WO2018155275A1 - Composé de triarylamine à pont d'oxygène, précurseur de celui-ci et matériau électroluminescent - Google Patents

Composé de triarylamine à pont d'oxygène, précurseur de celui-ci et matériau électroluminescent Download PDF

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WO2018155275A1
WO2018155275A1 PCT/JP2018/005028 JP2018005028W WO2018155275A1 WO 2018155275 A1 WO2018155275 A1 WO 2018155275A1 JP 2018005028 W JP2018005028 W JP 2018005028W WO 2018155275 A1 WO2018155275 A1 WO 2018155275A1
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group
ring
carbon atoms
atom
independently
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PCT/JP2018/005028
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小野洋平
松本直樹
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東ソー株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to an oxygen-bridged triarylamine compound, a precursor thereof, and a light emitting material.
  • Patent Documents 1 and 2 have both a skeleton excellent in hole transport ability such as carbazole, diarylamine, or a bridged triarylamine, and a skeleton excellent in electron transport ability such as triazine and pyrimidine. Compounds are disclosed.
  • One embodiment of the present invention provides an oxygen-bridged triarylamine compound that has favorable bipolar properties, contributes to the formation of an organic electroluminescent device with low voltage and high luminous efficiency, and a precursor and a light-emitting material thereof. For the purpose.
  • a first embodiment of the present invention is a compound represented by the formula (1):
  • Ring A, Ring B and Ring C are each independently An aryl ring having 6 to 18 carbon atoms, or A heteroaryl ring having 3 to 13 carbon atoms;
  • the aryl ring or the heteroaryl ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, a naphthyl group, a biphenylyl group, a 9-phenylcarbazolyl group, a dibenzofuranyl group.
  • the compound represented by the formula (1) has at least one substituent Z;
  • L is independently A divalent group selected from the group consisting of a phenylene group, a biphenyldiyl group, a naphthalenediyl group, a fluorenediyl group, a spirobifluorenediyl group, a dibenzothiophenediyl group, a dibenzofurandiyl group, and a 9-phenylcarbazole diyl group.
  • the divalent group is composed of a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms.
  • Hy is independently a carbon number composed of at least one atom selected from the group consisting of a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and a nitrogen atom that forms a multiple bond.
  • the nitrogen-containing heteroaromatic group includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms, It may be substituted with at least one selected from the group consisting of
  • the second aspect of the present invention is A ring, B ring and C ring are each independently one ring selected from the group consisting of benzene ring, naphthalene ring, phenanthrene ring, triphenylene ring, anthracene ring and chrysene ring,
  • the ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothionyl group,
  • the compound according to the first aspect which may be substituted with at least one selected from the group consisting of the substituent Z.
  • the third aspect of the present invention is A ring, B ring and C ring are each independently one ring selected from a benzene ring and a naphthalene ring;
  • the ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothionyl group,
  • the compound according to the first or second aspect which may be substituted with at least one selected from the group consisting of the substituent Z.
  • the fourth aspect of the present invention is The compound according to the first aspect, which is a compound represented by any one of formulas (1-1) to (1-26):
  • R is each independently a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, a naphthyl group, a biphenylyl group, a 9-phenylcarbazolyl group, a dibenzofuran group. Represents a nyl group or a dibenzothionyl group; Z is synonymous with the formula (2).
  • the fifth aspect of the present invention is L is independently Single bond or The compound according to any one of the first to fourth aspects, which is a group represented by any one of formulas (L-1) to (L-11):
  • each R 1 independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or 6 to 6 carbon atoms. Represents a 25 aryl group or a heteroaryl group having 3 to 20 carbon atoms.
  • the sixth aspect of the present invention is Hy is each independently a pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, carbolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, benzoquinazolinyl group , A benzothienopyrimidinyl group, and a benzofuroprimidinyl group, one group selected from the group consisting of The group is selected from the group consisting of a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms.
  • the compound according to any one of the first to fifth aspects which may be substituted with at least one selected from the above.
  • the seventh aspect of the present invention is The compound according to any one of the first to sixth aspects, wherein Hy is each independently a group represented by any one of formulas (Hy-1) to (Hy-9) Is:
  • each R 2 independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or 6 to 6 carbon atoms. Represents a 25 aryl group or a heteroaryl group having 3 to 20 carbon atoms.
  • the eighth aspect of the present invention is A luminescent material comprising the compound according to any one of the first to seventh aspects.
  • the ninth aspect of the present invention is A chlorine compound represented by the formula (1-a):
  • Ring A, Ring B and Ring C are each independently An aryl ring having 6 to 18 carbon atoms, or A heteroaryl ring having 3 to 13 carbon atoms;
  • the aryl ring or the heteroaryl ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, a naphthyl group, a biphenylyl group, a 9-phenylcarbazolyl group, a dibenzofuranyl group.
  • the compound represented by the formula (1-a) has at least one chlorine atom.
  • the tenth aspect of the present invention is A ring, B ring and C ring are each independently one ring selected from the group consisting of benzene ring, naphthalene ring, phenanthrene ring, triphenylene ring, anthracene ring and chrysene ring,
  • the ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothionyl group,
  • the chlorine compound according to the ninth aspect which may be substituted with at least one selected from the group consisting of chlorine atoms.
  • the eleventh aspect of the present invention is A ring, B ring and C ring are each independently one ring selected from a benzene ring and a naphthalene ring;
  • the ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothionyl group,
  • the chlorine compound according to the ninth or tenth aspect which may be substituted with at least one selected from the group consisting of chlorine atoms.
  • the twelfth aspect of the present invention is The chlorine compound according to the ninth aspect, which is a chlorine compound represented by any one of formulas (1-a1) to (1-a23):
  • each R independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, or a naphthyl group.
  • an oxygen-bridged triarylamine compound that has favorable bipolar properties, contributes to the formation of an organic electroluminescence device having low voltage and high luminous efficiency, a precursor thereof, and a light emitting material are provided. can do.
  • oxygen-bridged triarylamine compound according to one embodiment of the present invention, a precursor thereof (hereinafter also referred to as a chlorine compound), and a light-emitting material will be described in detail.
  • the oxygen-bridged triarylamine compound is a compound represented by the formula (1):
  • Ring A, Ring B and Ring C are each independently An aryl ring having 6 to 18 carbon atoms, or A heteroaryl ring having 3 to 13 carbon atoms;
  • the aryl ring or the heteroaryl ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, a naphthyl group, a biphenylyl group, a 9-phenylcarbazolyl group, a dibenzofuranyl group.
  • the compound represented by the formula (1) has at least one substituent Z;
  • L is independently A divalent group selected from the group consisting of a phenylene group, a biphenyldiyl group, a naphthalenediyl group, a fluorenediyl group, a spirobifluorenediyl group, a dibenzothiophenediyl group, a dibenzofurandiyl group, and a 9-phenylcarbazole diyl group.
  • the divalent group is composed of a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms.
  • Hy is independently a carbon number composed of at least one atom selected from the group consisting of a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and a nitrogen atom that forms a multiple bond.
  • the nitrogen-containing heteroaromatic group includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms, It may be substituted with at least one selected from the group consisting of
  • the A ring, the B ring and the C ring are each independently an aryl ring having 6 to 18 carbon atoms or a heteroaryl ring having 3 to 13 carbon atoms. These aryl rings or heteroaryl rings may be substituted with at least one substituent X1.
  • at least one substituent X1 is a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzo It is at least one selected from the group consisting of a furanyl group, a dibenzothionyl group, and a substituent Z represented by the formula (2).
  • the aryl ring having 6 to 18 carbon atoms can be expressed as a monocyclic or condensed aryl ring having 6 to 18 carbon atoms, or a monocyclic or condensed aromatic ring having 6 to 18 carbon atoms.
  • the aryl ring having 6 to 18 carbon atoms is not particularly limited, and examples thereof include a benzene ring, naphthalene ring, phenanthrene ring, triphenylene ring, anthracene ring, and chrysene ring.
  • the heteroaryl ring having 3 to 13 carbon atoms can be written as a monocyclic or condensed heteroaryl ring having 3 to 13 carbon atoms, or a monocyclic or condensed heteroaromatic ring having 3 to 13 carbon atoms. .
  • the heteroaryl ring having 3 to 13 carbon atoms is not particularly limited, and examples thereof include a pyrrole ring, an imidazole ring, a triazine ring, a pyrazine ring, a pyrimidine ring, a pyridine ring, a quinoline ring, an isoquinoline ring, a phenazine ring, Examples include an acridine ring, furan ring, thiophene ring, pyrrole ring, thiazole ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, and dibenzothiophene ring.
  • the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms in the substituent X1 is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, and an n-butyl group. , Sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group and the like.
  • the A ring, B ring and C ring are preferably independently an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 3 to 10 carbon atoms from the viewpoint of excellent bipolar properties.
  • the aryl ring having 6 to 10 carbon atoms or the heteroaryl ring having 3 to 10 carbon atoms may be substituted with at least one substituent X1.
  • the aryl ring having 6 to 10 carbon atoms is also referred to as a monocyclic or condensed aryl ring having 6 to 10 carbon atoms or a monocyclic or condensed aromatic hydrocarbon ring having 6 to 10 carbon atoms.
  • the heteroaryl ring having 3 to 10 carbon atoms is also referred to as a monocyclic or condensed heteroaryl ring having 3 to 10 carbon atoms, or a monocyclic or condensed heteroaromatic ring having 3 to 10 carbon atoms.
  • a ring, B ring and C ring are each independently a benzene ring, naphthalene ring, phenanthrene ring, triphenylene ring, anthracene ring, chrysene ring, pyridine ring, pyrrole ring, thiophene ring, quinoline ring, and isoquinoline ring. It is preferably one ring selected from the group consisting of The ring may be substituted with at least one substituent X1.
  • the A ring, the B ring, and the C ring are each independently one ring selected from the group consisting of a benzene ring, a naphthalene ring, a phenanthrene ring, a triphenylene ring, an anthracene ring, and a chrysene ring.
  • the ring may be substituted with at least one substituent X1.
  • the A ring, the B ring, and the C ring are each independently one ring selected from the group consisting of a benzene ring and a naphthalene ring.
  • the ring may be substituted with at least one substituent X1.
  • the compound represented by the formula (1) has at least one substituent Z.
  • the substituent Z is preferably substituted with one, two, or three hydrogen atoms in the formula (1), and more preferably substituted with one or two hydrogen atoms. Preferably, it is more preferably substituted with one hydrogen atom.
  • the oxygen-bridged triarylamine compound represented by the formula (1) is not particularly limited.
  • the compound represented by any one of the formulas (1-1) to (1-26) Can be mentioned.
  • each R independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, or a naphthyl group. , Biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, and dibenzothionyl group.
  • Z is synonymous with the formula (2).
  • the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms in the formulas (1-1) to (1-26) is a linear, branched or cyclic group having 1 to 18 carbon atoms in the substituent X1. It is synonymous with a cyclic alkyl group.
  • R is preferably a hydrogen atom, a deuterium atom, a phenyl group, a biphenyl group, or a naphthyl group independently from the viewpoint of not impairing the bipolar property of the compound.
  • each L independently represents a phenylene group, a biphenyldiyl group, a naphthalenediyl group, a fluorenediyl group, a spirobifluorenediyl group, a dibenzothiophenediyl group, a dibenzofuran.
  • a divalent group selected from the group consisting of a diyl group and a 9-phenylcarbazolediyl group; or a single bond.
  • the divalent group may be substituted with at least one substituent X2.
  • at least one substituent X2 is a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heterogeneous group having 3 to 20 carbon atoms. It is at least one selected from the group consisting of an aryl group.
  • the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms in the substituent X2 has the same meaning as the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms in the substituent X1.
  • the aryl group having 6 to 25 carbon atoms in the substituent X2 is not particularly limited, and examples thereof include a phenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, and a 1-naphthyl group.
  • the heteroaryl group having 3 to 20 carbon atoms in the substituent X2 is not particularly limited, and examples thereof include a benzothienyl group, a benzofuranyl group, a benzimidazolyl group, an indazolyl group, a benzothiazolyl group, and a benzoisothiazolyl group.
  • L is a divalent group independently selected from the group consisting of a phenylene group, a biphenyldiyl group, a naphthalenediyl group, a dibenzothiophenediyl group, and a dibenzofurandiyl group, in that L is excellent in the bipolar property of the compound; Or it is preferable that they are a single bond;
  • the divalent group may be substituted with at least one substituent X2.
  • each L is independently a single bond or a group represented by any one of formulas (L-1) to (L-11).
  • each R 1 independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or 6 to 6 carbon atoms. Represents a 25 aryl group or a C 3-20 heteroaryl group.
  • a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms are These are synonymous with the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, the aryl group having 6 to 25 carbon atoms, and the heteroaryl group having 3 to 20 carbon atoms, respectively, in the substituent X2.
  • L is a divalent group selected from the group consisting of a phenylene group, a biphenyldiyl group, a naphthalenediyl group, a dibenzothiophenediyl group, and a dibenzofurandiyl group, each of which is excellent in the bipolar property of the compound. Group; or preferably a single bond.
  • the divalent group is a deuterium atom, methyl group, ethyl group, phenyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, 1-naphthyl group, 2-naphthyl group, carbazolyl group, dibenzothienyl. It may be substituted with at least one selected from the group consisting of a group and a dibenzofuranyl group.
  • L is more preferably a single bond; or a group represented by any one of formulas (L-1) to (L-11), each having an excellent bipolar property. preferable.
  • each R 1 independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a phenyl group, a 2-biphenyl group, a 3-biphenyl group, 4 -Represents a biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a carbazolyl group, a dibenzothienyl group, or a dibenzofuranyl group.
  • Hy each independently represents at least one atom selected from the group consisting of a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and It represents a nitrogen-containing heteroaromatic group having 3 to 12 carbon atoms, which is composed of nitrogen atoms forming multiple bonds.
  • the nitrogen-containing heteroaromatic group may be substituted with at least one substituent X2.
  • the nitrogen-containing heteroaromatic group having 3 to 12 carbon atoms is not particularly limited, and examples thereof include pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, carbolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group.
  • Hy is independently a pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, carbolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, benzoquinazolinyl group It is preferably one group selected from the group consisting of benzothienopyrimidinyl group and benzofuroprimidinyl group. The group may be substituted with the substituent X2.
  • each Hy is independently a group represented by any one of formulas (Hy-1) to (Hy-9).
  • each R 2 independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or 6 to 25 carbon atoms. And any one selected from a heteroaryl group having 3 to 20 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 25 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms are These are synonymous with the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, the aryl group having 6 to 25 carbon atoms, and the heteroaryl group having 3 to 20 carbon atoms, respectively, in the substituent X2.
  • R 2 is preferably any one selected from the group consisting of a hydrogen atom, a deuterium atom, a phenyl group, a biphenyl group, and a naphthyl group.
  • Hy is each independently a pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, carbolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, benzoquinazolinyl group.
  • a group selected from a nyl group, a benzothienopyrimidinyl group, and a benzofuroprimidinyl group is preferable.
  • the group is a deuterium atom, methyl group, ethyl group, phenyl group, biphenyl group, naphthyl group, terphenyl group, triphenylenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, It may be substituted with at least one selected from the group consisting of 9,9′-spirobifluorenyl group, phenanthryl group, carbazolyl group, dibenzothienyl group, and dibenzofuranyl group.
  • R 2 in the formulas (Hy-1) to (Hy-9) each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, or a triphenylenyl group.
  • Hy is each independently a pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, carbolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, benzoquinazolinyl group. It is preferably one group selected from the group consisting of a nyl group, a benzothienopyrimidinyl group, and a benzofuroprimidinyl group.
  • the group includes deuterium atom, methyl group, ethyl group, phenyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, 1-naphthyl group, 2-naphthyl group, m-terphenyl-5′-.
  • each R 2 is independently a hydrogen atom, deuterium atom, methyl group, ethyl group, phenyl group, 2-biphenyl group, 3-biphenyl group, 4 -Biphenyl group, 1-naphthyl group, 2-naphthyl group, m-terphenyl-5'-yl group, triphenylene-1-yl group, triphenylene-2-yl group, 9,9-dimethylfluoren-1-yl group 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, 9,9-diphenylfluoren-1-yl group, 9 , 9-diphenylfluoren-2-yl group, 9,9-diphenylfluoren-3-yl group, 9,9-diphenylfluoren-4-yl group, 9,9-diphenylfluoren-1-yl group
  • Preferred compounds are exemplified below, but the oxygen-bridged triarylamine compound is not limited to these compounds.
  • the oxygen-bridged triarylamine compound represented by the formula (1) can be synthesized, for example, by the following route.
  • Ak each independently represents a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms. Ak is preferably a methyl group or an ethyl group in terms of easy availability of raw materials.
  • Step (1) Aryl halide having ortho groups on both sides substituted with fluorine is subjected to a coupling reaction of an aryl halide having an alkoxy group at the ortho position such as 2-iodoanisole using a palladium catalyst or a copper catalyst, A secondary amine is obtained.
  • Step (2) The secondary amine obtained in step (1) is further reacted with an aryl halide having an alkoxy group at the ortho position to obtain a tertiary amine.
  • Step (3) After cleaving the alkyl of the alkoxy group by a conventional method, an oxygen-bridged triarylamine compound having a coupling reactive group such as a chloro group is obtained by a nucleophilic substitution reaction.
  • Step (4) From the Suzuki coupling reaction of the oxygen-bridged triarylamine compound having a coupling reactive group and the boronic acid compound or boronic ester compound of the substituent Z, the oxygen represented by the formula (1) A crosslinked triarylamine compound can be obtained.
  • the oxygen-bridged triarylamine compound is used as a boronic acid compound or a boronic acid ester compound, , And may be reacted with a halide of substituent Z.
  • Negishi coupling reaction or Kumada / Tamao coupling reaction can be used instead of Suzuki coupling reaction.
  • an oxygen-bridged triarylamine compound can be synthesized by appropriately changing the substituent of each ring.
  • an oxygen-bridged triarylamine compound can be synthesized using the B ring and C ring alkoxy groups as the A ring and the fluorinated aryl as the B ring and C ring.
  • the substituent Z is defined by the formula (2), but the boronic acid compound or boronic ester compound of the substituent Z can be synthesized based on a known method.
  • Ring A, Ring B and Ring C are each independently An aryl ring having 6 to 18 carbon atoms, or A heteroaryl ring having 3 to 13 carbon atoms;
  • the aryl ring or the heteroaryl ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, a naphthyl group, a biphenylyl group, a 9-phenylcarbazolyl group, a dibenzofuranyl group.
  • the compound represented by the formula (1-a) has at least one chlorine atom.
  • an aryl ring having 6 to 18 carbon atoms, a heteroaryl ring having 3 to 13 carbon atoms, and a linear, branched or cyclic group having 1 to 18 carbon atoms The definition of the alkyl group is as follows.
  • the aryl ring having 6 to 18 carbon atoms, the heteroaryl ring having 3 to 13 carbon atoms, and the 1 to 18 carbon atoms in the A ring, the B ring, and the C ring in the formula (1) are the same as the definition of the linear, branched or cyclic alkyl group, and the preferred range is also the same.
  • a ring, B ring and C ring are each independently selected from the group consisting of benzene ring, naphthalene ring, phenanthrene ring, triphenylene ring, anthracene ring and chrysene ring.
  • One ring is preferred.
  • the ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothionyl group, And may be substituted with at least one selected from the group consisting of chlorine atoms.
  • the A ring, B ring and C ring in the general formula (1-a) are each independently one ring selected from a benzene ring and a naphthalene ring.
  • the ring includes a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, phenyl group, naphthyl group, biphenylyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothionyl group, And may be substituted with at least one selected from the group consisting of chlorine atoms.
  • the chlorine compound represented by the formula (1-a) has at least one chlorine atom.
  • the chlorine compound represented by the formula (1-a) is preferably a chlorine compound represented by any one of the formulas (1-a1) to (1-a23).
  • each R independently represents a hydrogen atom, a deuterium atom, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a phenyl group, or a naphthyl group.
  • the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms in R in the formulas (1-a1) to (1-a23) is a linear, branched or cyclic group having 1 to 18 carbon atoms in the formula (1). The same applies to the preferred range.
  • each R is independently a hydrogen atom, a deuterium atom, a phenyl group, or biphenyl from the viewpoint that the bipolar property of the compound is not impaired. Or a naphthyl group.
  • a light-emitting material according to one embodiment of the present invention includes the above-described compound (oxygen-bridged triarylamine compound).
  • the oxygen-bridged triarylamine compound represented by the formula (1) can be used in each layer of an organic electroluminescence element (organic EL element), but can be preferably used as a light-emitting host material or a light-emitting dopant material. .
  • the oxygen-bridged triarylamine compound represented by the formula (1) has bipolar properties, can transport holes and electrons stably, and has excellent light emission characteristics. When used as a material for the light emitting layer, it is possible to achieve high efficiency and long life of the organic EL element.
  • the oxygen-bridged triarylamine compound represented by the formula (1) When used as a material for the light emitting layer of the organic EL device, the oxygen-bridged triarylamine compound may be used alone, The light emitting host material may be doped and used, or a known light emitting dopant may be doped.
  • a known method such as a vacuum deposition method, a spin coating method, or a casting method can be applied. .
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are preferable. May be omitted or may be added conversely.
  • the anode and cathode of the organic EL element are connected to a power source through an electrical conductor.
  • the organic EL element operates by applying a potential between the anode and the cathode.
  • the organic EL element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate.
  • the electrode in contact with the substrate is called the lower electrode for convenience.
  • the lower electrode is an anode, but the organic EL element according to one embodiment of the present disclosure is not limited to such a form.
  • the substrate may be light transmissive or opaque depending on the intended emission direction.
  • the light transmission characteristics can be confirmed by electroluminescence emission through the substrate.
  • transparent glass or plastic is used as the substrate in such a case.
  • the substrate may be a composite structure including multiple material layers. When the electroluminescent emission is confirmed through the anode, the anode is formed by passing or substantially passing through the emission.
  • the transparent material used for the anode is not particularly limited.
  • ITO indium-tin oxide
  • IZO indium-zinc oxide
  • tin oxide aluminum -Metal oxides such as doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide
  • metal nitrides such as gallium nitride
  • metal selenides such as zinc selenide
  • metal sulfides such as zinc sulfide
  • the anode can be modified with plasma deposited fluorocarbon.
  • the transmission characteristic of the anode is not important, and any transparent, opaque or reflective conductive material can be used as the anode material.
  • materials used for the anode in this case include gold, iridium, molybdenum, palladium, platinum, and the like.
  • a plurality of hole transporting layers such as a hole injection layer and a hole transport layer can be provided between the anode and the light emitting layer.
  • the hole injection layer and the hole transport layer have a function of transmitting holes injected from the anode to the light emitting layer.
  • the hole injection layer and the hole transport layer are often used in a lower electric field. Holes can be injected into the light emitting layer.
  • hole injection materials and hole transport materials can be used as the hole transport layer and / or hole injection layer.
  • hole injection materials and hole transport materials include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives.
  • the hole injecting material and the hole transporting material those described above can be used, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound, or a styrylamine compound, and an aromatic tertiary amine compound. It is particularly preferable to use
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′.
  • Inorganic compounds such as p-type-Si and p-type-SiC can also be used as a hole injection material and a hole transport material.
  • the hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the above materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.
  • the light emitting layer contains the above-described oxygen-bridged triarylamine compound.
  • a known light-emitting material (light-emitting host material, fluorescent dopant, phosphorescent dopant) can be selected and combined with the oxygen-bridged triarylamine compound.
  • Examples of the luminescent host material include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthranyl group.
  • DPVBi 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl
  • BCzVBi 4,4′-bis (9-ethyl-3-carbazovinylene) 1,1′-biphenyl
  • TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene
  • ADN (9,10-di (2-naphthyl) anthracene
  • CBP 4,4′-bis (carbazole-9) -Yl) biphenyl
  • CDBP 4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl
  • fluorescent dopants examples include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium or thiapyrylium compound, fluorene derivative, perifuranthene derivative, indenoperylene derivative, Examples thereof include bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
  • phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.
  • dopants examples include Ir (PPy) 3 (tris (2-phenylpyridine) iridium (III), FirPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium ( III), Ir (piq) 2 (acac) bis (1-phenylisoquinoline) (acetylacetonato) iridium (III), Ir (piq) 3tris (1-phenylisoquinoline) iridium (III) and the like.
  • a single layer or a plurality of electron transport layers are provided between the cathode and the light emitting layer.
  • the electron transporting material contained in the electron transporting layer include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes.
  • the alkali metal complex, alkaline earth metal complex, and earth metal complex include 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinato) copper.
  • a hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance.
  • Desirable compounds as a material for the hole blocking layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2-methyl-8-quinolinolato) -4- (phenylphenolato) aluminum), bis (10-hydroxybenzo [h] quinolinato) beryllium) and the like.
  • an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, light emission efficiency, constant voltage driving, high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. Is mentioned.
  • the above metal complexes alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO 2 , AlO, SiN, SiON, AlON, GeO, Various oxides such as LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C, and inorganic compounds such as nitrides and oxynitrides can also be used.
  • the cathode can be formed from any conductive material if light emission is only confirmed through the anode.
  • Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • Another object of one embodiment of the present disclosure is to provide an organic electroluminescence device having a low voltage, high luminous efficiency, and long life using the above-described specific oxygen-bridged triarylamine compound.
  • An organic EL device having at least one light emitting layer containing an oxygen-bridged triarylamine compound facilitates both electron injection and hole injection into the light emitting layer, and recombines electrons and holes in the light emitting layer. Efficiency is improved. Therefore, according to one embodiment of the present disclosure, it is possible to provide an organic EL element that has high luminance and high efficiency and excellent lifetime.
  • the chlorine compound has an effect that the reaction selectivity is high and the generation of impurities is less than that of a conventionally known oxygen-bridged triarylamine halogen compound, and for organic EL devices that require extremely high purity. Industrially important as a material production intermediate.
  • Example 5 (Device Evaluation of Compound (1-3-1))
  • 4,4′-bis [N- (9-phenylcarbazol-3-yl) -N-phenyl] biphenyl was vapor-deposited at a vapor deposition rate of 0.3 nm / sec on an ITO transparent electrode to form a 65 nm hole injection layer. It was.
  • the weight ratio of 9,10-di (naphthalen-2-yl) -2- [4- (1-phenyl-1H-benzimidazol-2-yl) phenyl] anthracene and lithium quinolinol is 50:50.
  • co-evaporation was performed at a deposition rate of 0.15 nm / second to obtain a 30 nm electron transport layer.
  • silver and magnesium were co-deposited at a deposition rate of 0.5 nm / second to a weight ratio of 1:10 to form a cathode.
  • a sealing glass plate was bonded with a UV curable resin to obtain an organic EL element for evaluation.
  • a current of 20 mA / cm 2 was applied to the device thus fabricated, and driving voltage, current efficiency, and luminance reduction time of 20% were measured. The results are shown in Table 1.
  • Comparative Examples 1 to 3 The same organic as in Example 5 except that the compound (1-3-1) was changed to 4,4′-bis (carbazol-9-yl) biphenyl (CBP), comparative compound (a) or comparative compound (b) An EL element was produced.
  • Table 1 shows the driving voltage, current efficiency, and luminance reduction time of 20% when a current of 20 mA / cm 2 was applied.
  • reaction solution was cooled to room temperature, inorganic salts were removed by suction filtration, and then passed through a silica gel short pass column.
  • the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane), and a white solid of 2,6-difluoro-N- (2-chloro-6-methoxyphenyl) aniline was obtained as 32.
  • Isolated 0.0 g (118.7 mmol). (Yield 79%).
  • the obtained solid was purified by silica gel column chromatography (mixed solvent of toluene and hexane), and 10.5 g of 4-chloro- [1,4] benzoxazino [2,3,4-kl] phenoxazine white solid (34 -1 mmol) was isolated.
  • Example 11 In a 200 mL three-necked flask under a nitrogen stream, 2.0 g (5.6 mmol) of 4-chloro- [1,4] benzoxazino [2,3,4-kl] phenoxazine obtained in Example 11 was used. The obtained 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2,4-diphenylquinazoline 3.0 g (7.3 mmol), palladium acetate 40 mg (0.
  • Example 14 (Device evaluation of compound (1-2-1)) The structural formulas and abbreviations of the compounds used for device evaluation are shown below.
  • a substrate having an anode on its surface a glass substrate with an ITO transparent electrode in which an indium tin oxide (ITO) film (thickness 110 nm) having a width of 2 mm was patterned in a stripe shape was prepared. Next, the substrate was cleaned with isopropyl alcohol, and then surface treatment was performed by ozone ultraviolet cleaning.
  • ITO indium tin oxide
  • each layer was vacuum-deposited by a vacuum deposition method on the substrate that had been subjected to the surface treatment after the cleaning, and each layer was laminated.
  • the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa.
  • each layer was produced according to the film-forming conditions of each layer in the following order.
  • HIL was deposited to a thickness of 55 nm on the ITO transparent electrode at a rate of 0.15 nm / second to produce a hole injection layer.
  • HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second to produce a charge generation layer.
  • HTL-1 was deposited to a thickness of 15 nm at a rate of 0.15 nm / second to produce a first hole transport layer.
  • HTL-2 was deposited to a thickness of 50 nm at a rate of 0.15 nm / second to produce a second hole transport layer.
  • bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate ((piq) 2Ir (acac)) as a light-emitting dopant material and compound (1-2-1) as a host material have a weight ratio of 5 Was co-evaporated at a deposition rate of 0.18 nm / second so as to obtain a light emitting layer of 35 nm.
  • ETL and Liq were deposited in a thickness of 30 nm at a ratio of 50:50 (mass ratio) to produce an electron transport layer. The deposition rate was 0.15 nm / second.
  • a metal mask was arranged so as to be orthogonal to the ITO stripe on the substrate, and a cathode was formed.
  • the cathode silver / magnesium (mass ratio 1/10) and silver were formed in this order at 80 nm and 20 nm, respectively, to form a two-layer structure.
  • the film formation rate of silver / magnesium was 0.5 nm / second, and the film formation rate of silver was 0.2 nm / second.
  • an organic electroluminescence device having a light emission area of 4 mm 2 was produced.
  • Each film thickness was measured with a stylus type film thickness meter (DEKTAK, manufactured by Bruker).
  • this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less. Sealing was performed using a bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation) with a glass sealing cap and a film formation substrate (element).
  • a bisphenol F type epoxy resin manufactured by Nagase ChemteX Corporation
  • Table 2 shows the drive voltage and current efficiency when a current of 10 mA / cm 2 was applied to the organic electroluminescent device produced as described above.
  • Example 15 Device Evaluation of (Compound 1-342) The same method as in Example 14, except that the compound (1-3-42) was used instead of the compound (1-2-1) in Example 14. An organic electroluminescent device was prepared and evaluated. The obtained measurement results are shown in Table 2.
  • Example 16 Device evaluation of (Compound 1-5-1) In Example 14, the same method as in Example 14 except that Compound (1-5-1) was used instead of Compound (1-2-1). An organic electroluminescent device was prepared and evaluated. The obtained measurement results are shown in Table 2.
  • Example 17 Device evaluation of (Compound 1-5-39) In Example 14, the same method as in Example 14 except that Compound (1-5-39) was used instead of Compound (1-2-1). An organic electroluminescent device was prepared and evaluated. The obtained measurement results are shown in Table 2.
  • Comparative Example 4 Device Evaluation of Comparative Compound (c) An organic electroluminescent device was prepared in the same manner as in Example 14 except that Comparative Compound (c) was used instead of Compound (1-2-1) in Example 14. Prepared and evaluated. The obtained measurement results are shown in Table 2.
  • the organic EL device containing the oxygen-bridged triarylamine compound according to one embodiment of the present invention having good bipolar properties can be expected to improve the recombination efficiency of electrons and holes in the light emitting layer. . Therefore, the oxygen-bridged triarylamine compound according to one embodiment of the present invention can provide an organic EL element with high luminance and efficiency and excellent lifetime.

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Abstract

L'invention concerne un composé de triphénylamine à pont d'oxygène qui est approprié pour un matériau électroluminescent d'un élément électroluminescent organique. Le composé de l'invention est représenté par la formule (1) [dans laquelle le cycle A, le cycle B et le cycle C représentent indépendamment chacun un cycle aryle ayant 6-18 atomes de carbone ou un cycle hétéroaryle ayant 3-13 atomes de carbone, chaque cycle ayant un substituant défini].
PCT/JP2018/005028 2017-02-21 2018-02-14 Composé de triarylamine à pont d'oxygène, précurseur de celui-ci et matériau électroluminescent WO2018155275A1 (fr)

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JP2021028309A (ja) * 2019-08-09 2021-02-25 東ソー株式会社 ベンゾオキサジノフェノキサジン化合物、有機電界発光素子用材料および有機電界発光素子用正孔輸送材料

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