WO2014132636A1 - Monomère polymérisable, matériau pour dispositif organique comprenant ledit polymère, matériau d'injection/de transport de trou, matériau pour élément électroluminescent organique et élément électroluminescent organique - Google Patents

Monomère polymérisable, matériau pour dispositif organique comprenant ledit polymère, matériau d'injection/de transport de trou, matériau pour élément électroluminescent organique et élément électroluminescent organique Download PDF

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WO2014132636A1
WO2014132636A1 PCT/JP2014/001018 JP2014001018W WO2014132636A1 WO 2014132636 A1 WO2014132636 A1 WO 2014132636A1 JP 2014001018 W JP2014001018 W JP 2014001018W WO 2014132636 A1 WO2014132636 A1 WO 2014132636A1
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group
substituted
carbon atoms
polymerizable functional
ring
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加藤　朋希
藤山　高広
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出光興産株式会社
三井化学株式会社
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
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    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • 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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a polymerizable monomer, an organic device material containing the polymer, a hole injecting and transporting material, an organic electroluminescent element material, and an organic electroluminescent element.
  • organic EL elements organic electroluminescence elements
  • cost reduction and large screen are cited as major issues. Therefore, the expectation from the conventional vacuum evaporation type organic EL element to the (solution) coating type organic EL element is increasing.
  • the coating type is used, the material utilization efficiency is high, and large-screen film formation is facilitated. Furthermore, since a vacuum system is unnecessary, the cost of the manufacturing apparatus is expected to be low.
  • the coating type organic EL material includes a low molecular weight type and a high molecular weight type, but a high molecular weight type is preferable from the viewpoint of solubility, coating uniformity, and formation of a laminated element.
  • a polymer-based hole transport (injection) layer material that can be a common layer for displays and lighting devices.
  • a polymer hole transport (injection) layer material a polymer having a repeating unit obtained by substituting a vinyl group for a low molecular hole transport material is known.
  • the applicant of the present application has proposed a polymerizable monomer and a polymer useful as a coating-type organic device material (see, for example, Patent Documents 1 and 2).
  • a polymerizable monomer represented by the following formula (1) is provided.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • the substituents that Ar 1 and Ar 2 may have are substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a polymerizable functional group which may be substituted with a polymerizable functional group.
  • the number of carbons formed is 6-14
  • R 1 and R 2 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Or an unsubstituted trialkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having 8 to 15 carbon atoms, substituted Alternatively, it represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, a polymerizable functional group, a halogen atom, or a cyano group.
  • R 11 and R 12 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Or an unsubstituted trialkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having 8 to 15 carbon atoms, substituted Alternatively, it represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, a polymerizable functional group, a halogen atom, or a cyano group.
  • R 3 and R 4 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Alternatively, it represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or a polymerizable functional group.
  • R 3 and R 4 may combine with each other to form a saturated or unsaturated divalent group that forms a ring.
  • n 1 and n 2 each independently represents an integer of 0 to 4.
  • n 1 and m 2 each independently represents an integer of 0 to 3.
  • n 1 is 2 to 4
  • a plurality of R 1 may be the same or different from each other, and a plurality of adjacent R 1 are bonded to each other to form a saturated or unsaturated divalent group that forms a ring. It may be formed.
  • n 2 is 2 to 4
  • a plurality of R 2 may be the same or different from each other, and a plurality of adjacent R 2 are bonded to each other to form a saturated or unsaturated divalent group that forms a ring. It may be formed.
  • a plurality of R 11 may be the same or different from each other, and a plurality of adjacent R 11 are bonded to each other to form a saturated or unsaturated divalent group that forms a ring. It may be formed.
  • a plurality of R 12 may be the same or different from each other, and a plurality of adjacent R 12 are bonded to each other to form a saturated or unsaturated divalent group forming a ring. It may be formed.
  • Two or more of R 1 to R 4 , R 11 , R 12 , Ar 1 and Ar 2 contain a polymerizable functional group.
  • a novel polymerizable monomer and a coating-type organic device material obtained by thermal polymerization or the like can be provided. According to the present invention, it is possible to provide a coating type organic EL element having a long lifetime and high luminous efficiency.
  • the polymerizable monomer of the present invention is represented by the following formula (1).
  • the molecular structure represented by the above formula (1) that is, a structure in which a carbazole skeleton, a fluorene skeleton, and an arylamine skeleton are connected (hole transporting structure) has a high hole transporting property. Therefore, the polymerizable monomer of the present invention can be used as a material for a hole transport layer of an organic EL device, for example. Since the polymerizable monomer of Patent Document 1 described above has a structure in which two or more hole transporting structures are connected via a linking group, there is a problem that the solubility is low. In the present invention, the solubility of the monomer can be improved by providing one hole transporting structure for one polymerizable monomer. Thereby, the film-forming property of the film
  • the polymerizable monomer of the present invention includes two or more polymerizable functional groups among R 1 to R 4 , R 11 , R 12 , Ar 1 and Ar 2 in the formula (1). Thereby, the heat resistance and smoothness of the film obtained by polymerizing the polymerizable monomer are improved.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms. Represents.
  • the substituent that Ar 1 and Ar 2 may have is substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, which may be substituted with a polymerizable functional group, or a polymerizable functional group.
  • R 1 and R 2 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Or an unsubstituted trialkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having 8 to 15 carbon atoms, substituted Alternatively, it represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, a polymerizable functional group, a halogen atom, or a cyano group.
  • R 11 and R 12 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Or an unsubstituted trialkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having 8 to 15 carbon atoms, substituted Alternatively, it represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, a polymerizable functional group, a halogen atom, or a cyano group.
  • R 3 and R 4 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Alternatively, it represents an unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or a polymerizable functional group.
  • R 3 and R 4 may combine with each other to form a saturated or unsaturated divalent group that forms a ring.
  • R 3 and R 4 are each preferably a substituted or unsubstituted linear alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. Thereby, the solubility of a polymerizable monomer improves.
  • n 1 and n 2 each independently represents an integer of 0 to 4.
  • m 1 and m 2 each independently represents an integer of 0 to 3.
  • n 1 is 2 to 4
  • a plurality of R 1 may be the same or different from each other, and a plurality of adjacent R 1 are bonded to each other to form a saturated or unsaturated divalent group that forms a ring. It may be formed.
  • n 2 is 2 to 4
  • a plurality of R 2 may be the same or different from each other, and a plurality of adjacent R 2 are bonded to each other to form a saturated or unsaturated divalent group that forms a ring. It may be formed.
  • a plurality of R 11 may be the same or different from each other, and a plurality of adjacent R 11 are bonded to each other to form a saturated or unsaturated divalent group that forms a ring. It may be formed.
  • a plurality of R 12 may be the same or different from each other, and a plurality of adjacent R 12 are bonded to each other to form a saturated or unsaturated divalent group forming a ring. It may be formed.
  • R 1 to R 4 , R 11 , R 12 , Ar 1 and Ar 2 contain a polymerizable functional group.
  • the number of polymerizable functional groups is preferably 2 to 4 because the heat resistance and smoothness of the film obtained by polymerizing the polymerizable monomer are improved.
  • Ar 1 and Ar 2 are a group represented by the following formula (3) or (4).
  • a glass transition temperature improves by inserting a rigid structure
  • membrane stability improves.
  • reduction resistance electron resistance
  • durability and lifetime of an organic device, especially an organic EL element improve.
  • L 1 represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  • L 2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  • the substituent that L 1 and L 2 may have is substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and a polymerizable functional group which may be substituted with a polymerizable functional group.
  • the number of carbon atoms formed is 6 to 14.), an aryl group having 6 to 50 ring carbon atoms that may be substituted with a polymerizable functional group, and a ring atom number 5
  • X is a substituted or unsubstituted heteroatom.
  • the substituent is an alkyl group having 1 to 20 carbon atoms which may be substituted with a polymerizable functional group, or a carbon group having 3 to 10 carbon atoms which may be substituted with a polymerizable functional group.
  • a cycloalkyl group an aryl group having 6 to 30 ring carbon atoms which may be substituted with a polymerizable functional group, an aralkyl group having 7 to 31 carbon atoms which may be substituted with a polymerizable functional group (ring of the aryl moiety) And one or more groups selected from the group consisting of heterocyclic groups having 6 to 30 carbon atoms and 3 to 30 ring-forming atoms optionally substituted with a polymerizable functional group.
  • R 13 to R 16 are each independently substituted with a polymerizable functional group, a linear or branched alkyl group having 1 to 30 carbon atoms which may be substituted with a polymerizable functional group, or a polymerizable functional group.
  • a is an integer of 0 to 3.
  • b to d are each independently an integer of
  • the group containing the polymerizable functional group contained in the polymerizable monomer of the present invention is preferably a group containing a vinyl group, vinylidene group, vinylene group or ethynylene group represented by the following formula (i);
  • R 11 , R 12 and R 13 are each independently a hydrogen atom, a fluorine atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring-forming carbon number. 6 to 24 aryl groups.
  • L 11 is a divalent linking group. n is an integer of 0 or 1, and when n is 0, L 11 is a single bond) (In the formula, L 11 is a divalent linking group. n is an integer of 0 or 1, and when n is 0, L 11 is a single bond) (In the formula, L 11 is a divalent linking group.
  • n is an integer of 0 or 1, and when n is 0, L 11 is a single bond)
  • L 11 is a divalent linking group. n is an integer of 0 or 1, and when n is 0, L 11 is a single bond
  • R 14 is a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms.
  • L 11 is a divalent linking group. n is an integer of 0 or 1, and when n is 0, L 11 is a single bond)
  • the divalent linking group of L 11 is preferably —L 12 —, —O—, —C ( ⁇ O) —, —C ( ⁇ O) O—, —OC.
  • L 12 represents a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 3 to 24 ring atoms, a substituted or unsubstituted carbon group having 1 to 20 carbon atoms.
  • R 15 to R 17 is independently a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms
  • L 11 selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms and a linking group as described above improves the solubility of the monomer in the coating solvent. ,polymerization ⁇ high, reduce the unreacted monomers, the organic device can be improved particularly the durability and lifetime of the organic EL element.
  • L 12 is preferably a linking group containing a substituted or unsubstituted linear or branched alkylene group having 3 to 12 carbon atoms.
  • L 12 contains a linear or branched alkylene group having 3 to 12 carbon atoms, the solubility of the monomer in the coating solvent can be improved.
  • the group (vi) is preferably a group having a substituted or unsubstituted epoxy group or oxetane group.
  • the group containing a polymerizable functional group is the group (vi)
  • the polymerization reaction can be performed at a low temperature, and adverse effects due to heat on the hole injection / transport unit can be reduced.
  • R 1 and R 2 in the above formula (1) when at least one of R 1 and R 2 in the above formula (1) has a polymerizable functional group, charge injection hopping transport between molecules is advantageous due to the proximity of the hole injection transport units. This is preferable because hole transport is promoted.
  • the polymerizable functional group when at least one of R 3 and R 4 has a polymerizable functional group, the polymerizable functional group can be separated from the hole injecting and transporting unit, and the radical and / or cation that is a reactive species of the polymerization The adverse effect on the hole injecting and transporting unit can be reduced.
  • the freedom degree of a polymeric functional group increases, since a polymerization reaction rate is high, an unreacted monomer reduces, and durability and lifetime of an organic device, especially an organic EL element can be improved, it is preferable.
  • the hole injection and transport units come close to each other, which makes charge hopping transport between molecules advantageous and facilitates hole transport. Therefore, it is preferable.
  • At least one of R 1 and R 2 in the formula (1) has a polymerizable functional group, and at least one of R 3 , R 4 , R 11 , R 12 , Ar 1 and Ar 2 is a polymerizable functional group. It preferably has a group. Also, at least one of R 3 , R 4 , R 11 , and R 12 has a polymerizable functional group, and at least one of R 1 , R 2 , Ar 1, and Ar 2 has a polymerizable functional group Is preferred. Furthermore, it is preferable that at least one of Ar 1 and Ar 2 has a polymerizable functional group, and at least one of R 1 to R 4 , R 11 , and R 12 has a polymerizable functional group. In the above case, the polymerizable functional group crosslinks the molecules on the network, and as a result of improving the film formability, the organic device, particularly the organic EL element can be driven at a low voltage, and the durability and life are improved. Can do.
  • the aryl group includes a monocyclic aromatic hydrocarbon ring group and a condensed aromatic hydrocarbon ring group in which a plurality of hydrocarbon rings are condensed
  • the heteroaryl group is a monocyclic heteroaromatic group.
  • a hetero-fused aromatic ring group in which a plurality of heteroaromatic rings are condensed and a hetero-fused aromatic ring group in which an aromatic hydrocarbon ring and a heteroaromatic ring are condensed.
  • Ring-forming carbon means a carbon atom constituting an aromatic ring, and ring-forming atom (nuclear atom) constitutes a heterocyclic ring (including a saturated ring, an unsaturated ring and an aromatic heterocyclic ring). Means carbon and heteroatoms.
  • the “carbon number ab” in the expression “substituted or unsubstituted X group having carbon number ab” represents the number of carbons when the X group is unsubstituted, and the X group is substituted. The carbon number of the substituent in the case where it is present is not included.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
  • aryl groups include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 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-3-
  • phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl 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, o-tolyl group, m-tolyl group, p-tolyl group, fluorene-2- Yl group and fluoren-3-yl group are preferable, and phenyl group, 1-naphthyl group, 2-naphthyl group, m-tolyl group, p-tolyl group, fluoren-2-yl group and fluoren-3-yl group are more preferable. preferable.
  • arylene groups Each of the aryl groups is selected from divalent groups obtained by removing one aromatic hydrogen. Among them, 1,4-phenylene group, 1,3-phenylene group, 1,4-naphthylene group, 1,10-anthrylene group, 4,4′-biphenylylene group, 3,4′-biphenylylene group, 4,3 ′ -Biphenylylene group, 4,4 "-p-terphenylylene group, 3,4" -p-terphenylylene group, 4,3 "-p-terphenylylene group, 1,4-tolylene group, 4,4" -fluorenylene group, 3 , 3 "-fluorenylene group is preferred, 1,4-phenylene group, 1,4-naphthylene group, 1,10-anthrylene group, 4,4'-biphenylylene group, 3,4'-biphenylylene group, 4,4" -P-terphenylylene group, 2,7-fluorenylene group
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n- Heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3- And dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, and the like, preferably methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, A tert-butyl group. Of these, methyl group, ethyl group, propyl group, isopropyl group
  • cycloalkyl group examples include, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, a 4-fluorocyclohexyl group, a 1-adamantyl group, and a 2-adamantyl group.
  • Group, 1-norbornyl group, 2-norbornyl group and the like, and a cyclopentyl group and a cyclohexyl group are preferable.
  • An alkoxy group, a cycloalkoxy group, and an aryloxy group are groups in which an O atom is interposed at the substitution site of the alkyl group, cycloalkyl group, or aryl group.
  • Aralkyl group is a group in which the aryl group is substituted for the alkyl group.
  • trialkylsilyl group examples include, for example, a trimethylsilyl group, a vinyldimethylsilyl group, a triethylsilyl group, a tripropylsilyl group, a propyldimethylsilyl group, a tributylsilyl group, a t-butyldimethylsilyl group, a tripentylsilyl group, Examples thereof include a triheptylsilyl group and a trihexylsilyl group, and a trimethylsilyl group and a triethylsilyl group are preferable.
  • the alkyl group substituted by the silyl group may be the same or different.
  • triarylsilyl group examples include, for example, a triphenylsilyl group and a trinaphthylsilyl group.
  • Triphenylsilyl group Preferably, Triphenylsilyl group.
  • the aryl groups substituted on the silyl group may be the same or different.
  • dialkylarylsilyl group examples include, for example, dimethylphenylsilyl group, diethylphenylsilyl group, dipropylphenylsilyl group, dibutylphenylsilyl group, dipentylphenylsilyl group, diheptylphenylsilyl group, dihexylphenylsilyl group, dimethyl Naphthylsilyl group, dipropylnaphthylsilyl group, dibutylnaphthylsilyl group, dipentylnaphthylsilyl group, diheptylnaphthylsilyl group, dihexylnaphthylsilyl group, dimethylanthrylsilyl group, diethylanthrylsilyl group, dipropylanthrylsilyl group, Examples include dibutylanthrylsilyl group, dipentylanthrylsilyl group, diheptyl
  • alkyldiarylsilyl group examples include, for example, methyldiphenylsilyl group, ethyldiphenylsilyl group, propyldiphenylsilyl group, butyldiphenylsilyl group, pentyldiphenylsilyl group, heptyldiphenylsilyl group, and the like.
  • a methyldiphenylsilyl group and an ethyldiphenylsilyl group examples include, for example, methyldiphenylsilyl group, ethyldiphenylsilyl group, propyldiphenylsilyl group, butyldiphenylsilyl group, pentyldiphenylsilyl group, heptyldiphenylsilyl group, and the like.
  • a methyldiphenylsilyl group and an ethyldiphenylsilyl group examples include, for example, methyldiphenylsilyl
  • heteroaryl group examples include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group.
  • the mono- or dialkylamino group is a group in which the alkyl group is substituted on the amino group.
  • a mono or diarylamino group is a group obtained by substituting the aryl group for an amino group.
  • An alkylarylamino group is a group obtained by substituting the alkyl group and aryl group for an amino group.
  • halogen atom examples include fluorine, chlorine and bromine. Of these, fluorine is preferred. The reason is that since the surface tension of the obtained polymer is lowered, a more uniform coating film can be formed.
  • a hydrogen atom may be substituted with a halogen atom.
  • halogen atoms a fluorine atom is preferred. The reason is that since the surface tension of the obtained polymer is lowered, a more uniform coating film can be formed.
  • the polymerizable monomer of the present invention can be synthesized by referring to, for example, International Publication No. 2010/103765.
  • the polymer of this invention is a polymer containing the structural unit derived from the polymerizable monomer of this invention mentioned above, and consists of either of the following.
  • A a homopolymer having a repeating unit derived from one type selected from the polymerizable monomers of the present invention described above
  • b two or more types selected from the polymerizable monomers of the present invention described above
  • the unit derived from the polymerizable monomer of the present invention preferably contains 10 mol% or more, more preferably 30 mol% or more, and more preferably 50 mol%. More preferably, it is contained. By containing 70 mol% or more of units derived from the polymerizable monomer of the present invention, the effects obtained using the polymerizable monomer of the present invention are sufficiently exhibited, which is particularly preferable.
  • copolymers (b) and (c) there is no particular limitation on the bonding mode, and random copolymers, alternating copolymers, block copolymers, graft copolymers, random block copolymers, comb shapes Any of a copolymer, a star copolymer and the like may be used.
  • the other monomer of the copolymer (c) is preferably a polymerization in which a monoamine aromatic compound, a diamine aromatic compound, and a triamine aromatic compound shown below are substituted with a group containing a polymerizable functional group.
  • Monomer. wherein, Ar a to Ar e are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, L a and L b are each independently a substituted or unsubstituted arylene group having 6 to 40 ring carbon atoms. Examples of Ar a to Ar e and the aryl and arylene groups of L a and L b are the same as those described above.
  • the substitution group of the Ar a ⁇ Ar e and L a and L b are each independently an alkyl group having 1 to 20 carbon atoms, having 3 to 10 carbon atoms a cycloalkyl group, ring-forming carbon number of 6 to 30
  • Rusilyl group (the aryl portion has 6 to 20 ring carbon atoms), 8 to 30 alkyl arylamino group (the aryl portion has 6 to 20 ring carbon atoms), halogen atom, nitro group, cyano group and hydroxyl group
  • the group containing a polymerizable functional group is preferably substituted with the terminal aromatic group of Ar a to Ar e of the above-described amine-based aromatic compound.
  • the group containing a polymerizable functional group on the terminal aromatic group is more preferably a para-position to the moiety other than the terminal aromatic group in the above formula (for example, 1 if the terminal aromatic group is a phenylene group). , 4 position). This is because the interaction between the side chains is reduced and the occurrence of excimers and exciplexes can be reduced, so that the device performance such as the hole transport ability of the polymer is improved, the polymerization reaction rate is high, and the unreacted single unit. This is because the mass is reduced and the durability and life of the organic device, particularly the organic EL element, are improved.
  • the solubility of the resulting polymer in a coating solvent can be improved, and hole injection characteristics and transport characteristics can be improved.
  • the number average molecular weight (Mn) is preferably 10 3 to 10 8 , more preferably 10 3 to 10 6 .
  • the weight average molecular weight (Mw) is preferably 10 3 to 10 8 , more preferably 10 3 to 10 6 .
  • the molecular weight distribution represented by Mw / Mn is not particularly limited, but is preferably 10 or less, and more preferably 3 or less.
  • the molecular weight is too large, it becomes impossible to form a uniform film in forming the device due to gelation, and if the molecular weight is too small, it is difficult to control the solubility. Both molecular weights are obtained by calibration with standard polystyrene using size exclusion chromatography (SEC).
  • SEC size exclusion chromatography
  • the polymer of the present invention can be produced by addition, cyclization or ring-opening polymerization of a monomer.
  • the polymerization method is not particularly limited, but can be carried out by heating, light irradiation, or addition of a reaction initiator.
  • the polymerization method of the polymer of the present invention is not limited, and examples thereof include a radical polymerization method, an ionic polymerization method, a living polymerization method, a radical living polymerization method, and coordination polymerization.
  • radical polymerization or cationic polymerization is preferred.
  • the radical polymerization initiator include azo compounds and peroxides, and azobisisobutyronitrile (AIBN), azobisisobutyric acid diester derivatives, and dibenzoyl peroxide (BPO) are preferable.
  • AIBN azobisisobutyronitrile
  • BPO dibenzoyl peroxide
  • As the initiator for cationic polymerization various strong acids (p-toluenesulfonic acid, trifluoromethanesulfonic acid, etc.) and Lewis acids are preferable.
  • the polymerization solvent is not particularly limited.
  • aromatic hydrocarbon solvents such as toluene and chlorobenzene, halogenated hydrocarbon solvents such as methylene chloride and dichloroethane and chloroform, ether solvents such as tetrahydrofuran and dioxane, dimethylformamide and the like.
  • Amide solvents alcohol solvents such as methanol, ester solvents such as ethyl acetate, ketone solvents such as acetone, and the like.
  • solution polymerization for polymerization in a homogeneous system and precipitation polymerization for precipitation of the produced polymer can also be carried out.
  • 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 monomer concentration is 0.1 to 90% by weight, more preferably 1 to 50% by weight.
  • the 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, it is preferably 1 hour or longer, more preferably 2 to 500 hours.
  • the polymer product can be obtained by a known method, for example, by adding a reaction solution to a lower alcohol such as methanol and filtering and drying the resulting precipitate.
  • a reaction solution such as methanol
  • a lower alcohol such as methanol
  • filtering and drying the resulting 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. By purifying in this way, impurities such as unreacted monomers and polymerization catalyst are removed, so that the durability and life of the organic device, particularly the organic EL element, are improved.
  • the polymer of the present invention obtained as described above and the polymerizable monomer of the present invention are suitable for the following organic device materials, hole injection transport materials, and organic electroluminescence element materials.
  • Organic devices, especially organic EL elements, that can be used in applications have excellent element characteristics such as lifetime and light emission efficiency, and are suitable for practical use with little deterioration even after practical high-temperature driving for displays and lighting applications.
  • An organic EL element can be provided.
  • the hole injecting and transporting layer can be uniformly formed by a coating method, it is suitable for reducing the cost or increasing the screen size for displays and lighting applications.
  • examples of organic devices include organic TFTs, photoelectric conversion elements such as organic TFTs and organic solar cells, image sensors, and the like.
  • organic EL elements are flat light emitters such as flat panel displays for wall-mounted televisions, general or special lighting, copying machines, printers, light sources such as backlights for liquid crystal displays or instruments, display boards, indicator lights, etc. it can.
  • the polymer of the present invention can also be used as a material for an electrophotographic photoreceptor.
  • an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between a cathode and an anode, and at least one of the organic thin film layers contains the polymer of the present invention.
  • the organic thin film layer includes one or both of a hole transport layer and a hole injection layer, and the polymer of the present invention is either the hole transport layer or the hole injection layer. Or it is preferable to contain in both.
  • the light emitting layer preferably contains one or both of a styrylamine compound and an arylamine compound.
  • the organic EL element of the present invention may be a fluorescent light emitting type or a phosphorescent light emitting type. Although there is no restriction
  • An organic EL element that emits blue light generally has a short element life. However, when the polymer of the present invention is used for an organic thin film layer, the life is hardly lowered even when it is practically driven with high brightness and high temperature.
  • the organic EL element of the present invention is produced by laminating a plurality of layers having the above various layer structures on a light-transmitting substrate.
  • the translucent substrate referred to here is a substrate that supports the organic EL element, and is not limited as long as it has mechanical and thermal strength and transparency, but a visible region of 400 to 700 nm.
  • a smooth substrate with a light transmittance of 50% or more is preferred.
  • a glass plate, a polymer plate, a transparent resin film, etc. are mentioned. Examples of the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • polymer plate examples include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfone, and polysulfone.
  • Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone.
  • a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
  • ⁇ Cathode> As the conductive material used for the cathode, those having a work function smaller than 4 eV are suitable, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.
  • This cathode can be produced by forming a thin film of the above-described conductive material by a method such as vapor deposition or sputtering.
  • a method such as vapor deposition or sputtering.
  • the transmittance with respect to the light emitted from the cathode is larger than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, and oxide. Germanium, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like may be used, and a mixture or laminate of these may be used.
  • the organic EL device of the present invention may have a light emitting layer containing a fluorescent light emitting material, that is, a fluorescent light emitting layer.
  • a fluorescent light emitting layer known fluorescent light emitting materials can be used.
  • the fluorescent material is preferably at least one selected from anthracene derivatives, fluoranthene derivatives, styrylamine derivatives and arylamine derivatives, and more preferably anthracene derivatives and arylamine derivatives.
  • an anthracene derivative is preferable as the host material
  • an arylamine derivative is preferable as the dopant.
  • suitable materials described in International Publication Nos. 2010/134350 and 2010/134352 are selected.
  • the organic EL device of the present invention may have a light emitting layer containing a phosphorescent material, that is, a phosphorescent layer.
  • a material for the phosphorescent light emitting layer a known phosphorescent light emitting material can be used. Specifically, International Publication No. 2005/079118 may be referred to.
  • the phosphorescent materials preferred examples include iridium (Ir), osmium (Os), or platinum (Pt) metal orthometalated complexes, and iridium (Ir) orthometalated complexes are more preferred.
  • the host material is preferably a compound containing a carbazolyl group, more preferably a compound containing a carbazolyl group and a triazine skeleton, and a compound having a carbazolyl group and a pyrimidine skeleton, and two carbazolyl groups and a triazine skeleton. And a compound having two carbazolyl groups and one pyrimidine skeleton are more preferable.
  • the light emitting layer of the organic EL element has the following functions (1) to (3).
  • Injection function a function capable of injecting holes from an anode or a hole injection layer when an electric field is applied, and a function capable of injecting electrons from a cathode or an electron injection layer
  • transport function injected charge (electrons)
  • Light-emitting function A function to provide a recombination field between electrons and holes and connect it to light emission.
  • the ease with which holes are injected and the injection of electrons There may be a difference in ease, and the transport ability represented by the mobility of holes and electrons may be large or small, but it is preferable to move one of the charges.
  • the polymer of the present invention can be used as necessary. Furthermore, known light emitting materials, doping materials, hole injection materials and electron injection materials can be used, and the polymer of the present invention can also be used as a doping material.
  • the organic EL element can prevent the brightness
  • the layer that injects holes from the electrode is a hole injection layer
  • the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer.
  • a layer that injects electrons from an electrode is referred to as an electron injection layer
  • a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
  • Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
  • Examples of host materials or doping materials that can be used in the light emitting layer together with the polymer of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene.
  • Condensed aromatic compounds such as fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and their derivatives ,
  • Organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinato) aluminum, triarylamine derivatives, styrylamine derivatives , Stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole derivatives, acridone derivatives, quinacridone derivatives, fluoranthen
  • 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 5.6 eV or less.
  • a hole injecting / transporting layer a material that transports holes to the light emitting layer with lower electric field strength is preferable.
  • the mobility of holes is, for example, when an electric field of 10 4 to 10 6 V / cm is applied.
  • the polymer of the present invention is particularly preferably used as a hole injection / transport layer.
  • the hole transport material of the present invention alone may form a hole injection / transport layer, or may be used in combination with other materials.
  • Other materials for forming the hole injection / transport layer by mixing with the polymer of the present invention are not particularly limited as long as they have the above-mentioned preferable properties. Any material commonly used as a material and known materials used for a hole injection / transport layer of an organic EL element can be selected and used.
  • a material that has a hole transporting ability and can be used in the hole transporting zone is referred to as a hole transporting material.
  • phthalocyanine derivatives examples include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazoles, oxadiazoles, triazoles, imidazoles, imidazolones, imidazolethiones, pyrazolines.
  • more effective hole injection materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
  • aromatic tertiary amine derivative include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4 '-Diamine, N, N, N', N '-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N', N '-(4-methylphenyl) ) -1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-( Methylpheny
  • phthalocyanine (Pc) derivative examples include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc—O—GaPc.
  • the organic EL device of the present invention includes a layer containing these aromatic tertiary amine derivatives and / or phthalocyanine derivatives, for example, the hole transport layer or the hole injection layer, between the light emitting layer and the anode. Preferably formed.
  • the organic EL device of the present invention as a material for forming the hole injection layer other than the polymer of the present invention, in addition to the above-mentioned compounds, for example, carbazole derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, Starburst amines, styrylamine compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, organic silane derivatives, and polymers containing one or more selected from these, vanadium oxide, tantalum oxide, tungsten oxide, molybdenum oxide , Conductive metal oxides such as ruthenium oxide and aluminum oxide; conductive polymers and oligomers such as polyaniline, aniline copolymers, thiophene oligomers and polythiophenes; poly (3,4-ethylenedioxythiophene), polystyrenesulfonic acid , Polypyro Organic conductive materials such as ruthenium and polymers containing
  • the material may be a single component or a composition comprising a plurality of components.
  • the hole injection layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • examples of the method for forming the hole injection layer include a vacuum deposition method, a sputtering method, and an ion plating method.
  • examples of the method for producing the hole injection layer include a vacuum deposition method, a transfer method, and a film formation method from a solution.
  • a method for producing the hole injection layer when the material for the hole injection layer is a polymer organic material a method by film formation from a solution is exemplified.
  • 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.
  • an electrode in this case, a cathode
  • the electron transport layer is appropriately selected with a film thickness of several nm to several ⁇ m. However, particularly when the film thickness is thick, in order to avoid a voltage increase, 10 4 to 10 6 V / It is preferable that the electron mobility is at least 10 ⁇ 5 cm 2 / Vs or more when an electric field of cm is applied.
  • materials used for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthra. Examples thereof include, but are not limited to, quinodimethane, anthrone, and the like. Further, it can be sensitized by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.
  • more effective electron injection materials are metal complex compounds and nitrogen-containing five-membered ring derivatives.
  • the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, and tris.
  • nitrogen-containing five-membered derivative for example, oxazole, thiazole, oxadiazole, thiadiazole, and triazole derivatives are preferable.
  • the organic EL device of the present invention in the light emitting layer, in addition to the polymer of the present invention, at least one of a light emitting material, a doping material, a hole injection material and an electron injection material may be contained in the same layer. .
  • a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.
  • the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device.
  • the substrate is also preferably transparent.
  • the transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering.
  • the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
  • each layer of the organic EL device of the present invention a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied.
  • a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied.
  • the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • Examples of a method for forming a layer containing the polymer of the present invention include a method of forming a polymer solution.
  • Film formation methods include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, slit coating, wire bar coating, dip coating, spray coating, and screen printing. , Flexographic printing method, offset printing method, ink jet method, nozzle printing method, and the like. In the case of pattern formation, screen printing method, flexographic printing method, offset printing method, and ink jet printing method are preferable. Film formation by these methods can be performed under conditions well known to those skilled in the art, and details thereof are omitted.
  • the solvent may be removed by vacuum and heating (at most 200 ° C.) to remove the solvent, and a polymerization reaction by heating with light and high temperature (200 ° C. or more) is unnecessary. Therefore, performance degradation due to light and high temperature heating is suppressed.
  • the film-forming solution only needs to contain at least one polymer of the present invention.
  • other hole transport materials, electron transport materials, light-emitting materials, acceptor materials, solvents, stabilizers, and the like may be included.
  • the content of the polymer 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.
  • Film-forming solutions are additives for adjusting viscosity and / or surface tension, such as thickeners (high molecular weight compounds, poor solvents for polymers of the present invention, etc.), viscosity reducing agents (low molecular weight compounds, etc.) Further, it may contain a surfactant or the like. Moreover, in order to improve storage stability, you may contain antioxidants which do not influence the performance of organic EL elements, such as a phenolic antioxidant and phosphorus antioxidant.
  • High molecular weight compounds that can be used include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and copolymers thereof, poly-N-vinyl.
  • insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and copolymers thereof, poly-N-vinyl.
  • photoconductive resins such as carbazole and polysilane
  • conductive resins such as polythiophene and polypyrrole.
  • Examples of the solvent for the film-forming solution include chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, ethers such as tetrahydrofuran, dioxane, dioxolane and anisole. Solvents; aromatic hydrocarbon solvents such as toluene and xylene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.
  • chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene
  • ethers such as tetrahydrofur
  • Aliphatic hydrocarbon solvents such as acetone, methyl ethyl ketone, cyclohexanone, benzophenone, and acetophenone; Ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; ethylene glycol , Ethylene glycol monobuty Polyhydric alcohols such as ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol and derivatives thereof; methanol, Examples include alcohol solvents such as ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvent
  • organic solvents can be used alone or in combination.
  • aromatic hydrocarbon solvents ethylbenzene, diethylbenzene, trimethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzene, isobutylbenzene, 5-butylbenzene, n-hexylbenzene, cyclohexylbenzene, 1-methylnaphthalene, tetralin, 1, 3-dioxane, 1,4-dioxane, 1,3-dioxolane, anisole, ethoxybenzene, cyclohexane, bicyclohexyl, cyclohexenylcyclohexanan
  • An organic EL device is formed by forming an anode, a light emitting layer, a hole injecting / transporting layer if necessary, an electron injecting / transporting layer if necessary, and further forming a cathode by various materials and layer forming methods exemplified above. Can be produced. Moreover, an organic EL element can also be produced from the cathode to the anode in the reverse order.
  • Synthesis Example 2 A polymerizable monomer H-2 was synthesized according to the following synthesis scheme.
  • Synthesis Example 3 A polymerizable monomer H-3 was synthesized according to the following synthesis scheme.
  • the concentrated residue was purified by silica gel column chromatography.
  • the obtained crude product was recrystallized with toluene, collected by filtration, and dried to obtain 1.7 g (yield 54%) of a white solid.
  • the product was identified as polymerizable monomer H-3 by FD-MS analysis.
  • Synthesis Example 4 A polymerizable monomer H-4 was synthesized according to the following synthesis scheme.
  • Synthesis Example 5 A polymerizable monomer H-5 was synthesized according to the following synthesis scheme.
  • Example 1 (Production and evaluation of organic EL element) A glass substrate with an ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm (manufactured by Geomatic Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. On the glass substrate with a transparent electrode after cleaning, a film of polyethylene dioxythiophene / polystyrene sulfonic acid (PEDOT: PSS) used for the hole injection layer by spin coating is formed to a thickness of 10 nm, and the hole injection layer is formed. (PSS is an acceptor).
  • PEDOT polyethylene dioxythiophene / polystyrene sulfonic acid
  • a xylene solution (1.0 wt%) of the following monomer H-1 obtained in Synthesis Example 1 was formed into a film having a thickness of 40 nm by a spin coat method.
  • the hole transport layer was formed by drying and heat curing at 30 ° C. for 30 minutes.
  • a xylene solution (1.0 wt%) in which the following compound EM1 (host) and the following amine compound D1 (dopant) having a styryl group are mixed at a solid content weight ratio of 95: 5 is spin-coated to 40 nm.
  • a light emitting layer was formed by drying at 150 ° C. for 30 minutes.
  • Alq was deposited on this film to a thickness of 10 nm by vapor deposition.
  • This layer functions as an electron injection layer.
  • Li Li source: manufactured by Saesgetter Co.
  • Alq Alq
  • Alq Alq
  • Metal Al was vapor-deposited on the Alq: Li film to form a metal cathode, which was sealed with glass in nitrogen to produce an organic EL device.
  • Example 1 was carried out except that the following monomers H-2 to H-5 synthesized in Synthesis Examples 2 to 5 shown in Table 1 were used instead of the monomer H-1 as the hole transport material in Example 1.
  • An organic EL device was produced and evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • Example 1 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the following comparative compounds 1 and 2 were used instead of the monomer H-1. The results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Emergency Medicine (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Ledit monomère polymérisable est représenté par la formule (1).
PCT/JP2014/001018 2013-03-01 2014-02-26 Monomère polymérisable, matériau pour dispositif organique comprenant ledit polymère, matériau d'injection/de transport de trou, matériau pour élément électroluminescent organique et élément électroluminescent organique WO2014132636A1 (fr)

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WO2016194714A1 (fr) * 2015-05-29 2016-12-08 出光興産株式会社 Composé à poids moléculaire élevé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
EP3138858A1 (fr) * 2015-09-01 2017-03-08 Samsung Electronics Co., Ltd. Polymère amino-fluorène et dispositif électroluminescent organique l'incluant
JP2017048290A (ja) * 2015-09-01 2017-03-09 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． アミノフルオレンポリマー、有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子
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WO2018000175A1 (fr) * 2016-06-28 2018-01-04 Dow Global Technologies Llc Procédé de fabrication d'un film organique de transport de charge
JP2019518847A (ja) * 2016-06-28 2019-07-04 ダウ グローバル テクノロジーズ エルエルシー 有機電荷輸送膜を作製するためのプロセス
US11053229B2 (en) 2017-03-08 2021-07-06 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
KR20190090213A (ko) * 2018-01-24 2019-08-01 주식회사 엘지화학 중합체, 이를 포함하는 코팅 조성물 및 이를 이용한 유기 발광 소자
WO2019146978A1 (fr) * 2018-01-24 2019-08-01 주식회사 엘지화학 Polymère, composition de revêtement le comprenant, et dispositif électroluminescent organique l'utilisant
CN111225930A (zh) * 2018-01-24 2020-06-02 株式会社Lg化学 聚合物、包含其的涂覆组合物和使用其的有机发光器件
TWI705978B (zh) * 2018-01-24 2020-10-01 南韓商Ｌｇ化學股份有限公司 聚合物、包含其的覆蓋組成物與使用其的有機發光裝置
KR20190090211A (ko) * 2018-01-24 2019-08-01 주식회사 엘지화학 중합체, 이를 포함하는 코팅 조성물 및 이를 이용한 유기 발광 소자
KR102295248B1 (ko) 2018-01-24 2021-08-27 주식회사 엘지화학 중합체, 이를 포함하는 코팅 조성물 및 이를 이용한 유기 발광 소자
US11374175B2 (en) 2018-01-24 2022-06-28 Lg Chem, Ltd. Polymer, coating composition comprising same, and organic light-emitting device using same
KR102428980B1 (ko) 2018-01-24 2022-08-03 주식회사 엘지화학 중합체, 이를 포함하는 코팅 조성물 및 이를 이용한 유기 발광 소자
US11472901B2 (en) 2018-01-24 2022-10-18 Lg Chem, Ltd. Polymer, coating composition comprising same, and organic light-emitting device using same
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