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WO2025041780A1 - Composé, matériau électroluminescent et élément électroluminescent - Google Patents

Composé, matériau électroluminescent et élément électroluminescent Download PDF

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Publication number
WO2025041780A1
WO2025041780A1 PCT/JP2024/029573 JP2024029573W WO2025041780A1 WO 2025041780 A1 WO2025041780 A1 WO 2025041780A1 JP 2024029573 W JP2024029573 W JP 2024029573W WO 2025041780 A1 WO2025041780 A1 WO 2025041780A1
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Japanese (ja)
Inventor
侑 山根
ヨンジュ ジョ
基樹 戸叶
汐音 藤本
正貴 山下
直美 嶋村
良平 八木
京 森本
祐子 下位
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Kyulux Inc
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Kyulux Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers

Definitions

  • the present invention relates to a compound useful as a light-emitting material and a light-emitting device using the compound.
  • organic electroluminescence elements organic electroluminescence elements
  • various efforts have been made to improve luminous efficiency by developing and combining newly developed electron transport materials, hole transport materials, and luminescent materials that make up organic electroluminescence elements.
  • organic electroluminescence elements that use delayed fluorescent materials.
  • Delayed fluorescent materials are materials that emit fluorescence when they undergo reverse intersystem crossing from an excited triplet state to an excited singlet state in an excited state, and then return from that excited singlet state to the ground state. Fluorescence from this route is observed later than fluorescence from an excited singlet state that occurs directly from the ground state (normal fluorescence), and is therefore called delayed fluorescence.
  • delayed fluorescence when a luminescent compound is excited by injecting carriers, the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency when only the fluorescence from the directly generated excited singlet state is used.
  • delayed fluorescent materials can use not only the excited singlet state but also the excited triplet state for fluorescence emission via the above-mentioned route via reverse intersystem crossing, resulting in a higher luminous efficiency than normal fluorescent materials.
  • the inventors have conducted extensive research with the aim of providing compounds that are more useful as delayed fluorescent materials for light-emitting devices. They have also conducted intensive research with the aim of deriving and generalizing a general formula for compounds that are more useful as delayed fluorescent materials.
  • a compound represented by the following general formula (1) [In general formula (1), 1 to 3 of R 1 to R 5 are donor groups, 0 to 1 of R 1 to R 5 are cyano groups, 0 to 3 of R 1 to R 5 are hydrogen atoms or deuterium atoms, 0 to 2 of R 1 to R 5 are substituted or unsubstituted aryl groups, and the remaining R 1 to R 5 are substituted or unsubstituted alkyl groups.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may be bonded to each other to form a cyclic structure.
  • L represents a single bond or a linking group.
  • X 1 represents N or C-R 6
  • X 2 represents N or C-R 7.
  • R 6 and R 7 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • Y represents a substituted or unsubstituted carbazol-9-yl group, or a substituted or unsubstituted aryl group, provided that when Y is a substituted or unsubstituted aryl group, 0 to 2 of R 1 to R 5 are hydrogen atoms or deuterium atoms.
  • a light-emitting material comprising the compound according to any one of [1] to [12].
  • a delayed fluorescent material comprising the compound according to any one of [1] to [12].
  • a film comprising the compound according to any one of [1] to [12].
  • An organic semiconductor device comprising the compound according to any one of [1] to [12].
  • An organic light-emitting device comprising the compound according to any one of [1] to [12].
  • the organic light-emitting device according to [17] wherein the device has a layer containing the compound, the layer also containing a host material.
  • the layer containing the compound contains a delayed fluorescent material in addition to the compound and the host material, and the minimum excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.
  • the organic light-emitting element according to [18].
  • the organic light-emitting device according to [18] 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 compounds of the present invention exhibit excellent luminescence properties. They are useful as materials for organic light-emitting devices.
  • substituted means an atom or atomic group other than hydrogen atoms and deuterium atoms.
  • substituted or unsubstituted means that hydrogen atoms may be substituted with deuterium atoms or substituents.
  • R 1 to R 5 are donor groups, 0 to 1 of R 1 to R 5 are cyano groups, 0 to 3 of R 1 to R 5 are hydrogen atoms or deuterium atoms, 0 to 2 of R 1 to R 5 are substituted or unsubstituted aryl groups, and the remaining R 1 to R 5 are substituted or unsubstituted alkyl groups.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may be bonded to each other to form a cyclic structure.
  • L represents a single bond or a linking group.
  • X 1 represents N or C-R 6
  • X 2 represents N or C-R 7.
  • R 6 and R 7 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • Y represents a substituted or unsubstituted carbazol-9-yl group, or a substituted or unsubstituted aryl group. However, when Y is a substituted or unsubstituted aryl group, 0 to 2 of R 1 to R 5 are hydrogen atoms or deuterium atoms.
  • R 1 to R 5 are donor groups.
  • the donor groups which can be R 1 to R 5 do not include substituted or unsubstituted aryl groups.
  • the "donor group” can be selected from groups with a negative Hammett ⁇ p value.
  • the "acceptor group” can be selected from groups with a positive Hammett ⁇ p value.
  • the Hammett ⁇ p value was proposed by L. P. Hammett, and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative.
  • k 0 is the rate constant of a benzene derivative having no substituent
  • K 0 is the equilibrium constant of a benzene derivative having no substituent
  • K is the equilibrium constant of a benzene derivative substituted with a substituent
  • ⁇ is a reaction constant determined by the type and conditions of the reaction.
  • the donor group which can be R 1 to R 5 has a ⁇ p of preferably ⁇ 0.3 or less, more preferably ⁇ 0.5 or less, and further preferably ⁇ 0.7 or less. For example, it may be selected from the range of ⁇ 0.9 or less, or ⁇ 1.1 or less.
  • the donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group, or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group.
  • the substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • the substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.
  • the two aryl groups constituting the diarylamino group here may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.
  • the donor group which can be represented by R 1 to R 5 is preferably a group represented by the following general formula (a).
  • Z 1 represents C-R 14 or N
  • Z 2 represents C-R 15 or N
  • Z 3 represents C-R 16 or N
  • Z 4 represents C-R 17 or N
  • Z 5 represents C or N
  • Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring.
  • R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be bonded to each other to form a cyclic structure.
  • the number of N is preferably 0 to 3, and more preferably 0 to 2. In one aspect of the present invention, among Z 1 to Z 4 , the number of N is 1. In one aspect of the present invention, among Z 1 to Z 4 , the number of N is 0.
  • R 14 to R 17 each independently represent a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. When two or more of R 14 to R 17 represent substituents, those two or more substituents may be the same or different.
  • R 14 to R 17 are substituents, and for example, one may be a substituent or none may be a substituent (R 14 to R 17 are hydrogen atoms or deuterium atoms).
  • R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be bonded to each other to form a cyclic structure.
  • the cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a ring condensed with these.
  • An aromatic ring or a heteroaromatic ring is preferable.
  • An example of the aromatic ring is a substituted or unsubstituted benzene ring.
  • the benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring.
  • the heteroaromatic ring means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted.
  • a furan ring, a thiophene ring, or a pyrrole ring may be adopted as the heteroaromatic ring.
  • the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole.
  • the benzofuran, benzothiophene, and indole mentioned here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or 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, or may be substituted with a substituent selected from the substituent group E.
  • a substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the substituent include a substituent selected from any of the groups A to E.
  • the cyclic structure may be a substituted or unsubstituted cyclopentadiene ring.
  • a pair of R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 are bonded to each other to form a cyclic structure.
  • R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 are not bonded to each other to form a cyclic structure.
  • Z5 represents C or N
  • Ar5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring.
  • Z5 is C
  • Ar5 is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring.
  • Z5 is N
  • Ar5 is a substituted or unsubstituted heteroaromatic ring.
  • An example of the aromatic ring that Ar 5 can take is a benzene ring.
  • the benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring.
  • the heteroaromatic ring that Ar 5 can take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted.
  • a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring may be adopted as the heteroaromatic ring.
  • Z 5 is C
  • the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline.
  • Z5 is N
  • the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole, or an imidazole ring of substituted or unsubstituted benzimidazole.
  • the benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole mentioned here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or 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, or may be substituted with a substituent selected from the substituent group E.
  • Z 5 in formula (a) is C, it is preferably a group represented by the following formula (b).
  • Z 1 represents C-R 14 or N
  • Z 2 represents C-R 15 or N
  • Z 3 represents C-R 16 or N
  • Z 4 represents C-R 17 or N
  • Z 6 represents C-R 18 or N
  • Z 7 represents C-R 19 or N
  • Z 8 represents C-R 20 or N
  • Z 9 represents C-R 21 or N.
  • R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , and R 20 and R 21 may be bonded to each other to form a cyclic structure.
  • the corresponding explanations for general formula (a) can be referred to.
  • Z 6 to Z 9 and R 18 to R 21 in general formula (b) correspond to Z 1 to Z 4 and R 14 to R 17 in general formula (a) in that order, and for the contents thereof, the explanations for Z 1 to Z 4 and R 14 to R 17 in general formula (a) can be referred to.
  • the number of N groups among Z 1 to Z 4 and Z 6 to Z 9 is preferably 0 to 2, and is preferably 0 or 1.
  • the number of N groups among Z 1 to Z 4 and Z 6 to Z 9 is 1.
  • the number of N groups among Z 1 to Z 4 and Z 6 to Z 9 is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.
  • the donor group which R 1 to R 5 can take is preferably a substituted or unsubstituted carbazol-9-yl group.
  • the carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or 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, or may be substituted with a substituent selected from the substituent group E.
  • one or more rings may be further condensed to the two benzene rings constituting the carbazol-9-yl group.
  • the donor group which R 1 to R 5 can take is a carbazol-9-yl group which may be substituted with a group selected from the substituent group E, or may have one or more rings condensed thereto.
  • a compound having a short emission wavelength it is preferable to adopt a carbazol-9-yl group substituted with a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group.
  • the substitution position is not particularly limited, but is preferably at least one of the 2- to 7-positions, more preferably at least one of the 3- or 6-positions, and even more preferably the 3- and 6-positions.
  • the donor group which can be taken by R 1 to R 5 is a carbazol-9-yl group to which one or more rings are fused, and hereinafter this is referred to as a "ring-fused carbazol-9-yl group".
  • the ring-fused carbazol-9-yl group which can be taken by R 1 to R 5 may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or 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, or may be substituted with a substituent selected from the substituent group E.
  • the ring-fused carbazol-9-yl group is unsubstituted.
  • the ring-fused carbazol-9-yl group is substituted with an aryl group which may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group in combination of two or more atoms selected from the group consisting of an alkyl group and an aryl group.
  • the total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7.
  • the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).
  • the ring-fused carbazole-9-yl group is a group bonded through a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole.
  • the fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, and may also be a ring in which these are further fused.
  • An aromatic hydrocarbon ring or an aromatic heterocycle is preferable.
  • An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring.
  • the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole.
  • the nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from the substituent group E (excluding the case where only a deuterium atom is present), and more preferably bonded to an aryl group which may be substituted with an alkyl group or an aryl group.
  • a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms is fused.
  • a carbazol-9-yl group in which a benzofuro structure is fused a carbazol-9-yl group in which a benzothieno structure is fused, or a carbazol-9-yl group in which an indolo structure is fused can be preferably employed.
  • the compound has at least one carbazol-9-yl group in which a benzofuro structure is fused, for example, two or more carbazol-9-yl groups. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group condensed with a benzothieno structure, for example, two or more.
  • a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group can also be used.
  • the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or may be, for example, 2.
  • either the 3-position or the 6-position of the ring-fused carbazol-9-yl group is substituted.
  • the ring-fused carbazol-9-yl group has at least one substituent at the para position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.
  • the ring-fused carbazol-9-yl group has at least one substituent only at the para position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has a substituent at all of the substitutable para positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.
  • donor groups that can be taken by R 1 to R 5 in general formula (1) are shown below.
  • the specific examples shown here are substituted or unsubstituted carbazole-9-yl groups (the carbazole ring may be further condensed with a ring), but the donor groups that can be employed in the present invention are not limited to the specific examples below.
  • Ph represents a phenyl group (C 6 H 5 ), and * represents the bonding position.
  • Methyl groups are not shown, so for example, D2 has one methyl group. However, a deuterated methyl group is represented as CD 3.
  • C 6 D 5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.
  • the compounds D722 to D1180 are obtained by replacing all hydrogen atoms in the above D1 to D459 with deuterium atoms.
  • D1233 to D1260 are disclosed as compounds obtained by substituting all hydrogen atoms present in the above D1181 to D1208 with deuterium atoms.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D1 to D1260.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D1 to D1180.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D17 to D76, D83 to D118, D185 to D298, D359 to D453, D472 to D519, D526 to D653, and D704 to D710.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D77 to D82, D119 to D184, D299 to D358, D455 to D459, D520 to D525, D654 to D703, and D712 to D721.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D460 to D1180 and D1214 to D1260.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D460 to D1180.
  • the donor groups which can be represented by R 1 to R 5 are D1 to D13, D17 to D22, D37, D47 to D52, D77 to D82, D119 to D131, D134, D137, D140, D146, D149, D152, D155, D158, D161, D164, D167, D170, D173, D176, D179, D182, D198, D454, D466 to D471, D521 to D525, D5 43, D712 to D716, D722 to D734, D739 to D743, D758, D768 to D773, D798 to D803, D840 to D852, D855, D858, D861, D867, D870, D873, D876, D879, D882, D885, D888, D891, D894, D897, D900, D903, D919, and D1175.
  • the donor groups which can be represented by R 1 to R 5 are selected from the group consisting of D1, D8, D9, D19, D37, D50, D77, D198, D543, D722, D729, D730, D740, D758, D771, D798, and D919.
  • one of R 1 to R 5 is a donor group. In one embodiment of the present invention, two of R 1 to R 5 are donor groups. In one embodiment of the present invention, three of R 1 to R 5 are donor groups. In a preferred embodiment of the present invention, at least R5 is a donor group. In one embodiment of the present invention, only R5 is a donor group. In one embodiment of the present invention, at least R3 and R5 are donor groups. In one embodiment of the present invention, at least R3 and R5 are donor groups. In one embodiment of the present invention, only R3 , R4 and R5 are donor groups. In one embodiment of the present invention, at least R3 is a donor group. In one embodiment of the present invention, at least R4 is a donor group.
  • R 1 to R 5 are cyano groups.
  • R 2 is a cyano group.
  • R 1 is a cyano group.
  • R 3 is a cyano group.
  • R 1 to R 5 are not cyano groups.
  • R 1 to R 5 are hydrogen atoms or deuterium atoms, preferably 1 to 3 are hydrogen atoms or deuterium atoms, and more preferably 1 to 2 are hydrogen atoms or deuterium atoms.
  • only one of R 1 to R 5 is a hydrogen atom or a deuterium atom.
  • only two of R 1 to R 5 are hydrogen atoms or deuterium atoms.
  • three of R 1 to R 5 are hydrogen atoms or deuterium atoms.
  • none of R 1 to R 5 is a hydrogen atom or a deuterium atom.
  • At least R1 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R1 and R3 are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, only R1 and R3 are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, only R1 and R2 are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, R1 , R2 and R3 are hydrogen atoms or deuterium atoms.
  • R 1 to R 5 are substituted or unsubstituted aryl groups.
  • the aryl group that R 1 to R 5 can take may be a single ring or a fused ring in which two or more rings are fused.
  • the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4.
  • Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring.
  • the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, and is preferably a substituted or unsubstituted phenyl group.
  • the substituent of the aryl group may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E.
  • the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom.
  • the aryl group is substituted with at least one deuterium atom.
  • the aryl group is unsubstituted.
  • substituted or unsubstituted aryl groups that can be R 1 to R 5 are given below.
  • the aryl groups that can be employed in the present invention should not be construed as being limited to the following specific examples.
  • * indicates a bonding position.
  • methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.
  • the aryl group which R 1 to R 5 may take is selected from the group consisting of Ar1 to Ar69.
  • the aryl group which R 1 to R 5 may take is selected from the group consisting of Ar1, Ar2, Ar5, Ar7, Ar10, Ar12, Ar14, Ar19, Ar20, Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64.
  • the aryl group which R 1 to R 5 may take is selected from the group consisting of Ar26 to Ar69. In a preferred embodiment of the present invention, the aryl group which R 1 to R 5 may take is selected from the group consisting of Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64.
  • R 1 to R 5 are substituted or unsubstituted aryl groups, and preferably 0 to 1 are substituted or unsubstituted aryl groups. In one embodiment of the present invention, only one of R 1 to R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, only two of R 1 to R 5 are substituted or unsubstituted aryl groups. In one embodiment of the present invention, none of R 1 to R 5 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, at least R 4 is a substituted or unsubstituted aryl group.
  • At least R 3 is a substituted or unsubstituted aryl group.
  • at least R 2 is a substituted or unsubstituted aryl group.
  • R 3 and R 4 are substituted or unsubstituted aryl groups.
  • R 2 and R 4 are substituted or unsubstituted aryl groups.
  • R 1 to R 5 may each be a substituted or unsubstituted alkyl group.
  • the alkyl group that can be R 1 to R 5 may be linear, branched, or cyclic. In addition, two or more of the linear portion, the cyclic portion, and the branched portion may be mixed.
  • the number of carbon atoms of the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. In addition, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • the alkyl group as a substituent may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom.
  • the substituent of the alkyl group is one or more selected from the group consisting of an aryl group and a deuterium atom.
  • the alkyl group is unsubstituted and may be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.
  • R 1 to R 5 in general formula (1) are substituted or unsubstituted alkyl groups.
  • only one of R 1 to R 5 is a substituted or unsubstituted alkyl group.
  • only two of R 1 to R 5 are substituted or unsubstituted alkyl groups.
  • only three of R 1 to R 5 are substituted or unsubstituted alkyl groups.
  • four of R 1 to R 5 are substituted or unsubstituted alkyl groups.
  • none of R 1 to R 5 is a substituted or unsubstituted alkyl group.
  • at least R 4 is a substituted or unsubstituted alkyl group.
  • at least R 3 is a substituted or unsubstituted alkyl group.
  • at least R 2 is a substituted or unsubstituted alkyl group.
  • at least R 1 is a substituted or unsubstituted alkyl group.
  • R 3 and R 4 are substituted or unsubstituted alkyl groups.
  • R 2 and R 4 are substituted or unsubstituted alkyl groups.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may be bonded to each other to form a cyclic structure.
  • the above description of the cyclic structure formed by R 14 and R 15 can be referred to.
  • one pair of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 are bonded to each other to form a cyclic structure.
  • none of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 are bonded to each other to form a cyclic structure.
  • L represents a single bond or a divalent linking group.
  • the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group.
  • L is a single bond.
  • L is a substituted or unsubstituted arylene group.
  • L is a substituted or unsubstituted heteroarylene group.
  • the description of the aryl group and the preferred range thereof in the above description of R 1 to R 5 can be referred to.
  • heteroarylene group examples include a linking group in which at least one of the ring skeleton carbon atoms constituting the arylene group is replaced with a nitrogen atom.
  • L Specific examples of L are given below. However, L that can be employed in the present invention should not be construed as being limited by these specific examples. Note that in the following specific examples, methyl groups are omitted. For this reason, for example, L3 to L5 are substituted with methyl groups. * indicates the bond position. L1 is a single bond.
  • L is selected from the group consisting of L1 to L25. In one aspect of the present invention, L is selected from the group consisting of L1 to L7, and L14 to L19. In one aspect of the present invention, L is selected from the group consisting of L1, L8 to L13, and L20 to L25. In one aspect of the present invention, L is selected from the group consisting of L2 to L25. In one aspect of the present invention, L is L1.
  • Y represents a substituted or unsubstituted carbazol-9-yl group or a substituted or unsubstituted aryl group. In one embodiment of the present invention, Y is a substituted or unsubstituted carbazol-9-yl group. In one embodiment of the present invention, Y is a substituted or unsubstituted aryl group.
  • the substituted or unsubstituted carbazol-9-yl group which Y may take corresponds to the case where none of Z 1 to Z 4 and Z 6 to Z 9 in the above general formula (b) is N.
  • Z 1 in general formula (b) represents C-R 14
  • Z 2 represents C-R 15
  • Z 3 represents C-R 16
  • Z 4 represents C- R 17
  • Z 6 represents C-R 18
  • Z 7 represents C-R 19
  • Z 8 represents C-R 20
  • Z 9 represents C-R 21.
  • the substituted or unsubstituted carbazol-9-yl group which Y may take may be a carbazol-9-yl group having one or more condensed rings.
  • the substituted or unsubstituted carbazol-9-yl group including such a ring-fused carbazol-9-yl group the corresponding descriptions of R 1 to R 5 can be referred to.
  • substituted or unsubstituted carbazol-9-yl group that Y can take include the above-mentioned D1 to D1180, and the above descriptions related to D1 to D1180 can be referred to for the group that can be selected as Y and the preferred group.
  • the substituted or unsubstituted carbazol-9-yl group represented by Y has the same structure as the donor group represented by at least one of R 1 to R 5.
  • the substituted or unsubstituted carbazol-9-yl group represented by Y has the same structure as all the donor groups represented by R 1 to R 5.
  • the substituted or unsubstituted carbazol-9-yl group represented by Y has a different structure from the donor groups represented by R 1 to R 5 .
  • the substituted or unsubstituted aryl group that Y may take the explanation and preferred range of the substituted or unsubstituted aryl group represented by R 1 to R 5 can be referred to.
  • Specific examples of the substituted or unsubstituted aryl group that Y may take include the above Ar1 to Ar69, and for the group that can be selected as Y and the preferred group, the above description related to Ar1 to Ar69 can be referred to.
  • the substituted or unsubstituted aryl group represented by Y has the same structure as the substituted or unsubstituted aryl group represented by at least one of R 1 to R 5. In one aspect of the present invention, the substituted or unsubstituted aryl group represented by Y has the same structure as all of the substituted or unsubstituted aryl groups represented by R 1 to R 5. In one aspect of the present invention, the substituted or unsubstituted aryl group represented by Y is different from the structure of the substituted or unsubstituted aryl group represented by R 1 to R 5 .
  • Y When Y is a substituted or unsubstituted aryl group, 0 to 2 of R 1 to R 5 are hydrogen atoms or deuterium atoms. A compound in which 0 to 2 of R 1 to R 5 are hydrogen atoms or deuterium atoms exhibits more favorable effects than a compound in which Y is a substituted or unsubstituted aryl group and 3 or more of R 1 to R 5 are hydrogen atoms or deuterium atoms. When Y is a substituted or unsubstituted aryl group, for example, 2 of R 1 to R 5 are hydrogen atoms or deuterium atoms.
  • R 1 to R 5 When Y is a substituted or unsubstituted aryl group, for example, one of R 1 to R 5 is a hydrogen atom or deuterium atom. When Y is a substituted or unsubstituted aryl group, for example, none of R 1 to R 5 is a hydrogen atom or a deuterium atom.
  • X 1 represents N or C-R 6
  • X 2 represents N or C-R 7.
  • X 1 is N
  • X 2 is C-R 7.
  • X 1 is C-R 6
  • X 2 is N.
  • both X 1 and X 2 are N.
  • R 6 and R 7 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • the substituent may be selected from the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E.
  • R is a hydrogen atom or a deuterium atom.
  • R is an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, R is a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group.
  • one of R 1 to R 5 is a donor group, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R 5 is a donor group, R 2 is a cyano group, R 4 is a substituted or unsubstituted aryl group, and R 1 and R 3 are each independently a hydrogen atom or a deuterium atom.
  • Y and R 5 may be the same or different.
  • one of R 1 to R 5 is a donor group, two are each independently a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R 5 is a donor group, R 3 and R 4 are each independently a substituted or unsubstituted aryl group, and R 1 and R 2 are each independently a hydrogen atom or a deuterium atom.
  • R 3 and R 4 may be the same or different.
  • Y and R 5 may be the same or different.
  • R 1 to R 5 are donor groups, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining one is a hydrogen atom or a deuterium atom
  • R 3 and R 5 are each independently a donor group
  • R 2 is a cyano group
  • R 4 is a substituted or unsubstituted aryl group
  • R 1 is a hydrogen atom or a deuterium atom.
  • Y, R 3 , and R 5 may all be the same or all be different, or only Y and R 3 may be the same, only Y and R 5 may be the same, or only R 3 and R 5 may be the same.
  • R 1 to R 5 are each independently a donor group, one is a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R 3 and R 5 are each independently a donor group, R 4 is a substituted or unsubstituted aryl group, and R 1 and R 2 are each independently a hydrogen atom or a deuterium atom.
  • Y, R 3 , and R 5 may all be the same or all different, or only Y and R 3 may be the same, only Y and R 5 may be the same, or only R 3 and R 5 may be the same.
  • R 1 to R 5 are each independently a donor group, one is a cyano group, and the remaining one is a hydrogen atom or a deuterium atom, for example, R 3 , R 4 , and R 5 are each independently a donor group, R 2 is a cyano group, and R 1 is a hydrogen atom or a deuterium atom.
  • Y, R3 , R4 , and R5 may all be the same or all different, or only R3 and R4 may be the same, or only R4 and R5 may be the same, or only R3 and R5 may be the same, or only R3 , R4 , and R5 may be the same.
  • Y in general formula (1) is a substituted or unsubstituted carbazol-9-yl group, X1 is CH, X2 is N, and L is a single bond.
  • Y in general formula (1) is a substituted or unsubstituted carbazol-9-yl group, X1 is N, X2 is CH, and L is a single bond.
  • X1 is N
  • X2 is CH
  • L is a single bond.
  • Y in general formula (1) is a substituted or unsubstituted aryl group
  • X 1 and X 2 are N
  • L is a single bond.
  • R 5 is a donor group.
  • R 2 is a cyano group.
  • R 4 is a substituted or unsubstituted aryl group.
  • R 3 is a substituted or unsubstituted aryl group.
  • one of R 1 to R 5 is a donor group, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R 5 is a donor group, R 2 is a cyano group, R 4 is a substituted or unsubstituted aryl group, and R 1 and R 3 are each independently a hydrogen atom or a deuterium atom.
  • Y and R 4 may be the same or different.
  • one of R 1 to R 5 is a donor group, one is a cyano group, two are each independently substituted or unsubstituted aryl groups, and the remaining one is a hydrogen atom or a deuterium atom, for example, R 5 is a donor group, R 2 is a cyano group, R 3 and R 4 are each independently substituted or unsubstituted aryl groups, and R 1 is a hydrogen atom or a deuterium atom.
  • Y, R 3 , and R 4 may all be the same or all be different, or only Y and R 3 may be the same, only Y and R 4 may be the same, or only R 3 and R 4 may be the same.
  • one of R 1 to R 5 is a donor group, two are each independently a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R 5 is a donor group, R 3 and R 4 are each independently a substituted or unsubstituted aryl group, and R 1 and R 2 are each independently a hydrogen atom or a deuterium atom.
  • Y, R 3 , and R 4 may all be the same or all different, or only Y and R 3 may be the same, only Y and R 4 may be the same, or only R 3 and R 4 may be the same.
  • R 5 is a donor group
  • R 2 and R 4 are each independently a substituted or unsubstituted aryl group
  • R 1 and R 3 are each independently a hydrogen atom or a deuterium atom.
  • Y, R 2 and R 4 may all be the same or all different, or only Y and R 2 may be the same, or only Y and R 4 may be the same, or only R 2 and R 4 may be the same.
  • R 1 to R 5 are each independently a donor group, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining one is a hydrogen atom or a deuterium atom
  • R 3 and R 5 are each independently a donor group
  • R 2 is a cyano group
  • R 4 is a substituted or unsubstituted aryl group
  • R 1 is a hydrogen atom or a deuterium atom.
  • R 3 and R 5 may be the same or different.
  • Y and R 4 may be the same or different.
  • R 1 to R 5 are donor groups, one is a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R 3 and R 5 are each independently a donor group, R 4 is a substituted or unsubstituted aryl group, and R 1 and R 2 are each independently a hydrogen atom or a deuterium atom.
  • R 3 and R 5 may be the same or different.
  • Y and R 4 may be the same or different.
  • R 1 to R 5 are each independently a donor group, one is a cyano group, and the remaining one is a hydrogen atom or a deuterium atom, for example, R 3 , R 4 , and R 5 are each independently a donor group, R 2 is a cyano group, and R 1 is a hydrogen atom or a deuterium atom.
  • R3 , R4 and R5 may all be the same or all be different, or only R3 and R4 may be the same, or only R4 and R5 may be the same, or only R3 and R5 may be the same.
  • Y in general formula (1) is a substituted or unsubstituted aryl group, X1 is CH, X2 is N, and L is a single bond.
  • Y in general formula (1) is a substituted or unsubstituted aryl group, X1 is N, X2 is CH, and L is a single bond.
  • X1 is N
  • X2 is CH
  • L is a single bond.
  • a compound that has a deuterium atom a carbazol-9-yl group substituted with an aryl group that may be substituted with an alkyl group or an aryl group in the molecule, and also has a cyano group.
  • the compound represented by the general formula (1) preferably does not contain metal atoms, and may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms.
  • the compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms.
  • the compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen ... and nitrogen atoms. Furthermore, the compound represented by the general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.
  • substituted group A refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means
  • substituted group B means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms).
  • an alkyl group e.g., having 1 to 40 carbon atoms
  • an alkoxy group e.g., having 1 to 40 carbon atoms
  • an aryl group e.g., having 6 to 30 carbon
  • substituted group C means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms).
  • an alkyl group e.g., having 1 to 20 carbon atoms
  • an aryl group e.g., having 6 to 22 carbon atoms
  • a heteroaryl group e.g., having 5 to 20 ring skeleton atoms
  • diarylamino group e.g., having 12 to 20 carbon atoms
  • substituted group D means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms).
  • substituted group E means one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms) and an aryl group (e.g., having 6 to 22 carbon atoms).
  • substituent when it is described as “substituted or unsubstituted” or “optionally substituted", the substituent may be selected, for example, from Substituent Group A, or may be selected from Substituent Group B, or may be selected from Substituent Group C, or may be selected from Substituent Group D, or may be selected from Substituent Group E.
  • Table 1 shows specific examples of compounds represented by general formula (1) in which Y is a perdeuterated carbazol-9-yl group (D722), X1 and X2 are both N, L is a single bond, R1 and R3 are hydrogen atoms, R2 is a cyano group, R4 is a phenyl group (Ar1), and R5 is D1 to D1260. That is, the structures of compounds 1 to 1260 are individually specified by showing R5 of compounds having the following structures in order in Table 1.
  • the structures of compounds 1 to 86940 are shown as variations of the structures shown in Table 1.
  • Table 2 specific examples of compounds represented by general formula (1) in which Y is a perdeuterated carbazol-9-yl group (D722), X1 and X2 are both N, L is a single bond, R1 and R3 are hydrogen atoms, R2 is a cyano group, R4 is Ar1 to Ar69, and R5 is D1 to D1260 are shown. That is, the structures of compounds 1 to 86940 are individually specified by showing R4 and R5 of compounds having the following structures in order in Table 2.
  • Y is fixed to D722
  • X 1 and X 2 are fixed to N
  • L is fixed to a single bond
  • R 1 and R 3 are fixed to a hydrogen atom
  • R 2 is fixed to a cyano group
  • R 4 is fixed to Ar2
  • R 5 is D1 to D1260 in order, and these are identified as compounds 1261 to 2520 in that order.
  • Y is fixed to D722
  • X 1 and X 2 are fixed to N
  • L is fixed to a single bond
  • R 1 and R 3 are fixed to a hydrogen atom
  • R 2 is fixed to a cyano group
  • R 4 is fixed to Ar3
  • R 5 is D1 to D1260 in that order, and these are identified as compounds 2521 to 3780 in that order.
  • the structures of the compounds are specified in the same manner in the subsequent rows.
  • Y is fixed to D722
  • X1 and X2 are fixed to N
  • L is fixed to a single bond
  • R1 and R3 are fixed to hydrogen atoms
  • R2 is fixed to a cyano group
  • R4 is fixed to Ar69
  • R5 is D1 to D1260 in that order, and these compounds are specified as compounds 85681 to 86940 in that order.
  • the structures of compounds 1 to 5708388 are shown as variations of the structures shown in Table 2.
  • the structures are specified by showing Y, X 1 , X 2 , L, and R 1 to R 5 of general formula (1).
  • "-" represents a single bond.
  • compounds 1 to 86940 in Table 3 compounds 1 to 86940 are specified as compounds 1 to 86940 in which Y is fixed to D722, X 1 and X 2 are fixed to N, L is fixed to a single bond, R 1 and R 3 are fixed to hydrogen atoms, R 2 is fixed to a cyano group, R 4 is any one of Ar1 to Ar69, and R 5 is any one of D1 to D1260.
  • R 4 varies from Ar1 to Ar69, and R 5 varies from D1 to D1260.
  • the one that appears first (the one listed to the left of Table 3) is fixed first, and the one that appears later (the one listed to the right of Table 3) is varied, and the compound numbers are assigned in order. That is, R 4 that appears first is first fixed to Ar1, and R 5 that appears later is set to D1 to D1260 in order, and these are identified as compounds 1 to 1260 in order.
  • R 4 is fixed to Ar2, and R 5 is set to D1 to D1260 in order, and these are identified as compounds 1261 to 2520 in order.
  • R 4 is fixed to Ar3, and R 3 is set to D1 to D1260 in order, and these are identified as compounds 2521 to 3780 in order.
  • R 4 is finally fixed to Ar69, and R 5 is sequentially set to D1 to D1260, which are identified as compounds 85681 to 86940 in order. That is, the columns of compounds 1 to 86940 in Table 3 show the structures of compounds 1 to 86940 in Table 2 all together in one column. From the columns of compounds 86941 to 173880 in Table 3, the structures of the compounds are identified in the same manner for compounds 5707129 to 5708388 in the bottom column. Note that, as shown in the rightmost column of Table 3, for example, compounds 5707129 to 5708388 in the bottom column have the same R 3 , R 4 , and R 5 .
  • compound 1(1) shows a compound having a structure in which Y in compound 1 is replaced with D1.
  • compound 2(1) shows a compound having a structure in which Y in compound 2 is replaced with D1.
  • compound 3370794(1) shows a compound having a structure in which Y in compound 3370794 is replaced with D1.
  • the structures of compounds 1(2) to 3370794(2) onward in the third row are specified in the same manner as in the second row.
  • the compound is selected from the group of compounds consisting of compounds 1 to 5708388 and compounds 1(n) to 3370794(n) [wherein n is 1 to 209]. In one embodiment of the present invention, the compound is selected from the group of compounds consisting of compounds 1 to 3370794 and compounds 1(n) to 3370794(n) [wherein n is 1 to 141]. In one embodiment of the present invention, the compound is selected from the group of compounds consisting of compounds 3370795 to 5708388 and compounds 1(n) to 3370794(n) [wherein n is 142 to 209].
  • the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, and even more preferably 1000 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 the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using the coating method, it is possible to form a film even with a compound having a relatively large molecular weight.
  • the compound represented by the general formula (1) has the advantage that it is easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify to increase the purity.
  • a polymerizable group may be present in the structure represented by the general formula (1) in advance, and the polymerizable group may be polymerized to obtain a polymer, which may be used as a light-emitting material.
  • a monomer containing a polymerizable functional group at any site of the general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, which may be used as a light-emitting material.
  • compounds having a structure represented by the general formula (1) may be coupled together to obtain a dimer or trimer, which may be used as a light-emitting material.
  • Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure 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 a linking group.
  • the number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10.
  • the linking group preferably has a structure represented by -X 11 -L 11 -.
  • X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • L 11 represents a linking group, and is preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenylene group.
  • R 101 , R 102 , R 103 and R 104 each independently represent a substituent, preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and further 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 L1 and L2 can be bonded to any site of the general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • repeating unit examples include structures represented by the following formulas.
  • a polymer having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any site of general formula (1), reacting the hydroxyl group as a linker with the compound below to introduce a polymerizable group, and polymerizing the polymerizable group.
  • a polymer containing a structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having a structure represented by general formula (1), or may be a polymer containing repeating units having other structures.
  • the repeating units having a structure represented by general formula (1) contained in the polymer may be of a single type, or of two or more types.
  • Examples of repeating units not having a structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.
  • the compound represented by the general formula (1) is a light-emitting material.
  • the compounds represented by the general formula (1) include compounds having a long light-emitting lifetime.
  • the compounds represented by the general formula (1) can improve the light-emitting properties when used in an organic light-emitting device.
  • the compounds represented by the general formula (1) include compounds that can extend the device lifetime when used in an organic light-emitting device.
  • the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence.
  • the compounds represented by the general formula (1) include compounds having a large proportion of delayed fluorescence components.
  • the compounds include compounds having delayed fluorescence components in an amount of 80% or more of the total emission, for example, compounds having delayed fluorescence components in an amount of 90% or more of the total emission.
  • the compounds represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, red region of the visible spectrum (e.g., from about 420 nm to about 500 nm, from about 500 nm to about 600 nm, or from about 600 nm to about 700 nm), or the near infrared region when excited by thermal or electronic means.
  • the compounds represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., from about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by thermal or electronic means.
  • the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., from about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet region of the spectrum (eg, 280-400 nm) when excited by thermal or electronic means.
  • compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 ⁇ m) when excited by thermal or electronic means.
  • an organic semiconductor element can be prepared using a compound represented by general formula (1).
  • the organic semiconductor element may be an organic optical element in which light is mediated, or an organic element in which light is not mediated.
  • 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 in which energy transfer occurs by light within the element.
  • an organic optical element such as an organic electroluminescence element or a solid-state imaging element (e.g., a CMOS image sensor) can be prepared using a compound represented by general formula (1).
  • a CMOS complementary metal oxide semiconductor
  • a compound represented by general formula (1) can be prepared using a compound represented by general formula (1).
  • the electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemical calculations, for example, the Hartree-Fock equations (TD-DFT/B3LYP/6-31G*) can be solved using time-dependent density functional theory with 6-31G* as a basis and a family of functions known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with HOMOs above a particular threshold and LUMOs below a particular threshold.
  • TD-DFT/B3LYP/6-31G* time-dependent density functional theory with 6-31G* as a basis and a family of functions known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with HOMOs above a particular threshold and LUMOs below a particular threshold.
  • the donor moiety (“D") can be selected, for example, for its HOMO energy (e.g., ionization potential) of -6.5 eV or greater
  • the acceptor moiety (“A") can be selected, for example, for its LUMO energy (e.g., electron affinity) of -0.5 eV or less.
  • the bridging moiety (“B") prevents overlap between the pi-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly restrict the acceptor and donor moieties to specific conformations.
  • the compound library is screened using one or more of the following properties: 1. Emission near a particular wavelength2. Calculated triplet state above a particular energy level3.
  • the difference between the lowest singlet excited state and the lowest triplet excited state ( ⁇ E ST ) at 77K 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 ⁇ E ST 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 compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.
  • the compounds represented by the general formula (1) include novel compounds.
  • the compound represented by the general formula (1) can be synthesized by combining known reactions.
  • one to three of R 1 to R 5 are donor groups, and for example, a compound of the general formula (1) in which a substituted or unsubstituted carbazol-9-yl group is a donor group can be synthesized by reacting a precursor in which the donor group site is a fluorine atom with a substituted or unsubstituted carbazole.
  • the synthesis examples described later can be referred to.
  • the compound of formula (1) is combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compound to form a solid film or layer.
  • the compound of formula (1) can be combined with an electroactive material to form a film.
  • the compound of formula (1) can be combined with a hole transport polymer.
  • the compound of formula (1) can be combined with an electron transport polymer.
  • the compound of formula (1) can be combined with a hole transport polymer and an electron transport polymer.
  • the compound of formula (1) can be combined with a copolymer having both a hole transport moiety and an electron transport moiety.
  • electrons and/or holes formed in the solid film or layer can interact with the compound of formula (1).
  • the film containing the compound represented by general formula (1) can be formed by a wet process.
  • a solution containing the composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent.
  • the wet process include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing.
  • a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used.
  • a substituent e.g., an alkyl group
  • a substituent that increases the solubility in organic solvents can be introduced into the compound contained in the composition.
  • the film containing the compound of the present invention can be formed by a dry process.
  • the dry process can be a vacuum deposition method, but is not limited thereto.
  • the compounds constituting the film may be co-deposited from individual deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed.
  • a single deposition source is used, a mixed powder in which the powders of the compounds are mixed may be used, or a compression molded body in which the mixed powder is compressed may be used, or a mixture in which each compound is heated, melted, and cooled may be used.
  • a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source can be formed by performing co-deposition under conditions in which the deposition rates (weight reduction rates) of the multiple compounds contained in a single deposition source are the same or almost the same. If a multiple compound is mixed in the same composition ratio as the composition ratio of the film to be formed and used as a deposition source, a film having a desired composition ratio can be easily formed.
  • a temperature at which each compound to be co-deposited has the same weight reduction rate can be specified, and the temperature can be adopted as the temperature during co-deposition.
  • the compound represented by the general formula (1) is useful as a material for an organic light-emitting device, and is particularly preferably used for an organic light-emitting diode.
  • Organic Light-Emitting Diode One aspect of the present invention relates to the use of a compound represented by the general formula (1) of the present invention as a light-emitting material of an organic light-emitting device.
  • the compound represented by the 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 the general formula (1) includes a delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence.
  • the present invention provides a delayed fluorescent material having a structure represented by the general formula (1).
  • the present invention relates to the use of a compound represented by the general formula (1) as a delayed fluorescent material.
  • the present invention can use a compound represented by the general formula (1) as a host material and can be used together with one or more light-emitting materials, and the light-emitting material can be a fluorescent material, a phosphorescent material, or a TADF.
  • the compound represented by the general formula (1) can also be used as a hole transport material.
  • the compound represented by the general formula (1) can be used as an electron transport material.
  • the present invention relates to a method for generating delayed fluorescence from a compound represented by the general formula (1).
  • an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency.
  • the light-emitting layer comprises a compound represented by formula (1), and the compound represented by formula (1) is aligned parallel to the substrate.
  • the substrate is a film-forming surface.
  • the orientation of the compound represented by formula (1) relative to the film-forming surface affects or dictates the propagation direction of light emitted by the aligned compound.
  • the organic light-emitting device includes an emitting layer.
  • the emitting layer includes a compound represented by general formula (1) as a light-emitting material.
  • the organic light-emitting device is an organic photoluminescence device (organic PL device).
  • the organic light-emitting device is an organic electroluminescence device (organic EL device).
  • the compound represented by general formula (1) assists the light emission of other light-emitting materials included in the emitting layer (as a so-called assist dopant).
  • the compound represented by general formula (1) included in the emitting layer is at its lowest excited singlet energy level, and is included between the lowest excited singlet energy level of the host material included in the emitting layer and the lowest excited singlet energy level of the other light-emitting materials included in the emitting layer.
  • the organic photoluminescent device includes at least one light-emitting layer.
  • the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic layer includes at least a light-emitting layer. In some embodiments, the organic layer includes only a light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.
  • the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, only the light-emitting material is used as the light-emitting layer. In some embodiments, the light-emitting layer includes a light-emitting material and a host material. In some embodiments, the light-emitting material is one or more compounds represented by general formula (1).
  • a host material is used in the light-emitting layer in addition to the light-emitting material.
  • the host material is an organic compound.
  • the organic compound has an excited singlet energy and an excited triplet energy, at least one of which is higher than those of the light-emitting material of the present invention.
  • the singlet excitons and triplet excitons generated in the light-emitting material of the present invention are trapped in the molecules of the light-emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently trapped to improve the light emission efficiency. In some embodiments, the singlet and triplet excitons are not sufficiently trapped, although a high light emission efficiency is still obtained, i.e., a host material that can achieve a high light emission efficiency can be used in the present invention without any particular limitation. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence.
  • the emitted light includes the emitted light from the host material. In some embodiments, the emitted light consists of the emitted light from the host material. In some embodiments, the emitted light includes the emitted light from the compound represented by formula (1) and the emitted light from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.
  • various compounds can be adopted as a light-emitting material (preferably a fluorescent material).
  • a light-emitting material preferably a fluorescent material.
  • exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined with each other. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) are given below.
  • Further preferred light-emitting materials include compounds represented by the following general formula (2).
  • R 1 , R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 2 represents an acceptor group, or R 1 and R 2 are bonded together to form an acceptor group, or R 2 and R 3 are bonded together to form an acceptor group.
  • 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 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , and R 15 and R 16 may be bonded together to form a cyclic structure.
  • X 1 represents O or NR
  • R represents a substituent.
  • at least one of X 3 and X 4 is O or NR, and the remaining may be O or NR or may not be linked.
  • both ends independently represent a hydrogen atom, a deuterium atom or a substituent.
  • C-R 1 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
  • R7 is an acceptor group
  • R6 and R7 are bonded to each other to form an acceptor group
  • R7 and R8 are bonded to each other to form an acceptor group
  • X3 is O or NR
  • R10 is an acceptor group
  • R9 and R10 are bonded to each other to form an acceptor group
  • R10 and R11 are bonded to each other to form an acceptor group
  • R15 is an acceptor group
  • R14 and R15 are bonded to each other to form an acceptor group
  • R15 and R16 are bonded to each other to form an acceptor group.
  • R when X2 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding to the carbon atom to which R8 is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group.
  • R when X3 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding to the carbon atom to which R9 is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group.
  • R when X4 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding to the carbon atom to which R16 is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group.
  • X1 when X1 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding with the carbon atom to which R1 is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (wherein the 3-position is on the phenyl group).
  • the compound is represented by the following general formula (2a).
  • R 1 , R 3 , R 6 to R 11 , and R to R 16 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R 2 represents an acceptor group, or R 1 and R 2 are bonded to each other to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group.
  • R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 14 and R 15 , and R 15 and R 16 may be bonded to each other to form a cyclic structure.
  • X 1 represents O or NR, and R represents a substituent.
  • X 3 and X 4 are O or NR, and the remaining may be O or NR or may not be linked.
  • both ends each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • C-R 1 , C-R 3 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
  • Further preferred light-emitting materials include compounds represented by the following general formula (3).
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R 1 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 2 , R 2 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 1 may be bonded to each other to form a cyclic structure.
  • C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
  • R1 and R2 are each independently a substituted or unsubstituted phenyl group which may be condensed with another ring.
  • R3 and R10 are each independently a substituted amino group.
  • at least one combination of R1 and R3 , and R2 and R10 are bonded to each other to form a cyclic structure.
  • the cyclic structure includes a benzoazaborine ring.
  • Further preferred light-emitting materials include compounds represented by the following general formula (4).
  • Z1 and Z2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R1 to R9 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R1 and R2 , R2 and R3 , R3 and R4 , R4 and R5 , R5 and R6 , R7 and R8 , and R8 and R9 may be bonded to each other to form a cyclic structure.
  • At least one of Z 1 , Z 2 , the ring formed by bonding R 1 and R 2 together, the ring formed by bonding R 2 and R 3 together, the ring formed by bonding R 4 and R 5 together, and the ring formed by bonding R 5 and R 6 together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and at least one of R 1 to R 9 is a substituted or unsubstituted aryl group or an acceptor group, or at least one of Z 1 and Z 2 is a ring having an aryl group or an acceptor group as a substituent.
  • a substitutable carbon atom may be substituted with a nitrogen atom.
  • C-R 1 , C-R 2 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 and C-R 9 may be substituted with N.
  • Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring.
  • R 1 to R 9 are each independently a substituted or unsubstituted aryl group or an acceptor group, or one or more rings selected from the group consisting of a ring formed by R 1 and R 2 bonding together, a ring formed by R 2 and R 3 bonding together, a ring formed by R 4 and R 5 bonding together, and a ring formed by R 5 and R 6 bonding together are a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring.
  • R 8 is a substituted or unsubstituted aryl group or an acceptor group.
  • the compound contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.
  • Further preferred light-emitting materials include compounds having a fused ring structure A (wherein a hydrogen atom in the structure may be substituted with a deuterium atom or a substituent) in which a carbon-carbon bond a in the following structure ⁇ is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring,
  • X1 and X2 each independently represent a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom;
  • Z represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring;
  • R1 represents a hydrogen atom, a deuterium atom, or a substituent; and Z and X2 may be bonded to each other to form a cyclic structure.
  • the fused to b and X 1 , the structure fused to b and Z, and Z and X 2 may be bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (5).
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 1 represents a hydrogen atom, a deuterium atom, or a substituent
  • R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 are bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (6).
  • X3 represents an oxygen atom or a sulfur atom
  • Z2 and Z3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R1 and R4 to R7 each independently represent a hydrogen atom, a deuterium atom or a substituent
  • R2 and R3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • R2 and Z2 , Z2 and Z3 , Z3 and R3 , R4 and R5 , R5 and R6 , and R6 and R7 may be bonded to each other to form a cyclic structure. However, at least one pair of R2 and Z2 , Z2 and Z3 , and Z3 and R3 are bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (7).
  • R2 and Z2 , Z2 and Z3 , Z3 and R3 , R4a and R5a , R5a and R6a , R6a and R7a , and R7a and R1 may be bonded to each other to form a cyclic structure.
  • at least one pair of R2 and Z2 , Z2 and Z3 , and Z3 and R3 are bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (8).
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 and R 8 to R 14 each independently represent a hydrogen atom, a deuterium atom, or a substituent
  • R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure.
  • Z 1 and Z 4 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 and R 15 to R 17 each independently represent a hydrogen atom, a deuterium atom, or a substituent
  • R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , and Z 3 and R 3 may be
  • Z 1 and Z 5 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 represents a hydrogen atom, a deuterium atom, or a substituent
  • R 2 and R 3 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 are bonded to each other to form a cyclic structure.
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring;
  • Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring;
  • R 1 and R 21 to R 27 each independently represent a hydrogen atom, a deuterium atom, or a substituent; and R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R1 and Z1 , R2 and Z2 , Z2 and R21 , R21 and R22 , R22 and R23 , R23 and R24 , R24 and R25 , R25 and R26 , and R26 and R27 may be bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (12).
  • Z 1 and Z 6 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 and R 28 to R 30 each independently represent a hydrogen atom, a deuterium atom, or a substituent
  • R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , and R 30 and Z 6 may be
  • Further preferred light-emitting materials include compounds represented by the following general formula (13).
  • Z 1 and Z 7 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 represents a hydrogen atom, a deuterium atom, or a substituent
  • R 2 and R 3 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 2 and Z 2 , Z 2 and Z 7 , and Z 7 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 7 , and Z 7 and R 3 are bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (14).
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 31 to R 44 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , and R 43 and R 44 may be bonded to each other to form a cyclic structure.
  • Z 1 and Z 8 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 51 to R 60 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R 1 and Z 1 , R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , and R 60 and Z 8 may be bonded to each other to form a cyclic structure.
  • Z 1 , Z 8 and Z 9 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 61 to R 66 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , and R 66 and Z 8 may be bonded to each other to form a cyclic structure.
  • Z 1 , Z 9 and Z 10 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 67 to R 69 each independently represent a hydrogen atom, a deuterium atom or a substituent
  • R 70 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , Z 9 and R 67 , R 67 and R 68 , R 68 and R 69 , R 69 and Z 10 , and Z 10 and R 70 may be bonded to each other to form a cyclic structure.
  • Z 1 , Z 11 , and Z 12 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring;
  • R 1 and R 72 to R 74 each independently represent a hydrogen atom, a deuterium atom, or a substituent;
  • R 71 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 71 and Z 11 , Z 11 and R 72 , R 72 and R 73 , R 73 and Z 74 , and R 74 and Z 12 may be bonded to each other to form a cyclic structure.
  • Z 1 and Z 11 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 76 to R 82 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • R 75 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R 78 and R 79 , R 79 and R 80 , R 80 and R 81 , and R 81 and R 82 may be bonded to each other to form a cyclic structure.
  • Further preferred light-emitting materials include compounds represented by the following general formula (20).
  • X5 represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded;
  • R101 to R130 each independently represent a hydrogen atom, a deuterium atom, or a substituent;
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 3 to R 9 each independently represent a hydrogen atom, a deuterium atom, or a substituent, provided that at least one of R 1 , R 2 , Z 1 , and Z 2 contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring.
  • R1 and Z1 , Z1 and R3 , R3 and R4 , R4 and R5 , R5 and Z2 , Z2 and R2 , R2 and R6 , R6 and R7 , R7 and R8 , R8 and R9 , and R9 and R1 may be bonded to each other to form a ring structure.
  • the substitutable carbon atoms may be substituted with a nitrogen atom.
  • C- R3 , C - R4 , C- R5 , C-R6, C- R7 , C- R8 , and C- R9 in the general formula (21) may be substituted with N.
  • R 1 and R 2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring.
  • Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring.
  • R 1 and Z 1 are bonded to each other to form a cyclic structure.
  • R 1 and Z 1 are bonded to each other to form a cyclic structure.
  • one of X1 and X2 is a nitrogen atom and the other is a boron atom.
  • R1 to R26 , A1 and A2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R1 and R2 , R2 and R3 , R3 and R4 , R4 and R5 , R5 and R6 , R6 and R7 , R7 and R8 , R8 and R9 , R9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R19 , R19 and R20 , R20 and R21 , R21 and R22 , R22 and R23 , R23 and R24 , R24 and R25 , R25 and R 26 may be bonded to each other to form a cyclic structure.
  • R 1 to R 6 is a substituted or unsubstituted aryl group, or any of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 are bonded to each other to form an aromatic ring or a heteroaromatic ring.
  • the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 20% by weight or less.
  • the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 10% by weight or less.
  • the host material of the light-emitting layer is an organic compound that has hole transport and electron transport functions.
  • the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing.
  • the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.
  • the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule.
  • the concentration of the first TADF molecule in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material.
  • the composition in the light-emitting layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecule, and 0.1 to 30% by weight of the second TADF molecule.
  • the composition in the light-emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule.
  • the light-emitting layer can contain three types of TADF molecules with different structures.
  • the compound of the present invention may be any of the multiple TADF compounds contained in the light-emitting layer.
  • the light-emitting layer can be made of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms.
  • the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.
  • the TADF material may be a known delayed fluorescent material.
  • Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955, and paragraph 0008 of WO2013/081088.
  • JP 2013-256490 A paragraphs 0009 to 0046 and 0093 to 0134; JP 2013-116975 A, paragraphs 0008 to 0020 and 0038 to 0040; WO 2013/133359 A, paragraphs 0007 to 0032 and 0079 to 0084; WO 2013/161437 A, paragraph 0 No. 008 to 0054 and No.
  • the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.
  • the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof.
  • the metal, alloy, or conductive compound has a high work function (4 eV or more).
  • the metal is Au.
  • the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2 , and ZnO.
  • an amorphous material capable of forming a transparent conductive film such as IDIXO ( In2O3 - ZnO ), is used.
  • the anode is a thin film.
  • the thin film is made by evaporation or sputtering.
  • the film is patterned by a photolithography method.
  • the pattern may be formed using a mask with a shape suitable for evaporation or sputtering on the electrode material.
  • a wet film formation method such as a printing method or a coating method, is used.
  • 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 anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.
  • the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron injecting metal), an alloy, a conductive compound, or a combination thereof.
  • the electrode material is selected from sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al 2 O 3 ) mixtures, indium, lithium-aluminum mixtures, and rare earth elements.
  • a mixture of an electron injecting metal and a second metal is used, the second metal being a stable metal with a higher work function than the electron injecting metal.
  • 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.
  • the mixture improves electron injection properties and resistance to oxidation.
  • the cathode is fabricated by forming the electrode material as a thin film by evaporation or sputtering.
  • the cathode has a sheet resistance of a few hundred ohms or less per unit area. In some embodiments, the cathode has a thickness of 10 nm to 5 ⁇ m. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semi-transparent to allow the emitted light to pass through. In some embodiments, a transparent or semi-transparent electroluminescent device enhances light radiance.
  • the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode, hi some embodiments, an element includes an anode and a cathode, both of which are transparent or semi-transparent.
  • An injection layer is a layer between an electrode and an organic layer.
  • the injection layer reduces the driving voltage and enhances the light radiance.
  • the injection layer includes a hole injection layer and an electron injection layer.
  • the injection layer can be disposed between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.
  • an injection layer is present. In some embodiments, an injection layer is not present. 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 outside the light-emitting layer.
  • an electron barrier layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer.
  • a hole barrier layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer.
  • a barrier layer prevents excitons from diffusing outside the light-emitting layer.
  • the electron barrier layer and the hole barrier layer constitute an exciton barrier layer.
  • the term "electron barrier layer" or "exciton barrier layer” includes layers that have both the functions of an electron barrier layer and of an exciton barrier layer.
  • Hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer.
  • the materials used for the hole blocking layer can be the same materials as those 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, during hole transport, the electron blocking layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer.
  • the materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron blocking material are given below.
  • Exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, the layer may be present between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer.
  • the layer when the exciton blocking layer is present on the cathode side, the layer may be present between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the light-emitting 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 excited triplet energy, respectively, of the light-emitting material.
  • the hole transport layer comprises a hole transport material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one of the following properties: hole injection or transport property and electron blocking 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, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof.
  • 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 hole transport materials are given below.
  • the electron transport layer comprises an electron transport material.
  • the electron transport layer is a single layer.
  • the electron transport layer has multiple layers.
  • the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer.
  • the electron transport material also functions as a hole-blocking material.
  • electron transport layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole 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 electron transport materials are given below.
  • the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet.
  • an electronic device includes an OLED having an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode.
  • the compositions described herein may be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
  • compositions may be useful in facilitating charge or energy transfer within devices and/or as hole transport materials, such as organic light emitting diodes (OLEDs), organic integrated circuits (OICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light emitting fuel cells (LECs), or organic laser diodes (O-lasers).
  • OLEDs organic light emitting diodes
  • OICs organic integrated circuits
  • O-FETs organic field effect transistors
  • OF-TFTs organic thin film transistors
  • O-LETs organic light emitting transistors
  • O-SCs organic solar cells
  • organic optical detectors organic photoreceptors, organic field-quench devices (O-FQDs), light emitting fuel cells (LECs), or organic laser diodes (O-lasers
  • the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode.
  • the device includes OLEDs of different colors.
  • the device includes an array including a combination of OLEDs.
  • the combination of OLEDs is a three-color combination (e.g., RGB).
  • the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green).
  • the combination of OLEDs is a two-color, four-color, or more-color combination.
  • the device comprises: a circuit board having a first side having a mounting surface and an opposing second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture.
  • the OLED light comprises a plurality of OLEDs mounted on a circuit board such that light is emitted in a plurality of directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.
  • the light-emitting layer of the present invention can be used in a screen or display.
  • the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching to provide pixels with unique aspect ratios.
  • the screen also called a mask
  • the corresponding artwork pattern design allows for the placement of very steep narrow tie bars between pixels in the vertical direction, as well as large wide angled openings in the horizontal direction.
  • the internal patterning of the pixel allows for the construction of three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in the pixel area protects etching in certain areas until those particular patterns are undercut and removed from the substrate. At that point, all pixel areas are treated with similar etch rates, but the depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with different protection rates within the pixel, allowing for the localized deep etching required to create steep vertical bevels.
  • the preferred material for the deposition mask is Invar.
  • the screen or display pattern is a pixel matrix on a substrate.
  • the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).
  • the screen or display pattern is fabricated using wet chemical etching.
  • the screen or display pattern is fabricated using plasma etching.
  • OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating a planarizing film on the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel.
  • TFT thin film transistor
  • a method for manufacturing an organic light emitting diode (OLED) display comprising the steps of: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in the form of a cell panel; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels.
  • the barrier layer is an inorganic film, for example made of SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic.
  • the organic film helps the mother panel to be cut softly into cell panels.
  • the thin film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source/drain electrodes.
  • Each of the plurality of display units may have a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed at the same time as the planarization film.
  • the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization 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 the encapsulation layer.
  • each of the organic film and the planarization film may comprise one of polyimide and acrylic.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide.
  • the method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide prior to forming a barrier layer on the other surface of the base substrate, and 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 disposed on the TFT layer for covering the TFT layer.
  • the planarization film is an organic film formed on the passivation layer.
  • the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.
  • the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source/drain electrode of a TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image.
  • a display unit an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.
  • the encapsulation layer that covers the display units and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated.
  • the organic film applied to the interface portion is disposed at an interval with each of the plurality of display units.
  • the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the end of the barrier layer.
  • the OLED display is flexible and uses a flexible base substrate formed from polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed from a glass material, and the carrier substrate is then separated.
  • a barrier layer is formed on a surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is 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 grooves.
  • the manufacturing method further includes a step of cutting along the interface, where a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, and the groove 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 disposed on the TFT layer to cover the TFT layer.
  • the planarization film for example made of polyimide or acrylic
  • the groove of the interface is covered with an organic film, for example made of polyimide or acrylic.
  • the interface grooves between the barrier layers are covered with an organic film to absorb shocks that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers.
  • the organic film and planarizing film covering the interface grooves are spaced apart from each other.
  • the organic film and planarizing film were connected to each other as one layer, there would be a risk of external moisture penetrating the display unit through the planarizing film and the remaining organic film, so the organic film and planarizing film are spaced apart from each other such that the organic film is spaced apart from the display unit.
  • the display unit is formed by forming a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit.
  • the carrier substrate carrying the base substrate is separated from the base substrate.
  • the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate.
  • the mother panel is cut into individual cell panels.
  • the mother panel is cut along the interface between the cell panels using a cutter.
  • the grooves of the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting.
  • the barrier layer is prevented from cracking during cutting. In some embodiments, the methods reduce product defect rates and stabilize product quality.
  • Another aspect is an OLED display having 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 film applied to the edges of the barrier layer.
  • Carbazole-1,2,3,4,5,6,7,8-d8 (1.93 g, 11.0 mmol) and potassium carbonate (2.07 g, 15.0 mmol) were added to a mixture of intermediate b (3.27 g, 5.00 mmol) and N,N-dimethylformamide (DMF, 100 mL), and the mixture was stirred at 150° C. for 1 hour.
  • the reaction solution was cooled to room temperature, and the solid was filtered and washed with toluene.
  • the filtrate was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. After removing the solvent, the solid was reprecipitated with toluene/hexane, and the resulting solid was collected.
  • Carbazole-1,2,3,4,5,6,7,8-d8 (15.82 g, 90.3 mmol) and tripotassium phosphate (31.9 g, 150.5 mmol) were added to a mixture of intermediate e (9.62 g, 37.6 mmol) and DMF (380 mL), and the mixture was stirred at 120° C. for 20 hours.
  • the reaction vessel was cooled to room temperature, ion-exchanged water was added, the mixture was extracted with acetic acid, and the mixture was washed with saturated saline, then dried over magnesium sulfate and filtered.
  • intermediate f (9.90 g, 24.1 mmol) was weighed into a three-neck flask, degassed and replaced with nitrogen gas, then THF (96 mL) was added and cooled to -78 ° C., and n-butyl lithium 2.3 M hexane solution (11.5 ml) was slowly added. After stirring at -78 ° C. for 30 minutes, trimethylboronic acid was added and stirred for another 30 minutes, and then stirred at room temperature for 1 hour.
  • the reaction solution was cooled to room temperature, ion-exchanged water was added, and then the organic phase and the aqueous phase were separated.
  • the aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated saline.
  • the mixture was dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated.
  • Carbazole-1,2,3,4,5,6,7,8-d8 (1.93 g, 11.0 mmol) and potassium carbonate (2.07 g, 15.0 mmol) were added to a mixture of intermediate r (2.82 g, 5.00 mmol) and DMF (100 mL), and the mixture was stirred at 150° C. for 1 hour.
  • the reaction solution was cooled to room temperature, the solid was removed by celite filtration, and the celite was washed with ethyl acetate.
  • the obtained filtrate was concentrated, and methanol was added to precipitate a solid. This solid was filtered off and washed with methanol and hexane.
  • a 0.5M lithium chloride THF solution (2.5mL) was added to a THF solution (80mL) of compound s (5.0g, 25mmol) at room temperature.
  • the mixed solution was cooled to -78°C, and a 1M lithium diisopropylamide (LDA) THF/hexane solution (27mL) was slowly added dropwise.
  • LDA lithium diisopropylamide
  • a 1M zinc chloride THF solution 31mL was added, and the mixture was stirred for another 30 minutes and then returned to room temperature.
  • Example 1 Preparation and Evaluation of Thin Film Using Compound A
  • Compound A and Compound H1 were co-deposited on a quartz substrate by vacuum deposition at a vacuum degree of 5.0 ⁇ 10 ⁇ 5 Pa to form a thin film.
  • the concentration of Compound A was 30% by weight.
  • the lifetime ⁇ 2 of the delayed fluorescent component is shorter for compounds A to J than for comparative compounds A and B, demonstrating that these compounds can contribute to the stability of the device.
  • the proportion of delayed fluorescent components in the total light emission was calculated, the thin films using compounds A to H had a higher proportion of delayed fluorescent components than the thin film using comparative compound B.
  • Example 11 Preparation and evaluation of organic electroluminescence element On a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, each thin film was laminated by vacuum deposition at a vacuum degree of 5.0 ⁇ 10 ⁇ 5 Pa.
  • ITO indium tin oxide
  • NPD was formed thereon to a thickness of 30 nm
  • TrisPCz was further formed thereon to a thickness of 10 nm
  • H1 was formed thereon to a thickness of 5 nm.
  • H1 and compound A were co-deposited from different deposition sources to form a layer with a thickness of 40 nm to serve as an emitting layer.
  • the concentration of the compound in the emitting layer was 30% by weight.
  • SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different deposition sources to form a layer with a thickness of 30 nm.
  • the concentrations of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively.
  • Liq was then formed to a thickness of 2 nm, and aluminum (Al) was then vapor-deposited to a thickness of 100 nm to form a cathode, thereby completing an organic electroluminescence element.

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  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé qui est représenté par la formule générale et qui présente une longue durée de vie. Dans la formule générale, un à trois fragments parmi R1 à R5 sont chacun un groupe donneur, les autres sont chacun H, D, un groupe cyano, un groupe aryle ou un groupe alkyle, L est une liaison simple ou un groupe de liaison, X1 est N ou C, et Y est un groupe carbazol-9-yle ou un groupe aryle.
PCT/JP2024/029573 2023-08-22 2024-08-21 Composé, matériau électroluminescent et élément électroluminescent Pending WO2025041780A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019119723A (ja) * 2018-01-11 2019-07-22 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用組成物、及び有機エレクトロルミネッセンス素子
WO2022096869A1 (fr) * 2020-11-03 2022-05-12 University Court Of The University Of St Andrews Composés organiques destinés à être utilisés dans des dispositifs électroluminescents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019119723A (ja) * 2018-01-11 2019-07-22 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用組成物、及び有機エレクトロルミネッセンス素子
WO2022096869A1 (fr) * 2020-11-03 2022-05-12 University Court Of The University Of St Andrews Composés organiques destinés à être utilisés dans des dispositifs électroluminescents

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