JP2009242746A - Macromolecule compound and organic electroluminescent element comprising the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a macromolecule compound which can be suitably used for an organic electroluminescent element, and an organic electroluminescent element using the compound. <P>SOLUTION: The macromolecule compound has at least one repeating unit expressed by general formula (1) in a macromolecule chain. In the formula, Ar expresses a bivalent aromatic group which is substituted or not substituted, n expresses an integer of at least one, and when n is an integer of at least two, Ar may be different mutually. In addition, Ar<SP>1</SP>and Ar<SP>2</SP>express a bivalent aromatic group which is substituted or not substituted and may be mutually same or different, and Ar<SP>1</SP>and Ar<SP>2</SP>may mutually join to form a ring. Ar<SP>3</SP>and Ar<SP>4</SP>express a monovalent aromatic group which is substituted or not substituted and may be mutually same or different, and Ar<SP>3</SP>and Ar<SP>4</SP>may mutually join to form a ring. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a novel polymer compound and an organic electroluminescent device containing the compound.

 In recent years, research and development of functional materials using organic compounds has been actively conducted. Recently, development of an organic electroluminescence element (organic electroluminescence element: organic EL element) using an organic compound as a constituent material of the element has been vigorously advanced.

  An organic electroluminescent device has a structure in which a thin film containing a light-emitting organic compound is sandwiched between an anode and a cathode, and excitons (exingtons) are formed by injecting electrons and holes into the thin film and recombining them. ) And emits light using light emitted when the exciton is deactivated. The organic electroluminescent element can emit light at a low direct current voltage of several volts to several tens of volts, and various colors (for example, red, blue, green, etc.) can be selected by selecting the type of the luminescent organic compound. ) Can be emitted. The organic electroluminescent device having such characteristics is expected to be applied to various light emitting devices and display devices.

 In an organic electroluminescent device, a light-emitting layer is used between electrodes, or a hole transport layer and an electron transport layer are stacked on the light-emitting layer. The hole transport material used for the hole transport layer and the electron transport material used for the electron transport layer are called charge transport materials. The charge transporting material is required to be capable of accepting charges for either or both of electrons and holes in a neutral state, to have a high charge transporting ability, and to be easily formed into a film. Further, since it is used as a uniform thin film, it is also important that the film quality of the thin film is stable in an amorphous state.

  As a method for forming a thin film of a charge transporting material, when a thin film having a film thickness of 1 μm or less is formed using a low molecular compound, a vacuum vapor deposition method is generally used, but an expensive vapor deposition apparatus is required. In addition, the production efficiency is not high, it is difficult to increase the area of the substrate, and when a low molecular weight compound is used alone, the mechanical strength and thermal stability of the thin film are inferior. Therefore, recently, an organic electroluminescent element (polymer) using a conjugated light-emitting polymer as a light-emitting organic compound as a material advantageous for large screen TV panels and flexible sheet displays due to the feature that patterning by a printing method is possible. The development of organic electroluminescent elements (polymer organic EL elements) has been energetically advanced.

The present inventors have also developed and proposed a novel polymer compound containing a thiophene derivative in the main chain (see, for example, Patent Document 1).
JP 2006-316224 A

  The polymer organic EL device has the above-described advantages, but has a problem that the light emission efficiency is lower than that of the organic EL device using a low molecular compound. As a factor that the luminous efficiency of the polymer organic EL device is low, the charge transport ability of the polymer compound is lower than that of the low-molecular compound. That is, in the case of an organic EL device using a low molecular compound, the charge transport layer is composed of a single material, and the intermolecular charge is likely to move because the intermolecular distance is small. In this case, since it is difficult to achieve high purity compared to low molecular weight compounds, residual impurities may become traps for charge transfer, and structural defects may occur during polymerization, which is disadvantageous for charge transfer. It is considered that charge transfer is less likely to occur.

  Further, the organic electroluminescence device using the novel polymer compound containing thiophene in the main chain has been desired to be further improved in terms of efficiency and lifetime.

  An object of the present invention is to provide a novel polymer compound suitable for an organic electroluminescence device, and an organic electroluminescence device containing the compound.

  As a result of intensive studies to achieve the above-mentioned problems, the present inventors have found that a polymer compound having a specific structure has a high charge transporting ability and can form a homogeneous thin film. As a result, it was found that an organic electroluminescence device with high efficiency and long life can be obtained, and the present invention has been completed.

That is, the present invention provides the following [1] to [8].
[1] A polymer compound having at least one repeating unit represented by the general formula (1) in the polymer chain.

[In the formula, Ar represents a substituted or unsubstituted divalent aromatic group. n represents an integer of 1 or more, and Ar may be different from each other when n is an integer of 2 or more. Ar ¹ and Ar ² represent a substituted or unsubstituted divalent aromatic group which may be the same or different from each other, and Ar ¹ and Ar ² may be bonded to each other to form a ring. . Ar ³ and Ar ⁴ represent a substituted or unsubstituted monovalent aromatic group which may be the same or different from each other, and Ar ³ and Ar ⁴ may be bonded to each other to form a ring. . ]

[2] In the general formula (1), Ar and Ar ^{1 to} Ar ⁴ are carbocyclic aromatic groups having 6 to 30 carbon atoms in the aromatic ring constituting the aromatic group or aromatic rings constituting the aromatic ring. The polymer compound according to [1], which is a heterocyclic aromatic group having 2 to 30 carbon atoms.

[3] An organic electroluminescence device comprising at least one layer containing at least one polymer compound according to [1] or [2] sandwiched between a pair of electrodes.

[4] The organic electroluminescence device according to [3], wherein the layer containing the polymer compound is a charge injection transport layer.

[5] The organic electroluminescence device according to [4], wherein the charge injection / transport layer is a hole injection / transport layer.

[6] The organic electroluminescent element according to [3], wherein the layer containing the polymer compound is a light emitting layer.

[7] The organic electroluminescence device according to any one of [3] to [6], wherein the light emitting layer has a layer containing a compound having a light emitting function other than the polymer compound between the pair of electrodes.

[8] The organic electroluminescence device according to any one of [3] to [7], having a layer containing a compound having an electron injecting and transporting function other than the polymer compound as an electron injecting and transporting layer between a pair of electrodes .

  According to the present invention, it is possible to provide a high molecular compound suitable for an organic electroluminescent device and a high-efficiency, long-life organic electroluminescent device, which has a high charge transport capability and can form a uniform thin film.

Hereinafter, the present invention will be described in detail.
The polymer compound of the present invention is a polymer compound having at least one repeating unit represented by the general formula (1) in the polymer chain.
General formula (1):

[In the formula, Ar represents a substituted or unsubstituted divalent aromatic group. n represents an integer of 1 or more, and Ar may be different from each other when n is an integer of 2 or more. Ar ¹ and Ar ² represent a substituted or unsubstituted divalent aromatic group which may be the same or different from each other, and Ar ¹ and Ar ² may combine with each other to form a ring. . Ar ³ and Ar ⁴ represent a substituted or unsubstituted monovalent aromatic group which may be the same or different from each other, and Ar ³ and Ar ⁴ may be bonded to each other to form a ring. . ]

  In the general formula (1), Ar represents a substituted or unsubstituted divalent aromatic group, and includes a divalent carbocyclic aromatic group or a divalent heterocyclic aromatic group.

  The carbocyclic aromatic group is an aromatic group made of a cyclic compound in which all atoms constituting the aromatic ring are carbon atoms. In the present invention, the aromatic ring constituting the carbocyclic aromatic group is a carbocyclic aromatic ring. The carbocyclic aromatic ring is composed of a five-membered ring or a six-membered ring. Preferably, 1 to 5 aromatic rings are condensed and configured, more preferably 1 to 4 aromatic rings are condensed.

6-60 are preferable and, as for carbon number which comprises a carbocyclic aromatic ring, 6-30 are more preferable.
Specific examples of such carbocyclic aromatic rings include condensed polycyclic aromatic rings such as pentalene ring, phenalene ring, triphenylene ring, perylene ring, indene ring, azulene ring, phenanthrene ring, pyrene ring, and picene ring. Benzene ring, naphthalene ring, anthracene ring, naphthacene ring, pentacene ring and other acene-type aromatic rings.

    Next, Ar in the general formula (1) may be a polycyclic system. Specifically, it is a polycyclic system in which a plurality of ring systems are connected one-dimensionally by one single bond as shown in the general formula (2). Here, m is an integer of 0-2. A preferred number of m is 0 or 1, and a more preferred number is 0.

  In the general formula (1), Ar includes a divalent aromatic group in which aromatic rings are connected by an alkylene group as the divalent aromatic group. The alkylene group may be unsubstituted or substituted. The substituted or unsubstituted alkylene group is a linear, branched or cyclic alkylene group.

  As an alkylene group, a C1-C6 alkylene group is preferable and a C1-C3 alkylene group is more preferable.

Examples of the substituent on the alkylene group include an alkyl group, an aromatic group, and an aralkyl group.
The alkyl group on the alkylene group is a substituted or unsubstituted linear, branched or cyclic alkyl group. Specific examples include methyl group, trifluoromethyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso -Pentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, 2-ethylhexyl group, n-heptyl group, 1-methyl Hexyl group, n-octyl group, 1-methylheptyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5- Trimethylhexyl group, n-decyl group, 1-ethyloctyl group, n-dodecyl group, 1-methyldecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n Pentadecyl group, 1-hexyl-octyl group, n- hexadecyl group,
Cyclohexyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, (2-isopropylcyclohexyl) ethyl group, cyclopentyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1-dimethylhexyl group, bornel Group, isobornel group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, 1 -Methylcyclopentyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4 -Dimethylcyclohexyl group 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3-tert-butylcyclohexyl Groups, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclododecyl group, cyclotetradecyl group and the like.

  The aromatic group on the alkylene group includes a substituted or unsubstituted carbocyclic aromatic group or heterocyclic aromatic group. As the substituted or unsubstituted carbocyclic aromatic group, those having 6 to 30 carbon atoms constituting the ring are preferable. As the substituted or unsubstituted heterocyclic aromatic group, those having 3 to 30 carbon atoms constituting the ring are preferable.

  Specific examples of the aromatic group include phenyl group, 1-naphthyl group, 2-naphthyl group, 15-acenaphthylenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, indenyl group, and azulenyl. Group, fluorenyl group, anthryl group, pyrenyl group, perylenyl group and other carbocyclic aromatic groups, 4-quinolyl group, 2-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-pyrimidyl group Group, 4-pyrimidyl group, 5-pyrimidyl group, 3-pyridazinyl group, 4-pyridazinyl group, 2-pyrazinyl group, 3-furyl group, 2-furyl group, 2-benzofuryl group, 4-dibenzofuranyl group, 2 -Dibenzofuranyl group, 3-thienyl group, 2-thienyl group, dibenzothiophen-4-yl group, dibenzothiophen-2-yl group, 2- Kisazoriru group, 2-thiazolyl, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, and a heterocyclic aromatic group such as carbazol-3-yl group.

  Examples of the substituent on the carbocyclic aromatic group or heterocyclic aromatic group include those similar to the above carbocyclic aromatic group or heterocyclic aromatic group.

  The aralkyl group on the alkylene group is preferably a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms. Specific examples of the aralkyl group include those shown as the D ′ aralkyl group described later.

  Specific examples of the substituted or unsubstituted alkylene group include, for example, a methylene group, ethylene group, propylene group, 1,1-cyclopropylene group, 1,2-cyclopropylene group, 1,1-cyclobutylene group, 1, 1-cyclopentylene group, 1,2-cyclopentylene group, 1,1-cyclohexylene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 3-methyl-1,1 -Cyclohexylene group, 3,3,5-trimethyl-1,1-cyclohexylene group, octahydro-4,7-methano-5H-indene-5,5-ylene group, 1,1-cycloheptylene group 1,1-diphenylmethylene group, 1,1-dibenzylmethylene group and the like.

The case where Ar is a heterocyclic aromatic group in the general formula (1) will be described.
The heterocyclic aromatic group is an aromatic group composed of a cyclic compound in which the atoms constituting the aromatic ring are two or more elements. In the present invention, the aromatic ring constituting the heterocyclic aromatic group is a heterocyclic aromatic ring. Examples of the atom of two or more elements include a carbon atom, an oxygen atom, a phosphorus atom, a sulfur atom, and a nitrogen atom. Preferably, it is composed of 2 to 5 element atoms, and more preferably is composed of 2 to 4 element atoms. Note that atoms other than carbon atoms are referred to as heteroatoms.

The heterocyclic aromatic ring is composed of a 5-membered ring or a 6-membered ring. Preferably, 1-4 aromatic rings are condensed and configured, and more preferably, 1 to 3 aromatic rings are condensed.
2-60 are preferable and, as for carbon number contained in a heterocyclic aromatic ring, 2-30 are more preferable.
Furthermore, it describes as a specific example of a preferable heterocyclic aromatic ring.

    First, a five-membered ring containing one heteroatom shown in the general formula (3) is mentioned. In the general formula (3), a furan ring with Z = O, a thiophene ring with Z = S, and a pyrrole ring with Z = NH can be mentioned. Among these, a thiophene ring and a furan ring are preferable, and a thiophene ring is more preferable.

  Moreover, general formula (4) which the benzene ring condensed to general formula (3) is mentioned. In the general formula (4), Z = NH indole ring, Z = O benzofuran ring, and Z = S benzothiophene ring. Among these, a benzofuran ring and a benzothiophene ring are preferable, and a benzothiophene ring is more preferable.

  Moreover, the general formula (5) in which an aromatic ring is condensed to the Z = S thiophene ring in the general formula (3) can be given. Among these, an isothianaphthene ring, a thienothiadiazole ring, and a thieno [3,2-b] thiophene ring are preferable, and a thieno [3,2-b] thiophene ring is more preferable.

Next, a five-membered ring containing two heteroatoms shown in the general formula (6) can be mentioned. In the general formula _{(6), Z} 1 = O oxazole _ring, thiazole ring of _Z 1 = _S, imidazole ring of Z 1 = NH. _Further, isoxazole ring of _Z 2 = _O, isothiazole ring of _Z 2 = _S, include pyrazole ring of Z 2 = NH. Among these, an oxazole ring and a thiazole ring are preferable, and a thiazole ring is more preferable.

Moreover, general formula (7) which the benzene ring condensed to the five-membered ring of general formula (6) is mentioned. In the general formula _(7), a benzoxazole ring of _Z 1 = _O, benzothiazole ring of _Z 1 = _S, include a benzimidazole ring of Z 1 = NH. In the general formula _(7), benzisoxazole ring of _Z 2 = _O, benzisothiazole ring _Z 2 = _S, include benzopyrazole ring Z 2 = NH. Among these, a benzothiazole ring and a benzoisothiazole ring are preferable, and a benzothiazole ring is more preferable.

  As five-membered rings containing 3 or more heteroatoms, n-triazole ring, s-triazole ring, 1,2,4-oxadiazole ring, 1,3,5-oxadiazole ring, 1,2,5-oxa Examples thereof include a diazole ring, 1,2,4-thiadiazole ring, 1,3,5-thiadiazole ring, 1,2,5-thiadiazole ring, and tetrazole ring. Among these, a 1,3,5-oxadiazole ring and a 1,3,5-thiadiazole ring are preferable, and a 1,3,5-thiadiazole ring is more preferable.

A pyridine ring is mentioned as a 6-membered ring containing 1 hetero atom. Furthermore, a quinoline ring and an isoquinoline ring in which a benzene ring is condensed with a pyridine ring can be mentioned.
Next, examples of the six-membered ring containing two heteroatoms include a pyridazine ring, a pyrimidine ring, and a pyrazine ring. In addition, a benzo [d] pyridazine ring, a benzo [c] pyridazine ring, a quinazoline ring, and a quinoxaline ring in which a benzene ring is condensed to these six-membered rings are exemplified.
Furthermore, a triazine ring is mentioned as a 6-membered ring containing 3 hetero atoms.

  Moreover, Ar which is a heterocyclic aromatic group in General formula (1) may be a polycyclic system. Specifically, it is a polycyclic system in which a plurality of ring systems are connected one-dimensionally by one single bond as shown in the general formula (8). Here, Z represents an oxygen atom or a sulfur atom. Moreover, m represents the integer of 0-2. Of these, Z is preferably a sulfur atom. A preferred number of m is 0 or 1, and a more preferred number is 0.

Further, Ar in the general formula (1) may have a structure as shown in the general formula (9). Specific examples include Z ₆ ═NH carbazole ring, Z ₆ ═O dibenzofuran ring, Z ₆ ═S dibenzothiophene ring, Z ₆ ═CH ₂ fluorene ring, Z ₆ ═CO fluorenone ring, Z _6. A dibenzothiophenesulfone ring of ═SO ₂ . Z ₇ = NH indenocarbazole ring, Z ₇ = O benzobisbenzofuran ring, Z ₇ = S benzobisbenzothiophene ring, Z ₇ = CH ₂ indenofluorene ring, Z ₇ = CO indenofluorene A dione ring is mentioned. Among these, preferably dibenzothiophene ring, fluorene ring, fluorenone ring, indenocarbazole ring, benzobisbenzothiophene ring, indenofluorene ring, more preferably dibenzothiophene ring, fluorene ring, indenocarbazole ring, A benzobisbenzothiophene ring and an indenofluorene ring.

  In addition, the aromatic group corresponding to Ar may have a substituent, specifically, an aryl group, aryloxy group, arylthio group, alkyl group, alkyloxy group, alkylthio group, hydroxyalkyl group, alkoxyalkyl group. Group, monosubstituted amino group, disubstituted amino group, halogenated alkyl group, alkoxycarbonylalkyl group, carboxyalkyl group, halogen atom, amino group, hydroxy group, optionally esterified carboxyl group, hydroxyl group, sulfo group , A phosphoryl group, a cyano group, etc., an alkyl group which may have a substituent having 1 to 4 carbon atoms, an alkoxy group which may have a substituent having 1 to 6 carbon atoms, and the general formula (1 ′ a) to (3′a):

-(O) _L'- D '(1'a)
-O (C = O) -D '(2'a)
-(C = O) OD '(3'a)

[Wherein D ′ represents a substituted or unsubstituted linear, branched or cyclic alkyl group, a substituted or unsubstituted monovalent aromatic group, a substituted or unsubstituted aralkyl group, and L ′ represents Indicates 0 or 1]
And so on. In addition, the substitution position of these substituents is not particularly limited.

  The aryl group represents a monovalent aromatic group. Specific examples include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 15-acenaphthylenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, 4- Phenylphenyl group, indenyl group, azulenyl group, fluorenyl group, anthryl group, pyrenyl group, perylenyl group and other carbocyclic aromatic groups, 4-quinolyl group, 2-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 3-pyridazinyl group, 4-pyridazinyl group, 2-pyrazinyl group, 3-furyl group, 2-furyl group, 2-benzofuryl group, 4-dibenzofuranyl group, 2-dibenzofuranyl group, 3-thienyl group, 2-thienyl group, dibenzothiophen-4-yl group, dibenzothio Heterocyclic aromatic groups such as phen-2-yl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, carbazol-3-yl group Can be mentioned.

  The aryloxy group has a structure in which monovalent aromatic groups are linked by an ether bond, and examples of the aromatic group include those specifically exemplified above.

  The arylthio group has a structure in which monovalent aromatic groups are connected by a thioether bond, and examples of the aromatic group include those specifically exemplified above.

  The alkyl group may be linear, branched or cyclic, and is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group. And decyl group.

  The alkyloxy group may be linear, branched or cyclic, and is preferably an alkyloxy group having 1 to 20 carbon atoms, more preferably an alkyloxy group having 1 to 10 carbon atoms. Specific examples include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, Examples include 2-ethylhexyloxy group, nonyloxy group, decyloxy group and the like.

  The alkylthio group may be linear, branched or cyclic, and is preferably an alkylthio group having 1 to 20 carbon atoms, more preferably an alkylthio group having 1 to 10 carbon atoms. Specific examples include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group. Group, nonylthio group, decylthio group and the like.

  The hydroxyalkyl group has a structure in which a hydroxyl group is substituted with an alkyl group, a hydroxyalkyl group having 1 to 20 carbon atoms is preferable, and a hydroxyalkyl group having 1 to 10 carbon atoms is more preferable. Specific examples include hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, 2-hydroxyethyl group and the like.

  The alkoxyalkyl group has a structure in which an alkoxyl group is substituted with an alkyl group, preferably an alkoxyalkyl group having 1 to 20 carbon atoms, more preferably an alkoxyalkyl group having 1 to 10 carbon atoms. Specific examples include methoxymethyl group, ethoxymethyl group, butoxymethyl group, ethoxyethyl group, butoxyethyl group, 2-methoxyethyl group and the like. The substitution position on the alkyl group of the alkoxyl group is not particularly limited, and may be on any carbon atom of the alkyl chain such as the middle or terminal of the alkyl group.

  The monosubstituted amino group and the disubstituted amino group have a structure in which an alkyl group and / or an aryl group is substituted with an amino group. When the alkyl group is substituted, an alkylamino group having 1 to 20 carbon atoms is preferable, and an alkylamino group having 1 to 10 carbon atoms is more preferable. When the aryl group is substituted, an arylamino group having 1 to 40 carbon atoms is preferable, and an arylamino group having 1 to 20 carbon atoms is more preferable. Specific examples include N-methylamino group, N-ethylamino group, N-phenylamino group, N- (1-naphthyl) amino group, N- (2-naphthyl) amino group, and N, N-dimethylamino group. N, N-diethylamino group, N, N-diphenylamino group, 9H-carbazol-9-yl group and the like. Of the monosubstituted amino group and disubstituted amino group, a disubstituted amino group is more preferable.

  The halogenated alkyl group has a structure in which a halogen atom is substituted with an alkyl group, preferably a halogenated alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl halide having 1 to 10 carbon atoms. Specific examples include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2-fluoroethyl group, and a 2-chloroethyl group. The halogen atom may be any of a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, but is preferably a fluorine atom or a chlorine atom. The number of halogen atoms is not particularly limited, but is 1 or more. For example, all hydrogen atoms may be substituted with halogen atoms like perfluoroalkyl groups.

  The alkoxycarbonylalkyl group is preferably an alkoxycarbonylalkyl group having 1 to 20 carbon atoms, and more preferably an alkoxycarbonylalkyl group having 1 to 10 carbon atoms. Specific examples include a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propoxycarbonylmethyl group, an n-butoxycarbonylmethyl group, a methoxycarbonylethyl group, and a methoxycarbonylpropyl group.

  The carboxyalkyl group has a structure in which a carboxyl group is substituted with an alkyl group, preferably a carboxyalkyl group having 1 to 20 carbon atoms, and more preferably a carboxyalkyl group having 1 to 10 carbon atoms. Specific examples include a carboxymethyl group and a 2-carboxyethyl group.

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Preferably they are a fluorine atom or a chlorine atom.

The substituted or unsubstituted linear, branched or cyclic alkyl group represented by D ′ in the general formulas (1′a) to (3′a) is preferably an alkyl group having 1 to 20 carbon atoms. Specific examples of these alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso- Pentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, 2-ethylhexyl group, n-heptyl group, 1-methylhexyl Group, n-octyl group, 1-methylheptyl group, 2-propylpentyl group, 2,2-dimethylhexyl group, 2,6-dimethyl-4-hexyl group, 3,5,5-trimethylpentyl group,
Cyclohexyl group, cyclohexylmethyl group, cyclopentyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1-dimethylhexyl group, 1-norbornyl group, 2-norbornanemethyl group,
Cyclobutyl group, 1-methylcyclopentyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, cycloheptyl group, cyclooctyl group,
Methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-iso-propoxyethyl group, 2-n-butoxyethyl group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2 -(2'-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group, 2-cyclohexyloxyethyl group, 2 -Methoxypropyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-iso-propoxy Propyl group, 3- (n-butoxy) propyl group, 3- (n-pentyloxy) propyl group, 3- (n-hexyloxy) propyl group, 3- (2′-ethylbutoxy) propyl group, 3- (n -Octyloxy) propyl group, 3- (2'-ethylhexyloxy) propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-iso- Propoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4-n-octyloxybutyl group, 5-methoxypentyl group,
5-ethoxypentyl group, 5-n-ethoxypentyl group, 6-ethoxyhexyl group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-n-hexyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-methoxyoctyl group, tetrahydrofurfuryl group, 2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butoxyethoxy) ethyl group, 3- (2′-ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4′-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2′-hexenyloxy) propyl group, 3- (2′-heptenyloxy) propyl group, 3- (1′-cyclohexenyloxy) Ii) propyl group, 4-allyloxybutyl group, benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4'-methylbenzyloxy) ethyl group, 2- (2'- Methylbenzyloxy) ethyl group, 2- (4′-fluorobenzyloxy) ethyl group, 2- (4′-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4′-methoxybenzyloxy) Propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) ethyl group, 2- (4′-methylbenzyloxymethoxy) ethyl group, phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methyl Phenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluoro Phenyloxymethyl group, 4-chlorophenyloxymethyl group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl Group, 2- (4′-methoxyphenyloxy) ethyl group, 2- (4′-chlorophenyloxy) ethyl group, 2- (4′-bromophenyloxy) ethyl group, 2- (1′-naphthyloxy) ethyl Group, 2- (2′-naphthyloxy) ethyl group, 3-phenyloxypropyl group, 3- (2′-naphthyloxy) propyl group, 4-phenyloxybutyl group, 4- (2′-ethylphenyloxy) Butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl Group, 2- (2′-phenyloxyethoxy) ethyl group, 3- (2′-phenyloxyethoxy) propyl group, 4- (2′-phenyloxyethoxy) butyl group, n-butylthiomethyl group, n- Hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2-n-octylthioethyl group, 2-n-decyl Thioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group, 4-n-butylthiobutyl group 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2′-me Xylethylthio) ethyl group, 4- (3′-ethoxypropylthio) butyl group, 2- (2′-ethylthioethylthio) ethyl group, 2-allylthioethyl group, 2-benzylthioethyl group, 3- (4 '-Methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2'-benzyloxyethylthio) ethyl group, 3- (3'-benzylthiopropylthio) propyl group, 2-phenylthioethyl group 2- (4′-methoxyphenylthio) ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) propyl group, 2-hydroxyethyl group, 2- Hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8 -A hydroxy octyl group, 2-hydroxy cyclohexyl group, etc. can be mentioned.

  In the general formulas (1′a) to (3′a), the aromatic group of D ′ includes a monovalent carbocyclic aromatic group or a monovalent heterocyclic aromatic group. These groups may be substituted or unsubstituted. When these groups are substituted or unsubstituted carbocyclic aromatic groups, the number of carbon atoms constituting the ring of the group is preferably 6 to 12. On the other hand, when these groups are substituted or unsubstituted heterocyclic aromatic groups, the number of carbon atoms constituting the ring of the group is preferably 4 to 12.

  Specific examples of the aromatic group of D ′ include phenyl group, 1-naphthyl group, 2-naphthyl group, 15-acenaphthylenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and indenyl. Group, azulenyl group, fluorenyl group, anthryl group, pyrenyl group, perylenyl group and other carbocyclic aromatic groups, 4-quinolyl group, 2-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 3-pyridazinyl group, 4-pyridazinyl group, 2-pyrazinyl group, 3-furyl group, 2-furyl group, 2-benzofuryl group, 4-dibenzofuranyl Group, 2-dibenzofuranyl group, 3-thienyl group, 2-thienyl group, dibenzothiophen-4-yl group, dibenzothiophen-2-yl group, Examples thereof include heterocyclic aromatic groups such as 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group and carbazol-3-yl group.

Examples of the substituent on the aromatic group of D ′ in the general formulas (1′a) to (3′a) include a sulfo group, a carboxyl group, a phosphoryl group, a hydroxyl group, a halogen atom, and a linear, branched or cyclic group. Of the alkyl group.
Here, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  The linear, branched or cyclic alkyl group may be substituted or unsubstituted. As an alkyl group, a C1-C16 thing is preferable and a C1-C8 thing is more preferable. Specific examples of the substituted or unsubstituted linear, branched or cyclic alkyl group include those shown as the alkyl group for D ′.

  In the general formulas (1′a) to (3′a), the substituted or unsubstituted aralkyl group of D ′ is preferably an aralkyl group having 7 to 20 carbon atoms. Specific examples of these aralkyl groups include benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α -Dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert -Butylbenzyl group, 2-tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4-allylbenzyl group, 4 -Benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, 4- (4'-methylphenyl) benzyl Group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n- Tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxy Methylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group, 4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4-hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group Examples include 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, etc. be able to.

Moreover, Ar < ¹ >, Ar < ² > in General formula (1) shows the substituted or unsubstituted bivalent aromatic group which may mutually be same or different. The divalent aromatic group includes a divalent carbocyclic aromatic group or a divalent heterocyclic aromatic group. Specific examples of the divalent carbocyclic aromatic group or divalent heterocyclic aromatic group include the specific examples of Ar described above. Ar ¹ and Ar ² may be bonded to each other to form a ring.

In the general formula (1), Ar ³ and Ar ⁴ represent a substituted or unsubstituted monovalent aromatic group which may be the same or different from each other. The monovalent aromatic group includes a monovalent carbocyclic aromatic group or a monovalent heterocyclic aromatic group. Specific examples of the monovalent carbocyclic aromatic group or the monovalent heterocyclic aromatic group include the specific examples of Ar described above. Ar ³ and Ar ⁴ may be bonded to each other to form a ring.

  Further, the number average molecular weight of the polymer compound having at least one repeating unit represented by the general formula (1) in the polymer chain is not particularly limited, but is 1000 to 1000000 in terms of polystyrene. Preferably it is 3000-500000. More preferably, it is 4000-200000.

  In addition, a polymer compound having at least one repeating unit represented by the general formula (1) in the polymer chain has a terminal functional group substituted or unsubstituted carbocyclic aromatic group, disubstituted amino group, The terminal treatment may be performed by substitution with a chain, branched or cyclic alkyl group, an alkyloxy group having a linear, branched or cyclic alkyl group, a carboxyl group, an alkoxycarbonyl group, a hydroxyl group, or the like.

  Specific examples of the polymer compound represented by the general formula (1) of the present invention are illustrated below, for example, but the present invention is not limited to these specific examples.

  Next, the manufacturing method of the high molecular compound which has at least one repeating unit represented by General formula (1) of this invention in a polymer chain is demonstrated.

Examples of the polymer compound having at least one repeating unit represented by the general formula (1) in the polymer chain include, for example, the general formula (10):
_{(HO) 2 B-Ar-} B (OH) 2 (10)
(In the formula, Ar is as in the general formula (1).)
An aromatic boron compound represented by the general formula (11):

(In the formula, Q represents a halogen atom, and Ar ^{1 to} Ar ⁴ are as described above.)
Can be produced by polymerizing by a coupling reaction (Suzuki coupling) in the presence of a transition metal catalyst.
Examples of the halogen atom for Q include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The polymer compound according to the present invention in which at least one of the substituents of Ar and Ar ^{1 to} Ar ⁴ is a sulfo group has, for example, at least one repeating unit represented by the general formula (1) in the polymer chain. It can be produced by sulfonating a polymer compound.

Examples of the sulfonating agent used for sulfonation include sulfuric acid, fuming sulfuric acid, sulfur trioxide, sulfur trioxide complex, chlorosulfuric acid, fluorosulfuric acid, and amidosulfuric acid, and the amount of the sulfonating agent to be used is not particularly limited.
The sulfur trioxide complex is a complex with Lewis acids such as ethers, amines, sulfides, N, N-dimethylformamide / sulfur trioxide complex, dioxane / sulfur trioxide complex, pyridine / sulfur trioxide complex, Examples include triethylamine / sulfur trioxide complex, trimethylamine / sulfur trioxide complex, and the like.

  The reaction can be carried out without solvent or in a solvent. The solvent used in the reaction is not particularly limited as long as it does not affect the reaction, but chlorinated organic solvents such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, tetrachloroethane; liquid sulfur dioxide, carbon disulfide Acetic acid, acetic anhydride; esters such as ethyl acetate; ethers such as diethyl ether; benzene, toluene, xylene, nitromethane, nitrobenzene, n-butyl alcohol, iso-butyl alcohol, tert-butyl alcohol, acetonitrile, tetrahydrofuran, dioxane Dimethylformamide, dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, N-methylpyrrolidone and the like.

  The reaction temperature may be selected from the range of −20 ° C. to 150 ° C. (representing Celsius temperature; hereinafter the same), and the reaction time is several minutes to 96 hours. It can also be obtained by synthesizing sulfonyl chloride with chlorosulfuric acid and hydrolyzing it.

  The method for isolating the polymer compound of the present invention is not particularly limited. If the product is precipitated from the reaction solvent, it can be isolated by filtration or centrifugation, and if dissolved in the reaction solvent, a method of distilling the solvent under reduced pressure or a suitable solvent can be used. In addition, a method of precipitation, filtration, or centrifugation can be employed.

  If the reaction product forms a sulfate salt, the excess sulfonating agent is removed by washing with water after filtration, and the sulfuric acid is removed by neutralizing the resulting sulfate salt with a base. Can do. As the base, hydroxides such as alkali metals and alkaline earth metals, ion exchange resins, and the like can be used.

  When purification is required for the polymer compound of the present invention, a well-known method can be employed. For example, a recrystallization method, a reprecipitation method, a column chromatography method, washing with a solvent ( Sludge), an adsorption treatment using activated carbon, an ion exchange resin treatment, an ion exchange membrane, a dialysis membrane, a reverse osmosis membrane, a treatment method using an ultrafiltration membrane, and the like.

Next, the organic electroluminescent element of the present invention will be described.
The organic electroluminescent element of the present invention is obtained by sandwiching at least one layer containing at least one polymer compound of the present invention or an intermediate polymer compound thereof between a pair of electrodes. An organic electroluminescent element is usually formed by sandwiching at least one light emitting layer containing at least one light emitting component between a pair of electrodes. A hole injection / transport layer and / or an electron injection containing a hole injection component as desired, considering the functional level of the hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer. An electron injecting and transporting layer containing components can also be provided.

  For example, when the compound used for the light emitting layer has a good hole injection function, hole transport function and / or electron injection function, and electron transport function, the light emitting layer is a hole injection transport layer and / or electron injection transport. As a type of element configuration that also serves as a layer, a single-layer type element configuration can be adopted. In addition, when the light emitting layer is poor in the hole injection function and / or the hole transport function, a two-layer device configuration in which a hole injection transport layer is provided on the anode side of the light emitting layer can be obtained. When the layer is poor in the electron injection function and / or the electron transport function, a two-layer element configuration in which an electron injection transport layer is provided on the cathode side of the light emitting layer can be obtained. Furthermore, a three-layer device structure in which the light-emitting layer is sandwiched between a hole injecting and transporting layer and an electron injecting and transporting layer can be used.

  In addition, each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single layer structure or a multilayer structure, and the hole injecting and transporting layer and the electron injecting and transporting layer The layer having an injection function and the layer having a transport function can be separately provided.

  In the organic electroluminescence device of the present invention, the polymer compound of the present invention is preferably used as a constituent component of the charge injection transport layer and / or the light emitting layer, and the hole injection transport layer and the electron injection are used as the charge injection transport layer. Although a transport layer is mentioned, a hole injection transport layer is particularly preferable.

  In the organic electroluminescent element of the present invention, the polymer compound of the present invention may be used alone or in combination.

  The configuration of the organic electroluminescent device of the present invention is not particularly limited. For example, (EL-1) anode 2 / hole injection transport layer 3 / light emitting layer 4 / electron injection transport layer 5 / cathode 6 Type device (FIG. 1), (EL-2) anode 2 / hole injection transport layer 3 / light emitting layer 4 / cathode 6 type device (FIG. 2), (EL-3) anode 2 / light emitting layer 4 / electron injection transport Layer 5 / cathode 6 type element (FIG. 3), (EL-4) anode 2 / light emitting layer 4 / cathode 6 type element (FIG. 4), and the like. Further, (EL-5) anode 2 / hole injection / transport layer 3 / second hole injection / transport layer 3 "/ light-emitting layer 4 / electron injection / transport layer 5 in a form in which a plurality of hole injection / transport layers are stacked. / Cathode 6 type element (FIG. 5) The element structure of (EL-4) type is a type in which a light emitting component is sandwiched between a pair of electrodes as a light emitting layer 4. (EL-6) A device of a type sandwiched between a pair of electrodes in a single layer form in which a hole injection / transport component 3a, a light emitting component 4a and an electron injection component 5a are mixed as the light emitting layer 4 (FIG. 6), EL-7) A device of a type sandwiched between a pair of electrodes in a single layer form in which a hole injection transport component 3a and a light emitting component 4a are mixed as the light emitting layer 4 (FIG. 7), and (EL-8) as the light emitting layer 4 The light emitting component 4a and the electron injecting component 5a were mixed and sandwiched between a pair of electrodes. It may be any of elements (Fig. 8).

The organic electroluminescent device of the present invention is not limited to these device configurations, and each type of device can be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers. Further, in each type of device, the hole injection / transport layer is disposed between the light emitting layer, the hole injection / transport component and the light emitting component mixed layer and / or the light emitting layer and the electron injection / transport layer between the light emitting component and the light emitting component. And a mixed layer of electron injecting and transporting components can be provided.
A preferred organic electroluminescent element is an (EL-1) type element, an (EL-2) type element, an (EL-5) type element, an (EL-6) type element or an (EL-7) type element. More preferably, it is an (EL-1) type element, an (EL-2) type element, or an (EL-5) type element.

  Hereinafter, the components of the organic electroluminescence device of the present invention will be described in detail. As an example, (EL-1) anode / hole injection / transport layer / light-emitting layer / electron injection / transport layer / cathode type element shown in FIG. 1 will be described.

  In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer, 5 is an electron injection / transport layer, 6 is a cathode, and 7 is a power source.

The organic electroluminescent element of the present invention is preferably supported by the substrate 1, and the substrate is not particularly limited, but a transparent or translucent substrate is preferable, and the material is soda lime glass, Examples thereof include glass such as borosilicate glass and transparent polymers such as polyester, polycarbonate, polysulfone, polyethersulfone, polyacrylate, polymethyl methacrylate, polypropylene, and polyethylene. Further, a substrate made of a translucent plastic sheet, quartz, transparent ceramics, or a composite sheet in which these are combined can also be used. Furthermore, for example, a color filter film, a color conversion film, and a dielectric reflection film can be combined with the substrate to control the emission color.

As the anode 2, it is preferable to use a metal, alloy or conductive compound having a relatively large work function as an electrode material. Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In ₂ O ₃ ), tin oxide (SnO ₂ ), zinc oxide, ITO ( Indium tin oxide (Indium Tin Oxide), polythiophene, polypyrrole, etc. can be mentioned. These electrode materials may be used alone or in combination. For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition or sputtering. Further, the anode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the anode is preferably set to several hundred Ω or less, more preferably about 5 to 50 Ω. The thickness of the anode is generally about 5 to 1000 nm, more preferably about 10 to 500 nm, although it depends on the material of the electrode material used.

  The hole injection transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes.

  The hole injecting and transporting layer of the organic electroluminescence device of the present invention is composed of the polymer compound of the present invention and / or other compounds having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, Oxazole derivatives, hydrazone derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, and the like). The compounds having a hole injecting and transporting function may be used alone or in combination.

  The organic electroluminescence device of the present invention preferably contains the polymer compound of the present invention in the hole injection transport layer. In the organic electroluminescence device of the present invention, other compounds having a hole injecting and transporting function that can be used include triarylamine derivatives (for example, 4,4′-bis [N-phenyl-N- (4 ” -Methylphenyl) amino] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methoxyphenyl) amino] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (1" -naphthyl) amino] -1,1 ' -Biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] -1,1'-biphenyl, 1,1-bis [4 '-[ N, N-di (4 "-methylphenyl) amino] phenyl] cyclohexane, 9 10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 ", 4" '-bis [N', N'-di (4-methylphenyl) amino] biphenyl-4-yl] aniline, N, N'-bis [4 -(Diphenylamino) phenyl] -N, N'-diphenyl-1,3-diaminobenzene, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,4-diamino Benzene, 5,5 "-bis [4- (bis [4-methylphenyl] amino) phenyl-2,2 ': 5', 2" -terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4 ', 4 "-Tris (9H-carbazole- 9-yl) triphenylamine, 4,4 ', 4 "-tris [N, N-bis (4"'-tert-butylbiphenyl-4 ""-yl) amino] triphenylamine, 1,3,5 -Tris [N- (4'-diphenylamino) benzene] and the like), polythiophene and derivatives thereof, poly-N-vinylcarbazole and derivatives thereof are more preferable.

  When the polymer compound of the present invention and another compound having a hole injection / transport function are used in combination, the content of these polymer compounds in the hole injection / transport layer is preferably 0.1% by mass or more, More preferably, it is 0.5-99.9 mass%, More preferably, it is 3-97 mass%.

  When the polymer compound of the present invention and another compound having a hole injection / transport function are used in combination, a layer composed of the polymer compound of the present invention and a layer composed of another compound having a hole injection / transport function are laminated. May be. In the case of stacking, it is preferable to stack a layer made of another compound having a hole injecting and transporting function on a layer made of the polymer compound of the present invention.

In the hole injecting and transporting layer, a compound having a hole injecting and transporting function and an electron accepting compound may be used in combination. Examples of the electron-accepting compound include TBPAH (tris (4-bromophenyl) aluminum hexachloroantimonate) described in JP-A No. 11-283750, FeCl ₃ , and tris (penta) described in JP-A No. 2003-31365. Lewis acids such as boron compounds such as (fluorophenyl) borane. When using an electron-accepting compound together, it is preferable that content of an electron-accepting compound is 0.1-50 mass% with respect to a positive hole injection transport layer.

  The light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.

  The light emitting layer can be formed using at least one of the polymer compound of the present invention and / or a compound having another light emitting function.

  Examples of other compounds having a light emitting function include acridone derivatives, quinacridone derivatives, diketopyrrolopyrrole derivatives, polycyclic aromatic compounds [for example, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenyl Cyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthenyl) benzene, 4,4′-bis (9 "-Ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1,2,3-cd: 1 ', 2', 3'-lm] perylene derivatives], triarylamine derivatives (eg hole injection Examples of the compound having a transport function include the aforementioned compounds), organometallic complexes For example, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine, 3-hydroxyflavone Zinc salt, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [for example, 1,1,4,4-tetraphenyl-1,3-butadiene, 4,4′-bis (2 , 2-diphenylvinyl) biphenyl, 4,4′-bis [(1,1,2-triphenyl) ethenyl] biphenyl], coumarin derivatives (eg, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, Coumarin 138, Coumarin 151, Coumarin 152, Coumarin 153, Coumarin 3 07, Coumarin 311, Coumarin 314, Coumarin 334, Coumarin 338, Coumarin 343, Coumarin 500), pyran derivatives (for example, DCM1, DCM2), oxazone derivatives (for example, Nile Red), benzothiazole derivatives, benzoxazole derivatives, benzimidazole Derivatives, pyrazine derivatives, cinnamic acid ester derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polybiphenylene vinylene and derivatives thereof, Examples include polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, polythienylene vinylene and its derivatives. Can. In particular, an acridone derivative, a quinacridone derivative, a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex, and a stilbene derivative are preferable, and a polycyclic aromatic compound and an organometallic complex are more preferable.

The organic electroluminescent element of the present invention preferably contains the polymer compound of the present invention in the light emitting layer. Furthermore, a layer containing a compound having a light emitting function other than the polymer compound may be included as a light emitting layer between the pair of electrodes.
When the polymer compound of the present invention and another compound having a light emitting function are used in combination, the proportion of these polymer compounds in the light emitting layer is preferably adjusted to 0.001 to 99.999% by mass.

  The light emitting layer can also be formed from a host compound and a guest compound (dopant) as described in J. Appl. Phys., 65, 3610 (1989) and Japanese Patent Laid-Open No. 5-214332.

  The polymer compound of the present invention can be used as a host compound for the light emitting layer, and can also be used as a guest compound. When the light emitting layer is formed using the polymer compound of the present invention as a host compound, examples of the guest compound include compounds having other light emitting functions described above, and among them, polycyclic aromatic compounds are preferable.

  When the light emitting layer is formed using the polymer compound of the present invention as a host compound, the guest compound is preferably 0.001 to 40% by mass, more preferably 0.01 to 30% by mass with respect to the host compound. More preferably, 0.1-20 mass% is used. The light emitting layer can be formed using the polymer compound of the present invention as a host material and at least one compound having a light emitting function as a guest material.

The organic electroluminescent element of the present invention preferably contains the polymer compound of the present invention as a host material in the light emitting layer.
When the polymer compound of the present invention is used in combination with another compound having a light emitting function as a host material, the polymer compound of the present invention in the light emitting layer is preferably 40.0 to 99.9% by mass. More preferably, it is 60.0-99.9 mass%.

  The usage-amount of a guest material is 0.001-40 mass% with respect to the high molecular compound of this invention, Preferably, it is 0.01-30 mass%, More preferably, it is 0.1-20 mass%. Moreover, a guest material may be used independently and may be used together.

  When the light emitting layer is formed using the polymer compound of the present invention as a guest material, the host material is preferably a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex, or a stilbene derivative, and the polycyclic aromatic compound An organometallic complex is more preferable.

  When the polymer compound of the present invention is used as a guest material, the compound is preferably 0.001 to 40% by mass, more preferably 0.01 to 30% by mass, and still more preferably 0.1 to 20%. Use mass%.

The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating injection of electrons from the cathode and / or a function of transporting injected electrons.
Furthermore, a layer containing a compound having an electron injecting and transporting function other than the polymer compound may be included as an electron injecting and transporting layer between the pair of electrodes.

  Examples of the compound having an electron injecting function used in the electron injecting and transporting layer include organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenones. Derivatives, thiopyrandioxide derivatives and the like. Examples of organometallic complexes include organoaluminum complexes such as tris (8-quinolinolato) aluminum, organic beryllium complexes such as bis (10-benzo [h] quinolinolato) beryllium, beryllium salts of 5-hydroxyflavone, 5- Examples thereof include an aluminum salt of hydroxyflavone. Preferred is an organoaluminum complex, and more preferred is an organoaluminum complex having an unsubstituted or substituted 8-quinolinolate ligand. Examples of the organoaluminum complex having an unsubstituted or substituted 8-quinolylate ligand include compounds represented by general formula (a) to general formula (c).

(G) ₃ -Al (a)
(In the formula, G represents an unsubstituted or substituted 8-quinolinolato ligand.)
(G) ₂ -Al-OM (b)
(In the formula, as described above, OM represents a phenolate ligand, and M represents a hydrocarbon group having 6 to 24 carbon atoms having a phenyl group.)
(G) _2- Al-O-Al- (G) ₂ (c)
(In the formula, G is as described above.)

Specific examples of organoaluminum complexes having an unsubstituted or substituted 8-quinolinolato ligand include, for example, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl). -8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) Aluminum, screw (2-mesh Ru-8-quinolinolato) (4-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8) -Quinolinolate) (2,6-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5- Dimethylphenolate) aluminum, bis (2-methyl-8-ki) Linoleate) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2 , 4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,4 5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4 -Dimethyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis ( , 4-Dimethyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) ) (3,5-dimethylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) aluminum -Μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, bis (2-Methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxy -Bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolato) ) Aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl) Mention may be made of -8-quinolinolato) aluminum- [mu] -oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum.

  A compound having an electron injection function may be used alone or in combination.

As the cathode 6, it is preferable to use a metal, an alloy or a conductive compound having a relatively small work function as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, yttrium, and aluminum. , Aluminum-lithium alloy, aluminum-calcium alloy, aluminum-magnesium alloy, lithium fluoride, and graphite thin film. These electrode materials may be used alone,
A plurality of them may be used in combination.

  For the cathode, these electrode materials can be formed on the electron injecting and transporting layer by, for example, vapor deposition, sputtering, ion vapor deposition, ion plating, or cluster ion beam.

  The cathode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the cathode is preferably several hundred Ω or less. The thickness of the cathode is usually 5 to 1000 nm, preferably 10 to 500 nm, although it depends on the electrode material used. In order to efficiently extract light emitted from the organic electroluminescent device of the present invention, at least one of the anode and the cathode is preferably transparent or translucent, and generally has a transmittance of emitted light of 70% or more. It is preferable to set the material and thickness of the anode or cathode.

  The organic electroluminescent device of the present invention may contain a singlet oxygen quencher in at least one of the hole injection transport layer, the light emitting layer, and the electron injection transport layer. Although it does not specifically limit as a singlet oxygen quencher, For example, rubrene, a nickel complex, diphenylisobenzofuran is mentioned, Preferably it is rubrene.

  The polymer compound of the present invention can be used not only as a charge injecting and transporting material and a light emitting material, but also as an organic semiconductor material, an optical material, or a conductive material by doping.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to a following example.
In addition, the molecular weight in each Example measured the number average molecular weight of polystyrene conversion by gel permeation chromatography (GPC).

(GPC analysis conditions)
Apparatus: Gel permeation chromatograph GPC 101 (manufactured by Shodex)
Detector: differential refractometer column: GPC K-806LX3 (8.0 mm I.D. × 30 cm, manufactured by Shodex)
Column temperature: 40 ° C Solvent: Chloroform Injection volume: 100 μl
Flow rate: 1ml / min
Standard substance: Monodispersed polystyrene (manufactured by Shodex)

  Evaluation of film formability was confirmed by observing the surface roughness with an atomic force microscope (AFM).

(AFM measurement conditions)
Device: Seiko Instruments Scanning Probe Microscope SPI-3800N
Analysis conditions:
Measurement mode DFM
Cantilever SI-DF20
Measurement range 5μm × 5μm

[Example 1]
Production of polymer compound represented by exemplary compound number [A-1] 9.6 g (18.5 mmol) of halogenated tetraphenylbutadiene compound (formula 12), 4,4′-biphenyldiboronic acid under nitrogen atmosphere 4.8 g (20.0 mmol) was dissolved in 180 g of toluene, and 72.6 mg (0.063 mmol) of tetrakis (triphenylphosphine) palladium was further added. After stirring for 10 minutes at room temperature, 72 ml of a 20% tetraethylammonium hydride aqueous solution was added, and the temperature was raised to 110 ° C. and reacted for 18 hours while stirring. Thereafter, 5.03 g (31.97 mmol) of bromobenzene was dissolved in 18 mL of toluene and added to the reaction solution, followed by stirring at 110 ° C. for 2 hours. Thereafter, 3.95 g (26.76 mmol) of phenylboronic acid was added to the reaction solution, and the mixture was stirred at 110 ° C. for 2 hours. After cooling to 50 ° C., the organic layer was added dropwise to 3.5 L of a methanol / water (1/1) mixture and stirred for 1 hour. The precipitate was filtered, washed with methanol and ion exchange water, and dried under reduced pressure. Then, it melt | dissolved in 600 mL of toluene, and refine | purified through the silica gel column (silica amount 200mL). The purified solution was added dropwise to 2.5 L of methanol and stirred for 1 hour, and the precipitate was filtered and dried under reduced pressure to obtain the desired product. The yield of the obtained target product was 10.3 g.
The polystyrene equivalent weight average molecular weight of the target product [A-1] was 19,400.

[Example 2]
Production of Polymer Compound Represented by Exemplary Compound Number [A-6] 9.6 g (18.5 mmol) of a halogenated tetraphenylbutadiene compound (Formula 12) represented by Formula (12) under a nitrogen atmosphere, 9.6 g (20.0 mmol) of 9-dioctylfluorene-2,7-diboronic acid (manufactured by Aldrich) was dissolved in 180 g of toluene, and further 72.6 mg (0.063 mmol) of tetrakis (triphenylphosphine) palladium. Was added. After stirring at room temperature for 10 minutes, 72 ml of a 20% tetraethylammonium hydride aqueous solution was added, and the temperature was raised to 110 ° C. and the reaction was continued. Thereafter, the same treatment as in Example 1 was performed to obtain the target product. The yield of the obtained target product was 14.8 g.
The weight average molecular weight in terms of polystyrene of the target product [A-6] was 22500.

[Example 3]
Production of Polymer Compound Represented by Exemplary Compound Number [B-1] 9.6 g (18.5 mmol) of a halogenated tetraphenylbutadiene compound (Formula 12) represented by Formula (12) under a nitrogen atmosphere, N— It was dissolved in octylcarbazole-3,6-diboronic acid 7.3 g (20.0 mmol) and toluene 200 g, and tetrakis (triphenylphosphine) palladium 72.6 mg (0.063 mmol) was further added. After stirring at room temperature for 10 minutes, 72 ml of a 20% tetraethylammonium hydride aqueous solution was added, and the temperature was raised to 110 ° C. and the reaction was continued. Thereafter, the same treatment as in Example 1 was performed to obtain the target product. The yield of the obtained target product was 14.2 g.
The weight average molecular weight in terms of polystyrene of the target product [B-1] was 14500.

[Example 4]
Production of polymer compound represented by exemplified compound number [B-30] 15.7 g (18.5 mmol) of halogenated tetraphenylbutadiene (formula 13), dibenzofuran-2,7-diboronic acid under nitrogen atmosphere 1 g (20.0 mmol) was dissolved in 200 g of toluene, and 72.6 mg (0.063 mmol) of tetrakis (triphenylphosphine) palladium was further added. After stirring at room temperature for 10 minutes, 72 ml of a 20% tetraethylammonium hydride aqueous solution was added, and the temperature was raised to 110 ° C. and the reaction was continued. Thereafter, the same treatment as in Example 1 was performed to obtain the target product. The yield of the obtained target product was 15.5 g.
The weight average molecular weight in terms of polystyrene of the target product [B-30] was 24000.

[Example 5] Preparation and evaluation of organic EL element A glass substrate (sputtered film-formed product; sheet resistance 15 Ω) having a patterned ITO transparent electrode with a thickness of 150 nm was mixed with a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), Ultra After cleaning in the order of ultrasonic cleaning with pure water, acetone, and isopropyl alcohol, drying was performed with nitrogen blowing, and finally ultraviolet ozone cleaning was performed. Subsequently, PEDOT / PSS (Formula 14) was formed into a film with a thickness of 65 nm by a spin coat method, and dried under reduced pressure (200 ° C., 1 hour) on a hot plate to form a first hole injection transport layer. Next, a toluene solution (1.5% by weight) of the polymer compound synthesized in Example 1 was formed into a film having a thickness of 50 nm by spin coating, and heat treatment was performed in a nitrogen atmosphere on a hot plate (180 C., 1 hour), a second hole injection transport layer was formed.

  Next, after rinsing the second hole injecting and transporting layer with toluene, a xylene solution (1.2% by weight) of polyfluorene (formula 15) is formed into a film having a thickness of 60 nm by a spin coating method. The plate was dried under reduced pressure (140 ° C., 30 minutes) to form a light emitting layer. Next, the glass substrate is fixed to the substrate holder of the vapor deposition apparatus, lithium fluoride (LiF) is deposited on the light emitting layer, and the film thickness is 0.5 nm at a vapor deposition rate of 0.2 nm / second using a molybdenum boat. Then, aluminum (Al) was heated with a tungsten boat to form an aluminum layer having a thickness of 100 nm at a deposition rate of 2.0 nm / sec to complete the cathode. As described above, an organic electroluminescent element having a light emitting area portion having a size of 2 mm × 2 mm was obtained. In this organic electroluminescence device, light emission was observed through a glass substrate by applying a direct current voltage using ITO as an anode and LiF / Al as a cathode. The luminance was measured with a Topcon luminance meter BM-8.

A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, blue light emission of 4.7 V and a luminance of 155 cd / cm ² was confirmed. When continuous driving was performed for 200 hours from an initial luminance of 500 cd / cm ² , the luminance reduction rate was 20%. The results are shown in Table 1.

[Example 6] to [Example 8]
In Example 5, in forming the second hole injection transport layer, instead of using the polymer compound obtained in Example 1, the polymer compound obtained in Examples 2 to 4 was used. According to the operation described in Example 5, an organic electroluminescent element was produced. Further, in the same manner as in Example 5, a DC voltage was applied to the device, the characteristics of the device were measured, and the results are shown in Table 1.

[Comparative Example 1]
In Example 5, in forming the second hole injecting and transporting layer, instead of using the polymer compound obtained in Example 1, polymer compound ADS259BE (formula 16) manufactured by American DyeSource was used, According to the operation described in Example 5, an organic electroluminescent element was produced. Further, in the same manner as in Example 5, a DC voltage was applied to the device, the characteristics of the device were measured, and the results are shown in Table 1.

[Comparative Example 2]
In Example 5, when forming the second hole injecting and transporting layer, instead of using the polymer compound obtained in Example 1, it is represented by the formula (17) described in JP-A-2006-316224. An organic electroluminescent device was produced according to the procedure described in Example 5 except that a polymer compound composed of repeating units was used. Further, in the same manner as in Example 5, a DC voltage was applied to the device, the characteristics of the device were measured, and the results are shown in Table 1.

  As is clear from Table 1, the organic EL device of the present invention using the polymer compound of the present invention as a hole injecting and transporting material has high emission luminance and excellent luminous efficiency, and further has a low luminance reduction rate and device lifetime. It was excellent at.

  The organic electroluminescent element obtained by using the polymer compound of the present invention can be used as a panel-type light source, various light-emitting elements, display elements, labels, and sensors.

It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element.

Explanation of symbols

1: substrate 2: anode 3: hole injection / transport layer 3 ": second hole injection / transport material 3a: hole injection / transport component 4: light-emitting layer 4a: light-emitting component 5: electron injection / transport layer 5a: electron injection / transport Component 6: Cathode 7: Power supply

Claims (8)

A polymer compound having at least one repeating unit represented by the general formula (1) in a polymer chain.

[In the formula, Ar represents a substituted or unsubstituted divalent aromatic group. n represents an integer of 1 or more, and Ar may be different from each other when n is an integer of 2 or more. Ar ¹ and Ar ² represent a substituted or unsubstituted divalent aromatic group which may be the same or different from each other, and Ar ¹ and Ar ² may be bonded to each other to form a ring. .
Ar ³ and Ar ⁴ represent a substituted or unsubstituted monovalent aromatic group which may be the same or different from each other, and Ar ³ and Ar ⁴ may be bonded to each other to form a ring. . ] In the general formula (1), Ar and Ar ^{1 to} Ar ⁴ are carbocyclic aromatic groups having 6 to 30 carbon atoms in the aromatic ring constituting the aromatic group or carbon numbers in the aromatic ring constituting the aromatic group. The polymer compound according to claim 1, wherein is a heterocyclic aromatic group having 2 to 30. An organic electroluminescent element comprising at least one layer containing at least one polymer compound according to claim 1 or 2 sandwiched between a pair of electrodes. The organic electroluminescent element according to claim 3, wherein the layer containing the polymer compound is a charge injection transport layer. The organic electroluminescent device according to claim 4, wherein the charge injection transport layer is a hole injection transport layer. The organic electroluminescent element according to claim 3, wherein the layer containing the polymer compound is a light emitting layer. The organic electroluminescent element according to any one of claims 3 to 6, further comprising a layer containing a compound having a light emitting function other than the polymer compound as a light emitting layer between the pair of electrodes. The organic electroluminescent element according to any one of claims 3 to 7, which has a layer containing a compound having an electron injecting and transporting function other than the polymer compound as an electron injecting and transporting layer between the pair of electrodes.

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