WO2024117003A1 - Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique Download PDF

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WO2024117003A1
WO2024117003A1 PCT/JP2023/042041 JP2023042041W WO2024117003A1 WO 2024117003 A1 WO2024117003 A1 WO 2024117003A1 JP 2023042041 W JP2023042041 W JP 2023042041W WO 2024117003 A1 WO2024117003 A1 WO 2024117003A1
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substituted
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unsubstituted
ring
carbon atoms
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将太 田中
佑典 高橋
裕 工藤
啓太郎 山田
清香 水谷
賢悟 岸野
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出光興産株式会社
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  • the present invention relates to a novel compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device.
  • an organic electroluminescence element hereinafter also referred to as an organic EL element
  • holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer.
  • the injected holes and electrons recombine to form excitons.
  • the object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing such an organic EL element.
  • R 1 to R 4 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
  • R 1 to R 4 that are not bonded to each other each independently represent Hydrogen atoms, It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • R 21 to R 27 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 21 to R 27 that are not bonded to each other are each independently a hydrogen atom or a substituent R.
  • R 28 and R 29 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, provided that when R 28 and R 29 are bonded to each other to form a substituted or unsubstituted fused ring, they do not form a 9,9 -spirobifluorene ring together with the fluorene ring to which they are bonded.
  • At least one of R 28 and R 29 that are not bonded to each other is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 28 and R 29 which are not bonded to each other and are not the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, each independently represent a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • One or more pairs of adjacent two or more of R 31 to R 37 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
  • R 31 to R 37 that are not bonded to each other are each independently a hydrogen atom or a substituent R.
  • R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or are not bonded to each other, provided that when R 38 and R 39 are bonded to each other to form a substituted or unsubstituted fused ring, they do not form a 9,9 -spirobifluorene ring together with the fluorene ring to which they are bonded.
  • At least one of R 38 and R 39 that are not bonded to each other is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 38 and R 39 which are not bonded to each other and are not the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, each independently represent a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • L 11 , L 21 and L 31 each independently represent It is a single bond, or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • n11 is an integer from 0 to 3. When n11 is 0, (L 11 ) n11 is a single bond.
  • n11 is 2 or 3
  • a plurality of L 11 are linked to each other in series, and the tricyclic fused skeleton is bonded to the L 11 that is the most distant from the benzene skeleton.
  • a plurality of L 11 may be the same or different.
  • n21 is an integer from 0 to 3.
  • n21 is 0, (L 21 )
  • n21 is a single bond.
  • n21 is 2 or 3
  • n31 is an integer from 0 to 3.
  • n31 When n31 is 0, (L 31 ) n31 is a single bond. When n31 is 2 or 3, a plurality of L 31 are linked to each other in series, and the fluorene skeleton is bonded to the L 31 that is the furthest from the nitrogen atom. A plurality of L 31 may be the same or different.
  • the substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si( R901 )( R902 )( R903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • the present invention provides a high-performance organic EL element and a compound capable of realizing the organic EL element.
  • FIG. 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.
  • hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
  • any possible bonding position that is not explicitly indicated with a symbol such as "R” or "D” representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded to it.
  • the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a compound having a structure in which atoms are bonded in a ring for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
  • the carbon contained in the substituent is not included in the number of ring carbon atoms.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • a 9,9-diphenylfluorenyl group has 13 ring carbon atoms
  • a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring.
  • the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) and atoms contained in a substituent when the ring is substituted with a substituent are not included in the number of ring atoms.
  • a compound e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound
  • Atoms that do not constitute a ring e.g., a
  • the "number of ring atoms" described below is the same unless otherwise specified.
  • the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5.
  • the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.
  • a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring atoms of a quinazoline ring. Therefore, the number of ring atoms in the quinazoline ring to which the hydrogen atom or substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon numbers XX to YY” refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • "YY” means an integer of 2 or more.
  • the "atomic number XX to YY” in the expression “substituted or unsubstituted ZZ group having atomic number XX to YY” refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituents when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • “YY” means an integer of 2 or more.
  • unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is an "unsubstituted ZZ group”
  • substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is a "substituted ZZ group”.
  • unsubstituted in the case of "a substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
  • substitution in the case of "a substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "a BB group substituted with an AA group” means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the "unsubstituted aryl group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted heterocyclic group” described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
  • the "unsubstituted alkyl group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described in this specification is, unless otherwise specified in this specification, 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the "unsubstituted cycloalkyl group” described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted arylene group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
  • the "unsubstituted alkylene group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B).
  • unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group”
  • substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is a "substituted aryl group”.
  • aryl group simply refers to both an "unsubstituted aryl group” and a "substituted aryl group”.
  • substituted aryl group refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group” are replaced with a substituent.
  • substituted aryl group include the "unsubstituted aryl group” in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below.
  • the examples of the "unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the "substituted aryl group” described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group” in the specific example group G1B below is further replaced with a substituent.
  • Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group,
  • Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, A meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, triphenyls
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom.
  • the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • the “heterocyclic groups” described herein are either monocyclic or fused ring groups.
  • the “heterocyclic group” described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B).
  • the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group"
  • the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group”.
  • substituted heterocyclic group refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in this specification also includes the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
  • Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, A pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl
  • Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanap
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
  • Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, A phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
  • Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2 .
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B).
  • the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group"
  • the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group” is a "substituted alkyl group”.
  • substituted alkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
  • specific examples of the "substituted alkyl group” include the following "unsubstituted alkyl group” (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B).
  • the alkyl group in the "unsubstituted alkyl group” refers to a chain-like alkyl group.
  • the "unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the "substituted alkyl group” described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group” in the specific example group G3B is further replaced with a substituent.
  • Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-Butyl group, and t-butyl group.
  • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
  • Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B).
  • the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group” is an "unsubstituted alkenyl group", and the "substituted alkenyl group” refers to the case where the "substituted or unsubstituted alkenyl group” is a "substituted alkenyl group”.
  • alkenyl group when the term “alkenyl group” is simply used, it includes both an "unsubstituted alkenyl group” and a "substituted alkenyl group”.
  • substituted alkenyl group refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B).
  • the examples of the "unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” listed here are merely examples, and the "substituted alkenyl group” described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group” in specific example group G4B is further replaced with a substituent.
  • Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, A 2-butenyl group, and a 3-butenyl group.
  • Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
  • the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group” is an "unsubstituted alkynyl group."
  • alkynyl group refers to an "unsubstituted alkynyl group” in which one or more hydrogen atoms have been replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include the following "unsubstituted alkynyl group” (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is an "unsubstituted cycloalkyl group”
  • substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group” is a "substituted cycloalkyl group”.
  • substituted cycloalkyl group refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B).
  • the examples of the "unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group” in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group” in the specific example group G6B is further replaced with a substituent.
  • Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
  • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.
  • G7 of the group represented by --Si(R 901 )(R 902 )(R 903 ) described in this specification include: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)(G6)
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • the multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
  • the multiple G2s in —Si(G1)(G2)(G2) are the same as or different from each other.
  • the multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
  • the multiple G2s in —Si(G2)(G2)(G2) are the same as or different from each other.
  • the multiple G3s in —Si(G3)(G3)(G3) are the same as or different from each other.
  • the multiple G6s in —Si(G6)(G6)(G6) are the same as or different from each other.
  • G8 of the group represented by -O-(R 904 ) described in this specification include: -O(G1), -O (G2), -O(G3) and -O(G6)
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 A group represented by -S-(R 905 )
  • Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S(G3) and -S(G6)
  • Examples include: here, G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G10 A group represented by -N(R 906 )(R 907 )
  • Specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: here, G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • the multiple G1s in -N(G1)(G1) are the same or different from each other.
  • the multiple G2s in -N(G2)(G2) are the same or different from each other.
  • the multiple G3s in -N(G3)(G3) are the same or different.
  • -N(G6)(G6) may be the same or different from each other.
  • halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • substituted or unsubstituted fluoroalkyl groups means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with fluorine atoms.
  • the number of carbon atoms in the "unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
  • substituted fluoroalkyl group means a group in which one or more hydrogen atoms in the "fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents include the examples of groups in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • substituted or unsubstituted haloalkyl group means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
  • substituted haloalkyl group means a group in which one or more hydrogen atoms in the "haloalkyl group” are replaced with a substituent.
  • substituted haloalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group” are further replaced with a substituent.
  • substituents in the "substituted haloalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted haloalkyl group” include the examples of the group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
  • a specific example of the "substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • Substituted or unsubstituted alkylthio group A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • a specific example of the "trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.
  • the number of carbon atoms in each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group” described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an “aralkyl group” is a group in which a hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one aspect of a “substituted alkyl group”.
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms of the "unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
  • substituted or unsubstituted aralkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a o-terphenyl-4-yl group, a o-terphenyl-3-yl group, a o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a
  • the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothi
  • zadibenzothiophenyl group diazadibenzothiophenyl group
  • (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group)
  • (9-biphenylyl)carbazolyl group (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
  • carbazolyl group is specifically any of the following groups:
  • the (9-phenyl)carbazolyl group is specifically any of the following groups:
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.
  • the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group".
  • Specific examples of the "substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1.
  • the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group".
  • Specific examples of the "substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the substituted or unsubstituted arylene group described herein is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a binding site.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a binding site.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • * represents a binding site.
  • the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
  • Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
  • the pair of adjacent two that constitutes one group includes the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926 , the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .
  • one or more pairs means that two or more pairs of the adjacent two or more pairs may simultaneously form a ring.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent rings forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded.
  • it means the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , and a set of three adjacent rings (R 921 , R 922 and R 923 ) are bonded to each other to form a ring, which is condensed to the anthracene skeleton.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “fused ring” formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even if “one of the pairs of adjacent two" forms a “monocyclic ring” or a “fused ring", the “monocyclic ring” or the “fused ring” can form a saturated ring or an unsaturated ring.
  • the ring Q A and the ring Q B formed in the general formula (TEMP-104) are “monocyclic rings” or “fused rings", respectively.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the ring Q A and the ring Q C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q A and the ring Q C. If the ring Q A in the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. When ring Q 1 A in the above general formula (TMEP-104) is a naphthalene ring, ring Q 1 A is a fused ring.
  • the "unsaturated ring” includes aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond in the ring structure, i.e., a double bond and/or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.).
  • the "saturated ring” includes an aliphatic hydrocarbon ring having no unsaturated bond, or a non-aromatic heterocycle having no unsaturated bond.
  • aromatic hydrocarbon ring examples include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom.
  • aromatic heterocycle examples include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
  • the ring QA formed by bonding R 921 and R 922 to each other in the general formula (TEMP-104) means a ring formed by the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary atoms.
  • R 921 and R 922 form a ring QA
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • the "arbitrary atom” is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below.
  • the ring formed is a heterocycle.
  • the "one or more any atoms" constituting the single ring or the fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
  • the "monocyclic ring” and the “condensed ring” the "monocyclic ring” is preferred.
  • the "saturated ring” and the “unsaturated ring” the “unsaturated ring” is preferred.
  • a "monocyclic ring” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more of a set of two or more adjacent rings combine with each other to form a substituted or unsubstituted monocyclic ring” or “combine with each other to form a substituted or unsubstituted fused ring
  • one or more of a set of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the substituent is, for example, the “optional substituent” described later.
  • specific examples of the substituent are the substituents described in the above-mentioned section “Substituents described in this specification”.
  • the substituent is, for example, the “optional substituent” described later.
  • substituents in the case of "substituted or unsubstituted” are, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si( R901 )( R902 )( R903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted
  • the two or more R 901 are the same or different from each other
  • the two or more R 902 are present, the two or more R 902 are the same or different from each other
  • the two or more R 903 are present, the two or more R 903 are the same or different from each other
  • the two or more R 904 are present, the two or more R 904 are the same or different from each other
  • the two or more R 905 are present, the two or more R 905 are the same or different from each other
  • two or more R 906 are present, the two or more R 906 are the same or different from each other
  • the two or more R 907 are present, the two or more R 907 are the same or different.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 50 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 18 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
  • the optional substituent may further have a substituent.
  • the substituent that the optional substituent further has is the same as the optional substituent described above.
  • a numerical range expressed using "AA-BB” refers to a range that includes the number AA written before “AA-BB” as the lower limit and the number BB written after "AA-BB” as the upper limit.
  • a compound according to one embodiment of the present invention is a compound represented by the following formula (1).
  • X11 is an oxygen atom or a sulfur atom.
  • R 11 to R 17 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 11 to R 17 that are not bonded to each other are each independently a hydrogen atom or a substituent R.
  • R 1 to R 4 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 1 to R 4 that are not bonded to each other each independently represent Hydrogen atoms, It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • R 21 to R 27 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 21 to R 27 that are not bonded to each other are each independently a hydrogen atom or a substituent R.
  • R 28 and R 29 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, provided that when R 28 and R 29 are bonded to each other to form a substituted or unsubstituted fused ring, they do not form a 9,9 -spirobifluorene ring together with the fluorene ring to which they are bonded.
  • At least one of R 28 and R 29 that are not bonded to each other is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 28 and R 29 which are not bonded to each other and are not the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, each independently represent a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • One or more pairs of adjacent two or more of R 31 to R 37 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other.
  • R 31 to R 37 that are not bonded to each other are each independently a hydrogen atom or a substituent R.
  • R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, provided that when R 38 and R 39 are bonded to each other to form a substituted or unsubstituted fused ring, they do not form a 9,9 -spirobifluorene ring together with the fluorene ring to which they are bonded.
  • At least one of R 38 and R 39 that are not bonded to each other is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 38 and R 39 which are not bonded to each other and are not the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, each independently represent a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • L 11 , L 21 and L 31 each independently represent It is a single bond, or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.
  • n11 is an integer from 0 to 3. When n11 is 0, (L 11 ) n11 is a single bond.
  • n11 is 2 or 3
  • a plurality of L 11 are linked to each other in series, and the tricyclic fused skeleton is bonded to the L 11 that is the most distant from the benzene skeleton.
  • a plurality of L 11 may be the same or different.
  • n21 is an integer from 0 to 3.
  • n21 is 0, (L 21 )
  • n21 is a single bond.
  • n21 is 2 or 3
  • n31 is an integer from 0 to 3.
  • n31 When n31 is 0, (L 31 ) n31 is a single bond. When n31 is 2 or 3, a plurality of L 31 are linked to each other in series, and the fluorene skeleton is bonded to the L 31 that is the furthest from the nitrogen atom. A plurality of L 31 may be the same or different.
  • the substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si( R901 )( R902 )( R903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • the compound according to one embodiment of the present invention has a specific structure represented by formula (1), and when used in an organic EL device, it can improve the device performance. Specifically, it can realize an organic EL device that can be driven at a lower voltage and is highly efficient.
  • the ring is formed by the carbon atom on the fluorene skeleton to which R 28 and R 29 are bonded and any atom (preferably at least one atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom).
  • the ring is spiro-bonded to the fluorene skeleton to which R 28 and R 29 are bonded, as shown in the following formula (E1). In the following formula, R 21 to R 27 are omitted.
  • the ring is each independently selected from the rings represented by the following formulas (1a) to (1r).
  • C spiro represents a carbon atom of the fluorene ring to which R 28 and R 29 are bonded, or a carbon atom of the fluorene ring to which R 38 and R 39 are bonded.
  • the carbon atoms constituting the ring have a hydrogen atom or a substituent R at a bondable position.
  • the substituent R is as defined in formula (1).
  • C spiro represents a carbon atom of the fluorene ring to which R 28 and R 29 are bonded, or a carbon atom of the fluorene ring to which R 38 and R 39 are bonded.”
  • C spiro means a spiro carbon atom, that is, the rings represented by the formulae (1a) to (1r) are bonded to the fluorene ring to form a spiro cyclic group.
  • the group bonded to the nitrogen atom via (L 21 ) n21 is a spirocyclic group represented by the following formula (E4) (a substituted or unsubstituted spiro[9H-fluorene-9,1'-cyclopentan]-2-yl group), in which R 21 to R 27 have been omitted.
  • the rings represented by the formulae (1a) to (1r) and the fluorene ring are bonded only at C spiro , and no other bridges are present.
  • R 28 and R 29 are joined to each other to form a substituted or unsubstituted monocyclic or fused ring. In one embodiment, R 28 and R 29 are not bonded to each other, R 28 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 29 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 28 and R 29 are not bonded to each other, R 28 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and R 29 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.
  • R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic or fused ring. In one embodiment, R 38 and R 39 are not bonded to each other, R 38 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 39 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 38 and R 39 are not bonded to each other, R 38 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and R 39 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.
  • R 28 and R 29 are not bonded to each other, R 28 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 29 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 38 and R 39 are not bonded to each other, R 38 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 39 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 28 and R 29 are not bonded to each other, R 28 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, R 29 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, R 38 and R 39 are not bonded to each other, R 38 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and R 39 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.
  • R 28 and R 29 are not bonded to each other, R 28 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 29 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.
  • R 28 and R 29 are not bonded to each other, R 28 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, R 29 is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.
  • R 28 and R 29 are bonded together to form a substituted or unsubstituted monocyclic ring or to form a substituted or unsubstituted fused ring;
  • R 38 and R 39 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring.
  • R 21 to R 27 and R 31 to R 37 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 21 to R 27 are hydrogen atoms. In one embodiment, R 31 to R 37 are hydrogen atoms.
  • R 21 to R 27 and R 31 to R 37 are hydrogen atoms.
  • X 11 is an oxygen atom.
  • R 11 to R 17 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 11 to R 17 are hydrogen atoms.
  • R 1 to R 4 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms.
  • R 1 to R 4 are hydrogen atoms.
  • L 11 , L 21 and L 31 are each independently a single bond or a substituted or unsubstituted phenylene group.
  • L 11 is a single bond. In one embodiment, L 21 is a single bond. In one embodiment, L 31 is a single bond.
  • L 11 , L 21 and L 31 are single bonds.
  • the compound represented by formula (1) is a compound represented by the following formula (1-1).
  • formula (1-1 X 11 , n11, n21, n31, L 11 , L 21 , L 31 , R 28 , R 29 , R 38 , and R 39 are as defined in formula (1).
  • the compound represented by formula (1) is a compound represented by formula (1-11) below.
  • X 11 , n11, n21, n31, L 11 , L 21 and L 31 are as defined in formula (1).
  • R 128 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 129 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 138 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 139 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by formula (1) is a compound represented by formula (1-21) below.
  • formula (1-21) X 11 , n11, n21, n31, L 11 , L 21 and L 31 are as defined in formula (1).
  • R 228 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 229 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R 238 and R 239 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to each other to form a substituted or unsubstituted fused ring.
  • R 238 and R 239 are bonded to each other to form a substituted or unsubstituted fused ring, there is no case where R 238 and R 239 are bonded to a fluorene ring together to form a 9,9-spirobifluorene ring.
  • the term "hydrogen atom” as used herein includes protium, deuterium, and tritium atoms.
  • the compounds of the invention may contain naturally occurring deuterium atoms.
  • deuterium atoms may be intentionally introduced into the compound of the invention by using compounds in which some or all of the raw materials are deuterated.
  • the compound represented by formula (1) contains at least one deuterium atom. That is, the compound of this embodiment may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.
  • R 11 to R 17 when R 11 to R 17 form a ring, a hydrogen atom possessed by the ring; R 11 to R 17 are hydrogen atoms; a hydrogen atom held by R 11 to R 17 which are the substituents R; when R 1 to R 4 form a ring, a hydrogen atom possessed by the ring; R 1 to R 4 are hydrogen atoms; a hydrogen atom held by the alkyl groups R 1 to R 4 ; a hydrogen atom held by the cycloalkyl groups R 1 to R 4 ; when R 21 to R 27 form a ring, a hydrogen atom possessed by the ring; R 21 to R 27 are hydrogen atoms; a hydrogen atom held by R 21 to R 27 which are the substituents R; when R 28 and R 29 form a ring, a hydrogen atom possessed by the ring; a hydrogen atom held by the alkyl groups R 28 and R 29 ; a hydrogen atom held by R 28 and R 29 which are aryl groups
  • R 1 to R 4 when R 1 to R 4 form a ring, a hydrogen atom possessed by the ring; R 1 to R 4 are hydrogen atoms; At least one hydrogen atom selected from the hydrogen atoms possessed by R 1 to R 4 which are alkyl groups and the hydrogen atoms possessed by R 1 to R 4 which are cycloalkyl groups may be a deuterium atom.
  • At least one hydrogen atom selected from R 1 to R 4 may be a deuterium atom.
  • the deuteration rate of a compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a certain deuteration rate is used, a certain proportion of naturally occurring light hydrogen isotopes may be contained. Therefore, the deuteration rate includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio that can be calculated by simply counting the number of deuterium atoms represented by the chemical formula. In one embodiment, the deuteration rate of the compound is, for example, 1% or more, 3% or more, 5% or more, 10% or more, or 50% or more.
  • the compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials that are appropriate for the target product.
  • the compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in a hole transport region of an organic EL device.
  • Organic EL element An organic EL element according to one embodiment of the present invention will be described.
  • the organic EL element according to one embodiment of the present invention has a cathode, an anode, an emitting layer disposed between the cathode and the anode, and a first layer (also called a "hole transport layer") disposed between the emitting layer and the anode, and the first layer contains a compound according to one embodiment of the present invention (a compound represented by formula (1)).
  • the first layer has, from the anode side, a first layer A and a first layer B, and at least one of the first layer A and the first layer B contains the compound according to one aspect of the present invention (the compound represented by formula (1)).
  • the first layer has, from the anode side, a first layer A and a first layer B, and the first layer B contains the compound according to one aspect of the present invention (the compound represented by formula (1)).
  • an ionization potential Ip A of the first layer A and an ionization potential Ip B of the first layer B satisfy the following formula (E1).
  • the ionization potential Ip A of the first layer A means the ionization potential of the material that constitutes the first layer A.
  • the ionization potential Ip A of the first layer B means the ionization potential of the material constituting the first layer B.
  • the ionization potential Ip A of the first layer A and the ionization potential Ip B of the first layer B can each be measured by the method described in the Examples.
  • an ionization potential Ip A of the first layer A and an ionization potential Ip B of the first layer B satisfy any one of the following formulas.
  • the refractive index n A of the first layer A and the refractive index n B of the first layer B satisfy the following formula (E2).
  • the refractive index n A of the first layer A means the refractive index of the material constituting the first layer A.
  • the refractive index n B of the first layer B means the refractive index of the material constituting the first layer B.
  • the refractive index nA of the first layer A and the refractive index nB of the first layer B can each be measured by the method described in the Examples.
  • the refractive index of the constituent material of the layer can be measured by the method described in the Examples using a film obtained by co-evaporating multiple compounds as the material to be measured onto a glass substrate, or a film obtained by vapor-depositing a mixture containing multiple compounds as the material to be measured.
  • the refractive index n A of the first layer A and the refractive index n B of the first layer B satisfy any one of the following formulas.
  • an ionization potential Ip A of the first layer A and an ionization potential Ip B of the first layer B satisfy the following formula (E1):
  • the refractive index n A of the first layer A and the refractive index n B of the first layer B satisfy the following formula (E2).
  • the organic EL element according to one aspect of the present invention has a second layer (also called an "electron barrier layer") between the first layer and the light-emitting layer.
  • the second layer may have the structure of a hole transport layer, which will be described later.
  • the organic EL element according to one aspect of the present invention has a third layer (also called a "hole injection layer") between the anode and the first layer.
  • the third layer may have the structure of a hole injection layer, which will be described later.
  • the third layer contains a compound according to one aspect of the present invention (a compound represented by formula (1)).
  • the third layer may contain a material other than the compound according to one embodiment of the present invention (for example, a doping compound).
  • materials other than the compound according to one embodiment of the present invention include materials for the hole injection layer described below.
  • Dope Compound By including a dopant compound in the third layer, it is expected that the hole injection properties from the anode to the first layer will be improved.
  • the doped compound is a compound including at least one of a first ring structure represented by the following formula (P11) and a second ring structure represented by the following formula (P12).
  • the first ring structure represented by formula (P11) is condensed in the molecule of the doped compound with at least one of the following ring structures: a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
  • R 11 to R 14 and R 1101 to R 1110 each independently represent Hydrogen atoms, Halogen atoms, Hydroxy groups, Cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by —O—(R 904 ), A group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ); It is a substituted or unsubstit
  • Z 1 to Z 5 each independently represent Nitrogen atom, It is the carbon atom bonded to R 15 or to another atom in the molecule of the doped compound. However, at least one of Z 1 to Z 5 is a carbon atom bonded to another atom in the molecule of the doping compound.
  • R15 is Hydrogen atoms, Halogen atoms, Cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by —O—(R 904 ), A group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ); a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substitute
  • R 901 to R 907 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • the plurality of R 901 may be the same or different.
  • the plurality of R 902 may be the same or different.
  • the plurality of R 903 may be the same or different.
  • the plurality of R 904 s may be the same or different.
  • the plurality of R 905 may be the same or different.
  • the plurality of R 906 may be the same or different.
  • the plurality of R 907 s may be the same or different.
  • the ester group is at least one group selected from the group consisting of an alkyl ester group and an aryl ester group.
  • R E is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
  • the aryl ester group is represented, for example, by —C( ⁇ O)OR 4 Ar , where R 4 Ar is, for example, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the siloxanyl group is a silicon compound group via an ether bond, for example, a trimethylsiloxanyl group.
  • the carbamoyl group is represented by -CONH2 .
  • the substituted carbamoyl group is represented, for example, by -CONH-Ar C or -CONH-R C.
  • Ar C is, for example, at least one group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably 6 to 10 ring carbon atoms) and a heterocyclic group having 5 to 50 ring atoms (preferably 5 to 14 ring atoms).
  • Ar C may be a group in which a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is bonded to a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 3 C is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
  • any group described as "substituted or unsubstituted” is an "unsubstituted” group.
  • Specific examples of the doping compound include the following compounds, but the doping compound is not limited to these specific examples.
  • the third layer contains a compound according to one aspect of the present invention in an amount of 70% by weight or more, 80% by weight or more, 90% by weight or more, 95% by weight or more, or 98% by weight or more of the total weight of the third layer.
  • the organic EL element according to one aspect of the present invention has an electron transport zone between the cathode and the light-emitting layer.
  • a typical element configuration of the organic EL element is, for example, a structure in which the following structures are laminated on a substrate.
  • the hole transporting region is usually composed of a hole transporting layer and may include one or more layers selected from a hole injection layer and an electron blocking layer.
  • the electron transporting region is usually composed of one or more layers selected from an electron injection layer and an electron transporting layer.
  • the hole transport zone may include two or more hole transport layers.
  • the electron-transporting zone may include two or more electron-transporting layers.
  • An organic EL element 1 includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole transporting region 4 between the anode 3 and the emitting layer 5, and an electron transporting region 6 between the emitting layer 5 and the cathode 10.
  • the substrate is used as a support for the light-emitting element.
  • glass, quartz, plastic, etc. can be used as the substrate.
  • a flexible substrate may also be used.
  • a flexible substrate is a substrate that can be bent (flexible), and examples of the flexible substrate include plastic substrates made of polycarbonate and polyvinyl chloride.
  • anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more).
  • a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function specifically, 4.0 eV or more.
  • Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene.
  • ITO indium oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide indium oxide containing zinc oxide
  • graphene graphene
  • Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride).
  • the hole injection layer is a layer containing a substance having a high hole injection property.
  • the substance having a high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, and polymer compounds (oligomers, dendrimers, polymers, etc.).
  • the hole injection layer may or may not contain the above-mentioned other substances in addition to the compound according to one embodiment of the present invention (the compound represented by formula (1)).
  • the hole transport layer is a layer containing a substance with high hole transport properties.
  • an aromatic amine compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • other substances may be used as long as they have a higher hole transport property than electron transport properties.
  • the layer containing the substance with high hole transport properties may be not only a single layer, but also a laminate of two or more layers made of the above substances.
  • the hole transport layer may or may not contain the above-mentioned other substances in addition to the compound according to one embodiment of the present invention (the compound represented by formula (1)).
  • the light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as a highly light-emitting substance.
  • a fluorescent compound is a compound that can emit light from a singlet excited state
  • a phosphorescent compound is a compound that can emit light from a triplet excited state.
  • blue-based fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, azaborine derivatives, arylborane derivatives, triarylamine derivatives, etc.
  • green-based fluorescent materials that can be used in the light-emitting layer include azaborine derivatives, arylborane derivatives, aromatic amine derivatives, etc.
  • red-based fluorescent materials that can be used in the light-emitting layer include tetracene derivatives, diamine derivatives, etc.
  • metal complexes such as iridium complexes, osmium complexes, platinum complexes, etc. are used.
  • green phosphorescent materials usable in the light-emitting layer iridium complexes, etc. are used.
  • metal complexes such as iridium complexes, platinum complexes, terbium complexes, europium complexes, etc. are used.
  • the light-emitting layer includes an azaborine derivative.
  • the light-emitting layer comprises a compound represented by the following formula (D1):
  • Ring a, ring b, and ring c each independently represent It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
  • R D601 and R D602 each independently bond to the ring a, ring b or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
  • R and R which do not form a substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • Ring a, ring b, and ring c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) that are fused to the central fused two-ring structure of formula (D1) that is composed of a boron atom and two nitrogen atoms.
  • aromatic hydrocarbon rings of rings a, b, and c have the same structure as a compound in which a hydrogen atom has been introduced into an "aryl group.”
  • the "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
  • the "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of formula (D1) as ring-forming atoms.
  • substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms include compounds in which a hydrogen atom has been introduced into the "aryl group” described in specific example group G1.
  • heterocycles of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group.”
  • the "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (D1) as ring-forming atoms.
  • the "heterocycle” of rings b and c contains two carbon atoms on the central fused bicyclic structure of formula (D1) as ring-forming atoms.
  • Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring-forming atoms” include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.
  • R D601 and R D602 may each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle.
  • the heterocycle in this case includes the nitrogen atom on the fused two-ring structure in the center of formula (D1).
  • the heterocycle in this case may include a heteroatom other than a nitrogen atom.
  • R D601 and R D602 bond to the ring a, ring b, or ring c means that an atom constituting the ring a, ring b, or ring c is bonded to an atom constituting R D601 and R D602 .
  • R D601 may bond to the ring a to form a two-ring fused (or three-ring or more fused) nitrogen-containing heterocycle in which the ring containing R D601 is fused to the ring a.
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring fused or more heterocyclic groups in the specific example group G2.
  • R D601 and R D602 each independently may not be bonded to ring a, ring b, or ring c.
  • the rings a, b, and c in formula (D1) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
  • the rings a, b, and c in formula (D1) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
  • R and R in formula (D1) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferred.
  • the compound represented by formula (D1) is a compound represented by the following formula (D1-1) or formula (D1-2).
  • R D601A combines with one or more selected from the group consisting of R D611 and R D622 to form a substituted or unsubstituted heterocycle, or does not form said heterocycle.
  • R D602A combines with one or more selected from the group consisting of R D613 and R D614 to form a substituted or unsubstituted heterocycle, or does not form said heterocycle.
  • R D601A and R D602A which do not form a heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R D611 to R D622 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other.
  • R D611 , R D613 , R D614 , and R D622 which do not form the heterocycle, the monocycle, or the fused ring, and R D612 and R D615 to R D621 which do not form the monocycle or the fused ring are each independently a hydrogen atom or a substituent R.
  • X D601 is an oxygen atom or a sulfur atom.
  • R D602A combines with one or more selected from the group consisting of R D613 and R D614 to form a substituted or unsubstituted heterocycle, or does not form said heterocycle.
  • R D603A combines with one or more selected from the group consisting of R D611 and R D634 to form a substituted or unsubstituted heterocycle, or does not form said heterocycle.
  • R D602A and R D603A which do not form a heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R D611 to R D617 and R D631 to R D634 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R D611 , R D613 , R D614 , and R D634 which do not form the heterocycle, the monocycle, or the fused ring
  • R D612 , R D615 to R D617 , and R D631 to R D633 which do not form the monocycle or the fused ring, are each independently a hydrogen atom or a substituent R.
  • the substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si( R901 )( R902 )( R903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • the compound represented by formula (D1) is a compound represented by the following formula (D1-1-1) or formula (D1-2-1).
  • R 1 D601B and R 1 D602B each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R D612A , R D616A , R D619A , and R D633A are each independently Hydrogen atoms, It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or -N(R 906 )(R 907 ).
  • R 906 and R 907 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • each of the two or more R 906 and R 907 may be the same or different.
  • Specific examples of the compound represented by formula (D1) include the following compounds. However, the compound represented by formula (D1) is not limited to these specific examples.
  • the light-emitting layer may have a structure in which the highly light-emitting substance (guest material) described above is dispersed in another substance (host material).
  • a substance for dispersing the highly light-emitting substance various substances can be used, and it is preferable to use a substance having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly light-emitting substance.
  • a substance (host material) for dispersing a highly luminescent substance 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative.
  • the light-emitting layer comprises an anthracene derivative having a heterocyclic group.
  • the heterocyclic group include the above-mentioned specific examples G2.
  • the light-emitting layer comprises a compound represented by formula (H1): [In formula (H1), X H11 is an oxygen atom, a sulfur atom, or NR H100 .
  • L H1 and L H2 each independently represent Single bond, It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
  • Ar H1 is It is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.
  • R H11 to R H18 and R H100 represents a bond to L H2 (* represents the bonding position of any one of R H11 to R H18 and R H100 to L H2 ).
  • One or more pairs of adjacent two or more of R H11 to R H18 that do not represent a bond to L H2 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R H1 to R H8 , as well as R H11 to R H18 and R H100 which are not bonded to L H2 and are not bonded to each other, are each independently a hydrogen atom or the substituent A.
  • the substituent A is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • R H11 -R H18 and R H100 that do not represent a bond to L H2 are all hydrogen atoms. In one embodiment, only one of R H11 -R H18 and R H100 that does not represent a bond to L H2 is an A substituent.
  • Ar H1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • Ar H1 is selected from groups represented by the following formulas (Ha1) to (Ha4).
  • * represents the bonding position to L H1 .
  • bH1 is an integer of 0 to 4.
  • bH2 is an integer from 0 to 5.
  • bH3 is an integer from 0 to 7.
  • the multiple R H110 may be the same as or different from each other.
  • each of bH1 to bH3 is 2 or more, one or more pairs of adjacent two or more of the multiple R H110 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R H110 which are not bonded to each other are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si( R901 )( R902 )( R903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • L H1 and L H2 each independently represent a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms.
  • At least one of L H1 and L H2 is a single bond.
  • the compound represented by formula (H1) is a compound represented by the following formula (H1-1) or formula (H1-2).
  • H1-1 L H1 , L H2 , Ar H1 , and R H1 to R H8 are as defined in formula (H1).
  • XH21 is an oxygen atom, a sulfur atom, or NR H100 . Any one of R H21 to R H30 and R H100 represents a bond to L H2 (* represents the bonding position of any one of R H21 to R H30 and R H100 to L H2 ).
  • R H21 to R H30 that do not represent a bond to L H2 , one or more pairs of adjacent two or more are not bonded to each other and do not form a substituted or unsubstituted monocyclic or condensed ring.
  • R H21 to R H30 and R H100 that do not represent a bond to L H2 each independently represent a hydrogen atom or a substituent A.
  • L H1 , L H2 , Ar H1 , and R H1 to R H8 are as defined in formula (H1).
  • XH21 is an oxygen atom, a sulfur atom, or NR H100 .
  • R H31 to R H40 and R H100 represents a bond to L H2 (* represents the bonding position of any one of R H31 to R H40 and R H100 to L H2 ).
  • R H31 to R H40 that do not represent a bond to L H2 one or more pairs of adjacent two or more are not bonded to each other, and do not form a substituted or unsubstituted monocyclic or fused ring.
  • R H31 to R H40 and R H100 that do not represent a bond to L H2 each independently represent a hydrogen atom or a substituent A.
  • the substituent A is as defined in formula (H1).
  • the compound represented by formula (H1) is a compound represented by the following formula (H1-1-1) or formula (H1-2-1).
  • L H1 , L H2 , Ar H1 , and R H1 to R H8 are as defined in formula (H1).
  • one of the carbon atoms constituting the naphthobenzofuran skeleton is bonded to L H2 via a single bond.
  • L H2 is a single bond
  • one of the carbon atoms constituting the naphthobenzofuran skeleton is bonded to the anthracene skeleton via a single bond.
  • the compound represented by formula (H1) is a compound represented by the following formula (H1-1-2) or formula (H1-2-2).
  • L H1 , L H2 and Ar H1 are as defined in formula (H1).
  • one of the carbon atoms constituting the naphthobenzofuran skeleton is bonded to L H2 via a single bond.
  • L H2 is a single bond
  • one of the carbon atoms constituting the naphthobenzofuran skeleton is bonded to the anthracene skeleton via a single bond.
  • the electron transport layer is a layer containing a substance having high electron transport properties, and may be formed using 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.
  • a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.
  • the electron injection layer is a layer containing a substance with high electron injection properties, and may be made of a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or 8-hydroxyquinolinolato-lithium (Liq), an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
  • a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), or 8-hydroxyquinolinolato-lithium (Liq)
  • an alkali metal such as lithium oxide (LiO x ), an alkaline earth metal, or a compound thereof.
  • cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a small work function (specifically, 3.8 eV or less).
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • the cathode is usually formed by a vacuum deposition method or a sputtering method. When a silver paste or the like is used, a coating method or an inkjet method can be used.
  • the cathode can be formed using various conductive materials, such as aluminum, silver, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.
  • the thickness of each layer is not particularly limited, but in general, a thickness in the range of several nm to 1 ⁇ m is preferable in order to suppress defects such as pinholes, keep the applied voltage low, and improve the light emission efficiency.
  • each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
  • Each layer, such as the light-emitting layer can be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or coating methods such as dipping a solution dissolved in a solvent, spin coating, casting, bar coating, and roll coating.
  • MBE molecular beam deposition
  • An electronic device includes the organic EL element according to an aspect of the present invention.
  • Specific examples of electronic devices include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.
  • Example 1 Preparation of Organic EL Element> An organic EL device was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus.
  • ITO transparent electrode anode
  • compound 1 and HI-1 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, so that the ratio of compound HI-1 was 1 mass %, thereby forming a first hole transport layer (hole injection layer) with a thickness of 10 nm.
  • Compound 1 was deposited on the first hole transport layer to form a second hole transport layer (hole transport layer) having a thickness of 77.5 nm.
  • the compound HT-1 was evaporated to form a third hole transport layer (electron blocking layer) having a thickness of 7.5 nm.
  • compound BH-1 host material
  • compound BH-2 host material
  • compound BD-1 dopant material
  • the compound ET-1 was evaporated to form a first electron transport layer having a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited such that the proportion of Liq was 33 mass %, to form a second electron transport layer with a thickness of 25 nm.
  • Metal Yb was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • the percentages in parentheses indicate the ratio (mass %) of the latter compound in the layer.
  • Example 2 An organic EL device was produced and evaluated in the same manner as in Example 1, except that in forming the first hole transport layer and the second hole transport layer, the compounds shown in Table 1 were used instead of Compound 1. The results are shown in Table 1.
  • Comparative Examples 1 to 2 An organic EL device was produced and evaluated in the same manner as in Example 1, except that in forming the first hole transport layer and the second hole transport layer, the compounds shown in Table 1 were used instead of Compound 1. The results are shown in Table 1.
  • Example 3 Preparation of Organic EL Element> An organic EL device was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus.
  • ITO transparent electrode anode
  • compound 1 and HI-1 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, so that the ratio of compound HI-1 was 2 mass %, thereby forming a first hole transport layer (hole injection layer) with a thickness of 10 nm.
  • Compound 1 was deposited on the first hole transport layer to form a second hole transport layer (hole transport layer) having a thickness of 77.5 nm.
  • the compound HT-1 was evaporated to form a third hole transport layer (electron blocking layer) having a thickness of 7.5 nm.
  • compound BH-1 host material
  • compound BH-2 host material
  • compound BD-1 dopant material
  • the compound ET-1 was evaporated to form a first electron transport layer having a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited such that the proportion of Liq was 33 mass %, to form a second electron transport layer with a thickness of 25 nm.
  • Metal Yb was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
  • the numbers in parentheses indicate the film thickness (unit: nm).
  • the percentages in parentheses indicate the ratio (mass %) of the latter compound in the layer.
  • Example 4 Organic EL devices were prepared and evaluated in the same manner as in Example 3, except that in forming the first hole transport layer and the second hole transport layer, the compounds shown in Table 2 were used instead of Compound 1. The results are shown in Table 2.
  • Comparative Examples 3 to 4 Organic EL devices were prepared and evaluated in the same manner as in Example 3, except that in forming the first hole transport layer and the second hole transport layer, the compounds shown in Table 2 were used instead of Compound 1. The results are shown in Table 2.
  • Example 5 Preparation of Organic EL Element> An organic EL device was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus.
  • ITO transparent electrode anode
  • compound 1 and HI-1 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, so that the ratio of compound HI-1 was 2 mass %, thereby forming a first hole transport layer (hole injection layer) with a thickness of 10 nm.
  • Compound 1 was deposited on the first hole transport layer to form a second hole transport layer (hole transport layer) having a thickness of 80 nm.
  • the compound HT-2 was evaporated to form a third hole transport layer (electron blocking layer) having a thickness of 7.5 nm.
  • compound BH-1 host material
  • compound BD-2 dopant material
  • compound ET-3 was evaporated to form a first electron transport layer having a thickness of 5 nm.
  • compound ET-4 and Liq were co-deposited such that the proportion of Liq was 50 mass %, to form a second electron transport layer with a thickness of 30 nm.
  • Metal Yb was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 50 nm.
  • the device configuration of the organic EL device of Example 5 is shown in schematic form as follows. ITO(130)/Compound 1:HI-1(10:2%)/Compound 1(80)/HT-2(7.5)/BH-1:BD-2(20:1%)/ET-3(5)/ET-4:Liq(30:50%)/Yb(1)/Al(50)
  • the numbers in parentheses indicate the film thickness (unit: nm), and the percentages in parentheses indicate the proportion (mass %) of the latter compound in the layer.
  • the organic EL devices thus fabricated were subjected to the following evaluations. The results are shown in Table 3.
  • Refractive Index The refractive index (n 2 ) of the material (compound) constituting the second hole transport layer was measured as follows. The material to be measured was vacuum-deposited on a glass substrate to a thickness of about 50 nm, and incident light (ultraviolet, visible, and near-infrared) was irradiated at measurement angles of 45° to 75° at 5° intervals using a spectroscopic ellipsometry device ("M-2000UI", manufactured by J.A. Woollam Co., Ltd.) to measure the change in the polarization state of the light reflected from the sample surface.
  • M-2000UI spectroscopic ellipsometry device
  • the transmission spectrum in the normal direction of the substrate was also measured using the same device. Similarly, the same measurement was performed on only the glass substrate on which the material to be measured was not deposited.
  • the obtained measurement information was fitted using analysis software (Complete EASE) manufactured by J.A. Woollam Co., Ltd. As the fitting condition, a uniaxial rotationally symmetric anisotropic model was used, and the parameter MSE indicating the root mean square error in the software was set to 3.0 or less to calculate the in-plane and normal direction refractive index, in-plane and normal direction extinction coefficient, and order parameter of the organic film formed on the substrate.
  • the order parameter was calculated by the peak wavelength of S1, with the peak of the extinction coefficient (in-plane direction) on the long wavelength side being taken as S1.
  • an isotropic model was used as the fitting condition for the glass substrate.
  • a film of a low molecular weight material vacuum-deposited on a substrate usually has uniaxial rotational symmetry with the normal direction of the substrate as the axis of rotation symmetry.
  • the method for forming the thin film is a vacuum deposition method.
  • the order parameter S' obtained from multi-angle spectroscopic ellipsometry measurement is 1.0 when all molecules are oriented parallel to the substrate, and 0.66 when the molecules are not oriented but random.
  • the refractive index at 2.7 eV in the direction parallel to the substrate (ordinary direction) measured above is defined as the refractive index of the material to be measured.
  • the refractive index at 2.7 eV corresponds to the refractive index at 460 nm.
  • Examples 6 and 8 Organic EL devices were prepared and evaluated in the same manner as in Example 5, except that in forming the light-emitting layer, the compound BH-1 was replaced with a compound shown in Table 3. The results are shown in Table 3.
  • Example 7 An organic EL device was prepared and evaluated in the same manner as in Example 5, except that in forming the light-emitting layer, instead of compound BH-1, compound BH-1 and compound BH-3 (host material) were used in a ratio (parts by mass) of 50:50. The results are shown in Table 3.
  • Comparative Example 5 Organic EL devices were prepared and evaluated in the same manner as in Example 5, except that in forming the first hole transport layer and the second hole transport layer, the compounds shown in Table 3 were used instead of Compound 1. The results are shown in Table 3.
  • Example 9 Preparation of Organic EL Element> An organic EL device was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder of a vacuum deposition apparatus.
  • first hole transport layer hole injection layer
  • second hole transport layer hole transport layer
  • third hole transport layer hole transport layer
  • fourth hole transport layer electrostatic blocking layer
  • compound BH-5 host material
  • compound BD-3 dopant material
  • the compound ET-5 was evaporated to form a first electron transport layer having a thickness of 10 nm.
  • the compound ET-6 and metallic Li were co-deposited so that the proportion of metallic Li was 4 mass %, to form a second electron transport layer having a thickness of 20 nm.
  • Metallic Al was evaporated onto the second electron transport layer to form a cathode having a thickness of 80 nm.
  • the numbers in parentheses indicate the film thickness (unit: nm), and the percentages in parentheses indicate the proportion (mass %) of the latter compound in the layer.
  • the organic EL devices thus fabricated were subjected to the following evaluations. The results are shown in Table 4.
  • Driving Voltage The initial characteristics of the organic EL element were measured at room temperature by driving with a DC (direct current) constant current of 10 mA/cm 2 . External quantum efficiency A voltage was applied to the organic EL element so that the current density was 10 mA/ cm2 , and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (%) was calculated.
  • Comparative Examples 6 to 8 An organic EL device was prepared and evaluated in the same manner as in Example 9, except that in forming the third hole transport layer, a compound shown in Table 4 was used instead of Compound 1. The results are shown in Table 4.
  • the device of Example 9 has a low driving voltage and a high external quantum efficiency. This is believed to be because the device of Example 9, in which the difference ( ⁇ Ip 2-3 ) between the ionization potential of the material constituting the second hole transport layer and the ionization potential of the material constituting the third hole transport layer is small, has improved hole injection properties compared to the device of Comparative Example 6, in which ⁇ Ip 2-3 is large.

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Abstract

L'invention concerne un composé représenté par la formule (1).
PCT/JP2023/042041 2022-12-01 2023-11-22 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique WO2024117003A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019185061A1 (fr) * 2018-03-29 2019-10-03 江苏三月光电科技有限公司 Composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation
WO2020009518A1 (fr) * 2018-07-05 2020-01-09 주식회사 엘지화학 Composé polycyclique et diode électroluminescente organique le comprenant
US20210147375A1 (en) * 2018-04-04 2021-05-20 Merck Patent Gmbh Materials for electronic devices
WO2021227655A1 (fr) * 2020-05-11 2021-11-18 北京鼎材科技有限公司 Composé, dispositif électroluminescent organique et dispositif d'affichage

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019185061A1 (fr) * 2018-03-29 2019-10-03 江苏三月光电科技有限公司 Composé à base de bis(diméthylfluorène), son procédé de préparation et son utilisation
US20210147375A1 (en) * 2018-04-04 2021-05-20 Merck Patent Gmbh Materials for electronic devices
WO2020009518A1 (fr) * 2018-07-05 2020-01-09 주식회사 엘지화학 Composé polycyclique et diode électroluminescente organique le comprenant
WO2021227655A1 (fr) * 2020-05-11 2021-11-18 北京鼎材科技有限公司 Composé, dispositif électroluminescent organique et dispositif d'affichage

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