124)
314

618
1
68



(125)
317

652
1
62



(126)
319

652
2
61



(127)
320

652
1
37



(128)
339

652
1
64



(129)
340

652
1
35



(130)
341

659
1
78



(131)
342

639
1
36



(132)
347

639
1
87



(133)
417

659
1
45



(134)
461

639
1
84



(135)
462

660
1
35



(136)
529

639
1
84



(137)
 7/36
1/1
639
1
36



(138)
 7/43
1/1
639
1
63



(139)
 7/44
1/2
589
1
47



(140)
 7/53
1/1
606
2
56



(141)
 7/85
1/1
600
1
59



(142)
20/85
1/2
600
1
65



(143)
57/90
1/1
606
1
43



(144)
57/92
1/2
589
1
15



(145)
57/94
5/1
589
1
34



(146)
 57/127
1/1
600
1
44



(147)
127/196
1/2
606
1
48



(148)
176/340
6/1
606
1
37



(149)
243/376
2/1
589
1
39



(150)
7/20/57
1/2/4
589
1
57











[0183]

104










TABLE 104













Monomer

Fluorscent
















Compound
A1
Ratio
Y2
Z2
material
T
m
p


















(151)
2

—(CH2)6

585
—CH2
1
65


(152)
2

—(CH2)6

587
—CH2CH2
1
84


(153)
4

—(CH2)6

587
—CH2
1
38


(154)
6

—(CH2)6

587
—CH2
1
64


(155)
7

—(CH2)6

587
—CH2CH2
1
36





(156)
7



1330






587
—CH2CH2
1
55





(157)
9

—(CH2)6

587
—CH2CH2
1
36





(158)
9



1331






587
—CH2CH2
1
63





(159)
19



1332






587
—CH2CH2
1
65





(160)
19


—CH2CH2
587
—CH2CH2
1
43


(161)
41

—(CH2)6

587
—CH2CH2
1
36


(162)
42

—(CH2)6

587
—CH2CH2
1
28





(163)
44



1333






600
—CH2
1
35










[0184]

105










TABLE 105













Monomer

Fluorscent
















Compound
A1
Ratio
Y2
Z2
material
T
m
p





























(164)
44



1334






600
—CH2
1
47





(165)
46

—(CH2)6

600
—CH2
1
62


(166)
53

—(CH2)6

600
—CH2
1


(167)
54

—(CH2)6

600
—CH2CH2
1
45





(168)
54



1335






606
—CH2
1
40





(169)
80


—CH2CH2
606
—CH2
1
75


(170)
88

—(CH2)6

606
—CH2
1
61


(171)
92

—(CH2)6

606
—CH2
1
43


(172)
127

—(CH2)6

606
—CH2
1
88





(173)
127



1336






606
—CH2
1
47





(174)
156

—(CH2)6

606
—CH2
1
71


(175)
175

—(CH2)6

616
—CH2
1
22


(176)
176

—(CH2)6

616
—CH2CH2
1
54


(177)
178

—(CH2)6

616
—CH2CH2
1
36


(178)
182

—(CH2)6

616
—CH2CH2
1
57


(179)
183

—(CH2)6

616
—CH2CH2
1
85










[0185]

106










TABLE 106













Monomer

Fluorscent
















Compound
A1
Ratio
Y2
Z2
material
T
m
p


















(180)
185

—(CH2)6

616
—CH2CH2
1
63


(181)
188

—(CH2)6

616
—CH2CH2
1
41


(182)
192

—(CH2)6

616
—CH2CH2
1
52


(183)
209

—(CH2)6

616
—CH2CH2
1
67


(184)
220

—(CH2)6

616
—CH2CH2
1
52


(185)
221

—(CH2)6

616
—CH2CH2
1
36


(186)
222

—(CH2)6

616
—CH2CH2
1
78


(187)
243

—(CH2)6

618
—CH2CH2
1
45


(188)
244

—(CH2)6

618
—CH2CH2
1
74


(189)
247

—(CH2)6

618
—CH2CH2
1
98


(190)
249

—(CH2)6

618
—CH2CH2
1
78


(191)
254

—(CH2)6

618
—CH2CH2
1
58


(192)
256

—(CH2)6

618
—CH2CH2
1
98


(193)
262

—(CH2)6

618
—CH2CH2
1
62


(194)
297

—(CH2)6

618
—CH2CH2
1
85


(195)
303

—(CH2)6

652
—CH2CH2
1
47


(196)
305

—(CH2)6

652
—CH2CH2
1
65


(197)
313


—CH2CH2
652
—CH2CH2
1
69










[0186]

107










TABLE 107













Monomer

Fluorscent
















Compound
A1
Ratio
Y2
Z2
material
T
m
p


















(198)
340

—(CH2)6

652
—CH2CH2
1
77


(199)
376


—CH2CH2
652
—CH2CH2
1
48


(200)
377

—(CH2)6

659
—CH2CH2
1
85


(201)
379

—(CH2)6

639
—CH2CH2
1
25


(202)
7/43
1/1
—(CH2)6

639
—CH2CH2
1
76


(203)
7/44
1/1
—(CH2)6

659
—CH2CH2
1
87


(204)
7/53
1/1
—(CH2)6

639
—CH2CH2
1
47


(205)
57/127
1/1
—(CH2)6

660
—CH2CH2
1
74










[0187] A method of synthesizing the non-conjugated polymer used in the invention is not particularly limited, but the known methods can be utilized by combining them depending on a desired structure, and examples thereof are explained below. The following specific examples explain in detail the cases where a non-conjugated polymer comprising a repetition unit containing at least one partial structure selected from the group consisting of the above general formulas (I-1) and (I-2) is a polyester represented by the above general formula (II-1) or (II-2), a polyether represented by the above general formula (III-1), or a polyurethane represented by the above general formula (IV-1) or (IV-2).


[0188] I) In the Case of Polyester


[0189] When the non-conjugated polymer used in the invention is polyester represented by the above general formula (II-1) or (II-2), the non-conjugated polymer can be synthesized by polymerizing a monomer represented by the following general formula (II-3), for example, by the known method described in 4th edition, Experimental Chemical Course, vol. 28 (Maruzen Co., Ltd., 1992).


A′—A1—A′  (II-3)


[0190] In the general formula (II-3), A1 represents at least one selected from the structures represented by the general formulas (I-1) and (I-2), A′ represents a hydroxyl group, a halogen atom, or a group —O—R18, and R18 represents an alkyl group, a substituted or unsubstituted aryl group, or an aralkyl group.


[0191] That is, polyester represented by the above general formula (II-1) or (II-2) can be synthesized as follows:


[0192] 1) When A′ is a hydroxy group, a divalent alcohol represented by HO—(Y—O)m—H is mixed with a monomer at an approximately equivalent amount, and this is polymerized using an acid catalyst. As an acid catalyst, catalysts which are used for a normal esterification reaction such as sulfuric acid, toluenesulfonic acid, trifluoroacetic acid and the like can be used, and are used in the range of 1/10,000 to 1/10 parts by weight, preferably 1/1,000 to 1/50 parts by weight relative to 1 part by weight of a monomer. In addition, as a solvent, it is preferable to use a solvent which can be azeotroped with water in order to remove water produced during polymerization, toluene, chlorobenzene, 1-chloronaphthalene and the like are effective, and the solvent is used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight relative to 1 part by weight of a monomer. A reaction temperature can be set arbitrarily, but in order to remove water produced during polymerization, it is preferable that a reaction is performed at a boiling point of a solvent.


[0193] After completion of the reaction, when a solvent was not used, the reaction soultion is dissolved in a solvent which can dissolve the reaction solution. When a solvent was used, the reaction solution is added as it is dropwise to a poor solvent in which a polymer is hardly dissolved, such as alcohols such as methanol, ethanol and the like, acetone and the like, to precipitate polyester. Then, precipitated polyester is separated, washed with water or an organic solvent well, and is dried. Further, if necessary, polyester is dissolved in a suitable organic solvent, the solution is added dropwise to a poor solvent, and re-precipitating treatment for precipitating polyester may be repeated. Re-precipitating treatment is preferably performed while effectively stirring with a mechanical stirrer or the like. A solvent which dissolves polyester upon re-precipitating treatment is used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight relative to 1 part by weight of polyester. In addition, a poor solvent is used in the range of 1 to 1,000 parts by weight, preferably 10 to 500 parts by weight relative to 1 part by weight of polyester.


[0194] 2) When A′ is halogen, polymerization is performed by adding an organic basic catalyst such as pyridine and triethylamine to a mixture solution obtained by mixing a monomer and a divalent alcohol represented by HO—(Y—O)m—H at an approximately equivalent amount. An organic basic catalyst is used in the range of 1 to 10 equivalent, preferably 2 to 5 equivalent relative to 1 equivalent of a monomer. As a solvent, methylene chloride, tetrahydrofuran (THF), toluene, chlorobenzene, 1-chloronaphthalene and the like are effective, and the solvent is used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight relative to 1 part by weight of a monomer. A reaction temperature can be set arbitrarily. After polymerization, the reaction is subjected to re-precipitating treatment as described above, and is purified.


[0195] In addition, in the case of a divalent alcohol having the high acidity such as bisphenol, an interface polymerization method may be used. That is, polymerization can be performed by adding a divalent alcohol to water, adding an equivalent amount of a base to dissolve them, and adding a monomer solution at the same equivalent as that of a divalent alcohol while vigorously stirring. Upon this, water is used in the range of 1 to 1,000 parts by weight, preferably 2 to 500 parts by weight relative to 1 part by weight of a divalent alcohol. As a solvent which dissolves a monomer, methylene chloride, dichloroethane, trichloroethane, toluene, chlorobenzene, 1-chloronaphthalene and the like are effective. A reaction temperature can be set arbitrarily and, in order to promote a reaction, it is effective to use a phase transfer catalyst such as ammonium salt, sulfonium salt and the like. A phase transfer catalyst is used in the range of 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight relative to 1 part by weight of a monomer.


[0196] 3) When A′ is —O—R18, transesterification is available for polymerization. Such transesterification can be performed by heating a reaction solution which include a monomer, an excessive amount of a divalent alcohol [represented by HO—(Y—O)m—H] relative to the monomer, and a catalyst such as titanium alkoxide, acetate or carbonate of calcium and cobalt, or oxide of zinc or lead. A divalent alcohol is used in the range of 2 to 100 equivalent, preferably 3 to 50 equivalent relative to 1 equivalent of a monomer. A catalyst is used in the range of 1/10,000 to 1 parts by weight, preferably 1/1,000 to I-2 parts by weight relative to 1 part by weight of a monomer. A reaction is performed at a reaction temperature of 200 to 300° C. and, after completion of transesterification from a group —O—R18 to a group —O—(Y—O)m—H, it is preferable to perform a reaction under reduced pressure in order to promote polymerization by leaving of HO—(Y—O)m—H. Alternatively, a reaction may be performed while removing HO—(Y—O)m—H by azeotropy under a normal pressure using a high boiling point solvent such as 1-chloronaphthalene which can be azeotroped with HO—(Y—O)m—H.


[0197] Alternatively, polyester may be synthesized as follows: In aforementioned respective cases, after a compound represented by the following general formula (II-4) is produced by a reaction by adding an excessive amount of a divalent alcohol and, by using this compound in place of a monomer represented by the above general formula (II-3), the compound may be reacted with divalent carboxylic acid or divalent carboxylic halide according to the aforementioned method, whereby, polyester can be obtained.
1337


[0198] In the general formula (II-4), A1 represents at least one selected from the structures represented by the above general formulas (I-1) and (I-2), Y1 represents a divalent alcohol residue, and m represents an integer from 1 to 5.


[0199] 4) Introduction of a fluorescent substance is not particularly limited, but there are following methods. That is, when A′ is a hydroxy group, a fluorescent substance can be introduced in a polymer by copolymerizing monocarboxylic acid of a fluorescent substance, or after a polymerization reaction for a polymer, using monocarboxylic acid of a fluorescent substance to react them. In addition, when A′ is halogen, a fluorescent substance can be introduced into a polymer by copolymerizing monoacid chloride of a fluorescent substance, or after a polymerization reaction for a polymer, using monoacid chloride of a fluorescent substance to react them. When A′ is —O—R18, a fluorescent substance can be introduced into a polymer by copolymerizing monoester of a fluorescent substance, or after a polymerization reaction for a polymer, placing monoester of a fluorescent substance to react them.


[0200] II) In the Case of Polyether


[0201] When the non-conjugated polymer used in the invention is polyether represented by the above general formula (III-1), the non-conjugated polymer can be easily prepared by condensing between molecules of a compound having a hydroxyl group represented by the following general formulas (III-2).


HO—A1—OH  (III-2)


[0202] In the general formula (III-2), A1 represents at least one selected from the structures represented by the above general formulas (I-1) and (I-2).


[0203] Polyether represented by the above general formula (III-1) can be specifically synthesized, for example, by the following method.


[0204] 1) The aforementioned polyether can be synthesized by a method of heating and dehydration-condensing a monomer having two hydroxyl groups on both ends of a structure represented by A1, as in the above general formula (III-2). In this case, it is desirable that a monomer is heated to melt without using a solvent, and a reaction is performed under reduced pressure in order to promote a polymerization reaction by leaving of water. In addition, when a solvent is used, in order to remove water, it is effective to use a solvent which is azeotoped with water, for example, trichloroethane, toluene, chlorobenzene, dichlorobenzene, nitrobenzene, 1-chloronaphthalene and the like. In this case, a solvent is used in the range of 1 to 100 equivalent, preferably 2 to 50 equivalent relative to 1 equivalent of a monomer. In addition, a reaction temperature can be set arbitrarily, but in order to remove water produced during polymerization, it is preferable to perform a reaction at a boiling point of a solvent. When polymerization does not proceed, a solvent may be removed from a reaction system, and the reaction may be heated to stir at the viscous state.


[0205] 2) The aforementioned polyether may be synthesized by a method of performing dehydration-condensation using, as an acid catalyst, protonic acids such as p-toluenesulfonic acid, hydrochloric acid, sulfuric acid, trifluoroacetic acid and the like, or Lewis acids such as zinc chloride and the like. In this case, an acid catalyst is used in the range of 1 to 1/10000 to 1/10 equivalent, preferably 1/1000 to 1/50 equivalent relative to 1 equivalent of a monomer. In order to remove water produced during polymerization, it is preferable to use a solvent which can be azeotroped with water. As such a solvent, toluene, chlorobenzene, dichlorobenzene, nitrobenzene, 1-chloronaphthalene and the like are effective, and they are used in the range of 1 to 100 equivalent, preferably 2 to 50 equivalent relative to 1 equivalent of a monomer. A reaction temperature can be set arbitrarily, but in order to remove water during a polymerization, a reaction is preferably performed at a boiling point of a solvent.


[0206] 3) The aforementioned monomer can be also synthesized by a method using a condensing agent such as alkyl isocyanate such as cyclohexyl isocyanate and the like, alkyl cyanate such as cyclohexyl cyanate and the like, cyanate ester such as p-tolyl cyanate, 2,2-bis(4-cyanatophenyl)propane and the like, dichlorohexylcarbodiimide (DCC), trichloroacetonitrile and the like. In this case, a condensing agent is used in the range of I-2 to 10 equivalent, preferably 1 to 3 equivalent relative to 1 equivalent of a monomer. As a solvent, toluene, chlorobenzene, dichlorobenene, 1-chloronaphthalene and the like are effective, and they are used in the range of 1 to 100 equivalent, preferably 2 to 50 equivalent. A reaction temperature can be set arbitrarily, but it is preferable that a reaction is performed at room temperature to a boiling point of a solvent. Among synthesizing methods 1) to 3) explained regarding polyester, the synthesizing method 1) or 3) is preferable because isomerization and side reactions are hardly caused. In particular, the synthesizing method 3) is preferable because the reaction condition is milder.


[0207] After completion of the reaction, when a solvent was not used, the reaction solution is dissolved as it is in a solvent which can dissolve it. When a solvent was used, the reaction solution is added as it is dropwise to a poor solvent which hardly dissolves a non-conjugated polymer, such as alcohols such as methanol, ethanol and the like, acetone or the like, to precipitate polyether, and polyether is separate, washed with water or an organic solvent well, and dried. Further, if necessary, re-precipitating treatment be repeated in which polyether is dissolved in a suitable organic solvent, and the solution is added dropwise to a poor solvent to precipitate a monomer. Upon re-precipitating treatment, it is preferable to perform treatment while stirring effectively with a mechanical stirrer or the like. A solvent which dissolves a monomer upon re-precipitating treatment is used in the range of 1 to 100 equivalent, preferably 2 to 50 equivalent relative to 1 equivalent of polyether. In addition, a poor solvent is used in the range of 1 to 1000 equivalent, preferably 10 to 500 equivalent relative to 1 equivalent of polyether. Further, in the aforementioned reaction, it is possible to copolymerize using two or more kinds of, preferably 2 to 5 kinds of, more preferably 2 to 3 kinds of monomers. By copolymerizing different monomers, the electric property, the film forming property, the solubility and the fluorescent property can be controlled.


[0208] When a polymerization degree of polyether is too low, the film forming property is inferior, and a firm film is hardly obtained. On the other hand, a polymerization degree is too high, solubility in a solvent is reduced, and the processibility is deteriorated in some cases. Therefore, a polymerization degree is preferably in the range of 5 to 5000, more preferably in the range of 10 to 3000, further preferably in the range of 15 to 1000.


[0209] In order to introduce L1, as in a monomer, a hydroxyl group, that is, a terminal group R may be a hydrogen atom. However, when the polymer physical properties such as the solubility, the film forming property, the mobility and the like are adversely influenced, a terminal group R can be modified to control the physical property. For example, a terminal hydroxyl group can be alkyletherized with alkyl sulfate, alkyl iodide or the like. A specific reagent can be arbitrarily selected from dimethyl sulfate, diethyl sulfate, methyl iodide, ethyl iodide and the like, and is used in the range of 1 to 3 equivalent, preferably in the range of 1 to 2 equivalent relative to a terminal hydroxyl group. Upon this, a base catalyst can be used, and can be selected from sodium hydroxide, potassium hydroxide, sodium hydride, sodium metal and the like, and is used in a range of to 3 equivalent, preferably in the range of 1 to 2 equivalent relative to a terminal hydroxyl group.


[0210] A reaction can be performed at 0° C. to a boiling point of a solvent to be used. In addition, as a solvent used thereupon, a single solvent selected from inert solvents such as benzene, toluene, methylene chloride, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like, or a mixed solvent of 2 to 3 of them can be used. In addition, depending on a reaction, a quaternary ammonium salt such as tetra-n-butylammonium iodide and the like may be used as a phase transfer catalyst. Alternatively, a terminal hydroxyl group may be acylated using acid halide to convert a terminal group R into an acyl group.


[0211] Examples of acid halide are not particularly limited, but include acryoyl chloride, crotonoyl chloride, methacryloyl chloride, n-butyl chloride, 2-furoyl chloride, benzoyl chloride, cyclohexanecarbonyl chloride, enantyl chloride, phenylacethyl chloride, o-toluoyl chloride, m-toluoyl chloride, p-toluoyl chloride and the like. They are used in the range of 1 to 3 equivalent, preferably 1 to 2 equivalent relative to a terminal hydroxyl group. Upon this, a base catalyst can be used, and can be selected arbitrarily from pyridine, dimethylaminopyridine, trimethylamine, triethylamine and the like, and is used in the range of 1 to 3 equivalent, preferably 1 to 2 equivalent relative to acid chloride. Examples of a solvent to be used thereupon include benzene, toluene, methylene chloride, tetrahydrofuran, methyl ethyl ketone and the like.


[0212] A reaction can be performed at 0° C. to a boiling point of the solvent, preferably, in the range of 0° C. to 30° C. Further, acylation may be also performed using acid anhydride such as acetic anhydride and the like. When a solvent is used, specifically, inert solvents such as benzene, toluene, chlorobenzene and the like can be used. A reaction can be performed at 0° C. to a boiling point of the solvent, preferably, 40° C. to a boiling point of a solvent.


[0213] Besides, an urethane residue (—CONH—R′) can be introduced into a terminal end using monoisocyatnate. Specifically, monoisocyanate can be arbitrarily selected from benzyl isocyanate, n-butyl isocyanate, t-butyl isocyanate, cyclohexyl isocianate, 2,6-dimethyl isocyanate, ethyl isocyanate, isopropyl isocyanate, 2-methoxyphenyl isocyanate, 4-methoxyphenyl isocyanate, n-octadecyl isocyanate, phenyl isocyanate, I-propyl isocyanate, m-tolyl isocyanate, p-tolyl isocyanate, 1-naphthyl isocyanate and the like. Monoisocyanate is used in the range of 1 to 3 equivalent, preferably 1 to 2 equivalent relative to a terminal hydroxyl group.


[0214] Examples of a solvent to be used upon this include benzene, toluene, chlorobenzene, dichlorobenzene, methylene chloride, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like. A reaction can be performed at a temperature of 0° C. to a boiling point of a solvent to be used. When a reaction hardly proceeds, metal compounds such as dibutyltin (II) dilaurate, tin (II) octylate, lead naphthenate and the like, or tertiary amines such as triethylamine, trimethylamine, pyridine, dimethylaminopyridine and the like may be added as a catalyst.


[0215] In addition, introduction of a fluorescent substance is not particularly limited, but the following methods are exemplified. That is, a method of acylating a terminal hydroxyl group by a monoacid salt compound of a fluorescent substance, and a method of introducing an urethane residue into a terminal hydroxyl group by using monoisocyanate of a fluorescent substance can be applied.


[0216] III) In the Case of Polyurethane


[0217] When the non-conjugated polymer used in the invention is polyurethane represented by the above general formula (IV-1) or (IV-2), the non-conjugated polymer can be synthesized by polymerizing monomers represented by the following general formulas (IV-3) to (IV-6) by the known method, for example, described in 4th Experimental Chemical Course, vol. 28 (Maruzen Co., Ltd., 1992), New Polymer Experiment, vol. 2 (Kyouritsushupan) 1995 and the like.


HO—A1—OH  (IV-3)


NCO—A1—OCN  (IV-4)


[0218]

1338




 H2N—A1—NH2  (IV-5)


[0219] In the general formulas (IV-3) to (IV-6), A1 represents at least one selected from the structures represented by the above general formulas (I-1) and (I-2).


[0220] Specifically, for example, when monomers represented by the general formulas (IV-3) and (IV-4) are used, polyurethane can be synthesized as follows.


[0221] When a monomer is a divalent alcohol represented by the general formula (IV-3), the monomer is mixed with diisocyanate represented by the OCN—Y—NCO at an equivalent amount and, when a monomer is diisocyanate represented by the general formula (IV-4), the monomer is mixed with a divalent alcohol represented by HO—Y—OH at an equivalent amount, whereby, polyaddition is performed.


[0222] As the catalyst, catalysts which are used in a reaction of synthesizing polyurethane by normal polyaddition, such as organometal compounds such as dibutyltin (II) dilaurate, dibutyltin (II) diacetate, lead naphthenate and the like can be used. In addition, when aromatic diisocyanate is used in synthesis of polyurethane, tertiary amines such as triethylenediamine and the like can be used as a catalyst. These organometal compounds and tertiary amines may be used by mixing them as a catalyst. An amount of a catalyst is in the range of 1/10,000 to 1/10 parts by weight, preferably 1/1,000 to 1/50 parts by weight relative to 1 part by weight of a monomer. Any solvents may be used as far as they dissolve a monomer and diisocyanate, or divalent alcohols. However, in view of the reactivity, it is preferable to use a solvent having the low polarity or a solvent forming no hydrogen bond to alcohols, and toluene, chlorobenzene, dichlorobenzene, 1-chloronaphthalene are effective. An amount of a solvent is in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight relative to 1 part by weight of a monomer. A reaction temperature can be arbitrarily set.


[0223] After completion of the reaction, the reaction solution is added as it is dropwise to a poor solvent in which a polymer is hardly dissolved, such as alcohols such as methanol, ethanol and the like, acetone and the like, and polyurethane is precipitated and separated from the reaction solution, washed with water or an organic solvent well, and is dried. Further, if necessary, re-precipitating treatment may be repeated in which polyurethane is dissolved in a suitable organic solvent, and the solution is added dropwise to a poor solvent, to precipitate polyurethane. Upon re-precipitated treatment, it is preferable to perform the treatment while effectively stirring with a mechanical stirrer or the like. A solvent which dissolves polyurethane upon re-precipitating treatment is used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight relative to 1 part by weight of polyurethane. In addition, a poor solvent is used in the range of 1 to 1,000 parts by weight, preferably 10 to 500 parts by weight relative to 1 part by weight of charge transporting polyurethane.


[0224] On the other hand, when monomers represented by the general formulas (IV-5) and (IV-6) are used, polyurethane can be synthesized as follows:


[0225] That is, when a monomer is bischloroformate represented by the general formula (IV-5), synthesis of polyurethane can be performed by mixing with diamine represented by 2HN—Y2—NH2 at an equivalent amount and conducting polycondensation. In addition, when a monomer is diamine represented by the general formula (IV-6), synthesis of polyurethane can be performed by mixing with bischloroformate represented by ClOCO—Y2—OCOCl at an equivalent amount and conducting polycondensation.


[0226] As a solvent, methylene chloride, dichloroethane, trichloroethane, tetrahydrofuran (THF), toluene, chlorobenzene, 1-chlorohaphthalene and the like are effective, and they are used in the range of 1 to 100 parts by weight, preferably 2 to 50 parts by weight relative to 1 part by weight of a monomer. A reaction temperature can be arbitrarily set. After polymerization, polyurethane is purified by re-precipitating treatment as described above.


[0227] In addition, when basicity of diamine represented by 2HN—Y—NH2 is high, an interface polymerization method may be used. That is, polymerization can be performed by adding water to diamine, adding an equivalent amount of an acid to dissolve the material, and adding diamine and a solution of an equivalent amount of a monomer represented by the aforementioned general formula (IV-5) while vigorously stirring. Upon this, water is used in the range of 1 to 1,000 parts by weight, preferably 10 to 500 parts by weight relative to 1 part by weight of diamine.


[0228] As a solvent which dissolves a monomer, methylene chloride, dichloroethane, trichloroethane, toluene, chlorobenzene, 1-chlorohaphthalene and the like are effective. A reaction temperature can be arbitrarily set. In addition, in order to promote a reaction, it is effective to use a phase transfer catalyst such as ammonium salt, sulfonium salt and the like. A phase transfer catalyst is used in the range of 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight relative to 1 part by weight of a monomer.


[0229] In addition, introduction of a fluorescent substance is not particularly limited, but following methods are exemplified. When a monomer represented by the general formula (IV-3) is used, a fluorescent substance can be introduced by copolymerizing a monovalent alcohol of a fluorescent substance, or after a polymerization reaction of a polymer, using a monovalent alcohol of a fluorescent substance to conduct a reaction.s


[0230] When a monomer represented by the general formula (IV-4) is used, a fluorescent substance can be introduced by copolymerizing monoisocyanate of a fluorescent substance, or after a polymerization reaction of a polymer, using monoisocyanate of a fluorescent substance to conduct a reaction.


[0231] When a monomer represented by the general formula (IV-5) is used, a fluorescent substance can be introduced by copolymerizing a monovalent carboxyilic acid of a fluorescent substance, or after a polymerization reaction of a polymer, using monovalent carboxyilic acid of a fluorescent substance to conduct a reaction.


[0232] When a monomer represented by the general formula (IV-6) is used, a fluorescent substance can be introduced by copolymerizing monoamine of a fluorescent substance, or after a polymerization reaction of a polymer, using monoamine of a fluorescent substance to conduct a reaction.


[0233] Then, a layer construction of the organic electroluminescent element of the invention will be described in detail.


[0234] A layer construction of the organic electroluminescent element of the invention is not particularly limited as far as the element comprises at least one pair of electrodes comprising an anode and a cathode, at least one of which having light transmissive, and at least one organic compound layer held by the electrodes, and the aforementioned non-conjugated polymer is contained in the at least one organic compound layer.


[0235] In the organic electroluminescent element of the invention, when the at least one organic compound layer is a single layer, this organic compound layer means a light emitting layer having the charge transporting function, and this light emitting layer having the charge transporting function contains the aforementioned non-conjugated polymer.


[0236] On the other hand, when the at least one organic compound layer is composed of a plurality of layers (that is, when this organic compound layer is function-separated type that functions of respective layers are different), at least one layer comprises a light emitting layer, and this light emitting layer may be a light emitting layer having a charge transporting function. In this case, examples of a layer construction comprising the aforementioned light emitting layer or the light emitting layer having the charge transporting function, and other layers include (1) a layer construction comprising a light emitting layer, an electron transporting layer and/or an electron injecting layer, (2) a layer construction comprising a hole transporting layer and/or a hole injecting layer, a light emitting layer, and an electron transporting layer and/or an electron injecting layer, and (3) a layer construction comprising a hole transporting layer and/or a hole injecting layer, and a light emitting layer having the charge transporting function. Layers other than the light emitting layer and the light emitting layer having the charge transporting function in these layer constructions (1) to (3) have function as a charge transporting layer or a charge injecting layer.


[0237] In addition, in any layer construction of the layer constructions (1) to (3), the non-conjugated polymer may be contained in any one layer, and it is preferable that the non-conjugated polymer is contained in a light emitting layer in the layer construction (1) and (2) and it is preferable that the non-conjugated polymer is contained in a light emitting layer having the electron transporting function in the layer construction (3).


[0238] In addition, the light emitting layer having the charge transporting layer, the hole transporting layer, the hole injecting layer, the electron transporting layer and the electron injecting layer may further contain a charge transporting compound (hole transporting material, electron transporting material) other than the aforementioned non-conjugated polymer. The details of such a charge transporting compound will be described below.


[0239] Hereinafter, the invention will be explained in detail by referring to the drawings, but is not limited to them.


[0240] FIGS. 1 to 4 are schematic cross-sectional views for explaining a layer construction of the organic electroluminescent element of the invention. FIGS. 1-2 and 4 show one example of the case where the organic compound layer comprises a plurality of layers, and FIG. 3 shows an example of the case where the organic compound layer comprises one layer. In FIGS. 1 to 4, the same symbol is given to a member having the same function.


[0241] In the organic electroluminescent element shown in FIG. 1, a transparent electrode 2, a light emitting layer 4, an electron transporting layer and/or an electron injecting layer 5, and a rear surface electrode 7 are deposited in this order on a transparent insulating substrate 1. When a layer shown by the symbol 5 comprising an electron transforming layer and an electron injecting layer, an electron transporting layer, an electron injecting layer and a rear surface electrode 7 are deposited in this order on a side where a rear surface electrode 7 of a light emitting layer 4 is provided.


[0242] In the organic electroluminescent element shown in FIG. 2, a transparent electrode 2, a hole transporting layer and/or a hole injecting layer 3, a light emitting layer 4, an electron transporting layer and/or an electron injecting layer 5, and a rear surface electrode 7 are deposited in this order on transparent insulating substrate 1. When a layer shown by the symbol 3 comprises a hole transporting layer and a hole injecting layer, a hole injecting layer, a hole transporting layer and a light emitting layer 4 are deposited in this order on a side where a rear electrode 7 of a transparent electrode 2 is provided. In addition, when a layer shown by the symbol 5 comprises an electron transporting layer and an electron injecting layer, an electron transporting layer, an electron injecting layer, and a rear surface electrode 7 are deposited in this order on a side where a rear electrode 7 of a light emitting layer 4 is provided.


[0243] In the organic electroluminescent element shown in FIG. 3, a transparent electrode 2, a light emitting layer 6 having the charge transporting function, and a rear surface electrode 7 are deposited in this order on a transparent insulating substrate 1. In the organic electroluminescent element shown in FIG. 4, a transparent electrode 2, a hole transporting layer and/or a hole injecting layer 3, a light emitting layer 6 having the charge transporting function, and a rear electrode 7 are deposited in this order on a transparent insulating substrate 1. When a layer shown by the symbol 3 comprises a hole transporting layer and a hole injecting layer, a hole injecting layer, a hole transporting layer, and a light emitting layer 6 having the charge transporting function are deposited in this order on a side where a rear electrode 7 of a transparent electrode 2 is provided. Each constituent member will be explained in detail below.


[0244] In the case of a layer construction of the organic electroluminescent element shown in FIGS. 1 to 4, a transparent insulating substrate 1 is preferably transparent for taking out the emitted light and glass, plastic film and the like are used. The transparency means that transmittance of the light in a visible region is 10% or more, and further, it is preferable that this transmittance is 75% or more.


[0245] A transparent electrode 2 is transparent for taking out the emitted light as in the transparent insulating substrate, and it is preferable that the electrode has the large work function for carrying out the injection of holes. It is preferable that the value of this work function is 4 eV or more. Examples of the transparent electrode 2 include oxidized films such as tin indium oxide (ITO), tin oxide (NESA), indium oxide, zinc oxide, indium zinc oxide and the like, and gold, platinum, palladium and the like formed by deposition or sputtering. A lower sheet resistance of a transparent electrode 2 is desirable, a few hundreds Ω/□ or less is preferable, further 100 Ω/□ or less is more preferable. In addition, in a transparent electrode 2, transmittance of the light in a visible region is 10% or more as in the transparent insulating substrate, and further, it is preferable that this transmittance is 75% or more.


[0246] In addition, for the purpose of improving the durability or the light emitting efficiency of the organic electroluminescent element, a hole transporting material other than the aforementioned non-conjugated polymer for regulating the hole mobility may be mixed and dispersed in the range of 0.1% by weight to 50% by weight relative to the non-conjugated polymer used in the invention. Examples of such a hole transporting material include a tetraphenylenediamine derivative, a triphenylamine derivative, a carbazole derivative, a stilbine derivative, an arylhydrazone derivative and a porphyrin compound. Among them, a tetraphenylenediamine derivative and a triphenylamine derivative are preferable because they have the better compatibility with the non-conjugated polymer.


[0247] In addition, similarly, when the electron mobility is adjusted, an electron transporting material may be mixed and dispersed in the range of 0.1% by weight to 50% by weight relative to the non-conjugated polymer. Examples of such a electron transporting material include an oxadiazole derivative, a nitro-substituted fluorenone derivative, a diphenoquinone derivative, a thiopyrandioxide derivative, a fluorenylidenmethane derivative and the like.


[0248] In addition, when both of the hole mobility and the electron mobility are required to be adjusted, both of the hole transporting material and the electron transporting material may be mixed into the non-conjugated polymer.


[0249] Further, for the purpose of improvement of the film forming property and prevention of pinhole, a suitable resin (polymer) and additive may be added. As a resin, for example, a polycarbonate resin, polyester resin, a methacryl resin, an acryl resin, a polyvinyl chloride resin, a cellulose resin, an urethane resin, an epoxy resin, a polystyrene resin, a polyvinyl acetate resin, a styrene butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, a vinyl chloride-vinyl acetate-maleic anhydride copolymer, a silicon resin, a poly-N-vinylcarbazole resin, and a polysilane resin, and electrically conducting resins such as polythiophene and polypyrrole can be used. In addition, as an additive, the known antioxidant, ultraviolet ray absorber, plasticizer and the like can be used.


[0250] In addition, for improving the light emitting intensity and adjusting the color purity and the light emitting spectrum, different dye compounds as a guest material may be doped. A dye compound to be doped may be an organic low-molecular compound or an organic high-molecular compound.


[0251] When a dye compound to be doped is an organic low-molecular compound, preferable example of this organic low-molecular compound include a chelating type organic metal complex, a polynuclear aromatic ring compound, a condensation aromatic ring compound, a perylene derivative, a coumarin derivative, a styrylarylene derivative, a silol derivative, an oxazole derivative, a oxathiazole derivative, an oxadiazole derivative and the like. In addition, when a dye compound to be doped is a high-molecular compound, as this high-molecular compound, a polyparaphenylene derivative, a polyparaphenylenevinylene derivative, a polythiophene derivative, a polyacetylene derivative and the like are used. As a suitable example of a dye compound, the following dye compounds (V-1) to (V-15) are used, being not limiting. In addition, in dye compounds (V-13) to (V-15), n and x represent an integer of 1 or more.
133913401341


[0252] A ratio of doping of a dye compound is around 0.001% by weight to 40% by weight, preferably around 0.001% by weight to 10% by weight. As dye compound to be used for such a doping, organic compounds having the better compatibility with a light emitting material and do not prevent better film forming of a light emitting layer are used and, suitably, a DCM derivative, a quinacridone derivative, a rublene derivative, porphyrin and the like are used. Suitable examples include the following dye compounds (VI-1) to (VI-4), being not limiting.
1342


[0253] In the case of a layer construction of the organic electroluminescent element shown in FIGS. 1 to 4, a metal, metal oxide, metal fluoride and the like which can be vacuum-deposited and has small work function for carrying out electron injection are used in a rear surface electrode 7. Examples of the metal include magnesium, aluminum, silver, indium, lithium, calcium and alloys thereof. Examples of the metal oxide include lithium oxide, magnesium oxide and aluminum oxide. In addition, examples of the metal fluoride include lithium fluoride, magnesium fluoride, strontium fluoride, calcium fluoride and aluminum fluoride. Further, in order to prevent deterioration of an organic electroluminescent element due to water or oxide, a protecting layer may be provided on a rear surface electrode 7.


[0254] Examples of a material for the protecting layer include metals such as In, Sn, Pb, Au, Cu, Ag, Al and the like, metal oxides such as MgO, SiO2, TiO2 and the like, and resins such as a polyethylene, a polyurea resin, a polyimide resin and the like. For forming a protecting layer, a vacuum-deposition method, a sputtering method, a plasma polymerization method, a CVD method and a coating method can be applied.


[0255] These organic electroluminescent elements shown in FIGS. 1 to 4 can be prepared by first forming individual layers corresponding to a layer construction of each organic electroluminescent element, in this order, on a transparent electrode 2.


[0256] In addition, a hole transporting layer and/or a hole injecting layer 3, a light emitting layer 4 and an electron transporting layer and/or an electron injecting layer 5, or a light emitting layer 6 having the charge transporting function is formed using the aforementioned respective materials by a vacuum-deposition method, or is formed on a transparent electrode 2 using a coating solution obtained by dissolving or dispersing the aforementioned respective materials in a suitable organic solvent by a spin-coating method, a casting method, a dipping method or the like.


[0257] Thicknesses of a hole transporting layer and/or hole injecting layer 3, a light emitting layer 4, an electron transporting layer and/or an electron injecting layer 5, as well as a light emitting layer 6 having the charge transporting function are preferably in the range of 10 μm or smaller, particularly 0.001 to 5 μm, respectively. The dispersed state for the aforementioned respective materials (non-conjugated polymer, light emitting material etc.) may be the state where materials are dispersed at a molecular level, or the state where fine particles such as fine crystals are dispersed. In the case of a method of forming a film using a coating solution, in order to obtain the state of dispersion at a molecular level, it is necessary to select a dispersing solvent in view of the dispersing property and the solubility of the aforementioned respective materials. In order to obtain dispersion of fine particles, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer, ultrasound method and the like can be utilized.


[0258] Finally, in the case of the organic electroluminescent element shown in FIG. 1 and FIG. 2, the organic electroluminescent element of the invention is completed by forming a rear electrode 7 on an electron transporting layer and/or an electron injecting layer 5 by a vacuum-deposition method, or a sputtering method or the like. In addition, in the case of the organic electroluminescent element shown in FIGS. 3 and 4, the organic electroluminescent element of the invention is completed by forming a rear electrode 7 on a light emitting layer 6 having the charge transporting function by a vacuum-deposition method, a sputtering method or the like.



EXAMPLES

[0259] The present invention will be explained more specifically by way of Examples below. However, the invention is not limited the following Examples.



Example 1

[0260] By using a substrate (manufactured by Sanyosinku) in which an ITO film is formed on a glass substrate, subjecting this ITO film of a substrate to patterning by photolithography using a photomask on which a strip-like pattern is formed, and subjecting the patterned ITO film to etching treatment, a strip-like ITO electrode (width 2 mm) was formed. Then, this glass substrate equipped with an ITO electrode was washed with neutral detergent, pure water, acetone (for electronic industry, manufactured by Kanto Kagaku) and isopropanol (for electronic industry, manufactured by Kanto Kagaku) by adding ultrasound for each 5 minutes, and dried with a spin coater. Thereafter, the substrate was washed with ultraviolet-ray ozone.


[0261] Then, a solution obtained by filtering dichloroethane containing 5% by weight of a non-conjugated polymer [exemplified compound (11)] with a PTFE filter having an opening of 0.1 μm, was coated on the surface of an ITO electrode of a substrate equipped with the ITO electrode, whereby, a light emitting layer of a thickness of 0.100 μm having the charge transporting layer function was formed.


[0262] Finally, a metal mask on which a strip-like hole is provided was arranged on the surface of a light emitting layer having the charge transporting layer function, and a Mg—Ag alloy was deposited thereon by codeposition to form a rear electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross with the ITO electrode. An effective area of the formed organic electroluminescent element was 0.04 cm2.



Example 2

[0263] Dichloroethane containing 10% by weight of a mixture comprising 1 part by weight of the non-conjugated polymer [exemplified compound (11)] used in Example 1, 4 parts by weight of poly(N-vinylcarbazole) and 0.02 part by weight of the aforementioned dye compound (V-1), was filtered with a PTFE filter having an opening of 0.1 μm to prepare a solution.


[0264] Then, the above solution was coated on a surface of a side where an ITO electrode of a glass substrate equipped with an ITO electrode prepared and washed as in Example 1 was provided, by a spin coater method, to form a light emitting layer of a thickness of about 0.110 μm having the charge transporting function, which was sufficiently dried. Finally, a Mg—Ag alloy was deposited by codeposition on the surface of a light emitting layer having the charge transporting function as in Example 1, to form a rear electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross the ITO electrode. An effective area of the formed organic electroluminescent element was 0.04 cm2.



Example 3

[0265] A non-conjugated polymer [exemplified compound (15)] as a layer functioning as a hole transporting layer and a light emitting layer was formed at a thickness of 0.050 μm, on a surface of a side where an ITO electrode of a glass substrate equipped with an ITO electrode prepared and washed as in Example 1 was provided.


[0266] Then, a light emitting layer of a thickness of 0.065 μm containing the dye compound (V-1) and the dye compound (VI-1) was formed by a vacuum-deposition method and, further, on the surface of a light emitting layer, the following compound (VII-1) as an electron transporting layer was formed at a thickness of 0.030 μm by a vacuum deposition method.


[0267] Finally, a Mg—Ag alloy was deposited by codeposition, on the surface of an electron transporting layer as in Example 1, to form a rear electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross with the ITO electrode. An effective area of the formed organic electroluminescent element was 0.04 cm2.
1343



Example 4

[0268] According to the same manner as that of Example 1 except that an exemplified compound (59) was used in place of an exemplified compound (11) used in Example 1, an organic electroluminescent element was prepared.



Example 5

[0269] According to the same manner as that of Example 2 except that an exemplified compound (87) was used in place of an exemplified compound (11) used in Example 2, an organic electroluminescent element was prepared.



Example 6

[0270] According to the same manner as that of Example 3 except that an exemplified compound (103) was used in place of an exemplified compound (11) used in Example 1, an organic electroluminescent element was prepared.



Example 7

[0271] According to the same manner as that of Example 3 except that an exemplified compound (110) was used in place of an exemplified compound (11) used in Example 1, an organic electroluminescent element was prepared.



Example 8

[0272] According to the same manner as that of Example 3 except that an exemplified compound (165) was used in place of an exemplified compound (11) used in Example 1, an organic electroluminescent element was prepared.



Example 9

[0273] According to the same manner as that of Example 3 except that an exemplified compound (166) was used in place of an exemplified compound (11) used in Example 1, an organic electroluminescent element was prepared.



Example 10

[0274] According to the same manner as that of Example 3 except that an exemplified compound (190) was used in place of an exemplified compound (11) used in Example 1, an organic electroluminescent element was prepared.



Comparative Example 1

[0275] Dichloroethane containing 2% by weight of polyvinylcarbazole (PVK) was filtered with a PTFE filter having an opening of 0.1 μm to prepare a solution. Then, the above solution was coated on the surface of a side where an ITO electrode of a glass substrate equipped with an ITO electrode prepared and washed as in Example 1 was provided, by a dipping method, to form a hole transporting layer having a thickness of 0.06 μm, which was sufficiently dried. Then, a light emitting layer having a thickness of 0.05 μm comprising the dye compound (V-1) as a light emitting material was formed by a vacuum deposition method.


[0276] Finally, a Mg—Ag alloy was deposited by codeposition on the surface of this light emitting layer as in Example 1, to form a rear electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross with the ITO electrode. An effective area of the formed organic EL element was 0.04 cm .



Comparative Example 2

[0277] A dichloroethane solution containing 10% by weight of a mixture obtained by mixing 2 parts by weight of polyvinylcarbazole (PVK), 0.1 part by weight of the dye compound (VI-1) as a light emitting material, and 1 part by weight of the above compound (VII-1) as an electron transporting material, was filtered with a PTFE filter having an opening of 0.1 μm, to prepare a solution.


[0278] Then, the above solution was coated on the surface of a side where an ITO electrode of a glass substrate equipped with an ITO electrode prepared and washed as in Example 1 was provided, by a dipping method, to form a hole transporting layer having a thickness of 0.15 μm, which was sufficiently dried. Finally, a Mg—Ag alloy was deposited by codeposition on the surface of this hole transporting layer as in Example 1, to form a rear electrode having a width of 2 mm and a thickness of 0.15 μm so as to cross with the ITO electrode. An effective area of the formed organic EL element was 0.04 cm2.


[0279] -Assessment-


[0280] A direct voltage was applied to the thus prepared organic EL element in vacuum (133.3×10−3 Pa), in which an ITO electrode side was plus and a Mg—Ag rear electrode side was minus, and light emitting was measured, and the maximum luminance and the emission color were assessed. The results are shown in Table 108. In addition, a light emitting life of the organic EL element was measured in dry nitrogen. In assessment of a light emitting life, a current value was set so that the initial luminance became 100 cd/m2, and a time required for reduction of the luminance from an initial value to half by constant current driving was adopted as an element life (hour). The driving current density upon this is shown together with an element life in Table 108.
108TABLE 108DrivingcurrentElementEmissionLuminancedensitylifeColor(cd/m2)(mA/m2)(hour)Example 1Green11518175Example 2Green13020230Example 3Orange15018200Ecample 4Bluegreen14018170Example 5Bluegreen18021120Example 6Blue16520150Example 7Bluegreen10523210Example 8Blue20019260Example 9Green19024120Example 10Bluegreen15522150ComparativeGreen853180Example 1ComparativeGreen882990Example 2


[0281] As explained above, the organic electroluminescent element of the present invention is an electroluminescent element comprising one or more organic compound layers held between one pair of electrodes comprising an anode and a cathode, at least one of which is transparent or translucent, wherein at least one layer of the one or more organic compound layers contains at least one kind of non-conjugated polymer, and at least one of terminal groups of the non-conjugated polymer has a fluorescent substance emitting fluorescence in a solid state.


[0282] Thus, according to the invention, there can be provided an organic electroluminescent element which has the high luminance, the high efficiency and a long element life, and has little defect such as pinhole, and can be easily enlarged, using a light emitting non-conjugated polymer excellent in the heat resistance and solubility in and compatibility with a solvent and a resin.


Claims
  • 1. An organic electroluminescent element comprising at least one pair of electrodes comprising an anode and a cathode, at least one of which having light transmissive, and at least one organic compound layer disposed between the electrodes, wherein the at least one organic compound layer contains at least one kind of non-conjugated polymer having terminal groups, and at least one of terminal groups of the non-conjugated polymer contains a fluorescent substance emitting fluorescence in a solid state.
  • 2. An organic electroluminescent element according to claim 1, wherein the non-conjugated polymer is selected from the group consisting of polyester, polyether and polyurethane.
  • 3. An organic electroluminescent element according to claim 1, wherein the non-conjugated polymer is a hole transporting polymer.
  • 4. An organic electroluminescent element according to claim 1, wherein the non-conjugated polymer comprises a repetition unit containing at least one partial structure selected from the group consisting of -the following general formulas (I-1) and (I-2),
  • 5. An organic electroluminescent element according to claim 1, wherein the at least one organic compound layer comprises 2 or more layers including at least a light emitting layer, and the light emitting layer contains at least one kind of the non-conjugated polymer.
  • 6. An organic electroluminescent element according to claim 5, wherein the at least one organic compound layer has a construction selected from the group consisting of a construction comprising the light emitting layer and an electron transporting layer, a construction comprising the light emitting layer and an electron injecting layer, and a construction comprising the light emitting layer, an electron transporting layer and an electron injecting layer.
  • 7. An organic electroluminescent element according to claim 5, wherein the at least one organic compound layer has a construction selected from the group consisting of a construction comprising the light emitting layer and a hole transporting layer, a construction comprising the light emitting layer and a hole injecting layer, and a construction comprising the light emitting layer, a hole transporting layer and a hole injecting layer.
  • 8. An organic electroluminescent element according to claim 5, wherein the at least one organic compound layer has a construction selected from the group consisting of a construction comprising the light emitting layer, a hole transporting layer and an electron transporting layer, a construction comprising the light emitting layer, a hole transporting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole transporting layer, an electron transporting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole injecting layer and an electron transporting layer, a construction comprising the light emitting layer, a hole injecting layer and an electron injecting layer, a construction comprising a light emitting layer, a hole injecting layer, an electron transporting layer and an electron injecting layer, a construction comprising the light emitting layer, a hole transporting layer, a hole injecting layer and an electron transporting layer, a construction comprising the light emitting layer, a hole transporting layer, a hole injecting layer and an electron injecting layer, and a construction comprising the light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer and an electron injecting layer.
  • 9. An organic electroluminescent element according to claim 1, wherein the at least one organic compound layer is composed only of a light emitting layer having a charge transporting function, and the light emitting layer having the charge transporting function contains one or more kinds of non-conjugated polymers.
  • 10. An organic electroluminescent element according to claim 4, wherein the non-conjugated polymer is a polyester selected from the group consisting of the following general formulas (II-1) and (II-2),
  • 11. An organic electroluminescent element according to claim 4, wherein the non-conjugated polymer is a polyether represented by the following general formula (III-1),
  • 12. An organic electroluminescent element according to claim 4, wherein the non-conjugated polymer is a polyurethane selected from the group consisting of the following general formulas (IV-1) and (IV-2),
  • 13. An organic electroluminescent element according to claim 1, wherein the fluorescent substance is an organic fluorescent substance.
  • 14. An organic electroluminescent element according to claim 13, wherein the organic fluorescent substance is selected from the group consisting of a compound including an aromatic hydrocarbon having an aromatic ring number of 2 or more, and a chelating metal complex.
  • 15. An organic electroluminescent element according to claim 14, wherein the compound including an aromatic hydrocarbon having an aromatic ring number of 2 or more is an organic fluorescent substance selected from the group consisting of a polyacene derivative compound, a styrylamine compound, a quinacridone derivative compound, a rublene derivative compound, a coumarin derivative compound and a pyran derivative compound.
  • 16. An organic electroluminescent element according to claim 15, wherein the polyacene derivative compound is selected from the group consisting of a naphthalene derivative, an anthracene derivative, a tetracene derivative, a perylene derivative and a pyrene derivative.
  • 17. An organic electroluminescent element according to claim 14, wherein the chelating metal complex contains a metal selected from the group consisting of Al, Zn, Be, Mg, Eu, Ga, Pt and Ir.
  • 18. An organic electroluminescent element according to claim 1, wherein a maximum peak wavelength in a fluorescent spectrum of the fluorescent substance is in the visible light region.
  • 19. An organic electroluminescent element according to claim 1, wherein both terminal groups of the non-conjugated polymer contain a fluorescent substance emitting fluorescence in a solid state.
  • 20. An organic electroluminescent element according to claim 1, wherein emission colors of the fluorescent substances emitting fluorescence in a solid state and respectively contained in the terminal groups are different from each other.
Priority Claims (1)
Number Date Country Kind
2002-271831 Sep 2002 JP