WO2022027992A1 - 含氮化合物、电子元件和电子装置 - Google Patents
含氮化合物、电子元件和电子装置 Download PDFInfo
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- WO2022027992A1 WO2022027992A1 PCT/CN2021/085415 CN2021085415W WO2022027992A1 WO 2022027992 A1 WO2022027992 A1 WO 2022027992A1 CN 2021085415 W CN2021085415 W CN 2021085415W WO 2022027992 A1 WO2022027992 A1 WO 2022027992A1
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 36
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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Definitions
- the present invention claims the priority of the Chinese patent application with application number CN202010789251.8 submitted on August 7, 2020, and the full content of the disclosure of the above Chinese patent application is hereby cited as a part of this application.
- the present invention claims the priority of the Chinese patent application with application number CN202010956344.5 submitted on September 11, 2021, and the full content of the disclosure of the above Chinese patent application is hereby cited as a part of this application.
- the present application relates to the technical field of organic materials, and in particular, to a nitrogen-containing compound, an electronic component and an electronic device.
- organic electroluminescent material As a new generation of display technology, organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. It has been widely used in flat panel display, flexible display, solid-state lighting and vehicle display industries.
- the organic light-emitting phenomenon refers to a phenomenon in which an organic material is used to convert electrical energy into light energy.
- An organic light-emitting device utilizing an organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
- an organic light-emitting device structure when a voltage is applied between two electrodes, holes and electrons are injected into the organic material layer from the anode and cathode, respectively, excitons are formed when the injected holes meet electrons, and when these excitons return Lights up in the ground state.
- the object of the present invention is to provide a nitrogen-containing compound, an electronic component and an electronic device to improve the performance of the electronic component and the electronic device.
- X 1 , X 2 , and X 3 are the same or different, and are independently selected from C(R 0 ) or N, and at least one of them is N;
- Y1 is Y2 is Y3 is
- L 1 , L 2 and L 3 are the same or different from each other, and are each independently: a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylene group having 3 to 30 carbon atoms substituted heteroarylene;
- Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. base;
- Ad is 1-adamantyl
- m 1 to m 3 are represented by mi
- n 1 to n 3 are represented by n i
- q 1 to q 3 are represented by q i
- t 1 to t 3 are represented by t i
- i is a variable, which is selected from 1 and 2 or 3;
- m i represents the number of cyano groups on Li
- ni represents the number of Ads on Li
- qi represents the number of cyano groups on Ar i
- t i represents the number of cyano groups on Ar i
- Ads with
- m i is independently selected from 0, 1, 2 or 3, and when m i is greater than 1, any two m i are the same or different;
- ni is independently selected from 0, 1, 2 or 3, and when ni is greater than 1, any two nis are the same or different;
- q i is independently selected from 0, 1, 2 or 3, and when q i is greater than 1, any two q i are the same or different;
- ti is independently selected from 0, 1, 2 or 3, and when ti is greater than 1, any two ti are the same or different;
- Each R 0 is the same or different from each other, and is independently selected from hydrogen, deuterium, alkyl having 1-10 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, or 6-20 substituted or unsubstituted aryl groups;
- R 0 , L 1 -L 3 and Ar 1 -Ar 3 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, group A, and alkane having 1-10 carbon atoms base, haloalkyl with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, carbon Cycloalkenyl with 5-10 atoms, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio group with 1-10 carbon atoms, carbon atoms Aryloxy group with 6-18 carbon atoms, arylthio group with carbon number of 6-18, arylsilyl group with carbon number of 6-18, alkylsilyl group with carbon number of 3-12;
- the group A is selected from substituted or unsubstituted heteroaryl groups with 3-20 carbon
- the nitrogen-containing compound of the present invention uses a nitrogen-containing heteroaryl group as the parent nucleus, and the adamantyl group and the nitrile group are connected to the nitrogen-containing heteroaryl group through the aryl group or the heteroaryl group as the connecting group, and the existence of the cyano group makes the This partial structure has a high dipole moment, which increases the polarity of the material.
- the combination of cyano and heteroaryl groups can obtain organic materials with high electron mobility. When used as electron transport layers in electronic components, the efficiency, lifetime and operating voltage of devices can be improved.
- adamantyl itself can avoid the direct stacking of conjugated planes to form ⁇ aggregation, which can improve the film-forming properties of the material, and at the same time enhance the overall molecular weight and asymmetry of the compound, and improve the thermal stability of the molecule. It also improves the crystallinity of the material to a certain extent, which can improve the stability of the compound when it is used in electronic components, making the electronic components easier to use in mass production.
- an electronic component comprising an anode and a cathode disposed oppositely, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned nitrogen-containing compound.
- an electronic device includes the above-mentioned electronic components.
- FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
- FIG. 2 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
- FIG. 3 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
- FIG. 4 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
- Example embodiments will now be described more fully with reference to the accompanying drawings.
- Example embodiments can be embodied in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art.
- the described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided in order to give a thorough understanding of the embodiments of the present application.
- X 1 , X 2 , and X 3 are the same or different, and are independently selected from C(R 0 ) or N, and at least one of them is N;
- Y1 is Y2 is Y3 is
- L 1 , L 2 and L 3 are the same or different from each other, and are each independently: a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted arylene group having 3 to 30 carbon atoms substituted heteroarylene;
- Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. base;
- Ad is 1-adamantyl
- m 1 to m 3 are represented by mi
- n 1 to n 3 are represented by n i
- q 1 to q 3 are represented by q i
- t 1 to t 3 are represented by t i
- i is a variable, which is selected from 1 and 2 or 3;
- m i represents the number of cyano groups on Li
- ni represents the number of Ads on Li
- qi represents the number of cyano groups on Ar i
- t i represents the number of cyano groups on Ar i
- Ads with
- m i is independently selected from 0, 1, 2 or 3, and when m i is greater than 1, any two m i are the same or different;
- ni is independently selected from 0, 1, 2 or 3, and when ni is greater than 1, any two nis are the same or different;
- q i is independently selected from 0, 1, 2 or 3, and when q i is greater than 1, any two q i are the same or different;
- ti is independently selected from 0, 1, 2 or 3, and when ti is greater than 1, any two ti are the same or different;
- Each R 0 is the same or different from each other, and is independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a 6-20 substituted or unsubstituted aryl groups;
- R 0 , L 1 to L 3 and Ar 1 to Ar 3 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, group A, and alkane having 1 to 10 carbon atoms group, haloalkyl group with 1 to 10 carbon atoms, alkenyl group with 2 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, heterocycloalkyl group with 2 to 10 carbon atoms, carbon A cycloalkenyl group having 5 to 10 atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a carbon atom Aryloxy with 6-18 carbon atoms, arylthio group with 6-18 carbon atoms, arylsilyl group with 6-18 carbon atoms, alkylsilyl group with 3-12 carbon atoms; groups A
- the nitrogen-containing compound of the present invention uses a nitrogen-containing heteroaryl group as the core, and connects 1-adamantyl and nitrile to the nitrogen-containing heteroaryl core through a linking group.
- the existence of the cyano group makes this part of the structure have high dipole moment, which increases the polarity of the material.
- the combination of cyano and heteroaryl groups can obtain organic materials with high electron mobility. When used as electron transport layers in electronic components, the efficiency, lifetime and operating voltage of devices can be improved.
- adamantyl itself can avoid the direct stacking of conjugated planes to form ⁇ aggregation, which can improve the film-forming properties of the material, and at the same time enhance the overall molecular weight and asymmetry of the compound, and improve the thermal stability of the molecule. It also improves the crystallinity of the material to a certain extent, which can improve the stability of the compound when it is used in electronic components, making the electronic components easier to use in mass production. In addition, compared with the connection mode of 2-adamantyl, the overall molecular polarity of the compound can be improved, and the stability of the compound is better.
- the number of carbon atoms refers to the number of carbon atoms in the aryl or heteroaryl groups and the substituents on them.
- the total number of carbon atoms such as a substituted aryl group having 18 carbon atoms, means that the total number of carbon atoms in the aryl group and the substituent is 18.
- Ar 1 is 9-methyl-9-phenyl-fluorenyl, it is a substituted aryl group with 20 carbon atoms.
- L 1 -L 3 or Ar 1 -Ar 3 is selected from "substituted ()arylene group"
- the aryl group and all the substituents thereon are taken together as L 1 -L 3 or Ar 1 as a whole ⁇ any of Ar 3 .
- Y 1 is The meaning is that L 1 is connected with m 1 cyano group (CN) and n 1 adamantyl group (Ad), and Ar 1 is connected with q 1 cyano group (CN) and t 1 adamantyl group (Ad) It can be understood that when L 1 is a substituted aryl group, the cyano group and the adamantyl group can be connected to the aryl group or the substituent of the aryl group; Cyano and adamantyl on Ar 1 have the same meaning.
- cyano and adamantyl may be attached to either the aryl or heteroaryl, or the substituent of the aryl or heteroaryl.
- Ar 1 is selected from phenyl substituted naphthyl, wherein the cyano group can be attached to either the phenyl group or the naphthyl group.
- L 1 to L 3 are substituted arylene or heteroarylene, cyano and adamantyl can be connected either to arylene or heteroarylene, or to arylene or Substituents of heteroarylene.
- L 1 is selected from methyl-substituted phenylene, wherein the cyano group can be attached to either the methyl group or the phenylene group.
- Y 3 contains both a cyano group and an adamantyl group; in other embodiments, Y 1 contains a cyano group and Y 3 contains an adamantyl group.
- both the cyano group and the adamantyl group may be attached to Li, or both may be attached to Ar i , or one may be attached to Li and the other may be attached to Ar i .
- L 1 in Y 1 is attached to a monocyano group
- Ar 2 in Y 2 is attached to an adamantyl group. All in all, in Chemical Formula 1, there is at least one cyano group and one adamantyl group.
- the multiple cyano groups may be attached to the same Ar or the same L, or may be attached to different Ar or different L.
- a total of two cyano groups are included, with one cyano group attached to Ar 1 and the other cyano group attached to Ar 2 . In other embodiments, a total of two cyano groups are included, both of which are attached to Ar 1 .
- a total of two cyano groups are included, with one cyano group attached to L 1 and the other cyano group attached to L 2 . In other embodiments, a total of two cyano groups are included, both of which are attached to L 1 .
- the substituent contains multiple adamantyl groups
- the multiple adamantyl groups can be connected to the same Ar or the same L, or can be connected to different Ar or the same L.
- adamantyl is 1-adamantyl
- the adamantyl group is In this application, represent the same structure.
- C(R 0 ) means that a group R 0 is attached to the C atom.
- hetero refers to including at least one heteroatom selected from B, N, O, S, Se, Si and P in a functional group when no specific definition is otherwise provided.
- aralkoxy means alkoxy substituted by aryl
- alkoxycarbonyl means carbonyl substituted by alkoxy
- arcarbonylalkenyl means alkenyl substituted by arylcarbonyl
- aryloxy means alkenyl substituted by arylcarbonyl Hydroxyl substituted by an aryl group.
- aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
- the aryl group can be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups linked by A single-ring aryl group and a fused-ring aryl group linked by carbon-carbon bonds, and two or more fused-ring aryl groups linked by a carbon-carbon bond.
- Fused-ring aryl refers to two or more rings in which the two carbon atoms in the ring system are shared by two adjacent rings, wherein at least one of the rings is aromatic, for example the other rings may be naphthenic base, cycloalkenyl, aryl.
- aryl groups in this application may include, but are not limited to, phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10 ] phenanthrene, pyrene, benzofluoranthene, group, perylene group, fluorenyl group, triphenylene group, naphthacyl group, triphenylenyl and the like.
- the fluorenyl group may be substituted, and two substituent groups may be combined with each other to form a spiro ring structure. In the case where the above fluorenyl group is substituted, it can be:
- the substituted aryl group may be one or two or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group , alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
- a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group , alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
- heteroaryl substituted aryl groups include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothiophene substituted phenyl, carbazolyl substituted phenyl, pyridine substituted phenyl, and the like .
- the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituent on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and the substituted aryl group.
- the total number of carbon atoms in the base is 18.
- aryl groups as substituents may include, but are not limited to, phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, fluorenyl, dimethylfluorenyl, pyrenyl, perylene base.
- the number of carbon atoms of the aryl group may be selected from 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25 or 30.
- the aryl group is an aryl group with 6 to 30 carbon atoms, in other embodiments, the aryl group is an aryl group with 6 to 25 carbon atoms, and in other embodiments, the aryl group is a carbon atom an aryl group with 6-20 atoms, in other embodiments, the aryl group is an aryl group with 6-18 carbon atoms, in other embodiments, the aryl group is an aryl group with 6-15 carbon atoms, In other embodiments, the aryl group is an aryl group with 6-13 carbon atoms, and in other embodiments, the aryl group is an aryl group with 6-12 carbon atoms.
- the arylene group is a divalent group, and other than that, the above-mentioned description about the aryl group can be applied.
- heteroaryl refers to a monocyclic or polycyclic ring system containing at least one heteroatom independently selected from O, N, P, Si, Se, B, and S in the ring, and wherein at least one ring system is aromatic.
- Each ring system in a heteroaryl group contains a ring of 5-7 ring atoms with one or more points of attachment to the rest of the molecule.
- a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
- the ring system is an aromatic monocyclic ring or an aromatic fused ring.
- Fused ring heteroaryl refers to two or more rings in which the two atoms in the ring system are shared by two adjacent rings, wherein at least one of the rings is aromatic, for example the other ring may be a cycloalkane base, heterocyclyl, cycloalkenyl, aryl.
- heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, oxazolyl, furacyl, pyridyl, Bipyridyl, phenanthridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, Pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarb azolyl, benzothi
- thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
- N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
- Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
- a substituted heteroaryl group may be a heteroaryl group in which one or more than two hydrogen atoms are replaced by, for example, a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups.
- aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted carbazolyl, phenyl-substituted pyridine Base et al. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group. For example, a substituted heteroaryl group having 14 carbon atoms means that the total carbon number of the heteroaryl group and the substituent is 14.
- heteroaryl groups as substituents may include, but are not limited to, dibenzothienyl, dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, pyridyl, bipyridyl, Pyrimidyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, indolyl, phenanthroline.
- the number of carbon atoms of the heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
- the heteroaryl group is a heteroaryl group with 3 to 12 carbon atoms.
- the heteroaryl group is a heteroaryl group with 3 to 15 carbon atoms.
- the heteroaryl group is a heteroaryl group with 5-12 carbon atoms, and in other embodiments, the heteroaryl group is a heteroaryl group with 5-18 carbon atoms.
- the heteroarylene group is a divalent group, and other than that, the above description about the heteroaryl group can be applied.
- the halogen group as a substituent may be fluorine, chlorine, bromine or iodine.
- alkyl includes saturated linear or branched, monovalent or multivalent alkyl groups of 1 to 10 carbon atoms, wherein the alkyl group can be independently optionally substituted by one or more substituents described in the present invention replaced.
- the alkyl group contains 1-10 carbon atoms, in other embodiments, the alkyl group contains 1-8 carbon atoms, and in other embodiments, the alkyl group contains 1-6 carbon atoms In other embodiments, the alkyl group contains 1-4 carbon atoms, and in other embodiments, the alkyl group contains 1-3 carbon atoms.
- alkyl group having 1 to 4 carbon atoms as a substituent examples include, but are not limited to, methyl (Me, -CH 3 ), ethyl (Et, -CH 2 CH 3 ), n-propyl (n-Pr, -CH2CH2CH3 ), isopropyl (i - Pr, -CH( CH3 ) 2 ), n - butyl (n - Bu, -CH2CH2CH2CH3 ) , 2-methylpropyl or isobutyl (i-Bu, -CH2CH( CH3 ) 2 ), 1 -methylpropyl, sec-butyl (s-Bu, -CH( CH3 ) CH2CH 3 ), tert-butyl (t-Bu, -C(CH 3 ) 3 ) and the like.
- alkenyl refers to a linear or branched, monovalent or multivalent hydrocarbon group containing 2 to 10 carbon atoms, wherein there is at least one unsaturated site, that is, a carbon-carbon sp 2 double bond , wherein the alkenyl group may be optionally substituted with one or more substituents described herein, including the “cis” and “trans” positions, or the “E” and “Z” positions .
- the alkenyl group has 2 to 6 carbon atoms.
- alkenyl groups are vinyl, allyl, isopropenyl, 2-butenyl, 3-butenyl, 1-pentenyl Alkenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadiene, allyl, 1-phenylethen-1-yl, 2- Phenylethen-1-yl, 2,2-stilbene-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1 -yl) vinyl-1-yl, styryl, etc.
- alkoxy means that an alkyl group is attached to the rest of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein.
- alkoxy groups as substituents include, but are not limited to, methoxy (MeO, -OCH 3 ), ethoxy (EtO, -OCH 2 CH 3 ), 1-propoxy (n-PrO, n-Propoxy, -OCH 2 CH 2 CH 3 ), 2-propoxy (i-PrO, i-propoxy, -OCH(CH 3 ) 2 ), 1-butoxy (n-BuO, n-Butoxy, -OCH 2 CH 2 CH 2 CH 3 ), 2-methyl-l-propoxy (i-BuO, i-butoxy, -OCH 2 CH(CH 3 ) 2 ), 2 -Butoxy (s-BuO, s-butoxy, -OCH( CH3 ) CH2CH3 ), 2 -methyl-2-propoxy (
- alkylthio means that an alkyl group is attached to the rest of the molecule through a sulfur atom, wherein the alkyl group has the meaning as described herein.
- alkylthio groups as substituents include, but are not limited to, methylthio (MeS, -SCH3 ), ethylthio ( EtS , -SCH2CH3 ), 1-propylthio (n- PrS, n-propylthio, -SCH2CH2CH3 ), 2-propylthio (i-PrS, i-propylthio, -SCH(CH3)2 ) , and the like.
- alkylsilyl refers to Wherein, R G1 , R G2 and R G3 are independently alkyl groups, and specific examples of alkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl , propyldimethylsilyl;
- arylsilyl refers to Wherein, R G4 , R G5 , and R G6 are independently aryl groups, and specific examples of arylsilyl groups include, but are not limited to, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but not It is not limited to this.
- haloalkyl means an alkyl group substituted with one or more halogen atoms, wherein the alkyl group has the meaning as described herein.
- the haloalkyl group having 1 to 4 carbon atoms includes a fluorine substituted alkyl group having 1 to 4 carbon atoms, such examples include, but are not limited to, trifluoromethyl, difluoromethyl , 1-fluoro-2-chloroethyl, etc.
- cycloalkyl refers to a monocyclic or polycyclic saturated cyclic hydrocarbon group obtained by removing a hydrogen atom, and "cycloalkyl" may have one or more points of attachment to the rest of the molecule.
- the cycloalkyl group is a ring system containing 3-10 ring carbon atoms; in other embodiments, the cycloalkyl group is a cycloalkyl group containing 5-10 ring carbon atoms;
- the alkyl group is a cycloalkyl group containing 5-7 ring carbon atoms; in other embodiments, the cycloalkyl group is a cycloalkyl group containing 3-6 ring carbon atoms.
- cycloalkyl groups may independently be unsubstituted or substituted with one or more substituents described herein.
- cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- cycloalkenyl refers to a group obtained by removing a hydrogen atom from a monocyclic or polycyclic unsaturated cyclic olefin, and a "cycloalkenyl" may have one or more points of attachment to the rest of the molecule.
- the cycloalkenyl group is a cycloalkenyl group containing 2-10 ring carbon atoms; in other embodiments, the cycloalkenyl group is a cycloalkenyl group containing 5-10 ring carbon atoms.
- the cycloalkenyl groups may independently be unsubstituted or substituted with one or more substituents described herein. For example cyclohexenyl.
- Ring in this application includes saturated rings, unsaturated rings; saturated rings are cycloalkyl, heterocycloalkyl, unsaturated rings are cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
- a ring system formed by n ring atoms is an n-membered ring.
- phenyl is a 6-membered aryl group.
- a 5- to 10-membered aromatic ring refers to an aryl or heteroaryl group containing 5 to 10 ring atoms;
- a 5- to 10-membered aliphatic ring refers to a cycloalkyl or cycloalkenyl group containing 5 to 10 ring atoms.
- “5- to 13-membered aliphatic rings” include, but are not limited to, cyclopentane, cyclohexane, cycloheptane, adamantane, camphorane, etc.; “5- to 10-membered aliphatic rings” include but are not limited to , cyclopentane, cyclohexane, cycloheptane, adamantane; “5- to 6-membered aliphatic rings” such as cyclopentane, cyclohexane; “5- to 13-membered aromatic rings” in this application include but are not limited to pyrrole ring, furan, thiophene, benzene, naphthalene, pyridine, quinoline, quinoxaline, fluorene, etc., wherein fluorene is a 13-membered aromatic ring.
- any two adjacent substituents on L 1 to L 3 and Ar 1 to Ar 3 form a ring, which means that the cycloalkyl is connected to two substituents on the same atom to form a spiro, or is connected to Substituents on adjacent atoms are joined to form fused aryl rings.
- any two adjacent substituents form a ring means that two adjacent substituents may form a ring but need not form a ring, and this scheme includes the scenario where two substituents are joined to form a ring , also includes the situation where two substituents exist independently of each other.
- two adjacent substituents may exist in the form of a saturated or unsaturated ring, or may exist independently of each other.
- the non-positioning connecting bond refers to the single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule.
- the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. -1) to any possible connection method shown in formula (f-10).
- the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, which represents The meaning of , includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
- a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system.
- the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-positioning link, and the meanings it represents include such as formula (Y-1) ⁇ Any possible connection mode shown by formula (Y-7).
- At least one of X 1 , X 2 , and X 3 of the compounds of the present application is N.
- the meaning is that any one of X 1 , X 2 and X 3 can be N, and the other two can be selected from C(R 0 ) or N.
- At least two of X 1 , X 2 , and X 3 of the compounds of the present application are N.
- the meaning is that any two of X 1 , X 2 and X 3 can be N, and the other can be C(R 0 ); specifically, X 1 , X 2 are N, and X 3 is C(R 0 ) . ); X 2 , X 3 are N, X 1 is C(R 0 ); X 1 , X 3 are N, X 2 is C(R 0 ); X 1 , X 2 , X 3 are all N four cases .
- m 1 +m 2 +m 3 +q 1 +q 2 +q 3 in the compounds of the present application is 1, 2 or 3
- n 1 +n 2 +n 3 +t 1 +t 2 +t 3 is 1 or 2.
- the number of cyano groups and the number of adamantyl groups may or may not be equal.
- the total number of cyano substituents in the compounds of the present application is selected from 1, 2 or 3, optionally, the total number of cyano substituents in the compounds of the present application is selected from 1 or 2 Piece.
- the total number of adamantyl substituents in the compounds of the present application is selected from 1 or 2, optionally, the total number of adamantyl substituents in the compounds of the present application is one.
- the Ar 1 , Ar 2 , and Ar 3 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and 5-20 substituted or unsubstituted heteroaryl groups.
- the substituents in Ar 1 to Ar 3 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, group A, trioxane having 3 to 8 carbon atoms Silyl group, triphenylsilyl group, alkyl group with 1 to 4 carbon atoms, halogenated alkyl group with 1 to 4 carbon atoms, cycloalkyl group with 5 to 10 carbon atoms, and 1 to 1 carbon atoms alkoxy group of 4, alkylthio group with 1-4 carbon atoms, aryloxy group with carbon number of 6-15, arylthio group with carbon number of 6-15; the group A is selected from carbon atoms A substituted or unsubstituted heteroaryl group with 5-18 atoms or a substituted or unsubstituted aryl group with 6-20 carbon atoms, and the substituent in the group A is selected from deuterium, halogen group, cyano, alkyl with 1 to 4 carbon
- any two adjacent substituents are connected to each other to form an aliphatic ring, which means that two adjacent substituents connected to the same atom are connected to each other to form a spiro ring; any two adjacent substituents are connected to each other to form a spiro ring.
- Aromatic ring means that two adjacent substituents attached to adjacent atoms are connected to each other to form a fused ring.
- the substituents in Ar 1 to Ar 3 are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl , tert-butyl, trifluoromethyl, trimethylsilyl, methoxy, ethoxy, isopropoxy, methylthio, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl , naphthyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl; optional Typically, any two adjacent substituents form a 5- to 6-membered aliphatic ring or a 6- to 13-membered aromatic ring.
- the Ar 1 , Ar 2 , and Ar 3 are the same or different, and each is independently selected from the group consisting of the groups represented by the following formula i-1 to formula i-15:
- M 1 is selected from single bond or
- G 1 to G 5 are each independently selected from N or C(J 1 ), and at least one of G 1 to G 5 is selected from N; when two or more of G 1 to G 5 are selected from C(J 1 ) , any two J 1 are the same or different;
- G 6 to G 13 are each independently selected from N or C(J 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(J 2 ) , any two J 2 are the same or different;
- G 14 to G 23 are each independently selected from N or C(J 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(J 3 ) , any two J 3 are the same or different;
- G 24 to G 33 are each independently selected from N or C(J 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(J 4 ) , any two J 4 are the same or different;
- G 34 to G 37 are each independently selected from N or C(J 5 ), and when two or more of G 34 to G 37 are selected from C(J 5 ), any two J 5 are the same or different;
- Z 1 is selected from hydrogen, deuterium, halogen group, cyano group, alkylsilyl group with 3-8 carbon atoms, alkyl group with 1-6 carbon atoms, haloalkyl group with 1-6 carbon atoms, A cycloalkyl group with 5-10 carbon atoms, an alkoxy group with 1-6 carbon atoms, an alkylthio group with 1-6 carbon atoms, and a triphenylsilyl group;
- Z 2 to Z 9 and Z 21 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, alkylsilyl group having 3 to 8 carbon atoms, alkyl group having 1 to 6 carbon atoms, carbon Halogenated alkyl group having 1 to 6 atoms, cycloalkyl group having 5 to 10 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, triphenylsilane base, heteroaryl with 3 to 18 carbon atoms;
- Z 10 to Z 20 and J 1 to J 5 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, alkylsilyl group having 3 to 8 carbon atoms, and alkane having 1 to 6 carbon atoms group, haloalkyl group with 1 to 6 carbon atoms, cycloalkyl group with 5 to 10 carbon atoms, alkoxy group with 1 to 6 carbon atoms, alkylthio group with 1 to 6 carbon atoms, tris Phenylsilyl group, aryl group with 6-18 carbon atoms, heteroaryl group with 3-18 carbon atoms; optionally, two adjacent Z 19 are connected to each other to form a 5-10-membered aromatic ring or 5 ⁇ 10-membered heteroaromatic ring; optionally, two adjacent Z 20 are connected to each other to form a 5-10-membered aromatic ring or a 5-10-membered heteroaromatic ring;
- h 1 to h 21 are represented by h k
- Z 1 to Z 21 are represented by Z k
- k is a variable, representing any integer from 1 to 21
- h k represents the number of substituents Z k ; wherein, when k is selected from 5 or 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected from When from 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two Z k are the same or different;
- K 1 is selected from O, S, N(Z 22 ), C(Z 23 Z 24 ), Si(Z 23 Z 24 ); wherein Z 22 , Z 23 and Z 24 are each independently selected from: the number of carbon atoms is Aryl with 6-18, heteroaryl with 3-18 carbon atoms, alkyl with 1-6 carbon atoms or cycloalkyl with 5-10 carbon atoms, or Z 23 and Z 24 are mutually Connected to form a saturated or unsaturated ring with 5 to 13 carbon atoms with the atoms that are commonly connected to them;
- K 2 is selected from single bond, O, S, N(Z 25 ), C(Z 26 Z 27 ), Si(Z 26 Z 27 ); wherein Z 25 , Z 26 , Z 27 are each independently selected from: carbon An aryl group having 6 to 18 atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, or the above Z 26 and Z 27 are connected to each other to form a saturated or unsaturated ring having 5 to 13 carbon atoms with the atoms to which they are commonly connected.
- the number of carbon atoms in the ring can be a 5-membered ring, such as It can also be a 6-membered ring, e.g. It can also be a 13-membered ring, for example
- the number of carbon atoms on the ring formed by the interconnection of the two substituents Z 23 and Z 24 may also be other values, which will not be listed one by one here.
- the ring formed by the interconnection of Z 26 and Z 27 is similar to the above-mentioned Z 23 and Z 24 , and will not be repeated here.
- Ar 1 , Ar 2 , Ar 3 are the same or different, and each is independently selected from a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of group of:
- the substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, tri- Fluoromethyl, trimethylsilyl, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl base, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
- Ar 1 , Ar 2 , Ar 3 are the same or different, and are each independently selected from substituted or unsubstituted groups V', and unsubstituted groups V' are selected from the following groups
- the group consists of:
- the substituted group V' has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, Trifluoromethyl, trimethylsilyl, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, phenyl, biphenyl, triple Phenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
- the Ar 1 , Ar 2 , Ar 3 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl base, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted azadibenzothienyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted nitrogen Heterocarbazolyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted
- the Ar 1 , Ar 2 , Ar 3 are the same or different, and each is independently selected from the group consisting of the following groups:
- the Ar 1 , Ar 2 , and Ar 3 are the same or different, and each is independently selected from the group consisting of the following groups:
- the L 1 , L 2 , and L 3 are the same or different, and are each independently selected from a single bond, or from the groups represented by formula j-1 to formula j-14
- the group consists of:
- M 2 is selected from single bond or
- Q 1 to Q 5 are each independently selected from N or C(J 5 ), and at least one of Q 1 to Q 5 is selected from N; when two or more of Q 1 to Q 5 are selected from C(J 5 ), any two J 5 are the same or different;
- Q 6 to Q 13 are each independently selected from N or C(J 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(J 6 ), any two J 6 are the same or different;
- Q 14 to Q 23 are each independently selected from N, C or C(J 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C (J 7 ), any two J 7 are the same or different;
- Q 24 to Q 33 are each independently selected from N, C or C(J 8 ), and at least one of Q 24 to Q 33 is selected from N; when two or more of Q 24 to Q 33 are selected from C (J 8 ), any two J 8 are the same or different;
- E 1 to E 14 and J 5 to J 8 are independently selected from: hydrogen, deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, and aryl group with 6-20 carbon atoms , Alkylsilyl groups with 3 to 8 carbon atoms, triphenylsilyl groups, alkyl groups with 1 to 6 carbon atoms, halogenated alkyl groups with 1 to 6 carbon atoms, and alkyl groups with 2 to 6 carbon atoms Alkenyl group, cycloalkyl group having 5 to 10 carbon atoms, heterocycloalkyl group having 2 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, and alkyl sulfide having 1 to 6 carbon atoms base, aryloxy group with 6-18 carbon atoms, arylthio group with 6-18 carbon atoms;
- e 1 to e 14 are represented by er, E 1 to E 14 are represented by Er , r is a variable, representing any integer from 1 to 14, and er represents the number of substituents E r ; when r is selected from 1, 2, When 3, 4, 5, 6, 13 or 14, er is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, er is selected from 1, 2, 3, 4, 5 or 6; When r is 9 or 12, er is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, er is selected from 1, 2, 3, 4, 5, 6 , 7 or 8; when er is greater than 1, any two Er are the same or different;
- K 3 is selected from O, S, Se, N(E 15 ), C(E 16 E 17 ), Si(E 18 E 19 ); wherein, each of E 15 , E 16 , E 17 , E 18 and E 19 respectively Independently selected from the group consisting of hydrogen, an aryl group with 6 to 20 carbon atoms, a heteroaryl group with 3 to 20 carbon atoms, an alkyl group with 1 to 6 carbon atoms, and an alkene with 2 to 6 carbon atoms radicals, cycloalkyl groups with 5 to 10 carbon atoms, and heterocycloalkyl groups with 2 to 6 carbon atoms;
- E 16 and E 17 are interconnected to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly attached;
- E 18 and E 19 are interconnected to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly attached;
- Each K 4 is independently selected from single bond, O, S, Se, N(E 20 ), C(E 21 E 22 ), Si(E 23 E 24 ); wherein, each of E 20 , E 21 , E 22 , E 23 and E 24 are each independently selected from the group consisting of hydrogen, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 6 carbon atoms, and an alkyl group having 1 to 6 carbon atoms. is an alkenyl group of 2 to 6, a cycloalkyl group of 5 to 10 carbon atoms, and a heterocycloalkyl group of 2 to 10 carbon atoms;
- E 21 and E 22 are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly connected;
- E 23 and E 24 are connected to each other to form a 5- to 13-membered aliphatic ring or a 5- to 13-membered aromatic ring with the atoms to which they are commonly connected.
- the L 1 , L 2 , and L 3 are the same or different, and each is independently selected from a single bond or a substituted or unsubstituted aryl group with 6 to 20 carbon atoms, a carbon A substituted or unsubstituted heteroaryl group having 5 to 18 atoms.
- the substituents in L 1 , L 2 , and L 3 are the same or different, and each is independently selected from deuterium, halogen group, cyano group, group A, tris having 3 to 8 carbon atoms Alkylsilyl group, triphenylsilyl group, alkyl group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, cycloalkyl group having 5 to 10 carbon atoms, and 1 carbon atom ⁇ 4 alkoxy groups, 1-4 carbon atoms alkylthio groups, 6-15 carbon atoms aryloxy groups, 6-15 carbon atoms arylthio groups; the group A is selected from A substituted or unsubstituted heteroaryl group with 5-12 carbon atoms or a substituted or unsubstituted aryl group with 6-15 carbon atoms, and the substituent in the group A is selected from deuterium, halogen group , cyano, alkyl with 1 to
- the substituents in the L 1 , L 2 , L 3 are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, trifluoromethyl, trimethylsilyl, methoxy, ethoxy, isopropoxy, methylthio, cyclopentyl, cyclohexyl, phenyl, biphenyl, Terphenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl , optionally, any two adjacent substituents form a 5- to 6-membered aliphatic ring or a 6- to 13-membered aromatic ring.
- L 1 , L 2 , L 3 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted group W, and the unsubstituted group W is selected from the following groups
- the group consists of:
- the substituents in the group W are each independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, isopropyl, n-propyl, tertiary Butyl group, alkoxy group having 1 to 4 carbon atoms, trifluoromethyl group, trimethylsilyl group, cyclopentyl group, cyclohexane group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, 9 , the group consisting of 9-dimethylfluorenyl, pyridyl, quinolinyl, isoquinolinyl, pyrimidinyl, dibenzofuranyl, dibenzothienyl, and carbazolyl; substitution in group W When the number of groups is more than one, the respective substituents are the same or different.
- the L 1 , L 2 , and L 3 are the same or different, and are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted doublet Phenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted spiro[cyclopentane-1,9'-fluorene]idene base, substituted or unsubstituted spiro[cyclohexane-1,9'-fluorene]idene, substituted or unsubstituted phenanthroline, substituted or unsubstituted quinolylene, substituted or unsubstituted pyridine radical, substituted or unsubstituted isoquinolinylene, substituted or unsubstituted carbazolylylene, substituted or
- L 1 and L 2 are the same or different, and are independently selected from the group consisting of a single bond or the following groups:
- L is selected from a single bond or the group consisting of:
- At least two of X 1 , X 2 , and X 3 are N, and at least one cyano group and at least one adamantyl group are attached to Y 1 , Y 2 , and Y 3 in total.
- Y 1 and Y 2 are each independently selected from the group consisting of:
- Y is selected from the group consisting of :
- Y 3 is attached to at least one cyano group, ie, m 3 +q 3 ⁇ 1, and/or, Y 3 is attached to at least one adamantyl group, ie, n 3 +t 3 ⁇ 1.
- the nitrogen-containing compound is selected from the group consisting of:
- reaction flasks are plugged with suitable rubber stoppers, and the substrate is injected through a syringe. Glassware is dry.
- the chromatographic column was a silica gel column, and silica gel (100-200 mesh) was purchased from Qingdao Ocean Chemical Factory.
- the measurement conditions of low-resolution mass spectrometry (MS) data are: Agilent 6120 quadrupole HPLC-M (column type: Zorbax SB-C18, 2.1 ⁇ 30 mm, 3.5 microns, 6 min, flow rate 0.6 mL/ min.
- Mobile phase 5%-95% (acetonitrile with 0.1% formic acid) in (water with 0.1% formic acid) using electrospray ionization (ESI) at 210nm/254nm with UV detection.
- ESI electrospray ionization
- Hydrogen nuclear magnetic resonance spectrum Bruker 400MHz nuclear magnetic instrument, at room temperature, with CDCl 3 or CD 2 Cl 2 as solvent (in ppm), with TMS (0 ppm) as reference standard. When multiplets are present, the following abbreviations will be used: s (singlet), d (doublet), t (triplet), m (multiplet).
- Target compounds were detected by UV at 210 nm/254 nm using Agilent 1260 pre-HPLC or Calesep pump 250 pre-HPLC (column type: NOVASEP 50/80 mm DAC).
- the white solid intermediate Sub 2-I-B1 (33.28g) was added to the flask, then potassium acetate was added, dissolved in DCM, trifluoromethanesulfonic anhydride was added dropwise at room temperature, pyridine was added after the dropwise addition, stirred for 5h, and then added to the flask.
- magnesium flakes (3.16 g, 131.85 mmol) and 30 ml of tetrahydrofuran were added to the three-necked flask, the temperature of the system was raised to 60 °C, and iodine (0.55 g, 2.19 mmol) was added to the system.
- the compound 4-bromoxynil (20.0 g, 109.87 mmol) was completely dissolved in 30 ml of THF solution, and was slowly added dropwise to the system within 30 min, and the temperature was controlled at 60° C. during the dropwise addition. After the dropwise addition was completed, the reaction was stirred at a temperature of 60 °C for 2 h.
- Sub 1-I-A1 (20.00 g, 68.32 mmol), p-chlorophenylboronic acid (10.89 g, 69.68 mmol), tetrakistriphenylphosphine palladium (1.57 g, 1.36 mmol), potassium carbonate (18.89 g, 136.64 mmol) , tetrabutylammonium bromide (0.44g, 1.36mmol), toluene (160mL), ethanol (80mL) and deionized water (40mL) were added to the three-necked flask, heated to 78°C under nitrogen protection, heated under reflux and stirred for 8h.
- NMR data of compound 46 1 H NMR (400MHZ, CD 2 Cl 2 ) ⁇ (ppm): 8.90(d, 2H), 8.81(d, 2H), 8.75(d, 2H), 7.90(d, 2H), 7.85(d, 2H), 7.65-7.58(m, 3H), 7.36-7.30(m, 4H), 2.19(s, 3H), 1.96(s, 6H), 1.86-1.73(m, 6H).
- the intermediate a-1 (35.0 g, 120.1 mmol) was added to the round-bottomed flask, and then 630 mL of dry THF was added to the flask, and the system was cooled to -80 °C to -90 °C with liquid nitrogen, and then the dropwise addition of positive Butyllithium (8.46 g, 132.1 mmol) was dripped and kept for 1 h.
- Trimethyl borate (13.7g, 14.7mL, 132.1mmol) was added dropwise, the dropping was completed, the temperature was kept at -80°C to -90°C, after 1 h of incubation, it was naturally raised to room temperature, the reaction was completed, and 100 mL of an aqueous solution of HCl (concentration) was added. 2mol/L), stirred for 0.5h.
- magnesium flakes (2.9g, 120.9mmol) and 30mL of tetrahydrofuran (THF) were added to the three-necked flask, the temperature of the system was raised to 80°C, and iodine (0.6g, 2.4mmol), 8-bromo was added to the system.
- Benzofuro[2,3-B]pyridine (30.0 g, 120.9 mmol) was completely dissolved in 30 mL of THF solvent, and was slowly added dropwise to the system within 30 min, and the temperature was controlled at 80° C. during the dropwise addition. After the dropwise addition was completed, the reaction was stirred at 80° C. for 2 h to obtain a mixed solution.
- magnesium flakes (1.6 g, 69.3 mmol) and 10 mL of tetrahydrofuran (THF) were added to the three-necked flask, the temperature of the system was raised to 80 °C, and iodine (0.3 g, 1.4 mmol), b-1 was added to the system. (30.0 g, 120.9 mmol) was completely dissolved in 15 mL of THF solvent, slowly added dropwise to the system within 30 min, and the temperature was controlled at 80° C. during the dropwise addition. After the dropwise addition was completed, the reaction was stirred at 80° C. for 2 h to obtain a mixed solution.
- THF tetrahydrofuran
- aI-1 (22.0 g, 69.3 mmol) dissolved in 50 mL of THF was added dropwise to the mixed solution, and the reaction was terminated after stirring for 3 h to obtain a reaction solution.
- toluene 200 mL was added to extract the reaction solution, the organic phases were combined, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated by distillation under reduced pressure; the crude product was purified by silica gel column chromatography, and methanol was recrystallized and filtered to obtain solid intermediate a. -2-2 (21.3 g, 54%).
- Preparation Examples 25-31 Referring to the preparation methods and operation procedures of the above compounds, using the purchased intermediates as raw materials, compound 55, compound 81, compound 216, compound 570, compound 577, compound 598, and compound 619 were also prepared.
- Preparation Example 25 Compound 55 was synthesized with reference to the preparation process of compound 63 to obtain solid compound 55 (5.70 g) MS (ESI, pos.ion) m/z: 520.18 [M+H] + .
- Preparation Example 27 Compound 216 was synthesized with reference to the preparation process of compound 483 to obtain solid compound 216 (3.70 g) MS (ESI, pos.ion) m/z: 575.13 [M+H] + .
- Preparation Example 28 Compound 570 was synthesized with reference to the preparation process of compound 482 to obtain solid compound 570 (5.35 g) MS (ESI, pos.ion) m/z: 549.25 [M+H] + .
- Embodiments of the present invention also provide an organic electroluminescent device, comprising an anode, a cathode, and a functional layer between the anode and the cathode, where the functional layer includes the above-mentioned nitrogen-containing compound of the present invention.
- the functional layer includes an electron transport layer
- the electron transport layer includes the above-mentioned nitrogen-containing compound of the present invention.
- the nitrogen-containing compound of the present invention is used as the material of the electron transport layer of the electronic element, the efficiency and life of the device can be improved and the working voltage can be reduced.
- the electronic component may be an organic electroluminescent device.
- the organic electroluminescent device may include an anode 100 , a hole transport layer 320 , an electron blocking layer 322 , an organic light emitting layer 330 serving as an energy conversion layer, a hole blocking layer 341 , and an electron transport layer, which are stacked in sequence. 340 and cathode 200.
- the hole transport layer 320 , the electron blocking layer 322 , the organic light-emitting layer 330 as the energy conversion layer, the hole blocking layer 341 , and the electron transport layer 340 together constitute the functional layer 300 .
- the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
- anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; 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 SnO2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. Preference is given to transparent electrodes comprising indium tin oxide (ITO) as anode.
- the hole transport layer 320 and the electron blocking layer 322 respectively comprise one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compound, which is not specifically limited in this application.
- the hole transport layer 320 may be composed of the compound NPB or the compound HT-01, and the electron blocking layer 322 may include the compound EB-01 or TCTA.
- the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a dopant material.
- the organic light-emitting layer 330 is composed of a host material and a dopant material.
- the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy.
- the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.
- the host material of the organic light-emitting layer 330 may be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application.
- the host material of the organic light-emitting layer 330 may be BH-01 or ⁇ , ⁇ -AND.
- the dopant material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not specially made in this application. limits.
- the dopant material of the organic light-emitting layer 330 may be BD-01.
- the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or other electron transport materials.
- the electron transport layer material contains the organic compound of the present application.
- the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
- cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
- a metal electrode comprising magnesium and silver is preferably included as the cathode.
- a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 320 to enhance the capability of injecting holes into the hole transport layer 320 .
- the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
- the hole injection layer 310 may be composed of F4-TCNQ or m-MTDATA.
- an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
- the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
- the electron injection layer 350 may include Yb.
- the electronic component may be a photoelectric conversion device.
- the photoelectric conversion device may include an anode and a cathode disposed oppositely, and a functional layer disposed between the anode and the cathode; the functional layer includes the nitrogen-containing compound provided in the present application.
- the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
- the hole transport layer 320 , the photoelectric conversion layer 360 , and the electron transport layer 340 constitute the functional layer 300 .
- the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
- a solar cell may include an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode that are stacked in sequence, wherein the electron transport layer includes the organic compound.
- a third aspect of the present application provides an electronic device including the electronic component described in the second aspect of the present application.
- the electronic device is a first electronic device 400
- the first electronic device 400 includes the above-mentioned organic electroluminescence device.
- the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
- the electronic device is a second electronic device 500
- the second electronic device 500 includes the above-mentioned photoelectric conversion device.
- the second electronic device 500 may be, for example, a solar power generation device, a photodetector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
- the anode is prepared by the following process: the thickness is The ITO substrate was cut into a size of 40mm x 40mm x 0.7mm, and a photolithography process was used to prepare it into a top emission experimental substrate with a cathode overlap area, an anode and an insulating layer pattern, using ultraviolet ozone and O 2 : N 2 plasma Surface treatment was performed to increase the work function of the anode (experimental substrate) and to clean the experimental substrate.
- m-MTDATA (4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine) was vacuum evaporated on the experimental substrate (anode) to form a thickness of A hole injection layer (HIL) of , and NPB was vacuum evaporated on the hole injection layer to form a thickness of The hole transport layer (HTL).
- HIL hole injection layer
- HTL The hole transport layer
- TCTA was evaporated on the hole transport layer to form a thickness of The electron blocking layer (EBL).
- ⁇ , ⁇ -ADN is used as the host, and BD-1 is doped at the same time.
- the host and dopant form a thickness of 30:3 with a film thickness ratio of 30:3.
- the compound 1 of the present invention was vapor-deposited on the light-emitting layer to form a thickness of The electron transport layer (ETL) of , Yb is evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
- ETL electron transport layer
- EIL electron injection layer
- An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compounds shown in Table 5 were each used in forming the electron transport layer (ETL).
- ETL electron transport layer
- the IVL data is compared with the test results under 10mA/cm 2 , and the lifespan is the test results under the current density of 20mA/cm 2 .
- Examples 1 to 31 prepared using the compounds of the present invention are comparable to Comparative Examples 1 to 31 using known Compound A, Compound B, Compound C, Compound E, Compound F, and Compound G.
- the driving voltage of the organic electroluminescent devices of Examples 1-31 is reduced by about 0.2V, the luminous efficiency (Cd/A) is increased by at least 12.7%, and the device lifetime is increased by at least about 16%.
- the organic electroluminescent devices prepared by using the compounds of the present invention in the electron transport layer (ETL) can achieve higher luminous efficiency, and the device lifetime will be significantly improved.
- the adamantyl group and the nitrile group are connected to the core nucleus of the nitrogen-containing heteroaryl group through the linking group, and the highly polar cyano group makes this part of the structure have a high dipole moment, so that the compound The polarity is improved, and an organic material with high electron mobility is obtained.
- the efficiency and lifespan of the device can be improved and the working voltage can be reduced.
- 1-adamantyl itself can avoid the direct stacking of conjugated planes to form ⁇ aggregation, which can improve the film-forming properties of the material, and at the same time enhance the overall molecular weight and asymmetry, and improve the molecular weight.
- the thermal stability also has a certain improvement in the crystallinity of the material, which improves the stability of the compound when applied to organic electroluminescent devices, increases the life of the device, and is easier to use in mass production; Examples 1 to 31 and Comparative Examples
- the test data of 4 shows that the 1-adamantyl group attached to the end of the compound is superior to the 2-adamantyl group in improving the polarity and thermal stability of the compound.
- the present invention evaluates the stability of the molecular structure of the compound of the present invention under prolonged heating during mass production evaporation by the following method:
- the compound of the present invention in high vacuum environments ( ⁇ 10 -6 Pa), and At the temperature corresponding to the vapor deposition rate per second, the compound of the present invention, the comparative compound D, the compound E, the compound A, and the compound G were respectively subjected to a 200-hour heat resistance test (heat preservation treatment).
- the purity decrease values of the nitrogen-containing compounds of the present disclosure after heating are all less than 0.4%, and most of them are less than 0.3%.
- the purity drop value of the compound exceeds 1%, the efficiency and lifetime of the device will be significantly reduced; the thermally unstable compound will lead to a large difference in the performance of the device prepared before, in the middle and later stages of mass production in actual mass production.
- the heat resistance test of the compounds confirms that the purity drop values of the compounds are all less than 0.4%, and the purity drop values of the compounds D, E, A and G of the comparative examples all exceed 2% at the vapor deposition temperature, exceeding the limit of 1% , so compared to the comparative compounds, the nitrogen-containing compounds of the present disclosure also have excellent thermal stability for mass production.
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Abstract
本申请提供了一种含氮化合物、电子元件和电子装置,属于有机材料技术领域。该含氮化合物通过连接基团将1-金刚烷基和腈基连接在含氮杂芳基母核上,分子整体具有高的偶极矩,可以得到高电子迁移率的有机材料,能够改善电子元件的电子传输性能,将其作为有机发光电致器件的电子传输层时,可以提升器件的发光效率、寿命并降低工作电压。
Description
相关申请的交叉引用
本发明要求于2020年8月7日递交的、申请号为CN202010789251.8的中国专利申请的优先权,在此引用上述中国专利申请公开的内容全文以作为本申请的一部分。本发明要求于2021年9月11日递交的、申请号为CN202010956344.5的中国专利申请的优先权,在此引用上述中国专利申请公开的内容全文以作为本申请的一部分。
本申请涉及有机材料技术领域,尤其涉及一种含氮化合物、电子元件和电子装置。
有机电致发光材料(OLED)作为新一代显示技术,具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点,已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
有机发光现象是指使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件通常具有这样的结构,其包括阳极、阴极和其间的有机材料层。有机发光器件结构中,当在两个电极之间施加电压时,空穴和电子分别从阳极和阴极注入有机材料层,当注入的空穴与电子相遇时形成激子,并且当这些激子返回基态时发光。
现有的有机电致发光器件中,最主要的问题为寿命和效率,随着显示器的大面积化,驱动电压随之提高,导致发光效率及电力效率下降,使用寿命下降。因此,有机材料必须要解决这些效率或寿命问题,需要不断地开发高效率、长寿命、适于量产的用于有机发光器件的新材料。
需要说明的是,在上述背景技术部分发明的信息仅用于加强对本发明的背景的理解,因此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
本发明的目的在于提供一种含氮化合物、电子元件和电子装置,以改善电子元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:
根据本发明的一个方面,提供一种含氮化合物,结构如式1所示:
其中,X
1、X
2、X
3相同或不同,且分别独立地选自C(R
0)或N,且其中至少有一个为N;
L
1、L
2和L
3彼此相同或不同,且分别独立地为:单键、碳原子数为6~30的取代或未取代的亚芳基、碳原子数为3~30的取代或未取代的亚杂芳基;
Ar
1、Ar
2、Ar
3彼此相同或不同,且分别独立地选自碳原子数为6~30的取代或未取代的芳基、碳原子数为3~30的取代或未取代的杂芳基;
Ad为1-金刚烷基;
m
1~m
3以m
i表示,n
1~n
3以n
i表示,q
1~q
3以q
i表示,t
1~t
3以t
i表示;i为变量,其选自1、2或3;
m
i表示L
i上带有的氰基的个数,n
i表示L
i上带有的Ad的个数,q
i表示Ar
i上带有的氰基的个数,t
i表示Ar
i上带有的Ad的个数;
m
i独立地选自0、1、2或3,当m
i大于1时,任意两个m
i相同或不同;
ni独立地选自0、1、2或3,当n
i大于1时,任意两个n
i相同或不同;
q
i独立地选自0、1、2或3,当q
i大于1时,任意两个q
i相同或不同;
t
i独立地选自0、1、2或3,当t
i大于1时,任意两个t
i相同或不同;
且m
1+m
2+m
3+q
1+q
2+q
3≥1,n
1+n
2+n
3+t
1+t
2+t
3≥1;
各R
0彼此相同或不同,且各自独立地选自氢、氘、碳原子数为1-10的烷基、碳原子数为3-20的取代或未取代的杂芳基或者碳原子数为6-20的取代或未取代的芳基;
R
0、L
1~L
3和Ar
1~Ar
3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为2-10的烯基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为5-10的环烯基、碳原子数为4-10的杂环烯基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基、碳原子数为6-18的芳氧基、碳原子数为6-18的芳硫基、碳原子数为6-18的芳基硅烷基、碳原子数为3-12的烷基硅烷基;所述基团A选自碳原子数为3-20的取代或未取代的杂芳基、碳原子数为6-20的取代或未取代的芳基,且所述基团A中的取代基选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基;任选地,任意两个相邻的取代基形成环。
本发明的含氮化合物以含氮杂芳基作为母核,通过芳基或杂芳基作为连接基团将金刚烷基和腈基连接在含氮杂芳基母核上,氰基的存在使得该部分结构具有高的偶极矩,从而使材料极性提高。氰基和杂芳基基团结合,可以得到高电子迁移率的有机材料,将其用作电子元件的电子传输层时,可以提升器件的效率、寿命并降低工作电压。金刚烷基本身作为刚性的大体积多环烷烃结构,可以避免共轭平面直接堆积形成π聚集,可以改善材料的成膜性能,同时使得化合物整体的分子量和不对称性增强,提高分子的热稳定性,也对于材料的结晶性有一定改善,能够提升化合物用于电子元件时的稳定性,使电子元件更易于量产使用。
根据本发明的第二个方面,提供一种电子元件,包括相对设置的阳极和阴极,以及设于所述阳极和所述阴极之间的功能层;所述功能层包含以上所述的含氮化合物。
根据本申请的第三个方面,提供一种电子装置,所述电子装置包括有上述电子元件。
应当理解的是,以上的一般描述和后文的细节描述仅是示例性和解释性的,并不能限制本发明。
此处的附图被并入说明书中并构成本说明书的一部分,示出了符合本发明的实施例,并与说明书一起用于解释本发明的原理。显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
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是本申请实施方式的光电转化器件的结构示意图。
图3是本申请一实施方式的电子装置的结构示意图。
图4是本申请另一实施方式的电子装置的结构示意图。
附图标记说明
100、阳极;200、阴极;300、功能层;310、空穴注入层;320、空穴传输层;322、电子阻挡层;330、有机发光层;340、电子传输层;341、空穴阻挡层;350、电子注入层;360、光电转化层;400、第一电子装置;500、第二电子装置。
现在将参考附图更全面地描述示例实施例。然而,示例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。
本申请实施方式的含氮化合物的结构式如式1所示:
其中,X
1、X
2、X
3相同或不同,且分别独立地选自C(R
0)或N,且其中至少有一个为N;
L
1、L
2和L
3彼此相同或不同,且分别独立地为:单键、碳原子数为6~30的取代或未取代的亚芳基、碳原子数为3~30的取代或未取代的亚杂芳基;
Ar
1、Ar
2、Ar
3彼此相同或不同,且分别独立地选自碳原子数为6~30的取代或未取代的芳基、碳原子数为3~30的取代或未取代的杂芳基;
Ad为1-金刚烷基;
m
1~m
3以m
i表示,n
1~n
3以n
i表示,q
1~q
3以q
i表示,t
1~t
3以t
i表示;i为变量,其选自1、2或3;
m
i表示L
i上带有的氰基的个数,n
i表示L
i上带有的Ad的个数,q
i表示Ar
i上带有的氰基的个数,t
i表示Ar
i上带有的Ad的个数;
m
i独立地选自0、1、2或3,当m
i大于1时,任意两个m
i相同或不同;
ni独立地选自0、1、2或3,当n
i大于1时,任意两个n
i相同或不同;
q
i独立地选自0、1、2或3,当q
i大于1时,任意两个q
i相同或不同;
t
i独立地选自0、1、2或3,当t
i大于1时,任意两个t
i相同或不同;
且m
1+m
2+m
3+q
1+q
2+q
3≥1,n
1+n
2+n
3+t
1+t
2+t
3≥1;
各R
0彼此相同或不同,且各自独立地选自氢、氘、碳原子数为1~10的烷基、碳原子数为3~20的取代或未取代的杂芳基或者碳原子数为6~20的取代或未取代的芳基;
R
0、L
1~L
3和Ar
1~Ar
3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为1~10的烷基、碳原子数为1~10的卤代烷基、碳原子数为2~10的烯基、碳原子数为3~10的环烷基、碳原子数为2~10的杂环烷基、碳原子数为5~10的环烯基、碳原子数为4~10的杂环烯基、碳原子数为1~10的烷氧基、碳原子数为1~10的烷硫基、碳原子数为6~18的芳氧基、碳原子数为6~18的芳硫基、碳原子数为6~18的芳基硅烷基、碳原子数为3~12的烷基硅烷基;基团A选自碳原子数为3~20的取代或未取代的杂芳基、碳原子数为6~20的取代或未取代的芳基,且基团A中的取代基选自氘、卤素基团、氰基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基;任选地,任意两个相邻的取代基形成环。
本发明的含氮化合物以含氮杂芳基作为母核,通过连接基团将1-金刚烷基和腈基连接在含氮杂芳基母核上,氰基的存在使得该部分结构具有高的偶极矩,从而使材料极性提高。氰基和杂芳基基团结合,可以得到高电子迁移率的有机材料,将其用作电子元件的电子传输层时,可以提升器件的效率、寿命并降低工作电压。金刚烷基本身作为刚性的大体积多环烷烃结构,可以避免共轭平面直接堆积形成π聚集,可以改善材料的成膜性能,同时使得化合物整体的分子量和不对称性增强,提高分子的热稳定性,也对于材料的结晶性有一定改善,能够提升化合物用于电子元件时的稳定性,使电子元件更易于量产使用。此外,采用1-金刚烷基的连接形式,相比于2-金刚烷基的连接方式,可以提高化合物整体的分子极性,并且化合物稳定性更好。
在本申请中,L
1~L
3、Ar
1~Ar
3选自取代的芳基或取代的杂芳基时的碳原子数,指的是芳基或杂芳基及其上的取代基的碳原子总数,例如碳原子数为18的取代的芳基,指的是芳基和取代基的总碳原子数为18。举例而言,若Ar
1为9-甲基-9-苯基-芴基,则其属于碳原子数位20的取代的芳基。
当L
1~L
3或Ar
1~Ar
3中的任一个选自“取代的(亚)芳基”时,该芳基及其上的全部取代基一起整体作为L
1~L
3或Ar
1~Ar
3中的任一个。
本申请中,Y
1为
含义是,L
1上连接有m
1个氰基(CN)和n
1个金刚烷基(Ad),Ar
1上连接有q
1个氰基(CN)和t
1个金刚烷基(Ad);可以理解的是,当L
1为取代的芳基时,氰基和金刚烷基既可以连接在所述芳基上,也可以连接在所述芳基的取代基上;同样的,连接在Ar
1上的氰基和金刚烷基具有相同的含义。当Ar
1~Ar
3为取代的芳基或杂芳基时,氰基和金刚烷基既可以连接在芳基或杂芳基上,也可以连接在芳基或杂芳基的取代基上。举例而言,Ar
1选自苯基取代的萘基,其中,氰基既可以连接在苯基上,也可以连接在萘基上。同理,当L
1~L
3为取代的亚芳基或亚杂芳基时,氰基和金刚烷基既可以连接在亚芳基或亚杂芳基上,也可以连接在亚芳基或亚杂芳基的取代基上。举例而言,L
1选自甲基取代的亚苯基,其中,氰基既可以连接在甲基上,也可以连接在亚苯基上。
本申请中,氰基和金刚烷基可以位于同一个连接基团Y
i上,也可以位于不同的连接基团Y
i上(i=1、2或3)。举例而言,在一些实施方式中,Y
3中既包含氰基又包含金刚烷基;在另一些实施方式中,Y
1中包含氰基,Y
3中包含金刚烷基。另一方面,氰基和金刚烷基可以都连接于L
i,也可以都连接于Ar
i,还可以一个连接在L
i上,另一个连接在Ar
i上。举例而言,在一些实施方式中,Y
1中L
1连接一氰基,Y
2中Ar
2上连接一金刚烷基。总而言之,在化学式1中,至少有一个氰基和一个金刚烷基。当该化合物包含多个氰基时,多个氰基可以连接于同一个Ar或同一个L,也可以连接于不同的Ar或不同的L。举例而言,在一些实施方案中,共包含两个氰基,其中一个氰基连接于Ar
1,另一个氰基连接于Ar
2。在另一些实施方案中,共包含两个氰基,两个氰基都连接于Ar
1。再举例而言,在一些实施方案中,共包含两个氰基,其中一个氰基连接于L
1,另一个氰基连接于L
2。在另一些实施方案中,共包含两个氰基,两个氰基都连接于L
1。同理,当取代基中包含多个金 刚烷基时,多个金刚烷基可以连接于同一个Ar或同一个L,也可以连接于不同的Ar或同一个L。
本申请中,C(R
0)表示在C原子上连接有基团R
0。
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一个选自B、N、O、S、Se、Si和P的杂原子。
本申请中,连续以前缀命名的情况意味着按照书写顺序罗列取代基。例如,芳烷氧基意味着被芳基取代的烷氧基,烷氧羰基意味着被烷氧基取代的羰基,芳羰基烯基意味着被芳羰基取代的烯基,芳氧基则是被芳基所取代的羟基。
在本申请中,“芳基”指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基或多环芳基,换言之,芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。稠环芳基是指环系统中的两个碳原子为两个邻接环所共用的两个或更多个环,其中所述环中的至少一者是芳香族的,例如其它环可以是环烷基、环烯基、芳基。本申请中的芳基的实例可以包括但不限于,苯基、萘基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
基、苝基、芴基、三亚苯基、并四苯基、次三苯基(triphenylenyl)等。本申请中,芴基可以被取代,2个取代基可以彼此结合而形成螺环结构。在上述芴基被取代的情况下,可以为:
在本申请中,取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、烷基硅烷基、芳基硅烷基、烷基、卤代烷基、环烷基、烷氧基、烷硫基等基团取代。例如,杂芳基取代的芳基的具体实例包括但不限于,二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、咔唑基取代的苯基、吡啶取代的苯基等。应当理解地是,取代的芳基的碳原子数,指的是芳基和芳基上的取代基的碳原子总数,例如碳原子数为18的取代的芳基,指的是芳基和取代基的总碳原子数为18。
本申请中,作为取代基的芳基的实例可以包括但不限于,苯基、萘基、蒽基、菲基、联苯基、三联苯基、芴基、二甲基芴基、芘基、苝基。
本申请中,在一些实施方案中,芳基的碳原子数可以选自6、10、12、13、14、15、16、17、18、20、25或30个。在一些实施方案中,芳基是碳原子数为6~30的芳基,另一些实施方式中,芳基是碳原子数为6~25的芳基,另一些实施方式中,芳基是碳原子数为6~20的芳基,另一些实施方式中,芳基是碳原子数为6~18的芳基,另一些实施方式中,芳基是碳原子数为6~15的芳基,另一些实施方式中,芳基的碳原子数为6~13的芳基,另一些实施方式中,芳基的碳原子数为6~12的芳基。
本申请中,亚芳基为2价基团,除此以外,可以适用上述关于芳基的说明。
在本申请中,杂芳基是指环中包含至少一个独立地选自O、N、P、Si、Se、B、和S的杂原子的单环或多环体系,且其中至少有一个环体系是芳香族的。杂芳基中每一个环体系包含5-7个环原子组成的环,且有一个或多个附着点与分子其余部分相连。杂芳基可以是单环杂芳基或多环杂芳基,换言之,杂芳基可以是单个芳香环体系,也可以是通过碳碳键共轭连接的多个芳香环体系,且任一芳香环体系为一个芳香单环或者一个芳香稠环。稠环杂芳基是指环系统中的两个原子为两个邻接环所共用的两个或更多个环,其中所述环中的至少一者是芳香族的,例如其它环可以是环烷基、杂环基、环烯基、芳基。
示例地,杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、异噻唑基、噁二唑基、三唑基、唑基、呋吖基、吡啶基、联吡啶基、菲啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等,而不限于此。其中,噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基,N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
在本申请中,取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。例如,芳基取代的杂芳基的具体实例包括但不限于,苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的咔唑基、苯基取代的吡啶基等。应当理解地是,取代的杂芳基的碳原子数,指的是杂芳基和杂芳基上的取代基的碳原子总数。例如碳原子数为14的取代的杂芳基,指的是杂芳基和取代基的总碳原子数为14。
本申请中,作为取代基的杂芳基的实例可以包括但不限于,二苯并噻吩基、二苯并呋喃基、咔唑基、N-苯基咔唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、喹啉基、异喹啉基、喹唑啉基、苯并咪唑基、吲哚基、菲咯啉基。
本申请中,在一些实施方案中,杂芳基的碳原子数可以选自3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、20、21、22、23、24、25、26、27、28、29或30个。在一些实施方案中,杂芳基是碳原子数为3~12的杂芳基,另一些实施方式中,杂芳基是碳原子数为3~15的杂芳基,另一些实施方式中,杂芳基是碳原子数为5~12的杂芳基,另一些实施方式中,杂芳基是碳原子数为5~18的杂芳基。
本申请中,亚杂芳基为2价基团,除此以外,可以适用上述关于杂芳基的说明。
本申请中,作为取代基的卤素基团,可以是氟、氯、溴或碘。
本申请中,“烷基”包括1~10个碳原子饱和直链或支链的、单价或多价烷基,其中烷基可以独立任选地被一个或多个本发明所描述的取代基所取代。其中一些实施例是,烷基基团含有1~10个碳原子,另外一些实施例是,烷基基团含有1~8个碳原子,另外一些实施例是,烷基基团含有1~6个碳原子,另外一些实施例是,烷基基团含有1~4个碳原子,另外一些实施例是,烷基基团含有1~3个碳原子。作为取代基的碳原子数为1~4的烷基基团的实例包括,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),2-甲基丙基或异丁基(i-Bu,-CH
2CH(CH
3)
2),1-甲基丙基,仲丁基(s-Bu,-CH(CH
3)CH
2CH
3),叔丁基(t-Bu,-C(CH
3)
3)等。
本申请中,“烯基”表示含有2~10个碳原子的直链或支链的、一价或多价烃基,其中至少有一个不饱和位点,即有一个碳-碳sp
2双键,其中,所述烯基基团可以任选地被一个或多个本发明所描述的取代基所取代,其包括“cis”和“trans”的定位,或者“E”和“Z”的定位。在一些实施方式,烯基的碳原子数为2至6。作为其非限制性例子,烯基有乙烯基(vinyl)、烯丙基(allyl)、异丙烯基(isopropenyl)、2-丁烯基(2-butenyl)、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯、烯丙基、1-苯基乙烯-1-基、2-苯基乙烯-1-基、2,2-二苯乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、苯乙烯基等。
本申请中,“烷氧基”表示烷基基团通过氧原子与分子其余部分相连,其中烷基基团具有如本发明所述的含义。作为取代基的烷氧基的实例包括,但并不限于,甲氧基(MeO、-OCH
3),乙氧基(EtO、-OCH
2CH
3),1-丙氧基(n-PrO、n-丙氧基、-OCH
2CH
2CH
3),2-丙氧基(i-PrO、i-丙氧基、-OCH(CH
3)
2),1-丁氧基(n-BuO、n-丁氧基、-OCH
2CH
2CH
2CH
3),2-甲基-l-丙氧基(i-BuO、i-丁氧基、-OCH
2CH(CH
3)
2),2-丁氧基(s-BuO、s-丁氧基、-OCH(CH
3)CH
2CH
3),2-甲基-2-丙氧基(t-BuO、t-丁氧基、-OC(CH
3)
3),等等。
本申请中,“烷硫基”表示烷基基团通过硫原子与分子其余部分相连,其中烷基基团具有如 本发明所述的含义。作为取代基的烷硫基基团的实例包括,但并不限于,甲硫基(MeS、-SCH
3),乙硫基(EtS、-SCH
2CH
3),1-丙硫基(n-PrS、n-丙硫基、-SCH
2CH
2CH
3),2-丙硫基(i-PrS、i-丙硫基、-SCH(CH
3)
2),等等。
本申请中,“卤代烷基”表示烷基基团被一个或多个卤素原子所取代,其中烷基基团具有如本发明所述的含义。在一实施方案中,碳原子数为1~4的卤代烷基包含碳原子数为1~4的氟取代的烷基,这样的实例包含,但并不限于,三氟甲基、二氟甲基、1-氟-2-氯乙基等。
本申请中,环烷基是指单环或多环饱和环状烃去除氢原子后得到的基团,“环烷基”可以有一个或多个连接点连接到分子的其余部分。在一些实施例中,环烷基是含3~10个环碳原子的环体系;另外一些实施例,环烷基是含5~10个环碳原子的环烷基;另外一些实施例,环烷基是含5~7个环碳原子的环烷基;另外一些实施例,环烷基是含3~6个环碳原子的环烷基。所述环烷基基团可以独立地未被取代或被一个或多个本发明所描述的取代基所取代。作为其非限制性例子,环烷基有环丙基、环丁基、环戊基、环己基、降冰片基(norbornyl)、金刚烷(adamantine)等。
本申请中,环烯基是指单环或多环不饱和环状烯烃去除氢原子后得到的基团,“环烯基”可以有一个或多个连接点连接到分子的其余部分。在一些实施例中,环烯基是含2~10个环碳原子的环烯基;另外一些实施例,环烯基是含5~10个环碳原子的环烯基。所述环烯基基团可以独立地未被取代或被一个或多个本发明所描述的取代基所取代。例如环己烯基。
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。
在本发明中,n个环原子形成的环体系,即为n元环。例如,苯基为6元芳基。5到10元芳香环就是指含有5到10个环原子的芳基或杂芳基;5到10元脂肪族环是指含有5到10个环原子的环烷基或环烯基。
本申请中,“5到13元脂肪族环”包括但不限于,环戊烷、环己烷、环庚烷、金刚烷、樟脑烷等;“5到10元脂肪族环”包括但不限于,环戊烷、环己烷、环庚烷、金刚烷;“5到6元脂肪族环”例如环戊烷、环己烷;本申请中“5到13元芳香环”包括但不限于吡咯环、呋喃、噻吩、苯、萘、吡啶、喹啉、喹喔啉、芴等,其中,芴为13元芳香环。
本申请中,L
1~L
3和Ar
1~Ar
3上任意两个相邻的取代基形成环,是指连接与同一原子上的两个取代基形成螺合的环烷基,或者连接在相邻原子上的取代基相互连接形成稠合芳香基环。
术语“任选”或者“任选地”意味着随后所描述的事件或者环境可以但不必发生,该说明包括该事情或者环境发生或者不发生的场合。例如,“任选地,任意两个相邻的取代基形成环”意味着两个相邻的取代基可以成环但不必须成环,该方案包括两个取代基相互连接形成成环的情景,也包括两个取代基相互独立地存在的情景。举例而言,两个相邻的取代基可以是以形成饱和或不饱和的环的形式存在,也可以是相互独立地存在。连接在同一个原子上的两个相邻的取代基成环的情况下,所形成的环与分子其他部分是螺合连接。连接在相邻原子上的两个相邻的取代基成环的情况下,所形成的环与分子其他部分是稠合连接。
举例而言,下式(f)中所示的,式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分 子其他位置连接,其所表示的含义,包括如式(f-1)~式(f-10)所示出的任一可能的连接方式。
再举例而言,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。
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。
下文中对于不定位连接或不定位取代的含义与此处相同,后续将不再进行赘述。
可选地,在一些实施方案中,本申请化合物的X
1、X
2、X
3中至少有一个为N。含义是X
1、X
2、X
3中可以有任意一个为N,另外两个任选自C(R
0)或N。包括:X
1为N,X
2、X
3各自独立地为C(R
0)或N;X
2为N,X
1、X
3各自独立地为C(R
0)或N;X
3为N,X
1、X
2各自独立地为C(R
0)或N;这三种情况。
可选地,在一些实施方案中,本申请化合物的X
1、X
2、X
3中至少有两个为N。其含义是,X
1、X
2、X
3中可以有任意两个为N,另一个为C(R
0);具体而言,包括X
1、X
2为N,X
3为C(R
0);X
2、X
3为N,X
1为C(R
0);X
1、X
3为N,X
2为C(R
0);X
1、X
2、X
3均为N四种情况。
可选地,在一些实施方案中,本申请化合物中的m
1+m
2+m
3+q
1+q
2+q
3为1、2或3,n
1+n
2+n
3+t
1+t
2+t
3为1或2。氰基的个数和金刚烷基的个数可以相等,也可以不等。在一些实施方案中,本申请的化合物中氰基取代基的总个数选自1、2或3个,可选地,本申请的化合物中氰基取代基的总个数选自1或2个。在一些实施方案中,本申请的化合物中金刚烷基取代基的总个数选自1或2个,可选地,本申请的化合物中金刚烷基取代基的总个数为1个。
可选地,在一些实施方案中,所述Ar
1、Ar
2、Ar
3相同或不同,且各自独立地选自碳原子数为6~25的取代或未取代的芳基、碳原子数为5~20的取代或未取代的杂芳基。在一些实施方案中,所述Ar
1~Ar
3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为3~8的三烷基硅基、三苯基硅基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~4的烷氧基、碳原子数为1~4的烷硫基、碳原子数为6~15的芳 氧基、碳原子数为6~15的芳硫基;所述基团A选自碳原子数为5~18的取代或未取代的杂芳基或者碳原子数为6~20的取代或未取代的芳基,且所述基团A中的取代基选自氘、卤素基团、氰基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基;任选地,任意两个相邻的取代基形成5到10元脂肪族环或5到13元芳香环。
可以理解的是,任意两个相邻取代基相互连接形成脂肪族环,指的是连接于同一原子上的两个相邻取代基相互连接形成螺环;任意两个相邻取代基相互连接形成芳香环,指的是连接于相邻原子上的两个相邻取代基相互连接形成稠合环。
在一些更具体的实施例中,所述Ar
1~Ar
3中的取代基相同或不同,且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、正丙基、叔丁基、三氟甲基、三甲基硅基、甲氧基、乙氧基、异丙氧基、甲硫基、环戊基、环己基、苯基、联苯基、三联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、喹啉基、异喹啉基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基;任选地,任意两个相邻的取代基形成5到6元脂肪族环或6到13元芳香环。
可选地,在一些实施方案中,所述Ar
1、Ar
2、Ar
3相同或不同,且各自独立地选自如下式i-1至式i-15所示的基团所组成的组:
G
1~G
5各自独立地选自N或者C(J
1),且G
1~G
5中至少一个选自N;当G
1~G
5中的两个以上选 自C(J
1)时,任意两个J
1相同或者不相同;
G
6~G
13各自独立地选自N或者C(J
2),且G
6~G
13中至少一个选自N;当G
6~G
13中的两个以上选自C(J
2)时,任意两个J
2相同或者不相同;
G
14~G
23各自独立地选自N或者C(J
3),且G
14~G
23中至少一个选自N;当G
14~G
23中的两个以上选自C(J
3)时,任意两个J
3相同或者不相同;
G
24~G
33各自独立地选自N或者C(J
4),且G
24~G
33中至少一个选自N;当G
24~G
33中的两个以上选自C(J
4)时,任意两个J
4相同或者不相同;
G
34~G
37各自独立地选自N或者C(J
5),当G
34~G
37中的两个以上选自C(J
5)时,任意两个J
5相同或者不相同;
Z
1选自氢、氘、卤素基团、氰基、碳原子数为3~8的烷基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、三苯基硅烷基;
Z
2~Z
9、Z
21各自独立地选自:氢、氘、卤素基团、氰基、碳原子数为3~8的烷基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、三苯基硅烷基、碳原子数为3~18的杂芳基;
Z
10~Z
20、J
1~J
5各自独立地选自:氢、氘、卤素基团、氰基、碳原子数为3~8的烷基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、三苯基硅烷基、碳原子数为6~18的芳基、碳原子数为3~18的杂芳基;任选地,两个相邻的Z
19相互连接形成5~10元芳环或5~10元杂芳环;任选地,两个相邻的Z
20相互连接形成5~10元芳环或5~10元杂芳环;
h
1~h
21以h
k表示,Z
1~Z
21以Z
k表示,k为变量,表示1~21的任意整数,h
k表示取代基Z
k的个数;其中,当k选自5或者17时,h
k选自1、2或者3;当k选自2、7、8、12、15、16、18或者21时,h
k选自1、2、3或者4;当k选自1、3、4、6、9或者14时,h
k选自1、2、3、4或者5;当k为13时,h
k选自1、2、3、4、5或者6;当k选自10或者19时,h
k选自1、2、3、4、5、6或者7;当k为20时,h
k选自1、2、3、4、5、6、7或者8;当k为11时,h
k选自1、2、3、4、5、6、7、8或9;且当h
k大于1时,任意两个Z
k相同或者不相同;
K
1选自O、S、N(Z
22)、C(Z
23Z
24)、Si(Z
23Z
24);其中,Z
22、Z
23、Z
24各自独立地选自:碳原子数为6~18的芳基、碳原子数为3~18的杂芳基、碳原子数为1~6的烷基或碳原子数为5~10的环烷基,或者上述Z
23和Z
24相互连接以与它们共同连接的原子形成碳原子数为5~13的饱和或不饱和的环;
K
2选自单键、O、S、N(Z
25)、C(Z
26Z
27)、Si(Z
26Z
27);其中,Z
25、Z
26、Z
27各自独立地选自:碳原子数为6~18的芳基、碳原子数为3~18的杂芳基、碳原子数为1~6的烷基或碳原子数为5~10的环烷基,或者上述Z
26和Z
27相互连接以与它们共同连接的原子形成碳原子数为5~13的饱和或不饱和的环。
例如,
中,当K
2为单键,M
1为单键,G
34~G
37为CH,Z
19为氢,K
1选自C(Z
23Z
24)时,当Z
23、Z
24形成环时,该环的碳原子数可以是5元环,例如
也可以是6元环,例如
还可以是13元环,例如
当然,两个取代基Z
23、Z
24相互连接形成的环上的碳原子数还可以为其他数值,此处不再一一列举。
Z
26和Z
27相互连接形成的环与上述Z
23和Z
24类同,此处不再赘述。
可选地,在一些实施方案中,Ar
1、Ar
2、Ar
3相同或不同,且各自独立地选自取代或未取代的基团V,未取代的基团V选自以下基团所组成的组:
取代的基团V上具有一个或两个以上取代基,所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、正丙基、叔丁基、三氟甲基、三甲基硅基、碳原子数为1~4的烷氧基、碳原子数为1~4的烷硫基、环戊基、环己基、苯基、联苯基、三联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、喹啉基、异喹啉基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基。
可选地,在另一些实施方案中,Ar
1、Ar
2、Ar
3相同或不同,且各自独立地选自取代或未取代的基团V’,未取代的基团V’选自以下基团所组成的组:
取代的基团V’上具有一个或两个以上取代基,所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、正丙基、叔丁基、三氟甲基、三甲基硅基、碳原子数为1~4的烷氧基、碳原子数为1~4的烷硫基、环戊基、环己基、苯基、联苯基、三联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、喹啉基、异喹啉基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基。
可选地,在一些实施方案中,所述Ar
1、Ar
2、Ar
3分别独立地选自取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的芴基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的氮杂二苯并噻吩基、取代或未取代的氮杂二苯并呋喃基、取代或未取代的氮杂咔唑基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的螺二芴基、取代或未取代的苯并呋喃[3,2-b]吡啶基、取代或未取代的苯氧茶碱基、取代或未取代的吩噻嗪基、取代或未取代的吩噁嗪基、取代或未取代的螺[环戊烷-1,9’- 芴]基、取代或未取代的螺[环己烷-1,9’-芴]基、取代或未取代的9H-9-硅杂芴基,或者为上述基团中两者或三者通过单键连接所形成的基团;Ar
1、Ar
2、Ar
3中的取代基彼此相同或不同,各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、联苯基、萘基、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基所组成的组。
可选地,在一些实施方案中,所述Ar
1、Ar
2、Ar
3相同或不同,且各自独立地选自以下基团组成的组:
可选地,在另一些实施方案中,所述Ar
1、Ar
2、Ar
3相同或不同,且各自独立地选自以下基团组成的组:
可选地,在一些实施方案中,所述L
1、L
2、L
3相同或不同,且分别独立地选自单键、或者选自式j-1至式j-14所示的基团所组成的组:
Q
1~Q
5各自独立地选自N或者C(J
5),且Q
1~Q
5中至少一个选自N;当Q
1~Q
5中的两个或者两个以上选自C(J
5)时,任意两个J
5相同或者不相同;
Q
6~Q
13各自独立地选自N或者C(J
6),且Q
6~Q
13中至少一个选自N;当Q
6~Q
13中的两个或者两个以上选自C(J
6)时,任意两个J
6相同或者不相同;
Q
14~Q
23各自独立地选自N、C或者C(J
7),且Q
14~Q
23中至少一个选自N;当Q
14~Q
23中的两个或者两个以上选自C(J
7)时,任意两个J
7相同或者不相同;
Q
24~Q
33各自独立地选自N、C或者C(J
8),且Q
24~Q
33中至少一个选自N;当Q
24~Q
33中的两个或者两个以上选自C(J
8)时,任意两个J
8相同或者不相同;
E
1~E
14、J
5~J
8分别独立地选自:氢、氘、卤素基团、氰基、碳原子数为3~20的杂芳基、碳原子数为6~20的芳基、碳原子数为3~8的烷基硅烷基、三苯基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为2~6的烯基、碳原子数为5~10的环烷基、碳原子数为2~6的杂环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、碳原子数为6~18的芳氧基、碳原子数为6~18的芳硫基;
e
1~e
14以e
r表示,E
1~E
14以E
r表示,r为变量,表示1~14的任意整数,e
r表示取代基E
r的数量;当r选自1、2、3、4、5、6、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9或12时,e
r选自1、2、3、4、5、6或者7;当r选自8或10时,e
r选自1、2、3、4、5、6、7或者8;当e
r大于1时,任意两个E
r相同或者不相同;
K
3选自O、S、Se、N(E
15)、C(E
16E
17)、Si(E
18E
19);其中,各E
15、E
16、E
17、E
18和E
19分别独立地选自:氢、碳原子数为6~20的芳基、碳原子数为3~20的杂芳基、碳原子数为1~6的烷基、碳原子数为2~6的烯基、碳原子数为5~10的环烷基、碳原子数为2~6的杂环烷基;
或者,任选地,上述E
16和E
17相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环;
或者,任选地,上述E
18和E
19相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环;
各K
4独立地选自单键、O、S、Se、N(E
20)、C(E
21E
22)、Si(E
23E
24);其中,各E
20、E
21、E
22、E
23、E
24分别独立地选自:氢、碳原子数为6~20的芳基、碳原子数为3~20的杂芳基、碳原子数为1~6的烷基、碳原子数为2~6的烯基、碳原子数为5~10的环烷基、碳原子数为2~10的杂环烷基;
或者,任选地,上述E
21和E
22相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环;
或者,任选地,上述E
23和E
24相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环。
可选地,在一些实施方案中,所述L
1、L
2、L
3相同或不同,且各自独立地选自单键或碳原子数为6~20的取代或未取代的芳基、碳原子数为5~18的取代或未取代的杂芳基。在一些实施方案中,L
1、L
2、L
3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为3~8的三烷基硅基、三苯基硅基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~4的烷氧基、碳原子数为1~4的烷硫基、碳原子数为6~15的芳氧基、碳原子数为6~15的芳硫基;所述基团A选自碳原子数为5~12的取代或未取代的杂芳基或碳原子数为6~15的取代或未取代的芳基,且所述基团A中的取代基选自氘、卤素基团、氰基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基;任选地,任意两个相邻的取代基形成5到10元脂肪族环或5到13元芳香环。
在一些更具体的实施例中,所述L
1、L
2、L
3中的取代基相同或不同,且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、正丙基、叔丁基、三氟甲基、三甲基硅基、甲氧基、乙氧基、异丙氧基、甲硫基、环戊基、环己基、苯基、联苯基、三联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、喹啉基、异喹啉基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基,任选地,任意两个相邻的取代基形成5到6元脂肪族环或6到13元芳香环。
可选地,在一些实施方案中,L
1、L
2、L
3相同或者不同,且分别独立地选自单键、取代或未取代的基团W,未取代的基团W选自由如下基团所组成的组:
基团W被一个或多个取代基所取代时,基团W中的取代基各自独立地选自由氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、碳原子数为1~4的烷氧基、三氟甲基、三甲基硅基、环戊烷基,环己烷基、苯基、联苯基、萘基、芴基、9,9-二甲基芴基、吡啶基、喹啉基、异喹啉基、嘧啶基、二苯并呋喃基、二苯并噻吩基、咔唑基所组成的组;基团W中的取代基数目多于1个时,各个取代基相同或不同。
可选地,在一些实施方案中,所述L
1、L
2、L
3相同或不同,且分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的螺[环戊烷-1,9’-芴]亚基、取代或未取代的螺[环己烷-1,9’-芴]亚基、取代或未取代的亚菲咯啉基、取代或未取代的亚喹啉基、取代或未取代的吡啶基、取代或未取代的亚异喹啉基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的苯并菲亚基,或者为上述亚基中两者或三者通过单键连接所形成的亚基基团;L
1、L
2、L
3中的取代基彼此相同或不同,且各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲 氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、联苯基、萘基、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基所组成的组。
可选地,在一些实施方案中,L
1、L
2相同或不同,且分别独立地选自单键或如下基团所组成的组:
可选地,在一些实施方案中,L
3选自单键或如下基团所组成的组:
可选地,在一些实施方案中,X
1、X
2、X
3中至少有两个为N,且Y
1、Y
2和Y
3上总共连接有至少一个氰基和至少一个金刚烷基。
可选地,在一些更具体的实施方案中,Y
1和Y
2各自独立地选自如下基团所组成的组:
可选地,在一些更具体的实施方案中,Y
3选自如下基团所组成的组:
可选地,在一些实施方案中,Y
3至少连接一个氰基,即m
3+q
3≥1,和/或,Y
3至少连接一个金刚烷基,即n
3+t
3≥1。
可选地,在一些实施方案中,所述含氮化合物选自以下化合物组成的组:
下文中,将参照实施例详细描述本发明。然而,根据本说明书的实施例可被修改成各种其他形式,并且本说明书的范围不解释为受限于以下描述的实施例。提供本说明书的实施例是为了更完整地向本领域技术人员描述本说明书。
实施例:
下面所描述的合成例中,除非另有声明,否则所有的温度的单位为摄氏度。部分试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa ChemicalCompany,除非另有声明,否则使用时都没有经过进一步纯化。无水四氢呋喃,二氧六环,甲苯,乙醚是经过金属钠回流干燥得到。无水二氯甲烷和氯仿是经过氢化钙回流干燥得到。乙酸乙酯,石油醚,正己烷,N,N-二甲基乙酰胺和N,N-二甲基甲酰胺是经无水硫酸钠事先干燥使用。
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。玻璃器皿都是干燥过的。
在纯化时,色谱柱是硅胶柱,硅胶(100-200目)购于青岛海洋化工厂。
在各个合成例中,低分辨率质谱(MS)数据的测定条件是:Agilent 6120四级杆HPLC-M(柱子型号:Zorbax SB-C18,2.1×30mm,3.5微米,6min,流速为0.6mL/min。流动相:5%-95%(含0.1%甲酸的乙腈)在(含0.1%甲酸的水)中的比例),采用电喷雾电离(ESI),在210nm/254nm下,用UV检测。
核磁共振氢谱:布鲁克(Bruker)400MHz核磁仪,室温条件下,以CDCl
3或CD
2Cl
2为溶剂(以ppm为单位),用TMS(0ppm)作为参照标准。当出现多重峰的时候,将使用下面的缩写:s(singlet,单峰)、d(doublet,双峰)、t(triplet,三重峰)、m(multiplet,多重峰)。
目标化合物使用Agilent 1260pre-HPLC或Calesep pump 250pre-HPLC(柱子型号:NOVASEP 50/80mm DAC),在210nm/254nm用UV检测。
制备例1.化合物3的制备
Sub 2-B1的合成
将1-金刚烷醇(50.00g,328.45mmol)、3-羟基苯甲腈(39.12g,328.45mmol)、二氯甲烷(500mL)加入圆底烧瓶中,氮气保护下降温至-5℃、-5℃下滴加三氟甲磺酸(73.93g,492.67mmol),保温搅拌3h;向反应液中加入去离子水(300mL)水洗至pH=7,加入二氯甲烷(100mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体Sub 2-I-B1(33.28g,40.00%)。
将白色固体中间体Sub 2-I-B1(33.28g)加入烧瓶中,再加入乙酸钾,用DCM溶清,室温下滴加三氟甲磺酸酐,滴加完毕后加入吡啶,搅拌5h,向反应液中加入去离子水(300mL)水洗至pH=7,加入二氯甲烷(100mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用二氯甲烷和正庚烷进行重结晶提纯,得到白色固体Sub 2-B1(32.9g,收率65%)。
化合物3的合成
将2-氯-4,6-二苯基-1,3,5-三嗪(5.36g,20.00mmol)、Sub 2-B1(7.71g,20.00mmol)、四三苯基膦钯(0.23g,0.20mmol)、碳酸钾(5.57g,40.07mmol)、四丁基氯化铵(0.64g,2.00mmol)、甲苯(87mL)、乙醇(18mL)和去离子水(18mL)加入三口烧瓶中,氮气保护下升温至75-80℃,加热回流搅拌8h。反应结束后,溶液冷却至室温,加入甲苯和(100mL)萃取反应溶液,合并 有机相,无水硫酸镁干燥有机层,过滤,进行浓缩;粗品利用硅胶柱色谱进行提纯,得到固体化合物3(7.51g,80%)。MS(ESI,pos.ion)m/z:469.23[M+H]
+。
制备例2.化合物14的制备
以与制备例1中相同的方式制备化合物14,不同之处在于使用2-(4-联苯基)-4-氯-6-苯基-1,3,5三嗪(6.50g,20.00mmol)替代制备例1中2-氯-4,6-二苯基-1,3,5-三嗪,得到化合物14(7.72g,75%)。MS(ESI,pos.ion)m/z:545.26[M+H]
+。
中间体的制备
<1.sub 1-A1的合成>
<反应式1>
1>sub 1-I-A1合成
N
2保护下,向三口烧瓶中加入镁片(3.16g,131.85mmol)和四氢呋喃30ml溶液,体系温度升至60℃,向体系中加入碘(0.55g,2.19mmol)。化合物4-溴苯腈(20.0g,109.87mmol)在30ml的THF溶液中溶解完全,30min内慢慢向体系中进行滴加,滴加过程中控制温度在60℃。滴加完毕,在60℃温度条件下搅拌反应2h。常温冷却后将溶解在80mlTHF的2,4-二氯-6-苯基-1,3,5-三嗪(24.83g,109.87mmol)滴加到混合溶液中,搅拌3h后结束反应。反应结束后,加入甲苯和(200mL)萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,减压蒸馏进行浓缩;粗品利用硅胶柱色谱进行提纯,重结晶过滤得到固体中间体sub 1-I-A1(20.58g,64%)。
2>sub 1-II-A1合成
将sub 1-I-A1(20.00g,68.32mmol)、对氯苯硼酸(10.89g,69.68mmol)、四三苯基膦钯(1.57g,1.36mmol)、碳酸钾(18.89g,136.64mmol)、四丁基溴化铵(0.44g,1.36mmol)、甲苯(160mL)、乙醇(80mL)和去离子水(40mL)加入三口烧瓶中,氮气保护下升温至78℃,加热回流搅拌8h。反应结束后,溶液冷却至室温,加入甲苯和(200mL)萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,进行浓缩;粗品利用硅胶柱色谱进行提纯,得到固体中间体sub1-II-A1(16.87g,67%)。
3>sub 1-A1合成
将sub 1-II-A1(15.00g,40.67mmol)、联硼酸频哪醇酯(15.49g,61.00mmol)、Pd
2(dba)
3(0.37g,0.40mmol)、X-phos(0.38g,0.81mmol)、KOAc(7.81g,81.34mmol)加入1,4-二氧六环(150mL),在80℃温度条件下回流反应12h。当反应结束时,使用CH
2Cl
2和水进行提取。利用MgSO
4来干燥和浓缩有机层,对所生成的化合物进行硅胶柱及再结晶,得到固体中间体sub 1-A1(12.16g收率:65%)。
以sub 1-A1中相同的方式制备中间体sub 1-A2到sub 1-A17,不同之处在于使用原料1替代中间体sub 1-I-A1合成中的2-苯基-4,6-二氯-1,3,5-三嗪,使用原料2替代制备例1里sub 1-I-A1合成中4-溴苯腈。使用原料3替代制备例1里sub 1-II-A1合成中对氯苯硼酸。
表1
表1中部分原料的制备方法:
将溴苯(110g,0.72mol)和1-金刚烷醇(106g,0.72mol)加入圆底烧瓶中,用1.0L的DCM溶清,降温至0-5℃,滴加三氟甲磺酸酐(162.65g,1.08mol),保温搅拌3h;反应结束后向反应液中加入去离子水(1.0L/次)水洗至pH=7,分液,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体a-1,97g,纯度99.8%,收率47.6%。
以与中间体a-1相同的方式制备中间体b-1到c-1,不同之处在于使用以下表2中的原料4替代制备原料溴苯。
表2
制备例3.化合物46的制备
将中间体sub 1-A1(10.00g,21.72mmol)、a-1(6.32g,21.72mmol)、四三苯基膦钯(0.50g,0.43mmol)、碳酸钾(6.00g,43.44mmol)、四丁基溴化铵(0.07g,0.21mmol)、甲苯(80mL)、乙醇(40mL)和去离子水(20mL)加入三口烧瓶中,氮气保护下升温至78℃,加热回流搅拌15h。反应结束后,溶液冷却至室温,加入甲苯(100mL)萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,进行浓缩;粗品利用硅胶柱色谱进行提纯,得到固体化合物46(6.70g,57%)。MS(ESI,pos.ion)m/z:545.26[M+H]
+。
化合物46的核磁数据:
1H NMR(400MHZ,CD
2Cl
2)δ(ppm):8.90(d,2H),8.81(d,2H),8.75(d,2H),7.90(d,2H),7.85(d,2H),7.65-7.58(m,3H),7.36-7.30(m,4H),2.19(s,3H),1.96(s,6H),1.86-1.73(m,6H)。
以与制备例3相似的方法合成下表3中所示的化合物,不同之处在于使用中间体sub 1-A2~sub 1-A17替代中间体sub 1-A1,中间体a-1由以下原料5代替:
表3
上表3中部分化合物的核磁数据如下表4:
表4
制备例23.化合物591的制备
将中间体a-1(35.0g,120.1mmol)加入圆底烧瓶中,再将630mL的干燥THF加入到烧瓶中,用液氮给体系降温至-80℃至-90℃,然后开始滴加正丁基锂(8.46g,132.1mmol),滴毕,保温1h。滴加硼酸三甲酯(13.7g,14.7mL,132.1mmol),滴毕,温度保持在-80℃至-90℃,保温1h后,自然升至室温,反应结束,加入HCl的水溶液100mL(浓度为2mol/L),搅拌0.5h。加入二氯甲烷和水进行分液萃取,有机相洗至中性pH=7,合并有机相,无水MgSO
4干燥10min后,过滤,滤液旋干,用正庚烷打浆2次得到得到白色固体中间体a-1-1(20.9g,68%)。
将中间体a-1-1(19.5g,76.1mmol)、9,10-二溴蒽(32.0g,95.2mmol)、四三苯基膦钯(2.2g,1.9mmol)、碳酸钾(26.3g,190.4mmol)、四丁基溴化铵(0.3g,0.9mmol)、甲苯(250mL)、乙醇(60mL)和去离子水(60mL)加入三口烧瓶中,氮气保护下升温至76℃,加热回流搅拌15h。反应结束后,溶液冷却至室温,加入甲苯和水萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,进行浓缩;粗品利用硅胶柱色谱进行提纯,得到固体中间体a-1-2(19.5g,55%)。
将中间体a-1-2(24.0g,51.3mmol),联硼酸频哪醇酯(19.5g,77.0mmol)、Pd(dppf)Cl
2(0.7g,1.0mmol)、KOAc(10.0g,102.6mmol),加入1,4-二氧六环(200mL)在80℃温度条件下回流反应12h。当反应结束时,降温至室温,使用CH
2Cl
2和水进行萃取。利用MgSO
4来干燥有机相中的水分和浓缩有机层,对所生成的化合物进行硅胶柱层析,获得中间体a-1-3(16.1g,收率:61%)。
将中间体a-1-3(14.6g,28.4mmol)、3'-(4-氯-6-苯基-1,3,5-三嗪-2-基)-[1,1'-联苯]-4-甲腈(10.0g, 27.1mmol)、四三苯基膦钯(0.6g,0.5mmol)、碳酸钾(7.5g,54.2mmol)、四丁基溴化铵(0.2g,0.6mmol)、甲苯(120mL)、乙醇(30mL)和去离子水(30mL)加入三口烧瓶中,氮气保护下升温至76℃,加热回流搅拌15h。反应结束后,溶液冷却至室温,加入甲苯和水萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,进行浓缩;粗品利用硅胶柱色谱进行提纯,得到固体化合物591(13.1g,67%)。
MS(ESI,pos.ion)m/z:721.33[M+H]
+.
制备例24.化合物590的制备
在N
2保护下,向三口烧瓶中加入镁片(2.9g,120.9mmol)和四氢呋喃(THF)30mL,体系温度升至80℃,向体系中加入碘(0.6g,2.4mmol)、8-溴苯并呋喃并[2,3-B]吡啶(30.0g,120.9mmol)在30mL的THF溶剂中溶解完全,30min内慢慢向体系中进行滴加,滴加过程中控制温度在80℃。滴加完毕,在80℃温度条件下搅拌反应2h,得到混合溶液。常温冷却后将溶解在80mL THF的2,4,6-三氯-1,3,5-三嗪(22.3g,120mmol)滴加到混合溶液中,搅拌3h后结束反应,得到反应溶液。反应结束后,加入甲苯(200mL)萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,减压蒸馏进行浓缩;粗品利用硅胶柱色谱进行提纯,甲醇重结晶过滤得到固体中间体a-2-1(22.6g,59%)。
在N
2保护下,向三口烧瓶中加入镁片(1.6g,69.3mmol)和四氢呋喃(THF)10mL,体系温度升至80℃,向体系中加入碘(0.3g,1.4mmol)、b-1(30.0g,120.9mmol)在15mL的THF溶剂中溶解完全,30min内慢慢向体系中进行滴加,滴加过程中控制温度在80℃。滴加完毕,在80℃温度条件下搅拌反应2h,得到混合溶液。常温冷却后将溶解在50mL THF的a-I-1(22.0g,69.3mmol)滴加到混合溶液中,搅拌3h后结束反应,得到反应溶液。反应结束后,加入甲苯(200mL)萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,减压蒸馏进行浓缩;粗品利用硅胶柱色谱进行提纯,甲醇重结晶过滤得到固体中间体a-2-2(21.3g,54%)。
将中间体a-2-2(21.0g,6.8mmol)、4-氰基-4-联苯硼酸(8.4g,37.6mmol)、四三苯基膦钯(0.8g,0.7mmol)、碳酸钾(10.1g,73.7mmol)、四丁基溴化铵(0.12g,0.37mmol)、甲苯(160mL)、乙醇(80mL)和去离子水(40mL)加入三口烧瓶中,氮气保护下升温至76℃,加热回流搅拌 15h。反应结束后,溶液冷却至室温,加入甲苯和水萃取反应溶液,合并有机相,无水硫酸镁干燥有机层,过滤,进行浓缩;粗品利用硅胶柱色谱进行提纯,得到固体化合物590(17.0g,65%)。MS(ESI,pos.ion)m/z:712.30[M+H]
+.
制备例25~31:参考上述化合物的制备方法和操作过程,以采购获得的中间体为原料,还制备得到化合物55、化合物81、化合物216、化合物570、化合物577、化合物598、化合物619。
制备例25:化合物55参考化合物63的制备过程进行合成,得到固体化合物55(5.70g)MS(ESI,pos.ion)m/z:520.18[M+H]
+。
制备例26:化合物81参考化合物63的制备过程进行合成,得到固体化合物81(5.50g)MS(ESI,pos.ion)m/z:695.28[M+H]
+。
制备例27:化合物216参考化合物483的制备过程进行合成,得到固体化合物216(3.70g)MS(ESI,pos.ion)m/z:575.13[M+H]
+。
制备例28:化合物570参考化合物482的制备过程进行合成,得到固体化合物570(5.35g)MS(ESI,pos.ion)m/z:549.25[M+H]
+。
制备例29:化合物577参考化合物30的制备过程进行合成,得到固体化合物577(8.45g)MS(ESI,pos.ion)m/z:667.25[M+H]
+。
制备例30:化合物598参考化合物483的制备过程进行合成,得到固体化合物598(5.80g)MS(ESI,pos.ion)m/z:710.32[M+H]
+。
制备例31:化合物619参考化合物483的制备过程进行合成,得到固体化合物619(8.27g)MS(ESI,pos.ion)m/z:721.33[M+H]
+。
本发明实施方式还提供了一种有机电致发光器件,包括阳极、阴极以及介于阳极和阴极之间的功能层,功能层包括本发明的上述含氮化合物。
在一种具体实施方式中,功能层包括电子传输层,电子传输层包括本发明的上述含氮化合物。本发明含氮化合物作为电子元件的电子传输层材料时,可以提升器件的效率、寿命并降低工作电压。
在一种具体实施方式中,电子元件可以为有机电致发光器件。如图1所示,有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层320、电子阻挡层322、作为能量转化层的有机发光层330、空穴阻挡层341、电子传输层340和阴极200。其中,空穴传输层320、电子阻挡层322、作为能量转化层的有机发光层330、空穴阻挡层341、电子传输层340共同组成功能层300。
可选地,阳极100包括以下阳极材料,其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数,work function)材料。阳极材料具体实例包括:金属如镍、铂、钒、铬、铜、锌和金或它们的合金;金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);组合的金属和氧化物如ZnO:Al或SnO
2:Sb;或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺,但不限于此。优选包含氧化铟锡(铟锡氧化物,indium tin oxide)(ITO)作为阳极的透明电极。
可选地,空穴传输层320和电子阻挡层322分别包括一种或者多种空穴传输材料,空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物,本申请对此不做特殊的限定。例如,空穴传输层320可以由化合物NPB或化合物HT-01组成,电子阻挡层322可以包含化合物EB-01或TCTA。
可选地,有机发光层330可以由单一发光材料组成,也可以包括主体材料和掺杂材料。可选地,有机发光层330由主体材料和掺杂材料组成,注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子,激子将能量传递给主体材料,主体材料将能量传递给掺杂材料,进而使得掺杂材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料,本申请对此不做特殊的限制。在本申请的一种实施方式中,有机发光层330的主体材料可以为BH-01或α,β-AND。
有机发光层330的掺杂材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料,本申请对此不做特殊的限制。在本申请的一种实施方式中,有机发光层330的掺杂材料可以为BD-01。
电子传输层340可以为单层结构,也可以为多层结构,其可以包括一种或者多种电子传输材料,电子传输材料可以选自但不限于,苯并咪唑衍生物、恶二唑衍生物、喹喔啉衍生物或者其他电 子传输材料。在本申请的一种实施方式中,电子传输层材料含有本申请的有机化合物。
本申请中,阴极200可以包括阴极材料,其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于,金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金;或多层材料如LiF/Al、Liq/Al、LiO
2/Al、LiF/Ca、LiF/Al和BaF
2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地,如图1所示,在阳极100和空穴传输层320之间还可以设置有空穴注入层310,以增强向空穴传输层320注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料,本申请对此不做特殊的限制。例如,空穴注入层310可以由F4-TCNQ或m-MTDATA组成。
可选地,如图1所示,在阴极200和电子传输层340之间还可以设置有电子注入层350,以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料,或者可以包括碱金属与有机物的络合物。例如,电子注入层350可以包括Yb。
按照另一种实施方式,电子元件可以为光电转化器件。该光电转化器件可以包括相对设置的阳极和阴极,以及设于阳极和阴极之间的功能层;功能层包含本申请所提供的含氮化合物。
按照一种具体的实施方式,如图2所示,光电转化器件可包括依次层叠设置的阳极100、空穴传输层320、光电转化层360、电子传输层340和阴极200。其中,空穴传输层320、光电转化层360、电子传输层340组成功能层300。
可选地,光电转化器件可以为太阳能电池,尤其是可以为有机薄膜太阳能电池。举例而言,在本申请的一种实施方式中,太阳能电池可以包括依次层叠设置的阳极、空穴传输层、有机发光层、电子传输层和阴极,其中,电子传输层包含有本申请的有机化合物。
本申请第三方面提供一种电子装置包含本申请第二方面所述的电子元件。
按照一种实施方式,如图3所示,所述电子装置为第一电子装置400,该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置,例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式,如图4所示,所述电子装置为第二电子装置500,第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
下面结合合成实施例来具体说明本申请的有机化合物的合成方法,但是本申请并不因此而受到任何限制。
以下给出具体的有机电致发光器件制备实施例。
实施例1:蓝色有机电致发光器件的制作
通过以下过程制备阳极:将厚度为
的ITO基板切割成40mm×40mm×0.7mm的尺寸,采用光刻工序,将其制备成具有阴极搭接区域、阳极以及绝缘层图案的顶发射实验基板,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)的功函数和清洗实验基板。
在实验基板(阳极)上真空蒸镀m-MTDATA(4,4',4”-三(N-3-甲基苯基-N-苯基氨基)三苯胺)以形成厚度为
的空穴注入层(HIL),并且在空穴注入层上真空蒸镀NPB,以形成厚度为
的空穴传输层(HTL)。
在发光层上蒸镀本发明化合物1形成厚度为
的电子传输层(ETL),将Yb蒸镀在电子传输层上以形成厚度为
的电子注入层(EIL),然后将镁(Mg)和银(Ag)以1:10的蒸镀速率混合,真空蒸镀在电子注入层上,形成厚度为
的阴极。
其中,m-MTDATA、NPB、TCTA、α,β-ADN、BD-1以及CP-1的结构式如下:
实施例2-31
除了在形成电子传输层(ETL)时各自使用表5中所示的化合物以外,采用与实施例1相同的方法制作有机电致发光器件。
比较例1-比较例6
在所述比较例1~比较例6中,除了使用了化合物A、化合物B、化合物C、化合物E、化合物F和化合物G作为电子传输层替代化合物1之外,采用与实施例1相同的方法制造有机电致发光器件。
其中IVL数据对比的是在10mA/cm
2下的测试结果,寿命是20mA/cm
2电流密度下的测试结果。
表5实施例1-31和比较例1-6的器件性能
根据上述表5的结果可知,使用本发明的化合物制备的实施例1~31,与使用已公知的化合物A、化合物B、化合物C、化合物E、化合物F和化合物G的比较例1~比较例6相比,实施例1~31的有机电致发光器件的驱动电压降低约0.2V,发光效率(Cd/A)至少提高了12.7%,且器件寿命至少提高约为16%。
总而言之,在电子传输层(ETL)中使用本发明的化合物制备的有机电致发光器件可实现较高的发光效率,并且器件寿命会有明显提升。本发明的含氮化合物结构中通过连接基团将金刚烷基和腈基连接在含氮杂芳基母核上,高极性的氰基使得该部分结构具有高的偶极矩,从而使化合物极性提高,得到高电子迁移率的有机材料,将该化合物作为有电子元件的电子传输层时,可以提升器件的效率、寿命并降低工作电压。1-金刚烷基本身作为刚性大体积的多环烷烃结构,可以避免共轭平面的直接堆积形成π聚集,可以改善材料的成膜性能,同时使得整体的分子量和不对称性增强,提高分子的热稳定性,也对于材料的结晶性有一定改善,提升该化合物应用于有机电致发光器件时的稳定性,使器件寿命提高,且更易于量产使用;由实施例1~31与比较例4的测试数据可知,连接在化合物末端的1-金刚烷基,在提高化合物极性和热稳定性方面优于2-金刚烷基。
化合物的热稳定性试验
化合物在用于量产制备器件时,需要在蒸镀条件下长时间受热。若化合物在受热条件下分子结构的热稳定性差,则在长时间受热条件下化合物的纯度会下降,导致量产前中后期制备的器件性能差异较大。
本发明通过如下方法评估本发明的化合物在量产蒸镀时长时间受热下分子结构的稳定性:
在高真空环境(<10
-6Pa),以及
每秒的蒸镀速度对应的温度下,对本发明化合物和对比化合物D、化合物E、化合物A、化合物G分别进行200小时耐热实验(保温处理)。通过耐热实验前后的纯度下降值判断本公开的化合物在量产条件下的稳定性,纯度下降值(%)=受热前纯度(%)-热处理后纯度(%)。
对比化合物D、化合物G:
表6含氮化合物的试验温度和纯度下降值
根据表6可知,本公开的含氮化合物在受热后的纯度下降值均小于0.4%,其中大部分均小于0.3%。化合物纯度下降值超过1%时,会导致器件的效率和寿命发生明显降低;热不稳定的化合物在实际量产使用中,会导致量产前中后期制备的器件性能存在较大差异。本发明中,化合物的耐热实验证实其纯度下降值均小于0.4%,对比例化合物D、化合物E、化合物A和化合物G在蒸镀温度下纯度下降均超过2%,超过了1%的限度,因此相比于对比化合物而言,本公开的含氮化合物还具有优秀的量产热稳定性。
本领域技术人员在考虑说明书及实践这里公开的发明后,将容易想到本发明的其它实施方案。本申请旨在涵盖本发明的任何变型、用途或者适应性变化,这些变型、用途或者适应性变化遵循本发明的一般性原理并包括本发明未公开的本技术领域中的公知常识或惯用技术手段。说明书和实施例仅被视为示例性的,本发明的真正范围和精神由所附的权利要求指出。
Claims (18)
- 一种含氮化合物,其中,结构如式1所示:其中,X 1、X 2、X 3相同或不同,且分别独立地选自C(R 0)或N,且其中至少有一个为N;L 1、L 2和L 3彼此相同或不同,且分别独立地为:单键、碳原子数为6~30的取代或未取代的亚芳基、碳原子数为3~30的取代或未取代的亚杂芳基;Ar 1、Ar 2、Ar 3彼此相同或不同,且分别独立地选自碳原子数为6~30的取代或未取代的芳基、碳原子数为3~30的取代或未取代的杂芳基;Ad为1-金刚烷基;m 1~m 3以m i表示,n 1~n 3以n i表示,q 1~q 3以q i表示,t 1~t 3以t i表示;i为变量,其选自1、2或3;m i表示L i上带有的氰基的个数,n i表示L i上带有的Ad的个数,q i表示Ar i上带有的氰基的个数,t i表示Ar i上带有的Ad的个数;m i独立地选自0、1、2或3,当m i大于1时,任意两个m i相同或不同;ni独立地选自0、1、2或3,当n i大于1时,任意两个n i相同或不同;q i独立地选自0、1、2或3,当q i大于1时,任意两个q i相同或不同;t i独立地选自0、1、2或3,当t i大于1时,任意两个t i相同或不同;且m 1+m 2+m 3+q 1+q 2+q 3≥1,n 1+n 2+n 3+t 1+t 2+t 3≥1;各R 0彼此相同或不同,且各自独立地选自氢、氘、碳原子数为1-10的烷基、碳原子数为3-20的取代或未取代的杂芳基或者碳原子数为6-20的取代或未取代的芳基;R 0、L 1~L 3和Ar 1~Ar 3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为2-10的烯基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为5-10的环烯基、碳原子数为4-10的杂环烯基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基、碳原子数为6-18的芳氧基、碳原子数为6-18的芳硫基、碳原子数为6-18的芳基硅烷基、碳原子数为3-12的烷基硅烷基;所述基团A选自碳原子数为3-20的取代或未取代的杂芳基、碳原子数为6-20的取代或未取代的芳基,且所述基团A中的取代基选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基;任选地,任意两个相邻的取代基形成环。
- 根据权利要求1所述的含氮化合物,其中,所述X 1、X 2、X 3中至少有两个为N。
- 根据权利要求1或2所述的含氮化合物,其中,所述m 1+m 2+m 3+q 1+q 2+q 3为1、2或3,所述n 1+n 2+n 3+t 1+t 2+t 3为1或2。
- 根据权利要求1~3任一项所述的含氮化合物,其中,所述Ar 1、Ar 2、Ar 3相同或不同,且各自独立地选自如下式i-1至式i-15所示的基团所组成的组:G 1~G 5各自独立地选自N或者C(J 1),且G 1~G 5中至少一个选自N;当G 1~G 5中的两个以上选自C(J 1)时,任意两个J 1相同或者不相同;G 6~G 13各自独立地选自N或者C(J 2),且G 6~G 13中至少一个选自N;当G 6~G 13中的两个以上选自C(J 2)时,任意两个J 2相同或者不相同;G 14~G 23各自独立地选自N或者C(J 3),且G 14~G 23中至少一个选自N;当G 14~G 23中的两个以上选自C(J 3)时,任意两个J 3相同或者不相同;G 24~G 33各自独立地选自N或者C(J 4),且G 24~G 33中至少一个选自N;当G 24~G 33中的两个以上选自C(J 4)时,任意两个J 4相同或者不相同;G 34~G 37各自独立地选自N或者C(J 5),当G 34~G 37中的两个以上选自C(J 5)时,任意两个J 5相同或者不相同;Z 1选自氢、氘、卤素基团、氰基、碳原子数为3~8的烷基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、三苯基硅烷基;Z 2~Z 9、Z 21各自独立地选自:氢、氘、卤素基团、氰基、碳原子数为3~8的烷基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~6的 烷氧基、碳原子数为1~6的烷硫基、三苯基硅烷基、碳原子数为3~18的杂芳基;Z 10~Z 20、J 1~J 5各自独立地选自:氢、氘、卤素基团、氰基、碳原子数为3~8的烷基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、三苯基硅烷基、碳原子数为6~18的芳基、碳原子数为3~18的杂芳基;任选地,两个相邻的Z 19相互连接形成5~10元芳环或5~10元杂芳环;任选地,两个相邻的Z 20相互连接形成5~10元芳环或5~10元杂芳环;h 1~h 21以h k表示,Z 1~Z 21以Z k表示,k为变量,表示1~21的任意整数,h k表示取代基Z k的个数;其中,当k选自5或者17时,h k选自1、2或者3;当k选自2、7、8、12、15、16、18或者21时,h k选自1、2、3或者4;当k选自1、3、4、6、9或者14时,h k选自1、2、3、4或者5;当k为13时,h k选自1、2、3、4、5或者6;当k选自10或者19时,h k选自1、2、3、4、5、6或者7;当k为20时,h k选自1、2、3、4、5、6、7或者8;当k为11时,h k选自1、2、3、4、5、6、7、8或9;且当h k大于1时,任意两个Z k相同或者不相同;K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 23Z 24);其中,Z 22、Z 23、Z 24各自独立地选自:碳原子数为6~18的芳基、碳原子数为3~18的杂芳基、碳原子数为1~6的烷基或碳原子数为5~10的环烷基,或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为5~13的饱和或不饱和的环;K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 26Z 27);其中,Z 25、Z 26、Z 27各自独立地选自:碳原子数为6~18的芳基、碳原子数为3~18的杂芳基、碳原子数为1~6的烷基或碳原子数为5~10的环烷基,或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为5~13的饱和或不饱和的环。
- 根据权利要求1~4任一项所述的含氮化合物,其中,所述Ar 1、Ar 2、Ar 3相同或不同,且各自独立地选自碳原子数为6~25的取代或未取代的芳基、碳原子数为5~20的取代或未取代的杂芳基;可选地,Ar 1~Ar 3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为3~8的烷基硅烷基、三苯基硅烷基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~4的烷氧基、碳原子数为1~4的烷硫基、碳原子数为6~15的芳氧基、碳原子数为6~15的芳硫基;所述基团A选自碳原子数为5~18的取代或未取代的杂芳基或者碳原子数为6~20的取代或未取代的芳基,且所述基团A中的取代基选自氘、卤素基团、氰基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基;任选地,任意两个相邻的取代基形成5到10元脂肪族环或5到13元芳香环。
- 根据权利要求1~8任一项所述的含氮化合物,其中,所述L 1、L 2、L 3相同或不同,且分别独立地选自单键或者选自式j-1至j-14所示的基团所组成的组:Q 1~Q 5各自独立地选自N或者C(J 5),且Q 1~Q 5中至少一个选自N;当Q 1~Q 5中的两个或者两个以上选自C(J 5)时,任意两个J 5相同或者不相同;Q 6~Q 13各自独立地选自N或者C(J 6),且Q 6~Q 13中至少一个选自N;当Q 6~Q 13中的两个或者两个以上选自C(J 6)时,任意两个J 6相同或者不相同;Q 14~Q 23各自独立地选自N、C或者C(J 7),且Q 14~Q 23中至少一个选自N;当Q 14~Q 23中的两个或者两个以上选自C(J 7)时,任意两个J 7相同或者不相同;Q 24~Q 33各自独立地选自N、C或者C(J 8),且Q 24~Q 33中至少一个选自N;当Q 24~Q 33中的两个或者两个以上选自C(J 8)时,任意两个J 8相同或者不相同;E 1~E 14、J 5~J 8分别独立地选自:氢、氘、卤素基团、氰基、碳原子数为3~20的杂芳基、碳原子数为6~20的芳基、碳原子数为3~8的烷基硅烷基、三苯基硅烷基、碳原子数为1~6的烷基、碳原子数为1~6的卤代烷基、碳原子数为2~6的烯基、碳原子数为5~10的环烷基、碳原子数为2~6的杂环烷基、碳原子数为1~6的烷氧基、碳原子数为1~6的烷硫基、碳原子数为6~18的芳氧基、碳原子数为6~18的芳硫基;e 1~e 14以e r表示,E 1~E 14以E r表示,r为变量,表示1~14的任意整数,e r表示取代基E r的数量;当r选自1、2、3、4、5、6、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9或12时,e r选自1、2、3、4、5、6或者7;当r选自8或10时,e r选自1、2、3、4、5、6、7或者8;当e r大于1时,任意两个E r相同或者不相同;K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19);其中,各E 15、E 16、E 17、E 18和E 19分别独立地选自:氢、碳原子数为6~20的芳基、碳原子数为3~20的杂芳基、碳原子数为1~6的烷基、碳原子数为2~6的烯基、碳原子数为5~10的环烷基、碳原子数为2~6的杂环烷基;或者,任选地,上述E 16和E 17相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环;或者,任选地,上述E 18和E 19相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环;各K 4独立地选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24);其中,各E 20、E 21、E 22、E 23、E 24分别独立地选自:氢、碳原子数为6~20的芳基、碳原子数为3~20的杂芳基、碳原子数为1~6的烷基、碳原子数为2~6的烯基、碳原子数为5~10的环烷基、碳原子数为2~10的杂环烷基;或者,任选地,上述E 21和E 22相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环;或者,任选地,上述E 23和E 24相互连接以与它们共同连接的原子形成5到13元脂肪族环或5到13元芳香环。
- 根据权利要求1~9任一项所述的含氮化合物,其中,所述L 1、L 2、L 3相同或不同,且各自独立地选自单键或碳原子数为6~20的取代或未取代的芳基、碳原子数为5~18的取代或未取代的杂芳基;可选地,L 1、L 2、L 3中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、基团A、碳原子数为3~8的三烷基硅基、三苯基硅基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基、碳原子数为5~10的环烷基、碳原子数为1~4的烷氧基、碳原子数为1~4的烷硫基、碳原子数为6~15的芳氧基、碳原子数为6~15的芳硫基;所述基团A选自碳原子数为5~12的取代或未取代的杂芳基或碳原子数为6~15的取代或未取代的芳基,且所述基团A中的取代基选自氘、 卤素基团、氰基、碳原子数为1~4的烷基、碳原子数为1~4的卤代烷基;任选地,任意两个相邻的取代基形成5到10元脂肪族环或5到13元芳香环。
- 根据权利要求1~10任一项所述的含氮化合物,其中,所述L 1、L 2、L 3相同或不同,且分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚萘基、取代或未取代的亚芴基、取代或未取代的螺[环戊烷-1,9’-芴]亚基、取代或未取代的螺[环己烷-1,9’-芴]亚基、取代或未取代的亚菲咯啉基、取代或未取代的亚喹啉基、取代或未取代的亚异喹啉基、取代或未取代的亚吡啶基、取代或未取代的亚咔唑基、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、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的苯并菲亚基,或者为上述亚基中两者或三者通过单键连接所形成的亚基基团;可选地,所述L 1、L 2、L 3中的取代基彼此相同或不同,且各自独立地选自氘、氟、氯、氰基、甲基、乙基、异丙基、正丙基、叔丁基、甲氧基、乙氧基、三氟甲基、三甲基硅烷基、苯基、联苯基、萘基、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基所组成的组。
- 一种电子元件,其特征在于,包括相对设置的阳极和阴极,以及设于所述阳极和所述阴极之间的功能层;所述功能层包括电子传输层,所述电子传输层包括权利要求1~15中任一项所述的含氮化合物。
- 根据权利要求16所述的电子元件,其特征在于,所述电子元件为有机电致发光器件或光电转化器件。
- 一种电子装置,其特征在于,包括权利要求16或17所述的电子元件。
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