WO2025013872A1 - 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 - Google Patents

化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 Download PDF

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WO2025013872A1
WO2025013872A1 PCT/JP2024/024827 JP2024024827W WO2025013872A1 WO 2025013872 A1 WO2025013872 A1 WO 2025013872A1 JP 2024024827 W JP2024024827 W JP 2024024827W WO 2025013872 A1 WO2025013872 A1 WO 2025013872A1
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carbon atoms
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佑典 高橋
清香 水谷
将太 田中
司 澤藤
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Priority to CN202480043932.6A priority patent/CN121419959A/zh
Publication of WO2025013872A1 publication Critical patent/WO2025013872A1/ja
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Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device including the organic electroluminescence device.
  • an organic electroluminescence element (hereinafter sometimes referred to as "organic EL element”) is composed of an anode, a cathode, and an organic layer sandwiched between the anode and cathode.
  • organic EL element When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region, where they recombine to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important in obtaining high-performance organic EL elements.
  • Patent documents 1 to 11 disclose compounds used as materials for organic electroluminescence devices.
  • the present invention has been made to solve the above problems, and aims to provide a compound that further improves the performance of an organic EL element, an organic EL element with improved element performance, and an electronic device that includes such an organic EL element.
  • the present inventors have conducted extensive research into the performance of organic EL devices containing the compounds described in the above patent documents and other compounds, and have found that monoamines represented by the following formulas (A), (B), (C) or (D) provide organic EL devices with improved device performance.
  • the present invention provides a compound represented by formula (A): (In formula (A), N * is the central nitrogen atom.
  • L a1 is a single bond or a group represented by the following formula (i) to (iii), when L a1 is a single bond, Ar a1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted naphthobenzothiophenyl group, or a substituted or unsubstituted 1-phenanthryl group, When L a1 is a group represented by the following formulas (i) to (iii
  • one selected from R a21 to R a25 is a single bond bonding to *a2
  • one selected from R a31 to R a38 is a single bond bonding to *a5
  • the other selected from R a31 to R a38 is a single bond bonding to *a6
  • One selected from R a41 to R a45 is a single bond bonding to *a9
  • the other selected from R a51 to R a55 is a single bond bonding to *a10.
  • the R a21 to R a25 which are not a single bond, the R a31 to R a38 which are not a single bond, the R a41 to R a45 which are not a single bond, and the R a51 to R a55 which are not a single bond are each independently a hydrogen atom, 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(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms,
  • *a1, *a4, and *8 represent the bonding positions to the central nitrogen atom N * ; *a3, *a7, and *11 represent the binding positions to Ar a1 .
  • Any two adjacent groups selected from among R a21 to R a25 which are not single bonds, R a31 to R a38 which are not single bonds, R a41 to R a45 which are not single bonds, and R a51 to R a55 which are not single bonds are not bonded to each other to form a ring.
  • Ar a2 is a group represented by any one of the following formulas (a1) to (a3). (In formula (a1), *a12 represents the bonding position to the central nitrogen atom N * .
  • R a101 to R a105 is a single bond bonding to *a13
  • R a106 to R a110 is a single bond bonding to *a14.
  • the R a101 to R a105 that are not a single bond, and the R a106 to R a110 that are not a single bond are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring carbon atoms.
  • R a111 to R a115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R a111 to R a115 are not bonded to each other to form a ring.
  • *a15 represents the bonding position to the central nitrogen atom N * .
  • R a131 to R a138 is a single bond bonded to *a16.
  • R a121 to R a124 and R a131 to R a138 that are not a single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R a121 to R a124 and R a131 to R a138 that are not single bonds are not bonded to each other to form a ring. (In formula (a3), *a17 represents the bonding position to the central nitrogen atom N * .
  • L a2 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.
  • X a1 is an oxygen atom or a sulfur atom.
  • R a141 to R a148 is a single bond bonded to *a18.
  • R a141 to R a148 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R a141 to R a148 that are not single bonds may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore not form a ring structure.
  • R a1 to R a4 are each a hydrogen atom.
  • R a11 to R a17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; Any two adjacent groups selected from R a11 to R a17 do not bond to each other to form a ring.
  • Ring A and ring B may or may not be bridged. When ring A and ring B are bridged, the ring structure formed by bridging the ring A and the ring B has at least one deuterium atom; When ring A and ring B are not bridged, At least one selected from R a1 to R a4 is a deuterium atom.
  • the present invention provides a compound represented by formula (B): (In the formula (B), N * is the central nitrogen atom.
  • L b1 is a single bond or a group represented by the following formula (iv) or (v).
  • one selected from R b41 to R b45 is a single bond bonded to *b2
  • One selected from R b51 to R b58 is a single bond bonded to *b5
  • the other selected from R b51 to R b58 is a single bond bonded to *b6.
  • R b41 to R b45 which are not single bonds and the R b51 to R b58 which are not single bonds are each independently a hydrogen atom, 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(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms; R 901 to R 905 each independently represent a hydrogen atom, a substituted
  • *b1 and *b4 represent the bonding positions to the central nitrogen atom N * , *b3 and *b7 represent the binding positions to Ar b1 . Any two adjacent ones selected from among R b41 to R b45 which are not a single bond and R b51 to R b58 which are not a single bond are not bonded to each other to form a ring.
  • AR b1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • R b1 to R b4 are each a hydrogen atom.
  • R b11 to R b17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; Any two adjacent groups selected from R b11 to R b17 are not bonded to each other to form a ring. Ring C and ring D may or may not be bridged.
  • R b21 to R b24 and R b31 to R b38 are each independently a hydrogen atom, 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(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms; R 901 to R 905 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group
  • the present invention provides a compound represented by formula (C): (In formula (C), N * is the central nitrogen atom.
  • L c1 is a single bond or a group represented by the following formula (vi) or (vii).
  • one selected from R c31 to R c35 is a single bond bonded to *c2
  • One selected from R c41 to R c48 is a single bond bonded to *c5
  • the other selected from R c41 to R c48 is a single bond bonded to *c6.
  • the R c31 to R c35 that are not single bonds and the R c41 to R c48 that are not single bonds are each independently a hydrogen atom, 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(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 to R 905 each independently represent a hydrogen atom, a substitute
  • *c1 and *c4 represent the bonding positions to the central nitrogen atom N * ;
  • *c3 and *c7 represent the bonding positions to ring G. Any two adjacent groups selected from among R c31 to R c35 which are not single bonds and R c41 to R c48 which are not single bonds are not bonded to each other to form a ring.
  • Ar c1 is a group represented by the following formula (c1) or (c2). (In formula (c1), *c8 represents the bonding position to the central nitrogen atom N * .
  • R c11 to R c17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; Any two adjacent groups selected from R c11 to R c17 are not bonded to each other to form a ring. Ring E and ring F may or may not be bridged.
  • R c21 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
  • *d2 represents the bonding position to the central nitrogen atom N * , and *d1 bonds to one selected from R d21 to R d28 . Any two adjacent groups selected from R d31 to R d35 that are not single bonds are not bonded to each other to form a ring.
  • Ar d1 is a group represented by any one of the following formulas (d1) to (d3).
  • *d7 represents the bonding position to the central nitrogen atom N * .
  • One selected from R d101 to R d105 is a single bond bonded to *d8, and one selected from R d106 to R d110 is a single bond bonded to *d9.
  • the R d101 to R d105 that are not single bonds, and the R d106 to R d110 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring carbon atoms. Any two adjacent R d101 to R d105 that are not single bonds are not bonded to each other to form a ring, Any two adjacent groups selected from R d106 to R d110 that are not single bonds are not bonded to each other to form a ring.
  • R d111 to R d115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R d111 to R d115 are not bonded to each other to form a ring. m is 0 or 1; n is 0 or 1.
  • *d10 represents the bonding position to the central nitrogen atom N * .
  • L d2 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.
  • R d121 to R d128 is a single bond bonding to *d11.
  • the R d121 to R d128 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R d121 to R d128 that are not single bonds are not bonded to each other to form a ring. (In formula (d3), *d12 represents the bonding position to the central nitrogen atom N * .
  • L d3 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.
  • Xd1 is an oxygen atom or a sulfur atom.
  • R d131 to R d138 is a single bond bonded to *a14.
  • R d131 to R d138 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent non-single bond R d131 to R d138 selected from each of the above may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore may not form a ring structure.
  • R d1 to R d4 are each a hydrogen atom.
  • R d11 to R d17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; Any two adjacent groups selected from R d11 to R d17 are not bonded to each other to form a ring. Ring H and Ring I may or may not be bridged.
  • R d21 to R d28 that are not single bonds bonded to d1 each independently represent a hydrogen atom or a substituted or unsubstituted aryl group having 6 ring carbon atoms, * At least one selected from R d21 to R d28 that is not a single bond bonded to d1 is the substituted or unsubstituted aryl group having 6 ring carbon atoms.
  • the present invention provides a material for an organic EL device comprising a compound represented by formula (A), (B), (C) or (D).
  • the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising an emitting layer, and at least one layer of the organic layer comprising a compound represented by formula (A), (B), (C) or (D).
  • the present invention provides an electronic device including the organic electroluminescence element.
  • Organic EL devices containing a compound represented by formula (A), (B), (C) or (D) exhibit improved device performance.
  • FIG. 1 is a schematic diagram illustrating an example of a layer structure of an organic EL element according to one embodiment of the present invention.
  • FIG. 2 is a schematic diagram showing another example of a layer structure of an organic EL element according to an embodiment of the present invention.
  • FIG. 2 is a schematic diagram showing still another example of a layer structure of an organic EL element according to an 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, deuterium atom, or 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) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly).
  • the number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent.
  • 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 or atoms constituting a substituent bonded to a pyridine ring is 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.
  • the number of ring atoms in a quinazoline ring to which a hydrogen atom or a 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, unless otherwise specified in this specification, is 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, unless otherwise specified 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.
  • 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).
  • heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group” is an "unsubstituted heterocyclic group"
  • substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group” is a "substituted heterocyclic group”.
  • heterocyclic group simply includes both an "unsubstituted heterocyclic group” and a "substituted heterocyclic group”.
  • 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 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, A (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 refers to 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.
  • R a161 to R a169 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R a161 to R a169 are not bonded to each other and therefore do not form a ring structure.
  • R a161 to R a169 are preferably hydrogen atoms.
  • Ar a2 is a group represented by any one of the following formulas (a1) to (a3).
  • *a12 represents the bonding position to the central nitrogen atom N * .
  • R a101 to R a105 is a single bond bonding to *a13
  • R a106 to R a110 is a single bond bonding to *a14.
  • the R a101 to R a105 that are not a single bond, and the R a106 to R a110 that are not a single bond are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring carbon atoms.
  • any two adjacent R a101 to R a105 which are not single bonds are not bonded to each other to form a ring, Any two adjacent groups selected from R a106 to R a110 that are not single bonds are not bonded to each other to form a ring.
  • the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R a101 to R a105 which are not a single bond and R a106 to R a110 which are not a single bond is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, or a decyl group, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group,
  • the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a101 to R a105 that are not a single bond and R a106 to R a110 that are not a single bond is, for example, a phenyl group, a biphenyl group, or a naphthyl group, preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, more preferably a phenyl group, or a 1- or 2-naphthyl group, and even more preferably a phenyl group.
  • Examples of the unsubstituted heterocyclic group having 5 to 12 ring atoms represented by R a101 to R a105 which are not a single bond and R a106 to R a110 which are not a single bond include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an isopropyl group, a phenyl ...
  • Indolyl group isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, the same applies hereinafter), isobenzothiophenyl group (isobenzothienyl group, the same applies hereinafter), dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or carbazolyl group, preferably pyrrolyl group, furyl group, thien
  • Examples of the substituted heterocyclic group having 5 to 12 ring atoms include a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a 9-phenylphenylcarbazolyl group, a 9-naphthylcarbazolyl group, a phenyldibenzofuranyl group, or a phenyldibenzothiophenyl group (a phenyldibenzothienyl group, the same applies below).
  • the above-mentioned substituted or unsubstituted heterocyclic group having 5 to 12 ring atoms includes isomeric groups, when present.
  • R a111 to R a115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R a111 to R a115 are not bonded to each other to form a ring.
  • the R a101 to R a105 that are not single bonds may all be hydrogen atoms
  • the R a106 to R a110 that are not single bonds may all be hydrogen atoms
  • R a111 to R a115 may all be hydrogen atoms.
  • *a14 represents *a12;
  • *a13 represents *a12;
  • *a14 represents *a13.
  • m is 0 and n is 0.
  • *a14 represents *a12
  • formula (a1) is represented by the following formula:
  • formula (a1) is represented by the following formula:
  • the group represented by formula (a1) is preferably represented by the following formula:
  • R has been omitted for simplicity.
  • R is the same as R a101 to R a105 which are not a single bond, and R a106 to R a110 which are not a single bond, or R a111 to R a115 which are not a single bond.
  • the group represented by formula (a1) is more preferably represented by the following formula:
  • *a15 represents the bonding position to the central nitrogen atom N * .
  • R a131 to R a138 is a single bond bonded to *a16.
  • R a121 to R a124 and R a131 to R a138 that are not a single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R a121 to R a124 and R a131 to R a138 which are not a single bond are not bonded to each other to form a ring.
  • one selected from R a132 , R a133 , R a136 , and R a137 is preferably a single bond bonded to *a16.
  • All of R a121 to R a124 may be hydrogen atoms, and all of R a131 to R a138 that are not single bonds may be hydrogen atoms.
  • At least one selected from R a121 to R a124 may be a deuterium atom.
  • L a2 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 12 ring atoms.
  • the unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L a2 is, for example, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a benzoanthrylene group, a phenanthrylene group, a benzophenanthrylene group, a phenalenylene group, a picenylene group, a pentaphenylene group, a pyrenylene group, a chrysenylene group, a benzochrysenylene group, a triphenylenylene group, a fluoranthenylene group, a fluorenylene group, or a 9,9'-spirobifluorenylene group, preferably a phenylene group, a biphenylene group, a terphenylene group, or a naphthylene group, more preferably a
  • the unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by L a2 is a divalent group obtained by removing one hydrogen atom from an unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • All of the hydrogen atoms in the compound represented by formula (A) may be deuterium atoms.
  • R 901 to R 905 Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • the R b41 to R b45 that are not single bonds may all be hydrogen atoms, and the R b51 to R b58 that are not single bonds may all be hydrogen atoms.
  • Ar b1 is preferably a group represented by any one of the following formulas (b1) to (b6), and more preferably a group represented by the following formula (b2).
  • *b8 is the bonding position to L b1 .
  • One selected from R b101 to R b105 is a single bond bonded to *b9, and one selected from R b106 to R b110 is a single bond bonded to *b10.
  • the R b101 to R b105 and R b106 to R b110 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. Any two adjacent groups selected from R b101 to R b105 that are not single bonds are not bonded to each other to form a ring. Any two adjacent groups selected from R b106 to R b110 that are not single bonds are not bonded to each other to form a ring.
  • R b111 to R b115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R b111 to R b115 are not bonded to each other to form a ring.
  • R b111 to R b115 Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R b111 to R b115 and preferred examples thereof are as described above for R a101 to R a105 which are not a single bond, and R a106 to R a110 which are not a single bond.
  • n is 0 or 1.
  • *b10 represents *b8.
  • *b9 represents *b8.
  • *b10 represents *b9.
  • m is 0 and n is 0.
  • *b10 represents *b8
  • formula (b1) is represented by the following formula.
  • n 0 and n is 1.
  • *b9 represents *b8
  • formula (b1) is represented by the following formula:
  • n 1 and n is 0.
  • *b10 represents *b9
  • formula (b1) is represented by the following formula:
  • formula (b1) is represented by the following formula:
  • n 2 and n is 0.
  • *b10 represents *b9
  • formula (b1) is represented by the following formula:
  • formula (b1) is represented by the following formula:
  • the group represented by formula (b1) is preferably represented by the following formula:
  • R has been omitted for simplicity.
  • R is the same as R b101 to R b105 and R b106 to R b110 , or R b111 to R b115 .
  • the group represented by formula (b1) is more preferably represented by the following formula:
  • *b11 is the bonding position to L b1 .
  • One selected from R b121 to R b128 is a single bond bonded to *b12.
  • the R b121 to R b128 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. Any two adjacent groups selected from R b121 to R b128 that are not single bonds are not bonded to each other to form a ring.
  • R b122 , R b123 , R b126 , and R b127 is a single bond bonding to *b12.
  • R b121 to R b128 that are not single bonds bonded to b12 may all be hydrogen atoms.
  • *b13 is the bonding position to L b1 .
  • One selected from R b131 to R b140 is a single bond bonded to *b14.
  • the R b131 to R b140 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. Any two adjacent groups selected from R b131 to R b140 that are not single bonds are not bonded to each other to form a ring.
  • R b137 , R b138 and R b139 is a single bond bonded to *b14.
  • R b131 to R b140 that are not a single bond bonded to b14 may all be hydrogen atoms.
  • *b15 is the bonding position to L b1 .
  • X b1 is an oxygen atom, a sulfur atom, CR A R B , or NR C.
  • R A and R B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 18, more preferably 3 to 10, and even more preferably 3 to 6 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, which may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore not form a ring.
  • the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R A and R B is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group, more preferably a methyl group, an
  • the unsubstituted monocyclic ring formed by R 2 A and R 2 B is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring.
  • the unsubstituted fused ring formed by R 2 A and R 2 B is, for example, a naphthalene ring or an anthracene ring.
  • R A and R B when R A and R B are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R A and R B may form a ring with the fluorene skeleton to which they are bonded to form a spiro ring.
  • the spiro ring is a hydrocarbon ring or a heterocyclic ring, and is selected from a monocyclic ring, a condensed ring, a bridged bicyclo ring, and a bridged tricyclo ring. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited to these. * indicates the bonding position of the fluorene skeleton to the benzene ring.
  • R C is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 13 ring atoms.
  • l is 0 or 1.
  • one selected from R A , R B , R C , and R b141 to R b148 is a single bond bonded to *b16, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which can be represented by R A or R B , a substituted or unsubstituted ring structure which can be formed by R A or R B bonding to each other, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which can be represented by R C is bonded to *b16 via a single bond.
  • R b141 and R b142 , R b142 and R b143 , or R b143 and R b144 is a single bond bonding to *a and the other is a single bond bonding to *b
  • the R b141 to R b148 that are not single bonds, and the R b200 to R b203 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from among R b141 to R b148 which are not a single bond, and R b200 to R b203 which are not a single bond, are not bonded to each other to form a ring.
  • the R b141 to R b148 that are not single bonds may all be hydrogen atoms, and the R b200 to R b203 that are not single bonds may all be hydrogen atoms.
  • *b17 is the bonding position to L b1 .
  • One selected from R b151 to R b155 is a single bond bonded to *b18, and the other selected from R b151 to R b155 is a single bond bonded to *b19.
  • the R b151 to R b155 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6, and more preferably 1 to 3 carbon atoms, or an unsubstituted phenyl group. Any two adjacent groups selected from R b151 to R b155 which are not single bonds are not bonded to each other to form a ring.
  • R b161 to R b165 and R b171 to R b175 each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. At least one adjacent two selected from R b161 to R b165 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring. At least one adjacent two selected from R b171 to R b175 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.
  • the R b151 to R b155 that are not single bonds may all be hydrogen atoms
  • the R b161 to R b165 that are not single bonds may all be hydrogen atoms
  • the R b171 to R b175 that are not single bonds may all be hydrogen atoms.
  • *b20 is the bonding position to L b1 .
  • One selected from R b181 to R b192 is a single bond bonded to *b21.
  • the R b181 to R b192 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. Any two adjacent groups selected from R b181 to R b192 that are not single bonds are not bonded to each other to form a ring.
  • All of R b181 to R b192 that are not single bonds may be hydrogen atoms.
  • R b1 to R b4 are each a hydrogen atom.
  • R b11 to R b17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50, preferably 1 to 20, and more preferably 1 to 6 carbon atoms; Any two adjacent groups selected from R b11 to R b17 are not bonded to each other to form a ring. Ring C and ring D may or may not be bridged.
  • All of R b11 to R b17 may be hydrogen atoms.
  • the ring structure formed by crosslinking ring C and ring D is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluoranthene structure, preferably a dibenzofuran structure.
  • R b21 to R b24 and R b31 to R b38 each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 50, preferably 1 to 20, and more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50, preferably 2 to 20, and more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50, preferably 2 to 20, and more preferably 2 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50, preferably 6 to 30, and more
  • R b21 to R b24 and R b31 to R b38 are as described above for R a21 to R a25 that are not a single bond, and R a31 to R a38 that are not a single bond.
  • R b21 to R b24 and R b31 to R b38 Details of the unsubstituted alkenyl group having 2 to 50 carbon atoms represented by R b21 to R b24 and R b31 to R b38 are as described above for R a21 to R a25 that are not a single bond, and R a31 to R a38 that are not a single bond.
  • R b21 to R b24 and R b31 to R b38 are as described above for R a21 to R a25 that are not a single bond, and R a31 to R a38 that are not a single bond.
  • halogen atoms represented by R b21 to R b24 and R b31 to R b38 are as described above for R a21 to R a25 that are not a single bond, and R a31 to R a38 that are not a single bond.
  • R 901 to R 905 Details of the unsubstituted alkyl group having 1 to 50 carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • R 901 to R 905 Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • the R b21 to R b24 and R b31 to R b38 are each independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R b21 to R b24 that are not single bonds may all be hydrogen atoms, and R b31 to R b38 may all be hydrogen atoms.
  • the compound represented by formula (B) may contain at least one deuterium atom.
  • at least one selected from R b1 to R b4 may be a deuterium atom
  • L b1 may have at least one deuterium atom
  • R b1 to R b4 may all be deuterium atoms
  • L b1 may be a group represented by formula (iv)
  • R b41 to R b45 may all be deuterium atoms.
  • invention compound (C) is represented by the following formula (C).
  • N * is the central nitrogen atom.
  • L c1 is a single bond or a group represented by the following formula (vi) or (vii).
  • one selected from R c31 to R c35 is a single bond bonded to *c2
  • One selected from R c41 to R c48 is a single bond bonded to *c5
  • the other selected from R c41 to R c48 is a single bond bonded to *c6.
  • R c33 is preferably a single bond bonded to *c2.
  • the R c31 to R c35 which are not single bonds and the R c41 to R c48 which are not single bonds each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 50, preferably 1 to 20, and more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50, preferably 2 to 20, and more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50, preferably 2 to 20, and more preferably 2 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group
  • *c1 and *c4 represent the bonding positions to the central nitrogen atom N * ;
  • *c3 and *c7 represent the bonding positions to ring G. Any adjacent two selected from among R c31 to R c35 which are not a single bond and R c41 to R c48 which are not a single bond are not bonded to each other to form a ring.
  • R c31 to R c35 which are not single bonds and R c41 to R c48 which are not single bonds are as described above for R a21 to R a25 which are not single bonds and R a31 to R a38 which are not single bonds.
  • R 901 to R 905 Details of the unsubstituted alkyl group having 1 to 50 carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • R 901 to R 905 Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • the R c31 to R c35 that are not single bonds, and the R c41 to R c48 that are not single bonds are each independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • the R c31 to R c35 that are not single bonds may all be hydrogen atoms, and the R c41 to R c48 that are not single bonds may all be hydrogen atoms.
  • L c1 is preferably a single bond. In another embodiment of the present invention, L c1 is preferably a group represented by formula (vi).
  • Ar c1 is a group represented by the following formula (c1) or (c2).
  • L c2 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 12 ring atoms.
  • L c2 is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, even more preferably a substituted or unsubstituted phenylene group, still more preferably a substituted or unsubstituted p-phenylene group, and still more preferably an unsubstituted p-phenylene group.
  • R c101 to R c108 is a single bond bonded to *c9.
  • the R c101 to R c108 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R c101 to R c108 that are not single bonds are not bonded to each other to form a ring.
  • L c2 is a substituted or unsubstituted phenylene group, and one selected from R c101 , R c104 , R c105 , and R c108 is a single bond bonded to *c9
  • the substituted or unsubstituted phenylene group represented by L c2 is a substituted or unsubstituted o-phenylene group, or a substituted or unsubstituted m-phenylene group.
  • one selected from R c102 , R c103 , R c106 , and R c107 is preferably a single bond bonded to *c9.
  • R c101 to R c108 which are not a single bond are as described above for R a101 to R a105 which are not a single bond, and R a106 to R a110 which are not a single bond.
  • All of the R c101 to R c108 that are not single bonds may be hydrogen atoms.
  • L c3 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 12 ring atoms.
  • L c3 is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, even more preferably a substituted or unsubstituted phenylene group, still more preferably a substituted or unsubstituted p-phenylene group, and still more preferably an unsubstituted p-phenylene group.
  • Ar c1 is preferably a group represented by the above formula (c1).
  • Xc1 is an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • R c111 to R c118 is a single bond bonded to *c11.
  • the R c111 to R c118 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R c111 to R c118 that are not single bonds may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore not form a ring structure.
  • the details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by the R c111 to R c118 that are not a single bond are as described above for the R a101 to R a105 that are not a single bond and the R a106 to R a110 that are not a single bond.
  • All of the R c111 to R c118 that are not single bonds may be hydrogen atoms.
  • R c1 to R c4 are each a hydrogen atom.
  • R c11 to R c17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50, preferably 1 to 20, and more preferably 1 to 6 carbon atoms; Any two adjacent groups selected from R c11 to R c17 are not bonded to each other to form a ring. Ring E and ring F may or may not be bridged.
  • All of R c11 to R c17 may be hydrogen atoms.
  • the ring structure formed by crosslinking ring E and ring F is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluoranthene structure, preferably a dibenzofuran structure.
  • R c21 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
  • R c21 is preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group.
  • R c22 to R c29 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • All of R c22 to R c29 may be hydrogen atoms.
  • the compound represented by formula (C) may contain at least one deuterium atom.
  • the compound represented by formula (C) contains a deuterium atom, at least one selected from R c1 to R c4 is a deuterium atom, Ar c1 is a group represented by formula (c1), L c2 may have at least one deuterium atom, R c1 to R c4 are all deuterium atoms, Ar c1 is a group represented by formula (c1), L c2 is an unsubstituted arylene group having 6 to 30 ring carbon atoms, and all of the hydrogen atoms possessed by the unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L c2 may be deuterium atoms.
  • invention compound (D) is represented by the following formula (D).
  • N * is the central nitrogen atom.
  • L d1 is a group represented by the following formula (viii).
  • R d31 and R d35 are a single bond bonding to *d3.
  • R d31 to R d35 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50, preferably 1 to 20, and more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50, preferably 2 to 20, and more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50, preferably 2 to 20, and more preferably 2 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50, preferably 6 to 30, and more preferably 6 to 18
  • *d2 represents the bonding position to the central nitrogen atom N * , *d1 bonds to one selected from R d21 to R d28 . Any two adjacent groups selected from R d31 to R d35 which are not single bonds are not bonded to each other to form a ring.
  • halogen atom represented by R d31 to R d35 which are not a single bond and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond and R a31 to R a38 which are not a single bond.
  • R 901 to R 905 Details of the unsubstituted alkyl group having 1 to 50 carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • R 901 to R 905 Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R 901 to R 905 and preferred examples thereof are as described above for R a21 to R a25 which are not a single bond, and R a31 to R a38 which are not a single bond.
  • the R d31 to R d35 that are not single bonds are each independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • All of R d31 to R d35 that are not single bonds may be hydrogen atoms.
  • Ar d1 is a group represented by any one of the following formulas (d1) to (d3), and is preferably a group represented by the following formula (d2).
  • *d7 represents the bonding position to the central nitrogen atom N * .
  • R d101 to R d105 is a single bond bonded to *d8
  • R d106 to R d110 is a single bond bonded to *d9.
  • the R d101 to R d105 and R d106 to R d110 that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
  • Any two adjacent groups selected from R d101 to R d105 that are not single bonds are not bonded to each other to form a ring. Any two adjacent groups selected from R d106 to R d110 that are not single bonds are not bonded to each other to form a ring.
  • R d101 to R d105 that are not single bonds
  • R d106 to R d110 that are not single bonds
  • R d111 to R d115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R d111 to R d115 are not bonded to each other to form a ring.
  • R d111 to R d115 Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R d111 to R d115 and preferred examples thereof are as described above for R a101 to R a105 which are not a single bond, and R a106 to R a110 which are not a single bond.
  • R d111 to R d115 Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R d111 to R d115 and preferred examples thereof are as described above for R a101 to R a105 which are not a single bond, and R a106 to R a110 which are not a single bond.
  • the R d101 to R d105 that are not single bonds may all be hydrogen atoms
  • the R d106 to R d110 that are not single bonds may all be hydrogen atoms
  • R d111 to R d115 may all be hydrogen atoms.
  • *d9 represents *d7;
  • *d8 represents *d7;
  • *d9 represents *d8.
  • n 0 and n is 0.
  • *d9 represents *d7
  • formula (d1) is represented by the following formula:
  • n 0 and n is 1.
  • *d8 represents *d7
  • formula (d1) is represented by the following formula:
  • formula (d1) is represented by the following formula:
  • n 2 and n is 0.
  • *d9 represents *d8
  • formula (d1) is represented by the following formula:
  • formula (d1) is represented by the following formula:
  • the group represented by formula (d1) is preferably represented by the following formula:
  • R is omitted for simplicity.
  • R is the same as R d101 to R d105 and R d106 to R d110 , or R d111 to R d115 .
  • the group represented by formula (d1) is more preferably represented by the following formula:
  • L d2 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 12 ring atoms.
  • L d2 is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, even more preferably a substituted or unsubstituted phenylene group, still more preferably a substituted or unsubstituted p-phenylene group, and still more preferably an unsubstituted p-phenylene group.
  • the R d121 to R d128 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. Any two adjacent groups selected from R d121 to R d128 that are not single bonds are not bonded to each other to form a ring.
  • R d122 , R d123 , R d126 , and R d127 is a single bond bonding to *b12.
  • R d121 to R d128 which are not single bonds bonded to d11 may all be hydrogen atoms.
  • L d3 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 12 ring atoms.
  • L d3 is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, even more preferably a substituted or unsubstituted phenylene group, still more preferably a substituted or unsubstituted p-phenylene group, and still more preferably an unsubstituted p-phenylene group.
  • Xd1 is an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • R d131 to R d138 is a single bond bonded to *c11.
  • the R d131 to R d138 that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, and more preferably 1 to 3, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. Any two adjacent groups selected from R d131 to R d138 that are not single bonds may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore not form a ring structure.
  • R d131 to R d138 which are not a single bond are as described above for R a101 to R a105 which are not a single bond, and R a106 to R a110 which are not a single bond.
  • All of R d131 to R d138 that are not single bonds may be hydrogen atoms.
  • R d1 to R d4 are each a hydrogen atom.
  • R d11 to R d17 each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50, preferably 1 to 20, and more preferably 1 to 6 carbon atoms; Any two adjacent groups selected from R d11 to R d17 are not bonded to each other to form a ring. Ring H and ring I may or may not be bridged.
  • All of R d11 to R d17 may be a hydrogen atom.
  • the ring structure formed by bridging ring H and ring I is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluoranthene structure, preferably a dibenzofuran structure.
  • R d21 to R d28 that are not single bonds bonded to d1 each independently represent a hydrogen atom or a substituted or unsubstituted aryl group having 6 ring carbon atoms
  • R d21 to R d28 that is not a single bond bonded to d1 is the above-mentioned substituted or unsubstituted aryl group having 6 ring carbon atoms.
  • the unsubstituted aryl group having 6 ring carbon atoms represented by R d21 to R d28 is, for example, a phenyl group.
  • At least one selected from R d21 , R d24 , R d25 , and R d28 is the substituted or unsubstituted aryl group having 6 ring carbon atoms, and it is more preferable that one selected from R d21 , R d24 , R d25 , and R d28 is the substituted or unsubstituted aryl group having 6 ring carbon atoms.
  • the compound represented by formula (D) may contain at least one deuterium atom.
  • at least one selected from R d1 to R d4 may be a deuterium atom
  • Ar d1 is a group represented by formula (d2)
  • L d2 may have at least one deuterium atom
  • R d1 to R d4 are all deuterium atoms
  • Ar d1 is a group represented by formula (d2)
  • L d2 is an unsubstituted arylene group having 6 to 30 ring carbon atoms
  • all of the hydrogen atoms possessed by the unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L d2 may be deuterium atoms.
  • 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 invention compound by using a compound in which some or all of the raw material compounds are deuterated.
  • the invention compound may be a compound represented by formula (A) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom
  • the invention compound may be a compound represented by formula (B) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom
  • the invention compound may be a compound represented by formula (C) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom
  • the invention compound may be a compound represented by formula (D) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.
  • At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom.
  • a hydrogen atom held by a group represented by any one of formulas (i) to (iii) represented by L a1 in formula (A) a hydrogen atom held by a phenyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group, or a naphthobenzothiophenyl group represented by Ar a1 in formula (A); a hydrogen atom held by a group represented by any one of formulas (a1) to (a3) represented by Ar a2 in formula (A); A hydrogen atom represented by any of R a1 to R a4 in formula (A); a hydrogen atom represented by any of R a1 to R a4 in formula (A); a hydrogen atom represented
  • the deuteration rate of the invention 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 of the invention compound 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.
  • the deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.
  • the invention compound may be a mixture containing deuterated and non-deuterated compounds, or a mixture of two or more compounds having different deuteration ratios, preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more, but less than 100%.
  • the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and still more preferably 10% or more and 100% or less.
  • substituted XX group included in the definition of each formula above is a substituted XX group
  • the details of the substituent are as described in "Substituents when “substituted or unsubstituted” is used", and are preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or a heterocyclic group (heteroaryl group) having 5 to 13 ring atoms, and more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms.
  • the details of each group are as described above.
  • D represents a deuterium atom.
  • the material for organic EL device of the present invention contains the compound of the present invention.
  • the content of the compound of the present invention in the material for organic EL device is 1 mass% or more (including 100%), preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), further preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%).
  • the material for organic EL device of the present invention is useful for manufacturing an organic EL device.
  • the organic EL device of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer comprises a light-emitting layer, and at least one of the organic layers comprises the compound of the present invention.
  • the organic layer containing the compound of the invention include, but are not limited to, a hole transport zone (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer, a light emitting layer, a spacer layer, an electron transport zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer, etc.
  • the compound of the invention is preferably used as a material for the hole transport zone or light emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transport zone, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.
  • the organic EL element of the present invention may be a monochromatic fluorescent or phosphorescent light-emitting element, a fluorescent/phosphorescent hybrid white light-emitting element, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and is preferably a fluorescent light-emitting element.
  • the term "light-emitting unit” refers to the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by recombining injected holes and electrons.
  • the light-emitting unit may be a multi-layer type having a plurality of phosphorescent or fluorescent light-emitting layers, in which case a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer.
  • a typical layer structure of a simple light-emitting unit is shown below. The layers in parentheses are optional.
  • the phosphorescent or fluorescent light-emitting layers may each emit light of a different color.
  • the light-emitting unit (f) may have a layer structure such as a hole injection layer/hole transport layer/first phosphorescent light-emitting layer (red light-emitting)/second phosphorescent light-emitting layer (green light-emitting)/spacer layer/fluorescent light-emitting layer (blue light-emitting)/electron transport layer.
  • an electron blocking layer (sometimes referred to as an electron block layer) may be provided between each light-emitting layer and the hole transport layer or the space layer as appropriate.
  • a hole blocking layer may be provided between each light-emitting layer and the electron transport layer as appropriate.
  • a hole transport layer adjacent to a light emitting layer in a multilayer structure including two or more hole transport layers may have a function as an electron blocking layer.
  • the hole transport layer adjacent to the light emitting layer in the multilayer structure can also be used as an electron blocking layer.
  • Representative element configurations of the tandem type organic EL element include the following.
  • the first light-emitting unit and the second light-emitting unit can be, for example, each independently selected from the light-emitting units described above.
  • the intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, or intermediate insulating layer, and can be made of a known material configuration that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.
  • FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element of the present invention.
  • the organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 arranged between the anode 3 and the cathode 4.
  • the light-emitting unit 10 has a light-emitting layer 5.
  • a hole transport zone 6 (hole injection layer, hole transport layer, etc.) is between the light-emitting layer 5 and the anode 3
  • an electron transport zone 7 electron injection layer, electron transport layer, etc.
  • an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. This allows electrons and holes to be trapped in the light-emitting layer 5, further increasing the efficiency of exciton generation in the light-emitting layer 5.
  • FIG. 2 is a schematic diagram showing another configuration of the organic EL element of the present invention.
  • the organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4.
  • the light-emitting unit 20 has a light-emitting layer 5.
  • the hole transport zone disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c.
  • the electron transport zone disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.
  • FIG. 3 is a schematic diagram showing another configuration of the organic EL element of the present invention.
  • the organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4.
  • the light-emitting unit 30 has a light-emitting layer 5.
  • the hole transport zone disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d.
  • the electron transport zone disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.
  • the substrate is used as a support for the organic EL element.
  • a plate such as glass, quartz, or plastic can be used as the substrate.
  • a flexible substrate may also be used.
  • a plastic substrate made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride can be used as the flexible substrate.
  • An inorganic deposition film can also be used.
  • 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, indium oxide containing tungsten oxide and zinc oxide, and graphene.
  • indium oxide-zinc oxide can be formed by sputtering using a target in which 1-10 wt% zinc oxide is added to indium oxide
  • indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target in which 0.5-5 wt% tungsten oxide and 0.1-1 wt% zinc oxide are added to indium oxide.
  • Other methods that can be used to form the films include vacuum deposition, coating, inkjet, and spin coating.
  • the organic layer may include a hole transport zone between the anode and the light emitting layer.
  • the hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport zone contains the invention compound. It is preferable that at least one of these layers constituting the hole transport layer contains the invention compound, and it is more preferable that the invention compound is contained in the hole transport layer.
  • the hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials that are commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and elements belonging to Group 1 or Group 2 of the periodic table) can be used.
  • electrode materials e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and elements belonging to Group 1 or Group 2 of the periodic table
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these
  • a vacuum deposition method or a sputtering method can be used.
  • silver paste a coating method, an inkjet method, or the like can be used.
  • the hole injection layer is a layer containing a material with high hole injection properties (hole-injecting material) and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.
  • hole injection materials examples 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, etc.
  • Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • examples include polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino ⁇ phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD).
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl
  • Polymer compounds to which an acid has been added such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.
  • PEDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • R 221 to R 226 each independently represent a cyano group, -CONH 2 , a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms).
  • R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 may be bonded to each other to form a group represented by -CO-O-CO-.
  • R 227 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the hole transport layer is a layer containing a material with high hole transport properties (hole transport material) and is formed between the anode and the light emitting layer, or, if present, between the hole injection layer and the light emitting layer.
  • the invention compound may be used in the hole transport layer alone or in combination with the following compounds:
  • the hole transport layer of the single layer structure is preferably adjacent to the light emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light emitting layer.
  • an electron blocking layer which will be described later, may be interposed between the hole transport layer and the light emitting layer of the single layer structure, or between the hole transport layer closest to the light emitting layer in the multilayer structure and the light emitting layer.
  • the hole transport layer has a two-layer structure
  • at least one of the first hole transport layer and the second hole transport layer contains the compound of the invention, i.e., the compound of the invention is contained only in the first hole transport layer, only in the second hole transport layer, or both in the first hole transport layer and the second hole transport layer.
  • the compound of the present invention is preferably contained in the second hole transport layer, i.e., the compound of the present invention is preferably contained only in the second hole transport layer, or the compound of the present invention is preferably contained in both the first hole transport layer and the second hole transport layer.
  • the hole transport layer has a three-layer structure
  • at least one of the first to third hole transport layers contains the compound of the invention.
  • the compound of the invention is contained in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), only two layers selected from the first to third hole transport layers (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer and the third hole transport layer), or all of the first to third hole transport layers.
  • the compound of the present invention is preferably contained in the third hole transport layer, i.e., the compound of the present invention is preferably contained only in the third hole transport layer, or the compound of the present invention is preferably contained in the third hole transport layer and one or both of the first hole transport layer and the second hole transport layer.
  • the invention compound contained in each of the hole transport layers is preferably a protium compound from the viewpoint of production cost.
  • the protium compound is an invention compound in which all hydrogen atoms are protium atoms.
  • the present invention includes an organic EL device in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure) and at least one of the first to third hole transport layers contain an invention compound substantially consisting of protium compounds.
  • invention compound substantially consisting of protium compounds means that the content of protium compounds relative to the total amount of the invention compound is 90 mol % or more, preferably 95 mol % or more, and more preferably 99 mol % or more (each including 100%).
  • aromatic amine compounds examples include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl] )-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphen
  • carbazole derivatives examples include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
  • anthracene derivatives examples include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).
  • Polymer compounds 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)
  • compounds other than those mentioned above may be used as long as they have a higher hole transporting property than an electron transporting property.
  • the first hole transport layer preferably contains one or more compounds represented by the following formula (11) or formula (12).
  • the organic EL element of the present invention having a three-layer hole transport layer structure it is preferable that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formula (11) or (12).
  • the organic EL element of the present invention having a hole transport layer of an n-layer structure (n is an integer of 4 or more), it is preferable that at least one of the first hole transport layer to the (n-1)th hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).
  • L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
  • k is 1, 2, 3 or 4;
  • L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
  • 2, 3, or 4 L E2 are identical or different from each other; when k is 2, 3 or 4, multiple L E2s are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring
  • A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
  • At least one of A1, B1, and C1 in formula (11), and at least one of A2, B2, C2, and D2 in formula (12) are a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
  • the fluorenyl group that can be A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group.
  • the substituents at the 9-position may form a ring together, for example, a fluorene skeleton or a xanthene skeleton together.
  • Blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc.
  • Aromatic amine derivatives and the like can be used as green fluorescent light-emitting materials that can be used in the light-emitting layer.
  • 2PCAPA N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine
  • 2PCABPhA N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine
  • 2DPAPA N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine
  • 2DPAPA N-[9 ,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine
  • 2DPAPA N-[9 ,10-bis(1,1'-b
  • Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials that can be used in the light-emitting layer.
  • Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc.
  • the light-emitting layer contains a fluorescent material (fluorescent dopant material).
  • Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer.
  • examples include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinato-N
  • Iridium complexes are used as green phosphorescent materials that can be used in the light-emitting layer.
  • examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).
  • organometallic complex examples include bis[2-(2'-benzo[4,5- ⁇ ]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,
  • rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propandionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electron transition between different multiplicities).
  • the light-emitting layer may have a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.
  • LUMO lowest unoccupied molecular orbital
  • HOMO lower highest occupied molecular orbital
  • Examples of the host material include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives, (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; (4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.
  • metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
  • Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives
  • Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene
  • metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl
  • the organic EL element when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer.
  • the dopant material contained in the first light-emitting layer may be different from the dopant material contained in the second light-emitting layer, or the host material contained in the first light-emitting layer may be different from the host material contained in the second light-emitting layer.
  • the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less (hereinafter, sometimes simply referred to as a "fluorescent compound").
  • the method for measuring the main peak wavelength of a compound is as follows. A 5 ⁇ mol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum is defined as the main peak wavelength. Note that in this specification, the main peak wavelength may be referred to as the fluorescent emission main peak wavelength (FL-peak).
  • the fluorescent compound may be the dopant material or the host material.
  • the light-emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent compound, or both of them may be the fluorescent compound.
  • the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side)
  • only one of the first light-emitting layer and the second light-emitting layer may contain the fluorescent compound, or both light-emitting layers may contain the fluorescent compound.
  • the first light-emitting layer includes the fluorescent compound
  • only one of the dopant material and the host material included in the first light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound.
  • the second light-emitting layer includes the fluorescent compound, only one of the dopant material and the host material included in the second light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound.
  • the electron transporting zone is composed of an electron injection layer, an electron transporting layer, a hole blocking layer, etc.
  • Any layer of the electron transporting zone, particularly the electron transporting layer preferably contains one or more selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex containing an alkali metal, an organic complex containing an alkaline earth metal, and an organic complex containing a rare earth metal.
  • the electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer.
  • the electron transport layer may be a single-layer structure or a multi-layer structure including two or more layers.
  • the electron transport layer may be a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side).
  • the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer.
  • a hole blocking layer which will be described later, may be interposed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.
  • metal complexes examples include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).
  • Alq tris(8-quinolinolato)aluminum(III)
  • heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2 ,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxa
  • polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).
  • the electron injection layer is a layer containing a material with high electron injection properties.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • rare earth metals such as europium (Eu), ytterbium (Yb)
  • compounds containing these metals can be used.
  • examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes.
  • a mixture of a plurality of these compounds can also be used.
  • a material having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq, etc. may be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the received electrons, and specifically, for example, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used.
  • the electron donor may be any material that exhibits electron donating properties to the organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of such materials include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferred, and examples of such materials include lithium oxide, calcium oxide, and barium oxide.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • Cathode For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof, each having a small work function (specifically, 3.8 eV or less).
  • cathode materials 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.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as
  • the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.
  • Insulating Layer Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to an ultra-thin film.
  • an insulating layer made of an insulating thin film may be inserted between a pair of electrodes.
  • materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Mixtures or laminates of these materials may also be used.
  • the space layer is a layer provided between a fluorescent light-emitting layer and a phosphorescent light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or for the purpose of adjusting the carrier balance, for example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are laminated.
  • the space layer can also be provided between a plurality of phosphorescent light-emitting layers. Since the spacer layer is provided between the light-emitting layers, it is preferable that the spacer layer is made of a material having both electron transport properties and hole transport properties.
  • the triplet energy is 2.6 eV or more.
  • materials used for the spacer layer include the same materials as those used for the hole transport layer described above.
  • Blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer.
  • the electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer
  • the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer.
  • the exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and trapping the excitons within the light-emitting layer.
  • the layers of the organic EL element can be formed by a conventionally known deposition method, coating method, etc.
  • they can be formed by a conventional deposition method such as vacuum deposition method or molecular beam deposition method (MBE method), or a coating method such as dipping method, spin coating method, casting method, bar coating method, roll coating method, etc., using a solution of a compound that forms the layer.
  • a conventional deposition method such as vacuum deposition method or molecular beam deposition method (MBE method)
  • MBE method molecular beam deposition method
  • a coating method such as dipping method, spin coating method, casting method, bar coating method, roll coating method, etc., using a solution of a compound that forms the layer.
  • each layer there are no particular limitations on the thickness of each layer, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, while if it is too thick, a high driving voltage is required, resulting in poor efficiency, so the thickness is usually 5 nm to 10 ⁇ m, and 10 nm to 0.2 ⁇ m is more preferable.
  • the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 30 nm or more, and is preferably 100 nm or less.
  • the ratio of the thickness D2 of the second hole transport layer to the thickness D1 of the first hole transport layer is preferably 0.3 ⁇ D2/D1 ⁇ 4.0, more preferably 0.5 ⁇ D2/D1 ⁇ 3.5, and even more preferably 0.75 ⁇ D2/D1 ⁇ 3.0.
  • the organic EL element according to one embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices.
  • display devices include display components such as organic EL panel modules, televisions, mobile phones, tablets, and personal computers.
  • light-emitting devices include lighting and vehicle lamps.
  • the organic EL element can be used in display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, etc., and electronic devices such as lighting and light-emitting devices for vehicle lamps.
  • Example 1 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm ⁇ 75 mm ⁇ 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 washed glass substrate with the ITO transparent electrode was attached to a substrate holder of a vacuum deposition apparatus, and the compounds HT-1 and HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm.
  • the mass ratio of the compounds HT-1 and HA was 97:3.
  • compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 85 nm.
  • the compound Inv-1 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm.
  • the compound BH-1 (host material) and the compound BD-1 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm.
  • the mass ratio of the compound BH-1 to the compound BD-1 was 99:1.
  • the compound ET-1 was evaporated on this light-emitting layer to form a first electron transport layer having a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 31 nm.
  • the mass ratio of the compound ET-2 to Liq (ET-2:Liq) was 50:50.
  • Liq was evaporated onto the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
  • metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 80 nm.
  • the layer structure of the thus obtained organic EL element (I) is shown below.
  • Examples 2 to 8 and Comparative Examples 1 and 2 An organic EL element (I) was prepared in the same manner as in Example 1, except that a compound shown in Table 1 was used instead of compound Inv-1 as the material for the second hole transport layer.
  • the organic EL element (I) containing the inventive compounds has a longer life than the organic EL element (I) containing the comparative compound Ref-1 or comparative compound Ref-2.
  • Example 9 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm ⁇ 75 mm ⁇ 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 glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound HT-2 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm.
  • the mass ratio of the compound HT-2 to the compound HA was 97:3.
  • compound HT-2 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 85 nm.
  • the compound Inv-4 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
  • the compound BH-1 (host material) and the compound BD-2 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm.
  • the mass ratio of the compound BH-1 to the compound BD-2 was 99:1.
  • the compound ET-1 was evaporated on this light-emitting layer to form a first electron transport layer having a thickness of 5 nm.
  • the compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 31 nm.
  • the mass ratio of the compound ET-2 to Liq (ET-2:Liq) was 50:50.
  • Liq was evaporated onto the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
  • metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 50 nm.
  • the layer structure of the thus obtained organic EL element (II) is shown below.
  • Examples 10 to 16 and Comparative Examples 3 to 5 An organic EL element (II) was prepared in the same manner as in Example 9, except that a compound shown in Table 2 was used instead of compound Inv-4 as the second hole transport layer material.
  • the organic EL element (II) thus obtained was driven with a direct current at a current density of 30 mA/ cm2 , and the time until the luminance decreased to 95% of the initial luminance was measured, which was taken as the 95% lifetime (LT95).
  • the results are shown in Table 2.
  • the organic EL element (II) containing the inventive compound has a longer life than the organic EL element (II) containing the comparative compound Ref-3, comparative compound Ref-4, or comparative compound Ref-5.
  • Synthesis Examples 2 to 17 Synthesis of invention compounds Inv-2 to Inv-17 Invention compounds Inv-2 to Inv-17 were obtained by the same procedure as in Synthesis Example 1, except that intermediates 1 and 2 were replaced with the compounds and amounts shown in Tables 4 to 6. The yields of invention compounds Inv-2 to Inv-17 are shown in Tables 4 to 6, respectively.

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