WO2023042814A1 - Composé, matériau électroluminescent et élément électroluminescent - Google Patents

Composé, matériau électroluminescent et élément électroluminescent Download PDF

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WO2023042814A1
WO2023042814A1 PCT/JP2022/034152 JP2022034152W WO2023042814A1 WO 2023042814 A1 WO2023042814 A1 WO 2023042814A1 JP 2022034152 W JP2022034152 W JP 2022034152W WO 2023042814 A1 WO2023042814 A1 WO 2023042814A1
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group
ring
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light
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サイダリム イウリムジヤン
ウママヘシュ バリジャパリ
琢哉 比嘉
裕太 綿引
善丈 鈴木
正貴 山下
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株式会社Kyulux
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Priority to KR1020247009171A priority Critical patent/KR20240068056A/ko
Priority to JP2023548465A priority patent/JPWO2023042814A1/ja
Priority to CN202280062390.8A priority patent/CN117940431A/zh
Publication of WO2023042814A1 publication Critical patent/WO2023042814A1/fr

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    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
    • 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
    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/16—Peri-condensed systems
    • 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
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
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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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission

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.
  • 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.
  • R 1 to R 10 each independently represent a hydrogen atom, a deuterium atom or a substituent. However, 1 or 2 of R 1 to R 10 represent a cyano group, and 1 to 4 of R 1 to R 10 represent a donor group bonded via a 5-membered ring.
  • 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 R 10 , and R 10 and R 1 may combine with each other to form a cyclic structure.
  • the ring-fused carbazol-9-yl group is a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom and a sulfur atom as a ring skeleton-constituting atom is condensed.
  • R 1 to R 10 are cyano groups, and two of R 1 to R 10 are substituted or unsubstituted ring-fused carbazol-9-yl groups [3] to [8]
  • a compound according to any one of [10] The compound according to any one of [3] to [9], wherein two of R 1 to R 10 are the same substituted or unsubstituted ring-fused carbazol-9-yl group.
  • R 1 to R 10 Two of R 1 to R 10 are cyano groups, and one of R 1 to R 10 is a substituted or unsubstituted ring-fused carbazol-9-yl group, [3] to [10]
  • a compound according to any one of [12] The compound according to any one of [1] to [11], wherein R 9 and R 10 are cyano groups.
  • R 13] The compound according to any one of [1] to [11], wherein R 2 and R 7 are cyano groups.
  • R 14 The compound according to any one of [1] to [13], which has an axisymmetric structure.
  • a luminescent material comprising the compound according to any one of [1] to [14].
  • a delayed phosphor comprising the compound according to any one of [1] to [14].
  • An organic semiconductor device comprising the compound according to any one of [1] to [14].
  • An organic light emitting device comprising the compound according to any one of [1] to [14].
  • the layer containing the compound also contains a delayed fluorescence material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound, [20] ].
  • the organic light-emitting device according to [20] wherein the device has a layer containing the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.
  • the compound of the present invention is useful as a luminescent material.
  • the compounds of the present invention also include compounds that emit delayed fluorescence.
  • organic light-emitting devices using the compound of the present invention include devices with high luminous efficiency, devices with high durability, and devices with low driving voltage.
  • R 1 to R 10 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • One or two of R 1 to R 10 represent a cyano group.
  • the number of cyano groups is one.
  • only R1 is a cyano group.
  • only R2 is a cyano group.
  • only R3 is a cyano group.
  • only R4 is a cyano group.
  • only R9 is a cyano group.
  • the number of cyano groups is two.
  • one of R 1 to R 4 and R 10 is a cyano group and one of R 5 to R 9 is a cyano group.
  • one of R 1 , R 2 and R 10 is a cyano group and one of R 7 to R 9 is a cyano group.
  • one of R2 and R10 is a cyano group and one of R7 and R9 is a cyano group.
  • one of R 1 to R 4 is a cyano group and one of R 5 to R 8 is a cyano group.
  • one of R 1 to R 3 is a cyano group and one of R 6 to R 8 is a cyano group.
  • one pair of R 1 and R 8 , R 2 and R 7 , R 3 and R 6 , R 9 and R 10 is a cyano group.
  • R 9 and R 10 are cyano groups.
  • R 2 and R 7 are cyano groups.
  • R 1 and R 8 are cyano groups.
  • R 3 and R 6 are cyano groups.
  • 1 to 4 of R 1 to R 10 represent donor groups bonded via a 5-membered ring. It is preferable that 1 to 3 of R 1 to R 10 are donating groups bonded via a 5-membered ring, and 1 or 2 of R 1 to R 10 are donating groups bonded via a 5-membered ring. more preferably a group.
  • only one of R 1 to R 10 is a donor group bonded via a 5-membered ring.
  • only one of R 1 -R 4 and R 5 -R 8 is a donor group attached in a 5-membered ring. For example, only R 1 or R 8 are donor groups attached to the 5-membered ring.
  • R 2 or R 7 are donor groups attached to the 5-membered ring.
  • R 3 or R 6 is a donor group attached to the 5-membered ring.
  • R 4 or R 5 are donor groups attached to the 5-membered ring.
  • only R 9 or R 10 is a donor group attached to the 5-membered ring.
  • only R 4 or R 5 are donor groups attached to the 5-membered ring.
  • R 9 and R 10 are cyano groups, and only one of R 1 to R 4 is a donor group bonded via a 5-membered ring.
  • R 9 and R 10 are cyano groups, and only R 1 is a donor group bonded via a 5-membered ring. In a preferred embodiment of the present invention, R 9 and R 10 are cyano groups, and only R 2 is a donor group bonded via a 5-membered ring. In a preferred embodiment of the present invention, R 9 and R 10 are cyano groups, and only R 3 is a donor group bonded via a 5-membered ring. In one aspect of the present invention, R 9 and R 10 are cyano groups, and only R 4 is a donor group bonded via a 5-membered ring.
  • two of R 1 to R 10 are donor groups bonded via a 5-membered ring.
  • the donor groups linked by the two 5-membered rings are identical.
  • two of R 1 to R 8 are donor groups bonded via a 5-membered ring.
  • one of R 1 to R 4 and one of R 5 to R 8 are donor groups that bond via a 5-membered ring.
  • one of R 2 and R 3 and one of R 6 and R 7 is a donor group linked via a 5-membered ring.
  • one of R 1 to R 8 and one of R 9 and R 10 is a donor group linked via a 5-membered ring.
  • R 1 and R 8 are donor groups that combine in a 5-membered ring.
  • R 2 and R 7 are donor groups that combine via a 5-membered ring.
  • R 3 and R 6 are donor groups that combine with a 5-membered ring.
  • R 9 and R 10 are donor groups that combine with a 5-membered ring.
  • R 9 and R 10 are cyano groups, and R 1 and R 8 are donor groups bonded via a 5-membered ring.
  • R 9 and R 10 are cyano groups, and R 2 and R 7 are donor groups bonded via a 5-membered ring. In a preferred embodiment of the present invention, R 9 and R 10 are cyano groups, and R 3 and R 6 are donor groups bonded via a 5-membered ring. In a preferred embodiment of the present invention, R 9 and R 10 are cyano groups, and R 2 and R 3 are donor groups bonded via a 5-membered ring. In one aspect of the present invention, three of R 1 to R 10 are donor groups bonded via a 5-membered ring. In a preferred embodiment of the invention, the donor groups linked by the three 5-membered rings are identical.
  • three of R 1 to R 8 are donor groups bonded via a 5-membered ring. In one aspect of the present invention, three of R 1 to R 4 are donor groups bonded via a 5-membered ring. In one aspect of the present invention, two of R 1 to R 4 and one of R 5 to R 8 are donor groups bonded via a 5-membered ring.
  • R 2 , R 3 and R 4 are donor groups that combine with a 5-membered ring.
  • R 2 , R 3 and R 6 are donor groups that combine with a 5-membered ring.
  • R 2 , R 3 and R 7 are donor groups that combine with a 5-membered ring.
  • R 9 and R 10 are cyano groups, and R 2 , R 3 and R 4 are donor groups that bond via a 5-membered ring. In one aspect of the present invention, R 9 and R 10 are cyano groups, and R 2 , R 3 and R 6 are donor groups that bond via a 5-membered ring. In one aspect of the present invention, R 9 and R 10 are cyano groups, and R 2 , R 3 and R 7 are donor groups that bond via a 5-membered ring. In one aspect of the present invention, four of R 1 to R 10 are donor groups bonded via a 5-membered ring. In a preferred embodiment of the invention, the donor groups linked by the four 5-membered rings are identical.
  • two out of R 1 to R 4 and two out of R 5 to R 8 are donor groups bonded via a 5-membered ring.
  • R 2 , R 3 , R 6 and R 7 are donor groups that combine with a 5-membered ring.
  • R 1 , R 3 , R 6 and R 8 are donor groups that combine in a 5-membered ring.
  • R 9 and R 10 are cyano groups, and R 2 , R 3 , R 6 and R 7 are donor groups that bond via a 5-membered ring.
  • R 9 and R 10 are cyano groups, and R 1 , R 3 , R 6 and R 8 are donor groups that bond via a 5-membered ring.
  • the donor group that bonds to the 5-membered ring is a group that bonds to any one of the five atoms forming the ring skeleton of the 5-membered ring and has a negative Hammett's ⁇ p value.
  • Hammett's ⁇ p value is defined by L.P. P. Proposed by Hammett, it quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives.
  • 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 donor group bonded via the 5-membered ring is preferably a group bonded via a nitrogen atom constituting the ring skeleton of the 5-membered ring.
  • the 5-membered ring is preferably ⁇ -conjugated.
  • a condensed carbazol-9-yl group, a substituted or unsubstituted benzimidazol-1-yl group, a substituted or unsubstituted ring-condensed benzimidazol-1-yl group, and the like can be mentioned.
  • fused ring as used herein means that rings are condensed.
  • a ring-fused carbazol-9-yl group means that a ring is fused to at least one of two benzene rings constituting carbazole.
  • the condensed ring may be an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, or an aliphatic heterocyclic ring, or may be a ring in which these are further condensed.
  • Preferred are aromatic hydrocarbon rings and aromatic heterocycles. Examples of aromatic hydrocarbon rings include substituted or unsubstituted benzene rings.
  • the benzene ring may be condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine 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. can be adopted.
  • a furan ring, a thiophene ring, or a pyrrole ring can be employed as the aromatic heterocyclic ring.
  • the fused rings are the furan ring of substituted or unsubstituted benzofuran, the thiophene ring of substituted or unsubstituted benzothiophene, and the pyrrole ring of substituted or unsubstituted indole.
  • the nitrogen atom of the pyrrole ring is preferably bonded with a substituent selected from the substituent group E, and is substituted with an aryl group that may be substituted with an alkyl group or an aryl group. is more preferred.
  • the donor group bonded to the 5-membered ring is preferably a group represented by the following general formula (2).
  • Z 1 represents C—R 11 or N
  • Z 2 represents C—R 12 or N
  • Z 3 represents C—R 13 or N
  • Z 4 represents C—R 14 or N
  • Z5 represents C or N
  • Ar represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring.
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 may combine with each other to form a cyclic structure.
  • the number of N is preferably 0 to 3, more preferably 0 to 2. In one aspect of the present invention, the number of Z 1 to Z 4 that are N is one. In one aspect of the present invention, the number of Z 1 to Z 4 that are N is zero.
  • Each of R 11 to R 14 independently represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, or the substituent group It may be selected from D, or may be selected from Substituent Group E. When two or more of R 11 to R 14 represent substituents, the two or more substituents may be the same or different.
  • R 11 to R 14 are preferably substituents . hydrogen atom).
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 may combine with each other to form a cyclic structure.
  • the cyclic structure may be an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, or an aliphatic heterocyclic ring, or may be a ring in which these are condensed.
  • the benzene ring may be condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine 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. can be adopted.
  • a furan ring, a thiophene ring, or a pyrrole ring can be employed as the aromatic heterocyclic ring.
  • the cyclic structure is the furan ring of substituted or unsubstituted benzofuran, the thiophene ring of substituted or unsubstituted benzothiophene, or the pyrrole ring of substituted or unsubstituted indole.
  • Benzofuran, benzothiophene, and indole here may be unsubstituted, may be substituted with a substituent selected from Substituent Group A, or may be substituted with a substituent selected from Substituent Group B.
  • a substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and the substituent is, for example, a substituent selected from any one of the substituent groups A to E. can be mentioned.
  • the cyclic structure may be a substituted or unsubstituted cyclopentadiene ring.
  • one pair of R 11 and R 12 , R 12 and R 13 , and R 13 and R 14 are bonded together to form a cyclic structure. In one aspect of the present invention, none of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 are bonded to each other to form a cyclic structure.
  • Z5 represents C or N
  • Ar represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring.
  • Z 5 is C and Ar is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle.
  • Z 5 is N and Ar is a substituted or unsubstituted heteroaromatic ring.
  • a benzene ring can be mentioned as an aromatic hydrocarbon ring that Ar can take.
  • the benzene ring may be condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring.
  • the aromatic heterocyclic ring that Ar can take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be employed.
  • a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring can be employed as the aromatic heterocyclic ring.
  • Z 5 is C, and the aromatic heterocycle is the furan ring of substituted or unsubstituted benzofuran, the thiophene ring of substituted or unsubstituted benzothiophene, the pyridine ring of substituted or unsubstituted quinoline, or a pyridine ring of substituted or unsubstituted isoquinoline.
  • Z 5 is N and the aromatic heterocycle is the pyrrole ring of substituted or unsubstituted indole or the imidazole ring of substituted or unsubstituted benzimidazole.
  • Benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole herein may be unsubstituted or substituted with a substituent selected from Substituent Group A, or selected from Substituent Group B. It may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D. , and a substituent selected from the substituent group E.
  • Z 5 in general formula (2) is C, it is preferably a group represented by general formula (3) below.
  • Z 1 represents C—R 11 or N
  • Z 2 represents C—R 12 or N
  • Z 3 represents C—R 13 or N
  • Z 4 represents C—R 14 or N
  • Z 6 represents C—R 16 or N
  • Z 7 represents C—R 17 or N
  • Z 8 represents C—R 18 or N
  • Z 9 represents C—R 19 or N represents R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 may combine with each other to form a cyclic structure.
  • the corresponding explanations in general formula (2) can be referred to.
  • Z 6 to Z 9 and R 16 to R 19 in general formula (3) correspond to Z 1 to Z 4 and R 11 to R 14 in general formula (2) in order.
  • the description of Z 1 to Z 4 and R 11 to R 14 in (2) can be referred to.
  • the number of N among Z 1 to Z 4 and Z 6 to Z 9 is preferably 0 to 2, preferably 0 or 1.
  • the number of Z 1 to Z 4 and Z 6 to Z 9 that are N is one.
  • the number of N among Z 1 to Z 4 and Z 6 to Z 9 is zero. When 0, it represents a substituted or unsubstituted carbazol-9-yl group.
  • the carbazol-9-yl group may be unsubstituted, optionally substituted with a substituent selected from the substituent group A, or substituted with a substituent selected from the substituent group B may be substituted with a substituent selected from substituent group C, may be substituted with a substituent selected from substituent group D, or may be substituted with a substituent selected from substituent group E It may be substituted with a substituent.
  • the donor group bonded to the 5-membered ring is a carbazol-9-yl group substituted with a group containing at least one substituted or unsubstituted aryl group, for example, at least one It is a carbazol-9-yl group substituted with a substituted or unsubstituted aryl group.
  • at least one of the 2- and 7-positions is a substituted or unsubstituted aryl group.
  • at least one of the 3- and 6-positions is a substituted or unsubstituted aryl group.
  • the aryl group referred to herein may be unsubstituted, may be substituted with a substituent selected from substituent group A, or may be substituted with a substituent selected from substituent group B. may be substituted with a substituent selected from substituent group C, may be substituted with a substituent selected from substituent group D, or may be substituted with a substituent selected from substituent group E may be substituted with a group.
  • the donor group bonded to the 5-membered ring is a substituted or unsubstituted indol-1-yl group, and the indole ring constituting the indol-1-yl group is fused with a ring, thereby forming a ring It may form a condensed ring with 4 or more.
  • 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 the 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. Preferred is when 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 heteroatoms contained as ring skeleton-constituting atoms of the heterocyclic 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 heterocyclic 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 heterocyclic ring preferably has two or more conjugated double bonds, and the condensed heterocyclic ring preferably extends the conjugated system of the indole ring (i.e., has aromaticity). is preferred).
  • heterocyclic ring examples include furan ring, thiophene ring and pyrrole ring.
  • 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 heterocyclic ring is directly condensed with the benzene ring or pyrrole ring that constitutes the indol-1-yl group.
  • the fused rings that make up the ring-fused 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, thiophene, pyrrole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, pyrrole, pyrazole and imidazole rings.
  • 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.
  • the wavy line represents the binding position.
  • 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.
  • the benzofuran-fused indol-1-yl group, the benzothiophene-fused indol-1-yl group, the indole-fused indol-1-yl group, and the sylindene-fused indol-1-yl group are substituted or unsubstituted. substituted with a substituted aryl group; It is preferably substituted with a substituted or unsubstituted phenyl group.
  • a group selected from any one of the substituent groups A to E can be selected, and preferably selected from the substituent group E.
  • the aryl group and phenyl group referred to here are preferably unsubstituted.
  • the ring-fused indol-1-yl group is a benzofuran-fused indol-1-yl group substituted with a substituted or unsubstituted aryl group.
  • the donor group bonded via a 5-membered ring that can be employed in general formula (1) is not limited to the following specific examples.
  • Ph represents a phenyl group
  • D represents a deuterium atom
  • * indicates a bonding position.
  • the display of the methyl group is omitted.
  • D2 represents a 3-methylcarbazol-9-yl group.
  • R 1 to R 10 in general formula (1), those that are neither a cyano group nor a donor group bonded via a 5-membered ring (hereinafter referred to as “the remaining R 1 to R 10 ”) are hydrogen atoms, It is a deuterium atom, or a substituent that is neither a cyano group nor a donor group bonded to a 5-membered ring (hereinafter referred to as "remaining substituents").
  • the remaining R 1 to R 10 may all be hydrogen atoms or deuterium atoms, for example all hydrogen atoms or all deuterium atoms.
  • the number of remaining substituents is preferably 0 to 6, for example 0 to 4 or 0 to 3. , may be in the range of 0 to 2.
  • the remaining substituents may be selected from Substituent Group A below, may be selected from Substituent Group B below, or may be selected from Substituent Group C below. , may be selected from Substituent Group D below, or may be selected from Substituent Group E below.
  • the other substituents are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups.
  • the other substituent is a substituted or unsubstituted aryl group, such as a phenyl group optionally substituted with an alkyl group or an aryl group.
  • 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 substituents of the aryl group and the heteroaryl group may be selected from the following substituent group A, may be selected from the following substituent group B, or may be selected from the following substituent group C, may be selected from Substituent Group D below, or may be selected from Substituent Group E below.
  • 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 R 10 , R 10 and R 1 may be bonded to each other to form a cyclic structure.
  • the description and specific examples of the cyclic structure referred to herein the description and specific examples of the condensed rings in the above description of "ring condensation" can be referred to.
  • R 9 and R 10 are combined with each other to form a ring structure.
  • at least one pair of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 are They combine to form a ring structure.
  • R 9 and R 10 are linked together to form a cyclic structure.
  • none of R 4 and R 5 , R 8 and R 9 , R 10 and R 1 are bonded together to form a cyclic structure. In one aspect of the present invention, none of R 8 and R 9 , R 9 and R 10 , R 10 and R 1 are bonded to each other to form a cyclic structure. In one aspect of the present invention, none of R 3 and R 4 , R 4 and R 5 , R 5 and R 6 are bonded together to form a cyclic structure. In one aspect of the present invention, R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 8 and R 9 , R 9 and R 10 , R 10 and R 1 are all bonded together to form a cyclic ring.
  • 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 Neither 8 and R 9 nor R 10 and R 1 are bonded to each other to form a cyclic structure.
  • 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 None of 8 and R 9 , R 9 and R 10 , R 10 and R 1 are bonded to each other to form a cyclic structure.
  • 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.
  • it may have an axisymmetric structure.
  • R 1 and R 8 in general formula (1) are the same
  • R 2 and R 7 are the same
  • R 3 and R 6 are the same
  • R 4 and R 5 are the same
  • R 9 and R 10 are the same.
  • the compound represented by general formula (1) has an asymmetric structure.
  • 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).
  • 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 or a combination of two or more groups selected from the group consisting of diarylamino groups (eg, 12 to 20 carbon atoms).
  • 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). It means one group selected from the group consisting of or a combination of two or more groups.
  • 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.
  • 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.
  • Table 1 shows the structures of compounds 1 to 30 individually by specifying R 1 to R 10 in general formula (1) for each compound.
  • Table 2 shows the structures of compounds 1 to 1008962 by collectively displaying R 1 to R 10 of a plurality of compounds in each row.
  • R 1 , R 3 to R 8 are fixed to H (hydrogen atom), and R 9 and R 10 are fixed to CN (cyano group).
  • Compounds in which R 2 is D1 to D447 are designated as compounds 1 to 447 in order.
  • R 1 , R 2 , R 4 to R 8 are fixed to H (hydrogen atom), and R 9 and R 10 are fixed to CN (cyano group).
  • Compounds in which R 3 is D1 to D447 are designated as compounds 448 to 894 in order.
  • compounds 895-1788 and compounds 806025-806918 are also identified.
  • R 1 , R 3 to R 6 and R 8 are fixed to H (hydrogen atom), and R 9 and R 10 are fixed to CN (cyano group).
  • compounds 1007175-1008962 are also identified. wherein R 2 , R 3 and R 7 are the same in compounds 1007175-1007621; R 2 , R 3 and R 6 are the same in compounds 1007622-1008068; R 6 and R 7 are the same, and R 1 and R 3 and R 6 and R 8 are the same in compounds 1008516-1008962.
  • R 1 and R 3 and R 6 and R 8 are the same in compounds 1008516-1008962.
  • compounds 1-1008962 are individually structurally identified and specifically disclosed herein. Compounds 1 to 30 are specified in both Tables 1 and 2.
  • 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 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 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.
  • 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 polymer having a repeating unit is obtained by preparing a monomer containing a polymerizable functional group at any site of general formula (1) and polymerizing it alone or copolymerizing it with other monomers. It is conceivable to obtain and use the polymer as a light-emitting material. Alternatively, it is conceivable to obtain 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 either of the following two general formulas.
  • Q represents a group containing a 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 part of general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or network structure.
  • Polymers having repeating units containing these formulas are obtained by introducing a hydroxy group into one of the sites of general formula (1), reacting it with the following compound as a linker to introduce a polymerizable group, and It can be synthesized by polymerizing a 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 regions 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 (eg, 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.
  • 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.
  • 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.
  • the compound represented by general formula (1) emits light in the region of 520 nm and above when excited by thermal or electronic means.
  • a preferred embodiment of the present invention emits light of 520 nm or more and less than 560 nm, especially in the green region.
  • another preferred embodiment of the present invention emits light between 560 nm and 640 nm.
  • an organic semiconductor device using the compound represented by general formula (1) can be produced.
  • the organic semiconductor element referred to here may be an organic optical element in which light is interposed, or an organic element in which light is not interposed.
  • the organic optical element may be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element that causes energy transfer by light within the element.
  • the compound represented by formula (1) can be used to fabricate organic optical devices such as organic electroluminescence devices and solid-state imaging devices (for example, CMOS image sensors).
  • CMOS complementary metal oxide semiconductor
  • a CMOS (complementary metal oxide semiconductor) or the like using the compound represented by general formula (1) can be fabricated.
  • 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 compounds represented by general formula (1) include novel compounds.
  • the compound represented by general formula (1) can be synthesized by combining known reactions.
  • a cyanophenanthrene substituted with a substituted or unsubstituted carbazol-9-yl group can be synthesized by reacting a phenanthrene having a cyano group and a halogen atom with a substituted or unsubstituted carbazole.
  • Synthesis Examples described later can be referred to.
  • 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).
  • a film comprising a compound 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.
  • the compound represented by formula (1) is useful as a material for organic light-emitting devices. In particular, it is preferably used for organic light-emitting diodes and the like.
  • 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. It is contained between the lowest excited singlet energy levels of other light-emitting materials 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. In some embodiments, the organic layers include only the emissive layer.
  • the organic layers include one or more organic layers in addition to the emissive layer.
  • 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 one embodiment, the luminescent material is one or more compounds represented by 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 and has a lower excited singlet energy than the host material in the emissive layer and a higher excited singlet energy than the emissive material in the emissive layer.
  • 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 having the structure represented by the general formula (1) are described 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 concentration of the first TADF molecules in the light-emitting layer is higher than the concentration of the second TADF molecules.
  • the concentration of the host material in the light-emitting layer is preferably higher than the concentration of the second TADF molecules.
  • the concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration 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 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.
  • the emissive layer does not contain metallic elements.
  • 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.
  • 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 (greater than 4 eV).
  • 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 materials 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-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 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;
  • 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 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 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 directly contacts the base substrate and a remaining portion of the organic film surrounds the edge of the barrier layer while contacting 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.
  • the features of the present invention will be more specifically described below with reference to Synthesis Examples and Examples.
  • the materials, processing details, processing procedures, etc. described below can be changed as appropriate without departing from the gist of the present invention. Therefore, the scope of the present invention should not be construed to be limited by the specific examples shown below.
  • the emission characteristics were evaluated using a source meter (manufactured by Keithley: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies: E5273A), an optical power meter measuring device (manufactured by Newport: 1930C), and an optical spectrometer.
  • intermediate k Dimethylsulfoxide (150 mL) was added to a mixture of intermediate j (3.94 g, 14.9 mmol) and copper (I) chloride (0.295 g, 2.98 mmol). A 70% tert-butyl hydroperoxide solution (6.13 mL, 44.7 mmol) was added dropwise to this solution, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, water was added to perform filtration and extraction. The obtained mixture was purified by silica gel column chromatography and then recrystallized to obtain intermediate k (0.97 g, yield 25%).
  • Example 1 Preparation and evaluation of thin film Compound 15 and mCBP were vapor-deposited from different vapor deposition sources at a vacuum degree of less than 1 ⁇ 10 -3 Pa on a quartz substrate by a vacuum vapor deposition method, and the concentration of compound 15 was A thin film of 20% by weight was formed with a thickness of 100 nm. Thin films were formed in the same manner using compounds 185, 632, 894, 21949, 34941, 35837, 8061, 434559 and 806951 instead of compound 15, respectively. The emission maximum wavelength ( ⁇ max) and photoluminescence quantum yield (PLQY) were measured when each formed thin film was irradiated with excitation light of 300 nm. HOMO energy and LUMO energy were also measured. Table 3 shows the results.
  • Example 2 Fabrication and evaluation of organic electroluminescence device
  • ITO indium tin oxide
  • Lamination was performed at 0 ⁇ 10 ⁇ 5 Pa.
  • HAT-CN was formed to a thickness of 10 nm on ITO
  • NPD was formed thereon to a thickness of 30 nm.
  • Tris-PCz was formed to a thickness of 10 nm
  • EBL1 was formed to a thickness of 5 nm.
  • EBL1 and compound 15 were co-deposited from different vapor deposition sources to form a layer with a thickness of 40 nm, which was used as a light-emitting layer.
  • the concentration of compound 15 in the light-emitting layer was set to 40% 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 concentrations of Liq and SF3-TRZ in this layer were 30% and 70% by weight, 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, thereby forming an organic electroluminescence device.
  • An organic electroluminescence device was produced by the same procedure using 185, 632, 806951, 806993 and 8061 instead of compound 15, respectively.
  • the emission intensity of each organic electroluminescence element decreases to 95% of the starting value when continuously energized at a driving voltage of 2 mA/cm 2 , maximum external quantum efficiency (EQE), and 5.5 mA/cm 2 .
  • the time (LT95) required for each was measured. Table 4 shows the results. LT95 is shown as a relative value when compound 632 is set to 1.
  • An organic electroluminescent device using compound 8061 also showed a high EQE of 9.7%.
  • the compound represented by the general formula (1) has a high photoluminescence quantum yield and is excellent as a light-emitting material. Further, the organic electroluminescence device using the compound represented by the general formula (1) has high luminous efficiency, low driving voltage, and long life.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Un composé représenté par la formule générale est utile en tant que matériau électroluminescent. R1 à R10 représentent un atome d'hydrogène, un atome de deutérium ou un substituant, à condition qu'un ou deux parmi R1 à R10 représentent un groupe cyano et un à quatre parmi R1 à R10 représentent un groupe donneur lié dans un cycle à 5 chaînons.
PCT/JP2022/034152 2021-09-16 2022-09-13 Composé, matériau électroluminescent et élément électroluminescent WO2023042814A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015118958A (ja) * 2013-12-16 2015-06-25 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2015111942A2 (fr) * 2014-01-23 2015-07-30 주식회사 두산 Composé organique et élément électroluminescent organique le contenant
CN105131938A (zh) * 2015-07-29 2015-12-09 中节能万润股份有限公司 一种有机电致发光材料及其应用
WO2016017514A1 (fr) * 2014-07-31 2016-02-04 コニカミノルタ株式会社 Élément électroluminescent organique, film mince émetteur de lumière, dispositif d'affichage et dispositif d'éclairage
WO2018123924A1 (fr) * 2016-12-26 2018-07-05 出光興産株式会社 Composition, matériau pour élément électroluminescent organique, film de composition, élément électroluminescent organique, et appareil électronique
WO2018123923A1 (fr) * 2016-12-26 2018-07-05 出光興産株式会社 Élément électroluminescent organique, et appareil électronique
JP2018163975A (ja) * 2017-03-24 2018-10-18 出光興産株式会社 組成物、有機エレクトロルミネッセンス素子用材料、組成物膜、有機エレクトロルミネッセンス素子、及び電子機器
CN108727390A (zh) * 2017-04-21 2018-11-02 北京鼎材科技有限公司 芘衍生物及其在有机发光材料中的应用
JP2018177647A (ja) * 2017-04-03 2018-11-15 国立大学法人九州大学 ジシアノペンタヘリセン化合物、発光材料およびそれを用いた発光素子
KR20200012792A (ko) * 2018-07-27 2020-02-05 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015118958A (ja) * 2013-12-16 2015-06-25 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2015111942A2 (fr) * 2014-01-23 2015-07-30 주식회사 두산 Composé organique et élément électroluminescent organique le contenant
WO2016017514A1 (fr) * 2014-07-31 2016-02-04 コニカミノルタ株式会社 Élément électroluminescent organique, film mince émetteur de lumière, dispositif d'affichage et dispositif d'éclairage
CN105131938A (zh) * 2015-07-29 2015-12-09 中节能万润股份有限公司 一种有机电致发光材料及其应用
WO2018123924A1 (fr) * 2016-12-26 2018-07-05 出光興産株式会社 Composition, matériau pour élément électroluminescent organique, film de composition, élément électroluminescent organique, et appareil électronique
WO2018123923A1 (fr) * 2016-12-26 2018-07-05 出光興産株式会社 Élément électroluminescent organique, et appareil électronique
JP2018163975A (ja) * 2017-03-24 2018-10-18 出光興産株式会社 組成物、有機エレクトロルミネッセンス素子用材料、組成物膜、有機エレクトロルミネッセンス素子、及び電子機器
JP2018177647A (ja) * 2017-04-03 2018-11-15 国立大学法人九州大学 ジシアノペンタヘリセン化合物、発光材料およびそれを用いた発光素子
CN108727390A (zh) * 2017-04-21 2018-11-02 北京鼎材科技有限公司 芘衍生物及其在有机发光材料中的应用
KR20200012792A (ko) * 2018-07-27 2020-02-05 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WANG RUI, MENG QING-YU, WANG YI-LEI, QIAO JUAN: "Negative Charge Management to Make Fragile Bonds Less Fragile toward Electrons for Robust Organic Optoelectronic Materials", CCS CHEMISTRY, vol. 4, no. 1, 1 January 2022 (2022-01-01), pages 331 - 343, XP093049112, ISSN: 2096-5745, DOI: 10.31635/ccschem.021.202100778 *

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