WO2022188514A1 - Composé organique, élément électronique le comprenant et dispositif électronique - Google Patents

Composé organique, élément électronique le comprenant et dispositif électronique Download PDF

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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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carbon atoms
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substituted
unsubstituted
organic compound
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岳娜
华正伸
金荣国
李应文
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陕西莱特光电材料股份有限公司
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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

La présente invention concerne le domaine technique de l'électroluminescence organique et concerne un composé organique, un élément électronique le comprenant, ainsi qu'un dispositif électronique. Le composé organique a une structure telle que représentée dans la formule (1) et le composé organique présente d'excellentes performances photoélectriques, peut améliorer l'efficacité lumineuse, l'efficacité quantique externe et la durée de vie d'un appareil, et peut réduire la tension de travail.
PCT/CN2021/142183 2021-03-12 2021-12-28 Composé organique, élément électronique le comprenant et dispositif électronique WO2022188514A1 (fr)

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CN114230433B (zh) * 2021-12-27 2023-10-20 郑州海阔光电材料有限公司 一种2-溴-4’-氯-1,1’-联苯的合成方法
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CN115466184A (zh) * 2022-09-20 2022-12-13 北京八亿时空液晶科技股份有限公司 一种有机化合物及其应用
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