WO2021228111A1 - 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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WO2021228111A1
WO2021228111A1 PCT/CN2021/093160 CN2021093160W WO2021228111A1 WO 2021228111 A1 WO2021228111 A1 WO 2021228111A1 CN 2021093160 W CN2021093160 W CN 2021093160W WO 2021228111 A1 WO2021228111 A1 WO 2021228111A1
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carbon atoms
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French (fr)
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张孔燕
马天天
曹佳梅
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陕西莱特光电材料股份有限公司
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Priority to US17/913,193 priority Critical patent/US11910709B2/en
Publication of WO2021228111A1 publication Critical patent/WO2021228111A1/zh

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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.
  • This type of electronic components usually includes a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
  • an organic electroluminescence device as an example, it generally includes an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer, and a cathode that are stacked in sequence.
  • the two electrodes When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light emitting layer. The electrons and holes are combined in the electroluminescent layer. Excitons are formed, and the excitons are in an excited state to release energy outward, which in turn makes the electroluminescent layer emit light to the outside.
  • organic electroluminescent devices has problems such as reduced luminous efficiency and shortened lifespan, resulting in a decrease in the performance of organic electroluminescent devices.
  • the purpose of this application is to provide an organic compound and an electronic component and electronic device using the same.
  • the organic compound is used in an organic electroluminescent device to improve the performance of the organic electroluminescent device.
  • the present application provides an organic compound, the organic compound having the structure shown in the following formula I:
  • Z is selected from O, S, C (R 3 R 4 ) or N (R 5 ), Si (R 3 R 4 ), Se, wherein R 3 , R 4 and R 5 are the same or different, and are each independently Selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or the above R 3 And R 4 can form a ring with the atoms to which they are connected together;
  • X 1 , X 2 and X 3 are the same or different, and are each independently selected from CH or N, and at least one of X 1 , X 2 and X 3 is N;
  • R 1 and R 2 are the same or different, and are each independently selected from deuterium, halogen groups, alkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and 3- 12 trialkylsilyl groups, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, and alkane groups with 1-10 carbon atoms Oxy; n 1 represents the number of R 1 , n 2 represents the number of R 2 ; R 1 and R 2 are represented by R i , n 1 ⁇ n 2 are represented by n i , i is a variable, which means 1 or 2, Each n i is independently selected from 0, 1, 2, 3 or 4; and when n i is greater than 1, any two n i are the same or different; optionally, any two adjacent R i form a ring;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms;
  • L 1 , L 2 and L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 35 carbon atoms, and a substituted or unsubstituted with 3 to 30 carbon atoms ⁇ heteroarylene;
  • R 1 ⁇ R 5 , L 1 ⁇ L 3 and Ar 1 ⁇ Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, group A, three carbon atoms of 3-12 Alkylsilyl, triarylsilyl with 18-24 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkane with 3-10 carbon atoms Group, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms , The arylthio group with 6-18 carbon atoms, the alkenyl group with 2-6 carbon atoms; the group A is selected from substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms or the number of carbon atoms is 6-20 substituted or unsubstituted aryl groups, the substituents
  • Ad represents an adamantyl group, and q is selected from 1, 2 or 3.
  • the 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 includes the organic compound described in the first aspect of the present application .
  • 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 organic compound of the present application uses azabenzene as the core, and the aromatic heterocyclic group is connected around it, which destroys the crystallinity of the molecule and avoids the aggregation between the molecules.
  • Adamantane is introduced into the molecular structure by connecting to the aromatic group and then to the nucleus.
  • the rigid non-conjugated structure formed effectively interrupts the conjugation and electron transfer of different functional groups, and greatly
  • the access of steric hindrance groups avoids the aggregation of compounds and the direct accumulation of conjugated planes to form ⁇ aggregations or excimer associations.
  • the application of this organic compound to organic electroluminescent devices can ensure that the device has a low While driving the voltage, the luminous efficiency is improved.
  • this structure can improve the film-forming properties of the material, and at the same time increase the overall molecular weight and asymmetry, and improve the thermal stability of the molecule.
  • the compound of the present application has good film-forming properties and fluorescence quantum efficiency.
  • the electron donor and electron acceptor contained in the molecule can increase the orbital overlap and improve the luminous efficiency, and the intramolecularly connected aromatic heterocyclic group helps to obtain HOMO , LUMO space separated charge transfer state material. Accordingly, when the organic compound of the present application is used in the light-emitting layer of an organic electroluminescent device, the device efficiency of the device can be effectively improved, and the life of the organic electroluminescent device can be prolonged.
  • 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 an electronic device according to an embodiment of the present application.
  • Anode; 200 cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light emitting layer 340, electron transport layer; 350, electron injection layer; 400, electronic device.
  • the present application provides an organic compound, the organic compound having a structure shown in the following formula I:
  • Z is selected from O, S, C(R 3 R 4 ), N(R 5 ), Si(R 3 R 4 ), Se, wherein R 3 , R 4 and R 5 are the same or different, and are each independently Selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or the above R 3 And R 4 can form a ring with the atoms to which they are connected together;
  • X 1 , X 2 and X 3 are the same or different, and are each independently selected from CH or N, and at least one of X 1 , X 2 and X 3 is N;
  • R 1 and R 2 are the same or different, and are each independently selected from deuterium, halogen groups, alkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and 3- 12 trialkylsilyl groups, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, and alkane groups with 1-10 carbon atoms Oxy; n 1 represents the number of R 1 , n 2 represents the number of R 2 ; R 1 and R 2 are represented by R i , n 1 ⁇ n 2 are represented by n i , i is a variable, which means 1 or 2, Each n i is independently selected from 0, 1, 2, 3 or 4; and when n i is greater than 1, any two n i are the same or different; optionally, any two adjacent R i form a ring, for example Any two adjacent R i form a benzene ring
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms;
  • L 1 , L 2 and L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 35 carbon atoms, and a substituted or unsubstituted with 3 to 30 carbon atoms ⁇ heteroarylene;
  • R 1 ⁇ R 5 , L 1 ⁇ L 3 and Ar 1 ⁇ Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, group A, three carbon atoms of 3-12 Alkylsilyl, triarylsilyl with 18-24 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkane with 3-10 carbon atoms Group, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms , The arylthio group with 6-18 carbon atoms, the alkenyl group with 2-6 carbon atoms; the group A is selected from substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms or the number of carbon atoms is 6-20 substituted or unsubstituted aryl groups, the substituents
  • Ad represents an adamantyl group, and q is selected from 1, 2 or 3.
  • Formula I Indicates that the group L 3 can be attached to the structure On any benzene ring in, that is, L 3 can be connected to In any position shown by 1, 2, 3, 4, a, b, c, d, for example, when L 3 is connected to the benzene ring corresponding to R 2,
  • the structure can include It should be understood that when L 3 is connected to the benzene ring corresponding to R 1 , n 1 is selected from 0, 1, 2 or 3, and when L 3 is connected to the benzene ring corresponding to R 2 , n 2 is selected from 0 , 1, 2 or 3.
  • the group L 3 is optionally connected to the fused ring.
  • the group L 3 can be attached to any position of the two naphthalene rings.
  • "-(Ad)q” means that with There are a total of q Ad connected in the structure.
  • Ad can be connected to L 1 , L 2 and L 3 (L 1 , L 2 and L 3 are not single bonds), can also be connected to Ar 1 and Ar 2 , or can be connected to The benzene ring structure shown (that is, connected to any position shown in 1, 2, 3, 4, a, b, c, d), R 1 , R 2 and Z.
  • Ad when there is a substituted group, Ad can be attached to the main body of the group or to a substituent.
  • Ar 1 is a heteroaryl substituted aryl group
  • Ad may be attached to the aryl main body, or attached to the heteroaryl group as a substituent.
  • each q" is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine", and its meaning is:
  • formula Q-1 represents q" substituents on the benzene ring R", each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 means that each benzene ring of biphenyl has q "substituents R" and two benzene rings The number of substituents q" of R" on the above can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.
  • the terms “optional” and “optionally” mean that the event or environment described later can but need not occur, and the description includes occasions where the event or environment occurs or does not occur.
  • “optionally, two adjacent substituents ⁇ form a ring;” means that these two substituents can form a ring but do not necessarily form a ring, including: the situation where two adjacent substituents form a ring and two A situation where adjacent substituents do not form a ring.
  • 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
  • substituted or unsubstituted aryl group refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc can be, for example, deuterium, halogen group, substituted or unsubstituted heteroaryl, substituted or unsubstituted aryl, trialkylsilyl, triarylsilyl, alkyl, haloalkyl, etc.
  • substituent R C itself is selected from substituted or unsubstituted heteroaryl, substituted or unsubstituted aryl, it means that the substituent Rc is selected from heteroaryl, substituted heteroaryl, aryl, and substituted aryl. .
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is selected from a substituted arylene group having 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 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.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthryl, pyrenyl, benzofluoranthene, Base etc.
  • the arylene group referred to refers to a divalent group formed by further losing one hydrogen atom of an aryl group.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • 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.
  • a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof.
  • the heteroatom may be at least one of B, O, 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 through 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, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofur
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings conjugated through carbon-carbon bonds.
  • System type of heteroaryl In this application, the involved heteroarylene group refers to a divalent group formed by the heteroaryl group further losing one hydrogen atom.
  • the substituted heteroaryl group can be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, ring Alkyl, 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.
  • any two adjacent substituents may include two substituents on the same atom, and may also include two adjacent atoms each having A substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom to which they are connected together; when two adjacent atoms each have a substituent When, these two substituents can be fused to form a ring.
  • 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 its meaning includes the following formula (f -1) Any possible connection mode shown in formula (f-10).
  • the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage 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'-4).
  • the non-positional 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 connected at any possible position in the ring system.
  • the substituent R'represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and its meaning includes the following formula (Y-1) to Any possible connection mode shown in formula (Y-7).
  • the alkyl group having 1 to 10 carbon atoms may include a straight chain alkyl group having 1 to 10 carbon atoms and a branched chain alkyl group having 3 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1, 2. , 3, 4, 5, 6, 7, 8, 9, 10.
  • alkyl groups having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isoamyl Base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • the halogen group may include fluorine, iodine, bromine, chlorine and the like.
  • the number of carbon atoms of the aryl group having 6 to 20 carbon atoms is, for example, 6 (phenyl), 10 (naphthyl), 12 (for example, biphenyl), 14, 15, 16, and the like.
  • 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.
  • trialkylsilyl groups having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • cycloalkyl groups having 3 to 10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
  • the cycloalkyl group having 5 to 10 carbon atoms may be, for example, a cyclopentyl group or a cyclohexyl group.
  • the organic compound has a structure shown in any one of Formula 2-1 to Formula 2-12:
  • R 1 'and R 2 ' are the same or different, and are each independently selected from deuterium, halogen groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, and It is a 3-12 trialkylsilyl group, a substituted or unsubstituted aryl group with 6-20 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-20 carbon atoms; R 1 'and R 2
  • the substituents in ' are each independently selected from deuterium, fluorine, trialkylsilyl groups having 3-7 carbon atoms, cycloalkyl groups having 5-10 carbon atoms, and haloalkyl groups having 1-4 carbon atoms , Alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, n 1 'represents the number of R 1 ', n 2 ' represents the number of R 2 '; n 1 ' And
  • the entire structure shown in Formula I includes at most 3 Ad.
  • the organic compound has a structure shown in any one of Formula 3-1 to Formula 3-8:
  • Formula 3-1 In Formula 3-1, Formula 3-2, and Formula 3-6, each has and only one Ad; in Formula 3-3, Formula 3-4, and Formula 3-7, each has and only two Ad, and Formula 3- 5. In formulas 3-8, there are only three Ad.
  • Ad can be 1-adamantyl
  • Ad can also be 2-adamantyl
  • Ad is 1-adamantyl.
  • X 1 , X 2 and X 3 are not N at the same time, for example , two of X 1 , X 2 and X 3 are N, or X 1 , X 2 and X 3 are One is N. In other embodiments, X 1 , X 2 and X 3 are N at the same time.
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from the group consisting of the groups represented by the following formula i-1 to formula i-15:
  • M 1 is selected from a single bond or
  • G 1 to G 5 are each independently selected from N or C(J 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(J 1 ) , Any two J 1s are the same or different;
  • G 6 to G 13 are each independently selected from N or C(J 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(J 2 ) , Any two J 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(J 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(J 3 ) , Any two J 3 are the same or different;
  • G 24 to G 33 are each independently selected from N or C(J 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(J 4 ) , Any two J 4 are the same or different;
  • Z 1 is selected from hydrogen, deuterium, halogen group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, carbon atom A cycloalkyl group having 3-10, an alkoxy group having 1-10 carbon atoms, an alkylthio group having 1-10 carbon atoms, and a triarylsilyl group having 18-24 carbon atoms;
  • Z 2 to Z 9 and Z 21 are each independently selected from: hydrogen, deuterium, halogen groups, trialkylsilyl groups having 3 to 12 carbon atoms, alkyl groups having 1 to 10 carbon atoms, and the number of carbon atoms It is a haloalkyl group having 1 to 10, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and a carbon number of 1 to 10 alkylthio groups, heteroaryl groups having 3 to 18 carbon atoms;
  • Z 10 to Z 20 and J 1 to J 4 are each independently selected from: hydrogen, deuterium, halogen groups, trialkylsilyl groups having 3 to 12 carbon atoms, alkyl groups having 1 to 10 carbon atoms, C1-C10 haloalkyl group, C3-C10 cycloalkyl group, C1-C10 alkoxy group, C1-C10 alkylthio group, C1-C10 Is an aryl group having 6 to 18, a heteroaryl group having 3 to 18 carbon atoms; optionally, any two adjacent Z 19 form a ring; optionally, any two adjacent Z 20 form a ring;
  • h 1 ⁇ h 21 are represented by h k
  • Z 1 ⁇ Z 21 are represented by Z k
  • k is a variable, representing any integer from 1 to 21
  • h k is the number of substituents Z k ; wherein, when k is selected from 5 Or when 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected When 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 Or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two Z k are the same or different;
  • K 1 is selected from O, S, N (Z 22 ), C (Z 23 Z 24 ), Si (Z 23 Z 24 ); wherein, Z 22 , Z 23 , and Z 24 are each independently selected from: the number of carbon atoms is 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 23 and Z 24 are mutually Connect to form a saturated or unsaturated ring with 3 to 15 carbon atoms with the atoms that are connected to them in common;
  • K 2 is selected from a single bond, O, S, N (Z 25 ), C (Z 26 Z 27 ), Si (Z 26 Z 27 ); wherein, Z 25 , Z 26 , and Z 27 are each independently selected from: carbon An aryl group having 6 to 18 atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or the above-mentioned Z 26 and Z 27 is 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.
  • J 2 to J 4 can be represented by J j , where j is a variable and represents 2, 3, or 4.
  • J j refers to J 2 . It should be appreciated that, when not connected to the positioning linkage C (J j) a, C (J j) in the absence of J j.
  • formula i-13 when When connected to G 12 , G 12 can only represent the C atom, that is, the structure of formula i-13 is specifically:
  • the following refers to the formula j-10 to formula j-12 of L 1 to L 3, when When connected to Q (e.g., Q 1 ) of each C-containing group (e.g., C(J 5 )), Q represents a C atom.
  • the ring formed by connecting two groups in each group may be saturated or unsaturated with 3 to 15 carbon atoms.
  • the ring For example, in formula i-10, when K 2 and M 1 are both single bonds, Z 19 is hydrogen, and K 1 is C (Z 23 Z 24 ), Z 23 and Z 24 are connected to each other to share them When the connected atoms form a 5-membered ring, the formula i-10 is Similarly, formula i-10 can also represent That is, Z 23 and Z 24 are connected to each other to form a partially unsaturated 13-membered ring with the atoms with which they are commonly connected.
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heterocyclic groups having 5 to 20 carbon atoms.
  • Aryl is the same or different, and is each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heterocyclic groups having 5 to 20 carbon atoms.
  • Ar 1 and Ar 2 are the same or different, and each is independently selected from the substituted or unsubstituted group V 1 , and the unsubstituted group V 1 is selected from the group consisting of the following groups:
  • the substituted group V 1 has one or more substituents, and the substituents are independently selected from deuterium, fluorine, alkyl groups having 1 to 4 carbon atoms, and fluoroalkyl groups having 1 to 4 carbon atoms ( For example, trifluoromethyl), trialkylsilyl groups with 3-7 carbon atoms, alkoxy groups with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, cyclopentyl, ring Hexyl, pyridyl, phenyl.
  • the number of substituents is greater than 1, the substituents are the same or different.
  • two adjacent substituents can be fused to form a ring.
  • At least one of Ar 1 and Ar 2 is selected from substituted or unsubstituted
  • the substituent is phenyl.
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from the group consisting of the following groups:
  • L 1 , L 2 and L 3 are the same or different, and are each independently a single bond, or are selected from the group consisting of groups represented by formula j-1 to formula j-12:
  • M 2 is selected from a single bond or Represents a chemical bond
  • Q 1 to Q 5 are each independently selected from N or C(J 5 ), and at least one of Q 1 to Q 5 is selected from N; when two or more of Q 1 to Q 5 are selected from C(J 5 ) , Any two J 5s are the same or different;
  • Q 6 to Q 13 are each independently selected from N or C(J 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(J 6 ) , Any two J 6 are the same or different;
  • Q 14 to Q 23 are each independently selected from N or C(J 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C(J 7 ) , Any two J 7s are the same or different;
  • E 1 to E 14 and J 5 to J 7 are each independently selected from: hydrogen, deuterium, halogen group, group B, trialkylsilyl group having 3 to 12 carbon atoms, and 1 to 10 carbon atoms Alkyl group, haloalkyl group having 1-10 carbon atoms, alkenyl group having 2-6 carbon atoms, cycloalkyl group having 3-10 carbon atoms, heterocycloalkyl group having 2-10 carbon atoms , Alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, arylthio with 6-18 carbon atoms, carbon A triarylsilyl group with 18-24 atoms; group B is selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 20 carbon atoms, The substituents in group B are selected from alkyl groups with 1 to 4 carbon
  • E r represents any integer of 1 to 14, E r E r represents the number of substituents; when r is selected from 1,2, When 3, 4, 5, 6, 9, 13, or 14, e r is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, e r is selected from 1, 2, 3, 4, 5 or 6; when r is 12, e r is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, e r is selected from 1, 2, 3, 4, 5, 6 , 7 or 8; when e r is greater than 1, any two E r are the same or different;
  • K 3 is selected from O, S, Se, N (E 15 ), C (E 16 E 17 ), Si (E 16 E 17 ); wherein, E 15 , E 16 , and E 17 are each independently selected from: carbon atoms An aryl group having 6 to 20, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a carbon number of 2 to 10 heterocycloalkyl, or E 16 and E 17 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms;
  • K 4 is selected from a single bond, O, S, Se, N (E 18 ), C (E 19 E 20 ), Si (E 19 E 20 ); wherein, E 18 to E 20 are each independently selected from: carbon atoms An aryl group having 6 to 20, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a carbon number of 2 to The heterocycloalkyl group of 10, or E 19 and E 20 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms.
  • L 1 , L 2 and L 3 are the same or different, and are each independently a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, or a carbon atom The number is 3-30 substituted or unsubstituted heteroarylene.
  • L 1 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;
  • L 2 and L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 20 carbon atoms Aryl.
  • L 1 is selected from the group consisting of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terylene Phenyl, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted carbazolylidene, substituted or unsubstituted dibenzofuran Group, substituted or unsubstituted dibenzothienylene group, substituted or unsubstituted pyridylene group; the substituents in L 1 are each independently selected from the group C, deuterium, fluorine, and those with 1-4 carbon atoms Alkyl groups, trialkylsilyl groups with 3-7 carbon atoms, cycloalkyl groups with
  • L 1 is a substituted or unsubstituted phenylene group, and the substituent is selected from an arylene group having 6-15 carbon atoms and a heteroarylene group having 5-18 carbon atoms.
  • substituents include, but are not limited to, phenyl, naphthyl, biphenyl, pyridyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazide Azole and so on.
  • L 2 and L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted phenylene group.
  • L 1 is a single bond, or a substituted or unsubstituted group T 1 , and the unsubstituted group T 1 is selected from the group consisting of the following groups:
  • the substituted group T 1 has one or more substituents, and the substituents in the substituted group T 1 are independently selected from deuterium, fluorine, alkyl groups with 1-4 carbon atoms, and the number of carbon atoms Is an alkoxy group having 1-4, an alkylthio group having 1-4 carbon atoms, a fluoroalkyl group having 1-4 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, and the number of carbon atoms is 3-7 trialkylsilyl, naphthyl. When the number of substituents is greater than 1, the substituents are the same or different.
  • L 1 is selected from a single bond or selected from the group consisting of the following groups:
  • L 2 is selected from a single bond, a substituted or unsubstituted group T 2 , and the unsubstituted group T 2 is selected from the group consisting of the following groups:
  • the substituted group T 2 has one or two or more substituents, and the substituents in the substituted group T 2 are independently selected from deuterium, fluorine, alkyl groups having 1 to 4 carbon atoms, and the number of carbon atoms Is an alkoxy group having 1-4, an alkylthio group having 1-4 carbon atoms, a fluoroalkyl group having 1-4 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, and the number of carbon atoms is 3-7 trialkylsilyl, phenyl. When the number of substituents is greater than 1, the substituents are the same or different.
  • L 2 is selected from a single bond or from the group consisting of the following groups:
  • L 3 is a single bond, or a substituted or unsubstituted group T 3 , and the unsubstituted group T 3 is selected from the group consisting of the following groups:
  • the substituted group T 3 has one or more than two substituents, and the substituents in the substituted group T 3 are independently selected from deuterium, fluorine, alkyl groups with 1 to 4 carbon atoms, and the number of carbon atoms Is an alkoxy group having 1-4, an alkylthio group having 1-4 carbon atoms, a fluoroalkyl group having 1-4 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, and the number of carbon atoms is 3-7 trialkylsilyl groups. When the number of substituents is greater than 1, the substituents are the same or different.
  • L 3 is selected from a single bond or selected from the group consisting of the following groups:
  • R 1 and R 2 are the same or different, and are each independently selected from deuterium, fluorine, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, carbon atom Alkoxy groups with 1-4, trialkylsilyl groups with 3-7 carbon atoms, group D, wherein group D is selected from substituted or unsubstituted aryl groups with 6-20 carbon atoms , Substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms, the substituents in group D are selected from deuterium, fluorine, alkyl groups with 1-4 carbon atoms, and those with 5-10 carbon atoms Cycloalkyl group, trialkylsilyl group having 3-7 carbon atoms.
  • any two adjacent R 1 can be condensed to form a ring
  • any two adjacent R 2 can be condensed to form a
  • R 1 and R 2 include, but are not limited to, deuterium, fluorine, cyano, methyl, tert-butyl, cyclopentyl, cyclohexyl, trimethylsilyl, trifluoromethyl, phenyl , Naphthyl, biphenyl, pyridyl, dibenzofuranyl, substituted phenyl, substituted naphthyl, substituted biphenyl; and, in substituted phenyl, substituted naphthyl, substituted biphenyl In the group, the substituent may be deuterium, fluorine, cyano, methyl, tert-butyl, trimethylsilyl, trifluoromethyl, and the like.
  • R 3 and R 4 are the same or different, and are each independently selected from an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, or 3 to 12 carbon atoms.
  • the heteroaryl group or the above-mentioned R 3 and R 4 can form a saturated or unsaturated ring with 5-15 carbon atoms together with the atoms to which they are connected together.
  • Specific examples of R 3 and R 4 include, but are not limited to, methyl, ethyl, n-propyl, phenyl and the like.
  • R 5 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, and the substituents in R 5 are selected from From deuterium, fluorine, C1-4 alkyl groups, C5-10 cycloalkyl groups, and C3-7 trialkylsilyl groups.
  • R 5 include, but are not limited to, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, substituted phenyl, substituted naphthyl, substituted biphenyl
  • the substituent may be deuterium, fluorine, cyano, methyl, tert-butyl, trimethylsilyl, trifluoromethyl Wait.
  • Ad connected to it, and there is an Ad connected to it Selected from the group consisting of the following groups:
  • the structure of L 1 , L 2 , Ar 1 and Ar 2 does not include
  • L 3 may be a phenylene group.
  • the organic compound in the organic compound, at least one of L 1 , L 2 and L 3 is X 1 , X 2 and X 3 are all N.
  • the application of the organic compound to the red light device can further improve the performance of the device.
  • organic compound is selected from the group consisting of the following 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 invention 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, including an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; the functional layer includes the organic compound described in the first aspect of the present application .
  • the organic compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the efficiency characteristics and lifetime characteristics of electronic components.
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound.
  • the organic light-emitting layer may include a host material and a guest material, wherein the host material includes the organic compound of the present application.
  • the electronic component is an organic electroluminescent device, such as a green light device, a blue light device, or a red light device.
  • the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, and an electron transport layer 340 which are sequentially stacked. And the 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 metal and oxide such as ZnO:Al or SnO 2 :Sb; or conductive polymer 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 first hole transport layer 321 and the second hole transport layer 322 respectively include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers and carbazole-linked triarylamines. Compounds or other types of compounds.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, and may also include a host material and a guest material.
  • the host material of the organic light-emitting layer may contain the organic compound of the present application.
  • the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy. To the host material, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the guest 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 for this. limit.
  • the organic electroluminescent device is a green light device, wherein the organic light-emitting layer includes a host material and a guest material, and the host material is a dual-host light-emitting material, that is, includes a p-type host Materials and n-type host materials, the organic compound of the present application may be, for example, n-type host materials.
  • the organic electroluminescent device is a red light device.
  • 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 340 may be composed of ET-1 (the structure is shown in Table 7) and LiQ.
  • the electron transport layer 340 may be composed of DBimiBphen and LiQ together.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates the 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 a cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first 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 HAT-CN, 1T-NATA, NATA, or NPAPF.
  • 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 LiQ, Yb, or a combination including Mg and LiF.
  • 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 an electronic device 400, which includes the above-mentioned organic electroluminescent device.
  • the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • the compounds of the synthesis method not mentioned in this application are all raw materials obtained through commercial channels.
  • magnesium flakes (2.9 g, 120 mmol) and 30 mL of tetrahydrofuran (THF) were added to the three-necked flask.
  • the temperature of the system was raised to 80° C., and iodine (0.6 g, 2.4 mmol) and 4-bromobis were added to the system.
  • Benzofuran (30.0g, 120mmol) was completely dissolved in 30mL of THF solvent, and slowly dripped into the system within 30min, and the temperature was controlled at 80°C during the dripping process. After the dropwise addition is completed, the reaction is stirred at 80°C for 2h to obtain a mixed solution.
  • magnesium flakes (1.52 g, 63.7 mmol) and 30 mL of THF were added to the three-necked flask, the temperature of the system was raised to 80° C., and iodine (0.32 g, 1.26 mmol) was added to the system.
  • the compound 4-bromodibenzofuran (15.73g, 63.7mmol) was completely dissolved in 30mL of THF solvent, and slowly dripped into the system within 30min, and the temperature was controlled at 80°C during the dripping process. After the dropwise addition is completed, the reaction is stirred at 80°C for 2h to obtain a mixed solution.
  • the intermediate aI-1 (20.13 g, 63.7 mmol) dissolved in 40 mL of THF was added dropwise to the mixed solution, and the reaction was terminated after stirring for 3 hours to obtain a reaction solution.
  • toluene 200 mL was added to extract the reaction solution, the organic phases were combined, the organic layer was dried with anhydrous magnesium sulfate, filtered, and concentrated by distillation under reduced pressure; the crude product was purified by silica gel column chromatography, and methanol was recrystallized and filtered to obtain a solid intermediate a -II-1 (22.5 g, yield: 79%).
  • each raw material A is used to replace the raw material bromobenzene in the process of preparing intermediate sub B-1.
  • the structure of raw material A, the synthesized target intermediate and its yield are shown in Table 1.
  • the intermediates sub A-6 (10.0g, 16.4mmol), sub B-1 (4.7g, 16.4mmol), tetrakistriphenylphosphine palladium (0.9g, 0.8mmol), potassium carbonate (4.9g, 36.0mmol) , Tetrabutylammonium bromide (0.05g, 0.16mmol), toluene (80mL), ethanol (40mL) and deionized water (20mL) were added to a three-necked flask, heated to 75-80°C under nitrogen protection, heated under reflux and stirred for 8h .
  • intermediate sub AX the intermediates sub A-7 to sub A-11 (hereinafter collectively referred to as intermediate sub AX) were synthesized.
  • the difference is , Replace phenylboronic acid in step 2) with raw material D, and the yield of the obtained intermediate and the final step are shown in Table 4.
  • intermediate a-II-7 is used instead of preparation in step 2)
  • the raw material 4-bromodibenzofuran in the intermediate a-II-1 was used to obtain the intermediate sub A-12 (13.0 g, yield 55%).
  • step 5 of Preparation Example 1 to prepare compound 100.
  • the difference is that sub A-12 is used instead of intermediate sub A-1 in Preparation Example 1, and the raw material sub B-5 is used instead of sub B-1 in Preparation Example 1. , Thereby obtaining compound 100 (9.5 g, yield 57%).
  • Mass spectrum: m/z 776.32 [M+H] + .
  • Step 2 Refer to the method of Preparation Example 21 (Step 2)-Step 4)) to synthesize the compounds shown in Table 5 below, except that the raw material E is used to replace the raw material 6-bromo-2-iodo dibenzofuran in step 2). F replaces the intermediate 1-1 in step 2), and the intermediate sub B-5 in step 4) is replaced by each intermediate sub BI.
  • the main raw materials used, the synthesized compound, and the yield and mass spectrum of the last step The characterization is shown in Table 5.
  • Step 2) of Preparation Example 21 to synthesize intermediate a-II-12 except that 4-iodo-2-bromo-dibenzofuran is used instead of 6-bromo-2-iodo-dibenzofuran to obtain Intermediate a-II-12 (10 g, yield 43%).
  • step 5) in Preparation Example 1 the compounds in Table 6 were synthesized, except that the intermediate sub AI synthesized above was used to replace the intermediate sub A-1, and the intermediate a-II-11 to the intermediate a-II- were used. One of 13 replaces the intermediate sub B-1, thereby synthesizing the compound.
  • the main raw materials and compounds used and their yields and mass spectrum results are shown in Table 6.
  • the NMR data of compound 354 are: 1 HNMR (400MHz, CD 2 Cl 2 ) ⁇ (ppm): 8.87 (d, 1H), 8.80 (d, 1H), 8.62 (s, 1H), 8.23 to 8.22 (d, 2H) ), 8.07(m,3H),7.75(d,1H),7.66(d,1H),7.61-7.51(m,7H),7.45-7.37(m,4H),2.09(s,3H),1.99( s, 6H), 1.82-1.75 (m, 6H).
  • NMR data of compound 365 1 H NMR (400MHz, CD 2 Cl 2 ) ⁇ (ppm): 8.86-8.82 (d, 2H), 8.78-8.76 (d, 1H), 8.50-8.47 (d, 1H), 8.40 -8.38(d,1H),8.30-8.27(m,3H),8.05-8.03(d,1H),7.98-7.96(d,1H),7.77-7.75(d,1H),7.68-7.52(m, 8H), 7.49-7.46 (d, 2H), 7.3-7.30 (m, 1H), 2.13 (s, 3H), 1.95 (s, 6H), 1.82-1.75 (m, 6H).
  • NMR data of compound 384 1 HNMR (400MHz, CD 2 Cl 2 ) ⁇ (ppm): 8.87 (s, 1H), 8.79 (s, 1H), 8.77-8.75 (d, 1H), 8.60-8.57 (m, 2H),8.35-8.33(d,1H),8.25-8.21(d,1H),8.05-8.03(d,1H),7.86-7.83(d,1H),7.60-7.56(m,4H),7.50- 7.41 (m, 9H), 7.10-7.06 (m, 2H), 2.12 (s, 3H), 1.96 (s, 6H), 1.82-1.76 (m, 6H).
  • the anode is prepared by the following process: the thickness of the ITO is The ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process is used to prepare it into an experimental substrate with a cathode lap area, an anode and an insulating layer pattern, and it can be used Ultraviolet ozone and O 2 :N 2 plasma are used for surface treatment to increase the work function of the anode, and organic solvents are used to clean the surface of the ITO substrate to remove impurities and grease on the surface of the ITO substrate.
  • HIL Hole injection layer
  • NPB The first hole transport layer
  • HT-02 Vacuum evaporate HT-02 on the first hole transport layer to form a thickness of The second hole transport layer (HTL2).
  • GHp1 Compound 82: fac-Ir(ppy) 3 was co-evaporated at a film thickness ratio of 45%: 45%: 10% to form a thickness of The green light-emitting layer (EML).
  • EML green light-emitting layer
  • ET-1 and LiQ are mixed at a weight ratio of 1:1 and formed by evaporation
  • the electron transport layer (ETL), Yb is vapor-deposited on the electron transport layer to form a thickness of
  • the electron injection layer (EIL) then, magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a thickness of The cathode.
  • the thickness of the vacuum evaporation on the above cathode is CP-1, thus completing the manufacture of organic electroluminescent devices.
  • Example 8 Except that the compounds shown in Table 8 were used to replace the compound 82 in Example 1 when forming the light-emitting layer, the same method as in Example 1 was used to fabricate an organic electroluminescent device.
  • Example 1 Except that when forming the light-emitting layer, Compound C to Compound F shown in Table 7 were used instead of Compound 82 in Example 1, respectively, and an organic electroluminescence device was fabricated in the same manner as in Example 1.
  • Examples 1-14 prepared by using the compound of the present invention as the host material of the green light-emitting layer have the effect of improving the efficiency and lifetime of the device.
  • the compound of the present invention is used as an n-type luminescent material
  • the device efficiency and T95 lifetime of Examples 1-14 are compared with those of Comparative Examples 1-4 when compared with those of Comparative Examples 1-4.
  • the device efficiency is increased by at least 12.9%
  • the T95 lifetime is increased by at least 8.3%.
  • the anode is prepared by the following process: the thickness of the ITO is
  • the ITO substrate was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (T), and a photolithography process was used to prepare it into an experimental substrate with anode and cathode overlap areas and insulating layer patterns.
  • a photolithography process was used to prepare it into an experimental substrate with anode and cathode overlap areas and insulating layer patterns.
  • Use ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode.
  • Organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil on the surface of the ITO substrate.
  • HIL Hole injection layer
  • NPAPF NPAPF
  • HT-02 Vacuum evaporate HT-02 on the first hole transport layer to form a thickness of The second hole transport layer (HTL2).
  • GhP1 Compound 1: fac-Ir(ppy) 3 was co-evaporated at a film thickness ratio of 45%: 45%: 10% to form a thickness of The green light-emitting layer (EML).
  • EML green light-emitting layer
  • ET-1 and LiQ are mixed at a weight ratio of 1:1 and formed by evaporation Thick electron transport layer (ETL). Then the Mg:LiF is co-evaporated according to the film thickness ratio of 1:1 to form a thickness of The electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) were mixed at a vapor deposition rate of 1:9, and vacuum vapor-deposited on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • magnesium (Mg) and silver (Ag) were mixed at a vapor deposition rate of 1:9, and vacuum vapor-deposited on the electron injection layer to form a thickness of The cathode.
  • the thickness of the vacuum evaporation on the above cathode is CP-1, thus completing the manufacture of organic electroluminescent devices.
  • Example 21 Except that when forming the light-emitting layer, the compounds shown in Table 10 were used to replace the compound 352 in Example 21, respectively, an organic electroluminescence device was fabricated in the same manner as in Example 21.
  • Example 15-30 and Comparative Examples 5-9 Preparation of the resultant green organic electroluminescent device performance testing, the specific tests IVL performance of the device at 10mA / cm 2 is, lifetime of the device in the T95 20mA / cm 2 of The test is carried out under the conditions, and the test results are shown in Table 10.
  • Examples 15-30 prepared by using the compound of the present invention as the n-type host material of the green light-emitting layer have the effect of improving the efficiency and lifetime of the device.
  • the driving voltage is almost the same, the device efficiency is increased by at least 13.3%, and the T95 lifetime is increased by at least 10.5%.
  • the organic compound of the present application when used to prepare a green organic electroluminescent device, it can effectively extend the life of the organic electroluminescent device and greatly improve the luminous efficiency of the organic electroluminescent device.
  • the anode is prepared by the following process: the thickness of the ITO is
  • the ITO substrate manufactured by Corning
  • Using ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • HIL The hole injection layer
  • HTL1 The first hole transport layer
  • the second hole transport layer (HTL2).
  • the compound 362: RH-P: Ir(MDQ) 2 (acac) was co-evaporated at a ratio of 45%:55%:3% (evaporation rate) to form a thickness of Organic light-emitting layer (EML).
  • DBimiBphen and LiQ are mixed at a weight ratio of 1:1 and evaporated to form a thickness of The electron transport layer (ETL), and then vacuum evaporation of a layer of Yb on the electron transport layer to form a thickness of The electron injection layer (EIL);
  • magnesium (Mg) and silver (Ag) were mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a thickness of The cathode.
  • the thickness of the vapor deposited on the above cathode is CP-1, forming a capping layer (CPL), thereby completing the manufacture of organic light-emitting devices.
  • Example 31 Except that when the light-emitting layer was formed, the compound shown in Table 11 was used instead of the compound 362 in Example 31, and an organic electroluminescent device was fabricated in the same manner as in Example 31.
  • Example 31 Except that when the light-emitting layer was formed, the compound 362 in Example 31 was replaced with Compound G and Compound H, respectively, an organic electroluminescent device was fabricated in the same manner as in Example 31.
  • Examples 31-43 prepared by using the compound of the present invention as the n-type host material of the red light-emitting layer have the effect of improving the efficiency and lifetime of the device.
  • the driving voltage is equivalent, the device efficiency is increased by at least 13.4%, and the T95 lifetime is increased by at least 10.1%.
  • the organic compound of the present application when used in an organic electroluminescent device, it can effectively extend the life of the organic electroluminescent device and improve the luminous efficiency of the organic electroluminescent device.

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Abstract

本申请属于有机材料技术领域，涉及一种有机化合物以及使用其的电子元件和电子装置，该有机化合物具有如下式I所示的结构。本申请的有机化合物能提高电子元件的性能。

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5月12日递交的申请号为202010398845.6的中国专利申请以及2020年8月28日递交的申请号为202010889735.X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
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子元器件的应用范围越来越广泛。该类电子元器件通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括能量转化层、位于能量转化层与阳极之间的空穴传输层、位于能量转化层与阴极之间的电子传输层。
以有机电致发光器件为例，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。
目前，有机电致发光器件的使用过程中存在发光效率降低和寿命缩短等问题，导致有机电致发光器件的性能下降。
发明内容
针对现有技术存在的上述问题，本申请的目的在于提供一种有机化合物以及使用其的电子元件和电子装置，该有机化合物用于有机电致发光器件中，提高有机电致发光器件的性能。
为了实现上述目的，本申请提供一种有机化合物，所述有机化合物具有如下式I所示的结构：
Figure PCTCN2021093160-appb-000001
其中，Z选自O、S、C(R 3R 4)或N(R 5)、Si(R 3R 4)、Se，其中R 3、R 4和R 5相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-30的取代或未取代的芳基或者碳原子数为2-30的取代或未取代的杂芳基，或者上述R 3和R 4能够与它们共同连接的原子一起形成环；
X 1、X 2和X 3相同或不同，且各自独立地选自CH或N，且X 1、X 2和X 3中至少一个为N；
R 1和R 2相同或不同，且各自独立地选自氘、卤素基团、碳原子数为1-10的烷基、碳原子数 为3-10的环烷基、碳原子数为3-12的三烷基硅基、碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基、碳原子数为1-10的烷氧基；n 1表示R 1的个数，n 2表示R 2的个数；R 1和R 2以R i表示，n 1～n 2以n i表示，i为变量，表示1或2，n i各自独立地选自0、1、2、3或4；且当n i大于1时，任意两个n i相同或不同；任选地，任意两个相邻的R i形成环；
Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6-40的取代或未取代的芳基，或者碳原子数为2-30的取代或未取代的杂芳基；
L 1、L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-35的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
R 1～R 5、L 1～L 3和Ar 1～Ar 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、基团A、碳原子数为3-12的三烷基硅基、碳原子数为18-24的三芳基硅基、碳原子数为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2-10的杂环烷基、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的芳氧基、碳原子数为6-18的芳硫基、碳原子数为2-6的烯基；基团A选自碳原子数为3-20的取代或未取代的杂芳基或碳原子数为6-20的取代或未取代的芳基，基团A中的取代基选自氘、卤素基团、碳原子数为1-4的烷基；任选地，任意两个相邻的取代基形成环；
Ad表示金刚烷基，q选自1、2或3。
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的有机化合物。
本申请第三方面提供一种电子装置，包含本申请第二方面所述的电子元件。
本申请的有机化合物以氮杂苯为母核，周围连接芳香杂环基团，破坏分子的结晶性，避免了分子间的聚集。金刚烷通过与芳香性基团连接后再与母核连接这种结构引入到该分子结构中，所形成的刚性的非共轭结构有效打断不同功能基团的共轭和电子转移，并且大位阻基团的接入避免了化合物的聚集，避免共轭平面的直接堆积形成π聚集或激基缔合物，将该有机化合物应用到有机电致发光器件中，可以在保证器件具有较低驱动电压的同时，提高发光效率。另外，这种结构可以改善材料的成膜性能，同时使得整体的分子量和不对称性增强，提高分子的热稳定性。本申请的化合物具有好的成膜性和荧光量子效率，分子内包含的电子给体与电子受体可以增加轨道重叠、提高发光效率，并且分子内连接的芳香杂环基团有助于获得HOMO、LUMO空间分离的电荷转移态材料。据此，本申请的有机化合物用于有机电致发光器件的发光层时，可以有效地提升器件的器件效率，并延长有机电致发光器件的寿命。
附图说明
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、空穴传输层；321、第一空穴传输层；322、第二空穴传输层；330、有机发光层；340、电子传输层；350、电子注入层；400、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。
第一方面，本申请提供一种有机化合物，所述有机化合物具有如下式I所示的结构：
Figure PCTCN2021093160-appb-000002
其中，Z选自O、S、C(R 3R 4)、N(R 5)、Si(R 3R 4)、Se，其中R 3、R 4和R 5相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-30的取代或未取代的芳基或者碳原子数为2-30的取代或未取代的杂芳基，或者上述R 3和R 4能够与它们共同连接的原子一起形成环；
X 1、X 2和X 3相同或不同，且各自独立地选自CH或N，且X 1、X 2和X 3中至少一个为N；
R 1和R 2相同或不同，且各自独立地选自氘、卤素基团、碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为3-12的三烷基硅基、碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基、碳原子数为1-10的烷氧基；n 1表示R 1的个数，n 2表示R 2的个数；R 1和R 2以R i表示，n 1～n 2以n i表示，i为变量，表示1或2，n i各自独立地选自0、1、2、3或4；且当n i大于1时，任意两个n i相同或不同；任选地，任意两个相邻的R i形成环，例如任意两个相邻的R i形成苯环；
Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6-40的取代或未取代的芳基，或者碳原子数为2-30的取代或未取代的杂芳基；
L 1、L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-35的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
R 1～R 5、L 1～L 3和Ar 1～Ar 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、基团A、碳原子数为3-12的三烷基硅基、碳原子数为18-24的三芳基硅基、碳原子数为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2-10的杂环烷基、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的芳氧基、碳原子数为6-18的芳硫基、碳原子数为2-6的烯基；基团A选自碳原子数为3-20的取代或未取代的杂芳基或碳原子数为6-20的取代或未取代的芳基，基团A中的取代基选自氘、卤素基团、碳原子数为1-4的烷基；任选地，任意两个相邻的取代基形成环；
Ad表示金刚烷基，q选自1、2或3。
在本申请中，式I中，
Figure PCTCN2021093160-appb-000003
表示基团L 3可以连接在结构
Figure PCTCN2021093160-appb-000004
中的任意苯环上，即L 3可以连接在
Figure PCTCN2021093160-appb-000005
中的1、2、3、4、a、b、c、d所示的任意位置上， 举例来讲，当L 3连接在R 2所对应的苯环上时，
Figure PCTCN2021093160-appb-000006
的结构可以包括
Figure PCTCN2021093160-appb-000007
应当理解地是，当L 3连接在R 1对应的苯环上时，n 1选自0、1、2或3，当L 3连接在R 2对应的苯环上时，n 2选自0、1、2或3。另外，当
Figure PCTCN2021093160-appb-000008
的苯环上还包括形成的稠合环时，基团L 3还可选地连接在稠合的环上。举例来讲，当
Figure PCTCN2021093160-appb-000009
为
Figure PCTCN2021093160-appb-000010
时，基团L 3可连接在两个萘环的任意位置上。
在本申请中，式I中，“-(Ad)q”表示在
Figure PCTCN2021093160-appb-000011
和
Figure PCTCN2021093160-appb-000012
的结构上总共连接有q个Ad。其中，Ad可以连接在L 1、L 2和L 3(L 1、L 2和L 3不为单键)，也可以连接在Ar 1和Ar 2上，还可以连接在
Figure PCTCN2021093160-appb-000013
所示的苯环结构(即连接在1、2、3、4、a、b、c、d所示的任意位置上)、R 1、R 2和Z上。另外，上述各个基团中，当存在取代的基团时，Ad可以连接在基团主体上，也可以连接在取代基上，举例来讲，当Ar 1为杂芳基取代的芳基时，Ad可以连接在芳基主体上，也可以连接在作为取代基的杂芳基上。
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 PCTCN2021093160-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，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，两个相邻取代基××形成环；”意味着这两个取代基可以形成环但不是必须形成环，包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
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Rc例如可以为氘、卤素基团、取代或未取代的杂芳基、取代或未取代的芳基、三烷基硅基、三芳基硅基、烷基、卤代烷基等，其中取代基R C本身选自取代或未取代的杂芳基、取代或未取代的芳基时，是指取代基Rc选自杂芳基、取代的杂芳基、芳基、取代的芳基。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L 1选自碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。
在本申请中，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，联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021093160-appb-000015
基等。本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。
在本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。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、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以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-苯基咔唑基、N-吡啶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，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、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。
在本申请中，“任意两个相邻的取代基形成环”中，“任意两个相邻”可以包括同一个原子上具有两个取代基，还可以包括两个相邻的原子上分别具有一个取代基；其中，当同一个原子上 具有两个取代基时，两个取代基可以与其共同连接的该原子形成饱和或不饱和的环；当两个相邻的原子上分别具有一个取代基时，这两个取代基可以稠合成环。
本申请中，涉及的不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021093160-appb-000016
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 PCTCN2021093160-appb-000017
再举例而言，如下式(X')中所示地，式(X')所表示的菲基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2021093160-appb-000018
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，如下式(Y)中所示地，式(Y)所表示的取代基R'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 PCTCN2021093160-appb-000019
本申请中，碳原子数为1～10的烷基可以包括碳原子数1～10的直链烷基和碳原子数为3～10的支链烷基，碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1～10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
本申请中，卤素基团可以包括氟、碘、溴、氯等。
本申请中，碳原子数为6～20的芳基的碳原子数例如为6(苯基)、10(萘基)、12(例如联苯基)、14、15、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。
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、三乙基硅基等。
在本申请中，碳原子数为3～10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。碳原子数为5-10的环烷基例如可以为环戊基、环己基。
在一些实施方式中，所述有机化合物具有式2-1至式2-12中任意一项所示的结构：
Figure PCTCN2021093160-appb-000020
Figure PCTCN2021093160-appb-000021
其中，R 1'和R 2'相同或不同，且各自独立地选自氘、卤素基团、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3-12的三烷基硅基、碳原子数为6-20的取代或未取代的芳基、碳原子数为3-20的取代或未取代的杂芳基；R 1'和R 2'中的取代基各自独立地选自氘、氟、碳原子数为3-7的三烷基硅基、碳原子数为5-10的环烷基、碳原子数为1-4的卤代烷基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基，n 1'表示R 1'的个数，n 2'表示R 2'的个数；n 1'和n 2'各自独立地为0、1或2。
可选地，整个式I所示的结构中至多包括3个Ad。
在一些实施方式中，所述有机化合物具有式3-1至式3-8中任意一项所示的结构：
Figure PCTCN2021093160-appb-000022
Figure PCTCN2021093160-appb-000023
式3-1、式3-2、式3-6中，分别有且只有一个Ad；式3-3、式3-4、式3-7中，分别有且只有两个Ad，式3-5、式3-8中，有且只有三个Ad。
本申请中，Ad可以为1-金刚烷基
Figure PCTCN2021093160-appb-000024
也可以为2-金刚烷基
Figure PCTCN2021093160-appb-000025
可选地，Ad为1-金刚烷基。
本申请中，在一些实施方式中，X 1、X 2和X 3不同时为N，例如X 1、X 2和X 3中有两个为N，或者X 1、X 2和X 3中有一个为N。在另一些实施方式中，X 1、X 2和X 3同时为N。
本申请中，在一些实施方式中，Ar 1和Ar 2相同或不同，且各自独立地选自如下式i-1至式i-15所示基团所组成的组：
Figure PCTCN2021093160-appb-000026
其中，M 1选自单键或者
Figure PCTCN2021093160-appb-000027
G 1～G 5各自独立地选自N或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
G 6～G 13各自独立地选自N或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
G 14～G 23各自独立地选自N或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
G 24～G 33各自独立地选自N或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
Z 1选自氢、氘、卤素基团、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为18～24的三芳基硅基；
Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、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；
Z 10～Z 20、J 1～J 4各自独立地选自：氢、氘、卤素基团、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；任选地，任意两个相邻的Z 19形成环；任选地，任意两个相邻的Z 20形成环；
h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 23Z 24)；其中，Z 22、Z 23、Z 24各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 26Z 27)；其中，Z 25、Z 26、Z 27各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
式i-13至式i-15中，J 2至J 4可以以J j表示，其中的j为变量，表示2、3或4。举例来讲，当j为2时，J j是指J 2。应当理解地是，当不定位连接键连接到C(J j)上时，C(J j)中的J j不存在。例如，在式i-13中，当
Figure PCTCN2021093160-appb-000028
连接到G 12时，G 12只能表示C原子，即式i-13的结构具体为：
Figure PCTCN2021093160-appb-000029
同理，下文中涉及到L 1至L 3的式j-10至式j-12中，当
Figure PCTCN2021093160-appb-000030
连接到各个含C基团(例如C(J 5))的Q(例如Q 1)上时，Q表示C原子。
在本申请中，上述Z 23与Z 24、上述Z 26与Z 27两组中，每组中的两个基团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-10中，当K 2和M 1均为单键，Z 19为氢，且K 1为C(Z 23Z 24)时，Z 23与Z 24相互连接以与它们共同连接的原子形成5元环时，式i-10即为
Figure PCTCN2021093160-appb-000031
同样地，式i-10也可以代表
Figure PCTCN2021093160-appb-000032
即Z 23与Z 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。同理，下文中涉及到L 1至L 3的式j-8至式j-9中，E 16和E 17、E 19和E 20的每组中的两个基团相互连接所形成的环具有类似的解释，在此不再赘述。
可选地，Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6-25的取代或未取代的芳基，或者碳原子数为5-20的取代或未取代的杂芳基。
在一些实施方式中，Ar 1和Ar 2相同或不同，且各自独立地选自取代或未取代的基团V 1，未取代的基团V 1选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000033
取代的基团V 1中具有一个或两个以上取代基，取代基独立地选自氘、氟、碳原子数为1-4的烷基、碳原子数为1-4的氟代烷基(例如三氟甲基)、碳原子数为3-7的三烷基硅基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基、环戊基、环己基、吡啶基、苯基。当取代基的个数大于1时，取代基相同或不同，任选地，相邻的两个取代基可稠合成环。
还可选地，Ar 1和Ar 2中至少一个选自取代或未取代的
Figure PCTCN2021093160-appb-000034
取代基为苯基。
可选地，Ar 1和Ar 2相同或不同，且各自独立地选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000035
在一些实施方式中，L 1、L 2和L 3相同或不同，且各自独立地为单键，或者选自式j-1至式j-12所示的基团所组成的组：
Figure PCTCN2021093160-appb-000036
其中，M 2选自单键或者
Figure PCTCN2021093160-appb-000037
表示化学键；
Q 1～Q 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
Q 6～Q 13各自独立地选自N或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
Q 14～Q 23各自独立地选自N或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
E 1～E 14、J 5～J 7各自独立地选自：氢、氘、卤素基团、基团B、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2～6的烯基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、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的芳氧基、碳原子数为6～18的芳硫基、碳原子数为18-24的三芳基硅基；基团B选自碳原子数为6～20的取代或未取代的芳基、碳原子数为3～20的取代或未取代的杂芳基，基团B中的取代基选自碳原子数为1～4的烷基、氟、氘；任选地，任意两个相邻的E 11形成环；任选地，任意两个相邻的E 12形成环；
e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10 时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 16E 17)；其中，E 15、E 16、E 17各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 4选自单键、O、S、Se、N(E 18)、C(E 19E 20)、Si(E 19E 20)；其中，E 18至E 20各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 19和E 20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，可选地，L 1、L 2和L 3相同或不同，且各自独立地为单键、碳原子数为6-30的取代或未取代的亚芳基、或者为碳原子数为3-30的取代或未取代的亚杂芳基。
在一些实施方式中，L 1选自单键、碳原子数为6-30的取代或未取代的亚芳基、或者碳原子数为5-30的取代或未取代的亚杂芳基；L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-25的取代或未取代的亚芳基、或者碳原子数为3-20的取代或未取代的亚杂芳基。
在一些具体的实施方式中，L 1选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚咔唑基、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、取代或未取代的亚吡啶基；L 1中的取代基各自独立地选自基团C、氘、氟、碳原子数为1-4的烷基、碳原子数为3-7的三烷基硅基、碳原子数为5-10的环烷基；基团C选自碳原子数为6-15取代或未取代的芳基、碳原子数为5-15的取代或未取代的杂芳基，基团C中的取代基选自氘、氟、碳原子数为1-4的烷基。任选地，任意两个相邻的取代基形成环。
在另一些具体的实施方式中，L 1为取代或未取代的亚苯基，取代基选自碳原子数为6-15的亚芳基，碳原子数为5-18的亚杂芳基。取代基的具体实例包括但不限于，苯基、萘基、联苯基、吡啶基、9,9-二甲基芴基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基等。
在一些具体的实施方式中，L 2和L 3相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚咔唑基、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、取代或未取代的亚吡啶基；L 2和L 3中的取代基各自独立地选自氘、氟、碳原子数为1-4的烷基、碳原子数为3-7的三烷基硅基、碳原子数为5-10的环烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基。任选地，任意两个相邻的取代基形成环。
按照一种示例性的实施方式，L 1为单键，或者为取代或未取代的基团T 1，未取代的基团T 1选自如下基团所组成的组：
Figure PCTCN2021093160-appb-000038
其中，取代的基团T 1中具有一个或两个以上取代基，取代的基团T 1中的取代基独立地选自氘、氟、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的烷硫基、碳原子数为1-4的氟代烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基、萘基。取代基的个数大于1时，取代基相同或不同。
进一步可选地，L 1选自单键或者选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000039
按照一种示例性的实施方式，L 2选自单键、取代或未取代的基团T 2，未取代的基团T 2选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000040
其中，取代的基团T 2中具有一个或两个以上取代基，取代的基团T 2中的取代基独立地选自氘、氟、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的烷硫基、碳原子数为1-4的氟代烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基、苯基。取代基的个数大于1时，取代基相同或不同。
可选地，L 2选自单键或者选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000041
按照一种示例性的实施方式，L 3为单键，或者为取代或未取代的基团T 3，未取代的基团T 3选自如下基团所组成的组：
Figure PCTCN2021093160-appb-000042
其中，取代的基团T 3中具有一个或两个以上取代基，取代的基团T 3中的取代基独立地选自氘、氟、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的烷硫基、碳原子数为1-4的氟代烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基。取代基的个数大于1时，取代基相同或不同。
可选地，L 3选自单键或者选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000043
在一些实施方式中，R 1和R 2相同或不同，且各自独立地选自氘、氟、碳原子数为1-4的烷基、 碳原子数为5-10的环烷基、碳原子数为1-4的烷氧基、碳原子数为3-7的三烷基硅基、基团D，其中，基团D选自碳原子数为6-20的取代或未取代的芳基、碳原子数为3-20的取代或未取代的杂芳基，基团D中的取代基选自氘、氟、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基。任选地，当n 1的个数大于1时，任意相邻的两个R 1可以稠合成环，当n 2的个数大于1时，任意相邻的两个R 2可以稠合成环。
本申请中，R 1和R 2的具体实例包括但不限于氘、氟、氰基、甲基、叔丁基、环戊基、环己基、三甲基硅基、三氟甲基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、取代的苯基、取代的萘基、取代的联苯基；并且，在取代的苯基、取代的萘基、取代的联苯基中，取代基可以为氘、氟、氰基、甲基、叔丁基、三甲基硅基、三氟甲基等。
在一些实施方式中，R 3和R 4相同或不同，且各自独立地选自碳原子数为1-4的烷基、碳原子数为6-12的芳基或者碳原子数为3-12的杂芳基，或者上述R 3和R 4能够与它们共同连接的原子一起形成碳原子数为5-15的饱和或不饱和环。R 3、R 4的具体实例包括但不限于，甲基、乙基、正丙基、苯基等。
在一些实施方式中，R 5选自碳原子数为6-20的取代或未取代的芳基、碳原子数为3-20的取代或未取代的杂芳基，R 5中的取代基选自氘、氟、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基。R 5的具体实例包括但不限于，苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、取代的苯基、取代的萘基、取代的联苯基；并且，在取代的苯基、取代的萘基、取代的联苯基中，取代基可以为氘、氟、氰基、甲基、叔丁基、三甲基硅基、三氟甲基等。
可选地，R 5上连接有一个Ad。
可选地，式3-2、式3-3、式3-4、式3-5、式3-7和式3-8中，
Figure PCTCN2021093160-appb-000044
各自独立地选自以下结构所组成的组：
Figure PCTCN2021093160-appb-000045
Figure PCTCN2021093160-appb-000046
进一步可选地，
Figure PCTCN2021093160-appb-000047
各自独立地选自以下结构所组成的组：
Figure PCTCN2021093160-appb-000048
Figure PCTCN2021093160-appb-000049
在一种实施方式中，
Figure PCTCN2021093160-appb-000050
上连接有一个Ad，且连接有一个Ad的
Figure PCTCN2021093160-appb-000051
选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000052
可选地，连接有一个Ad的
Figure PCTCN2021093160-appb-000053
选自以下基团所组成的组：
Figure PCTCN2021093160-appb-000054
Figure PCTCN2021093160-appb-000055
在该实施方式中，可选地，L 1、L 2、Ar 1和Ar 2的结构上不包括
Figure PCTCN2021093160-appb-000056
可选地，式3-6至式3-8中，L 3可以为亚苯基。
在一种优选的实施方式中，所述有机化合物中，L 1、L 2和L 3中的至少一个为
Figure PCTCN2021093160-appb-000057
X 1、X 2和X 3均为N，这种情况下，所述有机化合应用到红光器件中，能进一步改善器件的性能。
在本申请中，可选地，所述有机化合物选自如下化合物组成的组：
Figure PCTCN2021093160-appb-000058
Figure PCTCN2021093160-appb-000059
Figure PCTCN2021093160-appb-000060
Figure PCTCN2021093160-appb-000061
Figure PCTCN2021093160-appb-000062
Figure PCTCN2021093160-appb-000063
Figure PCTCN2021093160-appb-000064
Figure PCTCN2021093160-appb-000065
Figure PCTCN2021093160-appb-000066
Figure PCTCN2021093160-appb-000067
Figure PCTCN2021093160-appb-000068
Figure PCTCN2021093160-appb-000069
Figure PCTCN2021093160-appb-000070
Figure PCTCN2021093160-appb-000071
Figure PCTCN2021093160-appb-000072
Figure PCTCN2021093160-appb-000073
Figure PCTCN2021093160-appb-000074
Figure PCTCN2021093160-appb-000075
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，本发明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，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的有机化合物。
本申请所提供的有机化合物可以用于形成功能层中的至少一个有机膜层，以改善电子元件的效率特性和寿命特性。
具体的一种实施方式中，所述功能层包括有机发光层，所述有机发光层包括所述有机化合物。通常地，所述有机发光层可以包含主体材料和客体材料，其中，所述主体材料包含本申请的有机化合物。
按照本申请的一种实施方式中，电子元件为有机电致发光器件，例如为绿光器件、蓝光器件、红光器件。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、第一空穴传输层321、第二空穴传输层322、作为能量转化层的有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，第一空穴传输层321和第二空穴传输层322分别包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。有机发光层的主体材料可以含有本申请的有机化合物。进一步可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。按照一种具体的实施方式，所述有机电致发光器件为绿光器件，其中的有机发光层包括主体材料和客体材料，其中所述主体材料为双主体发光材料，即，包括p type型主体材料和n type型主体材料，本申请的有机化合物例如可以为n type型主体材料。按照另一种具体的实施方式，所述有机电致发光器件为红光器件。
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、恶二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种示例性实施方式中，电子传输层340可以由ET-1(结构如表7所示)和LiQ组成。在本申请的另一种示例性实施方式中，电子传输层340可以由DBimiBphen和LiQ共同组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向第一空穴传输层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HAT-CN、1T-NATA、NATA或NPAPF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LiQ、Yb或者包括Mg和LiF的组合物。
本申请第三方面提供一种电子装置包含本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所述电子装置为电子装置400，包括上述有机电致发光器件。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。
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。
下面结合合成实施例来具体说明本申请的有机化合物的合成方法。
使用以下方法合成本发明中化合物
制备例1.化合物1的制备
Figure PCTCN2021093160-appb-000076
1)中间体a-I-1的合成
在N 2保护下，向三口烧瓶中加入镁片(2.9g，120mmol)和四氢呋喃(THF)30mL，体系温度升至80℃，向体系中加入碘(0.6g，2.4mmol)、4-溴二苯并呋喃(30.0g，120mmol)在30mL的THF溶剂中溶解完全，30min内慢慢向体系中进行滴加，滴加过程中控制温度在80℃。滴加完毕，在80℃温度条件下搅拌反应2h，得到混合溶液。常温冷却后将溶解在80mL THF的2,4,6-三氯-1,3,5-三嗪(22.3g，120mmol)滴加到混合溶液中，搅拌3h后结束反应，得到反应溶液。反应结束后，加入甲苯(200mL)萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，减压蒸馏进行浓缩；粗品利用硅胶柱色谱进行提纯，甲醇重结晶过滤得到固体中间体a-I-1(24.2g，收率：63％)。
2)中间体a-II-1的合成
在N 2保护下，向三口烧瓶中加入镁片(1.52g，63.7mmol)和THF 30mL，体系温度升至80℃，向体系中加入碘(0.32g，1.26mmol)。化合物4-溴二苯并呋喃(15.73g，63.7mmol)在30mL的THF溶剂中溶解完全，30min内慢慢向体系中进行滴加，滴加过程中控制温度在80℃。滴加完毕，在80℃温度条件下搅拌反应2h，得到混合溶液。常温冷却后将溶解在40mL THF的中间体a-I-1(20.13g，63.7mmol)滴加到混合溶液中，搅拌3h后结束反应，得到反应溶液。反应结束后，加入甲苯(200mL)萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，减压蒸馏进行浓缩；粗品利用硅胶柱色谱进行提纯，甲醇重结晶过滤得到固体中间体a-II-1(22.5g，收率：79％)。
3)中间体sub A-1合成
将中间体a-II-1(12.5g，27.9mmol)，联硼酸频哪醇酯(8.5g，33.5mmol)、Pd(dppf)Cl 2(0.20g，0.27mmol)、KOAc(6.8g，69.7mmol)，加入1,4-二氧六环(100mL)在80℃温度条件下回流反应12h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥和浓缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体sub A-1(9.2g，收率：61％)。
4)sub B-1合成
Figure PCTCN2021093160-appb-000077
将1-金刚烷醇(50.0g，328.4mmol)、溴苯(51.6g，328.4mmol)、二氯甲烷(500mL)加入圆底烧瓶中，氮气保护下降温至-5℃至0℃，在-5℃至0℃下滴加三氟甲磺酸(73.9g，492.6mmol)，保温搅拌3h；向反应液中加入去离子水(300mL)水洗至pH＝7，加入二氯甲烷(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到白色固体sub B-1(53.1g，收率：55％)。
5)化合物1的制备
Figure PCTCN2021093160-appb-000078
将中间体sub A-1(9.0g，15.8mmol)、sub B-1(4.6g，15.7mmol)、四三苯基膦钯(0.4g,0.13mmol)、碳酸钾(5.5g，39.7mmol)、四丁基溴化铵(0.1g，0.4mmol)、甲苯(48mL)、乙醇(24mL)和去离子水(12mL)加入三口烧瓶中，氮气保护下升温至75-80℃，加热回流搅拌8h。反应结束后，将所得反应溶液冷却至室温，加入甲苯(100mL)萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯，得到固体化合物1(6.0g，收率61％)。质谱：m/z＝624.26[M+H] +。
中间体sub B-I的合成
参照制备例1中sub B-1的制备方法制备表1所列的中间体sub B-I，不同之处在于，使用各个原料A替代制备中间体sub B-1过程中的原料溴苯，所采用的原料A、合成的目标中间体结构及其产率如表1所示。
表1
Figure PCTCN2021093160-appb-000079
中间体sub A-I的合成
参照制备例1的中间体sub A-1的制备方法(步骤1)至步骤3))制备表2所列的中间体sub A-I，不同之处在于，使用各个原料B替代制备中间体a-I-1中的原料4-溴二苯并呋喃，使用各个原料C代替制备中间体a-II-1中的原料4-溴二苯并呋喃，所采用的主要原料、合成的目标中间体及其结构和最后一步产率如表2所示。
表2
Figure PCTCN2021093160-appb-000080
Figure PCTCN2021093160-appb-000081
Figure PCTCN2021093160-appb-000082
Figure PCTCN2021093160-appb-000083
制备例2至13
参照制备例1的方法合成表3中化合物，不同之处在于，使用上述合成的中间体sub A-I替代中间体sub A-1，中间体sub B-I替代中间体sub B-1；所采用的主要原料以及化合物的收率、结构及质谱表征结果如表3所示。
表3
Figure PCTCN2021093160-appb-000084
Figure PCTCN2021093160-appb-000085
Figure PCTCN2021093160-appb-000086
制备例15 化合物56的制备
Figure PCTCN2021093160-appb-000087
1)中间体a-III-1的制备
中间体a-II-1(30.0g，66.9mmol)，3.5-二溴苯硼酸频哪醇酯(24.2g，66.9mmol)、Pd 2(dba) 3 (0.6g，0.6mmol)、x-phos(0.6g，1.3mmol)，KOAc(14.4g，147.36mmol)加入到三口烧瓶中，加入1,4-二氧六环(300mL)氮气保护下升在80℃温度条件下回流反应8h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥和缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体a-III-1(26.4g，收率：61％)。
2)中间体a-IV-1的制备
将中间体a-III-1(26.0g，40.1mmol)、苯硼酸(4.8g，40.1mmol)、四三苯基膦钯(2.3g，2.0mmol)、碳酸钾(12.2g，88.3mmol)、四丁基溴化铵(0.1g，0.4mmol)、甲苯(240mL)、乙醇(120mL)和去离子水(60mL)加入三口烧瓶中，氮气保护下升温至75-80℃，加热回流搅拌15h。反应结束后，将所得反应溶液冷却至室温，加入甲苯(200mL)萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯，得到中间体a-IV-1(13.5g，收率：52％)。
3)中间体sub A-6的制备
将中间体a-IV-1(18.0g，27.9mmol)加入圆底烧瓶中，180mL的THF经过除水后加入到烧瓶中，用液氮将体系降温至-80℃至-90℃，开始滴加正丁基锂(1.78g,27.9mmol)，滴毕，保温1h。滴加硼酸三甲酯(3.2g,30.7mmol)，温度保持在-80℃至-90℃，滴毕，保温1h后，自然升至室温，反应结束，加入HCl的水溶液20mL(浓度为2.5mol/L)，搅拌0.5h。加入二氯甲烷和水进行分液萃取，有机相洗至中性pH＝7，合并有机相，无水MgSO 4干燥10min后，过滤，滤液旋干，用正庚烷打浆2次得到白色固体中间体sub A-6(11.2g，收率：66％)。
4)化合物56的制备
Figure PCTCN2021093160-appb-000088
将中间体sub A-6(10.0g，16.4mmol)、sub B-1(4.7g，16.4mmol)、四三苯基膦钯(0.9g，0.8mmol)、碳酸钾(4.9g，36.0mmol)、四丁基溴化铵(0.05g，0.16mmol)、甲苯(80mL)、乙醇(40mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下升温至75-80℃，加热回流搅拌8h。反应结束后，将所得反应溶液冷却至室温，加入甲苯(100mL)萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯，得到固体化合物56(9.16g，收率：72％)。质谱：m/z＝776.32[M+H] +。
制备例16-20
1)制备中间体sub A-7至sub A-11
按照制备例15中的中间体sub A-6的合成方法(步骤2)至步骤3))中合成中间体sub A-7至sub A-11(以下统称为中间体sub A-X)，不同的是，将步骤2)中的苯硼酸替换为原料D，所得中间体及最后一步收率如表4所示。
2)制备化合物
按照制备例15中化合物56(步骤4))的合成方法，制备表4中化合物，不同之处在于使用表4中所列的中间体sub A-X替代中间体sub A-6制备化合物，所合成的化合物及其最后一步收率和 质谱表征结果如表4所示。
表4
Figure PCTCN2021093160-appb-000089
制备例21.化合物100的制备
1)中间体1-1的制备
Figure PCTCN2021093160-appb-000090
将中间体sub B-1(35.0g,120.1mmol)加入圆底烧瓶中，630mL的THF经过除水后加入到烧瓶中，给体系用液氮降温至-80℃至-90℃，开始滴加正丁基锂(8.46g,132.1mmol)，滴毕，保温1h。滴加硼酸三甲酯(13.7g,132.1mmol)，温度保持在-80℃至-90℃，滴毕，保温1h后，自然升至室温，反应结束，加入HCl的水溶液100mL(浓度为2mol/L)，搅拌0.5h。加入二氯甲烷和水进行分液萃取，有机相洗至中性pH＝7，合并有机相，无水MgSO 4干燥10min后，过滤，滤液旋干，用正庚烷打浆2次得到得到白色固体中间体1-1(20.9g，收率68％)。
2)中间体a-II-7的制备
Figure PCTCN2021093160-appb-000091
将6-溴-2-碘二苯并呋喃(15.0g，40.2mmol)、中间体1-1(10.3g，40.2mmol)、四三苯基膦钯(2.3g，2.0mmol)、碳酸钾(12.2g，88.4mmol)和四丁基溴化铵(0.13g，0.4mmol)加入三口烧瓶中，甲苯(120mL)、乙醇(60mL)和去离子水(30mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌18h。冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色产物中间体a-II-7(11.6g，收率62％)。
3)中间体sub A-12的制备
Figure PCTCN2021093160-appb-000092
参照制备例1中中间体sub A-1的制备方法(步骤2)至步骤3))制备中间体sub A-12，不同之处在于，步骤2)中使用中间体a-II-7代替制备中间体a-II-1中的原料4-溴二苯并呋喃，从而获得中间体sub A-12(13.0g，收率55％)。
4)化合物100的制备
Figure PCTCN2021093160-appb-000093
参照制备例1的步骤5)制备化合物100，不同之处在于使用sub A-12替代制备例1中的中间体sub A-1，使用原料sub B-5替代制备例1中的sub B-1，从而得到化合物100(9.5g，收率57％)。质谱：m/z＝776.32[M+H] +。
制备例22-29
参照制备例21的方法(步骤2)-步骤4))合成下表5所示化合物，不同之处在于以原料E替代步骤2)中的原料6-溴-2-碘二苯并呋喃，原料F代替步骤2)中的中间体1-1，步骤4)中的中间体sub B-5由各中间体sub B-I进行代替，所采用的主要原料、所合成的化合物及最后一步收率和质谱表征如表5所示。
表5
Figure PCTCN2021093160-appb-000094
Figure PCTCN2021093160-appb-000095
制备例30-35
1)中间体a-II-11的制备
Figure PCTCN2021093160-appb-000096
参照制备例21中的步骤2)合成中间体a-II-11，不同的是，用3-溴-5-碘-1,1'-联苯替代6-溴-2-碘二苯并呋喃，从而获得中间体a-II-11(12g，收率54％)。
2)中间体a-II-11的制备
Figure PCTCN2021093160-appb-000097
参照制备例21中的步骤2)合成中间体a-II-12，不同的是，用4-碘-2-溴-二苯并呋喃替代6-溴-2-碘二苯并呋喃，从而获得中间体a-II-12(10g，收率43％)。
3)中间体a-II-13的制备
Figure PCTCN2021093160-appb-000098
将2-溴咔唑(15.0g，60.9mmol)、sub B-1(17.5g，60.9mmol)、Pd 2(dba) 3(0.5g，0.6mmol)、x-phos(0.6g，1.2mmol)、叔丁醇钠(11.7g，121.8mmol)、二甲苯(300mL)加入三口烧瓶中，氮气保护下升温至140℃，加热回流搅拌10h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体a-II-13(12.5g，收率45％)。
4)化合物合成
按照制备例1中的步骤5)合成表6的化合物，不同的是，用上述合成的中间体sub A-I替换中间体sub A-1，用中间体a-II-11至中间体a-II-13之一替换中间体sub B-1，从而合成化合物。所采用的主要原料和化合物及其收率和质谱结果如表6所示。
表6
Figure PCTCN2021093160-appb-000099
Figure PCTCN2021093160-appb-000100
制备例36.化合物358的制备
Figure PCTCN2021093160-appb-000101
1)将中间体a-I-1(30.0g，94.9mmol)、中间体1-1(19.4g，75.9mmol)、四三苯基膦钯(5.5g，4.7mmol)、碳酸钾(26.2g,189.8mmol)、四丁基溴化铵(0.6g,1.9mmol)、甲苯(240mL)、乙醇(120mL)和去离子水(60mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌15h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和(200mL)萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体sub A-25(23.3g，收率50％)。
2)将中间体sub A-25(22.0g，44.8mmol)、咔唑(5.0g，29.9mmol)、DMF(200mL)加入三口烧瓶中，氮气保护下降温至0℃，加入NaH(0.8g，32.8mmol)后自然升至室温。反应结束后，将所得反应溶液体系中加入水，过滤得到固体产物，用少量乙醇进行淋洗，粗品利用甲苯进行重结晶，得到化合物358(11.4g，收率78％)。质谱：m/z＝623.27[M+H] +。
制备例37.化合物33的制备
Figure PCTCN2021093160-appb-000102
1)将4-羟基苯硼酸(50.0g，362.5mmol)、1-溴金刚烷(77.9g，362.5mmol)、二氯甲烷(500mL)加入圆底烧瓶中，氮气保护下降温至-5至0℃，在该温度下滴加三氟甲磺酸(81.6g，543.8mmol)，保温搅拌3h后自然升至室温；向反应液中加入去离子水(300mL)水洗至pH＝7，加入二氯甲烷(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到白色固体中间体1-a-1(54.2g，收率55％)。
2)将中间体1-a-1(50.0g，183.6mmol)、溴苯(23.0g，146.9mmol)、四三苯基膦钯(4.2g，3.6mmol)、碳酸钾(50.7g，367.3mmol)、四丁基溴化铵(1.2g，3.6mmol)、甲苯(480mL)、乙醇(240mL)和去离子水(120mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌15h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体1-b-1(34.6g，收率62％)。
3)将中间体1-b-1(30.0g，98.5mmol)、吡啶(23.4g，295.6mmol)、二氯甲烷(300mL)加入三口烧瓶中，氮气保护下降温至-5℃，缓慢加入三氟甲磺酸酐(36.1g，128.1mmol)，然后在0℃进行保温2h后，再自然升至室温进行搅拌。反应结束后，将所得反应溶液加入盐酸水溶液(2mmol/L)，洗至弱酸性(ph＝5-6)体系，以二氯甲烷和水进行分液萃取，MgSO 4干燥有机相二氯甲烷中的水，过滤，浓缩得到所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯(二氯甲烷/正庚烷)，获得中间体1-c-1(34.4g，收率80％)。
4)将中间体1-c-1(20.0g，45.8mmol)，联硼酸频哪醇酯(17.4g，68.7mmol)、Pd(dppf)Cl 2([1,1'-双(二苯基膦基)二茂铁]二氯化钯，1.6g，2.3mmol)、KOAc(8.9g，91.6mmol)，加入1,4-二氧六环(200mL)在80℃温度条件下回流反应12h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥有机相中的水分，浓缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体1-d-1(11.5g，收率：61％)。
5)将中间体1-d-1(9.7g，23.4mmol)、a-II-1(10.0g，22.3mmol)、四三苯基膦钯(0.5g,0.4mmol)、碳酸钾(6.1g,44.6mmol)、四丁基溴化铵(0.07g,0.2mmol)、甲苯(80mL)、乙醇(40mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌12h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到化合物33(10.4g，收率67％)。质谱：m/z＝700.29[M+H] +。
制备例38.化合物354的制备
Figure PCTCN2021093160-appb-000103
按照制备例37中的步骤合成化合物354，不同的是，将步骤2)中的原料溴苯用3-溴吡啶替换，从而合成化合物354(4.1g，收率47％)，质谱：m/z＝701.28[M+H] +。
化合物354的核磁数据为： 1HNMR(400MHz,CD 2Cl 2)δ(ppm)：8.87(d,1H),8.80(d,1H),8.62(s,1H),8.23-8.22(d,2H),8.07(m,3H),7.75(d,1H),7.66(d,1H),7.61-7.51(m,7H),7.45-7.37(m,4H),2.09(s,3H),1.99(s,6H),1.82-1.75(m,6H)。
制备例39.化合物87的制备
Figure PCTCN2021093160-appb-000104
1)将4-溴-2-氯-1-苯氧基苯(50.0g，176.3mmol)，K 2CO 3(24.3g，176.3mmol)、Pd(OAc) 2(1.97g，8.81mmol)和乙酸(500mL)加入圆底烧瓶中，氮气保护下升温至120℃，在该温度下反应50h。向反应液中加入去离子水(300mL)水洗至pH＝7，加入二氯甲烷(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到白色固体中间体1-b-3(19.8g，收率40％)。
2)将中间体1-b-3(19.0g，67.5mmol)、1-1(18.1g，70.8mmol)、四三苯基膦钯(3.8g，3.3mmol)、 碳酸钾(18.6g，134.9mmol)、四丁基溴化铵(0.2g，0.6mmol)、甲苯(160mL)、乙醇(40mL)和去离子水(40mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌12h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到固体中间体1-c-3(18.1g，收率65％)。
3)将中间体1-c-3(18.0g，43.5mmol)，联硼酸频哪醇酯(16.6g，65.3mmol)、Pd(dppf)Cl 2(1.5g，2.1mmol)、KOAc(0.6g，108.0mmol)，加入1,4-二氧六环(200mL)在100℃温度条件下回流反应12h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥有机相中的水分和浓缩有机层，对所生成的化合物进行硅胶柱层析纯化及重结晶，获得中间体1-d-3(12.9g，收率：59％)。
4)将a-I-1(20.0g，63.2mmol)、3-联苯硼酸(18.7g，94.4mmol)、四三苯基膦钯(3.6g，3.1mmol)、碳酸钾(21.8g，158.1mmol)、四丁基溴化铵(0.2g，0.6mmol)、甲苯(160mL)、乙醇(40mL)和去离子水(40mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌12h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到固体中间体1-e-3(18.3g，收率67％)。
5)将中间体1-e-3(9.0g，20.7mmol)、1-d-3(11.5g，22.8mmol)、四三苯基膦钯(1.2g,1.0mmol)、碳酸钾(7.1g,51.8mmol)、四丁基溴化铵(0.06g,0.2mmol)、甲苯(80mL)、乙醇(40mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌11h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到化合物87(9.5g，收率59％)。质谱：m/z＝776.32[M+H] +。
制备例40.化合物365的制备
Figure PCTCN2021093160-appb-000105
1)将1-溴-4-碘萘(50.0g，150.1mmol)，4-二苯并呋喃硼酸(31.8g，150.1mmol)、四三苯基膦钯(1.7g，1.5mmol)、碳酸钾(41.5g，300.3mmol)和四丁基溴化铵(0.5g，1.5mmol)加入 三口烧瓶中，甲苯(400mL)、乙醇(200mL)和去离子水(100mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌18h。冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色产物中间体1-b-4(37.5g，收率67％)。
2)将中间体1-b-4(30.0g，80.3mmol)，联硼酸频那醇酯(30.6g，120.5mmol)、Pd(dppf)Cl 2(1.1g，1.6mmol)、KOAc(15.7g，160.7mmol)，加入1,4-二氧六环(300mL)在100℃温度条件下回流反应12h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥有机相中的水分和浓缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体1-c-4(21.9g，收率：65％)。
3)将2,4-二氯-6-苯基-1,3,5-三嗪(20.0g，88.4mmol)，中间体1-1(18.1g，70.7mmol)、四三苯基膦钯(2.0g，1.7mmol)、碳酸钾(24.4g，176.9mmol)加入三口烧瓶中，THF(80mL)去离子水(20mL)加入三口烧瓶中，氮气保护下升温至66℃，加热回流搅拌18h。冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色产物中间体1-e-4(20.2g，收率71％)。
4)将中间体1-e-4(15.0g，37.3mmol)、(16.5g，39.1mmol)、四三苯基膦钯(0.8g,0.7mmol)、碳酸钾(10.3g,74.6mmol)、四丁基溴化铵(0.1g,0.37mmol)、甲苯(120mL)、乙醇(60mL)和去离子水(30mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌10h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到化合物365(14.7g，收率60％)；质谱：m/z＝660.29[M+H] +。化合物365的核磁数据： 1H NMR(400MHz,CD 2Cl 2)δ(ppm)：8.86-8.82(d,2H),8.78-8.76(d,1H),8.50-8.47(d,1H),8.40-8.38(d,1H),8.30-8.27(m,3H),8.05-8.03(d,1H),7.98-7.96(d,1H),7.77-7.75(d,1H),7.68-7.52(m,8H),7.49-7.46(d,2H),7.3-7.30(m,1H),2.13(s,3H),1.95(s,6H),1.82-1.75(m,6H)。
制备例41.化合物367的制备
按照制备例40中的步骤合成化合物367，不同的是，将合成中间体1-b-4中的原料4-二苯并呋喃硼酸用二苯并呋喃-2-硼酸替换，从而合成化合物367(11.2g，收率55％)，质谱：m/z＝660.28[M+H] +。
制备例42.化合物384的制备
Figure PCTCN2021093160-appb-000106
1)将1-溴-4-氯萘(49.3g，204.4mmol)、对氟苯硼酸(26.0g，185.8mmol)、四三苯基膦钯(2.1g，1.8mmol)、碳酸钾(51.3g,371.6mmol)、四丁基溴化铵(0.6g,1.8mmol)、甲苯(400mL)、乙醇(200mL)和去离子水(100mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌15h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体1-a-5(31.0g，收率65％)。
2)将中间体1-a-5(30.0g，116.8mmol)，联硼酸频哪醇酯(35.6g，140.2mmol)、Pd(dppf)Cl 2([1,1'-双(二苯基膦基)二茂铁]二氯化钯(0.8g，1.2mmol)、KOAc(22.9g，233.7mmol)，加入1,4-二氧六环(300mL)在100℃温度条件下回流反应10h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥有机相中的水分，浓缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体1-b-5(23.6g，收率：58％)。
3)将中间体1-b-5(20.0g，57.4mmol)、2,4-二氯-6-(4-氟苯基)-1,3,5-三嗪(15.4g，63.1mmol)、四三苯基膦钯(0.6g,0.5mmol)、碳酸钾(15.8g,114.8mmol)、四丁基溴化铵(0.2g,0.5mmol)、甲苯(200mL)、乙醇(100mL)和去离子水(50mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌8h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体1-c-5(15.7g，收率64％)。
4)将中间体a-II-12(25.0g，54.6mmol)，联硼酸频哪醇酯(16.6g，65.5mmol)、Pd(dppf)Cl 2([1,1'-双(二苯基膦基)二茂铁]二氯化钯(0.4g，0.5mmol)、KOAc(10.7g，109.3mmol)，加入1,4-二氧六环(250mL)在100℃温度条件下回流反应14h。当反应结束时，使用CH 2Cl 2和水进行提取。利 用MgSO 4来干燥有机相中的水分，浓缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体1-d-5(17.9g，收率65％)。
5)将中间体1-c-5(12.0g，27.9mmol)、1-d-5(15.5g，30.7mmol)、四三苯基膦钯(0.3g,0.3mmol)、碳酸钾(7.7g,55.8mmol)、四丁基溴化铵(0.17g,0.5mmol)、甲苯(96mL)、乙醇(48mL)和去离子水(24mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌12h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到化合物384(11.8g，收率55％)。质谱：m/z＝772.31[M+H] +。化合物384的核磁数据： 1HNMR(400MHz,CD 2Cl 2)δ(ppm)：8.87(s,1H),8.79(s,1H),8.77-8.75(d,1H),8.60-8.57(m,2H),8.35-8.33(d,1H),8.25-8.21(d,1H),8.05-8.03(d,1H),7.86-7.83(d,1H),7.60-7.56(m,4H),7.50-7.41(m,9H),7.10-7.06(m,2H),2.12(s,3H),1.96(s,6H),1.82-1.76(m,6H)。
制备例43.化合物385的制备
Figure PCTCN2021093160-appb-000107
1)将1-溴-4-氯萘(49.3g，204.3mmol)、3-氰基苯硼酸(27.3g，185.8mmol)、四三苯基膦钯(2.1g，1.8mmol)、碳酸钾(51.3g,371.5mmol)、四丁基溴化铵(0.6g,1.8mmol)、甲苯(400mL)、乙醇(200mL)和去离子水(100mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌15h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体1-a-6(32.8g，收率67％)。
2)将中间体1-a-6(30.0g，113.8mmol)，联硼酸频哪醇酯(34.6g，136.5mmol)、Pd(dppf)Cl 2([1,1'-双(二苯基膦基)二茂铁]二氯化钯(0.8g，1.2mmol)、KOAc(22.3g，227.5mmol)，加入1,4-二氧六环(300mL)在100℃温度条件下回流反应10h。当反应结束时，使用CH 2Cl 2和水进行提取。利用MgSO 4来干燥有机相中的水分，浓缩有机层，对所生成的化合物进行硅胶柱及再结晶，获得中间体1-b-6(24.2g，收率：60％)。
3)将中间体1-b-6(15.0g，42.2mmol)、2,4-二氯-6-苯基-1,3,5-三嗪(10.0g，44.3mmol)、四三苯基膦钯(0.5g,0.4mmol)、碳酸钾(11.6g,84.4mmol)、四丁基溴化铵(0.1g,0.4mmol)、甲 苯(200mL)、乙醇(100mL)和去离子水(50mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌8h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到中间体1-c-6(10.7g，收率61％)。
5)将中间体1-c-6(10.0g，23.8mmol)、1-d-5(13.2g，26.2mmol)、四三苯基膦钯(0.3g,0.2mmol)、碳酸钾(6.6g,47.7mmol)、四丁基溴化铵(0.07g,0.2mmol)、甲苯(80mL)、乙醇(40mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌12h。反应结束后，将所得反应溶液冷却至室温，加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯(二氯甲烷/正庚烷)，得到化合物385(9.0g，收率50％)。质谱：m/z＝761.32[M+H] +。
有机电致发光器件制备及评估
实施例1
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2021093160-appb-000108
的ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阴极搭接区域、阳极以及绝缘层图案的实验基板，并可利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极的功函数，并采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。
在实验基板(阳极)上真空蒸镀1T-NATA以形成厚度为
Figure PCTCN2021093160-appb-000109
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀NPB，以形成厚度为
Figure PCTCN2021093160-appb-000110
的第一空穴传输层(HTL1)。
在第一空穴传输层上真空蒸镀HT-02，形成厚度为
Figure PCTCN2021093160-appb-000111
的第二空穴传输层(HTL2)。
接着在第二空穴传输层上，将GHp1：化合物82：fac-Ir(ppy) 3按照45％：45％：10％的膜厚比进行共同蒸镀，形成厚度为
Figure PCTCN2021093160-appb-000112
的绿色发光层(EML)。
将ET-1和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2021093160-appb-000113
的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021093160-appb-000114
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 PCTCN2021093160-appb-000115
的阴极。
此外，在上述阴极上真空蒸镀厚度为
Figure PCTCN2021093160-appb-000116
的CP-1，从而完成有机电致发光器件的制造。
实施例2-实施例14
除了在形成发光层时，以表8中所示的化合物分别替代实施例1中的化合物82以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例1-比较例4
除了在形成发光层时，以表7中所示的化合物C～化合物F分别替代实施例1中的化合物82以外，利用与实施例1相同的方法制作有机电致发光器件。
其中，在制备有机电致发光器件时，上述比较例与实施例所使用的部分材料的结构式如表7所示。
表7
Figure PCTCN2021093160-appb-000117
对实施例1-14和比较例1-4制备所得的绿色有机电致发光器件进行性能测试，具体在10mA/cm 2的条件下测试器件的IVL性能，T95器件寿命在20mA/cm 2的条件下进行测试，测试结果如表8。
表8
Figure PCTCN2021093160-appb-000118
Figure PCTCN2021093160-appb-000119
如表8中器件性能测试结果可知，将本发明化合物用作绿色发光层主体材料制备的实施例1-14与比较例1-4相比，具有提升器件效率和寿命的作用。具体而言，将本发明的化合物用作n type发光材料时的实施例1-14与比较例1-4相比，实施例1-14的器件效率与T95寿命较比较例1-4均有所提高，在保证具有较低的驱动电压的情况下，器件效率至少提升了12.9％，T95寿命至少提升了8.3％。
实施例15：绿色有机电致发光器件
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2021093160-appb-000120
的ITO基板切割成40mm(长)×40mm(宽)×0.7mm(T)的尺寸，采用光刻工序，将其制备成具有阳极、阴极搭接区域以及绝缘层图案的实验基板。并利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极的功函数。并可采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。
在实验基板(阳极)上真空蒸镀1T-NATA以形成厚度为
Figure PCTCN2021093160-appb-000121
的空穴注入层(HIL)，并在空穴注入层上真空蒸镀NPAPF，以形成厚度为
Figure PCTCN2021093160-appb-000122
的第一空穴传输层(HTL1)。
在第一空穴传输层上真空蒸镀HT-02，形成厚度为
Figure PCTCN2021093160-appb-000123
的第二空穴传输层(HTL2)。
接着在第二空穴传输层上，将GhP1：化合物1：fac-Ir(ppy) 3按照45％：45％：10％的膜厚比进行共同蒸镀，形成厚度为
Figure PCTCN2021093160-appb-000124
的绿色发光层(EML)。
将ET-1和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2021093160-appb-000125
厚的电子传输层(ETL)。接着将Mg:LiF按照1:1的膜厚比进行共蒸，以形成厚度为
Figure PCTCN2021093160-appb-000126
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 PCTCN2021093160-appb-000127
的阴极。
此外，在上述阴极上真空蒸镀厚度为
Figure PCTCN2021093160-appb-000128
的CP-1，从而完成有机电致发光器件的制造。
实施例16-实施例20
除了在形成发光层时，以表10中所示的化合物分别替代实施例15中的化合物1以外，利用与实施例15相同的方法制作有机电致发光器件。
实施例21
除了在形成发光层时，按照GhP2：化合物352：fac-Ir(ppy) 3＝45％：45％：10％的膜厚比进行共同蒸镀，形成厚度为
Figure PCTCN2021093160-appb-000129
的绿色发光层以外，利用与实施例15相同的方法制作有机电致发光器件。
实施例22-实施例30
除了在形成发光层时，以表10中所示的化合物分别替代实施例21中的化合物352以外，利用与实施例21相同的方法制作有机电致发光器件。
比较例5-比较例6
除了在形成发光层时，以表9中所示的化合物A、化合物B分别替代实施例15中的化合物1以外，利用与实施例15相同的方法制作有机电致发光器件。
比较例7-比较例9
除了在形成发光层时，以表9中所示的化合物C、化合物D及化合物E分别替代实施例21中的化合物352以外，利用与实施例21相同的方法制作有机电致发光器件。
其中，在制备有机电致发光器件时，比较例5-9与实施例15-30所使用的部分材料的结构式如表9所示。
表9
Figure PCTCN2021093160-appb-000130
Figure PCTCN2021093160-appb-000131
对实施例15-30和比较例5-9制备所得的绿色有机电致发光器件进行性能测试，具体在10mA/cm 2的条件下测试了器件的IVL性能，T95器件寿命在20mA/cm 2的条件下进行测试，测试结果如表10。
表10 绿色有机电致发光器件的性能测试结果
Figure PCTCN2021093160-appb-000132
Figure PCTCN2021093160-appb-000133
由表10中器件性能测试结果可知，将本发明化合物用作绿色发光层的n type主体材料制备得到的实施例15-30与比较例5-9相比，具有提升器件效率和寿命的作用。其中，驱动电压几乎相当，器件效率至少提升了13.3％，T95寿命至少提升了10.5％。综上，本申请的有机化合物用于制备绿色有机电致发光器件时，可以有效地延长有机电致发光器件的寿命，并且大幅度提升有机电致发光器件的发光效率。
红色有机电致发光器件的制备
实施例31
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2021093160-appb-000134
的ITO基板(康宁制造)切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阳极、阴极搭接区域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NATA以形成厚度为
Figure PCTCN2021093160-appb-000135
的空穴注入层(HIL)，然后在空穴注入层上蒸镀一层NPAPF，形成厚度为
Figure PCTCN2021093160-appb-000136
的第一空穴传输层(HTL1)。
接着在第一空穴传输层上真空蒸镀PAPB，形成厚度为
Figure PCTCN2021093160-appb-000137
的第二空穴传输层(HTL2)。
然后在第二空穴传输层上，将化合物362：RH-P：Ir(MDQ) 2(acac)以45％：55％：3％的比例(蒸镀速率)进行共同蒸镀，形成厚度为
Figure PCTCN2021093160-appb-000138
的有机发光层(EML)。
将DBimiBphen和LiQ以1:1的重量比进行混合并蒸镀形成厚度为
Figure PCTCN2021093160-appb-000139
的电子传输层(ETL)，然后真空蒸镀一层Yb在电子传输层上形成厚度为
Figure PCTCN2021093160-appb-000140
的电子注入层(EIL)；
接着将镁(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 PCTCN2021093160-appb-000141
的阴极。
此外，在上述阴极上作为蒸镀了厚度为
Figure PCTCN2021093160-appb-000142
的CP-1，形成覆盖层(CPL)，从而完成有机发光器件的制造。
实施例32至43
除了在形成发光层时，以表11中所示的化合物分别替代实施例31中的化合物362以外，利用与实施例31相同的方法制作有机电致发光器件。
比较例10-11
除了在形成发光层时，以化合物G、化合物H分别替代实施例31中的化合物362以外，利用与实施例31相同的方法制作有机电致发光器件。
实施例31-43和比较例10-11中，所采用的主要材料的结构如下所示：
Figure PCTCN2021093160-appb-000143
对上述实施例31-43和比较例10-11的有机电致发光器件的性能(IVL和寿命)进行分析，结果如下表所示。其中，驱动电压、发光效率、外量子效率、色坐标是在恒定电流密度10mA/cm 2下进行测试，T95器件寿命在恒定电流密度20mA/cm 2下进行测试，结果如表11所示。
表11 红色有机电致发光器件性能
Figure PCTCN2021093160-appb-000144
Figure PCTCN2021093160-appb-000145
由表11中器件性能测试结果可知，将本发明化合物用作红色发光层的n type主体材料制备得到的实施例31-43与比较例10-11相比，具有提升器件效率和寿命的作用。其中，驱动电压相当，器件效率至少提升了13.4％，T95寿命至少提升了10.1％。
综上，本申请的有机化合物用于有机电致发光器件时，可以有效地延长有机电致发光器件的寿命，并且提升有机电致发光器件的发光效率。
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。
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下，可以通过任何合适的方式进行组合，为了避免不必要的重复，本公开对各种可能的组合方式不再另行说明。
此外，本公开的各种不同的实施方式之间也可以进行任意组合，只要其不违背本公开的思想，其同样应当视为本公开所公开的内容。

Claims (23)

  1. 一种有机化合物，其特征在于，所述有机化合物具有如下式I所示的结构：
    Figure PCTCN2021093160-appb-100001
    其中，Z选自O、S、C(R 3R 4)、N(R 5)、Si(R 3R 4)、Se，其中R 3、R 4和R 5相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-30的取代或未取代的芳基或者碳原子数为2-30的取代或未取代的杂芳基，或者上述R 3和R 4能够与它们共同连接的原子一起形成环；
    X 1、X 2和X 3相同或不同，且各自独立地选自CH或N，且X 1、X 2和X 3中至少一个为N；
    R 1和R 2相同或不同，且各自独立地选自氘、卤素基团、碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为3-12的三烷基硅基、碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基、碳原子数为1-10的烷氧基；n 1表示R 1的个数，n 2表示R 2的个数；R 1和R 2以R i表示，n 1～n 2以n i表示，i为变量，表示1或2，n i各自独立地选自0、1、2、3或4；且当n i大于1时，任意两个n i相同或不同；任选地，任意两个相邻的R i形成环；
    Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6-40的取代或未取代的芳基，或者碳原子数为2-30的取代或未取代的杂芳基；
    L 1、L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-35的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
    R 1～R 5、L 1～L 3和Ar 1～Ar 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、基团A、碳原子数为3-12的三烷基硅基、碳原子数为18-24的三芳基硅基、碳原子数为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2-10的杂环烷基、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的芳氧基、碳原子数为6-18的芳硫基、碳原子数为2-6的烯基；基团A选自碳原子数为3-20的取代或未取代的杂芳基或碳原子数为6-20的取代或未取代的芳基，基团A中的取代基选自氘、卤素基团、碳原子数为1-4的烷基；任选地，任意两个相邻的取代基形成环；
    Ad表示金刚烷基，q选自1、2或3。
  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式3-1至式3-8中任意一项所示的结构：
    Figure PCTCN2021093160-appb-100002
    Figure PCTCN2021093160-appb-100003
    式3-1、式3-2、式3-6中，分别有且只有一个Ad；式3-3、式3-4、式3-7中，分别有且只有两个Ad，式3-5、式3-8中，有且只有三个Ad。
  3. 根据权利要求1或2所述的有机化合物，其中，Ar 1和Ar 2相同或不同，且各自独立地选自如下式i-1至式i-15所示基团所组成的组：
    Figure PCTCN2021093160-appb-100004
    Figure PCTCN2021093160-appb-100005
    其中，M 1选自单键或者
    Figure PCTCN2021093160-appb-100006
    G 1～G 5各自独立地选自N或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
    G 6～G 13各自独立地选自N或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
    G 14～G 23各自独立地选自N或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
    G 24～G 33各自独立地选自N或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
    Z 1选自氢、氘、卤素基团、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为18～24的三芳基硅基；
    Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、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；
    Z 10～Z 20、J 1～J 4各自独立地选自：氢、氘、卤素基团、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；任选地，任意两个相邻的Z 19形成环；任选地，任意两个相邻的Z 20形成环；
    h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
    K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 23Z 24)；其中，Z 22、Z 23、Z 24各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
    K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 26Z 27)；其中，Z 25、Z 26、Z 27各自独立地选自：碳 原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
  4. 根据权利要求1或2所述的有机化合物，其中，Ar 1和Ar 2相同或不同，且各自独立地选自取代或未取代的基团V 1，未取代的基团V 1选自以下基团所组成的组：
    Figure PCTCN2021093160-appb-100007
    取代的基团V 1中具有一个或两个以上取代基，取代基各自独立地选自氘、氟、碳原子数为1-4的烷基、碳原子数为1-4的氟代烷基、碳原子数为3-7的三烷基硅基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基、环戊基、环己基、吡啶基、苯基。
  5. 根据权利要求1或2所述的有机化合物，其中，L 1、L 2和L 3相同或不同，且各自独立地为单键、或者选自式j-1至式j-12所示的基团所组成的组：
    Figure PCTCN2021093160-appb-100008
    Figure PCTCN2021093160-appb-100009
    其中，M 2选自单键或者
    Figure PCTCN2021093160-appb-100010
    表示化学键；
    Q 1～Q 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
    Q 6～Q 13各自独立地选自N或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
    Q 14～Q 23各自独立地选自N或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
    E 1～E 14、J 5～J 7各自独立地选自：氢、氘、卤素基团、基团B、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2～6的烯基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、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的芳氧基、碳原子数为6～18的芳硫基、碳原子数为18～24的三芳基硅基；基团B选自碳原子数为6～20的取代或未取代的芳基、碳原子数为3～20的取代或未取代的杂芳基，基团B中的取代基选自碳原子数为1～4的烷基、氟、氘；任选地，任意两个相邻的E 11形成环；任选地，任意两个相邻的E 12形成环；
    e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
    K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 16E 17)；其中，E 15、E 16、E 17各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3-15的饱和或不饱和的环；
    K 4选自单键、O、S、Se、N(E 18)、C(E 19E 20)、Si(E 19E 20)；其中，E 18至E 20各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的 环烷基、碳原子数为2～10的杂环烷基，或者E 19和E 20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。
  6. 根据权利要求1或2所述的有机化合物，其中，L 1选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为5-30的取代或未取代的亚杂芳基；
    L 2和L 3相同或不同，且各自独立地选自单键、碳原子数为6-25的取代或未取代的亚芳基、或者碳原子数为3-20的取代或未取代的亚杂芳基。
  7. 根据权利要求1或2所述的有机化合物，其中，L 1选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚咔唑基、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、取代或未取代的亚吡啶基；L 1中的取代基各自独立地选自基团C、氘、氟、碳原子数为1-4的烷基、碳原子数为3-7的三烷基硅基、碳原子数为5-10的环烷基；基团C选自碳原子数为6-15的取代或未取代的芳基、碳原子数为5-15的取代或未取代的杂芳基，基团C中的取代基选自氘、氟、碳原子数为1-4的烷基；
    L 2和L 3相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚咔唑基、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、取代或未取代的亚吡啶基；L 2和L 3中的取代基各自独立地选自氘、氟、碳原子数为1-4的烷基、碳原子数为3-7的三烷基硅基、碳原子数为5-10的环烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基。
  8. 根据权利要求1或2所述的有机化合物，其中，L 1为单键，或者为取代或未取代的基团T 1，未取代的基团T 1选自如下基团所组成的组：
    Figure PCTCN2021093160-appb-100011
    其中，取代的基团T 1中具有一个或两个以上取代基，取代的基团T 1中的取代基独立地选自氘、氟、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的烷硫基、碳原子数为1-4的氟代烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基、萘基。
  9. 根据权利要求1或2所述的有机化合物，其中，L 2选自单键、取代或未取代的基团T 2，未取代的基团T 2选自以下基团所组成的组：
    Figure PCTCN2021093160-appb-100012
    其中，取代的基团T 2中具有一个或两个以上取代基，取代的基团T 2中的取代基独立地选自氘、氟、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的烷硫基、碳原子数为1-4的氟代烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基、苯基。
  10. 根据权利要求1或2所述的有机化合物，其中，L 3为单键，或者为取代或未取代的基团T 3，未取代的基团T 3选自如下基团所组成的组：
    Figure PCTCN2021093160-appb-100013
    其中，取代的基团T 3中具有一个或两个以上取代基，取代的基团T 3中的取代基独立地选自氘、氟、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的烷硫基、碳原子数为1-4的氟代烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基。
  11. 根据权利要求1或2所述的有机化合物，其中，R 1和R 2相同或不同，且各自独立地选自氘、氟、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为1-4的烷氧基、碳原子数为3-7的三烷基硅基、基团D，其中，基团D选自碳原子数为6-20的取代或未取代的芳基、碳原子数为3-20的取代或未取代的杂芳基，基团D中的取代基选自氘、氟、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基。
  12. 根据权利要求1所述的有机化合物，其中，R 3和R 4相同或不同，且各自独立地选自碳原子数为1-4的烷基、碳原子数为6-12的芳基或者碳原子数为3-12的杂芳基，或者上述R 3和R 4能够与它们共同连接的原子一起形成碳原子数为5-15的饱和或不饱和环；
    R 5选自碳原子数为6-20的取代或未取代的芳基、碳原子数为3-20的取代或未取代的杂芳基，R 5中的取代基选自氘、氟、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为3-7的三烷基硅基。
  13. 根据权利要求2所述的有机化合物，其中，
    Figure PCTCN2021093160-appb-100014
    选自以下结构所组成的组：
    Figure PCTCN2021093160-appb-100015
  14. 根据权利要求2所述的有机化合物，其中，
    Figure PCTCN2021093160-appb-100016
    选自以下结构所组成的组：
    Figure PCTCN2021093160-appb-100017
    Figure PCTCN2021093160-appb-100018
  15. 根据权利要求1所述的有机化合物，其中，式I中，
    Figure PCTCN2021093160-appb-100019
    上连接有一个Ad，且连接有一个Ad的
    Figure PCTCN2021093160-appb-100020
    选自以下基团所组成的组：
    Figure PCTCN2021093160-appb-100021
  16. 根据权利要求1所述的有机化合物，其中，式I中，
    Figure PCTCN2021093160-appb-100022
    上连接有一个Ad，且连接有一个Ad的
    Figure PCTCN2021093160-appb-100023
    选自以下基团所组成的组：
    Figure PCTCN2021093160-appb-100024
  17. 根据权利要求1所述的有机化合物，其中，式I中，
    Figure PCTCN2021093160-appb-100025
    上连接有一个Ad，且连接有一个Ad的
    Figure PCTCN2021093160-appb-100026
    选自以下基团所组成的组：
    Figure PCTCN2021093160-appb-100027
  18. 根据权利要求1所述的有机化合物，其中，式I中，L 1、L 2和L 3中的至少一个为
    Figure PCTCN2021093160-appb-100028
    X 1、X 2和X 3均为N。
  19. 根据权利要求1所述的有机化合物，其中，所述有机化合物选自如下化合物组成的组：
    Figure PCTCN2021093160-appb-100029
    Figure PCTCN2021093160-appb-100030
    Figure PCTCN2021093160-appb-100031
    Figure PCTCN2021093160-appb-100032
    Figure PCTCN2021093160-appb-100033
    Figure PCTCN2021093160-appb-100034
    Figure PCTCN2021093160-appb-100035
    Figure PCTCN2021093160-appb-100036
    Figure PCTCN2021093160-appb-100037
    Figure PCTCN2021093160-appb-100038
    Figure PCTCN2021093160-appb-100039
    Figure PCTCN2021093160-appb-100040
    Figure PCTCN2021093160-appb-100041
    Figure PCTCN2021093160-appb-100042
    Figure PCTCN2021093160-appb-100043
    Figure PCTCN2021093160-appb-100044
    Figure PCTCN2021093160-appb-100045
  20. 一种电子元件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含权利要求1-19中任意一项所述的有机化合物。
  21. 根据权利要求20所述的电子元件，其特征在于，所述功能层包括有机发光层，所述有机发光层包含所述有机化合物。
  22. 根据权利要求20或21所述的电子元件，其中，所述电子元件为有机电致发光器件；
    优选地，所述有机电致发光器件为绿色器件；
    优选地，所述有机电致发光器件为红色器件。
  23. 一种电子装置，包含权利要求20-22中任意一项所述的电子元件。
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