WO2021135183A1 - 有机化合物、有机电致发光器件和电子装置 - Google Patents

有机化合物、有机电致发光器件和电子装置 Download PDF

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WO2021135183A1
WO2021135183A1 PCT/CN2020/104581 CN2020104581W WO2021135183A1 WO 2021135183 A1 WO2021135183 A1 WO 2021135183A1 CN 2020104581 W CN2020104581 W CN 2020104581W WO 2021135183 A1 WO2021135183 A1 WO 2021135183A1
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carbon atoms
group
substituted
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unsubstituted
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French (fr)
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马林楠
马天天
南朋
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陕西莱特光电材料股份有限公司
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Priority to KR1020217043434A priority Critical patent/KR102454692B1/ko
Priority to US17/623,772 priority patent/US11492314B2/en
Publication of WO2021135183A1 publication Critical patent/WO2021135183A1/zh

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Definitions

  • This application relates to the technical field of organic materials, in particular to an organic compound, an organic electroluminescent device using the organic compound, and an electronic device using the organic electroluminescent device.
  • Organic electroluminescent devices also known as organic light-emitting diodes, refer to the phenomenon that organic light-emitting materials are excited by current to emit light under the action of an electric field. It is a process of converting electrical energy into light energy.
  • organic electroluminescent diodes OLED have the advantages of active light emission, large optical path range, low driving voltage, high brightness, high efficiency, low energy consumption, and simple manufacturing process. It is precisely because of these advantages that organic light-emitting materials and devices have become one of the most popular scientific research topics in the scientific and industrial circles.
  • Organic electroluminescence devices generally include an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer, and a cathode that are stacked in sequence.
  • the two electrodes When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, the holes on the anode side also move to the light emitting layer, and the electrons and holes are combined in the electroluminescent layer.
  • Excitons are formed, and the excitons are in an excited state to release energy to the outside, so that the electroluminescent layer emits light to the outside.
  • CN106206964, WO2011010843, etc. disclose light-emitting layer materials that can be prepared in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of this application is to provide an organic compound, organic electroluminescent device and electronic device to improve the performance of the organic electroluminescent device and electronic device.
  • an organic compound is provided, and the structure of the organic compound is shown in Chemical Formula 1:
  • L is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon atom number Heteroarylene group of 3-30, substituted or unsubstituted cycloalkylene group of 3-20 carbon atoms;
  • Ar 1 is selected from substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted carbon atoms of 3 to 30 Heteroaryl
  • Each R 1 and R 2 are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, and optionally 0, 1, 2, 3, 4 or 5 selected from deuterium, fluorine, Cyano, methyl, ethyl, isopropyl, tert-butyl, and trimethylsilyl substituted aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms , An alkylsilyl group with 3 to 18 carbon atoms, a triarylsilyl group with 6 to 18 carbon atoms, an alkyl group with 1 to 12 carbon atoms, and an alkoxy group with 1 to 12 carbon atoms, C1-C12 haloalkyl, C2-C12 alkenyl, C3-C10 cycloalkyl, C2-C12 heterocycloalkyl, C2-C12 It is an alkylamino group having 1-10, an alkylthio group having 1
  • n 1 is the number of substituent R 1 , n 1 is selected from 0, 1, 2, 3 or 4, when n 1 is greater than 1, any two R 1 are the same or different; or;
  • n 2 is the number of substituents R 2 , n 2 is selected from 0, 1, 2 or 3, when n 2 is greater than 1, any two R 2 are the same or different;
  • the substituents in Ar 1 and L are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, optionally 0, 1, 2 or 3 selected from deuterium, fluorine , Cyano, methyl, and trimethylsilyl substituents substituted by aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms, and alkane with 3 to 18 carbon atoms Alkylsilyl group, arylsilyl group having 6 to 18 carbon atoms, alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms , Alkenyl with 2 to 12 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, heterocycloalkyl with 2 to 12 carbon atoms, alkylamino with 1 to 10 carbon atoms, carbon An alkylthio group having 1 to 10
  • This application combines the adamantane spirofluorene group and the anthracene group to obtain a novel compound for organic electroluminescence devices; in this compound, the adamantane in the adamantane spirofluorene is greatly increased through the hyperconjugation effect
  • the electron cloud density on the fluorene group makes the HOMO energy level of the compound shallower, and the hole mobility ability is improved.
  • Both the adamantane spirofluorene and the anthracene group have high hole mobility. When the two are connected, the overall molecular The hole mobility is further improved, which is conducive to reducing the working voltage of the device and improving the luminous efficiency.
  • the adamantyl group as a rigid polycyclic alkyl group, combined with a rigid conjugated planar anthracene group not only increases the electron density of the whole molecule, increases the carrier transmission rate, but also increases the triplet energy level (T 1 ), which is more suitable for luminescent host materials.
  • T 1 triplet energy level
  • the introduction of another aromatic group on the central anthracene group enhances molecular asymmetry, making the material difficult to crystallize and improving device stability. When this type of material is used as the host material of an organic electroluminescent device, the device can have a higher luminous efficiency and a long life.
  • an organic electroluminescent device comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer includes the above-mentioned organic Compound.
  • an electronic device including the above-mentioned organic electroluminescent device.
  • 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.
  • Electron transport layer 360, electron injection layer; 400, electronic device.
  • L is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon atom number Heteroarylene group of 3-30, substituted or unsubstituted cycloalkylene group of 3-20 carbon atoms;
  • Ar 1 is selected from substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted carbon atoms of 3 to 30 Heteroaryl
  • Each R 1 is the same or different from each other, and each R 2 is the same or different from each other, and is independently selected from deuterium, fluorine, chlorine, bromine, cyano, and is optionally substituted by 0, 1, 2, 3, 4 or 5.
  • a substituent selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, and trimethylsilyl substituted with an aryl group with 6 to 20 carbon atoms, and the number of carbon atoms is Heteroaryl groups having 3 to 18, alkylsilyl groups having 3 to 18 carbon atoms, triarylsilyl groups having 6 to 18 carbon atoms, alkyl groups having 1 to 12 carbon atoms, and 1 carbon atom ⁇ 12 alkoxy, C 1-12 haloalkyl, C 2-12 alkenyl, C 3-10 cycloalkyl, C 2-12 hetero Cycloalkyl, alkylamino group with 1-10 carbon atoms,
  • n 1 is the number of substituents R 1 , n 1 is selected from 0, 1, 2, 3 or 4, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 is the number of substituents R 2 , n 2 is selected from 0, 1, 2 or 3, when n 2 is greater than 1, any two R 2 are the same or different;
  • the substituents in Ar 1 and L are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, optionally 0, 1, 2 or 3 selected from deuterium, fluorine , Cyano, methyl, and trimethylsilyl substituents substituted by aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 18 carbon atoms, and alkane with 3 to 18 carbon atoms Alkylsilyl group, arylsilyl group having 6 to 18 carbon atoms, alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms , Alkenyl with 2 to 12 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, heterocycloalkyl with 2 to 12 carbon atoms, alkylamino with 1 to 10 carbon atoms, carbon An alkylthio group having 1 to 10
  • This application combines the adamantane spirofluorene group and the anthracene group to obtain a novel compound for organic electroluminescence devices; in this compound, the adamantane in the adamantane spirofluorene is greatly increased through the hyperconjugation effect
  • the electron cloud density on the fluorene group makes the HOMO energy level of the compound shallower, and the hole mobility ability is improved.
  • Both the adamantane spirofluorene and the anthracene group have high hole mobility. When the two are connected, the overall molecular The hole mobility is further improved, which is conducive to reducing the working voltage of the device and improving the luminous efficiency.
  • the adamantyl group as a rigid polycyclic alkyl group, combined with a rigid conjugated planar anthracene group not only increases the overall electron density of the molecule, increases the carrier transmission rate, but also increases the triplet energy level, which is more suitable It is used for luminous host material.
  • the introduction of another aromatic group on the central anthracene group enhances the asymmetry of the molecule, the rotation mode between the groups is increased, the molecular stacking is reduced, the space complexity is increased, and the molecule is in an amorphous state.
  • the difficulty in crystallization improves the film-forming properties of the material, thereby improving the stability of the device.
  • this type of material is used as the host material of an organic electroluminescent device, the device can have a higher luminous efficiency and a long life.
  • the number of carbon atoms of L and Ar 1 refers to the total number of carbon atoms.
  • L is selected from substituted arylene groups with 10 carbon atoms, all carbon atoms of the arylene group and the substituents thereon are 10, and if Ar 1 is a tert-butyl substituted phenyl group, Then, the Ar 1 is a substituted aryl group having 9 carbon atoms.
  • hetero refers to including at least one heteroatom selected from B, N, O, S, Se, Si, P, etc. in a functional group.
  • the unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent.
  • substituted or unsubstituted alkyl refers to a substituted alkyl group or an unsubstituted alkyl group.
  • Substituted means that it can be substituted by a substituent selected from the following groups: deuterium, halogen group, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, alkenyl, cycloalkyl, Heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, alkoxy, alkylthio, aryloxy, arylthio, triarylsilyl, alkylboron, alkylphosphono, etc.
  • alkyl may include linear or branched alkyl.
  • Alkyl groups can have 1 to 20 carbon atoms.
  • a numerical range such as “1 to 20” refers to each integer in the given range; for example, “1 to 20 carbon atoms” means that it can contain 1 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 atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms base.
  • the alkyl group may also be a medium-sized alkyl group having 1 to 10 carbon atoms.
  • the alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms.
  • 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 in the present invention.
  • 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 ), etc.
  • the alkyl group may be substituted or unsubstituted.
  • alkenyl refers to a hydrocarbon group containing one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups can be unsubstituted or substituted. Alkenyl groups can have 1 to 20 carbon atoms, and whenever appearing herein, a numerical range such as “1 to 20" refers to each integer in the given range; for example, "1 to 20 carbon atoms” means that Contains 1 carbon atom, 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 atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms or 20 carbon atoms ⁇ alkenyl.
  • the alkenyl group may be vinyl, butadiene,
  • cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and condensed ring structures.
  • Cycloalkyl groups can have 3-20 carbon atoms, and a numerical range such as “3 to 20" refers to each integer in the given range; for example, "3 to 20 carbon atoms” means that it can 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 atoms, 13 carbon atoms, A cycloalkyl group of 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms.
  • the cycloalkyl group may be a small ring, an ordinary ring, or a large ring having 3 to 20 carbon atoms. Cycloalkyl groups can also be classified as monocyclic-only one ring, bicyclic-two rings-or polycyclic-three or more rings. Cycloalkyl groups can also be divided into two rings sharing one carbon atom-a spiro ring, two rings sharing two carbon atoms-a fused ring, and two rings sharing two or more carbon atoms-a bridged ring. In addition, cycloalkyl groups may be substituted or unsubstituted. In some embodiments, the cycloalkyl group is a 5- to 10-membered cycloalkyl group.
  • the cycloalkyl group is a 5- to 8-membered cycloalkyl group.
  • examples of the cycloalkyl group may be, but are not limited to : Five-membered cycloalkyl is cyclopentyl, six-membered cycloalkyl is cyclohexyl, 10-membered polycyclic alkyl such as adamantyl, etc.
  • the "ring” in this application includes saturated rings and unsaturated rings; saturated rings are cycloalkyl, heterocycloalkyl, and unsaturated rings, namely cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
  • "aliphatic ring” includes saturated cycloalkyl and partially unsaturated cycloalkyl, for example, saturated cycloalkyl, cyclopentyl, cyclohexyl, adamantyl, etc., partially unsaturated cycloalkane Group, cyclobutene and so on.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by a carbon-carbon bond, through A monocyclic aryl group and a fused ring aryl group conjugated by carbon-carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application.
  • the aryl group does not contain heteroatoms.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[9,10 ]Phenanthryl, pyrenyl, benzofluoranthene, Group, perylene, 9,9 dimethyl fluorenyl, 9,9-diphenyl fluorenyl, spirobifluorenyl, indenyl, but not limited thereto.
  • the number of carbon atoms in the aryl group can be 6-25, in other embodiments the number of carbon atoms in the aryl group can be 6-18, and in other embodiments the number of carbon atoms in the aryl group
  • the number of carbon atoms can be 6-13.
  • the number of carbon atoms can be 6, 12, 13, 18, 20, 25, or 30.
  • the number of carbon atoms can also be other numbers, which will not be listed here.
  • 9,9 dimethyl fluorenyl, 9,9-diphenyl fluorenyl, and spirobifluorenyl are all regarded as aryl groups.
  • aryl in this application can have one or more points of attachment to the rest of the molecule.
  • the explanation of the aryl group can be applied to the arylene group.
  • a substituted aryl group means that one or more hydrogen atoms in the aryl group are replaced by other groups.
  • at least one hydrogen atom is covered by a deuterium atom, F, Cl, I, CN, hydroxyl, amino, branched alkyl, linear alkyl, cycloalkyl, alkoxy, alkylamino, alkylthio or other groups replace.
  • the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • the substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18.
  • 2-tert-butylphenyl is a substituted aryl group having 9 carbon atoms.
  • an aryl group with 6-25 ring carbon atoms in this application means that the number of carbon atoms in the main aromatic ring in the aryl group is 6-25, and the carbon in the substituent on the aryl group The number of atoms is not counted.
  • the number of ring-forming carbon atoms in the aryl group can also be 6-20, 6-18, 6-14, or 6-10, but is not limited thereto.
  • diphenylfluorenyl has 13 ring carbon atoms
  • spirobifluorenyl is an aryl group with 25 ring carbon atoms.
  • the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Se, Si, and S as a heteroatom.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated by carbon-carbon bonds, any aromatic ring
  • the system is an aromatic monocyclic ring or an aromatic condensed ring, and any aromatic ring system contains the heteroatom.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazole Group, benzothiazolyl, benzo, be
  • thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system, N-arylcarbazolyl, N-heteroarylcarbazolyl, phenyl substituted dibenzofuranyl, etc. It is a heteroaryl group of multiple aromatic ring systems conjugated through carbon-carbon bonds.
  • heteroaryl group can have one bond, two bonds or multiple bonds to connect to other parts of the molecule.
  • the substituted heteroaryl group with 3-30 carbon atoms means that the total number of carbon atoms of the heteroaryl group and the substituent on the heteroaryl group is 3-30.
  • a heteroaryl group with 4 to 18 ring carbon atoms means that the number of carbon atoms on the heteroaromatic ring in the heteroaryl group is 4 to 18, and the number of carbon atoms in the substituents on the heteroaryl group is not calculated Inside.
  • the number of carbon atoms on the heteroaryl group may be 3-18, 4-18, 3-12, 3-8, but it is not limited thereto.
  • a phenyl substituted pyridyl group has 5 ring carbon atoms
  • an N-phenylcarbazolyl group has 12 ring carbon atoms.
  • heteroaryl can be applied to heteroarylene.
  • the ring system formed by n atoms is an n-membered ring.
  • phenyl is a 6-membered aryl group.
  • the 6 to 10-membered aromatic ring refers to a benzene ring, an indene ring, a naphthalene ring, and the like.
  • aryl can be applied to arylene
  • heteroaryl can be applied to heteroarylene
  • alkyl can be applied to alkylene
  • cycloalkyl can be Applied to cycloalkylene
  • each q is independently 0, 1, 2 or 3
  • each R independently selected from hydrogen, fluorine, and chlorine in the description
  • formula Q-1 represents that there are q substituents R on the benzene ring ", each R” can be the same or different, and the options of each R" do not affect each other
  • formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and the two benzene rings
  • 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.
  • the non-positioned link in this application refers to the single bond extending from the ring system It means that one end of the link can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (X) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. ) ⁇ Any possible connection shown in formula (X-7).
  • the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of the benzene ring on one side. It includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
  • the non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system.
  • the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and its meaning includes the following formula (Y-1) to Any possible connection mode shown in formula (Y-7).
  • each R 1 is the same or different from each other, and each R 2 is 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 6-20.
  • the substituents in Ar 1 and L are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, aryl groups with 6 to 20 carbon atoms, and 6 to carbon atoms.
  • each R 1 in the compound of the present application is the same or different from each other
  • each R 2 is the same or different from each other
  • each R 1 and R 2 are independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, , Cyano groups, alkyl groups having 1 to 6 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkylamino groups having 1 to 4 carbon atoms, Alkylthio groups having 1 to 4 carbon atoms, aryl groups having 6 to 15 carbon atoms, heteroaryl groups having 3 to 15 carbon atoms, trialkylsilyl groups having 3 to 8 carbon atoms, three A phenylsilyl group, a cycloalkyl group having 5 to 10 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, and an arylthio group having 6 to 12 carbon atoms.
  • each of R 1 and R 2 are the same or different from each other, and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl , Tert-butyl, methoxy, ethoxy, isopropoxy, n-propoxy, cyclopentyl, cyclohexane, trifluoromethyl, trimethylsilyl, triphenylsilyl, Optional 0, 1, 2, 3, 4 or 5 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl Substituted phenyl, naphthyl, pyridyl, pyrimidinyl, dibenzothienyl, dibenzofuranyl or quinolinyl, and when the number of R 1 and R 2 is more than 1, any two Rs 1 or
  • each R 1 in the compound of the present application is the same or different from each other
  • each R 2 is the same or different from each other
  • each R 1 and R 2 are independently selected from deuterium, fluorine, cyano, and cyclohexane.
  • the compound of the present application has the structure shown in the following chemical formula 1-1 to chemical formula 1-3:
  • L in the compound of the present application is selected from substituted or unsubstituted arylene groups having 6 to 25 ring carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 18 ring carbon atoms
  • the substituents in the L are the same or different from each other, and are independently selected from: deuterium, fluorine, chlorine, bromine, cyano, alkyl having 1 to 6 carbon atoms, and 1 to 4 carbon atoms
  • L is selected from the group consisting of a single bond or a substituent represented by chemical formula j-1 to chemical formula j-13:
  • M 1 is selected from a single bond or
  • Q 1 to Q 5 are each independently selected from N or C(F 1 ), 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(F 1 ) When any two F 1 are the same or different;
  • Q 6 to Q 13 are each independently selected from N or C(F 2 ), 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(F 2 ) When any two F 2 are the same or different;
  • Q 14 to Q 23 are each independently selected from N or C(F 3 ), 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(F 3 ) When any two F 3 are the same or different;
  • Q 24 to Q 33 are each independently selected from N or C(F 4 ), 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(F 4 ) When any two F 4 are the same or different;
  • E 1 to E 14 and F 1 to F 4 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl groups having 3 to 18 carbon atoms, and those having 6 to 18 carbon atoms
  • e r is the number of substituent Er , and r is Any integer from 1 to 14; when
  • K 1 is selected from O, S, Se, N (E 15 ), C (E 16 E 17 ), Si (E 16 E 17 ); wherein, E 15 , E 16 , and E 17 are each independently selected from: carbon atoms An aryl group having 6 to 18, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a carbon number of 2 to 10 heterocycloalkyl, or E 16 and E 17 are connected to each other to form a saturated or unsaturated 5- to 12-membered aliphatic ring with the atoms to which they are commonly connected.
  • the number of carbon atoms in the ring can be a 5-membered ring, which means that It can also be a 6-membered ring, which forms It can also be a 13-membered ring, for example
  • the number of carbon atoms in the ring formed by the interconnection of E 16 and E 17 can also be other values, which will not be listed here.
  • K 2 is selected from a single bond, O, S, Se, N (E 18 ), C (E 19 E 20 ), Si (E 19 E 20 ); wherein, E 18 , E 19 , and E 20 are each independently selected from : C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group, C3-C10 cycloalkyl group, C3-C10 It is a heterocycloalkyl group of 2-10, or E 19 and E 20 are connected to each other to form a saturated or unsaturated 5- to 12-membered aliphatic ring.
  • E 19 and E 20 optionally form a ring is consistent with the understanding in other technical solutions of this application (when E 16 and E 17 are connected to each other to form a ring).
  • L is selected from a single bond, unsubstituted W 1 or substituted W 1 , wherein the unsubstituted W 1 is selected from the group consisting of the following substituents:
  • the substituted W 1 means that the unsubstituted W 1 is replaced by one or more selected from deuterium, fluorine, chlorine, cyano, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, carbon A haloalkyl group having 1 to 4 atoms, an alkylsilyl group having 3 to 9 carbon atoms, a triphenylsilyl group, a cycloalkyl group having 3 to 10 carbon atoms, and an aromatic group having 6 to 12 carbon atoms A group formed by substituting a substituent of a heteroaryl group or a heteroaryl group having 3 to 12 carbon atoms, and when a plurality of substituents are included on the substituted W 1 , any two substituents are the same or different.
  • the L is
  • the L in the compound of the application is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene Substituted naphthylene, substituted or unsubstituted dibenzofuran subunit, substituted or unsubstituted dibenzothiophene subunit, substituted or unsubstituted quinolinylene, substituted or unsubstituted carbazolylidene, Substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted perylene, substituted or unsubstituted Pyrylene, substituted or unsubstituted 9,9-dip
  • L is selected from a single bond, unsubstituted W 2 or substituted W 2 , wherein the unsubstituted W 2 is selected from the group consisting of the following substituents:
  • the substituted W 2 is an unsubstituted W 2 with one or more selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropyl Oxy, trifluoromethyl, triphenylsilyl, cyclopentyl, cyclohexane, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, pyridyl, dibenzothienyl, A group formed by substitution of substituents of dibenzofuranyl, quinolinyl, and isoquinolinyl, and when multiple substituents are included on the substituted W 2 , any two substituents are the same or different.
  • the L is
  • L is not limited to the above-mentioned groups.
  • L is selected from a single bond, unsubstituted W 3 or substituted W 3 , wherein the unsubstituted W 3 is selected from the group consisting of the following substituents:
  • the substituted W 3 is an unsubstituted W 3 with one or more selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropyl Oxy, trifluoromethyl, triphenylsilyl, cyclopentyl, cyclohexane, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, pyridyl, dibenzothienyl, A group formed by substitution of substituents of dibenzofuranyl, quinolinyl, and isoquinolinyl, and when the substituted W 3 includes multiple substituents, any two substituents are the same or different.
  • Ar 1 is selected from substituted or unsubstituted aryl groups having 6-25 ring carbon atoms, and substituted or unsubstituted heteroaryl groups having 4-18 ring carbon atoms.
  • the aryl group with 6-25 ring carbon atoms and the heteroaryl group with 4-18 ring carbon atoms are optionally substituted by 0, 1, 2, 3, 4 or 5.
  • One is selected from: deuterium, fluorine, chlorine, bromine, cyano, alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, carbon Alkylamino groups with 1 to 4 atoms, alkylthio groups with 1 to 4 carbon atoms, aryl groups with 6 to 15 carbon atoms, heteroaryl groups with 3 to 15 carbon atoms, and carbon atoms 3-8 trialkylsilyl groups, triphenylsilyl groups, cycloalkyl groups with 5-10 carbon atoms, aryloxy groups with 6-12 carbon atoms, arylsulfides with 6-12 carbon atoms
  • the substituents of the group are substituted, and any two substituents are the same or different.
  • Ar 1 is selected from the group consisting of substituents represented by formula S-1 to formula S-11:
  • M 2 is selected from a single bond or
  • n a and n d are each independently 2, 3 or 4, when a group contains two or more of R a, each R a is the same or different; and when a group contains two or more When there are R d , each R d is the same or different from each other; n b is selected from 1, 2, 3, 4, or 5, and when a group contains two or more R b , each R b is the same or different from each other;
  • V 1 to V 40 are each independently selected from C(R v ) and N.
  • any two R v are the same or different from each other;
  • V is selected from the group consisting of O, S, Se, N (R v1 ), C (R v2 R v3 ) and Si (R v2 R v3 );
  • K 1 and K 2 are each independently selected from O, S or N(R k );
  • Each of R a , R b , Rd , R k , R v1 , R v2 , and R v3 is independently hydrogen, 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, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms; or R v2 and R v3 connected to the same atom The atoms connected to each other to form a saturated or unsaturated 5- to 13-membered aliphatic ring with them.
  • the number of carbon atoms of the ring may be a 5-membered ring, for example It can also be a 6-membered ring, for example It can also be a 13-membered ring, for example
  • the number of carbon atoms on the ring formed by the interconnection of R v2 and R v3 can also be other values, which will not be listed here.
  • Each R v is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl groups having 3 to 18 carbon atoms, aryl groups having 6 to 18 carbon atoms, and 3 to 12 carbon atoms
  • Ar 1 is unsubstituted T 1 or substituted T 1 , wherein the unsubstituted T 1 is selected from the group consisting of the following substituents:
  • Substituted T 1 means that unsubstituted T 1 is substituted with one or more selected from deuterium, fluorine, chlorine, cyano, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, carbon A haloalkyl group having 1 to 4 atoms, an alkylsilyl group having 3 to 9 carbon atoms, a triphenylsilyl group, a cycloalkyl group having 5 to 10 carbon atoms, and an aromatic group having 6 to 15 carbon atoms group, carbon atoms, heteroaryl group having 3 to 12 substituted to form a substituted group, and when substituted the substituent group 1 comprises a plurality of arbitrary two T groups identical or different substituents.
  • Ar 1 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the substituted T 1 is an unsubstituted T 1 with one or more selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy , Ethoxy, isopropoxy, trifluoromethyl, triphenylsilyl, cyclopentyl, cyclohexane, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, pyridyl , 9,9-Dimethylfluorenyl, dibenzothienyl, dibenzofuranyl, quinolinyl, isoquinolinyl substituents are substituted and formed, and when the substituted T 1 includes In the case of multiple substituents, any two substituents are the same or different.
  • Ar 1 is selected from the group consisting of the following substituents:
  • Ar 1 is not limited to the above-mentioned groups.
  • Ar 1 is selected from the group consisting of the following substituents:
  • the Ar 1 is also selected from the following groups represented by formula S-12 and formula S-13:
  • V 41 to V 55 are each independently selected from C(R v4 ) and N, at least one of V 48 to V 55 is N, when the same group contains multiple R v4 , any two R v4 Be the same or different from each other;
  • T is selected from the group consisting of O, S, Se, N (R t1 ), C (R t2 R t3 ) and Si (R t2 R t3 );
  • Each of R t1 , R t2 , and R t3 is independently hydrogen, 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, and carbon A cycloalkyl group having 3 to 10 atoms and a heterocycloalkyl group having 2 to 10 carbon atoms; alternatively, R t2 and R t3 connected to the same atom are connected to each other to form a saturated or Unsaturated 5- to 13-membered ring;
  • Each R v4 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl groups having 3 to 18 carbon atoms, aryl groups having 6 to 18 carbon atoms, and 3 to 12 carbon atoms
  • An oxy group, an arylthio group having 6 to 18 carbon atoms, or any two adjacent R v4 are connected to each other to form a 6-10 membered aromatic ring or a 6-10 membere
  • the Ar 1 is selected from substituted or unsubstituted T 2 , wherein the unsubstituted T 2 is independently selected from the following groups:
  • the substituted T 2 means that the unsubstituted T 2 is substituted by one or more selected from deuterium, fluorine, chlorine, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, carbon A haloalkyl group having 1 to 4 atoms, an alkylsilyl group having 3 to 9 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and a carbon atom A group formed by substituting a substituent of an aryl group having 6 to 13 and a heteroaryl group having 3 to 12 carbon atoms, and when the substituted T 6 includes multiple substituents, any two substituents Same or different.
  • the Ar 1 is independently selected from the following groups:
  • the organic compound described in this application is selected from the group consisting of the following compounds:
  • the application also provides an organic electroluminescent device, which includes an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer includes the organic compound of the application.
  • an organic electroluminescent device includes an anode 100 and a cathode 200 disposed oppositely, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic Compound.
  • the functional layer 300 includes an organic electroluminescent layer 330, and the organic electroluminescent layer 330 includes the organic compound of the present application.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, and may also include a host material and a guest material. In some embodiments, the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. Transfer to the host material, the host material transfers energy to the guest material, so that the guest material can emit light.
  • the host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, which are not particularly limited in this application .
  • the host material of the organic light-emitting layer 330 may be the organic compound and BH-n1 of the present application.
  • the guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials.
  • the guest material of the organic light emitting layer 330 is BD-1.
  • the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, and an electron transport layer which are sequentially stacked. 350 and cathode 200.
  • the organic compound provided in this application can be applied to the organic electroluminescent layer 330 of an organic electroluminescent device, which can effectively improve the luminous efficiency and lifetime of the organic electroluminescent device, and reduce the driving voltage of the organic electroluminescent device.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (workfunction) that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ] (PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 321 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.
  • the hole transport layer 321 is composed of the compound NPB.
  • the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials may be selected from carbazole polymers or other types of compounds, which are not specifically limited in this application.
  • the electron blocking layer 322 is composed of PAPB.
  • the electron transport layer 350 may be a single layer structure or a multilayer structure, which may include one or more electron transport materials, which may be selected from benzimidazole derivatives and oxadiazoles. Derivatives, quinoxaline derivatives or other electron transport materials are not specifically limited in this application.
  • the electron transport layer 350 may be composed of compounds ET-06 and LiQ.
  • the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto. It is preferable to include a metal electrode containing magnesium and silver as a cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 321 to enhance the ability of injecting holes into the hole transport layer 321.
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 360 may be further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 350.
  • the electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances.
  • the electron injection layer 360 may be composed of metal Yb.
  • a hole blocking layer 340 may also be provided between the organic electroluminescent layer 330 and the electron transport layer 350.
  • the organic electroluminescent device of the present application is optionally a blue light device.
  • the embodiments of the present application also provide an electronic device, which includes the above-mentioned organic electroluminescent device. Since the electronic device has the above-mentioned organic electroluminescent device, it has the same beneficial effects, and the details are not repeated here in this application.
  • the present application provides an electronic device 400 including the above-mentioned organic electroluminescent device.
  • 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, etc. Since the electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects, which will not be repeated in this application.
  • reaction flask is plugged with a suitable rubber stopper, and the substrate is injected through a syringe.
  • a silica gel column is used as the chromatographic column. Silica gel (100-200 mesh) was purchased from Qingdao Ocean Chemical Plant.
  • the measurement conditions for low-resolution mass spectrometry (MS) data are: Agilent 6120 quadrupole HPLC-M (column model: Zorbax SB-C18, 2.1 ⁇ 30mm, 3.5 microns, 6min, flow rate 0.6mL/min.
  • Mobile phase 5 %-95% (CH3CN containing 0.1% formic acid) in (H 2 O containing 0.1% formic acid), using electrospray ionization (ESI), and UV detection at 210nm/254nm.
  • 1 H NMR spectra were recorded using a Bruker 400MHz or 600MHz nuclear magnetic resonance spectrometer.
  • 1 H NMR spectrum uses CDCl 3 , CD 2 Cl 2, D 2 O, DMSO-d 6 , CD 3 OD or acetone-d 6 as the solvent (in ppm), and uses TMS (0 ppm) or chloroform (7.26 ppm) As a reference standard.
  • R 1 in the intermediate compound has the same meaning as described in other parts of the specification.
  • the compounds having the structures shown in the following chemical formulas (Ia) and (Ib) can be synthesized according to the following general synthesis schemes (1) and (2), but are not limited thereto.
  • Ar 1 has the meaning as described in this application.
  • Table 1 Compound structure, preparation and characterization data
  • Ar 1 has the meaning described in this application.
  • Pyridine-2-boronic acid (6.146g, 50mmol), 10-bromoanthracene-9-boronic acid (15g, 50mmol), tetrakis (triphenylphosphine) palladium (0.58g, 0.5mmol), potassium carbonate (7.35g, 75mmol) ), tetrabutylammonium chloride (0.278g, 1mmol), toluene (80mL), ethanol (20mL) and deionized water (20mL) were added to a round bottom flask, heated to 78°C under nitrogen protection, and stirred for 8 hours; The reaction solution was cooled to room temperature, and toluene (50 mL) was added for extraction.
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, using ultraviolet ozone and O 2 :N 2 plasma. Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL), and the compound NPB is vacuum-evaporated on the hole injection layer to form a thickness of The hole transport layer (HTL).
  • HIL hole injection layer
  • HTL hole transport layer
  • Compound 1 was used as the main body on the EBL, and BD-1 was doped at the same time according to the film thickness ratio of 100:3 to form a thickness of The light-emitting layer (EML).
  • EML The light-emitting layer
  • the compounds ET-06 and LiQ are vapor-deposited on the EML as the electron transport layer (ETL), the film thickness ratio is 1:1, and the thickness is
  • the metal Yb is vapor-deposited on the ETL as the electron injection layer (EIL), the thickness is
  • a silver (Ag) and magnesium (Mg) doped film layer with a film thickness ratio of 10:1 was deposited on the EIL as a cathode (cathode) with a thickness of
  • the compound CP-5 is vapor-deposited on the cathode as the light extraction layer (CPL) with a thickness of An organic capping layer (CPL) is formed, thereby completing the manufacture of an organic light-emitting device.
  • the organic electroluminescence device was fabricated in the same manner as in Example 1, except that the compounds shown in Table 7 below were used in place of Compound 1 when forming the light-emitting layer.
  • the adamantane spirofluorene group and the anthracene group are connected and combined to obtain a novel compound for organic electroluminescence devices; in the compound, both the adamantane spirofluorene and the anthracene group have high voids.
  • Hole mobility when the two are connected, the overall hole mobility of the molecule is further improved, which is beneficial to reduce the working voltage of the device and improve the luminous efficiency; the adamantane spirofluoren group is introduced into the anthracene compound light-emitting host to improve the overall molecular
  • the electron density increases the carrier transmission rate.
  • the introduction of another aromatic group on the central anthracene group enhances the molecular asymmetry, making the material difficult to crystallize and improving the stability of the device.
  • this type of material is used as the host material of an organic electroluminescent device, the device can have a higher luminous efficiency and a long life.

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Abstract

本申请属于有机材料技术领域，提供了一种有机化合物，将金刚烷螺芴基团和蒽基基团连接组合，得到了一种用于有机电致发光器件的新型化合物。该化合物中，金刚烷螺芴中金刚烷通过超共轭效应大幅增加芴基上的电子云密度，使化合物HOMO能级变浅，空穴迁移能力提升，金刚烷螺芴和蒽基基团均具有高的空穴迁移率，将二者连接时，使得分子整体的空穴迁移率进一步提高，有利于降低器件工作电压并提升发光效率。本申请还提供包含所述化合物的电子元件和电子装置，该有机化合物能够改善电子元件的性能。

Description

有机化合物、有机电致发光器件和电子装置
相关申请的交叉引用
本申请要求于2019年12月30日递交的、申请号为CN201911404482.6的中国专利申请和于2020年06月09日递交的、申请号为CN202010526332.9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
本申请涉及有机材料技术领域，尤其涉及一种有机化合物、使用该有机化合物的有机电致发光器件和应用该有机电致发光器件的电子装置。
背景技术
有机电致发光器件又称为有机发光二极管，是指有机发光材料在电场作用下，受到电流的激发而发光的现象。它是一种将电能转换为光能的过程。相比于无机发光材料，有机电致发光二极管OLED具有主动发光、光程范围大、驱动电压低、亮度大、效率高、耗能少以及制作工艺简单等优点。正是由于这些优点，有机发光材料与器件已经成为科学界和产业界十分热门的科研课题之一。
有机电致发光器件一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。
现有技术中，CN106206964、WO2011010843等公开了可以在有机电致发光器件中制备的发光层材料。然而，依然有必要继续研发新型的材料，以进一步提高电子元器件的性能。
所述背景技术部分申请的上述信息仅用于加强对本申请的背景的理解，因此它可以包括不构成对本领域普通技术人员已知的现有技术的信息。
发明内容
本申请的目的在于提供一种有机化合物、有机电致发光器件和电子装置，以改善有机电致发光器件和电子装置的性能。
为实现上述发明目的，本申请采用如下技术方案：
根据本申请的第一个方面，提供一种有机化合物，所述有机化合物的结构如化学式1所示：
Figure PCTCN2020104581-appb-000001
其中，L选自单键、取代或未取代的碳原子数为1～20的亚烷基、取代或未取代的碳原子数为6～30的亚芳基、取代或未取代的碳原子数为3～30的亚杂芳基、取代或未取代的碳原子数为3～20的亚环烷基；
Ar 1选自取代或未取代的碳原子数为3～20的环烷基、取代或未取代的碳原子数为6～40的芳基、取代或未取代的碳原子数为3～30的杂芳基；
各R 1和R 2彼此相同或不同，且分别独立地选自氘，氟，氯，溴，氰基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基的取代基所取代的碳原子数为 6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为3～18的烷基硅烷基，碳原子数为6～18的三芳基硅烷基，碳原子数为1～12的烷基，碳原子数为1～12的烷氧基，碳原子数为1～12的卤代烷基，碳原子数为2～12的烯基，碳原子数为3～10的环烷基，碳原子数为2～12的杂环烷基，碳原子数为1～10的烷胺基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基；
n 1为取代基R 1的数量，n 1选自0、1、2、3或4，当n 1大于1时，任意两个R 1相同或不同；或者；
n 2为取代基R 2的数量，n 2选自0、1、2或3，当n 2大于1时，任意两个R 2相同或不同；
所述Ar 1和L中的取代基彼此相同或不同，且分别独立地选自：氘，氟，氯，溴，氰基，任选地被0、1、2或3个选自氘、氟、氰基、甲基、三甲基硅基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为3～18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的烷基，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2～12的烯基，碳原子数为3～10的环烷基，碳原子数为2～12的杂环烷基，碳原子数为1～10的烷胺基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基。
本申请将金刚烷螺芴基团和蒽基基团连接组合，得到了一种用于有机电致发光器件的新型化合物；该化合物中，金刚烷螺芴中金刚烷通过超共轭效应大幅增加芴基上的电子云密度，使化合物HOMO能级变浅，空穴迁移能力提升，金刚烷螺芴和蒽基基团均具有高的空穴迁移率，将二者连接时，使得分子整体的空穴迁移率进一步提高，有利于降低器件工作电压并提升发光效率。另外，本申请化合物中，金刚烷基作为刚性多环烷基，与刚性共轭平面蒽基组合，不仅提升分子整体的电子密度，提升载流子传输速率，而且提高三线态能级(T 1)，更适于用于发光主体材料。此外，在中心蒽基基团上引入的另一个芳香性基基团增强了分子不对称性，使得材料不易结晶从而提升器件稳定性。将该类材料作为有机电致发光器件主体材料使用时，可以使器件具有较高的发光效率以及长的寿命。
根据本申请的第二个方面，提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含上述的有机化合物。
根据本申请的第三个方面，提供一种电子装置，包括上述有机电致发光器件。
附图说明
通过参照附图详细描述其示例实施方式，本申请的上述和其它特征及优点将变得更加明显。
图1是本申请实施方式的有机电致发光器件的结构示意图。
图2是本申请一实施方式的电子装置的结构示意图。
图中主要元件附图标记说明如下：
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、电子阻挡层；330、有机电致发光层；340、空穴阻挡层；350、电子传输层；360、电子注入层；400、电子装置。
具体实施方式
现在将参考附图更全面地描述示例性实施例。然而，示例性实施例能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施例使得本申请将更加全面和完整，并将示例性实施例的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。
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。
所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多个实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。然而，本领域技术人员将意识到，可以实践本申请的技术方案而没有所述特定细节中的一个或更多个，或者可以采用其它的方法、组元、材料等。在其它情况下，不详细示出或描述公知结构、材料或者操作以避免模糊本申请的主要技术创意。
本申请提供一种有机化合物，所述有机化合物的结构如化学式1所示：
Figure PCTCN2020104581-appb-000002
其中，L选自单键、取代或未取代的碳原子数为1～20的亚烷基、取代或未取代的碳原子数为6～30的亚芳基、取代或未取代的碳原子数为3～30的亚杂芳基、取代或未取代的碳原子数为3～20的亚环烷基；
Ar 1选自取代或未取代的碳原子数为3～20的环烷基、取代或未取代的碳原子数为6～40的芳基、取代或未取代的碳原子数为3～30的杂芳基；
所述各R 1彼此相同或不同，各R 2彼此相同或不同，且分别独立地选自氘，氟，氯，溴，氰基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为3～18的烷基硅烷基，碳原子数为6～18的三芳基硅烷基，碳原子数为1～12的烷基，碳原子数为1～12的烷氧基，碳原子数为1～12的卤代烷基，碳原子数为2～12的烯基，碳原子数为3～10的环烷基，碳原子数为2～12的杂环烷基，碳原子数为1～10的烷胺基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基；
n 1为取代基R 1的数量，n 1选自0、1、2、3或4，当n 1大于1时，任意两个R 1相同或不同；
n 2为取代基R 2的数量，n 2选自0、1、2或3，当n 2大于1时，任意两个R 2相同或不同；
所述Ar 1和L中的取代基彼此相同或不同，且分别独立地选自：氘，氟，氯，溴，氰基，任选地被0、1、2或3个选自氘、氟、氰基、甲基、三甲基硅基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为3～18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的烷基，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2～12的烯基，碳原子数为3～10的环烷基，碳原子数为2～12的杂环烷基，碳原子数为1～10的烷胺基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基。
本申请将金刚烷螺芴基团和蒽基基团连接组合，得到了一种用于有机电致发光器件的新型化合物；该化合物中，金刚烷螺芴中金刚烷通过超共轭效应大幅增加芴基上的电子云密度，使化合物HOMO能级变浅，空穴迁移能力提升，金刚烷螺芴和蒽基基团均具有高的空穴迁移率，将二者连接时，使得分子整体的空穴迁移率进一步提高，有利于降低器件工作电压并提升发光效率。另外，本申请化合物中，金刚烷基作为刚性多环烷基，与刚性共轭平面蒽基组合，不仅提升分子整体的电子密度，提升载流子传输速率，而且提高三线态能级，更适于用于发光主体材料。此外，在中心蒽基基团上引入的另一个芳香性基基团增强了分子不对称性，基团之间的旋转方式增加，减少分子堆叠，空间复杂度提高，使得分子在无定形状态下不易结晶使得材料成膜性提高，进而提升器件稳定性。将该类材料作为有机电致发光器件主体材料使用时，可以使器件具有较高的发光效率以及长的寿命。
在本申请中，L和Ar 1的碳原子数，指的是所有碳原子数。举例而言，若L选自取代的碳原子数为10的亚芳基，则亚芳基及其上的取代基的所有碳原子数为10，若Ar 1为叔丁基取代的苯基，则该Ar 1为取代的碳原子数为9的芳基。
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个选自B、N、O、S、Se、Si或P等的杂原子。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”。
在本发明中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取 代基。例如，“取代或未取代的烷基”是指具有取代基的烷基或者非取代的烷基。“取代”是指可以被选自以下基团的取代基所取代：氘、卤素基团、杂芳基、芳基、三烷基硅基、烷基、卤代烷基、烯基、环烷基、杂环烷基、环烯基、杂环烯基、烷氧基、烷硫基、芳氧基、芳硫基、三芳基硅基、烷基硼基、烷基膦氧基等。
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20个碳原子，在本申请中，诸如“1至20”的数值范围是指给定范围中的各个整数；例如，“1至20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、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20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发明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。
在本申请中，“烯基”是指在直链或支链烃链中包含一个或多个双键的烃基。烯基可为未取代的或取代的。烯基可具有1至20个碳原子，每当在本文出现时，诸如“1至20”的数值范围是指给定范围中的各个整数；例如，“1至20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、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20个碳原子的烯基。例如，烯基可以为乙烯基、丁二烯或丙烯基等。
在本申请中，环烷基指的是含有脂环结构的饱和烃，包含单环和稠环结构。环烷基可具有3-20个碳原子，诸如“3至20”的数值范围是指给定范围中的各个整数；例如，“3至20个碳原子”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、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20个碳原子的环烷基。环烷基可为具有3至20个碳原子的小环、普通环或大环。环烷基还可分为单环-只有一个环、双环-两个环-或多环-三个或以上环。环烷基还可分为两个环共用一个碳原子-螺环、两个环共用两个碳原子-稠环和两个环共用两个以上碳原子-桥环。此外，环烷基可为取代的或未取代的。在一些实施方式中环烷基为5至10元环烷基，在另一些实施方式中，环烷基为5至8元环烷基，举例而言，环烷基的示例可以是，但不限于：五元环烷基即环戊基、六元环烷基即环己烷基、10元多环烷基如金刚烷基等。
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。本发明中“脂肪族环”包含饱和的环烷基和部分不饱和的环烷基，例如，饱和环烷基，环戊烷基、环己烷基、金刚烷基等，部分不饱和环烷基，环丁烯等。
在本申请中，芳基指的是衍生自芳香烃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，芳基中不含有杂原子。举例而言，在本申请中，联苯基、三联苯基等为芳基。芳基的示例可以包括苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、六联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2020104581-appb-000003
基、苝基、9,9二甲基芴基、9,9-二苯基芴基、螺二芴基、茚基，而不限于此。在一些实施例中，芳基中的碳原子数可以是6-25个，在另一些实施例中芳基中的碳原子数可以是6-18个，在另一些实施例中芳基中的碳 原子数可以是6-13个。举例而言，其碳原子数量可以是6个、12个、13个、18个、20个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。在本申请中，9,9二甲基芴基、9,9-二苯基芴基、螺二芴基均视为芳基。
本申请中的“芳基”上可以有一个或多个连接点与分子其余部分相连。在本申请中，对芳基的解释可应用于亚芳基。
在本申请中，取代的芳基，指的是芳基中的一个或者多个氢原子被其它基团所取代。例如至少一个氢原子被氘原子、F、Cl、I、CN、羟基、氨基、支链烷基、直链烷基、环烷基、烷氧基、烷胺基、烷硫基或者其他基团取代。可以理解的是，取代的芳基的碳原子数，指的是芳基及其芳基上的取代基的总碳原子数。例如，取代的碳原子数为18的芳基，指的是芳基和芳基上的取代基的碳原子总数为18个。举例而言，2-叔丁基苯基为碳原子数为9的取代的芳基。
在本申请中，本申请中成环碳原子数为6-25的芳基指的是芳基中位于主体芳香环上的碳原子数是6-25个，芳基上的取代基中的碳原子数不计算在内。芳基中的成环碳原子数还可以是6-20个、6-18个、6-14个或6-10个，但不限于此。例如二苯基芴基，成环碳原子数为13，螺二芴基属于成环碳原子数为25的芳基。
在本申请中，杂芳基可以是包括B、O、N、P、Se、Si和S中的至少一个作为杂原子的杂芳基。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，任一芳香环体系为一个芳香单环或者一个芳香稠环，，且任一芳香环体系中含有所述杂原子。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、N-芳基咔唑基、N-杂芳基咔唑基、N-烷基咔唑基、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、二苯并甲硅烷、二苯并呋喃基、苯基取代的二苯并呋喃基、苯氧茶碱基
Figure PCTCN2020104581-appb-000004
噻蒽基
Figure PCTCN2020104581-appb-000005
苯噁嗪基
Figure PCTCN2020104581-appb-000006
吩噻嗪
Figure PCTCN2020104581-appb-000007
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的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基、苯基取代的二苯并呋喃基等为通过碳碳键共轭连接的多个芳香环体系的杂芳基。
可以理解的是，“杂芳基”上可以有一个键、两个键或多个键与分子中其他部分相连接。
可以理解的是，“取代的碳原子数为3～30的杂芳基指的是杂芳基和杂芳基上的取代基的碳原子总数为3～30个。
成环碳原子数为4～18的杂芳基指的是杂芳基中位于杂芳环上的碳原子数是4～18个，杂芳基上的取代基中的碳原子数不计算在内。杂芳基上的碳原子数可以是3～18个、4～18个、3～12个、3～8个，但不限于此。例如苯基取代的吡啶基，成环碳原子数视为5，N-苯基咔唑基视为成环碳原子数为12。
在本申请中，对杂芳基的解释可应用于亚杂芳基。
在本发明中，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至10元芳环是指苯环、茚环和萘环等。
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 PCTCN2020104581-appb-000008
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。
本申请中的不定位连接键，是指从环体系中伸出的单键
Figure PCTCN2020104581-appb-000009
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-7)所示出的任一可能的连接方式。
Figure PCTCN2020104581-appb-000010
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 PCTCN2020104581-appb-000011
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 PCTCN2020104581-appb-000012
在一些实施方案中，其中，所述各R 1彼此相同或不同，各R 2彼此相同或不同，且分别独立地选自氘、氟、氯、溴、氰基、碳原子数为6～20的芳基、碳原子数为6～18的杂芳基、碳原子数为3～18的烷基硅烷基、碳原子数为6～18的三芳基硅烷基、碳原子数为1～12的烷基、碳原子数为1～12的烷氧基、碳原子数为1～12的卤代烷基、碳原子数为2～12的烯基、碳原子数为3～10的环烷基、碳原子数为2～12的杂环烷基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基；
所述Ar 1和L中的取代基彼此相同或不同，且分别独立地选自：氘、氟、氯、溴、氰基、碳原子数为6～20的芳基、碳原子数为6～18的杂芳基、碳原子数为3～18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的烷基、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2～12的烯基、碳原子数为3～10的环烷基、碳原子数为2～12的杂环烷基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基。
在一些实施方式中，本申请化合物中所述各R 1彼此相同或不同，各R 2彼此相同或不同，且各R 1和R 2分别独立地选自氢、氘、氟、氯、溴、、氰基、碳原子数为1～6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1～4的烷胺基、碳原子数为1～4的烷硫基、碳原子数为6～15的芳基、碳原子数为3～15的杂芳基、碳原子数为3～8的三烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳氧基、碳原子数为6～12的芳硫基。
在一些实施方式中在一些实施方案中，所述各R 1和R 2彼此相同或不同，且分别独立地选自氘，氟，氯，溴，氰基，甲基，乙基，异丙基，叔丁基，甲氧基，乙氧基，异丙氧基，正丙氧基，环戊烷基，环己烷基，三氟甲基，三甲基硅烷基，三苯基硅基，任选被0、1、2、3、4或5个选自氘、氟、氯、溴、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基的取代基所取代的苯基，萘基，吡啶基，嘧啶基，二苯并噻吩基，二苯并呋喃基或喹啉基，且当R 1和R 2的个数多于1时，任意两个R 1或R 2相同或者不相同。
在一些实施方式中，本申请化合物中所述各R 1彼此相同或不同，各R 2彼此相同或不同，且各R 1和R 2分别独立地选自氘、氟、氰基、环己烷基、环戊烷基、三甲基硅烷基、甲氧基、乙氧基、异丙氧基、甲基、乙基、异丙基、叔丁基、二异丙基硅烷基、苯基、萘基、吡啶基、喹啉基。
在一些实施方式中，本申请化合物具有以下化学式1-1至化学式1-3所示结构：
Figure PCTCN2020104581-appb-000013
在一些实施方式中，本申请化合物中L选自取代或未取代的成环碳原子数为6～25的亚芳基、取代或未取代的成环碳原子数为3～18的亚杂芳基；所述L中的取代基彼此相同或不同，且分别独立地选自：氘、氟、氯、溴、氰基、碳原子数为1～6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1～4的烷胺基、碳原子数为1～4的烷硫基、碳原子数为6～15的芳基、碳原子数为3～15的杂芳基、碳原子数为3～8的三烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳氧基、碳原子数为6～12的芳硫基。
在一些实施方式中，L选自单键或化学式j-1至化学式j-13所示的取代基所组成的组：
Figure PCTCN2020104581-appb-000014
其中，M 1选自单键或者
Figure PCTCN2020104581-appb-000015
Q 1～Q 5各自独立地选自N或者C(F 1)，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(F 1)时，任意两个F 1相同或者不相同；
Q 6～Q 13各自独立地选自N或者C(F 2)，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(F 2)时，任意两个F 2相同或者不相同；
Q 14～Q 23各自独立地选自N或者C(F 3)，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(F 3)时，任意两个F 3相同或者不相同；
Q 24～Q 33各自独立地选自N或者C(F 4)，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(F 4)时，任意两个F 4相同或者不相同；
E 1～E 14、F 1～F 4各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～18的杂芳基、碳原子数为6～18的芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～12的芳基甲硅烷基、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的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基；e r为取代基E r的数量，r为1～14的任意整数；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
K 1选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 16E 17)；其中，E 15、E 16、E 17各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 16和E 17相互连接以与它们共同连接的原子形成饱和或不饱和的5至12元脂肪族环。举例而言，式j-8中当K 2为单键、M 1为单键时，K 1为碳原子的情况中当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环时，该环的碳原子数可以是5元环，即形成
Figure PCTCN2020104581-appb-000016
也可以是6元环，即形成
Figure PCTCN2020104581-appb-000017
还可以是13元环，例如
Figure PCTCN2020104581-appb-000018
当然，E 16和E 17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。
K 2选自单键、O、S、Se、N(E 18)、C(E 19E 20)、Si(E 19E 20)；其中，E 18、E 19、E 20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、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 19和E 20相互连接以与它们共同连接的原子形成饱和或不饱和的5至12元脂肪族环。此处对于E 19和E 20任选地成环的理解，与本申请其他技术方案(当E 16和E 17相互连接以成环)中的理解一致。
在一些实施方式中，L选自单键、未取代的W 1或者取代的W 1，其中，未取代的W 1选自如下取代基所组成的组：
Figure PCTCN2020104581-appb-000019
Figure PCTCN2020104581-appb-000020
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、碳原子数为1～6的烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基、三苯基硅烷基、碳原子数为3～10的环烷基、碳原子数为6～12的芳基、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上包括多个取代基时，任意两个取代基相同或者不相同。还在一些实施方案中，所述L为
Figure PCTCN2020104581-appb-000021
在另一些实施方案，本申请化合物中所述L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的二苯并呋喃亚基、取代或未取代的二苯并噻吩亚基、取代或未取代的亚喹啉基、取代或未取代的亚咔唑基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚苝基、取代或未取代的亚芘基、取代或未取代的9,9-二苯基芴基、取代或未取代的螺二芴亚基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基、取代或未取代的亚嘧啶基、取代或者未取代的亚吡啶基、取代或者未取代的亚吡嗪基、取代或者未取代的亚喹啉基、取代或者未取代的亚异喹啉基、取代或者未取代的亚喹唑啉基，或者为它们中两者或三者通过单键连接形成的亚基基团；所述取代是指任选地被0、1、2、3或4个选自氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、丙氧基、三氟甲基、苯基、萘基、三甲基硅烷基、三苯基硅烷基的取代基所取代。
在一些实施方式中，L选自单键、未取代的W 2或者取代的W 2，其中，未取代的W 2选自如下取代基所组成的组：
Figure PCTCN2020104581-appb-000022
Figure PCTCN2020104581-appb-000023
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、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、三苯基硅烷基、环戊烷基、环己烷基、三氟甲基、三甲基硅烷基、苯基、萘基、吡啶基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基的取代基所取代而形成的基团，且当取代的W 2上包括多个取代基时，任意两个取代基相同或者不相同。
还在一些实施方案中，所述L为
Figure PCTCN2020104581-appb-000024
本申请化合物中，L不限于上述基团。
在一些实施方式中，L选自单键、未取代的W 3或者取代的W 3，其中，未取代的W 3选自如下取代基所组成的组：
Figure PCTCN2020104581-appb-000025
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、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、三苯基硅烷基、环戊烷基、环己烷基、三氟甲基、三甲基硅烷基、苯基、萘基、吡啶基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基的取代基所取代而形成的基团，且当取代的W 3上包括多个取代基时，任意两个取代基相同或者不相同。
在一些实施方式中，Ar 1选自取代或未取代的成环碳原子数为6-25的芳基、取代或未取代的成环碳原子数为4-18的杂芳基。
在一些实施方式中，所述成环碳原子数为6-25的芳基和成环碳原子数为4-18的杂芳基，任选地被0、1、2、3、4或5个选自：氘、氟、氯、溴、氰基、碳原子数为1～6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1～4的烷胺基、碳原子数为1～4的烷硫基、碳原子数为6～15的芳基、碳原子数为3～15的杂芳基、碳原子数为3～8的三烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳氧基、碳原子数为6～12的芳硫基的取代基所取代，任意两个取代基相同或者不相同。
在一些实施方式中，Ar 1选自式S-1至式S-11所示的取代基所组成的组:
Figure PCTCN2020104581-appb-000026
上述基团中，M 2选自单键或者
Figure PCTCN2020104581-appb-000027
n a和n d各自独立地为1、2、3或4，当一个基团中包含两个或多个R a时，各R a彼此相同或不同；当一个基团中包含两个或多个R d时，各R d彼此相同或不同；n b选自1、2、3、4或5，当一个基团中包含两个或多个R b时，各R b彼此相同或不同；
V 1～V 40各自独立地选自C(R v)和N，当一个基团中包含两个或多个R v时，任意两个R v彼此相同或不同；
V选自O、S、Se、N(R v1)、C(R v2R v3)和Si(R v2R v3)所构成的组；
K 1和K 2各自独立地选自O、S或N(R k)；
各R a、R b、R d、R k、R v1、R v2、R v3分别独立地为氢、碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基；或者，连接于同一个原子上的R v2和R v3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。举例而言，R v2和R v3相互连接形成环时，该环的碳原子数可以是5元环，例如
Figure PCTCN2020104581-appb-000028
也可以是6元环，例如
Figure PCTCN2020104581-appb-000029
还可以是13元环，例如
Figure PCTCN2020104581-appb-000030
当然，R v2和R v3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。
各R v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6～18的芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～18的芳基甲硅烷基、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的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基。
在一些实施方式中，本申请的有机化合物中，Ar 1为未取代的T 1或者取代的T 1，其中，未取代的T 1选自如下取代基所组成的组:
Figure PCTCN2020104581-appb-000031
Figure PCTCN2020104581-appb-000032
取代的T 1为未取代的T 1被一个或者多个选自氘、氟、氯、氰基、碳原子数为1～6的烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～15的芳基、碳原子数为3～12的杂芳基的取代基所取代而形成的基团，且当取代的T 1上包括多个取代基时，任意两个取代基相同或者不相同。
还在一些实施方案中，Ar 1为
Figure PCTCN2020104581-appb-000033
还在一些实施方案中，取代的T 1为未取代的T 1被一个或者多个选自氘、氟、氯、氰基、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、三苯基硅烷基、环戊烷基、环己烷基、三氟甲基、三甲基硅烷基、苯基、萘基、吡啶基、9,9-二甲基芴基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基的取代基所取代而形成的基团，且当取代的T 1上包括多个取代基时，任意两个取代基相同或者不相同。
在一些实施方式中，本申请的有机化合物，其中，Ar 1选自如下取代基所组成的组：
Figure PCTCN2020104581-appb-000034
Figure PCTCN2020104581-appb-000035
本申请化合物中，Ar 1不限于上述基团。
在一些实施方式中，本申请的有机化合物中，Ar 1选自如下取代基所组成的组：
Figure PCTCN2020104581-appb-000036
Figure PCTCN2020104581-appb-000037
还在一些实施方案中，所述Ar 1还选自如下式S-12、式S-13所示基团：
Figure PCTCN2020104581-appb-000038
其中，V 41～V 55各自独立地选自C(R v4)和N，V 48～V 55中至少有一个为N，当同一个基团中包含多个R v4时，任意两个R v4彼此相同或不同；
T选自O、S、Se、N(R t1)、C(R t2R t3)和Si(R t2R t3)所构成的组；
各R t1、R t2、R t3分别独立地为氢、碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基；或者，连接于同一个原子上的R t2和R t3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元环；
各R v4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6～18的芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～12的芳基甲硅烷基、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的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基，或者，任意两个相邻的R v4相互连接形成6～10元芳环或6～10元杂芳环。
还在一些实施方案中，所述Ar 1选自取代或者未取代的T 2，其中未取代的T 2独立地选自如下所示基团：
Figure PCTCN2020104581-appb-000039
Figure PCTCN2020104581-appb-000040
取代的T 2为未取代的T 2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1～4的卤代烷基、碳原子数为3～9的烷基硅烷基、碳原子数为6～18的芳基硅基、碳原子数为5～7的环烷基、碳原子数为6～13的芳基、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T 6上包括多个取代基时，任意两个取代基相同或者不相同。
还在一些实施方案中，所述Ar 1独立地选自如下所示基团：
Figure PCTCN2020104581-appb-000041
Figure PCTCN2020104581-appb-000042
在一些实施方式中，本申请所述有机化合物选自如下化合物所组成的组：
Figure PCTCN2020104581-appb-000043
Figure PCTCN2020104581-appb-000044
Figure PCTCN2020104581-appb-000045
Figure PCTCN2020104581-appb-000046
Figure PCTCN2020104581-appb-000047
Figure PCTCN2020104581-appb-000048
Figure PCTCN2020104581-appb-000049
Figure PCTCN2020104581-appb-000050
Figure PCTCN2020104581-appb-000051
本申请还提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请的有机化合物。
举例而言，如图1所示，有机电致发光器件包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的有机化合物。
在一些实施方式中，功能层300包括有机电致发光层330，有机电致发光层330包含本申请的有机化合物。
在一些实施方式中，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。在一些实施方式中，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的主体材料可以为金属螯合物类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的主体材料可以为本申请的有机化合物与BH-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，在本申请一些实施例中，有机发光层330的客体材料为BD-1。
在本申请的一种实施方式中，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、电子阻挡层322、作为能量转化层的有机电致发光层330、电子传输层350和阴极200。本申请提供的有机化合物可以应用于有机电致发光器件的有机电致发光层330，可以有效改善有机电致发光 器件的发光效率和寿命，降低有机电致发光器件的驱动电压。
在一些实施方式中，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，workfunction)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
在一些实施方式中，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。举例而言，在本申请的一种实施方式中，空穴传输层321由化合物NPB组成。
在一些实施方式中，电子阻挡层322包括一种或多种电子阻挡材料，电子阻挡材料可以选自咔唑多聚体或者其他类型化合物，本申请对此不特殊的限定。举例而言，在本申请的一些实施方式中，电子阻挡层322由PAPB组成。
在一些实施方式中，电子传输层350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苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，电子传输层350可以由化合物ET-06和LiQ组成。
在一些实施方式中，阴极200包括以下阴极材料，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：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，但不限于此。优选包括包含镁和银的金属电极作为阴极。
在一些实施方式中，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，空穴注入层310可以由F4-TCNQ组成。
在一些实施方式中，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360，以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。在本申请的一种实施方式中，电子注入层360可以由金属Yb组成。
在一些实施方式中，在有机电致发光层330和电子传输层350之间还可以设置有空穴阻挡层340。
本申请的有机电致发光器件可选地为蓝光器件。
本申请实施方式还提供一种电子装置，该电子装置包括上述有机电致发光器件。由于该电子装置具有上述有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
举例而言，如图2所示，本申请提供一种电子装置400，该电子装置200包括上述有机电致发光器件。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，因此具有相同的有益效果，本申请在此不再赘述。
以下，通过实施例对本申请进一步详细说明。但是，下述实施例仅是本申请的例示，而并非限定本申请。
化合物合成
所属领域的专业人员将认识到：本申请所描述的化学反应可以用来合适地制备许多本申请的其他化合物，且用于制备本申请的化合物的其它方法都被认为是在本申请的范围之内。例如，根据本 申请那些非例证的化合物的合成可以成功地被所属领域的技术人员通过修饰方法完成，如适当的保护干扰基团，通过利用其他已知的试剂除了本申请所描述的，或将反应条件做一些常规的修改。另外，本申请所申请的反应或已知的反应条件也公认地适用于本申请其他化合物的制备。
下面所描述的实施例，除非其他方面表明所有的温度定为摄氏度。本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料。试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa ChemicalCompany，使用时都没有经过进一步纯化，除非其他方面表明。一般的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，和青岛海洋化工厂购买得到。
以下反应一般是在氮气或氩气正压下或在无水溶剂上套一干燥管(除非其他方面表明)，反应瓶都塞上合适的橡皮塞，底物通过注射器打入。色谱柱使用硅胶柱。硅胶(100-200目)购于青岛海洋化工厂。
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CH3CN)在(含0.1％甲酸的H 2O)中的比例)，采用电喷雾电离(ESI)，在210nm/254nm下，用UV检测。
1H NMR谱使用Bruker 400MHz或600MHz核磁共振谱仪记录。 1H NMR谱以CDCl 3、CD 2Cl 2、D 2O、DMSO-d 6、CD 3OD或丙酮-d 6为溶剂(以ppm为单位)，用TMS(0ppm)或氯仿(7.26ppm)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)、br(broadened，宽峰)、dd(doublet ofdoublets，双二重峰)、ddd(doublet of doublet of doublets，双重双二重峰)、dddd(doublet of doublet of doublet of doublets，双双双二重峰)、dt(doublet oftriplets，双三重峰)、tt(triplet of triplets，三三重峰)。偶合常数J，用赫兹(Hz)表示。
下列一般合成方案(一)和(二)中，中间体化合物中的R 1具有如说明书其他部分所述的含义。
本申请化合物中具有如以下化学式(Ia)和(Ib)所示结构的化合物，可以按照以下一般合成方案(一)和(二)进行合成，但不受此限定。
合成方案(一):
Figure PCTCN2020104581-appb-000052
Figure PCTCN2020104581-appb-000053
其中，Ar 1具有如本申请所述的含义。
合成过程：2-溴-4'-氯联苯和金刚烷酮在正丁基锂作用下，生成中间体I-A-1,中间体I-A-1在酸性条件下成环，生成中间体I-A-2，频哪醇硼酸酯与中间体I-A-2在碱性条件下发生Suzuki反应，生成中间体I-A-3，10-溴蒽-9-硼酸与中间体I-A-3在碱性条件下，通过钯催化剂发生偶联反应，生成中间体I-A，带芳基溴代物与中间体I-A在碱性条件下，钯催化剂下发生偶联反应，生成最终具有式(Ia)所示结构的终产物。
本申请化合物1～18可采用上述一般合成方案(一)制备，为了便于理解，下面以具体化合物1的制备过程为例，示例性的示出本申请部分化合物的合成过程。
中间体I-A的合成
Figure PCTCN2020104581-appb-000054
在氮气的保护下，称取2-溴-4’-氯联苯(142g,530mmol),THF(852mL)于2L三口圆底烧瓶内，在-80℃～-90℃下溶解至澄清后，量取n-BuLi(254.75mL，2.5mol/L)逐滴缓慢滴加至反应体系中，在-80℃～-90℃下恒温反应50min后，称取金刚烷酮(63.78g,42.45mmol)，用THF(260mL)将金刚烷酮溶解后，逐滴缓慢滴加至反应体系中，在-80℃-90℃下恒温反应1h。待反应结束后，自然升温至室温，向反应液倒入5％盐酸至pH<7,充分搅拌后，加入DCM进行萃取，合并有机相，水洗至中性，用无水硫酸镁进行干燥，过滤后减压除去溶剂，将所得油状物，加入至有正庚烷的烧瓶内，加热回流至澄清溶液，置于-20℃下重结晶，得到白色固体中间体l-A-1(122g,产率68％)。
Figure PCTCN2020104581-appb-000055
在氮气的保护下，称取中间体l-A-1(122g,360mmol),并量取冰乙酸(1.5L)，在50℃-60℃下搅拌，待反应液完全澄清后，滴入浓硫酸(3.08mL)，继续升温至70℃-80℃，搅拌30min后，待反应液自然降温至室温，倒入去离子水(2L)，充分搅拌后过滤，将滤饼用去离子水淋洗至中性，放入真空干燥箱内烘料1h，用DCM将其溶解，加入无水硫酸钠干燥30min,过滤后减压除去溶剂，加入正庚烷，加入蒸出DCM， 将粗产物置于-20℃重结晶，过滤后于真空干燥箱内烘料，得白色固体中间体l-A-2(92.8g，收率80％)。
Figure PCTCN2020104581-appb-000056
将中间体l-A-2(104.8g,327.5mmol)，联硼酸频那醇酯(83.2g,327.5mmol)，三(二亚苄基丙酮)二钯(2.9g,3.28mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(2.7g,6.6mmol)以及醋酸钾(62g,655mmol)加入1，4-二氧六环(800mL)中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯，得到白色固体中间体l-A-3(108g,收率80％)。
Figure PCTCN2020104581-appb-000057
将中间体l-A-3(108g,262.3mmol)，10-溴蒽-9-硼酸(82.6g,275.2mmol)，醋酸钯(1.54g,2.62mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(2.5g,5.2mmol)以及碳酸钾(72.5g,524.6mmol)加入甲苯(400mL),无水乙醇(200mL)和去离子水(100mL)中，氮气保护下加热至80℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到白色固体中间体I-A(99g,收率75％).
化合物1的合成
Figure PCTCN2020104581-appb-000058
将中间体I-A(8g，15.8mmol)、2-溴萘(3.27g，15.8mmol)、四三苯基磷钯(0.365g，0.316mmol)、碳酸钾(4.8g，3.5mmol)、四丁基溴化铵(0.25g，0.79mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)、水(10mL)加入反应器中，80℃下回流12h,当反应结束时，使用CH 2Cl 2和水进行萃取，取有机相无水MgSO 4干燥，抽滤，浓缩有机层，粗产物硅胶过柱提纯，得到白色固体化合物1(6g，产率65％)
LC-MS(ESI,pos.ion)m/z:588.98[M+H] +
参照合成化合物1的合成方法，且使用表1中的原料2代替2-溴萘与中间体l-A反应，制备化合物2-化合物18。其中，化合物2-化合物18的编号、结构、原料、最后一步的合成收率、表征数据等展示在表1中：
表1：化合物结构、制备及表征数据
Figure PCTCN2020104581-appb-000059
Figure PCTCN2020104581-appb-000060
Figure PCTCN2020104581-appb-000061
Figure PCTCN2020104581-appb-000062
Figure PCTCN2020104581-appb-000063
1H NMR
化合物168
1H NMR(CD 2Cl 2,400MHz)δ(ppm):8.35(d,5H),8.26(d,1H),7.98(m,5H),7.86(d,1H),7.80-7.72(m,12H),7.48(t,1H),7.30(t,1H),3.00(d,2H),2.81(d,2H),2.21(s,1H),2.02(s,1H),1.94(s,2H),1.83(d,4H),1.72(s,2H).
化合物169
1H NMR(CD 2Cl 2,400MHz)δ(ppm):8.38(m,4H),8.33-8.29(m,2H),8.20-8.00(m,6H),7.80-7.65(m,10H),7.48(t,1H),7.30(t,1H),2.98(d,2H),2.83(d,2H),2.20(s,1H),2.01(s,1H),1.94(s,2H),1.84(d,4H),1.73(s,2H).
化合物188
1H NMR(CD 2Cl 2,400MHz)δ(ppm):8.56(m,4H),8.38(m,4H),8.29-8.00(m,5H),7.80-7.65(m,10H),7.48(t,1H),7.30(t,1H),3.01(d,2H),2.83(d,2H),2.22(s,1H),2.02(s,1H),1.95(s,2H),1.82(d,4H),1.74(s,2H).
化合物201
1H NMR(CD 2Cl 2,400MHz)δ(ppm):8.53(m,2H),8.38(m,4H),8.29-8.10(m,4H),7.80-7.65(m,13H),7.48(t,2H),7.30(t,2H),3.02(d,2H),2.80(d,2H),2.23(s,1H),2.04(s,1H),1.92(s,2H),1.84(d,4H),1.71(s,2H).
合成方案(二)
另一些化合物可以通过以下合成方案(二)合成。
Figure PCTCN2020104581-appb-000064
Figure PCTCN2020104581-appb-000065
其中，Ar 1具有本申请所述含义。
合成过程：中间体I-A-2与对氯苯硼酸在碱性条件下发生Suzuki反应，生成中间体II-A-1，联硼酸频那醇酯与中间体II-A-1在碱性条件下，通过钯催化剂发生Suzuki反应，生成中间体II-A-2，10-溴蒽-9-硼酸与中间体II-A-2在碱性条件下，钯催化剂下发生Suzuki反应，生成中间体II-A，芳基溴代物BrR 1与中间体II-A在碱性条件下，钯催化剂下发生偶联反应，生成具有式(Ib)所示结构的化合物。
本申请化合物81～82可采用上述一般合成方案(二)制备，为了便于理解，下面以具体化合物81的制备过程为例，示例性的示出本申请部分化合物的合成过程。
中间体II-A的合成
Figure PCTCN2020104581-appb-000066
将中间体Ⅰ-A-2(20g,62.34mmol)、对氯苯硼酸(9.75g,62.34mmol)、四(三苯基膦)钯(0.72g,0.62mmol)、碳酸钾(17.2g,124.6mmol)、四丁基氯化铵(0.34g,1.25mmol)、甲苯(160mL)、乙醇(40mL和去离子水(40mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体ll-A-1(18.6g，75％)。
Figure PCTCN2020104581-appb-000067
将中间体II-A-1(18.6g,46.7mmol)，联硼酸频那醇酯(11.9g,46.7mmol)，三(二亚苄基丙酮)二钯(0.4278g,0.467mmol)，2-二环己基磷-2’,4’,6’-三异丙基联苯(0.444g,0.934mmol)以及醋酸钾(9.17g,655mmol)加入1，4-二氧六环(160mL)中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯，得到白色固体中间体lI-A-2(18g,收率79％)。
Figure PCTCN2020104581-appb-000068
将中间体II-A-2(18g,36.8mmol)，10-溴蒽-9-硼酸(11g,36.8mmol)，醋酸钯(0.16g,0.736mmol)， 2-二环己基磷-2’,4’,6’-三异丙基联苯(0.175g,0.368mmol)以及碳酸钾(10.16g,73.6mmol)加入甲苯(80mL),无水乙醇(40mL)和去离子水(20mL)中，氮气保护下加热至80℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到白色固体中间体II-A(16g,收率72％)。
化合物81的合成
Figure PCTCN2020104581-appb-000069
将中间体II-A(9g，15.8mmol)、2-溴萘(3.27g，15.8mmol)、四三苯基磷钯(0.365g，0.316mmol)、碳酸钾(4.8g，3.5mmol)、四丁基溴化铵(0.25g，0.79mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)、水(10mL)加入反应器中，80℃下回流12h,当反应结束时，使用CH 2Cl 2和水进行萃取，取有机相无水MgSO 4干燥，抽滤，浓缩有机层，粗产物硅胶过柱提纯，得到白色固体化合物81(5.2g，产率50％)
LC-MS(ESI,pos.ion)m/z:665.01[M+H] +
化合物82的合成
Figure PCTCN2020104581-appb-000070
将中间体II-A(9g，15.8mmol)、4-溴联苯(3.68g，15.8mmol)、四三苯基磷钯(0.365g，0.316mmol)、碳酸钾(4.8g，3.5mmol)、四丁基溴化铵(0.25g，0.79mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)、水(10mL)加入反应器中，80℃下回流12h,当反应结束时，使用CH 2Cl 2和水进行萃取，有机相无水MgSO 4干燥，抽滤，浓缩有机层，粗产物硅胶过柱提纯，得到白色固体化合物82(6.65g，产率61％)
LC-MS(ESI,pos.ion)m/z:691.03[M+H] +
化合物119、化合物123、化合物141、化合物157的合成
中间体III-A-1的合成
Figure PCTCN2020104581-appb-000071
将吡啶-2-硼酸(6.146g,50mmol)、10-溴蒽-9-硼酸(15g,50mmol)、四(三苯基膦)钯(0.58g,0.5mmol)、碳酸钾(7.35g,75mmol)、四丁基氯化铵(0.278g,1mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(50mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相 进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体III-A-1(11.2g，75％)。
参照合成中间体III-A-1的合成方法，且使用表2中的原料1代替吡啶-2-硼酸，制备中间体IV-A-1,中间体V-A-1、中间体VI-A-1。其中，中间体IV-A-1,中间体V-A-1,中间体VI-A-1的编号、结构、原料、合成收率等展示在表2中：
表2：化合物结构、制备及表征数据
Figure PCTCN2020104581-appb-000072
中间体III-A-2的合成
Figure PCTCN2020104581-appb-000073
将中间体III-A-1(11.2g,50mmol)、3-溴-3'-氯-1,1'-联苯(13.4g,50mmol)、四(三苯基膦)钯(0.58g,0.5mmol)、碳酸钾(7.35g,75mmol)、四丁基氯化铵(0.278g,1mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(50mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体III-A-2(15.9g，72％)。
参照合成中间体III-A-2的合成方法，使用表3中的原料1替代中间体III-A-1，且使用原料2代替3-溴-3'-氯-1,1'-联苯，制备中间体IV-A-2,中间体V-A-2,中间体VI-A-2。其中，中间体IV-A-2,中间体V-A-2,中间体VI-A-2的编号、结构、原料、合成收率等展示在表3中：
表3：化合物结构、制备及表征数据
Figure PCTCN2020104581-appb-000074
Figure PCTCN2020104581-appb-000075
中间体III-A-3的合成
Figure PCTCN2020104581-appb-000076
将中间体III-A-2(15.9g,36.5mmol)，联硼酸频那醇酯(9.16g,36.5mmol)，三(二亚苄基丙酮)二钯(0.3346g,0.365mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(.03468g,0.73mmol)以及醋酸钾(9.8g,100mmol)加入1，4-二氧六环(150mL)中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯，得到白色固体中间体III-A-3(15.56g,收率80％)。
参照合成中间体III-A-3的合成方法，且使用表4中的原料1代替中间体III-A-2，制备中间体IV-A-3,中间体V-A-3,中间体VI-A-3。其中，中间体IV-A-3,中间体V-A-3,中间体VI-A-3的编号、结构、原料、合成收率等展示在表4中：
表4：化合物结构、制备及表征数据
Figure PCTCN2020104581-appb-000077
Figure PCTCN2020104581-appb-000078
化合物119的合成
Figure PCTCN2020104581-appb-000079
将中间体III-A-3(15.56g,28.1mmol)，中间体I-A-2(8.992g,28.1mmol)，醋酸钯(0.0629g,0.281mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(0.267g,0.56mmol)以及碳酸钾(4.5g,42mmol)加入甲苯(40mL),无水乙醇(20mL)和去离子水(10mL)中，氮气保护下加热至80℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯/正庚烷体系对粗品进行重结晶提纯，得到白色固体化合物119(14.56g,收率75％).
LC-MS(ESI,pos.ion)m/z:692.32[M+H] +
参照合成化合物119的合成方法，且使用表5中的原料1代替中间体III-A-3，与中间体I-A-2制备化合物123、化合物141、化合物157。其中，化合物123、化合物141、化合物157的编号、结构、原料、合成收率和表征数据等展示在表5中：
表5：化合物结构、制备及表征数据
Figure PCTCN2020104581-appb-000080
化合物112的合成
中间体IV-A-1的合成
Figure PCTCN2020104581-appb-000081
将10-(4-叔丁基苯)蒽-9硼酸(17.713.g,50mmol)、2-溴氯苯(9.57g,50mmol)、四(三苯基膦)钯(0.58g,0.5mmol)、碳酸钾(7.35g,75mmol)、四丁基氯化铵(0.278g,1mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(50mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用甲苯/正庚烷体系进行重结晶提纯，得到白色固体中间体IV-A-1(16.8g，80％)。
中间体IV-A-2的合成
Figure PCTCN2020104581-appb-000082
将中间体IV-A-1(16.8g,40mmol)，联硼酸频那醇酯(9.92g,40mmol)，三(二亚苄基丙酮)二钯(0.3663g,0.4mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(0.38g,0.8mmol)以及醋酸钾(5.8g,60mmol)加入1，4-二氧六环(150mL)中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯，得到白色固体中间体IV-A-2(15.56g,收率76％)。
中间体IV-A-3的合成
Figure PCTCN2020104581-appb-000083
在氮气的保护下，称取2-溴-2-溴联苯(14.2g,53mmol)，THF(85.2mL)于250L三口圆底烧瓶内，在-80℃--90℃下溶解至澄清后，量取n-BuLi(25.48mL)逐滴缓慢滴加至反应体系中，在-80℃--90℃下恒温反应50min后，称取金刚烷酮(6.378g,42.45mmol)，用THF(26mL)将金刚烷酮溶解后，逐滴缓慢滴加至反应体系中，在-80℃-90℃下恒温反应1h.待反应结束后，自然升温至室温，向反应液倒入5％盐酸至pH<7,充分搅拌后，加入DCM进行萃取，合并有机相，水洗至中性，用无水硫酸镁进行干燥，过滤后减压除去溶剂，将所得油状物，加入至有正庚烷的烧瓶内，加热回流至澄清溶液，置于-20℃下重结晶，得到白色固体中间体lV-A-3(12g,68％)。
中间体IV-A-4的合成
Figure PCTCN2020104581-appb-000084
在氮气的保护下，称取中间体lV-A-3(12.2g,36mmol),并量取冰乙酸(150mL)，在50℃-60℃下搅拌，待反应液完全澄清后，滴入浓硫酸(0.308mL)，继续升温至70℃-80℃，搅拌30min后，带反应液自然降温至室温，倒入去离子水(200L)，充分搅拌后过滤，将滤饼用去离子水淋洗至中性，放入真空干燥箱内烘料1h，用DCM将其溶解，加入无水硫酸钠干燥30min，过滤后减压除去溶剂，加入正庚烷，加入蒸出DCM，将粗产物置于-20℃重结晶，过滤后于真空干燥箱内烘料，得白色固体中间体lV-A-4(9.2g，80％)。
化合物112的合成
Figure PCTCN2020104581-appb-000085
将中间体IV-A-2(15.56g,30.4mmol)，中间体IV-A-4(11.1g,30.4mmol)，醋酸钯(0.068g,0.304mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(0.288g,0.608mmol)以及碳酸钾(4.38g,45.6mmol)加入甲苯(40mL),无水乙醇(20mL)和去离子水(10mL)中，氮气保护下加热至80℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯/正庚烷体系对粗品进行重结晶提纯， 得到白色固体化合物112(8.14g,收率40％).
LC-MS(ESI,pos.ion)m/z:671.36[M+H] +
化合物46的合成
中间体V-A-1的合成
Figure PCTCN2020104581-appb-000086
将2-溴苯基硼酸(10g,50mmol)、间氯溴苯(9.57g,50mmol)、四(三苯基膦)钯(0.58g,0.5mmol)、碳酸钾(7.35g,75mmol)、四丁基氯化铵(0.278g,1mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(50mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用甲苯/正庚烷体系进行重结晶提纯，得到白色固体中间体V-A-1(16.8g，80％)。
中间体V-A-2的合成
Figure PCTCN2020104581-appb-000087
在氮气的保护下，称取中间体V-A-1(16.8g,62.8mmol),THF(852mL)于2L三口圆底烧瓶内，在-80℃～90℃下溶解至澄清后，量取n-BuLi(5.26mL)逐滴缓慢滴加至反应体系中，在-80℃～-90℃下恒温反应50min后，称取金刚烷酮(9.43g,62.8mmol),用THF(160mL)将金刚烷酮溶解后，逐滴缓慢滴加至反应体系中，在-80℃～90℃下恒温反应1h.待反应结束后，自然升温至室温，向反应液倒入5％盐酸至pH<7,充分搅拌后，加入DCM进行萃取，合并有机相，水洗至中性，用无水硫酸镁进行干燥，过滤后减压除去溶剂，将所得油状物，加入至有正庚烷的烧瓶内，加热回流至澄清溶液，置于-20℃下重结晶，得到白色固体中间体V-A-2(14.9g,产率70％)。
中间体V-A-3的合成
Figure PCTCN2020104581-appb-000088
在氮气的保护下，称取中间体V-A-2(14.9g,43.9mmol),并量取冰乙酸(150L)，在50℃～60℃下搅拌，待反应液完全澄清后，滴入浓硫酸(0.5mL)，继续升温至70℃-80℃，搅拌30min后，待反应液自然降温至室温，倒入去离子水(200mL)，充分搅拌后过滤，将滤饼用去离子水淋洗至中性，放入真空干燥箱内烘料1h，用DCM将其溶解，加入无水硫酸钠干燥30min,过滤后减压除去溶剂，加入正庚烷，加入蒸出DCM，将粗产物置于-20℃重结晶，过滤后于真空干燥箱内烘料，得白色固体中间体V-A-3(14g，产率90％)。
中间体V-A-4的合成
Figure PCTCN2020104581-appb-000089
将中间体V-A-3(14g,44mmol)，联硼酸频那醇酯(11.2g,44mmol)，三(二亚苄基丙酮)二钯(0.403g,0.44mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(0.418g,0.88mmol)以及醋酸钾(8.624g,88mmol)加入1,4-二氧六环(140mL)中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯，得到白色固体中间体V-A-4(14.13g,收率78％)。
中间体V-A-5的合成
Figure PCTCN2020104581-appb-000090
将中间体V-A-4(14.13g,34.3mmol)，10-溴蒽-9-硼酸(10.3g,34.3mmol)，醋酸钯(0.034g,0.34mmol)，2-二环己基磷-2',4',6'-三异丙基联苯(0.323g,0.68mmol)以及碳酸钾(6.7g,68.6mmol)加入甲苯(40mL),无水乙醇(20mL)和去离子水(10mL)中，氮气保护下加热至80℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到白色固体中间体V-A(16.8g,收率85％).
化合物46的合成
Figure PCTCN2020104581-appb-000091
将中间体V-A(8g，15.8mmol)、4-溴联苯(3.68g，15.8mmol)、四三苯基磷钯(0.365g，0.316mmol)、碳酸钾(4.8g，3.5mmol)、四丁基溴化铵(0.25g，0.79mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)、水(10mL)加入反应器中，80℃下回流12h,当反应结束时，使用CH 2Cl 2和水进行萃取，取有机相无水MgSO 4干燥，抽滤，浓缩有机层，粗产物硅胶过柱提纯，得到白色固体化合物46(6.79g，产率70％)
LC-MS(ESI,pos.ion)m/z:615.3[M+H] +
参照制备例合成化合物46的合成方法，且使用原料2代替4-溴联苯，制备化合物47-化合物48。其中，化合物47-化合物48的编号、结构、原料、最后一步的合成收率、质谱数据等展示在表6中：
表6：化合物结构、制备及表征数据
Figure PCTCN2020104581-appb-000092
Figure PCTCN2020104581-appb-000093
有机电致发光器件制备及评估
实施例1
通过以下过程制备阳极：将厚度为
Figure PCTCN2020104581-appb-000094
的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2020104581-appb-000095
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀化合物NPB，以形成厚度为
Figure PCTCN2020104581-appb-000096
的空穴传输层(HTL)。
在HTL上蒸镀化合物PAPB作为电子阻挡层(EBL)，厚度为
Figure PCTCN2020104581-appb-000097
在EBL上将化合物1作为主体，按照膜厚比100:3同时掺杂BD-1，形成厚度为
Figure PCTCN2020104581-appb-000098
的发光层(EML)。
在EML上蒸镀化合物ET-06和LiQ作为电子传输层(ETL)，膜厚比以1:1蒸镀，厚度为
Figure PCTCN2020104581-appb-000099
在ETL上蒸镀金属Yb作为电子注入层(EIL)，厚度为
Figure PCTCN2020104581-appb-000100
在EIL上蒸镀膜厚比为10:1的银(Ag)、镁(Mg)掺杂膜层作为阴极(cathode)，厚度为
Figure PCTCN2020104581-appb-000101
在阴极上蒸镀化合物CP-5作为光引出层(CPL)，厚度为
Figure PCTCN2020104581-appb-000102
形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例2-实施例30
除了在形成发光层时，以下表7中所示的化合物替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例1
除了在形成发光层时，以下表7中所示的化合物A替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例2
除了在形成发光层时，以下表7中所示的化合物B替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例3
除了在形成发光层时，以下表7中所示的化合物C替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例4
除了在形成发光层时，以下表7中所示的化合物D替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
以上实施例和比较例使用的材料结构如下表所示：
Figure PCTCN2020104581-appb-000103
对如上制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的性能，其结果如表7所示。
表7有机电致发光器件的性能测试结果
Figure PCTCN2020104581-appb-000104
Figure PCTCN2020104581-appb-000105
根据上述表7的结果，可知，作为蓝光发光层(EML)主体材料的化合物1～18、化合物81、82、119、123、141、157、112、46～48、168、201与使用的比较例1～比较例4的化合物A、B、C、D相比较，本申请中使用的化合物1～18及81、82、化合物119、123、141、157、112、119、123、141、157、112、46～48、168、201作为蓝光发光层主体材料制备的上述有机电致发光器件的驱动电压至少降低了0.11V，电流效率(Cd/A)至少提高了13.29％，功率效率(lm/W)至少提高了16.63％，外量子效率至少提高了13.16％，寿命最少的提高了30％。
本申请将金刚烷螺芴基团和蒽基基团连接组合，得到了一种用于有机电致发光器件的新型化合物；该化合物中，金刚烷螺芴和蒽基基团均具有高的空穴迁移率，将二者连接时，使得分子整体的空穴迁移率进一步提高，有利于降低器件工作电压并提升发光效率；在蒽类化合物发光主体中引入金刚烷螺芴基，提升分子整体的电子密度，进而提升载流子传输速率，在中心蒽基基团上引入的另一个芳香性基基团增强了分子不对称性，使得材料不易结晶从而提升器件稳定性。将该类材料作为有机电致发光器件主体材料使用时，可以使器件具有较高的发光效率以及长的寿命。

Claims (21)

  1. 一种有机化合物，其中，所述有机化合物的结构如化学式1所示：
    Figure PCTCN2020104581-appb-100001
    其中，L选自单键、取代或未取代的碳原子数为1～20的亚烷基、取代或未取代的碳原子数为6～30的亚芳基、取代或未取代的碳原子数为3～30的亚杂芳基、取代或未取代的碳原子数为3～20的亚环烷基；
    Ar 1选自取代或未取代的碳原子数为3～20的环烷基、取代或未取代的碳原子数为6～40的芳基、取代或未取代的碳原子数为3～30的杂芳基；
    所述各R 1彼此相同或不同，各R 2彼此相同或不同，且分别独立地选自氘，氟，氯，溴，氰基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为3～18的烷基硅烷基，碳原子数为6～18的三芳基硅烷基，碳原子数为1～12的烷基，碳原子数为1～12的烷氧基，碳原子数为1～12的卤代烷基，碳原子数为2～12的烯基，碳原子数为3～10的环烷基，碳原子数为2～12的杂环烷基，碳原子数为1～10的烷胺基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基；
    n 1为取代基R 1的数量，n 1选自0、1、2、3或4，当n 1大于1时，任意两个R 1相同或不同；n 2为取代基R 2的数量，n 2选自0、1、2或3，当n 2大于1时，任意两个R 2相同或不同；
    所述Ar 1和L中的取代基彼此相同或不同，且分别独立地选自：氘，氟，氯，溴，氰基，任选地被0、1、2或3个选自氘、氟、氰基、甲基、三甲基硅基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～18的杂芳基，碳原子数为3～18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的烷基，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2～12的烯基，碳原子数为3～10的环烷基，碳原子数为2～12的杂环烷基，碳原子数为1～10的烷胺基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基。
  2. 根据权利要求1所述的有机化合物，其中，所述各R 1彼此相同或不同，各R 2彼此相同或不同，且分别独立地选自氘、氟、氯、溴、氰基、碳原子数为6～20的芳基、碳原子数为6～18的杂芳基、碳原子数为3～18的烷基硅烷基、碳原子数为6～18的三芳基硅烷基、碳原子数为1～12的烷基、碳原子数为1～12的烷氧基、碳原子数为1～12的卤代烷基、碳原子数为2～12的烯基、碳原子数为3～10的环烷基、碳原子数为2～12的杂环烷基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基；
    所述Ar 1和L中的取代基彼此相同或不同，且分别独立地选自：氘、氟、氯、溴、氰基、碳原子数为6～20的芳基、碳原子数为6～18的杂芳基、碳原子数为3～18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的烷基、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2～12的烯基、碳原子数为3～10的环烷基、碳原子数为2～12的杂环烷基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基。
  3. 根据权利要求1或2所述的有机化合物，其中，所述各R 1彼此相同或不同，各R 2彼此相同或不 同，且各R 1和R 2分别独立地选自氘、氟、氯、溴、氰基、碳原子数为1～6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1～4的烷胺基、碳原子数为1～4的烷硫基、碳原子数为6～15的芳基、碳原子数为3～15的杂芳基、碳原子数为3～8的三烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳氧基、碳原子数为6～12的芳硫基。
  4. 根据权利要求1至3中任一项所述的有机化合物，其中，L选自取代或未取代的成环碳原子数为6～25的亚芳基、取代或未取代的成环碳原子数为3～18的亚杂芳基；所述L中的取代基彼此相同或不同，且分别独立地选自：氘、氟、氯、溴、氰基、碳原子数为1～6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1～4的烷胺基、碳原子数为1～4的烷硫基、碳原子数为6～15的芳基、碳原子数为3～15的杂芳基、碳原子数为3～8的三烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳氧基、碳原子数为6～12的芳硫基。
  5. 根据权利要求1至4中任意一项所述的有机化合物，其中，L选自单键或化学式j-1至化学式j-13所示的基团所组成的组：
    Figure PCTCN2020104581-appb-100002
    其中，M 1选自单键或者
    Figure PCTCN2020104581-appb-100003
    Q 1～Q 5各自独立地选自N或者C(F 1)，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(F 1)时，任意两个F 1相同或者不相同；
    Q 6～Q 13各自独立地选自N或者C(F 2)，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(F 2)时，任意两个F 2相同或者不相同；
    Q 14～Q 23各自独立地选自N或者C(F 3)，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(F 3)时，任意两个F 3相同或者不相同；
    Q 24～Q 33各自独立地选自N或者C(F 4)，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(F 4)时，任意两个F 4相同或者不相同；
    E 1～E 14、F 1～F 4各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～18的杂芳基、碳原子数为6～18的芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～12的芳基甲硅烷基、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的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基；e r为取代基E r的数量，r为1～14的任意整数；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
    K 1选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 16E 17)；其中，E 15、E 16、E 17各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 16和E 17相互连接以与它们共同连接的原子形成饱和或不饱和的5至13元脂肪族环；
    K 2选自单键、O、S、Se、N(E 18)、C(E 19E 20)、Si(E 19E 20)；其中，E 18、E 19、E 20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、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基，或者E 19和E 20相互连接以与它们共同连接的原子形成饱和或不饱和的5至13元脂肪族环。
  6. 根据权利要求1至5中任意一项所述的有机化合物，其中，L选自单键、未取代的W 1或者取代的W 1，其中，未取代的W 1选自如下取代基所组成的组：
    Figure PCTCN2020104581-appb-100004
    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、碳原子数为1～6的烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基、三苯基硅烷基、 碳原子数为3～10的环烷基、碳原子数为6～12的芳基、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上包括多个取代基时，任意两个取代基相同或者不相同。
  7. 根据权利要求1至6中任意一项所述的有机化合物，其中，L选自单键、未取代的W 2或者取代的W 2，其中，未取代的W 2选自如下取代基所组成的组：
    Figure PCTCN2020104581-appb-100005
    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、叔丁基、甲氧基、乙氧基、异丙氧基、三氟甲基、三苯基硅烷基、环戊烷基、环己烷基、三氟甲基、三甲基硅烷基、苯基、萘基、吡啶基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基的取代基所取代而形成的基团，且当取代的W 2上包括多个取代基时，任意两个取代基相同或者不相同。
  8. 根据权利要求1至7中任意一项所述的有机化合物，其特征在于，Ar 1选自取代或未取代的成环碳原子数为6～25的芳基、取代或未取代的成环碳原子数为4～18的杂芳基。
  9. 根据权利要求1至8中任意一项所述的有机化合物，其中，Ar 1选自化学式S-1至化学式S-11所示的取代基所组成的组:
    Figure PCTCN2020104581-appb-100006
    上述基团中，M 2选自单键或者
    Figure PCTCN2020104581-appb-100007
    n a和n d各自独立地为1、2、3或4，当一个基团中包含两个或多个R a时，各R a彼此相同或不同；当一个基团中包含两个或多个R d时，各R d彼此相同或不同；n b选自1、2、3、4或5，当一个基团中包含两个或多个R b时，各R b彼此相同或不同；
    V 1～V 40各自独立地选自C(R v)和N，当一个基团中包含两个或多个R v时，任意两个R v彼此相同或不同；
    V选自O、S、Se、N(R v1)、C(R v2R v3)和Si(R v2R v3)所构成的组；
    K 1和K 2各自独立地选自O、S或N(R k)；
    各R a、R b、R d、R k、R v1、R v2、R v3分别独立地为氢、碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基；或者，连接于同一个原子上的R v2和R v3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；
    各R v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6～18的芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～18的芳基甲硅烷基、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的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基。
  10. 根据权利要求1至9中任意一项所述的有机化合物，其中，Ar 1为未取代的T 1或者取代的T 1，其中，未取代的T 1选自如下取代基所组成的组:
    Figure PCTCN2020104581-appb-100008
    取代的T 1为未取代的T 1被一个或者多个选自氘、氟、氯、氰基、碳原子数为1～6的烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的卤代烷基、碳原子数为3～9的烷基硅烷基、三苯基硅烷基、碳原子数为5～10的环烷基、碳原子数为6～15的芳基、碳原子数为3～12的杂芳基的取代基所取代而形成的基团，且当取代的T 1上包括多个取代基时，任意两个取代基相同或者不相同。
  11. 根据权利要求1至10中任意一项所述的有机化合物，其中，Ar 1选自如下取代基所组成的组：
    Figure PCTCN2020104581-appb-100009
    Figure PCTCN2020104581-appb-100010
  12. 根据权利要求1至11中任意一项所述的有机化合物，其中，所述Ar 1选自如下化学式S-12、化学式S-13所示基团：
    Figure PCTCN2020104581-appb-100011
    其中，V 41～V 55各自独立地选自C(R v4)和N，V 48～V 55中至少有一个为N，当同一个基团中包含多个R v4时，任意两个R v4彼此相同或不同；
    T选自O、S、Se、N(R t1)、C(R t2R t3)和Si(R t2R t3)所构成的组；
    各R t1、R t2、R t3分别独立地为氢、碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基；或者，连接于同一个原子上的R t2和R t3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元环；
    各R v4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6～18的芳基、碳原子数为3～12的三烷基硅基、碳原子数为8～12的芳基甲硅烷基、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 的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基，或者，任意两个相邻的R v4相互连接形成6～10元芳环或6～10元杂芳环。
  13. 根据权利要求1至12中任意一项所述的有机化合物，其中，所述Ar 1选自取代或者未取代的T 2，其中未取代的T 2独立地选自如下所示基团：
    Figure PCTCN2020104581-appb-100012
    取代的T 2为未取代的T 2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1～4的卤代烷基、碳原子数为3～9的烷基硅烷基、碳原子数为6～18的芳基硅基、碳原子数为5～7的环烷基、碳原子数为6～13的芳基、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T 6上包括多个取代基时，任意两个取代基相同或者不相同。
  14. 根据权利要求1至13中任意一项所述的有机化合物，其中，所述Ar 1独立地选自如下所示基团：
    Figure PCTCN2020104581-appb-100013
    Figure PCTCN2020104581-appb-100014
  15. 根据权利要求1至14中任意一项所述的有机化合物，其具有以下化学式1-1至化学式1-3中至少一者所示的结构：
    Figure PCTCN2020104581-appb-100015
  16. 根据权利要求1至15中任意一项所述的有机化合物，其中，所述各R 1和R 2彼此相同或不同，且分别独立地选自氘，氟，氯，溴，氰基，甲基，乙基，异丙基，叔丁基，甲氧基，乙氧基，异丙氧基，正丙氧基，环戊烷基，环己烷基，三氟甲基，三甲基硅烷基，三苯基硅基，任选被0、1、2、3、4或5个选自氘、氟、氯、溴、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基的取代基所取代的苯基，萘基，吡啶基，嘧啶基，，二苯并噻吩基，二苯并呋喃基或喹啉基，且当R 1和R 2的个数多于1时，任意两个R 1或R 2相同或者不相同。
  17. 根据权利要求1至16中任意一项所述的有机化合物，其中，所述有机化合物选自如下化合物所组成的组：
    Figure PCTCN2020104581-appb-100016
    Figure PCTCN2020104581-appb-100017
    Figure PCTCN2020104581-appb-100018
    Figure PCTCN2020104581-appb-100019
    Figure PCTCN2020104581-appb-100020
    Figure PCTCN2020104581-appb-100021
    Figure PCTCN2020104581-appb-100022
    Figure PCTCN2020104581-appb-100023
    Figure PCTCN2020104581-appb-100024
  18. 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1～17中任意一项所述的有机化合物。
  19. 根据权利要求18所述的有机电致发光器件，其中，所述功能层包括有机电致发光层，所述有机电致发光层包含权利要求1～17中任意一项所述的有机化合物。
  20. 根据权利要求19所述的有机电致发光器件，其中，所述有机电致发光层包含主体材料，所述主体材料含有权利要求1～17中任意一项所述的有机化合物。
  21. 一种电子装置，其中，包括权利要求18～20中任意一项所述的有机电致发光器件。
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