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WO2007058368A1 - Compose polymere et element electroluminescent polymere l’utilisant - Google Patents

Compose polymere et element electroluminescent polymere l’utilisant Download PDF

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Publication number
WO2007058368A1
WO2007058368A1 PCT/JP2006/323257 JP2006323257W WO2007058368A1 WO 2007058368 A1 WO2007058368 A1 WO 2007058368A1 JP 2006323257 W JP2006323257 W JP 2006323257W WO 2007058368 A1 WO2007058368 A1 WO 2007058368A1
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group
aryl
formula
ring
substituted
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PCT/JP2006/323257
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English (en)
Japanese (ja)
Inventor
Daisuke Fukushima
Yoshiaki Tsubata
Makoto Anryu
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Sumitomo Chemical Company, Limited
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Priority to GB0810612A priority Critical patent/GB2447173B/en
Priority to CN2006800513788A priority patent/CN101360773B/zh
Priority to DE112006002998T priority patent/DE112006002998T5/de
Publication of WO2007058368A1 publication Critical patent/WO2007058368A1/fr

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Definitions

  • the present invention relates to a polymer compound and a polymer light emitting device using the same.
  • the above polymer compound does not necessarily have sufficient heat resistance and fluorescence intensity, and a light emitting device using the above polymer compound does not necessarily have sufficient device characteristics such as device life and luminous efficiency. There was a problem.
  • An object of the present invention is a polymer compound that is useful as a light-emitting material or a charge transport material, and excellent in heat resistance, fluorescence intensity, and the like, and a polymer light-emitting device excellent in device characteristics such as device lifetime and light emission efficiency Is to provide.
  • the present invention provides a polymer compound comprising at least one repeating unit represented by the following formula (1) and at least one repeating unit selected from the following formulas (2) and (3): It is.
  • Ar 1 represents an optionally substituted aryl group or monovalent aromatic heterocyclic group.
  • a r 2 represents an arylene group or a divalent aromatic heterocyclic group which may have a substituent.
  • Z represents a divalent aromatic group having a condensed ring structure, and the group may have a substituent.
  • Two A r 1 may be the same or different, and two A r 2 may be the same or different.
  • a ring and B ring each independently represent an aromatic hydrocarbon ring which may have a substituent, but at least one of A ring and B ring is condensed with a plurality of benzene rings. It is an aromatic hydrocarbon ring, and two bonds are present on the A ring or B ring, and R w and R x are each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group.
  • aryloxy group arylalkyl group, arylalkylalkoxy group, arylalkylthio group, arylene alkenyl group, arylene alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, Represents an acyloxy, group, imine residue, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substituted carboxyl group or cyano group R w and R x may be bonded to each other to form a ring.
  • C ring and D ring each independently represent an aromatic ring which may have a substituent, and two bonds are present on C ring or D ring respectively.
  • Y is an oxygen atom
  • sulfur represents an atom or —O—C (R K ) 2 —
  • R K represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aryl group Alkoxy group, arylalkylthio group, arylenealkenyl group, arylenealkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imidate de group, monovalent heterocyclic group, a force Rupokishiru group, substituted carboxyl group,.
  • two R K representing a nitro
  • the polymer compound of the present invention contains one or more repeating units represented by the above formula (1).
  • Ar 1 represents an aryl group or a monovalent aromatic heterocyclic group which may have a substituent.
  • Two A r 1 may be the same or different.
  • a r 1 preferably represents an aryl group.
  • the aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and includes those having an independent benzene ring or condensed ring.
  • the aryl group usually has about 6 to 60 carbon atoms, preferably 6 to 48, more preferably 6 to 30, still more preferably 6 to 18, and still more preferably 6 to 1. 0, particularly preferably 6.
  • the carbon number does not include the carbon number of the substituent.
  • aryl groups include phenyl group, 1_naphthyl group, 2-naphthyl group, 1 monoanthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-phenanthryl group, 9-phenanthryl group, 1_naphthase group.
  • Group, 2-naphthacenyl group, etc. preferably phenyl group, 1_naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group. More preferably a phenyl group, a 1_naphthyl group, and a 2-naphthyl group, and even more preferably a phenyl group.
  • the monovalent aromatic heterocyclic group means a remaining atomic group obtained by removing one hydrogen atom from an aromatic heterocyclic compound, and usually has about 4 to 60 carbon atoms, preferably 4 to 20 carbon atoms. More preferably, it is 4-9, More preferably, it is 4-5.
  • the carbon number of the monovalent aromatic heterocyclic group does not include the carbon number of the substituent.
  • a heterocyclic compound is an organic compound having a cyclic structure in which not only carbon atoms but also hetero atoms such as oxygen, sulfur, nitrogen, phosphorus, and boron are included in the ring. This includes things.
  • the monovalent aromatic heterocyclic group examples include 2 mono-cenyl group, 3-cenyl group, 2-pyrrolyl group, 3-pyrrolyl group, 2-furyl group, 3-furyl group, 2-pyridyl group, 3 —Pyridyl group, 4-pyridyl group, 2_quinolyl group, 4 monoquinolyl group, 5-quinolyl group, 1-isoquinolyl group, 3_isoquinolyl group, 6-iso Quinolyl group, etc., 2—Cenyl group, 3—Cenyl group, 2—Pyridyl group, 3—Pyridyl group, 4—Pyridyl group, 2 —Quinolyl group, 4—Quinolyl group, 5—Quinolyl group, 1 unit
  • An isoquinolyl group, a 3-isoquinolyl group, and a 6-isoquinolyl group are preferable, and a 2_phenyl group, a 3-enyl group, a
  • the substituent is an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, Arylthio group, Arylalkyl group, Arylalkoxy group, Arylalkylthio group, Arylalkenyl group, Arylalkynyl group, Amino group, Substituted amino group, Silyl group, Substituted silyl group, Halogen atom, Acyl group, Asiloxy A group selected from a group, an imine residue, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, and a cyan group.
  • it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, a substituted amino group, a substituted silyl group, an acyl group, a substituted carboxyl group and a cyan group. More preferably, it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, and a substituent rupoxyl group, and more preferably an alkyl group, an alkoxy group, an aryl. Selected from groups, particularly preferably an alkyl group.
  • the alkyl group may be linear, branched or cyclic, and usually has about 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms.
  • Specific examples include methyl group, ethyl group, propyl group, i-propyl group, butyl group, i-butyl group, t-butyl group, pentyl group, isoamyl group, hexyl group, cyclohexyl group, heptyl group.
  • the alkoxy 'group may be linear, branched or cyclic, and usually has about 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms. Specific examples thereof include a methoxy group, an ethoxy group, Propyloxy group, i-Propyloxy group, Butoxy group, i-Butoxy group, t-Butoxy group, Pentyloxy group, Hexyloxy group, Cyclohexyloxy group, Heptyloxy group, Octyloxy group, 2_Ethylhexyloxy group, Nonyloxy group , Decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, rifluoromethoxy group, penoxyfluoroethoxy group, perfluorobutoxy group, perfluorohexyl group, perfluorooctyl group , Methoxymethyloxy group, 2-methoxyethyloxy group, 2-ethoxyethyloxy group,
  • the alkylthio group may be linear, branched or cyclic, and usually has about 1 to 20 carbon atoms, preferably 3 to 20 carbon atoms. Specific examples thereof include a methylthio group, an ethylthio group, and propylthio group.
  • the aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, having a condensed ring, two or more independent benzene rings or condensed rings bonded directly or through a group such as vinylene. Also included.
  • the aryl group usually has about 6 to 60 carbon atoms, preferably? ⁇ 4-8. Specific examples thereof include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracerenyl group, pentafluorophenyl group, and the like.
  • alkyl groups having 1 to 12 carbon atoms and / or alkoxy groups having 1 to 12 carbon atoms and / or alkyloxy A phenyl group having at least one carbonyl group as a substituent is preferable, and specific examples thereof include 3-methylphenyl group, 4-methylphenyl group, 3,5-dimethylphenyl group, 4-propylphenyl group, Mesityl group, 4-i-propylphenyl group, 4-butylbutyl group, 41-i-butylphenyl group, 4-t-butylphenyl group, 4-pentylphenyl group, 4-isoamylphenyl group, 4-to-1 Xylphenyl group, 2,6-dimethyl-4 t-butylphenyl group, 4-heptylphenyl group, 4-octylphenyl group, 4-nonylphenyl group, 4-decy
  • Ariruokishi group is usually about 6-6 0 carbon atoms, preferably 7-4 8, and specific examples thereof include phenoxy group, -C I 2 alkoxy phenoxyethanol group (C, -C I 2 is It indicates that the number of carbon atoms is 1 to 12. The same applies to the following:), C, to C I 2 alkylphenoxy group, 1 naphthyloxy group, 2_naphthyloxy group, penfluorofluorophenyloxy group, etc. From the viewpoints of solubility in an organic solvent, device characteristics, easiness of synthesis, and the like, a -C I 2 alkoxyphenoxy group and a C 1 -C I 2 alkylphenoxy group are preferable.
  • C, ⁇ C I 2 alkoxy include methoxy, ethoxy, propyloxy, i-propyloxy, butoxy, i-butoxy, t-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethyl Examples include hexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy, and the like.
  • C, ⁇ C I 2 alkylphenoxy groups include methylphenoxy group, ethylphenoxy group, dimethylphenoxy group, propylphenoxy group, 1,3,5-trimethylphenoxy group, Enoxy group, i-propyl phenoxy group, butyl phenoxy group, i_butyl phenoxy group, t-butyl phenoxy group, pentyl phenoxy group, isoamyl phenoxy group, hexyl phenoxy group, heptyl phenoxy group, octyl phenoxy group, nonyl phenoxy group Group, decylphenoxy group, dodecylphenoxy group and the like.
  • the arylthio group usually has about 3 to 60 carbon atoms. Specific examples thereof include a phenylthio group, Examples include alkoxyphenylthio groups, C, to C I 2 alkylphenylthio groups, 1-naphthylthio groups, 2_naphthylthio groups, pendefluorofluorothio groups, etc., solubility in organic solvents, device characteristics, synthesis From the viewpoint of easiness to perform, C, to C I 2 alkoxyphenylthio groups and 2- alkylphenylthio groups are exemplified.
  • the arylalkyl group usually has about 7 to 60 carbon atoms, preferably 7 to 48, and specific examples thereof include phenyl mono-C, -C I 2 alkyl groups, C, -C I 2 alkoxyphenols. Lou C, -C I 2 alkyl group, ⁇ 12 Arukirufue two root-alkyl groups, 1-naphthyl Chiru C, ⁇ C I 2 alkyl group, 2 - Nafuchiru C, such as -C I 2 alkyl groups and the like, organic From the standpoints of solubility in organic solvents, device characteristics, easiness of synthesis, etc., C, ⁇ C I 2 alkoxysilane C, ⁇ C I 2 alkyl group, J
  • the arylalkoxy group usually has about 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms. Specific examples thereof include a phenylmethoxy group, a phenylethoxy group, a phenylbutoxy group, and a phenylpentyloxy group. Phenyl hexyloxy group, phenyl heptoxy group, phenyloctyloxy group, etc. ⁇ Alkoxy group, same, ⁇ . , Arco Kishifueniru - C, ⁇ C I 2 alkoxy group, C, ⁇ C IZ Arukirufue two Lou C, ⁇ C I 2 alkoxy group, Ji 1 _ Nafuchiru!
  • ⁇ Alkoxy group, 2_naphthyl C, ⁇ C I 2 alkoxy group, etc. are exemplified. From the viewpoint of solubility in organic solvent, device characteristics, ease of synthesis, etc., C, ⁇ C I 2 alkoxy Examples include phenyl C, ⁇ C 1 Z alkoxy groups, C, ⁇ C I 2 alkylphenyls—alkoxy groups.
  • the arylalkylthio group usually has about 7 to 60 carbon atoms, and preferably 7 to 48 carbon atoms.
  • one Ruarukeniru group has a carbon number of usually about 8 to 60, and specific examples thereof include phenyl - C 2 ⁇ C I 2 alkenyl groups, Ji
  • the aryl alkynyl group usually has about 8 to 60 carbon atoms, and specific examples thereof include phenyl-C 2 -C I 2 alkynyl group, C, -C I 2 alkoxy phenyl-C 2 -C I 2 Alkynyl group, C, ⁇ C I2 alkylphenyl—C 2 -C I 2 alkynyl group, 1-naphthyl—C 2 -C 1 2 alkynyl group, 2-naphthyl—C 2 -C I 2 alkynyl group, etc.
  • 2- alkoxyphenyl—C 2 -C I 2 alkynyl group, C, -C I 2 alkylphenyl C 2 -C I 2 alkynyl group are preferred.
  • substituted amino group examples include an amino group substituted with one or two groups selected from an alkyl group, an aryl group, an aryl alkyl group or a monovalent heterocyclic group.
  • the group, aryl group, aryl alkyl group or monovalent heterocyclic group may have a substituent.
  • the carbon number of the substituted amino group is usually about 1 to 60, not including the carbon number of the substituent, Preferably, it has 2 to 48 carbon atoms.
  • Examples of the substituted silyl group include a silyl group substituted with 1, 2 or 3 groups selected from an alkyl group, aryl group, aryl alkyl group or monovalent heterocyclic group.
  • the substituted silyl group usually has about 1 to 60 carbon atoms, preferably 3 to 48 carbon atoms.
  • the alkyl group, aryl group, aryl alkyl group or monovalent heterocyclic group may have a substituent.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the acyl group usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms. Examples include a group, propionyl group, butylyl group, isoptylyl group, bivalyl group, benzoyl group, trifluoroacetyl group, and pendefluorofluorobenzoyl group.
  • the acyloxy group usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms, and specific examples thereof include an acetoxy group, a propionyloxy group, a petityloxy group, an isoptyryloxy group, a bivalyloxy group, a benzoyloxy group, Examples thereof include a trifluoroacetyloxy group and a pentafluorobenzoyloxy group.
  • the imine residue has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms. Specific examples thereof include groups represented by the following structural formulas.
  • the amide group usually has about 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms.
  • Examples of the amide group include a formamide group, a acetoamide group, a propioamide group, a ptylamide group, a benzamide group, a triflule. Fluoroacetamide group, Pentofluorobenzamide group, Diformamide group, Diacetoamide group, Dipropioamide group, Dibutyroamide group, Dibenzamide group, Ditrifluoroacetamido group, Dipentafluorine benzamide group, Etc. are exemplified.
  • Examples of the acid imide group include residues obtained by removing a hydrogen atom bonded to the nitrogen atom from an acid imide.
  • the number of carbon atoms is about 4 to 20, and specific examples include the groups shown below. Be done
  • the monovalent heterocyclic group means a remaining atomic group obtained by removing one hydrogen atom from a heterocyclic compound, and usually has about 4 to 60 carbon atoms, preferably 4 to 20 carbon atoms.
  • the carbon number of the heterocyclic group does not include the carbon number of the substituent.
  • the heterocyclic compound is an organic compound having a cyclic structure in which the elements constituting the ring include not only carbon atoms but also hetero atoms such as oxygen, sulfur, nitrogen, phosphorus, and boron in the ring.
  • chenyl group a C 1, to C 2 alkyl chain group, a pyrrolyl group, a furyl group, a pyridyl group, a CiC ⁇ alkylpyridyl group, a piperidyl group, a quinolyl group, an isoquinolyl group, Cenyl group, C 1, ⁇ C I 2 alkylcenyl group, pyridyl group, i, ⁇ .
  • Alkylpyridyl groups are preferred.
  • substituted carboxyl group examples include an alkyl group, an aryl group, an aryl alkyl group or a carboxyl group substituted with a monovalent heterocyclic group, and usually has about 2 to 60 carbon atoms, preferably 2 to 4 carbon atoms.
  • Specific examples thereof include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, i-propoxycarbonyl group, butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, pentyloxycarbonyl group, Hexyloxycarbonyl group, Cyclohexyloxycarbonyl group, Heptyloxycarbonyl group, Octyloxycarbonyl group, 2-Ethylhexyloxycarbonyl group, Nonyloxycarbonyl group, Decyloxycarbonyl group, 3, 7-Dimethyl group Ctyloxycarbonyl group, dodecylo Xyloxycarbonyl group, trifluoromethoxycarbonyl group, penoxyfluoroethoxycarbonyl group, perfluorobutoxycarbonyl group, perfluorohexoxycarbonyl group, perfluorooctyloxycarbonyl group, fluoro Enoxycarbonyl group,
  • a r z represents an arylene group or a divalent aromatic heterocyclic group which may have a substituent.
  • Two A r 2 may be the same or different.
  • a r 2 preferably represents an arylene group.
  • the arylene group is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, and includes those having an independent benzene ring or condensed ring.
  • the arylene group usually has about 6 to 60 carbon atoms, preferably 6 to 48, more preferably 6 to 30, even more preferably 6 to 18, still more preferably 6 to 10, 6 is preferred.
  • the carbon number does not include the carbon number of the substituent.
  • arylene groups include 1,4-monophenylene groups, 1,3-phenylene groups, 1,2-phenylene groups, 1,4-naphthylene groups, 1,5_ Naphtylene group, 2,6-Naphthylene group, 1,4-One anthracenylene group, 1,5-Anthracenylene group, 2,6_Anthracenylene group, 9,10-Anthracenylene group, 2,7_Phenanthrylene group, 1,7-Naphthalenylene Group, 2,8-naphthenylene group, etc., preferably 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 1,5-naphthylene group 2, 6-naphthylene group, 1,4 monoanthracenylene group, 1,5-anthracenylene group, 2,6-anthracenylene group, 9,10-anthracenylene group, more preferably 1, 4 1-phenylene group, 1, 3-phenylene
  • the divalent aromatic heterocyclic group refers to the remaining atomic group obtained by removing two hydrogen atoms from an aromatic heterocyclic compound, and usually has about 4 to 60 carbon atoms, preferably 4 to 20 carbon atoms. Preferably it is 4-9, More preferably, it is 4-5. Specific examples of the divalent aromatic heterocyclic group include 2,5-chenyl group, 2,5-pyrrolyl group, 2,5-furyl group, 2,4-pyridyl group, 2,6-pyridyl group, 2 , 4 monoquinolyl group, 2, 6-quinolyl group, 1, 4-isoquinolyl group, 1,5-isoquinolyl group, etc.
  • a lysyl group, 2,6-pyridyl group, 2,4-quinolyl group, 2,6-quinolyl group, 1,4-isoquinolyl group, 1,5-isoquinolyl group are preferred, 2,5-chenyl group, 2,4 — Pyridyl group and 2,6-pyridyl group are more preferable, and 2,4-pyridyl group and 2,6-pyridyl group are more preferable.
  • the substituent is an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, Arylthio group, Arylalkyl group, Arylalkoxy group, Arylalkylthio group, Arylalkenyl group, Arylalkynyl group, Amino group, Substituted amino group, Silyl group, Substituted silyl group, Halogen atom, Acyl group, Asiloxy A group selected from a group, an imine residue, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group and a cyan group.
  • it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkyloxy group, a substituted amino group, a substituted silyl group, an acyl group, a substituent force oxyl group, and a cyan group, More preferably, it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, and a substituent rupoxyl group, and more preferably an alkyl group, an alkoxy group, Selected from aryl groups, particularly preferably alkyl groups.
  • substituted silyl groups, halogen atoms, acyl groups, acyloxy groups, imine residues, amide groups, acid imide groups, monovalent heterocyclic groups, substituted carboxyl groups, and specific examples are shown in A in the above formula (1).
  • the definition of substituents in the case where r 1 has a substituent is the same as the specific examples.
  • Z in the formula (1) represents a divalent aromatic group having a condensed ring structure.
  • the group may have a substituent.
  • the divalent aromatic group having a condensed ring structure is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon compound or aromatic heterocyclic compound having a condensed ring.
  • the divalent aromatic group usually has about 6 to 60 carbon atoms, preferably 6 to 48, more preferably 10 to 30 and even more preferably 10 to 22. More preferably Is from 10 to 18, preferably from 1 to 16 and particularly preferably from 14. The carbon number does not include the carbon number of the substituent.
  • divalent aromatic group examples include 1,4 mononaphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 1,4-anthracenedyl group, 1,5-anthracenedyl group, 2,6--anthracenedyl group, 9,10-anthracenedyl group, 2,7-phenanthrylene group, 1,7-naphthacenylene group, 2,8-naphthacenylene group, 2,7-fluorenedyl group, 2,7- Pyrenezyl group, 4, 10-pyrenezyl group, 2, 6-quinoline diyl group, 1, 5-isoquinoline diyl group, 5, 8-quinoxaline diyl group, 4, 7-benzo [1,2,5] thiadiazole diyl group, 4, 7-Benzothiazole diyl group, 2, 7-force rubazol diyl group, 3, 7-dibenzofurandil group, 3, 7-dibenzothiophene diyl group, 3, 7
  • the substituents are alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, aryl group, aryl group, aryl group, arylalkylthio group, aryl alkenyl group, aryl group.
  • it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, and a substituted carboxyl group, and more preferably an alkyl group, an alkoxy group, an aryl group. And particularly preferably an alkyl group.
  • alkyl group an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an aryl alkyl group, an aryl alkyl group, an aryl alkylthio group, an aryl alkenyl group, an aryl alkynyl group, a substituted amino group
  • substituents in the case where A r 1 has a substituent and the specific examples are the same.
  • repeating unit of the formula (1) include the following (S-1 to S-5 1), and the following: an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group. Si group, arylthio group, aryl alkyl group, aryl alkyl group, aryl alkyl group, aryl alkenyl group, aryl alkyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, Examples thereof include those having a substituent such as an acyl group, an acyloxy group, an imine residue, an amido group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group.
  • the bond in the aromatic hydrocarbon ring represents that it can take any position.
  • OTS OTS
  • ITS As the repeating unit represented by the formula (1), preferably S—; ⁇ S_3, S-6 ⁇ S-9, S-1 1 ⁇ S-20, S-3 1 ⁇ S_34, S37 ⁇ S-40, S43 ⁇ S46, S-48, S-50 and S-1 to S-3, S-6 to S-9, S-1 1 to S-20, S-3 1 to S-34, S-37 to S-40, S-43 to S_46, S-48, and S-50 are each an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, aryl group, aryl group, aryl group, aryl group, aryl group, and aryl group.
  • Aryl alkynyl groups amino groups, substituted amino groups, silyl groups, substituted silyl groups, halogen atoms, acyl groups, acyloxy groups, imine residues, amide groups, acid imide groups, monovalent heterocyclic groups, It has a substituent such as a carboxyl group, a substituted carboxyl group or a cyan group, and more preferably S—l to S—3, S—6 to S—9, S-1 S-20, S-34, S-40, S—46, S—50 and S-1 to S—3, S_6 to S: —9, S-1 1 to S-20, S—34, S — 40, S-46, S-50
  • alkyl group alkoxy group, alkylthio group, aryl group, aryloxy group, aryl group, aryl group, aryl group, aryl group, aryl group, and aryl group.
  • Aryl alkynyl groups amino groups, substituted amino groups, silyl groups, substituted silyl groups, halogen atoms, acyl groups, acyloxy groups, imine residues, amide groups, acid imide groups, monovalent heterocyclic groups, Having a substituent such as a carboxyl group, a substituted carboxyl group, or a cyan group, and more preferably, each of S-1 to S-3, S-6 to S_9, and S-11 to S-20, respectively.
  • the substituent has a substituent such as a lupoxyl group or a cyano group.
  • S-9 and S-9 are alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, aryl alkyl group.
  • a substituent such as a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, or a cyano group, and examples thereof include a divalent group represented by the following formula (S-52).
  • R D, R E, R F, R G, the R H and are each independently an alkyl group, an alkoxy group, an alkylthio group, Ariru group, Ariruokishi group, Ariruchio group, Arirua alkyl group, ⁇ reel alkoxy Group, arylalkylthio group, arylarylalkenyl group, arylarylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imidic group Group, monovalent heterocycle Represents a group, a carboxyl group, a substituted carboxyl group or a cyano group.
  • R D , R E , R F , R c , R H and R may be the same as or different from each other.
  • d, e, f and g each independently represents an integer of 0 to 4, and h and i each independently represents an integer of 0 to 5.
  • R D , R E , R F , R G , R H and R represent an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryl group, an aryl group A rualkyl group, an aryloxy group, an arylalkylthio group, an arylalkylene group, an arylalkylinyl group, a substituted amino group, a substituted silyl group, a halogen atom, an acyl group, an acyloxy group, an imine residue, an amid group , Acid imide groups, monovalent heterocyclic groups, definitions of substituted carboxyl groups, and specific examples include those definitions and specific examples of substituents when Ar ′ in the above formula (1) has a substituent It is the same.
  • the substituents represented by R D , R E , R F , R c , R H and in formula (S—52) are preferably alkyl.
  • an alkoxy group Selected from a group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, and a substituted carboxyl group, and more preferably an alkyl group, an alkoxy group, and an aryl group, More preferred are an alkyl group and an alkoxy group, and particularly preferred is an alkyl group.
  • D, e, f and g in the formula (S-5 2) each independently represents an integer of 0 to 4, preferably an integer of 0 to 2, more preferably an integer of 0 to 1, More preferably 0.
  • H and i in the formula (S-5 2) each independently represents an integer of 0 to 5, and from the viewpoint of device characteristics, solubility, etc., preferably an integer of 1 to 3, more preferably 1. is there. From the viewpoint of the stability of the compound, and R H are preferably present in the para position of the nitrogen atom.
  • S—14 and S—14 are each an alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, Reelthio group, arylalkyl group, arylalkylalkoxy group, arylalkylthio group, arylenealkenyl group, arylene alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group , An imine residue, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group, and the like, for example, represented by the following formula (S-53) Bivalent groups can be mentioned.
  • R MI , R M 2 , R caution 3 and R caution 4 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aryl group.
  • Arylalkylthio group, aryl alkenyl group, aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, 1 Represents a valent heterocyclic group, force propyl group, substituted carboxyl group or cyan group, and when there are a plurality of R MI , R M 2 , R M 3 and R M4 , they may be the same or different from each other. good.
  • ml Contact and m 3 each independently represent an integer of 0 to 4, m 2 and m 4 each independently represents an integer of 0 ⁇ 5.
  • R U and R L 2 waso The respective independently represents an alkyl group, Ariru group, Ari Ruarukiru group or monovalent heterocyclic group.)
  • the definition and specific examples of the heterocyclic group and the substituted carboxyl group are the same as those definitions and specific examples of the substituent when Ar ′ in the above formula (1) has a substituent.
  • the substituents represented by R MI , R M 2 , R M 3 and RJH in formula (S-53) are preferably An alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, a substituted amino group, a substituted silyl group, an acyl group, a substituted carboxyl group, and a cyan group, and more preferably , An alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group and a substituted carboxyl group, more preferably an alkyl group, an alkoxy group and an aryl group. More preferably an alkyl group or an alkoxy group, and particularly preferably an alkyl group.
  • Ml and m 3 in the formula (S-5 3) each independently represents an integer of 0 to 4, preferably an integer of 0 to 2, more preferably an integer of 0 to 1, and still more preferably 0 It is.
  • M 2 and m 4 in the formula (S-5 3) each independently represent an integer of 0 to 5, and preferably an integer of 1 to 3 from the viewpoint of device characteristics, solubility, and the like.
  • definition of 1 a is formula (S- 5 3)
  • R u and R L 2 represents an alkyl group in, Ariru group, Ariruaruki group or monovalent heterocyclic group, specific examples, in the formula (1)
  • the definition of the substituent is the same as the specific example.
  • the substituent represented by R and R L 2 in formula (S-5 3) is preferably an alkyl group or an aryl group.
  • the polymer compound of the present invention contains one or more repeating units selected from the above formulas (2) and (3).
  • a ring and B ring each independently represent an aromatic hydrocarbon ring which may have a substituent, at least one of which is an aromatic hydrocarbon in which a plurality of benzene rings are condensed. It is a ring.
  • the aromatic hydrocarbon ring may be further condensed with an aromatic hydrocarbon ring other than a benzene ring and a non-aromatic hydrocarbon-based condensed cyclic compound.
  • the aromatic hydrocarbon ring in the A ring and the aromatic hydrocarbon ring in the B ring may have the same or different ring structures, but heat resistance, fluorescence intensity From this point of view, the aromatic hydrocarbon ring in the A ring and the aromatic hydrocarbon ring in the B ring are preferably aromatic hydrocarbon rings having different ring structures.
  • the aromatic hydrocarbon ring a benzene ring alone or a plurality of condensed benzene rings is preferable.
  • Examples thereof include a benzene ring, a naphthenic ring, an anthracene ring, a tetracene ring, a pendecacene ring, Aromatic hydrocarbon rings such as a pyrene ring and a phenanthrene ring are mentioned, and a benzene ring, a naphthenic ring, an anthracene ring, and a phenanthrene ring are preferable.
  • Combinations of A ring and B ring are preferably benzene ring and naphthalene ring, benzene ring and anthracene ring, benzene ring and phenanthrene ring, naphthalene ring and anthracene ring, naphthalene ring and phenanthrene ring, anthracene ring and phenanthrene ring
  • a combination of a benzene ring and a naphthalene ring is more preferable.
  • aromatic hydrocarbon ring in the A ring and the aromatic hydrocarbon ring in the B ring have different ring structures from each other.
  • the aromatic hydrocarbon ring in the A ring and that in the B ring are asymmetric with respect to the symmetry axis (dotted line) connecting the vertex of the 5-membered ring at the center of the structural formula and the midpoint of the side facing the vertex. It means that.
  • a ring and B ring are naphthalene rings
  • the ring structure is different between A ring and B ring.
  • a ring and B ring are naphthalene rings
  • a ring and B ring have the same ring structure.
  • the substituent is an alkyl group, an alkoxy group, an alkylthio group, an aryl group, from the viewpoint of solubility in an organic solvent, device characteristics, ease of synthesis, etc.
  • it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, a substituted amino group, a substituted silyl group, an acyl group, a substituted carboxyl group and a cyan group. More preferably, it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, and a substituted carboxyl group, and more preferably an alkyl group, an alkoxy group, an aryl group. And particularly preferably an alkyl group.
  • substituents in the case of having them is the same as the specific examples.
  • Rw and Rx are each independently a hydrogen atom, an alkyl group, an 'alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryl group, an aryl group, an aryl group, an aryl alkylthio group, an Reel alkenyl group, aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic ring Represents a group, a carboxyl group, a substituted carboxyl group or a cyano group, and 13 ⁇ 4 ⁇ and 11 may be bonded to each other to form a ring.
  • substituted amino group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, substituted carboxyl group specific examples are the above formula (1 In the case where A r 1 in A) has a substituent, the definition of the substituent is the same as in the specific example.
  • Rw and Rx form a ring having a total of 5 to 20 carbon or other elements.
  • the repeating unit of formula (2) the following (1A_1 to 1A—64, IB—1 to 1 B_64, 1 C—1 to 1 C—64, 1 D _ :! to 1 D — 18), alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, aryl group, aryl group, aryl group, aryl group, aryl group, aryl group, aryl group Alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substituted And those having a substituent such as a carboxyl group or a cyano group.
  • the bond in the aromatic hydrocarbon ring represents that it can take any position.
  • the repeating unit represented by the above formula (2) from the viewpoint of heat resistance, fluorescence intensity, etc., preferably two bonds are present on the A ring and the B ring, respectively.
  • the A ring and the B ring are a combination of a benzene ring and a naphthalene ring, respectively.
  • repeating units represented by the following formulas (1 — 1) and (1 — 2), and repeating units represented by (1-3) and (4) are preferred.
  • R pl , R ql , R p2 , R q2 , R p are R. 3 , R p4 and R q4 are each independently an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryl group, Group, aryl alkyl group, aryl alkyl alkoxy group, aryl alkyl thio group, aryl alkenyl group, aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group Represents an imine residue, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group or a cyano group, a represents an integer of 0 to 3, and b represents an integer of 0 to 5.
  • , R c RP 3 R q3 , R p4, and R q4 may be the same or different when there are multiple, R xl , R, 2 , R i2 , R, 3, R l3 ⁇ R, 4 and R, 4 is it Independently, a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an aryl alkyl group, an aryl alkyl group, an aryl alkylthio group, an aryl alkenyl group, an aryl alkynyl group.
  • Group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group Represents a monovalent heterocyclic group, carboxyl group, substituted carboxyl group or cyano group, and R, and R (2 , R, 3 and R ⁇ 3 , R * 4 and R > 4 are bonded to each other to form a ring. May be formed.
  • R p There R ql, R p2, R q2 , R p3, R q3, R p4 and R.
  • an alkyl group represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryl group, an aryl alkyl group, an aryl alkyl group, an aryl alkylthio group, a substituted amino group, a substituted silyl group, a fluorine atom, an acyl group, an Preferred are a siloxy group, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxy group and a cyano group, and an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, an alkyl group.
  • a reel alkoxy group and an arylalkylthio group are more preferable.
  • R, R>, R, 2 , R x 2 , R, 3 , R, 3 , and R x4 are alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, and arylalkyl.
  • aryloxy group, arylalkylthio group substituted amino group, substituted silyl group, fluorine atom, acyl group, acyloxy group, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substitution force lpoxyl group And an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, an aryl alkylthio group, an alkyl group, an alkoxy group, and an alkyl group. Si group and aryl group are more preferable.
  • alkyl group, alkoxy group, and aryl group methyl group, ethyl group, propyl group, i_propyl group, butyl group, i-butyl group, t-butyl group, pentyl group, isoamyl group, and Xyl, cyclohexyl, heptyl, cyclohexylmethyl, octyl, 2_ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, lauryl, trifluoromethyl, pen A linear, branched or cyclic alkyl group having usually about 1 to 20 carbon atoms such as a fluoroethyl group, a perfluorobutyl group, a perfluorinated hexyl group, a perfluorooctyl group; a methoxy group, an ethoxy group, Propyloki Si group,
  • ⁇ C alkoxy examples include methoxy, ethoxy, propyloxy, i-propyloxy, butoxy, i-butoxy, t-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethioxy
  • Examples include ruhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy and the like
  • specific examples of C, ⁇ C I2 alkylphenyl groups include methylphenyl, ethenylphenyl, and dimethylphenyl.
  • repeating units represented by the above formulas (1-1), (1-2), (1-3) and (1-4), and R, Rw2 and Rl2 , R, 3 and R, 3 , R, 4 and R, 4 are bonded to each other to form a ring.
  • R ,, and R xl are preferably alkyl groups, more preferably those having 3 or more carbon atoms, and more preferably 7 or more. Even more preferred is 8 or more. Particularly preferred is an n-year-old octyl group, which is a structure represented by the following formula (1 E-1).
  • C ring and D ring each independently represent an aromatic ring which may have a substituent.
  • aromatic ring examples include benzene ring, naphthalene ring, anthracene ring, tetracene ring, pentencene ring, pyrene ring, phenanthrene ring, and other aromatic hydrocarbon rings; pyridine ring, bipyridine ring, phenanthrene ring ring, Heteroaromatic rings such as quinoline ring, isoquinoline ring, thiophene ring, furan ring, pyrrole ring and the like can be mentioned.
  • the types of C-ring and D-ring aromatic rings may be the same or different.
  • the aromatic ring is preferably a benzene ring, a naphthalene ring, an anthracene ring, a tetracene ring, a pentacene ring, a pyrene ring, or a phenanthrene ring, more preferably a benzene ring, a naphthenic ring, or an anthracene ring.
  • a benzene ring is preferred.
  • the aromatic ring has a substituent, from the viewpoint of solubility in an organic solvent, device characteristics, ease of synthesis, etc., the substituent is an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group.
  • it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, a substituted amino group, a substituted silyl group, an acyl group, a substituted carboxyl group and a cyan group. More preferably, it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, and a substituted carboxyl group, and more preferably an alkyl group, an alkoxy group, an aryl group. And particularly preferably an alkyl group or an alkoxy group.
  • substituted silyl groups, halogen atoms, acyl groups, acyloxy groups, imine residues, amide groups, acid imide groups, monovalent heterocyclic groups, and substituent force loxyl groups are shown in A in the above formula (1).
  • the definition of substituents in the case where r 1 has a substituent is the same as the specific examples.
  • Y represents an oxygen atom, a sulfur atom, or —O—C (R K ) 2 —.
  • R in formula (3) represents —H1 C (R K ) 2 —
  • R K represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkyl group, Aryl group, aryl alkylthio group, aryl alkenyl group, aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, asil group, acyloxy group, imine residue, amid Represents a group, an acid imide group, a monovalent bicyclic group, a carboxyl group, a substituted carboxyl group, a nitro group or a cyano group.
  • Two R K may be be the same or different.
  • substituents in the case where A r 1 has a substituent is the same as the specific example.
  • repeating unit represented by the formula (3) include the following (G — 1 to G— 26, H — 1 to H — 26, K—1 to K — 2 6), Alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, aryl group, aryl group, aryl group, alkyl group, aryl group, alkenyl group, aryl group, alkynyl group, amino group , Substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substituted carboxyl group or cyano group The ones with the following substituents are listed
  • the bond in the aromatic ring represents that it can take any position.
  • R K is the formula (. Represents the same meaning as R K in 3)) as a repeating unit represented by formula (3), preferably G- 1 ⁇ G- 22, H_ 1 ⁇ H- 2 2 , K — 1 to K_22 and G—1 to G—22, H—1 to H—22, K — 1 to K—22, respectively, alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, Aryl group, aryl alkoxy group, aryl alkyl group, aryl alkenyl group, aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, Having a substituent such as an imine residue, an amide group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, or a cyan
  • R s and R ′ each independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, Reel alkyl group, aryl alkylthio group, aryl alkylthio group, aryl alkenyl group, aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue group, an amide group, Sani Mi de group, monovalent heterocyclic group, carboxyl group, if substituted carboxyl group, a nitro group or a Xia cyano group.
  • R s and R 1 represent an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryloxy group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an arylalkenyl group.
  • the substituent represented by Rs and R ′ in formula (G_27) is preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an arylalkyl.
  • aryloxy group substituted amino group, substituted silyl group, acyl group, substituted carboxyl group and cyano group, more preferably, alkyl group, alkoxy group, aryl group, aryloxy group, aryl group. It is selected from alkyl groups, arylalkoxy groups and substituted carboxyl groups, more preferably selected from alkyl groups, alkoxy groups and aryl groups, more preferably alkyl groups and alkoxy groups, and particularly preferably Is an alkoxy group.
  • M and n in the formula (G-27) each independently represents an integer of 0 to 3, preferably an integer of 1 to 2, and more preferably 1.
  • the ratio is usually from 1 to 100 mol%, preferably from 10 to 100 mol%, more preferably from 30 to 100 mol%, still more preferably from 40 to 100 mol%, still more preferably Is 40 to 80 mol%, still more preferably 40 to 70 mol%, and particularly preferably 40 to 60 mol%.
  • the total of the repeating unit represented by formula (1), the repeating unit represented by formula (2) and the repeating unit represented by formula (3) Is preferably 0.01: 99.99-70.00: 30.00, more preferably 0.10: 99.90 to 50.00: 50.00.
  • the polymer compound of the present invention has the viewpoint of changing the emission wavelength, the viewpoint of increasing the luminous efficiency, From the viewpoint of improving the properties, it is preferable to include one or more repeating units other than the repeating units represented by the above formulas (1), (2) and (3).
  • the above formulas (1), (2) and (3) are the above formulas (1), (2) and (3).
  • a repeating unit other than the repeating unit represented by (3) is preferably a repeating unit represented by the following formula (4) and / or (5).
  • Ar 3 represents a divalent aromatic group which may have a substituent.
  • a r 6 , Ar 7 , A r 8, and A r 9 each independently represents a 1,4-monophenylene group or a 4,4′-biphenylene group.
  • a r l ( ) , A ru u and A r 12 each independently represent an aryl group Ar 6 , A r 7 , A r 8 , A r 9 , Ar IG , A r 11 and A r 12 have a substituent.
  • X and y are each independently 0 or a positive integer.
  • Ar 3 represents a divalent aromatic group which may have a substituent.
  • the divalent aromatic group is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon compound or an aromatic heterocyclic compound.
  • the divalent aromatic group usually has about 5 to 60 carbon atoms, preferably 5 to 48, more preferably 6 to 30, still more preferably 6 to 22, and particularly preferably 6 to 14
  • the carbon number does not include the carbon number of the substituent.
  • divalent aromatic group examples include 1, 4 _phenylene group, 1, 3— phenylene group, 1, 2_ phenylene group, 1, 4_ naphthylene group, 1, 5— Naphthylene group, 2,6-naphthylene group, 1,4_anthracenedyl group, 1,5-anthracenedyl group, 2,6-anthracenedyl group, 9,10-anthracenedyl group, 2,7-phenanthrylene group, 1,7-naphthacenylene group, 2,8-naphthacenylene group, 2,7-fluorenedyl group, 2,7-pyreneyl group, 4,10-pyreneyl group, 2,6-pyridyl group, 2,5- Thiophenyl group, 2,5-furanyl group, 2,6-quinolinyl group, 1,5-isoquinoline group ', 5,8-quinoxaline group, 4,7-benz [1,2,5] thiadiazole Group, 4, 7-benz
  • the substituent is an alkyl group, an alkoxy group, an alkylthio group, an aryl — Group, aryloxy group, aryloxy group, arylalkyl group, arylylalkoxy group, arylalkylthio group, arylenealkenyl group, arylenealkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom
  • an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, a substituted amino group, a substituted silyl group, an acyl group, a substituted carboxyl group, and a cyano group More preferably, it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group and a substituted carboxyl group, and more preferably an alkyl group, an alkoxy group, an aryl. Is selected from the group.
  • the definitions and specific examples of the cyclic group and the substituted carboxyl group are the same as those defined and specific examples of the substituent when Ar ′ in the above formula (1) has a substituent.
  • a r 1 (1 , A r 1 1 and A r 1 2 each independently represents an aryl group, where an aryl group is an atom obtained by removing one hydrogen atom from an aromatic hydrocarbon.
  • a group having an independent benzene ring or condensed ring The aryl group usually has about 6 to 60 carbon atoms, preferably 6 to 48, more preferably 6 to 30 carbon atoms. And more preferably 6 to 18, more preferably 6 to 10, and particularly preferably 6.
  • the carbon number does not include the carbon number of the substituent.
  • phenyl group is an aryl group, where an aryl group is an atom obtained by removing one hydrogen atom from an aromatic hydrocarbon.
  • a group having an independent benzene ring or condensed ring The aryl group usually has about 6 to 60 carbon atoms, preferably 6 to 48, more preferably 6 to 30 carbon atoms. And more preferably 6 to 18, more preferably 6 to 10, and particularly preferably 6.
  • the carbon number does not include the
  • a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group more preferably a phenyl group, a 1-naphthyl group, and a 2-naphthyl group, and particularly preferably a phenyl group.
  • the substituent is an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryl group, an aryl alkyl group, an aryl alkoxy group, an aryl alkyl group, Arylene alkenyl group, arylene alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent complex It is preferably selected from a cyclic group, a carboxyl group, a substituted carboxyl group, and a cyan group.
  • an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkyl group, a substituted amino group, a substituted silyl group, an acyl group, a substituted carboxyl group and a cyan group are selected. More preferably, it is selected from an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aryl alkyl group, an aryl alkoxy group, and a substitutional force oxyl group, and more preferably an alkyl group, an alkoxy group.
  • substituted silyl groups, halogen atoms, acyl groups, acyloxy groups, imine residues, amide groups, acid imide groups, monovalent heterocyclic groups, and substituent force loxyl groups are shown in the above formula (1).
  • the definition of the substituent in the case where A r 1 has a substituent is the same as the specific example.
  • each R is independently a hydrogen atom or an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an aryl group, an aryl group, an aryl group, an aryl alkylthio group, an aryl alkenyl group, Aryl alkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group, imine residue, amide group, acid imide group, monovalent heterocyclic group, carboxyl group And a substituted carboxyl group and a cyano group.
  • the polymer compound of the present invention contains at least one type of repeating unit represented by formula (1) and one or more types of repeating unit represented by formula (2). 4) It is more preferable to include one or more types of repeating units represented by formula (1), including one type of repeating unit represented by formula (1), and one type of repeating unit represented by formula (2), and More preferably, it contains two types of repeating units represented by formula (4). As a more preferred combination, one type of repeating unit represented by the formula (S-52), one type of repeating unit represented by the formula (1 1 1), and one type of 2, 7-fluorenediyl group having a substituent And a combination of one type of 3, 7-phenoxazine diyl group having a substituent.
  • the number average molecular weight (Mn) in terms of polystyrene by size exclusion chromatography (hereinafter referred to as SEC) of the polymer compound of the present invention is usually about 10 3 to 10 8 , preferably 10 4 to 10 6 .
  • the weight average molecular weight (Mw) in terms of polystyrene is usually about 10 3 to 10 8 , and preferably 5X 10 4 to 5X 10 6 , more preferably from the viewpoint of film formability and efficiency when used as an element. Is from 10 5 to 10 6 .
  • the terminal group of the polymer compound of the present invention is protected with a stable group, because if the polymerization active group remains as it is, there is a possibility that the light emission characteristics and life of the device will be reduced.
  • Those having a conjugated bond continuous with the conjugated structure of the main chain are preferred, and examples thereof include a structure bonded to an aryl group or a heterocyclic group via a carbon-carbon bond.
  • the substituents described in Chemical formula 10 of JP-A-9_45478 are exemplified.
  • the polymer compound of the present invention When used as a light-emitting material, a charge transport material, or the like, it may be used in a mixture with other polymer compounds.
  • the polymer compound of the present invention includes, for example, a compound represented by the following formula (a), a compound represented by the following formula (b), and a compound represented by the following formula (c) as necessary. And can be produced by condensation polymerization.
  • a r Ar 2 and Z have the same meanings as Ar r ′, A r 2 and Z in formula (1), respectively.
  • Y ′ is independently a halogen atom, formula (a— 1) sulfonate group represented by 1), methoxy group, borate ester group, boric acid group, group represented by formula (a_2), group represented by formula (a-3), or formula (a- 4) represents a group represented by
  • Ar 13 represents a divalent group represented by formula (2) or formula (3).
  • Y 1 represents the same meaning as Y 1 in formula (a).
  • Ar 14 represents a divalent group represented by formula (4) or formula (5).
  • Y 1 represents the same meaning as Y ′ in formula (a).
  • R a represents an alkyl group or an aryl group which may have a substituent.
  • X A represents a halogen atom.
  • halogen atom a chlorine atom
  • X A represents a halogen atom.
  • halogen atom a chlorine atom
  • Formula (a), Y 1 is independently in (b), (c), a halogen atom , Formula (a— Sulfonate groups represented by 1), methoxy group, borate group, a boric acid group (i.e., one B (0H) group that represented by 2), a group represented by the formula (a- 2), formula ( a— a group represented by 3) or a group represented by the formula (a-4).
  • Examples of the halogen atom for Y 1 include a chlorine atom, a bromine atom, and an iodine atom.
  • boric acid ester group in Y ′ examples include groups represented by the following formulae. Defining alkyl or Ariru group in R a in the formula (a_ l), as specific examples, respectively, the definition of alkyl or Ari Le group when A r 1 in the formula (1) has a substituent, specifically Similar to the example.
  • Examples of the sulfonate group represented by the formula (a-1) include a methanesulfonate group, a trifluoromethanesulfonate group, a phenyl sulfonate group, a 4-methylphenyl sulfonate group, and the like.
  • Y 1 in the formulas (a), (b) and (c) is preferably a halogen atom, a boric acid ester group or a boric acid group from the viewpoint of ease of synthesis, ease of handling and toxicity.
  • condensation polymerization method examples include a method in which the monomers represented by the formulas (a), (b), and (c) are reacted using an appropriate catalyst or an appropriate base as necessary.
  • condensation polymerization catalysts include palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium complexes such as palladium acetate, nickel [tetrakis (triphenylphosphine)], [ 1,3-bis (diphenylphosphino) propane] dichloronickel, transition metal complexes such as [bis (1,4-cyclodogen)] nickel and other nickel complexes, and if necessary, triphenylphosphine, tri ( t_butylphosphine), tricyclohexylphosphine, diphenylphosphinopropane, bibilidyl and other catalysts.
  • palladium complexes such as palladium acetate, nickel [tetrakis (triphenylphosphine)], [ 1,
  • the catalyst one synthesized in advance can be used, or one prepared in a reaction system can be used. In the present invention, these catalysts can be used alone or in admixture of two or more.
  • the catalyst can be used in any amount, but in general, the amount of the transition metal compound relative to the sum of the number of moles of the compounds represented by the formulas (a), (b), (c) is 0.001. ⁇ 300 mol% is preferable, 0.005 to 50 mol% is more preferable, and 0.0 1 to 20 mol% is more preferable.
  • Bases include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride and tritium phosphate, tetrabutyl ammonium fluoride, tetrabutyl ammonium chloride, Examples include organic bases such as tetrabutylammonium bromide and tetrabutylammonium hydroxide.
  • the base can be used in any amount, but generally 0.5 to 20 equivalents are preferable with respect to the sum of the number of moles of the compounds represented by the formulas (a), (b) and (c). 1 to 10 equivalents are more preferable.
  • the condensation polymerization can be carried out in the absence of a solvent, but is usually carried out in the presence of an organic solvent.
  • organic solvent used examples include toluene, xylene, mesitylene, terahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide and the like. These organic solvents may be used alone or in combination of two or more.
  • the amount of organic solvent used is usually such that the monomer concentration is 0.1 to 90% by weight.
  • a preferable ratio is 1 to 50% by weight, and a more preferable ratio is 2 to 30% by weight.
  • the organic solvent varies depending on the compound used and the reaction, but it is generally desirable to perform deoxygenation treatment in order to suppress side reactions.
  • the reaction temperature for carrying out the condensation polymerization is not particularly limited as long as the reaction medium is kept in a liquid state. Absent.
  • a preferred temperature range is 1 1 00: to 20 0 0, more preferably 80 to 1 5 0, and even more preferably 0 to 1 2 O t :.
  • reaction time varies depending on the reaction conditions such as reaction temperature, it is usually 1 hour or longer, preferably 2 to 500 hours.
  • Conditions for condensation polymerization include, for example, a method of polymerization by Suzuk i reaction (Chem. Rev., Vol. 95, p. 2457 (1995)), a method of polymerization by Grignard reaction (Kyoritsu Publishing) , Polymer Functional Materials Series II, Polymer Synthesis and Reaction (2), pp. 432-433), Polymerization by Yamamoto Polymerization (Prog. Poly sym. Sci.), 17), pp. 153-1205, 1992), etc.
  • Post-treatment can be performed according to a known method.
  • a target polymer compound can be obtained by adding a reaction solution to a lower alcohol such as methanol and filtering and drying the resulting precipitate.
  • the purity of the polymer compound obtained by the post-treatment is low, it can be purified by usual methods such as recrystallization, continuous extraction with a Soxhlet extractor, and column chromatography.
  • the polymer light-emitting device of the present invention is characterized in that it has an organic layer between electrodes composed of an anode and a cathode, and the organic layer contains the polymer compound of the present invention.
  • the organic layer may be any one of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, an interlayer layer, and the like, but the organic layer is preferably a light emitting layer.
  • the light emitting layer refers to a layer having a function of emitting light
  • the hole transport layer refers to a layer having a function of transporting holes
  • the electron transport layer is a layer having a function of transporting electrons.
  • the interlayer layer is adjacent to the light emitting layer between the light emitting layer and the anode, and serves to isolate the light emitting layer and the anode or the light emitting layer from the hole injection layer or the hole transport layer. It is a layer that has.
  • the electron transport layer and the hole transport layer are collectively referred to as a charge transport layer. Also electronic
  • the injection layer and the hole injection layer are collectively referred to as a charge injection layer. Two or more light emitting layers, hole transport layers, hole injection layers, electron transport layers, and electron injection layers may be used independently.
  • the light emitting layer that is an organic layer may further contain a hole transporting material, an electron transporting material, or a light emitting material.
  • the light-emitting material refers to a material that exhibits fluorescence and Z or phosphorescence.
  • the mixing ratio of the hole transporting material is 1 wt% to 8 Ow t%, preferably 5 w t with respect to the whole mixture. % ⁇ 6 0w t%.
  • the mixing ratio of the electron transporting material to the whole mixture is lw t% to 80 w t%, preferably 5 w t% to 6 Ow t%.
  • the mixing ratio of the luminescent material to the whole mixture is lwt% to 8 Ow t%, preferably 5 w t% to 6 Ow t%.
  • the mixing ratio of the light emitting material is 1 wt% to 5 Ow t with respect to the entire mixture. %, Preferably 5 wt% to 4 O wt%, and the total amount of the hole transport material and the electron transport material is 1 wt% to 50 wt%, preferably 5 wt% to 4 O w t%. Therefore, the content of the polymer compound of the present invention is 98 wt% to 1 wt%, preferably 90 wt% to 20 wt%.
  • hole-transporting material electron-transporting material, and light-emitting material to be mixed
  • known low-molecular compounds, triplet light-emitting complexes, or high-molecular compounds can be used, but high-molecular compounds are preferably used.
  • fluorescent materials of low molecular weight compounds include naphthalene derivatives, anthracene or derivatives thereof, perylene or derivatives thereof, polymethine-based, xanthene-based, coumarin-based, cyanine-based pigments, 8-hydroxyquinoline or A metal complex of the derivative, an aromatic amine, tetraphenylcyclopentene or a derivative thereof, tetraphenylbutadiene or a derivative thereof, or the like can be used.
  • JP-A 57-5 1 781 and 59-1 94393 can be used.
  • triplet light-emitting complexes examples include Ir (ppy) 3 with iridium as the central metal, Btp 2 Ir (a cac), PtOEP with platinum as the central metal, Eu (TTA) 3 phen with europium as the central metal, etc. Is mentioned.
  • triplet light-emitting complexes include Nature, (1998), 395, 15 and Appl. Phys. Lett. (1999), 75 (1), 4, Proc. SPIE-Int. Soc. Opt. Eng. (2001), 4105 (0rganic Light-Emitting Materials and Devices IV), 119, J. Am. Chem. Soc., (2001), 123, 4304, Appl. Phys. Let (1997), 71 (18 ), 2596, Syn. Met., (1998), 94 (1), 103, Syn. Met., (1999), 99 (2), 1361, Adv. Mater., (1999), 11 (10), 852, Jpn. J. Appl. Phys., 34, 1883 (1995).
  • the polymer composition of the present invention contains at least one material selected from a hole transport material, an electron transport material, and a light emitting material and the polymer compound of the present invention, and is used as a light emitting material or a charge transport material. Can do.
  • At least one material selected from the hole transport material, electron transport material, and light emitting material may be determined according to the use, but in the case of the use of the light emitting material, the same content ratio as in the above light emitting layer is preferable.
  • the number average molecular weight in terms of polystyrene of the polymer composition of the present invention is usually about 10 3 to 10 s , preferably 10 4 to 10 6 . Further, the weight average molecular weight in terms of polystyrene is usually about 10 3 to 10 8 , and is preferably IX 10 4 to 5 X 10 6 from the viewpoints of film forming properties and efficiency when used as an element.
  • the average molecular weight of the polymer composition means a value obtained by analyzing a composition obtained by mixing two or more kinds of polymer compounds by GPC.
  • the polymer light emitting device of the present invention has The film thickness of the light-emitting layer varies depending on the material used, and may be selected so that the drive voltage and the light emission efficiency are moderate. For example, the thickness is from I nm to l / m, preferably from 2 nm to 500 nm, more preferably 5 nm to 200 nm.
  • Examples of the method for forming the light emitting layer include a method of forming a film from a solution.
  • the film formation method from solution includes spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, drive coating method, spray coating method,
  • Application methods such as a screen printing method, a flexographic printing method, an offset printing method, and an ink-jet printing method can be used.
  • Printing methods such as a screen printing method, a flexographic printing method, an offset printing method, and an ink jet printing method are preferable because pattern formation and multicolor coating are easy.
  • the solution (ink composition) used in the printing method or the like is only required to contain at least one polymer compound of the present invention.
  • a hole transport material and an electron transport material are used. It may contain additives such as materials, luminescent materials, solvents, and stabilizers.
  • the proportion of the polymer compound of the present invention in the ink composition is usually 20 wt% to 100 wt% with respect to the total weight of the composition excluding the solvent, preferably 40 wt% to 100 wt%. .
  • the proportion of the solvent is lwt% to 99.9 wt%, preferably 60 wt% to 99.5 wt%, based on the total weight of the composition. More preferably, it is 8 Ow t% to 99. Ow t%.
  • the viscosity of the ink composition depends on the printing method. If the ink composition such as the ink jet printing method passes through the discharge device, the viscosity will be reduced in order to prevent clogging and flight bending during discharge. In 25, it is preferably in the range of 1 to 2 O m Pa ⁇ s.
  • the solution of the present invention may contain an additive for adjusting the viscosity and / or surface tension in addition to the polymer compound of the present invention.
  • a high molecular weight polymer compound (thickener) for increasing the viscosity, a poor solvent, a low molecular weight compound for decreasing the viscosity, a surfactant for decreasing the surface tension, and the like are appropriately combined. Use it.
  • the high molecular weight polymer compound may be any compound that is soluble in the same solvent as the polymer compound of the present invention and does not inhibit light emission or charge transport.
  • high molecular weight polystyrene, polymethyl methacrylate, or a polymer compound of the present invention having a high molecular weight can be used.
  • the weight average molecular weight is preferably 500,000 or more, more preferably 100 million or more. preferable.
  • a poor solvent can also be used as a thickener. That is, the viscosity can be increased by adding a small amount of poor solvent for the solid content in the solution.
  • the type and amount of the solvent may be selected as long as the solid content in the solution does not precipitate.
  • the amount of the poor solvent is preferably 5 O wt% or less, more preferably 3 O wt% or less with respect to the whole solution.
  • the solution of the present invention may contain an antioxidant in addition to the polymer compound of the present invention in order to improve storage stability.
  • the antioxidant is not particularly limited as long as it is soluble in the same solvent as the polymer compound of the present invention and does not inhibit light emission or charge transport, and examples thereof include phenolic antioxidants and phosphorus antioxidants.
  • Chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, and ether solvents such as tetrahydrofuran, dioxane and anisole , Aromatic hydrocarbon solvents such as toluene and xylene, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.
  • Hydrocarbon solvent, acetone, methyl Ketone solvents such as ethyl ketone, cyclohexanone, benzophenone, and acetophenone
  • ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate
  • Alcohol and its derivatives alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol, sulfoxide solvents such as dimethyl sulfoxide, N-methyl-2-pyrrole , N, amide solvents such as N- dimethylformamidine de are exemplified. These organic solvents can be used alone or in combination.
  • Aromade solvents such as toluene, xylene, ethylbenzene, jetylbenzene, trimethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzen, isobutylbenzene, s-butylbenzene, n-hexylbenzene, cyclohexyl Rubenzene, 1-methylnaphthalene, tetralin, anisole, ethoxybenzene, cyclohexane, bicyclohexyl, cyclohexenylcyclohexanone, n-heptyl cyclohexyl, n-hexylcyclohexane, decalin, methyl
  • the types of solvents in the solution are preferably two or more, more preferably two to three, and even more preferably two, from the viewpoints of film forming properties and device characteristics. .
  • one of them may be in a solid state at 25 t :.
  • one kind of solvent is preferably a solvent having a boiling point of 180 or more, more preferably 20 or more.
  • viscosity in both of the two solvents, it is preferable that 1 wt% or more of the aromatic polymer is dissolved at 60, and one of the two types of solvents has 25 % Or more of the aromatic polymer is preferably dissolved.
  • the solvent having the highest boiling point is preferably 40 to 90 wt% of the weight of the total solvent in the solution, More preferably 50 to 90 wt%, more preferably 65 to 85 wt%
  • the aromatic polymer of the present invention contained in the solution may be one type or two or more types, A polymer compound other than the aromatic polymer of the present invention may be contained as long as the device characteristics and the like are not impaired.
  • the solution of the present invention may contain water, a metal and a salt thereof in a range of 1 to 100 ppm.
  • the metal include lithium, sodium, calcium, potassium, iron, copper, nickel, aluminum, zinc, chromium, manganese, cobalt, platinum, and iridium. Further, it may contain silicon, phosphorus, fluorine, chlorine, and Z or bromine in the range of 1 to 100 ⁇ pm.
  • Thin films can be produced by printing methods, flexographic printing methods, offset printing methods, ink-jet printing methods, and the like.
  • the solution of the present invention is preferably used for a film forming method by a screen printing method, a flexographic printing method, an offset printing method, and an ink jet printing method, and more preferably used for a film forming method by an ink jet method.
  • the glass transition temperature of the polymer compound contained in the solution is high, it is possible to bake at a temperature of 100 0 ⁇ or higher. Even if baking is performed at a low temperature, the degradation of device characteristics is very small. Further, depending on the type of the polymer compound, it can be baked at a temperature of 160 or higher.
  • Examples of the thin film that can be produced using the solution of the present invention include a light-emitting thin film, a conductive thin film, and an organic semiconductor thin film.
  • the conductive thin film of the present invention preferably has a surface resistance of 1 ⁇ or less.
  • the electrical conductivity can be increased by doping the thin film with a Lewis acid or an ionic compound.
  • the surface resistance is more preferably 100 ⁇ or less, and further preferably 10 ⁇ / mouth or less.
  • the organic semiconductor thin film of the present invention whichever of the electron mobility and hole mobility, the larger is preferably at 1 0- 5 crr ⁇ or ZVZ seconds. More preferably, it is l O ⁇ cn ⁇ ZVZ seconds or more, and more preferably 10 ⁇ 1 cn ⁇ ZVZ seconds or more.
  • Form forms a S i organic semiconductor thin film on a substrate formed with an insulation film and a gate electrode, such as S I_ ⁇ 2, by forming a source electrode and a drain electrode, etc.
  • a u be an organic transistor it can.
  • the polymer light-emitting device of the present invention preferably has a maximum external quantum yield of 1% or more when a voltage of 3.5 V or more is applied between the anode and the cathode from the viewpoint of device brightness and the like. 1. 5% or more is more preferable.
  • a polymer light-emitting device of the present invention a polymer light-emitting device in which an electron transport layer is provided between the cathode and the light-emitting layer, a polymer light-emitting device in which a hole transport layer is provided between the anode and the light-emitting layer, Examples thereof include a polymer light emitting device in which an electron transport layer is provided between the cathode and the light emitting layer and a hole transport layer is provided between the anode and the light emitting layer.
  • a structure in which an interlayer is provided adjacent to the light emitting layer between the light emitting layer and the anode is also exemplified. That is, the following structures a ′) to d ′) are exemplified.
  • the hole transport material used includes polyvinylcarbazole or a derivative thereof, polysilane or a derivative thereof, and an aromatic amine in the side chain or main chain.
  • JP-A-6 3-7 0 2 5 7, JP-A 6 3-1 7 5 8 6 0, JP-A 2 1 3 5 3 5 9 No. 2-1 3 5 3 6 No. 1-No. 2-2 0 9 9 8 8 No. 3-3 7 9 9 No. 2 No. 3-1 5 2 1 8 No. 4 Examples are described.
  • a hole transport material used for the hole transport layer polyvinyl carbazol or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine compound group in a side chain or a main chain
  • a polymer hole transporting material such as polyaniline or a derivative thereof, polythiophene or a derivative thereof, poly (p_phenylenevinylene) or a derivative thereof, or poly (2,5-Chenylenevinylene) or a derivative thereof.
  • Preferable are polyvinylcarbazol or a derivative thereof, polysilan or a derivative thereof, and a polysiloxane derivative having an aromatic amine in a side chain or main chain.
  • Examples of the hole transporting material of the low molecular weight compound include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, and triphenyldiamine derivatives.
  • a low molecular weight hole transporting material it is preferably used by being dispersed in a polymer binder.
  • polymer binder examples include poly (N-vinylcarbazole), polyaniline or a derivative thereof, polythiophene or a derivative thereof, poly (p-phenylenevinylene) or a derivative thereof, poly Examples thereof include (2,5-Chenylenevinylene) or derivatives thereof, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polychlorinated vinyl, polysiloxane, and the like.
  • Polyvinylcarbazole or a derivative thereof can be obtained, for example, from a vinyl monomer by cation polymerization or radical polymerization.
  • polysiloxane or a derivative thereof has almost no hole transporting property in the siloxane skeleton structure
  • those having the structure of the low molecular hole transporting material in the side chain or main chain are preferably used.
  • those having a hole transporting aromatic amine in the side chain or main chain are exemplified.
  • the method for forming the hole transport layer is not limited, but for a low molecular hole transport material, a method of forming a film from a mixed solution with a polymer binder is exemplified. In the case of a polymer hole transporting material, a method of film formation from a solution is exemplified.
  • a solvent capable of dissolving or uniformly dispersing a hole transporting material is preferable.
  • Chlorine form chlorine-based solvent such as methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, black-mouthed benzene, o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene
  • Aromatic hydrocarbon solvents such as xylene, cyclohexane, methylcyclohexane, n_pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.
  • Solvents such as acetone, methyl ethyl ketone and cyclohexanone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoester Tylether, ethylene glycol monomethyl ether, dimethyl Shetan, propylene glycol, jetoxymethane, triethylene glycol monoethyl ether, glycerin, polyhydric alcohols such as 1,2-hexanediol and their derivatives, methanol, ethanol, propanol, isopropanol, cyclohexanol, etc.
  • ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone
  • ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate
  • Alcohol solvents dimethyl Examples include sulfoxide solvents such as til sulfoxide and amide solvents such as N-methyl_2-pyrrolidone and N, N-dimethylform'amide. These organic solvents can be used alone or in combination.
  • film formation methods from solution include spin coating from solution, casting method, micro gravure coating method, gravure coating method, bar coat method, roll coating method, wire bar coating method, dip coating method, and spray coating.
  • Coating methods such as printing method, screen printing method, flexographic printing method, offset printing method, ink jet printing method, etc.
  • the optimum value for the film thickness of the hole transport layer differs depending on the material used. The ratio should be selected so as to have an appropriate value, but at least a thickness that does not cause pinholes is necessary. If the thickness is too large, the drive voltage of the element becomes high, which is not preferable. Therefore, the thickness of the hole transport layer is, for example, 1 nm to 1, preferably 2 ⁇ ! ⁇ 500 nm, more preferably 5 nm to 200 nm.
  • the electron transporting material such as oxadiazole derivative, anthraquinodimethane or derivative thereof, benzoquinone or derivative thereof, naphthoquinone or A derivative thereof, anthraquinone or a derivative thereof, tetracyananthraquinodimethane or a derivative thereof, a fluorenone derivative, a diphenyldisyanoethylene or a derivative thereof, a diphenoquinone derivative, or a metal complex of 8-hydroxyquinoline or a derivative thereof, Examples thereof include polyquinoline or a derivative thereof, polyquinoxaline or a derivative thereof, polyfluorene or a derivative thereof.
  • Examples include those described in JP-A-3-37992 and JP-A-3_152184.
  • oxadiazole derivatives benzoquinone or derivatives thereof, anthraquinone or derivatives thereof, or metal complexes of 8-hydroxyquinoline or derivatives thereof, polyquinoline or derivatives thereof, polyquinoxaline or derivatives thereof, poly Fluorene or its derivatives are preferred, 2- (4-biphenylyl) 1-5- (4t-butylphenol) 1,1,3,4-oxadiazol, benzoquinone, anthraquinone, tris (8-quinolinol) aluminum Polyquinoline is more preferable.
  • the method of forming the electron transport layer there are no particular restrictions on the method of forming the electron transport layer, but for low molecular weight electron transport materials, vacuum deposition from powder, or film deposition from solution or molten state, is not possible for polymer electron transport materials. Examples of the method include film formation from a solution or a molten state. When forming a film from a solution or a molten state, the above polymer binder may be used in combination.
  • a solvent capable of dissolving or uniformly dispersing an electron transport material and / or a polymer binder is preferable.
  • Chlorine form such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorine benzene, 0-dichlorobenzene, etc., ether solvents such as tetrahydrofuran, dioxane, etc.
  • Aromatic hydrocarbon solvents such as toluene and xylene, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.
  • Hydrocarbon solvents cane solvents such as acetone, methyl ethyl ketone, and cyclohexanone, ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol Recall monoethyl ether, ethylene glycol monomethyl ether, dimethoxy Polyhydric alcohols such as shetan, propylene glycol, doxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol and their derivatives, alcohols such as methanol, ethanol, propanol, isopropanol, cyclohexanol Examples thereof include sulfoxide solvents such as dimethyl sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These organic solvents can be
  • Examples of the film forming method from a solution or a molten state include a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire coating method, a dip coating method, and a spray. Coating methods such as a coating method, a screen printing method, a flexographic printing method, an offset printing method, and an inkjet printing method can be used.
  • the film thickness of the electron transport layer differs depending on the material used, and it may be selected so that the drive voltage and the light emission efficiency are appropriate values, but at least a thickness that does not cause pinholes is required. If the thickness is too thick, the drive voltage of the element increases, which is not preferable. Accordingly, the film thickness of the electron transport layer is, for example, 1 nm to 1, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • charge injection layer (hole injection layer).
  • the electron injection layer is sometimes commonly called.
  • the above-described charge injection layer or an insulating layer having a thickness of 2 nm or less may be provided adjacent to the electrode.
  • a thin buffer layer may be inserted at the interface between the charge transport layer and the light emitting layer in order to improve the properties and prevent mixing.
  • the order and number of layers to be laminated, and the thickness of each layer can be appropriately used in consideration of the light emission efficiency and the element lifetime.
  • a polymer light emitting device provided with a charge injection layer is a polymer light emitting device provided with a charge injection layer adjacent to the cathode, adjacent to the anode.
  • a polymer light emitting device provided with a charge injection layer is a polymer light emitting device provided with a charge injection layer adjacent to the cathode, adjacent to the anode.
  • Anode Z Charge injection layer / Hole transport layer Light emitting layer // Charge injection layer // Cathode
  • Electron transport layer Charge injection layer / z cathode
  • an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode.
  • the interlayer may also serve as a hole injection layer and / or a hole transport layer.
  • the charge injection layer include: a layer containing a conductive polymer; provided between the anode and the hole transport layer; and an intermediate between the anode material and the hole transport material contained in the hole transport layer.
  • a layer including a material having an ionization potential of a value of between, a material provided between the cathode and the electron transport layer, and a material having an electron affinity of a value intermediate between the cathode material and the electron transport material included in the electron transport layer Examples are layers.
  • the electric conductivity of the conducting polymer is preferably 1 0_ 5 SZcm least 10 3 or less, decreasing the leak current between light emitting pixels
  • the electric conductivity of the conducting polymer is preferably from 1 0- 5 SZcm least 10 3 SZcm, small leak current between light emitting pixels
  • To fence is more preferably less than 10 2 S / cm 10- 5 SZcm , more preferably less 10- 5 S cm or 10 'SZ cm.
  • the electrical conductivity of the conducting polymer to the 10_ 5 SZcm least 10 3 or less, a suitable amount of ions are doped into the conducting polymer.
  • the kind of ions to be doped is an anion for a hole injection layer and a cation for an electron injection layer.
  • anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, camphor sulfonate ions, etc.
  • cations include lithium ions, sodium ions, potassium ions, tetraptyl ammonium ions, etc. Is exemplified.
  • the material used for the charge injection container may be appropriately selected in relation to the material of the electrode and the adjacent layer, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene pinylene and derivatives thereof, Bolenchylene vinylene and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its derivatives, conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain, metal phthalocyanine (such as copper phthalocyanine), carbon Etc. are exemplified.
  • An insulating layer having a thickness of 2 nm or less has a function of facilitating charge injection.
  • the material for the insulating layer include metal fluorides, metal oxides, and organic insulating materials.
  • a polymer light emitting device having an insulating layer having a thickness of 2 nm or less is a polymer light emitting device having an insulating layer having a thickness of 2 nm or less adjacent to the cathode, and a film having a thickness of 2 nm or less adjacent to the anode.
  • One example is a polymer LED with an insulating layer.
  • Light emitting layer Electron transport layer Insulating layer / cathode with a thickness of 2 nm or less
  • Electron transport layer z Anode No. 2 nm or less insulating layer No hole transport layer Emissive layer Z Electron transport layer Cathode aa) Anode Z Hole transport layer Emission layer Electron transport layer Insulated layer 2 nm or less Cathode ab) Anode Z Insulating layer with a thickness of 2 nm or less Hole transport layer Light-emitting layer Electron transport layer / insulating layer with a thickness of 2 nm or less Further, for each one of these structures, a structure in which one interlayer is provided adjacent to the light emitting layer between the light emitting layer and the anode is also exemplified. In this case, the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.
  • the interlayer layer is provided between the anode and the light emitting layer, and the anode, the hole injection layer or the hole transport layer, and the light emission It is preferably composed of a material having an ionization potential intermediate to that of the polymer compound constituting the layer.
  • Materials used for the interlayer layer include aromatic amides such as polyvinyl carbazol or derivatives thereof, polyarylene derivatives having aromatic groups in the side chain or main chain, arylamine derivatives, triphenyldiamine derivatives, etc. Examples are polymers.
  • the method for forming the interlayer layer is not limited.
  • a method by film formation from a solution is exemplified.
  • a solvent that can dissolve or uniformly disperse a material used for an interlayer layer is preferable.
  • Chlorine form such as black mouth form, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, black mouth benzene, o-dichloro mouth benzene, etc., ether type such as tetrahydrofuran, dioxane, etc.
  • Aromatic hydrocarbon solvents such as toluene and xylene
  • fats such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane
  • Aromatic hydrocarbon solvents such as acetone, methyl ethyl ketone, and cyclohexanone
  • Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol Monoethyl ether, ethylene glycol monomethyl ether, dimethoxy Shetan, propylene glycol, jetoxymethane, triethylene glycol monoethyl ether, glycerin, polyhydric alcohols such as 1,2-hexanediol
  • Examples thereof include alcohol solvents, sulfoxide solvents such as dimethyl sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. Also these The organic solvents can be used alone or in combination.
  • film formation methods from solution examples include spin coating from solution, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spraying Coating methods, screen printing methods, flexographic printing methods, offset printing methods, ink jet printing methods, and other coating methods can be used.
  • the optimum value varies depending on the material used, and the driving voltage and light emission. What is necessary is just to select so that efficiency may become a moderate value. For example, 1 n m to 1, preferably 2 n rr! ⁇ 50 00 nm, more preferably 5 nm to 20 00 nm.
  • the inter-layer When the inter-layer is provided adjacent to the light emitting layer, particularly when both layers are formed by a coating method, the materials of the two layers are mixed and have an unfavorable effect on the characteristics of the device. There is a case.
  • the light emitting layer is formed by the coating method after the interlayer layer is formed by the coating method, as a method for reducing the mixing of the materials of the two layers, the interlayer layer is formed by the coating method, and then the interlayer is formed.
  • a method of forming a light emitting layer after heating one layer to insolubilize it in an organic solvent used for forming a light emitting layer can be mentioned.
  • the heating temperature is usually about 150 to ⁇ 300, and the time is usually about 1 minute to 1 hour.
  • the interlayer layer in order to remove components that have not been insolubilized by heating, the interlayer layer can be removed by rinsing with a solvent used for forming the light emitting layer after heating and before forming the light emitting layer.
  • solvent insolubilization is sufficiently performed by heating, rinsing with a solvent can be omitted.
  • the substrate for forming the polymer light-emitting device of the present invention may be any substrate that does not change when the electrode is formed and the organic layer is formed. Examples thereof include glass, plastic, polymer film, and silicon substrate.
  • the opposite electrode is preferably transparent or translucent.
  • At least one of the anode and the cathode of the polymer light-emitting device of the present invention is transparent or semi-transparent. It is clear.
  • the anode side is preferably transparent or translucent.
  • a conductive metal oxide film, a translucent metal thin film, or the like is used as the material of the anode.
  • a film made of indium oxide, zinc oxide, tin oxide, and a conductive glass made of indium tin oxide (ITO), indium, zinc oxide, etc., which is a composite thereof. (NESA, etc.), gold, platinum, silver, copper, etc. are used, and IT, indium / zinc'oxide, and tin oxide are preferred.
  • the production method include a vacuum deposition method, a sputtering method, an ion plating method, and a plating method.
  • an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof may be used as the anode.
  • the film thickness of the anode can be appropriately selected in consideration of light transmittance and electric conductivity.
  • the film thickness is 10 nm to 10 m, preferably 20 nm to 1; um. More preferably, it is 50 nm to 500 nm.
  • a layer with a thickness of 2 nm or less may be provided.
  • a material for the cathode used in the polymer light emitting device of the present invention is preferably a material having a small work function.
  • metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, Or an alloy of two or more of them, or one or more of them and one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, or Graphite or a graphite intercalation compound is used.
  • alloys include magnesium-silver alloy, magnesium-mudium indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-mu aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, high-strength aluminum alloy, and the like.
  • the cathode may have a laminated structure of two or more layers.
  • the film thickness of the cathode can be selected as appropriate in consideration of electrical conductivity and durability. 10 nm to 10 nm, preferably 20 nm to lzm, more preferably 50 n rr! ⁇ 5 '0 0 nm.
  • a vacuum deposition method, a sputtering method, or a laminating method in which a metal thin film is thermocompression bonded is used.
  • a layer made of a conductive polymer or a layer having an average film thickness of 2 nm or less made of a metal oxide, a metal fluoride, an organic insulating material, or the like may be provided between the cathode and the organic material layer.
  • a protective layer for protecting the polymer light emitting device may be attached. In order to stably use the polymer light emitting device for a long period of time, it is preferable to attach a protective layer and / or a protective cover in order to protect the device from the outside.
  • a polymer compound, metal oxide, metal fluoride, metal boride and the like can be used.
  • a metal plate, a glass plate, a plastic plate with a surface treated with low water permeability can be used, and the cover is bonded to the element substrate with a thermosetting resin or a photo-curing resin and sealed.
  • the method is preferably used. If the space is maintained using a spacer, it is easy to prevent the element from being damaged. If an inert gas such as nitrogen or argon is enclosed in the space, the cathode can be prevented from being oxidized. Further, a desiccant such as barium oxide is placed in the space to adsorb in the manufacturing process. It is easy to suppress damage to the device by a small amount of moisture that penetrates through the cured moisture or cured resin. Of these, it is preferable to take one or more measures.
  • the polymer light emitting device of the present invention can be used as a planar light source, a segment display device, a dot matrix display device, a backlight of a liquid crystal display device, and the like.
  • the planar anode and cathode may be arranged so as to overlap each other.
  • a method in which a mask having a pattern-like window is provided on the surface of the planar light-emitting element, an organic layer of a non-light-emitting portion is formed extremely thick and substantially non- There is a method of emitting light, a method of forming either one of the anode or the cathode, or both electrodes in a pattern.
  • both the anode and the cathode may be formed in a stripe shape and arranged so as to intersect each other.
  • Different types of polymer phosphors with different emission colors Depending on the method and color filter or fluorescence conversion filter, partial color display and multi-color display are possible.
  • the dot matrix element can be driven passively, or may be actively driven in combination with a TFT or the like.
  • planar light-emitting element is a self-luminous thin type and can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can also be used as a curved light source or display device.
  • the present invention will be described in more detail by way of examples, but the present invention is not limited thereto.
  • the number average molecular weight and the weight average molecular weight in terms of polystyrene were determined by GPC (manufactured by Shimadzu Corporation: L C-10 Av p).
  • the polymer to be measured was dissolved in tetrahydrofuran to a concentration of about 0.5 wt%, and 50 IL was injected into GPC.
  • Tetrahydrofuran was used as the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min.
  • two TSK gel SuH RH made by Tosohichi
  • TSKgel Super H2000 made by Tosohichi
  • a differential refractive index detector manufactured by Shimadzu Corp .: R ID — 1 OA was used as the detector.
  • the fluorescence spectrum was measured by the following method.
  • a polymer thin film was prepared by spin-coating a 0.8 wt% toluene solution of the polymer on quartz. The thin film was excited at a wavelength of 350 nm, and the fluorescence spectrum was measured using a fluorescence spectrophotometer (F 1 u o ro 1 o g manufactured by Horiba, Ltd.).
  • the intensity of the Raman line of water was used as a standard, and the fluorescence spectrum plotted with the wavenumber was integrated in the spectral measurement range, and the spectrophotometer (Carry 5E manufactured by Varian) ) was used to determine the value assigned by the absorbance at the excitation wavelength.
  • Glass-transition temperature The glass transition temperature was determined by DSC (DSC 2920, manufactured by TA Instrume nts). '
  • reaction solution was cooled to room temperature, neutralized with 318 mL of a 1N aqueous hydrochloric acid solution, 1 L of methanol was added with stirring, the precipitated crystals were filtered, and washed with MeH.
  • the crystal was dissolved in 90 OmL of toluene, 90 OmL of hexane was added, and the mixture was stirred for 2 hr.
  • the precipitated crystals were filtered and dried under reduced pressure to obtain 45.1 g of the target compound (J5) (yield 55 %, HPLC area percentage 99.0%).
  • phenylphosphoric acid 50 mg was added, and the mixture was further refluxed for 2 hours. Subsequently, an aqueous solution of sodium cetyldithia rubamate was added and stirred at 80 for 2 hours. After cooling, it was washed twice with water (52 ml), twice with 3% aqueous acetic acid (52 ml) and twice with water (52 ml), and the resulting solution was added dropwise to methanol (620 mL). A precipitate was obtained by filtration. The precipitate was dissolved in toluene (124 mL) and purified by passing through an alumina column and a silica gel column.
  • the obtained toluene solution was added dropwise to methanol (620 ml) and stirred, and then the resulting precipitate was collected by filtration and dried.
  • the yield of the obtained polymer compound 1 was 2.54 g.
  • the number average molecular weight in terms of polystyrene of the polymer compound 1 was 1.1 ⁇ 10 5
  • the weight average molecular weight in terms of polystyrene was 2.5 ⁇ 10 5
  • the fluorescence intensity was 4.5, and the glass transition temperature was 73.
  • the obtained toluene solution was added dropwise to methanol (620 ml) and stirred, and then the resulting precipitate was collected by filtration and dried.
  • the yield of the obtained polymer compound 2 was 2.55 g.
  • the polystyrene reduced number average molecular weight of the polymer compound 2 is 1. a 0X 10 5, polystyrene equivalent weight average molecular weight 2. was 3X 10 5.
  • the fluorescence intensity was 7.1, and the glass transition temperature was 136.
  • the polymer compound 2 according to the present invention has a strong fluorescence intensity and excellent heat resistance.
  • the polystyrene reduced number average molecular weight of the polymer compound 3 is 1. a 1 X 10 5, polystyrene-reduced weight average molecular weight was 3. 3X 10 5.
  • the compound (J10) was synthesized by the method described on page 90 of Japanese Patent Application Laid-Open No. 2004-59899.
  • a 1.2 wt% xylene solution of polymer compound 2 was prepared.
  • a glass substrate with an ITO film with a thickness of 1 50 nm formed by sputtering is spin-coated using a solution of poly (ethylenedioxythiophene) / polystyrene sulfonic acid (Bayer, Baytr onP) at 50 nm. And dried on a hot plate at 200 for 10 minutes. Next, a film was formed at a rotation speed of 900 rpm by spin coating using the xylene solution prepared above. The film thickness was about 100 nm.
  • a 1.0 wt% xylene solution of the polymer compound 3 was prepared, and an EL device was produced in the same manner as in Example 3.
  • the light emitting layer was formed by spin coating at a rotational speed of 4000 rpm.
  • the film thickness was about 80 nm.
  • green EL emission peak wavelength: 530 nm
  • the device emitted light of 100 cd Zm z at 6 V, and the maximum luminance was as high as about 12000 cdZm 2 or higher.
  • Example 3 a polymer compound 1 was used to prepare a 1.2% xylene solution, and an EL device was produced in the same manner as in Example 3 using this solution.
  • the light emitting layer The film was formed by pin coating at a rotational speed of 1300 rpm. By applying voltage to the resulting device, green EL emission (peak wavelength 525 nm) was obtained.
  • the obtained toluene solution was added dropwise to methanol (450 ml) and stirred, and then the resulting precipitate was collected by filtration and dried.
  • the yield of the obtained polymer compound 4 was 1.75 g.
  • the polystyrene equivalent number average molecular weight of the polymer compound 4 was 8.3 ⁇ 10 4 , and the polystyrene equivalent weight average molecular weight was 1.9 ⁇ 10 5 .
  • the fluorescence intensity was 4.5 and the glass transition temperature was 78.
  • the number average molecular weight in terms of polystyrene of the polymer compound 5 was 8.8 ⁇ 10 4
  • the weight average molecular weight in terms of polystyrene was 1.8 ⁇ 10 5
  • the fluorescence intensity was 8.1 and the glass transition temperature was 138.
  • the polymer compound 5 according to the present invention has strong fluorescence intensity and excellent heat resistance.
  • a 1.2 wt% xylene solution of polymer compound 5 was prepared, and an EL device was produced in the same manner as in Example 3.
  • the light emitting layer was formed by spin coating at a rotational speed of 1400 rpm.
  • the film thickness was about 80 nm.
  • green EL emission peak wavelength 520 nm
  • the device showed light emission of 100 cd Zm 2 at 5 V, and a maximum luminance of about 12000 cdZm 2 or higher was obtained.
  • the half-life was 3 hours.
  • Comparative Example 4 below which was driven at the same current density, the polymer compound 5 of the present invention had a longer lifetime and was a comparative example. 4>
  • Example 6 a polymer compound 4 was used to prepare a 1.2% xylene solution, and an EL device was produced in the same manner as in Example 3.
  • the light emitting layer was formed by spin coating at a rotation speed of 900 rpm. By applying voltage to the resulting device, green EL emission (peak wavelength 525 nm) was obtained.
  • the number average molecular weight in terms of polystyrene of the polymer compound 6 was 2.8 ⁇ 10 4
  • the weight average molecular weight in terms of polystyrene was 5.2 ⁇ 10 4
  • the fluorescence intensity was 4.9
  • the glass transition temperature was 125 ° C.
  • the compound (J 7) was synthesized by the method described on page 12 of International Publication No. WO 2005 049546.
  • An 1.8 wt% xylene solution of the polymer compound 6 was prepared, and an EL device was produced in the same manner as in Example 3.
  • the light emitting layer was formed by spin coating at a rotation speed of 900 rpm.
  • the film thickness was about 90 nm.
  • blue EL emission peak wavelength: 460 nm
  • a suspension of poly (3, 4) ethylenedioxythiophenopolystyrenesulfonic acid (by tr on P CH 8000) is spin-coated to 80 nm. And dried on a hot plate at 200 for 15 minutes, and then an interlayer layer was formed. Next, the high molecular compound 7 obtained in Example 9 was dissolved in xylene. At this time, the solid content was adjusted to about 1.5 wt%. A film having a thickness of 90 nm was formed by spin coating using this xylene solution. Then, after drying for 1 hour at 130 under a nitrogen atmosphere, barium was used as the cathode.
  • a suspension of poly (3,4) ethylenedioxythiophene polystyrene sulfonic acid (manufactured by Bayer, Bytron P CH 8000) was spin-coated to a thickness of 80 nm.
  • a film was formed and dried on a hot plate at 200 for 15 minutes, and then an interlayer was formed.
  • the polymer compound 8 was dissolved in xylene. At this time, the solid content was adjusted to about 1.5 wt%.
  • a film having a thickness of 85 nm was formed by spin coating using this xylene solution.
  • a glass substrate coated with an ITO film by sputtering is coated with a suspension of poly (3,4) ethylenedioxythiophenopolystyrenesulfonic acid (Bayer, Bytron P CH 8000), and spin-coated to a thickness of 80 nm. And then dried on a hot plate at 200 for 15 minutes, and then an interlayer was formed.
  • the following compound (J 4) 0.6 Ommo compound (J 14) 6.1 2 mmo 1 and compound (J 15) 5.4
  • Polymer compound 9 obtained by condensation polymerization of Ommo 1 was dissolved in xylene.
  • the solid content was adjusted to about 1.5 wt%.
  • the polymer compound 7 and the polymer compound 8 used in Example 10 and Example 12 were respectively
  • the polymer compound according to the present invention exhibits high efficiency and has excellent properties as a material used in a polymer light emitting device.
  • the polymer compound of the present invention is useful as a light-emitting material or a charge transport material, and is excellent in heat resistance, fluorescence intensity, and the like.
  • a light-emitting device using the polymer compound is excellent in performance such as device life and luminous efficiency. Therefore, the polymer LED containing the polymer compound of the present invention is a curved or flat light source for a liquid crystal display backlight or illumination, a segment type display element, a Dome Marix flat panel display, etc. Can be used for

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  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

La présente invention concerne un composé polymère ayant au moins un motif répétitif représenté par la formule (1) et au moins un motif répétitif représenté par une formule choisie parmi les formules (2) et (3) : (1) où Ar1 représente un groupe aryle ou un groupe hétérocyclique aromatique monovalent ; Ar2 représente un groupe arylène ou un groupe hétérocyclique aromatique divalent ; et Z représente un groupe aromatique divalent ayant une structure à cycle condensé ; (2) où les cycles A et B représentent indépendamment un cycle hydrocarboné aromatique, à condition qu’au moins un des cycles A et B représente un cycle hydrocarboné aromatique auquel deux ou plusieurs cycles benzène sont condensés ; et Rw et Rx représentent indépendamment un atome d’hydrogène, un groupe alkyle ou analogues ; et (3) où les cycles C et D représentent indépendamment un cycle aromatique ; et Y représente un atome d’oxygène, un atome de soufre ou -O-C(RK)2- où RK représente un atome d’hydrogène, un groupe alkyle ou analogues.
PCT/JP2006/323257 2005-11-18 2006-11-15 Compose polymere et element electroluminescent polymere l’utilisant WO2007058368A1 (fr)

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GB0810612A GB2447173B (en) 2005-11-18 2006-11-15 Polymer compound and polymer light emitting device using the same
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DE112006002998T DE112006002998T5 (de) 2005-11-18 2006-11-15 Polymerverbindung und Polymer enthaltende Licht ermittierende Vorrichtung, die diese verwendet

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GB0810612D0 (en) 2008-07-16
TW200724568A (en) 2007-07-01
CN101360773A (zh) 2009-02-04
DE112006002998T5 (de) 2008-09-18
GB2447173B (en) 2011-05-11
GB2447173A (en) 2008-09-03
KR20080068134A (ko) 2008-07-22

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