WO2022254965A1 - 化合物、発光材料および発光素子 - Google Patents

化合物、発光材料および発光素子 Download PDF

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WO2022254965A1
WO2022254965A1 PCT/JP2022/017166 JP2022017166W WO2022254965A1 WO 2022254965 A1 WO2022254965 A1 WO 2022254965A1 JP 2022017166 W JP2022017166 W JP 2022017166W WO 2022254965 A1 WO2022254965 A1 WO 2022254965A1
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substituted
ring
light
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善丈 鈴木
正貴 山下
琢哉 比嘉
侑 山根
昇 真田
幸誠 金原
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Kyulux Inc
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Kyulux Inc
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Priority to JP2023525646A priority patent/JP7758374B2/ja
Priority to CN202280039330.4A priority patent/CN117396486A/zh
Publication of WO2022254965A1 publication Critical patent/WO2022254965A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same.
  • organic electroluminescence elements organic electroluminescence elements
  • various attempts have been made to improve the luminous efficiency by newly developing and combining electron transporting materials, hole transporting materials, light emitting materials, and the like, which constitute organic electroluminescence elements.
  • research on organic electroluminescence elements using delayed fluorescence materials can also be seen.
  • a delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after reverse intersystem crossing from the excited triplet state to the excited singlet state occurs in the excited state. Fluorescence by such a pathway is called delayed fluorescence because it is observed later than the fluorescence from the excited singlet state directly generated from the ground state (ordinary fluorescence).
  • the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%.
  • the delayed fluorescence material not only the excited singlet state but also the excited triplet state can be used for fluorescence emission through the reverse intersystem crossing described above, so the emission is higher than that of ordinary fluorescent materials. Efficiency will be obtained.
  • delayed fluorescence materials have been discovered through various studies. However, a material that emits delayed fluorescence is not immediately useful as a light-emitting material. Among delayed fluorescence materials, there are those in which reverse intersystem crossing is relatively difficult to occur, and in which the lifetime of delayed fluorescence is long. In addition, there are some devices that accumulate excitons in a high current density region, resulting in a decrease in luminous efficiency, or rapidly degrade when driven for a long period of time. Therefore, the actual situation is that there are extremely many delayed fluorescence materials that have room for improvement in terms of practicality. Moreover, in recent years, the properties required for fluorescent materials have been increasing. Therefore, even excellent delayed fluorescence materials such as compounds having the following structures are required to further improve their properties (see Patent Document 1).
  • the present inventors conducted extensive research with the aim of providing compounds that are more useful as light-emitting materials for light-emitting devices. Then, intensive studies were carried out with the aim of deriving and generalizing the general formulas of compounds that are more useful as light-emitting materials.
  • the present inventors found that among terephthalonitrile derivatives, compounds having a structure that satisfies specific conditions are useful as light-emitting materials.
  • the present invention has been proposed based on these findings, and specifically has the following configurations.
  • R 1 to R 4 each independently represent a donor group, at least one of which is an indol-1-yl group with condensed rings.
  • the ring-fused indol-1-yl group forms a condensed ring having 4 or more rings by ring condensation with indole, and the condensed ring may be substituted.
  • 1 to 2 of R 1 to R 4 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded via a carbon atom.
  • the remaining R 1 to R 4 represent hydrogen atoms or deuterium atoms.
  • two of R 1 to R 4 are each independently a donor group, at least one of which is an indol-1-yl group to which the ring is condensed; one of R 1 to R 4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded at a carbon atom;
  • two of R 1 to R 4 are each independently a donor group, at least one of which is an indol-1-yl group to which the ring is condensed;
  • R 1 to R 4 are each independently a donor group, at least one of which is an indol-1-yl group to which the ring is condensed; The compound according to [1], wherein one of R 1 to R 4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded at a carbon atom.
  • R 1 and R 4 are each independently a donor group; The compound according to any one of [1] to [4], wherein R 3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group attached at a carbon atom.
  • R 2 and R 4 are each independently a donor group; The compound according to any one of [1] to [4], wherein R 3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group attached at a carbon atom. [7] The compound according to any one of [1] to [6], wherein the condensed ring has 5 or more rings. [8] The compound according to [7], wherein a carbon atom constituting the condensed ring skeleton having 4 or more rings is substituted with a substituted or unsubstituted aryl group.
  • the indol-1-yl group to which the rings are condensed has a structure in which heterocycles are condensed at positions 4 and 5 of the indole ring, according to any one of [1] to [12].
  • Compound. [14] The compound according to any one of [1] to [13], wherein Ar is a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group.
  • Ar is a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group.
  • the compound according to any one of [1] to [14] consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.
  • a luminescent material comprising the compound according to any one of [1] to [15].
  • a light-emitting device comprising the compound according to any one of [1] to [15].
  • the compound of the present invention is useful as a luminescent material. Further, the compounds of the present invention include compounds having a short delayed fluorescence lifetime. Furthermore, an organic light-emitting device using the compound of the present invention is useful because of its high device durability.
  • Two to three of R 1 to R 4 in general formula (1) each independently represent a donor group. At least one of the donor groups is a substituted or unsubstituted indol-1-yl group, and an indole ring constituting the indol-1-yl group is fused with a ring, thereby It forms a condensed ring with 4 or more rings.
  • a group satisfying this condition is referred to as a "ring-fused indol-1-yl group”.
  • the ring-fused indol-1-yl group may be a polycyclic ring having one ring condensed to the benzene ring or pyrrole ring that constitutes the indol-1-yl group, or may have two or more polycyclic or monocyclic rings.
  • the ring-fused indol-1-yl group may be a polycyclic ring having one ring condensed to the benzene ring or pyrrole ring that constitutes the indol-1-yl group, or may have two or more polycyclic or monocyclic rings.
  • Two condensed rings may be the same or different.
  • a condensed ring having 4 or more, 5 or more, or 6 or more rings may be formed, and a condensed ring having 5 or more rings is preferably formed.
  • a compound having a condensed ring having 4 rings, a compound having a condensed ring having 5 rings, a compound having a condensed ring having 6 rings, and a condensed ring having 8 rings A compound forming a ring may be employed.
  • the ring may be fused only at the 2,3-position (b), only the 4,5-position (e) or only the 5,6-position (f) of the indole ring.
  • any one of 4,5-position (e), 5,6-position (f) and 6,7-position (g) may be condensed at 2,3-position (b) (the following formula see, * indicates binding position).
  • a ring that is directly condensed to a benzene ring or pyrrole ring that constitutes an indol-1-yl group is Any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring may be used.
  • an aromatic hydrocarbon ring an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring
  • one or more rings selected from the group consisting of benzene rings and aromatic heterocycles are directly condensed.
  • a heterocycle as used herein is a ring containing a heteroatom.
  • the heteroatoms are preferably selected from oxygen, sulfur, nitrogen and silicon atoms, more preferably from oxygen, sulfur and nitrogen atoms.
  • the heteroatom is an oxygen atom.
  • the heteroatom is a sulfur atom.
  • the heteroatom is a nitrogen atom.
  • the number of hetero atoms contained as ring skeleton-constituting atoms of the hetero ring is 1 or more, preferably 1 to 3, more preferably 1 or 2. In one preferred embodiment, the number of heteroatoms is one. When the number of heteroatoms is two or more, they are preferably heteroatoms of the same type, but may be composed of heteroatoms of different types. For example, two or more heteroatoms may all be nitrogen atoms.
  • Ring skeleton atoms other than heteroatoms are carbon atoms.
  • the number of atoms constituting the ring skeleton constituting the hetero ring directly condensed to the benzene ring constituting the indol-1-yl group is preferably 4 to 8, more preferably 5 to 7, 5 or 6 is more preferred.
  • the heterocyclic ring has 5 ring skeleton-constituting atoms.
  • the hetero ring preferably has two or more conjugated double bonds, and the condensed hetero ring preferably expands the conjugated system of the indole ring (i.e., has aromaticity). is preferred).
  • Preferred examples of heterocycles include furan rings, thiophene rings and pyrrole rings.
  • the ring directly condensed to the benzene ring or pyrrole ring constituting the indol-1-yl group may be further condensed with another ring.
  • the condensed ring may be a monocyclic ring or a condensed ring.
  • condensed rings include aromatic hydrocarbon rings, aromatic heterocycles, aliphatic hydrocarbon rings, and aliphatic heterocycles.
  • at least one hetero ring is directly condensed with the benzene ring or pyrrole ring that constitutes the indol-1-yl group.
  • the condensed rings that make up the condensed indol-1-yl group contain two or more heterocycles.
  • a case containing two heterocycles and a case containing three heterocycles can be exemplified.
  • a benzene ring can be mentioned as an aromatic hydrocarbon ring in the present specification.
  • Aromatic heterocycles include furan ring, thiophene ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, pyrrole ring, pyrazole ring and imidazole ring.
  • a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring can be mentioned as the aliphatic hydrocarbon ring.
  • Examples of aliphatic heterocycles include piperidine ring, pyrrolidine ring and imidazoline ring.
  • condensed rings include naphthalene ring, anthracene ring, phenanthrene ring, pyran ring, tetracene ring, indole ring, isoindole ring, benzimidazole ring, benzotriazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, and cinnoline. rings can be mentioned.
  • the ring-fused indol-1-yl group is a benzofuran-fused indol-1-yl group, a benzothiophene-fused indol-1-yl group, an indole-fused indol-1-yl group, or a sylindene-fused indol-1-yl group.
  • the indol-1-yl group is a benzofuran-fused indol-1-yl group, a benzothiophene-fused indol-1-yl group, or an indole-fused indol-1-yl group.
  • a substituted or unsubstituted benzofuro[2,3-e]indol-1-yl group can be employed as the benzofuran-fused indol-1-yl group.
  • a substituted or unsubstituted benzofuro[3,2-e]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[2,3-f]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[3,2-f]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[2,3-g]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[3,2-g]indol-1-yl group can also be employed.
  • the condensed rings constituting these groups may or may not be further condensed.
  • a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be employed as the benzofuran-fused indol-1-yl group.
  • a substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can also be employed.
  • the condensed rings constituting these groups may or may not be further condensed.
  • Preferred benzofuran-fused indol-1-yl groups include groups having any of the structures below, and hydrogen atoms in the structures below may or may not be substituted.
  • those substituted with an aryl group such as a phenyl group, or those substituted at the 3-position of the carbazole ring can be preferably exemplified.
  • the benzene ring in the structure below may or may not be condensed with another ring.
  • a carbazol-9-yl group in which two benzofuran rings are condensed at the 2 and 3 positions can also be employed. Specifically, it is a group having any of the structures below, and hydrogen atoms in the structures below may or may not be substituted. Further, the benzene ring in the structure below may or may not be condensed with another ring.
  • a substituted or unsubstituted benzothieno[2,3-e]indol-1-yl group can be employed as the benzothiophene-fused indol-1-yl group.
  • a substituted or unsubstituted benzothieno[3,2-e]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-f]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[3,2-f]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-g]indol-1-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[3,2-g]indol-1-yl group can also be employed.
  • the condensed rings constituting these groups may or may not be further condensed.
  • a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be employed as the benzothiophene-fused indol-1-yl group.
  • a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be employed.
  • the condensed rings constituting these groups may or may not be further condensed.
  • Preferred benzothiophene-fused indol-1-yl groups include groups having any of the structures below, and hydrogen atoms in the structures below may or may not be substituted.
  • hydrogen atoms in the structures below may or may not be substituted.
  • those substituted with an aryl group such as a phenyl group, or those substituted at the 3-position of the carbazole ring can be preferably exemplified.
  • the benzene ring in the structure below may or may not be condensed with another ring.
  • a carbazol-9-yl group in which two benzothiophene rings are fused at the 2 and 3 positions can also be employed. Specifically, it is a group having any of the structures below, and hydrogen atoms in the structures below may or may not be substituted. Further, the benzene ring in the structure below may or may not be condensed with another ring.
  • a substituted or unsubstituted indolo[2,3-e]indol-1-yl group can be employed as the indole-fused indol-1-yl group.
  • a substituted or unsubstituted indolo[3,2-e]indol-1-yl group can also be employed.
  • a substituted or unsubstituted indolo[2,3-f]indol-1-yl group can also be employed.
  • a substituted or unsubstituted indolo[3,2-f]indol-1-yl group can also be employed.
  • a substituted or unsubstituted indolo[2,3-g]indol-1-yl group can also be employed.
  • a substituted or unsubstituted indolo[3,2-g]indol-1-yl group can also be employed.
  • the condensed rings constituting these groups may or may not be further condensed.
  • a substituted or unsubstituted indolo[2,3-a]carbazol-9-yl group can be employed as the indole-fused indol-1-yl group.
  • a substituted or unsubstituted indolo[3,2-a]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted indolo[2,3-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted indolo[3,2-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted indolo[2,3-c]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted indolo[3,2-c]carbazol-9-yl group can also be employed.
  • the condensed rings constituting these groups may or may not be further condensed.
  • Preferred indole-fused indol-1-yl groups include groups having any of the structures below, and hydrogen atoms in the structures below may or may not be substituted.
  • hydrogen atoms in the structures below may or may not be substituted.
  • those substituted with an aryl group such as a phenyl group, or those substituted at the 3-position of the carbazole ring can be preferably exemplified.
  • the benzene ring in the structure below may or may not be condensed with another ring.
  • alkyl group as used herein 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 a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom.
  • 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.
  • 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.
  • arylene group or heteroarylene group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 2-pyridyl group, 3-pyridyl group, 4 - pyridyl group.
  • the ring-fused indol-1-yl group preferably has 16 or more atoms other than hydrogen atoms and deuterium atoms, more preferably 20 or more atoms, and can have, for example, 26 or more atoms. Also, it is preferably 80 or less, more preferably 50 or less, and even more preferably 30 or less.
  • the number of ring-fused indol-1-yl groups selected from R 1 to R 4 may be one, two, or three. .
  • there may be one donor group other than the ring-fused indol-1-yl group hereinafter referred to as "another donor group”
  • another donor group may be two. When there are two, they may be the same or different.
  • there are two ring-fused indol-1-yl groups one or no other donor group may be present.
  • there are three ring-fused indol-1-yl groups there are no other donor groups.
  • Other donor groups are groups with negative Hammett ⁇ p values.
  • k is the rate constant of a benzene derivative without a substituent
  • k0 is the rate constant of a benzene derivative substituted with a substituent
  • K is the equilibrium constant of a benzene derivative without a substituent
  • K0 is a substituent.
  • the equilibrium constant of the benzene derivative substituted with ⁇ represents the reaction constant determined by the type and conditions of the reaction.
  • Hammett's ⁇ p value and the numerical value of each substituent in the present invention, refer to the description of the ⁇ p value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991). can.
  • a group having a negative Hammett's ⁇ p value tends to exhibit electron-donating properties (donor properties)
  • a group having a positive Hammett's ⁇ p value tends to exhibit electron-withdrawing properties (acceptor properties).
  • Another donor group in the present invention is preferably a group containing a substituted amino group.
  • the substituent bonded to the nitrogen atom of the amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. , a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • the substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.
  • the other donor group in the present invention may be a group that binds through the nitrogen atom of the substituted amino group, or a group that binds through the group to which the substituted amino group is bound.
  • the group to which the substituted amino group is bonded is preferably a ⁇ -conjugated group. More preferred are groups attached at the nitrogen atom of a substituted amino group.
  • a substituted or unsubstituted carbazol-9-yl group is particularly preferred as another donor group in the present invention.
  • the two benzene rings that make up the carbazol-9-yl group are not condensed.
  • Substituents for the carbazol-9-yl group include alkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkoxy groups, alkylthio groups, aryloxy groups, arylthio groups, heteroaryloxy groups, heteroarylthio groups, and substituted amino groups.
  • groups, and preferred substituents include alkyl groups, aryl groups, and substituted amino groups. For a description of substituted amino groups, reference can be made to the description in the previous paragraph.
  • the substituted amino group here includes a substituted or unsubstituted carbazolyl group, such as a substituted or unsubstituted carbazol-3-yl group and a substituted or unsubstituted carbazol-9-yl group.
  • Other donor groups in the present invention preferably have 8 or more atoms other than hydrogen atoms and deuterium atoms, more preferably 12 or more atoms, and can also have, for example, 16 or more atoms. Also, it is preferably 80 or less, more preferably 60 or less, and even more preferably 40 or less.
  • the ring-fused indol-1-yl group is limited to those containing two or more heterocycles in the condensed rings constituting the group, and other donor groups are defined as “other "donor group”.
  • Other donor groups are defined as “other "donor group”. Examples of condensed rings containing two or more heterocycles include D13 to D152 described later.
  • the ring-fused indol-1-yl group is limited to those in which at least one heterocyclic ring is directly fused to the benzene ring or pyrrole ring of the indole, and other donor properties The group is referred to as "another donor group”.
  • D1 and D2 in formula (1) can take are shown below.
  • D7 to D152 are specific examples of ring-fused indol-1-yl groups
  • D1 to D6 are specific examples of other donor groups.
  • Ph represents a phenyl group and * represents a bonding position.
  • CH 3 is omitted from the methyl group, and for example, D2 represents a 3-methylcarbazol-9-yl group.
  • D1d to D152d Those in which all hydrogen atoms in D1 to D152 are replaced with deuterium atoms are disclosed here as D1d to D152d.
  • D31d1 to D42d1 obtained by substituting the phenyl group represented by "Ph" in D31 to D42 and D61 to D79 with a pentadeuteriophenyl group (a group in which all the hydrogen atoms of the phenyl group are substituted with deuterium atoms) and D61d1-D79d1.
  • R 1 to 2 of R 1 to R 4 in general formula (1) each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded via a carbon atom.
  • R 1 to R 4 those which are not a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group bonded via a carbon atom, or a ring-fused indol-1-yl group are hydrogen atoms or deuterium atoms. represents an atom, which can be, for example, a hydrogen atom.
  • R 1 to R 4 Only one of R 1 to R 4 may be a substituted or unsubstituted aryl group, and only one of R 1 to R 4 is a substituted or unsubstituted hetero group attached at a carbon atom. It may be an aryl group. Two of R 1 to R 4 may be the same substituted or unsubstituted aryl group or different substituted or unsubstituted aryl groups. Two of R 1 to R 4 may be the same substituted or unsubstituted heteroaryl group, or may be different substituted or unsubstituted heteroaryl groups.
  • R 1 to R 4 may be a substituted or unsubstituted aryl group and the other one may be a substituted or unsubstituted heteroaryl group bonded via a carbon atom. In a preferred embodiment of the present invention, only one of R 1 to R 4 is a substituted or unsubstituted aryl group, or two of R 1 to R 4 are each independently substituted or unsubstituted aryl is the base.
  • the ⁇ EST difference between the lowest excited singlet energy and the lowest excited triplet energy of the donor-substituted terephthalonitrile is reduced, and the usefulness as a delayed phosphor (luminous efficiency, etc.) can be improved.
  • a heteroaryl group is a heteroaryl group attached at a carbon atom.
  • the aryl group substituents and the heteroaryl group substituents include alkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkoxy groups, alkylthio groups, aryloxy groups, arylthio groups, heteroaryloxy groups, and heteroarylthio groups. , cyano groups, and combinations of these groups.
  • Preferred groups of substituents include alkyl groups, aryl groups, alkoxy groups, alkylthio groups, and cyano groups.
  • the aryl and heteroaryl groups are substituted with alkyl groups or unsubstituted. Examples include an unsubstituted phenyl group and a phenyl group substituted with an alkyl group.
  • Ar1d to Ar81d in which all the hydrogen atoms of Ar1 to Ar81 are replaced with deuterium atoms are disclosed here.
  • the compound represented by the general formula (1) preferably does not contain a metal atom, and consists only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom and a sulfur atom. It may be a compound that is In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms. Further, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and sulfur atoms.
  • the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms and nitrogen atoms.
  • the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms and nitrogen atoms.
  • the compound represented by general formula (1) may be a compound containing no hydrogen atom and containing a deuterium atom.
  • the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.
  • the compound represented by general formula (1) has a symmetrical structure. For example, it may have a line-symmetrical structure or a rotationally-symmetrical structure.
  • Tables 1 to 6 show the structures of compounds by specifying D 1 , D 2 , D 3 , Ar, Ar 1 and Ar 2 for each compound.
  • D 1 , D 2 , D 3 , Ar, Ar 1 and Ar 2 for each compound.
  • Ar is fixed to Ar1 and D 1 has the same structure as D 2 .
  • Compounds 1 to 125 are those in which D 1 and D 2 are D7 to D20, D22 to D30, D36 to D48, D50 to D60, D67 to D73, and D79 to D149 in this order.
  • Compounds 856 to 2451 where D 1 is D 2 is D21, and Ar is Ar2 to Ar21, Ar25 to Ar52, and Ar54 to Ar81 in that order are compounds 856 to 931, and D 1 is D 2 is D31 wherein Ar is Ar2 to Ar21, Ar25 to Ar52, and Ar54 to Ar81 are numbered in order as compounds 931 to 1006, and finally D1 is D2 is D152, Compounds 2376 to 2451 are those in which Ar is Ar2 to Ar21, Ar25 to Ar52, and Ar54 to Ar81 in order.
  • Tables 1-6 compounds 1-25053 are individually identified in structure and specifically disclosed herein.
  • 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 1200 or less, more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1).
  • the compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. If a coating method is used, it is possible to form a film even with a compound having a relatively large molecular weight.
  • the compound represented by the general formula (1) has the advantage of being easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) can be easily applied to the coating method, and can be easily purified to increase its purity. Since the compound represented by the general formula (1) has a short delayed fluorescence lifetime ( ⁇ 2), it can improve the luminous efficiency of the organic light-emitting device and suppress roll-off. Therefore, it is possible to provide an organic light-emitting device that is efficient and excellent in stability (durability).
  • a compound containing a plurality of structures represented by general formula (1) in its molecule as a light-emitting material.
  • a polymerizable group is preliminarily present in the structure represented by the general formula (1), and a polymer obtained by polymerizing the polymerizable group is used as the light-emitting material.
  • a monomer containing a polymerizable functional group in any one of R 1 to R 4 of general formula (1) and polymerizing it alone or copolymerizing it with other monomers, It is conceivable to obtain a polymer having repeating units and use the polymer as a light-emitting material.
  • a dimer or trimer by coupling compounds having a structure represented by general formula (1) and use them as a light-emitting material.
  • polymers having repeating units containing the structure represented by general formula (1) include polymers containing structures represented by the following general formula (2) or (3).
  • Q represents a group containing the structure represented by general formula (1)
  • L 1 and L 2 represent linking groups.
  • the number of carbon atoms in the linking group is preferably 0-20, more preferably 1-15, still more preferably 2-10.
  • the linking group preferably has a structure represented by -X 11 -L 11 -.
  • X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted A phenylene group is more preferred.
  • R 101 , R 102 , R 103 and R 104 each independently represent a substituent.
  • substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms, and halogen atoms, more preferably unsubstituted alkyl groups having 1 to 3 carbon atoms.
  • an unsubstituted alkoxy group having 1 to 3 carbon atoms a fluorine atom or a chlorine atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms.
  • the linking groups represented by L 1 and L 2 can be bonded to any of R 1 to R 4 constituting Q in general formula (1). Two or more linking groups may be linked to one Q to form a crosslinked structure or network structure.
  • repeating unit examples include structures represented by the following formulas (4) to (7).
  • Polymers having repeating units containing these formulas (4) to (7) are obtained by introducing a hydroxy group into any of R 1 to R 4 in general formula (1), and using it as a linker, the following compounds are prepared. It can be synthesized by reacting to introduce a polymerizable group and polymerizing the polymerizable group.
  • the polymer containing the structure represented by general formula (1) in the molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may have other structures. It may be a polymer containing a repeating unit having Moreover, the repeating unit having the structure represented by the general formula (1) contained in the polymer may be of a single type, or may be of two or more types. Examples of repeating units having no structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples thereof include repeating units derived from monomers having ethylenically unsaturated bonds such as ethylene and styrene.
  • the compound represented by general formula (1) is a luminescent material. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In certain embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, is in the UV region, blue, green, yellow, orange, red region of the visible spectrum (eg, about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or can emit light in the near-infrared region.
  • the compound represented by general formula (1) when excited by thermal or electronic means, is in the UV region, blue, green, yellow, orange, red region of the visible spectrum (eg, about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or can emit light in the near-infrared region.
  • compounds represented by general formula (1) when excited by thermal or electronic means, exhibit a red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1), when excited by thermal or electronic means, exhibit an orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm). In certain embodiments of the present disclosure, the compound represented by general formula (1) is in the green region of the visible spectrum (eg, about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. Can emit light.
  • the compound represented by general formula (1) is in the blue region of the visible spectrum (eg, about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. Can emit light. In certain embodiments of the present disclosure, compounds of general formula (1) are capable of emitting light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds of general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm-2 ⁇ m) when excited by thermal or electronic means.
  • Electronic properties of small molecule chemical substance libraries can be calculated using known ab initio quantum chemical calculations.
  • the Hartree-Fock equations using time-dependent density functional theory with 6-31G* as the basis and a family of functions known as Becke's three-parameter, Lee-Yang-Parr hybrid functionals (TD-DFT/B3LYP/6-31G*) can be analyzed to screen for molecular fragments (parts) with HOMO above a certain threshold and LUMO below a certain threshold.
  • the donor moiety (“D”) can be selected when there is a HOMO energy (eg, ionization potential) of ⁇ 6.5 eV or higher.
  • acceptor moieties can be selected when there is a LUMO energy (eg, electron affinity) of ⁇ 0.5 eV or less.
  • the bridging moiety (“B”) is, for example, a strongly conjugated system that can tightly constrain the acceptor and donor moieties to specific conformations, thereby allowing overlap between the ⁇ -conjugated systems of the donor and acceptor moieties. to prevent
  • compound libraries are screened using one or more of the following properties. 1. Emission around a specific wavelength2. Calculated triplet states above a particular energy level;3. ⁇ EST values below a specified value;4. quantum yield above a specified value;5. HOMO level6.
  • the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV or less than about 0.1 eV.
  • the ⁇ EST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV. , less than about 0.02 eV or less than about 0.01 eV.
  • the compound represented by general formula (1) comprises more than 25% of , about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.
  • the compound represented by general formula (1) is a novel compound.
  • the compound represented by general formula (1) can be synthesized by combining known reactions. For example, a (hetero)aryldifluoroterephthalonitrile substituted with a fluorine atom at the position where the donor group D 1 or D 2 is to be introduced is treated with D 1 -H or D 2 -H in tetrahydrofuran in the presence of sodium hydride. It is possible to synthesize by reacting. When D 1 and D 2 are different from each other, the reaction with D 1 —H and D 2 —H may be carried out in two steps. Specific reaction conditions and reaction procedures can be referred to Examples described later.
  • a compound represented by general formula (1) is combined with, dispersed with, covalently bonded with, coated with, supported with, or associated with the compound 1 Used with one or more materials (eg, small molecules, polymers, metals, metal complexes, etc.) to form a solid film or layer.
  • a compound represented by general formula (1) can be combined with an electroactive material to form a film.
  • compounds of general formula (1) may be combined with hole-transporting polymers.
  • a compound of general formula (1) may be combined with an electron transport polymer.
  • compounds of general formula (1) may be combined with hole-transporting and electron-transporting polymers.
  • compounds of general formula (1) may be combined with copolymers having both hole-transporting and electron-transporting moieties.
  • electrons and/or holes formed in the solid film or layer can interact with the compound represented by general formula (1).
  • films comprising compounds of the present invention represented by general formula (1) can be formed in a wet process.
  • a solution of a composition containing a compound of the invention 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.
  • suitable organic solvents are selected and used that are capable of dissolving compositions containing the compounds of the present invention.
  • compounds included in the composition can be introduced with substituents (eg, alkyl groups) that increase their solubility in organic solvents.
  • films comprising compounds of the 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.
  • 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.
  • Organic Light Emitting Diode One aspect of the present invention relates to use of the compound represented by general formula (1) of the present invention as a light-emitting material for an organic light-emitting device.
  • the compound represented by general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device.
  • the compound represented by general formula (1) contains delayed fluorescence that emits delayed fluorescence (delayed phosphor).
  • the present invention provides a delayed phosphor having a structure represented by general formula (1).
  • the present invention relates to the use of compounds represented by general formula (1) as delayed phosphors.
  • the present invention provides that the compound represented by general formula (1) can be used as a host material and can be used with one or more luminescent materials, wherein the luminescent material is a fluorescent material, It can be a phosphorescent material or TADF.
  • the compound represented by general formula (1) can also be used as a hole transport material.
  • the compound represented by general formula (1) can be used as an electron transport material.
  • the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1).
  • an organic light-emitting device containing a compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency.
  • the emissive layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate.
  • the substrate is a film-forming surface.
  • the orientation of the compounds of general formula (1) with respect to the film-forming surface affects or dictates the direction of propagation of light emitted by the aligning compounds.
  • aligning the propagation direction of light emitted by compounds represented by general formula (1) improves light extraction efficiency from the emissive layer.
  • One aspect of the present invention relates to an organic light emitting device.
  • 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 represented by general formula (1) assists (as a so-called assist dopant) the light emission of other light-emitting materials contained in the light-emitting layer.
  • the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet energy level and is at the lowest excited singlet energy level of the host material contained in the light-emitting layer.
  • 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 emissive layer is the layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only emissive materials are used as emissive layers. In some embodiments, the emissive layer includes an emissive material and a host material. In some embodiments, the emissive material is one or more compounds of general formula (1). In one embodiment, singlet and triplet excitons generated in the luminescent material are confined within the luminescent material to improve the light emission efficiency of the organic electroluminescent and organic photoluminescent devices.
  • a host material is used in addition to the emissive material in the emissive layer.
  • the host material is an organic compound.
  • the organic compound has excited singlet energies and excited triplet energies, at least one of which is higher than those of the light-emitting materials of the present invention.
  • the singlet and triplet excitons generated in the luminescent material of the invention are confined within the molecules of the luminescent material of the invention. In certain embodiments, singlet and triplet excitons are sufficiently confined to improve light emission efficiency.
  • singlet and triplet excitons are not sufficiently confined, although high light emission efficiency can still be obtained, i.e., host materials that can achieve high light emission efficiency are particularly limited. can be used in the present invention without
  • light emission occurs in the emissive material in the emissive layer of the device of the invention.
  • emitted light includes both fluorescence and delayed fluorescence.
  • the emitted light includes emitted light from the host material.
  • the emitted light consists of emitted light from the host material.
  • the emitted light includes emitted light from the compound represented by general formula (1) and emitted light from the host material.
  • a TADF molecule and a host material are used.
  • TADF is an assisting dopant.
  • the compound represented by formula (1) When the compound represented by formula (1) is used as the assist dopant, various compounds can be employed as the luminescent material (preferably fluorescent material).
  • the luminescent 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.
  • These exemplified skeletons may or may not have a substituent. Also, these exemplary skeletons may be combined. Examples of light-emitting materials that can be used in combination with the assist dopant represented by the general formula (1) are given below.
  • the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 1% or more by weight. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 20% by weight or less.
  • the amount of the compound of the invention as the light-emitting material contained in the light-emitting layer is 10% by weight or less.
  • the host material of the emissive layer is an organic compound with hole-transporting and electron-transporting functionality.
  • the host material of the emissive layer is an organic compound that prevents the wavelength of emitted light from increasing.
  • the host material of the emissive layer is an organic compound with a high glass transition temperature.
  • the host material is selected from the group consisting of:
  • the emissive layer comprises two or more structurally different TADF molecules.
  • the light-emitting layer can be made to contain three kinds of materials in which the excited singlet energy level is higher in the order of the host material, the first TADF molecule, and the second TADF molecule.
  • the difference ⁇ EST between the lowest excited singlet energy level and the lowest excited triplet energy level at 77K is preferably 0.3 eV or less, and 0.25 eV or less.
  • the content of the first TADF molecules in the light-emitting layer is preferably higher than the content of the second TADF molecules. Also, the content of the host material in the light-emitting layer is preferably higher than the content of the second TADF molecules. The content of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the content of the host material.
  • the composition within the emissive layer may be 10-70% by weight of the host material, 10-80% by weight of the first TADF molecule, and 0.1-30% by weight of the second TADF molecule. In some embodiments, the composition within the emissive layer may be 20-45% by weight of the host material, 50-75% by weight of the first TADF molecule, and 5-20% by weight of the second TADF molecule.
  • the luminescence quantum yield ⁇ PL2(100) due to optical excitation of the film satisfies the relational expression ⁇ PL2(B)> ⁇ PL2(100).
  • the emissive layer can include three structurally different TADF molecules.
  • the compound of the present invention can be any of a plurality of TADF compounds contained in the emissive layer.
  • the emissive layer can be composed of materials selected from the group consisting of host materials, assisting dopants, and emissive materials. In some embodiments, the emissive layer does not contain metallic elements. In some embodiments, the emissive layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms. Alternatively, the light-emitting layer can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms.
  • the light-emitting layer can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms.
  • the TADF material may be a known delayed fluorescence material.
  • Preferred delayed fluorescence materials include paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, and paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955.
  • 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 the functionality of both 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. 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 transport layer comprises a hole transport 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 the 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 a mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating the TFT with a planarizing film, pixel electrodes, and 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 a mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating the TFT with a planarizing film, pixel electrodes, and 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, and The applied organic film is made of the same material as that 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 includes attaching a carrier substrate made of a glass material to another surface of a base substrate made of polyimide before forming a barrier layer on the other 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 an 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 a remaining portion of the organic film is , 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 a 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.
  • 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.
  • Example 2 Synthesized in the same manner as in Example 1, the yield was 25%.
  • Example 3 Synthesized in the same manner as in Example 1, the yield was 50%.
  • 1 H NMR 400MHz, CDCl3 , d): 8.87-8.83 (m, 4H), 7.66-7.59 (m, 8H), 7.55-7.42 (m, 14H), 7.33-7.28 (m, 2H), 7.17- 7.15 (m, 4H), 7.06-6.96 (m, 6H).
  • Example 4 Synthesized in the same manner as in Example 1, the yield was 34%.
  • Example 7 Synthesized in the same manner as in Example 5, the yield was 82%.
  • 1 H NMR 400MHz, CDCl 3 , d): 8.67 (s, 2H), 8.02-7.99 (m, 4H), 7.77-7.74 (m, 4H), 7.51-7.33 (m, 6H), 7.26-7.21 ( m, 2H).
  • the compounds of Examples 1 to 10 were purified by sublimation and then used for thin film formation and device fabrication.
  • Example 1 (Preparation and evaluation of thin film)
  • the compound of Example 1 and mCBP were vapor-deposited from different vapor deposition sources on a quartz substrate by a vacuum vapor deposition method at a degree of vacuum of less than 1 ⁇ 10 ⁇ 3 Pa, and the concentration of the compound of Example 1 was 20% by weight.
  • a thin film having a thickness of 100 nm was formed as a doped thin film.
  • doped thin films were formed in the same manner using the compounds of Examples 2 to 10 instead of Example 1.
  • a compound of Comparative Example 1 having the following structure was used to form a doped thin film in the same manner.
  • Each thin film is laminated at a degree of vacuum of 1 ⁇ 10 ⁇ 6 Pa by a vacuum evaporation method on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 100 nm is formed.
  • ITO indium tin oxide
  • HATCN is formed on ITO to a thickness of 10 nm
  • NPD is formed thereon to a thickness of 30 nm.
  • TrisPCz is formed thereon to a thickness of 10 nm
  • H1 is further formed thereon to a thickness of 5 nm.
  • the compound of Example 1 and H1 are co-deposited from different deposition sources to form a 30 nm thick emitting layer.
  • the concentration of the compound of Example 1 is 35% by weight.
  • SF3TRZ is formed thereon to a thickness of 10 nm, and SF3TRZ and Liq are co-deposited thereon from different vapor deposition sources to form a thickness of 30 nm.
  • SF3TRZ:Liq (weight ratio) is 7:3.
  • a cathode is formed by forming Liq to a thickness of 2 nm and then depositing aluminum (Al) to a thickness of 100 nm.
  • organic electroluminescence devices are produced in the same manner. All of the produced organic electroluminescence devices have a short lifetime ( ⁇ 2) of delayed fluorescence.

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WO2021066059A1 (ja) * 2019-10-01 2021-04-08 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019107932A1 (ko) * 2017-11-28 2019-06-06 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
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