WO2022188514A1 - 一种有机化合物及包含其的电子元件和电子装置 - Google Patents
一种有机化合物及包含其的电子元件和电子装置 Download PDFInfo
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- WO2022188514A1 WO2022188514A1 PCT/CN2021/142183 CN2021142183W WO2022188514A1 WO 2022188514 A1 WO2022188514 A1 WO 2022188514A1 CN 2021142183 W CN2021142183 W CN 2021142183W WO 2022188514 A1 WO2022188514 A1 WO 2022188514A1
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- 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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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/76—Dibenzothiophenes
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- 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
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- Y02E10/549—Organic PV cells
Definitions
- the present application relates to the technical field of organic electroluminescence, and in particular, to an organic compound and electronic components and electronic devices comprising the same.
- This type of electronic device usually includes a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode.
- the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
- the mechanism of organic electroluminescence is that driven by an external electric field, the cathode and anode of the light-emitting device inject electrons and holes into the organic functional thin film layer between the electrodes, respectively, and the electrons injected by the cathode and the holes injected by the anode are transported from the electrons respectively.
- the layer and the hole transport layer migrate to the light-emitting layer and approach each other under the Coulomb attraction, and part of the electrons and holes are finally captured by each other to form excitons.
- the excitons migrate under the action of the electric field, transfer energy to the light-emitting layer, and make them excited to transition from the ground state to the excited state.
- the development of stable and efficient hole transport materials has important practical application value for reducing the driving voltage of the device, improving the luminous efficiency of the device, and prolonging the life of the device.
- An object of the present disclosure is to provide an organic compound, which can improve the luminous efficiency of a device and prolong the life of the device, and an electronic component and electronic device including the same.
- a first aspect of the present application provides an organic compound having the structure shown in formula 1:
- Ar 1 is selected from one of formula I, formula II, formula III and formula IV:
- Ar 2 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
- L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are the same or different, and are independently selected from deuterium, halogen, cyano, and alkyl groups having 1 to 5 carbon atoms. , a trialkylsilyl group with a carbon number of 3 to 12, a triphenylsilyl group, an aryl group with a carbon number of 6 to 12, and a heteroaryl group with a carbon number of 3 to 12;
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are represented by R i
- n 1 to n 8 are represented by n i
- n i is the number of R i s
- i is a variable , representing 1, 2, 3, 4, 5, 6, 7 and 8, when i is 1, 3, 5, 7, n i is selected from 0, 1, 2, 3 or 4; when i is 2, 4 , 6, 8, n i is selected from 0, 1, 2 or 3; and when n i is greater than 1, any two R i are the same or different;
- the substituents in Ar 2 , L 1 and L 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group , an alkyl group with 1 to 5 carbon atoms, an aryl group with 6 to 12 carbon atoms optionally substituted by an alkyl group with 1 to 5 carbon atoms, and a heteroaryl group with 3 to 12 carbon atoms , haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms; optionally, in Ar 2 , any two adjacent The substituents form 3-15-membered rings.
- the organic compound of the present application is a triarylamine structure connected to a specific aromatic group, and the triarylamine structure includes a 1,8-diphenyl-substituted naphthyl group, and the di-substituted naphthyl group has a large steric hindrance and is a necessary group
- One of the groups can adjust the spatial configuration of organic compound molecules, thereby effectively avoiding stacking between molecules and improving film formation.
- the electron distribution effect of this group can also improve hole mobility.
- the organic compound of the triarylamine structure also contains a cycloalkyl spiro fluorenyl group, which has high hole mobility and good stability compared with the fluorenyl group.
- the compounds of the present application have excellent hole transport efficiency and film-forming properties, and can be used in organic electroluminescent devices to significantly improve the luminous efficiency and lifetime of the devices.
- a second aspect of the present application provides an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the above-mentioned organic compound.
- a third aspect of the present application provides an electronic device, including the above electronic component.
- FIG. 1 is a schematic structural diagram of an embodiment of the organic electroluminescent device of the present application.
- FIG. 2 is a schematic structural diagram of an embodiment of the electronic device of the present application.
- anode 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 330, electron blocking layer; 340, organic electroluminescence layer; 350, electron transport layer; 360, electron An injection layer; 400, an electronic device.
- a first aspect of the present application provides an organic compound having the structure shown in formula 1:
- Ar 1 is selected from one of formula I, formula II, formula III and formula IV:
- Ar 2 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
- L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are the same or different, and are independently selected from deuterium, halogen, cyano, and alkyl groups having 1 to 5 carbon atoms. , a trialkylsilyl group with a carbon number of 3 to 12, a triphenylsilyl group, an aryl group with a carbon number of 6 to 12, and a heteroaryl group with a carbon number of 3 to 12;
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are represented by R i
- n 1 to n 8 are represented by n i
- n i is the number of R i s
- i is a variable , representing 1, 2, 3, 4, 5, 6, 7 and 8, when i is 1, 3, 5, 7, n i is selected from 0, 1, 2, 3 or 4; when i is 2, 4 , 6, 8, n i is selected from 0, 1, 2 or 3; and when n i is greater than 1, any two R i are the same or different;
- the substituents in Ar 2 , L 1 and L 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group , an alkyl group with 1 to 5 carbon atoms, an aryl group with 6 to 12 carbon atoms optionally substituted by an alkyl group with 1 to 5 carbon atoms, and a heteroaryl group with 3 to 12 carbon atoms , haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms; optionally, in Ar 2 , any two adjacent
- the substituents of 1 form a 3-15 membered ring, for example, any two adjacent substituents form a cyclopentyl group, a cyclohexyl group, and the like.
- each q is independently 0, 1, 2 or 3
- each R is independently selected from hydrogen, deuterium, fluorine, chlorine
- formula Q-1 represents that there are q substituents R" on the benzene ring.
- each R" can be the same or different, and the options of each R" do not affect each other;
- formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the R" on the two benzene rings " The number q of substituents can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.
- an aryl group having 6 to 12 carbon atoms optionally substituted by an alkyl group having 1 to 5 carbon atoms means that the aryl group may be replaced by one of the alkyl groups having 1 to 5 carbon atoms.
- One or more substitutions may not be substituted by an alkyl group having 1 to 5 carbon atoms, and when the number of substituents on the aryl group is greater than or equal to 2, the substituents may be the same or different.
- substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc).
- substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
- substituent namely Rc
- Rc can be, for example, deuterium, halogen group, cyano group, trialkylsilyl group with 3 to 12 carbon atoms, alkyl group with 1 to 5 carbon atoms, optionally replaced by carbon atoms aryl group with 6-12 carbon atoms substituted by alkyl group of 1-5, heteroaryl group with 3-12 carbon atoms, haloalkyl group with 1-10 carbon atoms, 3- Cycloalkyl of 10, alkoxy of 1 to 10 carbon atoms, triarylsilyl, optionally, any two of the substituents are connected to each other to form a 3- to 15-membered atom together with the atoms to which they are connected.
- the "substituted" functional group may be substituted by one or more than two substituents in the above Rc; when two substituents Rc are attached to the same atom, the two substituents Rc may exist independently or Connected to each other to form a ring with the atoms; when there are two adjacent substituents Rc on a functional group, the adjacent two substituents Rc may exist independently or be condensed to form a ring with the functional group to which they are connected.
- the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 2 is selected from a substituted arylene group having 12 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 12. For example: Ar 2 is Then the number of carbon atoms is 10; L 2 is Its carbon number is 12.
- hetero means that a functional group includes at least one heteroatom such as B, N, O, S, P, Si or Se and the remaining atoms are carbon and hydrogen.
- alkyl may include straight-chain or branched-chain alkyl groups.
- An alkyl group may have 1 to 5 carbon atoms, and herein, a numerical range such as “1 to 5" refers to each integer in the given range;
- Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
- an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
- Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation.
- the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
- aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, Base et al.
- biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.
- the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
- the substituted aryl group may be one or more than two hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, a tert-butyl group, a trifluoromethyl group, a heteroaryl group, a trimethyl silicon group group, alkyl, cycloalkyl, alkoxy, alkylthio and other groups.
- a group such as a deuterium atom, a halogen group, a cyano group, a tert-butyl group, a trifluoromethyl group, a heteroaryl group, a trimethyl silicon group group, alkyl, cycloalkyl, alkoxy, alkylthio and other groups.
- the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents.
- the total number of carbon atoms of the substituents is 18.
- heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms can be B, O, N, P At least one of , Si, Se, and S.
- 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.
- heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thieny
- 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.
- the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
- a substituted heteroaryl group may be one or more than two hydrogen atoms in the heteroaryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trimethylsilyl group, an alkyl group , 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, a trimethylsilyl group, an alkyl group , cycloalkyl, alkoxy, alkylthio and other groups are substituted.
- the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
- the number of carbon atoms of the aryl group as a substituent may be 6-12, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, and specific examples of the aryl group as a substituent include But not limited to, phenyl, biphenyl, naphthyl.
- the number of carbon atoms of the heteroaryl group as a substituent may be 3 to 12, for example, the number of carbon atoms may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, as a substituent
- Specific examples of heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinoline Linyl.
- halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
- trialkylsilyl includes, but is not limited to, trimethylsilyl, triethylsilyl, and the like.
- a non-positioned connecting bond refers to a 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, and the meaning it represents, Any possible connection modes shown by formula (X'-1) to formula (X'-4) are included.
- a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system.
- the substituent R' group represented by the formula (Y) is connected to the quinoline ring through a non-positioning link, and the meanings it represents include the formula (Y-1) ⁇ Any possible connection mode shown by formula (Y-7).
- L 1 and L 2 are the same or different, and are each independently selected from a single bond, or from the group consisting of groups represented by formula i-1 to formula i-7:
- M 1 is selected from single bond or represents a chemical bond
- G 1 to G 13 are the same or different, and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 5 carbon atoms, and alkyl halide having 1 to 10 carbon atoms radicals, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, aryl groups with 3 to 12 carbon atoms, and heteroaryl groups with 3 to 12 carbon atoms;
- g 1 to g 13 are represented by gr
- G 1 to G 13 are represented by Gr
- r is a variable, representing any integer from 1 to 13, and gr represents the number of substituents Gr; when r is selected from 1, 2, When 3, 4, 5, 6, 9 or 13, g r is selected from 1, 2, 3 or 4; when r is selected from 7, g r is selected from 1, 2 or 3; when r is selected from 8, g r is selected from 1, 2, 3, 4 or 5; when r is selected from 10, g r is selected from 1, 2, 3, 4, 5 or 6; when r is selected from 11 or 12, g r is selected from 1 , 2, 3, 4, 5, 6, 7 or 8; when gr is greater than 1, any two Gr are the same or different.
- L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms, or a substituted or unsubstituted heteroarylene group with 3-20 carbon atoms Aryl.
- L 1 and L 2 are each independently selected from single bonds, substitutions with carbon atoms of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 Or unsubstituted arylene, or substituted with 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 or unsubstituted heteroarylene.
- L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
- L 1 and L 2 are each independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted anthracylene, substituted or unsubstituted terphenylene.
- the substituents in L 1 and L 2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, pyridyl, phenyl, Naphthyl, Biphenyl.
- L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted group P, and the unsubstituted group P is selected from the following groups:
- the substituted group P has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl group, pyridyl group, phenyl group, naphthyl group, biphenyl group, and when the number of substituent groups is greater than 1, each substituent group is the same or different.
- L 1 and L 2 are each independently selected from the group consisting of a single bond and the following groups:
- Ar 2 is selected from the group consisting of groups represented by formula j-1 to formula j-9:
- M 2 is selected from single bond or
- E 1 is selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, and ring with 3-10 carbon atoms Alkyl, triphenylsilyl;
- E 2 to E 9 and E 18 are the same or different, and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, and an alkyl group having 1 to 5 carbon atoms.
- E 10 to E 17 are the same or different, and are each independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, alkyl having 1 to 5 carbon atoms, and alkyl halide having 1 to 5 carbon atoms base, cycloalkyl group with 3-10 carbon atoms, aryl group with 6-12 carbon atoms, heteroaryl group with 3-12 carbon atoms;
- e 1 to e 18 are represented by e k
- E 1 to E 18 are represented by E k
- k is a variable, representing any integer from 1 to 18, and e k represents the number of substituents E k ; wherein, when k is selected from 8 or 15, ek is selected from 1, 2 or 3; when k is selected from 2, 5, 6, 11, 13, 14 or 18, ek is selected from 1, 2, 3 or 4; when k is selected from 1 , 3, 4, 7 or 9, e k is selected from 1, 2, 3, 4 or 5; when k is 12, e k is selected from 1, 2, 3, 4, 5 or 6; when k is selected from When 10 or 16, ek is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 17, ek is selected from 1, 2, 3, 4, 5, 6, 7 or 8; and When e k is greater than 1, any two E k are the same or different;
- K 1 is selected from O, S, N(E 19 ), C(E 20 E 21 ), Si(E 22 E 23 ); wherein, E 19 , E 20 , E 21 , E 22 , E 23 are the same or different, and are independently selected from alkyl groups with 1 to 5 carbon atoms, aryl groups with 6 to 12 carbon atoms optionally substituted by methyl, ethyl, isopropyl and tert-butyl groups, and aryl groups with carbon atoms of 6 to 12.
- E 20 and E 21 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms
- E 22 and E 23 are connected to each other to form a saturated or unsaturated ring with the atoms they are commonly connected to.
- the atoms to which they are connected together form a saturated or unsaturated ring with 3 to 15 carbon atoms;
- K 2 is selected from single bond, O, S, N(E 24 ), C(E 25 E 26 ), Si(E 27 E 28 ); wherein, E 24 , E 25 , E 26 , E 27 , and E 28 are the same or different, and each is independently selected from an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms.
- the ring formed by the interconnection of two groups in each group may be carbon A saturated or unsaturated ring having 3 to 15 atoms.
- formula j-8 when both K 2 and M 2 are single bonds, E 16 is hydrogen, and K 1 is C (E 20 E 21 ), when E 20 and E 21 are connected to each other to form a 5-membered ring with the atoms they are commonly connected to , the formula j-8 is Similarly, formula j-8 can also represent That is, E 20 and E 21 are interconnected to form a partially unsaturated 13-membered ring with the atoms to which they are commonly attached.
- Ar 2 is selected from a substituted or unsubstituted aryl group with 6-25 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3-18 carbon atoms.
- Ar 2 is selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 substituted or unsubstituted aryl, or substituted or unsubstituted with 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms Heteroaryl.
- Ar 2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, Substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted or unsubstituted 9,9'-spirobifluorenyl.
- the substituents in Ar 2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl , pyridyl, carbazolyl, triphenylsilyl.
- Ar 2 is selected from substituted or unsubstituted group T, and unsubstituted group T is selected from the group consisting of:
- the substituted group T has one or more than two substituents, each of which is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tertiary Butyl group, pyridyl group, carbazolyl group, phenyl group, naphthyl group, biphenyl group, triphenylsilyl group, and when the number of substituent groups is greater than 1, each substituent group is the same or different.
- substituents each of which is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tertiary Butyl group, pyridyl group, carbazolyl group, phenyl group, naphthyl group, biphenyl group, triphenylsilyl group, and when the number of substituent groups is greater than 1, each substituent group is the same or different.
- Ar is selected from the group consisting of :
- Ar 2 is selected from the group that the following groups are formed:
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are the same or different, and are independently selected from deuterium, fluorine, cyano, Methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyrimidinyl, pyridyl, quinolyl, carbazolyl, dibenzofuranyl, Dibenzothienyl, triphenylsilyl.
- the organic compound is selected from the group consisting of:
- a second aspect of the present application provides an electronic component for realizing photoelectric conversion or electro-optical conversion.
- the electronic component includes an anode and a cathode disposed opposite to each other, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound of the present application.
- the electronic element may be an organic electroluminescence device or a photoelectric conversion device.
- the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode and the cathode.
- the functional layer 300 includes a hole injection layer 310, a hole Transport layer 320, electron blocking layer 330, organic electroluminescence layer 340, electron transport layer 350 and electron injection layer 360; hole injection layer 310, hole transport layer 320, electron blocking layer 330, organic electroluminescence layer 340, The electron transport layer 350 and the electron injection layer 360 may be sequentially formed on the anode 100 , and the hole transport layer 320 may contain the organic compound described in the first aspect of the present application, preferably at least one of compounds 1-608.
- 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. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
- ITO indium tin oxide
- hole transport layer 320 may include one or more hole transport materials.
- the hole transport layer 320 is composed of the organic compound provided by the present application.
- the electron blocking layer 330 is used to block electrons transmitted from the organic electroluminescent layer 340, thereby ensuring that electrons and holes can be recombined in the organic electroluminescent layer 340 efficiently; at the same time, the electron blocking layer 330 can also block The excitons diffused from the organic electroluminescent layer 340 reduce triplet quenching of the excitons, thereby ensuring the luminous efficiency of the organic electroluminescent device.
- the compound of the electron blocking layer 330 has a relatively high LUMO value, which can effectively block the transmission and diffusion of electrons and excitons from the organic electroluminescent layer 340 to the direction of the anode 100 .
- the electron blocking layer 330 may be a compound having an aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic nitrogen-containing derivative or other materials, which are not particularly limited in this application.
- the electron blocking layer 330 may be composed of EB-01.
- the material of the organic electroluminescent layer 340 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 organic electroluminescent layer 340 may be composed of BH-01 and BD-01.
- the electron transport layer 350 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 benzimidazole derivatives, oxadiazole derivatives, quinoxaline Derivatives or other electron transport materials, which are not specifically limited in this application.
- the electron transport layer 350 may be composed of ET-06 and LiQ.
- the cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
- cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto. It is preferable to include a metal electrode including silver and magnesium as the cathode 200 .
- 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 is composed of F4-TCNQ.
- an electron injection layer 360 may also be disposed between the cathode 200 and the electron transport layer 350 to enhance the capability of injecting electrons into the electron transport layer 350 .
- the electron injection layer 360 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 360 is LiQ.
- a third aspect of the present application provides an electronic device including the electronic component described in the present application.
- the electronic device provided by the present application is a first electronic device 400
- the first electronic device 400 includes any organic electroluminescent device described in the above organic electroluminescent device embodiment.
- the electronic device may be a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects, and details are not described herein again.
- the IMA-X listed in Table 1 was synthesized with reference to the method of IMA-1, and the raw material 1 was used to replace 1-bromo-3-iodobenzene, wherein the main raw materials used, the synthesized intermediates and their yields were shown in Table 1.
- the IMC-X listed in table 3 is synthesized with reference to the method for IMC-1, the difference is that raw material 3 is used to replace 2-bromofluorene, wherein, the main raw material used, the synthetic intermediate and the yield thereof are shown in table 3 .
- the intermediate shown in Table 5 is synthesized with reference to the method of IM BM-1, the difference is that raw material 6 is used to replace IM B-1, wherein, raw material 6, the synthesized intermediate and the yield thereof are as shown in Table 5.
- Extract and separate the organic phase with toluene 500 mL
- IM EN-X listed in table 7 is synthesized with reference to the method for IM EN-1, the difference is that the raw material 9 is used to replace the 3-bromophenylboronic acid, and the raw material 10 is used to replace the 2-bromophenanthrene, wherein the main raw materials used, the synthetic The intermediates and their yields are shown in Table 7.
- the organic phase was separated by extraction with dichloromethane and water, and the organic phase was dried using anhydrous magnesium sulfate. After filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was recrystallized using a dichloromethane/n-heptane system to obtain IM AZ-1 (11.00 g, 76% yield).
- the IM AZ-Y listed in Table 8 is synthesized with reference to the method of IM AZ-1, the difference is that the raw material 11 is used to replace the IM A-1, and the raw material 12 is used to replace the aniline, wherein, the main raw material used, the synthetic intermediate and The yields thereof are shown in Table 8.
- IM AZ-Y listed in Table 9 is synthesized with reference to the method of IM AZ-1, the difference is that raw material 13 is used to replace aniline, and raw material 14 is used to replace IM A-1, wherein the main intermediate used, the synthesized intermediate and their yields are shown in Table 9.
- the compound Y listed in Table 10 is synthesized with reference to the method of compound 25, the difference is that the raw material 15 is used to replace IM AZ-1, and the raw material 16 is used to replace IM B-1, wherein the main raw materials used, the synthesized compounds and their yields are used.
- the rates and mass spectra are shown in Table 10.
- the anode ITO substrate was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns.
- N 2 plasma was used for surface treatment to increase the work function of the anode (experimental substrate), and organic solvent was used to clean the surface of the ITO substrate to remove scum and oil stains on the surface of the ITO substrate.
- HIL hole injection layer
- EB-01 was vacuum evaporated on the hole transport layer to form a thickness of The electron blocking layer (EBL).
- EBL electron blocking layer
- EML electron blocking layer
- ET-06 and LiQ are mixed in a weight ratio of 1:1, and can be formed by a vacuum evaporation process Thick electron transport layer (ETL). Subsequently, LiQ was evaporated on the electron transport layer to form a thickness of the electron injection layer (EIL).
- ETL Thick electron transport layer
- Magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1:9 and vacuum-evaporated on the electron injection layer (EIL) to form a thickness of the cathode.
- a layer thickness of vapor deposition as a protective layer on the cathode is of CP-05 to form a capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.
- a blue organic electroluminescent device was prepared in the same manner as in Example 1, except that the compounds in Table 13 were respectively used instead of Compound 25 in Example 1 when forming the hole transport layer.
- a blue organic electroluminescent device was prepared by the same method as in Example 1, except that Compound A, Compound B, and Compound C were respectively used instead of Compound 25 in Example 1 when forming the hole transport layer.
- the operating voltage of the organic electroluminescent device is reduced by at least 4.0% compared with the device Comparative Examples 1-3 corresponding to the compound of the hole transport layer in Examples 1-93 and the known compounds , the luminous efficiency (Cd/A) is increased by at least 10.1%, the external quantum efficiency is increased by at least 10.4%, and the lifetime is increased by at least 13%. Therefore, the compound of the present application has the characteristics of improving both the luminous efficiency and the lifetime. It can be seen from the above data that using the organic compound of the present application as the hole transport layer of the electronic device can significantly improve the luminous efficiency (Cd/A), external quantum efficiency (EQE) and lifetime (T95) of the electronic device. Therefore, organic electroluminescent devices with high luminous efficiency and long lifetime can be prepared by using the organic compounds of the present application in the hole transport layer.
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Abstract
本申请涉及一种有机化合物及其电子元件和电子装置,属于有机电致发光技术领域。所述有机化合物的具有式(1)所示的结构,该有机化合物具有优异的光电性能,可以提高器件的发光效率、外量子效率和使用寿命,并能够降低工作电压。
Description
相关申请的交叉引用
本申请要求于2021年3月12日递交的申请号为202110304679.3的中国专利申请的优先权,在此引用上述中国专利申请的内容全文以作为本申请的一部分。
本申请涉及有机电致发光技术领域,具体地涉及一种有机化合物及包含其的电子元件和电子装置。
随着电子技术的发展和材料科学的进步,用于实现电致发光或者光电转化的电子器件的应用范围越来越广泛。该类电子器件通常包括相对设置的阴极和阳极,以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成,且一般包括能量转化层、位于能量转化层与阳极之间的空穴传输层、位于能量转化层与阴极之间的电子传输层。
一般地,有机电致发光的机理是在外加电场驱动下,发光器件的阴极和阳极分别向电极间的有机功能薄膜层注入电子和空穴,阴极注入的电子和阳极注入空穴分别从电子传输层和空穴传输层向发光层迁移,在Coulomb引力下彼此靠近,其中一部分的电子和空穴最后相互俘获而形成激子。激子在电场的作用下迁移,将能量传递给发光层,并使其受到激发从基态跃迁至激发态,当受激发的分子从激发态回到基态时辐射跃迁而发光。随着市场的不断发展,对有机电致发光器件的发光效率、使用寿命等性能的要求越来越高。
目前报道的空穴传输材料由于玻璃化温度较低,在材料使用过程中,反复充电放电,材料容易结晶,薄膜的均一性被破坏,从而影响材料使用寿命。因此,开发稳定高效空穴传输材料,对降低器件的驱动电压,提高器件的发光效率,延长器件的寿命,具有很重要的实际应用价值。
发明内容
本公开的目的在于提供一种有机化合物及包含其的电子元件和电子装置,所述有机化合物可提高器件发光效率并延长器件寿命。
本申请的第一方面提供一种有机化合物,其具有式1所示的结构:
其中,Ar
1选自式I、式II、式III和式IV中的一个:
Ar
2选自碳原子数为6~40的取代或未取代的芳基、或者碳原子数为3~30的取代或未取代的杂芳基;
L
1和L
2相同或不同,且各自独立地选自单键、碳原子数为6~30的取代或未取代的亚芳基、或者碳原子数为3~30的取代或未取代的亚杂芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8相同或不同,且分别独立地选自氘、卤素、氰基、碳原子数为1~5的烷基、碳原子数为3~12的三烷基硅基、三苯基硅基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8以R
i表示,n
1~n
8以n
i表示,n
i表示R
i的个数,i为变量,表示1、2、3、4、5、6、7和8,当i为1、3、5、7时,n
i选自0、1、2、3或4;当i为2、4、6、8时,n
i选自0、1、2或3;且当n
i大于1时,任意两个R
i相同或不同;
Ar
2、L
1和L
2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,碳原子数为3~12的三烷基硅基,三苯基硅基,碳原子数为1~5的烷基,任选地被碳原子数为1~5的烷基取代的碳原子数为6~12的芳基,碳原子数为3~12的杂芳基,碳原子数为1~10的卤代烷基,碳原子数为3~10的环烷基,碳原子数为1~10的烷氧基;任选地,在Ar
2中,任意两个相邻的取代基形成3~15元环。
本申请的有机化合物为连接特定芳香基团的三芳胺结构,该三芳胺结构包含1,8-二苯基取代的萘基,该二取代的萘基具有较大的位阻,为必选基团之一,能够调整有机化合物分子的空间构型,从而有效避免分子之间的堆叠,提高成膜性,该基团的电子分布效应还可提升空穴迁移率。此外,三芳胺结构的有机化合物中还包含环烷基螺合芴基,相比于芴基,该基团具有高的空穴迁移率,并且稳定性好。整体而言,本申请化合物具有优异的空穴传输效率和成膜性,用于有机电致发光器件中,可以显著提升器件的发光效率和寿命。
本申请的第二方面提供一种电子元件,包括阳极、阴极、以及介于所述阳极和所述阴极之间的至少一层功能层,所述功能层包含上述的有机化合物。
本申请的第三方面提供一种电子装置,包括上述的电子元件。
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,并不能限制本公开。
附图是用来提供对本申请的进一步理解,并且构成说明书的一部分,与下面的具体实施方式一起用于解释本申请,但并不构成对本申请的限制。
在附图中:
图1是本申请的有机电致发光器件的一实施方式的结构示意图。
图2是本申请的电子装置的一实施方式的结构示意图。
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;330、电子阻挡层;340、有机电致发光层;350、电子传输层;360、电子注入层;400、电子装置。
现在将参考附图更全面地描述示例性实施方式。然而,示例性实施方式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,提供这些实施方式使得本申请将更加全面和完整,并将示例性实施方式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方式中。在下面的描述中,提供许多具体细节从而给出对本公开的实施方式的充分理解。
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。
本申请的第一方面提供一种有机化合物,其具有式1所示的结构:
其中,Ar
1选自式I、式II、式III和式IV中的一个:
Ar
2选自碳原子数为6~40的取代或未取代的芳基、或者碳原子数为3~30的取代或未取代的杂芳基;
L
1和L
2相同或不同,且各自独立地选自单键、碳原子数为6~30的取代或未取代的亚芳基、或者碳原子数为3~30的取代或未取代的亚杂芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8相同或不同,且分别独立地选自氘、卤素、氰基、碳原子数为1~5的烷基、碳原子数为3~12的三烷基硅基、三苯基硅基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8以R
i表示,n
1~n
8以n
i表示,n
i表示R
i的个数,i为变量,表示1、2、3、4、5、6、7和8,当i为1、3、5、7时,n
i选自0、1、2、3或4;当i为2、4、6、8时,n
i选自0、1、2或3;且当n
i大于1时,任意两个R
i相同或不同;
Ar
2、L
1和L
2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,碳原子数为3~12的三烷基硅基,三苯基硅基,碳原子数为1~5的烷基,任选地被碳原子数为1~5的烷基取代的碳原子数为6~12的芳基,碳原子数为3~12的杂芳基,碳原子数为1~10的卤代烷基,碳原子数为3~10的环烷基,碳原子数为1~10的烷氧基;任选地,在Ar
2中,任意两个相邻的取代基形成3~15元环,举例而言,任意两个相邻的取代基形成环戊烷基、环己烷基等。
本申请中,所采用的描述方式“……各自独立地为”与“……分别独立地为”和“……独立地选自”可以互换,均应做广义理解,其既可以是指在不同基团中,相同符号之间所表达的具体选项之间互相不影响,也可以表示在相同的基团中,相同符号之间所表达的具体选项之间互相不影响。例如“
其中,各q独立地为0、1、2或3,各R”独立地选自氢、氘、氟、氯”,其含义是:式Q-1表示苯环上有q个取代基R”,各个R”可以相同也可以不同,每个R”的选项之间互不影响;式Q-2表示联苯的每一个苯环上有q个取代基R”,两个苯环上的R” 取代基的个数q可以相同或不同,各个R”可以相同也可以不同,每个R”的选项之间互不影响。
在本申请中,“任选地被碳原子数为1~5的烷基取代的碳原子数为6~12芳基”是指芳基可以被碳原子数为1~5的烷基中的一个或多个取代,也可以不被碳原子数为1~5的烷基取代,且当芳基上的取代基的个数大于等于2时,取代基可以相同或不同。
本申请中,“取代或未取代的”这样的术语是指,在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述,将取代基统称为Rc)。例如,“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘,卤素基团,氰基,碳原子数为3~12的三烷基硅基,碳原子数为1~5的烷基,任选地被碳原子数为1~5的烷基取代的碳原子数为6~12的芳基,碳原子数为3~12的杂芳基,碳原子数为1~10的卤代烷基,碳原子数为3~10的环烷基,碳原子数为1~10的烷氧基,三芳基硅基,任选地,任意两个所述取代基相互连接以与它们所连接的原子一起形成3~15元的饱和或不饱和环。本申请中,“取代的”官能团可以被上述Rc中的一个或2个以上的取代基取代;当同一个原子上连接有两个取代基Rc时,这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环;当官能团上存在两个相邻的取代基Rc时,相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
本申请中,取代或未取代的官能团的碳原子数,指的是所有碳原子数。举例而言,若L
2选自取代的碳原子数为12的亚芳基,则亚芳基及其上的取代基的所有碳原子数为12。例如:Ar
2为
则其碳原子数为10;L
2为
其碳原子数为12。
本申请中,当没有另外提供具体的定义时,“杂”是指在一个官能团中包括至少1个B、N、O、S、P、Si或Se等杂原子且其余原子为碳和氢。
本申请中,“烷基”可以包括直链烷基或支链烷基。烷基可具有1至5个碳原子,本申请中,诸如“1至5”的数值范围是指给定范围中的各个整数;例如,“1至5个碳原子的烷基”是指可包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子的烷基。具体施例包括但不限于,甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基和戊基。
本申请中,芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基,换言之,芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即,除非另有说明,通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中,稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基的实例可以包括但不限于,苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
基等。本申请中,联苯基可以理解为苯基取代的芳基,也可以理解为未取代的芳基。
本申请中,涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
本申请中,取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、叔丁基、三氟甲基、杂芳基、三甲基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是,取代的芳基的碳原子数,指的是芳基和芳基上的取代基的碳原子总数,例如碳原子数为18的取代的芳基,指的是芳基及其取代基的总碳原子数为18。
本申请中,杂芳基是指环中包含1、2、3、4、5、6或7个杂原子的一价芳香环或其衍生物,所述杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基,换言之,杂芳基可以是单个芳香环体系,也可以是通过碳碳键共轭连接的多个芳香环 体系,且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地,杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、***基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等,而不限于此。其中,噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基,N-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。
本申请中,涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
本申请中,取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三甲基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是,取代的杂芳基的碳原子数,指的是杂芳基和杂芳基上的取代基的碳原子总数。
本申请中,作为取代基的芳基的碳原子数可以为6~12,例如碳原子数可以为6、7、8、9、10、11、12,作为取代基的芳基的具体实例包括但不限于,苯基、联苯基、萘基。
本申请中,作为取代基的杂芳基的碳原子数可以为3~12,例如碳原子数可以为3、4、5、6、7、8、9、10、11、12,作为取代基的杂芳基的具体实例包括但不限于,吡啶基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、喹唑啉基、喹喔啉基、异喹啉基。
本申请中,卤素基团可以包括氟、碘、溴、氯等。
本申请中,三烷基硅基包括但不限于,三甲基硅基、三乙基硅基等。
举例而言,如下式(f)中所示地,式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接,其所表示的含义,包括如式(f-1)~式(f-10)所示出的任一可能的连接方式。
例如,下式(X’)中所示的,式(X’)所表示的菲基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接,其所表示的含义,包括如式(X’-1)~式(X’-4)所示出的任一可能的连接方式。
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。
在本申请的一种实施方式中,L
1和L
2相同或不同,且各自独立地选自单键、或者选自式i-1至式i-7所示的基团所组成的组:
G
1~G
13相同或不同,且各自独立地选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~10的卤代烷基、碳原子数为3~10的环烷基、碳原子数为1~10的烷氧基、碳原子数为3~12的芳基、碳原子数为3~12的杂芳基;
g
1~g
13以g
r表示,G
1~G
13以G
r表示,r为变量,表示1~13的任意整数,g
r表示取代基G
r的数量;当r选自1、2、3、4、5、6、9或13时,g
r选自1、2、3或者4;当r选自7时,g
r选自1、2或者3;当r选自8时,g
r选自1、2、3、4或者5;当r选自10时,g
r选自1、2、3、4、5或者6;当r选自11或12时,g
r选自1、2、3、4、5、6、7或者8;当g
r大于1时,任意两个G
r相同或不同。
可选地,L
1和L
2各自独立地选自单键、碳原子数为6~20的取代或未取代的亚芳基、或者碳原子数为3~20的取代或未取代的亚杂芳基。例如,L
1和L
2各自独立地选自单键,碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20的取代或未取代的亚芳基,或者碳原子数为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20的取代或未取代的亚杂芳基。
可选地,L
1和L
2各自独立地选自单键、碳原子数为6~12的取代或未取代的亚芳基。
可选地,L
1和L
2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的亚三联苯基。
优选地,L
1和L
2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、甲基、乙基、异丙 基、叔丁基、吡啶基、苯基、萘基、联苯基。
可选地,L
1和L
2各自独立地选自单键、取代或未取代的基团P,未取代的基团P选自如下基团:
其中,取代的基团P中具有一个或两个以上的取代基,所述取代基各自独立地选自氘、氟、氰基、三甲基硅基、甲基、乙基、异丙基、叔丁基、吡啶基、苯基、萘基、联苯基,且当取代基个数大于1时,各取代基相同或不同。
进一步可选地,L
1和L
2各自独立地选自单键、如下基团所组成的组:
在本申请的一种实施方式中,Ar
2选自由式j-1至式j-9所示的基团所组成的组:
E
1选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~5的卤代烷基、碳原子数为3~10的环烷基、三苯基硅基;
E
2~E
9、E
18相同或不同,且各自独立地选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5 的烷基、碳原子数为1~5的卤代烷基、碳原子数为3~10的环烷基、碳原子数为3~12的杂芳基;
E
10~E
17相同或不同,且各自独立地选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~5的卤代烷基、碳原子数为3~10的环烷基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基;
e
1~e
18以e
k表示,E
1~E
18以E
k表示,k为变量,表示1~18的任意整数,e
k表示取代基E
k的个数;其中,当k选自8或者15时,e
k选自1、2或者3;当k选自2、5、6、11、13、14或者18时,e
k选自1、2、3或者4;当k选自1、3、4、7或者9时,e
k选自1、2、3、4或者5;当k为12时,e
k选自1、2、3、4、5或者6;当k选自10或者16时,e
k选自1、2、3、4、5、6或者7;当k为17时,e
k选自1、2、3、4、5、6、7或者8;且当e
k大于1时,任意两个E
k相同或不同;
K
1选自O、S、N(E
19)、C(E
20E
21)、Si(E
22E
23);其中,E
19、E
20、E
21、E
22、E
23相同或不同,且各自独立地选自碳原子数为1~5的烷基,任选地被甲基、乙基、异丙基、叔丁基取代的碳原子数为6~12的芳基,碳原子数为3~12的杂芳基,或者E
20与E
21相互连接以与它们共同连接的原子形成碳原子数为3~15的饱和或不饱和的环,或者E
22与E
23相互连接以与它们共同连接的原子形成碳原子数为3~15的饱和或不饱和的环;
K
2选自单键、O、S、N(E
24)、C(E
25E
26)、Si(E
27E
28);其中,E
24、E
25、E
26、E
27、E
28相同或不同,且各自独立地选自碳原子数为1~5的烷基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基。
本申请中,E
20和E
21、E
22和E
23、E
25和E
26、E
27和E
28四组基团中,每组中的两个基团相互连接所形成的环可以是碳原子数为3~15的饱和或不饱和的环。举例来讲,式j-8
中,当K
2和M
2均为单键,E
16为氢,且K
1为C(E
20E
21)时,E
20与E
21相互连接以与它们共同连接的原子形成5元环时,式j-8即为
同样地,式j-8也可以代表
即E
20与E
21相互连接以与它们共同连接的原子形成部分不饱和的13元环。
可选地,Ar
2选自碳原子数为6~25的取代或未取代的芳基、或者碳原子数为3~18的取代或未取代的杂芳基。例如,Ar
2选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25的取代或未取代的芳基,或者碳原子数为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18的取代或未取代的杂芳基。
可选地,Ar
2选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的三联苯基、取代或未取代的芴基、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、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的咔唑基、取代或未取代的9,9'-螺二芴基。
优选地,Ar
2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、咔唑基、三苯基硅基。
可选地,Ar
2选自取代或未取代的基团T,未取代的基团T选自如下基团所组成的组:
其中,取代的基团T具有一个或两个以上的取代基,所述取代基各自独立地选自氘、氟、氰基、三甲基硅基、甲基、乙基、异丙基、叔丁基、吡啶基、咔唑基、苯基、萘基、联苯基、三苯基硅基,且当取代基个数大于1时,各取代基相同或不同。
可选地,Ar
2选自如下基团所组成的组:
进一步可选地,Ar
2选自如下基团所组成的组:
在本申请的一种实施方式中,R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8相同或不同,且分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、苯基、萘基、联苯基、嘧啶基、吡啶基、喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基、三苯基硅基。
可选地,所述有机化合物选自如下化合物所组成的组:
本申请的第二方面提供一种电子元件,用于实现光电转换或者电光转化。该电子元件包括相对设置的阳极和阴极,以及介于阳极和阴极之间的至少一层功能层,该功能层包含本申请的有机化合物。
在本申请的一种具体实施方式中,所述电子元件可以为有机电致发光器件或光电转换器件。如图1所示,本申请的有机电致发光器件包括阳极100、阴极200、以及介于阳极和阴极之间的至少一层功能层300,该功能层300包括空穴注入层310、空穴传输层320、电子阻挡层330、 有机电致发光层340、电子传输层350以及电子注入层360;空穴注入层310、空穴传输层320、电子阻挡层330、有机电致发光层340、电子传输层350以及电子注入层360可以依次形成在阳极100上,空穴传输层320可以含有本申请第一方面所述的有机化合物,优选含有化合物1~608中的至少一种。
可选地,阳极100包括以下阳极材料,其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数,work function)材料。阳极材料具体实例包括:金属如镍、铂、钒、铬、铜、锌和金或它们的合金;金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);组合的金属和氧化物如ZnO∶Al或SnO
2∶Sb;或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺,但不限于此。优选包括包含氧化铟锡(铟锡氧化物,indium tin oxide)(ITO)作为阳极的透明电极。
可选地,空穴传输层320可以包括一种或者多种空穴传输材料。在本申请的一种实施方式中,空穴传输层320由本申请所提供的有机化合物组成。
可选地,电子阻挡层330用于阻挡有机电致发光层340传输过来的电子,进而保证电子和空穴能够很高效地在有机电致发光层340复合;同时,电子阻挡层330还可以阻挡有机电致发光层340扩散过来的激子,减少激子的三线态淬灭,进而保证有机电致发光器件的发光效率。电子阻挡层330的化合物具有比较高的LUMO值,其可以有效阻挡电子和激子从有机电致发光层340向阳极100方向的传输和扩散。电子阻挡层330可以为具有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、芳香族含氮衍生物或者其他材料,本申请对此不做特殊的限制。举例而言,在本申请的一种实施方式中,电子阻挡层330可以由EB-01组成。
有机电致发光层340的材料可以为金属螯类化合物、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,有机电致发光层340可以由BH-01和BD-01组成。
电子传输层350可以为单层结构,也可以为多层结构,其可以包括一种或者多种电子传输材料,电子传输材料可以选自苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料,本申请对此不做特殊的限定。举例而言,在本申请的一种实施方式中,电子传输层350可以由ET-06和LiQ组成。
可选地,阴极200包括以***极材料,其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括:金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金;或多层材料如LiF/Al、Liq/Al、LiO
2/Al、LiF/Ca、LiF/Al和BaF
2/Ca,但不限于此。优选包括包含银和镁的金属电极作为阴极200。
可选地,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。举例而言,在本申请的一种实施方式中,空穴注入层310由F4-TCNQ组成。
可选地,在阴极200和电子传输层350之间还可以设置有电子注入层360,以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料,或者可以包括碱金属与有机物的络合物。举例而言,在本申请的一种实施方式中,电子注入层360为LiQ。
本申请的第三方面提供一种电子装置,该电子装置包括本申请所述的电子元件。
举例而言,如图2所示,本申请提供的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实施方式所描述的任意一种有机电致发光器件。该电子装置可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置,例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。由于第一电子装置400具有上述有机电致发光器件,因此具有相同的有益效果,本申请在此不再赘述。
下面将结合实施例详细描述本发明,但是,以下描述是用于解释本发明,而不是以任意方式限制本发明的范围。
合成实施例
1、IM M-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加入1,8-二溴萘(44g,153.86mmol)、苯基硼酸(18.76g,153.83mmol)、Na
2CO
3(70.16g,307.72mmol)、THF(264mL)、H
2O(88mL)、Pd(PPh
3)
4(1.776g,1.5386mmol)和四丁基溴化铵(TBAB)(0.99g,3.0772mmol),开启搅拌,升温至75℃~85℃反应5h,反应结束后,冷却至室温。用二氯甲烷萃取分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液减压蒸馏除去溶剂;使用己烷/甲苯体系对粗品进行硅胶色谱提纯,得到淡黄色固体IM M-1(33.8g,收率75%)。
2、IM N-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入IM M-1(30.6g,107.86mmol)、THF(184mL),降温至-75℃~-80℃,滴加溶有正丁基锂(n-BuLi)的己烷溶液(10mL),搅拌约50min;保持-75℃~-80℃,然后滴加溶有B(OMe)
3(61.2g)的THF溶液(20mL),搅拌约50min。升温至室温,反应3h。反应结束后,向反应液中加入饱和的NH
4Cl水溶液,分离并采集有机层,并减压蒸馏除去溶剂。用己烷洗涤生成物,得到白色固体IM N-1(19.6g,收率73%)。
3、IM A-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加入IM N-1(19.0g,77.3mmol)、1-溴-3-碘苯(21.86g,77.3mmol)、Na
2CO
3(35.24g,154.6mmol)、THF(120mL)、H
2O(40mL)、Pd(PPh
3)
4(0.9g,0.773mmol)和四丁基溴化铵(0.5g,1.546mmol),开启搅拌,升温至75℃~85℃反应5h,反应结束后,冷却至室温。用二氯甲烷萃取分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液减压蒸馏除去溶剂;使用己烷/甲苯体系对粗品进行硅胶色谱提纯,得到淡黄色固体IM A-1(20.0g,收率72%)。
参照IMA-1的方法合成表1所列的IM A-X,使用原料1代替1-溴-3-碘苯,其中,使用的主要原料、合成的中间体及其收率示于表1中。
表1
4、IM B-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入2-溴芴(33.0g,134.63mmol)、50wt%氢氧化钠水溶液(23.1g)、二甲基亚砜(DMSO)(340mL),苄基三乙基氯化铵(76.67g,336.58mmol),升温至155℃~165℃,滴加1,4-二溴丁烷(29.07g,134.63mmol),反应3h,反应结束后,冷却至室温。用甲苯和水萃取,过柱纯化,得到淡黄色液体IM B-1(32.23g,收率80%)。
参考IM B-1的方法合成表2所列的IM B-X,不同之处在于,使用原料2代替2-溴芴,其中,使用的主要原料、合成的中间体及其收率示于表2中。
表2
5、IM C-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入2-溴芴(33.0g,134.63mmol)、50wt%氢氧化钠水溶液(23.1g)、二甲基亚砜(340mL),苄基三乙基氯化铵(76.67g,336.58mmol),升温至155~165℃,滴加1,5-二溴戊烷(30.96g,134.63mmol),反应3h,反应结束后,冷却至室温。用甲苯和水萃取,过柱纯化,得到淡黄色液体IM C-1(34.58g,收率82%)。
参考IM C-1的方法合成表3所列的IM C-X,不同之处在于,使用原料3代替2-溴芴,其中,使用的主要原料、合成的中间体及其收率示于表3中。
表3
6、IM BD-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入2-溴-3'-氯-1,1'-联苯基(25g,93.44mmol)、THF(200mL),降温至-80℃~-90℃,滴加正丁基锂(7.18g),滴加结束后保温1h,取样检测,待锂盐反应完成后,然后滴加2-降冰片(10.29g,93.44mmol)的THF溶液,滴加过程中保持温度为-80℃~-90℃,滴加结束后,保温1h,升温至 室温,反应12h。反应结束后,向反应液中加入5%盐酸至pH<7,搅拌1h,加H
2O(500mL)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为流动相进行硅胶柱色谱提纯,得到IM BD-1(22.62g,收率81%)。
7、IM D-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入IM BD-1(20g,66.93mmol)和冰醋酸(12.05g,200.79mmol),升温至50~55℃,缓慢滴加浓硫酸(98%)的醋酸溶液,滴加完毕后升至75~85℃,搅拌反应1h,反应结束后,冷却至室温,加二氯甲烷进行萃取,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/正庚烷体系进行硅胶柱色谱提纯,得到白色固体IM D-1(8.46g,收率45%)。
参考IM D-1的方法合成表4所列的IM D-X,不同之处在于,使用原料4代替2-溴-3'-氯-1,1'-联苯基,其中,使用的主要原料、合成的中间体及其最后一步收率如表4所示。
表4
8、IM ZD-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入2-溴-3'-氯-1,1'-联苯基(25g,93.44mmol)、THF(200mL),降温至-80℃~-90℃,滴加正丁基锂(7.18g),滴加结束后保温1h,取样检测,待锂盐反应完成后,然后滴加AZ-1(10.29g,93.44mmol)的THF溶液,滴加过程中保持温度为-80℃~-90℃,滴加结束后,保温1h,升温至室温,反应12h。反应结束后,向反应液中加入5%盐酸至pH<7,搅拌1h,加H
2O(500mL)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 甲烷为流动相进行硅胶柱色谱提纯,得到IM ZD-1(22.06g,收率79%)。
9、IM Z-1的合成
向装有机械搅拌、温度计、恒压滴加漏斗的三口瓶中通氮气(0.100L/min)置换15min,加入IM ZD-1(20g,66.93mmol)和冰醋酸(12.05g,200.79mmol),升温至50~55℃,缓慢滴加浓硫酸(98%)的醋酸溶液,滴加完毕后升至75~85℃,搅拌反应1h,反应结束后,冷却至室温,加二氯甲烷进行萃取,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/正庚烷体系进行硅胶柱色谱提纯,得到白色固体IM Z-1(8.84g,收率47%)。
参照IM Z-1的方法合成表11所列的中间体,不同之处在于,使用原料5代替2-溴-3'-氯-1,1'-联苯基,其中,使用的主要原料、合成的中间体及其最后一步收率如表11所示。
表11
10、IM BM-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加入IM B-1(25g,83.554mmol)、联硼酸频哪醇酯(21.22g,83.554mmol)、三(二亚苄基丙酮)二钯(0.7651g,0.8355mmol)、X-phos(0.7898g,1.671mmo)、醋酸钾(12.30g,125.33mmol)和1,4-二氧六环(136mL),升温至105~115℃,回流搅拌反应5h,反应结束后,冷却至室温。反应液水洗后分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液减压蒸馏除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯,得到白色固体IM BM-1(21.12g,收率73%)。
参照IM BM-1的方法合成表5所示的中间体,不同之处在于,使用原料6代替IM B-1,其中,使用原料6、合成的中间体及其收率如表5所示。
表5
11、IM BN-1
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加入IM BM-1(18g,51.981mmol)、对溴碘苯(14.71g,51.981mmol)、四(三苯基膦)钯(0.60g,0.5198mmol)、碳酸钾(10.78g,77.97mmol)、四丁基溴化铵(0.335g,1.039mmol),然后加入甲苯(108mL)、乙醇(36mL)和去离子水(36mL)混合溶剂,开启搅拌,升温至75℃~85℃反应12h,反应结束后,冷却至室温。用甲苯(100mL)萃取分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液减压蒸馏除去溶剂;使用正庚烷为流动相对粗品进行硅胶色谱提纯,再使用二氯甲烷/乙酸乙酯体系进行重结晶,得到IM BN-1(14.24g,收率73%)。
参照IM BN-1的方法合成表6所列的中间体,不同之处在于,使用原料7代替IM BM-1,使用原料8代替对溴碘苯,其中,使用的主要原料、合成的中间体及其收率示于表6中。
表6
12、IM EN-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加入3-溴苯硼酸(18g,89.63mmol)、2-溴菲(23.05g,89.63mmol)、四(三苯基膦)钯(1.04g,0.8963mmol)、碳酸钾(17.75g,134.45mmol)、四丁基溴化铵(0.577g,1.7926mmol),然后加入甲苯(108mL)、乙醇(36mL)和去离子水(36mL)混合溶剂,开启搅拌,升温至75~85℃反应2h,反应结束后,冷却至室温。用甲苯(500mL)萃取分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液减压蒸馏除去溶剂;使用正庚烷为流动相对粗品进行硅胶色谱提纯,再使用二氯甲烷/乙醇体系进行重结晶,得到淡黄色固体IM EN-1(20.89g,收率70%)。
参照IM EN-1的方法合成表7所列的IM EN-X,不同之处在于,使用原料9代替3-溴苯硼酸,使用原料10代替2-溴菲,其中,使用的主要原料、合成的中间体及其收率示于表7中。
表7
13、IM AZ-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加入IM A-1(14g,38.97mmol)、苯胺(3.63g,38.97mmol)、三(二亚苄基丙酮)二钯(0.3569g, 0.3897mmol)、X-phos(0.3685g,0.7794mmol)、叔丁醇钠(5.62g,58.455mmol)和甲苯溶剂(70mL),开启搅拌,升温至105~115℃反应3h,反应结束后,冷却至室温。用二氯甲烷和水萃取分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液通过短硅胶柱,减压除去溶剂,使用二氯甲烷/正庚烷体系对粗品进行重结晶,得到IM AZ-1(11.00g,收率76%)。
参照IM AZ-1的方法合成表8所列的IM AZ-Y,不同之处在于,使用原料11代替IM A-1,使用原料12代替苯胺,其中,使用的主要原料、合成的中间体及其收率示于表8中。
表8
参考IM AZ-1的方法合成表9所列的IM AZ-Y,不同之处在于,使用原料13代替苯胺,使用原料14代替IM A-1,其中,使用的主要中间体、合成的中间体及其收率示于表9中。
表9
14、化合物25的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min,加 入IM AZ-1(9g,24.23mmol)、IM B-1(7.25g,24.23mmol)、三(二亚苄基丙酮)二钯(0.222g,0.2423mmol)、S-phos(0.1989g,0.4846mmol)、叔丁醇钠(3.492g,36.345mmol)和甲苯溶剂(72mL),开启搅拌,升温至105~115℃反应3h,反应结束后,冷却至室温。用二氯甲烷和水萃取分离有机相,使用无水硫酸镁干燥有机相,过滤后将滤液通过短硅胶柱,减压除去溶剂,使用二氯甲烷/正庚烷体系对粗品进行重结晶,得到化合物25(10.72g,收率75%),质谱(m/z)=589.2[M+H]
+。
参照化合物25的方法合成表10所列的化合物Y,不同之处在于,使用原料15代替IM AZ-1,使用原料16代替IM B-1,其中,使用的主要原料、合成的化合物及其收率和质谱示于表10中。
表10
部分化合物核磁数据如下表11所示
表11
有机电致发光器件的制备和性能评估
实施例1
蓝色有机电致发光器件
将厚度为
的阳极ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸,采用光刻工序,将其制备成具有阴极、阳极以及绝缘层图案的实验基板,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,并采用有机溶剂清洗ITO基板表面,以清除ITO基板表面的浮渣及油污。
实施例2~93
除了在形成空穴传输层时,分别使用表13的化合物代替实施例1中的化合物25之外,采用与实施例1相同的方法制备蓝色有机电致发光器件。
对比例1~3
除了在形成空穴传输层时,分别使用化合物A、化合物B、化合物C代替实施例1中的化合物25之外,采用与实施例1相同的方法制备蓝色有机电致发光器件。
在实施例和比较例中,所采用的主要材料的结构式如下:
表12
其中,IVL(电压、效率、功率)性能、T95寿命是在15mA/cm
2的电流密度下进行测试的,测试结构见表13。
表13
根据上述表13的结果可知,作为空穴传输层的化合物的实施例1-93与已公知的化合物所对应的器件比较例1-3相比有机电致发光器件的工作电压至少降低了4.0%,发光效率(Cd/A)至少提高了10.1%,外量子效率至少提高了10.4%,寿命最少提高了13%。因此本申请化合物具有兼顾提高发光效率及提高寿命的特点。由上述数据可知,采用本申请的有机化合物作为电子元件的空穴传输层,该电子元件的发光效率(Cd/A)、外量子效率(EQE)以及寿命(T95)都有显著的提高。因此,在空穴传输层中使用本申请的有机化合物可制备得到高发光效率、长寿命的有机电致发光器件。
应可理解的是,本申请能够具有其他实施方式,并且能够以多种方式实现并且执行。前述变形形式和修改形式落在本申请的范围内。应可理解的是,本说明书公开和限定的本申请延伸到文中和/或附图中提到或明显的两个或两个以上单独特征的所有可替代组合。所有这些不同的组合构成本申请的多个可替代方面。
Claims (14)
- 一种有机化合物,其具有式1所示的结构:其中,Ar 1选自式I、式II、式III和式IV中的一个:Ar 2选自碳原子数为6~40的取代或未取代的芳基、或者碳原子数为3~30的取代或未取代的杂芳基;L 1和L 2相同或不同,且各自独立地选自单键、碳原子数为6~30的取代或未取代的亚芳基、或者碳原子数为3~30的取代或未取代的亚杂芳基;R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8相同或不同,且分别独立地选自氘、卤素、氰基、碳原子数为1~5的烷基、碳原子数为3~12的三烷基硅基、三苯基硅基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基;R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8以R i表示,n 1~n 8以n i表示,n i表示R i的个数,i为变量,表示1、2、3、4、5、6、7和8,当i为1、3、5、7时,n i选自0、1、2、3或4;当i为2、4、6、8时,n i选自0、1、2或3;且当n i大于1时,任意两个R i相同或不同;Ar 2、L 1和L 2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,碳原子数为3~12的三烷基硅基,三苯基硅基,碳原子数为1~5的烷基,任选地被碳原子数为1~5的烷基取代的碳原子数为6~12的芳基,碳原子数为3~12的杂芳基,碳原子数为1~10的卤代烷基,碳原子数为3~10的环烷基,碳原子数为1~10的烷氧基;任选地,在Ar 2中,任意两个相邻的取代基形成3~15元环。
- 根据权利要求1所述的有机化合物,其中,L 1和L 2相同或不同,且各自独立地选自单键、或者选自式i-1至式i-7所示的基团所组成的组:G 1~G 13相同或不同,且各自独立地选自:氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~10的卤代烷基、碳原子数为3~10的环烷基、碳原子数为1~10的烷氧基、碳原子数为3~12的芳基、碳原子数为3~12的杂芳基;g 1~g 13以g r表示,G 1~G 13以G r表示,r为变量,表示1~13的任意整数,g r表示取代基G r的数量;当r选自1、2、3、4、5、6、9或13时,g r选自1、2、3或者4;当r选自7时,g r选自1、2或者3;当r选自8时,g r选自1、2、3、4或者5;当r选自10时,g r选自1、2、3、4、5或者6;当r选自11或12时,g r选自1、2、3、4、5、6、7或者8;当g r大于1时,任意两个G r相同或不同。
- 根据权利要求1所述的有机化合物,其中,L 1和L 2各自独立地选自单键、碳原子数为6~20的取代或未取代的亚芳基、或者碳原子数为3~20的取代或未取代的亚杂芳基。
- 根据权利要求1所述的有机化合物,其中,L 1和L 2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的亚三联苯基;优选地,L 1和L 2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、甲基、乙基、异丙基、叔丁基、吡啶基、苯基、萘基、联苯基。
- 根据权利要求1所述的有机化合物,其中,Ar 2选自由式j-1至式j-9所示的基团所组成的组:E 1选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~5的卤代烷基、碳原子数为3~10的环烷基、三苯基硅基;E 2~E 9、E 18相同或不同,且各自独立地选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~5的卤代烷基、碳原子数为3~10的环烷基、碳原子数为3~12的杂芳基;E 10~E 17相同或不同,且各自独立地选自氢、氘、氟、氰基、三甲基硅基、碳原子数为1~5的烷基、碳原子数为1~5的卤代烷基、碳原子数为3~10的环烷基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基;e 1~e 18以e k表示,E 1~E 18以E k表示,k为变量,表示1~18的任意整数,e k表示取代基E k的个数;其中,当k选自8或者15时,e k选自1、2或者3;当k选自2、5、6、11、13、14或者18时,e k选自1、2、3或者4;当k选自1、3、4、7或者9时,e k选自1、2、3、4或者5;当k为12时,e k选自1、2、3、4、5或者6;当k选自10或者16时,e k选自1、2、3、4、5、6或者7;当k为17时,e k选自1、2、3、4、5、6、7或者8;且当e k大于1时,任意两个E k相同或不同;K 1选自O、S、N(E 19)、C(E 20E 21)、Si(E 22E 23);其中,E 19、E 20、E 21、E 22、E 23相同或不同,且各自独立地选自碳原子数为1~5的烷基,任选地被甲基、乙基、异丙基、叔丁基取代的碳原子数为6~12的芳基,碳原子数为3~12的杂芳基,或者E 20与E 21相互连接以与它们共同连接的原子形成碳原子数为3~15的饱和或不饱和的环,或者E 22与E 23相互连接以与它们共同连接的原子形成碳原子数为3~15的饱和或不饱和的环;K 2选自单键、O、S、N(E 24)、C(E 25E 26)、Si(E 27E 28);其中,E 24、E 25、E 26、E 27、E 28相同或不同,且各自独立地选自碳原子数为1~5的烷基、碳原子数为6~12的芳基、碳原子数为3~12的杂芳基。
- 根据权利要求1所述的有机化合物,其中,Ar 2选自碳原子数为6~25的取代或未取代的芳基、或者碳原子数为3~18的取代或未取代的杂芳基。
- 根据权利要求1所述的有机化合物,其中,Ar 2选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的三联苯基、取代或未取代的芴基、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、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的咔唑基、取代或未取代的9,9'-螺二芴基;优选地,Ar 2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、咔唑基、三苯基硅基。
- 根据权利要求1所述的有机化合物,其中,R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8相同或不同,且分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、苯基、萘基、联 苯基、嘧啶基、吡啶基、喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基、三苯基硅基。
- 一种电子元件,包括阳极、阴极、以及介于所述阳极与所述阴极之间的至少一层功能层,所述功能层包含权利要求1-11中任一项所述的有机化合物;优选地,所述功能层包括空穴传输层,所述空穴传输层包括所述有机化合物。
- 根据权利要求12所述的电子元件,其中,所述电子元件为有机电致发光器件或光电转换器件。
- 一种电子装置,包括权利要求12或13所述的电子元件。
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