WO2024204430A1 - 有機発光素子 - Google Patents

有機発光素子 Download PDF

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WO2024204430A1
WO2024204430A1 PCT/JP2024/012428 JP2024012428W WO2024204430A1 WO 2024204430 A1 WO2024204430 A1 WO 2024204430A1 JP 2024012428 W JP2024012428 W JP 2024012428W WO 2024204430 A1 WO2024204430 A1 WO 2024204430A1
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substituted
ring
general formula
unsubstituted
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French (fr)
Japanese (ja)
Inventor
ヨンジュ ジョ
桃子 森尾
善丈 鈴木
ソンヘ ファン
寛晃 小澤
幸誠 金原
伊織 鈴木
太郎 ▲濱▼▲崎▼
祐子 下位
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Kyulux Inc
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Kyulux Inc
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Application filed by Kyulux Inc filed Critical Kyulux Inc
Priority to JP2024539715A priority Critical patent/JP7584198B1/ja
Priority to CN202480022468.2A priority patent/CN120958990A/zh
Priority to KR1020257032549A priority patent/KR20250164754A/ko
Priority to EP24780531.0A priority patent/EP4694635A4/en
Publication of WO2024204430A1 publication Critical patent/WO2024204430A1/ja
Priority to JP2024188924A priority patent/JP2025010245A/ja
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Definitions

  • the present invention relates to organic light-emitting devices such as organic electroluminescence devices.
  • Organic light-emitting elements are light-emitting elements that use organic materials, can be manufactured by coating, and have attracted attention in recent years because they do not use rare elements.
  • organic electroluminescence elements organic electroluminescence elements
  • organic EL elements have the advantage that they can be made into lightweight and flexible elements because they emit light by themselves and do not require a backlight. They also have the characteristics of fast response and high visibility, and are expected to be the next-generation light source. For this reason, research on the development of materials useful for organic light-emitting elements, including organic electroluminescence elements, is being actively carried out. In particular, research on light-emitting materials is being actively conducted.
  • Fluorescent materials, phosphorescent materials, and fluorescent materials have long been known as light-emitting materials, but fluorescent materials have the problem of low luminous efficiency, and phosphorescent materials contain rare metals, making them expensive and difficult to emit deep blue light. In recent years, delayed fluorescent materials have been developed as light-emitting materials that address these issues.
  • 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 of the present invention have conducted extensive research with the aim of providing compounds that are more useful as delayed fluorescent materials for light-emitting devices. They have then derived and generalized a general formula for compounds that are more useful as delayed fluorescent materials, and have pursued intensive research with the aim of using such compounds in organic light-emitting devices.
  • the present inventors have found that a compound having a structure that satisfies certain conditions is useful as a light-emitting material and makes it possible to provide an excellent organic light-emitting device.
  • the present invention has been proposed based on this finding, and specifically has the following configuration.
  • An organic light-emitting device comprising a compound represented by the following general formula (1) and a host material or a dopant material in the same layer:
  • R 1 to R 5 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the following general formula (2).
  • R 2 or R 3 is a group represented by the following general formula (2), and two or more of R 1 to R 5 are donor groups.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • X 1 to X 3 each independently represent N or C(R), but at least one of X 1 to X 3 is N.
  • R represents a hydrogen atom, a deuterium atom, or a substituent.
  • Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • L 1 represents a single bond or a divalent linking group. * represents a bonding position.
  • At least one of R 1 to R 5 is a donor group having a condensed ring structure of four or more rings
  • at least one of Ar 1 to Ar 4 is a substituted or unsubstituted heteroaryl group (excluding a nitrogen-containing 6-membered ring group)
  • R 1 to R 5 and Ar 1 to Ar 4 satisfy both of these conditions.
  • R 1 to R 5 in the general formula (1) is a donor group represented by the following general formula (3):
  • X represents O, S or N-R 14.
  • R 11 to R 13 each independently represent a deuterium atom or a substituent.
  • R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group.
  • 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.
  • X 1 is a boron atom
  • X 2 is a nitrogen atom
  • R 7 and R 8 , and R 17 and R 18 are bonded together to form a cyclic structure containing a boron atom
  • the cyclic structure is a 5- to 7-membered ring, and when it is a 6-membered ring, R 7 and R 8 , and R 17 and R 18 are bonded together to form -B(R 32 )-, -CO-, -CS-, or -N(R 27 )-.
  • R 27 represents a hydrogen atom, a deuterium atom, or a substituent.
  • a 11 and A 12 each independently represent a benzene ring, a furan ring, a thiol ring, a pyrrole ring or a cyclopentadiene ring, which may be further condensed with other rings or may be substituted.
  • R 111 to R 114 , R B , and R C each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group.
  • R 115 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond to L.
  • R A represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L.
  • R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 , and R B and R C may be bonded to each other to form a cyclic structure.
  • n represents an integer of either 3 or 4.
  • L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group to which two or more of these are bonded.
  • the organic light-emitting device of the present invention exhibits excellent light-emitting properties.
  • 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 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the following general formula (2).
  • R 2 or R 3 is a group represented by the following general formula (2), and two or more of R 1 to R 5 are donor groups.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 to R 5 are donor groups having a condensed ring structure of four or more rings
  • one or more of Ar 1 to Ar 4 are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing six-membered ring groups), or R 1 to R 5 and Ar 1 to Ar 4 satisfy both of these conditions.
  • Ar 3 and Ar 4 are groups present in general formula (2).
  • 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.
  • the aryl group that can be R 1 to R 5 , Ar 1, and Ar 2 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.
  • R 1 to R 5 , Ar 1 , and Ar 2 Specific examples of substituted or unsubstituted aryl groups that can be used by R 1 to R 5 , Ar 1 , and Ar 2 are given below.
  • the aryl groups that can be used 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.
  • groups in which all hydrogen atoms present in Ar1 to Ar26 are replaced with deuterium atoms are exemplified here as Ar47 to Ar72, in that order.
  • the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar1 to Ar72.
  • the aryl group which R 1 to R 5 can take is Ar1 or Ar47.
  • the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar2 to Ar11, Ar27 to Ar36, and Ar48 to 57.
  • the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar12 to Ar20, Ar37 to Ar45, and Ar58 to Ar66. In one embodiment of the present invention, the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar22 to Ar26, and Ar68 to Ar72. In a preferred embodiment of the present invention, the aryl group which can be represented by R 1 to R 5 is selected from the group consisting of Ar1, Ar12 to Ar15, Ar24, Ar37 to Ar40, Ar47, Ar58 to Ar61, and Ar70. In one embodiment of the present invention, the aryl group that Ar 1 or Ar 2 can take is selected from the group consisting of Ar 1 to Ar 72.
  • the aryl group that Ar 1 or Ar 2 can take is Ar 1 or Ar 47. In one embodiment of the present invention, the aryl group that Ar 1 or Ar 2 can take is selected from the group consisting of Ar 2 to Ar 11, Ar 27 to Ar 36, and Ar 48 to 57. In one embodiment of the present invention, the aryl group that Ar 1 or Ar 2 can take is selected from the group consisting of Ar 12 to Ar 20, Ar 37 to Ar 45, and Ar 58 to Ar 66. In a preferred embodiment of the present invention, the aryl group that R 1 to R 5 can take is selected from the group consisting of Ar 1, Ar 12 to Ar 14, Ar 37 to Ar 40, Ar 47, and Ar 58 to Ar 61.
  • R 1 to R 5 in the general formula (1) 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 can be taken by R 1 to R 5 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 can be taken by R 1 to R 5 is a carbazol-9-yl group which may be substituted with a group selected from the substituent group E, or may be condensed with one or more rings.
  • 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 or 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 benzene ring may be further fused with another benzene ring, or may be fused with a heterocycle such as a pyridine ring.
  • the aromatic heterocycle means a ring that exhibits aromaticity and contains 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 can be adopted.
  • a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the aromatic heterocycle.
  • 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.
  • 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.
  • the compounds D55 to D85 are those in which all hydrogen atoms present in the above D1 to D31 have been replaced with deuterium atoms.
  • the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D86 to D695, D704 to D1133, and D1142 to D1210. In one embodiment of the present invention, the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D696 to D703, and D1134 to D1141.
  • R 1 to R 5 in general formula (1) are donor groups.
  • two or three of R 1 to R 5 are donor groups.
  • two of R 1 to R 5 are donor groups.
  • three of R 1 to R 5 are donor groups.
  • at least R 3 is a donor group.
  • at least R 4 is a donor group.
  • at least R 5 is a donor group.
  • only R 3 is a donor group.
  • only R 4 is a donor group.
  • only R 5 is a donor group.
  • R 3 and R 5 are donor groups. In one embodiment of the present invention, only R 2 and R 5 are donor groups. In one embodiment of the present invention, only R 2 and R 4 are donor groups. In one embodiment of the invention, only R3 , R4 and R5 are donor groups. In one embodiment of the invention, only R2 , R4 and R5 are donor groups. When two or more of R1 to R5 are donor groups, they may be the same or different.
  • the number of hydrogen atoms or deuterium atoms among R 1 to R 5 is 0 to 2, preferably 0 or 1, for example 1, for example 0.
  • R 1 is a hydrogen atom or a deuterium atom.
  • the compound exhibits better luminescence properties than a compound in which the number of hydrogen atoms or deuterium atoms among R 1 to R 5 is 3.
  • the number of substituted or unsubstituted aryl groups among R 1 to R 5 is 0 or 1, preferably 1. It may be 0.
  • the number of substituted or unsubstituted alkyl groups among R 1 to R 5 is 0 to 3, preferably 0 to 2, and may be 1 or 0.
  • R 1 to R 5 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a donor group, and a group represented by general formula (2).
  • R 1 to R 5 are each independently selected from a hydrogen atom, a deuterium atom, a donor group, and a group represented by general formula (2). In one embodiment of the present invention, R 1 to R 5 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted carbazol-9-yl group which may be fused, and a group represented by general formula (2).
  • the heteroaryl group that can be Ar 1 and Ar 2 in the general formula (1) 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 pyridine ring, a pyrimidine ring, and a pyrrole ring, and these rings may be further fused with another ring.
  • heteroaryl group examples include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a carbazol-1-yl group, a carbazol-2-yl group, a carbazol-3-yl group, and a carbazol-4-yl group.
  • the number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected within the range of 5 to 16 or 5 to 12.
  • Ar 1 and Ar 2 are substituted or unsubstituted aryl groups.
  • X 1 to X 3 each independently represent N or C(R), with at least one of X 1 to X 3 being N.
  • R represents a hydrogen atom, a deuterium atom, or a substituent.
  • Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • L 1 represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • * represents a bonding position.
  • L 1 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 1 is a single bond.
  • L 1 is a substituted or unsubstituted arylene group.
  • L 1 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.
  • L1 Specific examples of L1 are given below. However, L1 that can be employed in the present invention should not be construed as being limited by these specific examples. Note that in the specific examples below, methyl groups are omitted. For example, L3 to L5 are substituted with methyl groups. * indicates the bond position. L1 is a single bond.
  • L1 is selected from the group consisting of L1 to L25. In one aspect of the present invention, L1 is selected from the group consisting of L1 to L7, and L14 to L19. In one aspect of the present invention, L1 is selected from the group consisting of L1, L8 to L13, and L20 to L25. In one aspect of the present invention, L1 is selected from the group consisting of L2 to L25.
  • X 1 to X 3 each independently represent N or C(R). However, at least one of X 1 to X 3 is N.
  • R represents 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.
  • X 1 to X 3 are N.
  • X 1 and X 3 are N
  • X 2 is C(R).
  • X 1 and X 2 are N
  • X 3 is C(R).
  • X 1 is N, and X 2 and X 3 are C(R). In one embodiment of the present invention, X 2 is N, and X 1 and X 3 are C (R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group optionally substituted with a deuterium atom. In one embodiment of the present invention, R is an aryl group optionally substituted with a deuterium atom, an alkyl group, or an aryl group.
  • Ar 1 and Ar 3 are the same.
  • Ar 1 and Ar 3 are the same, and Ar 2 and Ar 4 are the same.
  • Ar 1 to Ar 4 are the same.
  • X 1 to X 3 are N and L 1 is a single bond.
  • X 1 to X 3 are N and L 1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6).
  • X 1 to X 3 are N, L 1 is a single bond, and Ar 3 and Ar 4 are the same.
  • X 1 to X 3 are N, L 1 is a single bond, and Ar 3 and Ar 4 are each independently a substituted or unsubstituted aryl group.
  • X 1 to X 3 are N, L 1 is a single bond, and Ar 3 and Ar 4 are each independently a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably a donor heteroaryl group bonded via a nitrogen atom, and more preferably a substituted or unsubstituted carbazol-9-yl group.
  • X 1 to X 3 are N, L 1 is a single bond, Ar 3 is a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably a donor heteroaryl group bonded via a nitrogen atom, more preferably a substituted or unsubstituted carbazol-9-yl group, and Ar 4 is a substituted or unsubstituted aryl group.
  • only R2 is a group represented by formula (2).
  • only R3 is a group represented by formula (2).
  • one of R1 , R3 , R4 , and R5 and only R2 are each independently a group represented by formula (2).
  • one of R1 , R2 , R4 , and R5 and only R3 are each independently a group represented by formula (2).
  • R 1 to R 5 is a donor group having a fused ring structure with four or more rings
  • one or more of Ar 1 to Ar 4 is a substituted or unsubstituted heteroaryl group (excluding a nitrogen-containing 6-membered ring group)
  • R 1 to R 5 and Ar 1 to Ar 4 satisfy both of these conditions.
  • the "donor group having a condensed ring structure of four or more rings” as used herein refers to a donor group having a condensed ring structure of four or more rings and bonded via one of the atoms constituting the ring skeleton of the condensed ring structure.
  • the one atom is preferably a carbon atom or a nitrogen atom, and more preferably a nitrogen atom.
  • the donor group as used herein refers to a group having a negative Hammett ⁇ p value.
  • the donor group having a fused ring structure of 4 or more rings preferably has a fused ring structure of 5 or more rings, and more preferably has a fused ring structure of 5 to 7 rings, for example, a fused ring structure of 5 rings or a fused ring structure of 7 rings.
  • the donor group having a fused ring structure of 4 or more rings is preferably a ring-fused carbazol-9-yl group. Specific examples include D86 to D1210. In particular, a group having a structure represented by the following general formula (3) is preferred.
  • X represents O, S or N-R 14.
  • R 11 to R 13 each independently represent a deuterium atom or a substituent.
  • R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group.
  • R 11 's, R 12 's and R 13 's may be bonded to each other to form a cyclic structure.
  • n11 and n13 each independently represent an integer of 0 to 4, and n12 represents an integer of 0 to 2.
  • X represents O, S or N-R 14.
  • R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group.
  • the aryl group as a substituent of the aryl group and the alkyl group can be selected, for example, from an aryl group having 6 to 22 carbon atoms
  • the alkyl group as a substituent of the alkyl group and the aryl group can be selected, for example, from an alkyl group having 1 to 20 carbon atoms.
  • X is O.
  • X is N-R 14.
  • R 14 of N-R 14 is an aryl group (e.g., having 6 to 22 carbon atoms).
  • the aryl group may be substituted or unsubstituted with one or more atoms or 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).
  • X may be an oxygen atom or a sulfur atom.
  • the two bonds on one benzene ring of the carbazole ring are bonded to adjacent positions on the benzene ring to form a fused ring structure between the carbazole ring and a hetero fused ring containing X.
  • a benzofurocarbazole ring is formed as a fused ring structure
  • a benzothienocarbazole ring is formed as a fused ring structure
  • an indolocarbazole ring is formed as a fused ring structure.
  • the positions to which the two bonds are bonded may be the 1st and 2nd positions, the 2nd and 3rd positions, or the 3rd and 4th positions of the carbazole ring.
  • the position to which the bond of X is bonded may be the 1st or 2nd position
  • the position to which the bond of X is bonded may be the 2nd or 3rd position
  • the position to which the bond of X is bonded may be the 3rd or 4th position.
  • * represents a bonding position.
  • R 11 to R 13 each independently represent a deuterium atom or a substituent.
  • R 11 , R 12 , and R 13 may be bonded to each other to form a cyclic structure, but R 11 does not bond to any of R 12 to R 14 to form a cyclic structure, R 12 does not bond to any of R 13 and R 14 to form a cyclic structure, and R 13 does not bond to R 14 to form a cyclic structure.
  • the substituent 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 means one group selected from the group consisting of an alkyl group (e.g., 1 to 20 carbon atoms) and an aryl group (e.g., 6 to 22 carbon atoms) or a group consisting of a combination of two or more groups.
  • n11 and n13 each independently represent an integer of 0 to 4, and n12 represents an integer of 0 to 2.
  • n11 is 2 or more, two or more R 11 may be the same or different.
  • n13 is 2 or more, two or more R 13 may be the same or different.
  • two R 12 may be the same or different.
  • n11 and n13 may be any number of 0, 1, 2, 3, or 4, and n12 may be any number of 0, 1, or 2.
  • R 11 may be a deuterium atom or a substituent.
  • n11 is 2 or more, two or more R 11 may all be deuterium atoms or all be substituents, or a part of them may be deuterium atoms and the rest may be substituents.
  • n13 is 1, R 13 may be a deuterium atom or a substituent.
  • all of the two or more R 13 may be deuterium atoms or all of them may be substituents, or some of them may be deuterium atoms and the rest may be substituents.
  • R 12 may be a deuterium atom or a substituent.
  • both of the two R 12 may be deuterium atoms or both of them may be substituents, or one of the two may be a deuterium atom and the other may be a substituent.
  • the donor group has a fused ring structure of four or more rings
  • two or more of R 1 to R 5 are donor groups having a fused ring structure of four or more rings, for example, two, for example, three.
  • they may be the same or different, but are preferably the same.
  • at least R 3 is a donor group having a fused ring structure of four or more rings.
  • at least R 4 is a donor group having a fused ring structure of four or more rings.
  • At least R 5 is a donor group having a fused ring structure of four or more rings.
  • R 3 and R 5 are donor groups having a fused ring structure of four or more rings.
  • R 3 , R 4, and R 5 are donor groups having a fused ring structure of four or more rings.
  • one or more of Ar 1 to Ar 4 are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups).
  • the substituted or unsubstituted heteroaryl groups may be only one, two, three, or all of Ar 1 to Ar 4. When there are two or more, they may be the same or different, but are preferably the same.
  • the substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups) is preferably a heteroaryl group bonded at a nitrogen atom that is one of the ring skeleton constituent atoms, is preferably a heteroaryl group having a 5-membered ring bonded at a nitrogen atom (a group bonded at the nitrogen atom of a pyrrole ring, the pyrrole ring may be substituted, and is preferably a condensed ring), and is more preferably a substituted or unsubstituted carbazol-9-yl group.
  • the carbazol-9-yl group may be substituted with an alkyl group or an aryl group which may be substituted with a group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or may be substituted with a deuterium atom.
  • a group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group or may be substituted with a deuterium atom.
  • R 1 to R 5 may take, the descriptions of the ring-fused carbazol-9-yl groups, and specific examples D1 to D1210.
  • Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group.
  • Ar 1 to Ar 4 may all be the same, and may be, for example, an unsubstituted phenyl group or a perdeuterated phenyl group.
  • R 1 to R 5 are donor groups having a condensed ring structure of four or more rings.
  • the number of donor groups having a condensed ring structure of four or more rings may be two or more, for example, two, for example, three.
  • donor groups having a condensed ring structure of four or more rings specific examples D86 to D1210 can be referred to.
  • donor groups having a condensed ring structure of five or more rings for example, five rings, for example, seven rings
  • Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group
  • one or more of R 1 to R 5 have a deuterium atom.
  • it may have a donor group having a deuterated three-ring condensed ring structure (e.g., a perdeuterated carbazol-9-yl group), or it may have a deuterated aryl group (e.g., a perdeuterated phenyl group).
  • a donor group having a deuterated three-ring condensed ring structure e.g., a perdeuterated carbazol-9-yl group
  • a deuterated aryl group e.g., a perdeuterated phenyl 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 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).
  • the 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.
  • R 2 is a group represented by general formula (2)
  • Ar 1 and Ar 3 are perdeuterated carbazol-9-yl groups (D55)
  • Ar 2 and Ar 4 are perdeuterated phenyl groups (Ar47)
  • X 1 to X 3 are nitrogen atoms (N)
  • L 1 is a single bond (L1)
  • R 1 is a hydrogen atom
  • R 3 to R 5 are groups specified in Table 1 are shown individually as structures of compounds 1 to 170.
  • R 3 to R 5 of a plurality of compounds are displayed together in each row to show the structures of compounds 1 to 442987.
  • R 4 is fixed to D1 (carbazol-9-yl group), R 3 and R 5 are the same, and D1 to D85 are compounds 1 to 85, in that order.
  • D1 to D85 are compounds 1 to 85, in that order.
  • R 4 is fixed to D2 (3-methylcarbazol-9-yl group), R 3 and R 5 are the same, and D1 to D85 are compounds 86 to 170, in that order. That is, the row of compounds 1 to 85 and the row of compounds 86 to 170 in Table 2 are compounds 1 to 170 specified in Table 1 displayed together in two rows.
  • R 4 is fixed to D3 (3,6-dimethylcarbazol-9-yl group)
  • R 3 and R 5 are the same
  • D1 to D85 are identified in that order as compounds 171 to 255.
  • Compounds 256 to 442987 in Table 2 are also identified in the same manner.
  • compounds 1 to 636657 are displayed in the first row, and compounds 636658 to 1257639 are displayed in the second row.
  • compounds 1 to 636657 in which Ar 1 and Ar 3 are both D1 are sequentially designated as compounds 1(1) to 636657(1).
  • compound 1(1) indicates a compound having a structure in which Ar 1 and Ar 3 of compound 1 are replaced with D1.
  • compound 2(1) indicates a compound having a structure in which Ar 1 and Ar 3 of compound 2 are replaced with D1.
  • Compound 636657(1) shows a compound having a structure in which Ar 1 and Ar 3 of compound 636657 are replaced with D1.
  • compounds 1 to 636657 in which Ar 1 and Ar 3 are both D7 are designated as compounds 1(2) to 636657(2) in order.
  • compounds 1 to 636657 in which Ar 1 and Ar 3 , and Ar 2 and Ar 4 are those listed in Table 8 are specified in order.
  • X 1 to X 3 are all nitrogen atoms (N)
  • L 1 is a single bond (L1)
  • R 1 is a hydrogen atom.
  • Ar 1 and Ar 3 are the same, and Ar 2 and Ar 4 are the same.
  • Compounds 1 to 636657 (371) in Table 8 are compounds in which R 1 in general formula (1) is a hydrogen atom. Compounds having structures in which R 1 in these compounds is replaced with a deuterium atom are referred to as Compounds 1d to 636657 (371) d, respectively. Compounds having structures in which R 1 in these compounds is replaced with a perdeuterated phenyl group (Ar47) are referred to as Compounds 1D to 636657 (371) D, respectively.
  • the compounds identified by numbers in Tables 1 to 8, Compound 1d to Compound 636657(371)d, and Compound 1D to Compound 636657(371)D are all considered to be individually disclosed.
  • the compound is selected from the group of compounds identified in Table 8.
  • the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less.
  • the lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1).
  • the compound represented by 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 bonded 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.
  • the polymer containing the structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures.
  • the repeating units having the 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 the 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 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.
  • at least two 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 carbazole-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 organic light-emitting device of the present invention contains a compound represented by general formula (1) and a host material or a dopant material in the same layer.
  • the same layer is preferably an emission layer.
  • the compound represented by general formula (1) and a host material are contained in the same layer.
  • the host material is used at a higher concentration than the compound represented by general formula (1), and preferably has a higher minimum excited singlet energy than the compound represented by general formula (1).
  • the compound represented by general formula (1) and a dopant material are contained in the same layer.
  • the dopant material is used at a lower concentration than the compound represented by general formula (1), and preferably has a lower minimum excited singlet energy than the compound represented by general formula (1).
  • the compound represented by the general formula (1) is used for phosphorescence sensitized fluorescence.
  • the compound represented by formula (1) functions as a light-emitting material in an organic light-emitting device.
  • the compound represented by formula (1) functions as a light-emitting material that emits delayed fluorescence in an organic light-emitting device.
  • 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.
  • 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. In certain embodiments of the present disclosure, 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.
  • 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.
  • 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.
  • 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
  • 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 mixed powder in which the powders of the compounds are mixed may be used, 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 used as the temperature during co-deposition.
  • the organic light-emitting element is an organic photoluminescence element (organic PL element). In some embodiments, the organic light-emitting element is an organic electroluminescence element (organic EL element). In some embodiments, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In some embodiments, the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet energy level and is included between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-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.
  • the organic layer includes only a light-emitting layer.
  • 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.
  • the hole transport layer may be a hole injection transport layer having a hole injection function
  • 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.
  • the light-emitting layer includes a light-emitting material that is a dopant material and a host material.
  • the light-emitting material is a compound represented by general formula (1).
  • singlet excitons and triplet excitons generated in the light-emitting material are trapped in the light-emitting material.
  • 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.
  • the singlet and triplet excitons are sufficiently trapped to improve the light emission efficiency.
  • 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.
  • light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention.
  • the emitted light includes both fluorescence and delayed fluorescence.
  • the emitted light includes the emitted light from the host material.
  • the emitted light consists of the emitted light from the host material.
  • the emitted light includes the emitted light from the compound represented by formula (1) and the emitted light from the host material.
  • a TADF molecule and a host material are used.
  • 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.
  • a light-emitting material preferably a fluorescent material
  • various compounds can be adopted as a light-emitting material (preferably a fluorescent material) which is a dopant 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 dopant materials (light-emitting materials) that can be used in combination with the compound represented by formula (1) are given below.
  • a dopant material (light-emitting material) that can be used in combination with the compound represented by formula (1)
  • a compound represented by the following formula (4) can be particularly preferably used.
  • one of X1 and X2 is a nitrogen atom and the other is a boron atom.
  • X1 is a nitrogen atom and X2 is a boron atom.
  • R17 and R18 are bonded to each other to form a single bond to form a pyrrole ring.
  • X1 is a boron atom and X2 is a nitrogen atom.
  • R21 and R22 are bonded to each other to form a single bond to form a pyrrole ring.
  • R 1 to R 26 , A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • 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 together to form a ring structure.
  • the cyclic structure formed by bonding with R 7 and R 8 includes a boron atom and four carbon atoms as ring skeleton constituent atoms.
  • the cyclic structure formed by bonding with R 17 and R 18 includes a boron atom and four carbon atoms as ring skeleton constituent atoms when X 1 is a boron atom.
  • X 1 is a nitrogen atom
  • the cyclic structure is limited to a pyrrole ring.
  • the cyclic structure formed by bonding with R 21 and R 22 includes a boron atom and four carbon atoms as ring skeleton constituent atoms when X 2 is a boron atom.
  • the cyclic structure is limited to a pyrrole ring.
  • R 7 and R 8 , R 17 and R 18 , or R 21 and R 22 bond together to form a cyclic structure containing a boron atom
  • the cyclic structure is preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring, and even more preferably a 6-membered ring.
  • R 7 and R 8 , R 17 and R 18 , and R 21 and R 22 are bonded to each other, they are preferably bonded to each other to form a single bond, -O-, -S-, -N(R 27 )-, -C(R 28 )(R 29 )-, -Si(R 30 )(R 31 )-, -B(R 32 )-, -CO-, or -CS-, more preferably to form -O-, -S-, or -N(R 27 )-, and even more preferably to form -N(R 27 )-.
  • R 27 to R 32 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • substituent a group selected from any of the substituent groups A to E may be adopted, but it is preferable that it is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and it is particularly preferable that R 27 is a substituted or unsubstituted aryl group.
  • R 27 to R 32 are substituents, R 27 to R 32 in the ring formed by R 7 and R 8 may be bonded to at least one of R 6 and R 9 to further form a cyclic structure, R 27 to R 32 in the ring formed by R 17 and R 18 may be bonded to at least one of R 16 and R 19 to further form a cyclic structure, and R 27 to R 32 in the ring formed by R 21 and R 22 may be bonded to at least one of R 20 and R 23 to further form a cyclic structure. In one embodiment of the present invention, only one pair of R 7 and R 8 , R 17 and R 18 , and R 21 and R 22 are bonded to each other.
  • R 7 and R 8 , R 17 and R 18 , and R 21 and R 22 are bonded to each other. In one embodiment of the invention, R 7 and R 8 , R 17 and R 18 , and R 21 and R 22 are all bonded to each other.
  • the cyclic structure formed by bonding together may be an aromatic ring or an aliphatic ring, may contain a heteroatom, and may further be condensed with one or more other rings.
  • the heteroatom here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.
  • the cyclic structure formed include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoline ring, a furan ring, a thiophene ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cycloheptene
  • the cyclic structure is a substituted or unsubstituted benzene ring (which may further be condensed with a ring), for example, a benzene ring which may be substituted with an alkyl group or an aryl group.
  • the cyclic structure is a substituted or unsubstituted heteroaromatic ring, and is preferably a furan ring of benzofuran or a thiophene ring of benzothiophene.
  • the number of combinations that are bonded to each other to form a cyclic structure may be 0, or may be any of 1 to 6, for example.
  • R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 are bonded to each other to form a cyclic structure.
  • R 5 and R 6 are bonded to each other to form a cyclic structure.
  • a pair selected from R 9 and R 10 , R 10 and R 11 , and R 11 and R 12 are bonded to each other to form a cyclic structure.
  • R 1 and R 2 , R 13 and R 14 are all bonded to each other to form a cyclic structure.
  • a pair selected from R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 are bonded to each other to form a cyclic structure, and R 5 and R 6 are bonded to each other to form a cyclic structure.
  • R 5 and R 6 , and R 19 and R 20 are all bonded together to form a cyclic structure.
  • R 1 to R 26 that are not bonded to adjacent R n are a hydrogen atom, a deuterium atom, or a substituent.
  • a group selected from any one of the substituent groups A to E can be adopted.
  • Preferred substituents that R 1 to R 26 can take are substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups.
  • the substituent may be a substituted or unsubstituted aryl group, or the substituent may be a substituted or unsubstituted alkyl group.
  • the substituents of the alkyl group, aryl group, and heteroaryl group mentioned here can also be groups selected from any of the substituent groups A to E, but are preferably one or more groups selected from the group consisting of alkyl groups, aryl groups, and heteroaryl groups, and are more preferably groups of the substituent group E, and may be unsubstituted.
  • at least one of R 1 to R 6 is a substituent, preferably a group of the substituent group E.
  • at least one of R 2 to R 6 is a substituent, preferably a group of the substituent group E.
  • at least one of R 5 and R 6 is a substituent, preferably a group of the substituent group E.
  • At least one of R 3 and R 6 is a substituent, more preferably both are substituents, and are preferably groups of the substituent group E.
  • X 1 is a nitrogen atom
  • at least one of R 15 and R 20 is a substituent, more preferably both are substituents, and preferably a group of the substituent group E.
  • R 17 and R 18 are bonded to each other to form a single bond.
  • at least one of R 19 and R 24 is a substituent, more preferably both are substituents, and preferably a group of the substituent group E.
  • R 21 and R 22 are bonded to each other to form a single bond.
  • at least one of R 8 and R 12 is a substituent, and preferably both are substituents.
  • R 8 , R 10 and R 12 are substituents.
  • an unsubstituted alkyl group is preferable.
  • R 8 and R 12 are alkyl groups having 2 or more carbon atoms (preferably alkyl groups having 3 or more carbon atoms, more preferably alkyl groups having 3 to 8 carbon atoms, and even more preferably alkyl groups having 3 or 4 carbon atoms), the orientation is high when the film is made, which is preferable.
  • R 8 and R 12 are substituents (preferably alkyl groups, more preferably alkyl groups having 2 or more carbon atoms, even more preferably alkyl groups having 3 or more carbon atoms, even more preferably alkyl groups having 3 to 8 carbon atoms, and particularly preferably alkyl groups having 3 or 4 carbon atoms), and at least one of R 1 to R 6 is a substituent (preferably a group of the substituent group E).
  • R 1 to R 6 is a substituent (preferably a group of the substituent group E).
  • X 1 is a boron atom
  • at least one of R 13 and R 17 is a substituent, and preferably both are substituents.
  • R 13 , R 15 , and R 17 are substituents.
  • the substituents of R 13 to R 17 are preferably unsubstituted alkyl groups.
  • R 22 and R 26 are substituents.
  • R 22 , R 24 and R 26 are substituents.
  • the substituents of R 22 to R 26 are preferably unsubstituted alkyl groups.
  • the boron atom represented by B in the general formula (4) and the group bonded to the boron atom represented by X 1 or X 2 are listed below.
  • the group bonded to the boron atom that can be adopted in the present invention is not limited to the following specific examples.
  • the CH 3 is omitted for the methyl group. * indicates the bonding position.
  • R 1 to R 26 in general formula (4) are given below.
  • Y1 to Y9 are preferred for R 1 to R 7 , R 13 to R 21 when X 1 is a nitrogen atom, and R 18 to R 26 when X 2 is a nitrogen atom
  • Y1 to Y7 are preferred for R 8 to R 12 , R 22 to R 26 when X 1 is a nitrogen atom, and R 13 to R 17 when X 2 is a nitrogen atom.
  • D represents a deuterium atom. * represents a bonding position.
  • a 1 and A 2 are a hydrogen atom, a deuterium atom or a substituent.
  • substituent a group selected from any one of the substituent groups A to E can be adopted.
  • a 1 and A 2 are each independently a hydrogen atom or a deuterium atom.
  • a 1 and A 2 are hydrogen atoms.
  • a 1 and A 2 are deuterium atoms.
  • One of A1 and A2 may be a substituent.
  • A1 and A2 may each independently be a substituent.
  • a preferred substituent that A1 and A2 may have is an acceptor group.
  • the acceptor group is a group having a positive Hammett ⁇ p value.
  • the acceptor group that A 1 and A 2 can take is more preferably a group having a Hammett ⁇ p value of more than 0.2.
  • groups having a Hammett ⁇ p value of more than 0.2 include a cyano group, an aryl group substituted with at least a cyano group, a group containing a fluorine atom, and a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom.
  • the aryl group substituted with at least a cyano group may be substituted with a substituent other than a cyano group (e.g., an alkyl group or an aryl group), but may also be an aryl group substituted only with a cyano group.
  • the aryl group substituted with at least a cyano group is preferably a phenyl group substituted with at least a cyano group.
  • the number of cyano group substitutions is preferably 1 or 2, for example, it may be 1 or 2.
  • groups containing fluorine atoms include fluorine atoms, fluorinated alkyl groups, and aryl groups substituted with at least a fluorine atom or a fluorinated alkyl group.
  • the fluorinated alkyl group is preferably a perfluoroalkyl group, and the number of carbon atoms is preferably 1 to 6, more preferably 1 to 3.
  • the heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after condensation is preferably 2 to 6, and can be selected from 2 to 4, or can be 2.
  • the ring constituting the heteroaryl group examples include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a naphthyridine ring other than a quinazoline ring or a quinoxaline ring.
  • the ring constituting the heteroaryl group may be substituted with a deuterium atom or a substituent, and examples of the substituent include one group selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group, or a group formed by combining two or more groups.
  • a cyano group is particularly preferable as the acceptor group that A 1 and A 2 can take.
  • at least one of A 1 and A 2 is an acceptor group.
  • only one of A 1 and A 2 is an acceptor group.
  • both A 1 and A 2 are the same acceptor group.
  • a 1 and A 2 are different acceptor groups.
  • a 1 and A 2 are cyano groups.
  • a 1 and A 2 are halogen atoms, for example bromine atoms.
  • acceptor groups that can be used in the present invention are shown below. However, the acceptor groups that can be used in the present invention should not be construed as being limited to the following specific examples.
  • the CH3 symbol is omitted for methyl groups. Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups.
  • “D” represents a deuterium atom. * represents a bond position.
  • R 1 to R 6 is a substituted or unsubstituted aryl group, or any one 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 is bonded to each other to form an aromatic ring (a substituted or unsubstituted benzene ring which may be condensed) or a heteroaromatic ring (preferably a furan ring of a substituted or unsubstituted benzofuran which may be condensed, or a thiophene ring of a substituted or unsubstituted benzothiophene
  • X1 is a boron atom
  • X2 is a nitrogen atom
  • R7 and R8 , and R17 and R18 are bonded to each other to form a cyclic structure containing the boron atom
  • the cyclic structure is a 5- to 7-membered ring, and when it is a 6-membered ring, R7 and R8 , and R17 and R18 are bonded to each other to form -B( R32 )-, -CO-, -CS- or -N( R27 )-.
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • the light-emitting layer comprises two or more kinds of TADF molecules with different structures.
  • the light-emitting layer may comprise three kinds of materials, with the excited singlet energy level being higher in the order of the host material, the first TADF molecule, and the second TADF molecule.
  • the difference ⁇ E ST between the lowest excited singlet energy level and the lowest excited triplet energy level at 77K of both the first TADF molecule and the second TADF molecule is preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and especially preferably 0.01 eV or less.
  • the concentration of the first TADF molecule in the light-emitting layer is preferably greater than the concentration of
  • 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 amount of the compound represented by formula (1) is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound represented by formula (1) as the 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 represented by formula (1) as the 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 represented by formula (1) as the light-emitting material contained in the light-emitting layer is 20% by weight or less.
  • the amount of the compound represented by formula (1) as the 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 host material is selected from the group consisting of:
  • the host material used together with the compound represented by formula (1) is a compound having a structure represented by the following formula (5).
  • X11 represents O, S, N( RA ) or C( RB )( RC ). In one embodiment of the present invention, X11 is O, S or N( RA ). In one embodiment of the present invention, X11 is O or S. In one embodiment of the present invention, X11 is N( RA ). In one embodiment of the present invention, X11 is O. In one embodiment of the present invention, X11 is S. When X11 is O, S or C( RB )( RC ), L is bonded to the benzene ring to which ( R115 )n is bonded.
  • L is bonded to the benzene ring to which ( R115 )n is bonded or to N represented by X11 .
  • the bond extending to the right from L is meant to be bonded to the benzene ring to which (R 115 ) n is bonded, or to X 11 (i.e., N) when X 11 is N, as described herein.
  • a 11 and A 12 are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring, and these rings may be further condensed with other rings or may be substituted.
  • a 11 is a benzene ring.
  • a 12 is a benzene ring.
  • a 11 and A 12 are both benzene rings.
  • At least one of A 11 and A 12 is a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring. In one embodiment of the present invention, at least one of A 11 and A 12 is a furan ring. In one embodiment of the present invention, at least one of A 11 and A 12 is a thiol ring. In one embodiment of the present invention, at least one of A 11 and A 12 is a pyrrole ring. In one embodiment of the present invention, at least one of A 11 and A 12 is a cyclopentadiene ring.
  • the benzene ring, furan ring, thiol ring, pyrrole ring, and cyclopentadiene ring may further be condensed with another ring.
  • the condensed ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, and may be a ring in which two or more of these are condensed.
  • An aromatic hydrocarbon ring, an aromatic heterocycle, or a ring in which two or more of these are condensed is preferable.
  • An example of the aromatic hydrocarbon ring is a benzene ring.
  • the aromatic heterocycle means a ring exhibiting aromaticity that contains 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 can be adopted.
  • a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the aromatic heterocycle.
  • the aliphatic hydrocarbon ring is preferably a hydrocarbon ring that does not exhibit aromaticity, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted.
  • a cyclopentadiene ring can be adopted.
  • the aliphatic heterocycle means a ring that contains a heteroatom as a ring skeleton-constituting atom and does not exhibit aromaticity, and is preferably a 5- to 7-membered ring.
  • a 5-membered ring or a 6-membered ring can be adopted.
  • a 11 is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring fused with two or more of these.
  • a 11 is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, or a ring fused with two or more of these.
  • a 11 is a benzene ring, and the benzene ring is further fused with a furan ring of benzofuran or a thiophene ring of benzothiophene.
  • a 11 is fused with a furan ring of benzofuran.
  • a 11 is fused with a thiophene ring of benzothiophene.
  • a 12 is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring fused with two or more of these.
  • a 12 is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, or a ring fused with two or more of these.
  • a 12 is a benzene ring, and the benzene ring is fused with a furan ring of benzofuran or a thiophene ring of benzothiophene. In one embodiment of the present invention, A 12 is fused with a furan ring of benzofuran. In one embodiment of the present invention, A 12 is fused with a thiophene ring of benzothiophene.
  • the hydrogen atoms of the rings constituting A 11 and A 12 may be substituted with deuterium atoms or substituents. The substituents may be selected from any of the substituent groups A to E, for example, from the substituent group E.
  • the rings constituting A 11 and A 12 may be substituted with one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, and a cyano group.
  • the rings constituting A 11 and A 12 may be substituted with a deuterium atom, an alkyl group, an aryl group, or a combination of these.
  • At least one ring constituting A 11 and A 12 is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination of these.
  • a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group is preferably bonded to a nitrogen atom constituting the ring skeleton of the pyrrole ring (the same applies to the nitrogen atom of the indole ring described below).
  • two or more hydrogen atoms of the ring constituting A 11 or A 12 are substituted, they may be substituted with the same atom or group, or may be substituted with different atoms or groups.
  • R 111 to R 114 , R B , and R C each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group.
  • R 115 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond with L (i.e., a single bond to L).
  • R A represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L (i.e., a single bond to L).
  • aryl group, the heteroaryl group, and the alkyl group the above explanations of "aryl group”, “heteroaryl group”, and “alkyl group” can be referred to.
  • the number of carbon atoms of the aryl group is preferably 6 to 14, and examples thereof include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • the heteroaryl group is preferably a 5-membered or 6-membered ring, and examples of the heteroaryl group include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a dibenzofuryl group, and a dibenzothienyl group.
  • the alkyl group preferably has 1 to 6 carbon atoms, and examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.
  • aryl groups, heteroaryl groups, and alkyl groups may be substituted, and when substituted, are preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, and a cyano group, or a combination of two or more of these, and more preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group, or a combination of two or more of these.
  • R 112 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group.
  • R 111 to R 114 are each independently a hydrogen atom or a deuterium atom.
  • R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 , and R B and R C may be bonded to each other to form a cyclic structure.
  • a pair of R 111 and R 112 , R 112 and R 113 , or R 113 and R 114 are bonded to each other to form a benzofuran ring (fused with a furan ring), a benzothiophene ring (fused with a thiophene ring), or an indole ring (fused with a pyrrole ring).
  • the group bonded to L from the left in general formula (5) is a substituted or unsubstituted carbazol-9-yl group.
  • it is a carbazol-9-yl group in which at least one (preferably both) of the 3-position and the 6-position is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof.
  • it may be an unsubstituted carbazol-9-yl group.
  • the group bonded to L from the left in general formula (5) is a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group.
  • the group bonded to L from the left in general formula (5) is 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.
  • the group bonded to L from the left in general formula (5) is a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group.
  • the group bonded to L from the right in general formula (5) may also be any of the groups exemplified above as the group bonded to L from the left, provided that the group is not an unsubstituted carbazol-9-yl group.
  • groups in which all hydrogen atoms of the alkyl groups Z2, Z3, Z5, Z7 to Z12, Z87 to Z104, and Z179 to Z196 are substituted with deuterium atoms are exemplified here as Z2(m), Z3(m), Z5(m), Z7(m) to Z12(m), Z87(m) to Z104(m), and Z179(m) to Z196(m), respectively.
  • groups in which the phenyl groups (C 6 H 5 ) of Z4 to Z6, Z19 to Z86, and Z111 to Z178 are substituted with deuterated C 6 D 5 are exemplified here as Z4(p) to Z6(p), Z19(p) to Z86(p), and Z111(p) to Z178(p), respectively.
  • groups in which all hydrogen atoms in Z1 to Z196 are deuterated are exemplified herein as Z1(D) to Z196(D), respectively.
  • groups in which the methyl groups (CH 3 ) of X31 to X33 and X64 to X79 are replaced with deuterated CD 3 are exemplified here as X31(m) to X33(m) and X64(m) to X79(m), respectively.
  • Groups in which the phenyl groups (C 6 H 5 ) of X5 to X21, X38 to X54 and X68 to X70 are replaced with deuterated C 6 D 5 are exemplified here as X5(p) to X21(p), X38(p) to X54(p) and X68(p) to X70(p), respectively.
  • groups in which all hydrogen atoms of X1 to X79 are deuterated are exemplified here as X1(D) to X79(D), respectively.
  • n represents an integer of 3 or 4.
  • X11 is O, S or C( RB )( RC )
  • L is bonded to the benzene ring to which ( R115 )n is bonded, so n is 3.
  • X11 is N( RA ) and L is bonded to the benzene ring to which ( R115 )n is bonded, n is 3, and when X11 is N( RA ) and L is bonded to N represented by X11 , n is 4.
  • the n R115 may be the same or different from each other.
  • L in the general formula (5) represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group to which two or more of these are bonded.
  • aryl structure of the arylene group and the heteroaryl structure of the heteroarylene group the above explanations of "aryl group” and “heteroaryl group” can be referred to.
  • the arylene group and the heteroarylene group may be substituted, and if substituted, they are preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, and a cyano group, or a group combining two or more of these, and more preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group, or a group combining two or more of these. If substituted, they are preferably methyl, ethyl, isopropyl, tert-butyl, phenyl, or deuterated versions thereof.
  • L is an unsubstituted arylene group. 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.
  • the group bonded from the left of L in general formula (5) is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (Aspect 1).
  • the group bonded from the left of L is selected from Z1 to Z12 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (Aspect 2).
  • the group bonded from the left of L is selected from Z13 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (Aspect 3).
  • the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X66 and their deuterated forms (Aspect 4).
  • the group attached to the left of L is selected from Z1 to Z196 and their deuterated versions, and the group attached to the right of L is selected from X1 to X33 and their deuterated versions (Aspect 5).
  • the group attached to the left of L is selected from Z1 to Z196 and their deuterated versions
  • the group attached to the right of L is selected from X1 to X21, X31 to X33 and their deuterated versions
  • the group attached to the left of L is selected from Z1 to Z196 and their deuterated versions
  • the group attached to the right of L is selected from X22 to X30 and their deuterated versions (Aspect 7).
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1.
  • L is L1. In one aspect of the invention, in aspect 6, L is L1. In one aspect of the invention, in aspect 7, L is L1. In one aspect of the invention, in aspect 1, L is L6. In one aspect of the invention, in aspect 2, L is L6. In one aspect of the invention, in aspect 3, L is L6. In one aspect of the invention, in aspect 4, L is L6. In one aspect of the invention, in aspect 5, L is L6. In one aspect of the invention, in aspect 6, L is L6. In one aspect of the invention, in aspect 7, L is L6. In one aspect of the invention, in aspect 1, L is L14. In one aspect of the invention, in aspect 2, L is L14. In one aspect of the invention, in aspect 3, L is L14.
  • L is L14. In one aspect of the invention, in aspect 5, L is L14. In one aspect of the invention, in aspect 6, L is L14. In one aspect of the invention, in aspect 7, L is L14. In one aspect of the invention, in aspect 1, L is L16. In one aspect of the invention, in aspect 2, L is L16. In one aspect of the invention, in aspect 3, L is L16. In one aspect of the invention, in aspect 4, L is L16. In one aspect of the invention, in aspect 5, L is L16. In one aspect of the invention, in aspect 6, L is L16. In one aspect of the invention, in aspect 7, L is L16.
  • H1(d) to H13(d) compounds in which all hydrogen atoms in the substituted or unsubstituted carbazol-9-yl groups in H1 to H13 are replaced with deuterium atoms are exemplified here as H1(d) to H13(d), respectively.
  • Compounds in which all hydrogen atoms in H1 to H13 are replaced with deuterium atoms are exemplified here as H1(D) to H13(D), respectively.
  • the molecular weight of the compound represented by general formula (5) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 800 or less, and may be, for example, 600 or less, when it is intended to use an organic layer containing the compound represented by general formula (5) by forming the layer by a vapor deposition method.
  • the lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (5).
  • the compound represented by general formula (5) is preferably one having a smaller dipole moment, since this increases the orientation when the film is formed.
  • the dipole moment is preferably smaller than 2.3, more preferably smaller than 2.0, even more preferably smaller than 1.7, and even more preferably smaller than 1.4.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms can be selected.
  • the 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 photolithographic 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-injecting 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 driving voltage and enhances light radiance.
  • the injection layer comprises 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 may be present adjacent only to one of the anode side and the cathode side of the light-emitting layer, or one exciton blocking layer may be present adjacent to the anode side of the light-emitting layer and another exciton blocking layer may be present adjacent to the cathode side of the light-emitting layer.
  • the layer 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. In some embodiments, 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.
  • 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 the emissive layer on the cathode side.
  • the exciton blocking layer has 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 emissive material.
  • the hole transport layer comprises a hole transport material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one 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
  • 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 the planarizing film covering the interface grooves are spaced apart from each other.
  • the organic film and the 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 portion of the organic film, so the organic film and the 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.
  • the emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K. C4334 type).
  • Phenyl-d5-boronic acid (6.2 g, 48.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.4 g, 2.0 mmol), and potassium carbonate (29.0 g, 210 mmol) were added to a mixed solution of 1,5-dibromo-2,4-difluoro-3-iodobenzene (15.8 g, 39.9 mmol) in toluene (100 mL) and ion-exchanged water (30 mL), and the mixture was stirred at 100° C. for 23 hours under a nitrogen atmosphere.
  • reaction mixture of compound j (2.1 g, 5.98 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.30 mmol), potassium acetate (4.1 g, 42.0 mmol), bis(pinacolato)diboron (7.1 g, 27.9 mmol), and 1,4-dioxane (60 mL) was stirred at 110°C for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through silica. The filtrate was concentrated, and the resulting reaction mixture was dissolved in methylene chloride and filtered through silica.
  • Carbazole-1,2,3,4,5,6,7,8-d8 (1.28 g, 7.30 mmol) and potassium carbonate (1.37 g, 9.91 mmol) were added to a mixture of compound n (2.85 g, 3.30 mmol) and DMF (65 mL), and the mixture was stirred at 150° C. for 3 hours.
  • the reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate.
  • the filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol.
  • reaction mixture of compound q (4.8 g, 9.40 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.36 g, 0.50 mmol), potassium acetate (6.5 g, 66.2 mmol), bis(pinacolato)diboron (12.1 g, 47.6 mmol), and 1,4-dioxane (100 mL) was stirred at 110°C for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through silica. The filtrate was concentrated, and the resulting reaction mixture was dissolved in methylene chloride and filtered through silica.
  • Carbazole-1,2,3,4,5,6,7,8-d8 (1.16 g, 6.61 mmol) and potassium carbonate (1.24 g, 8.97 mmol) were added to a mixture of compound s (3.06 g, 3.00 mmol) and DMF (60 mL), and the mixture was stirred at 150° C. for 3 hours.
  • the reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate.
  • the filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol.
  • Example 1 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. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 30 nm, TrisPCz was further formed thereon to a thickness of 10 nm, and H1 was formed thereon to a thickness of 5 nm.
  • ITO indium tin oxide
  • H1, compound C1, and dopant EM1 were co-deposited from different deposition sources to form a layer with a thickness of 40 nm to serve as an emission layer.
  • the concentration of H1 in the emission layer was 44.2% by mass
  • the concentration of compound C1 was 55.0% by mass
  • the concentration of EM1 was 0.8% by mass.
  • SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation 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 further formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, thereby forming an organic electroluminescence element.
  • Al aluminum
  • the voltage measured when driven at 6.3 mA/ cm2 was 3.82 V.
  • the external quantum efficiency (EQE) measured when driven at 6.3 mA/ cm2 showed a high value of 24.7%.
  • Example 2 Preparation and evaluation of organic electroluminescence element
  • H2, compound C1, and dopant EM1 were co-evaporated from different deposition sources to form a 40 nm-thick light-emitting layer with a H2 concentration of 64.2 mass%, a compound C1 concentration of 35.0 mass%, and an EM1 concentration of 0.8 mass%.
  • an organic electroluminescence element was prepared according to the same procedure as in Example 1.
  • H2, compound C3, and dopant EM1 were co-evaporated from different deposition sources to form a 40 nm thick light-emitting layer with a concentration of H2 of 74.2 mass%, a concentration of compound C3 of 25.0 mass%, and a concentration of EM1 of 0.8 mass%.
  • the organic electroluminescence element was otherwise produced according to the same procedure as in Example 1.
  • organic electroluminescence elements were produced in the same manner using compounds C4, C5, C12, C14, and comparative compound A instead of compound C3.
  • Each of these devices was driven at 25.2 mA/ cm2 , and the time (LT95) from the start of driving until the luminous intensity reached 95% was measured.
  • the measurement results are shown in Table 9 as relative values when the LT95 of the organic electroluminescence device using comparative compound A is set to 1.
  • the results in Table 9 show that the organic light-emitting device using the compound represented by general formula (1) has a long life and is excellent.

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Citations (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013011955A1 (ja) 2011-07-15 2013-01-24 国立大学法人九州大学 遅延蛍光材料およびそれを用いた有機エレクトロルミネッセンス素子
WO2013011954A1 (ja) 2011-07-15 2013-01-24 国立大学法人九州大学 有機エレクトロルミネッセンス素子およびそれに用いる化合物
WO2013081088A1 (ja) 2011-12-02 2013-06-06 国立大学法人九州大学 有機発光素子ならびにそれに用いる遅延蛍光材料および化合物
JP2013116975A (ja) 2011-12-02 2013-06-13 Kyushu Univ 遅延蛍光材料、有機発光素子および化合物
WO2013133359A1 (ja) 2012-03-09 2013-09-12 国立大学法人九州大学 発光材料および有機発光素子
WO2013154064A1 (ja) 2012-04-09 2013-10-17 国立大学法人九州大学 有機発光素子ならびにそれに用いる発光材料および化合物
WO2013161437A1 (ja) 2012-04-25 2013-10-31 国立大学法人九州大学 発光材料および有機発光素子
JP2013253121A (ja) 2011-07-15 2013-12-19 Kyushu Univ 遅延蛍光材料、それを用いた有機エレクトロルミネッセンス素子および化合物
JP2013256490A (ja) 2012-05-17 2013-12-26 Kyushu Univ 化合物、発光材料および有機発光素子
JP2014009352A (ja) 2012-07-03 2014-01-20 Kyushu Univ 発光材料、化合物および有機発光素子
JP2014009224A (ja) 2012-07-03 2014-01-20 Kyushu Univ 発光材料、化合物および有機発光素子
WO2014034535A1 (ja) 2012-08-30 2014-03-06 国立大学法人九州大学 発光材料、化合物、およびそれらを用いた有機発光素子
WO2014115743A1 (ja) 2013-01-23 2014-07-31 国立大学法人九州大学 発光材料およびそれを用いた有機発光素子
WO2014122895A1 (ja) 2013-02-07 2014-08-14 保土谷化学工業株式会社 ジアザトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子
WO2014126200A1 (ja) 2013-02-18 2014-08-21 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014133121A1 (ja) 2013-03-01 2014-09-04 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014136758A1 (ja) 2013-03-05 2014-09-12 国立大学法人九州大学 電荷輸送材料、ホスト材料、薄膜および有機発光素子
WO2014136860A1 (ja) 2013-03-08 2014-09-12 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014168101A1 (ja) 2013-04-10 2014-10-16 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2014189122A1 (ja) 2013-05-24 2014-11-27 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014196585A1 (ja) 2013-06-05 2014-12-11 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2014203840A1 (ja) 2013-06-21 2014-12-24 国立大学法人九州大学 赤色発光材料、有機発光素子および化合物
WO2015002213A1 (ja) 2013-07-03 2015-01-08 国立大学法人九州大学 発光材料、遅延蛍光体、有機発光素子および化合物
WO2015008580A1 (ja) 2013-07-16 2015-01-22 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2015016200A1 (ja) 2013-08-01 2015-02-05 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2015019725A1 (ja) 2013-08-09 2015-02-12 国立大学法人九州大学 有機金属錯体、発光材料、遅延蛍光体および有機発光素子
WO2015022974A1 (ja) 2013-08-14 2015-02-19 国立大学法人九州大学 有機エレクトロルミネッセンス素子
WO2015072470A1 (ja) 2013-11-12 2015-05-21 国立大学法人九州大学 発光材料、並びに、これを用いた遅延蛍光体および有機発光素子
WO2015072537A1 (ja) 2013-11-18 2015-05-21 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015080182A1 (ja) 2013-11-28 2015-06-04 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015080183A1 (ja) 2013-11-28 2015-06-04 国立大学法人九州大学 発光材料、有機発光素子および化合物
JP2015129240A (ja) 2014-01-08 2015-07-16 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015108049A1 (ja) 2014-01-17 2015-07-23 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015129714A1 (ja) 2014-02-28 2015-09-03 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015129715A1 (ja) 2014-02-28 2015-09-03 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015133501A1 (ja) 2014-03-07 2015-09-11 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015137244A1 (ja) 2014-03-11 2015-09-17 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015137136A1 (ja) 2014-03-12 2015-09-17 国立大学法人九州大学 発光材料及びそれを用いた有機ｅｌ素子
WO2015136880A1 (ja) 2014-03-11 2015-09-17 保土谷化学工業株式会社 アザフルオレン環構造を有するスピロ化合物、発光材料および有機エレクトロルミネッセンス素子
WO2015137202A1 (ja) 2014-03-11 2015-09-17 国立大学法人九州大学 有機発光素子、ホスト材料、発光材料および化合物
WO2015146541A1 (ja) 2014-03-27 2015-10-01 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015159541A1 (ja) 2014-04-18 2015-10-22 保土谷化学工業株式会社 テトラアザトリフェニレン環構造を有する化合物、発光材料および有機エレクトロルミネッセンス素子
CN105481845A (zh) * 2015-12-25 2016-04-13 上海天马有机发光显示技术有限公司 有机电致发光化合物及其有机光电装置
JP2017119663A (ja) 2015-12-28 2017-07-06 株式会社Ｋｙｕｌｕｘ 化合物、発光材料および有機発光素子
JP2017119664A (ja) 2015-12-28 2017-07-06 株式会社Ｋｙｕｌｕｘ 化合物、発光材料および有機発光素子
JP2017222623A (ja) 2016-06-17 2017-12-21 株式会社Ｋｙｕｌｕｘ 化合物および有機発光素子
JP2017226838A (ja) 2016-06-17 2017-12-28 株式会社Ｋｙｕｌｕｘ 発光材料、有機発光素子および化合物
WO2018047853A1 (ja) 2016-09-06 2018-03-15 株式会社Ｋｙｕｌｕｘ 有機発光素子
KR20180047306A (ko) * 2016-10-31 2018-05-10 성균관대학교산학협력단 지연형광 재료 및 이를 포함하는 유기 발광장치
JP2018100411A (ja) 2016-12-21 2018-06-28 国立大学法人九州大学 発光材料、化合物および有機発光素子
WO2018237385A1 (en) * 2017-06-23 2018-12-27 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
WO2019191665A1 (en) 2018-03-30 2019-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
WO2020189117A1 (ja) * 2019-03-18 2020-09-24 コニカミノルタ株式会社 π共役系化合物、π共役系化合物の製造方法、インク組成物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜及び有機エレクトロルミネッセンス素子
WO2021040467A1 (ko) * 2019-08-28 2021-03-04 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
JP2022500481A (ja) * 2018-11-27 2022-01-04 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
JP2022501333A (ja) * 2018-11-27 2022-01-06 エルジー・ケム・リミテッド 新規な化合物およびこれを含む有機発光素子
WO2022168956A1 (ja) 2021-02-04 2022-08-11 株式会社Kyulux 化合物、発光材料および有機発光素子
WO2022270354A1 (ja) 2021-06-23 2022-12-29 株式会社Kyulux 化合物、発光材料および有機発光素子
CN115894457A (zh) * 2021-08-16 2023-04-04 北京鼎材科技有限公司 一种有机化合物及其应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102532378B1 (ko) * 2017-06-23 2023-05-15 가부시키가이샤 큐럭스 유기 발광 다이오드에 이용되는 조성물
KR102102042B1 (ko) * 2017-08-14 2020-04-17 주식회사 엘지화학 함질소 고리 화합물 및 이를 포함하는 유기 발광 소자
CN107935915A (zh) * 2017-12-13 2018-04-20 长春海谱润斯科技有限公司 一种二苯并咔唑类化合物及其有机发光器件
US11498914B2 (en) * 2018-03-30 2022-11-15 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
CN112409240A (zh) * 2020-11-20 2021-02-26 清华大学 一种有机化合物及其应用及采用该化合物的有机电致发光器

Patent Citations (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013011955A1 (ja) 2011-07-15 2013-01-24 国立大学法人九州大学 遅延蛍光材料およびそれを用いた有機エレクトロルミネッセンス素子
WO2013011954A1 (ja) 2011-07-15 2013-01-24 国立大学法人九州大学 有機エレクトロルミネッセンス素子およびそれに用いる化合物
JP2013253121A (ja) 2011-07-15 2013-12-19 Kyushu Univ 遅延蛍光材料、それを用いた有機エレクトロルミネッセンス素子および化合物
WO2013081088A1 (ja) 2011-12-02 2013-06-06 国立大学法人九州大学 有機発光素子ならびにそれに用いる遅延蛍光材料および化合物
JP2013116975A (ja) 2011-12-02 2013-06-13 Kyushu Univ 遅延蛍光材料、有機発光素子および化合物
WO2013133359A1 (ja) 2012-03-09 2013-09-12 国立大学法人九州大学 発光材料および有機発光素子
WO2013154064A1 (ja) 2012-04-09 2013-10-17 国立大学法人九州大学 有機発光素子ならびにそれに用いる発光材料および化合物
WO2013161437A1 (ja) 2012-04-25 2013-10-31 国立大学法人九州大学 発光材料および有機発光素子
JP2013256490A (ja) 2012-05-17 2013-12-26 Kyushu Univ 化合物、発光材料および有機発光素子
JP2014009352A (ja) 2012-07-03 2014-01-20 Kyushu Univ 発光材料、化合物および有機発光素子
JP2014009224A (ja) 2012-07-03 2014-01-20 Kyushu Univ 発光材料、化合物および有機発光素子
WO2014034535A1 (ja) 2012-08-30 2014-03-06 国立大学法人九州大学 発光材料、化合物、およびそれらを用いた有機発光素子
WO2014115743A1 (ja) 2013-01-23 2014-07-31 国立大学法人九州大学 発光材料およびそれを用いた有機発光素子
WO2014122895A1 (ja) 2013-02-07 2014-08-14 保土谷化学工業株式会社 ジアザトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子
WO2014126200A1 (ja) 2013-02-18 2014-08-21 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014133121A1 (ja) 2013-03-01 2014-09-04 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014136758A1 (ja) 2013-03-05 2014-09-12 国立大学法人九州大学 電荷輸送材料、ホスト材料、薄膜および有機発光素子
WO2014136860A1 (ja) 2013-03-08 2014-09-12 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014168101A1 (ja) 2013-04-10 2014-10-16 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2014189122A1 (ja) 2013-05-24 2014-11-27 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2014196585A1 (ja) 2013-06-05 2014-12-11 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2014203840A1 (ja) 2013-06-21 2014-12-24 国立大学法人九州大学 赤色発光材料、有機発光素子および化合物
WO2015002213A1 (ja) 2013-07-03 2015-01-08 国立大学法人九州大学 発光材料、遅延蛍光体、有機発光素子および化合物
WO2015008580A1 (ja) 2013-07-16 2015-01-22 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2015016200A1 (ja) 2013-08-01 2015-02-05 国立大学法人九州大学 化合物、発光材料および有機発光素子
WO2015019725A1 (ja) 2013-08-09 2015-02-12 国立大学法人九州大学 有機金属錯体、発光材料、遅延蛍光体および有機発光素子
WO2015022974A1 (ja) 2013-08-14 2015-02-19 国立大学法人九州大学 有機エレクトロルミネッセンス素子
WO2015072470A1 (ja) 2013-11-12 2015-05-21 国立大学法人九州大学 発光材料、並びに、これを用いた遅延蛍光体および有機発光素子
WO2015072537A1 (ja) 2013-11-18 2015-05-21 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015080182A1 (ja) 2013-11-28 2015-06-04 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015080183A1 (ja) 2013-11-28 2015-06-04 国立大学法人九州大学 発光材料、有機発光素子および化合物
JP2015129240A (ja) 2014-01-08 2015-07-16 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015108049A1 (ja) 2014-01-17 2015-07-23 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015129714A1 (ja) 2014-02-28 2015-09-03 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015129715A1 (ja) 2014-02-28 2015-09-03 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015133501A1 (ja) 2014-03-07 2015-09-11 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015137244A1 (ja) 2014-03-11 2015-09-17 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015136880A1 (ja) 2014-03-11 2015-09-17 保土谷化学工業株式会社 アザフルオレン環構造を有するスピロ化合物、発光材料および有機エレクトロルミネッセンス素子
WO2015137202A1 (ja) 2014-03-11 2015-09-17 国立大学法人九州大学 有機発光素子、ホスト材料、発光材料および化合物
WO2015137136A1 (ja) 2014-03-12 2015-09-17 国立大学法人九州大学 発光材料及びそれを用いた有機ｅｌ素子
WO2015146541A1 (ja) 2014-03-27 2015-10-01 国立大学法人九州大学 発光材料、有機発光素子および化合物
WO2015159541A1 (ja) 2014-04-18 2015-10-22 保土谷化学工業株式会社 テトラアザトリフェニレン環構造を有する化合物、発光材料および有機エレクトロルミネッセンス素子
CN105481845A (zh) * 2015-12-25 2016-04-13 上海天马有机发光显示技术有限公司 有机电致发光化合物及其有机光电装置
JP2017119663A (ja) 2015-12-28 2017-07-06 株式会社Ｋｙｕｌｕｘ 化合物、発光材料および有機発光素子
JP2017119664A (ja) 2015-12-28 2017-07-06 株式会社Ｋｙｕｌｕｘ 化合物、発光材料および有機発光素子
JP2017222623A (ja) 2016-06-17 2017-12-21 株式会社Ｋｙｕｌｕｘ 化合物および有機発光素子
JP2017226838A (ja) 2016-06-17 2017-12-28 株式会社Ｋｙｕｌｕｘ 発光材料、有機発光素子および化合物
WO2018047853A1 (ja) 2016-09-06 2018-03-15 株式会社Ｋｙｕｌｕｘ 有機発光素子
KR20180047306A (ko) * 2016-10-31 2018-05-10 성균관대학교산학협력단 지연형광 재료 및 이를 포함하는 유기 발광장치
JP2018100411A (ja) 2016-12-21 2018-06-28 国立大学法人九州大学 発光材料、化合物および有機発光素子
WO2018237385A1 (en) * 2017-06-23 2018-12-27 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
WO2019191665A1 (en) 2018-03-30 2019-10-03 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
JP2022500481A (ja) * 2018-11-27 2022-01-04 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
JP2022501333A (ja) * 2018-11-27 2022-01-06 エルジー・ケム・リミテッド 新規な化合物およびこれを含む有機発光素子
WO2020189117A1 (ja) * 2019-03-18 2020-09-24 コニカミノルタ株式会社 π共役系化合物、π共役系化合物の製造方法、インク組成物、有機エレクトロルミネッセンス素子材料、発光材料、電荷輸送材料、発光性薄膜及び有機エレクトロルミネッセンス素子
WO2021040467A1 (ko) * 2019-08-28 2021-03-04 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
WO2022168956A1 (ja) 2021-02-04 2022-08-11 株式会社Kyulux 化合物、発光材料および有機発光素子
WO2022270354A1 (ja) 2021-06-23 2022-12-29 株式会社Kyulux 化合物、発光材料および有機発光素子
CN115894457A (zh) * 2021-08-16 2023-04-04 北京鼎材科技有限公司 一种有机化合物及其应用

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HANSCH, C., CHEM. REV., vol. 91, 1991, pages 165 - 195
See also references of EP4694635A1

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2023032402A (ja) * 2021-08-27 2023-03-09 株式会社Kyulux 化合物、発光材料および有機発光素子
JP7792679B2 (ja) 2021-08-27 2025-12-26 株式会社Kyulux 化合物、発光材料および有機発光素子

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