WO2022267661A1 - 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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WO2022267661A1
WO2022267661A1 PCT/CN2022/088176 CN2022088176W WO2022267661A1 WO 2022267661 A1 WO2022267661 A1 WO 2022267661A1 CN 2022088176 W CN2022088176 W CN 2022088176W WO 2022267661 A1 WO2022267661 A1 WO 2022267661A1
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carbon atoms
substituted
group
unsubstituted
independently selected
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French (fr)
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贾志艳
刘云
金荣国
李应文
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陕西莱特光电材料股份有限公司
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Priority to US18/027,991 priority Critical patent/US11807616B2/en
Publication of WO2022267661A1 publication Critical patent/WO2022267661A1/zh

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Definitions

  • the present application relates to the technical field of organic electroluminescence, and specifically provides an organic compound, an electronic component and an electronic device using the same.
  • Organic electroluminescent technology is regarded as the next generation of display and lighting technology due to its advantages of active light emission, high luminous efficiency, low power consumption, light weight, thinness, fast response speed, and large viewing angle.
  • An organic electroluminescent device consists of a substrate, an anode, a hole injection layer, a hole transport layer, a hole adjustment layer and an electron blocking layer, an organic light-emitting layer, an electron transport layer and a hole blocking layer, an electron injection layer, and a cathode. Electrons and holes are injected from the cathode and anode respectively, and then recombine in the organic light-emitting layer through the electron transport layer and the hole transport layer to form excitons, and the excitons return to the ground state to emit light.
  • OLEDs organic electroluminescent devices
  • the currently reported materials for the organic hole-adjusting layer are generally small in molecular weight and have a low glass transition temperature. During the use of the material, repeated charging and discharging will easily crystallize the material and destroy the uniformity of the film, thereby affecting the service life of the material. Therefore, it is of great practical application value to develop stable and efficient organic hole adjustment layer materials to improve charge mobility, reduce driving voltage, improve device luminous efficiency, and prolong device life.
  • the purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the organic compound.
  • Using the organic compound in an organic electroluminescent device can improve the performance of the device.
  • the first aspect of the present application provides an organic compound having a structure as shown in formula I:
  • R 1 and R 2 are the same or different, and are each independently selected from hydrogen, deuterium, methyl or phenyl;
  • n is selected from 1 or 2;
  • X is selected from C(R 5 R 6 ), O or S;
  • R 5 and R 6 are the same or different, and each independently selected from an alkyl group with 1 to 10 carbon atoms and an aryl group with 6 to 20 carbon atoms; optionally, R 5 and R 6 are connected to each other to form a saturated Or an unsaturated 5-15 membered ring;
  • L is selected from single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups with 3 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups with 1 to 10 carbon atoms. alkyl;
  • L 1 and L 2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted heterogeneous group with 3 to 30 carbon atoms Aryl;
  • Ar 1 and Ar 2 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;
  • R 3 and R 4 are the same or different, and are independently selected from deuterium, cyano, halogen, alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, and aryl with 6 to 12 carbon atoms, Heteroaryl group with 3 to 12 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms or haloalkyl group with 1 to 10 carbon atoms;
  • n 1 represents the number of R 3 , selected from 0, 1 or 2, when n 1 is 2, each R 3 is the same or different;
  • n 2 represents the number of R 4 , selected from 0, 1, 2 or 3, When n 2 is greater than 1, each R 4 is the same or different;
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, cyano, halogen, alkyl with 1 to 10 carbon atoms, and Haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms Or a cycloalkyl group with 3-10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring.
  • the organic compound of the present application is based on a substituted cycloalkyl fused specific dibenzo five-membered ring as the core, which is combined with triarylamine to make the spatial configuration of the molecule more three-dimensional, thereby increasing T1 ( triplet state energy level) Level, effectively blocking the diffusion of excitons, improving the life of the device; in addition, the organic compound of the present application has better hole mobility, which improves the matching between the hole transport layer and the organic light-emitting layer, thereby improving the device life. luminous efficiency. Therefore, using the organic compound of the present application in the hole adjustment layer of organic electroluminescent devices, especially red light devices, can effectively improve the luminous efficiency and life of the device while maintaining a low driving voltage.
  • the second aspect of the present application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer contains the above-mentioned organic compound;
  • a third aspect of the present application provides an electronic device, including the above-mentioned electronic component.
  • Fig. 1 is a schematic structural view of an organic electroluminescence device according to an embodiment of the present application.
  • Fig. 2 is a schematic diagram of a first electronic device according to an embodiment of the present application.
  • Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
  • Fig. 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.
  • the first aspect of the present application provides an organic compound having a structure as shown in Formula I:
  • R 1 and R 2 are the same or different, and are each independently selected from hydrogen, deuterium, methyl or phenyl;
  • n is selected from 1 or 2;
  • X is selected from C(R 5 R 6 ), O or S;
  • R 5 and R 6 are the same or different, and each independently selected from an alkyl group with 1 to 10 carbon atoms and an aryl group with 6 to 20 carbon atoms; optionally, R 5 and R 6 are connected to each other to form a saturated Or an unsaturated 5-15 membered ring;
  • L is selected from single bonds, substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups with 3 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups with 1 to 10 carbon atoms. alkyl;
  • L 1 and L 2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted heterogeneous group with 3 to 30 carbon atoms Aryl;
  • Ar 1 and Ar 2 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;
  • R 3 and R 4 are the same or different, and are independently selected from deuterium, cyano, halogen, alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, and aryl with 6 to 12 carbon atoms, Heteroaryl group with 3 to 12 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms or haloalkyl group with 1 to 10 carbon atoms;
  • n 1 represents the number of R 3 , selected from 0, 1 or 2, when n 1 is 2, each R 3 is the same or different;
  • n 2 represents the number of R 4 , selected from 0, 1, 2 or 3, When n 2 is greater than 1, each R 4 is the same or different;
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, cyano, halogen groups (such as fluorine), and alkyl groups with 1 to 10 carbon atoms , a haloalkyl group with 1 to 10 carbon atoms, a trialkylsilyl group with 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group with 6 to 20 carbon atoms, and a 3 to 20 carbon atom group A heteroaryl group or a cycloalkyl group with 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15 membered ring.
  • halogen groups such as fluorine
  • R5 and R6 are the same or different, and are independently selected from alkyl groups with 1 to 10 carbon atoms and aryl groups with 6 to 20 carbon atoms.
  • R5 and R 6 are connected to each other to form a saturated or unsaturated 5-15 -membered ring
  • this expression is the same as or different from “ R5 and R6, and each is independently selected from an alkyl group with 1-10 carbon atoms, and the number of carbon atoms is 6-20 aryl groups, or R 5 and R 6 are connected to each other to form a saturated or unsaturated 5-15 membered ring” means the same.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as R c ).
  • substituent hereinafter, for convenience of description, the substituent is collectively referred to as R c ).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • substituent ie, Rc
  • Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group, aryl group, trialkylsilyl group, triphenylsilyl group, alkyl group, haloalkyl group, cycloalkyl group and the like.
  • the number of substituent R c may be one or more.
  • substituents R c When two substituents R c are connected to the same atom, these two substituents R c may exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituents R c on the functional group When, the adjacent substituents R c can exist independently or be fused with the functional group to which they are connected to form a ring.
  • the terms “optionally” and “optionally” mean that the subsequently described event or circumstance may but need not occur, and that the description includes instances where the event or circumstance occurs or does not occur.
  • “optionally, two adjacent substituents form a ring” means that these two substituents may but not necessarily form a ring, including: the situation where two adjacent substituents form a ring and two phases Situations where adjacent substituents do not form a ring.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is:
  • Formula Q-1 represents that there are q substituents R" on the benzene ring , each R" can be the same or different, and the options of each R" do not affect each other;
  • Formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings The number q of "substituents may be the same or different, each R" may be the same or different, and the options of each R" do not affect each other.
  • the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is a substituted arylene group with 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocycle.
  • the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group, in other words, the aryl group can be a single-ring aryl group, a condensed ring aryl group, two or more single-ring aryl groups connected by carbon-carbon bond conjugation. Cyclic aryl groups, single-ring aryl groups and condensed-ring aryl groups connected through carbon-carbon bond conjugation, and two or more fused-ring aryl groups connected through carbon-carbon bond conjugation.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as a phenanthrenyl, a fluorenyl, anthracenyl) and the like.
  • aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl , Base etc.
  • the arylene group referred to refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
  • the substituted aryl group can be that one or more than two hydrogen atoms in the aryl group are replaced by such as deuterium atom, halogen group, -CN, aryl group, heteroaryl group, trialkylsilyl group, triphenylsilyl group, etc. Substituted by groups such as radicals, alkyls, cycloalkyls, haloalkyls, etc.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuryl-substituted phenyl groups, dibenzothienyl-substituted phenyl groups, pyridyl-substituted phenyl groups, and the like. It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituent on the aryl group, for example, a substituted aryl group with 18 carbon atoms refers to the aryl group and the substituted The total number of carbon atoms in the group is 18.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing at least one heteroatom in the ring, and the heteroatom can 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, in other words, a heteroaryl group can be a single aromatic ring system, or a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic
  • the ring system is an aromatic single ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, Acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridine Azinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuryl, phen
  • thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings linked by carbon-carbon bonds. System type heteroaryl.
  • the heteroarylene referred to refers to a divalent group formed by further loss of a hydrogen atom from the heteroaryl group.
  • the substituted heteroaryl group can be that one or more than two hydrogen atoms in the heteroaryl group are replaced by such as deuterium atom, halogen group, -CN, aryl group, heteroaryl group, trialkylsilyl group, triphenyl Substituted by groups such as silicon groups, alkyl groups, cycloalkyl groups, and haloalkyl groups.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuryl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms is 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 , 19, 20, specific examples of aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, base.
  • the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 20, for example, the number of carbon atoms is 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, specific examples of heteroaryl as substituents include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl Linyl, quinazolinyl, quinoxalinyl, isoquinolinyl.
  • the alkyl group having 1 to 10 carbon atoms may include straight chain alkyl groups having 1 to 10 carbon atoms and branched chain alkyl groups having 3 to 10 carbon atoms.
  • the number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
  • alkyl group examples include, but are not limited to, methyl, ethyl, n-propyl, iso Propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-Dimethyloctyl, etc.
  • the halogen group may be, for example, fluorine, chlorine, bromine, iodine, preferably fluorine.
  • trialkylsilyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, and the like.
  • haloalkyl examples include, but are not limited to, trifluoromethyl.
  • cycloalkyl examples include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
  • a non-positioning linkage refers to a 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 runs through, 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 unpositioned linkages that run through the bicyclic ring, and the meanings represented include the formula (f -1) to any possible connection shown in formula (f-10).
  • the phenanthrenyl group represented by the formula (X') is connected to other positions of the molecule through a non-positioning link extending from the middle of the benzene ring on one side. It includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
  • a non-positioning substituent in the present application refers to a substituent connected through a single bond protruding 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 group represented by the formula (Y) is connected to the quinoline ring through an unpositioned link, and the meanings represented include the formula (Y-1) ⁇ Any possible connection mode shown in formula (Y-7).
  • formula I may have the structure shown in formula I-1 or formula I-2:
  • two R 1 may be the same or different, and two R 2 may be the same or different.
  • X is selected from C(R 5 R 6 ) or O.
  • R1 and R2 are the same or different, and are each independently selected from hydrogen or methyl.
  • R and R are the same or different, and each independently selected from methyl, ethyl, isopropyl, tert - butyl, phenyl, naphthyl or biphenyl ; optionally, R and R 6 are connected to each other to form a cyclopentane, cyclohexane, norbornane or fluorene ring.
  • R and R are the same or different, and are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert - butyl, phenyl, naphthyl, biphenyl, Pyridyl, dibenzofuryl, dibenzothienyl, carbazolyl, trimethylsilyl or trifluoromethyl.
  • n 1 +n 2 0, 1 or 2.
  • the structure of the organic compound is selected from the group consisting of the following structural formulas:
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, cyano, halogen groups (such as fluorine), and the number of carbon atoms is 1 to 5 alkyl groups, fluoroalkyl groups with 1 to 5 carbon atoms, trialkylsilyl groups with 3 to 7 carbon atoms, aryl groups with 6 to 15 carbon atoms, 5 to 15 carbon atoms heteroaryl or cycloalkyl with 5 to 10 carbon atoms.
  • substituents in L, L 1 , L 2 , Ar 1 and Ar 2 include, but are not limited to, deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl , tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuryl, dibenzothienyl, quinolinyl, cyclopentyl, Cyclohexyl or adamantyl; optionally, any two adjacent substituents form a fluorene ring, cyclopentane or cyclohexane.
  • L is selected from single bonds, substituted or unsubstituted arylene groups with 6 to 15 carbon atoms, substituted or unsubstituted heteroarylene groups with 3 to 12 carbon atoms .
  • L is selected from single bonds, substituted or unsubstituted arylene groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 carbon atoms, and 3, 4, 5 carbon atoms , 6, 7, 8, 9, 10, 11, 12 substituted or unsubstituted heteroarylene groups.
  • L is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene.
  • L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 15 carbon atoms, a substituted or unsubstituted arylene group with 5 to 12 carbon atoms Unsubstituted heteroarylene.
  • L and L are each independently selected from single bonds, substituted or unsubstituted arylene groups with 6, 7, 8, 9, 10, 11, 12, 13 , 14 , 15 carbon atoms, carbon atoms 5, 6, 7, 8, 9, 10, 11, 12 substituted or unsubstituted heteroarylene groups.
  • L and L are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted A fluorenylene group, a substituted or unsubstituted dibenzofurylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted carbazolylidene group.
  • the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trimethylsilyl or phenyl.
  • L, L and L are each independently selected from a single bond or a group A ; wherein, the group A is selected from the following groups:
  • Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 20 carbon atoms base.
  • Ar 1 and Ar 2 are each independently selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 substituted or unsubstituted aryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms Substituted or unsubstituted heteroaryl.
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, cyano, fluorine, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, and A trialkylsilyl group with 3 to 7 carbon atoms, an aryl group with 6 to 12 carbon atoms, a heteroaryl group with 5 to 12 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms; optionally, Any two adjacent substituents form a fluorene ring, cyclopentane or cyclohexane.
  • Ar and Ar are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridine substituted or unsubstituted quinolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted terphenylene.
  • Ar and Ar are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted Quinolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrene substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene.
  • the substituents in Ar and Ar are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert - butyl, trifluoromethyl, trimethylsilyl, Phenyl, naphthyl, cyclopentyl, cyclohexyl or adamantyl; optionally, any two adjacent substituents form a fluorene ring, cyclopentane or cyclohexane.
  • Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted group V, or a substituted or unsubstituted group W; the unsubstituted group V is selected from the following groups :
  • the substituted group V has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethane group, trimethylsilyl, phenyl, naphthyl, cyclopentyl, cyclohexyl or adamantyl; when the number of substituents is greater than 1, each substituent is the same or different;
  • the unsubstituted group W is selected from the following groups:
  • the substituted group W has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl or tert-butyl; when the substituent When the number of is greater than 1, each substituent is the same or different.
  • Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted group V'; the unsubstituted group V' is selected from the following groups:
  • the substituted group V' has one or more than two substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl group, trimethylsilyl, phenyl, naphthyl, cyclopentyl, cyclohexyl or adamantyl; when the number of substituents is greater than 1, each substituent is the same or different.
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • the organic compound is selected from the group consisting of the following compounds:
  • the second aspect of the present application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the organic compound of the present application.
  • the electronic component is an organic electroluminescent device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescent device
  • the functional layer includes a hole adjusting layer, wherein the hole adjusting layer includes the organic compound of the present application.
  • the organic electroluminescence device may be a red light device, a blue light device or a green light device.
  • the organic electroluminescent device is a red light device.
  • the electronic component is a photoelectric conversion device
  • the functional layer includes a hole transport layer, wherein the hole transport layer includes the organic compound of the present application.
  • the electronic component is an organic electroluminescence device, and as shown in FIG. 1, the organic electroluminescence device may include an anode 100, a hole transport layer 321, a hole adjustment layer 322 , organic light emitting layer 330 , electron transport layer 340 and cathode 200 .
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It preferably includes a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 321 includes one or more hole transport materials, and the hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. No special restrictions are made.
  • the hole transport layer 321 may be composed of the compound NPB, and the hole adjustment layer 322 may contain the compound of the present application.
  • the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a dopant material.
  • the organic light-emitting layer 330 is composed of a host material and a dopant 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 dopant material, thereby enabling the dopant material to emit light.
  • the host material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not particularly limited in this application.
  • the host material of the organic light emitting layer 330 is CBP.
  • the dopant material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials, and this application does not make a special statement about it. limits.
  • the dopant material of the organic light emitting layer 330 is Ir(piq) 2 (acac).
  • the electron transport layer 340 can be a single-layer structure or a multilayer structure, and it can include one or more electron transport materials.
  • the electron transport material can be selected from but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or electron transport materials such as ET-01, TPBi, LiQ, etc.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 may also be 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 compounds.
  • the electron injection layer 350 may include Yb.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in this application.
  • the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 which are sequentially stacked.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • a solar cell may include an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode that are sequentially stacked, wherein the hole transport layer contains the organic compounds.
  • a third aspect of the present application provides an electronic device, including the electronic component provided in the second aspect of the present application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lights, optical modules, etc.
  • the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera or other types of electronic devices.
  • the compounds of the synthetic methods not mentioned in this application are all raw material products obtained through commercial channels.
  • IM YM-x listed in Table 1 was synthesized according to the method of IM YM-1, except that starting material 1 was used instead of 5-bromo-6-fluoro-2,3-dihydro-1,1,3,3-tetra Methyl-1H-indene, using raw material 2 instead of 3-chloro-2 hydroxyphenylboronic acid, wherein, the main raw material used, the synthesized IM YM-x and its yield are shown in Table 1.
  • IM YM-1 (20g, 62.7mmol) in 200mL of N-methyl-2-pyrrolidone, then add K 2 CO 3 (17.3g, 125.4mmol), under nitrogen atmosphere, Heated to 200°C and refluxed overnight. After the reaction was completed, the reaction liquid was lowered to room temperature, and the solvent was distilled off. Then, water was added to the reaction solution, and the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated by rotary evaporation. Finally, column chromatography was used for separation and purification to obtain IM A-1 (13.5 g, yield 72.1%).
  • the IMA-y listed in Table 2 is synthesized with reference to the method of IMA-1, the difference is that raw material 3 is used instead of IM YM-1, wherein the main raw material used, the synthesized IMA-y and its yield are shown in Table 2 .
  • IM YM-9 (20g, 55mmol) in 50mL of THF, cool to -78°C, then add n-BuLi (22mL, 2.5M, 55mmol) dropwise, react for 4h, then add diphenyl Methanone (10 g, 55 mmol) was incubated for 30 min, then raised to room temperature and reacted for 30 min. The reaction was quenched with methanol, and the solvent was removed under reduced pressure.
  • the reactant 2,5-dichloro-2,5-dimethylhexane (10g, 54.6mmol) was dissolved in 50mL of N-dichloroethane (DCE), and then the reaction solution Decrease to 0°C, add AlCl 3 (7.3g, 54.6mmol), and add 1-bromo-9,9-dimethyl-9H-fluorene (14.9g, 54.6mmol) in DCE (50mL) dropwise under nitrogen atmosphere solution, after reacting for 30 minutes, the temperature of the reaction solution was raised to 80° C. for 12 hours. After cooling down to room temperature, ice (100 g) and HCl (20 mL) were added and stirred for 20 min.
  • DCE N-dichloroethane
  • IM C-w listed in Table 4 was synthesized with reference to the method of IM C-1, the difference being that raw material 5 was used instead of 1-bromo-9,9-dimethyl-9H-fluorene, wherein the main raw material used, the synthesized IM C-w and its yield are shown in Table 4.
  • IM YM-15 (15g, 43.6mmol) to a 10L three-necked flask, start to heat up to IM YM-15 melting, then add sublimed sulfur (25.8g, 100.5mmol), at this time the system is yellow, continue Raise the temperature to 115-120°C, and then add aluminum trichloride (0.35g, 2.6mmol) in batches. During the process of adding aluminum trichloride, the system gradually turns black and releases a large amount of hydrogen sulfide gas. After keeping warm for 4 hours, start to slowly raise the temperature to 200-210°C.
  • IM F-x listed in Table 6 is synthesized with reference to the method of IM F-1, the difference is that raw material 6 is used instead of IMA-6, and raw material 7 is used instead of 4-fluorophenylboronic acid, wherein the main raw material used, the synthesized IM F-x and its yield are shown in Table 6.
  • the IMD-x listed in Table 7 is synthesized with reference to the method of IMD-1, the difference is that raw material 8 is used instead of 4-bromo-p-terphenyl, and raw material 9 is used instead of aniline, wherein the main raw materials used, the synthesized IMD-x and Its yield is shown in Table 7.
  • the compound X listed in Table 8 is synthesized with reference to the method of compound 4, and the difference is that raw material 10 is used instead of IMA-1, and raw material 11 is used instead of IM D-1, wherein, the main raw material used, the compound X synthesized and its The yield and mass spectrum are shown in Table 8.
  • Embodiment 1 red organic electroluminescent device
  • the ITO substrate (manufactured by Corning) was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (height), and it was prepared into an experimental substrate with an anode and an insulating layer pattern by using a photolithography process, and it can be used 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 oil stains on the surface of the ITO substrate.
  • F4-TCNQ was evaporated on the anode of the experimental substrate by vacuum evaporation method to form thick hole injection layer, and then vapor-deposit NPB on the hole injection layer to form a thickness of hole transport layer.
  • Compound 4 of the present application is vacuum evaporated on the hole transport layer to form a thickness of hole adjustment layer.
  • CBP and Ir(piq) 2 (acac) were evaporated at a weight ratio of 98%:2% to form a thickness of organic light-emitting layer.
  • ET-01 and LiQ were vapor-deposited at a weight ratio of 1:1 to form a thickness of The electron transport layer, and then Yb is evaporated on the electron transport layer to form a thickness of The electron injection layer, and then magnesium (Mg) and silver (Ag) were vacuum evaporated on the electron injection layer with a deposition rate of 1:9 to form a thickness of of the cathode.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that compounds shown in Table 10 below were used instead of Compound 4 when forming the hole adjusting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound A, Compound B, Compound C, and Compound D were used instead of Compound 4 when forming the hole adjustment layer.

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Abstract

本申请属于有机材料领域，涉及一种有机化合物以及使用其的电子元件和电子装置，所述有机化合物具有如式I所示的结构，所述有机化合物应用于有机电致发光器件中，可显著改善器件的性能。

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2021年6月25日递交的申请号为202110713428.0的中国专利申请，以及2021年8月20日递交的申请号为202110963124.X的中国专利申请的优先权，上述中国专利申请的全部内容通过引用并入本申请中。
技术领域
本申请涉及有机电致发光技术领域，具体提供一种有机化合物以及使用其的电子元件和电子装置。
背景技术
有机电致发光技术由于具有主动发光、发光效率较高、功耗低、轻、薄、响应速度快，可视角度大等优点被视为下一代显示和照明技术。有机电致发光器件由基板、阳极、空穴注入层、空穴传输层、空穴调整层及电子阻挡层、有机发光层、电子传输层及空穴阻挡层、电子注入层以及阴极等组成。电子和空穴分别从阴极和阳极注入，然后通过电子传输层和空穴传输层在有机发光层复合形成激子，激子回到基态而发光。
虽然现在有机电致发光器件(OLED)已经被广泛应用，但是由于优异的传输材料、高效的发光材料、注入材料的稀缺，导致器件的发光效率、使用寿命等性能和产品的应用要求相比还有待进一步提升。目前报道的有机空穴调整层材料由于分子量普遍较小，材料的玻璃化温度较低，在材料使用过程中，反复充电放电，材料容易结晶，薄膜的均一性被破坏，从而影响材料使用寿命。因此，开发稳定高效的有机空穴调整层材料，从而改善电荷迁移率，降低驱动电压，提高器件发光效率，延长器件寿命，具有很重要的实际应用价值。
发明内容
本申请的目的是提供一种有机化合物以及使用其的电子元件和电子装置，将所述有机化合物用于有机电致发光器件可以提升器件的性能。
本申请第一方面提供一种有机化合物，其具有如式I所示的结构：
Figure PCTCN2022088176-appb-000001
其中，R 1和R 2相同或不同，且各自独立地选自氢、氘、甲基或苯基；
n选自1或2；
X选自C(R 5R 6)、O或S；
R 5和R 6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6～20的芳基；任选地，R 5和R 6相互连接形成饱和或不饱和的5～15元环；
L选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基、碳原子数为1～10的亚烷基；
L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
R 3和R 4相同或不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基、碳原子数为3～12的三烷基硅基或碳原子数为1～10的卤代烷基；
n 1表示R 3的个数，选自0、1或2，当n 1为2时，各R 3相同或不同；n 2表示R 4的个数，选自0、1、2或3，当n 2大于1时，各R 4相同或不同；
L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、氰基、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、三苯基硅基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～10的环烷基；任选地，任意两个相邻的取代基形成饱和或不饱和的3～15元环。
本申请的有机化合物以取代的环烷基稠合特定的二苯并五元环为核心，将其与三芳胺结合，使得分子的空间构型更立体，从而提高T 1(三线态能级)水平，有效阻挡激子的扩散，提高器件的寿命；此外，本申请的有机化合物具有更好的空穴的迁移率，提高了空穴传输层与有机发光层之间的匹配性，从而提高器件的发光效率。因此将本申请的有机化合物用于有机电致发光器件，特别是红光器件中的空穴调整层，可以在维持较低驱动电压的前提下，有效提升器件的发光效率和寿命。
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；其中，所述功能层包含上述有机化合物；
本申请第三方面提供一种电子装置，包括上述电子元件。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的示意图。
图3是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、空穴调整层；330、有机发光层；340、电子传输层；350、电子注入层；320、空穴传输层；360、光电转化层；400、第一电子装置；500、第二电子装置。
具体实施方式
以下结合附图对本申请的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。
本申请的第一方面提供一种有机化合物，其具有如式I所示的结构：
Figure PCTCN2022088176-appb-000002
其中，R 1和R 2相同或不同，且各自独立地选自氢、氘、甲基或苯基；
n选自1或2；
X选自C(R 5R 6)、O或S；
R 5和R 6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6～20的芳基；任选地，R 5和R 6相互连接形成饱和或不饱和的5～15元环；
L选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基、碳原子数为1～10的亚烷基；
L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
R 3和R 4相同或不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基、碳原子数为3～12的三烷基硅基或碳原子数为1～10的卤代烷基；
n 1表示R 3的个数，选自0、1或2，当n 1为2时，各R 3相同或不同；n 2表示R 4的个数，选自0、1、2或3，当n 2大于1时，各R 4相同或不同；
L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、氰基、卤素基团(例如氟)、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、三苯基硅基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～10的环烷基；任选地，任意两个相邻的取代基形成饱和或不饱和的3～15元环。
本申请中，“R 5和R 6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6～20的芳基，任选地，R 5和R 6相互连接形成饱和或不饱和的5～15元环”，该表述与“R 5和R 6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6～20的芳基，或者R 5和R 6相互连接形成饱和或不饱和的5～15元环”意思相同。
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R c)。举例来讲，“取代或未取代的芳基”是指具有取代基Rc的芳基或者没有取代的芳基。其中上述的取代基即R c例如可以为氘、卤素基团、氰基、杂芳基、芳基、三烷基硅基、三苯基硅基、烷基、卤代烷基、环烷基等。取代基R c的个数可以是一个，也可以是多个。当同一个原子上连接有两个取代基R c时，这两个取代基R c可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基R c时，相邻的个取代基R c可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，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，两个相邻的取代基形成环”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。
本申请中，所采用的描述方式“各自独立地为”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 PCTCN2022088176-appb-000003
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。
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为碳原子数为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。
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。芳基的实例包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2022088176-appb-000004
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。
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、-CN、芳基、杂芳基、三烷基硅基、三苯基硅基、烷基、环烷基、卤代烷基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩基取代的苯基、吡啶基取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。
本申请中，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、吩噻嗪基、硅芴基、二苯并呋喃基以及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。
本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、三苯基硅基、烷基、环烷基、卤代烷基等基团取代。芳基取代的杂 芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
本申请中，作为取代基的芳基的碳原子数可以为6～20，例如碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20，作为取代基的芳基的具体实例包括但不限于，苯基、联苯基、萘基、蒽基、菲基、
Figure PCTCN2022088176-appb-000005
基。
本申请中，作为取代基的杂芳基的碳原子数可以为3～20，例如碳原子数为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20，作为取代基的杂芳基的具体实例包括但不限于，吡啶基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、喹唑啉基、喹喔啉基、异喹啉基。
本申请中，碳原子数为1～10的烷基可以包括碳原子数1至10的直链烷基和碳原子数3至10的支链烷基。烷基的碳原子数例如可以为1、2、3、4、5、6、7、8、9、10，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、正己基、正庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
本申请中，卤素基团例如可以为氟、氯、溴、碘，优选为氟。
本申请中，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。
本申请中，卤代烷基的具体实例包括但不限于，三氟甲基。
本申请中，环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基。
本申请中，
Figure PCTCN2022088176-appb-000006
是指与其他取代基或结合位置结合的连接键。
本申请中，不定位连接键涉及的是从环体系中伸出的单键
Figure PCTCN2022088176-appb-000007
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 PCTCN2022088176-appb-000008
例如，下式(X’)中所示的，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 PCTCN2022088176-appb-000009
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，下式(Y)中所示的，式(Y)所表示的取代基R基通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式。
Figure PCTCN2022088176-appb-000010
在本申请中，式I可以具有式I-1或式I-2所示的结构：
Figure PCTCN2022088176-appb-000011
式I-2中，两个R 1可以相同或不同，两个R 2可以相同或不同。
优选地，X选自C(R 5R 6)或O。
可选地，R 1和R 2相同或不同，且各自独立地选自氢或甲基。
可选地，R 5和R 6相同或不同，且各自独立地选自甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基；任选地，R 5和R 6相互连接形成环戊烷、环己烷、降冰片烷或芴环。
可选地，R 3和R 4相同或不同，且各自独立地选自氘、氰基、氟、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、三甲基硅基或三氟甲基。
可选地，n 1+n 2＝0、1或2。
在本申请的一种实施方案中，所述有机化合物的结构选自以下结构式所组成的组：
Figure PCTCN2022088176-appb-000012
Figure PCTCN2022088176-appb-000013
可选地，L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、氰基、卤素基团(例如氟)、碳原子数为1～5的烷基、碳原子数为1～5的氟代烷基、碳原子数为3～7的三烷基硅基、碳原子数为6～15的芳基、碳原子数为5～15的杂芳基或碳原子数为5～10的环烷基。
本申请中，L、L 1、L 2、Ar 1和Ar 2中的取代基的具体实例分别包括但不限于，氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、三氟甲基、三甲基硅基、苯基、萘基、联苯基、咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、环戊基、环己基或金刚烷基；任选地，任意两个相邻的取代基形成芴环、环戊烷或环己烷。
在本申请的一种实施方案中，L选自单键、碳原子数为6～15的取代或未取代的亚芳基、碳原子数为3～12的取代或未取代的亚杂芳基。例如，L选自单键，碳原子数为6、7、8、9、10、11、12、13、14、15的取代或未取代的亚芳基，碳原子数为3、4、5、6、7、8、9、10、11、12的取代或未取代的亚杂芳基。
可选地，L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基。
在本申请的一种实施方案中，L 1和L 2各自独立地选自单键、碳原子数为6～15的取代或未取代的亚芳基、碳原子数为5～12的取代或未取代的亚杂芳基。例如，L 1和L 2各自独立地选自单键，碳原子数为 6、7、8、9、10、11、12、13、14、15的取代或未取代的亚芳基，碳原子数为5、6、7、8、9、10、11、12的取代或未取代的亚杂芳基。
可选地，L 1和L 2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚咔唑基。
可选地，L、L 1和L 2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～5的烷基、三甲基硅基或苯基。
在本申请的一种具体实施方案中，L、L 1和L 2各自独立地选自单键或者基团A；其中，所述基团A选自如下基团：
Figure PCTCN2022088176-appb-000014
在本申请的一些实施方案中，Ar 1和Ar 2各自独立地选自碳原子数为6～25的取代或未取代的芳基、碳原子数为5～20的取代或未取代的杂芳基。例如，Ar 1和Ar 2各自独立地选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25的取代或未取代的芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20的取代或未取代的杂芳基。
可选地，Ar 1和Ar 2中的取代基各自独立地选自氘、氰基、氟、碳原子数为1～5的烷基、碳原子数为1～5的卤代烷基、碳原子数为3～7的三烷基硅基、碳原子数为6～12的芳基、碳原子数为5～12的杂芳基或碳原子数为5～10的环烷基；任选地，任意两个相邻的取代基形成芴环、环戊烷或环己烷。
在本申请的一些实施方案中，Ar 1和Ar 2各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的芴基、取代或未取代的咔唑基、取代或未取代的菲基、取代或未取代的螺二芴基、取代或未取代的三亚苯基、取代或未取代的三联苯基。
优选地，Ar 1和Ar 2各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的芴基、取代或未取代的咔唑基、取代或未取代的菲基、取代或未取代的螺二芴基、取代或未取代的三亚苯基。
可选地，Ar 1和Ar 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三甲基硅基、苯基、萘基、环戊基、环己基或金刚烷基；任选地，任意两个相邻的取代基形成芴环、环戊烷或环己烷。
在本申请的一种实施方案中，Ar 1和Ar 2各自独立地选自取代或未取代的基团V、或者取代或未取代的基团W；未取代的基团V选自如下基团：
Figure PCTCN2022088176-appb-000015
Figure PCTCN2022088176-appb-000016
其中，
Figure PCTCN2022088176-appb-000017
表示化学键；取代的基团V中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三甲基硅基、苯基、萘基、环戊基、环己基或金刚烷基；当取代基的个数大于1时，各取代基相同或不同；
未取代的基团W选自如下基团：
Figure PCTCN2022088176-appb-000018
其中，
Figure PCTCN2022088176-appb-000019
表示化学键；取代的基团W中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基或叔丁基；当取代基的个数大于1时，各取代基相同或不同。
优选地，Ar 1和Ar 2各自独立地选自取代或未取代的基团V’；未取代的基团V’选自如下基团：
Figure PCTCN2022088176-appb-000020
其中，取代的基团V’中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三甲基硅基、苯基、萘基、环戊基、环己基或金刚烷基；当取代基的个数大于1时，各取代基相同或不同。
可选地，Ar 1和Ar 2各自独立地选自如下基团组成的组：
Figure PCTCN2022088176-appb-000021
Figure PCTCN2022088176-appb-000022
优选地，Ar 1和Ar 2各自独立地选自如下基团组成的组：
Figure PCTCN2022088176-appb-000023
进一步可选地，Ar 1和Ar 2各自独立地选自如下基团组成的组：
Figure PCTCN2022088176-appb-000024
Figure PCTCN2022088176-appb-000025
优选地，Ar 1和Ar 2各自独立地选自如下基团组成的组：
Figure PCTCN2022088176-appb-000026
Figure PCTCN2022088176-appb-000027
可选地，所述有机化合物选自以下化合物所组成的组：
Figure PCTCN2022088176-appb-000028
Figure PCTCN2022088176-appb-000029
Figure PCTCN2022088176-appb-000030
Figure PCTCN2022088176-appb-000031
Figure PCTCN2022088176-appb-000032
Figure PCTCN2022088176-appb-000033
Figure PCTCN2022088176-appb-000034
Figure PCTCN2022088176-appb-000035
Figure PCTCN2022088176-appb-000036
Figure PCTCN2022088176-appb-000037
Figure PCTCN2022088176-appb-000038
Figure PCTCN2022088176-appb-000039
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，其中，所述功能层包含本申请的有机化合物。
可选地，所述电子元件为有机电致发光器件或光电转换器件。
在一种实施方式中，所述电子元件为有机电致发光器件，所述功能层包括空穴调整层，其中，所述空穴调整层包含本申请的有机化合物。
本申请中，所述有机电致发光器件可以为红光器件、蓝光器件或绿光器件。优选地，所述有机电致发光器件为红光器件。
在另一种实施方式中，所述电子元件为光电转换器件，所述功能层包括空穴传输层，其中，所述空穴传输层包含本申请的有机化合物。
在一种具体的实施方式中，电子元件为有机电致发光器件，且如图1所示，所述有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、空穴调整层322、有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO∶Al或SnO 2∶Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层321包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。例如，空穴传输层321可以由化合物NPB组成，空穴调整层322可以含有本申请的化合物。
可选地，有机发光层330可以由单一发光层材料组成，也可以包括主体材料和掺杂材料。可选地，有机发光层330由主体材料和掺杂材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给掺杂材料，进而使得掺杂材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的主体材料为CBP。
有机发光层330的掺杂材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的掺杂材料为Ir(piq) 2(acac)。
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者ET-01、TPBi、LiQ等电子传输材料。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入材料至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞 菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。例如，电子注入层350可以包括Yb。
按照另一种具体的实施方式，电子元件为光电转化器件。如图3所示，该光电转化器件可以包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的有机化合物。
按照一种具体的实施方式，如图3所示，光电转化器件可包括依次层叠设置的阳极100、空穴传输层320、光电转化层360、电子传输层340和阴极200。
可选地，光电转化器件可以为太阳能电池，尤其是可以为有机薄膜太阳能电池。举例而言，在本申请的一种实施方式中，太阳能电池可以包括依次层叠设置的阳极、空穴传输层、有机发光层、电子传输层和阴极，其中，空穴传输层包含有本申请的有机化合物。
本申请的第三方面提供一种电子装置，包括本申请第二方面提供的电子元件。
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
下面结合合成例来具体说明本申请的有机化合物的合成方法，但是本公开并不因此而受到任何限制。
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。
合成例
1、IM YM-1的合成
Figure PCTCN2022088176-appb-000040
在氮气氛围下，向500mL的三口烧瓶中投入5-溴-6-氟-2,3-二氢-1,1,3,3-四甲基-1H-茚(20g，73.8mmol)、3-氯-2羟基苯硼酸(15.3g，88.6mmol)、四(三苯基膦)钯(0.17g，0.15mmol)、碳酸钾(25.5g，184.5mmol)、160mL甲苯、80mL乙醇和40mL水，加热至70～80℃，回流过夜。将反应液冷却到室温后，水洗三遍，最后用饱和氯化铵水溶液萃取，合并有机相，用无水硫酸镁干燥后，旋蒸浓缩。将获得的固体物质用乙醇重结晶，得到IM YM-1(13.8g，收率58.9％)。
参照IM YM-1方法合成表1所列的IM YM-x，不同之处在于，使用原料1代替5-溴-6-氟-2,3-二氢-1,1,3,3-四甲基-1H-茚，使用原料2代替3-氯-2羟基苯硼酸，其中，使用的主要原料、合成的IM YM-x及其收率如表1所示。
表1
Figure PCTCN2022088176-appb-000041
Figure PCTCN2022088176-appb-000042
Figure PCTCN2022088176-appb-000043
2、IM A-1的合成
Figure PCTCN2022088176-appb-000044
在250mL三口瓶中，将IM YM-1(20g，62.7mmol)溶于200mL的N-甲基-2-吡咯烷酮中，再加入K 2CO 3(17.3g，125.4mmol)，在氮气氛围下，加热至200℃，回流过夜。反应完成，将反应液降至室温，蒸馏除去溶剂。然后，将水加入到反应液中，并用二氯甲烷萃取混合物，使用无水硫酸镁干燥后，旋蒸浓缩。最后，使用柱色谱分离纯化，得到IM A-1(13.5g，收率72.1％)。
参照IM A-1的方法合成表2所列的IM A-y，不同之处在于，使用原料3代替IM YM-1，其中，使用的主要原料、合成的IM A-y及其收率如表2所示。
表2
Figure PCTCN2022088176-appb-000045
Figure PCTCN2022088176-appb-000046
3、IM B-1的合成
Figure PCTCN2022088176-appb-000047
在三口瓶中，将IM YM-9(20g，55mmol)溶于50mL的THF中，冷却至-78℃，然后滴加n-BuLi(22mL，2.5M，55mmol)，反应4h后，加入二苯甲酮(10g，55mmol)，保温30min后，升至室温反应30min，用甲醇猝灭反应，并减压除去溶剂。然后加入冰醋酸(100mL)和25mL盐酸，回流24h后，降至室温，将反应液水洗至中性，过滤沉淀物，将沉淀物烘干得到IM B-1(15.4g，收率62.3％)。
参照IM B-1的方法合成表3所列的IM B-z，不同之处在于，使用IM YM-x代替IM YM-9，使用原料4代替二苯甲酮，其中，使用的主要原料、合成的IM B-z及其收率如表3所示。
表3
Figure PCTCN2022088176-appb-000048
4、IM C-1的合成
Figure PCTCN2022088176-appb-000049
在250mL三口瓶中，将反应物2,5-二氯-2,5-二甲基己烷(10g，54.6mmol)溶于50mL的N-二氯乙烷(DCE)中，然后将反应溶液降至0℃，加入AlCl 3(7.3g，54.6mmol)，在氮气氛围下，滴加1-溴-9,9-二甲基-9H-芴(14.9g，54.6mmol)的DCE(50mL)溶液，反应30min后，将反应溶液的温度升至80℃反应12h。之后降至室温，加入冰(100g)和HCl(20mL)，搅拌20min。使用二氯甲烷将反应液萃取三次，用无水硫酸镁干燥后，过硅胶柱得到粗产品，最后使用DCM∶MeOH＝1∶1(v/v)重结晶，得到IM C-1(16.5g，收率78.6％)。
参照IM C-1的方法合成表4所列的IM C-w，不同之处在于，使用原料5代替1-溴-9,9-二甲基-9H-芴，其中，使用的主要原料、合成的IM C-w及其收率如表4所示。
表4
Figure PCTCN2022088176-appb-000050
5、IM D-1的合成
Figure PCTCN2022088176-appb-000051
在氮气气氛下，向10L三口瓶中加入IM YM-15(15g，43.6mmol)，开始升温至IM YM-15熔融，然后加入升华硫(25.8g，100.5mmol)，此时体系呈黄色，继续升温至115～120℃，而后分批加入三氯化铝(0.35g，2.6mmol)，在加三氯化铝的过程中，体系逐渐变成黑色，放出大量硫化氢气体，三氯化铝加完后保温4h后，开始缓慢升温至200～210℃，反应4h后趁热将反应液倒入到250mL的单口瓶中，减压蒸馏，油泵真空度约40Pa，收集120～130℃之间的馏分，得到8.2g白色晶体，将固体按1g:3mL乙醇溶解，在-20℃下结晶，重复两次，得到IM YD-1(7.9g，收率48.5％)。
参照IM YD-1的方法合成表5所列的IM YD-2，不同之处在于，使用IM YM-16代替IM YM-15，其中，使用的主要原料、合成的IM YD-2及其收率如表5所示。
表5
Figure PCTCN2022088176-appb-000052
6、IM F-1的合成
Figure PCTCN2022088176-appb-000053
在氮气氛围下，向250mL的三口烧瓶中投入IM A-6(10g，31.9mmol)、4-氯苯硼酸(6.0g，38.4mmol)、四(三苯基膦)钯(0.18g，0.16mmol)、K 2CO 3(11.0g，79.8mmol)和100mL的甲苯，加热至70～80℃回流过夜。反应结束后冷却到室温，将反应液水洗三遍，合并有机相，用无水硫酸镁干燥后，减压浓缩。将获得的固体用乙醇重结晶，得到IM F-1(5.3g，收率42.8％)。
参照IM F-1的方法合成表6所列的IM F-x，不同之处在于，使用原料6代替IM A-6，使用原料7代替4-氟苯硼酸，其中，使用的主要原料、合成的IM F-x及其收率如表6所示。
表6
Figure PCTCN2022088176-appb-000054
Figure PCTCN2022088176-appb-000055
7、IM D-1的合成
Figure PCTCN2022088176-appb-000056
在氮气气氛下，将4-溴对三联苯(23.3g，75.5mmol)、苯胺(7.03g，75.5mmol)、150mL超干甲苯投入250mL三口烧瓶中，升温至70℃，依次加入叔丁醇钠(10.9g，113.3mmol)、X-Phos(0.63g，1.51mmol)、Pd 2(dba) 3(0.70g，0.76mmol)，然后升温至110℃回流反应1h，降至室温，将反应液水洗三次，用无水硫酸镁干燥，静置30min，抽滤、减压浓缩、过柱层析色谱柱得到IM D-1(19.5g，收率80.2％)。
参照IM D-1的方法合成表7所列的IM D-x，不同之处在于，使用原料8代替4-溴对三联苯，使用原料9代替苯胺，其中，使用的主要原料、合成的IM D-x及其收率如表7所示。
表7
Figure PCTCN2022088176-appb-000057
Figure PCTCN2022088176-appb-000058
Figure PCTCN2022088176-appb-000059
Figure PCTCN2022088176-appb-000060
Figure PCTCN2022088176-appb-000061
Figure PCTCN2022088176-appb-000062
8、化合物4的合成
Figure PCTCN2022088176-appb-000063
在氮气气氛下，将IM A-1(5g，16.7mmol)、IM D-1(5.4g，16.7mmol)、50mL甲苯投入100mL的三口烧瓶中，升温至70℃，依次加入叔丁醇钠(2.4g，25.05mmol)、S-Phos(0.14g，0.33mmol)、Pd 2(dba) 3(0.16g，0.17mmol)，然后升温至110℃回流反应2h，降至室温，将反应液水洗三次，用无水硫酸镁干燥静置30min，抽滤、减压浓缩、过柱层析色谱柱，最后使用正庚烷重结晶，得到化合物4(5.5g，收率56.2％)；质谱(m/z)＝584.29[M+H] +。
参照化合物4的方法合成表8所列的化合物X，不同之处在于，使用原料10代替IM A-1，使用原料11代替IM D-1，其中，使用的主要原料、合成的化合物X及其收率和质谱如表8所示。
表8
Figure PCTCN2022088176-appb-000064
Figure PCTCN2022088176-appb-000065
Figure PCTCN2022088176-appb-000066
Figure PCTCN2022088176-appb-000067
Figure PCTCN2022088176-appb-000068
Figure PCTCN2022088176-appb-000069
Figure PCTCN2022088176-appb-000070
Figure PCTCN2022088176-appb-000071
化合物4的核磁数据：
1H-NMR(CDCl 3,400MHz):7.66-7.51(m,13H),7.43-7.21(m,4H),6.65-6.47(m,6H),2.04(s,2H),1.43-1.40(d,12H)。
化合物81的核磁数据：
1H-NMR(CDCl 3,400MHz):7.63-7.38(m,16H),7.25-7.21(m,1H),7.15(s,1H),6.71-6.69(d,1H),6.50-6.48(d,4H),1.94-1.86(m,2H),1.75-1.66(m,2H),1.47-1.44(d,12H)。
实施例1：红色有机电致发光器件
将
Figure PCTCN2022088176-appb-000072
的ITO基板(康宁制造)切割成40mm(长)×40mm(宽)×0.7mm(高)的尺寸，采用光刻工序，将其制备成具有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。
首先，利用真空蒸镀法在实验基板阳极上蒸镀F4-TCNQ，形成
Figure PCTCN2022088176-appb-000073
厚的空穴注入层，再在空穴注入层上蒸镀NPB，形成厚度为
Figure PCTCN2022088176-appb-000074
的空穴传输层。
在空穴传输层上真空蒸镀本申请的化合物4，形成厚度为
Figure PCTCN2022088176-appb-000075
的空穴调整层。
在空穴调整层上，将CBP和Ir(piq) 2(acac)别以98％∶2％的重量比进行蒸镀形成厚度为
Figure PCTCN2022088176-appb-000076
的有机发光层。
在有机发光层上，将ET-01和LiQ以1∶1的重量比进行蒸镀形成厚度为
Figure PCTCN2022088176-appb-000077
的电子传输层，再将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2022088176-appb-000078
的电子注入层，然后将镁(Mg)和银(Ag)以1∶9的蒸镀速率真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2022088176-appb-000079
的阴极。
最后，在阴极上蒸镀CP-1，形成厚度为
Figure PCTCN2022088176-appb-000080
的有机覆盖层，从而完成有机发光器件的制造。
实施例2～56
除了在形成空穴调整层时，以下表10中所示的化合物替代化合物4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1～4
除了在形成空穴调整层时，分别以化合物A、化合物B、化合物C、化合物D替代化合物4以外， 利用与实施例1相同的方法制作有机电致发光器件。
以上实施例和对比例使用的主要材料结构如下表9所示。
表9
Figure PCTCN2022088176-appb-000081
在20mA/cm 2的条件下分析了如上制得的有机电致发光器件的性能，其结果示于下表10所示。
表10
Figure PCTCN2022088176-appb-000082
Figure PCTCN2022088176-appb-000083
由表10的结果可知，采用本申请的化合物的实施例1～56与使用公知的化合物所对应的器件比较例1～4相比，以本申请的有机化合物作空穴调整层制备的上述有机电致发光器件的发光效率(Cd/A)至少提高了17.8％，外量子效率至少提高了18.9％，寿命至少提高了15.1％；此外，实施例1～56制备的器件的也兼具较低的驱动电压。
以上结合附图详细描述了本申请的优选实施方式，但是，本申请并不限于上述实施方式中的具体细 节，在本申请的技术构思范围内，可以对本申请的技术方案进行多种简单变型，这些简单变型均属于本申请的保护范围。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，本申请对各种可能的组合方式不再另行说明。此外，本申请的各种不同的实施方式之间也可以进行任意组合，只要其不违背本申请的思想，其同样应当视为本申请所公开的内容。

Claims (17)

  1. 有机化合物，所述有机化合物具有如式I所示的结构：
    Figure PCTCN2022088176-appb-100001
    其中，R 1和R 2相同或不同，且各自独立地选自氢、氘、甲基或苯基；
    n选自1或2；
    X选自C(R 5R 6)、O或S；
    R 5和R 6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6～20的芳基；任选地，R 5和R 6相互连接形成饱和或不饱和的5～15元环；
    L选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基、碳原子数为1～10的亚烷基；
    L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
    Ar 1和Ar 2相同或不同，且各自独立地选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
    R 3和R 4相同或不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基、碳原子数为3～12的三烷基硅基或碳原子数为1～10的卤代烷基；
    n 1表示R 3的个数，选自0、1或2，当n 1为2时，各R 3相同或不同；n 2表示R 4的个数，选自0、1、2或3，当n 2大于1时，各R 4相同或不同；
    L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、氰基、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、三苯基硅基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～10的环烷基；任选地，任意两个相邻的取代基形成饱和或不饱和的3～15元环。
  2. 根据权利要求1所述的有机化合物，其中，L选自单键、碳原子数为6～15的取代或未取代的亚芳基、碳原子数为3～12的取代或未取代的亚杂芳基。
  3. 根据权利要求1所述的有机化合物，其中，L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基。
  4. 根据权利要求1所述的有机化合物，其中，L 1和L 2各自独立地选自单键、碳原子数为6～15的取代或未取代的亚芳基、碳原子数为5～12的取代或未取代的亚杂芳基。
  5. 根据权利要求1所述的有机化合物，其中，L 1和L 2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚萘基、取代或未取代的亚芴基、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、取代或未取代的亚咔唑基。
  6. 根据权利要求1所述的有机化合物，其中，L、L 1和L 2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～5的烷基、三甲基硅基或苯基。
  7. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2各自独立地选自碳原子数为6～25的 取代或未取代的芳基、碳原子数为5～20的取代或未取代的杂芳基；
    优选地，Ar 1和Ar 2中的取代基各自独立地选自氘、氰基、氟、碳原子数为1～5的烷基、碳原子数为1～5的卤代烷基、碳原子数为3～7的三烷基硅基、碳原子数为6～12的芳基、碳原子数为5～12的杂芳基或碳原子数为5～10的环烷基；任选地，任意两个相邻的取代基形成芴环、环戊烷或环己烷。
  8. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2各自独立地选自取代或未取代的基团V、或者取代或未取代的基团W；
    未取代的基团V选自如下基团：
    Figure PCTCN2022088176-appb-100002
    其中，
    Figure PCTCN2022088176-appb-100003
    表示化学键；取代的基团V中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三甲基硅基、苯基、萘基、环戊基、环己基或金刚烷基；当取代基的个数大于1时，各取代基相同或不同；
    未取代的基团W选自如下基团：
    Figure PCTCN2022088176-appb-100004
    其中，
    Figure PCTCN2022088176-appb-100005
    表示化学键；取代的基团W中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基或叔丁基；当取代基的个数大于1时，各取代基相同或不同。
  9. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2各自独立地选自如下基团组成的组：
    Figure PCTCN2022088176-appb-100006
    Figure PCTCN2022088176-appb-100007
  10. 根据权利要求1所述的有机化合物，其中，R 5和R 6各自独立地选自甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基；任选地，R 5和R 6相互连接形成环戊烷、环己烷、降冰片烷或芴环。
  11. 根据权利要求1所述的有机化合物，其中，R 3和R 4各自独立地选自氘、氰基、氟、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、三甲基硅基或三氟甲基。
  12. 根据权利要求1所述的有机化合物，其中，所述有机化合物的结构选自以下结构所组成的组：
    Figure PCTCN2022088176-appb-100008
    Figure PCTCN2022088176-appb-100009
    优选地，R 1和R 2相同或不同，且各自独立地选自氢或甲基；
    优选地，n 1+n 2＝0、1或2。
  13. 根据权利要求1所述的有机化合物，其中，所述有机化合物选自以下化合物所组成的组：
    Figure PCTCN2022088176-appb-100010
    Figure PCTCN2022088176-appb-100011
    Figure PCTCN2022088176-appb-100012
    Figure PCTCN2022088176-appb-100013
    Figure PCTCN2022088176-appb-100014
    Figure PCTCN2022088176-appb-100015
    Figure PCTCN2022088176-appb-100016
    Figure PCTCN2022088176-appb-100017
    Figure PCTCN2022088176-appb-100018
    Figure PCTCN2022088176-appb-100019
    Figure PCTCN2022088176-appb-100020
    Figure PCTCN2022088176-appb-100021
    Figure PCTCN2022088176-appb-100022
  14. 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；其中，所述功能层包含权利要求1～13中任一项所述的有机化合物。
  15. 根据权利要求14所述的电子元件，其中，所述电子元件为有机电致发光器件或光电转换器件。
  16. 根据权利要求14所述的电子元件，其中，所述电子元件为有机电致发光器件，所述功能层包括空穴调整层，所述空穴调整层包含所述有机化合物。
  17. 电子装置，包括权利要求14～16中任一项所述的电子元件。
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CN113773290B (zh) 2021-06-25 2022-07-29 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置
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CN115368294B (zh) * 2022-03-21 2024-02-27 北京莱特众成光电材料科技有限公司 有机化合物及包含其的电子元件和电子装置

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