WO2009084548A1 - Composé polymère et dispositif électroluminescent organique l'employant - Google Patents

Composé polymère et dispositif électroluminescent organique l'employant Download PDF

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WO2009084548A1
WO2009084548A1 PCT/JP2008/073474 JP2008073474W WO2009084548A1 WO 2009084548 A1 WO2009084548 A1 WO 2009084548A1 JP 2008073474 W JP2008073474 W JP 2008073474W WO 2009084548 A1 WO2009084548 A1 WO 2009084548A1
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group
substituted
unsubstituted
carbon atoms
nuclear carbon
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Japanese (ja)
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Mitsunori Ito
Yumiko Mizuki
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Idemitsu Kosan Co., Ltd.
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Definitions

  • the present invention relates to a polymer compound containing a repeating unit having a function as a dopant and a repeating unit having a function as a host, and an organic electroluminescence device (organic EL device) using the same.
  • the polymer electroluminescent material has an advantage that a film can be formed by a method of applying and printing the solution, and various studies have been made.
  • a polymer compound containing an aromatic unit having a diarylamino group and a unit having a structure such as fluorene, dibenzofuran, dibenzothiophene has been reported (Patent Documents 1 and 2).
  • Patent Documents 1 and 2 a light emitting device using the above polymer compound has a problem that device characteristics such as lifetime (half life) and luminous efficiency are not always sufficient.
  • An object of the present invention is to provide a polymer compound that is useful as a light-emitting material and can realize a polymer EL device having excellent device characteristics such as lifetime and light emission efficiency, and an organic electroluminescence device using the polymer compound. is there.
  • R 1 to R 14 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted, Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 nuclear carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 nuclear carbon atoms, substituted or unsubstituted nuclear carbon An arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 7 to 30 nuclear carbon atoms, or a substituted or unsubstituted carbon
  • Ar 1 to Ar 3 are each independently a divalent group derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms. Represents a divalent group derived from a heterocyclic group.
  • Ar 4 and Ar 5 each independently represents a substituted or unsubstituted aryl group.
  • R is a substituted or unsubstituted aryl group having 6 to 40 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 40 nuclear atoms, or a substituted or unsubstituted group.
  • An alkyl group having 1 to 50 carbon atoms a is an integer of 0 to 12, b is an integer of 0 to 14, c is an integer of 0 to 10, d is an integer of 0 to 22, and e is an integer of 0 to 6 , F represents an integer of 0 to 18, and when each of a to f is 2 or more, the plurality of R may be the same or different from each other.
  • A is a substituted or unsubstituted divalent saturated group that forms a 5- to 8-membered ring with carbons at positions 1 to 4 forming a benzene ring;
  • B is 2, 3, 5, and A substituted or unsubstituted divalent saturated group which forms a 5- to 8-membered ring with the 6-position carbon, and may be the same as or different from A; when p is 0 or 1, and p is 0 There is no bond between the 5th and 6th carbons; the ring structure formed by the A and 1-4th carbons and / or the B, 2, 3, 5 and 6th carbons The ring structure may include a spiro ring structure. )
  • derived from the compound represented by these is provided.
  • the present invention relates to the above-described repeating unit A and the following formulas (16) and (17):
  • the C ring and the D ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted nuclear atom number of 3
  • R1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted nuclear carbon number 6 to Represents 60 aryl groups.
  • derived from the compound represented by these is provided.
  • the present invention comprises an anode, a cathode, and an organic compound layer comprising at least one layer sandwiched between the anode and the cathode, and at least one of the organic compound layers is a light emitting layer, and the light emission
  • An organic electroluminescence device having a layer containing the polymer compound is provided.
  • the polymer compound of the present invention is useful as a light emitting material, and can provide an organic EL device excellent in performance such as life and luminous efficiency.
  • the polymer compound of the present invention has the following formulas (1) to (7):
  • R 1 to R 14 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted nuclear carbon number of 3 to 20 A cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 nuclear carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 nuclear carbon atoms, substituted Or an unsubstituted arylamino group having 6 to 30 nuclear carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylalkylamino group having 7 to 30 nuclear carbon atoms, An unsubstituted alkenyl group having 8 to 30 carbon atoms, the adjacent substitu
  • Examples of the substituted or unsubstituted alkyl group represented by R 1 to R 14 in the formulas (1) to (7) include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, t-Butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, ⁇ -phenoxybenzyl group, ⁇ , ⁇ - Examples include dimethylbenzyl group, ⁇ , ⁇ -methylphenylbenzyl group, ⁇ , ⁇ -ditrifluoromethylbenzyl group, triphenylmethyl group, ⁇ -benzyloxybenzyl group and the like.
  • Examples of the substituted or unsubstituted cycloalkyl group represented by R 1 to R 14 in the formulas (1) to (7) include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, and the like.
  • Examples of the substituted or unsubstituted alkoxy group represented by R 1 to R 14 in the formulas (1) to (7) include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, an s-butoxy group, Examples thereof include t-butoxy group, pentyloxy group (including isomers), hexyloxy group (including isomers) and the like.
  • Examples of the substituted or unsubstituted aryl group represented by R 1 to R 14 in the formulas (1) to (7) include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, and a 2-anthryl group.
  • 9-anthryl group 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group 2-pyrenyl group, 4-pyrenyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, p-terphenyl-4-yl group, p-terphenyl-3-yl Group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tol group Group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl
  • Examples of the substituted or unsubstituted aryloxy group represented by R 1 to R 14 in the formulas (1) to (7) include a phenoxy group, a tolyloxy group, and a naphthyloxy group.
  • Examples of the substituted or unsubstituted arylamino group represented by R 1 to R 14 in the formulas (1) to (7) include mono- or diphenylamino group, mono- or ditolylamino group, mono- or dinaphthylamino group, naphthylphenylamino Groups and the like.
  • Examples of the substituted or unsubstituted alkylamino group represented by R 1 to R 14 in the formulas (1) to (7) include a mono or dimethylamino group, a mono or diethylamino group, a mono or dihexylamino group, and the like. .
  • Examples of the substituted or unsubstituted arylalkylamino group represented by R 1 to R 14 in the formulas (1) to (7) include groups in which a part of the alkylamino group described above is substituted with the aryl group described above Is mentioned.
  • Examples of the substituted or unsubstituted alkenyl group represented by R 1 to R 14 in the formulas (1) to (7) include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1 , 3-butanedienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1 -Phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group Etc.
  • Examples of the aromatic hydrocarbon group represented by Ar 1 , Ar 2 and Ar 3 in the formulas (2) and (3) include divalent residues such as benzene, naphthalene, anthracene, phenanthrene, pyrene, perylene, chrysene, biphenyl, etc. Among these, divalent residues of benzene and naphthalene are preferable.
  • Examples of the aromatic heterocyclic group represented by Ar 1 , Ar 2 and Ar 3 in the formulas (2) and (3) include pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, acridine, imidazopyridine and imidazopyrimidine.
  • Ar 4 and Ar 5 are each independently a substituted or unsubstituted aryl group having the following formula: It is preferable that it is represented by either.
  • R 21 to R 23 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, —NR 24 R 25 , —OR 26 , —S (O) n R 24 , —Se (O) n R 24 (n is an integer of 0 to 3) or a substituted or unsubstituted aryl group having 6 to 30 nuclear carbon atoms, and R 24 and R 25 are each independently hydrogen, substituted or unsubstituted carbon number
  • X is carbon or nitrogen, but when it is nitrogen, R 1 described above does not exist.
  • the optional substituents include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a nucleus having 6 to 30 carbon atoms.
  • nuclear carbon means a carbon atom constituting a saturated ring, unsaturated ring or aromatic ring
  • nuclear atom constitutes a heterocycle (including saturated ring, unsaturated ring and aromatic ring). Means carbon atoms and heteroatoms.
  • repeating unit A Specific examples of the repeating unit A are shown below, but are not limited thereto.
  • the polymer compound of the present invention contains one or more divalent repeating units (repeating units B) derived from compounds represented by the following formulas (8) to (15), or 1 type or more of the bivalent repeating unit (repeating unit B ') induced
  • R is a substituted or unsubstituted aryl group having 6 to 40 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 40 nuclear atoms, or a substituted or unsubstituted group.
  • A is an integer of 0 to 12
  • b is an integer of 0 to 14
  • c is an integer of 0 to 10
  • d is an integer of 0 to 22
  • e is an integer of 0 to 6
  • f Represents an integer of 0 to 18, and when each of a to f is 2 or more, a plurality of R may be the same or different from each other.
  • the two valences are any of the formulas On the benzene ring.
  • the two valences may be on different benzene rings or on the same benzene ring.
  • a in the above formula (13) is a substituted or unsubstituted divalent saturated group that forms a 5- to 8-membered ring with the 1- to 4-position carbons that form a benzene ring; B forms a benzene ring A substituted or unsubstituted divalent saturated group which forms a 5- to 8-membered ring with the 2, 3, 5 and 6-position carbons, and may be the same as or different from A; p is 0 or 1 , P is 0, there is no bond between the 5th and 6th carbons; the ring structure formed by A and the 1st to 4th carbons and / or B and 2, 3, 5 And the ring structure formed by the 6-position carbon may contain a spiro ring structure.
  • the atoms forming A or B are C, Si, O, S, N, B, P, and combinations thereof. Specific examples of A and B are shown below, but are not limited thereto.
  • the C ring and the D ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted nuclear atom number of 3 Represents up to 40 aromatic heterocycles.
  • Rw and Rx are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted amino group, Substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group having 1 to 50 nuclear carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted 6 to 50 nuclear carbon atoms An arylthio group, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 nuclear carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group, and these groups are bonded to each other to form a ring.
  • Y represents an oxygen atom, a substituted or unsubstituted nitrogen atom, a substituted or unsubstituted silicon atom, a substituted or unsubstituted phosphorus atom, a sulfur atom, —O—C (Rk) 2 — and —N (Rl) —C (Rm) 2 — is represented.
  • Rk and Rm are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted amino group, substituted or unsubstituted Silyl group, substituted or unsubstituted alkoxy group having 1 to 50 nuclear carbon atoms, substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, Substituted or unsubstituted C1-C50 alkoxycarbonyl group, halogen atom, cyano group, nitro group, hydroxyl group, arylalkenyl group, arylalkynyl group, imine residue, amide group, acid imide group or carboxyl group Each of these groups may be bonded to each other
  • Rl represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms.
  • repeating units B and B ′ are shown below, but are not limited thereto.
  • the compound of the above formula (10) is preferably the following compound.
  • Ar and Ar ′ are each a substituted or unsubstituted aryl group having 6 to 40 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 40 nuclear atoms, a substituted or unsubstituted benzyl group, or These are substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and are appropriately selected from the above-mentioned substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, and substituted or unsubstituted alkyl groups.
  • FA and FA ' are each a substituted or unsubstituted aryl group having 6 to 30 nuclear carbon atoms, and are appropriately selected from the above-described substituted or unsubstituted aryl groups.
  • FA and FA ' may be a fused aryl group.
  • Examples of the compounds of the formulas (4), (5) and (7) include, for example, JP 2002-243545 A, JP 2003-401038 A, JP 2003-423317 A, WO 01/172673, Examples include compounds described in WO2007 / 004364.
  • the aromatic hydrocarbon ring is preferably a benzene ring alone or a condensed benzene ring, and may be substituted with a benzene ring or a naphthalene ring.
  • Aromatic hydrocarbon rings such as anthracene ring, tetracene ring, pentacene ring, pyrene ring and phenanthrene ring.
  • Examples of the substituted or unsubstituted arylalkenyl group having 8 to 30 carbon atoms represented by Rw, Rx, Rk, and Rm in the formulas (16) and (17) include a phenyl-C2 to C12 alkenyl group and a Cl to C12 alkoxyphenyl-C2
  • Illustrative examples include —C12 alkenyl group, Cl—C12 alkylphenyl-C2 to C12 alkenyl group, 1-naphthyl-C2 to C12 alkenyl group, and 2-naphthyl-C2 to C12 alkenyl group.
  • Examples of the substituted or unsubstituted arylalkynyl group having 8 to 30 carbon atoms represented by Rw, Rx, Rk, and Rm in the formulas (16) and (17) include phenyl-C2 to C12 alkynyl group, Cl to C12 alkoxyphenyl-C2 Illustrative examples include —C12 alkynyl group, Cl—C12 alkylphenyl-C2 to C12 alkynyl group, 1-naphthyl-C2 to C12 alkynyl group, and 2-naphthyl-C2 to C12 alkynyl group.
  • Rw, Rx, Rk, Rm of the formulas (16) and (17) are mono-, di- or tri-substituted silyl groups having 1 to 30 carbon atoms, such as trimethylsilyl group, triethylsilyl group, trifluoropropylsilyl group, tri-1-propyl Silyl group, dimethyl-1-propylyl group, diethyl-1-propylsilyl group, t-butylsilyldimethylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2- Ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl-dimethylsilyl group, lauryldimethylsilyl group,
  • Rw, Rx, Rk, Rm substituted or unsubstituted imine residues having 2 to 30 carbon atoms in formulas (16) and (17) are, for example, the following imine compounds: Is a group derived from
  • Rw, Rx, Rk, Rm in formulas (16) and (17) are substituted or unsubstituted amide groups having 2 to 30 carbon atoms such as formamide group, acetamide group, propioamide group, butyroamide group, benzamide group, trifluoro Examples include an acetamide group, a pentafluorobenzamide group, a diformamide group, a diacetamide group, a dipropioamide group, a dibutyroamide group, a dibenamide group, a ditrifluoroacetamido group, and a dipentafluorobenzamide group.
  • Rw, Rx, Rk, Rm substituted or unsubstituted acid imide groups having 3 to 30 carbon atoms of the formulas (16) and (17) are represented by, for example, the following formulas: It is group represented by these.
  • Rw, Rx, Rk, Rm and other substituents of formulas (16) and (17) are selected from the substituents described for R 1 to R 14 .
  • the two valences are on any benzene ring in the formula.
  • the two valences may be on different benzene rings or on the same benzene ring.
  • the two valences may be on either the C ring or the D ring, and the two valences may be on different rings, They may be on the same ring.
  • the polymer compound of the present invention comprises a random copolymer containing a repeating unit A and a repeating unit B or a repeating unit B '(-ABBABBBAAABA- (when the repeating units are A and B)), an alternating copolymer (-ABABABABABAB -(When the repeating unit is A and B)), a block copolymer (-AAAAAABBBBBB- (when the repeating unit is A and B)), a graft copolymer (the repeating unit A and the repeating unit B or the repeating unit B ') Either of which may be the main chain or which may be the side chain.
  • the number average molecular weight (Mn) of the polymer compound of the present invention is preferably 10 3 to 10 8 , more preferably 10 4 to 10 6 .
  • the weight average molecular weight (Mw) is preferably 10 3 to 10 8 , more preferably 10 5 to 10 6 . Both molecular weights were obtained by calibration with standard polystyrene using size exclusion chromatography (SEC).
  • the molar ratio of the repeating unit A to the repeating unit B or the repeating unit B ′ is preferably 0.1: 99.9 to 99.9: 0.1, preferably 0.1 to 50 More preferably, 0.1 to 40 is more preferable, and 1 to 40 is particularly preferable.
  • the polymer compound of the present invention includes, for example, the following formula (16): Y 1- (Repeating unit A) -Y 2 (16) And a compound represented by the following formula (17): Y 1- (Repeating unit B or repeating unit B ′)-Y 2 (17) It can manufacture by carrying out condensation polymerization of the compound represented by these.
  • Y 1 and Y 2 are each independently a halogen atom (chlorine atom, bromine atom, iodine atom) or sulfonate group (—OSO 2 R 1 , R 1 is A group selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted alkyl group), a methoxy group, a boric acid ester group, a boric acid group (—B (OH) 2 ), —MgX 1 (X 1 is chlorine Atoms, halogen atoms such as bromine atoms and iodine atoms), —ZnX 1 (X 1 is the same as above), —SnR 1 (R 1 is the same as above), preferably halogen atoms, borate groups, boric acid Represents a group.
  • R 1 is A group selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted alkyl group
  • borate group examples include the following groups.
  • Condensation polymerization is performed in the presence of a catalyst and a base as necessary.
  • the catalyst include palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium complexes such as palladium acetate, nickel [tetrakis (triphenylphosphine)], [1,3- Transition metal complexes such as bis (diphenylphosphino) propane] dichloronickel and nickel complexes such as [bis (1,4-cyclooctadiene)] nickel and, if necessary, triphenylphosphine and tri (t-butylphosphine) ),
  • a catalyst composed of a ligand such as tricyclohexylphosphine, diphenylphosphinopropane, or bipyridyl.
  • catalysts can be used alone or in admixture of two or more.
  • the amount of the catalyst used is preferably from 0.001 to 300 mol%, more preferably from 0.01 to 20 mol%, based on the total number of moles of the compounds of formulas (9) and (10).
  • Examples of the base include sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tribasic ammonium phosphate, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, And organic bases such as tetrabutylammonium hydroxide.
  • the amount of the base used is preferably 0.5 to 20 equivalents, more preferably 1 to 10 equivalents, relative to the total number of moles of the compounds of formulas (9) and (10).
  • the condensation polymerization may be performed in the presence of an organic solvent.
  • organic solvent include toluene, xylene, mesitylene, tetrahydrofuran, 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 the organic solvent used is preferably such that the concentration of the monomer (compounds of formulas (9) and (10)) is 0.1 to 90% by weight, more preferably 1 to 50% by weight.
  • the condensation polymerization temperature is not particularly limited as long as the reaction medium is kept in a liquid state. ⁇ 100 to 200 ° C. is preferable, and 0 to 120 ° C. is more preferable.
  • the reaction time varies depending on the reaction conditions such as reaction temperature, but is preferably 1 hour or longer, more preferably 2 to 500 hours.
  • the desired polymer compound can be obtained from the condensation polymerization product by a known method, for example, by adding a reaction solution to a lower alcohol such as methanol and filtering and drying the deposited precipitate.
  • a reaction solution for example, by adding a reaction solution to a lower alcohol such as methanol and filtering and drying the deposited precipitate.
  • a lower alcohol such as methanol
  • filtering and drying the deposited precipitate When the purity of the polymer compound is low, it may be purified by a usual method such as recrystallization, Soxhlet continuous extraction, force ram chromatography or the like.
  • an organic compound layer composed of at least one layer is sandwiched between a pair of electrodes. At least one of the organic compound layers is a light emitting layer.
  • the thickness of the light emitting layer is preferably 5 to 200 nm, and more preferably 10 to 40 nm because the applied voltage of the device can be lowered.
  • the polymer compound of the present invention is contained in at least one of the organic compound layers, preferably in the light emitting layer.
  • Various intermediate layers are preferably interposed between the electrode and the organic compound layer. Examples of such an intermediate layer include a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. As materials for forming these layers, various organic and inorganic compounds are known.
  • the light emission color of the organic EL element is preferably red.
  • Organic EL elements are usually produced on a translucent substrate.
  • This light-transmitting substrate is a substrate that supports the organic EL element.
  • the light transmittance in the visible region of 400 to 700 nm is 50% or more, and a smoother substrate is used.
  • a translucent substrate for example, a glass plate, a synthetic resin plate, or the like is preferably used.
  • the glass plate include plates formed of soda lime glass, barium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz, and the like.
  • the synthetic resin plate include polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, and polysulfone resin.
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • an electrode substance include metals such as Au, and conductive materials such as CuI, ITO (indium tin oxide), SnO 2 , ZnO, and In—Zn—O.
  • the anode is formed by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is desirable that the transmittance of the anode for light emission is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / square or less.
  • the film thickness of the anode is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm, although it depends on the material.
  • the cathode a material having a work function (4 eV or less) metal, alloy, electrically conductive compound and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-strium alloy, magnesium, lithium, magnesium silver alloy, aluminum / aluminum oxide, Al / Li 2 O, Al / LiO 2 , Al / LIF, aluminum lithium alloy , Indium, and rare earth metals.
  • the cathode is formed by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the organic compound layer is taken out from the cathode, the transmittance for light emission from the cathode is preferably larger than 10%.
  • the sheet resistance of the cathode is preferably several hundred ⁇ / square or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • a chalcogenide layer, a metal halide layer, and a metal oxide layer are formed on at least one surface of the pair of electrodes thus prepared. It is preferable to arrange at least one layer selected from Specifically, a metal force rucogenide (including oxide) layer such as silicon or aluminum is formed on the anode surface on the organic compound layer side, and a metal halide layer or metal oxide layer is formed on the cathode surface on the organic compound layer side. It is good to arrange. Thereby, the drive can be stabilized.
  • Preferred examples of the chalcogenide include SiOx (1 ⁇ x ⁇ 2), AlOx (1 ⁇ x ⁇ 1.5), SiON, SiAlON, and the like.
  • Examples of the metal halide include LIF, MgF 2 , and CaF. 2 and rare earth metal fluorides are preferable, and examples of the metal oxide include Cs 2 O, Li 2 O, MgO, SrO, BaO, and CaO.
  • a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidizing dopant is provided on at least one surface of the pair of electrodes thus prepared. It is also preferable to arrange them. If it does in this way, an electron transfer compound will be reduced and it will become an anion, and it will become easier for a mixed field to inject and transmit an electron to a luminescent medium.
  • the hole transfer compound is oxidized and becomes force thione, which makes it easier for the mixed region to inject and transfer holes to the luminescent medium.
  • Preferred oxidizing dopants include various Lewis acids and acceptor compounds.
  • Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and compounds thereof.
  • the light emitting layer is (I) Injection function: a function capable of injecting holes from the anode or hole injection layer when an electric field is applied, and a function capable of injecting electrons from the cathode or electron injection layer (ii) transport function: injected charge (electrons And (iii) light emission function: a function of providing a field for recombination of electrons and holes and connecting it to light emission.
  • Examples of a method for forming a layer (organic compound layer, particularly a light emitting layer) containing the polymer compound of the present invention include a method of forming a film of the polymer compound solution.
  • Examples of the film forming method include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing. Screen printing method, flexographic printing method, offset printing method, and ink jet printing method are preferable in that pattern formation is easy. Film formation by these methods can be performed under conditions well known to those skilled in the art, and details thereof are omitted.
  • the film forming solution only needs to contain at least one polymer compound of the present invention, and in addition to the polymer compound, a hole transport material, an electron transport material, a light emitting material, a solvent, a stabilizer, and the like are added.
  • An agent may be included.
  • the content of the polymer compound in the film-forming solution is preferably 20 to 100% by weight, more preferably 40 to 100% by weight, based on the total weight of the composition excluding the solvent.
  • the proportion of the solvent is preferably 1 to 99.9% by weight of the film-forming solution, and more preferably 80 to 99% by weight.
  • the film-forming solution includes additives for adjusting viscosity and / or surface tension, such as thickeners (high molecular weight compounds, poor solvents for the high molecular compounds of the present invention), viscosity reducing agents (low molecular weight compounds, etc.). ), A surfactant and the like may be contained. Moreover, in order to improve storage stability, you may contain antioxidants which do not affect the performance of an organic EL element, such as a phenolic antioxidant and a phosphorus antioxidant.
  • Examples of the solvent for the film-forming solution include chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, and ether-based solvents such as tetrahydrofuran, dioxane and anisole.
  • chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene
  • ether-based solvents such as tetrahydrofuran, dioxane and anisole.
  • Aromatic hydrocarbon solvents such as toluene and xylene; aliphatics such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane Hydrocarbon solvents; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, benzophenone, acetophenone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; ethylene glycol, ethylene Glycol monobutyl ether Polyhydric alcohols such as lenglycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol
  • organic solvents can be used alone or in combination.
  • aromatic hydrocarbon solvents ether solvents, aliphatic hydrocarbon solvents, ester solvents, ketone solvents are preferred from the viewpoints of solubility, film formation uniformity, viscosity characteristics, etc., toluene, Xylene, ethylbenzene, diethylbenzene, trimethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzene, isobutylbenzene, 5-butylbenzene, n-hexylbenzene, cyclohexylbenzene, 1-methylnaphthalene, tetralin, anisole, Ethoxybenzene, cyclohexane, bicyclohexyl, cyclohexenylcyclohexanone, n-heptylcyclohexane, n-hexylcyclohexane,
  • the light emitting layer may optionally contain an organic compound other than the polymer compound, or the light emitting layer containing the polymer compound of the present invention.
  • another light emitting layer containing a known organic compound may be stacked.
  • the light emitting layer comprises a compound represented by formulas (1) to (7), a homopolymer composed of repeating unit A, a copolymer containing repeating unit A, formula (8 ) To (15), a homopolymer consisting of repeating unit B, a copolymer containing repeating unit B, a compound represented by formulas (16) and (17), and a single unit consisting of repeating unit B ′ It may contain at least one compound selected from a polymer and a copolymer containing the repeating unit B ′.
  • the light emitting layer may contain 0.1 to 20 parts by weight of a known fluorescent or phosphorescent dopant with respect to 100 parts by weight of the polymer compound.
  • a known fluorescent or phosphorescent dopant include amine compounds, chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc. It is chosen together.
  • the phosphorescent dopant is preferably a metal complex compound containing at least one metal selected from Ir, Ru, Pd, Pt, Os and Re.
  • the ligand is a phenylpyridine skeleton, It preferably has at least one skeleton selected from a bipyridyl skeleton and a phenanthroline skeleton.
  • metal complex compounds include tris (2-phenylpyridine) iridium, tris (2-phenylpyridine) ruthenium, tris (2-phenylpyridine) palladium, bis (2-phenylpyridine) platinum, tris (2 -Phenylpyridine) osmium, tris (2-phenylpyridine) rhenium, octaethylplatinum porphyrin, octaphenylplatinum porphyrin, octaethylpalladium porphyrin, octaphenylpalladium porphyrin, and the like.
  • An appropriate complex is selected from the relationship with the luminescent color, device performance, and polymer compound.
  • the light emitting layer may contain 0.1 to 50 parts by weight of an arylamine compound and / or a styrylamine compound with respect to 100 parts by weight of the polymer compound.
  • the arylamine compound include WO02 / 20459, JP2006-140235, JP2006-306745, WO2004 / 09211, WO2004 / 044088, JP2006-256979, JP 2007-230960, WO 2004/083162, JP 2006-298793, WO 02/20460, WO 02/20460, JP 2007-137824, JP 2007-45725, JP 2005-068087.
  • the compound disclosed in Japanese Patent Publication No. Gazette and the like and the styrylamine compound include compounds disclosed in WO02 / 20459.
  • the light emitting layer may contain 0.1 to 50 parts by weight of the metal complex compound with respect to 100 parts by weight of the polymer compound. Thereby, the light emission luminance and the light emission efficiency are further improved.
  • the hole injection transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 55 eV or less.
  • a hole injecting and transporting layer a material that transports holes to the light emitting layer with a lower electric field strength is preferable.
  • an electric field having a hole mobility of 10 4 to 10 6 V / cm is applied, Those having at least 10 ⁇ 6 cm 2 / V ⁇ sec are preferred.
  • an arbitrary material is conventionally selected from those conventionally used as a charge transport material for holes in optical transmission materials and known materials used for hole injection layers of organic EL elements. Can be used.
  • the hole injecting and transporting material may be thinned by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
  • the thickness of the hole injecting and transporting layer is not particularly limited, but is usually 5 nm to 5 ⁇ m.
  • the electron injection layer transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility. It is a layer made of a material with good adhesion.
  • a metal complex of 8-hydroxyquinoline or a derivative thereof is preferable. Specific examples of the above-mentioned metal complexes of 8-hydroxyquinoline or its derivatives include metal chelate oxinoid compounds containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline) such as tris (8-quinolinol) aluminum. It can be used as an injection material.
  • the organic EL element of the present invention applies an electric field to the ultrathin film, pixel defects due to leakage or short-circuiting are likely to occur.
  • an insulating thin film layer may be inserted between the pair of electrodes.
  • the material used for the insulating layer for example, aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, oxidizing power lucium, fluorinated power Lucium, aluminum nitride, titanium oxide, Examples thereof include silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. A mixture or laminate of these may be used.
  • the organic EL device of the present invention includes, for example, an anode, a light emitting layer, a hole injection layer as necessary, and an electron injection layer as necessary by the above materials and methods, and finally a cathode. It is manufactured by forming. Moreover, you may manufacture in the reverse order to the above from a cathode to an anode.
  • Example 1 (Monomer synthesis) 1-Bromophenyl-3-phenylisobenzofuran was synthesized as follows by the synthesis method shown in the following formula.
  • Dicyclopenta [cd, lm] perylene (intermediate) was synthesized by the synthesis method shown in the following formula as follows.
  • reaction solution was cooled to room temperature and 15cm 3 added thereto methanol 50 cm 3 and 45% aqueous hydrochloric acid.
  • the precipitate was collected by filtration and washed with sufficient water and methanol.
  • the filtrate was dissolved in 300 cm 3 of chloroform, and impurities were removed through silica gel. Thereafter, purification was performed by a reprecipitation method using dichloromethane and hexane. As a result, 0.9 g of black purple crystals were obtained (yield 38%).
  • MS + : 300 was confirmed.
  • Dibromo-dibenzo [f, f ′] diindeno [1,2,3, -cd: 1 ′, 2 ′, 3′-lm] perylene was synthesized by the synthesis method shown in the following formula as follows.
  • a 1.2 wt% xylene solution of polymer compound 1 was prepared.
  • a glass substrate having an ITO film with a thickness of 150 nm formed by sputtering is formed into a film with a thickness of 50 nm by spin coating using a PEDOT / PSS aqueous solution (Bayer, Bayton P), and is heated on a hot plate at 200 ° C. for 10 minutes. Dried.
  • a film was formed at 900 rpm by spin coating using the prepared xylene solution. The film thickness was about 100 nm. This was dried at 130 ° C. for 1 hour in an argon atmosphere, and further vacuum-dried.
  • Examples 2 to 11 A polymer compound was synthesized according to Example 1 except that the monomers 1 to 3 listed in Tables 1 and 2 below were used.
  • an organic EL device was produced in the same manner as in Example 1 except that the polymer compound and the electron transport material were used, and the device performance was evaluated. The results are shown in Tables 3 and 4.
  • the synthetic reaction formula of the monomer 1 used in Example 5 and the monomer 2 used in Example 6 is as follows.

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Abstract

L'invention concerne un composé polymère contenant un motif répété dérivé d'un composé représenté par l'une des formules (1)-(7) et un motif répété dérivé d'un composé aromatique ayant une structure spécifique. Elle concerne également un dispositif électroluminescent organique employant le composé polymère. [Dans les formules, R1-R14 représentent indépendamment un atome d'hydrogène, un groupe alkyle substitué ou non substitué contenant 1-20 atomes de carbone ou un groupe similaire; Ar1, Ar2 et Ar3 représentent indépendamment un groupe aryle substitué ou non substitué contenant 6-50 atomes de carbone nucléaires ou un groupe similaire; et Ar4 et Ar5 représentent indépendamment un certain groupe.]
PCT/JP2008/073474 2007-12-28 2008-12-24 Composé polymère et dispositif électroluminescent organique l'employant WO2009084548A1 (fr)

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