WO2022270602A1 - 有機発光素子および膜 - Google Patents

有機発光素子および膜 Download PDF

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WO2022270602A1
WO2022270602A1 PCT/JP2022/025197 JP2022025197W WO2022270602A1 WO 2022270602 A1 WO2022270602 A1 WO 2022270602A1 JP 2022025197 W JP2022025197 W JP 2022025197W WO 2022270602 A1 WO2022270602 A1 WO 2022270602A1
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substituted
general formula
ring
atom
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French (fr)
Japanese (ja)
Inventor
誠 吉▲崎▼
ソンヘ ファン
京 森本
礼隆 遠藤
公之 黒瀧
幸誠 金原
勇人 垣添
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Kyulux Inc
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Kyulux Inc
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Priority to EP22828518.5A priority Critical patent/EP4362120A4/en
Priority to JP2023530130A priority patent/JPWO2022270602A1/ja
Priority to US18/572,986 priority patent/US20250133962A1/en
Priority to CN202280043922.3A priority patent/CN117561805A/zh
Priority to KR1020237044674A priority patent/KR20240026148A/ko
Publication of WO2022270602A1 publication Critical patent/WO2022270602A1/ja
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to organic light-emitting devices and films having good light-emitting properties.
  • Non-Patent Document 1 compounds exhibiting multiple resonance effects such as 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (DABNA-1) It is described that heat-activated delayed fluorescence due to the reverse intersystem crossing process is exhibited by using , and light emission with a narrow half-value width and high color purity is realized. Such luminescence is useful in display-oriented applications because high luminous efficiency can be achieved.
  • DABNA-1 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine
  • Non-Patent Documents 1 and 2 describe that by modifying DABNA-1, energy levels such as the highest transcribed molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are adjusted, and also contribute to light emission. It is described that the fluorescence emission process and the reverse intersystem crossover process are promoted to improve the electroluminescence quantum efficiency.
  • HOMO highest transcribed molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • the present inventors found that among compounds exhibiting a multiple resonance effect, those having a specific structure have excellent luminescence properties. The inventors have also found that the excellent light-emitting properties can be further improved by using them in combination with a material having a specific structure.
  • the present invention has been proposed based on such findings, and has the following configurations.
  • General formula (1) one of X 1 and X 2 is a nitrogen atom, and the other is a boron atom.
  • R 1 to R 26 , A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 are bonded together to form a cyclic It may form a structure.
  • X 1 is a nitrogen atom
  • R 7 and R 8 and R 21 and R 22 are bonded through the nitrogen atom to form a 6-membered ring
  • R 17 and R 18 are bonded together to form a single bond at least one of R 1 to R 6 is a substituted or unsubstituted aryl group, or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R5 and R6 are bonded to each other to form an aromatic ring or heteroaromatic ring.
  • X 11 represents O, S, N(R A ), or C(R B )(R C ).
  • a 11 and A 12 are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring or a cyclopentadiene ring, and these rings may be condensed with other rings or substituted.
  • R 111 to R 114 , R B , and R C are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano represents a group.
  • Each R 115 independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond with L;
  • RA represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L;
  • R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 s, and R B and R C may combine with each other to form a cyclic structure.
  • n represents an integer of either 3 or 4;
  • L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group in which two or more of these are bonded.
  • R 115 or at least one group bonded to the ring represented by A 12 is a substituted or unsubstituted aryl group, substituted or It is an unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a cyano group.
  • R 7 and R 8 and R 17 and R 18 in the general formula (1) are bonded to each other to form -B(R 32 )-, where each R 32 is independently a hydrogen atom and a deuterium atom; Or the organic light-emitting device according to any one of [1] to [4], which represents a substituent.
  • the organic light-emitting device according to any one of [1] to [9], wherein the compound represented by formula (1) has a rotationally symmetric structure.
  • the organic light emitting device according to any one of [1] to [11], wherein the group bonded to the right side of L in general formula (2) contains a dibenzofuran structure.
  • L in formula (2) is a metaphenylene group.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 are bonded together to form a cyclic It may form a structure.
  • X 1 is a nitrogen atom
  • R 7 and R 8 and R 21 and R 22 are bonded through the nitrogen atom to form a 6-membered ring
  • R 17 and R 18 are bonded together to form a single bond at least one of R 1 to R 6 is a substituted or unsubstituted aryl group, or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R5 and R6 are bonded to each other to form an aromatic ring or heteroaromatic ring.
  • X represents O, S, N(R A ) or C(R B )(R C ).
  • a 1 and A 2 are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring or a cyclopentadiene ring, and these rings may be condensed with other rings or substituted.
  • R 111 to R 115 , R B , and R C each independently represent a hydrogen atom, deuterium atom, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group, or cyano represents a group.
  • RA represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group.
  • R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 s, and R B and R C may combine with each other to form a cyclic structure.
  • n represents an integer of either 3 or 4;
  • L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group in which two or more of these are bonded.
  • the light-emitting material exhibits excellent orientation and can be suitably used for organic light-emitting devices. Also, the organic light-emitting device of the present invention exhibits excellent light-emitting properties. In particular, the organic light-emitting device of the present invention is excellent in that it has high luminous efficiency and low driving voltage.
  • substituted means an atom or group of atoms other than a hydrogen atom and a deuterium atom.
  • substituted or unsubstituted means that hydrogen atoms may be replaced with deuterium atoms or substituents.
  • one of X 1 and X 2 is a nitrogen atom and the other is a boron atom.
  • X 1 is a nitrogen atom and X 2 is a boron atom.
  • R 17 and R 18 combine with each other to form a single bond to form a pyrrole ring.
  • X 1 is a boron atom and X 2 is a nitrogen atom.
  • R 21 and R 22 combine with each other to form a single bond to form a pyrrole ring.
  • R 1 to R 26 , A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 are bonded together to form a cyclic It may form a structure.
  • the cyclic structure formed by combining R 7 and R 8 contains a boron atom and 4 carbon atoms as ring skeleton-constituting atoms.
  • the cyclic structure formed by combining R 17 and R 18 contains a boron atom and 4 carbon atoms as ring skeleton constituent atoms when X 1 is a boron atom.
  • X 1 is a nitrogen atom
  • the cyclic structure is limited to pyrrole rings.
  • the cyclic structure formed by combining R 21 and R 22 contains a boron atom and 4 carbon atoms as ring skeleton constituent atoms when X 2 is a boron atom.
  • the cyclic structure is limited to pyrrole rings.
  • R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded together to form a cyclic structure containing a boron atom, the cyclic structure is preferably a 5- to 7-membered ring.
  • a 6-membered ring is more preferred, and a 6-membered ring is even more preferred.
  • R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded to each other, they are bonded to form a single bond, —O—, —S—, —N(R 27 )—, —C( R 28 )(R 29 )—, —Si(R 30 )(R 31 )—, —B(R 32 )—, —CO—, —CS—, are preferably formed, and —O—, —S It is more preferred to form - or -N(R 27 )-, and more preferred to form -N(R 27 )-.
  • R 27 to R 32 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 27 is particularly preferably a substituted or unsubstituted aryl group.
  • R 27 to R 32 in the ring formed by combining R 17 and R 18 may combine with at least one of R 16 and R 19 to further form a cyclic structure
  • R 21 and R R 27 to R 32 in the ring formed by combining 22 with each other may further combine with at least one of R 20 and R 23 to form a cyclic structure.
  • only one pair of R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bound together.
  • only two pairs of R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are attached to each other.
  • all of R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded together.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , and R 25 and R 26 may be bonded to each other to form a cyclic structure, which may be an aromatic ring or an aliphatic ring, It may also contain a heteroatom, and may be condensed with one or more other rings.
  • heteroatoms referred to here are preferably those selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms.
  • cyclic structures formed include benzene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, imidazoline ring, furan ring, thiophene ring, oxazole ring, and isoxazole ring.
  • the cyclic structure is a substituted or unsubstituted benzene ring (the ring may be further condensed), for example, a benzene ring optionally substituted with an alkyl group or an aryl group. .
  • the cyclic structure is a substituted or unsubstituted heteroaromatic ring, preferably a furan ring of benzofuran or a thiophene ring of benzothiophene.
  • any one of 1 to 4 can be selected, and 1 can be selected, 2 can be selected, 3 or 4 can be selected.
  • a pair selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded together to form a cyclic structure.
  • R 5 and R 6 are linked together to form a cyclic structure.
  • a pair selected from R 9 and R 10 , R 10 and R 11 , and R 11 and R 12 are bonded together to form a cyclic structure.
  • both R 1 and R 2 and R 13 and R 14 are bonded together to form a cyclic structure.
  • a pair selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded to each other to form a cyclic structure, and R 5 and R 6 are bonded to each other to form a ring structure.
  • both R 5 and R 6 and R 19 and R 20 are bonded together to form a cyclic structure.
  • R 1 to R 26 that are not bonded to adjacent R n are hydrogen atoms, deuterium atoms or substituents.
  • substituents a group selected from any of Substituent Groups A to E described later can be employed.
  • Preferred substituents that R 1 to R 26 can take are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, for example, the substituent is a substituted or unsubstituted aryl groups and, for example, substituents may be substituted or unsubstituted alkyl groups.
  • the substituents of the alkyl group, aryl group, and heteroaryl group referred to herein can also adopt a group selected from any one of the substituent groups A to E, but preferably an alkyl group, an aryl group, and a heteroaryl group. It is one or more groups selected from the group consisting of, more preferably a group of substituent group E, which may be unsubstituted.
  • at least one of R 1 to R 6 is a substituent, preferably a group of substituents E.
  • at least one of R 2 to R 6 is a substituent, preferably a group of substituent group E.
  • At least one of R 5 and R 6 is a substituent, preferably a group of substituent group E.
  • at least one of R 3 and R 6 is a substituent, more preferably both are substituents, preferably a group of substituents E.
  • when X 1 is a nitrogen atom at least one of R 15 and R 20 is a substituent, more preferably both are substituents, preferably a group of substituent group E be. At this time, R17 and R18 are bonded to each other to form a single bond.
  • R19 and R24 are substituents, more preferably both are substituents, preferably a group of substituent group E be.
  • R 21 and R 22 are bonded together to form a single bond.
  • at least one of R 8 and R 12 is a substituent, preferably both are substituents.
  • R 8 , R 10 and R 12 are substituents. Unsubstituted alkyl groups are preferred as substituents for R 8 to R 12 .
  • R 8 and R 12 are alkyl groups with 2 or more carbon atoms (preferably alkyl groups with 3 or more carbon atoms, more preferably alkyl groups with 3 to 8 carbon atoms, still more preferably alkyl groups with 3 or 4 carbon atoms). In some cases, the orientation becomes high when formed into a film, which is preferable.
  • R 8 and R 12 are substituent groups (preferably alkyl groups, more preferably alkyl groups having 2 or more carbon atoms, still more preferably alkyl groups having 3 or more carbon atoms, still more preferably alkyl groups having 3 to 8 carbon atoms).
  • R 1 to R 6 is a substituent (preferably a group of substituent group E).
  • R 13 and R 17 are substituents when X 1 is a boron atom.
  • R 13 , R 15 and R 17 are substituents when X 1 is a boron atom.
  • the substituents of R 13 to R 17 are preferably unsubstituted alkyl groups.
  • X2 is a boron atom
  • at least one of R22 and R26 is a substituent, preferably both are substituents.
  • R 22 , R 24 and R 26 are substituents when X 2 is a boron atom.
  • the substituents of R 22 to R 26 are preferably unsubstituted alkyl groups.
  • Specific examples of the boron atom represented by B in the general formula (1) and the groups bonded to the boron atom represented by X 1 or X 2 are shown below.
  • the groups bonded to boron atoms that can be employed in the present invention are not limitedly interpreted by the following specific examples.
  • CH3 is omitted from the methyl group. * represents a binding position.
  • R 1 to R 26 in formula (1) Specific examples of R 1 to R 26 in formula (1) are given below.
  • R 1 to R 7 and R 13 to R 21 when X 1 is a nitrogen atom, and R 18 to R 26 when X 2 is a nitrogen atom are preferably Z1 to Z9, and R 8 to R 12 and X 1 Z1 to Z7 are preferred as R 22 to R 26 when is a nitrogen atom, and R 13 to R 17 when X 2 is a nitrogen atom.
  • the groups bonded to boron atoms that can be employed in the present invention are not limitedly interpreted by the following specific examples.
  • D represents a deuterium atom. * represents a binding position.
  • a 1 and A 2 are hydrogen atoms, deuterium atoms or substituents.
  • substituent a group selected from any of Substituent Groups A to E described later can be employed.
  • a 1 and A 2 are each independently a hydrogen atom or a deuterium atom.
  • a 1 and A 2 are hydrogen atoms.
  • a 1 and A 2 are deuterium atoms.
  • One of A 1 and A 2 may be a substituent.
  • a 1 and A 2 may each independently be a substituent.
  • a preferred substituent that A 1 and A 2 can take is an acceptor group.
  • the acceptor group is a group having a positive Hammett ⁇ p value.
  • k 0 is the rate constant of the benzene derivative without a substituent
  • k is the rate constant of the benzene derivative substituted with a substituent
  • K 0 is the equilibrium constant of the benzene derivative without the substituent
  • K is the substituent
  • the equilibrium constant of the benzene derivative substituted with ⁇ represents the reaction constant determined by the type and conditions of the reaction.
  • the acceptor group that A 1 and A 2 can take is more preferably a group having a Hammett's ⁇ p value of greater than 0.2.
  • Groups having a Hammett's ⁇ p value of greater than 0.2 include a cyano group, an aryl group substituted with at least a cyano group, a group containing a fluorine atom, and a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom. can be mentioned.
  • the aryl group substituted with at least a cyano group here may be substituted with a substituent other than a cyano group (for example, an alkyl group or an aryl group), but it is an aryl group substituted only with a cyano group.
  • the aryl group substituted with at least a cyano group is preferably a phenyl group substituted with at least a cyano group.
  • the number of substituents of the cyano group is preferably 1 or 2, and may be 1 or 2, for example.
  • the group containing a fluorine atom includes a fluorine atom, a fluorinated alkyl group, and an aryl group substituted with at least a fluorine atom or a fluorinated alkyl group.
  • the fluorinated alkyl group is preferably a perfluoroalkyl group and preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
  • a heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom may be a monocyclic ring or a condensed ring in which two or more rings are condensed.
  • the number of rings after condensed is preferably 2 to 6, and can be selected from 2 to 4, or can be 2, for example.
  • Specific examples of the ring constituting the heteroaryl group include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, naphthyridine ring other than quinazoline ring and quinoxaline ring. .
  • the ring constituting the heteroaryl group may be substituted with a deuterium atom or a substituent, and the substituent is, for example, one or two groups selected from the group consisting of alkyl groups, aryl groups and heteroaryl groups Groups formed by combining two or more groups can be mentioned.
  • a cyano group is particularly preferred as an acceptor group that A 1 and A 2 can take.
  • at least one of A 1 and A 2 is an acceptor group.
  • only one of A 1 and A 2 is an acceptor group.
  • both A 1 and A 2 are the same acceptor group.
  • a 1 and A 2 are different acceptor groups.
  • a 1 and A 2 are cyano groups.
  • a 1 and A 2 are halogen atoms, for example bromine atoms.
  • acceptor group that can be employed in the present invention
  • the acceptor group that can be used in the present invention is not limited to the following specific examples.
  • the methyl group omits the indication of CH3 . Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups.
  • "D" represents a deuterium atom. * represents a binding position.
  • X 1 is a nitrogen atom
  • R 7 and R 8 are bonded via a nitrogen atom to form a 6-membered ring
  • R 21 and R 22 are bonded via a nitrogen atom to form a 6-membered ring.
  • R 17 and R 18 are joined together to form a single bond
  • at least one of R 1 to R 6 is a substituted or unsubstituted aryl group, or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 are bonded to each other to form an aromatic ring (optionally condensed substituted or unsubstituted benzene ring) or heteroaromatic It forms a ring (preferably a furan ring of optionally condensed substituted or unsubstituted benzofuran, or a thiophene ring of optionally condensed substituted or unsubstituted benzothiophene).
  • X 1 is a boron atom
  • X 2 is a nitrogen atom
  • R 7 and R 8 and R 17 and R 18 are bonded to each other to form a cyclic structure containing a boron atom
  • the cyclic structure is It is a 5- to 7-membered ring, and in the case of a 6-membered ring, R 7 and R 8 , R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS- or -N( R 27 )—.
  • R27 preferably represents a hydrogen atom, a deuterium atom or a substituent.
  • Each hydrogen atom in skeletons (1a) and (1b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (1) compounds in which phenyl groups bonded to boron atoms in skeletons (1a) and (1b) are both substituted with mesityl groups, 2,6-diisopropylphenyl groups or 2,4,6-triisopropylphenyl groups; can be exemplified.
  • each hydrogen atom in skeletons (1a) and (1b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 1 to Ar 4 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R 41 and R 42 each independently represent a substituted or unsubstituted alkyl group.
  • n1 and m2 each independently represent an integer of 0 to 5; n1 and n3 each independently represent an integer of 0 to 4; n2 and n4 each independently represent an integer of 0 to 3; A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent. At least one of n1 to n4 is 1 or more, and m1 and m2 are each independently preferably an integer of 1 to 5. In one aspect of the present invention, each of n1-n4 independently represents an integer of 0-2.
  • n1 to n4 is 1 or more, preferably at least one of n1 and n2 is 1 or more, and at least one of n3 and n4 is 1 or more.
  • n1 and n3 are each independently 1 or 2, and n2 and n4 are 0.
  • n2 and n4 are each independently 1 or 2
  • n1 and n3 are 0.
  • n1-n4 are each independently 1 or 2.
  • n1 and n3 are equal and n2 and n4 are equal.
  • n1 and n3 are 1 and n2 and n4 are 0. In one aspect of the invention, n1 and n3 are 0 and n2 and n4 are 1. In one aspect of the present invention, n1 to n4 are all 1.
  • the bonding positions of Ar 1 to Ar 4 may be at least one of the 3- and 6-positions of the carbazole ring, at least one of the 2- and 7-positions, or at least one of the 1- and 8-positions. It may be one or at least one of the 4th and 5th positions.
  • the bonding positions of Ar 1 to Ar 4 may be both 3 and 6 positions, both 2 and 7 positions, or both 1 and 8 positions of the carbazole ring. and may be both 4th and 5th.
  • positions 3 and 6 can be preferably selected, or both positions 3 and 6 can be more preferably selected.
  • Ar 1 to Ar 4 are all the same group.
  • Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group or naphthyl group, still more preferably a substituted or unsubstituted is the phenyl group of Examples of the substituent include a group selected from any one of Substituent Groups A to E described below, but an unsubstituted phenyl group is also preferred.
  • Ar 1 to Ar 4 include a phenyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group and a terphenyl group.
  • m1 and m2 are each independently 0.
  • m1 and m2 are each independently an integer from 1 to 5.
  • m1 and m2 are equal.
  • R 41 and R 42 are alkyl groups having 1 to 6 carbon atoms and can be selected, for example, from alkyl groups having 1 to 3 carbon atoms, or can be selected as methyl groups. .
  • substitution positions of the alkyl group are 2-position only, 3-position only, 4-position only, 3-position and 5-position, 2-position and 4-position, 2-position and 6-position with the carbon atom bonded to the boron atom as 1-position.
  • 2-position, 4-position and 6-position can be exemplified, preferably at least 2-position, more preferably at least 2-position and 6-position.
  • a 1 and A 2 reference can be made to the corresponding description of general formula (1).
  • Ar 5 to Ar 8 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R43 and R44 each independently represent a substituted or unsubstituted alkyl group.
  • n5 and n8 each independently represent an integer of 0 to 3; n5 and n7 each independently represent an integer of 0 to 4; A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the descriptions of m2, n1 to n4, A 1 and A 2 can be referred to.
  • At least one of n5 to n8 is 1 or more, and each of m3 and m4 is preferably an integer of 1 to 5 independently.
  • the compound of the present invention has, for example, the following skeleton (2a) when X 1 is a nitrogen atom, and X When 2 is a nitrogen atom, it has, for example, the following skeleton (2b). Ph is a phenyl group. Skeleton (2a)
  • Each hydrogen atom in skeletons (2a) and (2b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (1) At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in skeleton (2a) is substituted with a substituted or unsubstituted aryl group.
  • each hydrogen atom in skeletons (2a) and (2b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 9 to Ar 14 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n9, n11, n12 and n14 each independently represent an integer of 0 to 4;
  • n10 and n13 each independently represent an integer of 0 to 2; However, at least one of n9, n10, n12, and n13 is 1 or more.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • each of n9-n14 independently represents an integer of 0-2. In one aspect of the present invention, at least one of n9 to n14 is 1 or more.
  • n9 and n12 can be 1 or more, and n10 and n13 can be 1 or more. In a preferred embodiment of the present invention, at least one of n9, n10, n12 and n13 is 1 or more.
  • n9 and n12 are each independently 1 or 2
  • n10, n11, n13 and n14 are 0.
  • n10 and n13 are each independently 1 or 2
  • n9, n11, n12 and n14 are 0.
  • n9 and n12 are each independently 1 or 2
  • n10 and n13 are each independently 1 or 2
  • n11 and n14 are 0.
  • n9-n14 are all 1.
  • the binding positions of Ar 9 to Ar 14 can be the 3,6 positions of the carbazole ring or other positions.
  • Ar 9 to Ar 14 are all the same group.
  • Ar 15 to Ar 20 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n15, n17, n18 and n20 each independently represent an integer of 0 to 4;
  • n16 and n19 each independently represent an integer of 0 to 2;
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the compound of the present invention has, for example, the following skeleton (3a) when X 1 is a nitrogen atom, and X 2 is a nitrogen atom, it has, for example, the following skeleton (3b).
  • Each hydrogen atom in skeletons (3a) and (3b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (1) each hydrogen atom in skeletons (3a) and (3b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 21 to Ar 26 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n21, n23, n24 and n26 each independently represent an integer of 0 to 4; n22 and n25 each independently represent an integer of 0 to 2;
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 9 to Ar 14 , n9 to n14, A 1 and A 2 in formula (2a) can be referred to.
  • Ar 27 to Ar 32 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n27, n29, n30 and n32 each independently represent an integer of 0 to 4;
  • n28 and n31 each independently represent an integer of 0 to 2;
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • a compound is selected in which two benzene rings constituting the carbazole partial structure present in general formula (1) are condensed with another ring.
  • a compound in which a benfuran ring is condensed, a compound in which a benzothiophene ring is condensed, and a compound in which a benzene ring is condensed can be particularly preferably selected. Compounds in which these rings are condensed will be described below with specific examples.
  • Preferred examples include compounds in which a benzofuran ring or a benzothiophene ring is condensed with a benzene ring to which a boron atom is not directly bonded, of the two benzene rings constituting the carbazole partial structure present in general formula (1).
  • Examples of such compounds include compounds having the following skeleton (4a) and compounds having the following skeleton (4b).
  • Y 1 to Y 4 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • the two hydrogen atoms here indicate a state in which two benzene rings bonded to the boron atom are not connected to each other.
  • Y 1 and Y 2 are preferably the same, and Y 3 and Y 4 are preferably the same, but they may be different.
  • Y 1 -Y 4 are single bonds.
  • Y 1 -Y 4 are N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 1 to Z 4 each independently represent an oxygen atom or a sulfur atom.
  • Z 1 and Z 2 are preferably the same, and Z 3 and Z 4 are preferably the same, but they may be different.
  • Z 1 -Z 4 are oxygen atoms.
  • the furan ring of benzofuran is fused to the benzene ring that constitutes the carbazole partial structure in (4a) and (4b).
  • the orientation of the condensed furan ring is not restricted.
  • Z 1 -Z 4 are sulfur atoms.
  • the thiophene ring of benzothiophene is fused to the benzene ring that constitutes the carbazole partial structure in (4a) and (4b).
  • the orientation of the fused thiophene rings is not restricted.
  • Each hydrogen atom in skeletons (4a) and (4b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with adjacent hydrogen atoms to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (1) each hydrogen atom in skeletons (4a) and (4b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 51 and Ar 52 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R51 and R52 each independently represent a substituted or unsubstituted alkyl group.
  • m51 and m52 each independently represent an integer of 0 to 4; n51 and n52 each independently represent an integer of 0 to 2; Y 1 to Y 4 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 1 to Z 4 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n51 and n52 are the same number.
  • n51 and n52 may be 0, and n51 and n52 may be 1.
  • m51 and m52 are the same number.
  • m51 and m52 are integers from 0-3.
  • m51 and m52 may be 0, m51 and m52 may be 1, m51 and m52 may be 2, and m51 and m52 may be 3.
  • Preferred groups for Ar 51 , Ar 52 , R 51 , R 52 , A 1 and A 2 are the corresponding descriptions for Ar 1 to Ar 4 , R 41 to R 42 , A 1 and A 2 in general formula (1a) can be referred to.
  • Ar 53 and Ar 54 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R53 and R54 each independently represent a substituted or unsubstituted alkyl group.
  • m53 and m54 each independently represent an integer of 0 to 4; n53 and n54 each independently represents an integer of 0 to 2; Y 3 and Y 4 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z3 and Z4 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 53 , Ar 54 , R 53 , R 54 , m53, m54, n53, n54, A 1 and A 2 refer to Ar 51 , Ar 52 , R 51 , R 52 , m51, The descriptions of m52, n51, n52, A 1 and A 2 can be referred to.
  • a compound in which a benzofuran ring or a benzothiophene ring is condensed with a benzene ring to which a boron atom is directly bonded among the two benzene rings constituting the carbazole partial structure present in general formula (1) can be preferably mentioned.
  • Examples of such compounds include compounds having the following skeleton (5a) and compounds having the following skeleton (5b).
  • Y 5 to Y 8 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Z 5 to Z 8 each independently represent an oxygen atom or a sulfur atom.
  • each hydrogen atom in skeletons (5a) and (5b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 55 and Ar 56 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R55 and R56 each independently represent a substituted or unsubstituted alkyl group.
  • m55 and m56 each independently represents an integer of 0 to 4;
  • n55 and n56 each independently represent an integer of 0 to 4;
  • Y 5 and Y 6 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z5 and Z6 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n55 and n56 are integers from 0-2.
  • n55 and n56 may be 0 and n55 and n56 may be 1.
  • m51 and m52 are the same number. For details of m55 and m56, the description of m51 and m52 in general formula (4a) can be referred to.
  • Ar 57 and Ar 58 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R57 and R58 each independently represent a substituted or unsubstituted alkyl group.
  • m57 and m58 each independently represent an integer of 0 to 4; n57 and n58 each independently represent an integer of 0 to 4; Y7 and Y8 each independently represent two hydrogen atoms, a single bond or N( R27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z7 and Z8 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 57 , Ar 58 , R 57 , R 58 , m57, m58, n57, n58, A 1 and A 2 refer to Ar 55 , Ar 56 , R 55 , R 56 , m55, The descriptions of m56, n55, n56, A 1 and A 2 can be referred to.
  • a compound in which a benzofuran ring or a benzothiophene ring is condensed to both of the two benzene rings constituting the carbazole partial structure present in general formula (1) can be preferably mentioned.
  • Examples of such compounds include compounds having the following skeleton (6a) and compounds having the following skeleton (6b).
  • Y 9 to Y 12 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Z 9 to Z 16 each independently represent an oxygen atom or a sulfur atom.
  • Z 9 to Z 16 are preferably the same, but may be different.
  • Z 9 -Z 16 are oxygen atoms.
  • Z 9 -Z 16 are sulfur atoms.
  • each hydrogen atom in skeletons (6a) and (6b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 59 and R 60 each independently represent a substituted or unsubstituted alkyl group.
  • m59 and m60 each independently represents an integer of 0 to 4;
  • Y9 and Y10 each independently represent two hydrogen atoms, a single bond or N( R27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 9 to Z 12 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the compound represented by formula (6a) is not limited to the following specific examples.
  • compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • R 61 and R 62 each independently represent a substituted or unsubstituted alkyl group.
  • m61 and m60 each independently represents an integer of 0 to 4;
  • Y 11 and Y 12 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 13 to Z 16 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the compound represented by formula (6b) is not limited to the following specific examples.
  • compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • a compound in which a benzene ring is condensed with a benzene ring to which a boron atom is not directly bonded can be preferably mentioned.
  • examples of such compounds include compounds having the following skeleton (7a) and compounds having the following skeleton (7b).
  • Y 21 to Y 24 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Y 21 to Y 24 the descriptions of Y 1 to Y 4 in skeletons (4a) and (4b) can be referred to.
  • each hydrogen atom in skeletons (7a) and (7b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 71 to Ar 74 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n71 and n73 each independently represents an integer of 0 to 2;
  • n72 and n74 each independently represents an integer of 0 to 4;
  • Y 21 and Y 22 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n71-n74 are integers from 0-2.
  • n71 and n73 are the same number
  • n72 and n74 are the same number.
  • n71 to n74 may be the same number.
  • n71-n74 may be zero.
  • All of n71 to n74 may be 1.
  • n71 and n73 may be 0, and n72 and n74 may be 1, for example.
  • the corresponding descriptions of Ar 1 to Ar 4 , A 1 and A 2 in general formula (1a) can be referred to.
  • Ar 75 to Ar 78 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n75 and n77 each independently represent an integer of 0 to 2;
  • n76 and n78 each independently represents an integer of 0 to 4;
  • Y 23 and Y 24 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • n75 to n78 the description of n71 to n74 in general formula (7a) can be referred to.
  • the description of n71 to n74 in general formula (7a) can be referred to.
  • the description of Ar 75 to Ar 78 the corresponding descriptions of Ar 1 to Ar 4 in general formula (1a) can be referred to.
  • a compound in which a benzene ring is condensed with a benzene ring to which a boron atom is directly bonded can be preferably mentioned.
  • examples of such compounds include compounds having the following skeleton (8a) and compounds having the following skeleton (8b).
  • Y 25 to Y 28 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Y 25 -Y 28 For details of Y 25 -Y 28 , reference can be made to the corresponding descriptions of skeletons (4a) and (4b).
  • each hydrogen atom in skeletons (8a) and (8b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 79 and Ar 80 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R71 and R72 each independently represent a substituted or unsubstituted alkyl group.
  • m71 and m72 each independently represents an integer of 0 to 4;
  • n79 and n80 each independently represent an integer of 0 to 4;
  • Y 25 and Y 26 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n79 and n80 are integers from 0-2. In one aspect of the present invention, n79 and n80 are the same number, for example both may be 0 or both may be 1.
  • m71 and m72 are integers from 0-2. In one aspect of the invention, m71 and m72 are the same number, for example both may be 0 or both may be 1.
  • Ar 81 and Ar 82 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R73 and R74 each independently represent a substituted or unsubstituted alkyl group.
  • m73 and m74 each independently represent an integer of 0 to 4;
  • n81 and n82 each independently represent an integer of 0 to 4;
  • Y 27 and Y 28 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • m73, m74, n81 and n82 the description of m71, m72, n79 and n80 in general formula (8a) can be referred to.
  • Ar 81 , Ar 82 , R 73 , R 74 , A 1 and A 2 corresponding descriptions of Ar 1 , Ar 3 , R 41 , R 42 , A 1 and A 2 in general formula (1a) can be referred to.
  • a compound in which benzene rings are condensed to both of the two benzene rings constituting the carbazole partial structure present in general formula (1) can be preferably mentioned.
  • Examples of such compounds include compounds having the following skeleton (9a) and compounds having the following skeleton (9b).
  • Y 29 to Y 32 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Y 29 -Y 32 For details of Y 29 -Y 32 , reference can be made to the corresponding descriptions of skeletons (4a) and (4b).
  • each hydrogen atom in skeletons (9a) and (9b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 75 and R 76 each independently represent a substituted or unsubstituted alkyl group.
  • m75 and m76 each independently represents an integer of 0 to 4;
  • Y 29 and Y 30 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the descriptions of R 71 , R 72 , m71, m72, A 1 and A 2 in general formula (8a) can be referred to.
  • R 77 and R 78 each independently represent a substituted or unsubstituted alkyl group.
  • m77 and m78 each independently represent an integer of 0 to 4;
  • Y 31 and Y 32 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the description of R 71 , R 72 , m71, m72, A 1 and A 2 in general formula (8a) can be referred to.
  • Each hydrogen atom in skeleton (10) may be replaced by a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • a deuterium atom or a substituent may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 1 to R 26 A 1 and A 2 in general formula (1).
  • At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in skeleton (10) is substituted with a substituted or unsubstituted aryl group.
  • each hydrogen atom in skeleton (10) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 91 to Ar 94 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n91 and n93 each independently represent an integer of 0-4, and n92 and n94 each independently represent an integer of 0-3.
  • ⁇ ring, ⁇ ring, ⁇ ring, and ⁇ ring may be substituted, and at least one ring is substituted with a substituted or unsubstituted aryl group, or optionally substituted benzene ring is condensed or the furan ring of substituted or unsubstituted benzofuran or the thiophene ring of substituted or unsubstituted thiophene are condensed.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n91-n94 are integers from 0-2.
  • n91 and n93 are the same number, and n92 and n94 are the same number. All of n91 to n94 may be the same number, for example, all may be 0 or all may be 1.
  • Ar 91 to Ar 94 the corresponding descriptions of Ar 1 to Ar 4 in general formula (1a) can be referred to.
  • the ⁇ and ⁇ rings have the same substituents or have the same condensed structure, and the ⁇ and ⁇ rings have the same substituents or have the same condensed structure. have.
  • both the ⁇ ring and the ⁇ ring are substituted with a substituted or unsubstituted aryl group, an optionally substituted benzene ring is condensed, or a substituted or unsubstituted furan ring of benzofuran Alternatively, the thiophene rings of substituted or unsubstituted thiophene are condensed.
  • both the ⁇ ring and the ⁇ ring are substituted with a substituted or unsubstituted aryl group, an optionally substituted benzene ring is condensed, or a substituted or unsubstituted furan ring of benzofuran Alternatively, the thiophene rings of substituted or unsubstituted thiophene are condensed.
  • all of the ⁇ ring, ⁇ ring, ⁇ ring, and ⁇ ring are substituted with a substituted or unsubstituted aryl group, or condensed with an optionally substituted benzene ring, or substituted
  • the furan ring of unsubstituted benzofuran or the thiophene ring of substituted or unsubstituted thiophene is condensed.
  • a 1 and A 2 reference can be made to the corresponding description of general formula (1).
  • the compound represented by the general formula (1) may have an asymmetric skeleton.
  • it may be a compound having an asymmetric skeleton such as the following skeleton (11a) or the following skeleton (11b).
  • Z17 and Z18 each independently represent an oxygen atom or a sulfur atom.
  • each hydrogen atom in skeletons (11a) and (11b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 83 to Ar 85 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R83 and R84 each independently represent a substituted or unsubstituted alkyl group.
  • Z17 represents an oxygen atom or a sulfur atom.
  • m83 and m84 each independently represents an integer of 0 to 5; n83 represents an integer of 0 to 4, and n84 and n85 each independently represents an integer of 0 to 3.
  • Ar 83 to Ar 85 , R 83 , R 84 , m83, m84 and n83 to n85 refer to Ar 1 , Ar 2 , Ar 4 , R 41 , R 42 , m1 in general formula (1a) , m2, n1, n2, and n4.
  • the compound represented by the general formula (11a) is not limitedly interpreted by the following specific examples.
  • a compound in which all Xs in the molecule are oxygen atoms and a compound in which all Xs in the molecule are sulfur atoms are disclosed.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • Ar 86 to Ar 88 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R86 and R87 each independently represent a substituted or unsubstituted alkyl group.
  • Z18 represents an oxygen atom or a sulfur atom.
  • m86 and m87 each independently represents an integer of 0 to 5; n86 represents an integer of 0 to 4, and n87 and n88 each independently represents an integer of 0 to 3.
  • Ar 86 to Ar 88 , R 86 , R 87 , m86, m87, n86 to n88 refer to Ar 1 , Ar 2 , Ar 4 , R 41 , R 42 , m1 in general formula (1a) , m2, n1, n2, and n4.
  • the compound represented by the general formula (11b) is not limitedly interpreted by the following specific examples.
  • a compound in which all Xs in the molecule are oxygen atoms and a compound in which all Xs in the molecule are sulfur atoms are disclosed.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • a compound in which R 5 is a donor group can be preferably employed as the compound represented by the general formula (1).
  • a compound in which R5 is a donor group tends to have a high molar absorption coefficient and high luminous efficiency. For example , it exhibits superior luminescence properties compared to compounds in which R3 is a donor group.
  • R 3 is not a donor group.
  • R 5 is a donor group, or neither of them is a donor group (particularly a donor group with a ⁇ p value of ⁇ 0.2 or less).
  • the donor group is a group having a negative Hammett ⁇ p value.
  • the ⁇ p value of the donor group of R 5 is preferably ⁇ 0.2 or less, may be ⁇ 0.4 or less, or may be ⁇ 0.6 or less, for example.
  • Preferred donor groups include substituted amino groups, preferably substituted or unsubstituted diarylamino groups.
  • the aryl group may be a monocyclic ring or a condensed ring in which two or more rings are condensed. In the case of condensed rings, the number of rings after condensed is preferably 2 to 6, and can be selected from 2 to 4, or can be 2, for example.
  • Two aryl groups constituting a diarylamino group may be the same or different. Also, two aryl groups may be linked by a single bond or a linking group.
  • a substituted or unsubstituted diphenylamino group is preferable as the substituted or unsubstituted diarylamino group.
  • a substituted or unsubstituted carbazol-9-yl group in which two phenyl groups are bonded by a single bond may be employed, or a substituted or unsubstituted diphenylamino group in which two phenyl groups are not bonded by a single bond. may be adopted.
  • any one of R 1 to R 7 in general formula (1) is a substituted amino group, at least R 5 is preferably a substituted amino group, more preferably only R 5 is a substituted amino group. In one aspect of the invention , R3 is not a substituted amino group.
  • R 16 or R 19 is preferably a donor group, more preferably R 19 is a donor group.
  • all of the other R 1 to R 26 may be, for example, hydrogen atoms or deuterium atoms, and for example, at least one of R 3 , R 6 , R 15 and R 20 may be a substituent (preferably substituted or an unsubstituted alkyl group, or a substituted or unsubstituted aryl group), and others may be hydrogen atoms or deuterium atoms.
  • R 20 or R 23 is preferably a donor group, more preferably R 20 is a donor group.
  • all of the other R 1 to R 26 may be, for example, hydrogen atoms or deuterium atoms, and for example, at least one of R 3 , R 6 , R 19 and R 24 may be a substituent (preferably substituted or an unsubstituted alkyl group, or a substituted or unsubstituted aryl group), and others may be hydrogen atoms or deuterium atoms.
  • R 5 is a donor group
  • compounds represented by the following general formula (12a) and compounds represented by the following general formula (12b) can be exemplified.
  • Ar 1 to Ar 8 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group;
  • a substituted or unsubstituted alkyl group can be preferably selected, and a substituted or unsubstituted aryl group can be preferably selected.
  • R5 represents a donor group.
  • R 41 to R 44 each independently represent a substituted or unsubstituted alkyl group.
  • n1 to m4 each independently represent an integer of 0 to 5; n1, n3, n5 and n7 each independently represent an integer of 0-4, n4 and n8 represent an integer of 0-3, and n2' and n6' represent an integer of 0-2.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 1 bonded to adjacent carbon atoms, Ar 3 bonded to adjacent carbon atoms, Ar 5 bonded to adjacent carbon atoms, and Ar 5 bonded to adjacent carbon atoms Ar 7 may be bonded to each other to form a cyclic structure, preferably benzofuran (condensed with furan ring) or benzothiophene (condensed with thiophene ring).
  • each compound is defined by identifying R, Ar and X in formulas F1-F56 in the table.
  • R is selected from A to D listed below
  • Ar is selected from a to d listed below
  • X is selected from ⁇ to ⁇ .
  • a compound of 1 is a compound having a structure in which R is A and Ar is a in Formula F1.
  • the skeletons (1a) to (12b) are skeletons to which other rings are not further condensed. In one aspect of the present invention, the skeletons (1a) to (12b) are skeletons to which other rings may be further condensed.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R9 , R9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R18 and R19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 are linked to each other to form a ring structure. be able to.
  • a 1 and A 2 in general formula (1) are acceptor groups.
  • examples thereof include compounds having acceptor groups at positions A 1 and A 2 and having any of skeletons (1a) to (12b).
  • the description and specific examples of the acceptor group the description and specific examples of the acceptor groups of A 1 and A 2 in formula (1) above can be referred to.
  • Specific examples of compounds in which A 1 and A 2 are acceptor groups are given below.
  • the compounds in which A 1 and A 2 are acceptor groups that can be used in the present invention are not limited to the following specific examples.
  • the following specific examples have a structure in which both A 1 and A 2 are "A", and the structure of each compound is specified by individually specifying "A".
  • a compound having a rotationally symmetric structure is selected as the compound represented by General Formula (1).
  • a compound having an axisymmetric structure is selected as the compound represented by General Formula (1).
  • a compound having an asymmetric structure is selected as the compound represented by general formula (1).
  • Specific examples of compounds having an asymmetric skeleton are given below.
  • the compound having an asymmetric skeleton and the compound having an asymmetric structure that can be used in the present invention are not limited to the following specific examples.
  • compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • R 3 in general formula (1) is not a diarylamino group (two aryl groups constituting the diarylamino group may be bonded to each other).
  • R3 in general formula ( 1 ) is a hydrogen atom, a deuterium atom or an acceptor group (not a donor group).
  • at least one of n1 to n4 in general formula (1a) is 1 or more.
  • at least one of m1 and m2 in general formula (1a) is 1 or more.
  • At least one of n1 to n4 in general formula (1a) is 1 or more, and at least one of m1 and m2 in general formula (1a) is 1 or more.
  • at least one of n5 to n8 in general formula (1b) is 1 or more.
  • at least one of m3 and m4 in general formula (1b) is 1 or more.
  • at least one of n5 to n8 in general formula (1b) is 1 or more, and at least one of m3 and m4 in general formula (1a) is 1 or more.
  • R 41 and R 42 and at least one of R 43 and R 44 are deuterium atoms;
  • An optionally substituted alkyl group is preferred, for example, all of R 41 to R 44 are alkyl groups optionally substituted with deuterium atoms.
  • at least one of n1 to n4 is 1 or more and at least one of n5 to n8 is 1 or more, at least one of Ar 1 to Ar 4 and at least one of Ar 5 to Ar 8 is deuterium It is preferably an aryl group which may be substituted with an atom or an alkyl group.
  • Ar 1 to Ar 8 are aryl groups which may be substituted with a deuterium atom or an alkyl group.
  • R 1 in general formula (1) is a boron atom and R 8 , R 10 , R 12 , R 13 , R 15 and R 17 are alkyl groups (or methyl groups)
  • R 1 At least one of to R 7 , R 18 to R 20 and R 23 to R 26 is a substituent, preferably a group of substituent group E, which may be substituted with, for example, a deuterium atom or an alkyl group. It is an aryl group.
  • R 1 At least one of to R 7 , R 13 to R 16 and R 19 to R 21 is a substituent, preferably a group of substituent group E, and may be substituted with, for example, a deuterium atom or an alkyl group. It is an aryl group.
  • X 1 in general formula (1) is a boron atom, any one set of R 8 and R 9 , R 9 and R 10 , and R 15 and R 16 , R 16 and R 17 when any one pair is bonded to each other to form an aromatic ring (or benzene ring), at least one of R 1 to R 7 , R 18 to R 20 and R 23 to R 26 is a substituent, Preferably, it is a group of substituent group E, such as an aryl group optionally substituted with a deuterium atom or an alkyl group.
  • X 2 in general formula (1) is a boron atom, any one set of R 8 and R 9 , R 9 and R 10 , and R 22 and R 23 , R 23 and R 24 when any one pair is bonded to each other to form an aromatic ring (or benzene ring), at least one of R 1 to R 7 , R 13 to R 16 and R 19 to R 21 is a substituent; Preferably, it is a group of substituent group E, such as an aryl group optionally substituted with a deuterium atom or an alkyl group.
  • R 9 and R 11 in general formula (1) are neither a cyano group nor an alkyl group.
  • R 9 and R 11 are hydrogen atoms, deuterium atoms, or substituents other than cyano and alkyl groups.
  • R 9 and R 11 in general formula (1) are neither a cyano group nor a tert-butyl group.
  • at least one of R 8 to R 12 in general formula (1) is a substituent.
  • R 3 in general formula (1) is neither a substituted amino group nor an aryl group.
  • R 3 in general formula (1) is neither a substituted amino group nor a phenyl group.
  • R 3 in general formula (1) is not a dimethylamino group, diphenylamino group or phenyl group.
  • at least one of R 1 to R 26 in general formula (1) is a substituent, more preferably at least one of R 1 to R 26 is an alkyl group, for example 1 to 4 alkyl groups.
  • the molecular weight of the compound represented by the general formula (1) is, for example, 1500 or less when the organic layer containing the compound represented by the general formula (1) is intended to be formed by a vapor deposition method and used. It is preferably 1,200 or less, more preferably 1,000 or less, and even more preferably 900 or less.
  • the lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). Preferably it is 624 or more.
  • the compound represented by general formula (1) preferably does not contain a metal atom.
  • a boron atom is not contained in the metal atom here.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, sulfur atoms and boron atoms can be selected. can be done.
  • a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen and boron atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, sulfur and boron atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and boron atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms and boron atoms can be selected.
  • the compound represented by general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized by using a ring closure reaction or by using a substitution reaction.
  • the "alkyl group” may be linear, branched, or cyclic. Moreover, two or more of the linear portion, the cyclic portion and the branched portion may be mixed.
  • the number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group.
  • alkyl group as a substituent may be further substituted with an aryl group.
  • An "alkenyl group” may be linear, branched, or cyclic. Moreover, two or more of the linear portion, the cyclic portion and the branched portion may be mixed.
  • the number of carbon atoms in the alkenyl group can be, for example, 2 or more and 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkenyl groups include ethenyl, n-propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, and 2-ethylhexenyl groups. can be mentioned.
  • the alkenyl group as a substituent may be further substituted with a substituent.
  • the “aryl group” and “heteroaryl group” may be monocyclic or condensed rings in which two or more rings are condensed. In the case of condensed rings, the number of condensed rings is preferably 2 to 6, and can be selected from 2 to 4, for example.
  • rings include benzene ring, pyridine ring, pyrimidine ring, triazine ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, quinoline ring, pyrazine ring, quinoxaline ring, and naphthyridine ring, which are condensed. It may be a circular ring.
  • aryl or heteroaryl groups include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 2-pyridyl, 3-pyridyl, 4 - pyridyl group.
  • the number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, selected within the range of 6 to 14, or selected within the range of 6 to 10.
  • the number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, selected within the range of 5 to 14, or selected within the range of 5 to 10. You may "Arylene group” and "heteroaryl group” can be read by changing the valence number from 1 to 2 in the description of the aryl group and heteroaryl group.
  • substituted group A refers to a hydroxyl group, a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), an alkyl group (e.g., 1 to 40 carbon atoms), an alkoxy group (e.g., 1 to 40), alkylthio groups (eg, 1 to 40 carbon atoms), aryl groups (eg, 6 to 30 carbon atoms), aryloxy groups (eg, 6 to 30 carbon atoms), arylthio groups (eg, 6 to 30 carbon atoms), Heteroaryl group (eg, 5 to 30 ring atoms), heteroaryloxy group (eg, 5 to 30 ring atoms), heteroarylthio group (eg, 5 to 30 ring atoms), acyl group ( For example, 1 to 40 carbon atoms), alkenyl groups (eg, 1 to 40 carbon atoms), alkenyl groups (eg, 1 to 40
  • substituted group B means an alkyl group (eg, 1 to 40 carbon atoms), an alkoxy group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), an aryloxy group (eg for example, 6 to 30 carbon atoms), heteroaryl groups (eg, 5 to 30 ring atoms), heteroaryloxy groups (eg, 5 to 30 ring atoms), diarylaminoamino groups (eg, 0 to 30 carbon atoms).
  • 20) is one group selected from the group consisting of 20) or a group formed by combining two or more groups.
  • substituted group C refers to an alkyl group (eg, 1 to 20 carbon atoms), an aryl group (eg, 6 to 22 carbon atoms), a heteroaryl group (eg, 5 to 20 ring skeleton atoms), It means one group selected from the group consisting of diarylamino groups (eg, 12 to 20 carbon atoms) or a group formed by combining two or more groups.
  • substituted group D refers to an alkyl group (eg, 1 to 20 carbon atoms), an aryl group (eg, 6 to 22 carbon atoms) and a heteroaryl group (eg, 5 to 20 ring skeleton atoms).
  • substituted group E refers to one group selected from the group consisting of an alkyl group (eg, 1 to 20 carbon atoms) and an aryl group (eg, 6 to 22 carbon atoms), or a combination of two or more means a group formed by
  • substituent when described as “substituent” or “substituted or unsubstituted” may be selected from, for example, substituent group A, or selected from substituent group B may be selected from Substituent Group C, may be selected from Substituent Group D, or may be selected from Substituent Group E.
  • X 11 represents O, S, N(R A ) or C(R B )(R C ). In one aspect of the invention, X 11 is O, S or N(R A ). In one aspect of the invention, X 11 is O or S. In one aspect of the invention, X 11 is N(R A ). In one aspect of the invention, X 11 is O. In one aspect of the invention, X 11 is S. When X 11 is O, S or C(R B )(R C ), L is attached to the benzene ring to which (R 115 )n is attached.
  • L is bonded to the benzene ring to which (R 115 )n is bonded or to N represented by X 11 .
  • the bond extending to the right from L is either attached to the benzene ring to which (R 115 )n is attached, as described herein, or X 11 when X 11 is N (i.e., N) means to bind to
  • a 11 and A 12 are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring or a cyclopentadiene ring, and these rings are further condensed with other rings. may also be substituted.
  • a 11 is a benzene ring.
  • a 12 is a benzene ring.
  • both A 11 and A 12 are benzene rings.
  • at least one of A 11 and A 12 is a furan ring, thiol ring, pyrrole ring or cyclopentadiene ring.
  • At least one of A 11 and A 12 is a furan ring. In one aspect of the invention, at least one of A 11 and A 12 is a thiol ring. In one aspect of the invention, at least one of A 11 and A 12 is a pyrrole ring. In one aspect of the invention, at least one of A 11 and A 12 is a cyclopentadiene ring.
  • the benzene ring, furan ring, thiol ring, pyrrole ring and cyclopentadiene ring referred to herein may be condensed with another ring.
  • the condensed ring may be an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, or an aliphatic heterocyclic ring, and a ring in which two or more of these are condensed.
  • An aromatic hydrocarbon ring, an aromatic heterocyclic ring, or a ring in which two or more of these are condensed is preferred.
  • a benzene ring can be mentioned as an aromatic hydrocarbon ring.
  • the aromatic heterocyclic ring means an aromatic ring containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring, such as a 5-membered ring or a 6-membered ring.
  • a furan ring, a thiophene ring, or a pyrrole ring can be employed as the aromatic heterocyclic ring.
  • the aliphatic hydrocarbon ring is preferably a hydrocarbon ring that does not exhibit aromaticity, preferably a 5- to 7-membered ring, such as a 5-membered ring or a 6-membered ring. You can For example, a cyclopentadiene ring can be employed.
  • Aliphatic heterocycle means a ring that contains a heteroatom as a ring skeleton-constituting atom and does not exhibit aromaticity, and is preferably a 5- to 7-membered ring, such as a 5-membered ring or a 6-membered ring can be adopted.
  • a 11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are condensed.
  • a 11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are condensed.
  • a 11 is a benzene ring, and the benzene ring is condensed with a furan ring of benzofuran or a thiophene ring of benzothiophene.
  • a 11 is fused with the furan ring of a benzofuran.
  • a 11 is fused with the thiophene ring of a benzothiophene.
  • a 12 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are condensed.
  • a 12 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are condensed.
  • a 12 is a benzene ring, and the benzene ring is condensed with a furan ring of benzofuran or a thiophene ring of benzothiophene. In one aspect of the invention, A 12 is fused with the furan ring of a benzofuran. In one aspect of the invention, A 12 is fused with the thiophene ring of a benzothiophene.
  • a hydrogen atom in a ring constituting A 11 or A 12 may be substituted with a deuterium atom or a substituent. The substituent can be selected from any one of Substituent Groups A to E, and is selected from Substituent Group E, for example.
  • the rings constituting A 11 and A 12 are a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, and a cyano group. may be substituted with one atom or group selected from the group consisting of or a combination of two or more groups. In one aspect of the present invention, the ring constituting A 11 or A 12 may be substituted with a deuterium atom, an alkyl group, an aryl group, or a group combining these.
  • At least one ring constituting A 11 or A 12 is substituted with a deuterium atom, an alkyl group, an aryl group, or a group combining these.
  • the ring skeleton-constituting nitrogen atom of the pyrrole ring includes a deuterium atom, an aryl optionally substituted with an alkyl group or an aryl group. It is preferable that the group is bonded (the same applies to the nitrogen atom of the indole ring described later).
  • two or more hydrogen atoms of the rings constituting A 11 and A 12 are substituted, they may be substituted with the same atom or group, or may be substituted with different atoms or groups.
  • R 111 to R 114 , R B , and R C each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted represents a substituted alkyl group or cyano group.
  • Each R 115 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond with L (i.e., L single bond to ).
  • RA represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L (that is, a single bond to L).
  • aryl group, heteroaryl group, and alkyl group the above description of "aryl group”, “heteroaryl group”, and “alkyl group” can be referred to.
  • the aryl group preferably has 6 to 14 carbon atoms, and examples thereof include phenyl, 1-naphthyl and 2-naphthyl groups.
  • the heteroaryl group is preferably composed of a 5- or 6-membered ring, and includes a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a dibenzofuryl group and a dibenzothienyl group.
  • the alkyl group preferably has 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, isopropyl and tert-butyl groups.
  • aryl groups, heteroaryl groups, and alkyl groups may be substituted, and when substituted, 1 selected from the group consisting of deuterium atoms, aryl groups, heteroaryl groups, alkyl groups, and cyano groups preferably substituted by one atom or group or a combination of two or more groups, one atom or group or two or more selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group and an alkyl group; is more preferably substituted with a group that is a combination of
  • R 112 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group.
  • R 111 -R 114 are each independently a hydrogen atom or a deuterium atom.
  • R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 s, and R B and R C may combine with each other to form a cyclic structure.
  • the description of the ring further condensed to the benzene ring in the explanation columns of A11 and A12 can be referred to.
  • one set of R 111 and R 112 , R 112 and R 113 , R 113 and R 114 are bonded to each other to form a benzofuran ring (condensed with a furan ring), a benzothiophene ring (condensed with a thiophene ring), ) or an indole ring (condensed with a pyrrole ring).
  • the group bonded to L from the left in general formula (2) is a substituted or unsubstituted carbazol-9-yl group.
  • it is a carbazol-9-yl group substituted with a deuterium atom, an alkyl group, an aryl group, or a combination of these at least one (preferably both) of the 3- and 6-positions. It may also be an unsubstituted carbazol-9-yl group.
  • the groups bonded to L from the left in general formula (2) are benzofuro[2,3-a]carbazol-9-yl group, benzofuro[3,2-a]carbazole-9 -yl group, benzofuro[2,3-b]carbazol-9-yl group, benzofuro[3,2-b]carbazol-9-yl group, or benzofuro[2,3-c]carbazol-9-yl group (these groups may be substituted, but are, for example, unsubstituted).
  • the group bonded to L from the left in general formula (2) is a benzothieno[2,3-a]carbazol-9-yl group, benzothieno[3,2-a]carbazol-9 -yl group, benzothieno[2,3-b]carbazol-9-yl group, benzothieno[3,2-b]carbazol-9-yl group, benzothieno[2,3-c]carbazol-9-yl group, benzothieno [3,2-c]carbazol-9-yl group (these groups may be substituted, but are, for example, unsubstituted).
  • the group bonded to L from the left in general formula (2) is an indolo[2,3-a]carbazol-9-yl group, an indolo[3,2-a]carbazol-9 -yl group, indolo[2,3-b]carbazol-9-yl group, indolo[3,2-b]carbazol-9-yl group, indolo[2,3-c]carbazol-9-yl group, indolo [3,2-c]carbazol-9-yl group (these groups may be substituted, but are, for example, unsubstituted).
  • the group exemplified as the group bonded to L from the left can also be employed for the group bonded to L from the right in general formula (2). However, it is not an unsubstituted carbazol-9-yl group.
  • X 11 in general formula (2) is N and L is bonded to the N, at least one of R 115 or at least one group bonded to the ring represented by A 12 is a substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group or cyano group.
  • the group bonded to L from the right is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted At least one substituted alkyl or cyano group is present.
  • groups obtained by substituting all hydrogen atoms of alkyl groups D2, D3, D5, D7 to D12, D87 to D104 and D179 to D196 with deuterium atoms are represented by D2(m) and D3, respectively.
  • groups obtained by substituting the phenyl groups (C 6 H 5 ) of D4 to D6, D19 to D86 and D111 to D178 with deuterated C 6 D5 are represented by D4(p) to D6(p) and D19, respectively.
  • Specific examples of the group that can be taken as the group bonded from the right side of L in the general formula (2) include the following specific examples in addition to the above D2 to D196 and deuterium atom-substituted products thereof. can.
  • groups that can be employed in the present invention are not limitedly interpreted by these specific examples. In the following specific examples, the illustration of methyl groups is omitted. * indicates the binding position to L.
  • groups in which the methyl groups (CH 3 ) of X31 to X33 and X64 to X79 are substituted with deuterated CD 3 are respectively X31(m) to X33(m) and X64(m ) through X79(m).
  • groups obtained by substituting the phenyl groups (C 6 H 5 ) of X5 to X21, X38 to X54 and X68 to X70 with deuterated C 6 D5 are represented by X5(p) to X21(p) and X38, respectively.
  • (p)-X54(p), X68(p)-X70(p) are exemplified here.
  • groups in which all hydrogen atoms of X1 to X79 are deuterated are exemplified here as X1(D) to X79(D), respectively.
  • n in the general formula (2) represents an integer of 3 or 4;
  • n is 3 because L is bonded to the benzene ring to which (R 115 )n is bonded.
  • X 11 is N(R A ) and L is bonded to the benzene ring to which (R 115 )n is bonded, n is 3, and X 11 is N(R A ) and n is 4 if L is attached to N represented by X 11 .
  • the n R 115 may be the same or different.
  • L in general formula (2) represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group in which two or more of these are bonded.
  • aryl structure of the arylene group and the heteroaryl structure of the heteroarylene group the above descriptions of the "aryl group” and the “heteroaryl group” can be referred to.
  • Arylene and heteroarylene groups may be substituted and, if substituted, one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, a cyano group, or It is preferably substituted with two or more groups in combination, with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group and an alkyl group, or two or more groups in combination. Substitution is more preferred. When substituted, it is preferably a methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, or a deuterated form thereof.
  • L is an unsubstituted arylene group. Specific examples of L are given below. However, L that can be employed in the present invention is not limitedly interpreted by these specific examples. In the following specific examples, the illustration of methyl groups is omitted. For this reason, for example, L3 to L5 are substituted with methyl groups. * indicates the binding position. L1 is a single bond.
  • the groups bonded from the left of L in general formula (2) are selected from D1 to D196 and deuterated forms thereof, and the groups bonded from the right of L are X1 to X79 and their heavy It is selected from hydrides (embodiment 1).
  • the groups attached to the left of L are selected from among D1 to D12 and deuterated forms thereof, and the groups attached to the right of L are selected from among X1 to X79 and deuterated forms thereof.
  • the groups attached to the left of L are selected from among D13 to D196 and deuterated forms thereof, and the groups attached to the right of L are selected from among X1 to X79 and deuterated forms thereof.
  • the groups attached to the left of L are selected from among D1 to D196 and deuterated forms thereof, and the groups attached to the right of L are selected from among X1 to X66 and deuterated forms thereof.
  • Select (Mode 4) In one aspect of the present invention, the groups attached to the left of L are selected from among D1 to D196 and deuterated versions thereof, and the groups attached to the right of L are selected from among X1 to X33 and deuterated versions thereof.
  • L is L1. In one aspect of the present invention, in aspect 5, L is L1. In one aspect of the present invention, in aspect 6, L is L1. In one aspect of the present invention, in aspect 7, L is L1. In one aspect of the present invention, in aspect 1, L is L6. In one aspect of the present invention, in aspect 2, L is L6. In one aspect of the present invention, in aspect 3, L is L6. In one aspect of the present invention, in aspect 4, L is L6. In one aspect of the present invention, in aspect 5, L is L6. In one aspect of the present invention, in aspect 6, L is L6. In one aspect of the present invention, in aspect 7, L is L6. In one aspect of the present invention, in aspect 1, L is L14.
  • L is L14. In one aspect of the present invention, in aspect 3, L is L14. In one aspect of the present invention, in aspect 4, L is L14. In one aspect of the present invention, in aspect 5, L is L14. In one aspect of the present invention, in aspect 6, L is L14. In one aspect of the present invention, in aspect 7, L is L14. In one aspect of the present invention, in aspect 1, L is L16. In one aspect of the present invention, in aspect 2, L is L16. In one aspect of the present invention, in aspect 3, L is L16. In one aspect of the present invention, in aspect 4, L is L16. In one aspect of the present invention, in aspect 5, L is L16. In one aspect of the present invention, in aspect 6, L is L16. In one aspect of the present invention, in aspect 7, L is L16.
  • a compound represented by the following general formula is selected as the compound represented by general formula (2).
  • R 141 to R 147 each independently represent a hydrogen atom, a deuterium atom, or a substituent, and at least one of R 141 to R 147 is a substituted or unsubstituted aryl group.
  • Q represents a substituted or unsubstituted 12H-benzofurocarbazol-12-ylphenyl group.
  • R 141 to R 147 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
  • each of R 141 to R 147 is independently a hydrogen atom, a deuterium atom, or one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or two or more is an aryl group optionally substituted with a group formed by combining
  • only one of R 141 to R 147 is one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group formed by combining two or more is an aryl group optionally substituted with, and the remainder are each independently a hydrogen atom or a deuterium atom.
  • one of R 141 to R 147 is selected from P1 to P14 given below.
  • Q is optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group formed by combining two or more. -benzofurocarbazol-12-ylphenyl group.
  • Q is an unsubstituted 12H-benzofurocarbazol-12-ylphenyl group.
  • Q is selected from Q1 to Q18 given below. Specific examples of the compounds represented by the above general formula are shown below in tabular form.
  • Table 1 identifies the structures of the compounds by indicating Q and R 141 -R 147 for each compound.
  • compound 141-1-1 is a compound in which Q is Q1, R 141 is P1, and R 142 to R 147 are hydrogen atoms
  • compound 141-1-2 is a compound in which Q is Q1.
  • R 141 is P2 is a compound in which Q is Q1.
  • R 141 is P2 is P2
  • R 142 to R 147 are hydrogen atoms.
  • 14 types of structures are collectively specified in one column.
  • a compound in which Q is Q1, R 141 is P1 to P14, and R 142 to R 147 are hydrogen atoms are collectively identified in order as compounds 141-1-1 to 141-1-14.
  • the structures of Compounds 141-1-1 to 141-1-14 collectively shown here correspond to the structures of Compounds 141-1-1 to 141-1-14 identified in Table 1.
  • Table 2 there is In the row of "141-2-1 to 141-2-14" in Table 2, a compound in which Q is Q2, R 141 is P1 to P14, and R 142 to R 147 are hydrogen atoms, They are collectively specified as compounds 141-2-1 to 141-2-14 in order. Subsequent steps specify the structure of each compound in the same manner.
  • Each compound identified in Table 2 shall be individually disclosed herein.
  • the molecular weight of the compound represented by the general formula (2) is, for example, 1500 or less when the organic layer containing the compound represented by the general formula (2) is intended to be formed by a vapor deposition method and used. It is preferably 1200 or less, more preferably 1000 or less, even more preferably 800 or less, and may be, for example, 600 or less.
  • the lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (2).
  • the compound represented by the general formula (2) preferably has a smaller dipole moment because the orientation becomes higher when the film is formed. This tendency is particularly conspicuous in the region where the dipole moment is 0.9 to 2.5.
  • the dipole moment is preferably less than 2.3, more preferably less than 2.0, and may be selected, for example, from the region of less than 1.7 or from the region of less than 1.4. . Also, it may be selected from a range of 0.4 or more, or selected from a range of 0.9 or more.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms can be selected as the compound represented by the general formula (2).
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms can be selected.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and sulfur atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms and nitrogen atoms can be selected.
  • the membrane of the present invention is a membrane containing the compound represented by the general formula (1) and the compound represented by the general formula (2).
  • the membrane of the present invention may be composed only of the compound represented by the general formula (1) and the compound represented by the general formula (2), or may contain other materials.
  • the membrane of the present invention may contain two or more compounds represented by the general formula (1).
  • the film of the present invention may contain two or more compounds represented by the general formula (2).
  • the membrane of the present invention contains one compound represented by general formula (1) and one compound represented by general formula (2). It is preferable that the membrane of the present invention contains more of the compound represented by the general formula (2) than the compound represented by the general formula (1).
  • the content of the compound represented by the general formula (1) is 0.01 to 49 parts by weight, preferably is 0.1 to 30 parts by weight, for example 1 to 20 parts by weight.
  • the film of the present invention contains a material (hereinafter referred to as "other material") other than the compound represented by the general formula (1) and the compound represented by the general formula (2)
  • the other material is
  • Such compounds can be used as assist dopants.
  • the assist dopant is preferably a delayed fluorescence material.
  • the content of the assist dopant is preferably greater than that of the compound represented by general formula (1) and less than that of the compound represented by general formula (2).
  • the assist dopant is preferably 0.5 to 40 parts by weight. , more preferably 1 to 35 parts by weight, for example, 5 to 30 parts by weight.
  • the delayed fluorescence material that can be used for the film of the present invention preferably has a difference ⁇ EST between the lowest excited singlet energy and the lowest excited triplet energy at 77 K, preferably 0.3 eV or less, more preferably 0.25 eV or less. It is more preferably 0.2 eV or less, more preferably 0.15 eV or less, still more preferably 0.1 eV or less, even more preferably 0.07 eV or less, and 0.2 eV or less. It is more preferably 05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less.
  • thermally activated delayed fluorescence material absorbs the heat emitted by the device and relatively easily undergoes reverse intersystem crossing from the excited triplet state to the excited singlet state, and efficiently contributes the excited triplet energy to light emission. can be done.
  • the lowest excited singlet energy (E S1 ) and the lowest excited triplet energy (E T1 ) of the compound in the present invention are values determined by the following procedure.
  • ⁇ E ST is a value obtained by calculating E S1 -E T1 .
  • (2) Lowest excited singlet energy (E S1 ) A thin film or a toluene solution (concentration 10 ⁇ 5 mol/L) of the compound to be measured is prepared and used as a sample. The fluorescence spectrum of this sample is measured at room temperature (300K). In the fluorescence spectrum, the vertical axis is light emission and the horizontal axis is wavelength.
  • the maximum point with a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and is closest to the maximum value on the short wavelength side.
  • the tangent line drawn at the point where the value is taken is taken as the tangent line to the rise on the short wavelength side of the phosphorescence spectrum.
  • a compound (cyanobenzene derivative) having a cyanobenzene structure in which the benzene ring is substituted with one cyano group is used as the delayed fluorescence material.
  • a compound (dicyanobenzene derivative) having a dicyanobenzene structure in which two cyano groups are substituted on the benzene ring is used as the delayed fluorescence material.
  • a compound (azabenzene derivative) having an azabenzene structure in which at least one carbon atom constituting the ring skeleton of a benzene ring is substituted with a nitrogen atom is used as the delayed fluorescence material.
  • a compound in which a benzene ring is substituted with a diaryltriazinyl group is used as the delayed fluorescence material.
  • delayed fluorescence material that can be used in the present invention are shown below.
  • the delayed fluorescence material that can be used in the present invention is not limited to the following specific examples.
  • known delayed fluorescence materials other than those described above can be used in appropriate combination with the compound represented by general formula (1). Moreover, even unknown delayed fluorescence materials can be used.
  • the delayed fluorescence material paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955, Paragraphs 0008 to 0071 and 0118 to 0133 of WO2013/081088, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975, WO2013 / Paragraphs 0007 to 0032 and 0079 to 0084 of 133359, paragraphs 0008 to 0054 and 0101 to 0121 of WO2013/161437, paragraphs 0007 to 0041 and 0060
  • JP 2013-253121, WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895, WO2014/126200, WO2014/136758, WO2014/133121 Publications, WO2014/136860, WO2014/196585, WO2014/189122, WO2014/168101, WO2015/008580, WO2014/203840, WO2015/002213, WO2010/01620 WO2015/019725, WO2015/072470, WO2015/108049, WO2015/080182, WO2015/072537, WO2015/080183, JP 2015-129240, WO2015/129714, WO2015/129715, WO2015/133501, WO2015/136880, WO2015/137244, WO2015/137202, WO2015/137136, WO2015/146541, WO2015/159541
  • a luminescent material that emits delayed fluorescence can also be employed.
  • the delayed fluorescence material used in the present invention preferably does not contain metal atoms.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms can be selected.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms can be selected.
  • a compound composed of carbon atoms, hydrogen atoms and nitrogen atoms can be selected as the delayed fluorescence material.
  • the film of the present invention may contain, as another material, a luminescent material having an excited singlet energy lower than that of the compound represented by the general formula (1) or the compound represented by the general formula (2).
  • the compound represented by the general formula (1) functions as an assist dopant
  • the light-emitting material which is another material, mainly emits light.
  • a delayed fluorescence material may be selected as the light emitting material.
  • the content of the luminescent material is preferably less than the compound represented by the general formula (1) or the compound represented by the general formula (2). When the total amount of the compound represented by the general formula (1), the compound represented by the general formula (2) and the luminescent material is 100 parts by weight, the content of the luminescent material is 0.01 to 10 parts by weight.
  • Light-emitting materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene.
  • Derivatives fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives containing metals (Al, Zn), and the like can be used. These exemplified skeletons may or may not have a substituent. Also, these exemplary skeletons may be combined. Examples of luminescent materials that can be used in the film of the present invention are given below. Compounds described in paragraphs 0220 to 0239 of WO2015/022974 can also be employed.
  • the membranes of the present invention can be formed in a wet process.
  • a solution in which a composition containing the compound of the present invention is dissolved is applied to the surface, and a film is formed after removal of the solvent.
  • wet processes include spin coating, slit coating, inkjet (spray), gravure printing, offset printing, and flexographic printing, but are not limited to these.
  • an appropriate organic solvent capable of dissolving the composition containing the film-constituting materials such as the compound of general formula (1) and the compound of general formula (2) is selected and used.
  • films comprising compounds of the present invention can be formed in a dry process.
  • the dry process can be vacuum deposition, but is not limited to this.
  • the compounds forming the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed.
  • a single vapor deposition source a mixed powder obtained by mixing powders of compounds may be used, a compression molding obtained by compressing the mixed powder may be used, or each compound may be heated, melted, and cooled. Mixtures may also be used.
  • the composition ratio of the plurality of compounds contained in the vapor deposition source is reduced by performing co-deposition under conditions in which the vapor deposition rates (weight reduction rates) of the plurality of compounds contained in the single vapor deposition source match or substantially match. It is possible to form a film having a composition ratio corresponding to A film having a desired composition ratio can be easily formed by mixing a plurality of compounds at the same composition ratio as that of the film to be formed, and using this as an evaporation source. In one embodiment, the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified and used as the temperature during co-deposition. The thickness of the film of the present invention can be appropriately determined depending on the application.
  • the thickness when used for light emission, can be in the range of 0.5 to 100 ⁇ m.
  • the compound represented by general formula (1) has a high degree of orientation. Such high orientation can be achieved by using the compound represented by the general formula (2) in combination. In particular, by using in combination with a compound having a low dipole moment among the compounds represented by the general formula (2), even higher orientation can be achieved. Since the compound represented by the general formula (1) is horizontally aligned on the film surface, the luminous efficiency is increased. Orientation can be evaluated by an orientation value (S value). A larger negative value (a smaller value) means a higher orientation.
  • the orientation value (S value) is from Scientific Reports 2017, 7, 8405.
  • the orientation value of the compound represented by general formula (1) in the film of the present invention is preferably ⁇ 0.33 or less, more preferably ⁇ 0.38 or less, and ⁇ 0.41 or less. is more preferred.
  • the membranes of the present invention emit delayed fluorescence.
  • the films of the present invention when excited by thermal or electronic means, are in the UV region, the blue, green, yellow, orange, red regions of the visible spectrum (eg, from about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or in the near-infrared region.
  • the films of the present invention do not contain metallic elements.
  • the membranes of the present invention can be composed of materials consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, sulfur atoms and boron atoms. can.
  • the film of the present invention can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and boron atoms.
  • the organic light-emitting device of the present invention is an organic light-emitting device using the compound represented by the general formula (1) and the compound represented by the general formula (2).
  • the organic light emitting device includes an emissive layer.
  • the light-emitting layer contains a compound represented by general formula (1) as a light-emitting material.
  • the organic light emitting device is an organic photoluminescent device (organic PL device).
  • the organic light-emitting device is an organic electroluminescent device (organic EL device).
  • the compound of general formula (2) assists the light emitting material of general formula (1) to emit light.
  • the emissive layer is the inventive film described above.
  • the organic photoluminescent device includes at least one emissive layer.
  • an organic electroluminescent device includes at least an anode, a cathode, and an organic layer between said anode and said cathode.
  • the organic layers include at least the emissive layer.
  • the organic layers include only the emissive layer.
  • the organic layers include one or more organic layers in addition to the emissive layer. Examples of organic layers include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers and exciton blocking layers.
  • the hole transport layer may be a hole injection transport layer with hole injection functionality
  • the electron transport layer may be an electron injection transport layer with electron injection functionality.
  • the organic electroluminescent device of the present invention is held by a substrate, which is not particularly limited and commonly used in organic electroluminescent devices such as glass, transparent plastic, quartz and silicon. Any material formed by
  • the anode of the organic electroluminescent device is made from metals, alloys, conductive compounds, or combinations thereof.
  • the metal, alloy or conductive compound has a high work function (4 eV or greater).
  • the metal is Au.
  • the conductive transparent material is selected from CuI, indium tin oxide ( ITO), SnO2 and ZnO. Some embodiments use amorphous materials that can form transparent conductive films, such as IDIXO (In 2 O 3 —ZnO).
  • the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering.
  • the film is patterned by photolithographic methods. In some embodiments, if the pattern does not need to be highly precise (eg, about 100 ⁇ m or greater), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto the electrode material. In some embodiments, wet film forming methods such as printing and coating methods are used when coating materials such as organic conductive compounds can be applied.
  • the anode has a transmittance of greater than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode varies depending on the material used.
  • the cathode is made of electrode materials such as metals with a low work function (4 eV or less) (referred to as electron-injecting metals), alloys, conductive compounds, or combinations thereof.
  • the electrode material is sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum - aluminum oxide (Al2 O 3 ) mixtures, indium, lithium-aluminum mixtures and rare earth elements.
  • a mixture of an electron-injecting metal and a second metal that is a stable metal with a higher work function than the electron-injecting metal is used.
  • the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al 2 O 3 ) mixtures, lithium-aluminum mixtures and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation.
  • the cathode is manufactured by depositing or sputtering the electrode material as a thin film. In some embodiments, the cathode has a sheet resistance of no more than several hundred ohms per unit area. In some embodiments, the thickness of said cathode is between 10 nm and 5 ⁇ m. In some embodiments, the thickness of the cathode is 50-200 nm.
  • either one of the anode and cathode of the organic electroluminescent device is transparent or translucent to allow transmission of emitted light.
  • transparent or translucent electroluminescent elements enhance light radiance.
  • the cathode is formed of a conductive transparent material as described above for the anode, thereby forming a transparent or translucent cathode.
  • the device includes an anode and a cathode, both transparent or translucent.
  • the injection layer is the layer between the electrode and the organic layer. In some embodiments, the injection layer reduces drive voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be placed between the anode and the light-emitting layer or hole-transporting layer and between the cathode and the light-emitting layer or electron-transporting layer. In some embodiments, an injection layer is present. In some embodiments, there is no injection layer. Preferred examples of compounds that can be used as the hole injection material are given below.
  • a barrier layer is a layer that can prevent charges (electrons or holes) and/or excitons present in the light-emitting layer from diffusing out of the light-emitting layer.
  • an electron blocking layer is between the light-emitting layer and the hole-transporting layer to block electrons from passing through the light-emitting layer to the hole-transporting layer.
  • a hole blocking layer is between the emissive layer and the electron transport layer and blocks holes from passing through the emissive layer to the electron transport layer.
  • the barrier layer prevents excitons from diffusing out of the emissive layer.
  • the electron blocking layer and the hole blocking layer constitute an exciton blocking layer.
  • the terms "electron blocking layer” or “exciton blocking layer” include layers that have both the functionality of an electron blocking layer and an exciton blocking layer.
  • Hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer blocks holes from reaching the electron transport layer during electron transport. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the hole blocking layer can be the same materials as described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.
  • Electron barrier layer The electron blocking layer transports holes. In some embodiments, the electron blocking layer prevents electrons from reaching the hole transport layer during hole transport. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the electron blocking layer may be the same materials as described above for the hole transport layer. As compounds that can be used as electron barrier materials, compounds represented by the following general formulas can be exemplified. In the general formula above, Ar 11 to Ar 13 each independently represent a substituted or unsubstituted aryl group.
  • Examples include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, and a substituted or unsubstituted naphthalene-2-yl group.
  • Substituents for the hydrogen atoms of the aryl group include one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more thereof.
  • Examples of substituted aryl groups include 4-biphenylyl, 3-biphenylyl, and m-terphenyl-5'-yl groups. Specific examples of the compounds represented by the above general formula are shown below. Specific examples of preferred compounds that can be used as the electron barrier material are given below.
  • Exciton barrier layer The exciton blocking layer prevents diffusion of excitons generated through recombination of holes and electrons in the light emitting layer to the charge transport layer. In some embodiments, the exciton blocking layer allows effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, an exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides thereof. In some embodiments, when an exciton blocking layer is present on the anode side, it may be present between and adjacent to the hole-transporting layer and the light-emitting layer.
  • an exciton blocking layer when an exciton blocking layer is present on the cathode side, it may be between and adjacent to the emissive layer and the cathode. In some embodiments, a hole-injection layer, electron-blocking layer, or similar layer is present between the anode and an exciton-blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron blocking layer, hole blocking layer or similar layer is present between the cathode and an exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and triplet energy, respectively, of the emissive material.
  • the hole-transporting layer comprises a hole-transporting material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one property of a hole injection or transport property and an electron barrier property.
  • the hole transport material is an organic material.
  • the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolones.
  • the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as the hole-transporting material are given below.
  • the electron transport layer includes an electron transport material.
  • the electron transport layer is a single layer.
  • the electron transport layer has multiple layers.
  • the electron-transporting material need only function to transport electrons injected from the cathode to the emissive layer.
  • the electron transport material also functions as a hole blocking material.
  • electron-transporting layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxazide Azole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof.
  • the electron transport material is a thiadiazole derivative or a quinoxaline derivative.
  • the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as the electron-transporting material are given below.
  • examples of preferred compounds as materials that can be added to each organic layer are given.
  • it may be added as a stabilizing material.
  • Preferred materials that can be used in organic electroluminescence elements are specifically exemplified, but materials that can be used in the present invention are not limitedly interpreted by the following exemplified compounds. Moreover, even compounds exemplified as materials having specific functions can be used as materials having other functions.
  • the emissive layer is incorporated into the device.
  • devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones and tablets.
  • an electronic device includes an OLED having at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
  • the composition may be useful in facilitating charge or energy transfer within a device and/or as a hole transport material.
  • OLEDs organic light emitting diodes
  • OICs organic integrated circuits
  • O-FETs organic field effect transistors
  • O-TFTs organic thin film transistors
  • O-LETs organic light emitting transistors
  • O-SC organic solar cells.
  • O-SC organic optical detectors
  • O-FQD organic field-quench devices
  • LOC luminescent fuel cells
  • O-lasers organic laser diodes
  • an electronic device includes an OLED including at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • the device includes OLEDs of different colors.
  • the device includes an array including combinations of OLEDs.
  • said combination of OLEDs is a combination of three colors (eg RGB).
  • the combination of OLEDs is a combination of colors other than red, green, and blue (eg, orange and yellow-green).
  • said combination of OLEDs is a combination of two, four or more colors.
  • the device a circuit board having a first side with a mounting surface and a second opposite side and defining at least one opening; at least one OLED on the mounting surface, wherein the at least one OLED is configured to emit light, wherein the at least one OLED includes at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode; at least one OLED comprising a housing for a circuit board; at least one connector located at an end of said housing, said housing and said connector defining a package suitable for attachment to a lighting fixture.
  • the OLED light comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some light emitted in the first direction is polarized and emitted in the second direction. In some embodiments, a reflector is used to polarize light emitted in the first direction.
  • the emissive layers of the invention can be used in screens or displays.
  • the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, evaporation or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching to provide unique aspect ratio pixels.
  • Said screens also called masks
  • the corresponding artwork pattern design allows placement of very steep narrow tie-bars between pixels in the vertical direction as well as large and wide beveled openings in the horizontal direction.
  • the internal patterning of the pixels makes it possible to construct three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Further, the use of imaged "stripes" or halftone circles in pixel areas protects etching in specific areas until these specific patterns are undercut and removed from the substrate. All pixel areas are then treated with a similar etch rate, but their depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with varying degrees of protection within the pixel, allowing for the localized deep etching necessary to form steep vertical bevels. . A preferred material for the evaporation mask is Invar.
  • Invar is a metal alloy that is cold rolled into long thin sheets in steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask.
  • a suitable and low-cost method for forming the open areas in the deposition mask is by wet chemical etching.
  • the screen or display pattern is a matrix of pixels on a substrate.
  • screen or display patterns are fabricated using lithography (eg, photolithography and e-beam lithography).
  • the screen or display pattern is processed using wet chemical etching.
  • the screen or display pattern is fabricated using plasma etching.
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, and the TFT is coated with a planarization film, a pixel electrode, a light emitting layer , a counter electrode and an encapsulation layer, are sequentially formed and cut from the mother panel.
  • TFT thin film transistor
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, and the TFT is coated with a planarization film, a pixel electrode, a light emitting layer , a counter electrode and an encapsulation layer, are sequentially formed and cut from the mother panel.
  • TFT thin film transistor
  • an organic light emitting diode (OLED) display comprising: forming a barrier layer on the base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interfaces between the cell panels.
  • the barrier layer is an inorganic film, eg, made of SiNx, and the edges of the barrier layer are covered with an organic film, made of polyimide or acrylic.
  • the organic film helps the mother panel to be softly cut into cell panels.
  • a thin film transistor (TFT) layer has an emissive layer, a gate electrode, and source/drain electrodes.
  • Each of the plurality of display units may have a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film;
  • the applied organic film is made of the same material as the material of the planarizing film and is formed at the same time as the planarizing film is formed.
  • the light-emitting unit is coupled with the TFT layer by a passivation layer, a planarizing film therebetween, and an encapsulation layer that covers and protects the light-emitting unit.
  • the organic film is not connected to the display unit or encapsulation layer.
  • each of the organic film and the planarizing film may include one of polyimide and acrylic.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide. The method further comprises attaching a carrier substrate made of a glass material to one surface of a base substrate made of polyimide before forming a barrier layer on another surface of the base substrate; separating the carrier substrate from the base substrate prior to cutting along the interface.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film placed on the TFT layer to cover the TFT layer.
  • the planarizing film is an organic film formed over a passivation layer.
  • the planarizing film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarizing film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer such that a portion of the organic film is in direct contact with the base substrate and the remainder of the organic film is in contact with the base substrate. , in contact with the barrier layer while surrounding the edges of the barrier layer.
  • the emissive layer comprises a pixel electrode, a counter electrode, and an organic emissive layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrodes are connected to source/drain electrodes of the TFT layer.
  • a suitable voltage is formed between the pixel electrode and the counter electrode, causing the organic light emitting layer to emit light, thereby displaying an image. is formed.
  • An image forming unit having a TFT layer and a light emitting unit is hereinafter referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed into a thin encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin film-like encapsulation structure in which multiple thin films are stacked.
  • the organic film applied to the interface portion is spaced apart from each of the plurality of display units.
  • the organic film is formed such that a portion of the organic film is in direct contact with the base substrate and the remaining portion of the organic film is in contact with the barrier layer while surrounding the edges of the barrier layer. be done.
  • the OLED display is flexible and uses a flexible base substrate made of polyimide.
  • the base substrate is formed on a carrier substrate made of glass material, and then the carrier substrate is separated.
  • a barrier layer is formed on the surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of a mother panel, while barrier layers are formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the groove.
  • the manufacturing method further comprises cutting along the interface, wherein a groove is formed in the barrier layer, at least a portion of the organic film is formed with the groove, and the groove is Does not penetrate the base substrate.
  • a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on and cover the TFT layer.
  • the planarizing film eg made of polyimide or acrylic
  • the interface grooves are covered with an organic film, eg made of polyimide or acrylic. This prevents cracking by having the organic film absorb the impact that occurs when each cell panel is cut along the groove at the interface.
  • the grooves at the interfaces between the barrier layers are coated with an organic film to absorb shocks that might otherwise be transmitted to the barrier layers, so that each cell panel is softly cut and the barrier layers It may prevent cracks from forming.
  • the organic film covering the groove of the interface and the planarizing film are spaced apart from each other. For example, when the organic film and the planarizing film are connected to each other as a single layer, external moisture may enter the display unit through the planarizing film and the portion where the organic film remains. The organic film and planarizing film are spaced from each other such that the organic film is spaced from the display unit.
  • the display unit is formed by forming a light-emitting unit and an encapsulating layer is placed over the display unit to cover the display unit.
  • the carrier substrate carrying the base substrate is separated from the base substrate.
  • the carrier substrate separates from the base substrate due to the difference in coefficient of thermal expansion between the carrier substrate and the base substrate.
  • the mother panel is cut into cell panels.
  • the mother panel is cut along the interfaces between the cell panels using a cutter.
  • the interface groove along which the mother panel is cut is coated with an organic film so that the organic film absorbs impact during cutting.
  • the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces the reject rate of the product and stabilizes its quality.
  • Another embodiment includes a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic layer applied to the edges of the barrier layer.
  • An OLED display comprising a film.
  • carbazole (7.69 g, 46.0 mmol) was added to an N,N-dimethylformamide solution (160 mL) of sodium hydride (1.16 g, 29.0 mmol) and stirred at room temperature for 30 minutes.
  • ,5-dibromo-1,4-difluorobenzene (5.00 g, 18.4 mmol) was added and stirred at 60° C. for 16 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered.
  • n-butyllithium (1.6 mol/L hexane solution, 4.5 mL, 7.19 mmol) was added to a toluene solution (100 mL) of Intermediate A (1.00 g, 1.80 mmol) at -30°C. and stirred at room temperature for 1 hour.
  • the reaction mixture was cooled to ⁇ 30° C., boron tribromide (0.991 g, 3.96 mmol) was added, and the mixture was stirred at room temperature for 30 minutes.
  • 1,2,2,6,6-Pentamethylpiperidine (0.558 g, 3.60 mmol) was added to the reaction mixture and stirred at 120° C. for 17 hours.
  • n-butyl lithium (1.6 mol/L hexane solution, 2.9 mL, 4.60 mmol) was added to a toluene solution (300 mL) of Intermediate B (1.00 g, 1.15 mmol) at -30°C. and stirred at room temperature for 1 hour.
  • the reaction mixture was cooled to ⁇ 30° C., boron tribromide (0.633 g, 2.53 mmol) was added, and the mixture was stirred at room temperature for 30 minutes.
  • 1,2,2,6,6-Pentamethylpiperidine (0.357 g, 2.30 mmol) was added to the reaction mixture and stirred at 120° C. for 17 hours.
  • reaction mixture was cooled to room temperature, 2-mesitylmagnesium bromide (1.0 mol/L tetrahydrofuran solution, 3.4 mL, 3.40 mmol) was added and stirred at room temperature for 4 hours.
  • the obtained reaction mixture was filtered through a silica pad (toluene), and the solvent of the filtrate was distilled off. Ethyl acetate was added to the resulting viscous body and the precipitate was filtered to obtain Compound 2 (0.0710 g, 0.0732 mmol, yield 6%) as an orange solid.
  • reaction mixture was returned to room temperature, 2,4,6-triisopropylmagnesium bromide-lithium chloride complex (1.0 mol/L tetrahydrofuran solution, 17.7 mL, 17.7 mmol) was added, and the mixture was stirred at 120° C. for 4 hours.
  • Example 1 Preparation of thin film
  • the light-emitting materials listed in Table 3 and the host materials listed in Table 3 were different from each other under the condition of a degree of vacuum of less than 1 ⁇ 10 -3 Pa on a quartz substrate by vacuum deposition.
  • a thin film with a thickness of 100 nm was formed by evaporation from an evaporation source.
  • the content of the luminescent material was set to 30% by mass.
  • Table 3 shows the measurement results of the orientation value S of the light-emitting material of each formed thin film together with the dipole moment of each light-emitting material. It was confirmed that the orientation of the light-emitting material represented by the general formula (1) was enhanced by using the host material represented by the general formula (2). It was also confirmed that by using a host material having a dipole moment of less than 2.52, high orientation of the light-emitting material can be achieved.
  • Example 2 Preparation and evaluation of organic electroluminescence device
  • ITO indium tin oxide
  • the content of the luminescent material was set to 30% by mass.
  • Liq and SF3-TRZ were co-deposited from different vapor deposition sources to form a layer with a thickness of 30 nm.
  • the contents of Liq and SF3-TRZ in this layer were 30 mass % and 70 mass %, respectively.
  • Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode to form an organic electroluminescence device. When electricity was applied to each organic electroluminescence element, light emission was observed from any element.
  • the amount of light emitted from the light-emitting material was the largest among the materials contained in the light-emitting layer.
  • the external quantum efficiency (EQE) and driving voltage (V INT ) of each organic electroluminescence device at 6.3 mA/cm 2 were measured, and the results are shown in Table 3.
  • the organic electroluminescence devices of the present invention (devices 1 to 9) all showed high EQE and were excellent in low driving voltage.
  • the light-emitting material exhibits excellent orientation and can be suitably used for organic light-emitting devices.
  • the organic light-emitting device of the present invention has low driving voltage and high luminous efficiency, and thus has high industrial applicability.

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US12484435B2 (en) 2021-06-23 2025-11-25 Kyulux, Inc. Compound, light-emitting material and organic light-emitting element

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