WO2021244442A1 - 有机化合物以及使用其的电子元件和电子装置 - Google Patents

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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WO2021244442A1
WO2021244442A1 PCT/CN2021/096926 CN2021096926W WO2021244442A1 WO 2021244442 A1 WO2021244442 A1 WO 2021244442A1 CN 2021096926 W CN2021096926 W CN 2021096926W WO 2021244442 A1 WO2021244442 A1 WO 2021244442A1
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李林刚
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

  • This application belongs to the technical field of organic materials, and specifically provides an organic compound and an electronic component and an electronic device using the organic compound.
  • OLED Organic electroluminescent materials
  • Organic light-emitting devices generally include an anode, a cathode, and an organic material layer in between.
  • the organic material layer is usually formed in a multi-layer structure composed of different materials to improve the brightness, efficiency and life of the organic electroluminescent device.
  • the organic material layer may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and Electron injection layer and other components.
  • holes and electrons are injected into the organic material layer from the anode and the cathode respectively, and excitons are formed when the injected holes and electrons meet, and when these excitons return Glows in the ground state.
  • the purpose of this application is to provide an organic compound and an electronic component and electronic device using the organic compound, which can be used as a hole blocking layer and/or an electron transport layer of an organic electroluminescent device.
  • the first aspect of the present application provides an organic compound, the structural formula of the organic compound is as shown in formula (1):
  • R 1 and R 2 are the same or different from each other, and are each independently selected from substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted phenyl groups, when R 1 or When R 2 is a substituted alkyl group, the substituents in the substituted alkyl group are the same or different, and are each independently selected from the group consisting of deuterium, fluorine, chlorine, and cyano; when R 1 or R 2 is substituted In the case of the phenyl group, the substituents in the substituted phenyl groups are the same or different, and are independently selected from alkyl groups having 1 to 6 carbon atoms, cyano groups, halogen groups, deuterium, and trimethylsilyl groups.
  • Each R 3 is the same or different from each other, and is independently selected from deuterium, halogen group, cyano group, haloalkyl group having 1 to 12 carbon atoms, alkyl group having 1 to 12 carbon atoms, and 1 carbon atom ⁇ 12 alkoxy, 3-12 cycloalkyl, 1-12 alkylthio, 3-12 trialkylsilyl, optionally substituted by 0 , 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, chlorine, and cyano substituted with 6 to 20 carbon atoms, optionally 0, 1, 2, 3 to 4 or 5 substituents independently selected from the group consisting of deuterium, fluorine, chlorine, and cyano substituted by a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and a carbon atom
  • p is selected from 0, 1, 2, 3, 4, 5, 6 or 7;
  • Each Y is the same or different from each other, and each independently has the structure shown in formula (2), X 1 , X 2 , X 3 , X 4, and X 5 are the same or different from each other, and each independently is C(R 4 ) Or N, and at least one of X 1 , X 2 , X 3 , X 4 and X 5 is N; m is selected from 1 or 2; n is selected from 1 or 2;
  • each R 4 is the same or different, and each independently is H or Or two adjacent R 4 are connected to each other to form a substituted or unsubstituted 5-10 membered aromatic ring or a substituted or unsubstituted 5-10 membered heteroaromatic ring; the substituted 5-10 membered aromatic ring or a substituted 5
  • the substituents in the ⁇ 10-membered heteroaromatic ring are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, C1-C12 alkyl group, C1-C12 alkyl halide Group, alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, aryl group having 6 to 25 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, carbon The group consisting of a trialkylsilyl group having 3 to 12 atoms, an arylsilyl group having 8 to 18 carbon atoms
  • Each Ar is independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms, and substituted or unsubstituted carbon atoms of 1 to 12 Alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 12 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, and substituted or unsubstituted carbon atoms of 4 to 30 The group of heteroaralkyl groups;
  • Each of L 1 and L 2 is the same or different from each other, and is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 3 to 30 The group consisting of heteroarylene groups;
  • the substituents in each of L 1 , L 2 and Ar are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 12 carbon atoms, and 1 to 12 carbon atoms
  • An aryl group having 6 to 25 atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, and the number of carbon atoms is The group consisting of 3-12 trialkylsilyl groups, arylsilyl groups having 8-18 carbon atoms and cycloalkyl groups having 3-12 carbon atoms; in each
  • a second aspect of the present application provides an electronic component, including an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; the functional layer contains the organic compound provided in the first aspect of the present application;
  • the functional layer includes an electron transport layer, and the electron transport layer contains the organic compound according to the first aspect of the present disclosure
  • the functional layer includes a hole blocking layer, and the hole blocking layer contains the organic compound described in the first aspect of the present disclosure.
  • a third aspect of the present application provides an electronic device, and the electronic device includes the electronic component provided in the second aspect of the present application.
  • the 9-position methyl group, the phenyl group and the ortho-position oxygen atom can all provide electrons to the benzene ring through the conjugation/hyperconjugation effect, thereby Make the group have a high conjugated electron cloud density, and introduce a substituted electron-deficient heteroaryl group as an electron injection and transport group into the mother nucleus to enhance the polarity of the entire molecule, which is more conducive to the direction of the material molecule Alignment, thereby enhancing the injection and transmission of electrons, and improving the efficiency of the device.
  • the asymmetry and steric hindrance of the oxaphenanthrene group is greater than that of the general planar conjugated group, which makes it have lower crystallinity and good film-forming properties, so that it can be used in organic electroluminescence devices. Can effectively improve the life of the device.
  • the substituted nitrogen-containing heteroaryl group connected to the oxaphenanthrene core is an electron-deficient group, which is suitable for accepting electrons to form a negative ion center, and thus has excellent effects of transporting electrons and blocking holes. When the substituted nitrogen-containing heteroaryl structure contains cyano substituents, the molecular polarity and dipole moment are further improved, and the electron mobility is improved.
  • 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 photoelectric conversion device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
  • Anode 100.
  • Anode 200. Cathode; 300. Functional layer; 310.
  • Hole injection layer 320. First hole transport layer; 321.
  • the first aspect of the present application provides an organic compound, which has a structure represented by the following formula (1):
  • R 1 and R 2 are the same or different from each other, and are each independently selected from substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted phenyl groups, when R 1 or When R 2 is a substituted alkyl group, the substituents in the substituted alkyl group are the same or different, and are each independently selected from the group consisting of deuterium, fluorine, chlorine, and cyano; when R 1 or R 2 is substituted In the case of the phenyl group, the substituents in the substituted phenyl groups are the same or different, and are independently selected from alkyl groups having 1 to 6 carbon atoms, cyano groups, halogen groups, deuterium, and trimethylsilyl groups.
  • Each R 3 is the same or different from each other, and is independently selected from deuterium, halogen group, cyano group, haloalkyl group having 1 to 12 carbon atoms, alkyl group having 1 to 12 carbon atoms, and 1 carbon atom ⁇ 12 alkoxy, 3-12 cycloalkyl, 1-12 alkylthio, 3-12 trialkylsilyl, optionally substituted by 0 , 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, chlorine, and cyano substituted with 6 to 20 carbon atoms, optionally 0, 1, 2, 3 to 4 or 5 substituents independently selected from the group consisting of deuterium, fluorine, chlorine, and cyano substituted by a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and a carbon atom
  • p is selected from 0, 1, 2, 3, 4, 5, 6 or 7;
  • Each Y is the same or different from each other, and each independently has the structure shown in formula (2), X 1 , X 2 , X 3 , X 4, and X 5 are the same or different from each other, and each independently is C(R 4 ) Or N, and at least one of X 1 , X 2 , X 3 , X 4 and X 5 is N;
  • n is selected from 1 or 2;
  • each R 4 is the same or different from each other, and each independently is hydrogen or Or two adjacent R 4 are connected to each other to form a substituted or unsubstituted 5-10 membered aromatic ring or a substituted or unsubstituted 5-10 membered heteroaromatic ring, the substituted 5-10 membered aromatic ring or a substituted 5
  • the substituents in the ⁇ 10-membered heteroaromatic ring are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 12 carbon atoms, and haloalkane having 1 to 12 carbon atoms Group, alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, aryl group having 6 to 25 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, carbon The group consisting of a trialkylsilyl group having 3 to 12 atoms, an arylsily
  • Each Ar is independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms, and substituted or unsubstituted carbon atoms of 1 to 12 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 12 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, and substituted or unsubstituted carbon atoms of 4 to The group consisting of 30 heteroaralkyl groups, Represents a chemical bond;
  • Each of L 1 and L 2 is the same or different from each other, and is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 3 to 30 The group consisting of heteroarylene groups;
  • each L 1 is the same or different;
  • each L 2 is the same or different;
  • each Ar is the same or different;
  • the substituents in each of L 1 , L 2 and Ar are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 12 carbon atoms, and 1 to 12 carbon atoms
  • An aryl group having 6 to 25 atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, and the number of carbon atoms is The group consisting of 3-12 trialkylsilyl groups, arylsilyl groups having 8-18 carbon atoms and cycloalkyl groups having 3-12 carbon atoms; in each
  • each Y may be the same or different.
  • formula (2) Refers to where there are m positions on L 1 connected with heteroaryl groups And when m is 2, each heteroaryl group X 1 , X 2 , X 3 , X 4 and X 5 are the same as or different from each other.
  • L 1 means a substituent L 1, except that Substituents other than those.
  • m ⁇ n ⁇ 2 that is, in the compound
  • the number of groups is one or two.
  • the 9-position methyl group, phenyl group and oxygen can all provide electrons to the benzene ring through the conjugation/hyperconjugation effect, so that the group has a high degree of co-conjugation.
  • Conjugate electron cloud density introduce into the mother core the substituted electron-deficient heteroaryl group as an electron injection and transport group, so that the polarity of the whole molecule is enhanced, which is more conducive to the directional arrangement of the material molecules, thereby enhancing the electron Inject and transfer to improve device efficiency.
  • the asymmetry and steric hindrance of the oxaphenanthrene group is larger than that of the general planar conjugated group, which makes it have lower crystallinity and good film-forming properties, so that it can be used in electro-organic light-emitting devices. Can effectively improve the life of the device.
  • heterocyclic group optionally substituted by an alkyl group means that an alkyl group may but does not have to be present, and the description includes the scenario where the heterocyclic group is substituted by an alkyl group and the scenario where the heterocyclic group is not substituted by an alkyl group.
  • an aryl group with 6 to 20 carbon atoms optionally substituted with 0, 1, 2, 3, 4, or 5 substituents independently selected from deuterium, fluorine, chlorine, and cyano is It means that the aryl group having 6 to 20 carbon atoms may have 0, 1, 2, 3, 4, or 5 substituents, and these substituents are each independently selected from deuterium, fluorine, chlorine, and cyano. When the number of substituents is 0, the aryl group is an unsubstituted aryl group.
  • each... are independently” and “... are independently” and “... are independently selected from” are interchangeable, 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 the specific options expressed between the same symbols do not affect each other in the same group.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine
  • formula Q-1 represents 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 means that there are q substituents R" on each benzene ring of biphenyl, and R on two benzene rings
  • the number q of "substituents" may be the same or different, each R" may 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 ease of description, the substituents are collectively referred to as Rc).
  • Rc substituents
  • the "substituted or unsubstituted aryl group” refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc may be, for example, deuterium, halogen group, cyano group, alkyl group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms, and alkane having 1 to 12 carbon atoms.
  • An oxy group, an alkylthio group having 1 to 12 carbon atoms, an aryl group having 6 to 25 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, C6-20 arylthio group, C3-12 trialkylsilyl group, C8-18 arylsilyl group and C3-12 cycloalkyl group The group consisting of.
  • the "substituted" functional group can be substituted by one or more of the above-mentioned Rc substituents; when two substituents Rc are attached to the same atom, these two substituents Rc can exist independently Or they are connected to each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc may exist independently or be fused with the functional group to which they are connected to form a ring.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms in the functional group and the substituents on it. For example, if R 1 is selected from substituted aryl groups with 30 carbon atoms, all carbon atoms of the aryl group and the substituents thereon are 30; for another example, if L 1 is selected from alkyl groups If the substituted aryl group has 25 carbon atoms, all the carbon atoms of the aryl group and the alkyl group are 25.
  • the number of carbon atoms refers to the number of all carbon atoms.
  • L 1 is a substituted arylene group having 12 carbon atoms, and all carbon atoms of the arylene group and the substituents thereon are 12.
  • Ar is Then the number of carbon atoms is 7; L 1 is The number of carbon atoms is 12.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, or two or more single Cyclic aryl groups, monocyclic aryl groups and fused ring aryl groups conjugated through carbon-carbon bonds, and two or more fused ring aryl groups conjugated through carbon-carbon bonds.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (for example, a naphthyl group), a tricyclic fused aryl group (for example, a phenanthryl group, a fluorenyl group, an anthryl group), 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, 9,9-dimethylfluorenyl, spirobifluorenyl, indenyl, anthracenyl, phenanthryl, biphenyl, terphenyl Group, tetrabiphenyl, pentaphenyl, benzo[9,10]phenanthryl, pyrenyl, fluoranthene, benzofluoranthene, Base, perylene base, etc. There may be one or more linkages on the "aryl" in this application to connect to the rest of the molecule.
  • the substituted aryl group may be one or more of the hydrogen atoms in the aryl group, such as deuterium atom, halogen group, cyano group (-CN), aryl group, heteroaryl group, trialkylsilyl group , Alkyl, cycloalkyl, alkoxy, alkylthio and other groups substituted.
  • aryl group such as deuterium atom, halogen group, cyano group (-CN), aryl group, heteroaryl group, trialkylsilyl group , Alkyl, cycloalkyl, alkoxy, alkylthio and other groups substituted.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, and the like.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group.
  • the total number of carbon atoms of the group is 18.
  • the number of carbon atoms of the "substituted or unsubstituted aryl group" in this application is 6-40, and the number of carbon atoms can be, for example, 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 25. , 29, 30, 31, 32, 33, 34, 35, 36, 40, etc.
  • Specific examples of the aryl group include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthryl, fluorenyl, dimethylfluorenyl, spirobifluorenyl and the like.
  • the number of carbon atoms of the aryl group as a substituent is 6-25, and the number of carbon atoms may be 6, 10, 12, 14, 18, 20, 25, etc., for example.
  • Specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, anthryl, phenanthryl, fluorenyl, dimethylfluorenyl and the like.
  • the substituted or unsubstituted aryl group having 6 to 20 carbon atoms has, for example, 6 (phenyl), 10 (naphthyl), 12 (for example, biphenyl), 14, 15 ( Dimethyl fluorenyl), 16 and so on.
  • the number of carbon atoms of the heteroaryl group having 3 to 20 carbon atoms is, for example, 5, 8, 12, 15, 18 and the like.
  • the number of carbon atoms of the aryl group having 6 to 12 carbon atoms is, for example, 6 (phenyl), 10 (naphthyl), and 12 (for example, biphenyl).
  • the arylene group refers to a group formed by further losing a hydrogen atom of an aryl group.
  • the arylene group includes a group formed by the aryl group further losing one or two or more hydrogen atoms, such as an arylene group.
  • the definition of aryl can be applied to arylene and arylene.
  • arylene in formula (2), when m is 2, there are three chemical bonds connected to L 1 and one of the bonds is connected to the core The other two single bonds each have one Group connection.
  • L 1 is phenylene and m is 2, L 1 has the following The structure shown.
  • n is 1 and m is selected from 1, 2, or n is 2 and m is 1.
  • heteroaryl refers to a monovalent aromatic ring containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms or derivatives thereof, wherein the heteroatoms can be B, O, At least one of N, P, Si, Se, and S.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may 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 And thienyl, thieno
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds.
  • Heteroaryl group of ring system type is heteroaryl group of ring system type.
  • the number of carbon atoms of the "substituted or unsubstituted heteroaryl group" is 3-40, and the number of carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 25, 29, 30, 31, 32, 33, 34, 35, 36, 40, etc.
  • heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, benzoxazinyl, carbazolyl, indolyl, dibenzofuran Group, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, benzimidazolyl, benzoxazolyl, dibenzothioanthranyl, acridinyl, dibenzodioxinyl, benzene Oxyphylline, thioanthranyl, phenothiazinyl, benzoxazinyl, etc.
  • the involved heteroarylene group refers to a group formed by further losing a hydrogen atom of a heteroaryl group.
  • the heteroarylene group includes a group formed by further losing one or two or more hydrogen atoms of an aryl group, such as a heteroaryl group.
  • the definition of heteroaryl can be applied to heteroarylene and heteroarylene.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkane Group, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • a 5- to 10-membered heteroaromatic ring refers to a heteroaromatic ring with a total number of atoms of 5, 6, 7, 8, 9 or 10 on a heteroaromatic ring; for example, a quinoline ring is a 10-membered heteroaromatic ring ,
  • the pyrimidine ring is a 6-membered heteroaromatic ring
  • the pyridine ring is a 6-membered heteroaromatic ring
  • the pyrrole ring is a 5-membered heteroaromatic ring
  • the furan ring is a 5-membered heteroaromatic ring.
  • the heteroaromatic ring can also be a 5- to 10-membered heteroaromatic ring.
  • the number of carbon atoms of the heteroaryl group as a substituent is 3-20, and the number of carbon atoms may be 3, 4, 5, 7, 8, 9, 12, 18, 20, etc., for example.
  • Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
  • a 5- to 10-membered aromatic ring refers to an aromatic ring with a total number of atoms of 5, 6, 7, 8, 9 or 10; for example, a naphthalene ring is a 10-membered aromatic ring, and a benzene ring is 6.
  • the indene ring is a 9-membered aromatic ring.
  • the aromatic ring can also be a 6-10 membered aromatic ring.
  • trialkylsilyl groups having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl and the like.
  • cycloalkyl groups having 3 to 12 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
  • the cycloalkyl group is a cycloalkyl group having 5 to 7 carbon atoms, and the cycloalkyl group having 5 to 7 carbon atoms includes cyclopentyl, cyclohexyl, and cycloheptyl.
  • arylsilyl group having 8 to 18 carbon atoms include, but are not limited to, triphenylsilyl group.
  • alkyl refers to a saturated linear or branched monovalent hydrocarbon group, wherein the alkyl group may be optionally substituted with one or more substituents described in the present invention.
  • the alkyl group having 1 to 20 carbon atoms may be a linear alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms.
  • the number of carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, for example.
  • the alkyl group in the present invention contains 1-10 carbon atoms; in other embodiments, the alkyl group in the present invention contains 1-6 carbon atoms; in still other embodiments, the present invention The alkyl group in contains 1-4 carbon atoms; in other embodiments, the alkyl group in the present invention contains 1-3 carbon atoms.
  • alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 2-methylpentyl, 2-ethylbutyl, heptyl, n- Heptyl, octyl, n-octyl, tert-octyl, n-nonyl, decyl, etc., but not limited thereto.
  • alkyl groups with 1-4 carbon atoms in this application include but are not limited to: methyl (Me, -CH 3 ), ethyl (Et, -CH 2 CH 3 ), n-propyl (n-Pr, -CH 2 CH 2 CH 3 ), isopropyl (i-Pr, -CH(CH 3 ) 2 ), n-butyl (n-Bu, -CH 2 CH 2 CH 2 CH), tert-butyl (t- Bu,-C(CH 3 ) 3 ) and so on.
  • the halogen group can be fluorine, chlorine, bromine, or iodine.
  • connection key is used Express.
  • the non-positioned connecting bond refers to the single bond protruding from the ring system It means that one end of the link can be connected to any position in the ring system that the bond penetrates, 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 that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).
  • the fluorenyl group represented by the formula (X') is connected to other positions of the molecule through a non-localized bond extending from the middle of the benzene ring on one side, which represents The meaning of includes any possible connection modes shown in formula (X'-1) to formula (X'-5).
  • the non-positioned substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system.
  • the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-localized linking bond, and its meaning includes formulas (Y-1) to Any possible connection mode shown in formula (Y-7).
  • the organic compound has a structure represented by the following formula (1-1), formula (1-2), formula (1-3) or formula (1-4):
  • each X 1 is the same or different from each other
  • each X 2 is the same or different from each other
  • each X 3 is the same or different from each other
  • each X 4 is mutually the same or different.
  • each X 5 is the same or different from each other; in formula (1-3) and formula (1-4), each L 1 is the same or different from each other.
  • X 1 , X 3 and X 5 are N, X 2 and X 4 are C(R 4 ); each R 4 is the same or different from each other, and each is independently
  • R 1 and R 2 are the same or different from each other, and are each independently selected from a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group; the substituted methyl group is
  • the substituents of are each independently selected from the group consisting of cyano, fluorine, chlorine, and deuterium, and the substituents in the substituted phenyl are each independently selected from the group consisting of cyano, fluorine, chlorine, deuterium, methyl, and ethyl , Isopropyl, tert-butyl, trimethylsilyl group.
  • R 1 and R 2 are the same or different from each other, and are each independently selected from a methyl group, a substituted or unsubstituted phenyl group, and the substituents in the substituted phenyl group are each independently It is selected from the group consisting of cyano, fluorine, chlorine, deuterium, methyl, ethyl, isopropyl, tert-butyl, and trimethylsilyl.
  • the Y has a structure shown in the following formula (2-1):
  • X 1 , X 3 and X 5 are the same or different, and are each independently C(R 4 ) or N, and any one of X 1 , X 3 and X 5 is N, and any two are N or All are N; each R 4 is the same or different, and each independently is hydrogen or
  • the Y has a structure represented by the following formula (2-2):
  • X 1 , X 3 and X 5 are the same or different, and are each independently C(R 4 ) or N, and any one of X 1 , X 3 and X 5 is N, and any two are N or All are N; each R 4 is the same or different, and each independently is hydrogen or
  • the Y has a structure shown in the following formula (2-1-1) to formula (2-1-5):
  • Each R 4 is the same or different, and each independently is hydrogen or
  • the Y has a structure represented by the following formula (2-1-6):
  • Each R 4 is the same or different, and each independently is hydrogen or
  • each Ar is independently selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, or the following The group consisting of groups of formula (i-1) to formula (i-18):
  • M 1 is selected from a single bond or
  • T 1 to T 5 are each independently selected from N or C(Q 1 ), and at least one of T 1 to T 5 is selected from N; when two or more of T 1 to T 5 are selected from C(Q 1 ) , Any two Q 1 are the same or different;
  • T 6 to T 13 are each independently selected from N or C(Q 2 ), and at least one of T 6 to T 13 is selected from N; when two or more of T 6 to T 13 are selected from C(Q 2 ) , Any two Q 2 are the same or different;
  • T 14 to T 23 are each independently selected from N or C(Q 3 ), and at least one of T 14 to T 23 is selected from N; when two or more of T 14 to T 23 are selected from C(Q 3 ) , Any two Q 3s are the same or different;
  • T 24 to T 33 are each independently selected from N or C(Q 4 ), and at least one of T 24 to T 33 is selected from N; when two or more of T 24 to T 33 are selected from C(Q 4 ) , Any two Q 4 are the same or different;
  • T 34 to T 37 are each independently selected from N or C(Q 5 ), and at least one of T 34 to T 37 is selected from N; when two or more of T 34 to T 37 are selected from C(Q 5 ) , Any two Q 5 are the same or different; optionally, two adjacent Q 5s form a 6-10 membered aromatic ring or a 5-10 membered heteroaromatic ring;
  • T 38 to T 41 are each independently selected from N or C(Q 6 ), and at least one of T 38 to T 41 is selected from N; when two or more of T 38 to T 41 are selected from C(Q 6 ) , Any two Q 6 are the same or different; optionally, two adjacent Q 6s form a 6-10 membered aromatic ring or a 5-10 membered heteroaromatic ring;
  • T 42 to T 58 are each independently selected from N or C(Q 7 ), and at least one of T 42 to T 58 is selected from N; when two or more of T 42 to T 58 are selected from C(Q 7 ) , Any two Q 7 are the same or different; optionally, two adjacent Q 7s form a 6-10 membered aromatic ring or a 5-10 membered heteroaromatic ring;
  • E 1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, and those having 1 to 10 carbon atoms A halogenated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
  • E 2 to E 6 and E 21 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms Group, 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 Alkylthio groups having 1 to 10 atoms, heteroaryl groups having 3 to 18 carbon atoms;
  • E 7 to E 20 and Q 1 to Q 7 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, and 1 to carbon atoms 10 alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkyl sulfides having 1 to 10 carbon atoms Group, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms;
  • e 1 ⁇ e 21 are represented by e k
  • E 1 ⁇ E 21 are represented by E k
  • k is a variable, which represents any integer from 1 to 21
  • e k is the number of substituents E k;
  • e k is selected from 1, 2 or 3;
  • e k is selected from 1, 2, 3 or 4;
  • e k is selected from 1, 2, 3, 4 or 5;
  • e k is selected from 1, 2, 3, 4, 5 or 6;
  • e k is selected from 1, 2, 3, 4, 5, 6 or 7;
  • e k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when e k is greater than 1, any two E k are the same or different;
  • K 1 is selected from O, S, N (E 22 ), C (E 23 E 24 ), Si (E 23 E 24 ); wherein, E 22 , E 23 , and E 24 are each independently selected from: hydrogen, carbon atom An aryl group having 6 to 18, 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 E 23 and E 24 are 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;
  • K 2 is selected from single bond, O, S, N (E 25 ), C (E 26 E 27 ), Si (E 26 E 27 ); wherein, E 25 , E 26 , and E 27 are each independently selected from: hydrogen , C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group or C3-C10 cycloalkyl group, or the above E 26 and E 27 are connected to each other to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms connected to them in common.
  • the two groups in each group can exist independently of each other, or can be connected to each other to form a ring, and the ring formed by the connection can be It is a saturated or unsaturated ring with 3 to 15 carbon atoms.
  • formula (i-14) when K 2 and M 1 are both single bonds, each E 18 is hydrogen, T 34 ⁇ T 37 are all CH, and K 1 is C(E 23 E 24 ) When E 23 and E 24 are connected to each other to form a 5-membered ring with their common atoms, the formula (i-14) is Similarly, formula (i-14) can also represent That is, E 23 and E 24 are connected to each other to form a partially unsaturated 13-membered ring with the atoms they are commonly connected to. Of course, the number of ring atoms formed can also be other numbers, which will not be repeated here.
  • the above-mentioned "optionally, two adjacent Q 5 form a 6-10 membered aromatic ring or a 5-10 membered heteroaromatic ring” means that in formula (i-14), any two adjacent The Q 5 can exist independently of each other, or they can be connected to each other to form a fused aromatic ring or heteroaromatic ring, and the fused ring formed can be a 5-10 membered aromatic ring or a 5-10 membered heteroaromatic ring.
  • each E 18 is hydrogen
  • K 1 is -NH-
  • T 34 and T 37 are -CH-
  • T When 35 and T 36 are C(Q 5 ) and they are connected to each other to form a 6-membered aromatic ring, the formula (i-14) is Of course, the number of ring atoms formed can also be other numbers, which will not be repeated here.
  • two adjacent Q 6 form a 6-10 membered aromatic ring or a 5-10 membered heteroaromatic ring
  • two adjacent Q 7 form a 6-10 membered aromatic ring or 5
  • the meaning of " ⁇ 10-membered heteroaromatic ring” is the same as this, and will not be repeated here.
  • each Ar is independently selected from substituted or unsubstituted aryl groups having 6 to 19 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms, substituted or unsubstituted An alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms. Further, each Ar is independently selected from substituted or unsubstituted aryl groups having 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, or selected from carbon atoms It is a 3, 5, 8, 9, 12, 16, 18 substituted or unsubstituted heteroaryl group.
  • the substituents in each Ar are independently selected from alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, trifluoromethyl, trimethylsilyl, Triphenylsilyl, cycloalkyl having 5-7 carbon atoms, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, indolyl, The group consisting of benzimidazole groups.
  • each Ar is independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, propyl
  • each Ar is independently selected from a substituted or unsubstituted group W 3 , and the unsubstituted group W 3 is selected from the group consisting of the following groups:
  • the substituents in the group W 3 are selected from deuterium, fluorine, chlorine, cyano, alkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms.
  • each Ar is independently selected from: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted naphthyl, substituted or Unsubstituted fluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted
  • each Ar is independently selected from any of the following groups:
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond or the group consisting of the following formula (j-1) to formula (j-20):
  • M 2 is selected from a single bond or M 3 is selected from
  • G 1 to G 5 are each independently selected from N or C(F 1 ), and at least one of G 1 to G 5 is selected from N; when two or more of G 1 to G 5 are selected from C(F 1 ) , Any two F 1 are the same or different;
  • G 6 to G 13 are each independently selected from N or C(F 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(F 2 ) , Any two F 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(F 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(F 3 ) , Any two F 3 are the same or different;
  • G 24 to G 33 are each independently selected from N or C(F 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(F 4 ) , Any two F 4 are the same or different;
  • Z 1 to Z 2 are selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, and 1 carbon atom -10 haloalkyl groups, 3-10 cycloalkyl groups, 1-10 alkoxy groups, and 1-10 alkylthio groups;
  • Z 3 to Z 33 and F 1 to F 4 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and 1 to carbon atoms 10 alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkyl sulfides having 1 to 10 carbon atoms Group, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms;
  • h 1 ⁇ h 33 are represented by h k
  • Z 1 ⁇ Z 33 are represented by Z k
  • k is a variable, representing any integer from 1 to 33
  • h k is the number of substituents Z k;
  • h k is selected from 1, 2, 3, or 4;
  • h k is selected from 1, 2, 3, 4 or 5;
  • h k is selected from 1, 2 or 3;
  • h k is selected from 1 or 2;
  • h k is selected from 1, 2, 3, 4, 5 or 6;
  • h k is selected from 1, 2, 3, 4, 5, 6, 7 or 8;
  • h k is selected from 1, 2, 3, 4, 5, 6 or 7; and when h k is greater than 1, any two Z k are the same or different;
  • K 3 is selected from O, S, N (Z 24 ), C (Z 25 Z 26 ), Si (Z 25 Z 26 ); wherein, Z 24 , Z 25 , and Z 26 are each independently selected from: hydrogen, carbon atom An aryl group having 6 to 18, 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-mentioned Z 25 and Z 26 are connected to each other to form a ring with the atoms they are commonly connected to;
  • K 4 is selected from a single bond, O, S, N (Z 27 ), C (Z 28 Z 29 ), Si (Z 28 Z 29 ); wherein, Z 27 , Z 28 , and Z 29 are each independently selected from: hydrogen , C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group or C3-C10 cycloalkyl group, or the above-mentioned Z 28 and Z 29 are connected to each other to form a ring with the atoms to which they are commonly connected.
  • L 1 and L 2 are each independently selected from: substituted or unsubstituted arylene groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroarylene groups having 4 to 18 carbon atoms Group, or a subunit group formed by connecting the two through a single bond; preferably, the substituents in L 1 and L 2 are independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl Group, tert-butyl, methoxy, ethoxy, isopropoxy, propoxy, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophene Group consisting of carbazolyl, pyridyl, pyrimidinyl, and triphenylsilyl.
  • L 1 and L 2 are each independently selected from: substituted or unsubstituted arylene groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroarylene groups having 4 to 18 carbon atoms A group or a group formed by connecting the two through a single bond. Further, the L 1 and L 2 are each independently selected from substituted or unsubstituted arylene groups with carbon atoms of 6, 10, 12, 13, 14, 15, 16, 17, or 18, or selected from carbon atoms. A substituted or unsubstituted heteroarylene group having 4, 5, 8, 9, 10, 12, 16, or 18 atoms.
  • the substituents in L 1 and L 2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropyl
  • each of L 1 and L 2 is independently selected from: substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, Substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuran subunit, substituted or unsubstituted dibenzothiophene subunit, substituted or unsubstituted quinolinylene, substituted or unsubstituted carbene Azolyl, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted pyrimidinylene, substituted or Unsubstituted pyridinylene, substituted or unsubstituted pyrazinylene,
  • each L 1 is independently selected from a single bond or a substituted or unsubstituted group W 1 , the unsubstituted group W 1 choose from the group consisting of the following groups:
  • the substituents in the group W 1 are each independently selected from deuterium, fluorine, chlorine, cyano, and alkyl with 1 to 4 carbon atoms, Alkoxy with 1 to 4 carbon atoms, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexane, optionally selected from 0, 1, 2, 3, 4 or 5
  • each substituent is the same or different;
  • each L 1 is independently selected from a single bond or a substituted or unsubstituted group W 2 , and the unsubstituted group W 2 is selected from the group consisting of the following groups:
  • the substituents in the group W 2 are each independently selected from deuterium, fluorine, chlorine, cyano, and alkyl with 1 to 4 carbon atoms, Alkoxy with 1 to 4 carbon atoms, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexane, optionally selected from 0, 1, 2, 3, 4 or 5
  • each substituent is the same or different.
  • L 1 is a single bond or any one of the following groups:
  • each L 2 is independently selected from a single bond, a substituted or unsubstituted group W 4 , and the unsubstituted group W 4 is selected from the group consisting of the following groups:
  • the substituents in the group W 4 are each independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, normal Propyl, tert-butyl, alkoxy with 1 to 4 carbon atoms, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexane, phenyl, naphthyl and carbon atoms are A group consisting of 5-12 heteroaryl groups; when the number of substituents in the group W 4 is more than one, the substituents are the same or different.
  • L 2 is selected from a single bond or any one of the following groups:
  • each R 3 is independently selected from deuterium, fluorine, chlorine, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, and Is a haloalkyl group of 1 to 4, trimethylsilyl group, a cycloalkyl group of 5 to 7 carbon atoms, optionally 0, 1, 2, 3, 4 or 5 independently selected from deuterium, fluorine,
  • the substituent is substituted by a heteroaryl group having 3 to 18 carbon atoms; when the number of R 3 is more than one, each R 3 is the same or different.
  • each R 3 is independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, and those with 1 to 4 carbon atoms. Alkoxy, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexane, phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, dibenzothienyl , Dibenzofuranyl or N-phenylcarbazolyl; when the number of R 3 is more than one, each R 3 is the same or different.
  • R 1 and R 2 are the same and are selected from methyl or phenyl.
  • the organic compound is selected from the group consisting of the following organic compounds:
  • the application does not specifically limit the synthesis method of the organic compound provided, and those skilled in the art can determine a suitable synthesis method according to the organic compound of the application in combination with the preparation method provided in the synthesis example section.
  • the synthesis example part of the present application exemplarily provides a method 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 this application according to these exemplary preparation methods. All specific preparation methods for preparing the organic compounds will not be described in detail here, and those skilled in the art should not be construed as limiting the application.
  • the second aspect of the present application provides an electronic component, which includes an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; the functional layer contains the first aspect of the present application Of organic compounds.
  • the functional layer includes an electron transport layer, and the electron transport layer contains the organic compound.
  • the electron transport layer can be composed of the organic compounds provided in this application, or can be composed of the organic compounds provided in this application and other materials.
  • the electron transport layer may be one layer or two or more layers.
  • the functional layer includes a hole blocking layer, and the hole blocking layer contains the organic compound.
  • the electronic component is an organic electroluminescence device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescent device, such as a red light device, a green light device or a blue light device.
  • the electronic component may be an organic electroluminescent 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, a hole blocking layer 341, and an electron transport layer which are sequentially stacked. 340 and cathode 200.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; 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 SnO 2 : Sb; or conductive 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 containing indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 321 and the electron blocking layer 322 respectively include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of Compound, this application does not make any special limitation on this.
  • the hole transport layer 321 may be composed of the compound NPB or the compound HT-01, and the electron blocking layer 322 may include the compound HT-02.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a dopant material.
  • the organic light-emitting layer 330 is composed of a host material and a doping 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, which transfer energy To the host material, the host material transfers energy to the doped material, which in turn enables the doped material to emit light.
  • the host material of the organic light-emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application.
  • the host material of the organic light-emitting layer 330 may be BH-01.
  • the dopant material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, and this application does not make any special considerations to this. limits.
  • the dopant material of the organic light-emitting layer 330 may be BD-01.
  • the hole blocking layer 341 may include one or more hole blocking materials, and the hole blocking material may be selected from the compound of the present application or BCP.
  • the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials.
  • the electron transport materials can be selected from, but not limited to, benzimidazole derivatives and oxadiazole derivatives. , Quinoxaline derivatives or other electron transport materials.
  • the electron transport layer material contains the organic compound of the present application. In one embodiment of the present application, the electron transport layer material contains BCP.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates injection of electrons 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 their alloys; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferable to include a metal electrode containing magnesium and silver as the cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject 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 particularly limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 may be further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340.
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances.
  • the electron injection layer 350 may include Yb or LiQ.
  • the electronic component may be a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed oppositely, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.
  • the photoelectric conversion device may include an anode 100, a first hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200 which are sequentially stacked and arranged.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode that are sequentially stacked, wherein the electron transport layer includes the organic Compound.
  • 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 electroluminescent 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, etc.
  • the electronic device is a second electronic device 500, and the second electronic device 500 includes the aforementioned 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 chromatographic column was a silica gel column, and silica gel (100-200 mesh) was purchased from Qingdao Ocean Chemical Factory.
  • MS mass spectrometry
  • Proton nuclear magnetic resonance spectrum Bruker 400MHz nuclear magnetic instrument, at room temperature, with CDCl 3 as the solvent (in ppm), and TMS (0 ppm) as the reference standard. When multiple peaks appear, the following abbreviations will be used: s (singlet, singlet), d (doublet, doublet), t (triplet, triplet), m (multiplet, multiplet).
  • the target compound uses Agilent 1260pre-HPLC or Calesep pump 250pre-HPLC (column model: NOVASEP 50/80mm DAC), and UV detection at 210nm/254nm.
  • Methyl 2-iodobenzoate (10.0g, 38.2mmol), 4-chloro-2-methoxyphenylboronic acid (7.83g, 42.0mmol), potassium carbonate (10.54g, 76.4mmol), tetrabutyl bromide Ammonium (1.27g, 3.82mmol), toluene (50mL), ethanol (30mL) and deionized water (20mL) were added to a three-necked flask, stirred for 15min under nitrogen protection, and then added tetrakistriphenylphosphine palladium (0.44g, 0.0382mmol) The temperature was raised to 75-80°C and stirred for 5 hours; the reaction solution was cooled to room temperature, toluene (100 mL) was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, the organic phase was decompressed to remove the solvent, and the residue was directly Purified by flash silica gel column chromatography and
  • Intermediate I-A2 ⁇ Intermediate I-A10 in Table 1 were prepared by the same method as that of intermediate I-A1, except that the raw material 1 in Table 1 was used instead of the synthesis of intermediate I-A1.
  • the raw material 2-iodobenzoic acid methyl ester, raw material 2 was used instead of the raw material 4-chloro-2-methoxyphenylboronic acid used in the synthesis of intermediate I-A1.
  • Intermediate I-B2 ⁇ Intermediate I-B10 were prepared by the same method as the preparation of Intermediate I-B1, except that the raw material 3 (Intermediate IA) in Table 2 was used instead of the method used in the synthesis of Intermediate I-B1.
  • intermediates I-C3 to I-C18 were synthesized using the same method as the synthesis of intermediate I-C2, except that the intermediate IB in Table 3 was used to replace the raw material intermediate I- for the synthesis of intermediate I-C2.
  • B1 use raw material 4 to replace the raw material 3,5-dibromofluorobenzene in the synthesis of intermediate I-C2.
  • the intermediates I-D3 to I-D15 were prepared by the same method as the intermediate I-D2, except that the intermediate I-C in Table 4 was used instead of the raw material intermediate I-C2 for the synthesis of the intermediate I-D2.
  • the intermediate I-F1 was prepared by the same method as the intermediate I-D2, except that the raw material I-B1 used to synthesize the intermediate I-D2 was replaced with the intermediate I-E1.
  • intermediate I-F1 According to the synthesis steps of intermediate I-F1, only the raw material 13 in Table 6 was used to replace the intermediate I-E1, and the raw material 14 was used to replace 3,5-dibromobenzonitrile. The two raw materials in the preparation were used to obtain the intermediate I- F3 and intermediate I-F6.
  • intermediates II-A3 ⁇ II-A5 were synthesized by the same method as the synthesis of intermediate II-A1, except that the raw material 5 in Table 7 was used instead of the raw material 2,4- for the synthesis of intermediate II-A1.
  • Dichloro-6-phenyl-1,3,5-triazine, raw material 6 is used to replace the raw material intermediate II-A-1 used in the synthesis of intermediate II-A1.
  • Intermediate I-D16 is prepared using the above-prepared intermediate I-C18 according to the following synthesis method.
  • 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.
  • the photolithography process was used to prepare an experimental substrate with cathode, anode, and insulating layer patterns, using ultraviolet ozone and O 2 :N 2 plasma. Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • HIL hole injection layer
  • BH-01 and BD-01 were co-evaporated at a ratio of 98%: 2% (evaporation rate) to form a thickness of Organic light emitting layer (EML).
  • EML Organic light emitting layer
  • the compound BCP is vapor-deposited to form Thick hole blocking layer (a-ETL).
  • a-ETL Thick hole blocking layer
  • compound 2 and LiQ are mixed at a weight ratio of 1:1 and formed by evaporation Thick electron transport layer (ETL), LiQ is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at a deposition rate of 1:9, and then vacuum-evaporated on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • the vapor deposition thickness on the above cathode is CP-1 to form an organic cover layer (CPL) to complete the manufacture of organic light-emitting devices.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when the electron transport layer was formed, the compound shown in the following Table 11 was substituted for compound 2.
  • the organic electroluminescent device was produced by the same method as in Example 1, except that when the hole blocking layer was formed, compound 129 was used instead of BCP to be deposited on the organic light-emitting layer.
  • Thick hole blocking layer (a-ETL).
  • compound 2 Replace compound 2 with compound BCP, mix with LiQ at a weight ratio of 1:1 and vaporize to form Thick electron transport layer (ETL).
  • the organic electroluminescent device was prepared by the same method as in Example 33, except that when the hole blocking layer was formed, the compound shown in the following Table 11 was substituted for compound 129.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when the electron transport layer was formed, Compound A shown in Table 10 below replaced Compound 2.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when the electron transport layer was formed, Compound B shown in Table 10 below replaced Compound 2.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when the electron transport layer was formed, Compound C shown in Table 10 below replaced Compound 2.
  • the organic electroluminescence device was prepared by the same method as in Example 33, except that when the hole blocking layer was formed, compound A shown in Table 10 below replaced compound 129.
  • the organic electroluminescent device was prepared by the same method as in Example 33, except that when the hole blocking layer was formed, compound B shown in Table 10 below replaced compound 129.
  • the organic electroluminescence device was prepared by the same method as in Example 33, except that when the hole blocking layer was formed, compound C shown in Table 10 below replaced compound 129.
  • Examples 33-71 when the compound of the present invention is used as a hole blocking layer material, compared with Comparative Examples 4-6, the luminous efficiency and lifetime of the device are significantly improved, and the luminous efficiency is increased by at least 10.1%.
  • the quantum efficiency is increased by at least 11.2%, and the lifetime is increased by at least 22.8%.
  • the reason may be that the oxygen atoms in the compounds A and C are in the spirocyclic position, the spatial conformation is basically fixed, and the carrier transmission efficiency is insufficient, resulting in lower device efficiency than the compound of the present invention, and the compounds A and C are in the organic layer of the light-emitting device. In between, or between the organic layer and the metal electrode, more Joule heat is generated, which reduces the service life of the device to a certain extent.
  • the core of the comparative compound B has a carbonyl group, and the C-C bond in the core of the compound becomes weaker, which reduces the service life of the device to a certain extent.
  • the novel compound of the present application when used to prepare an organic electroluminescent device, the driving voltage of the device can be effectively reduced, and the lifetime of the device can be improved.
  • Tg is measured by a thermal weight loss analyzer (TGA)
  • Te is the compound in the vapor deposition machine
  • the vapor deposition rate is The evaporation temperature at the time.
  • the compound When the compound is used for mass production of devices, it needs to be heated for a long time under evaporation conditions. If the thermal stability of the molecular structure of the compound is poor under heated conditions, the purity of the compound will decrease under long-term heating conditions, resulting in large differences in the performance of devices prepared before, during, and after mass production.
  • the present disclosure uses the following methods to evaluate the stability of the molecular structure of the nitrogen-containing compound of the present disclosure under long-term heating during mass production evaporation:
  • the compound of the application and the comparative compound were subjected to a heat resistance test (heat preservation treatment) for 24 hours, respectively.
  • the stability of the nitrogen-containing compound of the present disclosure under mass production conditions is judged by the purity drop value before and after the heat resistance experiment.
  • the compound of the present application has a lower possibility of decomposition during the evaporation and film formation process of a high-temperature device, and has a higher resistance to crystallization in an electric Joule heat environment during device operation.
  • the compound of the present application has a lower vapor deposition temperature (Te) when the molecular weight is not much different.
  • Te vapor deposition temperature
  • the heat resistance experiment of the compound confirmed that the purity of the compound decreased by less than 0.1%, and the purity of the compound of the comparative example decreased by more than 1% at the test temperature (Te+70°C). Therefore, the compound of the present disclosure was compared with the compound of the comparative example. Has better thermal stability for mass production.

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Abstract

本申请涉及一种有机化合物，所述有机化合物具有如下式(1)所示的结构，其中，R1和R2彼此相同或者不同，且分别独立地为碳原子数为1～4的取代或未取代的烷基、取代或未取代的苯基；各Y相同或者不同，且各自独立地具有式(2)所示的结构，X1、X2、X3、X4和X5相同或不同，分别独立地为C(R4)或N，且X1、X 2、X3、X4和X5中至少一者为N；m选自1或2；n选自1或2。本申请的有机化合物可用作有机电致发光器件的空穴阻挡层和/或电子传输层。

Description

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6月5日递交的申请号为CN202010507151.1的中国专利申请以及2020年9月29日递交的申请号为CN202011056769.7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，具体地，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
有机电致发光材料(OLED)作为新一代显示技术，具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点，已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
有机发光器件通常包括阳极、阴极和其间的有机材料层。有机材料层通常以由不同材料构成的多层结构形成，以提高有机电致发光器件的亮度、效率和寿命，有机材料层可由空穴注入层、空穴传输层、发光层、电子传输层和电子注入层等构成。有机发光器件结构中，当在两个电极之间施加电压时，空穴和电子分别从阳极和阴极注入有机材料层，当注入的空穴与电子相遇时形成激子，并且当这些激子返回基态时发光。
现有的有机电致发光器件中，最主要的问题为寿命和效率，随着显示器的大面积化，驱动电压也随之提高，发光效率及电力效率也需要提高，因此，有必要继续研发新型的材料，以进一步提高有机电致发光器件的性能。
发明内容
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空穴阻挡层和/或电子传输层。
为了实现上述目的，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 PCTCN2021096926-appb-000001
式(1)中，R 1和R 2彼此相同或者不同，且分别独立地选自取代或未取代的碳原子数为1～4的烷基、取代或未取代的苯基，当R 1或R 2为取代的烷基时，所述取代的烷基中的取代基相同或不同，且各自独立地选自由氘、氟、氯、氰基所组成的组；当R 1或R 2为取代的苯基时，所述取代的苯基中的取代基相同或不同，且各自独立地选自由碳原子数为1～6的烷基、氰基、卤素基团、氘、三甲基硅基所组成的组；
各R 3彼此相同或者不同，且各自独立地选自由氘，卤素基团，氰基，碳原子数为1～12的卤代烷基，碳原子数为1～12的烷基，碳原子数为1～12的烷氧基，碳原子数为3～12的环烷基，碳原子 数为1～12的烷硫基，碳原子数为3～12的三烷基硅基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为6～20的芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为3～20的杂芳基，碳原子数为6～20的芳氧基，碳原子数为6～20的芳硫基，碳原子数为6～18的芳基硅基，碳原子数为1～12的烷基膦氧基所组成的组；
p选自0、1、2、3、4、5、6或7；
各Y彼此相同或者不同，且各自独立地具有式(2)所示的结构，X 1、X 2、X 3、X 4和X 5彼此相同或不同，且分别独立地为C(R 4)或N，且X 1、X 2、X 3、X 4和X 5中至少一者为N；m选自1或2；n选自1或2；
式(2)中，各R 4相同或者不同，且各自独立地为H或
Figure PCTCN2021096926-appb-000002
或者两个相邻的R 4相互连接形成取代或未取代的5～10元芳环或者取代或未取代的5～10元杂芳环；所述取代的5～10元芳环或取代的5～10元杂芳环中的取代基彼此相同或不同，且各自独立地选自由氘、卤素基团、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为1～12的烷硫基、碳原子数为6～25的芳基、碳原子数为3～20的杂芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组；
各Ar独立地选自由取代或未取代的碳原子数为6～40的芳基、取代或未取代的碳原子数为3～40的杂芳基、取代或未取代的碳原子数为1～12烷基、取代或未取代的碳原子数为3～12的环烷基、取代或未取代的碳原子数为7～30的芳烷基、取代或未取代的碳原子数为4～30的杂芳烷基所组成的组；
各L 1和L 2彼此相同或者不同，且各自独立地选自由单键、取代或未取代的碳原子数为6～30的亚芳基和取代或未取代的碳原子数为3～30的亚杂芳基所组成的组；
各L 1、L 2和Ar中的取代基彼此相同或不同，且各自独立地选自由氘，卤素基团，氰基，碳原子数为1～12的烷基，碳原子数为1～12的卤代烷基，碳原子数为1～12的烷氧基，碳原子数为1～12的烷硫基，任选地被选自氘、氟、氰基、烷基的取代基所取代的碳原子数为6～25的芳基，碳原子数为3～20的杂芳基，碳原子数为6～20的芳氧基，碳原子数为6～20的芳硫基，碳原子数为3～12的三烷基硅基，碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组；在各L 1、L 2和Ar中，当同一原子上具有两个取代基时，两个所述取代基任选地相互连接以与它们所共同连接的原子一起形成5～18元脂肪族环或5～18元芳香环。
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；所述功能层含有本申请第一方面提供的有机化合物；
可选地，所述功能层包括电子传输层，所述电子传输层含有本公开第一方面所述的有机化合物；
可选地，所述功能层包括空穴阻挡层，所述空穴阻挡层含有本公开第一方面所述的有机化合物。
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提供的电子元件。
通过上述技术方案，本申请提供的有机化合物在氧杂菲基团中，9位的甲基、苯基和邻位的氧原子均可向苯环通过共轭/超共轭效应提供电子，从而使该基团具有高的共轭电子云密度，向该母核中引入作为电子注入和传输基团的取代的缺电子杂芳基，使整个分子的极性增强，更有利于材料分子的方向性排列，从而增强电子的注入和传输，提升器件效率。氧杂菲基团的非对称性和位阻相比一般平面共轭基团更大，使其拥有较低的结晶性以及良好的成膜性，使其在应用于有机电致发光装置时，可以有效提升装置寿命。与氧杂菲母核相连接的、取代的含氮杂芳基部分属于缺电子基团，适于接受电子形成负离子中心，因而具有优良的传输电子和阻挡空穴的效果。取代的含氮杂芳基结构中含有氰基取代基时，分子极性、偶极矩均进一步提升，电子迁移率提高，相对而言具有更优的电子传输性能，更适于用于光电器件中的电子传输层；不含有氰基取代基时，空穴阻挡性能更佳，作为空穴阻挡层效果更优。氧杂菲母核上9位取代基体积较大且刚性过强时，热稳定性能 会有所下降，器件寿命会受到影响。
本公开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公开的进一步理解，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公开，但并不构成对本公开的限制。
图1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是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请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；320、第一空穴传输层；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；360、光电转化层；400、第一电子装置；500、第二电子装置。
具体实施方式
以下结合附图对本公开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公开，并不用于限制本公开。
本申请第一方面提供一种有机化合物，有机化合物具有如下式(1)所示的结构：
Figure PCTCN2021096926-appb-000003
式(1)中，R 1和R 2彼此相同或者不同，且分别独立地选自取代或未取代的碳原子数为1～4的烷基、取代或未取代的苯基，当R 1或R 2为取代的烷基时，所述取代的烷基中的取代基相同或不同，且各自独立地选自由氘、氟、氯、氰基所组成的组；当R 1或R 2为取代的苯基时，所述取代的苯基中的取代基相同或不同，且各自独立地选自由碳原子数为1～6的烷基、氰基、卤素基团、氘、三甲基硅基所组成的组；
各R 3彼此相同或者不同，且各自独立地选自由氘，卤素基团，氰基，碳原子数为1～12的卤代烷基，碳原子数为1～12的烷基，碳原子数为1～12的烷氧基，碳原子数为3～12的环烷基，碳原子数为1～12的烷硫基，碳原子数为3～12的三烷基硅基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为6～20的芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为3～20的杂芳基，碳原子数为6～20的芳氧基，碳原子数为6～20的芳硫基，碳原子数为6～18的芳基硅基，碳原子数为1～12的烷基膦氧基所组成的组；
p选自0、1、2、3、4、5、6或7；
各Y彼此相同或者不同，且各自独立地具有式(2)所示的结构，X 1、X 2、X 3、X 4和X 5彼此相同或不同，且分别独立地为C(R 4)或N，且X 1、X 2、X 3、X 4和X 5中至少一者为N；
m选自1或2；n选自1或2；
式(2)中，各R 4彼此相同或者不同，且各自独立地为氢或
Figure PCTCN2021096926-appb-000004
或者两个相邻的R 4相互连接形成取代或未取代的5～10元芳环或者取代或未取代的5～10元杂芳环，所述取代的5～10元芳环或取代的5～10元杂芳环中的取代基彼此相同或不同，且各自独立地选自由氘、卤素基团、 氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为1～12的烷硫基、碳原子数为6～25的芳基、碳原子数为3～20的杂芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组；
各Ar独立地选自由取代或未取代的碳原子数为6～40的芳基、取代或未取代的碳原子数为3～40的杂芳基、取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳原子数为3～12的环烷基、取代或未取代的碳原子数为7～30的芳烷基、取代或未取代的碳原子数为4～30的杂芳烷基所组成的组，
Figure PCTCN2021096926-appb-000005
表示化学键；
各L 1和L 2彼此相同或者不同，且各自独立地选自由单键、取代或未取代的碳原子数为6～30的亚芳基和取代或未取代的碳原子数为3～30的亚杂芳基所组成的组；
当式(1)化合物中含有多于1个L 1时，各L 1相同或不同；
当式(1)化合物中含有多于1个L 2时，各L 2相同或不同；
当式(1)化合物中含有多于1个Ar时，各Ar相同或不同；
各L 1、L 2和Ar中的取代基彼此相同或不同，且各自独立地选自由氘，卤素基团，氰基，碳原子数为1～12的烷基，碳原子数为1～12的卤代烷基，碳原子数为1～12的烷氧基，碳原子数为1～12的烷硫基，任选地被选自氘、氟、氰基、烷基的取代基所取代的碳原子数为6～25的芳基，碳原子数为3～20的杂芳基，碳原子数为6～20的芳氧基，碳原子数为6～20的芳硫基，碳原子数为3～12的三烷基硅基，碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组；在各L 1、L 2和Ar中，当同一原子上具有两个取代基时，两个所述取代基任选地相互连接以与它们所共同连接的原子一起形成5～18元脂肪族环或5～18元芳香环。
在本申请中，式中的
Figure PCTCN2021096926-appb-000006
是指式(1)中氧杂二氢菲母核上的共8个连接位置，其中n个位置连接有Y，R 3连接在氧杂二氢菲母核上没有连接Y的位置上。并且当n为2以上时，各Y可以相同或不同。
在本申请中，式(2)
Figure PCTCN2021096926-appb-000007
是指其中L 1上有m个位置连接有杂芳基
Figure PCTCN2021096926-appb-000008
并且当m为2时，各杂芳基
Figure PCTCN2021096926-appb-000009
中的X 1、X 2、X 3、X 4和X 5彼此相同或不同。在本申请中，L 1中的取代基是指L 1中除了
Figure PCTCN2021096926-appb-000010
之外的其他的取代基。
在本申请的一些实施方案中，m×n≤2，即化合物中
Figure PCTCN2021096926-appb-000011
基团的个数是1个或2个。
在本申请中，式(2)中，各R 4彼此相同或者不同，且各R 4独立地为氢或
Figure PCTCN2021096926-appb-000012
或者两个相邻的R 4相互连接形成环，两种情况可以并存；当相邻的两个R 4相互连接时，其形成的环是取代或未取代的5～10元芳环或者取代或未取代的5～10元杂芳环，例如当式(2)中，m＝1、L 1为单键、X 1和X 3为N，X 2为-CH-，X 4和X 5为CR 4，且两个R 4相互连接形成6元吡啶环时，式(2)结构为：
Figure PCTCN2021096926-appb-000013
本申请提供的有机化合物的氧杂菲基团中，9位的甲基、苯基和氧均可向苯环通过共轭/超共 轭效应提供电子，从而使该基团具有很高的共轭电子云密度，向该母核中引入作为电子注入和传输基团的取代的缺电子的杂芳基，使整个分子的极性增强，更有利于材料分子的方向性排列，从而增强电子的注入和传输，提升器件效率。氧杂菲基团的非对称性和位阻相比一般平面共轭基团更大，使其拥有较低的结晶性以及良好的成膜性，使其在应用于电致有机发光装置时，可以有效提升装置寿命。
本申请中，“任选”或者“任选地”意味着随后所描述的事件或者环境可以但不一定发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选被烷基取代的杂环基团”意味着烷基可以但不必须存在，该说明包括杂环基团被烷基取代的情景和杂环基团不被烷基取代的情景。例如“当同一原子上具有两个取代基时，两个所述取代基任选地相互连接以与它们所共同连接的原子一起形成5～18元脂肪族环或5～18元芳香环”，意味着当同一原子上具有两个取代基时，即包括两个所述取代基相互独立地存在的情景，也包括两个所述取代基相互连接与它们所共同连接的原子一起形成5～18元脂肪族环或5～18元芳香环的情景。再例如“任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为6～20的芳基”，是指碳原子数为6～20的芳基上可以带有0、1、2、3、4或5个取代基，这些取代基各自独立地选自氘、氟、氯、氰基。当取代基个数为0时，芳基为未取代的芳基。
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 PCTCN2021096926-appb-000014
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1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为1～12的烷硫基、碳原子数为6～25的芳基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳氧基、碳原子数为6～20的芳硫基、碳原子数为3～12的三烷基硅基、碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组。在本申请中，“取代的”官能团可以被上述Rc中的一个或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，指的是该官能团及其上的取代基中的所有碳原子数。举例而言，若R 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；再举例而言，若L 1选自烷基所取代的碳原子数为25的芳基，则芳基及其上烷基的所有的碳原子数为25。
在本申请中，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为
Figure PCTCN2021096926-appb-000015
则其碳原子数为7；L 1为
Figure PCTCN2021096926-appb-000016
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、9,9-二甲基芴基、螺二芴基、茚基、蒽基、菲基、二联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、荧蒽基、苯并荧蒽基、
Figure PCTCN2021096926-appb-000017
基、苝基等。本申请的“芳基”上可以有一个或多个连接键与分子其余部分相连。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(-CN)、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。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、吡啶取代的苯基等。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。
本申请中“取代或未取代的芳基”的碳原子数为6-40，碳原子数例如可以为6、10、12、13、14、15、16、17、18、19、20、25、29、30、31、32、33、34、35、36、40等。其中芳基的具体实例包括但不限于，苯基、萘基、联苯基、三联苯基、蒽基、菲基、芴基、二甲基芴基、螺二芴基等。
本申请中，作为取代基的芳基的碳原子数为6-25，碳原子数例如可以为6、10、12、14、18、20、25等。作为取代基的芳基的具体实例包括但不限于，苯基、萘基、联苯基、三联苯基、蒽基、菲基、芴基、二甲基芴基等。
本申请中，碳原子数为6～20的取代或未取代的芳基，其碳原子数例如为6(苯基)、10(萘基)、12(例如联苯基)、14、15(二甲基芴基)、16等。碳原子数为3～20的杂芳基的碳原子数例如为5、8、12、15、18等。
本申请中，碳原子数为6～12的芳基的碳原子数例如为6(苯基)、10(萘基)、12(例如联苯基)。
本申请中，涉及的亚芳基是指芳基进一步失去氢原子所形成的基团。在本发明的一些实施方案中，亚芳基包含芳基进一步失去一个或两个或更多个氢原子所形成的基团，例如次芳基。芳基的定义可以适用于亚芳基和次芳基。其中，式(2)中，当m为2时，L 1上连接有三个化学键，其中一个键连接母核
Figure PCTCN2021096926-appb-000018
另外两个单键分别各与一个
Figure PCTCN2021096926-appb-000019
基团连接。例如，当L 1为亚苯基且m为2时，L 1具有如
Figure PCTCN2021096926-appb-000020
所示的结构。
在一些实施方案中，n为1，m选自1、2，或者n为2，m为1。
在本申请中，杂芳基是指环中包含1、2、3、4、5、6或7个杂原子的一价芳香环或其衍生物，其中所述的杂原子可以是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、三唑基、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、N-苯基咔唑基、N-吡啶基咔唑基、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。
本申请中“取代或未取代的杂芳基”的碳原子数为3-40，碳原子数例如可以为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、25、29、30、31、32、33、34、35、36、40等。其中，杂芳基的具体实例包括但不限于，吡啶基、嘧啶基、三嗪基、喹啉基、异喹啉基、苯并噁嗪基、咔唑基、吲哚基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、苯并咪唑基、苯并噁唑基、二苯并噻蒽基、吖啶基、二苯并二噁英基、苯氧茶碱基、噻蒽基、吩噻嗪基、苯噁嗪基等。
可以理解的是，“杂芳基”上可以有一个键、两个键或多个键与分子中其他部分相连接。
本申请中，涉及的亚杂芳基是指杂芳基进一步失去氢原子所形成的基团。在本发明的一些实施方案中，亚杂芳基包含芳基进一步失去一个或两个或更多个氢原子所形成的基团，例如次杂芳基。杂芳基的定义可以适用于亚杂芳基和次杂芳基。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、-CN、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。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。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。
本申请中，5～10元杂芳环是指一个杂芳环上的总原子数为5、6、7、8、9或10的杂芳环；例如，喹啉环为10元杂芳环，嘧啶环为6元杂芳环、吡啶环为6元杂芳环、吡咯环为5元杂芳环、呋喃环为5元杂芳环。在另一些实施方案中，杂芳环还可以是5～10元杂芳环。
本申请中，作为取代基的杂芳基的碳原子数为3-20，碳原子数例如可以为3、4、5、7、8、9、12、18、20等。作为取代基的杂芳基的具体实例包括但不限于，吡啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基等。
本申请中，5～10元芳环是指一个芳香环上的总原子数为5、6、7、8、9或10的芳环；例如，萘环为10元芳环，苯环为6元芳环，茚环为9元芳环。在另一些实施方案中，芳环还可以是6～10元芳环。
在本申请中，碳原子数为3～12的三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基、叔丁基二甲基硅基等。
在本申请中，碳原子数为3～12的环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基等。在一些实施方案中，环烷基是碳原子数为5～7的环烷基，碳原子数为5～7的环烷基包括环戊基、环己基、环庚烷基。
在本申请中，碳原子数为8～18的芳基硅基具体实例包括但不限于，三苯基硅基。
在本申请中，“烷基”是指饱和的直链或支链一价烃基基团，其中，所述烷基可以任选地被一个或多个本发明描述的取代基所取代。具体而言，碳原子数为1～20的烷基可以为碳原子数1至20的直链烷基，或碳原子数3至20的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20。在一些实施方案中，本发明中的烷基含有1-10个碳原子；在另一些实施方案中，本发明中的烷基含有1-6个碳原子；在又一些实施方案中，本发明中的烷基含有1-4个碳原子；在另一些实施方案中，本发明中的烷基含有1-3个碳原子。烷基的具体实例包括甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、2-甲基戊基、2-乙基丁基、庚基、正庚基、辛基、正辛基、叔辛基、正壬基、癸基等，但并不限于此。本申请中的碳原子数1-4的烷基的实例包括但不限于：甲基(Me、-CH 3)、乙基(Et、-CH 2CH 3)、正丙基(n-Pr、-CH 2CH 2CH 3)、异丙基(i-Pr、-CH(CH 3) 2)、正丁基(n-Bu、-CH 2CH 2CH 2CH)、叔丁基(t-Bu,-C(CH 3) 3)等。
在本申请中，卤素基团可以为氟、氯、溴、碘。
本申请中，连接键用
Figure PCTCN2021096926-appb-000021
表示。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021096926-appb-000022
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)～式(f-10)所示出的任一可能的连接方式。
Figure PCTCN2021096926-appb-000023
再举例而言，如下式(X')中所示地，式(X')所表示的芴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'-5)所示出的任一可能的连接方式。
Figure PCTCN2021096926-appb-000024
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，下式(Y)中所示的，式(Y)所表示的取代基R基通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式。
Figure PCTCN2021096926-appb-000025
在本申请的一种具体实施方式中，所述有机化合物具有如下式(1-1)、式(1-2)、式(1-3)或式(1-4)所示的结构：
Figure PCTCN2021096926-appb-000026
Figure PCTCN2021096926-appb-000027
式(1-3)和式(1-4)中，p’选自0、1、2、3、4、5或6。式(1-2)、式(1-3)和式(1-4)中，各X 1彼此相同或不同、各X 2彼此相同或不同、各X 3彼此相同或不同、各X 4彼此相同或不同、各X 5彼此相同或不同；式(1-3)和式(1-4)中，各L 1彼此相同或不同。
在本申请的一种具体实施方式中，X 1、X 3和X 5为N，X 2和X 4为C(R 4)；各R 4彼此相同或者不同，且各自独立地为
Figure PCTCN2021096926-appb-000028
在本申请的一种具体实施方式中，R 1和R 2彼此相同或者不同，且分别独立地选自取代或未取代的甲基、取代或未取代的苯基；所述取代的甲基上的取代基各自独立地选自由氰基、氟、氯、氘所组成的组，所述取代的苯基中的取代基各自独立地选自由氰基、氟、氯、氘、甲基、乙基、异丙基、叔丁基、三甲基硅基所组成的组。
在本申请的一种具体实施方式中，R 1和R 2彼此相同或者不同，且分别独立地选自由甲基、取代或未取代的苯基，所述取代的苯基中的取代基各自独立地选自由氰基、氟、氯、氘、甲基、乙基、异丙基、叔丁基、三甲基硅基所组成的组。
在本申请的一种实施方式中，所述Y具有如下式(2-1)所示的结构：
Figure PCTCN2021096926-appb-000029
其中，X 1、X 3和X 5相同或不同，且分别独立地为C(R 4)或N，且X 1、X 3和X 5中的任意一者为N、任意两者为N或全部为N；各R 4相同或者不同，且各自独立地为氢或
Figure PCTCN2021096926-appb-000030
在本申请的另一种实施方式中，所述Y具有如下式(2-2)所示的结构：
Figure PCTCN2021096926-appb-000031
其中，X 1、X 3和X 5相同或不同，且分别独立地为C(R 4)或N，且X 1、X 3和X 5中的任意一者为N、任意两者为N或全部为N；各R 4相同或者不同，且各自独立地为氢或
Figure PCTCN2021096926-appb-000032
在本申请的一种具体实施方式中，所述Y具有如下式(2-1-1)至式(2-1-5)所示的结构：
Figure PCTCN2021096926-appb-000033
各R 4相同或者不同，且各自独立地为氢或
Figure PCTCN2021096926-appb-000034
在本申请的另一种具体实施方式中，所述Y具有如下式(2-1-6)所示的结构：
Figure PCTCN2021096926-appb-000035
各R 4相同或者不同，且各自独立地为氢或
Figure PCTCN2021096926-appb-000036
在本申请的一种实施方式中，各Ar独立地选自取代或未取代的碳原子数为1～6的烷基、取代或未取代的碳原子数为5～10的环烷基或者如下式(i-1)至式(i-18)基团所组成的组：
Figure PCTCN2021096926-appb-000037
Figure PCTCN2021096926-appb-000038
其中，M 1选自单键或者
Figure PCTCN2021096926-appb-000039
T 1～T 5各自独立地选自N或者C(Q 1)，且T 1～T 5中至少一个选自N；当T 1～T 5中的两个以上选自C(Q 1)时，任意两个Q 1相同或者不相同；
T 6～T 13各自独立地选自N或者C(Q 2)，且T 6～T 13中至少一个选自N；当T 6～T 13中的两个以上选自C(Q 2)时，任意两个Q 2相同或者不相同；
T 14～T 23各自独立地选自N或者C(Q 3)，且T 14～T 23中至少一个选自N；当T 14～T 23中的两个以上选自C(Q 3)时，任意两个Q 3相同或者不相同；
T 24～T 33各自独立地选自N或者C(Q 4)，且T 24～T 33中至少一个选自N；当T 24～T 33中的两个以上选自C(Q 4)时，任意两个Q 4相同或者不相同；
T 34～T 37各自独立地选自N或者C(Q 5)，且T 34～T 37中至少一个选自N；当T 34～T 37中的两个以上选自C(Q 5)时，任意两个Q 5相同或者不相同；任选地，两个相邻的Q 5形成6～10元芳环或5～10元杂芳环；
T 38～T 41各自独立地选自N或者C(Q 6)，且T 38～T 41中至少一个选自N；当T 38～T 41中的两个以上选自C(Q 6)时，任意两个Q 6相同或者不相同；任选地，两个相邻的Q 6形成6～10元芳环或5～10元杂芳环；
T 42～T 58各自独立地选自N或者C(Q 7)，且T 42～T 58中至少一个选自N；当T 42～T 58中的两个以上选自C(Q 7)时，任意两个Q 7相同或者不相同；任选地，两个相邻的Q 7形成6～10元芳环或5～10元杂芳环；
E 1选自氢、氘、氟、氯、溴、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；
E 2～E 6、E 21各自独立地选自：氢、氘、氟、氯、溴、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；
E 7～E 20、Q 1～Q 7各自独立地选自：氢、氘、氟、氯、溴、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6～18的芳基、碳原子数为3～18的杂芳基；
e 1～e 21以e k表示，E 1～E 21以E k表示，k为变量，表示1～21的任意整数，e k表示取代基E k的个数；
其中，当k选自5或者17时，e k选自1、2或者3；
当k选自2、7、8、12、15、16、18或者21时，e k选自1、2、3或者4；
当k选自1、3、4、6、9、14或者20时，e k选自1、2、3、4或者5；
当k为13时，e k选自1、2、3、4、5或者6；
当k选自10或者19时，e k选自1、2、3、4、5、6或者7；
当k为11时，e k选自1、2、3、4、5、6、7、8或9；且当e k大于1时，任意两个E k相同或者不相同；
K 1选自O、S、N(E 22)、C(E 23E 24)、Si(E 23E 24)；其中，E 22、E 23、E 24各自独立地选自：氢、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；
K 2选自单键、O、S、N(E 25)、C(E 26E 27)、Si(E 26E 27)；其中，E 25、E 26、E 27各自独立地选自：氢、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E 26和E 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。
在本申请中，上述E 23与E 24、上述E 26与E 27两组中，每组中的两个基团可以相互独立地存在，也可以相互连接形成环，相互连接所形成的环可以是碳原子数为3～15的饱和或不饱和的环。举例来讲，式(i-14)中，当K 2和M 1均为单键，各E 18均为氢，T 34～T 37均为CH，且K 1为C(E 23E 24)时，E 23与E 24相互连接以与它们共同连接的原子形成5元环时，式(i-14)即为
Figure PCTCN2021096926-appb-000040
同样地，式(i-14)也可以代表
Figure PCTCN2021096926-appb-000041
即E 23与E 24相互连接以与它们共同连接的原子形成部分不饱和的13元环。当然，所形成的环原子数还可以是其他数量，在此不再赘述。
本申请中，上述“任选地，两个相邻的Q 5形成6～10元芳环或5～10元杂芳环”，是指在式(i-14)中，任意两个相邻的Q 5可以相互独立地存在，也可以相互连接形成稠合的芳环或杂芳环，形成的稠合环可以是5～10元芳环或5～10元杂芳环。举例来讲，式(i-14)中，当K 2和M 1均为单键，各E 18均为氢，且K 1为-NH-时，T 34与T 37为-CH-，T 35和T 36为C(Q 5)且二者相互连接形成6元芳环时，式(i-14)即为
Figure PCTCN2021096926-appb-000042
当然，所形成的环原子数还可以是其他数量，在此不再赘述。“任选地，两个相邻的Q 6形成6～10元芳环或5～10元杂芳环”、“任选地，两个相邻的Q 7形成6～10元芳环或5～10元杂芳环”含义与此相同，不再赘述。
在一些实施方式中，各Ar独立地选自由取代或未取代的碳原子数为6～19的芳基、取代或未取代的碳原子数为5～18的杂芳基、取代或未取代的碳原子数为1～4的烷基、取代或未取代的碳原子数为5～7的环烷基。进一步地，各Ar各自独立地选自碳原子数为6、10、12、13、14、15、16、17、18、19、20的取代或未取代的芳基，或者选自碳原子数为3、5、8、9、12、16、18的取代或 未取代的杂芳基。
在一些实施方式中，各Ar中的取代基独立地选自由碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、三苯基硅基、碳原子数为5～7的环烷基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基、吲哚基、苯并咪唑基所构成的组。
进一步地，各Ar中的取代基独立地选自由氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、环戊烷基、环己烷基、三氟甲基、苯基、二联苯基、萘基、三甲基硅烷基、三苯基硅烷基所构成的组。
在本申请的一些具体实施方式中，各Ar独立地选自取代或未取代的基团W 3，所述未取代的基团W 3选自如下基团组成的组：
Figure PCTCN2021096926-appb-000043
所述基团W 3被取代时，基团W 3中的取代基选自由氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、三苯基硅基、碳原子数为5～7的环烷基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基、吲哚基、苯并咪唑基所组成的组；当所述基团W 3的取代基为多个时，各所述取代基彼此相同或不同。
在一些更具体的实施方式中，各Ar独立地选自：取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的喹啉基、取代或未取代的咔唑基、取代或未取代的萘基、取代或未取代的芴基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的嘧啶基、取代或者未取代的吡啶基、取代或者未取代的吡嗪基、取代或者未取代的喹啉基、取代或者未取代的异喹啉基、取代或者未取代的喹唑啉基、取代或者未取代的苯并噁嗪基、取代或者未取代的吲哚基、取代或未取代的苯并咪唑基、取代或未取代的苯并噁唑基、取代或未取代的二苯并噻蒽基、取代或未取代的吖啶基、取代或未取代的二苯并二噁英基、取代或未取代的苯氧茶碱基、取代或未取代的噻蒽基、取代或未取代的吩噻嗪基、取代或未取代的苯噁嗪基，或者为它们中两者或三者通过单键连接形成的基团；所述各Ar中的取代是指分别任选地被1、2、3、4、5、6、7、或8个选自氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、环戊烷基、环己烷基、三氟甲基、苯基、二联苯基、萘基、三甲基硅基、三苯基硅基的取代基所取代。
在一种更具体的实施方式中，各Ar独立地选自如下基团中的任意一个：
Figure PCTCN2021096926-appb-000044
Figure PCTCN2021096926-appb-000045
Figure PCTCN2021096926-appb-000046
在一种具体实施方式中，L 1和L 2相同或者不同，且各自独立地选自单键或者如下式(j-1)至式(j-20)所示的基团所组成的组：
Figure PCTCN2021096926-appb-000047
其中，M 2选自单键或者
Figure PCTCN2021096926-appb-000048
M 3选自
Figure PCTCN2021096926-appb-000049
Figure PCTCN2021096926-appb-000050
表示单键或不存在，当式(1)中m＝2时，L 1中的
Figure PCTCN2021096926-appb-000051
为单键，m＝1时，
Figure PCTCN2021096926-appb-000052
不存在；
G 1～G 5各自独立地选自N或者C(F 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(F 1)时，任意两个F 1相同或者不相同；
G 6～G 13各自独立地选自N或者C(F 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(F 2)时，任意两个F 2相同或者不相同；
G 14～G 23各自独立地选自N或者C(F 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(F 3)时，任意两个F 3相同或者不相同；
G 24～G 33各自独立地选自N或者C(F 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(F 4)时，任意两个F 4相同或者不相同；
Z 1～Z 2选自氢、氘、氟、氯、溴、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；
Z 3～Z 33、F 1～F 4各自独立地选自：氢、氘、氟、氯、溴、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6～18的芳基、碳原子数为3～18的杂芳基；
h 1～h 33以h k表示，Z 1～Z 33以Z k表示，k为变量，表示1～33的任意整数，h k表示取代基Z k的个数；
其中，当k选自1、2、3、4、5、6、8、12、14、15、16、18、25、32时，h k选自1、2、3或4；
当k选自3、9、22、24、27、28、30时，h k选自1、2、3、4或5；
当k选自7、17、21、23、26时，h k选自1、2或3；
当k为29时，h k选自1或2；
当k选自10、13、19、31时，h k选自1、2、3、4、5或6；
当k为11时，h k选自1、2、3、4、5、6、7或8；
当k选自20时，h k选自1、2、3、4、5、6或7；且当h k大于1时，任意两个Z k相同或者不相同；
K 3选自O、S、N(Z 24)、C(Z 25Z 26)、Si(Z 25Z 26)；其中，Z 24、Z 25、Z 26各自独立地选自：氢、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 25和Z 26相互连接以与它们共同连接的原子形成环；
K 4选自单键、O、S、N(Z 27)、C(Z 28Z 29)、Si(Z 28Z 29)；其中，Z 27、Z 28、Z 29各自独立地选自：氢、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 28和Z 29相互连接以与它们共同连接的原子形成环。
在一些实施方式中，L 1和L 2分别独立地选自：取代或未取代的碳原子数为6～18的亚芳基、取代或未取代的碳原子数为4～18的亚杂芳基、或者二者通过单键连接所形成的亚基基团；优选地，L 1和L 2中的取代基独立地选自由氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、三氟甲基、三甲基硅基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基、三苯基硅基所构成的组。
在一些实施方式中，L 1和L 2分别独立地选自：取代或未取代的碳原子数为6～18的亚芳基、取代或未取代的碳原子数为4～18的亚杂芳基、或者二者通过单键连接所形成的基团。进一步地，所述L 1和L 2分别独立地选自碳原子数为6、10、12、13、14、15、16、17、18的取代或未取代的亚芳基，或者选自碳原子数为4、5、8、9、10、12、16、18的取代或未取代的亚杂芳基。
在一些实施方式中，L 1和L 2中的取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、三甲基硅基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基所构成的组。
在一些更具体的实施方式中，各L 1和L 2分别独立地选自：取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的二苯并呋喃亚基、取代或未取代的二苯并噻吩亚基、取代或未取代的亚喹啉基、取代或未取代的亚咔唑基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲 基、取代或未取代的亚嘧啶基、取代或者未取代的亚吡啶基、取代或者未取代的亚吡嗪基、取代或者未取代的亚喹啉基、取代或者未取代的亚异喹啉基、取代或者未取代的亚喹唑啉基，或者为它们中两者或三者通过单键连接形成的亚基基团；所述各L 1和L 2中的取代是指分别独立地被1、2、3或4个选自氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、三氟甲基、苯基、咔唑基、萘基、三甲基硅基、三苯基硅基的取代基所取代。
在一种更具体的实施方式中，当式(1)中m＝1时，各L 1独立地选自单键或取代或未取代的基团W 1，所述未取代的基团W 1选自由如下基团所组成的组：
Figure PCTCN2021096926-appb-000053
所述基团W 1被一个或多个取代基所取代时，基团W 1中的取代基各自独立地选自由氘，氟，氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，三氟甲基，三甲基硅基，环戊烷基，环己烷基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、异丙基、叔丁基的取代基所取代的碳原子数为6～12的芳基或碳原子数为5～12的杂芳基所组成的组；所述基团W 1中的取代基数目多于1个时，各个取代基相同或不同；
当式(1)中m＝2时，各L 1独立地选自单键或取代或未取代的基团W 2，所述未取代的基团W 2选自由如下基团所组成的组：
Figure PCTCN2021096926-appb-000054
Figure PCTCN2021096926-appb-000055
所述基团W 2被一个或多个取代基所取代时，基团W 2中的取代基各自独立地选自由氘，氟，氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，三氟甲基，三甲基硅基，环戊烷基，环己烷基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、异丙基、叔丁基的取代基所取代的碳原子数为6～12的芳基或碳原子数为5～12的杂芳基所组成的组；所述基团W 2中的取代基数目多于1个时，各个取代基相同或不同。
在一些更具体的实施方式中，L 1为单键或者如下基团中的任意一个：
Figure PCTCN2021096926-appb-000056
Figure PCTCN2021096926-appb-000057
在一种具体的实施方式中，各L 2独立地选自单键、取代或未取代的基团W 4，所述未取代的基团W 4选自由如下基团所组成的组：
Figure PCTCN2021096926-appb-000058
所述基团W 4被一个或多个取代基所取代时，基团W 4中的取代基各自独立地选自由氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、环戊烷基，环己烷基、苯基、萘基和碳原子数为5～12的杂芳基所组成的组；所述基团W 4中的取代基数目多于1个时，各个取代基相同或不同。
在一种更具体的实施方式中，L 2选自单键或者如下基团中的任意一个：
Figure PCTCN2021096926-appb-000059
在一些具体实施方式中，各R 3分别独立地选自氘，氟，氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，碳原子数为1～4的卤代烷基，三甲基硅基，碳原子数为5～7的环烷基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为6～15的芳基或任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为3～18的杂芳基；所述R 3的数目多于1个时，各R 3相同或不同。
在一些具体实施方式中，各R 3分别独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、环戊烷基、环己烷基、苯基、联苯基、萘基、9,9-二甲基芴基、二苯并噻吩基、二苯并呋喃基或N-苯基咔唑基；R 3的数目多于1个时，各R 3相同或不同。
在一种具体的实施方式中，R 1和R 2相同，且选自甲基或苯基。
在一种具体的实施方式中，所述有机化合物选自如下有机化合物所组成的组：
Figure PCTCN2021096926-appb-000060
Figure PCTCN2021096926-appb-000061
Figure PCTCN2021096926-appb-000062
Figure PCTCN2021096926-appb-000063
Figure PCTCN2021096926-appb-000064
Figure PCTCN2021096926-appb-000065
Figure PCTCN2021096926-appb-000066
Figure PCTCN2021096926-appb-000067
Figure PCTCN2021096926-appb-000068
Figure PCTCN2021096926-appb-000069
Figure PCTCN2021096926-appb-000070
Figure PCTCN2021096926-appb-000071
Figure PCTCN2021096926-appb-000072
Figure PCTCN2021096926-appb-000073
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。
本申请第二方面提供一种电子元件，该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；所述功能层含有本申请第一方面所述的有机化合物。
在一种具体的实施方式中，所述功能层包括电子传输层，所述电子传输层含有所述有机化合物。电子传输层既可以由本申请所提供的有机化合物组成，也可以由本申请所提供的有机化合物和其他材料共同组成。所述电子传输层可以为一层或两层以上。
在一种具体的实施方式中，所述功能层包括空穴阻挡层，所述空穴阻挡层含有所述有机化合物。
在一种具体实施方式中，所述电子元件为有机电致发光器件或光电转化器件。
在一种具体实施方式中，所述电子元件为有机电致发光器件，例如为红光器件、绿光器件或蓝光器件。
在一种更具体实施方式中，电子元件可以为有机电致发光器件。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、空穴阻挡层341、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，本申请对此不做特殊的限定。例如，空穴传输层321可以由化合物NPB或化合物HT-01组成，电子阻挡层322可以包含化合物HT-02。
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掺杂材料。可选地，有机发光层330由主体材料和掺杂材料组成，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掺杂材料，进而使得掺杂材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、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BH-01。
有机发光层330的掺杂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。在本申请的一种实施方式中，有机发光层330的掺杂材料可以为BD-01。
空穴阻挡层341可以包括一种或多种空穴阻挡材料，空穴阻挡材料可选自本申请化合物或BCP。
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。在本申请的一种实施方式中，电子传输层材料含有本申请的有机化合物。在本申请的一种实施方式中，电子传输层材料含有BCP。
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。例如，电子注入层350可以包括Yb或LiQ。
按照另一种实施方式，电子元件可以为光电转化器件。如图3所示，该光电转化器件可以包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的有机化合物。
按照一种具体的实施方式，如图3所示，光电转化器件可包括依次层叠设置的阳极100、第一空穴传输层320、光电转化层360、电子传输层340和阴极200。
可选地，光电转化器件可以为太阳能电池，尤其是可以为有机薄膜太阳能电池。举例而言，在本申请的一种实施方式中，太阳能电池可以包括依次层叠设置的阳极、空穴传输层、光电转化层、电子传输层和阴极，其中，电子传输层包含有本申请的有机化合物。
本申请第三方面提供一种电子装置，包括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4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。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。
下面结合合成例来具体说明本申请的有机化合物的合成方法，但是本申请并不因此而受到任何限制。
合成例
下面所描述的合成例中，除非另有声明，否则所有的温度的单位为摄氏度。部分试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa ChemicalCompany，除非另有声明，否则使用时都没有经过进一步纯化。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。
在纯化时，色谱柱是硅胶柱，硅胶(100-200目)购于青岛海洋化工厂。
在各个合成例中，低分辨率质谱(MS)数据的测定条件是：Agilent 6120四级杆HPLC-M(柱子型号：Zorbax SB-C18,2.1×30mm,3.5微米,6min,流速为0.6mL/min。流动相：5％-95％(含0.1％甲酸的乙腈)在(含0.1％甲酸的水)中的比例)，采用电喷雾电离(ESI)，在210nm/254nm下，用UV检测。
核磁共振氢谱：布鲁克(Bruker)400MHz核磁仪，室温条件下，以CDCl 3为溶剂(以ppm为单位)，用TMS(0ppm)作为参照标准。当出现多重峰的时候，将使用下面的缩写：s(singlet，单峰)、d(doublet，双峰)、t(triplet，三重峰)、m(multiplet，多重峰)。
目标化合物使用Agilent 1260pre-HPLC或Calesep pump 250pre-HPLC(柱子型号：NOVASEP 50/80mm DAC)，在210nm/254nm用UV检测。
本申请中的中间体和化合物的分析检测使用ICP-7700质谱仪和M5000元素分析仪。
中间体I-A1～中间体I-A10的合成
步骤(1)：中间体I-1-A的合成
Figure PCTCN2021096926-appb-000074
将2-碘苯甲酸甲酯(10.0g，38.2mmol)、4-氯-2-甲氧基苯硼酸(7.83g，42.0mmol)、碳酸钾(10.54g，76.4mmol)、四丁基溴化铵(1.27g，3.82mmol)、甲苯(50mL)、乙醇(30mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下搅拌15min后加入四三苯基膦钯(0.44g，0.0382mmol)并升温至75-80℃，搅拌5小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相减压除去溶剂，残留物直接用快速硅胶柱色谱纯化，浓缩得到黄色油状物中间体I-1-A(9.50g，90％)。
步骤(2)：中间体I-1-B的合成
Figure PCTCN2021096926-appb-000075
将中间体I-1-A(5.54g，20mmol)和四氢呋喃(55mL)加入三口烧瓶中并开使搅拌，在氮气保护下缓慢滴加3M的甲基溴化镁的THF溶液(20mL，60mmol)，滴加完毕后在室温下搅拌1h，随后升温至60-66℃并且搅拌进行反应6h；将反应液冷却至室温，加入二氯甲烷(110mL)、搅拌下缓慢加入去离子水(55mL)，再缓慢加入1mol/L的稀盐酸(55mL)，在搅拌后静置分液，将有机相使用无水硫酸镁进行干燥，过滤，减压除去溶剂；得到淡黄色油状物中间体I-1-B(5g，90.25％)。
步骤(3)：中间体I-A1的合成
Figure PCTCN2021096926-appb-000076
将中间体I-1-B(5g，18mmol)和乙腈(50mL)加入三口烧瓶中，开始搅拌并使体系降温至0-10℃，然后滴加1M的三溴化硼的二氯甲烷溶液(18mL，18mmol)，将温度控制在0-10℃，1h后将体系自然升至室温，搅拌约5h；而后向反应液中加入去离子水(50mL)、二氯甲烷(50mL)，分液，将有机相用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得黄色油状粗品使用正庚烷进行硅胶柱色谱提纯，得到白色固体状中间体I-A1(3g，68.0％)。
GC-MS(pos.ion)m/z:244.10[M] +；
H 1 NMR(400MHz,CDCl 3):δ7.74-7.71(m,2H),7.40-7.37(m,2H),7.30(d,1H),7.05(dd,1H),6.99(d,1H),1.66(s,6H)ppm。
采用与制备中间体I-A1相同的方法制备表1中的中间体I-A2～中间体I-A10，不同之处仅在于，使用表1中的原料1代替合成中间体I-A1所采用的原料2-碘苯甲酸甲酯、使用原料2代替合成中间体I-A1所采用的原料4-氯-2-甲氧基苯硼酸。
表1
Figure PCTCN2021096926-appb-000077
中间体I-B1～中间体I-B10的合成：
Figure PCTCN2021096926-appb-000078
将中间体I-A1(2.5g,10.22mmol)、联硼酸频那醇酯(3.37g,13.28mmol)、三(二亚苄基丙酮)二钯(0.094g,0.10mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.15g,0.31mmol)、醋酸钾(2.51g,25.54mmol)和1,4-二氧六环(25mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；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；使用甲苯体系对粗品进行重结晶提纯，得到固体中间体I-B1(2.8g,收率81.5％)。
采用与制备中间体I-B1相同的方法制备中间体I-B2～中间体I-B10，不同之处仅在于，使用表2中的原料3(中间体I-A)代替合成中间体I-B1所采用的原料中间体I-A1。
表2
Figure PCTCN2021096926-appb-000079
Figure PCTCN2021096926-appb-000080
中间体I-D1～I-D15的合成
1、中间体I-D1的合成：
(1)
Figure PCTCN2021096926-appb-000081
将中间体I-B1(2.8g,8.33mmol)、3,5-二溴苄腈(2.17g,8.33mmol)、醋酸钯(0.0187g,0.0833mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.08g,0.17mmol)、碳酸钾(2.30g,16.65mmol)、甲苯(15mL)、无水乙醇(10mL)和去离子水(5mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌4h；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/正庚烷体系对粗品进行重结晶提纯，得到固体中间体I-C1(2.06g，收率63.6％)。
(2)
Figure PCTCN2021096926-appb-000082
将中间体I-C1(3.98g,10.22mmol)、联硼酸频那醇酯(3.37g,13.28mmol)、三(二亚苄基丙酮)二钯(0.094g,0.10mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.15g,0.31mmol)、醋酸钾(2.51g,25.54mmol)和1,4-二氧六环(25mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；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；使用甲苯体系对粗品进行重结晶提纯，得到固体中间体I-D1(3.61g,收率81％)。
2、中间体I-D2的合成：
(1)
Figure PCTCN2021096926-appb-000083
将中间体I-B1(2.8g,8.33mmol)、3,5-二溴氟苯(2.11g,8.33mmol)、醋酸钯(0.0187g,0.0833mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.08g,0.17mmol)、碳酸钾(2.30g,16.65mmol)、甲苯(15mL)、无水乙醇(10mL)和去离子水(5mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌4h；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/正庚烷体系对粗品进行重结晶提纯，得到固体中间体I-C2(1.81g，收率56.8％)。
(2)
Figure PCTCN2021096926-appb-000084
将中间体I-C2(3.91g,10.22mmol)、联硼酸频那醇酯(3.37g,13.28mmol)、三(二亚苄基丙酮)二钯(0.094g,0.10mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.15g,0.31mmol)、醋酸钾(2.51g,25.54mmol)和1,4-二氧六环(25mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；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；使用甲苯体系对粗品进行重结晶提纯，得到固体中间体I-D2(3.73g,收率85％)。
3、中间体I-D3～I-D15的合成
1)中间体I-C3～I-C18的合成：
采用与合成中间体I-C2相同的方法合成中间体I-C3～I-C18，不同之处在于，用表3中的中间体I-B代替用于合成中间体I-C2的原料中间体I-B1，用原料4代替合成中间体I-C2的原料3,5-二溴氟苯。
表3
Figure PCTCN2021096926-appb-000085
Figure PCTCN2021096926-appb-000086
2)中间体I-D3～I-D15的合成：
采用与制备中间体I-D2相同的方法制备中间体I-D3～I-D15，不同之处在于，用表4中的中间 体I-C代替合成中间体I-D2的原料中间体I-C2。
表4
Figure PCTCN2021096926-appb-000087
Figure PCTCN2021096926-appb-000088
中间体I-E1的合成
步骤(1)：
Figure PCTCN2021096926-appb-000089
将中间体I-1-A(5.54g，20mmol)和四氢呋喃(55mL)加入三口烧瓶中并开使搅拌，在氮气保护下缓慢滴加3M的苯基溴化镁的THF溶液(20mL，60mmol)，滴加完毕后在室温下搅拌1h，随后升温至60-66℃并且搅拌进行反应6h；将反应液冷却至室温，加入二氯甲烷(110mL)、搅拌下缓慢加入去离子水(55mL)，再缓慢加入1mol/L的稀盐酸(55mL)，在搅拌后静置分液，将有机相使用无水硫酸镁进行干燥，过滤，减压除去溶剂；得到淡黄色油状物中间体I-E1-A(6.57g，82％)。
步骤(2)：
Figure PCTCN2021096926-appb-000090
将中间体I-E1-A(6g，15mmol)和乙腈(50mL)加入三口烧瓶中，开始搅拌并使体系降温至0-10℃，然后滴加1M的三溴化硼的二氯甲烷溶液(18mL，18mmol)，将温度控制在0-10℃，1h后将体系自然升至室温，搅拌约5h；而后向反应液中加入去离子水(50mL)、二氯甲烷(50mL)， 分液，将有机相用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得黄色油状粗品使用正庚烷进行硅胶柱色谱提纯，得到白色固体状中间体I-E1-B(3.3g，60.0％)。
步骤(3)：
Figure PCTCN2021096926-appb-000091
将中间体I-E1-B(3.3g,8.62mmol)、联硼酸频那醇酯(2.84g,11.22mmol)、三(二亚苄基丙酮)二钯(0.08g,0.09mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.135g,0.25mmol)、醋酸钾(2.12g,21.45mmol)和1,4-二氧六环(25mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；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；使用甲苯体系对粗品进行重结晶提纯，得到固体中间体I-E1(3.37g,收率85％)。
按照中间体I-E1的合成步骤，只替换中间体I-1-A制备中的两个原料：用表5中的原料11和原料12反应得到不同的中间体，后续两步反应与中间体I-E1的合成反应相同，得到中间体I-E2、中间体I-E4～中间体I-E6。
表5
Figure PCTCN2021096926-appb-000092
中间体I-F1的合成
采用与合成中间体I-D2相同的方法制备中间体I-F1，不同之处仅在于，将用于合成中间体I-D2的原料I-B1换成中间体I-E1。
Figure PCTCN2021096926-appb-000093
Figure PCTCN2021096926-appb-000094
中间体I-F3和中间体I-F6的合成
按照中间体I-F1的合成步骤，仅用表6中的原料13替换中间体I-E1，用原料14替换3,5-二溴苯甲腈，制备中的两个原料得到中间体I-F3和中间体I-F6。
表6
Figure PCTCN2021096926-appb-000095
原料II的合成：
a、中间体II-A1的合成
Figure PCTCN2021096926-appb-000096
(1)称3'-氯-[1,1'-联苯基]-4-腈(CAS 5728-39-2,21.3g,100mmol)，联硼酸频哪醇酯(30.4g，120mmol)，乙酸钾(19.6g,200mmol)，1,4-二氧六环1000mL，升温至40℃～45℃，加入pd 2(dba) 3(0.28g，1mmol)，x-phos(0.14g，0.25mmol)，继续升温至80℃～85℃，保温2h停止反应。反应液倒入20L水中，搅拌下加入甲苯搅拌10min，静置10min，分液，水相用甲苯，萃取两次，合并有机相，水洗至pH＝7，有机相加无水硫酸钠干燥，有机相浓缩(T＝60～70℃，P＝0.075～0.09MPa)抽滤得固体，烘干得中间体II-A-1(24.4g，收率80％)。
Figure PCTCN2021096926-appb-000097
(2)2,4-二氯-6-苯基-1,3,5-三嗪(33.9g,150mmol)，中间体II-A-1(30.5g,100mmol)，碳酸钠 21.2g，四氢呋喃300mL，水150mL加入反应瓶，升温至40℃～45℃，加入四三苯基膦钯0.35g，继续升温至60℃～65℃，保温2h后停止反应。在搅拌下将反应液倒入水中搅拌降至室温，约30min，过滤，滤饼烘干。加二氯乙烷溶解清亮，过硅胶的层析柱(80～120目，常温常压)过柱完毕，用二氯乙烷淋洗，降至室温，抽滤得大量白色固体，烘料(鼓风烘箱，55～65℃，约5h)，得中间体II-A1(16.5g，收率45％)。
b、中间体II-A2的合成
Figure PCTCN2021096926-appb-000098
在氮气保护下，向A反应瓶内加入3,5-二苯基溴苯(30.9g,100mmol)，开启搅拌，升温至50～55℃，确认溶解清亮，快速加入镁粉(2.88g)，产生强烈回流，大约持续3min，溶液由淡黄色转变为粘稠状紫黑色，保温1小时，生成格氏试剂。在氮气保护下，向B反应瓶内加入三聚氯氰(10.4g,56.8mmol)，开启搅拌，溶清后，用冷冻乙醇给反应体系降温，当反应体系温度降至-15至-10℃时，用恒压滴液漏斗缓慢滴加制备好的格氏试剂，控制反应温度为-10±5℃，滴加完毕，反应2h之后，析出大量类白色固体，过滤，水洗固体，用甲苯重结晶得中间体II-A2(12.87g，收率45％)。
c、中间体II-A3～II-A5合成
采用与合成中间体II-A1相同的方法合成中间体II-A3～II-A5，不同之处仅在于，采用表7中的原料5代替用于合成中间体II-A1的原料2,4-二氯-6-苯基-1,3,5-三嗪，用原料6代替用于合成中间体II-A1的原料中间体II-A-1。
表7
Figure PCTCN2021096926-appb-000099
中间体II-A6、中间体II-A9、中间体II-A10、中间体II-A11的合成：
中间体II-A6、中间体II-A9、中间体II-A10、中间体II-A11的制备过程如下，反应操作参照上述中间体II-A1的合成过程。
Figure PCTCN2021096926-appb-000100
化合物的合成
(1)化合物124的合成
Figure PCTCN2021096926-appb-000101
将中间体I-B1(13.44g，40mmol)、中间体II-A1(16.19g，44.0mmol)、碳酸钾(11.04g，80mmol)、四丁基溴化铵(1.32g，4mmol)、甲苯(100mL)、乙醇(50mL)和去离子水(50mL) 加入三口烧瓶中，氮气保护下搅拌15min后加入四三苯基膦钯(0.46g，0.4mmol)并升温至75-80℃，搅拌5小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相减压除去溶剂，残留物直接用快速硅胶柱色谱纯化，浓缩得到类白色固体化合物124(16.9g，收率78％)。LC-MS(ESI,pos.ion)m/z:543.2[M+H] +。
(2)化合物76的合成
Figure PCTCN2021096926-appb-000102
将中间体1-F1(14.0g，25mmol)、原料C(16.2g，27.5mmol)、碳酸钾(6.9g，50mmol)、四丁基溴化铵(0.83g，2.5mmol)、甲苯(100mL)、乙醇(50mL)和去离子水(50mL)加入三口烧瓶中，氮气保护下搅拌15min后加入四三苯基膦钯(0.29g，0.24mmol)并升温至75-80℃，搅拌5小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相减压除去溶剂，残留物直接用快速硅胶柱色谱纯化，浓缩得到类白色固体化合物76(15.98g，收率72％)。LC-MS(ESI,pos.ion)m/z:888.3[M+H] +。
(3)化合物129的合成
Figure PCTCN2021096926-appb-000103
中间体I-B1(13.44g，40mmol)，3,5-二溴碘苯(14.47g，40mmol)，碳酸钾(11.04g，80mmol)、四丁基溴化铵(1.32g，4mmol)、甲苯(100mL)、乙醇(50mL)和去离子水(50mL)加入三口烧瓶中，氮气保护下搅拌15min后加入四三苯基膦钯(0.92g，0.08mmol)并升温至75-80℃，搅拌8小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相减压除去溶剂，残留物直接用快速硅胶柱色谱纯化，浓缩得到类白色固体中间体I-C12(12.08g，收率68％)。
Figure PCTCN2021096926-appb-000104
将中间体II-A7(5.7g,20mmol)、联硼酸频那醇酯(6.09g,24mmol)、三(二亚苄基丙酮)二钯(0.18g,0.20mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.19g,0.40mmol)、醋酸钾(3.84g,40mmol)和1,4-二氧六环(50mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌5h；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；使用甲苯体系对粗品进行重结晶提纯，得到固体中间体II-A8(3.92g，收率52％)。
按照中间体II-A8的制备方法，以2-氯-4,6-二苯基三嗪替代中间体II-A7制备以下中间体：
Figure PCTCN2021096926-appb-000105
Figure PCTCN2021096926-appb-000106
将中间体I-C12(8.88g，20mmol)、中间体II-A8(16.58g，44mmol)、碳酸钾(11.04g，80mmol)、四丁基溴化铵(1.32g，4mmol)、甲苯(100mL)、乙醇(50mL)和去离子水(50mL)加入三口烧瓶中，氮气保护下搅拌15min后加入四三苯基膦钯(0.92g，0.08mmol)并升温至75-80℃，搅拌8小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相减压除去溶剂，残留物直接用快速硅胶柱色谱纯化，浓缩得到类白色固体化合物129(8.15g，收率52％)。LC-MS(ESI,pos.ion)m/z:785.3[M+H] +。
(4)化合物12、15、22、23、28和288～319的合成
采用与合成化合物124相同的方法合成化合物12、15、22、23、28和288～319，不同之处在于，用表8中的原料7代替用于合成化合物124的中间体I-B1，用原料8代替用于合成化合物124的中间体II-A1。
其中，中间体
Figure PCTCN2021096926-appb-000107
Figure PCTCN2021096926-appb-000108
均由商购。
表8
Figure PCTCN2021096926-appb-000109
Figure PCTCN2021096926-appb-000110
Figure PCTCN2021096926-appb-000111
Figure PCTCN2021096926-appb-000112
Figure PCTCN2021096926-appb-000113
Figure PCTCN2021096926-appb-000114
(5)采用与合成化合物124相同的方法合成化合物2、5、63、66、86、89、97、99、103～111、123、131、132、136、137、141、157等，不同之处在于，用表9中的原料9代替用于合成化合物124的中间体I-B1，用原料10代替用于合成化合物124的中间体II-A1。下表9中的原料均商购获得。
中间体I-D16使用上述已制备的中间体I-C18，按照以下合成方法进行制备。
Figure PCTCN2021096926-appb-000115
表9
Figure PCTCN2021096926-appb-000116
Figure PCTCN2021096926-appb-000117
Figure PCTCN2021096926-appb-000118
Figure PCTCN2021096926-appb-000119
Figure PCTCN2021096926-appb-000120
上表部分化合物的核磁数据如下：
化合物2核磁数据： 1H-NMR(400MHz,CDCl 3):δ8.92-8.88(m,3H),8.68-8.62(m,3H),8.26(d,1H),8.24(d,1H),7.85-7.50(m,8H),7.38-7.29(m,3H),7.17(t,1H)1.66(s,6H)ppm。
化合物151核磁数据： 1H-NMR(400MHz,CDCl 3):δ8.90-8.88(d,2H),8.30-8.25(m,4H),7.98-7.88(m,5H),7.72-7.51(m,8H),7.42-7.29(m,4H),7.19(t,1H)7.16(s,1H)1.66(s,6H)ppm。
本申请中其他化合物均可按照上述合成例的合成方法进行合成。
器件制备实施例
实施例1蓝色有机电致发光器件
通过以下过程制备阳极：将厚度为
Figure PCTCN2021096926-appb-000121
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以形成厚度为的厚度为
Figure PCTCN2021096926-appb-000122
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-01，形成厚度为
Figure PCTCN2021096926-appb-000123
的空穴传输层。
在空穴传输层上真空蒸镀HT-02，形成厚度为
Figure PCTCN2021096926-appb-000124
的电子阻挡层。
在电子阻挡层上，将BH-01和BD-01以98％：2％的比例(蒸镀速率)进行共同蒸镀，形成厚度为
Figure PCTCN2021096926-appb-000125
的有机发光层(EML)。
在有机发光层上，将化合物BCP蒸镀形成
Figure PCTCN2021096926-appb-000126
厚的空穴阻挡层(a-ETL)。
在空穴阻挡层上，将化合物2和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2021096926-appb-000127
厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021096926-appb-000128
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1：9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021096926-appb-000129
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021096926-appb-000130
的CP-1，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例2～32
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，除了在形成电子传输层时，以下表11中所示的化合物替代化合物2。
实施例33
采用与实施例1相同的方法制作有机电致发光器件，不同之处在于，在形成空穴阻挡层时，以化合物129代替BCP蒸镀在有机发光层上形成
Figure PCTCN2021096926-appb-000131
厚的空穴阻挡层(a-ETL)。以化合物BCP代替化合物2，与LiQ以1：1的重量比进行混合并蒸镀形成
Figure PCTCN2021096926-appb-000132
厚的电子传输层(ETL)。
实施例34～71
采用与实施例33相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以下表11中所示的化合物替代化合物129。
比较例1
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成电子传输层时，以下表10中所示的化合物A替代化合物2。
比较例2
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成电子传输层时，以下表10中所示的化合物B替代化合物2。
比较例3
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成电子传输层时，以下表10中所示的化合物C替代化合物2。
比较例4
采用与实施例33相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以下表10中所示的化合物A替代化合物129。
比较例5
采用与实施例33相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以下表10中所示的化合物B替代化合物129。
比较例6
采用与实施例33相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以下表10中所示的化合物C替代化合物129。
以上实施例和对比例使用的主要材料结构如表10所示。
表10
Figure PCTCN2021096926-appb-000133
对上述实施例和对比例制得的有机电致发光器件，分析了在10mA/cm 2的条件下器件的光电性能，和20mA/cm 2的条件下器件的T95寿命性能，其结果示于下表11：
表11
Figure PCTCN2021096926-appb-000134
Figure PCTCN2021096926-appb-000135
Figure PCTCN2021096926-appb-000136
参考上表可知，实施例1-32将本发明化合物用作电子传输层材料时，与比较例1-3相比，对于器件的驱动电压和寿命有着较为明显的改善，其中发光效率至少提高了21.8％，外量子效率至少提高了13.1％，寿命至少提高了26.1％。
实施例33-71将本发明化合物用作空穴阻挡层材料时，与比较例4-6相比，对于器件的发光效率和寿命有着较为明显的改善，其中发光效率至少提高了10.1％，外量子效率至少提高了11.2％， 寿命至少提高了22.8％。
究其原因，可能是化合物A和C中氧原子邻位为螺环，空间构象基本固定，载流子传输效率不足，导致器件效率低于本发明化合物，并且化合物A和C在发光器件有机层之间，或有机层与金属电极之间产生的焦耳热较多，一定程度降低了器件使用寿命。对比化合物B的母核中带有羰基，化合物母核中C-C键变弱，一定程度上降低器件使用寿命。
因此，本申请的新型化合物用于制备有机电致发光器件时，可以有效地降低器件的驱动电压，同时对器件寿命也有提升效果。
化合物的热稳定性试验
部分材料热稳定性数据如下表12所示，其中Tg采用热失重分析仪(TGA)测试得到，Te为化合物在蒸镀机中，蒸镀速率为
Figure PCTCN2021096926-appb-000137
时的蒸镀温度。
化合物在用于量产制备器件时，需要在蒸镀条件下长时间受热。若化合物在受热条件下分子结构的热稳定性差，则在长时间受热条件下化合物的纯度会下降，导致量产前中后期制备的器件性能差异较大。
本公开通过如下方法评估本公开的含氮化合物在量产蒸镀时长时间受热下分子结构的稳定性：
在高真空环境(<10 -6Pa)，以及
Figure PCTCN2021096926-appb-000138
每秒的蒸镀速度对应的温度下，对本申请化合物和对比化合物分别进行24小时耐热实验(保温处理)。通过耐热实验前后的纯度下降值判断本公开的含氮化合物在量产条件下的稳定性。
对比化合物：
Figure PCTCN2021096926-appb-000139
表12:化合物的试验温度和纯度下降值
Figure PCTCN2021096926-appb-000140
Figure PCTCN2021096926-appb-000141
Figure PCTCN2021096926-appb-000142
由上表12可知，本申请化合物在高温器件蒸镀成膜过程中具有较低的分解可能性，并且在器件运行中具有在电焦耳热环境下更高的结晶抵抗性。
本申请化合物与对比例化合物相比，在分子量相差不大的情况下，本申请化合物蒸镀温度(Te)较低。根据表12可知，受热后本申请的含氮化合物的纯度下降值均小于0.1％。而在对比例中，纯度下降值超过1％，因此本申请化合物具有更好的热稳定性。
化合物纯度下降值超过1％时，会导致器件的效率和寿命发生明显降低；热不稳定的化合物在实际量产使用中，会导致量产前中后期制备的器件性能存在较大差异。本发明中，化合物的耐热实验证实其纯度下降值均小于0.1％，对比例化合物在测试温度(Te+70℃)下，纯度下降超过1％，因此本公开的化合物相比于对比例化合物具有更优秀的量产热稳定性。
以上结合附图详细描述了本公开的优选实施方式，但是，本公开并不限于上述实施方式中的具体细节，在本公开的技术构思范围内，可以对本公开的技术方案进行多种简单变型，这些简单变型均属于本公开的保护范围。

Claims (18)

  1. 一种有机化合物，所述有机化合物具有如下式(1)所示的结构：
    Figure PCTCN2021096926-appb-100001
    式(1)中，R 1和R 2彼此相同或者不同，且分别独立地选自取代或未取代的碳原子数为1～4的烷基、取代或未取代的苯基，当R 1或R 2为取代的烷基时，所述取代的烷基中的取代基相同或不同，且各自独立地选自由氘、氟、氯、氰基所组成的组；当R 1或R 2为取代的苯基时，所述取代的苯基中的取代基相同或不同，且各自独立地选自由碳原子数为1～6的烷基、氰基、卤素基团、氘、三甲基硅基所组成的组；
    各R 3彼此相同或者不同，且各自独立地选自由氘，卤素基团，氰基，碳原子数为1～12的卤代烷基，碳原子数为1～12的烷基，碳原子数为1～12的烷氧基，碳原子数为3～12的环烷基，碳原子数为1～12的烷硫基，碳原子数为3～12的三烷基硅基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为6～20的芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为3～20的杂芳基，碳原子数为6～20的芳氧基，碳原子数为6～20的芳硫基，碳原子数为6～18的芳基硅基，碳原子数为1～12的烷基膦氧基所组成的组；
    p选自0、1、2、3、4、5、6或7；
    各Y彼此相同或者不同，且各自独立地具有式(2)所示的结构，X 1、X 2、X 3、X 4和X 5彼此相同或不同，且分别独立地为C(R 4)或N，且X 1、X 2、X 3、X 4和X 5中至少一者为N；
    m选自1或2；n选自1或2；
    式(2)中，各R 4彼此相同或者不同，且各自独立地为氢或
    Figure PCTCN2021096926-appb-100002
    或者两个相邻的R 4相互连接形成取代或未取代的5～10元芳环或者取代或未取代的5～10元杂芳环；所述取代的5～10元芳环或取代的5～10元杂芳环中的取代基彼此相同或不同，且各自独立地选自由氘、卤素基团、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为1～12的烷硫基、碳原子数为6～25的芳基、碳原子数为3～20的杂芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组；
    各Ar独立地选自由取代或未取代的碳原子数为6～40的芳基、取代或未取代的碳原子数为3～40的杂芳基、取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳原子数为3～12的环烷基、取代或未取代的碳原子数为7～30的芳烷基、取代或未取代的碳原子数为4～30的杂芳烷基所组成的组；
    各L 1和L 2彼此相同或者不同，且各自独立地选自由单键、取代或未取代的碳原子数为6～30的亚芳基和取代或未取代的碳原子数为3～30的亚杂芳基所组成的组；
    各L 1、L 2和Ar中的取代基彼此相同或不同，且各自独立地选自由氘，卤素基团，氰基，碳原子数为1～12的烷基，碳原子数为1～12的卤代烷基，碳原子数为1～12的烷氧基，碳原子数为1～12的烷硫基，任选地被选自氘、氟、氰基、烷基的取代基所取代的碳原子数为6～25的芳基，碳原子数为3～20的杂芳基，碳原子数为6～20的芳氧基，碳原子数为6～20的芳硫基，碳原子数为3～12的三烷基硅基，碳原子数为8～18的芳基硅基和碳原子数为3～12的环烷基所组成的组；在各L 1、L 2和Ar中，当同一原子上具有两个取代基时，两个所述取代基任选地相互连接以与它们所共同连接的原子一起形成5～18元脂肪族环或5～18元芳香环。
  2. 根据权利要求1所述的有机化合物，其中，所述有机化合物具有如下式(1-1)、式(1-2)、 式(1-3)或式(1-4)所示的结构：
    Figure PCTCN2021096926-appb-100003
    式(1-3)和式(1-4)中，p’选自0、1、2、3、4、5或6。
  3. 根据权利要求1或2所述的有机化合物，其中，R 1和R 2彼此相同或者不同，且分别独立地选自甲基、取代或未取代的苯基，所述取代的苯基中的取代基各自独立地选自由氰基、氟、氯、氘、甲基、乙基、异丙基、叔丁基、三甲基硅基所组成的组。
  4. 根据权利要求1～3任一项所述的有机化合物，其中，所述Y具有如下式(2-1)所示的结构：
    Figure PCTCN2021096926-appb-100004
    其中，X 1、X 3和X 5相同或不同，且分别独立地为C(R 4)或N，且X 1、X 3和X 5中的任意一者为N、任意两者为N或全部为N；各R 4相同或者不同，且各自独立地为氢或
    Figure PCTCN2021096926-appb-100005
  5. 根据权利要求1～3任一项所述的有机化合物，其中，所述Y具有如下式(2-2)所示的结构：
    Figure PCTCN2021096926-appb-100006
    其中，X 1、X 3和X 5相同或不同，且分别独立地为C(R 4)或N，且X 1、X 3和X 5中的任意一者为N、任意两者为N或全部为N；各R 4相同或者不同，且各自独立地为氢或
    Figure PCTCN2021096926-appb-100007
  6. 根据权利要求1～5任一项所述的有机化合物，其中，各Ar独立地选自取代或未取代的碳原子数为6～19的芳基、取代或未取代的碳原子数为5～18的杂芳基、取代或未取代的碳原子数为1～4的烷基、取代或未取代的碳原子数为5～7的环烷基；优选地，各Ar中的取代基独立地选自由碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、三苯基硅基、碳原子数为5～7的环烷基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基、吲哚基、苯并咪唑基所构成的组。
  7. 根据权利要求1～5任一项所述的有机化合物，其中，各Ar独立地选自取代或未取代的基团W 3，所述未取代的基团W 3选自如下基团组成的组：
    Figure PCTCN2021096926-appb-100008
    所述基团W 3被取代时，基团W 3中的取代基选自由氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、三苯基硅基、碳原子数为5～7的环烷基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基、吲哚基、苯并咪唑基所组成的组；当所述基团W 3中的取代基为多个时，各所述取代基彼此相同或不同。
  8. 根据权利要求1～5任一项所述的有机化合物，其中，各Ar独立地选自：取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的喹啉基、取代或未取代的咔唑基、取代或未取代的萘基、取代或未取代的芴基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的嘧啶基、取代或者未取代的吡啶基、取代或者未取代的吡嗪基、取代或者未取代的喹啉基、取代或者未取代的异喹啉基、取代或者未取代的喹唑啉基、取代或者未取代的苯并噁嗪基、取代或者未取代的吲哚基、取代或未取代的苯并咪唑基、取代或未取代的苯并噁唑基、取代或未取代的 二苯并噻蒽基、取代或未取代的吖啶基、取代或未取代的二苯并二噁英基、取代或未取代的苯氧茶碱基、取代或未取代的噻蒽基、取代或未取代的吩噻嗪基、取代或未取代的苯噁嗪基，或者为它们中两者或三者通过单键连接形成的基团；所述各Ar中的取代是指分别任选地被1、2、3、4、5、6、7或8个选自氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、环戊烷基、环己烷基、三氟甲基、苯基、二联苯基、萘基、三甲基硅基、三苯基硅基的取代基所取代。
  9. 根据权利要求1～8任一项所述的有机化合物，其中，L 1和L 2分别独立地选自：取代或未取代的碳原子数为6～18的亚芳基、取代或未取代的碳原子数为4～18的亚杂芳基、或者二者通过单键连接所形成的亚基基团；优选地，L 1和L 2中的取代基独立地选自由氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、三氟甲基、三甲基硅基、苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑基、吡啶基、嘧啶基、三苯基硅基所构成的组。
  10. 根据权利要求1～9任一项所述的有机化合物，其中，各L 2各自独立地选自单键、取代或未取代的基团W 4，所述未取代的基团W 4选自由如下基团所组成的组：
    Figure PCTCN2021096926-appb-100009
    所述基团W 4被一个或多个取代基所取代时，基团W 4中的取代基各自独立地选自由氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、碳原子数为1～4的烷氧基、三氟甲基、三甲基硅基、环戊烷基，环己烷基、苯基、萘基和碳原子数为5～12的杂芳基所组成的组；所述基团W 4中的取代基数目多于1个时，各个取代基相同或不同。
  11. 根据权利要求1～9任一项所述的有机化合物，其中，当式(1)中m＝1时，各L 1独立地选自单键或取代或未取代的基团W 1，所述未取代的基团W 1选自由如下基团所组成的组：
    Figure PCTCN2021096926-appb-100010
    Figure PCTCN2021096926-appb-100011
    所述基团W 1被一个或多个取代基所取代时，基团W 1中的取代基各自独立地选自由氘，氟，氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，三氟甲基，三甲基硅基，环戊烷基，环己烷基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、异丙基、叔丁基的取代基所取代的碳原子数为6～12的芳基或碳原子数为5～12的杂芳基所组成的组；所述基团W 1中的取代基数目多于1个时，各个取代基相同或不同；
    当式(1)中m＝2时，各L 1独立地选自单键或取代或未取代的基团W 2，所述未取代的基团W 2选自由如下基团所组成的组：
    Figure PCTCN2021096926-appb-100012
    所述基团W 2被一个或多个取代基所取代时，基团W 2中的取代基各自独立地选自由氘，氟， 氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，三氟甲基，三甲基硅基，环戊烷基，环己烷基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、异丙基、叔丁基的取代基所取代的碳原子数为6～12的芳基或碳原子数为5～12的杂芳基所组成的组；所述基团W 2中的取代基数目多于1个时，各个取代基相同或不同。
  12. 根据权利要求1～9任一项所述的有机化合物，其中，各L 1和L 2分别独立地选自：取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚喹啉基、取代或未取代的亚咔唑基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚嘧啶基、取代或者未取代的亚吡啶基、取代或者未取代的亚吡嗪基、取代或者未取代的亚喹啉基、取代或者未取代的亚异喹啉基、取代或者未取代的亚喹唑啉基，或者为它们中两者或三者通过单键连接形成的亚基基团；所述各L 1和L 2中的取代是指分别独立地被1、2、3或4个选自氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、三氟甲基、苯基、咔唑基、萘基、三甲基硅基、三苯基硅基的取代基所取代。
  13. 根据权利要求1～12任一项所述的有机化合物，其中，各R 3分别独立地选自氘，氟，氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，碳原子数为1～4的卤代烷基，三甲基硅基，碳原子数为5～7的环烷基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为6～15的芳基或任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基的取代基所取代的碳原子数为3～18的杂芳基；所述R 3的数目多于1个时，各R 3相同或不同。
  14. 根据权利要求1～13任一项所述的有机化合物，其中，R 1和R 2相同，且选自甲基或苯基。
  15. 根据权利要求1～14任一项所述的有机化合物，其中，所述有机化合物选自如下有机化合物所组成的组：
    Figure PCTCN2021096926-appb-100013
    Figure PCTCN2021096926-appb-100014
    Figure PCTCN2021096926-appb-100015
    Figure PCTCN2021096926-appb-100016
    Figure PCTCN2021096926-appb-100017
    Figure PCTCN2021096926-appb-100018
    Figure PCTCN2021096926-appb-100019
    Figure PCTCN2021096926-appb-100020
    Figure PCTCN2021096926-appb-100021
    Figure PCTCN2021096926-appb-100022
    Figure PCTCN2021096926-appb-100023
    Figure PCTCN2021096926-appb-100024
    Figure PCTCN2021096926-appb-100025
    Figure PCTCN2021096926-appb-100026
  16. 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，所述功能层含有权利要求1-15中任一项所述的有机化合物；
    可选地，所述功能层包括电子传输层，所述电子传输层含有权利要求1-15中任一项所述的有机化合物；
    可选地，所述功能层包括空穴阻挡层，所述空穴阻挡层含有权利要求1-15中任一项所述的有机化合物。
  17. 根据权利要求16所述的电子元件，其特征在于，所述电子元件为有机电致发光器件或光电转化器件。
  18. 一种电子装置，其特征在于，包括权利要求16或17所述的电子元件。
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