WO2022068292A1 - 一种有机化合物以及使用其的电子元件和电子装置 - Google Patents

一种有机化合物以及使用其的电子元件和电子装置 Download PDF

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WO2022068292A1
WO2022068292A1 PCT/CN2021/102557 CN2021102557W WO2022068292A1 WO 2022068292 A1 WO2022068292 A1 WO 2022068292A1 CN 2021102557 W CN2021102557 W CN 2021102557W WO 2022068292 A1 WO2022068292 A1 WO 2022068292A1
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杨敏
南朋
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陕西莱特光电材料股份有限公司
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Definitions

  • the present application belongs to the technical field of organic materials, and specifically provides an organic compound and electronic components and electronic devices using the same.
  • the organic light-emitting phenomenon refers to the phenomenon of using organic substances to convert electrical energy into light energy.
  • An organic light-emitting element utilizing an organic light-emitting phenomenon generally has a structure including an anode and a cathode and an organic layer interposed therebetween.
  • the organic layer is often formed by a multilayer structure of different substances. For example, a hole injection layer, a hole transport layer, an organic An injection layer, etc. is formed.
  • a voltage when a voltage is applied between the two stages, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer. When the injected holes and electrons meet, an excitation is formed. When the exciton transitions to the ground state again, it emits light.
  • Prior art CN106206964, WO2011010843, etc. disclose organic light-emitting layer materials that can be used in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of the present application is to provide an organic compound and an electronic component and electronic device using the same, the organic compound can be used as an organic light-emitting layer of an organic electroluminescent device.
  • a first aspect of the present application provides an organic compound, and the structural formula of the organic compound is shown in Formula 1:
  • ring A and ring B are the same or different, each independently selected from a benzene ring or a condensed aromatic ring with 10 to 14 ring carbon atoms, and at least one of ring A and ring B is selected from ring carbon atoms Condensed aromatic rings with 10 to 14 atoms;
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
  • Each R 1 and R 2 are the same or different, and each is independently selected from: hydrogen, deuterium, halogen group, cyano group, haloalkyl group having 1 to 10 carbon atoms, and alkyl group having 1 to 10 carbon atoms , cycloalkyl group with 3 to 15 carbon atoms, alkoxy group with 1 to 4 carbon atoms, alkylthio group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms , a triarylsilyl group with 18 to 24 carbon atoms, an aryl group with 6 to 12 carbon atoms, a heteroaryl group with 4 to 12 carbon atoms, and a heteroaralkyl group with 5 to 13 carbon atoms;
  • n represents the number of R 1
  • q represents the number of R 2
  • m, q are independently selected from 1, 2, 3, 4, 5, 6, 7 or 8;
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in the L 1 , L 2 and Ar 1 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, optionally by Aryl having 6 to 20 carbon atoms and 1 carbon atom substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl ⁇ 10 alkyl groups, 1-10 carbon atoms haloalkyl groups, 3-10 carbon atoms cycloalkyl groups, 1-10 carbon atoms alkoxy groups, 1-10 carbon atoms alkanes Sulfur group, trialkylsilyl group with 3 to 12 carbon atoms, triarylsilyl group with 18 to 24 carbon atoms, and phosphineoxy group with 6 to 18 carbon atoms.
  • a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound described in the first aspect of the present disclosure ;
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound;
  • the organic light-emitting layer includes a host material and a guest material, and the host material includes the organic compound.
  • a third aspect of the present application provides an electronic device, and the electronic device includes the electronic element described in the second aspect of the present application.
  • the organic compound provided by the present application has a molecular structure in which an anthracene group is combined with benzoadamantane fluorene.
  • the molecular structure improves the overall electron density, carrier transport rate and triplet energy level of the molecule, and is suitable for use as a host material for an organic light-emitting layer; and the spiro adamantane structure is introduced into the molecular structure, which can improve the film performance, thereby increasing the service life of the film.
  • the molecular structure has a large molecular weight, which can effectively increase the glass transition temperature of the material, and the benzo structure and the aromatic group introduced on the rigid conjugated planar anthracene group can increase steric hindrance, thereby adjusting the structure. , improve the film-forming property of the material and the molecules are not easy to crystallize in an amorphous state, thereby improving the luminous efficiency of the organic electroluminescent device using the organic compound, and improving the conversion efficiency of the photoelectric conversion device using the organic compound.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of a second electronic device according to another embodiment of the present application.
  • a first aspect of the present application provides an organic compound, and the structural formula of the organic compound is shown in Formula 1:
  • ring A and ring B are the same or different, each independently selected from a benzene ring or a condensed aromatic ring with 10 to 14 ring carbon atoms, and at least one of ring A and ring B is selected from ring carbon atoms Condensed aromatic rings with 10 to 14 atoms;
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
  • Each R 1 and R 2 are the same or different, and each is independently selected from: hydrogen, deuterium, halogen group, cyano group, haloalkyl group having 1 to 10 carbon atoms, and alkyl group having 1 to 10 carbon atoms , cycloalkyl group with 3 to 15 carbon atoms, alkoxy group with 1 to 4 carbon atoms, alkylthio group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms , a triarylsilyl group with 18 to 24 carbon atoms, an aryl group with 6 to 12 carbon atoms, a heteroaryl group with 4 to 12 carbon atoms, and a heteroaralkyl group with 5 to 13 carbon atoms;
  • n represents the number of R 1
  • q represents the number of R 2
  • m, q are independently selected from 1, 2, 3, 4, 5, 6, 7 or 8;
  • Ar 1 is selected from: a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;
  • the substituents in the L 1 , L 2 and Ar 1 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, optionally by Aryl having 6 to 20 carbon atoms and 1 carbon atom substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl ⁇ 10 alkyl groups, 1-10 carbon atoms haloalkyl groups, 3-10 carbon atoms cycloalkyl groups, 1-10 carbon atoms alkoxy groups, 1-10 carbon atoms alkanes Sulfur group, trialkylsilyl group with 3 to 12 carbon atoms, triarylsilyl group with 18 to 24 carbon atoms, and phosphineoxy group with 6 to 18 carbon atoms.
  • the number of carbon atoms optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, chlorine, cyano, methyl, tert-butyl is "Aryl of 6-20" means that the aryl group may be substituted by one or more of deuterium, fluorine, chlorine, cyano, methyl, and tert-butyl, and may not be substituted by deuterium, fluorine, chlorine, cyano, methyl group, tert-butyl group, and when the number of substituent groups on the aryl group is greater than or equal to 2, the substituent groups may be the same or different.
  • the organic compound provided by the present application has a molecular structure in which an anthracene group is combined with a benzoadamantane spirofluorene.
  • the molecular structure improves the overall electron density of the molecule, improves the carrier transfer rate, and increases the triplet energy level, making the compound suitable for use as the host material of the organic light-emitting layer; on the other hand, the molecular structure has a large molecular weight, which can Effectively increase the glass transition temperature of the material.
  • the benzoadamantane structure and the aromatic group introduced on the rigid conjugated planar anthracene group can increase the steric hindrance, thereby adjusting the structure, improving the film-forming property of the material, and the molecule is not easy to crystallize in an amorphous state, thereby improving the application of this
  • the luminous efficiency of organic electroluminescent devices of organic compounds, and the conversion efficiency of photoelectric conversion devices using the organic compounds are improved.
  • the ring A and the ring B are the same or different, and each is independently selected from a benzene ring, a naphthalene ring, a phenanthrene ring or an anthracene ring, and the ring A or the ring B is not a benzene ring at the same time.
  • the organic compound is selected from the group consisting of the structures shown in the following formulas 2 to 21:
  • adamantane is a three-dimensional structure. In the compound structure diagram, due to different drawing angles, it will show different plane shapes.
  • the spiro ring structures formed on the cyclopentane in the fluorene ring are all adamantane, and the connection position is also identical. For example: the following structure are the same structure.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is: formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the R" on the two benzene rings The number q of "substituents" can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • substituent namely Rc
  • Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, optionally selected from 0, 1, 2, 3, 4 or 5 independently.
  • the "substituted" functional group may be substituted by one or more substituents in the above Rc; when two substituents Rc are attached to the same atom, the two substituents Rc may be independently Exist or connect to each other to form a ring with the atoms; when there are two adjacent substituents Rc on a functional group, the adjacent two substituents Rc may exist independently or be condensed to form a ring with the functional group to which they are connected.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is selected from a substituted aryl group having 30 carbon atoms, then all of the aryl group and the substituents thereon have 30 carbon atoms.
  • the number of carbon atoms of L 1 , L 2 , and Ar 1 refers to all the number of carbon atoms.
  • L 1 is a substituted arylene group with 12 carbon atoms, then all the carbon atoms of the arylene group and the substituents on it are 12.
  • Ar 1 is Then the number of carbon atoms is 7; L 1 is Its carbon number is 12.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation.
  • two or more aromatic groups linked by carbon-carbon bond conjugation may also be considered aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • phenyl and the like are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, Base et al.
  • the "substituted or unsubstituted aryl group" of the present application may contain 6 to 30 carbon atoms.
  • the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 25.
  • the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-18, and in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-13.
  • the number of carbon atoms can be 6, 12, 13, 14, 15, 18, 20, 25 or 30. Of course, the number of carbon atoms can also be other numbers. No more enumerating.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • condensed aromatic rings refer to polyaromatic rings formed by two or more aromatic or heteroaromatic rings sharing a ring edge, such as naphthalene, anthracene, phenanthrene, and pyrene.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituent on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group
  • substituted aryl groups include, but are not limited to: phenyl-substituted naphthyl, naphthyl-substituted phenyl, phenanthrenyl-substituted phenyl, phenyl-substituted biphenyl, dimethylfluorenyl Substituted phenyl, dibenzothienyl substituted phenyl, carbazolyl substituted phenyl, phenanthrolinyl substituted phenyl, and the like.
  • aryl groups as substituents include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthracenyl, dimethylfluorenyl, biphenyl, terphenyl and the like.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be B, O, N, P, Si, At least one of Se and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl , pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, diphenyl thienyl,
  • thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
  • the "substituted or unsubstituted heteroaryl" in the present application may contain 3-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3-25, in other In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3-20, and in other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12-20.
  • the number of carbon atoms can be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30. Of course, the number of carbon atoms can also be are other quantities, which will not be listed here.
  • a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, which may be at least one of B, O, N, P, Si, Se and S, and has at least one N.
  • the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
  • a substituted heteroaryl group may be a heteroaryl group in which one or more than two hydrogen atoms are replaced by, for example, a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups.
  • the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl groups as substituents include, but are not limited to, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, carbazolyl and the like.
  • the alkyl group having 1 to 10 carbon atoms may be a straight-chain alkyl group or a branched-chain alkyl group.
  • the alkyl group having 1 to 10 carbon atoms may be a straight chain alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl and the like.
  • the halogen group may be fluorine, chlorine, bromine, iodine.
  • a non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. Any possible connection methods shown in -1) to (f-10).
  • the dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of one side of the benzene ring,
  • the meaning represented by it includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • R 1 and R 2 are each independently selected from hydrogen.
  • the Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms.
  • the substituent in Ar 1 is selected from deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, and heteroaryl group with 3-20 carbon atoms , alkyl groups with 1 to 5 carbon atoms, haloalkyl groups with 1 to 4 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, trialkylsilyl groups with 3 to 7 carbon atoms, carbon A triarylsilyl group having 18 to 24 atoms.
  • Ar 1 is selected from a substituted or unsubstituted aryl group with 6-20 carbon atoms and a substituted or unsubstituted heteroaryl group with 3-20 carbon atoms.
  • the substituents in Ar 1 are selected from deuterium, fluorine, cyano, alkyl groups with 1 to 5 carbon atoms, aryl groups with 6 to 15 carbon atoms, and heteroaryl groups with 12 to 18 carbon atoms. base.
  • the substituents in Ar 1 include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl , anthracenyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.
  • the Ar 1 is selected from the groups shown in the following i-1 to i-15:
  • M 1 is selected from single bond or
  • G 1 to G 5 and G 1 ′ to G 4 ′ are each independently selected from N, C or C(J 1 ), and at least one of G 1 to G 5 is selected from N; when two of G 1 to G 5 are selected from N; When more than one is selected from C(J 1 ), any two J 1 are the same or different; when two or more of G 1 ' to G 4 ' are selected from C(J 1 ), any two J 1 are the same or different Not the same;
  • G 6 to G 13 are each independently selected from N, C or C(J 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(J 2 ) ), any two J 2 are the same or different;
  • G 14 to G 23 are each independently selected from N, C or C(J 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(J 3 ) ), any two J 3 are the same or different;
  • G 24 to G 33 are each independently selected from N, C or C(J 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(J 4 ) ), any two J 4 are the same or different;
  • Z 1 is selected from hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group with 3-12 carbon atoms, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms , cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio group with 1-10 carbon atoms, triarylsilyl with 18-24 carbon atoms;
  • Z 2 to Z 9 and Z 21 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, Halogenated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, carbon number is an alkylthio group of 1-10, a heteroaryl group with a carbon number of 3-18, a triarylsilyl group with a carbon number of 18-24;
  • Z 10 -Z 20 and J 1 -J 4 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3-12 carbon atoms, and Alkyl, halogenated alkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, An aryl group with 6 to 20 carbon atoms optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl groups, carbon Heteroaryl with 3 to 18 atoms, triarylsilyl with 18 to 24 carbon atoms;
  • h 1 to h 21 are represented by h k
  • Z 1 to Z 21 are represented by Z k
  • k is a variable, representing any integer from 1 to 21
  • h k represents the number of substituents Z k ; wherein, when k is selected from 5 or 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected from When from 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two Z k are the same or different;
  • K 1 is selected from O, S, N(Z 22 ), C(Z 23 Z 24 ), Si(Z 28 Z 29 ); wherein Z 22 , Z 23 , Z 24 , Z 28 , Z 29 are independently selected from each other From: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or the above Z 23 and Z 24 are connected to each other to form a saturated or unsaturated ring having 3 to 15 carbon atoms with their commonly connected atoms, or the above-mentioned Z 28 and Z 29 are connected to each other to form carbon atoms with their commonly connected atoms is a saturated or unsaturated ring of 3-15;
  • K 2 is selected from single bond, O, S, N(Z 25 ), C(Z 26 Z 27 ), Si(Z 30 Z 31 ); wherein Z 25 , Z 26 , Z 27 , Z 30 , Z 31 are each Independently selected from: aryl group with 6-18 carbon atoms, heteroaryl group with 3-18 carbon atoms, alkyl group with 1-10 carbon atoms, or cycloalkyl group with 3-10 carbon atoms , or the above-mentioned Z 26 and Z 27 are connected to each other to form a saturated or unsaturated ring with a carbon number of 3 to 15 with their commonly connected atoms, or the above-mentioned Z 30 and Z 31 are connected to each other to form with their commonly connected atoms A saturated or unsaturated ring having 3 to 15 carbon atoms.
  • the Ar 1 is selected from a substituted or unsubstituted group V 1 , and the unsubstituted group V 1 is selected from the group consisting of:
  • the substituted group V 1 has one or more substituents, and the substituents in the substituted group V 1 are independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, carbon A cycloalkyl group having 3 to 10 atoms and an aryl group having 6 to 12 carbon atoms.
  • Ar 1 is selected from the group consisting of:
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted carbon A heteroarylene group having 3 to 20 atoms.
  • the substituents in L 1 and L 2 are the same or different, and each is independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms, carbon atom An aryl group having 6 to 12 carbon atoms and a cycloalkyl group having 3 to 10 carbon atoms.
  • L 1 and L 2 are the same or different, and are each independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted Biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted Dibenzofuranyl, substituted or unsubstituted N-phenylcarbazolylylene, substituted or unsubstituted carbazolylylene.
  • the substituents in L 1 and L 2 are the same or different, and specific examples include but are not limited to: deuterium, halogen group, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group base, tert-butyl, phenyl, naphthyl, biphenyl, phenanthrenyl, anthracenyl.
  • L 1 and L 2 are the same or different, and each is independently selected from the group consisting of a single bond or the following groups represented by j-1 to j-13:
  • M 2 is selected from single bond or represents a chemical bond
  • Q 1 to Q 5 and Q' 1 to Q' 4 are each independently selected from N or C(J 5 ), and at least one of Q 1 to Q 5 is selected from N; when two or more of Q 1 to Q 5 are selected from N; When selected from C(J 5 ), any two J 5 are the same or different, and when two or more of Q' 1 to Q' 4 are selected from C(J 5 ), any two J 5 are the same or different ;
  • Q 6 to Q 13 are each independently selected from N, C or C(J 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(J 6 ) ), any two J 6 are the same or different;
  • Q 14 to Q 23 are each independently selected from N, C or C(J 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C(J 7 ) ), any two J 7 are the same or different;
  • Q 24 to Q 33 are each independently selected from N, C or C(J 8 ), and at least one of Q 24 to Q 33 is selected from N; when two or more of Q 24 to Q 33 are selected from C(J 8 ) ), any two J 8 are the same or different;
  • E 1 -E 14 , J 5 -J 8 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, optionally by 0, 1, 2, 3, 4 or 5 aryl groups independently selected from deuterium, fluorine, chlorine, cyano, methyl, tert-butyl substituted aryl groups with 6 to 20 carbon atoms, and trialkylsilyl groups with 3 to 12 carbon atoms , an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, a carbon atom A phosphino group with a number of 6-18, a triarylsilyl group with a carbon number of 18-24;
  • e 1 to e 14 are represented by er, E 1 to E 14 are represented by Er , r is a variable, representing any integer from 1 to 14, and er represents the number of substituents E r ; when r is selected from 1, 2, When 3, 4, 5, 6, 9, 13 or 14, er is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, er is selected from 1, 2, 3, 4, 5 or 6; when r is 12, er is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, er is selected from 1, 2, 3, 4, 5, 6 , 7 or 8; when er is greater than 1, any two Er are the same or different;
  • K 3 is selected from O, S, Se, N(E 15 ), C(E 16 E 17 ), Si(E 18 E 19 ); wherein, E 15 , E 16 , E 17 , E 18 and E 19 are each independently is selected from: an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms, an alkyl group with 1-10 carbon atoms, and a cycloalkyl group with 3-10 carbon atoms, Either E 16 and E 17 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms with their commonly connected atoms, or E 18 and E 19 are connected to each other to form carbon atoms with their commonly connected atoms is a saturated or unsaturated ring of 3-15;
  • K 4 is selected from single bond, O, S, Se, N(E 20 ), C(E 21 E 22 ), Si(E 23 E 24 ); wherein, E 20 to E 24 are each independently selected from: carbon atom Aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, or E 21 and E 22 Connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms with the atoms they are commonly connected to, or E 23 and E 24 are connected to each other to form a saturated ring with 3 to 15 carbon atoms with their commonly connected atoms or unsaturated rings.
  • L 1 and L 2 are each independently selected from a single bond or a substituted or unsubstituted group V 2 , and the unsubstituted group V 2 is selected from the group consisting of :
  • the substituted group V 2 has one or more substituents, and the substituents in the substituted group V 2 are independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, carbon An aryl group having 6 to 12 atoms.
  • L 1 and L 2 are each independently selected from the group consisting of a single bond or the following groups:
  • the organic compound is selected from the group consisting of the following compounds:
  • a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound described in the first aspect of the present application .
  • the organic compounds provided in the present application can be used to form at least one organic film layer in the functional layer, so as to improve the efficiency characteristics and lifetime characteristics of electronic components.
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound.
  • the organic light-emitting layer may include a host material and a guest material, wherein the host material includes the organic compound of the present application.
  • the electronic component is an organic electroluminescent device, such as a blue light device.
  • the organic electroluminescent device may include an anode 100 , a hole transport layer 321 , an electron blocking layer 322 , an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340 and a cathode 200 , which are sequentially stacked.
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 321 and the electron blocking layer 322 respectively comprise one or more hole transport materials, and the hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compound.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the host material of the organic light-emitting layer may contain the organic compound of the present application.
  • the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The energy is transferred to the host material, and the host material transfers the energy to the guest material, thereby enabling the guest material to emit light.
  • the host material of the organic light-emitting layer 330 can be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application .
  • the host material of the organic light-emitting layer 330 may be the organic compound of the present application.
  • the guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not specially made in this application. limit.
  • the organic electroluminescent device is a blue light device
  • the guest material of the organic light-emitting layer 330 is BD-1.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 may be composed of ET-06 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the capability of injecting holes into the hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 may be composed of metal Yb.
  • the organic electroluminescent device of the present application is a blue light device.
  • a hole blocking layer 341 may also be disposed between the organic light-emitting layer 330 and the electron transport layer 340 .
  • a third aspect of the present application provides an electronic device including the electronic component described in the second aspect of the present application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • the electronic device is a second electronic device 500
  • the second electronic device 500 includes a photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • the compounds of the synthetic methods not mentioned in this application are all raw materials obtained through commercial channels.
  • the analytical detection of the intermediates and compounds in this application uses an ICP-7700 mass spectrometer.
  • the synthesis method of the organic compounds provided in this application is not particularly limited, and those skilled in the art can determine a suitable synthesis method according to the preparation methods provided in the organic compounds combined with the synthesis examples section of the application.
  • the Synthesis Examples section of the present application exemplarily provides methods for preparing organic compounds, and the raw materials used can be obtained commercially or by methods well known in the art.
  • Those skilled in the art can obtain all the organic compounds provided in the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the organic compounds will not be described in detail here, and those skilled in the art should not interpret the present application as a limitation.
  • Y-1 (100 g, 398.5 mmol), Z-1 (96.3 g, 398.5 mmol), tetrakis(triphenylphosphine) palladium (2.3 g, 1.9 mmol), potassium carbonate (110.2 g, 797.1 mmol), tetrabutylene Ammonium chloride (0.55g, 1.9mmol), toluene (800mL), ethanol (400mL) and deionized water (200mL) were added to the three-necked flask, heated to 78°C under nitrogen protection, and stirred for 6 hours; the reaction solution was cooled to At room temperature, toluene (300 mL) was added for extraction, the organic phases were combined, the organic phase was dried with anhydrous magnesium sulfate, filtered to obtain a filtrate, and the filtrate was concentrated under reduced pressure to obtain a crude product; the obtained crude product was purified by silica gel column chromatography using n-heptane as the mobile
  • Y-2 (33.2 g, 272.2 mmol), Z-2 (100 g, 272.2 mmol), tetrakis(triphenylphosphine) palladium (9.4 g, 8.2 mmol), potassium carbonate (112.8 g, 816.5 mmol), tetrabutylene Ammonium chloride (0.75g, 2.72mmol), toluene (800mL), ethanol (400mL) and deionized water (200mL) were added to the three-necked flask, heated to 78°C under nitrogen protection, and stirred for 8 hours; the reaction solution was cooled to At room temperature, toluene (300 mL) was added for extraction, the organic phases were combined, the organic phase was dried with anhydrous magnesium sulfate, filtered to obtain a filtrate, and the filtrate was concentrated under reduced pressure to obtain a crude product; the obtained crude product was obtained using a dichloromethane/n-heptane system (volume ratio 1
  • Y-3 (100 g, 350.5 mmol), Z-3 (71.5 g, 350.5 mmol), tetrakis(triphenylphosphine) palladium (12.1 g, 10.5 mmol), potassium carbonate (145.3 g, 1051.5 mmol), tetrabutylene Ammonium chloride (0.97g, 3.5mmol), toluene (800mL), ethanol (400mL) and deionized water (200mL) were added to the three-necked flask, heated to 78°C under nitrogen protection, and stirred for 6 hours; the reaction solution was cooled to At room temperature, toluene (300 mL) was added for extraction, the organic phases were combined, the organic phase was dried with anhydrous magnesium sulfate, filtered to obtain a filtrate, and the filtrate was concentrated under reduced pressure to obtain a crude product; the obtained crude product was purified by silica gel column chromatography using n-heptane as the mobile
  • Intermediate IM-A-X was synthesized by referring to the method of intermediate IM-A-1, except that SMA-X/SM-X shown in Table 1 was used instead of SMA-1 to prepare intermediate IM-A-X, wherein, the obtained The intermediates IM-A-X are shown in Table 1.
  • Intermediate IM-B-X/Intermediate IM-B-X-0 were synthesized with reference to the synthesis method of Intermediate IM-B-1, except that Intermediate IM-A-X shown in Table 2 was used instead of Intermediate IM-A-1 to prepare intermediate IM-B-X/intermediate IM-B-X-0, wherein the prepared intermediate IM-B-X/intermediate IM-B-X-0 is shown in Table 2.
  • Intermediate IM-C-X/Intermediate IM-C-X-0 were synthesized by referring to Intermediate IM-C-1 method, except that Intermediate IM-B-X/Intermediate IM-B-X-0 shown in Table 3 were used instead of Intermediate Intermediate IM-C-X/Intermediate IM-C-X-0 is prepared by using body IM-B-1, wherein, the prepared Intermediate IM-C-X/Intermediate IM-C-X-0 is shown in Table 3.
  • Intermediate IM-M-X was synthesized according to the method of Intermediate IM-M-1, except that Intermediate IM-C-X/Intermediate IM-C-X-0 shown in Table 4 was used instead of Intermediate IM-C-1 to prepare for the intermediate IM-M-X, use SMA to replace p-bromophenylboronic acid, and the obtained intermediate IM-M-X is shown in Table 4.
  • Intermediate IM-D-X/Intermediate IM-D-X-0 were synthesized according to the method of Intermediate IM-D-1, except that Intermediate IM-C-X/Intermediate IM-C-X-0/Intermediate IM-M-X were used instead of Intermediate IM-C-1 is used to prepare intermediate IM-D-X/intermediate IM-D-X-0, wherein the prepared intermediate IM-D-X/intermediate IM-D-X-0 is shown in Table 5.
  • Compound X is synthesized with reference to the method of compound 1, the difference is that compound 1 is prepared by using intermediate IM-D-X/intermediate IM-D-X-0 instead of intermediate IM-D-1, and SMB is used instead of bromobenzene to obtain The compound X is shown in Table 6.
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers. Ultraviolet ozone and O 2 :N 2 plasma were used for Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of A hole injection layer (HIL) of , and compound NPB was vacuum-evaporated on the hole injection layer to form a thickness of The hole transport layer (HTL).
  • HIL hole injection layer
  • HTL The hole transport layer
  • Compound EB-01 was evaporated on HTL as electron blocking layer (EBL) with a thickness of
  • Compound 1 was used as the host on EBL, and BD-1 was simultaneously doped according to the film thickness ratio of 100:3 to form a thickness of The organic light-emitting layer (EML).
  • EML organic light-emitting layer
  • ET-06 and LiQ were evaporated on EML at a film thickness ratio of 1:1.
  • Thick electron transport layer (ETL) was evaporated on the electron transport layer to form a thickness of
  • magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer with a film thickness ratio of 1:9 to form a thickness of the cathode.
  • the thickness of the vapor deposition on the above-mentioned cathode is of CP-5 to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that the compounds shown in Table 10 below were substituted for Compound 1 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1 except that Compound A shown in the following Table 9 was substituted for Compound 1 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound B shown in Table 9 below was substituted for Compound 1 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound C shown in Table 9 below was substituted for Compound 1 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound D shown in the following Table 9 was substituted for Compound 1 in forming the organic light-emitting layer.

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Abstract

本申请涉及一种有机化合物以及使用其的电子元件和电子装置，所述有机化合物的结构式如式1所示。本申请提供的有机化合物，可以提高应用该有机化合物的有机致电发光器件的发光效率，以及提高应用该有机化合物的光电转化器件的转化效率。

Description

一种有机化合物以及使用其的电子元件和电子装置
相关申请的交叉引用
本申请要求于2020年9月30日递交的申请号为CN202011063177.8的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请属于有机材料技术领域，具体提供一种有机化合物以及使用其的电子元件和电子装置。
背景技术
有机发光现象是指利用有机物质使电能转变为光能的现象。利用有机发光现象的有机发光元件通常具有包含阳极和阴极以及位于它们之间的有机物层的结构。其中，为了提高有机发光元件的效率和稳定性，往往由各自不同的物质构成多层结构形成有机物层，例如，可以由空穴注入层、空穴传输层、有机发光层、电子传输层、电子注入层等形成。对于这样的有机发光元件的结构而言，如果在两级之间施加电压，则空穴从阳极注入至有机物层，电子从阴极注入至有机物层，当所注入的空穴和电子相遇时，形成激子，该激子再次跃迁至基态时，就会发出光。
现有技术CN106206964、WO2011010843等公开了可以在有机电致发光器件中使用的有机发光层材料。然而，依然有必要继续研发新型的材料，以进一步提高电子元器件的性能。
发明内容
针对现有技术存在的上述问题，本申请的目的是提供一种有机化合物以及使用其的电子元件和电子装置，该有机化合物可用作有机电致发光器件的有机发光层。
本申请第一方面提供一种有机化合物，所述有机化合物的结构式如式1所示：
Figure PCTCN2021102557-appb-000001
其中，环A和环B相同或不同，各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中的至少一者选自成环碳原子数为10～14的稠合芳环；
L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或者未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
各R 1和R 2相同或不同，且各分别独立地选自：氢、氘、卤素基团、氰基、碳原子数为1～10的卤代烷基、碳原子数为1～10的烷基、碳原子数为3～15的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为6～12的芳基、碳原子数为4～12的杂芳基、碳原子数为5～13的杂芳烷基；
m表示R 1的个数，q表示R 2的个数；m、q分别独立地选自1、2、3、4、5、6、7或8；
Ar 1选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
所述L 1、L 2和Ar 1中的取代基相同或者不同，且各自独立地选自：氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为6～18的膦氧基。
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层，所述功能层包含本公开第一方面所述的有机化合物；
优选地，所述功能层包括有机发光层，所述有机发光层包括所述有机化合物；
更优选地，所述有机发光层包含主体材料和客体材料，所述主体材料包含所述有机化合物。
本申请第三方面提供一种电子装置，所述电子装置包括本申请第二方面所述的电子元件。
本申请提供的有机化合物具有以蒽基基团与苯并金刚烷芴结合的分子结构。一方面，该分子结构提升分子整体的电子密度、载流子传输速率和三线态能级，适于用作有机发光层主体材料；并且该分子结构中引入了螺环金刚烷结构，可以改善薄膜性能，进而提高了薄膜的使用寿命。另一方面该分子结构具有大的分子量，可以有效地提升材料的玻璃化转变温度，并且苯并结构及刚性共轭平面蒽基上引入的芳香性基基团可以增加空间位阻，从而调整结构，提高材料成膜性且分子在无定形状态下不易结晶，从而提高应用该有机化合物的有机致电发光器件的发光效率，以及提高应用该有机化合物的光电转化器件的转化效率。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。在附图中：
图1是是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的结构示意图。
图3是本申请另一种实施方式的第二电子装置的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、电子阻挡层；330、有机发光层；341、空穴阻挡层、340、电子传输层；350、电子注入层；400、第一电子装置；500、第二电子装置。
具体实施方式
以下结合附图对本申请的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。
本申请第一方面提供一种有机化合物，所述有机化合物的结构式如式1所示：
Figure PCTCN2021102557-appb-000002
其中，环A和环B相同或不同，各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中的至少一者选自成环碳原子数为10～14的稠合芳环；
L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或者未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
各R 1和R 2相同或不同，且各分别独立地选自：氢、氘、卤素基团、氰基、碳原子数为1～10的卤代烷基、碳原子数为1～10的烷基、碳原子数为3～15的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为6～12的芳基、碳原子数为4～12的杂芳基、碳原子数为5～13的杂芳烷基；
m表示R 1的个数，q表示R 2的个数；m、q分别独立地选自1、2、3、4、5、6、7或8；
Ar 1选自：碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
所述L 1、L 2和Ar 1中的取代基相同或者不同，且各自独立地选自：氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为6～18的膦氧基。
在本申请中，“任选地被0、1、2、3、4或5个独立选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基”是指芳基可以被氘、氟、氯、氰基、甲基、叔丁基中的一个或多个取代，也可以不被氘、氟、氯、氰基、甲基、叔丁基取代，且当芳基上的取代基的个数大于等于2时，取代基可以相同或不同。
本申请提供的有机化合物，以蒽基基团与苯并金刚烷螺芴结合的分子结构。该分子结构一方面提升分子整体的电子密度，提升载流子传输速率，而且提高三线态能级，使化合物适于用于有机发光层主体材料；另一方面该分子结构具有大的分子量，可以有效地提升材料的玻璃化转变温度。而苯并金刚烷结构及刚性共轭平面蒽基上引入的芳香性基基团可以增加空间位阻，从而调整结构，提高材料成膜性且分子在无定形状态下不易结晶，从而提高应用该有机化合物的有机致电发光器件的发光效率，以及提高应用该有机化合物的光电转化器件的转化效率。
在本申请一种具体实施方式中，所述环A和环B相同或不同，各自独立地选自苯环、萘环、菲环或蒽环，且环A或环B不同时为苯环。
在本申请一种具体实施方式中，所述有机化合物选自如下式2至式21所示的结构组成的组：
Figure PCTCN2021102557-appb-000003
Figure PCTCN2021102557-appb-000004
在本申请中，金刚烷是立体结构，在化合物结构图中，因为绘图角度不同，会呈现不同的平面形状，芴环中环戊烷上所形成的螺环结构均为金刚烷，并且连接位置也是相同的。例如：以下结构
Figure PCTCN2021102557-appb-000005
均为同一种结构。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，
Figure PCTCN2021102557-appb-000006
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代 基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为6～18的膦氧基。在本申请中，“取代的”官能团可以被上述Rc中的1个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L 1选自取代的碳原子数为30的芳基，则芳基及其上的取代基的所有碳原子数为30。
在本申请中，L 1、L 2、Ar 1的碳原子数，指的是所有碳原子数。举例而言：L 1为取代的碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：Ar 1为
Figure PCTCN2021102557-appb-000007
则其碳原子数为7；L 1为
Figure PCTCN2021102557-appb-000008
其碳原子数为12。
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言，在本申请中，苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021102557-appb-000009
基等。
本申请的“取代或未取代的芳基”可含有6～30个碳原子，在一些实施例中，取代或未取代的芳基中的碳原子数可以是6～25个，在另一些实施例中取代或未取代的芳基中的碳原子数可以是6～18个，在另一些实施例中取代或未取代的芳基中的碳原子数可以是6～13个。举例而言，其碳原子数量可以是6个、12个、13个、14个、15个、18个、20个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，稠合芳环是指两个或两个以上芳环或杂芳环以共有环边而形成的多芳环，例如萘、蒽、菲、芘。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。
在本申请中，取代的芳基具体实例包括但不限于：苯基取代的萘基、萘基取代的苯基、菲基取代的苯基、苯基取代的联苯基、二甲基芴基取代的苯基、二苯并噻吩基取代的苯基、咔唑基取代的苯基、菲咯啉基取代的苯基等等。
在本申请中，作为取代基的芳基，具体实例包括但不限于：苯基、萘基、菲基、蒽基、二甲基芴基、联苯基、三联苯基等等。
本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，杂芳基是指环中包含1、2、3、4、5或6个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、***基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噻嗪基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
本申请的“取代或未取代的杂芳基”可含有3～30个碳原子，在一些实施例中，取代或未取代的杂芳基中的碳原子数可以是3～25个，在另一些实施例中取代或未取代的杂芳基中的碳原子数可以是3～20个，在另一些实施例中取代或未取代的杂芳基中的碳原子数可以是12～20个。举例而言，其碳原子数量可以是3个、4个、5个、7个、12个、13个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
在本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种，且至少具有一个N。
本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，作为取代基的杂芳基，具体实例包括但不限于：二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、咔唑基等等。
在本申请中，碳原子数为1～10的烷基可以为直链烷基或支链烷基。具体而言，碳原子数为1～10的烷基可以为碳原子数1至10的直链烷基，或碳原子数3至10的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1～10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
在本申请中，卤素基团可以为氟、氯、溴、碘。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021102557-appb-000010
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。
举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～(f-10)所示出的任一可能的连接方式。
Figure PCTCN2021102557-appb-000011
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2021102557-appb-000012
在本申请的一些实施方式中，式1中，
Figure PCTCN2021102557-appb-000013
选自如下所示的结构所组成的组：
Figure PCTCN2021102557-appb-000014
其中，
Figure PCTCN2021102557-appb-000015
表示上述结构用于与
Figure PCTCN2021102557-appb-000016
连接的化学键，
Figure PCTCN2021102557-appb-000017
表示上述结构用于与
Figure PCTCN2021102557-appb-000018
连接的化学键。
在本申请的一些实施方式中，
Figure PCTCN2021102557-appb-000019
中，q等于1时，
Figure PCTCN2021102557-appb-000020
选自如下所示的结构所组成的组：
Figure PCTCN2021102557-appb-000021
Figure PCTCN2021102557-appb-000022
其中，
Figure PCTCN2021102557-appb-000023
表示上述结构中用于与
Figure PCTCN2021102557-appb-000024
连接的化学键，
Figure PCTCN2021102557-appb-000025
表示上述结构中用于与
Figure PCTCN2021102557-appb-000026
连接的化学键。
在本申请的一些实施方式中，式1中，
Figure PCTCN2021102557-appb-000027
选自如下所示的结构所组成的组：
Figure PCTCN2021102557-appb-000028
其中，
Figure PCTCN2021102557-appb-000029
表示上述结构中用于与
Figure PCTCN2021102557-appb-000030
连接的化学键，
Figure PCTCN2021102557-appb-000031
表示上述结构中用于与
Figure PCTCN2021102557-appb-000032
连接的化学键。
在本申请的一些实施方式中，
Figure PCTCN2021102557-appb-000033
中，m等于1时，
Figure PCTCN2021102557-appb-000034
选自如下所示的结构所组成的组：
Figure PCTCN2021102557-appb-000035
其中，
Figure PCTCN2021102557-appb-000036
表示上述结构中用于与
Figure PCTCN2021102557-appb-000037
连接的化学键，
Figure PCTCN2021102557-appb-000038
表示上述结构中用于与
Figure PCTCN2021102557-appb-000039
连接的化学键。
在本申请的一些实施方式中，R 1和R 2分别独立地选自氢。
在本申请的一些实施方式中，所述Ar 1选自碳原子数为6～24的取代或未取代的芳基、碳原子数为3～24的取代或未取代的杂芳基。
在本申请的一些实施方式中，所述Ar 1中的取代基选自氘、卤素基团、氰基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～5的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～10的环烷基、碳原子数为3～7的三烷基硅基、碳原子数为18～24的三芳基硅基。
优选地，Ar 1选自碳原子数为6～20的取代或未取代的芳基、碳原子数为3～20的取代或未取代的杂芳基。
优选地，Ar 1中的取代基选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～15的芳基、碳原子数为12～18的杂芳基。
具体地，所述Ar 1中的取代基包括但不限于：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、蒽基、菲基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基。
在本申请的一些实施方式中，所述Ar 1选自如下i-1至i-15所示的基团：
Figure PCTCN2021102557-appb-000040
Figure PCTCN2021102557-appb-000041
其中，M 1选自单键或者
Figure PCTCN2021102557-appb-000042
G 1～G 5和G 1’～G 4’各自独立地选自N、C或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；当G 1’～G 4’中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
G 6～G 13各自独立地选自N、C或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
G 14～G 23各自独立地选自N、C或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
G 24～G 33各自独立地选自N、C或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
Z 1选自氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为18～24的三芳基硅基；
Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～10的烷硫基、碳原子数为3～18的杂芳基、碳原子数为18～24的三芳基硅基；
Z 10～Z 20、J 1～J 4各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为18～24的三芳基硅基；
h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者 21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 28Z 29)；其中，Z 22、Z 23、Z 24、Z 28、Z 29各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 28和Z 29相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 30Z 31)；其中，Z 25、Z 26、Z 27、Z 30、Z 31各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 30和Z 31相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
在本申请的一些实施方式中，所述Ar 1选自取代或未取代的基团V 1，所述未取代的基团V 1选自以下基团组成的组：
Figure PCTCN2021102557-appb-000043
取代的基团V 1上具有一个或两个以上的取代基，取代的基团V 1中的取代基独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为3～10的环烷基、碳原子数为6～12的芳基。
可选地，Ar 1选自以下基团组成的组：
Figure PCTCN2021102557-appb-000044
Figure PCTCN2021102557-appb-000045
在本申请的一些实施方式中，L 1和L 2相同或不同，且各自独立地选自单键、取代或未取代的碳原子数为6～20的亚芳基、取代或未取代的碳原子数为3～20的亚杂芳基。
在本申请的一些实施方式中，L 1和L 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基、碳原子数为3～10的环烷基。
在本申请的一些实施方式中，L 1和L 2相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚菲基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚N-苯基咔唑基、取代或未取代的亚咔唑基。
在本申请的一些实施方式中，L 1和L 2中的取代基相同或不同，具体实例包括但不限于：氘、卤素基团、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、蒽基。
在本申请的一些实施方式中，L 1和L 2相同或不同，且各自独立地选自单键或如下j-1至j-13所示基团所组成的组：
Figure PCTCN2021102557-appb-000046
Figure PCTCN2021102557-appb-000047
其中，M 2选自单键或者
Figure PCTCN2021102557-appb-000048
表示化学键；
Q 1～Q 5和Q’ 1～Q’ 4各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同，当Q’ 1～Q’ 4中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
Q 6～Q 13各自独立地选自N、C或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 33中至少一个选自N；当Q 24～Q 33中的两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
E 1～E 14、J 5～J 8各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氯、氰基、甲基、叔丁基取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的膦氧基，碳原子数为18～24的三芳基硅基；
e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19)；其中，E 15、E 16、E 17、E 18和E 19各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 18和E 19相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 4选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24)；其中，E 20至E 24各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基，或者E 21和E 22相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 23和E 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和 的环。
在本申请的一些实施方式中，L 1和L 2各自独立地选自单键或者取代或未取代的基团V 2，所述未取代的基团V 2选自如下基团所组成的组：
Figure PCTCN2021102557-appb-000049
取代的基团V 2上具有一个或两个以上的取代基，取代的基团V 2中的取代基独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基。
可选地，L 1和L 2各自独立地选自单键或如下基团组成的组：
Figure PCTCN2021102557-appb-000050
在本申请的一种具体实施方式中，所述有机化合物选自如下化合物组成的组：
Figure PCTCN2021102557-appb-000051
Figure PCTCN2021102557-appb-000052
Figure PCTCN2021102557-appb-000053
Figure PCTCN2021102557-appb-000054
Figure PCTCN2021102557-appb-000055
Figure PCTCN2021102557-appb-000056
Figure PCTCN2021102557-appb-000057
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的有机化合物。
本申请所提供的有机化合物可以用于形成功能层中的至少一个有机膜层，以改善电子元件的效率特性和寿命特性。
具体的一种实施方式中，所述功能层包括有机发光层，所述有机发光层包括所述有机化合物。通常地，所述有机发光层可以包含主体材料和客体材料，其中，所述主体材料包含本申请的有机化合物。
按照本申请的一种实施方式中，电子元件为有机电致发光器件，例如为蓝光器件。如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、电子阻挡层322、作为能量转化层的有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层321和电子阻挡层322分别包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。有机发光层的主体材料可以含有本申请的有机化合物。在本申请一些实施方式中，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的主体材料可以为金属螯合物类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的主体材料可以为本申请的有机化合物。
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请一些实施方式中，所述有机电致发光器件为蓝光器件，有机发光层330的客体材料为BD-1。
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种示例性实施方式中，电子传输层340可以由ET-06和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物 等无机材料，或者可以包括碱金属与有机物的络合物。在本申请一种实施方式中，电子注入层350可以由金属Yb组成。
可选地，本申请的有机电致发光器件为蓝光器件。
可选地，在有机发光层330和电子传输层340之间还可以设置有空穴阻挡层341。
本申请第三方面提供一种电子装置包含本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式，如图3所示，所述电子装置为第二电子装置500，第二电子装置500包括光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
本申请中的中间体和化合物的分析检测使用ICP-7700质谱仪。
下面结合合成实施例来具体说明本申请的有机化合物的合成方法。
本申请对提供的有机化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的有机化合物结合合成例部分提供的制备方法确定合适的合成方法。换言之，本申请的合成例部分示例性地提供了有机化合物的制备方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有有机化合物，在此不再详述制备该有机化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。
使用以下方法合成本申请中化合物
Figure PCTCN2021102557-appb-000058
将Y-1(100g,398.5mmol)、Z-1(96.3g,398.5mmol)、四(三苯基膦)钯(2.3g,1.9mmol)、碳酸钾(110.2g,797.1mmol)、四丁基氯化铵(0.55g,1.9mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(300mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/正庚烷体系(体积比1：3)进行重结晶提纯，得到SM-1(112.8g，收率77％)。
Figure PCTCN2021102557-appb-000059
将Y-2(33.2g,272.2mmol)、Z-2(100g,272.2mmol)、四(三苯基膦)钯(9.4g,8.2mmol)、碳酸钾(112.8g,816.5mmol)、四丁基氯化铵(0.75g,2.72mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(300mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤 液减压浓缩得到粗品；所得粗品使用二氯甲烷/正庚烷体系(体积比1:3)进行重结晶提纯，得到SM-2(64.8g，收率75％)。
Figure PCTCN2021102557-appb-000060
将Y-3(100g,350.5mmol)、Z-3(71.5g,350.5mmol)、四(三苯基膦)钯(12.1g,10.5mmol)、碳酸钾(145.3g,1051.5mmol)、四丁基氯化铵(0.97g,3.5mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(300mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/正庚烷体系(体积比1：3)进行重结晶提纯，得到SM-3(82.4g，收率74％)。
Figure PCTCN2021102557-appb-000061
将镁条(22.9,944.5mmol)和***(250mL)置于氮气保护下干燥的圆底烧瓶中，加入碘(250mg)。而后将溶有SMA-1(100g,314.4mmol)的***(500mL)溶液缓慢滴入烧瓶中，滴加完毕后升温至35℃，搅拌3小时；将反应液降温至0℃，向其中缓慢滴入溶有金刚烷酮(37.8g,252mmol)的***(500mL)溶液，滴加完毕后升温至35℃，继续搅拌6小时；将反应液冷却至室温，向其中加入5％盐酸至pH<7，搅拌1小时，加入***(500mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到固体中间体IM-A-1(78.5g，收率80％)。
参照中间体IM-A-1方法合成中间体IM-A-X，不同之处在于，使用表1所示的SMA-X/SM-X代替SMA-1来制备中间体IM-A-X，其中，制得的中间体IM-A-X如表1所示。
表1
Figure PCTCN2021102557-appb-000062
Figure PCTCN2021102557-appb-000063
Figure PCTCN2021102557-appb-000064
Figure PCTCN2021102557-appb-000065
向反应瓶中加入中间体IM-A-1(40g,102.8mmol)，三氟乙酸(400mL)，开启搅拌，然后逐渐升温至80℃，回流反应12h，反应完成后，将反应液倒入水中(600mL)，搅拌30min后过滤，用水淋洗，用乙醇淋洗，后得到粗品用二氯甲烷：正庚烷＝(体积比1：2)重结晶，得到中间体IM-B-1(30.5g，收率：80％)。
参照中间体IM-B-1的合成方法合成中间体IM-B-X/中间体IM-B-X-0，不同之处在于，使用表2所示的中间体IM-A-X代替中间体IM-A-1来制备中间体IM-B-X/中间体IM-B-X-0，其中，制得的中间体IM-B-X/中间体IM-B-X-0如表2所示。
表2
Figure PCTCN2021102557-appb-000066
Figure PCTCN2021102557-appb-000067
Figure PCTCN2021102557-appb-000068
Figure PCTCN2021102557-appb-000069
向反应瓶中投入中间体IM-B-1(15g，40.4mmol)、联硼酸频哪醇酯(10.3g，40.4mmol)、三(二亚苄基丙酮)二钯(0.74g，0.81mmol)、2-二环己基磷-2,4,6-三异丙基联苯(0.19g，0.40mmol)、醋酸钾(7.9g，80.8mmol)和1,4-二氧六环(150mL)，氮气保护下升温至110℃，加热回流搅拌5h。反应液冷却至室温后，利用二氯甲烷和水萃取反应溶液，有机层经无水硫酸镁干燥并过滤，过滤后将滤液通过短硅胶柱，减压除去溶剂，使用二氯甲烷/正庚烷(体积比1:3)体系对粗品进行重结晶提纯，得到中间体IM-C-1(14.0g，收率为：75％)。
参照中间体IM-C-1方法合成中间体IM-C-X/中间体IM-C-X-0，不同之处在于，使用表3所示的中间体IM-B-X/中间体IM-B-X-0代替中间体IM-B-1来制备中间体IM-C-X/中间体IM-C-X-0，其中，制得的中间体IM-C-X/中间体IM-C-X-0如表3所示。
表3
Figure PCTCN2021102557-appb-000070
Figure PCTCN2021102557-appb-000071
Figure PCTCN2021102557-appb-000072
Figure PCTCN2021102557-appb-000073
将中间体IM-C-1(10g,21.6mmol)，对溴苯硼酸(4.34g,21.6mmol)，醋酸钯(0.05g,0.22mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(0.21g,0.43mmol)以及碳酸钾(5.98g,43.2mmol)加入甲苯(80mL)，无水乙醇(40mL)和去离子水(20mL)中，氮气保护下加热至80℃，搅拌2h而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系(体积比1：3)对粗品进行重结晶提纯，得到IM-M-1(7.4g，收率75％)。
参照中间体IM-M-1方法合成中间体IM-M-X，不同之处在于，使用表4所示的中间体IM-C-X/中间体IM-C-X-0代替中间体IM-C-1来制备中间体IM-M-X，采用SM A代替对溴苯硼酸，制得的中间体IM-M-X如表4所示。
表4
Figure PCTCN2021102557-appb-000074
Figure PCTCN2021102557-appb-000075
将中间体IM-C-1(10g,21.6mmol)、10-溴蒽-9-硼酸(6.51g,21.6mmol)、醋酸钯(0.05g,0.22mmol)、2-二环己基磷-2',4',6'-三异丙基联苯(0.21g,0.43mmol)以及碳酸钾(5.98g,43.2mmol)加入甲苯(80mL)，无水乙醇(40mL)和去离子水(20mL)中，氮气保护下加热至80℃，搅拌2h而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系(体积比1：3)对粗品进行重结晶提纯，得到中间体IM-D-1(8.42g，收率70％)。
参照中间体IM-D-1方法合成中间体IM-D-X/中间体IM-D-X-0，不同之处在于，使用中间体IM-C-X/中间体IM-C-X-0/中间体IM-M-X代替中间体IM-C-1来制备中间体IM-D-X/中间体IM-D-X-0，其中，制得的中间体IM-D-X/中间体IM-D-X-0如表5所示。
表5
Figure PCTCN2021102557-appb-000076
Figure PCTCN2021102557-appb-000077
Figure PCTCN2021102557-appb-000078
Figure PCTCN2021102557-appb-000079
Figure PCTCN2021102557-appb-000080
将中间体IM-D-1(5g，8.98mmol)、溴苯(1.41g，8.98mmol)、四三苯基磷钯(0.52g，0.44mmol)、碳酸钾(3.71g，26.9mmol)、四丁基氯化铵(0.12g，0.45mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)、水(10mL)加入反应器中，80℃下回流12h，当反应结束时，使用二氯甲烷和水进行萃取，取有机相无水MgSO 4干燥，抽滤，浓缩有机层，粗产物硅胶过柱提纯，得到化合物1(4.23g，收率80％).
参照化合物1的方法合成化合物X，不同之处在于，使用中间体IM-D-X/中间体IM-D-X-0代替中间体IM-D-1来制备化合物1，使用SM B代替溴苯，制得的化合物X如表6所示。
表6
Figure PCTCN2021102557-appb-000081
Figure PCTCN2021102557-appb-000082
Figure PCTCN2021102557-appb-000083
Figure PCTCN2021102557-appb-000084
Figure PCTCN2021102557-appb-000085
Figure PCTCN2021102557-appb-000086
Figure PCTCN2021102557-appb-000087
表6中化合物的质谱数据如表7所示。
表7
化合物 质谱[M+H] + 化合物 质谱[M+H] +
1 589.3 136 695.3
2 639.3 162 679.3
5 665.3 175 755.3
6 665.3 182 665.3
7 679.3 186 679.3
35 639.3 152 679.3
45 695.3 212 715.3
49 705.3 317 729.3
75 755.3 231 711.3
73 689.3 247 639.3
70 715.3 260 681.3
88 665.3 316 681.3
107 771.3 276 805.3
119 715.3 291 791.3
148 665.3    
表6中部分化合物的核磁数据如表8所示。
表8
Figure PCTCN2021102557-appb-000088
器件实施例
实施例1
通过以下过程制备阳极：将厚度为
Figure PCTCN2021102557-appb-000089
的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2021102557-appb-000090
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀化合物NPB，以形成厚度为
Figure PCTCN2021102557-appb-000091
的空穴传输层(HTL)。
在HTL上蒸镀化合物EB-01作为电子阻挡层(EBL)，厚度为
Figure PCTCN2021102557-appb-000092
在EBL上将化合物1作为主体，按照膜厚比100:3同时掺杂BD-1，形成厚度为
Figure PCTCN2021102557-appb-000093
的有机发光层(EML)。
在EML上将ET-06和LiQ以1:1的膜厚比进行蒸镀形成了
Figure PCTCN2021102557-appb-000094
厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021102557-appb-000095
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1：9的膜厚比真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021102557-appb-000096
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021102557-appb-000097
的CP-5，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例2-实施例29
除了在形成有机发光层时，以下表10中所示的化合物替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例1
除了在形成有机发光层时，以下表9中所示的化合物A替代化合物1以外，利用与实施例1 相同的方法制作有机电致发光器件。
比较例2
除了在形成有机发光层时，以下表9中所示的化合物B替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例3
除了在形成有机发光层时，以下表9中所示的化合物C替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例4
除了在形成有机发光层时，以下表9中所示的化合物D替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
以上实施例1-29和比较例1-4中使用的化合物结构如下表9所示：
表9
Figure PCTCN2021102557-appb-000098
对以上实施例1-29和比较例1-4中制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的IVL性能，T95寿命在15mA/cm 2测试，其结果如表10所示。
表10
Figure PCTCN2021102557-appb-000099
根据表10的结果可知，作为发光主体材料的化合物的实施例1-29与已公知的化合物所对应 的器件比较例1-4，本申请中使用的化合物作为有机发光层制备的上述有机电致发光器件的发光效率(Cd/A)至少提高了6.64％，外量子效率(EQE％)至少提高了6.70％，寿命至少提高了11.76％，寿命最长可提高174h。

Claims (13)

  1. 一种有机化合物，其特征在于，所述有机化合物的结构式如式1所示：
    Figure PCTCN2021102557-appb-100001
    其中，环A和环B相同或不同，各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中的至少一者选自成环碳原子数为10～14的稠合芳环；
    L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
    各R 1和R 2相同或不同，且各分别独立地选自：氢、氘、卤素基团、氰基、碳原子数为1～10的卤代烷基、碳原子数为1～10的烷基、碳原子数为3～15的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为6～12的芳基、碳原子数为4～12的杂芳基、碳原子数为5～13的杂芳烷基；
    m表示R 1的个数，q表示R 2的个数；m、q分别独立地选自1、2、3、4、5、6、7或8；
    Ar 1选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
    所述L 1、L 2和Ar 1中的取代基相同或者不同，且各自独立地选自：氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为6～18的膦氧基。
  2. 根据权利要求1所述的有机化合物，其中，所述环A和环B相同或不同，各自独立地选自苯环、萘环、菲环或蒽环，且环A和环B不同时为苯环。
  3. 根据权利要求1所述的有机化合物，其中，式1中，
    Figure PCTCN2021102557-appb-100002
    选自如下所示的结构所组成的组：
    Figure PCTCN2021102557-appb-100003
    其中，
    Figure PCTCN2021102557-appb-100004
    表示上述结构用于与
    Figure PCTCN2021102557-appb-100005
    连接的化学键，
    Figure PCTCN2021102557-appb-100006
    表示上述结构用于与
    Figure PCTCN2021102557-appb-100007
    连接的化学键。
  4. 根据权利要求1所述的有机化合物，其中，式1中，
    Figure PCTCN2021102557-appb-100008
    选自如下所示的结构所组成的组：
    Figure PCTCN2021102557-appb-100009
    其中，
    Figure PCTCN2021102557-appb-100010
    表示上述结构中用于与
    Figure PCTCN2021102557-appb-100011
    连接的化学键，
    Figure PCTCN2021102557-appb-100012
    表示上述结构中用于与
    Figure PCTCN2021102557-appb-100013
    连接的化学键。
  5. 根据权利要求1所述的有机化合物，其中，所述Ar 1选自碳原子数为6～20的取代或未取代的芳基、碳原子数为3～20的取代或未取代的杂芳基；
    优选地，所述Ar 1中的取代基选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～15的芳基、碳原子数为12～18的杂芳基。
  6. 根据权利要求1所述的有机化合物，其中，所述Ar 1选自取代或未取代的基团V 1，所述未取代的基团V 1选自以下基团组成的组：
    Figure PCTCN2021102557-appb-100014
    取代的基团V 1上具有一个或两个以上的取代基，取代的基团V 1中的取代基独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为3～10的环烷基、碳原子数为6～12的芳基。
  7. 根据权利要求1所述的有机化合物，其中，L 1和L 2相同或不同，且各自独立地选自单键、取代或未取代的碳原子数为6～20的亚芳基、取代或未取代的碳原子数为3～20的亚杂芳基；
    优选地，L 1和L 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基、碳原子数为3～10的环烷基。
  8. 根据权利要求1所述的有机化合物，其中，L 1和L 2相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚菲基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚N-苯基咔唑基、取代或未取代的亚咔唑基；
    优选地，L 1和L 2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、蒽基。
  9. 根据权利要求1所述的有机化合物，其中，L 1和L 2各自独立地选自单键或者取代或未取代的基团V 2，所述未取代的基团V 2选自如下基团所组成的组：
    Figure PCTCN2021102557-appb-100015
    取代的基团V 2上具有一个或两个以上的取代基，取代的基团V 2中的取代基独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基。
  10. 根据权利要求1所述的有机化合物，其中，所述有机化合物选自以下化合物所组成的组：
    Figure PCTCN2021102557-appb-100016
    Figure PCTCN2021102557-appb-100017
    Figure PCTCN2021102557-appb-100018
    Figure PCTCN2021102557-appb-100019
    Figure PCTCN2021102557-appb-100020
    Figure PCTCN2021102557-appb-100021
    Figure PCTCN2021102557-appb-100022
    Figure PCTCN2021102557-appb-100023
  11. 一种电子元件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层，所述功能层包含权利要求1～10任一项所述的有机化合物；
    优选地，所述功能层包括有机发光层，所述有机发光层包括所述有机化合物；
    更优选地，所述有机发光层包含主体材料和客体材料，所述主体材料包含所述有机化合物。
  12. 根据权利要求11所述的电子元件，其中，所述电子元件为有机电致发光器件；
    优选地，所述有机电致发光器件为蓝光器件。
  13. 一种电子装置，其特征在于，包括权利要求11或12所述的电子元件。
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111848501B (zh) 2020-05-08 2021-06-01 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN112142548B (zh) * 2020-09-30 2021-09-24 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020046049A1 (ko) * 2018-08-31 2020-03-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
CN111018797A (zh) * 2019-12-26 2020-04-17 陕西莱特光电材料股份有限公司 有机化合物、包含该有机化合物的电子元件及电子装置
CN111377853A (zh) * 2019-12-27 2020-07-07 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
KR20200107855A (ko) * 2019-03-08 2020-09-16 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN111825518A (zh) * 2019-12-30 2020-10-27 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件和电子装置
CN111848588A (zh) * 2020-07-17 2020-10-30 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置
CN111925315A (zh) * 2020-04-07 2020-11-13 陕西莱特光电材料股份有限公司 含氮化合物、使用其的有机致电发光器件及电子装置
CN112142548A (zh) * 2020-09-30 2020-12-29 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6919473B2 (en) * 2002-09-17 2005-07-19 Cph Innovations Corporation Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US20090105488A1 (en) * 2007-10-22 2009-04-23 Chien-Hong Cheng Triptycene derivatives and their application
KR20110008892A (ko) 2009-07-21 2011-01-27 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
US8421346B2 (en) * 2011-01-28 2013-04-16 Semiconductor Energy Laboratory Co., Ltd. Composite material, light-emitting element, light-emitting device, lighting device, electronic device, and fluorene derivative
EP2720666B1 (en) * 2011-06-20 2019-03-20 The Procter and Gamble Company Personal care compositions comprising shaped abrasive particles
US9192552B2 (en) * 2011-07-07 2015-11-24 The Procter & Gamble Company Personal care compositions with improved solubility of a solid UV active
US9549891B2 (en) * 2012-03-19 2017-01-24 The Procter & Gamble Company Superabsorbent polymers and sunscreen actives for use in skin care compositions
US9271912B2 (en) * 2012-06-13 2016-03-01 The Procter & Gamble Company Personal care compositions comprising a pH tuneable gellant and methods of using
WO2014025370A1 (en) * 2012-08-10 2014-02-13 Hallstar Innovations Corp. Tricyclic energy quencher compounds for reducing singlet oxygen generation
US9145383B2 (en) * 2012-08-10 2015-09-29 Hallstar Innovations Corp. Compositions, apparatus, systems, and methods for resolving electronic excited states
JP6266632B2 (ja) * 2013-09-06 2018-01-24 出光興産株式会社 アントラセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
KR20150098181A (ko) * 2014-02-17 2015-08-27 삼성디스플레이 주식회사 유기 일렉트로루미네센스 소자
US20160351817A1 (en) 2015-05-27 2016-12-01 Samsung Display Co., Ltd. Organic light-emitting device
CA2988808C (en) * 2015-06-29 2021-05-25 The Procter & Gamble Company Superabsorbent polymers, waxes, oils, and starch powders for use in skincare compositions
JP2019024027A (ja) * 2015-10-20 2019-02-14 出光興産株式会社 有機エレクトロルミネッセンス素子
JP2019016614A (ja) * 2015-10-20 2019-01-31 出光興産株式会社 有機エレクトロルミネッセンス素子
WO2017130079A1 (en) * 2016-01-29 2017-08-03 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
KR102064990B1 (ko) * 2016-03-11 2020-03-02 주식회사 엘지화학 에틸렌 슬러리 중합용 혼성 담지 촉매 시스템 및 이를 이용한 에틸렌 중합체의 제조 방법
CN111454197B (zh) * 2019-12-31 2021-04-13 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和电子装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020046049A1 (ko) * 2018-08-31 2020-03-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR20200107855A (ko) * 2019-03-08 2020-09-16 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN111018797A (zh) * 2019-12-26 2020-04-17 陕西莱特光电材料股份有限公司 有机化合物、包含该有机化合物的电子元件及电子装置
CN111377853A (zh) * 2019-12-27 2020-07-07 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
CN111825518A (zh) * 2019-12-30 2020-10-27 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件和电子装置
CN111925315A (zh) * 2020-04-07 2020-11-13 陕西莱特光电材料股份有限公司 含氮化合物、使用其的有机致电发光器件及电子装置
CN111848588A (zh) * 2020-07-17 2020-10-30 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置
CN112142548A (zh) * 2020-09-30 2020-12-29 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置

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