WO2022016898A1 - 化合物、有机电致发光器件及电子装置 - Google Patents

化合物、有机电致发光器件及电子装置 Download PDF

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WO2022016898A1
WO2022016898A1 PCT/CN2021/083413 CN2021083413W WO2022016898A1 WO 2022016898 A1 WO2022016898 A1 WO 2022016898A1 CN 2021083413 W CN2021083413 W CN 2021083413W WO 2022016898 A1 WO2022016898 A1 WO 2022016898A1
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French (fr)
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郑奕奕
马天天
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陕西莱特光电材料股份有限公司
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Priority to US17/928,869 priority Critical patent/US20230192669A1/en
Publication of WO2022016898A1 publication Critical patent/WO2022016898A1/zh

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Definitions

  • the present application belongs to the technical field of organic electroluminescent materials, and specifically relates to a compound, an organic electroluminescent device and electronic device using the same.
  • An organic electroluminescent device such as an organic light emitting diode (OLED) generally includes a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer between the organic light-emitting layer and the anode, and an electron transport layer between the organic light-emitting layer and the cathode.
  • 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, and the electrons and holes combine in the electroluminescent layer.
  • Excitons are formed, and the excitons are in an excited state to release energy to the outside, thereby causing the electroluminescent layer to emit light to the outside.
  • CN104039778A etc. disclose materials that can prepare light-emitting layers in organic electroluminescent devices.
  • the current organic electroluminescent materials still have the problems of short luminescence lifetime and low luminous efficiency. Therefore, it is necessary to continue to develop new materials to further improve the lifetime and efficiency performance of organic electroluminescent devices.
  • the purpose of the present application is to provide an organic electroluminescent material with excellent performance, which can be used as a light-emitting layer in an organic electroluminescent device.
  • ring A and ring B are each independently an aromatic ring having 6 to 14 carbon atoms;
  • X is selected from O, S, Si (R 3 R 4), C (R 3 R 4);
  • Each R 1 is the same or different from each other, and is independently selected from the group consisting of: deuterium, halogen, cyano, alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, and 1 to 12 carbon atoms.
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-40 carbon atoms;
  • L 1 is selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-30 carbon atoms;
  • the substituents in Ar 1 and L 1 are the same or different from each other, and are each independently selected from: deuterium, cyano, halogen, nitro, group U, alkoxy with 1 to 12 carbon atoms, carbon Halogenated alkyl group with 1 to 12 atoms, alkyl group with 1 to 12 carbon atoms, cycloalkyl group with 3 to 12 carbon atoms, heterocyclic group with 3 to 12 carbon atoms, and 3 carbon atoms -12 alkylsilyl group, C6-18 arylsilyl group, C1-12 alkylthio group, C6-18 aryloxy group, C7-C7
  • each of L 1 and Ar 1 when there are two substituents on the same atom, optionally, two of said substituents are connected to each other to form a 5- to 18-membered aliphatic together with the atom to which they are commonly connected family ring or 5- to 18-membered aromatic ring;
  • Each R 2 is the same or different from each other, and is independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 12 carbon atoms, haloalkyl group with 1 to 12 carbon atoms, and 1 carbon atom Alkoxy group of ⁇ 12, cycloalkyl group of carbon number of 3 to 12, heterocyclic group of carbon number of 3 to 12, alkylsilyl group of carbon number of 3 to 12, carbon number of 6 Arylsilyl group with to 18 carbon atoms, alkylthio group with carbon number of 1 to 12, aryloxy group with carbon number of 6 to 18, arylthio group with carbon number of 6 to 18, and arylthio group with carbon number of 7 to 18 18 aralkyl or
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, or And the L 2 is not an anthracene group;
  • Ar 2 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms or And the Ar 2 is not anthracenyl;
  • Q and T are independently selected from O, S, C(R 7 R 8 ) or Si(R 7 R 8 ),
  • R 3 , R 4 , R 7 , and R 8 are the same or different from each other, and are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.
  • the substitution in refers to the substitution by deuterium, halogen group, cyano group, and alkyl group with 1-4 carbon atoms;
  • R 7 and R 8 are interconnected to atom to which they are attached form a 5-13 yuan aliphatic ring or aromatic ring of 5 to 13 yuan;
  • R 3 and R 4 are interconnected to atom to which they are attached form a 5-13 yuan aliphatic ring or aromatic ring of 5 to 13 yuan;
  • R 5 and R 6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms, Alkoxy group having 1 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, heterocyclic group having 3 to 12 carbon atoms, alkylsilyl group having 3 to 12 carbon atoms, and cycloalkyl group having 3 to 18 carbon atoms Arylsilyl group, alkylthio group with 1 to 12 carbon atoms, aryl group with 6 to 18 carbon atoms, dibenzothienyl or dibenzofuranyl;
  • n 1 represents the number of R 1
  • n 2 represents the number of R 2
  • n 5 represents the number of R 5
  • n 6 represents the number of R 6
  • n 1 , n 2 , n 5 , and n 6 are independent respectively is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n 1 is greater than 1, any two of said R 1 are the same or different, and when n 2 is greater than 1, any two of said R 1
  • the R 2 is the same or different, when n 5 is greater than 1, any two of the R 5 are the same or different, and when n 6 is greater than 1, any two of the R 6 are the same or different.
  • an organic electroluminescence device comprises an anode and a cathode disposed oppositely, and a functional layer disposed between the anode and the cathode; the function
  • the layers contain the compounds described above.
  • an electronic device including the organic electroluminescent device of the present application.
  • the structure of the compound of the present application is a structure formed by connecting adamantane spirofluorene as the main body and a dibenzo five-membered ring through a single bond; the macromolecular structure has strong rigidity, and the freely rotating ⁇ bond makes the two ring planes A certain twist angle is formed between them, so that the compound of the present application has a high first triplet energy level and a suitable HOMO energy level distribution, so it can be used as the host material of the light-emitting layer in organic electroluminescent materials to improve the Efficiency performance of organic electroluminescent devices.
  • the spiro combination of adamantyl and fluorenyl can greatly increase the electron cloud density of the large planar conjugated structure through the hyperconjugation effect, enhance the hole mobility of the compound, and help to promote the transport balance of holes and electrons in the light-emitting layer. Further, the recombination rate of electrons and holes in the organic light-emitting layer can be improved, and the transmission of electrons through the organic light-emitting layer to the hole transport layer can be reduced or avoided, so that the material of the hole transport layer can be effectively protected from the impact of electrons, and the efficiency of the hole transport layer can be improved. lifetime of electroluminescent devices.
  • the adamantyl group spiro-bonded to the fluorenyl group has a large steric volume and strong rigidity, so it can reduce the interaction force between the large planar conjugated structures, reduce the intermolecular ⁇ - ⁇ stacking, and adjust the intermolecular
  • the degree of stacking enables the compound to have a more stable amorphous state during film formation, improves the film-forming property of the compound, and further increases the lifespan of the organic electroluminescent device.
  • the dibenzo five-membered ring and the adamantane spirofluorenyl group are connected by a delta bond, and the dibenzo five-membered ring has a strong energy transfer effect, so when applied to the host material of the light-emitting layer, it can effectively promote light emission
  • the energy transfer between the layer host and the guest can reduce the energy loss and further improve the luminous efficiency.
  • 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 100, anode; 200, cathode; 310, hole injection layer; 321, hole transport layer; 322, electron blocking layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 400, electronic device .
  • the number of carbon atoms in the substituted aryl or heteroaryl group refers to aryl or
  • 2,4-diphenyl-1,3,5-triazinyl belongs to the substituted heteroaryl group with 15 carbon atoms.
  • the two expressions "substituted or unsubstituted aryl group having 6 to 40 carbon atoms" and “substituted or unsubstituted aryl group having 6 to 40 carbon atoms” have the same meaning, and both refer to aryl groups.
  • the total number of carbon atoms of the substituents thereon is 6-40.
  • the two expressions "substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms” and “substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms” have the same meaning, Both mean that the total carbon number of the heteroaryl group and the substituents thereon is 3-30.
  • hetero refers to a functional group including at least 1 heteroatom such as B, N, O, S, Se, Si or P and the remaining atoms are carbon and hydrogen .
  • An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can either refer to In different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, fluorine, chlorine” in the description, its meaning is:
  • formula Q-1 represents that there are q substituents R on the benzene ring ", each R” can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the two benzene rings have q substituents R".
  • the number q of R" substituents may be the same or different, and each R" may be the same or different, and the options of each R" do not affect each other.
  • a heterocyclic group optionally substituted with an alkyl group means that an alkyl group may, but need not, be present, and the description includes both instances in which the heterocyclic group is substituted with an alkyl group and instances in which the heterocyclic group is not substituted with an alkyl group .
  • Tropents attached to the same atom are attached to each other to form a saturated or unsaturated 5- to 18-membered aliphatic ring or a 5- to 18-membered aromatic ring with the atom to which they are commonly attached" means attached to the same atom
  • the two substituents on can form a ring but do not have to form a ring, including the situation where the two are connected to each other to form a saturated or unsaturated 5-18-membered aliphatic ring or a 5-18-membered aromatic ring, and also include the two independent of each other situation of existence.
  • substituted or unsubstituted means no substituents or substituted with one or more substituents.
  • the substituents include, but are not limited to, deuterium, halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio group, cycloalkyl, heterocyclyl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio.
  • alkyl may include straight or branched chain alkyl groups.
  • An alkyl group can have 1 to 12 carbon atoms, and in this application, a numerical range such as “1 to 12" refers to each integer in the given range; for example, “1 to 12 carbon atoms” means that 1 can be included carbon atoms, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms 12-carbon alkyl group.
  • the alkyl group can also be a medium sized alkyl group having 1 to 10 carbon atoms.
  • the alkyl group can also be a lower alkyl group having 1 to 6 carbon atoms. In still other embodiments, the alkyl group contains 1-4 carbon atoms; in still other embodiments, the alkyl group contains 1-3 carbon atoms.
  • the alkyl group may be optionally substituted with one or more substituents described herein.
  • alkyl groups include, but are not limited to, methyl (Me, -CH 3), ethyl (Et, -CH 2 CH 3) , n-propyl (n-Pr, -CH 2 CH 2 CH 3 ), isopropyl (i-Pr, -CH(CH 3 ) 2 ), n-butyl (n-Bu, -CH 2 CH 2 CH 2 CH 3 ), isobutyl (i-Bu, -CH 2 CH ) (CH 3 ) 2 ), sec-butyl (s-Bu, -CH(CH 3 )CH 2 CH 3 ), tert-butyl (t-Bu, -C(CH 3 ) 3 ) and the like. Furthermore, alkyl groups can be substituted or unsubstituted.
  • alkylsilyl refers to Wherein, R G1 , R G2 , R G3 are independently alkyl groups, and specific examples of alkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl , propyldimethylsilyl;
  • arylsilyl refers to Wherein, R G4 , R G5 , and R G6 are independently aryl groups, and specific examples of arylsilyl groups include, but are not limited to, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but not It is not limited to this.
  • halogen groups as substituents are, for example, fluorine, chlorine, bromine or iodine.
  • alkoxy means that an alkyl group is attached to the remainder of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein. Unless otherwise specified, the alkoxy groups contain 1 to 12 carbon atoms. In one embodiment, the alkoxy group contains 1 to 6 carbon atoms; in another embodiment, the alkoxy group contains 1 to 4 carbon atoms; in yet another embodiment, the alkoxy group The group contains 1 to 3 carbon atoms. The alkoxy group may be optionally substituted with one or more substituents described herein.
  • alkoxy groups include, but are not limited to, methoxy (MeO, -OCH 3 ), ethoxy (EtO, -OCH 2 CH 3 ), 1-propoxy (n-PrO, n- Propoxy, -OCH 2 CH 2 CH 3 ), 2-propoxy (i-PrO, i-propoxy, -OCH(CH 3 ) 2 ), 1-butoxy (n-BuO, n- Butoxy, -OCH 2 CH 2 CH 2 CH 3 ), 2-methyl-l-propoxy (i-BuO, i-butoxy, -OCH 2 CH(CH 3 ) 2 ), 2-butanyl Oxy (s-BuO, s-butoxy, -OCH(CH 3 )CH 2 CH 3 ), 2-methyl-2-propoxy (t-BuO, t-butoxy, -OC(CH 3 ) 3 ), etc.
  • alkylthio means that an alkyl group is attached to the remainder of the molecule through a sulfur atom, wherein the alkyl group has the meaning as described herein. Unless otherwise specified, the alkylthio group contains 1 to 12 carbon atoms. In one embodiment, the alkylthio group contains 1 to 6 carbon atoms; in another embodiment, the alkylthio group contains 1 to 4 carbon atoms; in yet another embodiment, the alkylthio group The group contains 1 to 3 carbon atoms. The alkylthio group may be optionally substituted with one or more substituents described herein.
  • alkylthio groups include, but are not limited, methylthio (MeS, -SCH 3), ethylthio (EtS, -SCH 2 CH 3) , 1- propylthio (n-PrS, n- propylthio, -SCH 2 CH 2 CH 3) , 2- propylthio (i-PrS, i- propylthio, -SCH (CH 3) 2) , and the like.
  • haloalkyl or “haloalkoxy” means an alkyl or alkoxy group substituted with one or more halogen atoms, wherein the alkyl and alkoxy groups have the meanings described herein , such examples include, but are not limited to, trifluoromethyl, trifluoromethoxy, and the like.
  • the number of carbon atoms a haloalkyl group containing 1 to 6 fluoro substituted C 1 -C 6 alkyl; In another embodiment, C 1 -C 4 haloalkyl containing fluorine substituted with a C 1 -C 4 alkyl; in another embodiment, C 1 -C 2 haloalkyl containing fluorine-substituted C 1 -C 2 alkyl.
  • cycloalkyl refers to a monocyclic or polycyclic saturated cyclic hydrocarbon group obtained by removing a hydrogen atom, and "cycloalkyl" may have one or more points of attachment to the rest of the molecule.
  • cycloalkyl is a ring system containing 3-12 ring carbon atoms; in other embodiments, cycloalkyl is a ring system containing 5-10 ring carbon atoms; in other embodiments, cycloalkane
  • cycloalkyl is a ring system containing 3-6 ring carbon atoms, for example, "cycloalkyl group of 3-12 carbon atoms" is a ring system containing 5-7 ring carbon atoms; Refers to may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon
  • cycloalkyl groups may independently be unsubstituted or substituted with one or more of the substituents described herein.
  • cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • heterocycle and “heterocyclyl” are used interchangeably, and both refer to a monocyclic, bicyclic or tricyclic ring system, wherein one or more atoms on the ring can be independently optionally substituted by a heteroatom, and the ring Can be fully saturated or contain one or more unsaturated bonds, but are never aromatic, with only one point of attachment to other molecules.
  • One or more ring hydrogen atoms are independently optionally substituted with one or more substituents described herein.
  • heterocycle Some examples of which are "heterocycle”, “heterocyclyl”, “heteroalicyclic” or “heterocyclic” groups are 3-7 membered monocyclic rings (1-6 carbon atoms and selected from 1, 2 or 3 heteroatoms of N, O, P, S, where S or P is optionally substituted by one or more oxygen atoms to give groups like SO, SO 2 , PO, PO 2 , when When the ring is a three-membered ring, which has only one heteroatom), or a 7-10-membered bicyclic ring (4-9 carbon atoms and 1, 2 or 3 heteroatoms selected from N, O, P, S) , where S or P are optionally substituted by one or more oxygen atoms to give groups like SO, SO 2 , PO, PO 2 ).
  • Ring sulfur atoms can optionally be oxidized to S-oxides.
  • the nitrogen atoms of the rings can be optionally oxidized to N-oxygen compounds.
  • heterocycles include, but are not limited to, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl, tetrahydrothienyl, tetrahydropyranyl, dihydropyranyl, tetrahydrothiopyranyl, piperidinyl, Morpholinyl, Thiomorpholinyl, Thioxanyl, Piperazinyl, Homopiperazinyl, Azacyclobutyl, Oxetanyl, Thietanyl, Homopiperidinyl, Glycidol Base, Azacycloheptyl, Oxeptyl, Thiepanyl, Oxazepinyl, Diazepanyl, Thiazepinyl, 2-Pyrrolino, 3-Pyrrolino, Indoline, 2H-pyranyl, 4H-pyranyl, dioxanyl, 1,3-dioxopentyl, pyrazolinyl, dithio
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups linked by A single-ring aryl group and a fused-ring aryl group linked by carbon-carbon bonds, and two or more fused-ring aryl groups linked by a carbon-carbon bond. That is, two or more aromatic groups linked by carbon-carbon bond conjugation can also be regarded as aryl groups in the present application.
  • fused-ring aryl refers to two or more rings in which two carbon atoms in the ring system are shared by two adjacent rings, wherein at least one of the rings is aromatic, for example, the other rings may be Cycloalkyl, cycloalkenyl, aryl.
  • 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 et al.
  • the number of carbon atoms of the aryl group may be selected from 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25 or 30.
  • the aryl group is an aryl group with 6 to 30 carbon atoms, in other embodiments, the aryl group is an aryl group with 6 to 15 carbon atoms, and in other embodiments, the aryl group is a carbon atom An aryl group with 6-18 atoms, and in other embodiments, an aryl group with 6-20 carbon atoms in the aryl group.
  • a substituted aryl group may be one or two or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group (-CN), an aryl group, a heteroaryl group, a trialkylsilyl group , alkyl, cycloalkyl, alkoxy, alkylthio, haloalkyl, aryloxy, arylthio, silyl, alkylamino, aryl, heterocyclic and other groups.
  • a group such as a deuterium atom, a halogen group, a cyano group (-CN), an aryl group, a heteroaryl group, a trialkylsilyl group , alkyl, cycloalkyl, alkoxy, alkylthio, haloalkyl, aryloxy, arylthio, silyl, alkylamino, aryl, heterocyclic and
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, and the like.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents. The total number of carbon atoms of the substituents is 18.
  • the fluorenyl group as an aryl group can be substituted, and the two substituent groups can be combined with each other to form a spiro structure.
  • Specific examples include but are not limited to the following structures:
  • the arylene group is a divalent group, and other than that, the above-mentioned description about the aryl group can be applied.
  • heteroaryl refers to a monocyclic or polycyclic ring containing 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from O, N, P, Si, Se, B, and S in the ring. ring systems, at least one of which is aromatic. Each ring system in a heteroaryl group contains a ring of 5-7 ring atoms with one or more points of attachment to the rest of the molecule.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • Fused ring heteroaryl refers to two or more rings in which the two atoms in the ring system are shared by two adjacent rings, wherein at least one of the rings is aromatic, for example the other ring may be a cycloalkane base, heterocyclyl, cycloalkenyl, aryl.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, oxazolyl, furacyl, pyridyl, Bipyridyl, phenanthridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, Pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarb azolyl, benzothi
  • thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
  • a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like.
  • 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.
  • a substituted heteroaryl group having 14 carbon atoms means that the total carbon number of the heteroaryl group and the substituent is 14.
  • the number of carbon atoms of the heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
  • the heteroaryl group is a heteroaryl group with 3 to 12 carbon atoms, in other embodiments, the aryl group is an aryl group with 3 to 15 carbon atoms, and in other embodiments, the aryl group is an aryl group having 5 to 12 carbon atoms.
  • heteroarylene group is a divalent group, and the above-mentioned description about the heteroaryl group can be applied other than that.
  • a heteroaryl group with a ring-forming carbon number of 3-n refers to the heteroaryl group having 3-n carbon atoms on the heteroaromatic ring, and the carbon atoms in the substituent on the heteroaryl group are 3-n. Atoms are not counted.
  • aryl can be applied to arylene
  • heteroaryl also applies to heteroarylene
  • the explanation for alkyl can be applied to alkylene
  • the explanation for cycloalkyl can be Applied to cycloalkylene.
  • a ring system formed by n atoms is an n-membered ring.
  • phenyl is a 6-membered aryl group.
  • the 6-13-membered aromatic ring refers to a benzene ring, an indene ring, and a naphthalene ring.
  • Ring in this application includes saturated rings, unsaturated rings; saturated rings are cycloalkyl, heterocycloalkyl, unsaturated rings are cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
  • the non-positioning connecting bond refers to the single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (X) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. ) to any possible connection mode shown by formula (X-10).
  • the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, and the meaning it represents, Any possible connection modes shown by formula (X'-1) to formula (X'-4) are included.
  • a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system.
  • the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-positioning link, and the meanings it represents include such as formula (Y-1) ⁇ Any possible connection mode shown by formula (Y-7).
  • ring A and ring B are each independently an aromatic ring having 6 to 14 carbon atoms;
  • X is selected from O, S, Si (R 3 R 4), C (R 3 R 4);
  • Each R 1 is the same or different from each other, and is independently selected from the group consisting of: deuterium, halogen, cyano, alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, and 1 to 12 carbon atoms.
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-40 carbon atoms;
  • L 1 is selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-30 carbon atoms;
  • the substituents in Ar 1 and L 1 are the same or different from each other, and are each independently selected from: deuterium, cyano, halogen, nitro, group U, alkoxy with 1 to 12 carbon atoms, carbon Halogenated alkyl group with 1 to 12 atoms, alkyl group with 1 to 12 carbon atoms, cycloalkyl group with 3 to 12 carbon atoms, heterocyclic group with 3 to 12 carbon atoms, and 3 carbon atoms -12 alkylsilyl group, C6-18 arylsilyl group, C1-12 alkylthio group, C6-18 aryloxy group, C7-C7
  • each of L 1 and Ar 1 when there are two substituents on the same atom, optionally, two of said substituents are connected to each other to form a 5- to 18-membered aliphatic together with the atom to which they are commonly connected family ring or 5- to 18-membered aromatic ring;
  • Each R 2 is the same or different from each other, and is independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 12 carbon atoms, haloalkyl group with 1 to 12 carbon atoms, and 1 carbon atom Alkoxy group of ⁇ 12, cycloalkyl group of carbon number of 3 to 12, heterocyclic group of carbon number of 3 to 12, alkylsilyl group of carbon number of 3 to 12, carbon number of 6 Arylsilyl group with to 18 carbon atoms, alkylthio group with carbon number of 1 to 12, aryloxy group with carbon number of 6 to 18, arylthio group with carbon number of 6 to 18, and arylthio group with carbon number of 7 to 18 18 aralkyl or
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with 3 to 30 carbon atoms, or And the L 2 is not an anthracene group;
  • Ar 2 is selected from substituted or unsubstituted aryl groups with 3 to 30 carbon atoms or And the Ar 2 is not anthracenyl;
  • Q and T are independently selected from O, S, C(R 7 R 8 ) or Si(R 7 R 8 ),
  • R 3 , R 4 , R 7 , and R 8 are the same or different from each other, and are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms.
  • the substitution in refers to the substitution by deuterium, halogen group, cyano group, and alkyl group with 1 to 4 carbon atoms;
  • R 7 and R 8 are interconnected to atom to which they are attached form a 5-13 yuan aliphatic ring or aromatic ring of 5 to 13 yuan;
  • R 3 and R 4 are interconnected to atom to which they are attached form a 5-13 yuan aliphatic ring or aromatic ring of 5 to 13 yuan;
  • R 5 and R 6 are the same or different from each other, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms, Alkoxy group having 1 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, heterocyclic group having 3 to 12 carbon atoms, alkylsilyl group having 3 to 12 carbon atoms, and cycloalkyl group having 3 to 18 carbon atoms Arylsilyl group, alkylthio group with 1 to 12 carbon atoms, aryl group with 6 to 18 carbon atoms, dibenzothienyl or dibenzofuranyl;
  • n 1 represents the number of R 1
  • n 2 represents the number of R 2
  • n 5 represents the number of R 5
  • n 6 represents the number of R 6
  • n 1 , n 2 , n 5 , and n 6 are independent respectively is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n 1 is greater than 1, any two of said R 1 are the same or different, and when n 2 is greater than 1, any two of said R 1
  • the R 2 is the same or different, when n 5 is greater than 1, any two of the R 5 are the same or different, and when n 6 is greater than 1, any two of the R 6 are the same or different.
  • ring A refers to Ring B refers to
  • Ring B refers to
  • ring A is a naphthalene ring, and the number of substituent R 1 is 0;
  • ring B is a naphthalene ring, X is oxygen, and the number of substituent R 2 is 0.
  • ring B includes at least one benzene ring structure, which makes the compound of the present application include at least one dibenzo five-membered condensed ring structure.
  • ring A or ring B in the compound is a condensed ring structure
  • the large plane conjugated structure of the compound is larger, the rigidity is stronger, and the electron cloud density is higher, which makes the compound have stronger hole transport ability, and can further Improve the recombination rate of electrons and holes in the organic light-emitting layer, reduce or prevent electrons from passing through the organic light-emitting layer and transfer to the hole transport layer, thereby effectively protecting the hole transport layer material from the impact of electrons, improving the organic electricity.
  • the lifetime of the luminescent device emits light.
  • the structure of the compound of the present application is a structure formed by connecting adamantane spirofluorene as the main body and a dibenzo five-membered ring through a single bond; the macromolecular structure has strong rigidity, and the freely rotating ⁇ bond makes the two ring planes A certain torsion angle is formed between them, so that the compound of the present application has a high first triplet energy level and a suitable HOMO energy level distribution, and the dibenzo five-membered fused ring has excellent energy transfer effect, which can effectively It promotes the energy transfer between the host material of the light-emitting layer and the guest material, so it can be used as the host material of the light-emitting layer in organic electroluminescent materials to improve the efficiency performance of organic electroluminescent devices.
  • the spiro combination of adamantyl and fluorenyl can greatly increase the electron cloud density of the large planar conjugated structure through the hyperconjugation effect, enhance the hole mobility of the compound, and help to promote the transport balance of holes and electrons in the light-emitting layer , thereby improving the recombination rate of electrons and holes in the organic light-emitting layer, reducing or avoiding the transport of electrons through the organic light-emitting layer to the hole transport layer, thereby effectively protecting the hole transport layer material from the impact of electrons, improving Lifetime of organic electroluminescent devices.
  • the adamantyl group spiro-bonded to the fluorenyl group has a large steric volume and strong rigidity, so it can reduce the interaction force between the large planar conjugated structures, reduce the intermolecular ⁇ - ⁇ stacking, and adjust the intermolecular
  • the degree of stacking enables the compound to have a more stable amorphous state during film formation, improves the film-forming property of the compound, and further increases the lifespan of the organic electroluminescent device.
  • the dibenzo five-membered ring and the adamantane spirofluorenyl group are connected by a delta bond, and the dibenzo five-membered ring has a strong energy transfer effect, so when applied to the host material of the light-emitting layer, it can effectively promote light emission
  • the energy transfer between the layer host and the guest can reduce the energy loss and further improve the luminous efficiency.
  • n 1 +n 2 1.
  • n 1 is 1, n 2 is 0, and R 1 is Alternatively , n 1 is 0, n 2 is 1, and R 2 is
  • X is selected from O, S, Si(R 3 R 4 ) or C(R 3 R 4 ), the R 3 and R 4 are the same, and R 3 , R is selected from methyl or phenyl; or R 3 and R 4 of the interconnecting atoms to which they are attached form a cyclopentane, cyclohexane or a fluorene ring.
  • Q and T are independently selected from O, S, C(R 7 R 8 ) or Si(R 7 R 8 ), and R 7 and R 8 are the same, and R 7 and R 8 are selected from methyl or phenyl; or the R 7 and R 8 are connected to each other to form a cyclopentane, cyclohexane or fluorene ring with the atoms they are commonly connected to.
  • ring A and ring B in the formula (1) are each independently a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring.
  • the ring A is selected from The ring B is selected from
  • ring C and ring D are naphthalene rings, and X, L 1 , L 2 , Ar 1 , and Ar 2 are defined as described in the specification.
  • the L 1 is selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms, a substituted or unsubstituted arylene group with 3-20 carbon atoms Substituted heteroarylene.
  • the L 1 is selected from a single bond, a substituted or unsubstituted arylene group with 6-18 carbon atoms, a substituted or unsubstituted arylene group with 4-18 carbon atoms Substituted heteroarylene.
  • the substituents in the L 1 are the same or different from each other, and each is independently selected from deuterium, fluorine, chlorine, bromine, cyano, and the number of carbon atoms is 1 ⁇ 4 alkyl groups, 1-4 carbon atoms haloalkyl groups, 3-9 carbon atoms trialkylsilyl groups, 5-7 carbon atoms cycloalkyl groups, 6-15 carbon atoms A group consisting of an aryl group and a heteroaryl group having 3 to 12 carbon atoms.
  • the substituents in L 1 are the same or different from each other, each independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl , n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, naphthyl group.
  • the L 1 is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene group, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted anthracylene, substituted or unsubstituted pyrenylene, spiro[ring Pentane-1,9'-fluorene] subunit, spiro[cyclohexane-1,9'-fluorene] subunit, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted Substituted 9,9-dimethyl-9H-9-silafluorenylidene, substituted or un
  • the L 1 is selected from a single bond, or is selected from the group consisting of groups represented by chemical formula (j-1) to chemical formula (j-12);
  • M 2 is selected from single bond or
  • 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 5 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, C or C(J 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C (J 7 ), any two J 7 are the same or different;
  • Q 24 to Q 33 are each independently selected from N, C or C(J 8 ), and at least one of Q 24 to Q 33 is selected from N; when two or more of Q 24 to Q 33 are selected from C (J 8 ), any two J 8 are the same or different;
  • E 1 to E 12 and J 5 to J 8 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3 to 18 carbon atoms, and a group with 6 to 20 carbon atoms.
  • E r E r represents the number of substituents; when r is selected from 1,2, When 3, 4, 5, 6 or 9, er is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, er is selected from 1, 2, 3, 4, 5 or 6; when r When it is 12, er is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, er is selected from 1, 2, 3, 4, 5, 6, 7 or 8 ; When er is greater than 1, any two Er are the same or different;
  • K 3 is selected from O, S, Se, N(E 15 ), C(E 16 E 17 ), Si(E 13 E 14 ); wherein, each of E 13 , E 14 , E 15 , E 16 and E 17 is respectively independently selected from: hydrogen, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms, and an alkyl group with 1-10 carbon atoms;
  • E 16 and E 17 are interconnected to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly attached;
  • E 13 and E 14 are interconnected to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly attached;
  • Each K 4 is independently selected from single bond, O, S, Se, N(E 20 ), C(E 21 E 22 ), Si(E 18 E 19 ); wherein, each of E 20 , E 21 , E 22 , E 18 and E 19 are independently selected from: hydrogen, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms, and an alkyl group with 1-10 carbon atoms;
  • E 21 and E 22 are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly connected;
  • E 18 and E 19 are interconnected to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly attached.
  • L 1 is , when M 2 and K 4 are single bonds, E 11 is both hydrogen, and K 3 is C (E 16 E 17 ), optionally, E 16 and E 17 connected to the same atom are connected to each other to connect with
  • the atoms to which they are connected together form a saturated or unsaturated 5- to 13-membered aliphatic ring, which means that E 16 and E 17 can be connected to each other to form a 5- to 13-membered ring, or they can exist independently of each other; when E 16 and E 17 form In the case of an aliphatic ring, the number of atoms in the ring may be a 5-membered ring, such as It can also be a 6-membered ring, e.g.
  • E 16 and E 17 can also be a 10-membered ring, e.g.
  • the number of atoms on the ring formed by the interconnection of E 16 and E 17 may also be other values, which will not be listed one by one here.
  • the ring formed by the interconnection of E 16 and E 17 can also be an aromatic ring, such as a 13-membered aromatic ring,
  • E 13 and E 14 are connected to each other to form a 5- to 13-membered aliphatic or aromatic ring with the atoms to which they are commonly connected, and have the same meanings as E 13 and E 14.
  • E 21 and E 22 are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly connected have the same meanings as E 16 and E 17 .
  • E 18 and E 19 are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly connected have the same meanings as E 16 and E 17 .
  • the L 1 is selected from a single bond, a substituted or unsubstituted W 1 wherein, the unsubstituted W 1 is selected from the group consisting of the following groups:
  • the substituted W 1 is the unsubstituted W 1 which is selected from one or more groups selected from the group consisting of deuterium, fluorine, chlorine, bromine, cyano, alkyl groups with 1 to 4 carbon atoms, and haloalkanes with 1 to 4 carbon atoms. radicals, trialkylsilyl groups with 3 to 9 carbon atoms, cycloalkyl groups with 5 to 7 carbon atoms, aryl groups with 6 to 15 carbon atoms, and heteroaryl groups with 3 to 12 carbon atoms
  • the substituted W 1 is an unsubstituted W 1 that is selected from one or more groups selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl
  • a group formed by substituting with substituents such as n-propyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, and naphthyl.
  • a "plurality" of substituents means more than one, which may be 2, 3, 4, 5, 6, 7 or 8.
  • the L 1 is selected from the group consisting of a single bond or the following groups:
  • L 1 is not limited to the above-mentioned groups.
  • Ar 1 is selected from the group consisting of groups represented by chemical formula i-1 to chemical formula i-18:
  • M 1 is selected from single bond or
  • G 1 to G 5 are each independently selected from N or C(F 1 ), and at least one of G 1 to G 5 is selected from N; when two or more of G 1 to G 5 are selected from C(F 1 ) , any two F 1 are the same or different;
  • G 6 to G 13 are each independently selected from N or C(F 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(F 2 ) , any two F 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(F 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(F 3 ) , any two F 3 are the same or different; or, optionally, two adjacent F 3 are connected to each other to form a 5-10-membered aromatic ring or a 5-10-membered heteroaromatic ring;
  • G 24 to G 33 are each independently selected from N or C(F 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(F 4 ) , any two F 4 are the same or different; or, optionally, two adjacent F 4 are connected to each other to form a 5-10-membered aromatic ring or a 5-10-membered heteroaromatic ring;
  • G 34 to G 37 are each independently selected from N or C(F 5 ), and when two or more of G 34 to G 37 are selected from C(F 5 ), any two F 5 are the same or different; or, Optionally, two adjacent F 5 are connected to each other to form a 5-10-membered aromatic ring or a 5-10-membered heteroaromatic ring;
  • G 38 to G 45 are each independently selected from N or C(F 6 ), and at least one of G 38 to G 45 is selected from N; when two or more of G 38 to G 45 are selected from C(F 6 ) , any two F 6 are the same or different;
  • G 46 to G 53 are each independently selected from N or C(F 7 ), and at least one of G 46 to G 53 is selected from N; when two or more of G 46 to G 53 are selected from C (F 7 ) 7 ), any two F 7 are the same or different; or, optionally, two adjacent F 7 are connected to each other to form a 5-10-membered aromatic ring or a 5-10-membered heteroaromatic ring;
  • D 1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl with 3 to 12 carbon atoms, alkyl with 1 to 10 carbon atoms, and 1 to 10 carbon atoms haloalkyl, cycloalkyl with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms, alkylthio group with 1-10 carbon atoms;
  • D 2 to D 9 and D 21 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms group, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, carbon Alkylthio groups with 1-10 atoms, aryl groups with 3-20 carbon atoms, and heteroaryl groups with 3-18 carbon atoms;
  • D 10 to D 20 and F 1 to F 7 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and 1 to 12 carbon atoms.
  • d 1 to d 21 are represented by d k
  • D 1 to D 21 are represented by D k
  • k is a variable, representing any integer from 1 to 21
  • d k represents the number of substituents D k ; wherein, when k is selected from 5 or 17, d k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, d k is selected from 1, 2, 3 or 4; When from 1, 3, 4, 6, 9 or 14, d k is selected from 1, 2, 3, 4 or 5; when k is 13, d k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, d k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, d k is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is 11, d k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when d k is greater than 1, any two D k are the same or different;
  • K 1 and K 6 are independently selected from O, S, N(D 22 ), C(D 23 D 24 ), Si(D 28 D 29 ); wherein each of D 22 , D 23 , D 24 , D 28 , D 29 are independently selected from: an aryl group with a carbon number of 6-18, a heteroaryl group with a carbon number of 3-18, an alkyl group with a carbon number of 1-10 or an alkyl group with a carbon number of 3-10 cycloalkyl;
  • D 23 and D 24 are interconnected to form a 5- to 14-membered aliphatic ring or a 5- to 14-membered aromatic ring with the atoms to which they are commonly attached;
  • D 28 and D 29 are interconnected to form a 5- to 14-membered aliphatic ring or a 5- to 14-membered aromatic ring with the atoms to which they are commonly attached;
  • K 2 is selected from single bond, O, S, N(D 25 ), C(D 26 D 27 ), Si(D 30 D 31 ); wherein, each of D 25 , D 26 , D 27 , D 30 , D 31 are independently selected from: aryl groups with 6-18 carbon atoms, heteroaryl groups with 3-18 carbon atoms, alkyl groups with 1-10 carbon atoms, or cycloalkanes with 3-10 carbon atoms base,
  • D 26 and D 27 are interconnected to form a 5- to 14-membered aliphatic ring or a 5- to 14-membered aromatic ring with the atoms to which they are commonly attached;
  • the D 30 and D 31 are interconnected to atom to which they are attached form a 5-14 yuan aliphatic ring or aromatic ring of 5 to 14 yuan;
  • K 5 is selected from O, S, Se, N(D 32 ), C(D 33 D 34 ), wherein D 32 , D 33 and D 34 are each independently selected from: an aryl group having 6 to 18 carbon atoms , a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.
  • two adjacent F 5 are connected to each other to form a 5-10-membered aromatic ring or a 5-10-membered heteroaromatic ring
  • i-16 when K 5 is O, G 34 and G 35 are both CH, G 36 and G 37 are both C (F 5 ) and both form a 6-membered aromatic ring, the formula i-16 is
  • the adjacent F 5 can also form other aromatic rings or heteroaromatic rings, which will not be listed here.
  • the meanings of two adjacent F 3 , F 4 or F 7 connected to each other to form a ring are the same as this, and will not be listed one by one.
  • D 23 and D 24 are connected to each other to form a 5- to 14-membered aliphatic ring or a 5- to 14-membered aromatic ring with the atoms to which they are commonly connected" means that D 23 and D 24 can be connected to each other to form a Rings can also exist independently of each other.
  • the ring can be a 5-membered aliphatic family rings, such as Can also be a 6-membered aliphatic ring, such as Can be a 13-membered aromatic ring such as It can also be a 14-membered heteroaromatic ring, such as
  • the number of carbon atoms on the ring formed by D 23 and D 24 being connected to each other may also be other values, which will not be listed one by one here.
  • D 26 and D 27 are interconnected to form a 5- to 14-membered aliphatic or aromatic ring with the atoms to which they are commonly attached have the same meanings as D 23 and D 24 .
  • D 28 and D 29 , D 26 and D 27 , D 30 and D 31 connected to each other to form a 5- to 14-membered aliphatic or aromatic ring with the atoms to which they are commonly attached have the same meanings as D 23 and D 24 same.
  • At least two of G 1 to G 5 are selected from N.
  • At least two of G 6 to G 13 are selected from N.
  • At least two of G 14 to G 23 are selected from N.
  • At least two of G 24 to G 33 are selected from N.
  • At least two of G 38 to G 45 are selected from N.
  • At least two of G 46 to G 53 are selected from N.
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6, 10, 12, 14, 15, 16, 18, 20, 25 carbon atoms, and 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, Substituted or unsubstituted heteroaryl of 30, 31, 32, 33, 34, 35, 36.
  • Ar 1 is selected from a substituted or unsubstituted aryl group having 6-18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 15-26 carbon atoms.
  • the substituents in Ar 1 are one or more, which are the same or different from each other, and are independently selected from deuterium, fluorine, chlorine, cyano, and 6 carbon atoms.
  • Ar 1 is selected from a substituted or unsubstituted group W 3 , wherein unsubstituted W 3 is selected from the group consisting of:
  • each T 1 , T 2 and T 3 are the same or different from each other, and are independently selected from hydrogen, an aryl group with 6 to 20 carbon atoms, and a heteroaryl group with 3 to 20 carbon atoms; any two T 1 is the same or different, any two T 2 are the same or different, any two T 3 are the same or different;
  • the substituted W 3 is the unsubstituted W 3 which is selected from one or more groups selected from the group consisting of deuterium, fluorine, chlorine, cyano, alkyl groups with 1 to 4 carbon atoms, and alkoxy groups with 1 to 4 carbon atoms.
  • cycloalkyl groups with 3 to 7 carbon atoms aryl groups with 6 to 15 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms, alkylthio groups with 1 to 4 carbon atoms, carbon atoms
  • alkylthio groups with 1 to 4 carbon atoms carbon atoms
  • substituted W 3 means that the unsubstituted W 3 is substituted by one or more substituents, and the substituent can replace the hydrogen atom at any position in the above-mentioned unsubstituted W 3 , for example, it can also be is any hydrogen atom in the groups T 1 , T 2 and T 3 .
  • T 1 , T 2 or T 3 when T 1 , T 2 or T 3 is hydrogen, it can also be connected to W 3 instead of T 1 , T 2 or T 3 without positioning the bond.
  • T 1 when T 1 is hydrogen, it can also represent
  • each T 1 , T 2 and T 3 are the same or different from each other, and are independently selected from: hydrogen, phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, fluorenyl, diphenyl thienyl, dibenzofuranyl, N-phenylcarbazolyl, carbazol-9-ylphenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl , benzoxazine, triphenylene, phenoline; substituted W 3 is unsubstituted W 3 is one or more selected from: fluorine, deuterium, cyano, trifluoromethyl, trimethylsilyl , methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoro
  • Ar 1 may be selected from an electron-deficient heteroaryl group (also known as an electron-poor heteroaryl group), and the heteroatoms on it can reduce the electron cloud density of the conjugated system of the heteroaryl group as a whole
  • an electron-deficient heteroaryl group also known as an electron-poor heteroaryl group
  • the heteroatoms on it can reduce the electron cloud density of the conjugated system of the heteroaryl group as a whole
  • the heteroatom makes the electron cloud density of the conjugated system due to the strong electronegativity. reduce.
  • electron deficient heteroaryl groups can include, but are not limited to, pyridyl, pyrimidinyl, s-triazinyl, quinolyl, isoquinolinyl, benzopyrazolyl, benzimidazolyl, quinoxalinyl, phenanthroline, etc.
  • Ar 1 can form the electron transport core group of the compound, so that the compound can effectively realize electron transport, and can effectively balance the transport rates of electrons and holes in the organic light-emitting layer.
  • the compound can be used as the host material of the bipolar organic light-emitting layer to simultaneously transport electrons and holes, and can also be used as the host material of the electron-type organic light-emitting layer in combination with the host material of the hole-type organic light-emitting layer.
  • the dibenzo five-membered ring with hole transport ability and the electron-deficient heteroaryl group (Ar 1 ) with electron transport ability are respectively connected with the core structure of adamantane spirofluorene through a single bond, which is more conducive to the compound
  • the balance of electron transport performance and hole transport performance; in addition, the compound connected in this way has a higher T 1 energy level, and has improved tolerance to excitons, and is more suitable as a host material for the light-emitting layer.
  • Ar 1 is selected from the following structures:
  • Ar 1 when R 2 is not , Ar 1 can also be selected from aryl or electron-rich heteroaryl. These electron-rich aromatic groups can increase the electron cloud density of the conjugated system as a whole, and can adjust the HOMO energy level of the compound, so the compound will have better hole transport ability, and dibenzofuranyl, dibenzofuranyl, dibenzofuran
  • the thiazolyl group also has excellent energy transfer function, when the compound is used as the host of the light-emitting layer, it can reduce the energy loss and improve the device efficiency.
  • Ar 1 is selected from the following structures:
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or And L 2 is not an anthracene group.
  • Q is selected from O, S, C(R 7 R 8 ) or Si(R 7 R 8 ), the R 7 and R 8 are the same, and R 7 , R 8 is selected from methyl or phenyl; or the R 7 and R 8 are connected to each other to form a cyclopentane, cyclohexane or fluorene ring with the atoms they are connected to in common, and each R 5 is independently selected from deuterium, fluorine, chlorine , cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, naphthyl.
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted arylene group Dibenzofuranylidene, substituted or unsubstituted dimethylfluoreneidene, substituted or unsubstituted 9,9-dimethyl-9H-9-silafluoreneidene, and L 2 is not anthracenylene.
  • the substituents in the L 2 are the same or different from each other, each independently selected from deuterium, fluorine, chlorine, cyano, alkyl with 1 to 4 carbon atoms, carbon Alkoxy group having 1 to 4 atoms, cycloalkyl group having 3 to 7 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 5 to 18 carbon atoms, 1 to 4 alkylthio groups, 1 to 4 carbon atoms halogenated alkyl groups, and 3 to 9 carbon atoms substituted alkylsilyl groups, and when the number of substituents in L 2 is When there are more than one, any two substituents are the same or different.
  • the L 2 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenylene, or Unsubstituted naphthylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted phenanthrene, spiro[cyclopentane-1,9'-fluorene] subunit, spiro[ Cyclohexane-1,9'-fluorene] subunit, substituted or unsubstituted 9,9-dimethyl-9H-9-silafluorene subunit, substituted or unsubstituted dibenzofuran subunit, substituted Or one of unsubstituted dibenzothiophene subunits, substituted or unsubsti
  • the L 2 is selected from a single bond, a substituted or unsubstituted W 2 wherein, the unsubstituted W 2 is selected from the group consisting of:
  • the substituted W 2 is the unsubstituted W 2 which is selected from one or more groups selected from the group consisting of deuterium, fluorine, chlorine, bromine, cyano, alkyl groups with 1 to 4 carbon atoms, and haloalkanes with 1 to 4 carbon atoms.
  • the substituted W 2 is the unsubstituted W 2 is selected from one or more deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl A group formed by substituting groups such as n-propyl group, n-propyl group, tert-butyl group, methoxy group, ethoxy group, trifluoromethyl group, trimethylsilyl group, phenyl group and naphthyl group.
  • L 2 is selected from the following structures:
  • L 2 is not limited to the above-mentioned groups.
  • Ar 2 is selected from a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or And Ar 2 is not an anthracene group.
  • T is selected from O, S, C(R 7 R 8 ) or Si(R 7 R 8 ), the R 7 and R 8 are the same, and R 7 , R 8 is selected from methyl or phenyl; or the R 7 and R 8 are connected to each other to form a cyclopentane, cyclohexane or fluorene ring with the atoms they are commonly connected to, and each R 6 is independently selected from deuterium, fluorine, chlorine , cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, trifluoromethyl, trimethylsilyl, phenyl, fluorenyl, cyano-substituted phenyl, Fluorine-substituted phenyl, naphthyl, dibenzothiophene, dibenzofuran, cyclohexyl, trimethylsilyl.
  • Ar 2 is selected from substituted or unsubstituted aryl with 6, 10, 12, 14, 15, 16, 18, 20 or 25 carbon atoms, substituted or unsubstituted diphenyl thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted 9,9-dimethyl-9H-9-silafluorenyl, and Ar 2 is not anthracenyl.
  • the substituents in Ar 2 are the same or different from each other, and each is independently selected from deuterium, fluorine, chlorine, cyano, and alkyl groups with 1 to 4 carbon atoms, Alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, optionally substituted by 0, 1, 2 or 3 substituents selected from deuterium, fluorine, cyano and methyl Substituted aryl group with 6-15 carbon atoms, optionally substituted by 0, 1, 2 or 3 substituents selected from deuterium, fluorine, cyano, methyl, with 5-18 carbon atoms A heteroaryl group, an alkylthio group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms, and an alkylsilyl group with 3 to 9 carbon atoms are substituted, and when When the number of substituents in Ar 2 is plural, any two substituents may be
  • Ar 2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted Unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted dibenzofuranylidene, substituted or unsubstituted dibenzothiopheneylidene, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted Substituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, spiro[cyclopentane-1,9'-fluorenyl], spiro
  • the Ar 2 is selected from a substituted or unsubstituted group W 4 , wherein the unsubstituted W 4 is selected from the group consisting of:
  • the substituted W 4 is the unsubstituted W 4 which is selected from one or more groups selected from the group consisting of deuterium, fluorine, chlorine, cyano, alkyl groups with 1 to 4 carbon atoms, and alkoxy groups with 1 to 4 carbon atoms.
  • cycloalkyl groups with 3 to 7 carbon atoms aryl groups with 6 to 14 carbon atoms, heteroaryl groups with 3 to 12 carbon atoms, alkylthio groups with 1 to 4 carbon atoms, carbon atoms
  • alkylthio groups with 1 to 4 carbon atoms carbon atoms
  • substituted W 4 is unsubstituted W 4 is selected from one or more groups selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy , trifluoromethyl, trimethylsilyl, phenyl, fluorenyl, cyano-substituted phenyl, fluorine-substituted phenyl, naphthyl, dibenzothiophene, dibenzofuran, cyclohexyl, tri A group formed by substituting a methylsilyl group.
  • each R 1 is the same or different from each other, and each is independently selected from: deuterium, fluorine, chlorine, cyano, alkyl having 1 to 4 carbon atoms, and 1 to 4 carbon atoms.
  • each R 1 is the same or different from each other, and each is independently selected from: fluorine, deuterium, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl radical, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, triphenyl Silane or
  • each R 2 is the same or different from each other, and is independently selected from deuterium, fluorine, chlorine, cyano, alkyl having 1 to 4 carbon atoms, and 1 to 4 carbon atoms.
  • each R 2 is the same or different from each other, and each is independently selected from: fluorine, deuterium, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl , tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclopentyl, cyclohexane, phenyl, triphenylsilyl or
  • Ar 2 is selected from aryl or electron-rich dibenzofuranyl, dibenzothiazolyl, these electron-rich aromatic groups as a whole can increase the electron cloud density of the conjugated system such as oxygen
  • the lone pairs of electrons on atoms and sulfur atoms can participate in the conjugated system to increase the electron cloud density of the conjugated system of heteroaryl. Since the aryl group and the electron-rich dibenzofuranyl group and the dibenzothiazolyl group can effectively enhance the electron cloud density of the compound and adjust the HOMO energy level of the compound, the compound will have better hole transport ability. And dibenzofuranyl, dibenzothiazolyl also have excellent energy transfer. In this way, the compound can be used as the host material of the hole-type organic light-emitting layer, and cooperate with the host material of the electron-type organic light-emitting layer for electron transport to form the host material of the organic light-emitting layer together.
  • Ar 2 is selected from the following structures:
  • Ar 2 is not limited to the above-mentioned groups.
  • the compound is selected from the group consisting of:
  • the present application also provides an organic electroluminescent device, the organic electroluminescent device includes an anode and a cathode disposed opposite to each other, and an organic light-emitting layer disposed between the anode and the cathode; the organic light-emitting layer comprises the above-mentioned compounds to improve the voltage characteristics, efficiency characteristics and lifetime characteristics of organic electroluminescent devices.
  • the compounds of the present application can be used as one-component host materials or as one of two-component hybrid host materials.
  • the organic electroluminescent device may include an anode 100 , a hole transport layer 321 , an organic light emitting layer 330 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
  • the compounds provided in the present application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device to improve the lifespan of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device or reduce the driving voltage of the organic electroluminescent device.
  • the anode 100 includes an anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (the IZO); a combination of metal and oxides such as ZnO: Al or SnO 2: Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2- oxy)thiophene] (PEDT), polypyrrole and polyaniline.
  • a transparent electrode comprising indium tin oxide (ITO) as the anode.
  • the hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. This does not make special restrictions.
  • the organic light-emitting layer 330 may include 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 may recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to Host material, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the host material may be composed of the compounds of the present application, especially the compounds containing electron-deficient aromatic heterocycles in the R 1 group.
  • Such compounds can simultaneously transport electrons and holes, and can balance the transport efficiency of holes and electrons, so that electrons and holes can be efficiently recombined in the organic light-emitting layer, thereby improving the light-emitting efficiency of organic electroluminescent devices.
  • the host material may be a composite material, for example, may include the compound of the present application and the host material of the electron-type organic light-emitting layer.
  • the compound of the present application can effectively transport holes, so that the hole transport efficiency is balanced with the electron transport efficiency of the organic light-emitting layer, so that the electrons and holes can be efficiently recombined in the organic light-emitting layer, and the light emission of the organic electroluminescent device is improved.
  • host materials can include compounds of the present application and GH-n1.
  • the guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not specially made in this application. limit.
  • the guest material of the organic light-emitting layer 330 may be Ir(piq) 2 (acac) or the like.
  • the guest material of the organic light-emitting layer 330 may be Ir(ppy) 3 or the like.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode comprising aluminum as the cathode.
  • the material of the cathode 200 may be magnesium-silver alloy.
  • a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the capability of injecting holes into the 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 specifically limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron blocking layer 322 may also be provided between the hole transport layer 321 and the organic light-emitting layer 330 to block electrons from being transported to the side of the hole transport layer 321 , thereby improving the electrons and holes in the organic light-emitting layer 321 .
  • the material of the electron blocking layer 322 may be a carbazole polymer, a carbazole-linked triarylamine compound, or other feasible structures.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 may include LiQ.
  • the present application further provides an electronic device 400 , as shown in FIG. 2 , the electronic device 400 includes any organic electroluminescent device described in the foregoing organic electroluminescent device embodiments.
  • the electronic device 400 may be 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. Since the electronic device 400 has any of the organic electroluminescence devices described in the above organic electroluminescence device embodiments, it has the same beneficial effects, and details are not described herein again.
  • the rest of the conventional reagents are from Shantou Xilong Chemical Factory, Guangdong Guanghua Chemical Reagent Factory, Guangzhou Chemical Reagent Factory, Tianjin Haoyuyu Chemical Co., Ltd., Tianjin Fuchen Chemical Reagent Factory, Wuhan Xinhuayuan Technology Development Co., Ltd., Qingdao Tenglong It can be purchased from Chemical Reagent Co., Ltd. and Qingdao Ocean Chemical Factory.
  • Anhydrous tetrahydrofuran, dioxane, toluene, ether and other anhydrous solvents are obtained by refluxing and drying with metallic sodium.
  • reaction in each synthesis example is generally carried out under the positive pressure of nitrogen or argon, or a drying tube is set on the anhydrous solvent (unless otherwise stated); in the reaction, the reaction flask is plugged with a suitable rubber stopper, The substrate is injected into the reaction vial via a syringe. All glassware used was dried.
  • the chromatographic column was a silica gel column, and silica gel (100-200 mesh) was purchased from Qingdao Ocean Chemical Factory.
  • the measurement conditions of low-resolution mass spectrometry (MS) data are: Agilent 6120 quadrupole HPLC-M (column type: Zorbax SB-C18, 2.1 ⁇ 30 mm, 3.5 microns, 6 min, flow rate 0.6 mL/ min.
  • Mobile phase 5%-95% (acetonitrile with 0.1% formic acid) in (water with 0.1% formic acid) using electrospray ionization (ESI) at 210nm/254nm with UV detection.
  • ESI electrospray ionization
  • Hydrogen nuclear magnetic resonance spectrum Bruker 400MHz nuclear magnetic instrument, at room temperature, with CDCl 3 as solvent (in ppm), with TMS (0 ppm) as reference standard. When multiplets are present, the following abbreviations will be used: s (singlet), d (doublet), t (triplet), m (multiplet).
  • Target compounds were detected by UV at 210 nm/254 nm using Agilent 1260 pre-HPLC or Calesep pump 250 pre-HPLC (column type: NOVASEP50/80 mmDAC).
  • the solution was raised to 80°C after the dropwise addition, and stirred for 2 hours; cooled to room temperature, the precipitated solid was filtered, the filter cake was rinsed with water and ethanol, the solid was collected, and dried to obtain the crude product; the dichloromethane/n-heptane system was used The crude product was purified by silica gel column chromatography to obtain intermediate c-1 (20.0 g, 75% yield) as a white solid.
  • Intermediate f was synthesized using a method similar to that used for the synthesis of intermediate f-1, using the compound shown in reactant A in Table 6 in place of intermediate e-1 and the compound shown in reactant B in place of 3-bromodibenzofuran -2 to f-14:
  • the organic phase is washed with water and then dried with anhydrous magnesium sulfate, and the solvent is removed under reduced pressure to obtain the crude product ;
  • the crude product was purified by silica gel column chromatography using a dichloromethane/n-heptane system to obtain a white solid intermediate I-1 (15.4 g, yield 60%).
  • ITO thickness was The ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and a photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can use ultraviolet ozone and O 2 : N 2 plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used to clean the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate. It should be noted that the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not specifically limited.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL), and HT-01 was evaporated on the hole injection layer to form a thickness of the first hole transport layer.
  • HIL hole injection layer
  • HT-02 was vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • compound 62:GH-n1:Ir(ppy) 3 was co-evaporated in a ratio of 52%:43%:5% (evaporation rate) to form a thickness of green emissive layer (EML).
  • EML green emissive layer
  • ET-01 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • the thickness of the vapor deposition on the above-mentioned cathode is The CP-01 is formed to form an organic capping layer (CPL), thereby completing the preparation of the entire organic light-emitting device.
  • CPL organic capping layer
  • An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the mixed components shown in Table 17 below were used instead of the mixed components in Example 1 when the light-emitting layer was formed.
  • An organic electroluminescent device was prepared in the same manner as in Example 1, except that the mixed components shown in Table 17 below were used instead of the mixed components in Example 1 when the light-emitting layer was formed.
  • the organic electroluminescent devices prepared in Examples 1 to 26 have basically similar driving voltages and at least improved luminous efficiency compared with the organic electroluminescent devices prepared in Comparative Examples 1 to 5. 16.3%, the device lifetime is improved by at least 20.3%. Therefore, when the compound of the present application is used as the organic light-emitting layer material of the organic electroluminescent device, especially when used as the host material of the organic light-emitting layer of the organic electroluminescent device, it can effectively improve the efficiency performance of the organic electroluminescent device. and longevity.
  • the adamantane spirofluorene ring is directly connected to a dibenzo five-membered ring in the structure of the compound of the present application, the energy transmission ability is improved, the exciton tolerance is improved, and it is more suitable as an electronic light emitting layer host material, while Compound A is more suitable for electron transport layers.
  • ITO thickness was The ITO substrate is cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and a photolithography process is used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, and can use ultraviolet ozone and O 2 : N 2 plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used to clean the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate. It should be noted that the ITO substrate can also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not specifically limited.
  • HT-04 was vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • EML red emissive layer
  • ET-01 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • the thickness of the vapor deposition on the above-mentioned cathode is The CP-01 was formed to form an organic capping layer (CPL), thereby completing the preparation of the organic light-emitting device.
  • CPL organic capping layer
  • An organic electroluminescent device was fabricated in the same manner as in Example 27, except that the mixed components shown in Table 18 below were used instead of the mixed components in Example 27 when forming the light-emitting layer.
  • An organic electroluminescent device was prepared in the same manner as in Example 27, except that the host of the light-emitting layer in Example 27 was replaced with the mixed components shown in Table 18 below when forming the light-emitting layer.
  • the organic electroluminescent devices prepared in Examples 27 to 34 have similar driving voltages and at least improved luminous efficiency compared with the organic electroluminescent devices prepared in Comparative Examples 6 to 8. 19.4%, and lifespan increased by at least 30.1%. Therefore, when the compound of the present application is used as the material of the organic light-emitting layer of the organic electroluminescent device, especially when used as the host material of the organic light-emitting layer of the organic electroluminescent device, the efficiency performance and life performance of the organic electroluminescent device can be improved. .
  • the dibenzo five-membered ring and the electron-deficient heteroaryl group in the structure of the compound of the present application are not directly connected, but are respectively connected with spirofluorene, so T 1 is significantly improved, The exciton tolerance is improved, and it is more suitable as the host material of the electron-type light-emitting layer, while the compound Z is more suitable for the electron transport layer.
  • the adamantyl group which is a part of the compound core, is spiro-bonded with the fluorenyl group to obtain adamantane spirofluorene, and the adamantane spirofluorene and the dibenzo five-membered condensed ring are connected by a single bond, so that the compound as a whole has strong rigidity
  • the compound of the present application have a high first triplet energy level, the macromolecular structure has strong rigidity, and the freely rotating delta bond forms a certain torsion angle between the two ring planes, so the compound of the present application is made.
  • the dibenzo five-membered fused ring has excellent energy transfer, which can effectively promote the energy transfer between the host and guest materials of the light-emitting layer. Therefore, It can be used as the host material of the light-emitting layer in the organic electroluminescent material to improve the efficiency performance of the organic electroluminescent device.
  • the spiro combination of adamantyl and fluorenyl can greatly increase the electron cloud density of the large planar conjugated structure through the hyperconjugation effect, enhance the hole mobility of the compound, and help to promote the transport balance of holes and electrons in the light-emitting layer , thereby improving the recombination rate of electrons and holes in the organic light-emitting layer, reducing or preventing electrons from passing through the organic light-emitting layer and transporting them to the hole transport layer, thereby effectively protecting the hole transport layer material from the impact of electrons, improving Lifetime of organic electroluminescent devices.
  • the adamantyl group spiro-bonded to the fluorene group has a large steric volume and strong rigidity, so it can reduce the interaction force between the large planar conjugated structures, reduce the intermolecular ⁇ - ⁇ stacking, and adjust the intermolecular
  • the degree of stacking enables the compound to have a more stable amorphous state during film formation, improves the film-forming property of the compound, and further increases the lifespan of the organic electroluminescent device.

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Abstract

本申请提供一种有机化合物、有机电致发光器件和电子装置，本申请的有机化合物的化学结构包含金刚烷螺芴环和二苯并五元环，该有机化合物具有优良的能量传递功能，可以用作致电发光器件中的发光层材料，改善有机电致发光器件的效率并提高有机电致发光器件的寿命。

Description

化合物、有机电致发光器件及电子装置
相关申请的交叉引用
本申请要求于2020年7月20日递交的、申请号为CN202010699979.1的中国专利申请的优先权，在此引用上述中国专利申请公开的内容全文以作为本申请的一部分。本申请要求于2020年8月19日递交的、申请号为CN202010835565.7的中国专利申请的优先权，在此引用上述中国专利申请公开的内容全文以作为本申请的一部分。
技术领域
本申请属于有机电致发光材料技术领域，具体涉及一种化合物、使用其的有机致电发光器件及电子装置。
背景技术
有机电致发光器件，例如有机发光二极管(OLED)，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，且一般包括有机发光层、位于有机发光层与阳极之间的空穴传输层、位于有机发光层与阴极之间的电子传输层。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。
现有技术中，CN104039778A等公开了可以在有机电致发光器件中制备发光层的材料。但是目前的有机致电发光材料依然存在发光寿命短、发光效率低的问题。因此，有必要继续研发新型的材料，以进一步提高有机电致发光器件的寿命和效率性能。
发明内容
本申请的目的在于提供一种性能优异的有机电致发光材料，可用作有机电致发光器件中的发光层层。
为了实现上述目的，本申请提供一种化合物，所述化合物的结构式如化学式1所示：
Figure PCTCN2021083413-appb-000001
其中，环A和环B各自独立地为碳原子数6～14的芳环；
X选自O、S、Si(R 3R 4)、C(R 3R 4)；
各R 1彼此相同或不同，且各自独立地选自：氘、卤素、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为3～12的的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12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7～18的芳烷氧基或
Figure PCTCN2021083413-appb-000002
Ar 1选自碳原子数为6～40的取代或未取代的芳基，碳原子数为3～40的取代或未取代的杂芳基；
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3～30的取代或未取代的亚杂芳基；
Ar 1和L 1中的取代基彼此相同或不同，且各自独立地选自：氘、氰基、卤素基团、硝基、基团U、碳原子数为1～12的烷氧基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷基、碳原子数为3～12的环烷基、碳原子数为3～12的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12的烷硫基、碳原子数为6～18的芳氧基、碳原子数为7～18的芳烷基或碳原子数为6～18的芳氧基构成的组，所述基团U选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基，所述芳基和杂芳基中的取代基选自氘、氰基、卤素基团、碳原子数为1～12的烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为1～12的卤代烷基、碳原子数为3～12的烷基硅烷基、碳原子数为6～20的芳基或碳原子数为3-18的杂芳基所构成的组；
或者，在各L 1和Ar 1中，当同一原子上具有两个取代基时，任选地，两个所述取代基相互连接，以与它们所共同连接的原子一起形成5到18元脂肪族环或5到18元芳香环；
各R 2彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为3～12的的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12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7～18的芳烷基或
Figure PCTCN2021083413-appb-000003
L 2选自单键、碳原子数为6-30的取代或未取代的亚芳基或
Figure PCTCN2021083413-appb-000004
且所述L 2不为亚蒽基；
Ar 2选自碳原子数为6-30的取代或未取代的芳基或
Figure PCTCN2021083413-appb-000005
且所述Ar 2不为蒽基；
其中，Q和T分别独立地选自O、S、C(R 7R 8)或Si(R 7R 8)，
R 3、R 4、R 7、R 8彼此相同或不同，且各自独立地选自氢、碳原子数1～12的取代或未取代的烷基、碳原子数1～12的取代或未取代的卤代烷基、碳原子数为6～18的取代或未取代的芳基、碳原子数为3～18的取代或未取代的杂芳基，所述R 3、R 4、R 7和R 8中的取代是指被氘、卤素基团、氰基、碳原子数为1-4的烷基所取代；
或者所述R 7和R 8相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
或者所述R 3和R 4相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
R 5和R 6彼此相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数1～12的烷基、碳原子数1～12的卤代烷基、碳原子数1～12的烷氧基、碳原子数3～12的环烷基、碳原子数为3～12的杂环基、碳原子数3～12的烷基硅烷基、碳原子数6～18的芳基硅烷基、碳原子数1～12的烷硫基、碳原子数为6～18的芳基、二苯并噻吩基或二苯并呋喃基；
n 1表示R 1的个数，n 2表示R 2的个数，n 5表示R 5的个数，n 6表示R 6的个数，且n 1、n 2、n 5、n 6分别独立地选自0、1、2、3、4、5、6、7或8；当n 1大于1时，任意两个所述R 1相同或者不同，当n 2大于1时，任意两个所述R 2相同或者不同，当n 5大于1时，任意两个所述R 5相同或者不同，当n 6大于1时，任意两个所述R 6相同或者不同。
根据本申请的第二个方面，提供一种有机电致发光器件，有机电致发光器件包括相对设置的阳极和阴极，以及设置于所述阳极和所述阴极之间的功能层；所述功能层包含上述的化合物。
根据本申请的第三个方面，提供一种电子装置，所述电子装置包括本申请的有机电致发光器件。
本申请的化合物结构是以作为主体的金刚烷螺芴与二苯并五元环通过单键连接而形成的结构；该大分子结构具有较强的刚性，自由旋转的δ键使两个环平面之间形成一定的扭转角度，因此使得本申请化合物拥有了高的第一三重态能级和合适的HOMO能级分布，因此可作为发光层主体材料应用于有机电致发光材料中，以改善有机电致发光器件的效率性能。金刚烷基与芴基螺合，可以通过超共轭效应而大幅增加大平面共轭结构的电子云密度，增强化合物的空穴迁移率，有助于促进发光层中空穴和电子的传输平衡，进而提高电子和空穴在有机发光层中的复合率，减少或者避免电子穿过有机发光 层向空穴传输层的传输，进而可以有效地保护空穴传输层材料免受电子的冲击，提高有机电致发光器件的寿命。螺合于芴基上的金刚烷基具有大的空间体积和较强的刚性，因此其可以降低大平面共轭结构之间的相互作用力，减小分子间π-π堆叠，调节分子间的堆叠程度，进而使得化合物在成膜时能够具有更为稳定的无定形态，改善化合物的成膜性，进而进一步提高有机电致发光器件的寿命。
本申请的化合物中二苯并五元环和金刚烷螺芴基通过δ键连接，二苯并五元环有很强的能量传递作用，因此应用于发光层主体材料时，可以有效的促进发光层主体和客体间的能量传递，减少能量损失，可以进一步提高发光效率。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。在附图中：
图1是根据本申请的一种实施方式的有机电致发光器件的结构示意图。
图2是根据本申请的一种实施方式的电子装置的结构示意图。
图中主要器件附图标记说明如下：
100、阳极；200、阴极；310、空穴注入层；321、空穴传输层；322、电子阻挡层；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。
在图中，为了清晰，可能夸大了区域和层的厚度。在图中相同的附图标记表示相同或类似的结构，因而将省略它们的详细描述。
在本申请中，
Figure PCTCN2021083413-appb-000006
含义一样，均是指与其他取代基或结合位置结合的位置。
在本申请中，L 1、L 2、R 1、R 2、R 5、R 6、Ar 1和Ar 2中，取代的芳基或杂芳基的的碳原子数，指的是芳基或杂芳基及其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。例如2,4-二苯基-1,3,5-三嗪基就属于碳原子数为15的取代的杂芳基。
在本说明书中“碳原子数为6～40的取代或未取代的芳基”和“取代或未取代的碳原子数为6～40的芳基”两种表述含义相同，均是指芳基及其上的取代基的总碳原子数为6～40。同样的，在本说明书中“碳原子数为3～30的取代或未取代的杂芳基”和“取代或未取代的碳原子数为3～30的杂芳基”两种表述含义相同，均是指杂芳基及其上的取代基的总碳原子数为3～30。
在本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个B、N、O、S、Se、Si或P等杂原子且其余原子为碳和氢。未取代的烷基可以是没有任何双键或三键的“饱和烷基基团”。
在本申请中所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。举例而言：在“
Figure PCTCN2021083413-appb-000007
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氟、氯”的描述中，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，“任选”或者“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括 该事情或者环境发生或者不发生的场合。例如，“任选被烷基取代的杂环基团”意味着烷基可以但不必须存在，该说明包括杂环基团被烷基取代的情景和杂环基团不被烷基取代的情景。“连接于同一原子上的两个取代基之间相互连接以与它们共同连接的原子形成饱和或不饱和的5～18元脂肪族环或5～18元芳香环”意味着连接于同一个原子上的两个取代基可以成环但不必须成环，包括二者相互连接成成饱和或不饱和的5～18元脂肪族环或5～18元芳香环的情景，也包括二者相互独立地存在的情景。
在本申请中，术语“取代或未取代的”是指没有取代基或者被一个或多个取代基取代。所述取代基包括但不限于，氘、卤素基团(F、Cl、Br)、氰基、烷基、烯基、炔基、卤代烷基、芳基、杂芳基、芳氧基、芳硫基、环烷基、杂环基、三烷基硅烷基、烷基、环烷基、烷氧基、烷硫基。
在本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至12个碳原子，在本申请中，诸如“1至12”的数值范围是指给定范围中的各个整数；例如，“1至12个碳原子”是指可包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子、11个碳原子、12个碳原子的烷基。烷基还可为具有1至10个碳原子的中等大小烷基。烷基还可为具有1至6个碳原子的低级烷基。在又一些实施方案中，烷基基团含有1-4个碳原子；还在一些实施方案中，烷基基团含有1-3个碳原子。所述烷基基团可以任选地被一个或多个本申请描述的取代基所取代。烷基基团的实例包含，但并不限于，甲基(Me、-CH 3)，乙基(Et、-CH 2CH 3)，正丙基(n-Pr、-CH 2CH 2CH 3)，异丙基(i-Pr、-CH(CH 3) 2)，正丁基(n-Bu、-CH 2CH 2CH 2CH 3)，异丁基(i-Bu、-CH 2CH(CH 3) 2)，仲丁基(s-Bu、-CH(CH 3)CH 2CH 3)，叔丁基(t-Bu、-C(CH 3) 3)等。此外，烷基可为取代的或未取代的。
本申请中，烷基硅烷基是指
Figure PCTCN2021083413-appb-000008
其中,R G1、R G2、R G3分别独立地为烷基，烷基硅烷基的具体实例，包括但不限于，三甲基硅烷基、三乙基硅烷基、叔丁基二甲基硅烷基、丙基二甲基硅烷基；
本申请中，芳基硅烷基是指
Figure PCTCN2021083413-appb-000009
其中，R G4、R G5、R G6分别独立地为芳基，芳基硅烷基的具体实例，包括但不限于，三苯基硅烷基、二苯基硅烷基、苯基硅烷基等，但并不限定于此。
本申请中，作为取代基的卤素基团，例如氟、氯、溴或碘。
本申请中，“烷氧基”表示烷基基团通过氧原子与分子其余部分相连，其中烷基基团具有如本申请所述的含义。除非另外详细说明，所述烷氧基基团含有1～12个碳原子。在一实施方案中，烷氧基基团含有1～6个碳原子；在另一实施方案中，烷氧基基团含有1～4个碳原子；在又一实施方案中，烷氧基基团含有1～3个碳原子。所述烷氧基基团可以任选地被一个或多个本申请描述的取代基所取代。
烷氧基基团的实例包括，但并不限于，甲氧基(MeO、-OCH 3)，乙氧基(EtO、-OCH 2CH 3)，1-丙氧基(n-PrO、n-丙氧基、-OCH 2CH 2CH 3)，2-丙氧基(i-PrO、i-丙氧基、-OCH(CH 3) 2)，1-丁氧基(n-BuO、n-丁氧基、-OCH 2CH 2CH 2CH 3)，2-甲基-l-丙氧基(i-BuO、i-丁氧基、-OCH 2CH(CH 3) 2)，2-丁氧基(s-BuO、s-丁氧基、-OCH(CH 3)CH 2CH 3)，2-甲基-2-丙氧基(t-BuO、t-丁氧基、-OC(CH 3) 3)，等等。
本申请中，“烷硫基”表示烷基基团通过硫原子与分子其余部分相连，其中烷基基团具有如本申请所述的含义。除非另外详细说明，所述烷硫基基团含有1～12个碳原子。在一实施方案中，烷硫基基团含有1～6个碳原子；在另一实施方案中，烷硫基基团含有1～4个碳原子；在又一实施方案中，烷硫基基团含有1～3个碳原子。所述烷硫基基团可以任选地被一个或多个本申请描述的取代基所取代。烷硫基基团的实例包括，但并不限于，甲硫基(MeS、-SCH 3)，乙硫基(EtS、-SCH 2CH 3)，1-丙硫基(n-PrS、n-丙硫基、-SCH 2CH 2CH 3)，2-丙硫基(i-PrS、i-丙硫基、-SCH(CH 3) 2)，等等。
本申请中，“卤代烷基”或“卤代烷氧基”表示烷基或烷氧基基团被一个或多个卤素原子所取代，其中烷基和烷氧基基团具有如本申请所述的含义，这样的实例包含，但并不限于，三氟甲基、三氟甲氧基等。在一实施方案中，碳原子数为1-6的卤代烷基包含氟取代的C 1-C 6烷基；在另一实施方案中，C 1-C 4卤代烷基包含氟取代的C 1-C 4烷基；在又一实施方案中，C 1-C 2卤代烷基包含氟取代的C 1-C 2烷基。
本申请中，环烷基是指单环或多环饱和环状烃去除氢原子后得到的基团，“环烷基”可以有一个或多个连接点连接到分子的其余部分。在一些实施例中，环烷基是含3～12个环碳原子的环体系；另外一些实施例，环烷基是含5～10个环碳原子的环体系；另外一些实施例，环烷基是含5～7个环碳原子的环体系；另外一些实施例，环烷基是含3～6个环碳原子的环体系，例如，“3至12个碳原子的环烷基”是指可包含3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子、11个碳原子、12个碳原子的环烷基。所述环烷基基团可以独立地未被取代或被一个或多个本申请所描述的取代基所取代。作为其非限制性例子，环烷基有环丙基、环丁基、环戊基、环己基、降冰片基(norbornyl)、金刚烷(adamantine)等。
本申请中，“杂环”，“杂环基”可交换使用，都是指单环，双环或三环体系，其中环上一个或多个原子可以独立任选地被杂原子所取代，环可以是完全饱和的或包含一个或多个不饱和键，但绝不是芳香族类，只有一个连接点连接到其他分子上去。一个或多个环上的氢原子独立任选地被一个或多个本申请所描述的取代基所取代。其中一些实施例是，“杂环”，“杂环基”，“杂脂环族”或“杂环的”基团是3-7元环的单环(1-6个碳原子和选自N，O，P，S的1，2或3个杂原子,在此S或P任选地被一个或多个氧原子所取代得到像SO，SO 2，PO，PO 2的基团，当所述的环为三元环时，其中只有一个杂原子)，或7-10元的双环(4-9个碳原子和选自N，O，P，S的1，2或3个杂原子,在此S或P任选地被一个或多个氧原子所取代得到像SO，SO 2，PO，PO 2的基团)。杂环基可以是碳基或氮基，且-CH 2-基团可以任选地被-C(＝O)-替代。环的硫原子可以任选地被氧化成S-氧化物。环的氮原子可以任选地被氧化成N-氧化合物。
杂环的实例包括，但并不限于，吡咯烷基，四氢呋喃基，二氢呋喃基，四氢噻吩基，四氢吡喃基，二氢吡喃基，四氢噻喃基,哌啶基，吗啉基，硫代吗啉基，噻噁烷基，哌嗪基，高哌嗪基，氮杂环丁基，氧杂环丁基，硫杂环丁基，高哌啶基，环氧丙基，氮杂环庚基，氧杂环庚基，硫杂环庚基，氧氮杂卓基，二氮杂卓基，硫氮杂卓基，2-吡咯啉基，3-吡咯啉基，二氢吲哚基，2H-吡喃基，4H-吡喃基，二氧杂环己基，1,3-二氧戊基，吡唑啉基，二噻烷基，二噻茂烷基，二氢噻吩基，吡唑烷基咪唑啉基，咪唑烷基，1,2,3,4-四氢异喹啉基。
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，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，稠环芳基是指环系统中的两个碳原子为两个邻接环所共用的两个或更多个环，其中所述环中的至少一者是芳香族的，例如其它环可以是环烷基、环烯基、芳基。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 PCTCN2021083413-appb-000010
基等。本说明书中，芳基的碳原子数可以选自6、10、12、13、14、15、16、17、18、20、25或30。在一些实施方案中，芳基是碳原子数为6～30的芳基，另一些实施方式中，芳基是碳原子数为6～15的芳基，另一些实施方式中，芳基是碳原子数为6～18的芳基，另一些实施方式中，芳基的碳原子数为6～20的芳基。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基(-CN)、芳基、杂芳基、三烷基硅烷基、烷基、环烷基、烷氧基、烷硫基、卤代烷基、芳氧基、芳硫基、硅烷基、烷胺基、芳基、杂环基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、吡啶取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基及其取代基的总碳原子数为18。
在本申请中，作为芳基的芴基可以被取代，两个取代基可以彼此结合形成螺结构，具体施例包括但不限于以下结构：
Figure PCTCN2021083413-appb-000011
本申请中，亚芳基为2价基团，除此以外，可以适用上述关于芳基的说明。
在本申请中，杂芳基是指环中包含1、2、3、4、5或6个独立地选自O、N、P、Si、Se、B、和S的杂原子的单环或多环体系，且其中至少有一个环体系是芳香族的。杂芳基中每一个环体系包含5-7个环原子组成的环，且有一个或多个附着点与分子其余部分相连。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。稠环杂芳基是指环系统中的两个原子为两个邻接环所共用的两个或更多个环，其中所述环中的至少一者是芳香族的，例如其它环可以是环烷基、杂环基、环烯基、芳基。
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、异噻唑基、噁二唑基、三唑基、唑基、呋吖基、吡啶基、联吡啶基、菲啶基、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、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅烷基、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。例如碳原子数为14的取代的杂芳基，指的是杂芳基和取代基的总碳原子数为14。
本申请中，杂芳基的碳原子数可以选自3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、20、21、22、23、24、25、26、27、28、29或30。在一些实施方案中，杂芳基是碳原子数为3～12的杂芳基，另一些实施方式中，芳基是碳原子数为3～15的芳基，另一些实施方式中，芳基是碳原子数为5～12的芳基。
本说明书中，亚杂芳基为2价基团，除此以外，可以适用上述关于杂芳基的说明。
在本申请中，成环碳原子数为3～n的杂芳基指的是杂芳基中位于杂芳环上的碳原子数是3～n个，杂芳基上的取代基中的碳原子数不计算在内。
在本申请中，对芳基的解释可应用于亚芳基，对杂芳基的解释同样应用于亚杂芳基，对烷基的解释可应用于亚烷基，对环烷基的解释可应用于亚环烷基。
在本申请中，n个原子形成的环体系，即为n元环。例如，苯基为6元芳基。6～13元芳环就是指苯环、茚环和萘环等。
本申请中的“环”包含饱和环、不饱和环；饱和环即环烷基、杂环烷基，不饱和环，即环烯基、杂环烯基、芳基和杂芳基。
本申请中的不定位连接键，是指从环体系中伸出的单键
Figure PCTCN2021083413-appb-000012
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。例如，下式(X)中所示的，式(X)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(X-1)～式(X-10)所示出的任一可能的连接方式。
Figure PCTCN2021083413-appb-000013
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 PCTCN2021083413-appb-000014
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 PCTCN2021083413-appb-000015
本申请提供一种化合物，所述化合物的结构式如化学式1所示：
Figure PCTCN2021083413-appb-000016
其中，环A和环B各自独立地为碳原子数6～14的芳环；
X选自O、S、Si(R 3R 4)、C(R 3R 4)；
各R 1彼此相同或不同，且各自独立地选自：氘、卤素、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为3～12 的的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12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7～18的芳烷氧基或
Figure PCTCN2021083413-appb-000017
Ar 1选自碳原子数为6～40的取代或未取代的芳基，碳原子数为3～40的取代或未取代的杂芳基；
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3～30的取代或未取代的亚杂芳基；
Ar 1和L 1中的取代基彼此相同或不同，且各自独立地选自：氘、氰基、卤素基团、硝基、基团U、碳原子数为1～12的烷氧基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷基、碳原子数为3～12的环烷基、碳原子数为3～12的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12的烷硫基、碳原子数为6～18的芳氧基、碳原子数为7～18的芳烷基或碳原子数为6～18的芳氧基构成的组，所述基团U选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基，所述芳基和杂芳基中的取代基(即基团U的取代基)选自氘、氰基、卤素基团、碳原子数为1～12的烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为1～12的卤代烷基、碳原子数为3～12的烷基硅烷基、碳原子数为6～20的芳基或碳原子数为3～18的杂芳基所构成的组；
或者，在各L 1和Ar 1中，当同一原子上具有两个取代基时，任选地，两个所述取代基相互连接，以与它们所共同连接的原子一起形成5到18元脂肪族环或5到18元芳香环；
各R 2彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为3～12的的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12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7～18的芳烷基或
Figure PCTCN2021083413-appb-000018
L 2选自单键、碳原子数为3～30的取代或未取代的亚芳基或
Figure PCTCN2021083413-appb-000019
且所述L 2不为亚蒽基；
Ar 2选自碳原子数为3～30的取代或未取代的芳基或
Figure PCTCN2021083413-appb-000020
且所述Ar 2不为蒽基；
其中，Q和T分别独立地选自O、S、C(R 7R 8)或Si(R 7R 8)，
R 3、R 4、R 7、R 8彼此相同或不同，且各自独立地选自氢、碳原子数1～12的取代或未取代的烷基、碳原子数1～12的取代或未取代的卤代烷基、碳原子数为6-18的取代或未取代的芳基、碳原子数为3～18的取代或未取代的杂芳基，所述R 3、R 4、R 7和R 8中的取代是指被氘、卤素基团、氰基、碳原子数为1～4的烷基所取代；
或者所述R 7和R 8相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
或者所述R 3和R 4相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
R 5和R 6彼此相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数1～12的烷基、碳原子数1～12的卤代烷基、碳原子数1～12的烷氧基、碳原子数3～12的环烷基、碳原子数为3～12的杂环基、碳原子数3～12的烷基硅烷基、碳原子数6～18的芳基硅烷基、碳原子数1～12的烷硫基、碳原子数为6～18的芳基、二苯并噻吩基或二苯并呋喃基；
n 1表示R 1的个数，n 2表示R 2的个数，n 5表示R 5的个数，n 6表示R 6的个数，且n 1、n 2、n 5、n 6分别独立地选自0、1、2、3、4、5、6、7或8；当n 1大于1时，任意两个所述R 1相同或者不同，当n 2大于1时，任意两个所述R 2相同或者不同，当n 5大于1时，任意两个所述R 5相同或者不同，当n 6大于1时，任意两个所述R 6相同或者不同。
在本申请中，环A指的是
Figure PCTCN2021083413-appb-000021
环B指的是
Figure PCTCN2021083413-appb-000022
举例而言，在化合物
Figure PCTCN2021083413-appb-000023
中，环A为萘环，取代基R 1个数为0；环B为萘环，X为氧，取代基R 2个数为0。可以理解的是，环B至少包括一个苯环结构，这使得本申请的化合物至少包括一个二苯并五元稠合环结构。
由于该化合物中环A或环B为稠合环结构时，因此该化合物的大平面共轭结构更大、刚性更强、电子云密度更高，这使得化合物的空穴传输能力更强，进而可以提高电子和空穴在有机发光层中的复合率，减少或者避免电子穿过有机发光层而向空穴传输层传输，进而可以有效地保护空穴传输层材料免受电子的冲击，提高有机电致发光器件的寿命发光。
本申请的化合物结构是以作为主体的金刚烷螺芴与二苯并五元环通过单键连接而形成的结构；该大分子结构具有较强的刚性，自由旋转的δ键使两个环平面之间形成一定的扭转角度，因此使得本申请化合物拥有了高的第一三重态能级和合适的HOMO能级分布，并且二苯并五元稠合环具有优秀的能量传递作用，可以有效促进发光层主体和客体材料间的能量传递，因此可作为发光层主体材料应用于有机电致发光材料中，以改善有机电致发光器件的效率性能。金刚烷基与芴基螺合，其可以通过超共轭效应而大幅增加大平面共轭结构的电子云密度，增强化合物的空穴迁移率，有助于促进发光层中空穴和电子的传输平衡，进而提高电子和空穴在有机发光层中的复合率，减少或者避免电子穿过有机发光层向空穴传输层的传输，进而可以有效地保护空穴传输层材料免受电子的冲击，提高有机电致发光器件的寿命。螺合于芴基上的金刚烷基具有大的空间体积和较强的刚性，因此其可以降低大平面共轭结构之间的相互作用力，减小分子间π-π堆叠，调节分子间的堆叠程度，进而使得化合物在成膜时能够具有更为稳定的无定形态，改善化合物的成膜性，进而进一步提高有机电致发光器件的寿命。
本申请的化合物中二苯并五元环和金刚烷螺芴基通过δ键连接，二苯并五元环有很强的能量传递作用，因此应用于发光层主体材料时，可以有效的促进发光层主体和客体间的能量传递，减少能量损失，可以进一步提高发光效率。
在本申请的一种可选的实施方式中，所述式(1)中，n 1+n 2＝1。
在本申请的一种可选的实施方式中，所述式(1)中n 1为1，n 2为0，且R 1为
Figure PCTCN2021083413-appb-000024
或者 ，n 1为0，n 2为1，且R 2为
Figure PCTCN2021083413-appb-000025
在本申请的一种可选的实施方式中，X选自O、S、Si(R 3R 4)或C(R 3R 4)，所述R 3和R 4相同，且R 3、R 4选自甲基或苯基；或者所述R 3和R 4相互连接以与它们共同连接的原子形成环戊烷、环己烷或芴环。
在本申请的一种可选的实施方式中，Q和T分别独立地选自O、S、C(R 7R 8)或Si(R 7R 8)，所述R 7和R 8相同，且R 7、R 8选自甲基或苯基；或者所述R 7和R 8相互连接以与它们共同连接的原子形成环戊烷、环己烷或芴环。
在一些实施方案中，本申请的化合物的结构式如式(f-1)～(f-16)中的任意一种所示：
Figure PCTCN2021083413-appb-000026
Figure PCTCN2021083413-appb-000027
在本申请的一种可选的实施方式中，所述式(1)中环A和环B各自独立地为苯环、萘环、蒽环或菲环。
在本申请的一种可选的实施方式中，所述式(1)中的
Figure PCTCN2021083413-appb-000028
分别独立地选自以下结构：
Figure PCTCN2021083413-appb-000029
进一步地，所述环A选自
Figure PCTCN2021083413-appb-000030
所述环B选自
Figure PCTCN2021083413-appb-000031
Figure PCTCN2021083413-appb-000032
在本申请的一种可选的实施方式中，本申请的化合物的结构式如化学式(q-1)～(q-12)中的任意一种所示：
Figure PCTCN2021083413-appb-000033
其中，环C和环D为萘环，X、L 1、L 2、Ar 1、Ar 2具有如说明书中所述定义。
在本申请的一种可选的实施方式中，所述L 1选自单键、碳原子数为6～20的取代或未取代的亚芳基，碳原子数为3～20的取代或未取代的亚杂芳基。
在本申请的一种可选的实施方式中，所述L 1选自单键、碳原子数为6～18的取代或未取代的亚芳基，碳原子数为4～18的取代或未取代的亚杂芳基。
进一步地，在本申请的一种可选的实施方式中，所述L 1中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、溴、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～9的三烷基硅烷基、碳原子数为5～7的环烷基、碳原子数为6～15的芳基、碳原子数为3～12的杂芳 基所构成的组。
进一步地，在本申请的一种可选的实施方式中，L 1中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基所组成的组。
在本申请的一种可选的实施方式中，所述L 1选自单键、取代或未取代的亚苯基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的亚芘基、螺[环戊烷-1,9’-芴]亚基、螺[环己烷-1,9’-芴]亚基、取代或未取代的亚吡啶基、取代或未取代的亚嘧啶基、取代或未取代的9,9-二甲基-9H-9-硅杂芴亚基、取代或未取代的二苯并呋喃亚基、取代或未取代二苯并噻吩亚基、取代或未取代的亚喹啉基、取代或未取代的亚异喹啉基、取代或未取代的亚咔唑基、取代或未取代的亚菲咯琳基、取代或未取代的螺二芴亚基中的一种，或者为上述亚基中两者或三者通过单键连接所形成的亚基基团；所述L 1中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基所组成的组。
在本申请的一种可选的实施方式中，所述L 1选自单键、或者选自化学式(j-1)至化学式(j-12)所示的基团所组成的组；
Figure PCTCN2021083413-appb-000034
Figure PCTCN2021083413-appb-000035
其中，M 2选自单键或者
Figure PCTCN2021083413-appb-000036
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中的两个或者两个以上选自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中的两个或者两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个或者两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 33中至少一个选自N；当Q 24～Q 33中的两个或者两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
E 1～E 12、J 5～J 8分别独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～18的杂芳基、碳原子数为6～20的芳基、碳原子数为3～9的三烷基硅烷基、碳原子数为8～12的芳基硅烷基、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6～12的芳氧基、碳原子数为6～12的芳硫基；
e 1～e 12以e r表示，E 1～E 14以E r表示，r为变量，表示1～12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或9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 13E 14)；其中，各E 13、E 14、E 15、E 16和E 17分别独立地选自：氢、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；
或者，任选地，上述E 16和E 17相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
或者，任选地，上述E 13和E 14相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
各K 4独立地选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 18E 19)；其中，各E 20、E 21、E 22、E 18、E 19分别独立地选自：氢、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、；
或者，任选地，上述E 21和E 22相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
或者，任选地，上述E 18和E 19相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环。
举例而言，L 1为
Figure PCTCN2021083413-appb-000037
时，当M 2和K 4为单键，E 11均为氢，K 3为C(E 16E 17)时，任选地，连接于同一个原子上的E 16和E 17相互连接以与它们共同连接的原子形成饱和或不饱和的5至13元脂肪族环指的是E 16和E 17可以相互连接形成一个5至13元环，也可以相互独立存在；当E 16和E 17形成脂肪族环时，该环的原子数可以是5元环，例如
Figure PCTCN2021083413-appb-000038
也可以是6元环，例如
Figure PCTCN2021083413-appb-000039
还可以是10元环，例如
Figure PCTCN2021083413-appb-000040
当然，E 16和E 17相互连接形成的环上的原子数还可以为其他数值，此处不再一一列举。同时，E 16和E 17相互连接形成的环还可以是芳香环，例如13元芳环，
Figure PCTCN2021083413-appb-000041
任选地，E 13和E 14相互连接以与它们共同连接的原子形成5到13元脂肪族环或芳香环的含义与E 13和E 14相同。任选地，E 21和E 22相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环的含义与E 16和E 17相同。任选地，E 18和E 19相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环的含义与E 16和E 17相同。
在本申请的一种可选的实施方式中，所述L 1选自单键、取代或未取代的W 1其中，未取代的W 1选自如下基团所组成的组：
Figure PCTCN2021083413-appb-000042
其中，取代的W 1为未取代的W 1被一个或者多个选自氘、氟、氯、溴、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～9的三烷基硅烷基、碳原子数为5～7的环烷基、碳原子数为6～15的芳基和碳原子数为3～12的杂芳基的取代基所取代而形成的基团，且当取代的W 1上的取代基数量为多个时，任意两个取代基之间相同或者不同。
进一步地，在本申请的一种可选的实施方式中，取代的W 1为未取代的W 1被一个或者多个选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基的取代基所取代而形成的基团。本申请中，取代基为“多个”意思是多于1个，可以是2个、3个、4个、5个、6个、7个或8个。
在本申请的一种可选的实施方式中，所述L 1选自单键或如下基团所组成的组：
Figure PCTCN2021083413-appb-000043
Figure PCTCN2021083413-appb-000044
L 1不限于上述基团。
在本申请的一些实施方案中，Ar 1选自化学式i-1至化学式i-18所示的基团所组成的组：
Figure PCTCN2021083413-appb-000045
其中，M 1选自单键或者
Figure PCTCN2021083413-appb-000046
G 1～G 5各自独立地选自N或者C(F 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(F 1)时，任意两个F 1相同或者不相同；
G 6～G 13各自独立地选自N或者C(F 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(F 2)时，任意两个F 2相同或者不相同；
G 14～G 23各自独立地选自N或者C(F 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(F 3)时，任意两个F 3相同或者不相同；或者，任选地，相邻的两个F 3相互连接形成5～10元芳环或5～10元杂芳环；
G 24～G 33各自独立地选自N或者C(F 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(F 4)时，任意两个F 4相同或者不相同；或者，任选地，相邻的两个F 4相互连接形成5～10元芳环或5～10元杂芳环；
G 34～G 37各自独立地选自N或者C(F 5)，当G 34～G 37中的两个以上选自C(F 5)时，任意两个F 5相同或者不相同；或者，任选地，相邻的两个F 5相互连接形成5～10元芳环或5～10元杂芳环；
G 38～G 45各自独立地选自N或者C(F 6)，且G 38～G 45中至少一个选自N；当G 38～G 45中的两个以上选自C(F 6)时，任意两个F 6相同或者不相同；
G 46～G 53各自独立地选自N或者C(F 7)，且G 46～G 53中至少一个选自N；当G 46～G 53中的两个或者两个以上选自C(F 7)时，任意两个F 7相同或者不相同；或者，任选地，相邻的两个F 7相互连接形成5～10元芳环或5～10元杂芳环；
D 1选自氢、氘、氟、氯、溴、氰基、碳原子数为3～12的三烷基硅烷基、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；
D 2～D 9、D 21各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～12的三烷基硅烷基、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3～20的芳基、碳原子数为3～18的杂芳基；
D 10～D 20、F 1～F 7各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～12的三烷基硅烷基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为3～9的烷基硅烷基、三苯基硅烷基或基团B，所述基团B选自碳原子数为6～25的取代或未取代的芳基、碳原子数为3～18的取代或未取代的杂芳基，所述芳基或杂芳基中的取代基各自独立地选自氘、氟、氯、氰基、碳原子数为1～6的烷基、碳原子数为1～6的烷氧基、碳原子数为3～7的环烷基、碳原子数为6～15的芳基、碳原子数为3～12的杂芳基、碳原子数为1～4的烷氧基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基所组成的组；
d 1～d 21以d k表示，D 1～D 21以D k表示，k为变量，表示1～21的任意整数，d k表示取代基D k的个数；其中，当k选自5或者17时，d k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，d k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，d k选自1、2、3、4或者5；当k为13时，d k选自1、2、3、4、5或者6；当k选自10或者19时，d k选自1、2、3、4、5、6或者7；当k为20时，d k选自1、2、3、4、5、6、7或者8；当k为11时，d k选自1、2、3、4、5、6、7、8或9；且当d k大于1时，任意两个D k相同或者不相同；
K 1和K 6分别独立地选自O、S、N(D 22)、C(D 23D 24)、Si(D 28D 29)；其中，各D 22、D 23、D 24、D 28、D 29分别独立地选自：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，任选地，上述D 23和D 24相互连接以与它们共同连接的原子形成5到14元脂肪族环或5到14元芳香环；
或者，任选地，上述D 28和D 29相互连接以与它们共同连接的原子形成5到14元脂肪族环或5到14元芳香环；
K 2选自单键、O、S、N(D 25)、C(D 26D 27)、Si(D 30D 31)；其中，各D 25、D 26、D 27、D 30、D 31分别独立地选自：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，任选地，上述D 26和D 27相互连接以与它们共同连接的原子形成5到14元脂肪族环或5到 14元芳香环；
或者，任选地，上述D 30和D 31相互连接以与它们共同连接的原子形成5到14元脂肪族环或5到14元芳香环；
K 5选自O、S、Se、N(D 32)、C(D 33D 34)，其中，D 32、D 33和D 34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。
式i-16中，“任选地，相邻的两个F 5相互连接形成5～10元芳环或5～10元杂芳环”意思是任意两个相邻的环原子，G 34和G 35或者G 35和G 36或者G 36和G 37，均为C(F 5)时，相邻的两个F 5可以相互独立地存在，也可以相互连接以与它们所连接的环原子一起形成一个稠合的芳环或杂芳环。举例而言，当i-16
Figure PCTCN2021083413-appb-000047
中，K 5为O,G 34和G 35均为CH,G 36和G 37均为C(F 5)且二者形成6元芳环时，即式i-16为
Figure PCTCN2021083413-appb-000048
相邻的F 5成环还可以是形成其他的芳环或杂芳环，在此不再一一列举。任选地，相邻的两个F 3、F 4或F 7相互连接成环的含义与此相同，不再一一列举。
“任选地，上述D 23和D 24相互连接以与它们共同连接的原子形成5到14元脂肪族环或5到14元芳香环”的意思是，D 23和D 24可以相互连接形成一个环，也可以相互独立存在。举例而言，在式
Figure PCTCN2021083413-appb-000049
中，当M 1为单键，K 2为单键，D 19均为氢，K 1为C(D 23D 24)时，当D 23和D 24形成环时，该环可以是5元脂肪族环，例如
Figure PCTCN2021083413-appb-000050
也可以是6元脂肪族环，例如
Figure PCTCN2021083413-appb-000051
可以是13元芳香环，例如
Figure PCTCN2021083413-appb-000052
还可以是14元杂芳环，例如
Figure PCTCN2021083413-appb-000053
当然，D 23和D 24相互连接形成的环上的碳原子数还可以为其他数值，此处不再一一列举。任选地，D 26和D 27相互连接以与它们共同连接的原子形成5到14元脂肪族环或芳香环的涵义与D 23和D 24相同。任选地，D 28和D 29，D 26和D 27，D 30和D 31，相互连接以与它们共同连接的原子形成5到14元脂肪族环或芳香环的涵义与D 23和D 24相同。
可选地，G 1～G 5中至少两个选自N。
可选地，G 6～G 13中至少两个选自N。
可选地，G 14～G 23中至少两个选自N。
可选地，G 24～G 33中至少两个选自N。
可选地，G 38～G 45中至少两个选自N。
可选地，G 46～G 53中至少两个选自N。
在本申请的一些具体实施方式中，Ar 1选自碳原子数为6、10、12、14、15、16、18、20、25的取代或者未取代的芳基，碳原子数为4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36的取代或者未取代的杂芳基。在本申请的一些实施方式中，Ar 1选自碳原子数为6～18的取代或者未取代的芳基，碳原子数为15～26的取代或者未取代的杂芳基。
可选地，在本申请的一些实施方案中，Ar 1中的取代基为一个或多个，彼此相同或不同，且各自独立地选自氘、氟、氯、氰基、碳原子数为6～20的芳基、碳原子数为3～18的取代或未取代的杂芳基、碳原子数为1～6的烷基、碳原子数为1～6的卤代烷基、碳原子数为1～6的烷氧基、碳原子数为1～6 的烷硫基、碳原子数为5～10的环烷基、碳原子数为3～9的三烷基硅烷基、碳原子数为6～20的芳氧基、碳原子数为6～20的芳硫基和碳原子数为6～18的芳基甲硅烷基。
在本申请的一些实施方案中，Ar 1选自取代或未取代的基团W 3，其中，未取代的W 3选自如下基团所组成的组：
Figure PCTCN2021083413-appb-000054
Figure PCTCN2021083413-appb-000055
其中，各T 1、T 2和T 3彼此相同或不同，分别独立地选自氢、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基；任意两个T 1相同或者不相同，任意两个T 2相同或者不相同,任意两个T 3相同或者不相同；
其中，取代的W 3为未取代的W 3被一个或者多个选自氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、碳原子数为3～7的环烷基、碳原子数为6～15的芳基、碳原子数为3～18的杂芳基、碳原子数为1～4的烷硫基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基的取代基所取代而形成的基团，且当W 3上的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
需要说明的是，“取代的W 3”为未取代的W 3被一个或者多个取代基所取代，所述取代基可以替代上述未取代的W 3中的任意位置的氢原子，例如也可以是基团T 1、T 2和T 3中的的任意氢原子。
还需要说明的是，在上述W 3中，当T 1、T 2或T 3为氢时，不定位连接键也可以替代T 1、T 2或T 3而连接在W 3上。例如，
Figure PCTCN2021083413-appb-000056
当T 1为氢时，也可以表示
Figure PCTCN2021083413-appb-000057
进一步地，各T 1、T 2和T 3彼此相同或不同，分别独立地选自：氢、苯基、萘基、蒽基、菲基、联苯基、三联苯基、芴基、二苯并噻吩基、二苯并呋喃基、N-苯基咔唑基、咔唑-9-基苯基、吡啶基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、苯并噁嗪、三亚苯基、菲咯琳基；取代的W 3为未取代的W 3被一个或者多个选自：氟、氘、氰基、三氟甲基、三甲基硅烷基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、环戊烷基、环己烷基、苯基、联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、嘧啶基、喹啉基、异喹啉基、咔唑基、N-苯基咔唑基、二苯并呋喃基、二苯并噻吩基、的取代基所取代而形成的基团；且当W 3上的取代基的数量为多个时，任意两个取代基相同或者不相同。
在本申请的一些实施例中，Ar 1可以选自为缺电子杂芳基(亦称贫电子杂芳基)，其上杂原子在整体上能够降低杂芳基的共轭体系的电子云密度而不是提高杂芳基的共轭体系的电子云密度，例如杂原子上的孤对电子不参与到共轭体系中，且杂原子由于较强的电负性而使得共轭体系的电子云密度降低。举例而言，缺电子杂芳基可以包括但不限于吡啶基、嘧啶基、均三嗪基、喹啉基、异喹啉基、苯并吡唑基、苯并咪唑基、喹喔啉基、菲啰啉基等。如此，Ar 1可以形成化合物的电子传输核心基团，使得化合物能够有效地实现电子传输，且能够有效的平衡电子和空穴在有机发光层的传输速率。如此，该化合物既可以作为双极性有机发光层主体材料同时传输电子和空穴，也可以作为电子型有机发光层主体材料而与空穴型有机发光层主体材料配合。在此类型化合物中，具有空穴传输能力的二苯 并五元环与具有电子传输能力的缺电子杂芳基(Ar 1)分别与金刚烷螺芴核心结构通过单键连接，这样更利于化合物电子传输性能和空穴传输性能的平衡；另外，这样连接方式的化合物T 1能级较高，且对激子的耐受能力提升，更适于作为发光层主体材料。
在本申请的一些更具体的实施例中，Ar 1选自如下结构：
Figure PCTCN2021083413-appb-000058
Figure PCTCN2021083413-appb-000059
Figure PCTCN2021083413-appb-000060
在本申请的另一些实施例中，当R 2不为
Figure PCTCN2021083413-appb-000061
时，Ar 1还可以选自为芳基或富电子杂芳基。这些富电子芳香基团整体上能够增加共轭体系的电子云密度，并能够调整化合物的HOMO能级，因此该化合物将具有更佳地空穴传输能力，并且二苯并呋喃基、二苯并噻唑基还具有优异的能量传递作用，化合物作为发光层主体时，可以减少能量损失，提高器件效率。
在本申请的一些更具体的实施例中，Ar 1选自如下结构：
Figure PCTCN2021083413-appb-000062
在本申请的一些实施方案中，L 2选自单键、碳原子数为6～18的取代或未取代的亚芳基、或
Figure PCTCN2021083413-appb-000063
且L 2不是亚蒽基。
在本申请的一种可选的实施方式中，Q选自O、S、C(R 7R 8)或Si(R 7R 8)，所述R 7和R 8相同，且R 7、R 8选自甲基或苯基；或者所述R 7和R 8相互连接以与它们共同连接的原子形成环戊烷、环己烷或芴环,各R 5独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基。
在本申请的一些实施方案中，L 2选自单键、碳原子数为6～18的取代或未取代的亚芳基、取代或未取代的二苯并噻吩亚基、取代或未取代的二苯并呋喃亚基、取代或未取代的二甲基芴亚基、取代或未取代的9,9-二甲基-9H-9-硅杂芴亚基，且L 2不是亚蒽基。
进一步地，在一些更具体实施方案中，所述L 2中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、碳原子数为3～7的环烷基、碳原子数为6～15的芳基、碳原子数为5～18的杂芳基、碳原子数为1～4的烷硫基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基所取代而形成的基团，且当L 2中的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
在本申请的一些实施方案中，所述L 2选自单键、取代或未取代的亚苯基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的9,9-二甲基芴亚基、取代或未取代的亚菲基、螺[环戊烷-1,9’-芴]亚基、螺[环己烷-1,9’-芴]亚基、取代或未取代的9,9-二甲基-9H-9-硅杂芴亚基、取代或未取代的二苯并呋喃亚基、取代或未取代二苯并噻吩亚基、取代或未取代的螺二芴亚基中的一种，或者为上述亚基中两者或三者通过单键连接所形成的亚基基团；所述L 2中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基所组成的组。
在本申请的一些实施方案中，所述L 2选自单键、取代或未取代的W 2其中，未取代的W 2选自如下基团所组成的组：
Figure PCTCN2021083413-appb-000064
其中，取代的W 2为未取代的W 2被一个或者多个选自氘、氟、氯、溴、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～9的三烷基硅烷基、碳原子数为5～7的环烷基和碳原子数为6～15的芳基的取代基所取代而形成的基团，且当取代的W 2上的取代基数量为多个时，任意两个取代基之间相同或者不同。
进一步地，在本申请的一种可选的实施方式中，取代的W 2为未取代的W 2被一个或者多个选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基的基团所取代而形成的基团。
在本申请的一些实施方案中，L 2选自以下结构：
Figure PCTCN2021083413-appb-000065
Figure PCTCN2021083413-appb-000066
L 2不限于上述基团。
在本申请的一些实施方案中，Ar 2选自碳原子数为6～25的取代或未取代的亚芳基、或
Figure PCTCN2021083413-appb-000067
且Ar 2不是亚蒽基。
在本申请的一种可选的实施方式中，T选自O、S、C(R 7R 8)或Si(R 7R 8)，所述R 7和R 8相同，且R 7、R 8选自甲基或苯基；或者所述R 7和R 8相互连接以与它们共同连接的原子形成环戊烷、环己烷或芴环，各R 6独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、三氟甲基、三甲基硅烷基、苯基、芴基、氰基取代的苯基、氟取代的苯基、萘基、二苯并噻吩、二苯并呋喃、环己烷基、三甲基硅烷基。
在本申请的一些实施方案中，Ar 2选自碳原子数为6、10、12、14、15、16、18、20或25的取代或未取代的芳基，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9,9-二甲基-9H-9-硅杂芴基，且Ar 2不是蒽基。
进一步地，在本申请的一些实施方案中，所述Ar 2中的取代基彼此相同或不同，各自独立地选自氘，氟，氯，氰基，碳原子数为1～4的烷基，碳原子数为1～4的烷氧基，碳原子数为3～7的环烷基，任选地被0、1、2或3个选自氘、氟、氰基、甲基的取代基所取代的碳原子数为6～15的芳基，任选地被0、1、2或3个选自氘、氟、氰基、甲基的取代基所取代的碳原子数为5～18的杂芳基，碳原子数为1～4的烷硫基，碳原子数为1～4的卤代烷基，碳原子数为3～9的烷基硅烷基所取代而形成的基团，且当Ar 2中的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
在本申请的一些实施方案中，Ar 2选自取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的芴基、取代或未取代的硅杂芴基、取代或未取代的二苯并呋喃亚基、取代或未取代二苯并噻吩亚基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、螺[环戊烷-1,9’-芴]基、螺[环己烷-1,9’-芴]基中的一种，或者为上述基团中两者或三者通过单键连接所形成的亚基基团；所述Ar 2中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、三氟甲基、三甲基硅烷基、苯基、芴基、氰基取代的苯基、氟取代的苯基、萘基、二苯并噻吩、二苯并呋喃、环己烷基、三甲基硅烷基所组成的组；Ar 2中的取代基有多个时，各取代基彼此相同或不同。
在本申请的一些实施方案中，所述Ar 2选自取代或未取代的基团W 4，其中，未取代的W 4选自如下基团所组成的组：
Figure PCTCN2021083413-appb-000068
Figure PCTCN2021083413-appb-000069
其中，取代的W 4为未取代的W 4被一个或者多个选自氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、碳原子数为3～7的环烷基、碳原子数为6～14的芳基、碳原子数为3～12的杂芳基、碳原子数为1～4的烷硫基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基的取代基所取代而形成的基团，且当W 4上的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
进一步地，取代的W 4为未取代的W 4被一个或者多个选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、三氟甲基、三甲基硅烷基、苯基、芴基、氰基取代的苯基、氟取代的苯基、萘基、二苯并噻吩、二苯并呋喃、环己烷基、三甲基硅烷基的取代基所取代而组成的基团。
在本申请的一些实施方案中，各R 1彼此相同或不同，且各自独立地选自：氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的烷氧基、碳原子数为5～10的环烷基、碳原子数为3～7的的杂环基、三甲基硅烷基、三苯基硅烷基、碳原子数为1～4的烷硫基或
Figure PCTCN2021083413-appb-000070
更具体地，在本申请的一些实施方案中，各R 1彼此相同或不同，且各自独立地选自：氟、氘、氰基、三氟甲基、三甲基硅烷基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、环戊烷基、环己烷基、苯基、三甲基硅烷基、三苯基硅烷基或
Figure PCTCN2021083413-appb-000071
在本申请的一些实施方案中，各R 2彼此相同或不同，且各自独立地选自氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的烷氧基、碳原子数为3～7的环烷基、碳原子数为3～8的烷基硅烷基、三苯基硅烷基、碳原子数为1～4的烷硫基或
Figure PCTCN2021083413-appb-000072
在本申请的一些实施方案中，各R 2彼此相同或不同，且各自独立地选自：氟、氘、氰基、三氟甲基、三甲基硅烷基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、环戊烷基、环己烷基、苯基、三苯基硅烷基或
Figure PCTCN2021083413-appb-000073
在本申请的一些实施例中，Ar 2选自芳基或富电子的二苯并呋喃基、二苯并噻唑基，这些富电子芳香基团整体上能够增加共轭体系的电子云密度例如氧原子和硫原子上的孤对电子可以参与到共轭体系中而增加杂芳基的共轭体系的电子云密度。由于芳基和富电子二苯并呋喃基、二苯并噻唑基均能够有效地增强化合物的电子云密度，并能够调整化合物的HOMO能级，因此该化合物将具有更佳地空穴传输能力，并且二苯并呋喃基、二苯并噻唑基还具有优异的能量传递作用。如此，该化合物可以作为空穴型有机发光层主体材料，与用于传输电子的电子型有机发光层主体材料配合，共同形成有机发光层的主体材料。
在本申请的一些实施例中，Ar 2选自以下结构：
Figure PCTCN2021083413-appb-000074
Figure PCTCN2021083413-appb-000075
Ar 2不限于上述基团。
可选地，所述化合物选自如下化合物所组成的组：
Figure PCTCN2021083413-appb-000076
Figure PCTCN2021083413-appb-000077
Figure PCTCN2021083413-appb-000078
Figure PCTCN2021083413-appb-000079
Figure PCTCN2021083413-appb-000080
Figure PCTCN2021083413-appb-000081
Figure PCTCN2021083413-appb-000082
Figure PCTCN2021083413-appb-000083
Figure PCTCN2021083413-appb-000084
Figure PCTCN2021083413-appb-000085
本申请还提供一种有机电致发光器件，有机电致发光器件包括相对设置的阳极和阴极，以及设置于所述阳极和所述阴极之间的有机发光层；所述有机发光层包含上述的化合物，以改善有机电致发光器件的电压特性、效率特性和寿命特性。
本申请的化合物可以作为单一组分的主体材料或双组分混合型主体材料之一。
举例而言，如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、有机发光层330、电子传输层340和阴极200。本申请提供的化合物可以应用于有机电致发光器件的有机发光层330，以提高有机电致发光器件的寿命、提高有机电致发光器件的发光效率或者降低 有机电致发光器件的驱动电压。
可选地，阳极100包括阳极材料，其可选地为有助于空穴注入至功能层中的具有大逸出功(功函数，work function)的材料。阳极材料的具体实例包括但不限于：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。可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可以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。
可选地，有机发光层330可以包括主体材料和客体材料，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。
在本申请的一种实施方式中，主体材料可以由本申请的化合物组成，尤其是由R 1基团中包括有缺电子芳杂环的化合物组成。该类化合物能够同时传输电子和空穴，且能够平衡空穴和电子的传输效率，因此电子和空穴能够在有机发光层内高效复合，提高有机电致发光器件的发光效率。
在本申请的另一种实施方式中，主体材料可以为复合材料，例如可以包括本申请的化合物和电子型有机发光层主体材料。本申请的化合物能够有效的传输空穴，使得空穴传输效率与有机发光层的电子传输效率相平衡，进而使得电子和空穴能够在有机发光层内高效复合，提高有机电致发光器件的发光效率。举例而言，主体材料可以包括本申请的化合物和GH-n1。
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的客体材料可以为Ir(piq) 2(acac)等。在本申请的另一种实施方式中，有机发光层330的客体材料可以为Ir(ppy) 3等。
可选地，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。
可选地，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。可选包括包含铝的金属电极作为阴极。在本申请的一种实施方式中，阴极200的材料可以为镁银合金。
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F4-TCNQ组成。
可选地，如图1所示，空穴传输层321和有机发光层330之间还可以设置有电子阻挡层322，以阻挡电子向空穴传输层321侧传输，提高电子和空穴在有机发光层330的复合率并保护空穴传输层321免受电子的冲击。电子阻挡层322的材料可以为咔唑多聚体、咔唑连接三芳胺类化合物或者其他可行的结构。
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。
本申请还提供一种电子装置400，如图2所示，该电子装置400包括上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件。该电子装置400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。由于该电子装置400具有上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
合成例：
下面所描述的合成例中，除非另有声明，否则所有的温度的单位为摄氏度。部分试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa ChemicalCompany，部分不能直接采购的中间体是通过商购原料经简单反应制备得到，除非另有声明，否则使用时都没有经过进一步纯化。其余的常规试剂从汕头西陇化工厂、广东光华化学试剂厂、广州化学试剂厂、天津好寓宇化学品有限公司、天津市福晨化学试剂厂、武汉鑫华远科技发展有限公司、青岛腾龙化学试剂有限公司和青岛海洋化工厂等处购买得到。无水四氢呋喃、二氧六环、甲苯、乙醚等无水溶剂是经过金属钠回流干燥得到。各合成例中的反应一般是在氮气或氩气正压下进行的，或者在无水溶剂上套一干燥管(除非另有声明)；在反应中，反应瓶都塞上合适的橡皮塞，底物通过注射器注入反应瓶中。所用到的各个玻璃器皿都是干燥过的。
在纯化时，色谱柱是硅胶柱，硅胶(100-200目)购于青岛海洋化工厂。
在各个合成例中，低分辨率质谱(MS)数据的测定条件是：Agilent 6120四级杆HPLC-M(柱子型号：Zorbax SB-C18,2.1×30mm,3.5微米,6min,流速为0.6mL/min。流动相：5％-95％(含0.1％甲酸的乙腈)在(含0.1％甲酸的水中的比例)，采用电喷雾电离(ESI)，在210nm/254nm下，用UV检测。
核磁共振氢谱：布鲁克(Bruker)400MHz核磁仪，室温条件下，以CDCl 3为溶剂(以ppm为单位)，用TMS(0ppm)作为参照标准。当出现多重峰的时候，将使用下面的缩写：s(singlet，单峰)、d(doublet，双峰)、t(triplet，三重峰)、m(multiplet，多重峰)。
目标化合物使用Agilent 1260pre-HPLC或Calesep pump 250pre-HPLC(柱子型号：NOVASEP50/80mmDAC)，在210nm/254nm用UV检测。
使用以下方法进行本申请的化合物的合成：
制备例1-13
1.中间体a-1合成
Figure PCTCN2021083413-appb-000086
将2-溴-4-氯-1-碘苯(80.0g；252.1mmol)、苯硼酸(33.8g；277.3mmol)、四(三苯基膦)钯(5.8g；5.0mmol)、碳酸钾(76.5g；554.6mmol)、四丁基溴化铵(16.2g；50.4mmol)加入烧瓶中，并加入甲苯(640mL)、乙醇(320mL)和水(160mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌8小时；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；使用正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到浅灰色固体产物中间体a-1(40.5g；收率60％)。
使用与合成中间体a-1类似的方法，使用表1中反应物A所示的化合物替代2-溴-4-氯-1-碘苯，反应物B所示化合物替代苯硼酸，合成中间体a-2～a-4：
表1：中间体a-2～中间体a-4的合成
Figure PCTCN2021083413-appb-000087
Figure PCTCN2021083413-appb-000088
2.中间体b-1的合成
Figure PCTCN2021083413-appb-000089
将中间体a-1(40.5g，151.37mmol)和四氢呋喃(320ml)加入烧瓶中，氮气保护下，降温至-78℃，于搅拌条件下，滴加正丁基锂的四氢呋喃(2.5M)溶液(72.6mL，181.6mmol)，滴加完毕后保温搅拌1小时，保持-78℃滴加溶有金刚烷酮(25.0g，166.5mmol)的四氢呋喃(100mL)溶液，滴加完毕后保温1小时后升至室温，搅拌24小时，向反应液中加入盐酸(12M)(22mL，272.4mmol)的水(120mL)溶液，搅拌0.5小时，分液，有机相使用水洗至中性，加入无水硫酸镁干燥，减压除去溶剂得到粗品，使用乙酸乙酯/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体b-1(28.2g，50％)。
使用与合成中间体b-1类似的方法，使用表2中所示的反应物A替代中间体a-1，合成中间体b-2至中间体b-4：
表2：中间体b-2至中间体b-4的合成
Figure PCTCN2021083413-appb-000090
3.中间体c-1的合成
Figure PCTCN2021083413-appb-000091
将中间体b-1(28.2g，83.2mmol)和冰醋酸(280mL)加入烧瓶中，氮气保护常温搅拌条件下缓慢滴加浓硫酸(98％)(1.7mL，16.7mmol)的醋酸(40mL)溶液，滴加完毕后升至80℃，搅拌2 小时；降至室温，过滤析出的固体，使用水和乙醇淋洗滤饼，收集固体，烘干得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体中间体c-1(20.0g，产率75％)。
以下表3中反应物A替代中间体b-1，使用上述类似的方法合成中间体c-2至c-4：
表3：中间体c-2至中间体c-4的合成
Figure PCTCN2021083413-appb-000092
4.中间体d-1的合成
Figure PCTCN2021083413-appb-000093
将中间体c-1(20.0g，62.3mmol)和溶剂DMF(N,N-二甲基甲酰胺)(160mL)加入烧瓶中，氮气保护下常温搅拌10min，加入N-溴代丁二酰亚胺(NBS)(16.6g，93.5mmol)，升温至80℃，保温搅拌4h；反应结束降至室温，将反应液用二氯甲烷和水萃取，取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/正庚烷体系作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体d-1(18.9；收率76％)。
以下表4中反应物A替代中间体c-1，使用上述类似的方法合成中间体d-2至d-4：
表4：中间体d-2至中间体d-4的合成
Figure PCTCN2021083413-appb-000094
Figure PCTCN2021083413-appb-000095
5.中间体e-1的合成
Figure PCTCN2021083413-appb-000096
将中间体d-1(18.9g，47.3mmol)和四氢呋喃(150ml)加入烧瓶中，氮气保护下，降温至-78℃，于搅拌条件下，滴加正丁基锂的四氢呋喃(2.5M)溶液(22.7mL，56.73mmol)，滴加完毕后保温搅拌1小时，保持-78℃滴加溶有硼酸三甲酯(5.4g，52mmol)的四氢呋喃(20mL)溶液，滴加完毕后保温1小时后升至室温，搅拌24小时，向反应液中加入盐酸(12M)(7.1mL，85.1mmol)的水(35.5mL)溶液，搅拌1小时，分液，有机相使用水洗至中性，加入无水硫酸镁干燥，减压除去溶剂得到粗品，使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体e-1(9.5g，55％)。
使用与合成中间体e-1类似的方法，使用表5中所示的反应物A替代中间体d-1，合成中间体e-2至中间体e-4：
表5：中间体e-2至中间体e-4的合成
Figure PCTCN2021083413-appb-000097
6.中间体f-1的合成
Figure PCTCN2021083413-appb-000098
将中间体e-1(9.5g；26.1mmol)、3-溴二苯并呋喃(6.1g；24.8mmol)、四(三苯基膦)钯(0.57g；0.5mmol)、碳酸钾(7.5g；54.6mmol)、四丁基溴化铵(1.6g；5.0mmol)加入烧瓶中，并加入甲苯(76mL)、乙醇(38mL)和水(19mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌8小时；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；使用正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体f-1(9.1g；收率75％)。
使用与合成中间体f-1类似的方法，使用表6中反应物A所示的化合物替代中间体e-1，反应物B所示的化合物代替3-溴二苯并呋喃，合成中间体f-2至f-14：
表6：中间体f-2至中间体f-14的合成
Figure PCTCN2021083413-appb-000099
Figure PCTCN2021083413-appb-000100
使用与合成中间体f-1类似的方法，使用表7中反应物C所示的化合物替代中间体e-1，反应物D所示的化合物代替3-溴二苯并呋喃，合成中间体h-1至h-9：
表7：中间体h-1至中间体h-9的合成
Figure PCTCN2021083413-appb-000101
Figure PCTCN2021083413-appb-000102
8.中间体g-1的合成
Figure PCTCN2021083413-appb-000103
将中间体f-1(9.1g，18.9mmol)，联硼酸频哪醇酯(5.7g，22.4mmol)、三(二亚苄基丙酮)二钯(0.17g，0.19mmol)、2-二环己基磷-2',4',6'-三异丙基联苯(0.17g，0.37mmol)、醋酸钾(4.4g，41.1mmol)和1,4-二氧六环(72mL)加入烧瓶中，氮气保护条件下于100℃回流搅拌18小时；降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体g-1(7.0g，65％)。
以下表8中反应物A替代中间体f-1，使用上述类似的方法合成中间体g-2至g-14：
表8：中间体g-2至中间体g-14的合成
Figure PCTCN2021083413-appb-000104
Figure PCTCN2021083413-appb-000105
9.化合物16的合成
Figure PCTCN2021083413-appb-000106
将中间体g-1(7.0g；12.1mmol)、2-氯-4,6-二苯基-1,3,5-三嗪(3.1g；11.5mmol)，四(三苯基膦)钯(0.27g；0.23mmol)，碳酸钾(3.5g；25.3mmol)，四丁基溴化铵(0.7g；2.3mmol)加入烧瓶中，并加入甲苯(56mL)、乙醇(28mL)和水(14mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌12小时；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/正庚烷混合溶剂作为流动相对粗品进行硅胶柱色谱提纯，得到固体产物化合物16(4g；收率50％)。
使用与合成制备例1类似的方法，使用表9中所示的反应物A替代中间体g-1，用表9中所示的 反应物B替代2-氯-4,6-二苯基-1,3,5-三嗪，合成表10中制备例2-14：
表9：制备例2-14
Figure PCTCN2021083413-appb-000107
Figure PCTCN2021083413-appb-000108
二.制备例15-23的合成
以制备例15为例：
Figure PCTCN2021083413-appb-000109
将中间体h-1(9g，19.0mmol)，4-二苯并呋喃(3.67g，17.3mmol)，Pd(OAc) 2(0.04g，0.17mmol)，K 2CO 3(5.25g，38.05mmol)，xphos(0.16g，0.34mmol)，加入甲苯(72mL)，无水乙醇(36mL)，去离子水(18mL)于三口烧瓶中，在78℃温度下回流反应12h，反应结束后，用二氯甲烷和水进行萃取，取有机相无水MgSO 4干燥，抽滤，浓缩有机层，粗产品硅胶过柱提纯，得到化合物62(5.5g，产率53％)。
使用与合成制备例15类似的方法，使用表10中所示的反应物A替代中间体h-1，用表10中所示的反应物B替代4-二苯并呋喃，合成表10所示制备例16-23：
表10：制备例16-23
Figure PCTCN2021083413-appb-000110
Figure PCTCN2021083413-appb-000111
三.制备例24-35的合成
1.中间体I-1的合成
Figure PCTCN2021083413-appb-000112
将中间体c-1(20g，62.3mmol)，联硼酸频哪醇酯(19.0g，74.8mmol)、三(二亚苄基丙酮)二钯(0.57g，0.62mmol)、2-二环己基磷-2',4',6'-三异丙基联苯(0.59g，1.25mmol)、醋酸钾(13.4g，137.1mmol)和1,4-二氧六环(160mL)加入烧瓶中，氮气保护条件下于100℃回流搅拌18小时；降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体I-1(15.4g，收率60％)。
以下表11中反应物A替代中间体c-1，使用上述类似的方法合成中间体I-2至I-3：
表11：中间体I-2至中间体I-3的合成
Figure PCTCN2021083413-appb-000113
2.中间体J-1的合成
Figure PCTCN2021083413-appb-000114
将中间体I-1(15g；36.4mmol)、2-溴-4-氯二苯并[B,D]呋喃(8.5g；30.3mmol)，四(三苯基膦)钯(0.7g；0.61mmol)，碳酸钾(9.2g；66.7mmol)，四丁基溴化铵(1.9g；6.1mmol)加入烧瓶中，并加入甲苯(120mL)、乙醇(60mL)和水(30mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌12小时；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/正庚烷混合溶剂作为流动相对粗品进行硅胶柱色谱提纯，得到固体产物中间体J-1(8.1g；收率55％)。
使用与合成中间体J-1类似的方法，使用表12中所示的反应物A替代中间体I-1，用表12中所示的反应物B替代2-溴-4-氯二苯并[B,D]呋喃，合成表12中所示中间体J-2至J-11：
表12：中间体J-2至J-11
Figure PCTCN2021083413-appb-000115
Figure PCTCN2021083413-appb-000116
Figure PCTCN2021083413-appb-000117
3.中间体k-1的合成
Figure PCTCN2021083413-appb-000118
将中间体J-1(8.1g，16.6mmol)，联硼酸频哪醇酯(5.1g，19.9mmol)、三(二亚苄基丙酮)二钯(0.15g，0.17mmol)、2-二环己基磷-2',4',6'-三异丙基联苯(0.15g，0.33mmol)、醋酸钾(3.6g，36.6mmol)和1,4-二氧六环(64mL)加入烧瓶中，氮气保护条件下于100℃回流搅拌18小时；降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体k-1(5.2g，54％)。
以下表13中反应物A替代中间体J-1，使用上述类似的方法合成中间体k-2至k-11：
表13：中间体k-2至k-11
Figure PCTCN2021083413-appb-000119
Figure PCTCN2021083413-appb-000120
4.制备例24(化合物29)合成
Figure PCTCN2021083413-appb-000121
将中间体k-1(5.2g；9.0mmol)、4-溴-1,1',3',1”-三联苯(2.3g；7.5mmol)，四(三苯基膦)钯(0.17g；0.15mmol)，碳酸钾(2.3g；16.5mmol)，四丁基溴化铵(0.5g；1.5mmol)加入烧瓶中，并加入甲苯(40mL)、乙醇(20mL)和水(10mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌12小时；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/正庚烷混合溶剂作为流动相对粗品进行硅胶柱色谱提纯，得到固体产物化合物29(3.0g；收率58％)。
使用与合成制备例24类似的方法，使用表14中所示的反应物A替代中间体k-1，用表14中所示的反应物B替代4-溴-1,1',3',1”-三联苯，合成表14所示制备例25-34：
表14：制备例25-34
Figure PCTCN2021083413-appb-000122
Figure PCTCN2021083413-appb-000123
Figure PCTCN2021083413-appb-000124
对以上化合物进行质谱分析，数据如下表15所示：
表15：质谱表征数据
Figure PCTCN2021083413-appb-000125
上述实施例中部分化合物的核磁数据：
表16：
Figure PCTCN2021083413-appb-000126
Figure PCTCN2021083413-appb-000127
有机电致发光器件的制备和性能评估
实施例1：绿色有机电致发光器件
使用以下方法进行绿色有机电致发光器件的制作：
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2021083413-appb-000128
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、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。需要说明的是，ITO基板还可以根据实际需要切割成其他尺寸，在此不对本申请中ITO基板的尺寸做特殊限定。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2021083413-appb-000129
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-01，形成厚度为
Figure PCTCN2021083413-appb-000130
的第一空穴传输层。
在第一空穴传输层上真空蒸镀HT-02，形成厚度为
Figure PCTCN2021083413-appb-000131
的第二空穴传输层。
在第二空穴传输层上，将化合物62：GH-n1：Ir(ppy) 3以52％：43％：5％(蒸镀速率)的比例进行共蒸，形成厚度为
Figure PCTCN2021083413-appb-000132
的绿色发光层(EML)。
将ET-01和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2021083413-appb-000133
厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021083413-appb-000134
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 PCTCN2021083413-appb-000135
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021083413-appb-000136
的CP-01，形成有机覆盖层(CPL)，从而完成整个有机发光器件的制备。
实施例2-实施例26
除了在形成发光层时，使用以下表17中所示的混合组分替代实施例1中的混合组分之外，采用与实施例1相同的方法制作有机电致发光器件。
比较例1-比较例5
除了在形成发光层时，使用以下表17中所示的混合组分替代实施例1中的混合组分以外，采用与实施例1相同的方法制备有机电致发光器件。
其中，在实施例1-26及比较例1-5中使用的材料结构如下所示：
Figure PCTCN2021083413-appb-000137
Figure PCTCN2021083413-appb-000138
对实施例1～26和比较例1～5所制备的有机电致发光器件，在20mA/cm 2的条件下进行性能测试，测试结果如下表17中。
表17：有机电致发光器件的性能测试结果
Figure PCTCN2021083413-appb-000139
Figure PCTCN2021083413-appb-000140
Figure PCTCN2021083413-appb-000141
根据表17所示的数据可知，实施例1～26所制备的有机电致发光器件相较于比较例1～5所制备的有机电致发光器件，其驱动电压基本相近，发光效率至少提高了16.3％，器件寿命至少提高了20.3％。因此，本申请的化合物用作有机电致发光器件的有机发光层材料时，尤其是用作有机电致发光器件的有机发光层的主体材料时，可以有效的改善有机电致发光器件的效率性能和寿命。
例如，相比于对比例1化合物而言，本申请化合物结构中金刚烷螺芴环上直接连接二苯并五元环，能量传输能力提高，激子耐受度提升，更适合作为电子型发光层主体材料，而化合物A则更适合用于电子传输层。
实施例27：红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 PCTCN2021083413-appb-000142
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、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。需要说明的是，ITO基板还可以根据实际需要切割成其他尺寸，在此不对本申请中ITO基板的尺寸做特殊限定。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为的厚度为
Figure PCTCN2021083413-appb-000143
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-03，形成厚度为
Figure PCTCN2021083413-appb-000144
的第一空穴传输层。
在第一空穴传输层上真空蒸镀HT-04，形成厚度为
Figure PCTCN2021083413-appb-000145
的第二空穴传输层。
在第二空穴传输层上，将化合物23：Ir(piq) 2(acac)＝85％：15％(蒸镀速率)的比例进行共同蒸镀，形成厚度为
Figure PCTCN2021083413-appb-000146
的红色发光层(EML)。
将ET-01和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021083413-appb-000147
厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021083413-appb-000148
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 PCTCN2021083413-appb-000149
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021083413-appb-000150
的CP-01，形成有机覆盖层(CPL)，从而完成有机发光器件的制备。
实施例28-实施例34
除了在形成发光层时，使用以下表18中所示的混合组分替代实施例27中的混合组分之外，采用与实施例27相同的方法制作有机电致发光器件。
比较例6-比较例8
除了在形成发光层时，使用以下表18中所示的混合组分替代实施例27中的发光层主体以外，采用与实施例27相同的方法制备有机电致发光器件。
其中，在实施例27-34及比较例6-8中使用的材料结构如下所示：
Figure PCTCN2021083413-appb-000151
对实施例27～34和比较例6-8所制备的有机电致发光器件，在20mA/cm 2的条件下进行性能测试，测试结果如下表18中。
表18：有机电致发光器件的性能测试结果
Figure PCTCN2021083413-appb-000152
Figure PCTCN2021083413-appb-000153
根据表18所示的数据可知，实施例27～34所制备的有机电致发光器件相较于比较例6～8所制备的有机电致发光器件，其驱动电压相近，器件发光效率至少提升了19.4％，寿命至少提高了30.1％。因此，本申请化合物用作有机电致发光器件的有机发光层材料时，尤其是用作有机电致发光器件的有机发光层的主体材料时，可以改善有机电致发光器件的效率性能和寿命性能。
例如，相比于对比例8化合物而言，本申请化合物结构中二苯并五元环与缺电子杂芳基之间未直接连接，而是分别与螺芴连接，因此T 1有明显提升，激子耐受度提升，更适合作为电子型发光层主体材料，而化合物Z则更适合用于电子传输层。
本申请化合物中，作为化合物核心中一部分的金刚烷基与芴基螺合得到金刚烷螺芴，金刚烷螺芴与二苯并五元稠合环单键连接，使化合物整体具有较强的刚性并使得本申请的化合物具有高的第一三重态能级，该大分子结构具有较强的刚性，自由旋转的δ键使两个环平面之间形成一定的扭转角度，因此使得本申请化合物拥有了高的第一三重态能级和合适的HOMO能级分布，并且二苯并五元稠合环具有优秀的能量传递作用，可以有效促进发光层主体和客体材料间的能量传递，因此可作为有机电致发光材料中的发光层主体材料，改善有机电致发光器件的效率性能。
金刚烷基与芴基螺合，其可以通过超共轭效应而大幅增加大平面共轭结构的电子云密度，增强化合物的空穴迁移率，有助于促进发光层中空穴和电子的传输平衡，进而提高电子和空穴在有机发光层中的复合率，减少或者避免电子穿过有机发光层而向空穴传输层传输，进而可以有效地保护空穴传输层材料免受电子的冲击，提高有机电致发光器件的寿命。螺合于芴基上的金刚烷基具有大的空间体积和较强的刚性，因此其可以降低大平面共轭结构之间的相互作用力，减小分子间π-π堆叠，调节分子间的堆叠程度，进而使得化合物在成膜时能够具有更为稳定的无定形态，改善化合物的成膜性，进而进一步提高有机电致发光器件的寿命。
以上结合附图详细描述了本申请的可选实施方式，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 (18)

  1. 一种化合物，其中，所述化合物的结构式如化学式1所示：
    Figure PCTCN2021083413-appb-100001
    其中，环A和环B各自独立地选自碳原子数6～14的芳环；
    X选自O、S、Si(R 3R 4)、C(R 3R 4)；
    各R 1彼此相同或不同，且各自独立地选自：氘、卤素、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为3～12的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12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7～18的芳烷氧基或
    Figure PCTCN2021083413-appb-100002
    Ar 1选自碳原子数为6～40的取代或未取代的芳基、碳原子数为3～40的取代或未取代的杂芳基；
    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3～30的取代或未取代的亚杂芳基；
    Ar 1和L 1中的取代基彼此相同或不同，且各自独立地选自：氘、氰基、卤素基团、硝基、基团U、碳原子数为1～12的烷氧基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷基、碳原子数为3～12的环烷基、碳原子数为3～12的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12的烷硫基、碳原子数为6～18的芳氧基、碳原子数为7～18的芳烷基或碳原子数为6～18的芳氧基构成的组，所述基团U选自碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基，所述芳基和杂芳基中的取代基选自氘、氰基、卤素基团、碳原子数为1～12的烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为1～12的卤代烷基、碳原子数为3～12的烷基硅烷基、碳原子数为6～20的芳基或碳原子数为3～18的杂芳基所构成的组；
    或者，在各L 1和Ar 1中，当同一原子上具有两个取代基时，任选地，两个所述取代基相互连接，以与它们所共同连接的原子一起形成5到18元脂肪族环或5到18元芳香环；
    各R 2彼此相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1～12的烷基、碳原子数为1～12的卤代烷基、碳原子数为1～12的烷氧基、碳原子数为3～12的环烷基、碳原子数为3～12的的杂环基、碳原子数为3～12的烷基硅烷基、碳原子数为6～18的芳基硅烷基、碳原子数为1～12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7～18的芳烷基或
    Figure PCTCN2021083413-appb-100003
    L 2选自单键、碳原子数为6～30的取代或未取代的亚芳基或
    Figure PCTCN2021083413-appb-100004
    且所述L 2不为亚蒽基；
    Ar 2选自碳原子数为6～30的取代或未取代的芳基或
    Figure PCTCN2021083413-appb-100005
    且所述Ar 2不为蒽基；
    其中，Q和T分别独立地选自O、S、C(R 7R 8)或Si(R 7R 8)，
    R 3、R 4、R 7、R 8彼此相同或不同，且各自独立地选自氢、碳原子数1～12的取代或未取代的烷基、碳原子数1～12的取代或未取代的卤代烷基、碳原子数为6～18的取代或未取代的芳基、碳原子数为3～18的取代或未取代的杂芳基，所述R 3、R 4、R 7和R 8中的取代是指被氘、卤素基团、氰基、碳原子数为1～4的烷基所取代；或者所述R 7和R 8相互连接以与它们共同连接的原子形成5到13元脂肪族 环或5到13元芳香环；或者所述R 3和R 4相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
    R 5和R 6彼此相同或不同，且各自独立地选自氢、氘、卤素基团、氰基、碳原子数1～12的烷基、碳原子数1～12的卤代烷基、碳原子数1～12的烷氧基、碳原子数3～12的环烷基、碳原子数为3～12的杂环基、碳原子数3～12的烷基硅烷基、碳原子数6～18的芳基硅烷基、碳原子数1～12的烷硫基、碳原子数为6～18的芳基、二苯并噻吩基或二苯并呋喃基；
    n 1表示R 1的个数，n 2表示R 2的个数，n 5表示R 5的个数，n 6表示R 6的个数，且n 1、n 2、n 5、n 6分别独立地选自0、1、2、3、4、5、6、7或8；当n 1大于1时，任意两个所述R 1相同或者不同，当n 2大于1时，任意两个所述R 2相同或者不同，当n 5大于1时，任意两个所述R 5相同或者不同，当n 6大于1时，任意两个所述R 6相同或者不同。
  2. 根据权利要求1所述的化合物，其中，n 1为1，n 2为0，且R 1为
    Figure PCTCN2021083413-appb-100006
    或者 ，n 1为0，n 2为1，且R 2为
    Figure PCTCN2021083413-appb-100007
  3. 根据权利要求1或2所述的化合物，其中，X选自O、S、Si(R 3R 4)或C(R 3R 4)，所述R 3和R 4相同，且R 3、R 4选自甲基或苯基；或者所述R 3和R 4相互连接以与它们共同连接的原子形成环戊烷、环己烷或芴环。
  4. 根据权利要求1～3任一项所述的化合物，其中，Q和T分别独立地选自O、S、C(R 7R 8)或Si(R 7R 8)，所述R 7和R 8相同，且R 7、R 8选自甲基或苯基；或者所述R 7和R 8相互连接以与它们共同连接的原子形成环戊烷、环己烷或芴环。
  5. 根据权利要求1所述的化合物，其中，所述化合物的结构式如式(f-1)～(f-16)中的任意一种所示：
    Figure PCTCN2021083413-appb-100008
    Figure PCTCN2021083413-appb-100009
  6. 根据权利要求1～5任一项所述的化合物，其中，所述L 1选自单键、取代或未取代的亚苯基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的9,9-二甲基芴亚基、取代或未取代的亚菲基、取代或未取代的亚蒽基、螺[环戊烷-1,9’-芴]亚基、螺[环己烷-1,9’-芴]亚基、取代或未取代的亚吡啶基、取代或未取代的亚嘧啶基、取代或未取代的9,9-二甲基-9H-9-硅杂芴亚基、取代或未取代的二苯并呋喃亚基、取代或未取代二苯并噻吩亚基、取代或未取代的亚喹啉基、取代或未取代的亚异喹啉基、取代或未取代的亚咔唑基、取代或未取代的亚菲咯琳基、取代或未取代的螺二芴亚基中的一种，或者为上述亚基中两者或三者通过单键连接所形成的亚基基团；所述L 1中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基所组成的组。
  7. 根据权利要求1～6任一项所述的化合物，其中，所述L 1选自单键、或者选自化学式(j-1)至化学式(j-12)所示的基团所组成的组；
    Figure PCTCN2021083413-appb-100010
    Figure PCTCN2021083413-appb-100011
    Figure PCTCN2021083413-appb-100012
    其中，M 2选自单键或者
    Figure PCTCN2021083413-appb-100013
    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中的两个或者两个以上选自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中的两个或者两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
    Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个或者两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
    Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 33中至少一个选自N；当Q 24～Q 33中的两个或者两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
    E 1～E 12、J 5～J 8分别独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～18的杂芳基、碳原子数为6～20的芳基、碳原子数为3～9的三烷基硅烷基、碳原子数为8～12的芳基硅烷基、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6～12的芳氧基、碳原子数为6～12的芳硫基；
    e 1～e 12以e r表示，E 1～E 14以E r表示，r为变量，表示1～12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或9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 13E 14)；其中，各E 13、E 14、E 15、E 16和E 17分别独立地选自：氢、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；
    或者，任选地，上述E 16和E 17相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
    或者，任选地，上述E 13和E 14相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
    各K 4独立地选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 18E 19)；其中，各E 20、E 21、E 22、E 18、E 19分别独立地选自：氢、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、；
    或者，任选地，上述E 21和E 22相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环；
    或者，任选地，上述E 18和E 19相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环。
  8. 根据权利要求1～7任一项所述的化合物，其中，所述L 1选自单键、取代或未取代的W 1其中，未取代的W 1选自如下基团所组成的组：
    Figure PCTCN2021083413-appb-100014
    其中，取代的W 1为未取代的W 1被一个或者多个选自氘、氟、氯、溴、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～9的三烷基硅烷基、碳原子数为5～7的环烷基、碳原子数为6～15的芳基和碳原子数为3～12的杂芳基的取代基所取代而形成的基团，且当取代的W 1上的取代基数量为多个时，任意两个取代基之间相同或者不同。
  9. 根据权利要求1～8任一项所述的化合物，其中，所述Ar 1选自取代或未取代的基团W 3，其中，未取代的W 3选自如下基团所组成的组：
    Figure PCTCN2021083413-appb-100015
    Figure PCTCN2021083413-appb-100016
    其中，各T 1、T 2和T 3彼此相同或不同，分别独立地选自氢、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基；任意两个T 1相同或者不相同，任意两个T 2相同或者不相同，任意两个T 3相同或者不相同；
    其中，取代的W 3为未取代的W 3被一个或者多个选自氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、碳原子数为3～7的环烷基、碳原子数为6～15的芳基、碳原子数为3～18的杂芳基、碳原子数为1～4的烷硫基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基所取代而形成的基团，且当W 3上的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
  10. 根据权利要求9所述的化合物，其中，各T 1、T 2和T 3彼此相同或不同，分别独立地选自：氢、苯基、萘基、蒽基、菲基、二联苯基、三联苯基、芴基、二苯并噻吩基、二苯并呋喃基、N-苯基咔唑基、咔唑-9-基苯基、吡啶基、嘧啶基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、苯并噁嗪、三亚苯基、菲咯琳基；
    取代的W 3为未取代的W 3被一个或者多个选自：氟、氘、氰基、三氟甲基、三甲基硅烷基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、环戊烷基、环己烷基、苯基、联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、嘧啶基、喹啉基、异喹啉基、咔唑基、N-苯基咔唑基、二苯并呋喃基、二苯并噻吩基的取代基所取代而形成的基团；且当W 3上的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
  11. 根据权利要求1～10任一项所述的化合物，其中，所述L 2选自单键、取代或未取代的亚苯基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的9,9-二甲基芴亚基、取代或未取代的亚菲基、螺[环戊烷-1,9’-芴]亚基、螺[环己烷-1,9’-芴]亚基、 取代或未取代的9,9-二甲基-9H-9-硅杂芴亚基、取代或未取代的二苯并呋喃亚基、取代或未取代二苯并噻吩亚基、取代或未取代的螺二芴亚基中的一种，或者为上述亚基中两者或三者通过单键连接所形成的亚基基团；所述L 2中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、萘基所组成的组。
  12. 根据权利要求1～11任一项所述的化合物，其中，所述L 2选自单键、取代或未取代的W 2，其中，未取代的W 2选自如下基团所组成的组：
    Figure PCTCN2021083413-appb-100017
    其中，取代的W 2为未取代的W 2被一个或者多个选自氘、氟、氯、溴、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～9的三烷基硅烷基、碳原子数为5～7的环烷基和碳原子数为6～15的芳基的取代基所取代而形成的基团，且当取代的W 2上的取代基数量为多个时，任意两个取代基之间相同或者不同。
  13. 根据权利要求1～12任一项所述的化合物，其中，所述Ar 2选自取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的芴基、取代或未取代的硅杂芴基、取代或未取代的二苯并呋喃亚基、取代或未取代二苯并噻吩亚基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、螺[环戊烷-1,9’-芴]基、螺[环己烷-1,9’-芴]基中的一种，或者为上述基团中两者或三者通过单键连接所形成的亚基基团；所述Ar 2中的取代基彼此相同或不同，各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、三氟甲基、三甲基硅烷基、苯基、芴基、氰基取代的苯基、氟取代的苯基、萘基、二苯并噻吩、二苯并呋喃、环己烷基、三甲基硅烷基所组成的组，Ar 2中的取代基有多个时，各取代基彼此相同或不同。
  14. 根据权利要求1～13任一项所述的化合物，其中，所述Ar 2选自取代或未取代的基团W 4，其中，未取代的W 4选自如下基团所组成的组：
    Figure PCTCN2021083413-appb-100018
    Figure PCTCN2021083413-appb-100019
    其中，取代的W 4为未取代的W 4被一个或者多个选自氘、氟、氯、氰基、碳原子数为1～4的烷基、碳原子数为1～4的烷氧基、碳原子数为3～7的环烷基、碳原子数为6～14的芳基、碳原子数为3～12的杂芳基、碳原子数为1～4的烷硫基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基的取代基所取代而形成的基团，且当W 4上的取代基的数量为多个时，任意两个取代基之间相同或者不相同。
  15. 根据权利要求1所述的化合物，其中，所述化合物选自如下化合物所组成的组：
    Figure PCTCN2021083413-appb-100020
    Figure PCTCN2021083413-appb-100021
    Figure PCTCN2021083413-appb-100022
    Figure PCTCN2021083413-appb-100023
    Figure PCTCN2021083413-appb-100024
    Figure PCTCN2021083413-appb-100025
    Figure PCTCN2021083413-appb-100026
    Figure PCTCN2021083413-appb-100027
    Figure PCTCN2021083413-appb-100028
    Figure PCTCN2021083413-appb-100029
  16. 一种有机电致发光器件，其中，包括相对设置的阳极和阴极，以及设置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1～15中任意一项所述的化合物。
  17. 根据权利要求16所述的有机电致发光器件，其中，所述功能层包括空穴注入层、空穴传输层、有机电致发光层、电子传输层以及电子注入层，所述有机电致发光层含有权利要求1～15中任一项所述的化合物。
  18. 一种电子装置，其中，该电子装置包括权利要求16或17所述的有机电致发光器件。
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