WO2022270592A1 - Matériau de barrière d'électrons, élément semi-conducteur organique et composé - Google Patents

Matériau de barrière d'électrons, élément semi-conducteur organique et composé Download PDF

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WO2022270592A1
WO2022270592A1 PCT/JP2022/025151 JP2022025151W WO2022270592A1 WO 2022270592 A1 WO2022270592 A1 WO 2022270592A1 JP 2022025151 W JP2022025151 W JP 2022025151W WO 2022270592 A1 WO2022270592 A1 WO 2022270592A1
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group
general formula
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substituted
independently represent
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PCT/JP2022/025151
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寛晃 小澤
桃子 森尾
亜衣子 後藤
京 森本
ソンヘ ファン
ヨン ジュ ジョ
貴弘 柏▲崎▼
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株式会社Kyulux
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Priority claimed from PCT/JP2022/023781 external-priority patent/WO2022270354A1/fr
Application filed by 株式会社Kyulux filed Critical 株式会社Kyulux
Priority to CN202280044336.0A priority Critical patent/CN117546634A/zh
Priority to JP2023530125A priority patent/JPWO2022270592A1/ja
Priority to PCT/JP2022/044014 priority patent/WO2023120062A1/fr
Publication of WO2022270592A1 publication Critical patent/WO2022270592A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound useful as an electron barrier material and an organic semiconductor device using the compound.
  • organic electroluminescence devices organic electroluminescence devices
  • the electron blocking material is provided between the light-emitting layer and the hole-transporting layer to prevent electrons present in the light-emitting layer from escaping from the light-emitting layer to the hole-transporting layer. It is a material for the electron barrier layer that has the function of transporting the holes of the electrons to the light-emitting layer.
  • Patent Document 1 proposes a compound having the following structure.
  • organic electroluminescence devices using the above compounds as electron barrier materials have room for improvement in terms of device life.
  • the present inventors have made intensive studies to provide an electron barrier material that can extend the device life when used in an organic electroluminescence device.
  • An electron barrier material containing a compound represented by the following general formula (1) [In the formula, R 1 to R 5 each independently represent a deuterium atom or a substituent containing no cyano group. R 1 to R 5 do not combine with other R 1 to R 5 or Ar to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton. good.
  • n1, n3 and n5 each independently represents an integer of 0 to 4, n2 represents an integer of 0 to 3, and n4 represents an integer of 0 to 2.
  • X represents an oxygen atom or a sulfur atom.
  • Ar represents a monocyclic arylene group or a monocyclic heteroarylene group, and the monocyclic arylene group and the monocyclic heteroarylene group may be substituted with a deuterium atom or a substituent that does not contain a cyano group.
  • R 1 to R 6 do not combine with other R 1 to R 6 to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton.
  • n1, n3 and n5 each independently represent an integer of 0 to 4
  • n2 and n6 each independently represent an integer of 0 to 3
  • n4 represents an integer of 0 to 2 .
  • X represents an oxygen atom or a sulfur atom.
  • R 1 to R 6 each independently represent a deuterium atom or a substituent containing no cyano group.
  • R 1 to R 6 do not combine with other R 1 to R 6 to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton.
  • n1, n3 and n5 each independently represent an integer of 0 to 4
  • n2 and n6 each independently represent an integer of 0 to 3
  • n4 represents an integer of 0 to 2 .
  • X represents an oxygen atom or a sulfur atom.
  • R 1 to R 6 each independently represent a deuterium atom or a substituent containing no cyano group.
  • R 1 to R 6 do not combine with other R 1 to R 6 to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton.
  • n1, n3 and n5 each independently represent an integer of 0 to 4
  • n2 and n6 each independently represent an integer of 0 to 3
  • n4 represents an integer of 0 to 2 .
  • n1+n3+n4+n5 is 1 or more.
  • One or two of R 1 and R 3 to R 5 represent an optionally deuterated alkyl group or a phenyl group optionally substituted with a deuterium atom.
  • X represents an oxygen atom or a sulfur atom.
  • R 1 to R 26 , A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 are bonded together to form a cyclic It may form a structure.
  • X 1 is a nitrogen atom
  • R 7 and R 8 and R 21 and R 22 are bonded through the nitrogen atom to form a 6-membered ring
  • R 17 and R 18 are When joined to form a single bond, at least one of R 1 to R 6 is a substituted or unsubstituted aryl group, or 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 are bonded to each other to form an aromatic or heteroaromatic ring.
  • X 1 is a boron atom
  • X 2 is a nitrogen atom
  • R 7 and R 8 and R 17 and R 18 are bonded to each other to form a cyclic structure containing a boron atom
  • the cyclic structure is a 5- to 7-membered ring
  • R 7 and R 8 , R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS - or -N(R 27 )-.
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • An organic semiconductor device comprising the electron barrier material according to any one of [1] to [7].
  • An organic electroluminescence device wherein the organic semiconductor device has at least two organic layers including an anode, a cathode, and an electron blocking layer containing the electron blocking material and a light-emitting layer between the anode and the cathode.
  • R 21 to R 23 represents a cyano group or a group represented by the following general formula (5), and the remaining two of R 21 to R 23 and R 24 and R 25 at least one of which represents a group represented by the following general formula (6), and the rest of R 21 to R 25 are hydrogen atoms or substituents (where the substituent here is a cyano group, the following general formula (5 ) is not a group represented by the following general formula (6).
  • L 1 represents a single bond or a divalent linking group
  • R 31 and R 32 each independently represent a hydrogen atom or a substituent
  • * represents a bonding position.
  • L 2 represents a single bond or a divalent linking group
  • R 33 and R 34 each independently represent a hydrogen atom or a substituent
  • * represents a bonding position.
  • the compound represented by general formula (1) is useful as an electron barrier material and can be effectively used in organic semiconductor devices.
  • the life of the device can be lengthened by using the compound of the present invention for the electron barrier layer of the organic electroluminescence device.
  • substituted means an atom or group of atoms other than a hydrogen atom and a deuterium atom.
  • the expressions "substituted or unsubstituted” and “optionally substituted” mean that a hydrogen atom may be substituted with a deuterium atom or a substituent.
  • the term “transparent” in the present invention means that the visible light transmittance is 50% or more, preferably 80% or more, more preferably 90% or more, and still more preferably 99% or more. Visible light transmittance can be measured with an ultraviolet/visible spectrophotometer.
  • R 1 to R 5 each independently represent a deuterium atom or a substituent containing no cyano group.
  • each of the substituents R 1 to R 5 independently has a Hammett's ⁇ p value in the range of ⁇ 0.3 to 0.3.
  • each of the substituents R 1 to R 5 independently has a Hammett's ⁇ p value in the range of ⁇ 0.2 to 0.2.
  • each of the substituents R 1 to R 5 independently has a Hammett's ⁇ p value in the range of ⁇ 0.1 to 0.1.
  • each of the substituents R 1 to R 5 independently has a Hammett's ⁇ p value in the range of greater than 0 and less than or equal to 0.3. In one aspect of the present invention, each of the substituents R 1 to R 5 independently has a Hammett's ⁇ p value in the range of ⁇ 0.3 or more and less than 0.
  • Hammett's ⁇ p value is defined by L.P. P. Proposed by Hammett, it quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives.
  • k 0 is the rate constant of the benzene derivative without a substituent
  • k is the rate constant of the benzene derivative substituted with a substituent
  • K 0 is the equilibrium constant of the benzene derivative without the substituent
  • K is the substituent
  • the equilibrium constant of the benzene derivative substituted with ⁇ represents the reaction constant determined by the type and conditions of the reaction.
  • each of R 1 to R 5 is independently a substituent having no lone pair. In one aspect of the present invention, each of R 1 to R 5 is independently a substituent having no ⁇ electrons.
  • each of R 1 to R 5 is independently one or a combination of two or more groups selected from the group consisting of alkyl groups and aryl groups (eg, 6 to 30 carbon atoms).
  • each of R 1 to R 5 is independently an alkyl group having 1 to 30 carbon atoms which may be substituted with an aryl group having 6 to 20 carbon atoms. In one aspect of the present invention, R 1 to R 5 are each independently an aryl group having 6 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 30 carbon atoms. In one aspect of the present invention, each of R 1 to R 5 is independently an unsubstituted alkyl group having 1 to 30 carbon atoms. In one aspect of the present invention, each of R 1 to R 5 is independently an unsubstituted aryl group having 6 to 20 carbon atoms.
  • R 1 to R 5 do not combine with other R 1 to R 5 or Ar to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton. good. Therefore, the dibenzofuran (three-ring structure) on the left side of the general formula (1) is not further condensed to form a structure of four or more rings.
  • the rings are not condensed.
  • the structure on the right side of general formula (1) is preferably a pentacyclic structure. That is, in a preferred embodiment of the present invention, R 3s do not combine with each other to form a cyclic structure.
  • n1, n3, and n5 each independently represent an integer of 0 to 4, n2 represents an integer of 0 to 3, and n4 represents an integer of 0 to 2.
  • n1-n5 are each independently an integer of 0-2.
  • n1 is zero.
  • n2 is zero.
  • n3 is 0 or 1.
  • n4 is 0 or 1.
  • n5 is 0 or 1.
  • n3+n4+n5 is 1 or more.
  • n3+n4+n5 is one.
  • n3+n4+n5 is two.
  • n1, n2, n4 and n5 are 0 and n3 is 1.
  • n1 to n3 and n5 are 0 and n4 is 1.
  • n1 to n4 are 0 and n5 is 1.
  • n1, n2 and n4 are 0 and n3 and n5 are 1.
  • n1, n2 and n5 are 0 and n3 and n4 are 1.
  • X represents an oxygen atom or a sulfur atom. In one aspect of the invention, X is a sulfur atom. In one preferred aspect of the invention, X is an oxygen atom.
  • a single bond extends downward to the left from the ortho position of the benzene ring bonded to the right side of X. This single bond may be attached to any of positions 1 to 4 of the carbazole structure located on the right side of Ar in general formula (1). Also, X may be bonded to any of the 1 to 4 positions of the carbazole structure located on the right side of Ar in general formula (1). However, the single bond and X are respectively bonded to adjacent carbon atoms forming the skeleton of the carbazole structure.
  • a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be employed as the benzofurocarbazol-9-yl group bonded to Ar in the general formula (1).
  • a substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be employed as the benzothienocarbazol-9-yl group bonded to Ar in the general formula (1).
  • a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be employed.
  • Employing a substituted or unsubstituted bisbenzofuro[2,3-a:2′,3′-f]carbazol-9-yl group as the bisbenzofurocarbazol-9-yl group bonded to Ar in the general formula (1) can do.
  • a substituted or unsubstituted bisbenzofuro[3,2-a:3',2'-f]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzofuro[2,3-b:2',3'-e]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzofuro[3,2-b:3′,2′-e]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzofuro[2,3-c:2',3'-d]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzofuro[3,2-c:3',2'-d]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzothieno[2,3-a:2′,3′-f]carbazol-9-yl group as the bisbenzothienocarbazol-9-yl group bonded to Ar in the general formula (1) can do.
  • a substituted or unsubstituted bisbenzothieno[3,2-a:3',2'-f]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzothieno[2,3-b:2',3'-e]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzothieno[3,2-b:3',2'-e]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzothieno[2,3-c:2',3'-d]carbazol-9-yl group can also be employed.
  • a substituted or unsubstituted bisbenzothieno[3,2-c:3',2'-d]carbazol-9-yl group can also be employed.
  • D1(D) to D64(D) are examples of the above D1 to D64 in which all the hydrogen atoms are replaced with deuterium atoms.
  • D7(R) to D18(R) and D37(R) to D48(R) are obtained by replacing only the hydrogen atoms bonded to the alkyl groups of D7 to D18 and D37 to D48 with deuterium atoms.
  • D19 (Ph) to D30 (Ph) and D49 (Ph) to D60 (Ph) are obtained by replacing only the hydrogen atoms bonded to the phenyl groups of D19 to D30 and D49 to D60 with deuterium atoms.
  • D19 (Ph) to D30 (Ph) and D49 (Ph) to D60 (Ph) are obtained by replacing only the hydrogen atoms bonded to the phenyl groups of D19 to D30 and D49 to D60 with deuterium atoms.
  • the substituted or unsubstituted benzofurocarbazol-9-yl group and the substituted or unsubstituted benzothienocarbazol-9-yl group bonded to Ar in the general formula (1) are D1 to D60. , D1 (D) ⁇ D60 (D), D7 (R) ⁇ D18 (R), D37 (R) ⁇ D48 (R), D19 (Ph) ⁇ D30 (Ph), D49 (Ph) ⁇ D60 (Ph) more preferably D1-D30, D1(D)-D30(D), D7(R)-D18(R), D19(Ph)-D30(Ph).
  • Ar represents a monocyclic arylene group or a monocyclic heteroarylene group.
  • the monocyclic arylene group as used herein means a non-condensed phenylene group.
  • a monocyclic heteroarylene group means an aromatic ring group having a single ring structure that is not condensed and containing a heteroatom as a ring skeleton-constituting atom.
  • the monocyclic heteroarylene group preferably has 5 to 7 ring skeleton atoms, more preferably 5 or 6 atoms. For example, 6 atoms can be employed.
  • the heteroatom constituting the ring skeleton of the monocyclic heteroarylene group can be exemplified by a nitrogen atom, an oxygen atom and a sulfur atom, preferably a nitrogen atom.
  • a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring can be mentioned as the ring constituting the monocyclic heteroarylene group.
  • the carbazole represented on the right side of the general formula (1) is bonded to the 1-position of the monocyclic ring that constitutes Ar
  • the dibenzofuran represented on the left side of the general formula (1) is any of the monocyclic rings that constitute Ar.
  • dibenzofuran is bonded to the 3- or 4-position of the monocyclic ring constituting Ar.
  • a dibenzofuran is bonded to the 3-position of the monocyclic ring constituting Ar (for example, when Ar is a substituted or unsubstituted 1,3-phenylene group), and dibenzofuran is attached to the 2- or 4-position. is better than when
  • the monocyclic arylene group and monocyclic heteroarylene group that Ar can take may be substituted with a deuterium atom or a substituent that does not contain a cyano group.
  • a substituent having a Hammett's ⁇ p value in the range of ⁇ 0.3 to 0.3 is selected as the substituent.
  • substituents having a Hammett's ⁇ p value in the range of ⁇ 0.3 to 0.3 reference can be made to the corresponding descriptions of R 1 to R 5 .
  • groups that do not have a lone pair of electrons are selected as substituents.
  • a group having no ⁇ -electrons is selected as a substituent.
  • an alkyl group having 1 to 30 carbon atoms is selected as the substituent.
  • Ar is a phenylene group optionally substituted with 1 to 4 alkyl groups having 1 to 20 carbon atoms, or substituted by 1 to 3 alkyl groups having 1 to 20 carbon atoms. is a good monocyclic heteroarylene group.
  • Ar is an unsubstituted phenylene group or an unsubstituted monocyclic heteroarylene group.
  • t-Bu represents a tert-butyl group and Ph represents an unsubstituted phenyl group.
  • Ar1(D) to Ar15(D) are examples of the above Ar1 to Ar15 in which all the hydrogen atoms are replaced with deuterium atoms.
  • Ar2(R) to Ar9(R) are examples in which only the hydrogen atoms bonded to the alkyl groups of Ar2 to Ar9 are substituted with deuterium atoms.
  • Ar10(Ph) in which only the hydrogen atom bonded to the phenyl group of Ar10 is substituted with a deuterium atom is exemplified here.
  • Ar in general formula (1) is selected from Ar1 to Ar9, Ar1(D) to Ar9(D), Ar2(R) to Ar9(R), more preferably Ar1 to Select from Ar9.
  • Ar in general formula (1) is Ar1 or Ar1(D), more preferably Ar1.
  • the dibenzofuran represented on the left side of general formula (1) may be bonded to Ar at any of the 1-4 positions.
  • dibenzofuran is attached to Ar at the 2-position.
  • the dibenzofuran is attached to Ar at the 1-position.
  • the dibenzofuran is attached to Ar at the 3-position.
  • the dibenzofuran is attached to Ar at the 4-position.
  • the 1-4 positions of dibenzofuran are as follows.
  • B1(D) to B12(D) are examples of the above B1 to B12 in which all the hydrogen atoms are replaced with deuterium atoms.
  • B2(R), B5(R), B8(R), and B11(R) are obtained by replacing only the hydrogen atoms bonded to the alkyl groups of B2, B5, B8, and B11 with deuterium atoms.
  • B3 (Ph), B6 (Ph), B9 (Ph), and B12 (Ph) are obtained by replacing only the hydrogen atoms bonded to the phenyl groups of B3, B6, B9, and B12 with deuterium atoms.
  • B3 (Ph), B6 (Ph), B9 (Ph), and B12 (Ph) are obtained by replacing only the hydrogen atoms bonded to the phenyl groups of B3, B6, B9, and B12 with deuterium atoms.
  • the dibenzofuryl group bonded to Ar in general formula (1) is selected from B1 to B3, B1(D) to B3(D), B2(R), and B3(Ph). , more preferably from B1 to B3.
  • the dibenzofuryl group bonded to Ar in the general formula (1) is selected from B1, B4, B7, B10, B1(D), B4(D), B7(D), and B10(D) and more preferably from B1, B4, B7 and B10.
  • alkyl group in the present application may be linear, branched or cyclic. Moreover, two or more of the linear portion, the cyclic portion and the branched portion may be mixed.
  • the number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopentyl, A cyclohexyl group and a cycloheptyl group can be mentioned.
  • the alkyl group has 1 to 4 carbon atoms.
  • the alkyl group is a methyl group.
  • the alkyl group is an isopropyl group.
  • the alkyl group is a tert-butyl group.
  • the alkyl groups may be the same or different. In one aspect of the present invention, all alkyl groups in the molecule represented by general formula (1) are the same.
  • the number of alkyl groups in the molecule represented by general formula (1) can be 0 or more, 1 or more, 2 or more, 4 or more, and 8 or more.
  • the number of alkyl groups in the molecule represented by formula (1) may be 20 or less, 10 or less, 5 or less, or 3 or less.
  • the number of alkyl groups in the molecule represented by general formula (1) may be zero.
  • the number of alkyl groups referred to here also includes the number of alkyl groups substituted by phenyl groups.
  • a phenyl group optionally substituted with an alkyl group in the present application means that at least one of the five hydrogen atoms present in the phenyl group may be substituted with an alkyl group.
  • the phenyl group is substituted with 0-3 alkyl groups. For example, substituted with 0-2 alkyl groups.
  • the phenyl group is not substituted with an alkyl group.
  • the number of carbon atoms in the alkyl group substituted on the phenyl group is preferably 1-6, more preferably 1-4.
  • alkyl group which may be deuterated in the present application means that at least one hydrogen atom of the alkyl group may be substituted with a deuterium atom. All hydrogen atoms in the alkyl group may be replaced with deuterium atoms.
  • optionally deuterated methyl groups include CH3 , CDH2 , CD2H , CD3.
  • optionally deuterated alkyl group is preferably an alkyl group that is not deuterated at all or an alkyl group in which all hydrogen atoms are substituted with deuterium atoms.
  • an alkyl group that is not deuterated at all is selected as the “optionally deuterated alkyl group”.
  • an alkyl group in which all hydrogen atoms are substituted with deuterium atoms is selected as the “optionally deuterated alkyl group”.
  • general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms. In a preferred embodiment of the present invention, general formula (1) consists only of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms.
  • the molecular weight of the compound represented by the general formula (1) is 499 or more, preferably 700 or less, more preferably 600 or less, for example, may be 550 or less, or 530 or less. good.
  • a compound represented by the following general formula (2A) can be preferably exemplified.
  • a compound represented by the following general formula (2B) can be preferably exemplified.
  • n6 in general formulas (2A) and (2B) is an integer of 0-3. n6 can be selected within the range of 0 to 2, can be 0 or 1, and is preferably 0. n1 to n6 in general formulas (2A) and (2B) can be independently selected within the range of 0 to 2, or can be 0 or 1. Further, all of n1 to n6 may be 0.
  • particularly preferred structures are those in which the phenylene group to which (R 6 ) n6 is bonded in general formulas (2A) and (2B) is 1, This structure is a 3-phenylene group (metaphenylene group).
  • a compound represented by the following general formula (3) can be particularly preferably exemplified.
  • R 1 to R 6 each independently represent a deuterium atom or a substituent containing no cyano group.
  • R 1 to R 6 do not combine with other R 1 to R 6 to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton.
  • n1, n3 and n5 each independently represent an integer of 0 to 4
  • n2 and n6 each independently represent an integer of 0 to 3
  • n4 represents an integer of 0 to 2 .
  • n1+n3+n4+n5 is 1 or more.
  • R 1 and R 3 to R 5 represent an optionally deuterated alkyl group or a phenyl group optionally substituted with a deuterium atom.
  • X represents an oxygen atom or a sulfur atom.
  • n1+n3+n4+n5 is 1 or more, and one or two of R 1 and R 3 to R 5 are an optionally deuterated alkyl group or a deuterium atom is different only in that it represents a phenyl group optionally substituted with (hereinafter referred to as "phenyl group A").
  • phenyl group A a phenyl group optionally substituted with
  • three or more of R 1 and R 3 to R 5 are not phenyl groups A.
  • only one R 1 is a phenyl group A.
  • only one R3 is a phenyl group A.
  • only one R4 is a phenyl group A.
  • only one R 5 is a phenyl group A.
  • only one R3 and one R4 is a phenyl group A.
  • only one R3 and one R5 is a phenyl group A.
  • only one R4 and one R5 is a phenyl group A.
  • only two R3's , only two R4 's or only two R5's may be phenyl groups A. When n3+n4+n5 is 0, R1 is preferably not an unsubstituted phenyl group.
  • At least one of R 3 to R 5 is a phenyl group A and n3+n4+n5 is 1 or more. At least one of the phenyl groups A of R 3 to R 5 is bonded to the meta position (2-position of the carbazole ring) when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole. In a preferred embodiment of the present invention, at least one of the phenyl groups A of R 3 to R 5 is bonded at the para-position (3-position of the carbazole ring) viewed from the bonding position of the nitrogen atom constituting the carbazole ring skeleton. ing.
  • the phenyl group A of R 3 to R 5 is bonded only at the meta-position (2-position of the carbazole ring) when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole. In a preferred embodiment of the present invention, the phenyl group A of R 3 to R 5 is bonded only at the para-position (3-position of the carbazole ring) when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole.
  • the phenyl group A of R 3 to R 5 is bonded only at the para position when viewed from the bonding position of the oxygen atom constituting the ring skeleton of the benzofuro structure or the sulfur atom constituting the ring skeleton of the benzothieno structure.
  • R 3 to R 5 have one phenyl group A at the para-position when viewed from the bonding position of the nitrogen atom constituting the ring skeleton of carbazole, and one oxygen group constituting the ring skeleton of the benzofuro structure.
  • the phenyl group A is a phenyl group optionally substituted with an optionally deuterated alkyl group.
  • the phenyl group A is a phenyl group optionally substituted with a deuterium atom.
  • the phenyl group A is an unsubstituted phenyl group.
  • n3 + n4 + n5 in the general formula (3) is an integer of 1 to 10, preferably an integer of 1 to 8, more preferably an integer of 1 to 6, 1 Any integer from ⁇ 4 is more preferable.
  • n3+n4+n5 is one. In one preferred aspect of the invention, n3+n4+n5 is two.
  • the molecular weight of the compound represented by the general formula (1) is, for example, 1500 or less when the organic layer containing the compound represented by the general formula (1) is intended to be formed by a vapor deposition method and used. It is preferably 1200 or less, more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1).
  • the compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. If a coating method is used, it is possible to form a film even with a compound having a relatively large molecular weight.
  • the compound represented by general formula (1) has the advantage of being easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) can be easily applied to the coating method, and can be easily purified to increase its purity.
  • the compound represented by general formula (1) preferably does not contain metal atoms or boron atoms.
  • a compound composed of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen 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, nitrogen atoms and oxygen atoms can be selected.
  • D in P6 to P14 represents a deuterium atom.
  • Compounds 1a (D) to 47n (D) in which all hydrogen atoms in Compounds 1a to 47n are replaced with deuterium atoms are exemplified here.
  • Compounds 1a (Ph) to 21d (Ph) in which only the hydrogen atoms bonded to the phenyl groups of compounds 1a to 21d are replaced with deuterium atoms are exemplified here.
  • compounds 1a to 21d can be mentioned as more preferable compounds than compounds 22 and 23.
  • it is selected from compounds na (where n is an integer from 1 to 21, where compound na represents the group consisting of compounds 1a, 2a, 3a . . . 21a).
  • nb (n represents an integer from 1 to 21). In one aspect of the invention, it is selected from compounds nc, where n represents an integer from 1 to 21. In one aspect of the invention, it is selected from compounds nd (n represents an integer from 1 to 21). In one aspect of the invention, it is selected from compounds 1a-5d. In one aspect of the invention, it is selected from compounds 7a-9d. In one aspect of the invention, it is selected from compounds 10a-12d. In one aspect of the invention, it is selected from compounds 13a-15d. In one aspect of the invention, it is selected from compounds 16a-18d. In one aspect of the invention, it is selected from compounds 19a-21d.
  • compounds 24a to 47n can be mentioned as more preferable compounds than compound 23, and compounds 24a to 27n can be mentioned as more preferable compounds.
  • it is selected from compounds 24a-24n.
  • it is selected from compounds 25a-25n.
  • it is selected from compounds 26a-26n.
  • it is selected from compounds 27a-27n.
  • it is selected from 24a, 25a, 26a, 27a, 24f, 25f, 26f, 27f.
  • the compound represented by general formula (1) is selected from the group of compounds below.
  • a compound represented by the following general formula (A) is also disclosed as a compound useful as an electron barrier material or a host material.
  • X1 represents an oxygen atom or a sulfur atom.
  • X2 represents an oxygen atom, a sulfur atom, N ( R7 ) or C ( R8 )(R9).
  • R 1 to R 6 independently represents one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more.
  • At least one R 1 is an aryl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more groups.
  • R 1 to R 6 do not combine with other R 1 to R 6 to form a cyclic structure, but adjacent R 3 may combine with each other to form a benzofuro skeleton or benzothieno skeleton.
  • n1 represents an integer of 1 to 4
  • n3, n5 and n6 each independently represents an integer of 0 to 4
  • n2 represents an integer of 0 to 3
  • n4 represents an integer of 0 to 2 represents an integer.
  • the benzene ring to which (R 5 ) n5 is bonded and the benzene ring to which (R 4 ) n4 is bonded are bonded by two bonds, a single bond and a linking group via X 2 .
  • X 1 and X 2 are the same. In one aspect of the invention, X 1 and X 2 are different. In a preferred embodiment of the present invention, both X 1 and X 2 are oxygen atoms. In one aspect of the invention, both X 1 and X 2 are sulfur atoms. In one aspect of the invention, X 1 is an oxygen atom and X 2 is a sulfur atom. In one aspect of the invention, X 1 is a sulfur atom and X 2 is an oxygen atom. In one aspect of the invention, X 1 is an oxygen atom and X 2 is N(R 7 ). In one aspect of the invention, X 1 is an oxygen atom and X 2 is C(R 8 )(R 9 ). In one preferred aspect of the invention, X 1 is an oxygen atom. In one preferred aspect of the invention, X2 is an oxygen atom or a sulfur atom, more preferably an oxygen atom.
  • R 1 to R 6 are each independently one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group combining two or more, preferably a deuterium atom, an alkyl group optionally substituted with a deuterium atom, or substituted with one atom or group or a combination of two or more groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group; is an aryl group that may be
  • each of R 1 to R 6 is independently a deuterium atom, or one atom or group selected from the group consisting of a deuterium atom and an aryl group, or a combination of two or more is an aryl group optionally substituted with
  • the number of carbon atoms in the alkyl group in the explanation of general formula (1) can be usually selected within the range of 1-40, preferably 1-15, more preferably 1-6, eg 1-3.
  • the number of carbon atoms in the aryl group can be selected generally within the range of 6-30, preferably 6-18, more preferably 6-14, for example 6-10.
  • R 3 are bonded together to form a benzofuro skeleton.
  • R3s are bonded together to form a benzothieno skeleton.
  • the benzofuro skeleton and benzothieno skeleton may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more groups.
  • R 3s do not combine with each other to form a cyclic structure.
  • At least one R 1 is an aryl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more groups, more preferably is a phenyl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more groups, more preferably a deuterium atom and It is a phenyl group optionally substituted with one atom or group selected from the group consisting of phenyl groups, or a combination of two or more groups.
  • such R 1 is an unsubstituted aryl group or an aryl group having all hydrogen atoms substituted with deuterium atoms, preferably an unsubstituted phenyl group. or a phenyl group in which all hydrogen atoms are replaced with deuterium atoms.
  • R 1 is substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a group combining two or more It is a good aryl group.
  • two R 1 are aryl optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or a combination of two or more groups. is the base.
  • groups that at least one R 1 can take include the above P1 to P14.
  • R 1 that can be employed in the present invention is not limitedly interpreted by these specific examples.
  • the group bonded from the right side of the benzene ring to which (R 5 ) n5 is bonded is benzofuro[3,2- a] carbazolyl group, R 1 is not an unsubstituted phenyl group.
  • a compound represented by the general formula (1) can be preferably applied to an organic semiconductor device.
  • a CMOS complementary metal oxide semiconductor
  • the compound represented by formula (1) can be used to fabricate organic optical devices such as organic electroluminescence devices and solid-state imaging devices (for example, CMOS image sensors).
  • the compound represented by the general formula (1) of the present invention can be used for organic light-emitting devices such as organic electroluminescence devices (organic EL devices).
  • organic EL devices organic electroluminescence devices
  • the compound represented by the general formula (1) of the present invention can be effectively used as an electron barrier material for organic light emitting devices.
  • the life of the device can be lengthened by using the compound represented by the general formula (1) of the present invention for the electron barrier layer.
  • An organic electroluminescence element has a structure in which at least an anode, a cathode, and an organic layer are formed between the anode and the cathode.
  • the organic layer includes at least a light-emitting layer, and preferably has one or more organic layers (especially an electron barrier layer) in addition to the light-emitting layer.
  • Organic layers constituting an organic electroluminescence device include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transporting layer, an exciton blocking layer, a base layer for a light emitting layer, and the like. can be mentioned.
  • 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 compound represented by general formula (1) is used for an electron barrier layer of an organic electroluminescence device.
  • the electron barrier layer may contain only the compound represented by the general formula (1), or may contain compounds other than the compound represented by the general formula (1).
  • the concentration of the compound represented by general formula (1) in the electron barrier layer is preferably 50% by weight or more, more preferably 90% by weight or more, and may be, for example, 99% by weight or more. .9% by weight or more.
  • the thickness of the electron barrier layer is preferably 1 nm or more, more preferably 3 nm or more, and can be, for example, 5 nm or more, or, for example, 10 nm or more.
  • the thickness of the electron barrier layer is preferably less than 30 nm, more preferably less than 20 nm, and can be, for example, 15 nm or less.
  • the thickness of the electron barrier layer is preferably smaller than the thickness of the light emitting layer.
  • the thickness of the electron barrier layer is preferably one-half or less, more preferably one-third or less, and can be, for example, one-fourth or less of the thickness of the light-emitting layer. Moreover, it is preferably 1/20 or more, and can be, for example, 1/10 or more, or, for example, 1/6 or more.
  • the electron barrier layer containing the compound represented by formula (1) is preferably provided between the light-emitting layer and the anode.
  • the light-emitting layer and the electron blocking layer are stacked so as to be in direct contact with each other.
  • One embodiment of the present invention includes a stacked structure in which an electron blocking layer containing the compound represented by general formula (1), a base layer, and a light-emitting layer are stacked in this order from the anode side.
  • the electron barrier layer and the base layer are laminated so as to be in direct contact, and the base layer and the light-emitting layer are laminated so as to be in direct contact, but the electron barrier layer and the light-emitting layer are not in contact.
  • the underlayer is formed for the purpose of improving the orientation of the light-emitting layer, and is a layer containing a hole-transporting material.
  • the base layer contains a compound having a common partial structure with the compound contained in the light-emitting layer.
  • the common partial structure here means that a partial structure consisting of 12 or more atoms other than hydrogen atoms and deuterium atoms is common, and 16 or more atoms other than hydrogen atoms and deuterium atoms
  • a partial structure consisting of 20 or more atoms other than a hydrogen atom and a deuterium atom may be common.
  • the base layer contains the same compound as the compound contained in the light-emitting layer.
  • the underlayer contains only the same compounds as those contained in the light-emitting layer.
  • the underlayer contains the same compound as the host material contained in the light-emitting layer.
  • the thickness of the underlayer is preferably 1 nm or more, more preferably 3 nm or more, and can be, for example, 5 nm or more.
  • the thickness of the adjacent layer is preferably less than 30 nm, more preferably less than 20 nm, and can be, for example, 10 nm or less, or 7 nm or less.
  • the thickness of the underlayer is preferably smaller than the thickness of the light-emitting layer.
  • the thickness of the underlayer is preferably one-half or less, more preferably one-third or less, and can be, for example, one-fourth or less of the thickness of the light-emitting layer. Moreover, it is preferably 1/20 or more, and can be, for example, 1/10 or more.
  • the thickness of the underlayer is preferably smaller than the thickness of the electron barrier layer.
  • the thickness of the underlayer can be, for example, three-fourths or less, for example, two-thirds or less, or, for example, one-half or less of the thickness of the electron barrier layer. Moreover, it is preferably 1/20 or more, and can be, for example, 1/10 or more, or, for example, 1/4 or more.
  • the light-emitting layer is a layer that emits light after recombination of holes and electrons injected from the anode and the cathode to generate excitons.
  • the light-emitting layer contains at least a light-emitting material.
  • a host material In order for an organic electroluminescence device to exhibit high luminous efficiency, it is important to confine the singlet excitons and triplet excitons of the luminescent material in the luminescent material. Therefore, it is preferable to use a host material in addition to the light-emitting material in the light-emitting layer.
  • an organic compound having an excited singlet energy higher than that of the light-emitting material of the present invention can be used, and an organic compound having both excited singlet energy and excited triplet energy higher than those of the light-emitting material. is preferably used.
  • the host material singlet excitons and triplet excitons generated in the light-emitting material can be confined in the molecules of the light-emitting material, and the light emission efficiency can be fully exploited. However, even if singlet excitons and triplet excitons cannot be confined sufficiently, it is possible to obtain high luminous efficiency in some cases.
  • the maximum amount of light emitted from the device is emitted from the light-emitting material contained in the light-emitting layer.
  • This emission includes fluorescence emission and may also include delayed fluorescence. However, the emission may be partly or partially emitted from the host material.
  • the concentration of the light-emitting material in the light-emitting layer is preferably 0.1% by weight or more, more preferably 1% by weight or more, and preferably 50% by weight or less. It is more preferably 10% by weight or less, more preferably 10% by weight or less.
  • an assist dopant may be used in the light-emitting layer.
  • the light-emitting layer is composed of a host material, an assist dopant, and a light-emitting material.
  • a host material having a higher lowest excited singlet energy level than the assist dopant is used, and a light-emitting material having a lower lowest excited singlet energy level than the assist dopant is used.
  • a delayed fluorescence material is the fluorescence emitted when a compound in an excited state returns from the excited singlet state to the ground state after reverse intersystem crossing occurs from the excited triplet state to the excited singlet state.
  • the target compound is the delayed fluorescence material.
  • the delayed fluorescent material is preferably a thermally activated delayed fluorescent material capable of causing reverse intersystem crossing by absorption of thermal energy.
  • a thermally activated delayed fluorescence material can be confirmed by the fact that the emission lifetime obtained by measuring the transient decay curve of emission becomes longer depending on the measurement temperature.
  • a delayed fluorescence material as an assist dopant, the energy of the excited singlet state generated by the direct transition from the ground state and the excited singlet energy due to the reverse intersystem crossing in the assist dopant are efficiently transferred to the light-emitting material. , can effectively assist the luminescence of the luminescent material.
  • the concentration of the assist dopant in the light-emitting layer is preferably lower than the content of the host material.
  • the content of the host material is 15% by weight or more and 99.9% by weight or less.
  • the content of the assist dopant is preferably 5.0% by weight or more and 50% by weight or less, and the content of the light-emitting material is 0.5% by weight or more and 5.0% by weight or less. is preferred.
  • the light-emitting layer does not contain an inorganic compound. Further, in one embodiment of the present invention, the light-emitting layer does not contain a metal atom. In one embodiment of the present invention, no phosphorescence is observed from the emissive layer at 300K.
  • the host material used in the light-emitting layer is preferably an organic compound that has hole-transporting ability and electron-transporting ability, prevents emission from becoming longer in wavelength, and has a high glass transition temperature.
  • a compound containing a carbazole structure can be preferably selected as the host material.
  • the host material contains two or more structures selected from the group consisting of a carbazole structure, a dibenzofuran structure and a dibenzothiophene structure, for example a compound containing two structures or a compound containing three structures.
  • a compound can be selected.
  • a compound containing a 1,3-phenylene structure can be selected as the host material.
  • a compound containing a biphenylene structure can be selected as the host material.
  • a compound having 5 to 8 benzene rings contained in the molecule can be selected as the host material. or a compound with 7 may be selected.
  • Preferred compounds that can be used as host materials are listed below, but the host materials that can be employed in the present invention are not limitedly interpreted by the following specific examples.
  • a delayed fluorescence material can be used as a light-emitting material or an assist dopant in the light-emitting layer. Also, different delayed fluorescence materials can be used as the light-emitting material and the assist dopant.
  • a fluorescence lifetime measurement system such as a streak camera system manufactured by Hamamatsu Photonics
  • fluorescence with an emission lifetime of 100 ns (nanoseconds) or more is usually observed.
  • the difference ⁇ EST between the lowest excited singlet energy and the lowest excited triplet energy at 77K is preferably 0.3 eV or less, more preferably 0.25 eV or less, and 0.2 eV or less.
  • thermoly activated delayed fluorescence material absorbs the heat emitted by the device and undergoes reverse intersystem crossing from the excited triplet state to the excited singlet relatively easily, and the excited triplet energy efficiently contributes to light emission. can be done.
  • the lowest excited singlet energy (E S1 ) and the lowest excited triplet energy (E T1 ) of the compound in the present invention are values determined by the following procedure.
  • ⁇ E ST is a value obtained by calculating E S1 -E T1 .
  • (2) Lowest excited singlet energy (E S1 ) A thin film or a toluene solution (concentration 10 ⁇ 5 mol/L) of the compound to be measured is prepared and used as a sample. The fluorescence spectrum of this sample is measured at room temperature (300K). In the fluorescence spectrum, the vertical axis is light emission and the horizontal axis is wavelength.
  • the maximum point with a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and is closest to the maximum value on the short wavelength side.
  • the tangent line drawn at the point where the value is taken is taken as the tangent line to the rise on the short wavelength side of the phosphorescence spectrum.
  • the delayed fluorescence material preferably does not contain metal atoms.
  • a compound composed 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 composed of carbon atoms, hydrogen atoms and nitrogen atoms may be selected as the delayed fluorescence material.
  • a typical delayed fluorescence material is a compound having a structure in which one or two acceptor groups and at least one donor group are bonded to a benzene ring.
  • acceptor group examples include groups containing a heteroaryl ring containing a nitrogen atom as a ring skeleton-constituting atom, such as a cyano group and a triazinyl ring.
  • a preferred example of the donor group is a substituted or unsubstituted carbazol-9-yl group.
  • a compound in which three or more substituted or unsubstituted carbazol-9-yl groups are bonded to the benzene ring, or a substituted or unsubstituted compound in at least one of the two benzene rings constituting the carbazol-9-yl group A benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted silaindene ring, and the like. be able to.
  • a compound represented by the following general formula (4) is used as the delayed fluorescence material.
  • one of R 21 to R 23 represents a cyano group or a group represented by general formula (5) below, and the remaining two of R 21 to R 23 and R 24 and R 25 At least one of them represents a group represented by the following general formula (6), and the rest of R 21 to R 25 are hydrogen atoms or substituents (the substituent here is a cyano group, the following general formula (5) is not a group represented by the following general formula (6)).
  • L1 represents a single bond or a divalent linking group
  • R31 and R32 each independently represent a hydrogen atom or a substituent
  • * represents a bonding position
  • L2 represents a single bond or a divalent linking group
  • R33 and R34 each independently represent a hydrogen atom or a substituent
  • * represents a bonding position
  • R 22 is a cyano group. In a preferred embodiment of the present invention, R 22 is a group represented by general formula (5). In one aspect of the present invention, R 21 is a cyano group or a group represented by general formula (5). In one aspect of the present invention, R 23 is a cyano group or a group represented by general formula (5). In one aspect of the invention, one of R 21 to R 23 is a cyano group. In one aspect of the present invention, one of R 21 to R 23 is a group represented by general formula (5).
  • L 1 in general formula (5) is a single bond.
  • L 1 is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group and more preferably a substituted or unsubstituted 1,4-phenylene group (eg, an alkyl group having 1 to 3 carbon atoms as a substituent).
  • R 31 and R 32 in general formula (5) are each independently an alkyl group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), a heteroaryl group (eg, one group selected from the group consisting of 5 to 30 ring skeleton atoms), an alkenyl group (eg, 1 to 40 carbon atoms) and an alkynyl group (eg, 1 to 40 carbon atoms), or a combination of two or more (these groups are hereinafter referred to as "substituent group A groups").
  • each of R 31 and R 32 is independently a substituted or unsubstituted aryl group (eg, having 6 to 30 carbon atoms), and the substituent of the aryl group is a group of Substituent Group A. can be mentioned.
  • R 31 and R 32 are the same.
  • L2 in general formula ( 6 ) is a single bond.
  • L2 is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group and more preferably a substituted or unsubstituted 1,4-phenylene group (for example, an alkyl group having 1 to 3 carbon atoms as a substituent).
  • R 33 and R 34 in general formula (6) are each independently a substituted or unsubstituted alkyl group (eg, 1 to 40 carbon atoms), a substituted or unsubstituted alkenyl group (eg, 1 to 40), a substituted or unsubstituted aryl group (eg, 6 to 30 carbon atoms), or a substituted or unsubstituted heteroaryl group (eg, 5 to 30 carbon atoms).
  • substituents of the alkyl group, alkenyl group, aryl group, and heteroaryl group referred to herein include hydroxyl group, halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (eg, C 1-40 ), an alkoxy group (eg, 1 to 40 carbon atoms), an alkylthio group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), an aryloxy group (eg, 6 to 30 carbon atoms), an arylthio group ( (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 ring atoms), heteroaryloxy groups (e.g., 5 to 30 ring atoms), heteroarylthio groups (e.g., ring atoms) 5 to 30), acyl groups (eg, 1 to 40 carbon atoms), alky
  • R 33 and R 34 may be bonded to each other via a single bond or a linking group to form a cyclic structure.
  • R 33 and R 34 are aryl groups, they are preferably bonded to each other via a single bond or a linking group to form a cyclic structure.
  • R 35 to R 37 each independently represent a hydrogen atom or a substituent.
  • a group of the substituent group A can be selected, or a group of the substituent group B below can be selected, preferably an alkyl group having 1 to 10 carbon atoms and a group having 6 to 14 carbon atoms. It is one group or a combination of two or more groups selected from the group consisting of aryl groups.
  • the group represented by general formula (6) is preferably a group represented by general formula (7) below.
  • L11 in general formula ( 7 ) represents a single bond or a divalent linking group.
  • the description and preferred range of L 11 can be referred to the description and preferred range of L 2 above.
  • Each of R 41 to R 48 in general formula (7) independently represents a hydrogen atom or a substituent.
  • R 41 and R 42 , R 42 and R 43 , R 43 and R 44 , R 44 and R 45 , R 45 and R 46 , R 46 and R 47 , R 47 and R 48 are bonded to each other to form a cyclic structure. may be formed.
  • the cyclic structure formed by bonding to each other may be an aromatic ring or an alicyclic ring, or may contain a heteroatom, and the cyclic structure may be a condensed ring of two or more rings.
  • the heteroatoms referred to here are preferably those selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms.
  • Examples of cyclic structures formed include benzene ring, naphthalene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, imidazoline ring, oxazole ring, isoxazole ring, thiazole ring, iso thiazole ring, cyclohexadiene ring, cyclohexene ring, cyclopentaene ring, cycloheptatriene ring, cycloheptadiene ring, cycloheptaene ring, furan ring, thiophene ring, naphthyridine ring, quinoxaline ring, quinoline ring and the like.
  • a ring formed by condensing a large number of rings such as a phenanthrene ring or a triphenylene ring may be formed.
  • the number of rings contained in the group represented by general formula (7) may be selected from the range of 3-5, or may be selected from the range of 5-7.
  • substituents that R 41 to R 48 can take include the groups of the above substituent group B, preferably unsubstituted alkyl groups having 1 to 10 carbon atoms or unsubstituted alkyl groups having 1 to 10 carbon atoms. It is an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group.
  • R 41 to R 48 are hydrogen atoms or unsubstituted alkyl groups having 1 to 10 carbon atoms. In a preferred embodiment of the present invention, R 41 to R 48 are hydrogen atoms or unsubstituted aryl groups having 6 to 10 carbon atoms. In a preferred embodiment of the present invention, all of R 41 to R 48 are hydrogen atoms.
  • * represents a bonding position.
  • a preferred embodiment of the present invention uses an azabenzene derivative as the delayed fluorescence material.
  • the azabenzene derivative has an azabenzene structure in which three of the ring skeleton-constituting carbon atoms of the benzene ring are substituted with nitrogen atoms.
  • an azabenzene derivative having a 1,3,5-triazine structure can be preferably selected.
  • the azabenzene derivative has an azabenzene structure in which two of the ring skeleton-constituting carbon atoms of the benzene ring are substituted with nitrogen atoms.
  • azabenzene derivatives having a pyridazine structure, a pyrimidine structure, and a pyrazine structure can be mentioned, and azabenzene derivatives having a pyrimidine structure can be preferably selected.
  • the azabenzene derivative has a pyridine structure in which one of the ring skeleton-constituting carbon atoms of the benzene ring is substituted with a nitrogen atom.
  • a compound represented by the following general formula (8) is used as the delayed fluorescence material.
  • at least one of Y 1 , Y 2 and Y 3 represents a nitrogen atom and the rest represent methine groups.
  • Y 1 is a nitrogen atom and Y 2 and Y 3 are methine groups.
  • Y 1 and Y 2 are preferably nitrogen atoms and Y 3 is preferably a methine group. More preferably, all of Y 1 to Y 3 are nitrogen atoms.
  • Z 1 to Z 3 each independently represent a hydrogen atom or a substituent, at least one of which is a donor substituent.
  • a donor substituent means a group having a negative Hammett's ⁇ p value.
  • at least one of Z 1 to Z 3 is a group containing a diarylamino structure (two aryl groups bonded to the nitrogen atom may be bonded to each other), more preferably the general formula (6 ), for example, a group represented by the general formula (7).
  • only one of Z 1 to Z 3 is a group represented by general formula (6) or (7).
  • only two of Z 1 to Z 3 are each independently a group represented by general formula (6) or (7).
  • all of Z 1 to Z 3 are each independently a group represented by general formula (6) or (7).
  • Z 1 to Z 3 that are not groups represented by general formulas (6) and (7) are substituted or unsubstituted aryl groups (eg, 6 to 40 carbon atoms, preferably 6 to 20 carbon atoms).
  • the substituents of the aryl group referred to herein include an aryl group (eg, 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms) and an alkyl group (eg, 1 to 20 carbon atoms, preferably 1 to 6).
  • aryl group eg, 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms
  • alkyl group eg, 1 to 20 carbon atoms, preferably 1 to 6
  • general formula (8) does not contain a cyano group.
  • a compound represented by the following general formula (9) is used as the delayed fluorescence material.
  • Ar 1 forms a cyclic structure that may be substituted with A 1 and D 1 below, and represents a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring.
  • Ar 2 and Ar 3 each may form a cyclic structure, and when they form a cyclic structure, they represent a benzene ring, a naphthalene ring, a pyridine ring, or a cyano-substituted benzene ring.
  • D 1 represents a substituted or unsubstituted 5H-indolo[3,2,1-de]phenazin-5-yl group or a substituted or unsubstituted heterocyclic condensed carbazolyl group containing no naphthalene structure; ), they may be the same or different. Also, the substituents of D 1 may be bonded to each other to form a cyclic structure.
  • delayed fluorescence materials include compounds represented by the following general formula (E1).
  • 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 joined together to form an acceptor group, or R 2 and R 3 are joined together to form an acceptor group.
  • R3 and R4 , R4 and R5 , R5 and R6 , R6 and R7 , R7 and R8 , R9 and R10 , R10 and R11 , R11 and R12 , R12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 may combine with each other to form a cyclic structure.
  • X 1 represents O or NR, and R represents a substituent.
  • X 3 and X 4 are O or NR, and the rest 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 in general formula (1) 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 and CR 16 may be substituted with N;
  • delayed fluorescence materials include compounds represented by the following general formula (E2).
  • 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 represents 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 , R 16 and R 1 are bonded to each other A cyclic structure may be formed.
  • 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 in general formula (1) 11 , CR 12 , CR 13 , CR 14 , CR 15 and CR 16 may be substituted with N;
  • delayed fluorescence materials include compounds represented by the following general formula (E3).
  • Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 1 to R 9 each independently represent a hydrogen atom, represents a deuterium atom or a substituent.
  • 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 7 and R 8 , R 8 and R 9 are bonded together to form a cyclic structure
  • You may have provided that Z 1 , Z 2 , a ring formed by bonding R 1 and R 2 together, a ring formed by bonding R 2 and R 3 together, a ring formed by bonding R 4 and R 5 together, and at least one of the rings 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 an aryl
  • delayed fluorescence materials include compounds represented by the following general formula (E4).
  • Z 1 is a furan ring condensed with a substituted or unsubstituted benzene ring, a thiophene ring condensed with a substituted or unsubstituted benzene ring, or an N- represents a substituted pyrrole ring
  • Z 2 and Z 3 each independently 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 2 , Z 2 and Z 3 , Z 3 and R 3 may combine with each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 are bonded to each other to form a cyclic structure.
  • delayed fluorescence materials include compounds represented by the following general formula (E5).
  • 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 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 3 to R 9 each independently represents a hydrogen atom, a deuterium atom or a substituent.
  • R 1 , R 2 , Z 1 and Z 2 includes a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring.
  • R 1 and Z 1 , Z 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and Z 2 , Z 2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , and R 9 and R 1 may be bonded to each other to form a cyclic structure.
  • Substitutable carbon atoms among the benzene ring skeleton-constituting carbon atoms constituting the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with a nitrogen atom.
  • C—R 3 , C—R 4 , C—R 5 , C—R 6 , C—R 7 , C—R 8 and C—R 9 in general formula (1) may be substituted with N good.
  • delayed fluorescence materials include compounds represented by the following general formula (E6).
  • R 201 to R 221 each independently represent a hydrogen atom, a deuterium atom or a substituent, preferably a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or an alkyl group and an aryl group represents a bonded group.
  • R201 and R202 , R202 and R203 , R203 and R204 , R205 and R206 , R206 and R207 , R207 and R208 , R214 and R215 , R215 and R216 , R216 and R 217 , R 218 and R 219 , R 219 and R 220 , R 220 and R 221 are bonded to each other to form a benzofuro structure or a benzothieno structure.
  • R 201 and R 202 , R 202 and R 203 , R 203 and R 204 , R 205 and R 206 , R 206 and R 207 , R 207 and R 208 and R 214 and R 215 , R 215 and R 216 , R 216 and R 217 , R 218 and R 219 , R 219 and R 220 , R 220 and R 221 are bonded together to form a benzofuro structure or It forms a benzothieno structure.
  • R 203 and R 204 are bonded together to form a benzofuro structure or a benzothieno structure, and even more preferably R 203 and R 204 and R 216 and R 217 are bonded together to form a benzofuro structure or a benzothieno structure.
  • R 203 and R 204 , R 216 and R 217 are bonded to each other to form a benzofuro structure or benzothieno structure
  • R 206 and R 219 are substituted or unsubstituted aryl groups (preferably substituted or unsubstituted a substituted phenyl group, more preferably an unsubstituted phenyl group).
  • General formula (E6) includes structures in which R 201 to R 208 and R 214 to R 221 may each independently be a deuterium atom, but are not a hydrogen atom ( 1 H). That is, when R 201 to R 208 and R 214 to R 221 contain atoms with one proton, the atoms are limited to deuterium atoms.
  • t-Bu represents a tertiary butyl group (tert-butyl group).
  • JP 2013-253121, WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895, WO2014/126200, WO2014/136758, WO2014/133121 Publications, WO2014/136860, WO2014/196585, WO2014/189122, WO2014/168101, WO2015/008580, WO2014/203840, WO2015/002213, WO2010/01620 WO2015/019725, WO2015/072470, WO2015/108049, WO2015/080182, WO2015/072537, WO2015/080183, JP 2015-129240, WO2015/129714, WO2015/129715, WO2015/133501, WO2015/136880, WO2015/137244, WO2015/137202, WO2015/137136, WO2015/146541, WO2015/159541
  • a luminescent material that emits delayed fluorescence can also be employed.
  • a compound having a lowest excited singlet energy lower than that of the assist dopant is used as the light-emitting material.
  • the light-emitting material used in combination with the assist dopant include compounds having multiple resonance effects of boron atoms and nitrogen atoms, and compounds containing condensed aromatic ring structures such as anthracene, pyrene, and perylene.
  • the delayed fluorescence materials exemplified so far can also be used.
  • a compound represented by General Formula (F1) below is used as a light-emitting material used in combination with an assist dopant.
  • Ar 1 to Ar 3 are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted, or the rings may be condensed.
  • a hydrogen atom is substituted, it is preferably substituted with one or a combination of two or more groups selected from the group consisting of deuterium atoms, aryl groups, heteroaryl groups and alkyl groups.
  • a benzene ring or a heteroaromatic ring for example, a furan ring, a thiophene ring, a pyrrole ring, etc.
  • R a and R a ' each independently represent a substituent, preferably one or a combination of two or more selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group and an alkyl group.
  • Ra and Ar 1 , Ar 1 and Ar 2 , Ar 2 and Ra′, Ra ′ and Ar 3 , and Ar 3 and Ra may combine with each other to form a cyclic structure.
  • the compound represented by general formula (F1) preferably contains at least one carbazole structure.
  • one benzene ring constituting the carbazole structure may be a ring represented by Ar 1
  • one benzene ring constituting the carbazole structure may be a ring represented by Ar 2
  • the carbazole structure may be a ring represented by Ar 3 .
  • a carbazolyl group may be bonded to one or more of Ar 1 to Ar 3 .
  • a substituted or unsubstituted carbazol-9-yl group may be attached to the ring represented by Ar 3 .
  • a condensed aromatic ring structure such as anthracene, pyrene, or perylene may be bonded to Ar 1 to Ar 3 .
  • the rings represented by Ar 1 to Ar 3 may be one ring constituting a condensed aromatic ring structure.
  • at least one of R a and R a ′ may be a group having a condensed aromatic ring structure.
  • a plurality of skeletons represented by general formula (F1) may be present in the compound.
  • the skeletons represented by general formula (F1) may have a structure in which they are bonded to each other via a single bond or a linking group.
  • the skeleton represented by the general formula (F1) may further have a structure exhibiting a multiple resonance effect in which benzene rings are linked to each other by a boron atom, a nitrogen atom, an oxygen atom, or a sulfur atom.
  • a compound containing a BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) structure is used as a light-emitting material used in combination with an assist dopant.
  • a compound represented by the following general formula (F2) is used.
  • R 1 to R 7 are each independently a hydrogen atom, a deuterium atom or a substituent. At least one of R 1 to R 7 is preferably a group represented by general formula (F3) below.
  • General formula (F3) In general formula (F3), R 11 to R 15 each independently represent a hydrogen atom, a deuterium atom or a substituent, and * represents a bonding position.
  • the group represented by general formula (F3) may be one, two, or three of R 1 to R 7 in general formula (F2). Also, it may be at least four, for example four or five. In a preferred embodiment of the present invention, one of R 1 to R 7 is a group represented by general formula (F3).
  • R 1 , R 3 , R 5 and R 7 are groups represented by general formula (F3). In a preferred embodiment of the present invention, only R 1 , R 3 , R 4 , R 5 and R 7 are groups represented by general formula (F3). In a preferred embodiment of the present invention, R 1 , R 3 , R 4 , R 5 and R 7 are groups represented by general formula (F3), R 2 and R 4 are hydrogen atoms, deuterium atoms, A substituted alkyl group (eg, 1 to 10 carbon atoms) or an unsubstituted aryl group (eg, 6 to 14 carbon atoms).
  • R 1 to R 7 are groups represented by general formula (F3).
  • R 1 and R 7 are the same.
  • R 3 and R 5 are the same.
  • R 2 and R 6 are the same.
  • R 1 and R 7 are the same, R 3 and R 5 are the same, and R 1 and R 3 are different from each other.
  • R 1 , R 3 , R 5 and R 7 are identical.
  • R 1 , R 4 and R 7 are the same and different from R 3 and R 5 .
  • R3 , R4 and R5 are the same and different from R1 and R7 .
  • R 1 , R 3 , R 5 and R 7 are all different from R 4 .
  • Substituents that can be taken by R 11 to R 15 in the general formula (F3) are, for example, selected from the following substituent group A, selected from the following substituent group B, or selected from the following substituent group C. , or the following substituent group D.
  • a substituted amino group is selected as a substituent, a disubstituted amino group is preferred, and the two substituents for the amino group are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted Alternatively, it is preferably an unsubstituted alkyl group, and particularly preferably a substituted or unsubstituted aryl group (diarylamino group).
  • Substituents that can be taken by the two aryl groups of the diarylamino group are, for example, selected from the following substituent group A, selected from the following substituent group B, selected from the following substituent group C, and the following substituents You can choose from group D.
  • the two aryl groups of the diarylamino group may be bonded to each other via a single bond or a linking group, and the linking group referred to here can be referred to the description of the linking group for R 33 and R 34 .
  • a specific example of the diarylamino group is, for example, a substituted or unsubstituted carbazol-9-yl group.
  • Examples of substituted or unsubstituted carbazol-9-yl groups include groups in which L 11 in the general formula (9) is a single bond.
  • R 13 in general formula (F3) is a substituent, and R 11 , R 12 , R 14 and R 15 are hydrogen atoms.
  • R 11 in general formula (F3) is a substituent, and R 12 , R 13 , R 14 and R 15 are hydrogen atoms.
  • R 11 and R 13 in general formula (F3) are substituents, and R 12 , R 14 and R 15 are hydrogen atoms.
  • R 1 to R 7 of general formula (F2) may include a group in which all of R 11 to R 15 of general formula (F3) are hydrogen atoms (ie, phenyl group).
  • R2 , R4 , R6 may be phenyl groups.
  • R 8 and R 9 each independently represent a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group (eg, 1 to 40 carbon atoms), an alkoxy group (eg, 1 to 40 carbon atoms), an aryloxy It is preferably one or a combination of two or more groups selected from the group consisting of a group (for example, 6 to 30 carbon atoms) and a cyano group.
  • R8 and R9 are the same .
  • R 8 and R 9 are halogen atoms, particularly preferably fluorine atoms.
  • the total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present in R 1 to R 9 of general formula (F2) is The number is preferably three or more, and for example, three compounds or four compounds can be employed. More preferably, the total number of substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted amino groups present in R 1 to R 7 in general formula (F2) is 3 or more. is preferable, and for example, a compound with three or a compound with four can be used.
  • an alkoxy group, an aryloxy group, or an amino group may not exist in R8 and R9. More preferably, a substituted or unsubstituted alkoxy group , a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino
  • the total number of groups is preferably 3 or more, and for example, a compound with 3 or a compound with 4 can be used.
  • R 2 , R 6 , R 8 and R 9 may be free of an alkoxy group, an aryloxy group and an amino group. In a preferred embodiment of the invention, there are 3 or more substituted or unsubstituted alkoxy groups.
  • each of R 1 , R 4 and R 7 is a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy. In a preferred embodiment of the present invention, each of R 1 , R 4 and R 7 has a substituted or unsubstituted alkoxy group.
  • the total number of substituents having a Hammett's ⁇ p value of less than ⁇ 0.2 in R 1 to R 9 of the general formula (F2) is 3 or more.
  • Hammett's ⁇ p value is less than -0.2 substituents, for example, methoxy group (-0.27), ethoxy group (-0.24), n-propoxy group (-0.25), isopropoxy group (- 0.45) and the n-butoxy group (-0.32).
  • fluorine atom (0.06), methyl group (-0.17), ethyl group (-0.15), tert-butyl group (-0.20), n-hexyl group (-0.15), cyclohexyl Groups such as ( ⁇ 0.15) are not substituents with a Hammett ⁇ p value of less than ⁇ 0.2.
  • a compound in which the number of substituents having a Hammett's ⁇ p value of less than ⁇ 0.2 in R 1 to R 9 of the general formula (F2) is three, or four can be employed.
  • the number of substituents having a Hammett's ⁇ p value of less than ⁇ 0.2 in R 1 to R 7 of the general formula (F2) is preferably 3 or more, for example, a compound having 3 can be employed, or a compound that is four. At this time, a substituent having a Hammett's ⁇ p value of less than ⁇ 0.2 may not be present in R 8 and R 9 . More preferably, the number of substituents having a Hammett's ⁇ p value of less than ⁇ 0.2 in R 1 , R 3 , R 4 , R 5 and R 7 in the general formula (F2) is 3 or more. Preferably, for example, three compounds can be employed, or four compounds can be employed.
  • each of R 1 , R 4 and R 7 has a Hammett's ⁇ p value of less than ⁇ 0.2.
  • a compound containing a carbazole structure may be selected as a light-emitting material used in combination with an assist dopant.
  • a compound that does not contain any of the carbazole structure, the dibenzofuran structure, and the dibenzothiophene structure may be selected as the light-emitting material used in combination with the assist dopant.
  • t-Bu represents a tertiary butyl group (tert-butyl group).
  • Derivatives of the above-exemplified compounds include compounds in which at least one hydrogen atom is replaced with a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, or a diarylamino group.
  • compounds described in paragraphs 0220 to 0239 of WO2015/022974 can also be preferably used as a light-emitting material used in combination with an assist dopant.
  • a compound represented by general formula (G) below is used in the light-emitting layer.
  • the compound represented by general formula (G) is preferably employed as a light-emitting material used in combination with an assist dopant.
  • a compound represented by the general formula (G) may be employed as an assist dopant.
  • one of X 1 and X 2 is a nitrogen atom and the other is a boron atom.
  • X 1 is a nitrogen atom and X 2 is a boron atom.
  • R 17 and R 18 combine with each other to form a single bond to form a pyrrole ring.
  • X 1 is a boron atom and X 2 is a nitrogen atom.
  • R 21 and R 22 combine with 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.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 are bonded together to form a cyclic It may form a structure.
  • the cyclic structure formed by combining R 7 and R 8 contains a boron atom and 4 carbon atoms as ring skeleton-constituting atoms.
  • the cyclic structure formed by combining R 17 and R 18 contains a boron atom and 4 carbon atoms as ring skeleton constituent atoms when X 1 is a boron atom.
  • X 1 is a nitrogen atom
  • the cyclic structure is limited to pyrrole rings.
  • the cyclic structure formed by combining R 21 and R 22 contains a boron atom and 4 carbon atoms as ring skeleton constituent atoms when X 2 is a boron atom.
  • the cyclic structure is limited to pyrrole rings.
  • R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded together to form a cyclic structure containing a boron atom, the cyclic structure is preferably a 5- to 7-membered ring.
  • a 6-membered ring is more preferred, and a 6-membered ring is even more preferred.
  • R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded to each other, they are bonded to form a single bond, —O—, —S—, —N(R 27 )—, —C( R 28 )(R 29 )—, —Si(R 30 )(R 31 )—, —B(R 32 )—, —CO—, —CS—, are preferably formed, and —O—, —S It is more preferred to form - or -N(R 27 )-, and more preferred to form -N(R 27 )-.
  • R 27 to R 32 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 27 is particularly preferably a substituted or unsubstituted aryl group.
  • R 27 to R 32 in the ring formed by combining R 17 and R 18 may combine with at least one of R 16 and R 19 to further form a cyclic structure
  • R 21 and R R 27 to R 32 in the ring formed by combining 22 with each other may further combine with at least one of R 20 and R 23 to form a cyclic structure.
  • only one pair of R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bound together.
  • only two pairs of R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are attached to each other.
  • all of R 7 and R 8 , R 17 and R 18 , R 21 and R 22 are bonded together.
  • 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 may be bonded to each other to form a cyclic structure, which may be an aromatic ring or an aliphatic ring, It may also contain a heteroatom, and may be condensed with one or more other rings.
  • heteroatoms referred to here are preferably those selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms.
  • cyclic structures formed include benzene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, imidazoline ring, furan ring, thiophene ring, oxazole ring, and isoxazole ring.
  • the cyclic structure is a substituted or unsubstituted benzene ring (the ring may be further condensed), for example, a benzene ring optionally substituted with an alkyl group or an aryl group. .
  • the cyclic structure is a substituted or unsubstituted heteroaromatic ring, preferably a furan ring of benzofuran or a thiophene ring of benzothiophene.
  • any one of 1 to 4 can be selected, and 1 can be selected, 2 can be selected, 3 or 4 can be selected.
  • a pair selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded together to form a cyclic structure.
  • R 5 and R 6 are linked together to form a cyclic structure.
  • a pair selected from R 9 and R 10 , R 10 and R 11 , and R 11 and R 12 are bonded together to form a cyclic structure.
  • both R 1 and R 2 and R 13 and R 14 are bonded together to form a cyclic structure.
  • a pair selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded to each other to form a cyclic structure, and R 5 and R 6 are bonded to each other to form a ring structure.
  • both R 5 and R 6 and R 19 and R 20 are bonded together to form a cyclic structure.
  • R 1 to R 26 that are not bonded to adjacent R n are hydrogen atoms, deuterium atoms or substituents.
  • substituents a group selected from any of Substituent Groups A to E described later can be employed.
  • Preferred substituents that R 1 to R 26 can take are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, for example, the substituent is a substituted or unsubstituted aryl groups and, for example, substituents may be substituted or unsubstituted alkyl groups.
  • the substituents of the alkyl group, aryl group, and heteroaryl group referred to herein can also adopt a group selected from any one of the substituent groups A to E, but preferably an alkyl group, an aryl group, and a heteroaryl group. It is one or more groups selected from the group consisting of, more preferably a group of substituent group E, which may be unsubstituted.
  • at least one of R 1 to R 6 is a substituent, preferably a group of substituents E.
  • at least one of R 2 to R 6 is a substituent, preferably a group of substituent group E.
  • At least one of R 5 and R 6 is a substituent, preferably a group of substituent group E.
  • at least one of R 3 and R 6 is a substituent, more preferably both are substituents, preferably a group of substituents E.
  • when X 1 is a nitrogen atom at least one of R 15 and R 20 is a substituent, more preferably both are substituents, preferably a group of substituent group E be. At this time, R17 and R18 are bonded to each other to form a single bond.
  • R19 and R24 are substituents, more preferably both are substituents, preferably a group of substituent group E be.
  • R 21 and R 22 are bonded together to form a single bond.
  • at least one of R 8 and R 12 is a substituent, preferably both are substituents.
  • R 8 , R 10 and R 12 are substituents. Unsubstituted alkyl groups are preferred as substituents for R 8 to R 12 .
  • R 8 and R 12 are alkyl groups with 2 or more carbon atoms (preferably alkyl groups with 3 or more carbon atoms, more preferably alkyl groups with 3 to 8 carbon atoms, still more preferably alkyl groups with 3 or 4 carbon atoms). In some cases, the orientation becomes high when formed into a film, which is preferable.
  • R 8 and R 12 are substituent groups (preferably alkyl groups, more preferably alkyl groups having 2 or more carbon atoms, still more preferably alkyl groups having 3 or more carbon atoms, still more preferably alkyl groups having 3 to 8 carbon atoms).
  • R 1 to R 6 is a substituent (preferably a group of substituent group E).
  • R 13 and R 17 are substituents when X 1 is a boron atom.
  • R 13 , R 15 and R 17 are substituents when X 1 is a boron atom.
  • the substituents of R 13 to R 17 are preferably unsubstituted alkyl groups.
  • X2 is a boron atom
  • at least one of R22 and R26 is a substituent, preferably both are substituents.
  • R 22 , R 24 and R 26 are substituents when X 2 is a boron atom.
  • the substituents of R 22 to R 26 are preferably unsubstituted alkyl groups.
  • Specific examples of the boron atom represented by B in the general formula (G) and the groups bonded to the boron atom represented by X 1 or X 2 are shown below.
  • the groups bonded to boron atoms that can be employed in the present invention are not limitedly interpreted by the following specific examples.
  • CH3 is omitted from the methyl group. * represents a binding position.
  • R 1 to R 26 in formula (G) Specific examples of R 1 to R 26 in formula (G) are given below.
  • R 1 to R 7 and R 13 to R 21 when X 1 is a nitrogen atom, and R 18 to R 26 when X 2 is a nitrogen atom are preferably Z1 to Z9, and R 8 to R 12 and X 1 Z1 to Z7 are preferred as R 22 to R 26 when is a nitrogen atom, and R 13 to R 17 when X 2 is a nitrogen atom.
  • D represents a deuterium atom. * represents a binding position.
  • a 1 and A 2 are hydrogen atoms, deuterium atoms or substituents.
  • substituent a group selected from any of Substituent Groups A to E described later can be employed.
  • a 1 and A 2 are each independently a hydrogen atom or a deuterium atom.
  • a 1 and A 2 are hydrogen atoms.
  • a 1 and A 2 are deuterium atoms.
  • One of A 1 and A 2 may be a substituent.
  • a 1 and A 2 may each independently be a substituent.
  • a preferred substituent that A 1 and A 2 can take is an acceptor group.
  • the acceptor group is a group having a positive Hammett ⁇ p value.
  • the acceptor group that A 1 and A 2 can take is more preferably a group having a Hammett's ⁇ p value of greater than 0.2.
  • Groups having a Hammett's ⁇ p value of greater than 0.2 include a cyano group, an aryl group substituted with at least a cyano group, a group containing a fluorine atom, and a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom. can be mentioned.
  • the aryl group substituted with at least a cyano group here may be substituted with a substituent other than a cyano group (for example, an alkyl group or an aryl group), but it is an aryl group substituted only with a cyano group.
  • the aryl group substituted with at least a cyano group is preferably a phenyl group substituted with at least a cyano group.
  • the number of substituents of the cyano group is preferably 1 or 2, and may be 1 or 2, for example.
  • the group containing a fluorine atom includes a fluorine atom, a fluorinated alkyl group, and an aryl group substituted with at least a fluorine atom or a fluorinated alkyl group.
  • the fluorinated alkyl group is preferably a perfluoroalkyl group and preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
  • a heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom may be a monocyclic ring or a condensed ring in which two or more rings are condensed.
  • the number of rings after condensed is preferably 2 to 6, and can be selected from 2 to 4, or can be 2, for example.
  • Specific examples of the ring constituting the heteroaryl group include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, naphthyridine ring other than quinazoline ring and quinoxaline ring. .
  • the ring constituting the heteroaryl group may be substituted with a deuterium atom or a substituent, and the substituent is, for example, one or two groups selected from the group consisting of alkyl groups, aryl groups and heteroaryl groups Groups formed by combining two or more groups can be mentioned.
  • a cyano group is particularly preferred as an acceptor group that A 1 and A 2 can take.
  • at least one of A 1 and A 2 is an acceptor group.
  • only one of A 1 and A 2 is an acceptor group.
  • both A 1 and A 2 are the same acceptor group.
  • a 1 and A 2 are different acceptor groups.
  • a 1 and A 2 are cyano groups.
  • a 1 and A 2 are halogen atoms, for example bromine atoms.
  • acceptor group that can be employed in the present invention
  • the acceptor group that can be used in the present invention is not limited to the following specific examples.
  • the methyl group omits the indication of CH3 . Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups.
  • "D" represents a deuterium atom. * represents a binding position.
  • X 1 is a nitrogen atom
  • R 7 and R 8 are bonded via a nitrogen atom to form a 6-membered ring
  • R 21 and R 22 are bonded via a nitrogen atom to form a 6-membered ring.
  • R 17 and R 18 are joined together to form a single bond
  • at least one of R 1 to R 6 is a substituted or unsubstituted aryl group, or 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 are bonded to each other to form an aromatic ring (optionally condensed substituted or unsubstituted benzene ring) or heteroaromatic It forms a ring (preferably a furan ring of optionally condensed substituted or unsubstituted benzofuran, or a thiophene ring of optionally condensed substituted or unsubstituted benzothiophene).
  • X 1 is a boron atom
  • X 2 is a nitrogen atom
  • R 7 and R 8 and R 17 and R 18 are bonded to each other to form a cyclic structure containing a boron atom
  • the cyclic structure is It is a 5- to 7-membered ring, and in the case of a 6-membered ring, R 7 and R 8 , R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS- or -N( R 27 )—.
  • R27 preferably represents a hydrogen atom, a deuterium atom or a substituent.
  • Each hydrogen atom in skeletons (1a) and (1b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (G) compounds in which phenyl groups bonded to boron atoms in skeletons (1a) and (1b) are both substituted with mesityl groups, 2,6-diisopropylphenyl groups or 2,4,6-triisopropylphenyl groups; can be exemplified.
  • each hydrogen atom in skeletons (1a) and (1b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 1 to Ar 4 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R 41 and R 42 each independently represent a substituted or unsubstituted alkyl group.
  • n1 and m2 each independently represent an integer of 0 to 5; n1 and n3 each independently represent an integer of 0 to 4; n2 and n4 each independently represent an integer of 0 to 3; A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent. At least one of n1 to n4 is 1 or more, and m1 and m2 are each independently preferably an integer of 1 to 5. In one aspect of the present invention, each of n1-n4 independently represents an integer of 0-2.
  • n1 to n4 is 1 or more, preferably at least one of n1 and n2 is 1 or more, and at least one of n3 and n4 is 1 or more.
  • n1 and n3 are each independently 1 or 2, and n2 and n4 are 0.
  • n2 and n4 are each independently 1 or 2
  • n1 and n3 are 0.
  • n1-n4 are each independently 1 or 2.
  • n1 and n3 are equal and n2 and n4 are equal.
  • n1 and n3 are 1 and n2 and n4 are 0. In one aspect of the invention, n1 and n3 are 0 and n2 and n4 are 1. In one aspect of the present invention, n1 to n4 are all 1.
  • the bonding positions of Ar 1 to Ar 4 may be at least one of the 3- and 6-positions of the carbazole ring, at least one of the 2- and 7-positions, or at least one of the 1- and 8-positions. It may be one or at least one of the 4th and 5th positions.
  • the bonding positions of Ar 1 to Ar 4 may be both 3 and 6 positions, both 2 and 7 positions, or both 1 and 8 positions of the carbazole ring. and may be both 4th and 5th.
  • positions 3 and 6 can be preferably selected, or both positions 3 and 6 can be more preferably selected.
  • Ar 1 to Ar 4 are all the same group.
  • Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group or naphthyl group, still more preferably a substituted or unsubstituted is the phenyl group of Examples of the substituent include a group selected from any one of Substituent Groups A to E described below, but an unsubstituted phenyl group is also preferred.
  • Ar 1 to Ar 4 include a phenyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group and a terphenyl group.
  • m1 and m2 are each independently 0.
  • m1 and m2 are each independently an integer from 1 to 5.
  • m1 and m2 are equal.
  • R 41 and R 42 are alkyl groups having 1 to 6 carbon atoms and can be selected, for example, from alkyl groups having 1 to 3 carbon atoms, or can be selected as methyl groups. .
  • substitution positions of the alkyl group are 2-position only, 3-position only, 4-position only, 3-position and 5-position, 2-position and 4-position, 2-position and 6-position with the carbon atom bonded to the boron atom as 1-position.
  • 2-position, 4-position and 6-position can be exemplified, preferably at least 2-position, more preferably at least 2-position and 6-position.
  • general formula (G) For descriptions and preferred ranges of A 1 and A 2 , reference can be made to the corresponding description of general formula (G).
  • Ar 5 to Ar 8 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R43 and R44 each independently represent a substituted or unsubstituted alkyl group.
  • n5 and n8 each independently represent an integer of 0 to 3; n5 and n7 each independently represent an integer of 0 to 4; A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the descriptions of m2, n1 to n4, A 1 and A 2 can be referred to.
  • At least one of n5 to n8 is 1 or more, and each of m3 and m4 is preferably an integer of 1 to 5 independently.
  • the compound of the present invention has, for example, the following skeleton (2a) when X 1 is a nitrogen atom, and X When 2 is a nitrogen atom, it has, for example, the following skeleton (2b). Ph is a phenyl group. Skeleton (2a)
  • Each hydrogen atom in skeletons (2a) and (2b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with adjacent hydrogen atoms to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (G) At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in skeleton (2a) is substituted with a substituted or unsubstituted aryl group.
  • each hydrogen atom in skeletons (2a) and (2b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 9 to Ar 14 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n9, n11, n12 and n14 each independently represent an integer of 0 to 4;
  • n10 and n13 each independently represent an integer of 0 to 2; However, at least one of n9, n10, n12, and n13 is 1 or more.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • each of n9-n14 independently represents an integer of 0-2. In one aspect of the present invention, at least one of n9 to n14 is 1 or more.
  • n9 and n12 can be 1 or more, and n10 and n13 can be 1 or more. In a preferred embodiment of the present invention, at least one of n9, n10, n12 and n13 is 1 or more.
  • n9 and n12 are each independently 1 or 2, and n10, n11, n13, and n14 are 0. In one aspect of the present invention, n10 and n13 are each independently 1 or 2, and n9, n11, n12 and n14 are 0.
  • n9 and n12 are each independently 1 or 2
  • n10 and n13 are each independently 1 or 2
  • n11 and n14 are 0.
  • n9-n14 are all 1.
  • the binding positions of Ar 9 to Ar 14 can be the 3,6 positions of the carbazole ring or other positions.
  • Ar 9 to Ar 14 are all the same group.
  • Ar 15 to Ar 20 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n15, n17, n18 and n20 each independently represent an integer of 0 to 4;
  • n16 and n19 each independently represent an integer of 0 to 2;
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the compound of the present invention has, for example, the following skeleton (3a) when X 1 is a nitrogen atom, and X 2 is a nitrogen atom, it has, for example, the following skeleton (3b).
  • Each hydrogen atom in skeletons (3a) and (3b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • a deuterium atom or a substituent may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 1 to R 26 A 1 and A 2 in general formula (G).
  • each hydrogen atom in skeletons (3a) and (3b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 21 to Ar 26 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n21, n23, n24 and n26 each independently represent an integer of 0 to 4; n22 and n25 each independently represent an integer of 0 to 2;
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 9 to Ar 14 , n9 to n14, A 1 and A 2 in formula (2a) can be referred to.
  • Ar 27 to Ar 32 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n27, n29, n30 and n32 each independently represent an integer of 0 to 4;
  • n28 and n31 each independently represent an integer of 0 to 2;
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • a compound is selected in which two benzene rings constituting the carbazole partial structure present in general formula (G) are fused with another ring.
  • a compound in which a benfuran ring is condensed, a compound in which a benzothiophene ring is condensed, and a compound in which a benzene ring is condensed can be particularly preferably selected. Compounds in which these rings are condensed will be described below with specific examples.
  • Preferred examples include compounds in which a benzofuran ring or a benzothiophene ring is condensed with a benzene ring to which a boron atom is not directly bonded, of the two benzene rings constituting the carbazole partial structure present in the general formula (G).
  • Examples of such compounds include compounds having the following skeleton (4a) and compounds having the following skeleton (4b).
  • Y 1 to Y 4 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • the two hydrogen atoms here indicate a state in which two benzene rings bonded to the boron atom are not connected to each other.
  • Y 1 and Y 2 are preferably the same, and Y 3 and Y 4 are preferably the same, but they may be different.
  • Y 1 -Y 4 are single bonds.
  • Y 1 -Y 4 are N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 1 to Z 4 each independently represent an oxygen atom or a sulfur atom.
  • Z 1 and Z 2 are preferably the same, and Z 3 and Z 4 are preferably the same, but they may be different.
  • Z 1 -Z 4 are oxygen atoms.
  • the furan ring of benzofuran is fused to the benzene ring that constitutes the carbazole partial structure in (4a) and (4b).
  • the orientation of the condensed furan ring is not restricted.
  • Z 1 -Z 4 are sulfur atoms.
  • the thiophene ring of benzothiophene is fused to the benzene ring that constitutes the carbazole partial structure in (4a) and (4b).
  • the orientation of the fused thiophene rings is not restricted.
  • Each hydrogen atom in skeletons (4a) and (4b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with adjacent hydrogen atoms to form a cyclic structure.
  • R 1 to R 26 , A 1 and A 2 in general formula (G) each hydrogen atom in skeletons (4a) and (4b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 51 and Ar 52 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, such as a substituted or unsubstituted can be preferably selected.
  • R51 and R52 each independently represent a substituted or unsubstituted alkyl group.
  • m51 and m52 each independently represent an integer of 0 to 4; n51 and n52 each independently represent an integer of 0 to 2; Y 1 to Y 4 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 1 to Z 4 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n51 and n52 are the same number.
  • n51 and n52 may be 0, and n51 and n52 may be 1.
  • m51 and m52 are the same number.
  • m51 and m52 are integers from 0-3.
  • m51 and m52 may be 0, m51 and m52 may be 1, m51 and m52 may be 2, and m51 and m52 may be 3.
  • Preferred groups for Ar 51 , Ar 52 , R 51 , R 52 , A 1 and A 2 are the corresponding descriptions for Ar 1 to Ar 4 , R 41 to R 42 , A 1 and A 2 in general formula (1a) can be referred to.
  • Ar 53 and Ar 54 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R53 and R54 each independently represent a substituted or unsubstituted alkyl group.
  • m53 and m54 each independently represent an integer of 0 to 4; n53 and n54 each independently represents an integer of 0 to 2; Y 3 and Y 4 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z3 and Z4 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 53 , Ar 54 , R 53 , R 54 , m53, m54, n53, n54, A 1 and A 2 refer to Ar 51 , Ar 52 , R 51 , R 52 , m51, The descriptions of m52, n51, n52, A 1 and A 2 can be referred to.
  • the compound represented by the general formula (4b) is not limited to the following specific examples.
  • compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • a compound in which a benzofuran ring or a benzothiophene ring is condensed with a benzene ring to which a boron atom is directly bonded, of the two benzene rings constituting the carbazole partial structure present in the general formula (G) can be preferably mentioned.
  • Examples of such compounds include compounds having the following skeleton (5a) and compounds having the following skeleton (5b).
  • Y 5 to Y 8 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Z 5 to Z 8 each independently represent an oxygen atom or a sulfur atom.
  • each hydrogen atom in skeletons (5a) and (5b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 55 and Ar 56 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R55 and R56 each independently represent a substituted or unsubstituted alkyl group.
  • m55 and m56 each independently represents an integer of 0 to 4;
  • n55 and n56 each independently represent an integer of 0 to 4;
  • Y 5 and Y 6 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z5 and Z6 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n55 and n56 are integers from 0-2.
  • n55 and n56 may be 0 and n55 and n56 may be 1.
  • m51 and m52 are the same number. For details of m55 and m56, the description of m51 and m52 in the general formula (4a) can be referred to.
  • Ar 57 and Ar 58 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R57 and R58 each independently represent a substituted or unsubstituted alkyl group.
  • m57 and m58 each independently represents an integer of 0 to 4; n57 and n58 each independently represent an integer of 0 to 4; Y7 and Y8 each independently represent two hydrogen atoms, a single bond or N( R27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z7 and Z8 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 57 , Ar 58 , R 57 , R 58 , m57, m58, n57, n58, A 1 and A 2 refer to Ar 55 , Ar 56 , R 55 , R 56 , m55, The descriptions of m56, n55, n56, A 1 and A 2 can be referred to.
  • a compound in which a benzofuran ring or a benzothiophene ring is condensed to both of the two benzene rings constituting the carbazole partial structure present in the general formula (G) can be preferably mentioned.
  • Examples of such compounds include compounds having the following skeleton (6a) and compounds having the following skeleton (6b).
  • Y 9 to Y 12 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Z 9 to Z 16 each independently represent an oxygen atom or a sulfur atom.
  • Z 9 to Z 16 are preferably the same, but may be different.
  • Z 9 -Z 16 are oxygen atoms.
  • Z 9 -Z 16 are sulfur atoms.
  • each hydrogen atom in skeletons (6a) and (6b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 59 and R 60 each independently represent a substituted or unsubstituted alkyl group.
  • m59 and m60 each independently represents an integer of 0 to 4;
  • Y9 and Y10 each independently represent two hydrogen atoms, a single bond or N( R27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 9 to Z 12 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the compound represented by the general formula (6a) is not limited to the following specific examples.
  • compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • R 61 and R 62 each independently represent a substituted or unsubstituted alkyl group.
  • m61 and m60 each independently represents an integer of 0 to 4;
  • Y 11 and Y 12 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • Z 13 to Z 16 each independently represent an oxygen atom or a sulfur atom.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the compound represented by the general formula (6b) is not limited to the following specific examples.
  • compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • a compound in which a benzene ring is condensed with a benzene ring to which a boron atom is not directly bonded can be preferably mentioned.
  • examples of such compounds include compounds having the following skeleton (7a) and compounds having the following skeleton (7b).
  • Y 21 to Y 24 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Y 21 to Y 24 the descriptions of Y 1 to Y 4 in skeletons (4a) and (4b) can be referred to.
  • each hydrogen atom in skeletons (7a) and (7b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 71 to Ar 74 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n71 and n73 each independently represents an integer of 0 to 2;
  • n72 and n74 each independently represents an integer of 0 to 4;
  • Y 21 and Y 22 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n71-n74 are integers from 0-2.
  • n71 and n73 are the same number
  • n72 and n74 are the same number.
  • n71 to n74 may be the same number.
  • n71-n74 may be zero.
  • All of n71 to n74 may be 1.
  • n71 and n73 may be 0, and n72 and n74 may be 1, for example.
  • the corresponding descriptions of Ar 1 to Ar 4 , A 1 and A 2 in general formula (1a) can be referred to.
  • Ar 75 to Ar 78 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n75 and n77 each independently represent an integer of 0 to 2;
  • n76 and n78 each independently represents an integer of 0 to 4;
  • Y 23 and Y 24 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • n75 to n78 the description of n71 to n74 in general formula (7a) can be referred to.
  • the description of n71 to n74 in general formula (7a) can be referred to.
  • the description of Ar 75 to Ar 78 the corresponding descriptions of Ar 1 to Ar 4 in general formula (1a) can be referred to.
  • a compound in which a benzene ring is condensed with a benzene ring to which a boron atom is directly bonded can be preferably mentioned.
  • examples of such compounds include compounds having the following skeleton (8a) and compounds having the following skeleton (8b).
  • Y 25 to Y 28 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Y 25 -Y 28 For details of Y 25 -Y 28 , reference can be made to the corresponding descriptions of skeletons (4a) and (4b).
  • each hydrogen atom in skeletons (8a) and (8b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 79 and Ar 80 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R71 and R72 each independently represent a substituted or unsubstituted alkyl group.
  • m71 and m72 each independently represents an integer of 0 to 4;
  • n79 and n80 each independently represents an integer of 0 to 4;
  • Y 25 and Y 26 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n79 and n80 are integers from 0-2. In one aspect of the present invention, n79 and n80 are the same number, for example both may be 0 or both may be 1.
  • m71 and m72 are integers from 0-2. In one aspect of the invention, m71 and m72 are the same number, for example both may be 0 or both may be 1.
  • Ar 81 and Ar 82 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R73 and R74 each independently represent a substituted or unsubstituted alkyl group.
  • m73 and m74 each independently represents an integer of 0 to 4;
  • n81 and n82 each independently represents an integer of 0 to 4;
  • Y 27 and Y 28 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • m73, m74, n81 and n82 the description of m71, m72, n79 and n80 in general formula (8a) can be referred to.
  • Ar 81 , Ar 82 , R 73 , R 74 , A 1 and A 2 corresponding descriptions of Ar 1 , Ar 3 , R 41 , R 42 , A 1 and A 2 in general formula (1a) can be referred to.
  • a compound in which benzene rings are condensed to both of the two benzene rings constituting the carbazole partial structure present in the general formula (G) can be mentioned preferably.
  • Examples of such compounds include compounds having the following skeleton (9a) and compounds having the following skeleton (9b).
  • Y 29 to Y 32 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • Y 29 -Y 32 For details of Y 29 -Y 32 , reference can be made to the corresponding descriptions of skeletons (4a) and (4b).
  • each hydrogen atom in skeletons (9a) and (9b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • R 75 and R 76 each independently represent a substituted or unsubstituted alkyl group.
  • m75 and m76 each independently represents an integer of 0 to 4;
  • Y 29 and Y 30 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the descriptions of R 71 , R 72 , m71, m72, A 1 and A 2 in general formula (8a) can be referred to.
  • R 77 and R 78 each independently represent a substituted or unsubstituted alkyl group.
  • m77 and m78 each independently represent an integer of 0 to 4;
  • Y 31 and Y 32 each independently represent two hydrogen atoms, a single bond or N(R 27 ).
  • R27 represents a hydrogen atom, a deuterium atom or a substituent.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • the description of R 71 , R 72 , m71, m72, A 1 and A 2 in general formula (8a) can be referred to.
  • Each hydrogen atom in skeleton (10) may be replaced by a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • a linking group together with an adjacent hydrogen atom to form a cyclic structure For details, reference can be made to the corresponding descriptions of R 1 to R 26 , A 1 and A 2 in general formula (G).
  • At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in skeleton (10) is substituted with a substituted or unsubstituted aryl group.
  • each hydrogen atom in skeleton (10) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 91 to Ar 94 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted
  • An aryl group can be preferably chosen.
  • n91 and n93 each independently represent an integer of 0-4, and n92 and n94 each independently represent an integer of 0-3.
  • ⁇ ring, ⁇ ring, ⁇ ring, and ⁇ ring may be substituted, and at least one ring is substituted with a substituted or unsubstituted aryl group, or optionally substituted benzene ring is condensed or the furan ring of substituted or unsubstituted benzofuran or the thiophene ring of substituted or unsubstituted thiophene are condensed.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • n91-n94 are integers from 0-2.
  • n91 and n93 are the same number, and n92 and n94 are the same number. All of n91 to n94 may be the same number, for example, all may be 0 or all may be 1.
  • Ar 91 to Ar 94 the corresponding descriptions of Ar 1 to Ar 4 in general formula (1a) can be referred to.
  • the ⁇ and ⁇ rings have the same substituents or have the same condensed structure, and the ⁇ and ⁇ rings have the same substituents or have the same condensed structure. have.
  • both the ⁇ ring and the ⁇ ring are substituted with a substituted or unsubstituted aryl group, an optionally substituted benzene ring is condensed, or a substituted or unsubstituted furan ring of benzofuran Alternatively, the thiophene rings of substituted or unsubstituted thiophene are condensed.
  • both the ⁇ ring and the ⁇ ring are substituted with a substituted or unsubstituted aryl group, an optionally substituted benzene ring is condensed, or a substituted or unsubstituted furan ring of benzofuran Alternatively, the thiophene rings of substituted or unsubstituted thiophene are condensed.
  • all of the ⁇ ring, ⁇ ring, ⁇ ring, and ⁇ ring are substituted with a substituted or unsubstituted aryl group, or condensed with an optionally substituted benzene ring, or substituted
  • the furan ring of unsubstituted benzofuran or the thiophene ring of substituted or unsubstituted thiophene is condensed.
  • the compound represented by the general formula (G) may have an asymmetric skeleton.
  • it may be a compound having an asymmetric skeleton such as the following skeleton (11a) or the following skeleton (11b).
  • Z17 and Z18 each independently represent an oxygen atom or a sulfur atom.
  • each hydrogen atom in skeletons (11a) and (11b) is not substituted with a linking group together with an adjacent hydrogen atom to form a cyclic structure.
  • Ar 83 to Ar 85 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R83 and R84 each independently represent a substituted or unsubstituted alkyl group.
  • Z17 represents an oxygen atom or a sulfur atom.
  • m83 and m84 each independently represents an integer of 0 to 5; n83 represents an integer of 0 to 4, and n84 and n85 each independently represents an integer of 0 to 3.
  • Ar 83 to Ar 85 , R 83 , R 84 , m83, m84 and n83 to n85 refer to Ar 1 , Ar 2 , Ar 4 , R 41 , R 42 , m1 in general formula (1a) , m2, n1, n2, and n4.
  • the compound represented by the general formula (11a) is not limitedly interpreted by the following specific examples.
  • a compound in which all Xs in the molecule are oxygen atoms and a compound in which all Xs in the molecule are sulfur atoms are disclosed.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • Ar 86 to Ar 88 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted An aryl group can be preferably chosen.
  • R86 and R87 each independently represent a substituted or unsubstituted alkyl group.
  • Z18 represents an oxygen atom or a sulfur atom.
  • m86 and m87 each independently represents an integer of 0 to 5; n86 represents an integer of 0 to 4, and n87 and n88 each independently represents an integer of 0 to 3.
  • Ar 86 to Ar 88 , R 86 , R 87 , m86, m87, n86 to n88 refer to Ar 1 , Ar 2 , Ar 4 , R 41 , R 42 , m1 , m2, n1, n2, and n4.
  • the compound represented by the general formula (11b) is not limitedly interpreted by the following specific examples.
  • a compound in which all Xs in the molecule are oxygen atoms and a compound in which all Xs in the molecule are sulfur atoms are disclosed.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be used.
  • a compound in which R 5 is a donor group can be preferably employed as the compound represented by the general formula (G).
  • a compound in which R5 is a donor group tends to have a high molar absorption coefficient and high luminous efficiency. For example , it exhibits superior luminescence properties compared to compounds in which R3 is a donor group.
  • R3 is not a donor group.
  • R 1 to R 7 only R 5 is a donor group, or neither of them is a donor group (particularly a donor group with a ⁇ p value of ⁇ 0.2 or less).
  • the donor group is a group having a negative Hammett ⁇ p value.
  • the ⁇ p value of the donor group of R 5 is preferably ⁇ 0.2 or less, may be ⁇ 0.4 or less, or may be ⁇ 0.6 or less, for example.
  • Preferred donor groups include substituted amino groups, preferably substituted or unsubstituted diarylamino groups.
  • the aryl group may be a monocyclic ring or a condensed ring in which two or more rings are condensed. In the case of condensed rings, the number of rings after condensed is preferably 2 to 6, and can be selected from 2 to 4, or can be 2, for example.
  • Two aryl groups constituting a diarylamino group may be the same or different. Also, two aryl groups may be linked by a single bond or a linking group.
  • a substituted or unsubstituted diphenylamino group is preferable as the substituted or unsubstituted diarylamino group.
  • a substituted or unsubstituted carbazol-9-yl group in which two phenyl groups are bonded by a single bond may be employed, or a substituted or unsubstituted diphenylamino group in which two phenyl groups are not bonded by a single bond. may be adopted.
  • any one of R 1 to R 7 in general formula (G) is a substituted amino group, at least R 5 is preferably a substituted amino group, more preferably only R 5 is a substituted amino group. In one aspect of the invention , R3 is not a substituted amino group.
  • R 16 or R 19 is preferably a donor group, more preferably R 19 is a donor group.
  • all of the other R 1 to R 26 may be, for example, hydrogen atoms or deuterium atoms, and for example, at least one of R 3 , R 6 , R 15 and R 20 may be a substituent (preferably substituted or an unsubstituted alkyl group, or a substituted or unsubstituted aryl group), and others may be hydrogen atoms or deuterium atoms.
  • R 20 or R 23 is preferably a donor group, more preferably R 20 is a donor group.
  • all of the other R 1 to R 26 may be, for example, hydrogen atoms or deuterium atoms, and for example, at least one of R 3 , R 6 , R 19 and R 24 may be a substituent (preferably substituted or an unsubstituted alkyl group, or a substituted or unsubstituted aryl group), and others may be hydrogen atoms or deuterium atoms.
  • R 5 is a donor group
  • compounds represented by the following general formula (12a) and compounds represented by the following general formula (12b) can be exemplified.
  • Ar 1 to Ar 8 each independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group;
  • a substituted or unsubstituted alkyl group can be preferably selected, and a substituted or unsubstituted aryl group can be preferably selected.
  • R5 represents a donor group.
  • R 41 to R 44 each independently represent a substituted or unsubstituted alkyl group.
  • n1 to m4 each independently represent an integer of 0 to 5; n1, n3, n5 and n7 each independently represent an integer of 0-4, n4 and n8 represent an integer of 0-3, and n2' and n6' represent an integer of 0-2.
  • a 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • Ar 1 bonded to adjacent carbon atoms, Ar 3 bonded to adjacent carbon atoms, Ar 5 bonded to adjacent carbon atoms, and Ar 5 bonded to adjacent carbon atoms Ar 7 may be bonded to each other to form a cyclic structure, preferably benzofuran (condensed with furan ring) or benzothiophene (condensed with thiophene ring).
  • each compound is defined by identifying R, Ar and X in formulas F1-F56 in the table.
  • R is selected from A to D listed below
  • Ar is selected from a to d listed below
  • X is selected from ⁇ to ⁇ .
  • a compound of 1 is a compound having a structure in which R is A and Ar is a in Formula F1.
  • the skeletons (1a) to (12b) are skeletons to which other rings are not further condensed. In one aspect of the present invention, the skeletons (1a) to (12b) are skeletons to which other rings may be further condensed.
  • 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 R9 , R9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R18 and R19 , 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 , R 25 and R 26 are linked to each other to form a ring structure. be able to.
  • a 1 and A 2 in general formula (G) are acceptor groups.
  • examples thereof include compounds having acceptor groups at positions A 1 and A 2 and having any of skeletons (1a) to (12b).
  • the description and specific examples of the acceptor group the description and specific examples of the acceptor groups of A 1 and A 2 in formula (G) above can be referred to.
  • Specific examples of compounds in which A 1 and A 2 are acceptor groups are given below.
  • the compounds in which A 1 and A 2 are acceptor groups that can be used in the present invention are not limited to the following specific examples.
  • the following specific examples have a structure in which both A 1 and A 2 are "A", and the structure of each compound is specified by individually specifying "A".
  • a compound having a rotationally symmetric structure is selected as the compound represented by general formula (G).
  • a compound having an axisymmetric structure is selected as the compound represented by General Formula (G).
  • a compound having an asymmetric structure is selected as the compound represented by general formula (G).
  • Specific examples of compounds having an asymmetric skeleton are given below.
  • the compound having an asymmetric skeleton and the compound having an asymmetric structure that can be used in the present invention are not limited to the following specific examples.
  • For specific examples containing X compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are disclosed, respectively.
  • a compound in which a part of X in the molecule is an oxygen atom and the rest is a sulfur atom can also be employed.
  • R 3 in general formula (G) is not a diarylamino group (two aryl groups constituting the diarylamino group may be bonded to each other).
  • R3 in general formula (G) is a hydrogen atom, a deuterium atom or an acceptor group (not a donor group).
  • at least one of n1 to n4 in general formula (1a) is 1 or more.
  • at least one of m1 and m2 in general formula (1a) is 1 or more.
  • At least one of n1 to n4 in general formula (1a) is 1 or more, and at least one of m1 and m2 in general formula (1a) is 1 or more.
  • at least one of n5 to n8 in general formula (1b) is 1 or more.
  • at least one of m3 and m4 in general formula (1b) is 1 or more.
  • at least one of n5 to n8 in general formula (1b) is 1 or more, and at least one of m3 and m4 in general formula (1a) is 1 or more.
  • R 41 and R 42 and at least one of R 43 and R 44 are deuterium atoms;
  • An optionally substituted alkyl group is preferred, for example, all of R 41 to R 44 are alkyl groups optionally substituted with deuterium atoms.
  • at least one of n1 to n4 is 1 or more and at least one of n5 to n8 is 1 or more, at least one of Ar 1 to Ar 4 and at least one of Ar 5 to Ar 8 is deuterium It is preferably an aryl group which may be substituted with an atom or an alkyl group.
  • Ar 1 to Ar 8 are aryl groups which may be substituted with a deuterium atom or an alkyl group.
  • X 1 in general formula (G) is a boron atom and R 8 , R 10 , R 12 , R 13 , R 15 and R 17 are alkyl groups (or methyl groups)
  • R 1 At least one of to R 7 , R 18 to R 20 and R 23 to R 26 is a substituent, preferably a group of substituent group E, which may be substituted with, for example, a deuterium atom or an alkyl group. It is an aryl group.
  • R 1 At least one of to R 7 , R 13 to R 16 and R 19 to R 21 is a substituent, preferably a group of substituent group E, and may be substituted with, for example, a deuterium atom or an alkyl group. It is an aryl group.
  • X 1 in general formula ( G ) is a boron atom ; when any one pair is bonded to each other to form an aromatic ring (or benzene ring), at least one of R 1 to R 7 , R 18 to R 20 and R 23 to R 26 is a substituent, Preferably, it is a group of substituent group E, such as an aryl group optionally substituted with a deuterium atom or an alkyl group.
  • X 2 in general formula (G) is a boron atom, any one set of R 8 and R 9 , R 9 and R 10 , and R 22 and R 23 , R 23 and R 24 when any one pair is bonded to each other to form an aromatic ring (or benzene ring), at least one of R 1 to R 7 , R 13 to R 16 and R 19 to R 21 is a substituent; Preferably, it is a group of substituent group E, such as an aryl group optionally substituted with a deuterium atom or an alkyl group.
  • R 9 and R 11 in general formula (G) are neither a cyano group nor an alkyl group.
  • R 9 and R 11 are hydrogen atoms, deuterium atoms, or substituents other than cyano and alkyl groups.
  • R 9 and R 11 in general formula (G) are neither a cyano group nor a tert-butyl group.
  • at least one of R 8 to R 12 in general formula (G) is a substituent.
  • R 3 in general formula (G) is neither a substituted amino group nor an aryl group.
  • R 3 in general formula (G) is neither a substituted amino group nor a phenyl group.
  • R 3 in general formula (G) is not a dimethylamino group, diphenylamino group or phenyl group.
  • at least one of R 1 to R 26 in general formula (G) is a substituent, more preferably at least one of R 1 to R 26 is an alkyl group, for example 1 to 4 alkyl groups.
  • the organic electroluminescent device of the present invention is held by a substrate, which is not particularly limited and commonly used in organic electroluminescent devices such as glass, transparent plastic, quartz and silicon. Any material formed by
  • the anode of the organic electroluminescent device is made from metals, alloys, conductive compounds, or combinations thereof.
  • the metal, alloy or conductive compound has a high work function (4 eV or greater).
  • the metal is Au.
  • the conductive transparent material is selected from CuI, indium tin oxide ( ITO), SnO2 and ZnO. Some embodiments use amorphous materials that can form transparent conductive films, such as IDIXO (In 2 O 3 —ZnO).
  • the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering.
  • the film is patterned by photolithographic methods. In some embodiments, if the pattern does not need to be highly precise (eg, about 100 ⁇ m or greater), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, wet film forming methods such as printing and coating methods are used when coating materials such as organic conductive compounds can be applied.
  • the anode has a transmittance of greater than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode varies depending on the materials used.
  • the cathode is made of electrode materials such as metals with a low work function (4 eV or less) (referred to as electron-injecting metals), alloys, conductive compounds, or combinations thereof.
  • the electrode material is sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum - aluminum oxide (Al2 O 3 ) mixtures, indium, lithium-aluminum mixtures and rare earth elements.
  • a mixture of an electron-injecting metal and a second metal that is a stable metal with a higher work function than the electron-injecting metal is used.
  • the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al 2 O 3 ) mixtures, lithium-aluminum mixtures and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation.
  • the cathode is manufactured by depositing or sputtering the electrode material as a thin film. In some embodiments, the cathode has a sheet resistance of no more than several hundred ohms per unit area. In some embodiments, the thickness of said cathode is between 10 nm and 5 ⁇ m. In some embodiments, the thickness of the cathode is 50-200 nm.
  • either one of the anode and cathode of the organic electroluminescent device is transparent or translucent to allow transmission of emitted light.
  • transparent or translucent electroluminescent elements enhance light radiance.
  • the cathode is formed of a conductive transparent material as described above for the anode, thereby forming a transparent or translucent cathode.
  • the device includes an anode and a cathode, both transparent or translucent.
  • the injection layer is the layer between the electrode and the organic layer. In some embodiments, the injection layer reduces drive voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be placed between the anode and the light-emitting layer or hole-transporting layer and between the cathode and the light-emitting layer or electron-transporting layer. In some embodiments, an injection layer is present. In some embodiments, there is no injection layer. Preferred examples of compounds that can be used as the hole injection material are given below.
  • a barrier layer is a layer that can prevent charges (electrons or holes) and/or excitons present in the light-emitting layer from diffusing out of the light-emitting layer.
  • an electron blocking layer is between the light-emitting layer and the hole-transporting layer to block electrons from passing through the light-emitting layer to the hole-transporting layer.
  • a hole blocking layer is between the emissive layer and the electron transport layer and blocks holes from passing through the emissive layer to the electron transport layer.
  • the barrier layer prevents excitons from diffusing out of the emissive layer.
  • the electron blocking layer and the hole blocking layer constitute an exciton blocking layer.
  • the terms "electron blocking layer” or "exciton blocking layer” include layers that have both the functionality of an electron blocking layer and an exciton blocking layer.
  • a hole blocking layer functions as an electron transport layer.
  • the hole blocking layer blocks holes from reaching the electron transport layer during electron transport.
  • the hole blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the hole blocking layer can be the same materials as described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.
  • exciton barrier layer The exciton blocking layer prevents diffusion of excitons generated through recombination of holes and electrons in the light emitting layer to the charge transport layer. In some embodiments, the exciton blocking layer allows effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, an exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides thereof. In some embodiments, when an exciton blocking layer is present on the anode side, it may be present between and adjacent to the hole-transporting layer and the light-emitting layer.
  • an exciton blocking layer when an exciton blocking layer is present on the cathode side, it may be between and adjacent to the emissive layer and the cathode. In some embodiments, a hole-injection layer, electron-blocking layer, or similar layer is present between the anode and an exciton-blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron blocking layer, hole blocking layer or similar layer is present between the cathode and an exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and triplet energy, respectively, of the emissive material.
  • the hole-transporting layer comprises a hole-transporting material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one property of a hole injection or transport property and an electron barrier property.
  • the hole transport material is an organic material.
  • the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolones.
  • the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as the hole-transporting material are given below.
  • the electron transport layer includes an electron transport material.
  • the electron transport layer is a single layer.
  • the electron transport layer has multiple layers.
  • the electron-transporting material need only function to transport electrons injected from the cathode to the emissive layer.
  • the electron transport material also functions as a hole blocking material.
  • electron-transporting layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxazide Azole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof.
  • the electron transport material is a thiadiazole derivative or a quinoxaline derivative.
  • the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as the electron-transporting material are given below.
  • examples of preferred compounds as materials that can be added to each organic layer are given.
  • it may be added as a stabilizing material.
  • Each organic layer of the organic electroluminescence device can be formed by a wet process.
  • a solution in which a composition containing a compound constituting the organic layer is dissolved is applied to the surface, and the layer is formed after removing the solvent.
  • wet processes include spin coating, slit coating, inkjet (spray), gravure printing, offset printing, and flexographic printing, but are not limited to these.
  • an appropriate organic solvent capable of dissolving the compound constituting the organic layer is selected and used.
  • a substituent for example, an alkyl group
  • the organic layer can be formed in a dry process.
  • the dry process can be vacuum deposition, but is not limited to this.
  • the compounds constituting the organic layer may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed.
  • the composition ratio of the plurality of compounds contained in the vapor deposition source is reduced by performing co-deposition under conditions in which the vapor deposition rates (weight reduction rates) of the plurality of compounds contained in the single vapor deposition source match or substantially match.
  • the vapor deposition rates (weight reduction rates) of the plurality of compounds contained in the single vapor deposition source match or substantially match.
  • can form an organic layer having a composition ratio corresponding to An organic layer having a desired composition ratio can be easily formed by mixing a plurality of compounds at the same composition ratio as that of the organic layer to be formed as a vapor deposition source.
  • the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified and used as the temperature during co-deposition.
  • the emissive layer is incorporated into the device.
  • devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones and tablets.
  • an electronic device includes an OLED having at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
  • the composition may be useful in facilitating charge or energy transfer within a device and/or as a hole transport material.
  • OLEDs organic light emitting diodes
  • OICs organic integrated circuits
  • O-FETs organic field effect transistors
  • O-TFTs organic thin film transistors
  • O-LETs organic light emitting transistors
  • O-SC organic solar cells.
  • O-SC organic optical detectors
  • O-FQD organic field-quench devices
  • LOC luminescent fuel cells
  • O-lasers organic laser diodes
  • an electronic device includes an OLED including at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • the device includes OLEDs of different colors.
  • the device includes an array including combinations of OLEDs.
  • said combination of OLEDs is a combination of three colors (eg RGB).
  • the combination of OLEDs is a combination of colors other than red, green, and blue (eg, orange and yellow-green).
  • said combination of OLEDs is a combination of two, four or more colors.
  • the device a circuit board having a first side with a mounting surface and a second opposite side and defining at least one opening; at least one OLED on the mounting surface, wherein the at least one OLED is configured to emit light, wherein the at least one OLED includes at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode; at least one OLED comprising a housing for the circuit board; at least one connector located at an end of said housing, said housing and said connector defining a package suitable for attachment to a lighting fixture.
  • the OLED light comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some light emitted in the first direction is polarized and emitted in the second direction. In some embodiments, a reflector is used to polarize light emitted in the first direction.
  • the emissive layers of the invention can be used in screens or displays.
  • the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, evaporation or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching to provide unique aspect ratio pixels.
  • Said screens also called masks
  • the corresponding artwork pattern design allows placement of very steep narrow tie-bars between pixels in the vertical direction as well as large and wide beveled openings in the horizontal direction.
  • the internal patterning of the pixels makes it possible to construct three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Further, the use of imaged "stripes" or halftone circles in pixel areas protects etching in specific areas until these specific patterns are undercut and removed from the substrate. All pixel areas are then treated with a similar etch rate, but their depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with varying degrees of protection within the pixel, allowing for the localized deep etching necessary to form steep vertical bevels. . A preferred material for the evaporation mask is Invar.
  • Invar is a metal alloy that is cold rolled into long thin sheets in steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask.
  • a suitable and low-cost method for forming the open areas in the deposition mask is by wet chemical etching.
  • the screen or display pattern is a matrix of pixels on a substrate.
  • screen or display patterns are fabricated using lithography (eg, photolithography and e-beam lithography).
  • the screen or display pattern is processed using wet chemical etching.
  • the screen or display pattern is fabricated using plasma etching.
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on a mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating the TFT with a planarizing film, pixel electrodes, and a light emitting layer. , a counter electrode and an encapsulation layer, are sequentially formed and cut from the mother panel.
  • TFT thin film transistor
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on a mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating the TFT with a planarizing film, pixel electrodes, and a light emitting layer. , a counter electrode and an encapsulation layer, are sequentially formed and cut from the mother panel.
  • TFT thin film transistor
  • an organic light emitting diode (OLED) display comprising: forming a barrier layer on the base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interfaces between the cell panels.
  • the barrier layer is an inorganic film, eg, made of SiNx, and the edges of the barrier layer are covered with an organic film, made of polyimide or acrylic.
  • the organic film helps the mother panel to be softly cut into cell panels.
  • a thin film transistor (TFT) layer has an emissive layer, a gate electrode, and source/drain electrodes.
  • Each of the plurality of display units may have a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light emitting unit formed on the planarization film, and The applied organic film is made of the same material as that of the planarizing film, and is formed at the same time as the planarizing film is formed.
  • the light-emitting unit is coupled with the TFT layer by a passivation layer, a planarizing film therebetween, and an encapsulation layer that covers and protects the light-emitting unit.
  • the organic film is not connected to the display unit or encapsulation layer.
  • each of the organic film and the planarizing film may include one of polyimide and acrylic.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide. The method further comprises attaching a carrier substrate made of a glass material to one surface of a base substrate made of polyimide before forming a barrier layer on another surface of the base substrate; separating the carrier substrate from the base substrate prior to cutting along the interface.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film placed on the TFT layer to cover the TFT layer.
  • the planarizing film is an organic film formed over a passivation layer.
  • the planarizing film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarizing film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer such that a portion of the organic film is in direct contact with the base substrate and the remainder of the organic film is in contact with the base substrate. , in contact with the barrier layer while surrounding the edges of the barrier layer.
  • the emissive layer comprises a pixel electrode, a counter electrode, and an organic emissive layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrodes are connected to source/drain electrodes of the TFT layer.
  • a suitable voltage is formed between the pixel electrode and the counter electrode, causing the organic light emitting layer to emit light, thereby displaying an image. is formed.
  • An image forming unit having a TFT layer and a light emitting unit is hereinafter referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed into a thin encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin film-like encapsulation structure in which multiple thin films are stacked.
  • the organic film applied to the interface portion is spaced apart from each of the plurality of display units.
  • the organic film is formed such that a portion of the organic film is in direct contact with the base substrate and the remaining portion of the organic film is in contact with the barrier layer while surrounding the edges of the barrier layer. be done.
  • the OLED display is flexible and uses a flexible base substrate made of polyimide.
  • the base substrate is formed on a carrier substrate made of glass material, and then the carrier substrate is separated.
  • a barrier layer is formed on the surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of a mother panel, while barrier layers are formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the groove.
  • the manufacturing method further comprises cutting along the interface, wherein a groove is formed in the barrier layer, at least a portion of the organic film is formed with the groove, and the groove is Does not penetrate the base substrate.
  • a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on and cover the TFT layer.
  • the planarizing film eg made of polyimide or acrylic
  • the interface grooves are covered with an organic film, eg made of polyimide or acrylic. This prevents cracking by having the organic film absorb the impact that occurs when each cell panel is cut along the groove at the interface.
  • the grooves at the interfaces between the barrier layers are coated with an organic film to absorb shocks that might otherwise be transmitted to the barrier layers, so that each cell panel is softly cut and the barrier layers It may prevent cracks from forming.
  • the organic film covering the groove of the interface and the planarizing film are spaced apart from each other. For example, when the organic film and the planarizing film are connected to each other as a single layer, external moisture may enter the display unit through the planarizing film and the portion where the organic film remains. The organic film and planarizing film are spaced from each other such that the organic film is spaced from the display unit.
  • the display unit is formed by forming a light-emitting unit and an encapsulating layer is placed over the display unit to cover the display unit.
  • the carrier substrate carrying the base substrate is separated from the base substrate.
  • the carrier substrate separates from the base substrate due to the difference in coefficient of thermal expansion between the carrier substrate and the base substrate.
  • the mother panel is cut into cell panels.
  • the mother panel is cut along the interfaces between the cell panels using a cutter.
  • the interface groove along which the mother panel is cut is coated with an organic film so that the organic film absorbs impact during cutting.
  • the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces the reject rate of the product and stabilizes its quality.
  • Another embodiment includes a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic layer applied to the edges of the barrier layer.
  • An OLED display comprising a film.
  • the emission characteristics were evaluated using a source meter (manufactured by Keithley: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies: E5273A), an optical power meter measuring device (manufactured by Newport: 1930C), and an optical spectrometer. (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3) and a streak camera (Hamamatsu Photonics, Model C4334).
  • N-bromosuccinimide (13.8 g, 77.7 mmol) was added to a chloroform solution (900 mL) of 12H-benzofuro[2,3-a]carbazole (20.0 g, 77.7 mmol) under an ice bath under a nitrogen atmosphere. , and stirred for 14 hours at room temperature. After removing the solvent, it was washed with methanol. The obtained solid was dissolved in heated toluene and filtered through a Buchner funnel covered with Celite/silica gel/Celite. After removing the solvent from the filtrate, recrystallization was performed with toluene and chlorobenzene to obtain intermediate M1 as a white solid (15.9 g, 61%).
  • intermediate M1 (15.8 g, 46.9 mmol), phenylboronic acid (6.8 g, 56.3 mmol), tripotassium phosphate (19.9 g, 93.9 mmol), tetrakis(triphenylphosphine).
  • Example 1 By laminating the following thin films at a degree of vacuum of 5.0 ⁇ 10 ⁇ 5 Pa by a vacuum deposition method on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm is formed.
  • An organic electroluminescence device was produced.
  • HAT-CN was formed to a thickness of 10 nm on ITO
  • NPD was formed thereon to a thickness of 30 nm
  • compound 1b was formed thereon to a thickness of 10 nm.
  • the host material (H1) and the delayed fluorescence material (T132) were co-deposited from different vapor deposition sources to form a layer with a thickness of 40 nm to form a light-emitting layer.
  • the content of the host material was 65% by mass, and the content of the delayed fluorescence material was 35% by mass.
  • Liq and SF3-TRZ were co-deposited from different vapor deposition sources to form a layer with a thickness of 30 nm.
  • the contents of Liq and SF3-TRZ in this layer were 30 mass % and 70 mass %, respectively.
  • Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescence device.
  • This element was designated as EL element 1.
  • EL devices 2 to 4 were prepared in the same manner except that compounds 6b, 19b and 22 were used instead of compound 1b. Further, the organic electroluminescence devices were prepared according to the same procedure except that the comparative compound A and the comparative compound B were used instead of the compound 1b.
  • T132 delayed fluorescence derived from the delayed fluorescence material
  • Each organic electroluminescence element was driven at a current density of 12.6 mA/cm 2 and the time (LT95) until the emission intensity reached 95% of that at the start of driving was measured.
  • Table 2 shows the measurement results. LT95 in Table 2 is shown as a relative value when LT95 of the comparative EL element 2 is set to 1. The measurement results show that the device life is significantly longer when the compound represented by the general formula (1) is used as the electron barrier material than the comparative compounds A and B, which are conventionally used as electron barrier materials. indicates that it will be longer.
  • Example 2 The light-emitting layer of Example 1 was co-deposited with the host material (H1), the delayed fluorescent material (T132), and the fluorescent material (E1) from different vapor deposition sources, and the contents were 64.2% by mass and 35.0% by mass in that order. %, 0.8% by mass, and an organic electroluminescence device was produced in the same manner as in Example 1, except that a light-emitting layer with a thickness of 40 nm was used. This element was designated as EL element 5 .
  • EL devices 6 and 7 were prepared by the same procedure except that compounds 2b and 19b were used instead of compound 1b. When each of the produced organic electroluminescence devices was energized, delayed fluorescence derived from the fluorescent material (E1) was observed.
  • the produced organic electroluminescence device was driven at 6.3 mA/cm 2 to measure the external quantum efficiency (EQE) and the initial drive voltage, and each organic electroluminescence device was driven at a current density of 12.6 mA/cm 2 Then, the time (LT95) until the emission intensity reaches 95% of that at the start of driving was measured.
  • Table 3 shows the measurement results. EQE and LT95 in Table 3 are shown as relative values when LT95 of EL element 7 is set to 1, and drive voltage is shown as a relative value with EL element 7 as a reference (0).
  • the measurement results show that even when a host material, a delayed fluorescence material, and a fluorescent material are used in the light-emitting layer, the device using the compound represented by the general formula (1) as an electron barrier material has high luminous efficiency. high, low drive voltage, and long device life.
  • Example 3 The light-emitting layer of Example 1 was co-deposited with the host material (H1) and the delayed fluorescent material (T136) from different vapor deposition sources, and the content was 65% by mass and 35% by mass in order to form a 40 nm-thick light-emitting layer.
  • An organic electroluminescence device was produced by the same procedure as in Example 1 except for the changed points. This element was designated as EL element 8 .
  • An EL device 9 was prepared by the same procedure except that the compound 2b was used instead of the compound 1b. When each of the produced organic electroluminescence devices was energized, delayed fluorescence derived from the delayed fluorescence material (T136) was observed.
  • the produced organic electroluminescence device was driven at 6.3 mA/cm 2 and the external quantum efficiency (EQE) and the initial driving voltage were measured.
  • each organic electroluminescence device was driven at a current density of 12.6 mA/cm 2 and the time (LT95) until the emission intensity reached 95% of that at the start of driving was measured.
  • Table 4 shows the measurement results. EQE and LT95 in Table 4 are shown as relative values when LT95 of EL element 9 is set to 1, and drive voltage is shown as a relative value with EL element 9 as a reference (0).
  • the measurement results show that, even when a delayed fluorescence material different from that in Example 1 is used, the device using the compound represented by the general formula (1) as an electron barrier material has high luminous efficiency and can be driven. This indicates that the voltage is low and the device life is long.
  • Example 4 By laminating the following thin films at a degree of vacuum of 5.0 ⁇ 10 ⁇ 5 Pa by a vacuum deposition method on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm is formed.
  • An organic electroluminescence device was produced.
  • HAT-CN was formed on ITO to a thickness of 60 nm
  • TrsPCz was formed thereon to a thickness of 30 nm
  • PYD2Cz was formed thereon to a thickness of 5 nm.
  • the host material (reference compound a) and the delayed fluorescence material (T3) were co-deposited from different vapor deposition sources to form a layer with a thickness of 30 nm to form a light-emitting layer.
  • the content of the host material was 70% by mass
  • the content of the delayed fluorescence material was 30% by mass.
  • Liq and SF3-TRZ were co-deposited from different vapor deposition sources to form a layer with a thickness of 30 nm.
  • the contents of Liq and SF3-TRZ in this layer were 30 mass % and 70 mass %, respectively.
  • Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescence device.
  • This device was designated as reference EL device 1.
  • the produced organic electroluminescence device was driven at 2 mA/cm 2 and the external quantum efficiency (EQE) was measured, it showed a high value of 21.9%. From this, it can be seen that the reference compound a is an excellent material as a host material.
  • a reference EL device 2 was an organic electroluminescence device fabricated by the same procedure except that compound 1a was used instead of PYD2Cz.
  • the compound represented by general formula (1) is useful as an electron barrier material and can be used in organic semiconductor devices.
  • the compound of the present invention in the electron barrier layer of an organic electroluminescence device, the life of the device can be extended. Therefore, the present invention has high industrial applicability.

Abstract

Ce composé représenté par la formule générale est utile en tant que matériau barrière aux électrons. R1 à R5 sont un atome de deutérium, un substituant autre qu'un groupe cyano ; n1, n3, n5 sont 0-4 ; n2 est 0-3 ; n4 est 0-2 ; X est O ou S ; et Ar est un groupe arylène monocyclique ou un groupe hétéroarylène monocyclique.
PCT/JP2022/025151 2021-06-23 2022-06-23 Matériau de barrière d'électrons, élément semi-conducteur organique et composé WO2022270592A1 (fr)

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