WO2024257751A1 - 有機発光素子 - Google Patents

有機発光素子 Download PDF

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Publication number
WO2024257751A1
WO2024257751A1 PCT/JP2024/021148 JP2024021148W WO2024257751A1 WO 2024257751 A1 WO2024257751 A1 WO 2024257751A1 JP 2024021148 W JP2024021148 W JP 2024021148W WO 2024257751 A1 WO2024257751 A1 WO 2024257751A1
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substituted
general formula
atom
unsubstituted
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French (fr)
Japanese (ja)
Inventor
善丈 鈴木
桃子 森尾
伊織 鈴木
ヨンジュ ジョ
幸誠 金原
ソンヘ ファン
祐子 下位
寛晃 小澤
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Kyulux Inc
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Kyulux Inc
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Priority to DE112024002499.8T priority Critical patent/DE112024002499T5/de
Priority to CN202480039152.4A priority patent/CN121312300A/zh
Priority to KR1020257041987A priority patent/KR20260022322A/ko
Publication of WO2024257751A1 publication Critical patent/WO2024257751A1/ja
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K2101/20—Delayed fluorescence emission

Definitions

  • the present invention relates to an organic light-emitting device that uses a compound having a skeleton in which multiple heteroaromatic rings containing nitrogen atoms are bonded to a benzene ring.
  • luminescent materials such as organic electroluminescent elements (organic EL elements)
  • organic EL elements organic electroluminescent elements
  • Fluorescent materials, phosphorescent materials, and fluorescent materials have long been known as luminescent 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.
  • delayed fluorescent materials have been developed as luminescent 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 the excited singlet state and the 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 present inventors have found that the light-emitting properties of an organic light-emitting device can be improved by using a compound having a structure that satisfies a specific condition in combination with a compound that satisfies another condition.
  • 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 light-emitting material having a boron atom (excluding boron complexes):
  • 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 non-fused carbazol-9-yl group which may be substituted with one or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl 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 at least one of R 1 to R 5 is the non-fused carbazol-9-yl group. At least one of X 1 to X 3 is N, and the remainder represents C(R 6 ). R 6 represents a hydrogen atom, a deuterium atom, or a substituent. Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group. In general formula (2), at least one of X4 to X6 is N, and the rest are C( R7 ). R7 represents a hydrogen atom, a deuterium atom, or a substituent. Ar3 and Ar4 each independently represent a substituted or unsubstituted aryl group.
  • L1 represents a single bond or a divalent linking group. * represents a bonding position.
  • [2] The organic light-emitting element according to [1], wherein R 2 is a group represented by the general formula (2).
  • [3] The organic light-emitting element according to [1], wherein R 3 is a group represented by the general formula (2).
  • [4] The organic light-emitting element according to any one of [1] to [3], wherein two or more of R 1 to R 5 are the non-condensed carbazol-9-yl group.
  • [5] The organic light-emitting element according to any one of [1] to [3], wherein three of R 1 to R 5 are the non-condensed carbazol-9-yl 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, provided that when X 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring, and when X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other to form a single bond to form
  • the organic light-emitting element of the present invention has 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 non-fused carbazol-9-yl group which may be substituted with one or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group represented by the general formula (2) described below.
  • R 2 or R 3 is a group represented by the general formula (2), and at least one of R 1 to R 5 is the non-fused carbazol-9-yl group.
  • At least one of X 1 to X 3 is N, and the remaining represents C(R 6 ).
  • R 6 represents a hydrogen atom, a deuterium atom, or a substituent.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group.
  • the alkyl group that can be R 1 to R 5 may be linear, branched, or cyclic. In addition, two or more of the linear portion, the cyclic portion, and the branched portion may be mixed.
  • the number of carbon atoms of the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. In addition, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • the alkyl group as a substituent may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom.
  • the substituent of the alkyl group is one or more selected from the group consisting of an aryl group and a deuterium atom.
  • the alkyl group is unsubstituted and may be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.
  • 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 Ar25 are substituted with deuterium atoms are exemplified here as Ar45 to Ar69, in that order.
  • the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar1 to Ar69.
  • the aryl group which R 1 to R 5 can take is Ar1 or Ar45.
  • the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, and Ar46 to 55.
  • the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, and Ar56 to Ar63. 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 Ar21 to Ar25, and Ar65 to Ar69. 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 Ar14, Ar23, Ar36 to Ar38, Ar45, Ar56 to Ar58, and Ar67. 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 Ar1 to Ar69.
  • the aryl group that Ar 1 or Ar 2 can take is Ar1 or Ar45. 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 Ar2 to Ar11, Ar26 to Ar35, and Ar46 to 55. 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 Ar12 to Ar19, Ar36 to Ar43, and Ar56 to Ar63. 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 Ar1, Ar12 to Ar14, Ar36 to Ar38, Ar45, and Ar56 to Ar58.
  • R 1 to R 5 in the general formula (1) may be a non-fused carbazol-9-yl group which may be substituted with a group consisting of one or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.
  • the non-fused carbazol-9-yl group here means a group in which another ring is not fused to the carbazole of a three-ring structure.
  • the non-fused carbazol-9-yl group which R 1 to R 5 can take may be unsubstituted or may be substituted with a group consisting of one or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.
  • all of the 10 hydrogen atoms present in the non-fused carbazol-9-yl group may be substituted, or only a part of them may be substituted.
  • Examples of the embodiment in which only a part of the 10 hydrogen atoms is substituted include an embodiment in which 1 to 5 are substituted, an embodiment in which 3 are substituted, an embodiment in which 2 are substituted, and an embodiment in which 1 is substituted.
  • examples of the substitution include an embodiment in which only the 3-position is substituted, an embodiment in which the 3-position and the 6-position are substituted, an embodiment in which the 1-position and the 8-position are substituted, and an embodiment in which the 2-position and the 7-position are substituted.
  • the non-fused carbazol-9-yl group may be substituted only with deuterium atoms, may be substituted only with unsubstituted alkyl groups, may be substituted only with partially or fully deuterated alkyl groups, may be substituted only with unsubstituted aryl groups, or may be substituted only with partially or fully deuterated aryl groups.
  • the non-fused carbazol-9-yl group may be substituted only with alkylaryl groups which may be partially or fully deuterated, or may be substituted only with arylalkyl groups which may be partially or fully deuterated.
  • the non-fused carbazol-9-yl group which can be represented by R 1 to R 5 is a carbazol-9-yl group in which at least one hydrogen atom is deuterated, and more preferably a carbazol-9-yl group in which all hydrogen atoms are deuterated.
  • at least one of the 3- and 6-positions is a carbazol-9-yl group which is an aryl group which may be substituted with one or two groups selected from the group consisting of a deuterium atom and an alkyl group.
  • at least one of the 3- and 6-positions is a carbazol-9-yl group which is an alkyl group which may be substituted with a deuterium atom.
  • non-fused carbazol-9-yl groups which may be represented by R 1 to R 5 in general formula (1) are shown below.
  • the non-fused carbazol-9-yl groups which may be employed in the present invention should not be construed as being limited by the following specific examples.
  • Ph represents a phenyl group (C 6 H 5 )
  • * represents a bonding position.
  • Methyl groups are not shown, so for example, D2 has one methyl group.
  • a deuterated methyl group is represented as CD 3.
  • C 6 D 5 represents a phenyl group in which all hydrogen atoms are deuterated.
  • D represents a deuterium atom.
  • D1 to D25 are disclosed as D26 to D50 in which all hydrogen atoms present therein have been replaced with deuterium atoms.
  • the non-fused carbazol-9-yl group which R 1 to R 5 may take is selected from the group consisting of D1 to D50. In one embodiment of the present invention, the non-fused carbazol-9-yl group which R 1 to R 5 may take is selected from the group consisting of D14 to D50. In one embodiment of the present invention, the non-fused carbazol-9-yl group which R 1 to R 5 may take is selected from the group consisting of D1 to D7, D14 to D19, D26 to 32, and D39 to D44. In one embodiment of the present invention, the non-fused carbazol-9-yl group which R 1 to R 5 may take is selected from the group consisting of D8 to D13, D20 to D25, D33 to D38, and D45 to D50.
  • At least one of R 1 to R 5 in general formula (1) is a non-fused carbazol-9-yl group which may be substituted with a group consisting of one or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.
  • R 1 is not the non-fused carbazol-9-yl group.
  • R 2 to R 5 are the non-fused carbazol-9-yl group.
  • at least R 2 or R 3 is the non-fused carbazol-9-yl group.
  • at least R 4 is the non-fused carbazol-9-yl group.
  • at least R 5 is the non-fused carbazol-9-yl group.
  • only R 5 is the non-fused carbazol-9-yl group.
  • only R 3 and R 5 are the non-fused carbazol-9-yl group.
  • R 2 and R 5 are the non-fused carbazol-9-yl group. In one embodiment of the present invention, only R 2 and R 4 are the non-fused carbazol-9-yl group. In one embodiment of the present invention, only R 3 , R 4 and R 5 are the non-fused carbazol-9-yl group. In one embodiment of the present invention, only R 2 , R 4 and R 5 are the non-fused carbazol-9-yl group. When two or more of R 1 to R 5 are the non-fused carbazol-9-yl group, 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, the non-fused carbazol-9-yl 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, the non-fused carbazol-9-yl 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 carbazol-9-yl group which may be substituted with a deuterium atom, and a group represented by general formula (2).
  • one to three of X 1 to X 3 are N, and the remaining are C(R 6 ).
  • R 6 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 2 are N
  • X 3 is C(R 6 ).
  • X 1 and X 3 are N, and X 2 is C(R 6 ).
  • X 1 is N, and X 2 and X 3 are C(R 6 ). In an embodiment of the present invention, X 3 is N, and X 1 and X 2 are C(R 6 ).
  • R6 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R6 is an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, R6 is a deuterium atom, an alkyl group or an aryl group which may be substituted with an aryl group.
  • X 1 to X 3 are N, and Ar 1 and Ar 2 are the same. In one embodiment of the present invention, X 1 to X 3 are N, and Ar 1 and Ar 2 are each independently an at least partially deuterated aryl group. In one embodiment of the present invention, X1 and X2 are N, X3 is C( R6 ), R6 is a hydrogen atom or a deuterium atom, and Ar1 and Ar2 are the same. In one embodiment of the present invention, X1 and X2 are N, X3 is C( R6 ), R6 is a hydrogen atom or a deuterium atom, and Ar1 and Ar2 are each independently an at least partially deuterated aryl group.
  • X1 and X3 are N, X2 is C( R6 ), R6 is a hydrogen atom or a deuterium atom, and Ar1 and Ar2 are the same.
  • X1 and X3 are N, X2 is C( R6 ), R6 is a hydrogen atom or a deuterium atom, and Ar1 and Ar2 are each independently an at least partially deuterated aryl group.
  • R2 or R3 is a group represented by the following general formula (2):
  • R1 , R4 , and R5 can also be a group represented by the following general formula (2).
  • 1 to 3 of X4 to X6 are N, and the rest are C( R7 ).
  • R7 represents a hydrogen atom, a deuterium atom, or a substituent.
  • Ar3 and Ar4 each independently represent a substituted or unsubstituted aryl group.
  • L1 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 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.
  • 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.
  • R 7 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 4 to X 6 are N.
  • X 4 and X 5 are N, and X 6 is C(R 7 ).
  • X 4 and X 6 are N, and X 5 is C(R 7 ) .
  • X 4 is N, and X 5 and X 6 are C(R 7 ) . In one embodiment of the present invention, X 6 is N, and X 4 and X 5 are C( R 7 ).
  • R 7 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R7 is an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, R7 is an aryl group which may be 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 4 to X 6 are N and L 1 is a single bond.
  • X 4 to X 6 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).
  • X4 and X5 are N
  • X6 is C( R7 )
  • R7 is a hydrogen atom or a deuterium atom
  • L1 is a single bond.
  • X4 and X5 are N, X6 is C( R7 ), R7 is a hydrogen atom or a deuterium atom, and L1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6).
  • X4 and X6 are N, X5 is C( R7 ), R7 is a hydrogen atom or a deuterium atom, and L1 is a single bond.
  • X4 and X6 are N
  • X5 is C( R7 )
  • R7 is a hydrogen atom or a deuterium atom
  • L1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6).
  • X 4 to X 6 are N, L 1 is a single bond, and Ar 3 and Ar 4 are the same.
  • X 4 to X 6 are N, L 1 is a single bond, and Ar 3 and Ar 4 are each independently an at least partially deuterated aryl group.
  • X4 and X5 are N, X6 is C( R7 ), R7 is a hydrogen atom or a deuterium atom, L1 is a single bond, and Ar3 and Ar4 are the same.
  • X4 and X5 are N, X6 is C( R7 ), R7 is a hydrogen atom or a deuterium atom, L1 is a single bond, and Ar3 and Ar4 are each independently an at least partially deuterated aryl group.
  • X4 and X6 are N, X5 is C( R7 ), R7 is a hydrogen atom or a deuterium atom, L1 is a single bond, and Ar3 and Ar4 are the same.
  • X4 and X6 are N
  • X5 is C( R7 )
  • R7 is a hydrogen atom or a deuterium atom
  • L1 is a single bond
  • Ar3 and Ar4 are each independently an at least partially deuterated aryl group.
  • X1 and X4 are the same, X2 and X5 are the same, X3 and X6 are the same, Ar1 and Ar3 are the same, and Ar2 and Ar4 are the same.
  • L1 is further a single bond.
  • two of X 1 to X 3 are N, and two of X 4 to X 6 are N.
  • X 1 , X 2 , X 4 , and X 5 are N.
  • only X 1 , X 3 , X 4 , and X 6 are N.
  • one of X 1 to X 3 is N, and two of X 4 to X 6 are N.
  • only X 1 , X 4 , and X 5 are N.
  • only X 1 , X 4 , and X 6 are N.
  • only X 3 , X 4 , and X 5 are N.
  • only X 3 , X 4 , and X 6 are N.
  • one of X 1 to X 3 is N
  • one of X 4 to X 6 is N.
  • only X 1 and X 4 are N.
  • only X3 and X6 are N.
  • 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).
  • the compound represented by the general formula (1) preferably does not contain metal atoms, and may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms.
  • the compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms.
  • the compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen ... and nitrogen atoms. Furthermore, the compound represented by the general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.
  • substituted group A refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means
  • substituted group B means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms).
  • an alkyl group e.g., having 1 to 40 carbon atoms
  • an alkoxy group e.g., having 1 to 40 carbon atoms
  • an aryl group e.g., having 6 to 30 carbon
  • substituted group C means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms).
  • an alkyl group e.g., having 1 to 20 carbon atoms
  • an aryl group e.g., having 6 to 22 carbon atoms
  • a heteroaryl group e.g., having 5 to 20 ring skeleton atoms
  • diarylamino group e.g., having 12 to 20 carbon atoms
  • substituted group D means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms).
  • substituted group E means one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms) and an aryl group (e.g., having 6 to 22 carbon atoms).
  • substituent when it is described as “substituted or unsubstituted” or “optionally substituted", the substituent may be selected, for example, from Substituent Group A, or may be selected from Substituent Group B, or may be selected from Substituent Group C, or may be selected from Substituent Group D, or may be selected from Substituent Group E.
  • each compound represented by general formula (1) is shown individually by specifying R 3 to R 5 in the following general formula (1a) for each compound. That is, structures in which R 2 is a group represented by general formula (2), Ar 1 to Ar 4 are perdeuterated phenyl groups (Ar45), X 1 to X 6 are nitrogen atoms (N), R 1 is a hydrogen atom, L 1 is a single bond (L1), and R 3 to R 5 are groups specified in Table 1 are shown individually as structures of compounds 1 to 250.
  • the structures of compounds 1 to 250 are shown by displaying R 3 to R 5 of a plurality of compounds together in each row.
  • compounds 1 to 50 are the same as R 3 to R 5 and D1 to D50.
  • compounds 51 to 100 are the same as R 4 , R 3 and R 5 , and D1 to D50.
  • compounds 101 to 150 in Table 2 compounds 101 to 150 are the same as R 4 , R 3 and R 5 , and D1 to D50.
  • compounds 151 to 250 in Table 2 are also specified. That is, the compounds in Table 2 are compounds 1 to 250 specified in Table 1, which are displayed together in five rows.
  • compound 2(1) indicates a compound having a structure in which Ar 2 and Ar 4 in compound 2 are replaced with Ar1.
  • Compound 2500(1) shows a compound having a structure in which Ar 2 and Ar 4 of compound 2500 are replaced with Ar1.
  • the compounds in which Ar 2 and Ar 4 of compounds 1 to 2500 are both Ar2 are designated as compounds 1(2) to 2500(2) in order.
  • the compounds in which Ar 1 and Ar 3 , and Ar 2 and Ar 4 of compounds 1 to 2500 are those listed in Table 12 are specified in order.
  • R 1 , R 6 , and R 7 of compounds 1(m) to 2500(m) (m is an integer of 1 to 138) are hydrogen atoms
  • L 1 is a single bond (L1).
  • the compound is selected from the group of compounds identified in Tables 1 to 12. In one aspect of the invention, the compound is selected from the group of compounds identified in Tables 1 to 11.
  • the molecular weight of the compound represented by general formula (1) is preferably 2000 or less, more preferably 1600 or less, and even more preferably 1400 or less, and may be, for example, 1300 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 general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • repeating unit examples include structures represented by the following formulas.
  • a polymer having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any site of general formula (1), reacting the hydroxyl group as a linker with the compound below to introduce a polymerizable group, and polymerizing the polymerizable group.
  • a polymer containing a structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having a structure represented by general formula (1), or may be a polymer containing repeating units having other structures.
  • the repeating units having a structure represented by general formula (1) contained in the polymer may be of a single type, or of two or more types.
  • Examples of repeating units not having a structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.
  • the electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemical calculations, for example, the Hartree-Fock equations (TD-DFT/B3LYP/6-31G*) can be solved using time-dependent density functional theory with 6-31G* as a basis and a family of functions known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with HOMOs above a particular threshold and LUMOs below a particular threshold.
  • TD-DFT/B3LYP/6-31G* time-dependent density functional theory with 6-31G* as a basis and a family of functions known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with HOMOs above a particular threshold and LUMOs below a particular threshold.
  • the donor moiety (“D") can be selected, for example, for a HOMO energy (e.g., ionization potential) of -6.5 eV or greater
  • the acceptor moiety (“A") can be selected, for example, for a LUMO energy (e.g., electron affinity) of -0.5 eV or less.
  • the bridging moiety (“B") prevents overlap between the pi-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly restrict the acceptor and donor moieties to specific conformations.
  • the compound library is screened using one or more of the following properties: 1. Emission near a particular wavelength 2. Calculated triplet state above a particular energy level 3.
  • the difference between the lowest singlet excited state and the lowest triplet excited state ( ⁇ E ST ) at 77K is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV.
  • the ⁇ E ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.
  • the compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.
  • the compound represented by the general formula (1) can be synthesized by combining known reactions.
  • at least one of R 1 to R 5 is a non-fused carbazol-9-yl group
  • a compound of the general formula (1) into which the non-fused carbazol-9-yl group has been introduced can be synthesized by reacting a precursor in which the site of the non-fused carbazol-9-yl group is a fluorine atom with a non-fused carbazole which may be substituted with a group consisting of one or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.
  • the organic light-emitting device of the present invention includes a compound represented by general formula (1) and a light-emitting material having a boron atom.
  • the minimum excited singlet energy of the light-emitting material having a boron atom is preferably lower than that of the compound represented by general formula (1).
  • the luminescent material having a boron atom can be a wide variety of boron compounds that can emit light when used in combination with a compound represented by general formula (1). However, in the present invention, boron complexes are not used. In the present invention, it is preferable to use a luminescent material that utilizes the multiple resonance effect of boron atoms and nitrogen atoms.
  • a compound having a structure in which boron atoms and nitrogen atoms are introduced into the skeleton of a polycyclic aromatic compound can be mentioned.
  • the boron atom and the nitrogen atom have a structure in which they are linked to each other via two carbon atoms that constitute the ring skeleton.
  • a compound represented by the following general formula (3) can be preferably used as the light-emitting material having a boron atom.
  • one of X 1 and X 2 is a nitrogen atom, and the other is a boron atom.
  • X 1 is a nitrogen atom
  • X 2 is a boron atom.
  • R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring.
  • X 1 is a boron atom
  • X 2 is a nitrogen atom.
  • R 21 and R 22 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.
  • R 3 and R 6 are all substituents.
  • R 8 , R 10 and R 12 are all substituents.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , and R 25 and R 26 are not bonded to each other to form a cyclic structure.
  • a compound having the following skeleton can also be preferably used.
  • the compound having the above skeleton is preferably a compound represented by the following general formula (4).
  • R 1 to R 10 each independently represent a deuterium atom or a substituent; n1 and n4 to n10 each independently represent an integer of 0 to 5; and n2 and n3 each independently represent an integer of 0 to 4. It is preferable that R 1 to R 10 are each independently a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group.
  • R 1 to R 10 are each independently a deuterium atom, an alkyl group which may be substituted with a deuterium atom, or an aryl group which may be substituted with a deuterium atom or an alkyl group. In one embodiment of the present invention, R 1 to R 10 are each independently a deuterium atom, or an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, no ring is further condensed to the skeleton of general formula (4). In one embodiment of the present invention, at least one of n1 to n10 is an integer of 1 or more. In one embodiment of the present invention, at least one of n1 to n10 is an integer of 1 or more, and at least one of R 1 to R 10 is a deuterium atom.
  • R 1 , R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 2 represents an acceptor group, or R 1 and R 2 are bonded together to form an acceptor group, or R 2 and R 3 are bonded together to form an acceptor group.
  • R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , and R 15 and R 16 may be bonded together to form a cyclic structure.
  • X 1 represents O or NR
  • R represents a substituent.
  • at least one of X 3 and X 4 is O or NR, and the remaining may be O or NR or may not be linked.
  • both ends independently represent a hydrogen atom, a deuterium atom or a substituent.
  • C-R 1 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 2 , R 2 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 1 may be bonded to each other to form a cyclic structure.
  • C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
  • Z1 and Z2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R1 to R9 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R1 and R2 , R2 and R3 , R3 and R4 , R4 and R5 , R5 and R6 , R7 and R8 , and R8 and R9 may be bonded to each other to form a cyclic structure.
  • At least one of Z 1 , Z 2 , the ring formed by bonding R 1 and R 2 together, the ring formed by bonding R 2 and R 3 together, the ring formed by bonding R 4 and R 5 together, and the ring formed by bonding R 5 and R 6 together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and at least one of R 1 to R 9 is a substituted or unsubstituted aryl group or an acceptor group, or at least one of Z 1 and Z 2 is a ring having an aryl group or an acceptor group as a substituent.
  • a substitutable carbon atom may be substituted with a nitrogen atom.
  • C-R 1 , C-R 2 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 and C-R 9 may be substituted with N.
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 1 represents a hydrogen atom, a deuterium atom, or a substituent
  • R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 are bonded to each other to form a cyclic structure.
  • X3 represents an oxygen atom or a sulfur atom
  • Z2 and Z3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R1 and R4 to R7 each independently represent a hydrogen atom, a deuterium atom or a substituent
  • R2 and R3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • R2 and Z2 , Z2 and Z3 , Z3 and R3 , R4 and R5 , R5 and R6 , and R6 and R7 may be bonded to each other to form a cyclic structure. However, at least one pair of R2 and Z2 , Z2 and Z3 , and Z3 and R3 are bonded to each other to form a cyclic structure.
  • X4 represents an oxygen atom or a sulfur atom
  • Z2 and Z3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R1 and R4a to R7a each independently represent a hydrogen atom, a deuterium atom or a substituent
  • R2 and R3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
  • R2 and Z2 , Z2 and Z3 , Z3 and R3 , R4a and R5a , R5a and R6a , R6a and R7a , and R7a and R1 may be bonded to each other to form a cyclic structure.
  • at least one pair of R2 and Z2 , Z2 and Z3 , and Z3 and R3 are bonded to each other to form a cyclic structure .
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 and R 8 to R 14 each independently represent a hydrogen atom, a deuterium atom, or a substituent
  • R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure.
  • Z 1 and Z 4 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 and R 15 to R 17 each independently represent a hydrogen atom, a deuterium atom, or a substituent
  • R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , and Z 3 and R 3 may be
  • Z 1 and Z 5 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 represents a hydrogen atom, a deuterium atom, or a substituent
  • R 2 and R 3 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 are bonded to each other to form a cyclic structure.
  • Z1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring;
  • Z2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring;
  • R1 and R21 to R27 each independently represent a hydrogen atom, a deuterium atom, or a substituent; and R2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R1 and Z1 , R2 and Z2 , Z2 and R21 , R21 and R22 , R22 and R23 , R23 and R24 , R24 and R25 , R25 and R26 , and R26 and R27 may be bonded to each other to form a cyclic structure .
  • Z 1 and Z 6 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 and R 28 to R 30 each independently represent a hydrogen atom, a deuterium atom, or a substituent
  • R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , and R 30 and Z 6 may be
  • Z 1 and Z 7 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
  • R 1 represents a hydrogen atom, a deuterium atom, or a substituent
  • R 2 and R 3 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 2 and Z 2 , Z 2 and Z 7 , and Z 7 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 7 , and Z 7 and R 3 are bonded to each other to form a cyclic structure.
  • Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 31 to R 44 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , and R 43 and R 44 may be bonded to each other to form a cyclic structure.
  • Z 1 and Z 8 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 51 to R 60 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
  • R 1 and Z 1 , R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , and R 60 and Z 8 may be bonded to each other to form a cyclic structure.
  • Z 1 , Z 8 and Z 9 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 61 to R 66 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , and R 66 and Z 8 may be bonded to each other to form a cyclic structure.
  • Z 1 , Z 9 and Z 10 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 67 to R 69 each independently represent a hydrogen atom, a deuterium atom or a substituent
  • R 70 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , Z 9 and R 67 , R 67 and R 68 , R 68 and R 69 , R 69 and Z 10 , and Z 10 and R 70 may be bonded to each other to form a cyclic structure.
  • Z 1 , Z 11 and Z 12 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 72 to R 74 each independently represent a hydrogen atom, a deuterium atom or a substituent
  • R 71 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 71 and Z 11 , Z 11 and R 72 , R 72 and R 73 , R 73 and Z 74 , and R 74 and Z 12 may be bonded to each other to form a cyclic structure.
  • Z 1 and Z 11 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
  • R 1 and R 76 to R 82 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • R 75 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R 78 and R 79 , R 79 and R 80 , R 80 and R 81 , and R 81 and R 82 may be bonded to each other to form a cyclic structure.
  • X5 represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded;
  • R101 to R130 each independently represent a hydrogen atom, a deuterium atom, or a substituent;
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 3 to R 9 each independently represent a hydrogen atom, a deuterium atom, or a substituent, provided that at least one of R 1 , R 2 , Z 1 , and Z 2 contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring.
  • R1 and Z1 , Z1 and R3 , R3 and R4 , R4 and R5 , R5 and Z2 , Z2 and R2 , R2 and R6 , R6 and R7, R7 and R8 , R8 and R9 , and R9 and R1 may be bonded to each other to form a ring structure.
  • the substitutable carbon atoms may be substituted with a nitrogen atom.
  • C- R3 , C- R4 , C- R5 , C-R6, C- R7 , C- R8 , and C- R9 in the general formula ( 24 ) may be substituted with N.
  • the content of the compound having a boron atom is preferably smaller than that of the compound represented by general formula (1).
  • the content of the compound having a boron atom may be selected within the range of 0.01 to 50% by weight, 0.1 to 30% by weight, or 0.5 to 10% by weight of the content of the compound represented by general formula (1).
  • the organic light-emitting device of the present invention may use two or more types of compounds represented by general formula (1) or two or more types of compounds having a boron atom.
  • the layer (light-emitting layer) containing the compound represented by the general formula (1) and the compound having a boron atom may further contain a host material.
  • the content of the host material in the layer is 20% by weight or more, preferably 30% by weight or more, for example 40% by weight or more.
  • the upper limit is 99% by weight or less, and may be, for example, 90% by weight or less, 70% by weight or less, or 50% by weight or less.
  • the host material of the light-emitting layer is an organic compound having hole transporting and electron transporting 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 having a high glass transition temperature.
  • the lowest excited singlet energy and the lowest excited triplet energy of the host material are preferably higher than those of the compound represented by general formula (1) and the compound having a boron atom.
  • the host material is selected from the group consisting of:
  • the host material is a compound having a structure represented by the following general formula (25):
  • 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 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 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 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 atoms 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 groups.
  • 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 groups.
  • 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 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- 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 (25) 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 (25) 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 (25) 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 (25) 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 (25) 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 (25) 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 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. 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 (25) is selected from Z1 to Z196 and their deuterated forms
  • the group bonded from the right of L is selected from X1 to X79 and their deuterated forms
  • the group bonded from the left of L is selected from Z1 to Z12 and their deuterated forms
  • 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 (25) 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 (25) 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 (25).
  • the compound represented by general formula (25) 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 light-emitting device of the present invention contains a compound represented by general formula (1) and a light-emitting material having a boron atom (excluding boron complexes).
  • the layer (light-emitting layer) containing the compound represented by general formula (1) and the light-emitting material having a boron atom may further contain a host material.
  • the compound represented by general formula (1) functions as an assist dopant.
  • a delayed fluorescent material other than the compound represented by the general formula (1) may be used in combination.
  • Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955, and paragraph 0008 of WO2013/081088.
  • JP 2013-256490 A paragraphs 0009 to 0046 and 0093 to 0134
  • JP 2013-116975 A paragraphs 0008 to 0020 and 0038 to 0040
  • WO 2013/133359 A paragraphs 0007 to 0032 and 0079 to 0084
  • WO 2013/161437 A paragraph 0 No. 008 to 0054 and No.
  • the organic light-emitting element of the present invention light emission from the compound represented by general formula (1) may be included.
  • the amount of light emitted from the compound represented by general formula (1) is 10% or less, for example 1% or less, for example 0.1% or less, of the amount of light emitted from the light-emitting material having boron atoms.
  • 90% or more of the amount of light emitted from the organic light-emitting element is light emission from the light-emitting material having boron atoms, for example 99% or more, for example 99.9% or more is light emission from the light-emitting material having boron atoms.
  • the light-emitting layer does not include a metal element (boron atoms are not included in the metal elements in the present invention).
  • 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, boron atoms, oxygen atoms, and sulfur 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, deuterium atoms, nitrogen atoms, boron atoms, and oxygen atoms.
  • the light-emitting layer can be made of a material that contains all of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, boron atoms, and oxygen atoms, and does not contain any other elements.
  • the compound represented by formula (1) may be used in a layer other than the light-emitting layer.
  • the compound represented by formula (1) may be used in a layer adjacent to the light-emitting layer.
  • 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 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 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 injection properties and resistance to oxidation.
  • the cathode is fabricated by forming the electrode material as a thin film by evaporation or sputtering.
  • the cathode has a sheet resistance of a few hundred ohms or less per unit area. In some embodiments, the cathode has a thickness of 10 nm to 5 ⁇ m. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either one of the anode and cathode of the organic electroluminescent device is transparent or semi-transparent to allow emitted light to pass through. In some embodiments, a transparent or semi-transparent electroluminescent device enhances light radiance.
  • the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode, hi some embodiments, an element includes an anode and a cathode, both of which are transparent or semi-transparent.
  • An injection layer is a layer between an electrode and an organic layer.
  • the injection layer reduces the driving voltage and enhances the light radiance.
  • the injection layer includes a hole injection layer and an electron injection layer.
  • the injection layer can be disposed between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.
  • an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as the hole injection material are given below.
  • a barrier layer is a layer that can prevent charges (electrons or holes) and/or excitons present in the light-emitting layer from diffusing outside the light-emitting layer.
  • an electron barrier layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer.
  • a hole barrier layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer.
  • a barrier layer prevents excitons from diffusing outside the light-emitting layer.
  • the electron barrier layer and the hole barrier layer constitute an exciton barrier layer.
  • the term "electron barrier layer" or "exciton barrier layer” includes layers that have both the functions of an electron barrier layer and of an exciton barrier layer.
  • Hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer.
  • the materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.
  • Electron Barrier Layer The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer.
  • the materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron blocking material are given below.
  • Exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, the layer may be present between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer.
  • the layer when the exciton blocking layer is present on the cathode side, the layer may be present between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.
  • the hole transport layer comprises a hole transport material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one of the following properties: hole injection or transport property and electron blocking property.
  • the hole transport material is an organic material.
  • the hole transport material is an inorganic material.
  • Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof.
  • the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are given below.
  • the electron transport layer comprises an electron transport material.
  • the electron transport layer is a single layer.
  • the electron transport layer has multiple layers.
  • the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer.
  • the electron transport material also functions as a hole-blocking material.
  • electron transport layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof.
  • the electron transport material is a thiadiazole derivative or a quinoxaline derivative.
  • the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are given below.
  • the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet.
  • an electronic device includes an OLED having an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode.
  • the compositions described herein may be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
  • compositions may be useful in facilitating charge or energy transfer within devices and/or as hole transport materials, such as organic light emitting diodes (OLEDs), organic integrated circuits (OICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light emitting fuel cells (LECs), or organic laser diodes (O-lasers).
  • OLEDs organic light emitting diodes
  • OICs organic integrated circuits
  • O-FETs organic field effect transistors
  • OF-TFTs organic thin film transistors
  • O-LETs organic light emitting transistors
  • O-SCs organic solar cells
  • organic optical detectors organic photoreceptors, organic field-quench devices (O-FQDs), light emitting fuel cells (LECs), or organic laser diodes (O-lasers
  • the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode.
  • the device includes OLEDs of different colors.
  • the device includes an array including a combination of OLEDs.
  • the combination of OLEDs is a three-color combination (e.g., RGB).
  • the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green).
  • the combination of OLEDs is a two-color, four-color, or more-color combination.
  • the device comprises: a circuit board having a first side having a mounting surface and an opposing second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive 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 the OLEDs emit light in a plurality of directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.
  • the light-emitting layer of the present invention can be used in a screen or display.
  • the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching to provide pixels with unique aspect ratios.
  • the screen also called a mask
  • the corresponding artwork pattern design allows for the placement of very steep narrow tie bars between pixels in the vertical direction, as well as large wide angled openings in the horizontal direction.
  • the internal patterning of the pixel allows for the construction of three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in the pixel area protects etching in certain areas until those particular patterns are undercut and removed from the substrate. At that point, all pixel areas are treated with similar etch rates, but the depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with different protection rates within the pixel, allowing for the localized deep etching required to create steep vertical bevels.
  • the preferred material for the deposition mask is Invar.
  • the screen or display pattern is a pixel matrix on a substrate.
  • the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).
  • the screen or display pattern is fabricated using wet chemical etching.
  • the screen or display pattern is fabricated using plasma etching.
  • OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating a planarizing film on the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel.
  • TFT thin film transistor
  • a method for manufacturing an organic light emitting diode (OLED) display comprising the steps of: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in the form of a cell panel; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels.
  • the barrier layer is an inorganic film, for example made of SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic.
  • the organic film helps the mother panel to be cut softly into cell panels.
  • the thin film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source/drain electrodes.
  • Each of the plurality of display units may have a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed at the same time as the planarization film.
  • the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit.
  • the organic film is not connected to the display unit or the encapsulation layer.
  • each of the organic film and the planarization film may comprise one of polyimide and acrylic.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide.
  • the method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide prior to forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate prior to cutting along the interface.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film disposed on the TFT layer for covering the TFT layer.
  • the planarization film is an organic film formed on the passivation layer.
  • the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.
  • the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source/drain electrode of a TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image.
  • a display unit an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.
  • the encapsulation layer that covers the display units and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated.
  • the organic film applied to the interface portion is disposed at an interval with each of the plurality of display units.
  • the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the end of the barrier layer.
  • the OLED display is flexible and uses a flexible base substrate formed from polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed from a glass material, and the carrier substrate is then separated.
  • a barrier layer is formed on a surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.
  • the manufacturing method further includes a step of cutting along the interface, where a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate.
  • a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on the TFT layer to cover the TFT layer.
  • the planarization film for example made of polyimide or acrylic
  • the groove of the interface is covered with an organic film, for example made of polyimide or acrylic.
  • the interface grooves between the barrier layers are covered with an organic film to absorb shocks that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers.
  • the organic film and planarizing film covering the interface grooves are spaced apart from each other.
  • the organic film and planarizing film were connected to each other as one layer, there would be a risk of external moisture penetrating the display unit through the planarizing film and the remaining organic film, so the organic film and planarizing film are spaced apart from each other such that the organic film is spaced apart from the display unit.
  • the display unit is formed by forming a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit.
  • the carrier substrate carrying the base substrate is separated from the base substrate.
  • the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate.
  • the mother panel is cut into individual cell panels.
  • the mother panel is cut along the interface between the cell panels using a cutter.
  • the grooves at 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).
  • 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', T1, and D1 were co-deposited from different deposition sources to form a layer with a thickness of 40 nm to serve as a light-emitting layer.
  • the concentration of H1' in the light-emitting layer was 34.2% by weight
  • the concentration of T1 was 65.0% by weight
  • the concentration of D1 was 0.8% by weight.
  • 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 weight and 70% by weight, respectively.
  • Comparative element 1 was prepared in the same manner except that comparative compound T was used in place of T1.
  • the fabricated elements were driven at 6.3 mA/ cm2 to measure the external quantum efficiency (EQE).
  • EQE external quantum efficiency
  • the orientation degree (S value) of the compound T1 and the comparative compound T in the light-emitting layer was measured.
  • the orientation degree was measured according to the method described in Scientific Reports 2017, The orientation of the light-emitting material in the light-emitting layer was determined by the method described in JP-A-2003-234558, and the results are shown in the following table. It was confirmed that the organic light-emitting device satisfying the conditions of the present invention has high orientation of the light-emitting material in the light-emitting layer and excellent light-emitting characteristics.
  • Example 2 Preparation of an Organic Electroluminescent Device An organic electroluminescent device, Device 2, is prepared according to the same procedure as in Example 1, except that D2 is used instead of D1.
  • Example 3 Preparation of Organic Electroluminescent Device An organic electroluminescent device, Device 3, is prepared following the same procedure as in Example 1, except that D3 is used instead of D1.
  • the present invention has a high industrial applicability.

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KR20190018397A (ko) * 2017-08-14 2019-02-22 주식회사 엘지화학 함질소 고리 화합물 및 이를 포함하는 유기 발광 소자
JP2019204947A (ja) * 2018-05-04 2019-11-28 サイノラ ゲゼルシャフト ミット ベシュレンクテル ハフツング 青色光を発光する有機エレクトロルミネセントデバイス
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CN113402537A (zh) * 2021-07-15 2021-09-17 清华大学 一种有机化合物及其应用
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WO2018237385A1 (en) * 2017-06-23 2018-12-27 Kyulux, Inc. Composition of matter for use in organic light-emitting diodes
KR20190018397A (ko) * 2017-08-14 2019-02-22 주식회사 엘지화학 함질소 고리 화합물 및 이를 포함하는 유기 발광 소자
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WO2023282224A1 (ja) * 2021-07-06 2023-01-12 株式会社Kyulux 有機発光素子およびその設計方法
CN113402537A (zh) * 2021-07-15 2021-09-17 清华大学 一种有机化合物及其应用

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