WO2022218112A1 - 有机化合物以及使用其的有机电致发光器件和电子装置 - Google Patents

有机化合物以及使用其的有机电致发光器件和电子装置 Download PDF

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WO2022218112A1
WO2022218112A1 PCT/CN2022/082341 CN2022082341W WO2022218112A1 WO 2022218112 A1 WO2022218112 A1 WO 2022218112A1 CN 2022082341 W CN2022082341 W CN 2022082341W WO 2022218112 A1 WO2022218112 A1 WO 2022218112A1
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carbon atoms
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substituted
unsubstituted
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French (fr)
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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 belongs to the technical field of organic materials, and specifically provides an organic compound and an organic electroluminescence device and electronic device using the same.
  • Organic electroluminescent materials are thin-film devices prepared from organic photoelectric functional materials that emit light under the excitation of an electric field.
  • OLED has been widely used in mobile phones, computers, lighting and other fields due to its advantages of high brightness, fast response and wide adaptability.
  • organic electroluminescent devices In addition to the electrode material layer, organic electroluminescent devices also need to be composed of different organic functional materials, and the ⁇ -bond or anti- ⁇ -bond orbitals of organic functional materials form shifted valence and conduction properties, and their overlap produces the highest occupation, respectively.
  • HOMO Orbital
  • LUMO Molecular Lowest Unoccupied Orbital
  • a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.
  • These organic layers have the ability to improve the injection efficiency of carriers (holes and electrons) at the interface of each layer and balance the ability of carrier transport between layers, thereby improving the brightness and efficiency of the device.
  • the purpose of the present application is to provide an organic compound and an organic electroluminescent device and electronic device using the same.
  • the organic compound of the present application is used in an electron transport layer and/or a light-emitting layer material of an electronic device, the light emission of the electronic device can be improved. Efficiency and service life.
  • a first aspect of the present application provides an organic compound, and the structure of the organic compound is shown in Formula 1:
  • R 5 and R 6 are the same or different from each other, and are independently selected from alkyl groups having 1 to 6 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, and alkyl groups having 3 to 10 carbon atoms.
  • Cycloalkyl, substituted or unsubstituted aryl group with 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 12 carbon atoms, or R 5 and R 6 are connected to each other to be common with them
  • the connected carbon atoms together form a 5-18-membered aliphatic ring, a substituted or unsubstituted 5-18-membered aromatic ring, and the substituents on the 5-18-membered aromatic ring are each independently selected from deuterium, halogen group or carbon
  • Each of R 1 , R 2 , R 3 and R 4 is the same as or different from each other, and is independently selected from the group represented by formula 2, the aryl group having 6 to 20 carbon atoms, and the aryl group having 3 to 20 carbon atoms.
  • Heteroaryl hydrogen, deuterium, halogen group, cyano group, alkyl group with 1 to 10 carbon atoms, halogenated alkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or a trialkylsilyl group having 3 to 12 carbon atoms, and the R 1 , R 2 , R 3 and Any one or two of R 4 are groups represented by formula 2;
  • Het is a 6-18-membered electron-deficient nitrogen-containing heteroarylene
  • L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms ;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms base;
  • n 1 and n 4 are the same or different from each other, respectively represent the number of R 1 and R 4 , and are independently selected from 1, 2, 3 or 4, and n 3 represents the number of R 3 , selected from 1 or 2; n 2 represents the number of R 2 , selected from 1, 2 or 3;
  • the substituents in the L 1 , L 2 , L 3 , Ar 1 , Ar 2 , R 5 and R 6 are the same or different, and are each independently selected from deuterium, cyano, halogen, and carbon atoms ranging from 1 to 1.
  • any two adjacent substituents form a substituted or unsubstituted 5- to 15-membered ring
  • the substituents on the 5- to 15-membered ring are independently selected from deuterium, cyano group, halogen group, alkyl group with 1 to 4 carbon atoms, haloalkyl group with 1 to 4 carbon atoms, deuterated alkyl group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 6 carbon atoms , an aryl group with 6-12 carbon atoms or a heteroaryl group with 5-12 carbon atoms.
  • a second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the device provided in the first aspect of the present application organic compounds.
  • the functional layer includes an electron transport layer and/or a light-emitting layer, and the electron transport layer and/or the light-emitting layer contains the organic compound.
  • a third aspect of the present application provides an electronic device, including the organic electroluminescent device of the second aspect of the present application.
  • the organic compound of the present application has a carbazolofluorene-type fused-ring parent nucleus, and the parent nucleus is bound with a nitrogen-containing electron transport group, wherein the parent nucleus structure has a large conjugated system, and its electron density distribution is conducive to enhancing the empty space. hole mobility.
  • the carbon atom of the fluorene ring on the parent nucleus has two substituents, which can adjust the spatial structure of the parent nucleus, effectively avoid stacking between molecules, and improve the stability of film formation.
  • the nitrogen-containing electron-deficient group with high electron mobility is used as the electron-injecting group, and it is connected to the benzene ring of the parent nucleus through a conjugated single bond, so that the dipole moment on both sides of the organic compound molecule is increased, and the triplet state
  • the energy level is increased, so the carrier migration stability can be improved.
  • the organic compound of the present application can be used as the host material of the electron transport layer and/or the light-emitting layer of the organic light-emitting device, which can effectively improve the lifespan and light-emitting efficiency of the device.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
  • hole transport layer 321 hole transport layer 322, hole adjustment layer 330, light-emitting layer
  • a first aspect of the present application provides an organic compound, and the structure of the organic compound is shown in Formula 1:
  • R 5 and R 6 are the same or different from each other, and are independently selected from alkyl groups having 1 to 6 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, and alkyl groups having 3 to 10 carbon atoms.
  • Cycloalkyl, substituted or unsubstituted aryl group with 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 12 carbon atoms, or R 5 and R 6 are connected to each other to be common with them
  • the connected carbon atoms together form a 5-18-membered aliphatic ring, a substituted or unsubstituted 5-18-membered aromatic ring, and the substituents on the 5-18-membered aromatic ring are each independently selected from deuterium, halogen group or carbon
  • Each of R 1 , R 2 , R 3 and R 4 is the same as or different from each other, and is independently selected from the group represented by Chemical Formula 2, an aryl group having 6 to 20 carbon atoms, and a group having 3 to 20 carbon atoms.
  • Heteroaryl hydrogen, deuterium, halogen group, cyano group, alkyl group with 1 to 10 carbon atoms, halogenated alkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or a trialkylsilyl group having 3 to 12 carbon atoms, and the R 1 , R 2 , R 3 and Any one or any two of R 4 is a group represented by formula 2:;
  • Het is a 6-18-membered electron-deficient nitrogen-containing heteroarylene
  • L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms ;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms base;
  • n 1 and n 4 are the same or different from each other, respectively represent the number of R 1 and R 4 , and are independently selected from 1, 2, 3 or 4, and n 3 represents the number of R 3 , selected from 1 or 2; n 2 represents the number of R 2 , selected from 1, 2 or 3;
  • the substituents in the L 1 , L 2 , L 3 , Ar 1 , Ar 2 , R 5 and R 6 are the same or different, and are each independently selected from deuterium, cyano, halogen, and carbon atoms ranging from 1 to 1.
  • any two adjacent substituents form a substituted or unsubstituted 5-15-membered ring
  • the substituents on the 5-15-membered ring are independently selected from deuterium, cyano group, halogen group, alkyl group with 1 to 4 carbon atoms, haloalkyl group with 1 to 4 carbon atoms, deuterated alkyl group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 6 carbon atoms , an aryl group with 6-12 carbon atoms or a heteroaryl group with 5-12 carbon atoms.
  • the organic compound of the present application has a fused ring structure of carbazolofluorene, which can form a large rigid planar structure, which can effectively improve the hole mobility of the material; and the structure of the 9-position double substituent of fluorene can effectively avoid stacking between compounds , improve the film formation stability and thermal stability, which can effectively improve the life of the device.
  • Connecting electron-deficient nitrogen-containing heteroaryl groups to the fused ring structure can greatly improve the material's ability to attract electrons and improve electron mobility. Electron and hole transport ability.
  • the organic compound of the present invention is used as the host material of the electron transport layer or the light-emitting layer of the organic light-emitting device, the light-emitting efficiency and service life of the device can be improved.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is: 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.
  • 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.
  • substituents namely Rc
  • Rc can be, for example, deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, and deuterated alkyl groups with 1 to 10 carbon atoms.
  • cycloalkyl with 3-10 carbon atoms aryl group with 6-20 carbon atoms, heteroaryl group with 3-20 carbon atoms, alkoxy group with 1-10 carbon atoms, 1- 10 alkylthio groups, 1-12 carbon atoms trialkylsilyl group, 6-18 carbon atoms arylsilyl group, 6-20 carbon atoms aryloxy group, 6 carbon atoms ⁇ 20 arylthio groups.
  • Substituted functional groups may be substituted by one or more of the above-mentioned Rc substituents; when two substituents Rc are attached to the same atom, the two substituents Rc may exist independently or be attached to each other to Form a ring; when there are two adjacent substituents Rc on a functional group, the two adjacent substituents Rc can exist independently or be condensed into a ring with the functional group to which they are connected. When two adjacent substituents Rc are connected to the same atom, the two substituents Rc can exist independently or form a ring by spiro 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.
  • Ar 1 is a substituted aryl group having 20 carbon atoms, all of the aryl group and the substituents thereon have 20 carbon atoms.
  • the number of carbon atoms of L 1 , L 2 , L 3 , Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 refers to all carbon atoms.
  • L 1 is a substituted arylene group with 12 carbon atoms, then the total number of carbon atoms in the arylene group and the substituents on it is 12.
  • Ar 1 is Then the number of carbon atoms is 15; L 1 is The number of carbon atoms is 12.
  • aryloxy means alkoxy substituted with aryl.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups linked by A single-ring aryl group and a fused-ring aryl group linked by carbon-carbon bonds, and two or more fused-ring aryl groups linked by a carbon-carbon bond.
  • Fused-ring aryl refers to two or more rings in which the two carbon atoms in the ring system are shared by two adjacent rings, wherein at least one of the rings is aromatic, for example the other rings may be naphthenic base, cycloalkenyl, aryl.
  • aryl groups in this application may include, but are not limited to, phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, group, perylene group, fluorenyl group, triphenylene group, naphthacyl group, triphenylenyl and the like.
  • condensed aromatic rings refer to polyaromatic rings formed by two or more aromatic or heteroaromatic rings sharing a ring edge, such as naphthalene, anthracene, phenanthrene, and pyrene.
  • the fluorenyl group may be substituted, and two substituent groups may be combined with each other to form a spiro ring structure.
  • the substituted fluorenyl group may be:
  • a substituted aryl group means that one or two or more hydrogen atoms in an aryl group are replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group , alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group , alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituent on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and the substituted aryl group.
  • the total number of carbon atoms in the base is 18.
  • aryl groups as substituents may include, but are not limited to, phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, fluorenyl, dimethylfluorenyl, pyrenyl, perylene base.
  • the aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and in other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms, In other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-20 carbon atoms, and in other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-18 carbon atoms, In other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-15 carbon atoms, and in other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-13 carbon atoms, In other embodiments, the aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • the number of carbon atoms of a substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 18, 20, 24, 25 or 30, of course, the number of carbon atoms can also be other numbers, which will not be listed here.
  • biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.
  • the arylene group is a divalent group, and other than that, the above-mentioned description about the aryl group can be applied.
  • heteroaryl refers to a monocyclic or polycyclic ring containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms independently selected from O, N, P, Si, Se, B and S in the ring. ring systems, at least one of which is aromatic. Each ring system in a heteroaryl group contains a ring of 5-7 ring atoms with one or more points of attachment to the rest of the molecule.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • Fused ring heteroaryl refers to two or more rings in which the two atoms in the ring system are shared by two adjacent rings, wherein at least one of the rings is aromatic, for example the other ring may be a cycloalkane base, heterocyclyl, cycloalkenyl, aryl.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, phenanthridine , pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyrido Pyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzocarbazolyl, benzothienyl, dibenzothiophene base, thieno
  • thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
  • a substituted heteroaryl group means that one or more than two hydrogen atoms in the heteroaryl group are replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl 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 trialkylsilyl 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.
  • a substituted heteroaryl group having 14 carbon atoms means
  • heteroaryl groups as substituents include, but are not limited to, dibenzothienyl, dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, pyridyl, bipyridyl, pyrimidine group, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, indolyl, phenanthroline.
  • the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 3 to 12 carbon atoms
  • the substituted or unsubstituted heteroaryl group is a carbon number is a substituted or unsubstituted heteroaryl group of 3 to 15, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group of 5 to 12 carbon atoms, and in other embodiments Among them, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.
  • the number of carbon atoms of the substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms may be 3, 4, 5, 7, 12, 13, 14, 15, 16, 18 one, 20, 24, 25 or 30, of course, the number of carbon atoms may also be other numbers, which will not be listed here.
  • an electron-deficient nitrogen-containing ()heteroaryl group refers to a ()heteroaryl group containing at least one sp 2 hybridized nitrogen atom, and the lone pair of electrons in the nitrogen atom in this type of heteroaryl group does not participate in the common yoke, so the overall electron density is lower.
  • "6-18-membered electron-deficient nitrogen-containing heteroarylene group” is a heteroaromatic ring formed by 6-18 atoms and containing sp 2 hybridized nitrogen atoms.
  • pyridyl pyrimidinyl, triazinyl, pyridazinyl, pyrazinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxa pyridinoline, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, benzimidazolyl, benzothiazolyl, phenanthroline and the like.
  • the heteroarylene group is a divalent or higher-valent group, and other than that, the above description about the heteroaryl group can be applied.
  • alkyl includes saturated linear or branched, monovalent or polyvalent hydrocarbon groups of 1 to 10 carbon atoms.
  • the alkyl group contains 1-10 carbon atoms; in other embodiments, the alkyl group contains 1-8 carbon atoms; in other embodiments, the alkyl group contains 1-6 carbon atoms; in other embodiments, the alkyl group contains 1-6 carbon atoms; In one embodiment, the alkyl group contains 1-4 carbon atoms; in other embodiments, the alkyl group contains 1-3 carbon atoms.
  • alkyl group having 1 to 4 carbon atoms as a substituent examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc.
  • the halogen group may be fluorine, chlorine, bromine, iodine.
  • alkoxy means that an alkyl group is attached to the rest of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein.
  • alkoxy groups as substituents include, but are not limited to, methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-methyl-1-propoxy oxy, 2-butoxy, 2-methyl-2-propoxy, and the like.
  • trialkylsilyl refers to Wherein, R G1 , R G2 and R G3 are independently alkyl groups, and specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl base, propyldimethylsilyl.
  • haloalkyl means an alkyl group substituted with one or more halogen atoms, wherein the alkyl group has the meaning as described herein.
  • the haloalkyl group having 1 to 4 carbon atoms includes a fluorine substituted alkyl group having 1 to 4 carbon atoms, examples of which include, but are not limited to, trifluoromethyl, difluoromethyl , 1-fluoro-2-chloroethyl, etc.
  • Ring in this application includes saturated ring, unsaturated ring; saturated ring, namely cycloalkyl, heterocycloalkyl; unsaturated ring, namely cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
  • n-membered ring a ring system formed by n ring atoms is referred to as an "n-membered ring".
  • phenyl is a 6-membered aryl group.
  • a 5- to 10-membered aromatic ring refers to an aryl or heteroaryl group containing 5 to 10 ring atoms;
  • a 5- to 10-membered aliphatic ring refers to a cycloalkyl or cycloalkenyl group containing 5 to 10 ring atoms.
  • the 5-15-membered ring is a ring system with 5-15 ring atoms, and the ring system can be an aliphatic ring or an aromatic ring, such as but not limited to cyclopentane, cyclohexane, and fluorene ring.
  • a 5- to 18-membered aromatic ring is a ring system having 5 to 18 ring atoms and including an aromatic ring.
  • the fluorene ring is a 13-membered aromatic ring. is a substituted 14-membered aromatic ring.
  • any two adjacent substituents form a ring means that two adjacent substituents may or may not form a ring, and this scheme includes the scenario where two substituents are connected to each other to form a ring, Scenarios where two substituents are present independently of each other are also included.
  • two adjacent substituents may exist in the form of a saturated or unsaturated ring, or may exist independently of each other.
  • a non-positioned connecting bond refers to a single bond extending from the ring system and 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 dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of one side of the benzene ring, which The meaning represented includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • the organic compound has the structure shown in the following formula 1-1, 1-2, 1-3 or 1-4:
  • each R 1 , R 2 , R 3 and R 4 are the same or different from each other, and are independently selected from hydrogen, deuterium, fluorine, cyano, phenyl, naphthyl, pyridyl, methyl, ethyl, tertiary Butyl, isopropyl, trifluoromethyl, trideuteromethyl or trimethylsilyl.
  • any one of R 1 , R 2 , R 3 and R 4 is the group shown in Chemical Formula 2, and the rest are hydrogen.
  • each of said R 5 and R 6 is independently methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, benzene base, naphthyl, biphenyl, fluorenyl, dimethylfluorenyl, anthracenyl, phenanthryl, pyridyl, dibenzothienyl, dibenzofuranyl or carbazolyl, or R 5 and R 6 are mutually linked to form a fluorene ring, cyclopentane, cyclohexane or
  • the R and R are each independently selected from methyl or the following groups:
  • R and R are attached to each other to form one of the following spiro rings together with the carbon atom to which they are commonly attached:
  • any one or two of R 1 , R 2 , R 3 and R 4 in the organic compound represented by formula 1 are groups represented by formula 2:
  • Het is a 6-18-membered electron-deficient nitrogen-containing heteroarylene.
  • the sp 2 hybridized nitrogen atom on Het can reduce the electron cloud density of the conjugated system of the heteroarylene as a whole instead of increasing the heteroarylene.
  • the electron cloud density of the conjugated system, the lone pair of electrons on the heteroatom does not participate in the conjugated system, and the electron cloud density of the conjugated system is reduced due to the strong electronegativity of the heteroatom.
  • the Het group can form the electron transport core group of the compound, so that the compound can effectively realize electron transport and can effectively balance the transport rates of electrons and holes in the light-emitting layer.
  • the compound can be used as the host material of the bipolar organic light-emitting layer to simultaneously transport electrons and holes, can also be used as the host material of the electron-type organic light-emitting layer in combination with the host material of the hole-type organic light-emitting layer, and can also be used as an electron transport material. .
  • the Het group is selected from the group consisting of triazinylene, pyridylene, pyrimidylene, quinolinylene, quinoxalylene, quinazolinylene, isoquinolinylene base, benzimidazolyl, benzothiazolyl, benzoxazolyl, phenanthroline, benzoquinazoline, phenanthroimidazolyl, benzofuranopyrimidinyl, phenanthroline benzothienopyrimidinyl or selected from the group consisting of:
  • Het is selected from the group consisting of:
  • Het is selected from the group consisting of the following nitrogen-containing heteroarylenes:
  • the Het group in Formula 1 is a triazine group
  • a better balance is achieved between the hole mobility and electron mobility of the compound, and when used in the light-emitting layer of the device, the efficiency of the device better.
  • the L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-18 carbon atoms, a 5-18 carbon atom The substituted or unsubstituted heteroarylene of 12.
  • the substituents in L 1 , L 2 and L 3 are each independently selected from deuterium, cyano, fluorine, alkyl with 1-5 carbon atoms, and haloalkane with 1-5 carbon atoms group, deuterated alkyl group having 1 to 5 carbon atoms, aryl group or pyridyl group having 6 to 12 carbon atoms.
  • the L 1 , L 2 and L 3 are each independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted Biphenylene, substituted or unsubstituted anthracylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted phenylene Dibenzofuranyl, substituted or unsubstituted carbazolylylene; the substituents in the L 1 , L 2 and L 3 are each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl radical, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, nap
  • the L 1 , L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted group W, and the unsubstituted group W is selected from the following groups:
  • substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n- Butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl or pyridyl.
  • the L 1 , L 2 and L 3 are each independently selected from a single bond or from the following groups:
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and 5-20 substituted or unsubstituted heteroaryl groups.
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, cyano, fluorine, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, carbon A deuterated alkyl group having 1 to 5 atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.
  • any two adjacent substituents form a substituted or unsubstituted 5-13-membered ring
  • the substituents on the 5-13-membered ring are selected from deuterium, cyano, halogen group, alkyl group with 1 to 4 carbon atoms, haloalkyl group with 1 to 4 carbon atoms, deuterated alkyl group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 6 carbon atoms, carbon atom An aryl group having 6 to 12 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms.
  • the number of carbon atoms of a substituted or unsubstituted aryl group may be selected from 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25, or 30 carbon atoms.
  • the number of carbon atoms of a substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 , 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Substituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobi Fluorenyl; the substituents
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted group Y, and unsubstituted group Y is selected from the following groups group:
  • substituents are independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, n- Butyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl or pyridyl.
  • the Ar 1 and Ar 2 are the same or different, and each is independently selected from the group consisting of hydrogen, deuterium or the following groups:
  • the organic compound is selected from the group consisting of the following organic compounds.
  • a second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the device provided in the first aspect of the present application the organic compound.
  • the functional layer includes an electron transport layer, and the electron transport layer contains the organic compound.
  • the electron transport layer may be composed of the organic compound provided in this application, or may be composed of the organic compound provided in this application and other materials, and the electron transport layer may be one layer or more than two layers.
  • the functional layer includes a light-emitting layer, and the light-emitting layer contains the organic compound.
  • the host material in the light-emitting layer may be composed of the organic compound provided in this application, or may be composed of the organic compound provided in this application and other materials.
  • the organic electroluminescence device may include an anode 100 , a first hole transport layer 321 , a hole adjustment layer 322 , a light emitting layer 330 as an energy conversion layer, an electron transport layer 340 and a cathode 200 , which are sequentially stacked. .
  • 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.
  • the electronic component comprises a transparent electrode with indium tin oxide (ITO) as the anode.
  • the first hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. There are no special restrictions on the application.
  • the first hole transport layer 321 is composed of the compound PAPB.
  • the hole adjustment layer 322 may include triarylamine compounds or other types of compounds.
  • the hole adjustment layer consists of PAPB.
  • the light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a dopant material.
  • the light-emitting layer 330 is composed of a host material and a dopant material, the holes injected into the light-emitting layer 330 and the electrons injected into the light-emitting layer 330 can recombine in the light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, The host material transfers energy to the dopant material, which in turn enables the dopant material to emit light.
  • the host material of the light-emitting layer 330 may be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials.
  • the host material of the light-emitting layer contains the compound described in this application.
  • the doping material of the light-emitting layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not specially made in this application. limit.
  • the light-emitting layer 330 contains the compound Ir(piq) 2 (acac) and the organic compound of the present application as the host of the light-emitting layer.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, the organic compounds of the present application, benzene imidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 consists of ET-06 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 contains LiQ.
  • a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the capability of injecting holes into the first hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 contains F4-TCNQ.
  • a third aspect of the present application provides an electronic device, including the organic electroluminescence device provided in the second aspect of the present application.
  • the electronic device is an electronic device 400
  • the electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • reaction in each synthesis example is generally carried out under the positive pressure of nitrogen or argon, or a drying tube is set on the anhydrous solvent (unless otherwise stated); in the reaction, the reaction flask is plugged with a suitable rubber stopper, The substrate is injected into the reaction vial via a syringe. All glassware used was dried.
  • the chromatographic column was a silica gel column, and silica gel (100-200 mesh) was purchased from Qingdao Ocean Chemical Factory.
  • the measurement conditions of low-resolution mass spectrometry (MS) data are: Agilent 6120 quadrupole HPLC-M (column type: Zorbax SB-C18, 2.1 ⁇ 30 mm, 3.5 microns, 6 min, flow rate 0.6 mL/ min.
  • Mobile phase 5%-95% (acetonitrile with 0.1% formic acid) in (water with 0.1% formic acid) using electrospray ionization (ESI) at 210nm/254nm with UV detection.
  • ESI electrospray ionization
  • Hydrogen nuclear magnetic resonance spectrum Bruker 400MHz nuclear magnetic instrument, at room temperature, with CDCl 3 as solvent (in ppm), with TMS (0 ppm) as reference standard. When multiplets are present, the following abbreviations will be used: s (singlet), d (doublet), t (triplet), m (multiplet).
  • Each intermediate SA-3-X listed in Table 1 was synthesized with reference to the synthesis method of intermediate SA-3-1 (X is a variable, representing an integer from 1 to 20, the same below), the difference is that SA-1 is used -X replaces raw material SA-1-1, and SA-2-X replaces SA-2-1.
  • SA-3-1 (209g, 641.44mmol), acetic acid (990mL) and phosphoric acid (55mL) were added to the three-necked flask, the temperature was raised to 50°C, stirred until clear, and reacted for 4h. NaOH aqueous solution was neutralized, ethyl acetate was added to the solution for extraction, the organic phase was collected, dried over anhydrous magnesium sulfate, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain intermediate SA-4- 1 (132.20 g, yield: 67%).
  • SB-1-1 (124 g, 366.86 mmol) and dry THF (744 mL) were added to the three-necked flask, and cooled to -10° C.
  • SB-3-1 (69.84 g, 385.20 mmol) was added, and the reaction was stirred continuously to make the reaction liter
  • saturated NH 4 Cl solution 500 mL was added for quenching
  • ethyl acetate was added to the reaction solution for extraction, and the organic phase was washed with water, then dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure.
  • the intermediate SB-4-X shown in the following table 4 was synthesized with reference to the synthetic method of the intermediate SB-4-1, the difference is that SB-1-X is used instead of SB-1-1, and SB-3-X is used Replaces SB-3-1.
  • SB-2-1 130 g, 401.21 mmol
  • SB-5-1 56.83 g, 401.21 mmol
  • dioxane, potassium tert-butoxide 112.34 g, 1003.03 mmol
  • Pd 2 (dba) 3 3.82 g, 4.01 mmol
  • iodomethane 56.95 g, 401.21 mmol
  • intermediate SB-3-2a 8 mL of hydrochloric acid solution was added dropwise to quench the reaction, extracted with ethyl acetate, the separated organic phase was washed with saturated brine, and the solvent was removed from the organic phase under reduced pressure to obtain intermediate SB-3-2a.
  • feed into a 2L dry three-necked flask add 1335mL of acetic acid and 20g of hydrochloric acid whose mass fraction is 36%, heat up to reflux and stir for 3h to complete the reaction. After cooling to room temperature, it was filtered, washed twice with water, dried, and purified by silica gel column chromatography to obtain intermediate SB-9-1 (123.40 g, yield: 57.5%).
  • the intermediate SC-3-2 shown in Table 8 was synthesized with reference to the synthesis method of the intermediate SC-3-1, except that SC-2-2 was used instead of SC-2-1.
  • the intermediate SC-4-2 shown in Table 9 below was synthesized according to the synthesis method of the intermediate SC-4-1, except that the intermediate SC-3-2 was used instead of the intermediate SC-3-1.
  • Each intermediate Y-1-X listed in Table 10 was synthesized with reference to the synthesis method of intermediate A-1-1 (Y is a variable, representing A, B or C), the difference is that each SY-X-X is used instead of SA-4-1.
  • A-1-1 (97.5 g, 357.75 mmol), A-2-1 (89.08 g, 357.75 mmol) were added to the three-necked flask, and THF (582 mL) and H 2 O (194 mL) were added, Heating and stirring until clear, then adding Pd(PPh 3 ) 4 (0.43 g, 3.76 mmol), K 2 CO 3 (77.78 g, 563.63 mmol), heating under reflux and stirring for 15 h, the reaction was complete.
  • A-3-1 (84.67 g, 242.05 mmol) was added to the three-necked flask, dissolved in 400 mL of o-dichlorobenzene, triphenylphosphine (1.27 g, 4.84 mmol) was added, and the temperature was heated at 170° C. to 190° C.
  • the reaction was stirred for 12-16 h, cooled to room temperature after the reaction was completed, filtered, the filtrate was evaporated to dryness under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain Intermediate A-5-1 (50 g, yield: 65.1%).
  • Each intermediate A-5-X, B-4-X, C-4-X listed in Table 12 was synthesized with reference to the synthesis method of intermediate A-5-1, except that intermediate A-3 was used -X or B-3-X or C-3-X in place of intermediate A-3-1.
  • Each intermediate A-7-X, B-6-X, C-6-X listed in Table 13 was synthesized with reference to the synthesis method of intermediate A-7-1, except that A-5-X or B-4-X or C-4-X was used in place of intermediate A-5-1 and A-6-X was used in place of A-6-1.
  • Each intermediate A-10-X, B-8-X, C-8-1 listed in Table 15 was synthesized with reference to the synthesis method of intermediate A-10-1, except that intermediate A-8 was used -X or B-7-X or C-7-1 in place of intermediate A-8-1.
  • intermediates A-13-X, B-13-X, C-13-1 listed in Table 17 were synthesized with reference to the synthesis method of intermediate A-13-1, except that intermediate A-12- X or B-10-X or C-10-1 replace intermediate A-12-1.
  • intermediates A-15-X, B-15-X, and C-15-1 listed in Table 18 were synthesized with reference to the synthesis method of intermediate A-15-1, except that starting material A was used instead of intermediate A -10-1.
  • Each intermediate A-17-X, B-17-X, C-17-X listed in Table 19 was synthesized with reference to the synthesis method of intermediate A-17-1, except that intermediate A-15 was used -X or B-15-X or C-15-X in place of intermediate A-15-1 and starting material A-16-X in place of A-16-1.
  • Each compound X listed in Table 20 was synthesized with reference to the synthesis method of compound 1, except that intermediate A-17-X or B-17-X or C-17-X was used instead of intermediate A-17-1 , using raw material A-16-X instead of raw material A-16-3.
  • Example 1 Red organic electroluminescent device
  • Anodes were prepared by the following process: ITO thickness was The substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers. UV ozone and O 2 : N 2 plasma were used for surface treatment. Treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL).
  • NPB was vacuum evaporated to form a thickness of the first hole transport layer (HTL-1), and vacuum evaporation of PAPB on the first hole transport layer to form the hole adjusting layer.
  • HTL-1 first hole transport layer
  • compound 1:Ir(piq) 2 (acac) was co-evaporated at a film thickness ratio of 97%:3% to form a thickness of The red light emitting layer (R-EML).
  • ET-06 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • CP-05 was vapor-deposited on the above-mentioned cathode to form a thickness of the organic capping layer (CPL), thereby completing the fabrication of organic electroluminescent devices.
  • CPL organic capping layer
  • the driving voltage of the organic electroluminescence device is at least A reduction of 0.1V increases the current efficiency (Cd/A) by at least 10.9% and the lifetime by at least 32%.

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Abstract

本申请涉及一种有机化合物，其结构中包含电子输注基团和共轭稠合杂芳环，可以用于有机电致发光器件的功能层中。本申请的有机化合物用于有机电致发光器件中可以提高器件的发光效率和使用寿命。

Description

有机化合物以及使用其的有机电致发光器件和电子装置
相关申请的交叉引用
本申请要求于2021年4月16日递交的申请号为CN202110414338.1的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本请属于有机材料技术领域，具体提供一种有机化合物以及使用其的有机电致发光器件和电子装置。
背景技术
有机电致发光材料是通过有机光电功能材料制备的薄膜器件在电场的激发下进行发光。目前，OLED由于其亮度高、响应快、适应性广等优点已广泛备用于手机、电脑、照明等领域。
有机电致发光器件除了电极材料膜层，还需要不同有机功能材料组成，而有机功能材料的π键或反π键轨道形成了移位的原子价和传导性能，其交迭分别产生了最高占据轨道(HOMO)和分子最低空轨道(LUMO)，通过分子间跳跃产生电荷传输。
为了提高有机电致发光器件的亮度、效率和寿命，一般采用多层结构，包括：空穴注入层、空穴传输层、发光层和电子传输层等。这些有机层具有提高载流子(空穴和电子)在各层界面间的注入效率，平衡载流子在各层之间传输的能力，从而提高器件的亮度和效率。
发明内容
本申请的目的是提供一种有机化合物以及使用其的有机电致发光器件和电子装置，将本申请的有机化合物用于电子装置的电子传输层和/或发光层材料时可以提高电子装置的发光效率和使用寿命。
本申请第一方面提供一种有机化合物，所述有机化合物的结构如式1所示：
Figure PCTCN2022082341-appb-000001
式1中，R 5和R 6彼此相同或不同，且分别独立地选自碳原子数为1～6的烷基、碳原子数为1～6的卤代烷基、碳原子数为3～10的环烷基、碳原子数为6～15的取代或未取代的芳基、碳原子数为3～12的取代或未取代的杂芳基，或者R 5和R 6相互连接以与它们所共同连接的碳原子一起形成5～18元脂肪族环、取代或未取代的5～18元芳香环，所述5～18元芳香环上的取代基各自独立地选自氘、卤素基团或碳原子数为1～6的烷基；
各R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自式2所示的基团、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、氢、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的烷氧基、碳原子数为3～10的环烷基或碳原子数为3～12的三烷基硅基，且所述R 1、R 2、R 3和R 4中有任意1个或任意2 个为式2所示的基团；
Figure PCTCN2022082341-appb-000002
Het为6～18元缺电子含氮亚杂芳基；
L 1、L 2和L 3各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
n 1和n 4彼此相同或不同，分别表示R 1和R 4的个数，且各自独立地选自1、2、3或4，n 3表示R 3的个数，选自1或2；n 2表示R 2的个数，选自1、2或3；
所述L 1、L 2、L 3、Ar 1、Ar 2、R 5和R 6中的取代基相同或者不同，且各自独立地选自氘、氰基、卤素基团、碳原子数1～10的烷基、碳原子数1～10的卤代烷基、碳原子数1～10的氘代烷基、碳原子数3～10的环烷基、碳原子数6～20的芳基、碳原子数3～20的杂芳基、碳原子数1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～12的三烷基硅基、碳原子数为6～18的芳基硅基、碳原子数为6～20的芳氧基或碳原子数为6～20的芳硫基；
任选地，Ar 1和Ar 2中，任意两个相邻的取代基形成取代或未取代的5到15元环，所述5到15元环上的取代基各自独立地选自氘、氰基、卤素基团、碳原子数1～4的烷基、碳原子数1～4的卤代烷基、碳原子数1～4的氘代烷基、碳原子数3～6的三烷基硅基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
本申请第二方面提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面提供的有机化合物。
优选地，所述功能层包括有电子传输层和/或发光层，所述电子传输层和/或发光层含有所述的有机化合物。
本申请第三方面提供一种电子装置，包括本申请第二方面的有机电致发光器件。
本申请的有机化合物具有咔唑并芴类型的稠环母核，并且该母核上结合有含氮的电子传输基团，其中母核结构具有大的共轭体系，其电子密度分布利于提升空穴迁移率。母核上芴环的碳原子具有两个取代基，可以调整母核的空间结构，有效避免分子之间的堆叠，提升成膜稳定性。采用具有高电子迁移率的含氮缺电子基团作为电子输注基团，并将其通过共轭单键连接在母核的苯环上，使得有机化合物分子两侧偶极矩提高，三线态能级提高，因此可提高载流子迁移稳定性。本申请的有机化合物用作有机发光器件的电子传输层和/或发光层主体材料可有效提高器件寿命和发光效率。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。在附图中：
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的电子装置的结构示意图。
附图标记说明
100、阳极        200、阴极             300、功能层         310、空穴注入层
320、空穴传输层  321、第一空穴传输层   322、空穴调整层     330、发光层
340、电子传输层  350、电子注入层       400、电子装置
具体实施方式
以下结合附图对本申请的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。
用语“该”和“所述”用以表示存在一个或多个要素/组成部分/等；用语“包括”“包含”和“含有”用以表示开放式的包括在内的意思并且是指除了列出的要素/组成部分/等之外还可存在另外的要素/组成部分/等。
本申请第一方面提供一种有机化合物，所述有机化合物的结构如式1所示：
Figure PCTCN2022082341-appb-000003
式1中，R 5和R 6彼此相同或不同，且分别独立地选自碳原子数为1～6的烷基、碳原子数为1～6的卤代烷基、碳原子数为3～10的环烷基、碳原子数为6～15的取代或未取代的芳基、碳原子数为3～12的取代或未取代的杂芳基，或者R 5和R 6相互连接以与它们所共同连接的碳原子一起形成5～18元脂肪族环、取代或未取代的5～18元芳香环，所述5～18元芳香环上的取代基各自独立地选自氘、卤素基团或碳原子数为1～6的烷基；
各R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自化学式2所示的基团、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、氢、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的烷氧基、碳原子数为3～10的环烷基或碳原子数为3～12的三烷基硅基，且所述R 1、R 2、R 3和R 4中有任意1个或任意2个为式2所示的基团：；
Figure PCTCN2022082341-appb-000004
Het为6～18元缺电子含氮亚杂芳基；
L 1、L 2和L 3各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
n 1和n 4彼此相同或不同，分别表示R 1和R 4的个数，且各自独立地选自1、2、3或4，n 3表示R 3的个数，选自1或2；n 2表示R 2的个数，选自1、2或3；
所述L 1、L 2、L 3、Ar 1、Ar 2、R 5和R 6中的取代基相同或者不同，且各自独立地选自氘、氰基、卤素基团、碳原子数1～10的烷基、碳原子数1～10的卤代烷基、碳原子数1～10的氘代烷基、碳原子数3～10的环烷基、碳原子数6～20的芳基、碳原子数3～20的杂芳基、碳原子数1～10的烷氧基、 碳原子数为1～10的烷硫基、碳原子数为1～12的三烷基硅基、碳原子数为6～18的芳基硅基、碳原子数为6～20的芳氧基或碳原子数为6～20的芳硫基；
任选地，Ar 1和Ar 2中，任意两个相邻的取代基形成取代或未取代的5～15元环，所述5～15元环上的取代基各自独立地选自氘、氰基、卤素基团、碳原子数1～4的烷基、碳原子数1～4的卤代烷基、碳原子数1～4的氘代烷基、碳原子数3～6的三烷基硅基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
本申请的有机化合物具有咔唑并芴的稠环结构，可以形成大的刚性平面结构，能有效提高材料空穴迁移率；并且芴的9位双取代基的结构可以有效避免化合物之间的堆叠，提高成膜稳定性和热稳定性，进而可有效提高器件寿命。在稠环结构上连接缺电子的含氮杂芳基基团，可使材料的吸引电子的能力大幅提升，提高电子迁移率，同时通过调整含氮杂芳基上的取代基团，可进一步调整电子和空穴的传输能力。将本发明的有机化合物作为有机发光电致器件的电子传输层或发光层主体材料时，可以提高器件的发光效率和使用寿命。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“
Figure PCTCN2022082341-appb-000005
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、氰基、卤素基团、碳原子数1～10的烷基、碳原子数1～10的卤代烷基、碳原子数1～10的氘代烷基、碳原子数3～10的环烷基、碳原子数6～20的芳基、碳原子数3～20的杂芳基、碳原子数1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～12的三烷基硅基、碳原子数为6～18的芳基硅基、碳原子数为6～20的芳氧基、碳原子数为6～20的芳硫基。“取代的”官能团可以被上述Rc中的1个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。当相邻的两个取代基Rc连接在同一个原子上时，两个取代基Rc可以独立地存在或者与其所连接的官能团螺合成环。
本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若Ar 1为碳原子数为20的取代的芳基，则芳基及其上的取代基的所有碳原子数为20。
本申请中，L 1、L 2、L 3、Ar 1、Ar 2、R 1、R 2、R 3、R 4、R 5和R 6的碳原子数，指的是所有碳原子数。举例而言：L 1为碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的碳原子总数为12。 例如：Ar 1为
Figure PCTCN2022082341-appb-000006
则其碳原子数为15；L 1为
Figure PCTCN2022082341-appb-000007
则其碳原子数为12。
本申请中，连续以前缀命名的情况意味着按照书写顺序罗列取代基。例如，芳氧基意味着被芳基取代的烷氧基。
本申请中，“芳基”指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。稠环芳基是指环系统中的两个碳原子为两个邻接环所共用的两个或更多个环，其中所述环中的至少一者是芳香族的，例如其它环可以是环烷基、环烯基、芳基。本申请中的芳基实例可以包括但不限于，苯基、萘基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2022082341-appb-000008
基、苝基、芴基、三亚苯基、并四苯基、次三苯基(triphenylenyl)等。在本申请中，稠合芳环是指两个或两个以上芳环或杂芳环以共有环边而形成的多芳环，例如萘、蒽、菲、芘。
本申请中，芴基可以被取代，2个取代基可以彼此结合而形成螺环结构。在上述芴基被取代的情况下，取代的芴基可以为：
Figure PCTCN2022082341-appb-000009
等，但并不限定于此。
在本申请中，取代的芳基是指芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、烷基硅烷基、芳基硅烷基、烷基、卤代烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。
本申请中，作为取代基的芳基的实例可以包括但不限于，苯基、萘基、蒽基、菲基、联苯基、三联苯基、芴基、二甲基芴基、芘基、苝基。
在一些实施方案中，芳基是碳原子数为6～30的取代或未取代的芳基，另一些实施方式中，芳基是碳原子数为6～25的取代或未取代的芳基，另一些实施方式中，芳基是碳原子数为6～20的取代或未取代的芳基，另一些实施方式中，芳基是碳原子数为6～18的取代或未取代的芳基，另一些实施方式中，芳基是碳原子数为6～15的取代或未取代的芳基，另一些实施方式中，芳基的碳原子数为6～13的取代或未取代的芳基，另一些实施方式中，芳基是碳原子数为6～12的取代或未取代的芳基。本申请中，取代或未取代的芳基的碳原子数量可以是6个、10个、12个、13个、14个、15个、16个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。在本申请中，联苯基可以理解为苯基取代的芳基，也可以理解为未取代的芳基。
本申请中，亚芳基为2价基团，除此以外，可以适用上述关于芳基的说明。
本申请中，杂芳基是指环中包含1、2、3、4、5、6或7个独立地选自O、N、P、Si、Se、B和S的杂原子的单环或多环体系，且其中至少有一个环体系是芳香族的。杂芳基中每一个环体系包含5-7个环原子组成的环，且有一个或多个附着点与分子其余部分相连。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。稠环杂芳基是指环系统中的两 个原子为两个邻接环所共用的两个或更多个环，其中所述环中的至少一者是芳香族的，例如其它环可以是环烷基、杂环基、环烯基、芳基。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、异噻唑基、噁二唑基、三唑基、吡啶基、联吡啶基、菲啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
本申请中，取代的杂芳基是指杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解的是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。例如碳原子数为14的取代的杂芳基，指的是杂芳基和取代基的总碳原子数为14。
本申请中，作为取代基的杂芳基的实例包括但不限于，二苯并噻吩基、二苯并呋喃基、咔唑基、N-苯基咔唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、喹啉基、异喹啉基、喹唑啉基、苯并咪唑基、吲哚基、菲咯啉基。
在一些实施方案中，取代或未取代的杂芳基是碳原子数为3～12的取代或未取代的杂芳基，另一些实施方式中，取代或未取代的杂芳基是碳原子数为3～15的取代或未取代的杂芳基，另一些实施方式中，取代或未取代的杂芳基是碳原子数为5～12的取代或未取代的杂芳基，另一些实施方式中，取代或未取代的杂芳基是碳原子数为5～18的取代或未取代的杂芳基。碳原子数为3～30的取代或未取代的杂芳基的碳原子数量可以是3个、4个、5个、7个、12个、13个、14个、15个、16个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
本申请中，缺电子含氮(亚)杂芳基指的是包含至少一个sp 2杂化氮原子的(亚)杂芳基，这类杂芳基中的氮原子中孤对电子不参与共轭，因此整体电子密度较低。“6～18元缺电子含氮亚杂芳基”就是由6～18个原子形成的含有sp 2杂化氮原子的杂芳环。例如，但不限于吡啶基、嘧啶基、三嗪基、哒嗪基、吡嗪基、苯并噁唑基、苯并咪唑基、苯并噻唑基、喹啉基、喹唑啉基、喹喔啉基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、苯并咪唑基、苯并噻唑基、菲咯啉基等。
本申请中，亚杂芳基为2价或更高价基团，除此以外，可以适用上述关于杂芳基的说明。
本申请中，“烷基”包括1～10个碳原子饱和直链或支链的、单价或多价烃基。一些实施方式中，烷基含有1～10个碳原；另外一些实施方式中，烷基含有1～8个碳原子；另外一些实施方式中，烷基含有1～6个碳原子；另外一些实施方式中，烷基含有1～4个碳原子；又一些实施方式中，烷基含有1～3个碳原子。作为取代基的碳原子数为1～4的烷基基团的实例包括但并不限于，甲基，乙基，正丙基，异丙基，正丁基，异丁基，仲丁基，叔丁基等。
在本申请中，卤素基团可以为氟、氯、溴、碘。
本申请中，“烷氧基”表示烷基基团通过氧原子与分子其余部分相连，其中烷基基团具有如本发明所述的含义。作为取代基的烷氧基的实例包括，但并不限于，甲氧基，乙氧基，1-丙氧基，2-丙氧基，1-丁氧基，2-甲基-l-丙氧基，2-丁氧基，2-甲基-2-丙氧基，等等。
本申请中，三烷基硅基是指
Figure PCTCN2022082341-appb-000010
其中，R G1、R G2、R G3分别独立地为烷基，三烷基硅基的具体实例，包括但不限于，三甲基硅基、三乙基硅基、叔丁基二甲基硅基、丙基二甲基硅基。
本申请中，“卤代烷基”表示烷基基团被一个或多个卤素原子所取代，其中烷基基团具有如本申请所述的含义。在一种实施方案中，碳原子数为1～4的卤代烷基包含碳原子数为1～4的氟取代的烷基，这样的实例包含但并不限于，三氟甲基、二氟甲基、1-氟-2-氯乙基等。
本申请中的“环”包含饱和环、不饱和环；饱和环即环烷基、杂环烷基；不饱和环，即环烯基、杂环烯基、芳基和杂芳基。
本申请中，n个环原子形成的环体系，即为“n元环”。例如，苯基为6元芳基。5～10元芳香环就是指含有5到10个环原子的芳基或杂芳基；5～10元脂肪族环是指含有5到10个环原子的环烷基或环烯基。5～15元环就是环原子数为5～15的环体系，且该环体系可以是脂肪族环也可以为芳香环，例如但不限于环戊烷、环己烷、芴环。
本申请中，5～18元芳香环是具有5至18个环原子且包含芳香环的环体系。例如芴环为13元芳香环。
Figure PCTCN2022082341-appb-000011
为取代的14元芳香环。
本申请中，术语“任选”或者“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，任意两个相邻的取代基形成环”意味着两个相邻的取代基可以成环也可以不成环，该方案包括两个取代基相互连接形成成环的情景，也包括两个取代基相互独立地存在的情景。举例而言，两个相邻的取代基可以形成饱和或不饱和的环的形式存在，也可以是相互独立地存在。连接在同一个原子上的两个相邻的取代基成环的情况下，所形成的环与分子其他部分就是螺合连接。连接在相邻原子上的两个相邻的取代基成环的情况下，所形成的环与分子其他部分就是稠合连接。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2022082341-appb-000012
和
Figure PCTCN2022082341-appb-000013
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2022082341-appb-000014
在一些实施方案中，所述有机化合物具有如下式1-1、1-2、1-3或1-4所示结构：
Figure PCTCN2022082341-appb-000015
Figure PCTCN2022082341-appb-000016
其中，各R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自氢、氘、氟、氰基、苯基、萘基、吡啶基、甲基、乙基、叔丁基、异丙基、三氟甲基、三氘代甲基或三甲基硅基。
在本申请的一些实施方案中，R 1、R 2、R 3和R 4中有任意一者为化学式2所示的基团，其余均为氢。
在本申请的一些实施方案中，所述R 5和R 6各自独立地为甲基、乙基、正丙基、异丙基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基、联苯基、芴基、二甲基芴基、蒽基、菲基、吡啶基、二苯并噻吩基、二苯并呋喃基或咔唑基，或者R 5和R 6相互连接以与它们所共同连接的碳原子一起形成芴环、环戊烷、环己烷或
Figure PCTCN2022082341-appb-000017
在本申请的一些更具体的实施方案中，所述R 5和R 6各自独立地选自甲基或以下基团：
Figure PCTCN2022082341-appb-000018
或者R 5和R 6相互连接以与它们所共同连接的碳原子一起形成以下螺环中的一种：
Figure PCTCN2022082341-appb-000019
可选地，式1所示有机化合物中的R 1、R 2、R 3和R 4中有任意1个或任意2个为式2所示的基团：
Figure PCTCN2022082341-appb-000020
其中Het为6～18元缺电子含氮亚杂芳基，Het上的sp 2杂化氮原子在整体上能够降低亚杂芳基的共轭体系的电子云密度而不是提高亚杂芳基的共轭体系的电子云密度，杂原子上的孤对电子不参与到共轭体系中，且杂原子由于较强的电负性而使得共轭体系的电子云密度降低。如此，Het基团可以形成化合物的电子传输核心基团，使得化合物能够有效地实现电子传输，且能够有效地平衡电子和空穴在发光层的传输速率。如此，该化合物既可以作为双极性有机发光层主体材料同时传输电子和空穴，也可以作为电子型有机发光层主体材料而与空穴型有机发光层主体材料配合，还可以作为电子传输材料。
在本申请的一些实施方案中，所述Het基团选自亚三嗪基、亚吡啶基、亚嘧啶基、亚喹啉基、亚喹喔啉基、亚喹唑啉基、亚异喹啉基、亚苯并咪唑基、亚苯并噻唑基、亚苯并噁唑基、亚菲咯啉基、亚苯并喹唑啉基、亚菲并咪唑基、亚苯并呋喃并嘧啶基、亚苯并噻吩并嘧啶基或选自以下基团所组成的组：
Figure PCTCN2022082341-appb-000021
在一些实施方式中，Het选自以下基团所组成的组：
Figure PCTCN2022082341-appb-000022
Figure PCTCN2022082341-appb-000023
其中，
Figure PCTCN2022082341-appb-000024
表示与L 3连接的键，其余两个连接键
Figure PCTCN2022082341-appb-000025
分别连接L 1和L 2。
在一些更具体的实施方式中，Het选自以下含氮亚杂芳基构成的组：
Figure PCTCN2022082341-appb-000026
其中，
Figure PCTCN2022082341-appb-000027
表示Het与L 3连接的位置，
Figure PCTCN2022082341-appb-000028
表示Het与L 1连接的位置，
Figure PCTCN2022082341-appb-000029
表示Het与L 2连接的位置，式中无
Figure PCTCN2022082341-appb-000030
的，代表基团Het连接的
Figure PCTCN2022082341-appb-000031
中，L 2为单键，Ar 2为氢。
在本申请中，式1中的所述Het基团为三嗪基时，化合物的空穴迁移率和电子迁移率之间达到更好的平衡，用于器件中的发光层时，器件的效率较好。
在本申请的一些实施方案中，所述L 1、L 2和L 3各自独立地选自单键、碳原子数为6～18的取代或者未取代的亚芳基、碳原子数为5～12的取代或者未取代的亚杂芳基。
可选地，所述L 1、L 2和L 3中的取代基各自独立地选自氘、氰基、氟、碳原子数为1～5的烷基、碳原子数为1～5的卤代烷基、碳原子数为1～5的氘代烷基、碳原子数6～12的芳基或吡啶基。
在本申请的一些实施方案中，所述L 1、L 2和L 3各自独立地选自单键、取代或者未取代的亚苯基、取代或者未取代的亚萘基、取代或者未取代的亚联苯基、取代或者未取代的亚蒽基、取代或者未取代的亚菲基、取代或者未取代的亚芴基、取代或者未取代的亚二苯并噻吩基、取代或者未取代的亚二苯并呋喃基、取代或者未取代的亚咔唑基；所述L 1、L 2和L 3中的取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基或吡啶基。
在一些具体的实施方案中，所述L 1、L 2和L 3各自独立地选自单键、取代或者未取代的基团W，未取代的基团W选自如下基团：
Figure PCTCN2022082341-appb-000032
其中，
Figure PCTCN2022082341-appb-000033
表示化学键；所述基团W被一个或多个取代基所取代时，所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基或吡啶基。
在本申请的一种更具体的实施方式中，所述L 1、L 2和L 3各自独立地选自单键或选自如下基团：
Figure PCTCN2022082341-appb-000034
在本申请的一些实施方案中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、碳原子数为6～25的取代或未取代的芳基、碳原子数为5～20的取代或未取代的杂芳基。可选地，所述Ar 1 和Ar 2中的取代基各自独立地选自氘、氰基、氟、碳原子数为1～5的烷基、碳原子数为1～5的卤代烷基、碳原子数为1～5的氘代烷基、碳原子数为6～15的芳基或碳原子数为5～12的杂芳基。任选地，Ar 1、Ar 2中，任意两个相邻的取代基形成取代或未取代的5～13元环，所述5～13元环上的取代基选自氘、氰基、卤素基团、碳原子数1～4的烷基、碳原子数1～4的卤代烷基、碳原子数1～4的氘代烷基、碳原子数3～6的三烷基硅基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
在一些实施方案中，取代或未取代的芳基的碳原子数可以选自6、10、12、13、14、15、16、17、18、20、25或30个。
在一些实施方案中，取代或未取代的杂芳基的碳原子数可以选自3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、20、21、22、23、24、25、26、27、28、29或30个。
在本申请的一些实施方案中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、取代或者未取代的苯基、取代或者未取代的联苯基、取代或者未取代的萘基、取代或者未取代的三联苯基、取代或者未取代的芴基、取代或者未取代的芘基、取代或者未取代的苝基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的吡啶基、取代或者未取代的二苯并噻吩基、取代或者未取代的二苯并呋喃基、取代或者未取代的咔唑基、取代或者未取代的螺二芴基；所述Ar 1和Ar 2中的取代基相同或者不同，且各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基、菲基、芴基、二苯并噻吩基、二苯并呋喃基、咔唑基或吡啶基。
在本申请一种具体实施方式中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、取代或者未取代的基团Y，未取代的基团Y选自如下基团：
Figure PCTCN2022082341-appb-000035
其中，
Figure PCTCN2022082341-appb-000036
表示化学键；所述基团Y被一个或多个取代基所取代时，所述取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基、苯基、萘基或吡啶基。
在本申请一种具体实施方式中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘或如下基团所组成的组：
Figure PCTCN2022082341-appb-000037
Figure PCTCN2022082341-appb-000038
在本申请一种具体实施方式中，其中，
Figure PCTCN2022082341-appb-000039
选自以下结构：
Figure PCTCN2022082341-appb-000040
Figure PCTCN2022082341-appb-000041
Figure PCTCN2022082341-appb-000042
在本申请一种具体实施方式中，所述有机化合物选自以下有机化合物所组成的组。
Figure PCTCN2022082341-appb-000043
Figure PCTCN2022082341-appb-000044
Figure PCTCN2022082341-appb-000045
Figure PCTCN2022082341-appb-000046
Figure PCTCN2022082341-appb-000047
Figure PCTCN2022082341-appb-000048
Figure PCTCN2022082341-appb-000049
Figure PCTCN2022082341-appb-000050
Figure PCTCN2022082341-appb-000051
Figure PCTCN2022082341-appb-000052
Figure PCTCN2022082341-appb-000053
本申请第二方面提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面提供的所述的有机化合物。
在一种具体的实施方式中，所述功能层包括电子传输层，所述电子传输层含有所述有机化合物。电子传输层既可以由本申请所提供的有机化合物组成，也可以由本申请所提供的有机化合物和其他材料共同组成，所述电子传输可以为一层或两层以上。
在一种具体的实施方式中，所述功能层包括发光层，所述发光层含有所述有机化合物。发光层中的主体材料既可以由本申请所提供的有机化合物组成，也可以由本申请所提供的有机化合物和其他材料共同组成。
如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、第一空穴传输层321、空穴调整层322、作为能量转化层的发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2：Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选地，电子元件包括以氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，第一空穴传输层321可以包括一种或者多种空穴传输材料，空穴传输材料可以选自 咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。例如，第一空穴传输层321由化合物PAPB组成。
可选地，空穴调整层322(也称“第二空穴传输层”)可以包括三芳胺类化合物或者其他类型的化合物。在一种实施方式中，空穴调整层由PAPB组成。
可选地，发光层330可以由单一发光材料组成，也可以包括主体材料和掺杂材料。可选地，发光层330由主体材料和掺杂材料组成，注入发光层330的空穴和注入发光层330的电子可以在发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给掺杂材料，进而使得掺杂材料能够发光。发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，在本申请的一种具体实施方式中，发光层主体材料含有本申请所述化合物。
发光层330的掺杂材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种具体实施方式中，发光层330含有化合物Ir(piq) 2(acac)和作为发光层主体的本申请的有机化合物。
可选地，电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，本申请的有机化合物、苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种实施方式中，电子传输层340由ET-06和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。例如，电子注入层350含有LiQ。
可选地，如图1所示，在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向第一空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310含有F4-TCNQ。
本申请第三方面提供一种电子装置，包括本申请第二方面提供的有机电致发光器件。
按照一种实施方式，如图2所示，所述电子装置为电子装置400，该电子装置400包括上述有机电致发光器件。电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
合成例：
下面所描述的合成例中，除非另有声明，否则所有的温度的单位为摄氏度。部分试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa ChemicalCompany，部分不能直接采购的中间体是通过商购原料经简单反应制备得到，本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
除非另有声明，否则使用时都没有经过进一步纯化。其余的常规试剂从汕头西陇化工厂、广东光华化学试剂厂、广州化学试剂厂、天津好寓宇化学品有限公司、天津市福晨化学试剂厂、武汉鑫华远科技发展有限公司、青岛腾龙化学试剂有限公司和青岛海洋化工厂等处购买得到。各合成例 中的反应一般是在氮气或氩气正压下进行的，或者在无水溶剂上套一干燥管(除非另有声明)；在反应中，反应瓶都塞上合适的橡皮塞，底物通过注射器注入反应瓶中。所用到的各个玻璃器皿都是干燥过的。
在纯化时，色谱柱是硅胶柱，硅胶(100～200目)购于青岛海洋化工厂。
在各个合成例中，低分辨率质谱(MS)数据的测定条件是：Agilent 6120四级杆HPLC-M(柱子型号：Zorbax SB-C18,2.1×30mm,3.5微米,6min,流速为0.6mL/min。流动相：5％-95％(含0.1％甲酸的乙腈)在(含0.1％甲酸的水)中的比例)，采用电喷雾电离(ESI)，在210nm/254nm下，用UV检测。
核磁共振氢谱：布鲁克(Bruker)400MHz核磁仪，室温条件下，以CDCl 3为溶剂(以ppm为单位)，用TMS(0ppm)作为参照标准。当出现多重峰的时候，将使用下面的缩写：s(singlet，单峰)、d(doublet，双峰)、t(triplet，三重峰)、m(multiplet，多重峰)。
合成例
Figure PCTCN2022082341-appb-000054
在氮气下，向三口烧瓶中加入原料SA-1-1(232.8g，933.07mmol)，SA-2-1(187.36g，933.07mmol)，加入THF(1397mL)和水(464mL)，升温搅拌至澄清并回流，加入Pd 2(PPh 3) 4(10.78，9.33mmol)，K 2CO 3(193.15g，1399.61mmol)，搅拌至澄清，回流反应24h后反应结束。待反应冷却至室温，加入二氯甲烷萃取，有机相用水洗至中性，分离有机层，用无水硫酸镁干燥，滤液减压浓缩后，所得残留物用硅胶柱色谱纯化，得到中间体SA-3-1(206.59g，收率：68％)。
参照中间体SA-3-1的合成方法合成表1所列的各中间体SA-3-X(X为变量，表示1～20的整数，下同)，不同之处在于，使用SA-1-X代替原料SA-1-1，采用SA-2-X代替SA-2-1。
表1
Figure PCTCN2022082341-appb-000055
Figure PCTCN2022082341-appb-000056
Figure PCTCN2022082341-appb-000057
向三口烧瓶中加入SA-3-1(209g，641.44mmol)、乙酸(990mL)和磷酸(55mL)，升温至50℃，搅拌至澄清后，反应4h，待反应结束后，冷却至室温，采用NaOH水溶液进行中和，向溶液中加入乙酸乙酯进行萃取，收集有机相，用无水硫酸镁进行干燥，滤液减压浓缩后，所得残留物经硅胶柱色谱纯化，得到中间体SA-4-1(132.20g，收率：67％)。
参照中间体SA-4-1的合成方法合成表2所列的各个中间体SA-4-X，不同之处在于，使用中间体SA-3-X代替中间体SA-3-1。
表2
Figure PCTCN2022082341-appb-000058
Figure PCTCN2022082341-appb-000059
向三口烧瓶中加入雷尼镍(8g)，水合肼(105mL，2166mmol)和原料SB-1-1(183g，541.42mmol)，加入甲苯(1098mL)，乙醇(366mL)，快速搅拌并升温至回流，反应2h，反应结束后旋干溶剂，所得残留物用硅胶柱色谱纯化，得到中间体SB-2-1(128.08g，收率：73％)。
参照中间体SB-2-1的合成方法合成下表3所示的各个中间体SB-2-X，不同之处在于，采用各SB-1-X代替SB-1-1。
表3
Figure PCTCN2022082341-appb-000060
Figure PCTCN2022082341-appb-000061
向三口烧瓶中加入SB-1-1(124g，366.86mmol)和干燥的THF(744mL)，并冷却至-10℃，加入SB-3-1(69.84g，385.20mmol)，不断搅拌使反应升至室温，然后加入饱和NH 4Cl溶液(500mL)进行淬灭，向反应液中加入乙酸乙酯萃取，并用水洗涤有机相，接着用无水硫酸钠干燥，滤液减压浓缩，所得残留物用甲苯和正庚烷进行重结晶，向残余物中加入苯并升温至50℃，然后滴加三氟甲磺酸(100mL)，滴完反应30min，然后用水洗涤反应液，并用无水硫酸钠进行干燥，有机相减压浓缩后，所得到的残留物用正庚烷/乙酸乙酯进行硅胶柱色谱纯化，得到中间体SB-4-1(130.7g，收率：75％)。
参照中间体SB-4-1的合成方法合成下表4所示的中间体SB-4-X，不同之处在于，采用SB-1-X代替SB-1-1，采用SB-3-X代替SB-3-1。
表4
Figure PCTCN2022082341-appb-000062
Figure PCTCN2022082341-appb-000063
Figure PCTCN2022082341-appb-000064
在氮气下，向三口烧瓶中加入SB-2-1(130g，401.21mmol)和SB-5-1(56.83g，401.21mmol)，加入二氧六环，叔丁醇钾(112.34g，1003.03mmol)，Pd 2(dba) 3(3.82g，4.01mmol)搅拌升温120℃，反应12h后，加入碘甲烷(56.95g，401.21mmol)，在室温下搅拌反应6h，反应结束，用水洗至中性，有机相减压浓缩后所得残留物用硅胶柱色谱纯化，采用石油醚/乙酸乙酯(体积比10:1)洗脱，得到中间体SB-6-1(126.3g，收率：76％)。
参照中间体SB-6-1的合成方法合成下表5所示的各个中间体SB-6-X，不同之处在于，采用SB-2-X代替中间体SB-2-1，采用SB-5-X代替中间体SB-5-1。
表5
Figure PCTCN2022082341-appb-000065
Figure PCTCN2022082341-appb-000066
Figure PCTCN2022082341-appb-000067
将SB-2-1(141g，435.19mmol)溶于含有干燥DMSO(845mL)的三口烧瓶中，在室温下加入叔丁醇钠(62.73g，652.79mmol)，加热搅拌使反应温度达到65℃，将原料SB-7-1(161.79g，478.71mmol)溶于干燥的DMSO中并滴加入三口烧瓶，滴加结束后，在65℃下保温30min，反应结束后加入300mL的NH 4OH水溶液并搅拌20min，过滤，用甲醇和水洗涤滤饼，粗品经硅胶柱色谱纯化得到中间体SB-8-1(126.28g，收率：74％)。
参照中间体SB-8-1的合成方法合成下表6所示的各个中间体SB-8-X，不同之处在于，采用中间体SB-2-X代替SB-2-1，采用原料SB-7-X代替SB-7-1。
表6
Figure PCTCN2022082341-appb-000068
Figure PCTCN2022082341-appb-000069
充分干燥的条件下，在氮气保护下，向1L四口烧瓶中加入2-溴-1,1-联苯(105.5g，452.58mmol)和600mL干燥的四氢呋喃，搅拌溶解后用液氮降温至-78℃以下，缓慢滴加n-BuLi正己烷溶液120mL(452.58mmol)；滴加结束后在-78℃下搅拌1h，然后在该温度下分批加入SB-1-1(152.97g，452.58mmol)，加入结束后在-78℃下保温Ih，然后升温至室温搅拌12h。待反应结束，滴加8mL盐酸溶液淬灭反应，用乙酸乙酯萃取，分出的有机相用饱和食盐水洗涤，有机相减压除去溶剂，得到中间体SB-3-2a。在不进行任何提纯的情况下，再投料到2L的干燥三口烧瓶中，加入1335mL乙 酸和20g质量分数为36％的盐酸，升温至回流搅拌3h，结束反应。冷却至室温后，过滤，用水洗涤两次，干燥，硅胶柱色谱提纯，得到中间体SB-9-1(123.40g，收率：57.5％)。
参照中间体SB-9-1的合成方法合成下表7所示的各个中间体SB-9-X，不同之处在于，采用SB-1-X代替SB-1-1。
表7
Figure PCTCN2022082341-appb-000070
Figure PCTCN2022082341-appb-000071
在氮气保护下，向三口反应瓶中加入SC-1-1(151g,679.3mmol)和THF(906mL)，开启搅拌，搅拌均匀后体系降温至-78℃，开始滴加正丁基锂(10.87g,169.83mmol)，滴加完毕后在-78℃下保温1h，然后将原料SC-2-1(215.40g,713.27mmol))用THF(430mL)稀释后滴加至体系中，滴加完毕后在-78℃下保温1h，然后自然升温至25℃搅拌12h。反应完全后，将反应液倒入水中(500mL)搅拌10min，然后加入二氯甲烷(500mL)进行萃取，操作2次，合并有机相，用无水硫酸镁干燥后过硅胶漏斗，然后将滤液减压浓缩，得中间体SC-3-1(192.12g，收率：63.5％)。
参照中间体SC-3-1的合成方法合成下表8所示的中间体SC-3-2，不同之处在于，采用SC-2-2代替SC-2-1。
表8
Figure PCTCN2022082341-appb-000072
Figure PCTCN2022082341-appb-000073
向单口瓶中加入中间体SC-3-1(191g,428.85mmol)和三氟乙酸(1146)，开启搅拌，然后升温至80℃回流反应11h，反应完成后，将反应液倒入水中(1：20，v/v)，搅拌30min后过滤，用水淋洗，用乙醇淋洗，所得粗品用二氯甲烷：正庚烷＝1：2(v/v)重结晶，得到中间体SC-4-1(130.13g，收率71％)。
按照中间体SC-4-1的合成方法合成下表9所示的中间体SC-4-2，不同之处在于，采用中间体SC-3-2代替中间体SC-3-1。
表9
Figure PCTCN2022082341-appb-000074
Figure PCTCN2022082341-appb-000075
将SA-4-1(128.65g，418.24mmol)溶解在THF(772mL)中之后，将温度降低至-78℃，并向其中缓慢添加叔丁基锂(t-BuLi)(60.83mL，627.36mmol)。在该温度下搅拌1h，向其中添加硼酸三异丙酯(78.63mL，418.24mmol)，然后在将温度逐渐升至室温并搅拌3h。向反应混合物中添加盐酸溶液(300mL)，继续在室温下搅拌1.5h。将产生的沉淀物过滤，依次用水和乙醚洗涤，然后在真空下干燥以得到中间体A-1-1(98.01g，产率：86％)。
参照中间体A-1-1的合成方法来合成表10所列的各中间体Y-1-X(Y为变量，表示A、B或C)，不同之处在于，使用各个SY-X-X代替SA-4-1。
表10
Figure PCTCN2022082341-appb-000076
Figure PCTCN2022082341-appb-000077
Figure PCTCN2022082341-appb-000078
Figure PCTCN2022082341-appb-000079
在氮气保护下，向三口烧瓶中加入A-1-1(97.5g，357.75mmol)，A-2-1(89.08g，357.75mmol)，并加入THF(582mL)和H 2O(194mL)，加热搅拌至澄清，然后加入Pd(PPh 3) 4(0.43g，3.76mmol)，K 2CO 3(77.78g，563.63mmol)，加热回流搅拌15h后，反应完全。待反应液冷却至室温，加入水洗至中性，收集有机相，减压浓缩，所得残留物经硅胶柱色谱纯化，得到中间体A-3-1(85.01g，产率：68％)。
参照中间体A-3-1的合成方法来合成表11所列的各个中间体A-3-X、B-3-X、C-3-X，不同之处在于，使用A-1-X或B-1-X或C-1-X代替中间体A-1-1，使用A-2-X代替A-2-1。
表11
Figure PCTCN2022082341-appb-000080
Figure PCTCN2022082341-appb-000081
Figure PCTCN2022082341-appb-000082
Figure PCTCN2022082341-appb-000083
在氮气保护下，向三口烧瓶中加入A-3-1(84.67g,242.05mmol)，采用400mL邻二氯苯溶解，加入三苯基膦(1.27g,4.84mmol)，在170℃～190℃下搅拌反应12～16h，反应结束后冷却至室温，过滤，滤液减压蒸干，所得残留物经硅胶柱色谱纯化，得中间体A-5-1(50g,收率：65.1％)。
参照中间体A-5-1的合成方法来合成表12所列的各个中间体A-5-X、B-4-X、C-4-X，不同之处在于，使用中间体A-3-X或B-3-X或C-3-X代替中间体A-3-1。
表12
Figure PCTCN2022082341-appb-000084
Figure PCTCN2022082341-appb-000085
Figure PCTCN2022082341-appb-000086
Figure PCTCN2022082341-appb-000087
将中间体A-5-1(49.79g,156.66mmol)、原料A-6-1(29.99g,156.66mmol)和甲苯(400mL)加入三口圆底烧瓶中，氮气保护下加热至回流，加入三(二亚苄基丙酮)二钯(1.44g,1.57mmol)、X-phos(1.5g,3.13mmol)和叔丁醇钠(22.58g,234.99mmol)搅拌3h；而后冷却至室温，反应液使用水洗后加入无水硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对所得粗品进行重结晶提纯，得到固体中间体A-7-1(51.0g,收率76％)。
参照中间体A-7-1的合成方法合成表13所列的各个中间体A-7-X、B-6-X、C-6-X，不同之处在于，使用A-5-X或B-4-X或C-4-X代替中间体A-5-1，使用A-6-X代替A-6-1。
表13
Figure PCTCN2022082341-appb-000088
Figure PCTCN2022082341-appb-000089
Figure PCTCN2022082341-appb-000090
Figure PCTCN2022082341-appb-000091
氮气保护下，向三口烧瓶中，加入A-7-1(50.50g,117.89mmol)，醋酸钯(0.26g,1.18mmol)，三环己基膦四氟硼酸盐(0.87g,2.36mmol)，碳酸铯(57.62g,176.84mmol)和邻二甲苯(303mL)，加热回流反应2h，反应结束后，反应液用氯仿萃取，有机相经减压旋蒸除去溶剂，硅胶柱色谱纯化得到中间体A-8-1(30.95g，收率：67％)。
参照中间体A-8-1的合成方法来合成表14所列的各个中间体A-8-X、B-7-X、C-7-X，不同之处在于，使用中间体A-7-X或B-6-X或C-6-X代替中间体A-7-1。
表14
Figure PCTCN2022082341-appb-000092
Figure PCTCN2022082341-appb-000093
Figure PCTCN2022082341-appb-000094
Figure PCTCN2022082341-appb-000095
将中间体A-8-1(30g,76.55mmol)、联硼酸频那醇酯(19.36g,76.55mmol)、三(二亚苄基丙酮)二钯(0.71g,0.77mmol)、X-Phos(0.72g,1.53mmol)、醋酸钾(11.25g,114.83mmol)和1,4-二氧六环(240mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对所得粗品进行重结晶提纯，得到固体中间体A-10-1(28.12g，收率76％)。
参照中间体A-10-1的合成方法来合成表15所列的各个中间体A-10-X、B-8-X、C-8-1，不同之处在于，使用中间体A-8-X或B-7-X或C-7-1代替中间体A-8-1。
表15
Figure PCTCN2022082341-appb-000096
Figure PCTCN2022082341-appb-000097
Figure PCTCN2022082341-appb-000098
Figure PCTCN2022082341-appb-000099
将中间体A-10-1(43.5g,89.98mmol)、原料A-9-1(21.46g,89.98mmol)、醋酸钯(0.20g,0.90mmol)、X-Phos(0.86g,1.80mmol)、碳酸钾(18.63g,134.8mmol)、甲苯(261mL)、无水乙醇(87mL)和去离子水(87mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌4h；而后冷却至室温，反应液使用水洗后加入无水硫酸镁干燥，过滤后将滤液减压除去溶剂；所得粗产物使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到固体中间体A-12-1(32.0g，收率76％)。
参照中间体A-12-1的合成方法来合成表16所列的各个中间体A-12-X、B-10-X、C-10-1，不同之处在于，使用中间体A-10-X或B-8-X或C-8-1代替中间体A-10-1，使用A-11-X或A-9-X代替A-9-1。
表16
Figure PCTCN2022082341-appb-000100
Figure PCTCN2022082341-appb-000101
Figure PCTCN2022082341-appb-000102
Figure PCTCN2022082341-appb-000103
将中间体A-12-1(27.5g,58.76mmol)、联硼酸频那醇酯(14.86g,58.76mmol)、三(二亚苄基丙酮)二钯(0.54g,0.59mmol)、X-Phos(0.55g,1.18mmol)、醋酸钾(8.64g,88.14mmol)和1,4-二氧六环(224mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对所得粗品进行重结晶提纯，得到固体中间体A-13-1(26.3g，收率80％)。
参照中间体A-13-1的合成方法来合成表17所列的中间体A-13-X、B-13-X、C-13-1，不同之处在于，使用中间体A-12-X或B-10-X或C-10-1代替中间体A-12-1。
表17
Figure PCTCN2022082341-appb-000104
Figure PCTCN2022082341-appb-000105
Figure PCTCN2022082341-appb-000106
在250mL三口瓶中，通入氮气，加入中间体A-10-1(26.25g，54.3mmol)，原料A-14-1(9.9g，54.3mmol)、THF(156mL)和H 2O(52mL)升温搅拌至回流，加入四三苯基膦钯(0.42g，0.362mmol)、碳酸钾(7.5g，54.3mmol)加热至回流，回流反应10h，反应完全。待反应体系自然冷却，加入80mL稀盐酸淬灭，水洗至中性，采用DCM萃取有机相，有机相减压浓缩后，所得残留物经硅胶柱色谱纯化，产物烘干，得到中间体A-15-1(18.30g，收率67％)。
参照中间体A-15-1的合成方法合成表18所列的各个中间体A-15-X、B-15-X、C-15-1，不同之处在于，使用原料A代替中间体A-10-1。
表18
Figure PCTCN2022082341-appb-000107
Figure PCTCN2022082341-appb-000108
Figure PCTCN2022082341-appb-000109
Figure PCTCN2022082341-appb-000110
Figure PCTCN2022082341-appb-000111
Figure PCTCN2022082341-appb-000112
在250mL三口瓶中，通入氮气，加入中间体A-15-1(11.75g，23.25mmol)，原料A-16-1(2.83g，23.25mmol)、THF(72mL)和H 2O(24mL)升温搅拌至回流，加入四三苯基膦钯(0.27g，0.23mmol)、碳酸钾(4.77g，34.88mmol)加热至回流，回流反应10h，取样点板，反应完全。待自然冷却，加入80mL稀盐酸淬灭，水洗至中性，采用DCM萃取有机相，有机相减压浓缩后，所得残留物经硅胶柱色谱纯化，产物烘干，得到中间体A-17-1(7.0g，收率55％)。
参照中间体A-17-1的合成方法来合成表19所列的各个中间体A-17-X、B-17-X、C-17-X，不同之处在于，使用中间体A-15-X或B-15-X或C-15-X代替中间体A-15-1，使用原料A-16-X代替A-16-1。
表19
Figure PCTCN2022082341-appb-000113
Figure PCTCN2022082341-appb-000114
Figure PCTCN2022082341-appb-000115
Figure PCTCN2022082341-appb-000116
化合物合成
制备例1：化合物1
Figure PCTCN2022082341-appb-000117
在250mL三口瓶中，通入氮气，加入中间体A-17-1(6.58g，12.03mmol)，原料A-16-3(2.38g，12.03mmol)、42mL的THF、14mL的H 2O升温搅拌至回流，加入四三苯基膦钯(0.14g，0.12mmol)、碳酸钾(2.49g，18.05mmol)加热至回流，回流反应10h，取样点板，反应完全。待自然冷却，加入80mL稀盐酸淬灭，水洗至中性，采用DCM萃取有机相，有机相减压浓缩后，所得残留物经硅胶柱色谱纯化，采用DCM和正庚烷对粗产物进行重结晶，产物过滤烘干，得到化合物1(5.36g,收率：67％)，质谱:m/z＝665.3[M+H] +。
参照化合物1的合成方法来合成表20所列举的各个化合物X，不同之处在于，使用中间体A-17-X或B-17-X或C-17-X代替中间体A-17-1，使用原料A-16-X代替原料A-16-3。
表20
Figure PCTCN2022082341-appb-000118
Figure PCTCN2022082341-appb-000119
Figure PCTCN2022082341-appb-000120
Figure PCTCN2022082341-appb-000121
Figure PCTCN2022082341-appb-000122
制备例32：
Figure PCTCN2022082341-appb-000123
将中间体A-13-1(9.60g，17.3mmol)、2-苯基-4-(4-氟苯基)-6-氯-1,3,5-三嗪(4.7g，16.5mmol)、四(三苯基膦)钯(0.19g，0.16mmol)、碳酸钾(5.0g；36.3mmol)、四丁基溴化铵(1.1g，3.3mmol)加入烧瓶中，并加入甲苯(80mL)、乙醇(40mL)和水(20mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌8h；冷却至室温，停止搅拌。反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物，即化合物305(9.4g，收率80％)，质谱:m/z＝683.2[M+H] +。
制备例33～45
参照制备例32的方法合成表21所列的各个化合物X，不同的是，使用反应物I替代中间体A-13-1，反应物J代替2-苯基-4-(4-氟苯基)-6-氯-1,3,5-三嗪。
表21
Figure PCTCN2022082341-appb-000124
Figure PCTCN2022082341-appb-000125
实施例1：红色有机电致发光器件
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2022082341-appb-000126
的基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2：N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2022082341-appb-000127
的空穴注入层(HIL)。
在空穴注入层上真空蒸镀NPB，形成厚度为
Figure PCTCN2022082341-appb-000128
的第一空穴传输层(HTL-1)，并在第一空穴传输层上真空蒸镀PAPB，形成
Figure PCTCN2022082341-appb-000129
的空穴调整层。
在空穴调整层上，将化合物1：Ir(piq) 2(acac)以97％：3％的膜厚比例进行共同蒸镀，形成厚度为
Figure PCTCN2022082341-appb-000130
的红光发光层(R-EML)。
将ET-06和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2022082341-appb-000131
厚的电子传输层(ETL)，将LiQ蒸 镀在电子传输层上以形成厚度为
Figure PCTCN2022082341-appb-000132
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1：9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2022082341-appb-000133
的阴极。
在上述阴极上蒸镀CP-05，形成厚度为
Figure PCTCN2022082341-appb-000134
的有机覆盖层(CPL)，从而完成有机电致发光器件的制造。
实施例2～实施例45
在形成红光发光层时，以表22中化合物X列所示的化合物替代实施例1中的化合物1，利用与实施例1相同的方法制作有机电致发光器件。
比较例1
在形成红光发光层时，以化合物A替代实施例1中的化合物1，按照与实施例1相同的方法制备有机电致发光器件。
比较例2
在形成红光发光层时，以化合物B替代实施例1中的化合物1，按照与实施例1相同的方法制备有机电致发光器件。
比较例3
在形成红光发光层时，以化合物C替代实施例1中的化合物1，按照与实施例1相同的方法制备有机电致发光器件。
比较例4
在形成红光发光层时，以化合物D替代实施例1中的化合物1，按照与实施例1相同的方法制备有机电致发光器件。
比较例5
在形成红光发光层时，以化合物E替代实施例1中的化合物1，按照与实施例1相同的方法制备有机电致发光器件。
在实施例1～45和比较例1～5中，所使用的各个材料的结构式如表22所示。
表22
Figure PCTCN2022082341-appb-000135
Figure PCTCN2022082341-appb-000136
对如上制得的有机电致发光器件，在15mA/cm 2的条件下分析了器件的性能，其结果示于下表23。
表23
Figure PCTCN2022082341-appb-000137
Figure PCTCN2022082341-appb-000138
根据表23的结果可知，将作为红光发光层的本申请的化合物的实施例1～45与已公知的化合物所对应的器件比较例1～5相比，有机电致发光器件的驱动电压至少降低0.1V，电流效率(Cd/A)至少提高了10.9％，寿命最少提高了32％。
以上结合附图详细描述了本申请的优选实施方式，但是，本申请并不限于上述实施方式中的具体细节，在本申请的技术构思范围内，可以对本申请的技术方案进行多种简单变型，这些简单变型均属于本申请的保护范围。

Claims (16)

  1. 有机化合物，所述有机化合物的结构如式1所示：
    Figure PCTCN2022082341-appb-100001
    其中，R 5和R 6彼此相同或不同，且分别独立地选自碳原子数为1～6的烷基、碳原子数为1～6的卤代烷基、碳原子数为3～10的环烷基、碳原子数为6～15的取代或未取代的芳基、碳原子数为3～12的取代或未取代的杂芳基，或者R 5和R 6相互连接以与它们所共同连接的碳原子一起形成5～18元脂肪族环、取代或未取代的5～18元芳香环，所述5～18元芳香环上的取代基选自氘、卤素基团或碳原子数为1～6的烷基；
    各R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自式2所示的基团、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、氢、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的烷氧基、碳原子数为3～10的环烷基、碳原子数为3～12的三烷基硅基，且所述R 1、R 2、R 3和R 4中有任意1个或任意2个为式2所示的基团，
    Figure PCTCN2022082341-appb-100002
    Het为6～18元缺电子含氮亚杂芳基；
    L 1、L 2和L 3各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
    Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
    n 1和n 4彼此相同或不同，分别表示R 1和R 4的个数，且各自独立地选自1、2、3或4；n 3表示R 3的个数，选自1或2；n 2表示R 2的个数，选自1、2或3；
    所述L 1、L 2、L 3、Ar 1、Ar 2、R 5和R 6中的取代基相同或者不同，且各自独立地选自氘、氰基、卤素基团、碳原子数1～10的烷基、碳原子数1～10的卤代烷基、碳原子数1～10的氘代烷基、碳原子数3～10的环烷基、碳原子数6～20的芳基、碳原子数3～20的杂芳基、碳原子数1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～12的三烷基硅基、碳原子数为6～18的芳基硅基、碳原子数为6～20的芳氧基或碳原子数为6～20的芳硫基；
    任选地，Ar 1和Ar 2中，任意两个相邻的取代基形成取代或未取代的5～15元环，所述5～15元环上的取代基各自独立地选自氘、氰基、卤素基团、碳原子数1～4的烷基、碳原子数1～4的卤代烷基、碳原子数1～4的氘代烷基、碳原子数3～6的三烷基硅基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
  2. 根据权利要求1所述的有机化合物，其中，所述R 5和R 6各自独立地为甲基、乙基、正丙基、异丙基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基、联苯基、芴基、二甲基芴基、蒽基、菲基、吡啶基、二苯并噻吩基、二苯并呋喃基或咔唑基，或者所述R 5和R 6相互连接以与它们所共 同连接的碳原子一起形成芴环、环戊烷、环己烷或
    Figure PCTCN2022082341-appb-100003
  3. 根据权利要求1所述的化合物，其中，所述Het选自亚三嗪基、亚吡啶基、亚嘧啶基、亚喹啉基、亚喹喔啉基、亚喹唑啉基、亚异喹啉基、亚苯并咪唑基、亚苯并噻唑基、亚苯并噁唑基、亚菲咯啉基、亚苯并喹唑啉基、亚菲并咪唑基、亚苯并呋喃并嘧啶基、亚苯并噻吩并嘧啶基或选自以下基团所组成的组：
    Figure PCTCN2022082341-appb-100004
  4. 根据权利要求1所述的有机化合物，其中，所述L 1、L 2和L 3各自独立地选自单键、碳原子数为6～18的取代或者未取代的亚芳基、碳原子数为5～12的取代或者未取代的亚杂芳基；
    可选地，所述L 1、L 2和L 3中的取代基各自独立地选自氘、氰基、氟、碳原子数为1～5的烷基、碳原子数为1～5的卤代烷基、碳原子数为1～5的氘代烷基、碳原子数6～12的芳基或吡啶基。
  5. 根据权利要求1所述的有机化合物，其中，所述L 1、L 2和L 3各自独立地选自单键、取代或者未取代的亚苯基、取代或者未取代的亚萘基、取代或者未取代的亚联苯基、取代或者未取代的亚蒽基、取代或者未取代的亚菲基、取代或者未取代的亚芴基、取代或者未取代的亚二苯并噻吩基、取代或者未取代的亚二苯并呋喃基、取代或者未取代的亚咔唑基；
    所述L 1、L 2和L 3中的取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基或吡啶基。
  6. 根据权利要求1所述的有机化合物，其中，所述L 1、L 2和L 3各自独立地选自单键、取代或者未取代的基团W，未取代的基团W选自如下基团：
    Figure PCTCN2022082341-appb-100005
    其中，
    Figure PCTCN2022082341-appb-100006
    表示化学键；所述基团W被一个或多个取代基所取代时，所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基或吡啶基。
  7. 根据权利要求1所述的有机化合物，其中，所述L 1、L 2和L 3各自独立地选自单键或如下基团：
    Figure PCTCN2022082341-appb-100007
    Figure PCTCN2022082341-appb-100008
  8. 根据权利要求1所述的有机化合物，其中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、碳原子数为6～25的取代或未取代的芳基、碳原子数为5～20的取代或未取代的杂芳基；
    可选地，所述Ar 1和Ar 2中的取代基各自独立地选自氘、氰基、氟、碳原子数为1～5的烷基、碳原子数为1～5的卤代烷基、碳原子数为1～5的氘代烷基、碳原子数为6～15的芳基、碳原子数为5～12的杂芳基，任选地，Ar 1、Ar 2中，任意两个相邻的取代基形成取代或未取代的5～13元环，所述5～13元环上的取代基选自氘、氰基、卤素基团、碳原子数1～4的烷基、碳原子数1～4的卤代烷基、碳原子数1～4的氘代烷基、碳原子数3～6的三烷基硅基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
  9. 根据权利要求1所述的有机化合物，其中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、取代或者未取代的苯基、取代或者未取代的联苯基、取代或者未取代的萘基、取代或者未取代的三联苯基、取代或者未取代的芴基、取代或者未取代的芘基、取代或者未取代的苝基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的吡啶基、取代或者未取代的二苯并噻吩基、取代或者未取代的二苯并呋喃基、取代或者未取代的咔唑基、取代或者未取代的螺二芴基；
    所述Ar 1和Ar 2中的取代基相同或者不同，且各自独立地选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基、二苯并噻吩基、二苯并呋喃基、咔唑基或吡啶基。
  10. 根据权利要求1所述的有机化合物，其中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘、取代或者未取代的基团Y，未取代的基团Y选自如下基团：
    Figure PCTCN2022082341-appb-100009
    Figure PCTCN2022082341-appb-100010
    其中，
    Figure PCTCN2022082341-appb-100011
    表示化学键；所述基团Y被一个或多个取代基所取代时，所述取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基、苯基、萘基或吡啶基。
  11. 根据权利要求1所述的有机化合物，其中，所述Ar 1和Ar 2相同或不同，且各自独立地选自氢、氘或如下基团所组成的组：
    Figure PCTCN2022082341-appb-100012
  12. 根据权利要求1所述的有机化合物，其中，
    Figure PCTCN2022082341-appb-100013
    选自以下结构：
    Figure PCTCN2022082341-appb-100014
    Figure PCTCN2022082341-appb-100015
    Figure PCTCN2022082341-appb-100016
  13. 根据权利要求1所述的有机化合物，其中，所述R 5和R 6各自独立地选自甲基或以下基团：
    Figure PCTCN2022082341-appb-100017
    或者R 5和R 6相互连接以与它们所共同连接的碳原子一起形成以下螺环中的一种：
    Figure PCTCN2022082341-appb-100018
  14. 根据权利要求1所述的有机化合物，其中，所述有机化合物选自以下有机化合物所组成的组：
    Figure PCTCN2022082341-appb-100019
    Figure PCTCN2022082341-appb-100020
    Figure PCTCN2022082341-appb-100021
    Figure PCTCN2022082341-appb-100022
    Figure PCTCN2022082341-appb-100023
    Figure PCTCN2022082341-appb-100024
    Figure PCTCN2022082341-appb-100025
    Figure PCTCN2022082341-appb-100026
    Figure PCTCN2022082341-appb-100027
    Figure PCTCN2022082341-appb-100028
    Figure PCTCN2022082341-appb-100029
  15. 有机电致发光器件，其包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；
    所述功能层包含权利要求1～14中任一项所述的有机化合物；
    优选地，所述功能层包括有电子传输层和/或发光层，所述电子传输层和/或发光层包含所述的有机化合物。
  16. 电子装置，包括权利要求15所述的有机电致发光器件。
PCT/CN2022/082341 2021-04-16 2022-03-22 有机化合物以及使用其的有机电致发光器件和电子装置 WO2022218112A1 (zh)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727398A (zh) * 2018-06-28 2018-11-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途
WO2020262853A1 (ko) * 2019-06-26 2020-12-30 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20210023223A (ko) * 2019-08-22 2021-03-04 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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TWI764984B (zh) * 2017-02-28 2022-05-21 南韓商羅門哈斯電子材料韓國公司 有機電致發光化合物及包含其之有機電致發光裝置
KR20190109261A (ko) * 2018-03-16 2019-09-25 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자용 복합 재료, 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727398A (zh) * 2018-06-28 2018-11-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途
WO2020000827A1 (zh) * 2018-06-28 2020-01-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途
WO2020262853A1 (ko) * 2019-06-26 2020-12-30 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20210023223A (ko) * 2019-08-22 2021-03-04 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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