JP5247024B2 - Organic light emitting device - Google Patents

Description

  The present invention relates to an organic light emitting device. More specifically, the present invention relates to an organic light-emitting device capable of obtaining high luminance and long life as well as high luminous efficiency by using a polymer compound containing a structural unit derived from a specific polymerizable compound having a hole transporting property. About.

  As an organic light-emitting device, a multi-layer device in which a light-emitting layer made of a phosphorescent low-molecular compound is provided between a hole transport layer and an electron transport layer is known. Low molecular weight compounds such as phenylamine derivatives are used (see Patent Document 1).

  However, when forming each layer as described above using a low molecular weight compound, a vacuum deposition method is generally used, but this requires vacuum equipment, and the film thickness of the layer tends to be uneven. There were problems such as difficulty in increasing the area. In addition, an organic light emitting device using a light emitting layer obtained from a phosphorescent low molecular weight compound has a problem of poor durability.

On the other hand, a phosphorescent polymer compound obtained by copolymerizing a phosphorescent polymerizable compound and a charge transporting polymerizable compound has also been developed. Use of such a phosphorescent polymer compound has an advantage that a light emitting layer can be formed by a coating method such as spin coating. For example, Patent Document 2 discloses a copolymer of a triphenylamine derivative and an iridium complex.
JP 2003-308978 A JP-A-2005-97589

However, although the above-described polymer compound can provide high luminous efficiency, there is room for improvement in terms of maximum brightness and life.
Accordingly, an object of the present invention is to provide an organic light emitting device having high luminance and long life as well as high luminous efficiency.

  As a result of diligent research to solve the above problems, the inventors of the present invention have achieved high luminance and long life as well as high luminous efficiency by a polymer compound containing a structural unit derived from a specific polymerizable compound having hole transportability. The present inventors have found that an organic light-emitting device having the above can be obtained, and have completed the present invention.

That is, the present invention is summarized as follows.
[1] In an organic light emitting device in which at least one organic compound layer including a light emitting layer is sandwiched between an anode and a cathode, and a phosphorescent compound contained in the light emitting layer emits light,
An organic light emitting device, wherein the light emitting layer is a light emitting layer containing a polymer compound having a structural unit derived from a polymerizable compound (A) represented by the following general formula (1).

(In formula (1), at least one of R ^{1 to} R ²⁴ represents a substituent having a polymerizable functional group,
R ^{1 to} R ²⁴ which are not substituents having the polymerizable functional group are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a carbazole group, and a silyl group, R ^{1 to} R ⁵ , In each of R ^{6 to} R ¹⁰ , R ^{11 to} R ¹⁵ , R ^{16 to} R ²⁰ and R ^{21 to} R ²³ , two groups bonded to adjacent carbon atoms on the benzene ring are bonded to each other and condensed. A ring may be formed. )
[2] The organic light-emitting element according to the above [1], wherein the polymer compound further has a structural unit derived from the phosphorescent polymerizable compound (B).

  [3] The polymer compound further includes a structural unit derived from a phosphorescent polymerizable compound (B) and a structural unit derived from an electron transporting polymerizable compound (C). 1].

  [4] The organic light-emitting device according to the above [2] or [3], wherein the phosphorescent polymerizable compound (B) is a complex represented by the following general formula (2-1): .

(In Formula (2-1), R ^{31 to} R ³⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 1 carbon atom. Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by 10 to 10 alkyl groups, an alkoxy group having 1 to 10 carbon atoms, and a silyl group, and R ³¹ and R ³² represent R ³² And R ³³ , R ³³ and R ³⁴ , R ³⁴ and R ³⁵ , R ³⁵ and R ³⁶ , R ³⁶ and R ³⁷ , R ³⁷ and R ³⁸ , A condensed ring may be formed, and L represents a bidentate ligand selected from the group consisting of the following general formulas (2-2) to (2-4).

(In Formula (2-2), at least one of R ^{41 to} R ⁴⁸ represents a substituent having a polymerizable functional group, and R ^{41 to} R ⁴⁸ that is not a substituent having the polymerizable functional group are: Each independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, R ⁴¹ and R ⁴² , R ⁴² and R ⁴³ , R ⁴³ and R ⁴⁴ , R ⁴⁴ And R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁴⁶ and R ⁴⁷ , and R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a condensed ring.

(In Formula (2-3), at least one of R ^{51 to} R ⁵³ represents a substituent having a polymerizable functional group, and R ^{51 to} R ⁵³ which is not a substituent having the polymerizable functional group is Each independently a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, represents 10 alkoxy groups, and atom or a substituent selected from the group consisting of silyl group, at the R ⁵¹ and R ^52, between R ⁵² and R ^53, may form a fused ring bond to each other .)

(In the formula (2-4), at least one of R ^{61 to} R ⁶⁴ represents a substituent having a polymerizable functional group, and R ^{61 to} R ⁶⁴ that are not a substituent having the polymerizable functional group are: Each independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, and R ⁶¹ and R ⁶² , R ⁶² and R ⁶³ , R ⁶³ and R ⁶⁴ are bonded to each other To form a condensed ring.)
[5] The organic light-emitting element according to the above [1], wherein the light-emitting layer further contains a phosphorescent compound (E).

[6] The light emitting layer further includes a phosphorescent compound (E), and the polymer compound further includes a structural unit derived from the electron transport polymerizable compound (C). Item 2. The organic light-emitting device according to Item 1.

  [7] The organic light-emitting device according to [3] or [6], wherein the electron-transporting polymerizable compound (C) is an oxadiazole derivative, a triazole derivative, or a triarylborane derivative.

[8] A surface-emitting light source using the organic light-emitting device according to any one of [1] to [7].
[9] An image display device using the organic light-emitting device according to any one of [1] to [7].

  [10] A polymer compound having a structural unit derived from a polymerizable compound (A) represented by the following general formula (1).

(In formula (1), at least one of R ^{1 to} R ²⁴ represents a substituent having a polymerizable functional group,
R ^{1 to} R ²⁴ which are not substituents having the polymerizable functional group are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a carbazole group, and a silyl group, R ^{1 to} R ⁵ , In each of R ^{6 to} R ¹⁰ , R ^{11 to} R ¹⁵ , R ^{16 to} R ²⁰ and R ^{21 to} R ²³ , two groups bonded to adjacent carbon atoms on the benzene ring are bonded to each other and condensed. A ring may be formed. )
[11] The above-mentioned [10], wherein the polymer compound has a structural unit derived from a phosphorescent polymerizable compound (B) represented by the following general formula (2-1): High molecular compound.

(In Formula (2-1), R ^{31 to} R ³⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 1 carbon atom. Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by 10 to 10 alkyl groups, an alkoxy group having 1 to 10 carbon atoms, and a silyl group, and R ³¹ and R ³² represent R ³² And R ³³ , R ³³ and R ³⁴ , R ³⁴ and R ³⁵ , R ³⁵ and R ³⁶ , R ³⁶ and R ³⁷ , R ³⁷ and R ³⁸ , A condensed ring may be formed, and L represents a bidentate ligand selected from the group consisting of the following general formulas (2-2) to (2-4).

(In formula (2-2), at least one of R ^{41 to} R ⁴⁸ represents a substituent having a polymerizable functional group, and R ^{41 to} R ⁴⁸ that are not substituents having the polymerizable functional group are Independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, or a carbon number Represents an atom or substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, R ⁴¹ and R ⁴² , R ⁴² and R ⁴³ , R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁴⁶ and R ⁴⁷ , and R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a condensed ring.

(In Formula (2-3), at least one of R ^{51 to} R ⁵³ represents a substituent having a polymerizable functional group, and each of R ^{51 to} R ⁵³ that is not a substituent having the polymerizable functional group is Independently, a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, or 1 to 10 carbon atoms of an alkoxy group, and atom or a substituent selected from the group consisting of silyl group, at the R ⁵¹ and R ^52, between R ⁵² and R ^53, may form a fused ring bond to each other. )

(In Formula (2-4), at least one of R ^{61 to} R ⁶⁴ represents a substituent having a polymerizable functional group, and R ^{61 to} R ⁶⁴ that are not a substituent having the polymerizable functional group are Independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, or a carbon number Represents an atom or a substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, R ⁶¹ and R ⁶² , R ⁶² and R ⁶³ , R ⁶³ and R ⁶⁴ bonded to each other; To form a condensed ring.)

  The organic light emitting device of the present invention has high luminance and long life as well as high luminous efficiency.

Hereinafter, the present invention will be specifically described.
1. Light emitting layer The organic light emitting device of the present invention comprises an organic light emitting device in which at least one organic compound layer including a light emitting layer is sandwiched between an anode and a cathode, and a phosphorescent compound contained in the light emitting layer emits light. The light emitting layer is a light emitting layer containing a specific polymer compound. The polymer compound is a novel polymer compound having a structural unit derived from the hole transport polymerizable compound (A) represented by the formula (1). The polymer compound may further have a structural unit derived from the phosphorescent polymerizable compound (B) and / or a structural unit derived from the electron-transporting polymerizable compound (C). These polymer compounds polymerize a hole transport polymerizable compound (A) and, if necessary, a phosphorescent polymerizable compound (B) and / or an electron transport polymerizable compound (C). Is obtained.

Specifically, the polymer compound is a polymer compound (I) polymerized using the polymerizable compound (A) represented by the formula (1) and the phosphorescent polymerizable compound (B). Even so,
A polymer compound (II) polymerized by using the polymerizable compound (A) represented by the above formula (1), the phosphorescent polymerizable compound (B) and the electron transporting polymerizable compound (C). Even so,
Even the polymer compound (III) polymerized using the polymerizable compound (A) represented by the above formula (1),
The polymer compound (IV) polymerized using the polymerizable compound (A) represented by the above formula (1) and the electron transporting polymerizable compound (C) may be used.

  When the polymer compound having a structural unit derived from the compound (A) also has a structural unit derived from the phosphorescent polymerizable compound (B) (for example, the polymer compound (I), (II In the case of), the light emitting layer can be formed by the polymer compound alone.

  On the other hand, when the polymer compound having a structural unit derived from the compound (A) does not have a structural unit derived from the phosphorescent polymerizable compound (B) (for example, the polymer compound (III), In the case of (IV), a light-emitting layer is formed using a phosphorescent low-molecular compound (E) together with the polymer compound.

  Like the polymer compounds (I) to (IV), the novel polymer compound having a structural unit derived from the compound (A) is excellent in hole transportability, and in any of the above cases, Since the polymer compound is used, an organic light-emitting device having high luminance and long lifetime with high luminous efficiency can be obtained.

In this specification, the hole-transporting polymerizable compound and the electron-transporting polymerizable compound are also collectively referred to as a “carrier-transporting polymerizable compound”.
In the compound (A) used in the present invention, at least one of R ^{1 to} R ²⁴ represents a substituent having a polymerizable functional group, and R ^{1 to} R ²⁴ which is not a substituent having the polymerizable functional group is Independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, The atom or substituent selected from the group which consists of a C1-C10 alkoxy group, a carbazole group, and a silyl group is represented. A compound (A) may be used independently or may be used in combination of 2 or more type.

As said halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is mentioned.
Examples of the alkyl group having 1 to 10 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, amyl group, hexyl group, octyl group, and decyl group. Can be mentioned.

Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a mesityl group, and a naphthyl group.
Examples of the amino group that may be substituted with the alkyl group having 1 to 10 carbon atoms include an amino group, a dimethylamino group, a diethylamino group, and a dibutylamino group.

  Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a t-butoxy group, a hexyloxy group, a 2-ethylhexyloxy group, and a decyloxy group. Etc.

The carbazole group may have a substituent such as a methyl group, an ethyl group, a t-butyl group, or a methoxy group.
Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, and a trimethoxysilyl group.

Among these, a hydrogen atom, a fluorine atom, a cyano group, a methyl group, a t-butyl group, a dimethylamino group, a methoxy group, and a carbazole group are preferable. Specifically, from the viewpoint of the lifetime and efficiency of the organic light emitting device, at least one of R ² , R ⁷ , R ¹² and R ¹⁷ is independently a methyl group, a dimethylamino group, a methoxy group or a carbazole group. R ^{1 to} R ²⁴ except for a group having a polymerizable functional group and R ^{1 to} R ²⁴ are preferably hydrogen atoms, R ² , R ⁷ ,
More preferably, R ¹² and R ¹⁷ are each independently a methyl group, a dimethylamino group, a methoxy group, or a carbazole group, and R ^{1 to} R ²⁴ excluding these groups and substituents having a polymerizable functional group are hydrogen atoms. preferable. From the viewpoint of the lifetime and efficiency of the organic light emitting device, at least one of R ³ , R ⁸ , R ¹³ and R ¹⁸ is independently a methyl group, a dimethylamino group, a methoxy group or a carbazole group. R ^{1 to} R ²⁴ excluding a substituent having a polymerizable functional group are preferably hydrogen atoms, and R ³ , R ⁸ , R ¹³ and R ¹⁸ are each independently a methyl group, a dimethylamino group, a methoxy group or a carbazole. It is more preferable that R ^{1 to} R ^{24 other} than the substituents having these groups and polymerizable functional groups are hydrogen atoms.

In each of R ^{1 to} R ⁵ , R ^{6 to} R ¹⁰ , R ^{11 to} R ¹⁵ , R ^{16 to} R ^20, and R ^{21 to} R ²³ , two groups bonded to adjacent carbon atoms on the benzene ring are , May combine with each other to form a condensed ring.

At least one of R ^{1 to} R ²⁴ represents a substituent having a polymerizable functional group.
The substituent is not particularly limited as long as it has a polymerizable functional group, and examples thereof include the substituents described above.

  The polymerizable functional group may be any of radical polymerizable, cationic polymerizable, anionic polymerizable, addition polymerizable, and condensation polymerizable functional groups. Of these, the radical polymerizable functional group is preferable because the production of the polymer is easy.

Examples of the polymerizable functional group include urethane (meth) acrylate groups such as allyl group, alkenyl group, acrylate group, methacrylate group, methacryloyloxyethyl carbamate group, vinylamide group, and derivatives thereof. Of these, alkenyl groups are preferred.

  Taking the case where the polymerizable functional group is an alkenyl group as an example, the compound (A) specifically has an alkenyl group as a substituent represented by the following formulas (a1) to (a13). Is more preferable. Among these, substituents represented by the following formulas (a1), (a5), (a8), (a12), and (a13) are more preferable because functional groups can be easily introduced into the compound.

When the polymerizable functional group is a functional group other than an alkenyl group, those in which the alkenyl group in the above formulas (a1) to (a13) is substituted with the functional group are preferable.
In the compound (A), R ²² is preferably a substituent having a polymerizable functional group.

Such a compound (A) can be produced, for example, by a palladium-catalyzed substitution reaction of an m-phenylenediamine derivative and an aryl halide, or a diarylamine and an m-dibromobenzene derivative. Specific methods of the substitution reaction are described in, for example, Tetrahedron Letters, 1998, Vol. 39, page 2367.

  The compound (B) used in the present invention is not particularly limited as long as it has a substituent having a polymerizable functional group and is a low molecular compound that can emit light from a triplet excited state at room temperature. Palladium complexes, osmium complexes, iridium complexes, platinum complexes and gold complexes containing a substituent having a polymerizable functional group are preferred, iridium complexes and platinum complexes are more preferred, and iridium complexes are most preferred. The substituent having the polymerizable functional group is synonymous with the substituent having the polymerizable functional group in the compound (A), and the preferred range is also the same. A compound (B) may be used independently or may be used in combination of 2 or more type.

As the iridium complex, a complex represented by the above formula (2-1) is preferably used.
In the above formula (2-1), R ^{31 to} R ³⁸ each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 1 carbon atom. Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by 10 to 10 alkyl groups, an alkoxy group having 1 to 10 carbon atoms, and a silyl group. Specific examples thereof include the atoms and substituents described above.

R ^{31 to} R ³⁸ are preferably a hydrogen atom, a fluorine atom, a cyano group, a methyl group, a t-butyl group, a dimethylamino group, a butoxy group, or a 2-ethylhexyloxy group. Specifically, R ³² is preferably a t-butyl group, and R ^{31 to} R ³⁸ except R ³² are preferably hydrogen atoms.

R ³¹ and R ³² , R ³² and R ³³ , R ³³ and R ³⁴ , R ³⁴ and R ³⁵ , R ³⁵ and R ³⁶ , R ³⁶ and R ³⁷ , R ³⁷ And R ³⁸ may be bonded to each other to form a condensed ring. Examples of such a condensed ring include a naphthalene ring, anthracene ring, phenanthrene ring, pyrene ring, perylene ring, quinoline ring, isoquinoline ring, and naphthyridine ring.

L represents a bidentate ligand selected from the group consisting of the above formulas (2-2) to (2-4).
In the above formula (2-2), at least one of R ^{41 to} R ⁴⁸ represents a substituent having a polymerizable functional group, and R ^{41 to} R ⁴⁸ which is not a substituent having the polymerizable functional group is: Each independently represents the same atom or substituent as R ³¹ .

R ^{41 to} R ⁴⁸ are preferably a hydrogen atom, a fluorine atom, a cyano group, a methyl group, a t-butyl group, a dimethylamino group, a butoxy group, or a 2-ethylhexyloxy group.
R ⁴¹ and R ⁴² , R ⁴² and R ⁴³ , R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁴⁶ and R ⁴⁷ , R ⁴⁷ And R ⁴⁸ may be bonded to each other to form a condensed ring.

At least one of R ^{41 to} R ⁴⁸ represents a substituent having a polymerizable functional group, and the substituent having the polymerizable functional group has the same meaning as the substituent having a polymerizable functional group in the compound (A). And the preferred range is also the same.

In the above formula (2-3), at least one of R ^{51 to} R ⁵³ represents a substituent having a polymerizable functional group, and R ^{51 to} R ⁵³ which is not a substituent having the polymerizable functional group is Each independently represents the same atom or substituent as R ³¹ (excluding a halogen atom).

R ^{51 to} R ⁵³ are preferably a methyl group, a t-butyl group, a dimethylamino group, or a methoxy group.
R ⁵¹ and R ⁵² , and R ⁵² and R ⁵³ may be bonded to each other to form a condensed ring.

At least one of R ^{51 to} R ⁵³ represents a substituent having a polymerizable functional group, and the substituent having the polymerizable functional group has the same meaning as the substituent having a polymerizable functional group in the compound (A). And the preferred range is also the same.

In the above formula (2-4), at least one of R ^{61 to} R ⁶⁴ represents a substituent having a polymerizable functional group, and R ^{61 to} R ⁶⁴ that are not a substituent having the polymerizable functional group are: Each independently represents the same atom or substituent as R ³¹ .

R ^{61 to} R ⁶⁴ are preferably a hydrogen atom, a fluorine atom, a cyano group, a methyl group, a t-butyl group, a dimethylamino group, a butoxy group, or a 2-ethylhexyloxy group.
R ⁶¹ and R ⁶² , R ⁶² and R ⁶³ , and R ⁶³ and R ⁶⁴ may be bonded to each other to form a condensed ring.

At least one of R ^{61 to} R ⁶⁴ represents a substituent having a polymerizable functional group, and the substituent having the polymerizable functional group has the same meaning as the substituent having a polymerizable functional group in the compound (A). And the preferred range is also the same.

  The iridium complex represented by the above formula (2-1) is produced, for example, as follows. First, a specific bidentate ligand is reacted with an iridium compound (0.5 equivalent) such as iridium chloride in a solvent such as 2-ethoxyethanol. Next, the obtained bidentate ligand having a metal complex and a polymerizable functional group is heated together with sodium carbonate in a solvent such as 2-ethoxyethanol, and then purified to obtain the above formula (2-1). The iridium complex represented is obtained. The bidentate ligand having a polymerizable functional group can be obtained by a known method.

  The compound (C) used in the present invention is not particularly limited as long as it contains a substituent having a polymerizable functional group, and a known electron transporting compound is used. Of these, oxadiazole derivatives, triazole derivatives or triarylborane derivatives are preferably used. A compound (C) may be used independently or may be used in combination of 2 or more type.

  Specific examples of the compound (C) include the following compounds (C1) to (C9).

The substituent having the polymerizable functional group is synonymous with the substituent having the polymerizable functional group in the compound (A), and the preferred range is also the same.
Such a compound (C) can be produced by a known method.

  In addition, when manufacturing the said high molecular compound, you may use another polymeric compound further. Examples of the other polymerizable compounds include compounds having no carrier transport properties such as (meth) acrylic acid alkyl esters such as methyl acrylate and methyl methacrylate, and styrene and derivatives thereof. It is not limited.

The method for producing the polymer compound may be any of radical polymerization, cationic polymerization, anionic polymerization and addition polymerization, but radical polymerization is preferred.
The weight average molecular weight of the polymer compound is usually 1,000 to 2,000,000, preferably 5,000 to 1,000,000. When the weight average molecular weight is in this range, the polymer compound is soluble in an organic solvent, and a uniform thin film can be obtained. Here, the weight average molecular weight is a value measured at 40 ° C. using tetrahydrofuran as a solvent by gel permeation chromatography (GPC).

  In the polymer compounds (I) and (II), the number of structural units derived from the compound (B) is m, and the number of structural units derived from the carrier transportable polymerizable compound (in the polymer compound (I) Is the total number of structural units derived from the compound (A). In the polymer compound (II), when the total number of structural units derived from the compound (A) and the compound (C) is n (m and n are The ratio of the number of structural units derived from the compound (B) to the total number of structural units, that is, the value of m / (m + n) is preferably in the range of 0.001 to 0.5. More preferably, it is in the range of 0.001 to 0.2. When the value of m / (m + n) is within this range, an organic light emitting device having high luminous efficiency with high carrier mobility and low influence of concentration quenching can be obtained.

In the polymer compounds (II) and (IV), when the number of structural units derived from the compound (A) is x and the number of structural units derived from the compound (C) is y (x and y are integers of 1 or more) And n = x + y is established between n and the above. The optimum value x / n of the number of structural units derived from the compound (A) and the ratio y / n of the number of structural units derived from the compound (C) to the number of structural units derived from the carrier transporting compound are It depends on the charge transport capacity and concentration of the structural unit. When forming the light emitting layer of an organic light emitting element only with this high molecular compound (II), it is preferable that the value of x / n and y / n is in the range of 0.05-0.95, respectively. More preferably, it is in the range of 20 to 0.80. When the light emitting layer is formed using the polymer compound (IV) and the phosphorescent low molecular compound (E), the values of x / n and y / n are 0.05 to 0.95, respectively. Is preferably in the range of 0.20 to 0.80. Here, x / n + y / n = 1 holds. The proportion of each structural unit in the polymer compound as described above is estimated by ICP elemental analysis and ¹³ C-NMR measurement.

  If the ratio of the compound (A), the compound (B) used as necessary, and the compound (C) is appropriately set, the desired polymer compound can be obtained, and the polymer compound is a random copolymer, Either a block copolymer or an alternating copolymer may be used.

  When the light emitting layer is formed using the polymer compound (I) obtained by polymerizing the compound (A) and the compound (B), an electron transport layer may be provided separately, but with the polymer compound (I) The light emitting layer is preferably formed using an electron transporting compound. The electron transporting compounds may be used alone or in combination of two or more. As the electron transporting compound, known compounds as described later are used, and oxadiazole derivatives and triarylborane derivatives are preferably used. In this case, the light emitting layer preferably contains the electron transporting compound in an amount of 5 to 95 parts by weight, more preferably 20 to 80 parts by weight with respect to 100 parts by weight of the polymer compound (I). desirable.

  Moreover, when forming a light emitting layer using the high molecular compound (II) obtained by superposing | polymerizing a compound (A), a compound (B), and a compound (C), a light emitting layer can be formed only with this high molecular compound. .

On the other hand, when forming a light emitting layer using polymer compound (III), it is preferable to form a light emitting layer using phosphorescent compound (E) with polymer compound (III). The phosphorescent compound (E) may be used alone or in combination of two or more. In addition, you may provide an electron carrying layer separately and you may form a light emitting layer using the said electron transport compound with the high molecular compound (III) and the said phosphorescence-emitting compound (E). As the phosphorescent compound (E), a known compound is used, and an iridium complex is preferably used. Specifically, the following complexes (E-1) to (E-39) are mentioned.

  In this case, the light emitting layer is preferably 1 to 50 parts by weight, more preferably 5 to 20 parts by weight of the phosphorescent low molecular weight compound (E) with respect to 100 parts by weight of the polymer compound (III). It is desirable to include by quantity. Further, when the light emitting layer further contains an electron transporting compound, the electron transporting compound is preferably 5 to 95 parts by weight, more preferably 20 parts by weight with respect to 100 parts by weight of the polymer compound (III). It is desirable to include it in an amount of ˜80 parts by weight.

  In the case where the light emitting layer is formed using the polymer compound (IV) obtained by polymerizing the compound (A) and the compound (C), as in the case of the polymer compound (III), the polymer compound ( It is preferable to form a light emitting layer using the phosphorescent compound (E) as described above together with IV). In this case, the light emitting layer is preferably 1 to 50 parts by weight, more preferably 5 to 20 parts by weight of the phosphorescent low molecular weight compound (E) with respect to 100 parts by weight of the polymer compound (IV). It is desirable to include by quantity.

  When forming a light emitting layer using polymer compound (I), it does not specifically limit as a manufacturing method of a light emitting layer, For example, it can manufacture as follows. First, a solution in which the polymer compound (I) and, if necessary, the electron transporting compound are dissolved is prepared. The solvent used for the preparation of the solution is not particularly limited. For example, a chlorine solvent such as chloroform, methylene chloride, dichloroethane, an ether solvent such as tetrahydrofuran and anisole, an aromatic hydrocarbon solvent such as toluene and xylene, Ketone solvents such as acetone and methyl ethyl ketone, and ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate are used. Next, the solution thus prepared is subjected to spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, and screen printing. The film is formed on the substrate by a wet film forming method such as a flexographic printing method, an offset printing method, or an ink jet printing method. For example, in the case of a spin coat method or a dip coat method, the solution may contain the polymer compound (I) in an amount of 0.5 to 5% by weight, depending on the compound used and the film formation conditions. Preferably, when the electron transporting compound is used, the compound is preferably contained in an amount of 0.1 to 3% by weight. Further, when the light emitting layer is formed using the polymer compound (II), the light emitting layer can be formed in the same manner as in the case of the polymer compound (I).

  On the other hand, when the light emitting layer is formed using the polymer compound (III), first, the polymer compound (III), the phosphorescent compound (E), and, if necessary, the electron transporting compound are dissolved. Prepare the solution. The solvent used for preparing the solution is the same as described above. Next, the solution prepared in this manner is formed on a substrate in the same manner as described above. For example, in the case of a spin coating method or a dip coating method, the solution contains the polymer compound (III) in an amount of 0.5 to 5% by weight and is phosphorescent. The luminescent compound (E) is preferably contained in an amount of 0.01 to 2% by weight, and when the above electron transporting compound is used, the compound may be contained in an amount of 0.1 to 3% by weight. preferable. Moreover, also when forming a light emitting layer using polymer compound (IV), a light emitting layer can be formed similarly to the case of polymer compound (III).

2. Organic Light-Emitting Element The organic light-emitting element according to the present invention includes at least one organic layer sandwiched between an anode and a cathode, and at least one of the organic layers includes a specific light-emitting layer as described above. In the present invention, the light emitting layer can be formed by a simple coating method as described above, and the area of the device can be increased.

  An example of the configuration of the organic light emitting device according to the present invention is shown in FIG. 1, but the configuration of the organic light emitting device according to the present invention is not limited thereto. In FIG. 1, the hole transport layer (3), the light emitting layer (4) and the electron transport layer (5) are disposed between the anode (2) and the cathode (6) provided on the transparent substrate (1). In order. In the organic light emitting device, for example, any of 1) a hole transport layer / the light emitting layer and 2) the light emitting layer / electron transport layer may be provided between the anode (2) and the cathode (6). 3) a layer containing a hole transport material, a light emitting material, an electron transport material, 4) a layer containing a hole transport material, a light emitting material, 5) a layer containing a light emitting material, an electron transport material, 6) Any one of the layers may be provided. Further, two or more light emitting layers may be stacked.

  In the element as described above, when the light emitting layer has both hole transporting property, electron transporting property and phosphorescent light emitting property, even if no other organic material layer is provided, organic light emitting having high light emitting efficiency and durability. An element can be manufactured. In addition, the manufacturing process can be further simplified.

  Each of the above layers may be formed by mixing a polymer material or the like as a binder. Examples of the polymer material include polymethyl methacrylate, polycarbonate, polyester, polysulfone, and polyphenylene oxide.

  In addition, the hole transport material and the electron transport material used in each of the above layers may be formed independently, or may be formed by mixing materials having different functions. Also in the light emitting layer in the organic light emitting device according to the present invention, in addition to the polymer compound according to the present invention, other hole transport materials and / or electron transport materials are further included for the purpose of supplementing the carrier transport property. Also good. Such a transport material may be a low molecular compound or a high molecular compound.

As the hole transport material forming the hole transport layer or the hole transport material mixed with the light emitting layer, for example, TPD (N, N′-dimethyl-N, N ′-(3-methylphenyl) -1 , 1′-biphenyl-4,4′diamine); α-NPD (4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl); m-MTDATA (4,4 ′, 4 Low molecular weight triphenylamine derivatives such as '' -tris (3-methylphenylphenylamino) triphenylamine); polyvinylcarbazole; a polymer compound obtained by polymerizing a triphenylamine derivative by introducing a polymerizable functional group; Examples thereof include fluorescent compounds such as phenylene vinylene and polydialkylfluorene. Examples of the polymer compound include a polymer compound having a triphenylamine skeleton disclosed in JP-A-8-157575. The above hole transport materials may be used singly or in combination of two or more, or different hole transport materials may be laminated and used. The thickness of the hole transport layer depends on the conductivity of the hole transport layer, but is usually preferably 1 nm to 5 μm, more preferably 5 nm to 1 μm, and particularly preferably 10 nm to 500 nm.

  Examples of the electron transport material forming the electron transport layer or the electron transport material mixed with the light emitting layer include quinolinol derivative metal complexes such as Alq3 (aluminum trisquinolinolate), oxadiazole derivatives, triazole derivatives, and imidazole derivatives. And low molecular compounds such as triazine derivatives and triarylborane derivatives; and polymer compounds obtained by introducing a polymerizable substituent into the above low molecular compounds. Examples of the polymer compound include poly PBD disclosed in JP-A-10-1665. The electron transport materials may be used singly or in combination of two or more, or different electron transport materials may be laminated and used. Although the thickness of the electron transport layer depends on the conductivity of the electron transport layer, etc., it is usually preferably 1 nm to 5 μm, more preferably 5 nm to 1 μm, and particularly preferably 10 nm to 500 nm.

  In addition, a hole / blocking layer is provided adjacent to the cathode side of the light emitting layer for the purpose of preventing holes from passing through the light emitting layer and efficiently recombining holes and electrons in the light emitting layer. It may be. For forming the hole blocking layer, a known material such as a triazole derivative, an oxadiazole derivative, or a phenanthroline derivative is used.

  A buffer layer may be provided between the anode and the hole transport layer or between the anode and the organic layer stacked adjacent to the anode in order to relax the injection barrier in hole injection. In order to form the buffer layer, a known material such as copper phthalocyanine, a mixture of polyethylene dioxythiophene and polystyrene sulfonic acid (PEDOT: PSS) is used.

  An insulating layer having a thickness of 0.1 to 10 nm is provided between the cathode and the electron transport layer or between the cathode and the organic layer laminated adjacent to the cathode in order to improve the electron injection efficiency. May be. In order to form the insulating layer, known materials such as lithium fluoride, sodium fluoride, magnesium fluoride, magnesium oxide, and alumina are used.

  As the anode material used for the organic light emitting device according to the present invention, for example, a known transparent conductive material such as ITO (indium tin oxide), tin oxide, zinc oxide, polythiophene, polypyrrole, polyaniline, or other conductive polymer is preferably used. Used. The surface resistance of the electrode formed of the transparent conductive material is preferably 1 to 50Ω / □ (ohm / square). The thickness of the anode is preferably 50 to 300 nm.

  Examples of the cathode material used in the organic light emitting device according to the present invention include alkali metals such as Li, Na, K, and Cs; alkaline earth metals such as Mg, Ca, and Ba; Al; MgAg alloys; AlLi, AlCa, and the like. A known cathode material such as an alloy of Al and an alkali metal or alkaline earth metal is preferably used. The thickness of the cathode is preferably 10 nm to 1 μm, more preferably 50 to 500 nm. When a highly active metal such as an alkali metal or alkaline earth metal is used, the thickness of the cathode is preferably 0.1 to 100 nm, more preferably 0.5 to 50 nm. In this case, a metal layer that is stable to the atmosphere is laminated on the cathode for the purpose of protecting the cathode metal. Examples of the metal forming the metal layer include Al, Ag, Au, Pt, Cu, Ni, and Cr. The thickness of the metal layer is preferably 10 nm to 1 μm, more preferably 50 to 500 nm.

  As the substrate of the organic light emitting device according to the present invention, an insulating substrate transparent to the emission wavelength of the light emitting material is preferably used. Specifically, in addition to glass, PET (polyethylene terephthalate), polycarbonate, etc. Transparent plastics are used.

  Examples of film formation methods for the hole transport layer and the electron transport layer include, for example, dry film formation methods such as resistance heating vapor deposition, electron beam vapor deposition, and sputtering, as well as spin coating, casting, and microgravure coating. , Gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, etc. Can be used. In the case of a low molecular compound, a dry film forming method is suitably used, and in the case of a polymer compound, a wet film forming method is suitably used.

  In addition, as a method for forming the anode material, for example, an electron beam evaporation method, a sputtering method, a chemical reaction method, a coating method, or the like is used. As a method for forming the cathode material, for example, a resistance heating evaporation method, An electron beam evaporation method, a sputtering method, an ion plating method, or the like is used.

3. Application The organic light-emitting device according to the present invention is suitably used in an image display device as a matrix-type or segment-type pixel by a known method. The organic light-emitting element is also suitably used as a surface light source without forming pixels.

  Specifically, the organic light emitting device according to the present invention is suitably used for displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like.

[Example]
EXAMPLES Hereinafter, although this invention is demonstrated further more concretely based on an Example, this invention is not limited to these Examples.

The polymer compound was analyzed by the following method.
(1) Molecular weight It carried out on the following conditions with the gel permeation chromatography (GPC) apparatus.
Column: Shodex KF-G + KF804L + KF802 + KF801
Eluent: Tetrahydrofuran (THF)
Temperature: 40 ° C
Detector: RI (Shodex RI-71)
(2) Composition analysis
¹³ C-NMR measurement was performed under the following conditions.
Device: JNM EX270 manufactured by JEOL
67.5MHz
Solvent: Deuterated chloroform ICP elemental analysis was performed under the following conditions.
Device: ICPS 8000 manufactured by Shimadzu Corporation
Moreover, the light emission external quantum efficiency, the maximum luminance, and the luminance half life of the obtained device were measured by the following methods.
(3) Light-emitting external quantum efficiency The produced organic light-emitting device was installed in a dark place, and a spectral radiance meter (CS-1000T, manufactured by Konica Minolta Co., Ltd.) was installed at a location 100 cm away in a direction perpendicular to the light-emitting surface. . A predetermined voltage was applied to the organic light emitting device for 1 second to emit light, and the current value supplied to the device, the front luminance observed from the anode side of the device, and the emission spectrum were measured in a 0.2 degree field of view. The applied voltage was increased in steps from 0 V to 0.1 V, and the current value, luminance, and emission spectrum immediately after the voltage was increased were measured. The light emission external quantum efficiency was calculated from these measured values, and the maximum value was defined as the light emission external quantum efficiency of the device.
(4) Maximum brightness The front brightness of the organic light-emitting device produced in the same manner as the measurement of the light-emitting external quantum efficiency is measured except that the increase width of the applied voltage is 0.5 V, and the highest measured value is determined. The highest brightness.
(5) Luminance half-life In the same manner as in the measurement of the light-emitting external quantum efficiency, the device was energized so that the luminance was 100 cd / m ² while measuring the front luminance of the produced organic light-emitting device. A silicon photodiode was brought into close contact with the anode side of the device, the photocurrent of the photodiode was measured while a constant current was passed through the device, and the time when the value of this photocurrent was halved was defined as the luminance half life.

  [Synthesis Example 1] (Synthesis of Compound (F))

  20 mL of tetrahydrofuran was added to 3.150 g (8.8 mmol) of methyltriphenylphosphonium bromide. Next, 0.989 g (8.8 mmol) of potassium tert-butoxide was added little by little while cooling with ice, and the mixture was stirred at room temperature for 1 hour. The obtained slurry was cooled to −78 ° C., and a 20 mL tetrahydrofuran solution of 1.519 g (5.8 mmol) of 3,5-dibromobenzaldehyde was added dropwise. The reaction solution was returned to room temperature and stirred for 1 hour, and then a saturated aqueous ammonium chloride solution was added. After extraction with ethyl acetate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.2 g (4.6 mmol) of 3,5-dibromostyrene.

  Next, 0.74 g (2.8 mmol) of 3,5-dibromostyrene, 1.11 g (5.6 mmol) of di-m-tolylamine, 0.038 g (0.17 mmol) of palladium acetate, tri-t-butylphosphine A mixture of 17 g (0.84 mmol), potassium-t-butoxide 0.65 g (5.8 mmol) and toluene 20 mL was heated to reflux for 3.5 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.33 g (2.7 mmol) of compound (F).

Identification data of the compound (F) is as follows.
Calcd _{(C 36 H 34 N 2)} C, 87.41; H, 6.93; N, 5.66.
Measurement C, 87.15; H, 7.02; N, 5.81.
Mass spectrometry (EI): 494 (M ⁺ ).
[Synthesis Example 2] (Synthesis of Compound (H))

  m-phenylenediamine 20 g (0.18 mol), 3-iodotoluene 81 g (0.37 mol), palladium acetate 0.50 g (2.2 mmol), tri-t-butylphosphine 1.4 g (6.9 mmol), potassium- A mixture of 45 g (0.40 mol) of t-butoxide and 300 mL of xylene was heated to reflux for 3 hours. The obtained reaction solution was cooled to room temperature, 40 g (0.18 mol) of 3-iodotoluene and 52 g (0.18 mol) of 3-bromoiodobenzene were added, and the mixture was further heated under reflux for 3 hours. After filtering the obtained reaction liquid, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2.7 g (5.1 mmol) of compound (G).

  Next, 2.0 g (3.7 mmol) of compound (G), 1.3 g (4.1 mmol) of tri-n-butyl (vinyl) tin, 0.10 g (0.14 mmol) of dichlorobis (triphenylphosphine) palladium, chloride A mixture of lithium (0.17 g, 4.0 mmol) and toluene (30 mL) was heated to reflux for 4 hours. The obtained reaction mixture was filtered to remove insoluble matters, and the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography gave 1.5 g (3.1 mmol) of compound (H).

Identification data of the compound (H) are as follows.
Calcd _{(C 35 H 32 N 2)} C, 87.46; H, 6.71; N, 5.83.
Measurements C, 87.59; H, 6.91; N, 5.50.
Mass spectrometry (EI): 480 (M ⁺ ).
In Examples and Comparative Examples, the following compounds (I) to (Q) were further used.

[Example 1] (Synthesis of polymer compound (1-1))
In a sealed container, 460 mg of compound (F) and 80 mg of iridium complex (M) were placed, and dehydrated toluene (5.0 mL) was added. Next, a toluene solution (0.1 M, 0.10 mL) of V-601 (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the freeze degassing operation was repeated 5 times. It sealed in vacuum and stirred at 60 ° C. for 60 hours. After the reaction, the reaction solution was dropped into 200 mL of acetone to obtain a precipitate. Further, reprecipitation purification with toluene-acetone was repeated twice, followed by vacuum drying at 50 ° C. overnight to obtain a polymer compound (1-1). The weight average molecular weight (Mw) of the high molecular compound (1-1) was 50200, and the molecular weight distribution index (Mw / Mn) was 2.19. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.10.

[Example 2] (Synthesis of polymer compound (2-1))
In a sealed container, 460 mg of compound (F), 80 mg of iridium complex (M) and 460 mg of compound (Q) were placed, and dehydrated toluene (9.9 mL) was added. Subsequently, a toluene solution (0.1 M, 198 μL) of V-601 (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the freeze degassing operation was repeated 5 times. It sealed in vacuum and stirred at 60 ° C. for 60 hours. After the reaction, the reaction solution was dropped into 500 mL of acetone to obtain a precipitate. Further, reprecipitation purification with toluene-acetone was repeated twice, followed by vacuum drying at 50 ° C. overnight to obtain a polymer compound (2-1). The weight average molecular weight (Mw) of the polymer compound (2-1) is 48000, and the molecular weight distribution index (Mw / Mn)
Was 1.95. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.055. In the polymer compound (2-1), the value of x / n was 0.54, and the value of y / n was 0.46.

[Example 3] (Synthesis of polymer compound (3-1))
In a sealed container, 460 mg of compound (H) and 460 mg of compound (P) were placed, and dehydrated toluene (9.9 mL) was added. Subsequently, a toluene solution (0.1 M, 198 μL) of V-601 (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the freeze degassing operation was repeated 5 times. It sealed in vacuum and stirred at 60 ° C. for 60 hours. After the reaction, the reaction solution was dropped into 500 mL of acetone to obtain a precipitate. Further, reprecipitation purification with toluene-acetone was repeated twice, followed by vacuum drying at 50 ° C. overnight to obtain a polymer compound (3-1). The polymer compound (3-1) had a weight average molecular weight (Mw) of 49200 and a molecular weight distribution index (Mw / Mn) of 1.89. The value of x / n in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.44, and the value of y / n was 0.56.

[Comparative Example 1] (Synthesis of polymer compound (1-2))
A polymer compound (1-2) was obtained in the same manner as in Example 1 except that the polymerizable compound (I) was used instead of the compound (F). The weight average molecular weight (Mw) of the high molecular compound (1-2) was 46300, and the molecular weight distribution index (Mw / Mn) was 2.07. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.12.

[Comparative Example 2] (Synthesis of polymer compound (2-2))
A polymer compound (2-2) was obtained in the same manner as in Example 2 except that the compound (J) was used instead of the compound (F). The weight average molecular weight (Mw) of the high molecular compound (2-2) was 46400, and the molecular weight distribution index (Mw / Mn) was 2.02. The m / (m + n) value of the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.050. In the polymer compound (2-2), the value of x / n was 0.49, and the value of y / n was 0.51.

[Comparative Example 3] (Synthesis of polymer compound (3-2))
A polymer compound (3-2) was obtained in the same manner as in Example 3 except that the compound (K) was used instead of the compound (H). The polymer compound (3-2) had a weight average molecular weight (Mw) of 52,000 and a molecular weight distribution index (Mw / Mn) of 1.96. The value of x / n in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.41, and the value of y / n was 0.59.

[Example 4] (Production and Evaluation of Organic Light-Emitting Element)
A substrate with ITO (manufactured by Nippon Electric Co., Ltd.) was used. This was a substrate in which two ITO (indium tin oxide) electrodes (anodes) having a width of 4 mm were formed in one stripe on one surface of a 25 mm square glass substrate.

First, poly (3,4-ethylenedioxythiophene) / polystyrenesulfonic acid (manufactured by Bayer Co., Ltd., trade name “BYTRON P”) on the above-mentioned ITO-attached substrate under conditions of a rotation speed of 3500 rpm and a coating time of 40 seconds. Then, it was applied by spin coating. Then, it dried for 2 hours at 60 degreeC under pressure reduction with the vacuum dryer, and formed the anode buffer layer. The film thickness of the obtained anode buffer layer was about 50 nm. Next, 48.6 mg of the polymer compound (1-1) and 41.4 mg of the compound (O) were dissolved in 2910 mg of toluene (special grade, manufactured by Wako Pure Chemical Industries, Ltd.), and this solution was filtered with a filter having a pore size of 0.2 μm. To prepare a coating solution. Next, the coating solution was coated on the anode buffer layer by spin coating under the conditions of a rotation speed of 3000 rpm and a coating time of 30 seconds. After the application, it was dried at room temperature (25 ° C.) for 30 minutes to form a light emitting layer. The film thickness of the obtained light emitting layer was about 100 nm.

  Next, the substrate on which the light emitting layer was formed was placed in a vapor deposition apparatus. Subsequently, barium and aluminum were co-evaporated at a weight ratio of 1:10, and two cathodes having a width of 3 mm were formed in stripes so as to be orthogonal to the extending direction of the anode. The film thickness of the obtained cathode was about 50 nm.

  Finally, lead wires (wirings) were attached to the anode and the cathode in an argon atmosphere, and four organic EL elements measuring 4 mm in length and 3 mm in width were produced. A voltage was applied to the organic EL element to emit light using a programmable DC voltage / current source (TR6143, manufactured by Advantest Corporation).

Maximum external quantum efficiency, maximum reached brightness, and initial brightness of 100 cd / m ^{2 of the} manufactured organic light emitting device
Table 1 shows the luminance half-life when the LED is turned on and driven at a constant current.
[Example 5] (Production and evaluation of organic light-emitting device)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 90 mg of the polymer compound (2-1) and 2910 mg of toluene. Table 1 shows the luminance half-life when the organic light-emitting device thus produced was driven at a constant current by lighting at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² .

[Example 6] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was prepared in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 82.8 mg of the polymer compound (3-1), 7.2 mg of iridium complex (L) and 2910 mg of toluene. Produced. Table 1 shows the luminance half-life when the organic light-emitting device thus produced was driven at a constant current by lighting at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² .

[Comparative Example 4] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 48.6 mg of the polymer compound (1-2), 41.4 mg of the compound (O) and 2910 mg of toluene. did. Table 1 shows the luminance half-life when the organic light-emitting device thus produced was driven at a constant current by lighting at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² .

[Comparative Example 5] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 90 mg of the polymer compound (2-2) and 2910 mg of toluene. Table 1 shows the luminance half-life when the organic light-emitting device thus produced was driven at a constant current by lighting at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² .

[Comparative Example 6] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was prepared in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 82.8 mg of the polymer compound (3-2), 7.2 mg of iridium complex (L) and 2910 mg of toluene. Produced. Table 1 shows the luminance half-life when the organic light-emitting device thus produced was driven at a constant current by lighting at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² .

[Synthesis Examples 3 and 4] (Synthesis of Compounds (R) and (S))
Compound (R) was synthesized in the same manner as in Synthesis Example 1, except that di-p-tolylamine was used instead of di-m-tolylamine. In addition, compound (S) was synthesized in the same manner as in Synthesis Example 1 except that di (4-methoxyphenyl) amine was used instead of di-m-tolylamine.

Identification data of the compound (R) are as follows.
Calcd _{(C 36 H 34 N 2)} C, 87.41; H, 6.93; N, 5.66.
Measurement C, 87.26; H, 6.83; N, 5.90.
Mass spectrometry (EI): 494 (M ⁺ ).
Identification data of the compound (S) is as follows.
Calcd _{(C 36 H 34 N 2 O} 4) C, 77.40; H, 6.13; N, 5.01. Measurement C, 77.65; H, 6.01; N, 4.97.
Mass spectrometry (EI): 558 (M ⁺ ).
[Synthesis Example 5] (Synthesis of Compound (U))

  4-amino-N, N-dimethylaniline 10.0 g (73 mmol), 4-bromo-N, N-dimethylaniline 15.0 g (75 mmol), palladium acetate 0.40 g (1.8 mmol), tri-t-butyl A mixture of 1.50 g (7.4 mmol) of phosphine, 10.0 g (89 mmol) of potassium tert-butoxide and 200 mL of toluene was heated to reflux for 3 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, and purified by silica gel column chromatography to obtain intermediate (T). Next, the obtained intermediate (T) 0.60 g (2.3 mmol), 3,5-dibromostyrene 0.30 g (1.1 mmol), palladium acetate 0.010 g (0.045 mmol), tri-t-butyl A mixture of 0.040 g (0.20 mmol) of phosphine, 0.40 g (3.6 mmol) of potassium tert-butoxide and 30 mL of toluene was heated to reflux for 5 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.40 g (0.65 mmol) of compound (U).

Identification data of the compound (U) are as follows.
Calcd _{(C 40 H 46 N 6)} C, 78.65; H, 7.59; N, 13.76
. Measurement C, 78.88; H, 7.30; N, 13.49.
Mass spectrometry (EI): 610 (M ⁺ ).
[Synthesis Example 6] (Synthesis of Compound (W))

  1,3-phenylenediamine 5.0 g (46 mmol), 9- (4-bromophenyl) carbazole 60 g (195 mmol), palladium acetate 1.0 g (4.5 mmol), tri-t-butylphosphine 3.6 g (18 mmol) , 30 g (267 mmol) of potassium-t-butoxide and 300 mL of toluene were heated to reflux for 5 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain intermediate (V). Next, 10 g (9.3 mmol) of the obtained intermediate (V) was dissolved in 100 ml of N, N-dimethylformamide, 0.75 g (9.6 mmol) of acetyl chloride was added, and 3.0 g (22 mmol) of aluminum chloride was further added. ) And stirred at room temperature for 12 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, 100 mL of xylene and 3.0 g (15 mmol) of triisopropoxyaluminum were added to the residue, and the mixture was heated to reflux again for 5 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.2 g (1.1 mmol) of compound (W).

Identification data of the compound (W) is as follows.
Calcd _{(C 80 H 54 N 6)} C, 87.40; H, 4.95; N, 7.64.
Measurement C, 87.73; H, 4.85; N, 7.51.
Mass spectrometry (EI): 1098 (M ⁺ ).
In the examples and comparative examples, the following compounds (X) to (Z) were further used.

[Example 7] (Synthesis of polymer compound (4-1))
The polymer compound (4-1) is synthesized in the same manner as in Example 1 except that the compound (R) is used instead of the compound (F) and the iridium complex (X) is used instead of the iridium complex (M). did. The weight average molecular weight (Mw) of the high molecular compound (4-1) was 72500, and the molecular weight distribution index (Mw / Mn) was 1.76. The m / (m + n) value of the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.11.

[Example 8] (Synthesis of polymer compound (5-1))
The polymer compound (5-1) is synthesized in the same manner as in Example 2, except that the compound (S) is used instead of the compound (F) and the iridium complex (Y) is used instead of the iridium complex (M). did. The polymer compound (5-1) had a weight average molecular weight (Mw) of 39800 and a molecular weight distribution index (Mw / Mn) of 2.20. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.060. In the polymer compound (5-1), the value of x / n was 0.52, and the value of y / n was 0.48.

[Example 9] (Synthesis of polymer compound (6-1))
A polymer compound (6-1) was synthesized in the same manner as in Example 3, except that the compound (W) was used instead of the compound (H) and the compound (Q) was used instead of the compound (P). The weight average molecular weight (Mw) of the high molecular compound (6-1) was 48400, and the molecular weight distribution index (Mw / Mn) was 2.55. ^In the polymer compound (6-1) estimated from the result of ¹³ C-NMR measurement, the value of x / n was 0.38, and the value of y / n was 0.62.

[Comparative Example 7] (Synthesis of polymer compound (4-2))
The polymer compound (4-2) was used in the same manner as in Example 1 except that the polymerizable compound (I) was used instead of the compound (F) and the iridium complex (X) was used instead of the iridium complex (M). Was synthesized. The weight average molecular weight (Mw) of the high molecular compound (4-2) was 63700, and the molecular weight distribution index (Mw / Mn) was 2.04. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.12.

[Comparative Example 8] (Synthesis of polymer compound (5-2))
The polymer compound (5-2) is synthesized in the same manner as in Example 2, except that the compound (J) is used instead of the compound (F) and the iridium complex (Y) is used instead of the iridium complex (M). did. The weight average molecular weight (Mw) of the high molecular compound (5-2) was 48000, and the molecular weight distribution index (Mw / Mn) was 2.15. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.065. In the polymer compound (5-2), the value of x / n was 0.53, and the value of y / n was 0.47.

[Comparative Example 9] (Synthesis of polymer compound (6-2))
A polymer compound (6-2) was synthesized in the same manner as in Example 3, except that the compound (K) was used instead of the compound (H) and the compound (Q) was used instead of the compound (P). The polymer compound (6-2) had a weight average molecular weight (Mw) of 59200 and a molecular weight distribution index (Mw / Mn) of 2.31. The value of x / n in the polymer compound estimated from the result of ¹³ C-NMR measurement was 0.50, and the value of y / n was 0.50.

[Example 10] (Production and evaluation of organic light-emitting device)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 48.6 mg of the polymer compound (4-1), 41.4 mg of the compound (O) and 2910 mg of toluene. did. The produced organic light emitting device showed yellow light emission. Table 2 shows the luminance half-life when the organic light-emitting device produced was lit at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² and driven at a constant current.

[Example 11] (Production and evaluation of organic light-emitting device)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 90 mg of the polymer compound (5-1) and 2910 mg of toluene. The produced organic light emitting device emitted orange light. Maximum external quantum efficiency of the organic light emitting device produced, maximum brightness and initial luminance 100 cd / m Table 2 luminance half life when the constant current drive by lighting with ²
It was shown to.

[Example 12] (Production and evaluation of organic light-emitting device)
An organic light emitting device was prepared in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 82.8 mg of the polymer compound (6-1), 7.2 mg of the iridium complex (Z) and 2910 mg of toluene. Produced. The produced organic light emitting device emitted red light. Table 2 shows the luminance half-life when the organic light-emitting device produced was lit at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² and driven at a constant current.

[Comparative Example 10] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 48.6 mg of the polymer compound (4-2), 41.4 mg of the compound (O) and 2910 mg of toluene. did. The produced organic light emitting device showed yellow light emission. Table 2 shows the luminance half-life when the organic light-emitting device produced was lit at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² and driven at a constant current.

[Comparative Example 11] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was produced in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 90 mg of the polymer compound (5-2) and 2910 mg of toluene. The produced organic light emitting device emitted orange light. Maximum external quantum efficiency of the organic light emitting device produced, maximum brightness and initial luminance 100 cd / m Table 2 luminance half life when the constant current drive by lighting with ²
It was shown to.

[Comparative Example 12] (Production and Evaluation of Organic Light-Emitting Element)
An organic light emitting device was prepared in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 82.8 mg of the polymer compound (6-2), 7.2 mg of the iridium complex (Z) and 2910 mg of toluene. Produced. The produced organic light emitting device emitted red light. Table 2 shows the luminance half-life when the organic light-emitting device produced was lit at the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ² and driven at a constant current.

  [Synthesis Example 7] Synthesis of Compound (AB)

1,3,5-tribromobenzene 10.0 g (32 mmol), di-m-tolylamine 12.5 g (63 mmol), palladium acetate 0.30 g (1.4 mmol), tri-t-butylphosphine 1.15 g (5 0.7 mmol), 8.0 g (71 mmol) of potassium t-butoxide and 200 ml of toluene were heated to reflux for 3.5 hours. The obtained reaction mixture was filtered through celite, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give compound (AA). Next, the obtained compound (AA) 2.
5 g (4.6 mmol), 4-vinylphenylboronic acid 0.68 g (4.6 mmol), tetrakis (triphenylphosphine) palladium 0.10 g (0.087 mmol), 1,2-dimethoxyethane 50 ml and potassium carbonate 2. A mixture of 0 g (14.5 mmol) of 20 ml aqueous solution was heated to reflux for 2 hours. The organic layer was extracted from the resulting reaction solution with ethyl acetate, the extract was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 2.2 g (3.9 mmol) of compound (AB).

Identification data of the compound (AB) are as follows.
Calcd _{(C 42 H 38 N 2)} C, 88.38; H, 6.71; N, 4.91.
Measurement C, 88.55; H, 6.49; N, 4.73.
Mass spectrometry (EI): 570 (M ⁺ ).
[Synthesis Example 8] Synthesis of Compound (AD)

Compound (AA) 2.5 g (4.6 mmol) obtained in Synthesis Example 7, 4-hydroxyphenylboronic acid 0.65 g (4.7 mmol), tetrakis (triphenylphosphine) palladium 0.10 g (0.087 mmol) A mixture of 50 ml of 1,2-dimethoxyethane and 2.0 g (14.5 mmol) of potassium carbonate in 20 ml was heated to reflux for 2 hours. 30 ml of 1N aqueous hydrochloric acid was added to the resulting reaction solution, the organic layer was extracted with ethyl acetate, and the extract was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain compound (AC). Next, 1.5 g (2.7 mmol) of the obtained compound (AC) was dissolved in 30 ml of dichloromethane, 0.40 g (4.0 mmol) of triethylamine was added, and then 0.36 g (3.4 mmol) of methacryloyl chloride was added. 5 ml of dichloromethane solution was added dropwise and stirred at room temperature for 2 hours. The obtained reaction solution was filtered through celite, the solvent was distilled off under reduced pressure, and then purified by silica gel column chromatography to obtain 1.5 g (2.4 mmol) of compound (AD).
Got.

Identification data of the compound (AD) is as follows.
Calcd _{(C 44 H 40 N 2 O} 2) C, 84.04; H, 6.41; N, 4.46. Measurement C, 83.82; H, 6.55; N, 4.81.
Mass spectrometry (EI): 628 (M ⁺ ).
[Example 13] Synthesis of polymer compound (7-1) Polymer compound (7-1) was synthesized in the same manner as in Example 2, except that compound (AB) was used instead of compound (F). . The polymer compound (7-1) had a weight average molecular weight (Mw) of 70900 and a molecular weight distribution index (Mw / Mn) of 2.41. The value of m / (m + n) in the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.058. In the polymer compound (7-1), the value of x / n was 0.49, and the value of y / n was 0.51.

[Example 14] Synthesis of polymer compound (8-1) A polymer compound (8-1) was synthesized in the same manner as in Example 2 except that the compound (AD) was used instead of the compound (F). . The polymer compound (8-1) had a weight average molecular weight (Mw) of 45100 and a molecular weight distribution index (Mw / Mn) of 2.85. The m / (m + n) value of the polymer compound estimated from the results of ICP elemental analysis and ¹³ C-NMR measurement was 0.070. In the polymer compound (8-1), the value of x / n was 0.53, and the value of y / n was 0.47.

[Example 15] Production and evaluation of organic light emitting device Organic light emitting device was prepared in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 90 mg of the polymer compound (7-1) and 2910 mg of toluene. Was made. The produced organic light emitting device emitted orange light. Table 3 shows the luminance half-life when the organic light-emitting device thus produced is driven at a constant current with the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ^2.
It was shown to.

[Example 16] Production and evaluation of organic light emitting device Organic light emitting device was prepared in the same manner as in Example 4 except that the coating solution used for forming the light emitting layer was prepared from 90 mg of the polymer compound (8-1) and 2910 mg of toluene. Was made. The produced organic light emitting device emitted orange light. Table 3 shows the luminance half-life when the organic light-emitting device thus produced is driven at a constant current with the maximum external quantum efficiency, the maximum reached luminance, and the initial luminance of 100 cd / m ^2.
It was shown to.

FIG. 1 is a cross-sectional view of an example of an organic light emitting device according to the present invention.

Explanation of symbols

1: Glass substrate 2: Anode 3: Hole transport layer 4: Light emitting layer 5: Electron transport layer 6: Cathode

Claims (11)

In an organic light emitting device in which at least one organic compound layer including a light emitting layer is sandwiched between an anode and a cathode, and a phosphorescent compound contained in the light emitting layer emits light,
The organic light-emitting device, wherein the light-emitting layer is a light-emitting layer containing a polymer compound having a structural unit derived from a polymerizable compound (A) represented by the following general formula (1).

(In the formula (1), at least one of R ^{1 to} R ²⁴ represents a substituent having a polymerizable functional group , and the substituent is represented by the above (a1) to (a13),
R ^{1 to} R ²⁴ which are not substituents having the polymerizable functional group are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a carbazole group, and a silyl group, R ^{1 to} R ⁵ , In each of R ^{6 to} R ¹⁰ , R ^{11 to} R ¹⁵ , R ^{16 to} R ²⁰ and R ^{21 to} R ²³ , two groups bonded to adjacent carbon atoms on the benzene ring are bonded to each other and condensed. A ring may be formed. )   The organic light-emitting device according to claim 1, wherein the polymer compound further has a structural unit derived from a phosphorescent polymerizable compound (B).   2. The polymer compound according to claim 1, further comprising a structural unit derived from a phosphorescent polymerizable compound (B) and a structural unit derived from an electron-transporting polymerizable compound (C). Organic light emitting device. The organic light-emitting device according to claim 2 or 3, wherein the phosphorescent polymerizable compound (B) is a complex represented by the following general formula (2-1).

(In Formula (2-1), R ^{31 to} R ³⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 1 carbon atom. Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by 10 to 10 alkyl groups, an alkoxy group having 1 to 10 carbon atoms, and a silyl group, and R ³¹ and R ³² represent R ³² And R ³³ , R ³³ and R ³⁴ , R ³⁴ and R ³⁵ , R ³⁵ and R ³⁶ , R ³⁶ and R ³⁷ , R ³⁷ and R ³⁸ , A condensed ring may be formed, and L represents a bidentate ligand selected from the group consisting of the following general formulas (2-2) to (2-4).

(In Formula (2-2), at least one of R ^{41 to} R ⁴⁸ represents a substituent having a polymerizable functional group, and R ^{41 to} R ⁴⁸ that is not a substituent having the polymerizable functional group are: Each independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, R ⁴¹ and R ⁴² , R ⁴² and R ⁴³ , R ⁴³ and R ⁴⁴ , R ⁴⁴ And R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁴⁶ and R ⁴⁷ , and R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a condensed ring.

(In Formula (2-3), at least one of R ^{51 to} R ⁵³ represents a substituent having a polymerizable functional group, and R ^{51 to} R ⁵³ which is not a substituent having the polymerizable functional group is Each independently a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, represents 10 alkoxy groups, and atom or a substituent selected from the group consisting of silyl group, at the R ⁵¹ and R ^52, between R ⁵² and R ^53, may form a fused ring bond to each other .)

(In the formula (2-4), at least one of R ^{61 to} R ⁶⁴ represents a substituent having a polymerizable functional group, and R ^{61 to} R ⁶⁴ that are not a substituent having the polymerizable functional group are: Each independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, and R ⁶¹ and R ⁶² , R ⁶² and R ⁶³ , R ⁶³ and R ⁶⁴ are bonded to each other To form a condensed ring.)   The organic light emitting device according to claim 1, wherein the light emitting layer further contains a phosphorescent compound (E).   The light emitting layer further includes a phosphorescent compound (E), and the polymer compound further includes a structural unit derived from an electron transporting polymerizable compound (C). The organic light emitting element as described. The organic light-emitting device according to claim 3, wherein the electron-transporting polymerizable compound (C) is an oxadiazole derivative, a triazole derivative, or a triarylborane derivative.   A surface-emitting light source using the organic light-emitting device according to claim 1.   An image display device using the organic light-emitting device according to claim 1. A polymer compound having a structural unit derived from a polymerizable compound (A) represented by the following general formula (1).

(In the formula (1), at least one of R ^{1 to} R ²⁴ represents a substituent having a polymerizable functional group , and the substituent is represented by the above (a1) to (a13),
R ^{1 to} R ²⁴ which are not substituents having the polymerizable functional group are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, carbon Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a carbazole group, and a silyl group, R ^{1 to} R ⁵ , In each of R ^{6 to} R ¹⁰ , R ^{11 to} R ¹⁵ , R ^{16 to} R ²⁰ and R ^{21 to} R ²³ , two groups bonded to adjacent carbon atoms on the benzene ring are bonded to each other and condensed. A ring may be formed. ) The polymer compound according to claim 10, wherein the polymer compound has a structural unit derived from a phosphorescent polymerizable compound (B) represented by the following general formula (2-1).

(In Formula (2-1), R ^{31 to} R ³⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 1 carbon atom. Represents an atom or substituent selected from the group consisting of an amino group optionally substituted by 10 to 10 alkyl groups, an alkoxy group having 1 to 10 carbon atoms, and a silyl group, and R ³¹ and R ³² represent R ³² And R ³³ , R ³³ and R ³⁴ , R ³⁴ and R ³⁵ , R ³⁵ and R ³⁶ , R ³⁶ and R ³⁷ , R ³⁷ and R ³⁸ , A condensed ring may be formed, and L represents a bidentate ligand selected from the group consisting of the following general formulas (2-2) to (2-4).

(In formula (2-2), at least one of R ^{41 to} R ⁴⁸ represents a substituent having a polymerizable functional group, and R ^{41 to} R ⁴⁸ that are not substituents having the polymerizable functional group are Independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, or a carbon number Represents an atom or substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, R ⁴¹ and R ⁴² , R ⁴² and R ⁴³ , R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁴⁶ and R ⁴⁷ , and R ⁴⁷ and R ⁴⁸ may be bonded to each other to form a condensed ring.

(In Formula (2-3), at least one of R ^{51 to} R ⁵³ represents a substituent having a polymerizable functional group, and each of R ^{51 to} R ⁵³ that is not a substituent having the polymerizable functional group is Independently, a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, or 1 to 10 carbon atoms of an alkoxy group, and atom or a substituent selected from the group consisting of silyl group, at the R ⁵¹ and R ^52, between R ⁵² and R ^53, may form a fused ring bond to each other. )

(In Formula (2-4), at least one of R ^{61 to} R ⁶⁴ represents a substituent having a polymerizable functional group, and R ^{61 to} R ⁶⁴ that are not a substituent having the polymerizable functional group are Independently, a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an amino group optionally substituted by an alkyl group having 1 to 10 carbon atoms, or a carbon number Represents an atom or a substituent selected from the group consisting of an alkoxy group of 1 to 10 and a silyl group, R ⁶¹ and R ⁶² , R ⁶² and R ⁶³ , R ⁶³ and R ⁶⁴ bonded to each other; To form a condensed ring.)

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