WO2021170008A1 - Composé contenant de l'azote, composant électronique et dispositif électronique - Google Patents

Composé contenant de l'azote, composant électronique et dispositif électronique Download PDF

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WO2021170008A1
WO2021170008A1 PCT/CN2021/077730 CN2021077730W WO2021170008A1 WO 2021170008 A1 WO2021170008 A1 WO 2021170008A1 CN 2021077730 W CN2021077730 W CN 2021077730W WO 2021170008 A1 WO2021170008 A1 WO 2021170008A1
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carbon atoms
group
groups
nitrogen
substituted
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PCT/CN2021/077730
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Chinese (zh)
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马天天
肖蛟
马占耿
李昕轩
喻超
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陕西莱特光电材料股份有限公司
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Priority claimed from CN202010777056.3A external-priority patent/CN113321589B/zh
Priority claimed from CN202011308317.3A external-priority patent/CN113321588B/zh
Application filed by 陕西莱特光电材料股份有限公司 filed Critical 陕西莱特光电材料股份有限公司
Publication of WO2021170008A1 publication Critical patent/WO2021170008A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C211/60—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 containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • This application relates to the technical field of organic materials, and in particular to a nitrogen-containing compound, an electronic component using the nitrogen-containing compound, and an electronic device including the electronic component.
  • Such electronic components usually include 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 electronic element when it is an organic electroluminescence device, it generally includes an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer, and a cathode that are stacked in sequence.
  • anode When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, the holes on the anode side also move to the light emitting layer, and the electrons and holes are combined in the electroluminescent layer. Excitons are formed, and the excitons are in an excited state to release energy to the outside, so that the electroluminescent layer emits light to the outside.
  • CN110467536A, KR1020130086757A, CN110183333A, etc. disclose materials that can prepare hole transport layers in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of this application is to provide a nitrogen-containing compound, an electronic component and an electronic device to improve the performance of the electronic component and the electronic device.
  • this application adopts the following technical solutions:
  • the first aspect of the present application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in formula I:
  • L is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 6-30 carbon atoms; the substituents in L are each independently selected from: deuterium , Halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, and those with 1-10 carbon atoms Haloalkyl, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkyl with 3-12 carbon atoms Silicon-based
  • Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms
  • the substituents in Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, and the number of carbon atoms is 3-18 heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and those with 1-10 carbon atoms Alkoxy group, alkylthio group having 1-10 carbon atoms, trialkylsilyl group having 3-12 carbon atoms;
  • R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, carbon atom Cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkoxy groups with 1-10 carbon atoms, and 1 carbon atoms -10 alkylthio group, trialkylsilyl group with 3-12 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3 or 4, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 represents the number of R 2 , n 2 is selected from 0, 1, 2 or 3, when n 2 is greater than 1, any two R 2 are the same or different.
  • the second aspect of the present application provides an electronic component, which includes an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; wherein, the functional layer includes the first The nitrogen-containing compound described in the aspect.
  • the electronic component is an organic electroluminescent device.
  • the electronic component is a photoelectric conversion device.
  • a third aspect of the present application provides an electronic device, which includes the electronic component described in the second aspect of the present application.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic diagram of the structure of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
  • Anode; 200 cathode; 300, functional layer; 310, hole injection layer; 320: hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • this application provides a nitrogen-containing compound, the structure of which is shown in formula I:
  • L is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 6-30 carbon atoms; the substituents in L are each independently selected from: deuterium , Halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, and those with 1-10 carbon atoms Haloalkyl, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkyl with 3-12 carbon atoms Silicon-based
  • Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms
  • the substituents in Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, and the number of carbon atoms is 3-18 heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and those with 1-10 carbon atoms Alkoxy group, alkylthio group having 1-10 carbon atoms, trialkylsilyl group having 3-12 carbon atoms;
  • R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, carbon atom Cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkoxy groups with 1-10 carbon atoms, and 1 carbon atoms -10 alkylthio group, trialkylsilyl group with 3-12 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3 or 4, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 represents the number of R 2 , n 2 is selected from 0, 1, 2 or 3, when n 2 is greater than 1, any two R 2 are the same or different.
  • the term “optionally” means that the event or environment described later can but need not occur, and the description includes occasions where the event or environment occurs or does not occur.
  • “optionally, two substituents ⁇ form a ring” means that these two substituents can form a ring but do not necessarily form a ring, including: the situation where two substituents form a ring and two substituents do not form a ring Scene.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine", and its meaning is:
  • formula Q-1 represents q substituents R" on the benzene ring , Each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and R on two benzene rings The number q of "substituents can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by a carbon-carbon bond, through A monocyclic aryl group and a fused ring aryl group conjugated by carbon-carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, and Si.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthryl, pyrenyl, benzofluoranthene, Base and so on.
  • the substituted aryl group can be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, ring Alkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl substituted aryl include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothienyl substituted phenyl, pyridyl substituted phenyl, carbazolyl substituted phenyl, etc.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group.
  • the total number of carbon atoms of the group is 18.
  • a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof.
  • the heteroatom may be at least one of B, O, N, P, Si, and S.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofur
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
  • N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings conjugated through carbon-carbon bonds.
  • System type of heteroaryl is
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl group, heteroaryl group, trialkylsilyl group, alkyl group. , Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • the non-positioned connecting bond refers to the single bond protruding from the ring system It means that one end of the link can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).
  • the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-localized bond extending from the middle of the benzene ring on one side, which represents The meaning of includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
  • the non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system.
  • the substituent R'represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and the meaning represented by it includes formulas (Y-1) to Any possible connection mode shown in formula (Y-7).
  • a cycloalkyl group with 3-10 carbon atoms can be used as a substituent of an aryl group and a heteroaryl group, and specific examples thereof include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
  • the alkyl group with 1-10 carbon atoms may include straight-chain alkyl groups with 1-10 carbon atoms and branched-chain alkyl groups with 3-10 carbon atoms.
  • the number of carbon atoms may be 1, for example. 2, 3, 4, 5, 6, 7, 8, 9, 10, specific examples of alkyl groups having 1-10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-propyl Butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc.
  • halogen may include fluorine, chlorine, bromine, and iodine.
  • the number of carbon atoms of the alkoxy group having 1-10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • Specific examples of the alkoxy group include but It is not limited to methoxy, ethoxy, n-propoxy and the like.
  • the haloalkyl group can be, for example, a fluoroalkyl group, and the number of carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples include, but are not limited to, trifluoromethyl base.
  • trialkylsilyl include but are not limited to trimethylsilyl, triethylsilyl, ethyldimethylsilyl and the like.
  • the number of carbon atoms of the aryl group as a substituent is 6-20 or 6-18, and the number of carbon atoms may be 6, 10, 12, 14, 18, 20, etc., for example.
  • Specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, phenanthryl, and the like.
  • the number of carbon atoms of the heteroaryl group as a substituent is 3-20 or 3-18, and the number of carbon atoms may be 3, 4, 5, 7, 8, 9, 12, 18, etc., for example.
  • Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
  • Ar 1 , Ar 2 and Ar 3 can each independently be selected from the group consisting of the groups represented by the following chemical formula i-1 to chemical formula i-14:
  • M 1 is selected from a single bond or
  • G 1 to G 5 are each independently selected from N or C(F 1 ), and at least one of G 1 to G 5 is selected from N; when two or more of G 1 to G 5 are selected from C(F 1 ) , Any two F 1 are the same or different;
  • G 6 to G 13 are each independently selected from N or C(F 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(F 2 ) , Any two F 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(F 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(F 3 ) , Any two F 3 are the same or different;
  • H 1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, alkyl groups having 1 to 10 carbon atoms, and those having 1 to 10 carbon atoms A halogenated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
  • H 2 to H 9 and H 21 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms Group, halogenated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, carbon Heteroaryl groups with 3 to 18 atoms;
  • H 10 to H 20 and F 1 to F 3 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, and 1 to carbon atoms 10 alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkyl sulfides having 1 to 10 carbon atoms Group, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms;
  • h 1 ⁇ h 21 are represented by h k
  • H 1 ⁇ H 21 are represented by H k
  • k is a variable, representing any integer from 1 to 21
  • h k is the number of substituents H k ; wherein, when k is selected from 5 Or when 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected When 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 Or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two H k are the same or different;
  • K 1 is selected from O, S, Se, N (H 22 ), C (H 23 H 24 ), Si (H 23 H 24 ); wherein, H 22 , H 23 , and H 24 are each independently selected from: carbon atoms An aryl group having 6 to 18, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above H 23 and H 24 are connected to each other to form a 5- to 13-membered saturated or unsaturated ring with the atoms they are commonly connected to;
  • K 2 is selected from a single bond, O, S, Se, N (H 25 ), C (H 26 H 27 ), Si (H 26 H 27 ); wherein, H 25 , H 26 , and H 27 are each independently selected from : C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group, C3-C10 cycloalkyl group, or the above H 26 and H 27 are connected to each other to form a 5- to 13-membered saturated or unsaturated ring with the atoms to which they are commonly connected.
  • the ring formed by connecting the two groups in each group may be a 5-13 membered saturated or unsaturated ring.
  • the ring formed by connecting the two groups in each group may be a 5-13 membered saturated aliphatic ring or an aromatic ring.
  • the two groups of H 23 and H 24 , H 26 and H 27 can respectively form a saturated aliphatic monocyclic ring of 5-8 members or an aromatic ring of 10-13 members.
  • F 2 to F 3 can be represented by F x , where x is a variable and represents 2 or 3.
  • F x refers to F 2 .
  • C (F x) when not connected to the positioning linkage C (F x) a, C (F x) in the absence of F x.
  • G 12 when connected to G 12 , G 12 can only represent C atom, that is, the structure of chemical formula i-13 is:
  • L is selected from the group shown in Chemical Formula 1-1;
  • R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, number of carbon atoms Cycloalkyl groups of 3-10, aryl groups of 6-20 carbon atoms, heteroaryl groups of 3-20 carbon atoms, alkoxy groups of 1-10 carbon atoms, 1- 10 alkylthio groups, trialkylsilyl groups with 3-12 carbon atoms;
  • R 3 is selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, number of carbon atoms Is an alkoxy group having 1-10, an alkylthio group having 1-10 carbon atoms, and a trialkylsilyl group having 3-12 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3 or 4, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 represents the number of R 2 , n 2 is selected from 0, 1, 2 or 3, when n 2 is greater than 1, any two R 2 are the same or different;
  • n 3 represents the number of R 3 , n 3 is selected from 0, 1, 2, 3 or 4, when n 3 is greater than 1, any two R 3 are the same or different;
  • Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms ;
  • the substituents in Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3-18 carbon atom Heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and alkoxy groups with 1-10 carbon atoms , Alkylthio groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms; in Ar 1 , Ar 2 , and Ar 3 , when there are two substituents on the same atom, Optionally, two substituents are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms to which they are commonly connected.
  • the nitrogen-containing compound having the structure shown in Chemical Formula 1 includes two aromatic amine groups connected to each other through a benzene ring, and one of the aromatic amine groups includes an adamantane spiro-bound fluorenyl group ,
  • This structure design makes the electron cloud density distribution more reasonable, so that the compound has a high hole mobility.
  • one of the four aromatic substituents in the diaromatic amine structure is a fluorenyl group spiro-coated with adamantane, which improves the asymmetry of the overall molecular structure.
  • the asymmetric structure brings low crystallinity and good film-forming ability. .
  • the structure of the nitrogen-containing compound can be selected from the group consisting of chemical formula 1-A to chemical formula 1-D:
  • the number of substituents may be one or two or more (ie one or more); when the number of substituents is two or more, the substitution
  • the base can be the same or different.
  • the saturated aliphatic ring or aromatic ring (including aromatic ring, heteroaromatic ring).
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, substituted or unsubstituted carbon atoms having 4 to 25 Heteroaryl.
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from carbon atoms 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 groups, or selected from 4, 5, 8, 9, 11, 12, 16, 18, 20, 21, 22, 23, 24, 25 substituted or unsubstituted heteroaryl.
  • the substituents in Ar 1 , Ar 2 , and Ar 3 are each independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, and 1 to 4 haloalkyl, carbon 5-10 cycloalkyl, carbon 6-15 aryl, carbon 5-12 heteroaryl, carbon 1-4 alkoxy Group, alkylthio group having 1 to 4 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms.
  • substituents in Ar 1 , Ar 2 , and Ar 3 include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, Cyclohexyl, phenyl, naphthyl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, methoxy, ethoxy, methylthio, ethylthio, trimethyl Silicon-based, trifluoromethyl, etc.
  • Ar 1 is a substituted or unsubstituted group Z 1
  • Ar 2 is a substituted or unsubstituted group Z 2
  • Ar 3 is a substituted or unsubstituted group Z 3 , where The substituted groups Z 1 , Z 2 and Z 3 are each independently selected from the group consisting of:
  • the substituted group Z 1 , the substituted group Z 2 and the substituted group Z 3 each independently have one or two or more substituents, and the substituents are independently selected from: deuterium, cyano, fluorine, carbon number It is an alkyl group having 1-4, a haloalkyl group having 1-4 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, an alkoxy group having 1-4 carbon atoms, and 1-4 carbon atoms
  • the number of substituents is two or more, any two substituents are the same or different.
  • substituents include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, methoxy, methylthio, ethoxy Group, trimethylsilyl, trifluoromethyl, etc.
  • Ar 1 , Ar 2 and Ar 3 may each independently be selected from the group consisting of the following groups:
  • Ar 2 and Ar 3 are each independently selected from the group consisting of the following groups:
  • Ar 1 is selected from the group consisting of the following groups:
  • Ar 1 is selected from an aryl group having 6-15 carbon atoms or a heteroaryl group having 5-18 carbon atoms.
  • Ar 1 is selected from aryl groups having 6-14 carbon atoms or heteroaryl groups having 8-12 carbon atoms.
  • R 1 and R 2 are each independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, carbon atom Cycloalkyl groups with 5-10 carbon atoms, aryl groups with 6-15 carbon atoms, heteroaryl groups with 3-15 carbon atoms, alkoxy groups with 1-4 carbon atoms, 1 carbon atoms -4 alkylthio group, trialkylsilyl group having 3-7 carbon atoms.
  • R 1 and R 2 are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, and 6-12 aryl, carbon 3-12 heteroaryl, carbon 1-4 alkoxy, carbon 1-4 alkylthio, carbon 3-7 The trialkylsilyl group.
  • R 1 and R 2 respectively include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthalene Group, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, methoxy, ethoxy, methylthio, ethylthio, trimethylsilyl.
  • n 1 is selected from 0, 1 or 2
  • n 2 is selected from 0 or 1.
  • R 3 is selected from deuterium, fluorine, cyano, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, and alkyl groups having 1 to 4 carbon atoms.
  • R 3 include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio , Trimethylsilyl, trifluoromethyl.
  • n 3 is selected from 0, 1, or 2.
  • the nitrogen-containing compound may be selected from the group consisting of the following compounds:
  • L is selected from substituted or unsubstituted groups Q with 7-30 carbon atoms
  • group Q is selected from: bicyclic fused arylene, tricyclic fused arylene, and bicyclic fused heteroarylene
  • group Q is selected from: bicyclic fused arylene, tricyclic fused arylene, and bicyclic fused heteroarylene
  • aryl and tricyclic fused heteroarylene or selected from: monocyclic arylene, monocyclic heteroarylene, bicyclic fused arylene, tricyclic fused arylene, bicyclic fused
  • at least two groups in the heteroarylene group and the tricyclic fused heteroarylene group are connected to each other by a single bond to form a divalent group;
  • the substituted group Q means that the group Q has one or more substituents, and the substituents are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms , Heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, number of carbon atoms Is an alkoxy group having 1-10, an alkylthio group having 1-10 carbon atoms, and a trialkylsilyl group having 3-12 carbon atoms;
  • Ar 1 , Ar 2 and Ar 3 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms ;
  • the substituents in Ar 1 , Ar 2 and Ar 3 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3-18 carbon atom Heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and alkoxy groups with 1-10 carbon atoms , Alkylthio groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms;
  • R 1 and R 2 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, number of carbon atoms Cycloalkyl groups of 3-10, aryl groups of 6-20 carbon atoms, heteroaryl groups of 3-20 carbon atoms, alkoxy groups of 1-10 carbon atoms, 1- 10 alkylthio groups, trialkylsilyl groups with 3-12 carbon atoms;
  • n 1 represents the number of substituents R 1 , n 1 is selected from 0, 1, 2, 3 or 4, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 represents the number of substituents R 2 , n 2 is selected from 0, 1, 2 or 3, when n 2 is greater than 1, any two R 2 are the same or different.
  • an adamantane spiro-bound fluorenyl group is combined with a triarylamine, wherein the adamantane spiro-bound fluorenyl group has electron-rich properties and strong rigidity ,
  • This group has a high hole mobility; when it is combined with triarylamine, a material suitable for the hole transport layer of organic electroluminescent devices can be obtained; and the nitrogen-containing compounds of the present application also exist and
  • the central triaromatic amine is another triaromatic amine group bound by a group such as biphenyl or terphenyl (ie, L in Chemical Formula 1), where L has an appropriate conjugation range (for hole transport materials) ), while further improving the hole mobility, reducing the symmetry of the molecule, increasing the degree of freedom of the molecular structure, so that the material can exist more stably in the amorphous state; for example, the nitrogen-containing compound is applied to organic electricity
  • the nitrogen-containing compound is applied to organic electricity
  • the structure of the nitrogen-containing compound shown in Chemical Formula 2 is selected from the group consisting of Chemical Formula 2-1 to Chemical Formula 2-4:
  • R 1 and R 2 are the same or different, and are independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, and 1 to 4 carbon atoms Halogenated alkyl groups, cycloalkyl groups having 5-10 carbon atoms, aryl groups having 6-15 carbon atoms, heteroaryl groups having 5-10 carbon atoms, alkoxy groups having 1-4 carbon atoms, The alkylthio group having 1 to 4 carbon atoms, and the trialkylsilyl group having 3 to 7 carbon atoms.
  • n 1 is selected from 0, 1 or 2
  • n 2 is selected from 0 or 1.
  • the expression "optionally at least two groups selected from: monocyclic arylene" can be understood to include at least two of the same group, and may also include different groups. At least two in the group.
  • Q when the group Q is a group formed by two or three of the same group through a single bond, and the same group is a phenylene group, Q can be a biphenylene group or a terphenylene group;
  • Q when the group Q is a group formed by two different groups through a single bond, and the two groups are phenylene and dibenzofuranyl, Q is
  • L when the structure of L includes a fused aromatic ring or a fused heteroaromatic ring, the number of benzene rings connected to each other in a fused manner does not exceed 3.
  • Such L has a more suitable conjugation range, such as conjugated with Compared with more benzene rings fused to each other in a larger range (for example, four benzene rings fused to each other), the L of the present application can avoid the energy band from being too narrow, making the nitrogen-containing compound suitable as a hole transport material and improving Device performance.
  • the number of carbon atoms of L is, for example, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 , 27, 28, 29, 30.
  • L is selected from substituted or unsubstituted groups Q with 8-25 carbon atoms. Also optionally, L is selected from substituted or unsubstituted groups Q with 10-25 carbon atoms.
  • the substituents in the substituted group Q are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, carbon An alkoxy group having 1 to 4 atoms, an alkylthio group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, and a phenyl group.
  • the number of substituents in the substituted group Q is not more than 2.
  • L is the following group substituted: a bicyclic fused arylene group, a tricyclic fused arylene group, a bicyclic fused heteroarylene group, or a tricyclic fused heteroarylene group, And the substituent is phenyl.
  • the group Q is composed of a phenylene group and a bicyclic fused arylene group, a tricyclic fused arylene group, a bicyclic fused heteroarylene group, and a tricyclic fused heteroarylene group.
  • L is selected from the group consisting of the groups shown in chemical formula j-1 to chemical formula j-9:
  • M 2 is selected from a single bond or
  • Q 1 to Q 5 are each independently selected from N or C(F 4 ), and at least one of Q 1 to Q 5 is selected from N; when two or more of Q 1 to Q 5 are selected from C(F 4 ) , Any two F 4 are the same or different;
  • Q 6 to Q 13 are each independently selected from N or C(F 5 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(F 5 ) , Any two F 5s are the same or different;
  • Q 14 to Q 23 are each independently selected from N or C(F 6 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C(F 6 ) , Any two F 6 are the same or different;
  • E 1 to E 10 and F 4 to F 6 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3 to 10 carbon atoms, and 6 to 12 carbon atoms
  • Aryl group trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms , C1-C10 alkoxy group, C1-C10 alkylthio group;
  • E 1 ⁇ E 10 are represented by E r
  • e 1 ⁇ e 10 are represented by e r
  • r represents a variable and is selected from any integer from 1 to 10; when r is selected from 1, 2, 3, 4, 5 or 10
  • r is selected from 1, 2, 3 or 4
  • e r is selected from 1, 2, 3, 4, 5 or 6
  • e r is selected from 1, 2, 3, 4, 5 or 6
  • e r is selected from 1 , 2, 3, 4, 5, 6 or 7
  • er is 7, e r is selected from 1, 2, 3, 4, 5, 6, 7 or 8
  • e r is greater than 1, any two E r is the same or not the same
  • any two E r is the same or not the same
  • K 3 is selected from O, S, Se, N (E 11 ), C (E 12 E 13 ), Si (E 12 E 13 ); wherein, E 11 , E 12 , and E 13 are each independently selected from: carbon atoms An aryl group having 6 to 12, a heteroaryl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above E 12 and E 13 are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms they are connected to together;
  • K 4 is selected from single bond, O, S, Se, N (E 14 ), C (E 15 E 16 ), Si (E 15 E 16 ); wherein, E 14 , E 15 , and E 16 are each independently selected from : C6-C12 aryl group, C3-C10 heteroaryl group, C1-C10 alkyl group, C3-C10 cycloalkyl group, or the above E 15 and E 16 are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms to which they are commonly connected.
  • the ring formed by connecting the two groups in each group may be a 5-13 membered saturated or unsaturated ring.
  • the ring formed by connecting the two groups in each group is a 5-13 membered saturated aliphatic ring or aromatic ring.
  • the two groups of E 12 and E 13 , and the above-mentioned E 15 and E 16 can respectively form a saturated aliphatic monocyclic ring of 5-8 members or an aromatic ring of 10-13 members.
  • F 4 to F 6 can be represented by F x , where x is a variable and represents 4, 5, or 6.
  • F x refers to F 4 .
  • C (F x) when not connected to the positioning linkage C (F x) a, C (F x) in the absence of F x.
  • Q 8 when connected to Q 8 , Q 8 can only represent C atom, that is, the structure of chemical formula j-8 is:
  • L is selected from a substituted or unsubstituted group Q, and the unsubstituted group Q is selected from the group consisting of the following groups:
  • the substituted group Q has one or more than two substituents, and the substituents are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, 5- 10 cycloalkyl, carbon 1-4 alkoxy, carbon 1-4 fluoroalkyl, carbon 1-4 alkylthio, carbon 3-7
  • L is selected from the group consisting of the following groups:
  • L is selected from the group consisting of the following groups:
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, and substituted or unsubstituted carbon atoms having 5-25 Heteroaryl.
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from carbon atoms 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 selected from carbon atoms of 5, 8, 9, 11, 12, 16, 18, 20, 21, 22, 23, 24, 25 Substituted or unsubstituted heteroaryl.
  • the substituents in Ar 1 , Ar 2 and Ar 3 are each independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, 1 to 1 4 haloalkyl, carbon 5-10 cycloalkyl, carbon 1-4 alkoxy, carbon 1-4 alkylthio, carbon 3-7 three Alkylsilyl.
  • substituents in Ar 1 , Ar 2 , and Ar 3 include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, Cyclohexyl, phenyl, naphthyl, pyridyl, methoxy, ethoxy, methylthio, ethylthio, trimethylsilyl, trifluoromethyl, etc.
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted group Z, wherein the unsubstituted group Z is selected from the group consisting of the following groups:
  • the substituted group Z has one or more substituents, and the substituents are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, alkyl halide with 1-4 carbon atoms Group, carbon atoms of 5-10 cycloalkyl, carbon atoms of 1-4 alkoxy, carbon atoms of 1-4 alkylthio, carbon atoms of 3-7 trialkylsilyl; when substituted When the number of groups is greater than 1, the substituents are the same or different.
  • substituents include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, methoxy, methylsulfide Group, ethoxy group, trimethylsilyl, ethyldimethylsilyl, trifluoromethyl, etc.
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of the following groups:
  • Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of the following groups:
  • the nitrogen-containing compound is selected from the group consisting of the following compounds:
  • the application does not specifically limit the synthesis method of the nitrogen-containing compound provided, and those skilled in the art can determine a suitable synthesis method according to the preparation method of the nitrogen-containing compound provided in the application in combination with the synthesis example.
  • the synthesis example part of the present application exemplarily provides a method for preparing nitrogen-containing compounds, and the raw materials used can be obtained by commercially available or well-known methods in the art. Those skilled in the art can obtain all the nitrogen-containing compounds provided in this application according to the preparation methods of these exemplary synthesis examples. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Limitations of the invention.
  • the present application provides an electronic component.
  • the electronic component includes an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; the functional layer includes the nitrogen-containing Compound.
  • the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound.
  • the electronic component may be an organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100, a first hole transport layer 321, and a second hole transport layer 322 (also referred to as an "electron blocking layer"), which are sequentially stacked and arranged as an energy conversion layer.
  • the organic light emitting layer 330, the electron transport layer 340, and the cathode 200 are formed.
  • the first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320.
  • the nitrogen-containing compound provided in the present application can be applied to the first hole transport layer 321.
  • the nitrogen-containing compound provided in the present application can be applied to the second hole transport layer 322.
  • the hole transport layer 320 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided in the present application and other materials.
  • the nitrogen-containing compound shown in Chemical Formula 1 is applied to the first hole transport layer 321, and the material of the second hole transport layer 322 can be selected from carbazole polymers or other types of compounds, which is not particularly limited in this application.
  • it can be composed of the compound TCTA.
  • the nitrogen-containing compound shown in Chemical Formula 2 is applied to the second hole transport layer 322 of the organic electroluminescence device, and the material of the first hole transport layer 321 may be NPB, for example.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ] (PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to The host material, the host material transfers energy to the guest material, so that the guest material can emit light.
  • the host material of the organic light-emitting layer 330 may be, for example, a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, etc., which are not particularly limited in this application.
  • the host material of the organic light emitting layer 330 may be ⁇ , ⁇ -ADN, CBP, or PVK.
  • the guest material of the organic light-emitting layer 330 may be, for example, a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, and this application does not make any special considerations to this. limits.
  • the guest material of the organic light emitting layer 330 may be TBPe or Ir(piq) 2 (acac).
  • the electron transport layer 340 may have a single-layer structure or a multilayer structure, which may include one or more electron-transporting materials.
  • the electron-transporting materials may be selected from, but not limited to, benzimidazole derivatives, oxacin Diazole derivatives, quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 may be composed of TPBi and LiQ, or composed of TPO and LiQ.
  • a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the hole transport layer.
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 may be composed of HAT-CN.
  • an electron injection layer 350 may be further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340.
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfides, alkali metal halides, and Yb, or may include complexes of alkali metals and organic substances.
  • the electron injection layer 350 may include LiQ or Yb.
  • the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto. It is preferable to include a metal electrode containing silver and magnesium as a cathode.
  • the hole injection layer 310, the first hole transport layer 321, the second hole transport layer 322, the organic light emitting layer 330, the electron transport layer 340, and the electron injection layer 350 constitute the functional layer 300 .
  • the organic electroluminescent device is a blue light device or a red light device.
  • the electronic component may be a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a function disposed between the anode 100 and the cathode 200.
  • Layer 300; The functional layer 300 includes the nitrogen-containing compound provided in the present application.
  • the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the nitrogen-containing compound of the present application.
  • the hole transport layer 320 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided in the present application and other materials.
  • the hole transport layer 320 may further include inorganic doping materials to improve the hole transport performance of the hole transport layer 320.
  • the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200 that are sequentially stacked.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the hole transport layer contains the nitrogen-containing compound of the present application.
  • the present application provides an electronic device, which includes the above-mentioned electronic component.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, etc.
  • the electronic device is a second electronic device 500, and the second electronic device 500 includes the aforementioned photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • the raw materials C and D were synthesized by referring to the method of raw material A, except that 2-bromo-4-fluoro-1-iodobenzene was replaced with each raw material I, so that raw materials C and D were obtained accordingly.
  • the specific structure of raw material I, the structure of raw materials C and D, and the yield are shown in Table 1.
  • each raw material II is used instead of 2-bromo-4'-chlorobiphenyl.
  • the main raw materials used, the corresponding intermediate structure, and the total yield of the intermediate synthesis are shown in Table 2.
  • the intermediate 1A-1 (104.8g, 326.6mmol), 4-aminobiphenyl (58g, 342.9mmol), tris(dibenzylideneacetone) two palladium (2.99g, 3.26mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (2.68g, 6.53mmol) and sodium tert-butoxide (47.08g, 489.9mmol) were added to toluene (800mL), heated to reflux (105- 108°C), stirred for 0.5h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate, filtered, and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was recrystallized and purified with toluene to obtain a white solid intermediate lB-1 ( 100.75g, yield 68%).
  • each intermediate 1-A-X is adjusted, and each raw material III is used instead of 2-aminobiphenyl.
  • the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 3.
  • the intermediate 1B-1 (100.75g, 222.09mmol), p-chlorobromobenzene (59.42g, 310.36mmol), tris(dibenzylideneacetone)dipalladium (2.033g, 2.22mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (1.82g, 4.44mmol) and sodium tert-butoxide (32.015g, 333.14mmol) were added to toluene (800mL), heated to reflux (105- 108°C), stirred for 1h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified with toluene to obtain a white solid intermediate lC-1 (86g) , The yield is 68.6%).
  • each intermediate 1-B-X is adjusted, and the raw material IV is used instead of p-chlorobromobenzene.
  • the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 4.
  • the intermediate 1B-1 (100.75g, 222.09mmol), 4'-chloro-4-bromobiphenyl (59.42g, 222.09mmol), tris(dibenzylideneacetone)dipalladium (2.033g) , 2.22mmol), 2-dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (1.82g, 4.44mmol) and sodium tert-butoxide (32.015g, 333.14mmol) were added to toluene (800mL), Heat to reflux (105-108°C), stir for 1h; then cool to room temperature, wash the reaction solution with water and add magnesium sulfate to dry, filter and remove the solvent from the filtrate under reduced pressure; use toluene to recrystallize and purify the crude product to obtain a white solid intermediate Body 1-D-1 (91 g, yield 64%).
  • each intermediate 1-B-X is adjusted, and raw material V is used instead of p-chlorobromobenzene.
  • the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 5.
  • the nuclear magnetic data of compound B184 1 H NMR (CDCl 3 , 400Hz): 8.10 (d, 1H), 7.98 (s, 1H), 7.91 (d, 1H), 7.80 (m, 4H), 7.68-7.40 ( m, 12H), 7.34-7.26 (m, 13H), 7.10-6.92 (d, 4H), 2.90 (d, 2H), 2.63 (d, 2H), 2.17 (s, 1H), 1.89 (s, 3H) , 1.77 (d, 2H), 1.70 (d, 2H), 1.60 (s, 2H) ppm.
  • the substrate containing the light reflection layer plated with metallic Ag and the ITO anode was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and the photolithography process was used to prepare it into an experiment with a pattern of cathode, anode and insulating layer
  • the substrate (luminescent pixel size is 3mm ⁇ 3mm), using ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode (experimental substrate) and remove scum;
  • HIL hole injection layer
  • compound A61 is vapor-deposited on the hole injection layer to form a hole transport layer (HTL) with a thickness of 100 nm;
  • HTL hole transport layer
  • EBL electron blocking layer
  • ⁇ , ⁇ -ADN was vapor-deposited on the above electron blocking layer, and TBPe was used as a dopant at 3% (weight ratio) to form a light-emitting layer (EML) with a thickness of 20 nm;
  • TPO and LiQ were vapor-deposited on the light-emitting layer at a weight ratio of 1:1 to form a 28nm electron transport layer (ETL);
  • ETL electron transport layer
  • Ytterbium Yb is vapor-deposited on the above electron transport layer to form an electron injection layer (EIL) with a thickness of 1.5 nm;
  • magnesium (Mg) and silver (Ag) were vapor-deposited in a weight ratio of 1:10 to form a cathode with a thickness of 12 nm;
  • N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-biphenyl-4 with a thickness of 65nm was deposited on the above cathode.
  • DNTPD 4'-Diamine
  • the vapor-deposited device is encapsulated with ultraviolet curable resin in a nitrogen glove box.
  • An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compounds listed in Table 9 were used instead of Compound A61 of Example 1 when forming the hole transport layer (HTL).
  • HTL hole transport layer
  • NPB hole transport layer
  • the current efficiency of the organic electroluminescent devices in Examples 1 to 36 is at least 9.5% higher than the highest current efficiency (5.59Cd/A) in Comparative Examples 1 to 3; the external quantum of the organic electroluminescent devices in Examples 1 to 36 The efficiency is improved by at least 9.6% compared with the highest external quantum efficiency (11.5%) in Comparative Examples 1 to 3; the T95 lifetime of the organic electroluminescent devices of Examples 1 to 36 is the highest (202h) than the T95 lifetime of Comparative Examples 1 to 3 This is an increase of at least 38.6%. Compared with Comparative Examples 2 and 3, when the driving voltages of Examples 1 to 36 are basically unchanged, the efficiency and life span have been greatly improved.
  • the organic electroluminescence device was prepared by the following process: the anode ITO substrate (thickness 15nm) plated with the Ag alloy light reflection layer was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and the photolithography process was used to prepare it to have a cathode,
  • the anode and the experimental substrate with the insulating layer pattern are surface treated with ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode (experimental substrate) and remove scum.
  • the compound HAT-CN was vacuum-evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL);
  • the compound NPB is vacuum-evaporated on the hole injection layer to form a thickness of The first hole transport layer (HTL1).
  • the compound B1 was evaporated on the first hole transport layer (HTL1) as the second hole transport material (HTL2) with a thickness of
  • PVK poly(9-vinylcarbazole, CAS number; 25067-59-8) is vapor-deposited on the second hole transport layer, doped with Ir(piq) 2 (acac) with a film thickness ratio of 3%, The formation thickness is Organic light emitting layer (EML).
  • EML Organic light emitting layer
  • ETL organic light-emitting layer
  • TPBi and LiQ doped with a film thickness ratio of 1:1 are deposited as the electron transport layer (ETL), and the thickness is
  • the Yb serves as the electron injection layer (EIL).
  • the electron injection layer (EIL) is vapor-deposited with silver (Ag) and magnesium (Mg) doped with a film thickness ratio of 9:1 as the cathode, and the thickness is
  • the compound CP-1 is vapor-deposited on the cathode as an organic covering layer (CPL) with a thickness of
  • CPL organic covering layer
  • the structure of the main materials used is as follows:
  • the organic electroluminescence device was fabricated in the same manner as in Example 37, except that the compounds listed in Table 10 were used instead of the compound B1 of Example 37 when forming the second hole transport material (HTL2).
  • HTL2 second hole transport material
  • the organic electroluminescent devices obtained in Examples 37 to 94 have the characteristics of high efficiency and long life when the color coordinate CIEx is equivalent. .
  • the current efficiency of the organic electroluminescent devices of Examples 37 to 94 is 30.3Cd/A to 34.6Cd/A, which is at least 7.1% higher than the highest (28.3Cd/A) in the devices of Comparative Examples 5 to 8
  • the T95 device lifetime of the organic electroluminescent devices in Examples 37-94 is 470h-510h, which is at least 17.2% higher than the highest (420h) in the devices of Comparative Examples 5-8.
  • the driving voltage of the organic electroluminescent devices in Examples 37 to 94 was 3.51V to 3.78V, which was at least 0.11V lower than the lowest driving voltage (3.89V) of the devices in Comparative Examples 5 to 8.
  • the nitrogen-containing compound of the present application is used as a hole transport material, so that the organic electroluminescent device can further improve the efficiency and lifetime of the device while ensuring a lower driving voltage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne le domaine technique des matériaux organiques, et concerne un composé contenant de l'azote, un composant électronique et un dispositif électronique. Le composé contenant de l'azote a une structure représentée dans la formule (I). Le composé contenant de l'azote peut améliorer les performances du composant électronique.
PCT/CN2021/077730 2020-02-28 2021-02-24 Composé contenant de l'azote, composant électronique et dispositif électronique WO2021170008A1 (fr)

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CN202010777056.3 2020-08-05
CN202010777056.3A CN113321589B (zh) 2020-02-28 2020-08-05 含氮化合物、电子元件和电子装置
CN202011308317.3A CN113321588B (zh) 2020-02-28 2020-11-20 含氮化合物、电子元件和电子装置
CN202011308317.3 2020-11-20

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KR20190118515A (ko) * 2018-04-10 2019-10-18 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
KR20190118514A (ko) * 2018-04-10 2019-10-18 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
CN110467536A (zh) * 2019-06-14 2019-11-19 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和光电转化器件
WO2020080849A1 (fr) * 2018-10-17 2020-04-23 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
WO2020159279A1 (fr) * 2019-02-01 2020-08-06 주식회사 엘지화학 Composé polycyclique et élément électroluminescent organique le comprenant
CN111699191A (zh) * 2018-10-18 2020-09-22 株式会社Lg化学 杂环化合物及包含其的有机发光器件
CN111875505A (zh) * 2019-12-20 2020-11-03 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和电子装置

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107459466A (zh) * 2016-06-02 2017-12-12 株式会社Lg化学 化合物及包含它的有机电子元件
KR20190118515A (ko) * 2018-04-10 2019-10-18 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
KR20190118514A (ko) * 2018-04-10 2019-10-18 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
WO2020080849A1 (fr) * 2018-10-17 2020-04-23 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
CN111699191A (zh) * 2018-10-18 2020-09-22 株式会社Lg化学 杂环化合物及包含其的有机发光器件
WO2020159279A1 (fr) * 2019-02-01 2020-08-06 주식회사 엘지화학 Composé polycyclique et élément électroluminescent organique le comprenant
CN110128279A (zh) * 2019-06-14 2019-08-16 陕西莱特光电材料股份有限公司 有机电致发光材料及包含该材料的有机电致发光器件
CN110467536A (zh) * 2019-06-14 2019-11-19 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和光电转化器件
CN111875505A (zh) * 2019-12-20 2020-11-03 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件和电子装置

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