Arylamine compound and organic electroluminescent device thereof
By using new aromatic amine compounds as hole transport materials and luminescent layer materials, the problem that existing materials are difficult to meet high-performance organic electroluminescent devices is solved, and higher luminescence efficiency and service life are achieved.
Patent Information
- Application Number
- CN202510205829.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-02-24
- Publication Date
- 2025-05-02
AI Technical Summary
The existing hole transport materials and luminescent layer materials are difficult to meet the requirements of high-performance organic electroluminescent devices, resulting in insufficient luminescence efficiency and service life.
A new aromatic amine compound is used as a hole transport material and a luminescent layer material, and the hole transport rate and injection efficiency are improved through its unique chemical structure, and the recombination of electrons and holes is promoted.
It improves the luminous efficiency and service life of organic electroluminescent devices, meets high-performance requirements, and has simple preparation methods and good industrialization prospects.
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Abstract
Description
Technical Field
[0001] The invention relates to the technical field of organic photoelectric materials, and in particular to an aromatic amine compound and an organic electroluminescent device thereof. Background Art
[0002] In the early years, inorganic electroluminescent materials developed rapidly, and devices based on inorganic electroluminescent materials have been applied to optoelectronic and display electronic equipment, including instrument panels, electronic boards, advertising boards, etc. However, inorganic electroluminescent material devices have high production costs, difficult processing, low efficiency, and it is difficult to achieve large-area high-resolution flat panel displays. Organic electroluminescent devices (OLEDs) are currently a research hotspot in the field of organic optoelectronics because of their active luminescence, lightness, thinness, good contrast, no viewing angle restrictions, and low energy consumption. They have broad application prospects in the fields of flat panel displays and solid-state lighting.
[0003] The structure of an organic electroluminescent device starts from the cathode, followed by the electron transport region, the light-emitting layer, the hole transport region, and the anode. After a certain voltage is applied to the cathode and the cathode, charges begin to be injected, the anode injects holes, and the cathode injects electrons. The electrons and holes injected into the organic layer are called carriers. The carriers are transferred between the organic molecules in the functional transport layer and move to the light-emitting layer. The electrons and holes recombine in the light-emitting molecules to form excitons, and then the excitons migrate within a certain range to transfer energy. The molecules that capture energy are excited and transition from a stable state to an unstable excited state. When they return to the stable ground state, they release energy. The energy decays in the form of radiation photons, resulting in luminescence.
[0004] The hole transport layer is between the anode and the light-emitting layer. Its main function is to increase the hole transmission rate in the device and reduce the energy barrier of the hole during the injection process, thereby improving the hole injection efficiency, which helps to improve the brightness and luminous efficiency of the OLED device and extend the service life of the device. The role of the light-emitting layer in the OLED is to promote the recombination of electrons and holes in the light-emitting layer to form excitons. The main material of the light-emitting layer usually has a hole transport or electron transport function, which can efficiently transfer energy to the doping material, thereby improving the luminous efficiency of the device. By controlling the structure and composition of the light-emitting layer material, specific color emission can be achieved, thereby enhancing the color purity and brightness of the OLED, and protecting the device from environmental factors, thereby extending the service life of the device.
[0005] As people's requirements for OLED performance continue to increase, existing hole transport materials and light-emitting layer materials are difficult to meet the requirements of higher performance of devices. R&D personnel need to continuously develop and optimize the structure of hole transport materials and light-emitting layer materials to continuously improve the luminous efficiency and service life of OLEDs to meet the market needs of different application scenarios. Summary of the invention
[0006] In order to solve the above problems, the present invention aims to provide an aromatic amine compound and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device and extend the service life of the device.
[0007] The present invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:
[0008]
[0009] Wherein, the x is independently selected from any one of CH and N;
[0010] The Ar 1 ,Ar 2 Any one independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring;
[0011] The L is selected from any one of the following groups or a combination of two or more of the following groups:
[0012]
[0013] The z is independently selected from any one of CH and N;
[0014] The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0015] The Y a , Y b , Y c independently selected from O, S, N(R s )
[0016] The Y d , Y e independently selected from O, S, C(R p R q )、N(R t )
[0017] The R b , R b 'Independently selected from any one of fluorine, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl;
[0018] The R p , Rq is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p , R q are connected to form a substituted or unsubstituted ring;
[0019] The R s , R t Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0020] The b 1 is selected from 0, 1, 2, 3 or 4; said b 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said b 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b 4 Selected from 0, 1 or 2; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; said b' 1 Selected from 0, 1 or 2; when there are two or more R b ', two or more R b ' are the same or different from each other; wherein each b 1 、b 2 、b 3 、b 4 , b' 1 At least one of them is not selected from 0;
[0021] The L 1 , L 2 Any one independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed cyclic group, a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed cyclic group;
[0022] The R 1 , R 2Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0023] The Ar 1 ,Ar 2 , L 1 , L 2 , R 1 , R 2 At least one of them contains one or more -Si(R n ) 3 ;
[0024] The R n Any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0025] The 1 Selected from 0, 1, 2, 3 or 4; when there are two or more R 1 When two or more R 1 The same or different from each other, or two adjacent R 1 are connected to each other to form a substituted or unsubstituted ring;
[0026] The 2 Selected from 0, 1, 2, 3 or 4; when there are two or more R 2 When two or more R 2 The same or different from each other, or two adjacent R 2 They are connected to each other to form a substituted or unsubstituted ring.
[0027] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or located on the side of the cathode away from the anode, wherein the organic layer contains at least one of the aromatic amine compounds described in the present invention.
[0028] Beneficial Effects
[0029] The present invention provides an aromatic amine compound, which can improve the hole transmission rate in the device when used as a hole transport material, and reduce the energy barrier of the hole in the injection process, thereby improving the hole injection efficiency, improving the brightness and luminous efficiency of the OLED device and extending the service life of the device. When the compound is used as a light-emitting layer material, it can promote the recombination of electrons and holes in the light-emitting layer to form excitons, thereby improving the luminous efficiency of the device and extending the service life of the device. The preparation method of the compound provided by the present invention is simple, the raw materials are easily available, can meet the industrialization needs, and has a good industrialization prospect. DETAILED DESCRIPTION
[0030] The following will be clearly and completely described in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. After reading the present invention, modifications of various equivalent forms of the present invention by those skilled in the art all fall within the scope defined by the present invention.
[0031] In the present specification, "-*" means a part connected to another substituent. "-*" can be connected to any optional position of the group / fragment to which it is connected.
[0032] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.
[0033] In the present specification, when the position of a substituent or a bonding site on a ring is not fixed, it means that it can be bonded to any one of any optional sites of the ring.
[0034] For example, Can be expressed Can be expressed Can be expressed And so on.
[0035] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine and iodine.
[0036] The alkyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from an alkane molecule, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, sec-butyl, tert-butyl, etc., but is not limited thereto.
[0037] The cycloalkyl group of the present invention refers to a monovalent group formed by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornyl, etc., but not limited thereto.
[0038] The heterocycloalkyl group of the present invention refers to a group formed by removing a hydrogen atom from a heterocyclic molecule whose ring atoms contain at least one heteroatom in addition to carbon atoms, wherein the heteroatom includes but is not limited to O, S, N, Si or P atoms, preferably having 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. For example, piperidinyl, piperazinyl, tetrahydropyrrolyl, oxiranyl, cyclothioranyl, propylene, morpholinyl, thiomorpholinyl, etc., but not limited thereto.
[0039] The aryl group of the present invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon of the aromatic compound molecule, which can be a monocyclic aryl group or a condensed ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. Among them, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, pyrenyl, triphenylene, fluoranthenyl, benzofluorenyl, spirobifluorenyl, benzofluoranthenyl, chrysene, etc., but not limited thereto.
[0040] The arylene group described in the present invention may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group. The arylene group refers to a divalent group formed by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule, preferably having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, for example, phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, phenylenefluorenyl, dibenzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, fluoranthenyl, etc., but are not limited thereto.
[0041] The heteroaryl group described in the present invention refers to a group formed by replacing one or more aromatic carbon atoms in the aromatic group with heteroatoms, which can be a monocyclic heteroaryl group or a condensed ring heteroaryl group, wherein the heteroatoms include but are not limited to oxygen, sulfur, nitrogen, silicon, and phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. These include pyridyl, pyrimidinyl, triazine, furanyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, quinazolinyl, quinoxalinyl, quinolyl, indolyl, azacarbazolyl, azafluorenyl, azaspirobifluorenyl, xanthracene, thioxanthracene, and the like, but are not limited thereto.
[0042] The heteroarylene group of the present invention refers to a group formed by replacing one or more aromatic carbon atoms in the arylene group with heteroatoms, and the heteroatoms include but are not limited to O, S, N, Si or P atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms, for example, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, carbazolylene, benzofuranylene, benzothienylene, benzocarbazolylene, dibenzofuranylene, dibenzothienylene, dibenzocarbazolylene, benzodibenzofuranylene, benzodibenzothienylene, isoquinolylene, bipyridylene, bipyrimidylene, phenylpyridylene, phenylpyrimidylene, etc., but not limited thereto.
[0043] The fused cyclic group of an alicyclic ring and an aromatic ring of the present invention refers to a monovalent group formed by removing a hydrogen atom from an alicyclic ring and an aromatic ring after the alicyclic ring and the aromatic ring are fused together. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, for example, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but is not limited thereto.
[0044] The fused cyclic radical of an alicyclic ring and an aromatic ring of the present invention refers to a divalent group formed by removing two hydrogen atoms after the alicyclic ring and the aromatic ring are fused together. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, for example, benzocyclopropylene, benzocyclobutylene, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, naphthocyclopropylene, naphthocyclobutylene, naphthocyclopentylene, naphthocyclohexylene, etc., but is not limited thereto.
[0045] The fused ring group of heterocycloalkane and aromatic ring of the present invention refers to a monovalent group formed by removing a hydrogen atom after the heterocycloalkane and aromatic ring are fused together. It preferably has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, for example, benzopyrrolyl, naphthopyrrolyl, phenanthropyrrolyl, benzazetidinyl, benzazepanyl, benzopiperidinyl, naphthopiperidinyl, phenanthropiperidinyl, etc., but is not limited thereto.
[0046] The fused ring group of an alicyclic ring and a heteroaromatic ring described in the present invention refers to a monovalent group formed by condensing an alicyclic ring and a heteroaromatic ring together and removing a hydrogen atom. It preferably has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, for example, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, dibenzothienocycloheptyl, carbazolylcyclopropyl, carbazolylcyclobutyl, carbazolylcyclopentyl, carbazolylcyclohexyl, carbazolylcycloheptyl, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl,
[0047] The sub-fused cyclic group of an alicyclic ring and a heteroaromatic ring described in the present invention refers to a divalent group formed by removing two hydrogen atoms after an alicyclic ring and a heteroaromatic ring are fused together. It preferably has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, for example, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, The following examples include, but are not limited to, dibenzothienocycloheptylene, carbazolylcyclopropylene, carbazolylcyclobutylene, carbazolylcyclopentylene, carbazolylcyclohexylene, carbazolylcycloheptylene, pyridocyclopropylene, pyridocyclobutylene, pyridocyclopentylene, pyridocyclohexylene, pyridobenzocycloheptylene, pyrimidocyclopropylene, pyrimidocyclobutylene, pyrimidocyclopentylene, pyrimidocyclohexylene, pyrimidobenzocycloheptylene, and the like, but are not limited to.
[0048] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R k ) 3 A group in which each R kThe same or different ones are any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring.
[0049] The substituents in the "substituted or unsubstituted" described in the present invention can be independently selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1~C12 alkyl, substituted or unsubstituted C3~C12 cycloalkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl, substituted or unsubstituted C1~C12 alkoxy, substituted or unsubstituted C1~C6 alkylthio, substituted or unsubstituted C1~C12 alkylamino, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C6~C30 arylamino, etc., but are not limited to these, or two adjacent substituents can be connected to form a ring. Deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C12 alkoxy, and specific examples include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, fluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9 ,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirobifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazolindolyl, pyrrolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazine, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, benzocyclobutane, benzocyclobutene, benzocyclopentane, benzocyclopentene, benzocyclohexane, benzocyclohexene, etc., but are not limited thereto. Or when there are multiple substituents, the multiple substituents may be the same as or different from each other; or adjacent substituents may be connected to form a ring.
[0050] The term "connected to form a ring" used in the present invention refers to two groups connected to each other by a chemical bond and optionally aromatized. For example:
[0051]
[0052] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanebenzophenone, cyclohexene, cyclohexane, cyclohexanebenzophenone, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
[0053] In the present invention, the term "at least one" includes one, two, three, four or more. The term "two" or more, when permitted, includes two, three, four or more.
[0054] The present invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:
[0055]
[0056] Wherein, the x is independently selected from any one of CH and N;
[0057] The Ar 1 ,Ar 2 Any one independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring;
[0058] The L is selected from any one of the following groups or a combination of two or more of the following groups:
[0059]
[0060] The z is independently selected from any one of CH and N;
[0061] The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0062] The Y a , Y b , Y c independently selected from O, S, N(R s )
[0063] The Y d , Y e independently selected from O, S, C(R p R q )、N(R t )
[0064] The R b , R b 'Independently selected from any one of fluorine, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl;
[0065] The R p , R q is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p , R q are connected to form a substituted or unsubstituted ring;
[0066] The R s , R t Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0067] The b 1 is selected from 0, 1, 2, 3 or 4; said b 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said b 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b 4 Selected from 0, 1 or 2; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; said b' 1 Selected from 0, 1 or 2; when there are two or more R b ', two or more R b ' are the same or different from each other; wherein each b 1 、b 2 、b 3 、b4 , b' 1 At least one of them is not selected from 0;
[0068] The L 1 , L 2 Any one independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed cyclic group, a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed cyclic group;
[0069] The R 1 , R 2 Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0070] The Ar 1 ,Ar 2 , L 1 , L 2 , R 1 , R 2 At least one of them contains one or more -Si(R n ) 3 ;
[0071] The R n Any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0072] The 1 Selected from 0, 1, 2, 3 or 4; when there are two or more R 1 When two or more R1 The same or different from each other, or two adjacent R 1 are connected to each other to form a substituted or unsubstituted ring;
[0073] The 2 Selected from 0, 1, 2, 3 or 4; when there are two or more R 2 When two or more R 2 The same or different from each other, or two adjacent R 2 They are connected to each other to form a substituted or unsubstituted ring.
[0074] Preferably, the Ar 1 ,Ar 2 Independently selected from any one of the following groups:
[0075]
[0076] The v is independently selected from any one of CH and N;
[0077] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;
[0078] The X 1 , X 2 independently selected from O, S, N(R v )
[0079] The X 3 , X 4 , X 5 independently selected from O, S, C(R x R y )、N(R z )
[0080] The R a , R a ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , any one of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C1-C25 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, a substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group;
[0081] The R x , Ry independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R x , R y are connected to form a substituted or unsubstituted ring;
[0082] The R v , R z independently selected from hydrogen, deuterium, tritium, -Si(R n ) 3 , any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0083] The a 1 is selected from 0, 1, 2, 3, 4 or 5; said a 2 is selected from 0, 1, 2, 3 or 4; said a 3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said a 4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; 5 is selected from 0, 1 or 2; said a 6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; 7 Selected from 0, 1, 2 or 3; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a are connected to each other to form a substituted or unsubstituted ring;
[0084] The a' 0 is selected from 0 or 1; said a' 1 Selected from 0, 1 or 2; when there are two or more R a ', two or more R a ' are the same as or different from each other.
[0085] More preferably, the Ar 1 ,Ar 2 Independently selected from any one of the following groups:
[0086]
[0087] The R a , R a ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , substituted or unsubstituted as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl , fluoranthene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;
[0088] The R x , R y independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , substituted or unsubstituted as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0089] The R v , R z independently selected from hydrogen, deuterium, tritium, -Si(R n ) 3, substituted or unsubstituted as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0090] The L' is selected from the following groups: single bond, substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, pyrenylene, perylene, fluoranthenylene, pyridylene, pyrimidylene, triazineylene, furanylene, thienylene, carbazolylene, benzofuranylene, benzothiophenylene, benzocarbazolylene, dibenzofuranylene, dibenzothiophenylene, dibenzo Any one of carbazolyl, benzodibenzofuranyl, benzodibenzothiophenylene, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzoxazolyl, dibenzothiazolyl, dibenzimidazolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, bipyridyl, bipyrimidyl, phenylpyridyl, and phenylpyrimidyl;
[0091] The a' 0 is selected from 0 or 1; said a' 1 is selected from 0, 1 or 2; said a' 2 is selected from 0, 1, 2, 3 or 4; said a' 3 is selected from 0, 1, 2, 3, 4, 5 or 6; said a' 4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said a' 5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R a ', two or more R a ' are the same as or different from each other.
[0092] More preferably, the Ar 1 ,Ar 2 Independently selected from any one of the following groups:
[0093]
[0094]
[0095]
[0096]
[0097]
[0098]
[0099] Preferably, Ar 1 ,Ar 2 At least one of the groups is selected from those including a “substituted or unsubstituted silyl group” among the aforementioned groups.
[0100] Preferably, L is selected from any one of the following groups or a combination of two or more of the following groups:
[0101]
[0102] The R b , R b 'Independently selected from fluorine, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl;
[0103] The R p , R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro ...
[0104] The R s , R tindependently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;
[0105] The b' 1 is selected from 0, 1 or 2; said b' 2 is selected from 0, 1, 2, 3 or 4; said b' 3 is selected from 0, 1, 2, 3, 4, 5 or 6; said b' 4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b' 5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R b ', two or more R b ' are the same or different from each other; wherein each b 1 、b 2 、b 3 、b 4 , b' 1 , b' 2 , b' 3 , b' 4 , b' 5 At least one of them is not selected from 0.
[0106] More preferably, L is selected from any one of the following groups or a combination of two or more of the following groups:
[0107]
[0108]
[0109] Preferably, the L 1 , L 2 Independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0110]
[0111] The u is independently selected from any one of CH and N;
[0112] The ring C is selected from a substituted or unsubstituted C3-C10 alicyclic ring;
[0113] The Y 1 , Y 2 independently selected from O, S, N(R m )
[0114] The Y 3 , Y 4 , Y 5 independently selected from O, S, C(R i R j )、N(R k )
[0115] The R c , R c ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , any one of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C1-C25 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, a substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group;
[0116] The R i , R j independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R i , R j are connected to form a substituted or unsubstituted ring;
[0117] The R m , R k independently selected from hydrogen, deuterium, tritium, -Si(R n ) 3, any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0118] Said p is selected from 1, 2, 3 or 4;
[0119] The c 1 is selected from 0, 1, 2, 3 or 4; said c 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said c 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c 4 Selected from 0, 1 or 2; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;
[0120] The c' 1 Selected from 0, 1 or 2; when there are two or more R c ', two or more R c ' are the same as or different from each other.
[0121] More preferably, the L 1 , L 2 Independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0122]
[0123]
[0124] The R c , R c ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3, substituted or unsubstituted as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl , fluoranthene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;
[0125] The R i , R j independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n ) 3 , substituted or unsubstituted as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0126] The R m , R k independently selected from hydrogen, deuterium, tritium, -Si(R n ) 3, substituted or unsubstituted as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0127] The c' 1 is selected from 0, 1 or 2; said c' 2 is selected from 0, 1, 2, 3 or 4; said c' 3 is selected from 0, 1, 2, 3, 4, 5 or 6; said c' 4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c' 5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R c ', two or more R c ' are the same as or different from each other.
[0128] More preferably, the L 1 , L 2 Independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0129]
[0130]
[0131] Preferably, Ar 1 or Ar 2 Contains 1, 2, 3 or 4 -Si(R n ) 3 .
[0132] Preferably, L 1 or L 2 Contains 1, 2, 3 or 4 -Si(R n ) 3 .
[0133] Preferably, R 1 or R 2 Selected from -Si(R n ) 3 .
[0134] Preferably, -Si(R n ) 3 Independently selected from trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl.
[0135] Preferably, the formula I contains 1-8 -Si(R n ) 3 , preferably containing 1, 2, 3, 4, 5, 6, 7 or 8 -Si(R n ) 3 , more preferably containing 1-4 -Si(R n ) 3 , most preferably containing 1-2 -Si(R n ) 3 .
[0136] Most preferably, the formula I is selected from any one of the following structures:
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154] Some specific structural forms of the aromatic amine compounds represented by Chemical Formula I of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all structures based on the structure shown in Chemical Formula I and having substituents as defined above should be included.
[0155] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or located on the side of the cathode away from the anode, wherein the organic layer contains at least one of the aromatic amine compounds described in the present invention.
[0156] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes at least one of a hole transport layer and a light-emitting layer, the hole transport layer is located between the anode and the cathode, the light-emitting layer is located between the hole transport layer and the cathode, and at least one of the hole transport layer and the light-emitting layer includes at least one of the aromatic amine compounds described in the present invention.
[0157] More preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprises at least one of the aromatic amine compounds described in the present invention.
[0158] More preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, the third hole transport layer is located between the second hole transport layer and the light-emitting layer, and at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer comprises at least one of the aromatic amine compounds described in the present invention.
[0159] More preferably, the light-emitting layer comprises a host material, and the host material comprises at least one of the aromatic amine compounds described in the present invention.
[0160] More preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generating layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generating layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generating layer comprises at least one of the aromatic amine compounds described in the present invention.
[0161] More preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, and the charge generation layer includes a P-type charge generation layer, and the P-type charge generation layer includes at least one of the aromatic amine compounds described in the present invention.
[0162] Preferably, the organic layer is located on a side of the cathode facing away from the anode, and the organic layer comprises a covering layer, and the covering layer comprises at least one of the aromatic amine compounds described in the present invention.
[0163] The anode of the present invention is preferably a high work function material that can promote hole injection into the organic layer. It may include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; laminated structures such as ITO / Ag / ITO, Al / Ag, etc., but are not limited thereto.
[0164] The hole injection layer of the present invention preferably has a material with good hole acceptance ability. In addition to the aromatic amine compound provided by the present invention, it can also include triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, radialene compounds and other substances with high hole injection properties, such as hexacyanohexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), 1,2,3-tri[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane, etc., but is not limited thereto. The aromatic amine compound of the present invention is preferred.
[0165] The hole transport layer of the present invention preferably has a material with excellent hole transport performance. In addition to the aromatic amine compound provided by the present invention, it can also include carbazole derivatives, fluorene derivatives, biphenyl diamine derivatives, triarylamine derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazatriphenylene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc., such as N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N, N'-diphenyl-N, N'-di (3-methylphenyl) -1, 1'-biphenyl-4, 4'-diamine (TPD), N, N'-di (4-biphenyl) -N, N'-diphenyl benzidine, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0166] The electron blocking layer of the present invention preferably has a material with good hole transport ability and the ability to block electrons. In addition to the aromatic amine compound provided by the present invention, aromatic amine derivatives, carbazole derivatives, etc. may also be included. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), etc., but are not limited thereto. The aromatic amine compound of the present invention is preferred.
[0167] The light-emitting layer of the present invention may include a guest material and a host material. In addition to the aromatic amine compound provided by the present invention, the host material of the light-emitting layer may also include naphthalene derivatives, pentacene derivatives, anthracene derivatives, pyrene derivatives, phenanthrene derivatives, fluoranthene derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, distyryl aryl derivatives, stilbene derivatives, etc., such as ADN, Alq 3 , BAlq, TPBi, TPD, CBP, TCTA, etc., and the guest material can use fluorescent luminescent materials and phosphorescent luminescent materials. Fluorescent luminescent materials are compounds that emit light from a singlet excited state, including aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc., such as BCzVBi, DPAVBi, etc., and phosphorescent luminescent materials can also be used, including metal complexes such as iridium complexes, osmium complexes, and platinum complexes, such as FIrpic, Ir(ppy) 3 、Ir(ppy) 2 (acac) etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0168] The hole blocking layer of the present invention is a layer that prevents holes from reaching the cathode, and can usually be formed using the same conditions as the hole injection layer. It can include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymer compounds, etc., such as TPBi, BAlq, etc., but not limited thereto.
[0169] The electron transport layer of the present invention is a layer containing a material with high electron transport properties (electron transport material). It can be a single-layer structure or a multi-layer structure, and can include metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives and other aromatic heterocyclic compounds, polymer compounds, etc., such as Alq 3 、BeBq 2 , BAlq, PBD, ZnPBO, PBD, BPhen, etc., but not limited to these.
[0170] The electron injection layer of the present invention is a layer containing a material with high electron injection property (electron injection material). It may include alkali metals, alkaline earth metals or their compounds, and other substances with high electron injection property, such as LiF, Yb, Mg, Ca, Li, Sr, CsF, CaF 2 、BaO、Li 2 CO 3 、CaCO 3 , Li 2 C 2 O 4 , Cs 2 C 2 O 4 , CsAlF 4 , LiOx, Tb, etc., but not limited to these.
[0171] The cathode of the present invention is preferably a low work function material, which may include metals, metal alloys or multilayer structures, such as alkali metals such as lithium and cesium, alkaline earth metals such as magnesium, calcium and strontium, alloys containing these metals (such as MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), alloys containing rare earth metals, etc., but are not limited thereto.
[0172] The cover layer material of the present invention is preferably a material having a light coupling function. In addition to the aromatic amine compound provided by the present invention, it may also include metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc., such as Alq 3 、LiF、CsF、MgF 2 , CaF 2 、CsCl、CuI、V2 O 5 , WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 , SiN, ZnS, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0173] The P-type charge generation layer material of the present invention includes an organic material doped with a metal or a P-type dopant. In addition to the aromatic amine compound provided by the present invention, it may also include an alloy of one or two of the group consisting of aluminum (Al), copper (Cu), iron (Fe), lead (Pb), zinc (Zn), gold (Au), platinum (Pt), tungsten (W), indium (In), molybdenum (Mo), nickel (Ni) and titanium (Ti). The P-type dopant may include F4-TCNQ, iodine (I), ferric chloride (FeCl 3 ), ferric fluoride (FeF 3 ) and antimony chloride (SbCl 5 ), the host may include at least one selected from the group consisting of NPB, TPD, TNB and HAT-CN, etc., but is not limited thereto. The aromatic amine compound of the present invention is preferred.
[0174] The N-type charge generation layer materials described in the present invention include N-type doped organic materials such as alkali metals such as Li, Na, K, Rb, Cs, Fr, etc.; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, Ra, etc.; Group 15 metals such as Bi (bismuth) and Sb (antimony); lanthanide metals such as La (lanthanum), Ce (cerium), Pr (praseodymium), Nd (neodymium), Pm (promethium), Sm (samarium), Gd (gadolinium), etc.; and more than one of the above metal compounds, etc. In addition, it can also be an organic N-type dopant that has electron-donating properties and can supply at least a portion of the electron charge to the organic host and form a charge transfer complex with the organic host. Examples thereof include BEDT-TTF, TTF, etc., but are not limited thereto.
[0175] The following is a method for preparing the compound represented by the chemical formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of the chemical formula I can be prepared by the reaction route shown below, the substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of substituents can be changed according to techniques known in the art.
[0176] [Synthetic route]
[0177] Preparation of compounds of formula I:
[0178]
[0179] Xa, Xb, and Xc are each independently selected from any one of Cl, Br, and I; 1 , R 2 、n 1 、n 2 ,L,L 1 , L 2 ,Ar 1 ,Ar 2 The limitations are the same as above.
[0180] Description of raw materials, reagents and characterization equipment:
[0181] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. The raw materials and reagents may be commercially available products or prepared by methods well known to those skilled in the art.
[0182] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;
[0183] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar of Germany, with a sample mass of 5 to 10 mg.
[0184] [Synthesis Example 1] Synthesis of Compound 13
[0185]
[0186] Synthetic intermediate c-13
[0187] Under nitrogen protection, d-13 (20.07 g, 120.00 mmol), e-13 (24.66 g, 120.00 mmol), palladium acetate (0.40 g, 1.80 mmol), sodium tert-butoxide (23.06 g, 240.00 mmol), tri-tert-butylphosphine (14.40 ml, 7.20 mmol) and toluene (600 mL) were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for 4 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / ethanol (10:1) to obtain intermediate c-13 (30.11 g, yield 86%), and the solid purity was ≥99.76% by HPLC. Mass spectrum m / z: 291.0831 (theoretical value: 291.0815).
[0188] Synthetic intermediate A-13
[0189] Under nitrogen protection, a-13 (13.22 g, 80.00 mmol), b-13 (19.13 g, 80.00 mmol), palladium acetate (0.27 g, 1.20 mmol), sodium tert-butoxide (15.38 g, 160.00 mmol), tri-tert-butylphosphine (9.60 ml, 4.80 mmol) and toluene (400 ml) were added to the reaction bottle, stirred for 5 hours under reflux conditions, cooled to room temperature, added with water, extracted with ethyl acetate, combined organic phases, dried with anhydrous magnesium sulfate, removed the solvent under reduced pressure, and recrystallized with toluene / ethanol (9:1) to obtain intermediate A-13 (22.52 g, yield 87%), HPLC detection solid purity ≥ 99.84%. Mass spectrum m / z: 323.2057 (theoretical value: 323.2069).
[0190] Synthesis of compound 13
[0191] Under nitrogen protection, A-13 (11.32 g, 35.00 mmol), c-13 (10.21 g, 35.00 mmol), sodium tert-butoxide (6.73 g, 70.00 mmol), tridibenzylideneacetone dipalladium (0.32 g, 0.35 mmol), x-phos (0.33 mL, 0.70 mmol), toluene (300 ml) were added to the reaction bottle, and the mixture was reacted for 8 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, water was added, the organic phase was separated, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the crude product was recrystallized from toluene to obtain compound 13 (15.80 g, yield 78%). The solid purity was ≥99.95% detected by HPLC. Mass spectrum m / z: 578.3127 (theoretical value: 578.3117). Theoretical element content (%) C 40 H 42 N 2 Si: C, 83.00; H, 7.31; N, 4.84. Measured element content (%): C, 83.02; H, 7.33; N, 4.81.
[0192] [Synthesis Example 2] Synthesis of Compound 37
[0193]
[0194] According to the preparation method of Synthesis Example 1, d-13 was replaced by an equal mole of d-37, and b-13 was replaced by an equal mole of b-37 to obtain compound 37 (17.98 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 684.3919 (theoretical value: 684.3900). Theoretical element content (%) C 48 H 52 N 2Si: C, 84.16; H, 7.65; N, 4.09. Measured element content (%): C, 84.15; H, 7.68; N, 4.06.
[0195] [Synthesis Example 3] Synthesis of Compound 53
[0196]
[0197] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-53, and b-13 was replaced by an equal mole of b-53 to obtain compound 53 (15.98 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: 600.2974 (theoretical value: 600.2961). Theoretical element content (%) C 42 H 40 N 2 Si: C, 83.95; H, 6.71; N, 4.66. Measured element content (%): C, 83.94; H, 6.74; N, 4.65.
[0198] [Synthesis Example 4] Synthesis of Compound 68
[0199]
[0200] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-68, a-13 was replaced by an equal mole of a-68, and b-13 was replaced by an equal mole of b-68 to obtain compound 68 (16.68 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 652.3256 (theoretical value: 652.3274). Theoretical element content (%) C 46 H 44 N 2 Si: C, 84.62; H, 6.79; N, 4.29. Measured element content (%): C, 84.64; H, 6.76; N, 4.27.
[0201] [Synthesis Example 5] Synthesis of Compound 86
[0202]
[0203] According to the preparation method of Synthesis Example 1, b-13 was replaced with an equal molar amount of b-86 to obtain Compound 86 (15.90 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 613.2532 (theoretical value: 613.2549). Theoretical element content (%) C 41 H 35 N 3OSi: C, 80.23; H, 5.75; N, 6.85. Measured element content (%): C, 80.26; H, 5.73; N, 6.84.
[0204] [Synthesis Example 6] Synthesis of Compound 97
[0205]
[0206] According to the preparation method of Synthesis Example 1, b-13 was replaced with an equal molar amount of b-97 to obtain compound 97 (16.91 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 661.2927 (theoretical value: 661.2913). Theoretical element content (%) C 46 H 39 N 3 Si: C, 83.47; H, 5.94; N, 6.35. Measured element content (%): C, 83.45; H, 5.91; N, 6.39.
[0207] [Synthesis Example 7] Synthesis of Compound 108
[0208]
[0209] According to the preparation method of Synthesis Example 1, a-13 was replaced by an equal mole of a-108, and b-13 was replaced by an equal mole of b-108 to obtain compound 108 (17.32 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 706.3763 (theoretical value: 706.3743). Theoretical element content (%) C 50 H 50 N 2 Si: C, 84.94; H, 7.13; N, 3.96. Measured element content (%): C, 84.98; H, 7.15; N, 3.93.
[0210] [Synthesis Example 8] Synthesis of Compound 111
[0211]
[0212] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-111, a-13 was replaced by an equal molar amount of a-111, and b-13 was replaced by an equal molar amount of b-53 to obtain Compound 111 (17.03 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: 648.2952 (theoretical value: 648.2961). Theoretical element content (%) C 46 H 40 N 2Si: C, 85.14; H, 6.21; N, 4.32. Measured element content (%): C, 85.11; H, 6.22; N, 4.34.
[0213] [Synthesis Example 9] Synthesis of Compound 131
[0214]
[0215] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-131, a-13 was replaced by an equal molar amount of a-108, and b-13 was replaced by an equal molar amount of b-37 to obtain Compound 131 (17.72 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 702.3447 (theoretical value: 702.3430). Theoretical element content (%) C 50 H 46 N 2 Si: C, 85.42; H, 6.60; N, 3.98. Measured element content (%): C, 85.43; H, 6.61; N, 3.95.
[0216] [Synthesis Example 10] Synthesis of Compound 140
[0217]
[0218] According to the preparation method of Synthesis Example 1, a-13 was replaced by an equal mole of a-108, and b-13 was replaced by an equal mole of b-140 to obtain compound 140 (17.60 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: 688.3262 (theoretical value: 688.3274). Theoretical element content (%) C 49 H 44 N 2 Si: C, 85.42; H, 6.44; N, 4.07. Measured element content (%): C, 85.45; H, 6.42; N, 4.06.
[0219] [Synthesis Example 11] Synthesis of Compound 148
[0220]
[0221] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-148, a-13 was replaced by an equal molar amount of a-108, and b-13 was replaced by an equal molar amount of b-148 to obtain Compound 148 (15.57 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 617.2926 (theoretical value: 617.2911). Theoretical element content (%) C 42 H31 D 5 N 2 OSi: C, 81.64; H, 6.69; N, 4.53. Measured element content (%): C, 81.61; H, 6.67; N, 4.57.
[0222] [Synthesis Example 12] Synthesis of Compound 167
[0223]
[0224] According to the preparation method of Synthesis Example 1, a-13 was replaced by an equal mole of a-167, and b-13 was replaced by an equal mole of b-167 to obtain compound 167 (16.34 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 666.3021 (theoretical value: 666.3004). Theoretical element content (%) C 46 H 34 D 4 N 2 OSi: C, 82.84; H, 6.35; N, 4.20. Measured element content (%): C, 82.81; H, 6.37; N, 4.22.
[0225] [Synthesis Example 13] Synthesis of Compound 177
[0226]
[0227] According to the preparation method of Synthesis Example 1, a-13 was replaced by an equal mole of a-108, and b-13 was replaced by an equal mole of b-177 to obtain compound 177 (19.97 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 826.3387 (theoretical value: 826.3379). Theoretical element content (%) C 59 H 46 N 2 OSi: C, 85.68; H, 5.61; N, 3.39. Measured element content (%): C, 85.65; H, 5.65; N, 3.36.
[0228] [Synthesis Example 14] Synthesis of Compound 181
[0229]
[0230] According to the preparation method of Synthesis Example 1, a-13 was replaced by an equal mole of a-181, and b-13 was replaced by an equal mole of b-37 to obtain compound 181 (15.91 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 622.2818 (theoretical value: 622.2804). Theoretical element content (%) C 44 H 38 N 2 Si: C, 84.84; H, 6.15; N, 4.50. Measured element content (%): C, 84.81; H, 6.16; N, 4.53.
[0231] [Synthesis Example 15] Synthesis of Compound 195
[0232]
[0233] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-195, a-13 was replaced by an equal molar amount of a-195, and b-13 was replaced by an equal molar amount of b-195 to obtain Compound 195 (16.76 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 683.2235 (theoretical value: 683.2227). Theoretical element content (%) C 44 H 34 FN 3 SSi: C, 77.27; H, 5.01; N, 6.14. Measured element content (%): C, 77.25; H, 5.04; N, 6.15.
[0234] [Synthesis Example 16] Synthesis of Compound 203
[0235]
[0236] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-203, and b-13 was replaced by an equal mole of b-203 to obtain Compound 203 (15.20 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 586.2815 (theoretical value: 586.2804). Theoretical element content (%) C 41 H 38 N 2 Si: C, 83.91; H, 6.53; N, 4.77. Measured element content (%): C, 83.93; H, 6.55; N, 4.73.
[0237] [Synthesis Example 17] Synthesis of Compound 208
[0238]
[0239] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-208, a-13 was replaced by an equal molar amount of a-208, and b-13 was replaced by an equal molar amount of b-203 to obtain Compound 208 (18.07 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 758.3101 (theoretical value: 758.3117). Theoretical element content (%) C 55 H 42 N 2 Si: C, 87.03; H, 5.58; N, 3.69. Measured element content (%): C, 87.06; H, 5.55; N, 3.68.
[0240] [Synthesis Example 18] Synthesis of Compound 277
[0241]
[0242] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-277, and b-13 was replaced by an equal mole of b-277 to obtain Compound 277 (16.23 g). The solid purity detected by HPLC was ≥ 99.93%. Mass spectrum m / z: 652.3231 (theoretical value: 652.3212). Theoretical element content (%) C 46 H 36 D 4 N 2 Si: C, 84.62; H, 6.79; N, 4.29. Measured element content (%): C, 84.65; H, 6.78; N, 4.27.
[0243] [Synthesis Example 19] Synthesis of Compound 288
[0244]
[0245] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-288, and b-13 was replaced by an equal mole of b-37 to obtain compound 288 (18.83 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: 746.4068 (theoretical value: 746.4056). Theoretical element content (%) C 53 H 54 N 2 Si: C, 85.21; H, 7.29; N, 3.75. Measured element content (%): C, 85.24; H, 7.27; N, 3.74.
[0246] [Synthesis Example 20] Synthesis of Compound 300
[0247]
[0248] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-300, and b-13 was replaced by an equal molar amount of b-300 to obtain Compound 300 (17.22 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 664.3291 (theoretical value: 664.3274). Theoretical element content (%) C 47 H 44 N 2 Si: C, 84.89; H, 6.67; N, 4.21. Measured element content (%): C, 84.87; H, 6.66; N, 4.24.
[0249] [Synthesis Example 21] Synthesis of Compound 328
[0250]
[0251] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-328, and b-13 was replaced by an equal mole of b-328 to obtain compound 328 (19.07 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: 812.3568 (theoretical value: 812.3587). Theoretical element content (%) C 59 H 48 N 2 Si: C, 87.15; H, 5.95; N, 3.45. Measured element content (%): C, 87.18; H, 5.93; N, 3.46.
[0252] [Synthesis Example 22] Synthesis of Compound 332
[0253]
[0254] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-332, and b-13 was replaced by an equal mole of b-332 to obtain compound 332 (17.49 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 703.2641 (theoretical value: 703.2631). Theoretical element content (%) C 45 H 36 F 3 N 3 Si: C, 76.79; H, 5.16; N, 5.97. Measured element content (%): C, 76.77; H, 5.18; N, 5.94.
[0255] [Synthesis Example 23] Synthesis of Compound 365
[0256]
[0257] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-365, a-13 was replaced by an equal molar amount of a-365, and b-13 was replaced by an equal molar amount of b-365 to obtain Compound 365 (18.27 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 724.3266 (theoretical value: 724.3274). Theoretical element content (%) C 52 H 44 N 2 Si: C, 86.15; H, 6.12; N, 3.86. Measured element content (%): C, 86.14; H, 6.15; N, 3.83.
[0258] [Synthesis Example 24] Synthesis of Compound 433
[0259]
[0260] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-433, a-13 was replaced by an equal molar amount of a-108, and b-13 was replaced by an equal molar amount of b-433 to obtain compound 433 (17.63 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 729.3572 (theoretical value: 729.3588). Theoretical element content (%) C 52 H 39 D 5 N 2 Si: C, 85.55; H, 6.76; N, 3.84. Measured element content (%): C, 85.51; H, 6.78; N, 3.87.
[0261] [Synthesis Example 25] Synthesis of Compound 460
[0262]
[0263] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-460, a-13 was replaced by an equal molar amount of a-108, and b-13 was replaced by an equal molar amount of b-460 to obtain Compound 460 (20.56 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 889.3872 (theoretical value: 889.3852). Theoretical element content (%) C 64 H 51 N 3Si: C, 86.35; H, 5.77; N, 4.72. Measured element content (%): C, 86.37; H, 5.74; N, 4.73.
[0264] [Synthesis Example 26] Synthesis of Compound 465
[0265]
[0266] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-465, a-13 was replaced by an equal mole of a-108, and b-13 was replaced by an equal mole of b-465 to obtain Compound 465 (20.91 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 932.4543 (theoretical value: 932.4526). Theoretical element content (%) C 68 H 60 N 2 Si: C, 87.51; H, 6.48; N, 3.00. Measured element content (%): C, 87.52; H, 6.44; N, 3.02.
[0267] [Synthesis Example 27] Synthesis of Compound 479
[0268]
[0269] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-479, a-13 was replaced by an equal mole of a-479, and b-13 was replaced by an equal mole of b-37 to obtain compound 479 (19.40 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 802.3734 (theoretical value: 802.3743). Theoretical element content (%) C 58 H 50 N 2 Si: C, 86.74; H, 6.28; N, 3.49. Measured element content (%): C, 86.75; H, 6.25; N, 3.48.
[0270] [Synthesis Example 28] Synthesis of Compound 498
[0271]
[0272] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-498, and b-13 was replaced by an equal mole of b-37 to obtain compound 498 (17.61 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 698.3103 (theoretical value: 698.3117). Theoretical element content (%) C 50 H42 N 2 Si: C, 85.92; H, 6.06; N, 4.01. Measured element content (%): C, 85.94; H, 6.03; N, 4.04.
[0273] [Synthesis Example 29] Synthesis of Compound 501
[0274]
[0275] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-501, and b-13 was replaced by an equal mole of b-37 to obtain Compound 501 (18.35 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 770.4038 (theoretical value: 770.4056). Theoretical element content (%) C 55 H 54 N 2 Si: C, 85.67; H, 7.06; N, 3.63. Measured element content (%): C, 85.64; H, 7.09; N, 3.65.
[0276] [Synthesis Example 30] Synthesis of Compound 514
[0277]
[0278] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal molar amount of e-514, a-13 was replaced by an equal molar amount of a-108, and b-13 was replaced by an equal molar amount of b-37 to obtain compound 514 (17.80 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: 736.3011 (theoretical value: 736.3022). Theoretical element content (%) C 51 H 40 N 4 Si: C, 83.12; H, 5.47; N, 7.60. Measured element content (%): C, 83.13; H, 5.45; N, 7.64.
[0279] [Synthesis Example 31] Synthesis of Compound 532
[0280]
[0281] According to the preparation method of Synthesis Example 1, a-13 was replaced by an equal mole of a-532, and b-13 was replaced by an equal mole of b-37 to obtain compound 532 (17.16 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 644.3051 (theoretical value: 644.3043). Theoretical element content (%) C43 H 44 N 2 Si 2 :C, 80.07; H, 6.88; N, 4.34. Measured element content (%): C, 80.06; H, 6.85; N, 4.37.
[0282] [Synthesis Example 32] Synthesis of Compound 588
[0283]
[0284] According to the preparation method of Synthesis Example 1, e-13 was replaced by an equal mole of e-588, and b-13 was replaced by an equal mole of b-588 to obtain Compound 588 (16.71 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 644.3056 (theoretical value: 644.3043). Theoretical element content (%) C 43 H 44 N 2 Si 2 :C, 80.07; H, 6.88; N, 4.34. Measured element content (%): C, 80.08; H, 6.85; N, 4.31.
[0285] [Synthesis Example 33] Synthesis of Compound 652
[0286]
[0287] According to the preparation method of Synthesis Example 1, d-13 was replaced by an equal molar amount of d-652, a-13 was replaced by an equal molar amount of a-652, and b-13 was replaced by an equal molar amount of b-652 to obtain compound 652 (18.42 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 740.3963 (theoretical value: 740.3982). Theoretical element content (%) C 50 H 56 N 2 Si 2 :C, 81.03;H, 7.62;N, 3.78. Measured element content (%): C, 81.02;H, 7.65;N, 3.76.
[0288] [Synthesis Example 34] Synthesis of Compound 654
[0289]
[0290] According to the preparation method of Synthesis Example 1, d-13 was replaced by an equal mole of d-654, a-13 was replaced by an equal mole of a-654, and b-13 was replaced by an equal mole of b-37 to obtain compound 654 (16.58 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: 648.2946 (theoretical value: 648.2961). Theoretical element content (%) C 46 H 40 N 2 Si: C, 85.14; H, 6.21; N, 4.32. Measured element content (%): C, 85.11; H, 6.23; N, 4.33.
[0291] [Synthesis Example 35] Synthesis of Compound 707
[0292]
[0293] According to the preparation method of Synthesis Example 1, d-13 was replaced by an equal molar amount of d-652, e-13 was replaced by an equal molar amount of e-707, and b-13 was replaced by an equal molar amount of b-37 to obtain compound 707 (19.88 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 834.4240 (theoretical value: 834.4221). Theoretical element content (%) C 55 H 62 N 2 Si 3 :C, 79.08; H, 7.48; N, 3.35. Measured element content (%): C, 79.06; H, 7.46; N, 3.38.
[0294] [Device Example]
[0295] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the luminous efficiency of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company.
[0296] [Example 1]
[0297] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine, and after washing, the substrate was transferred to an evaporator. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-1 was evaporated on the anode to form a thickness of The hole injection layer is formed by evaporating the compound 13 of the present invention on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is deposited on the hole transport layer. The light-emitting layer is formed by evaporating GH-1 as the main material of the light-emitting layer and doping 4wt% of GD-1 to form a layer with a thickness of ET-1:LiQ (mass ratio 1:1) was evaporated on the luminescent layer to form a layer with a thickness of The electron transport layer is formed by evaporating LiF on the electron transport layer to form a layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0298]
[0299] [Examples 2 to 35]
[0300] Compound 37, compound 53, compound 68, compound 86, compound 97, compound 108, compound 111, compound 131, compound 140, compound 148, compound 167, compound 177, compound 181, compound 195, compound 203, compound 208, compound 277, compound 288, compound 300, compound 328, compound 332, compound 365, compound 433, compound 460, compound 465, compound 479, compound 498, compound 501, compound 514, compound 532, compound 588, compound 652, compound 654, and compound 707 of the present invention were used to replace compound 13 in Example 1 as hole transport layer materials, except that an organic electroluminescent device was prepared by the same preparation method as Example 1.
[0301] [Comparative Examples 1 to 3]
[0302] Organic electroluminescent devices were prepared by the same preparation method as in Example 1 except that Compound P-1, Compound P-2 and Compound P-3 were used to replace Compound 13 in Example 1 as hole transport layer materials.
[0303] The test environment is an atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the devices 1 to 35 in the embodiments of the present invention and the comparative examples 1 to 3 are shown in Table 1 below.
[0304] Table 1:
[0305]
[0306]
[0307] From the results in Table 1, it can be seen that when the aromatic amine compound described in the present invention is applied to the hole transport layer of an organic electroluminescent device, compared with the comparative compounds P-1 to P-3, the device has higher luminous efficiency and longer service life. The aromatic amine compound of the present invention is a hole transport layer material with good performance.
[0308] [Example 36]
[0309] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, it was transferred to a plasma cleaning machine, and after washing, the substrate was transferred to an evaporator. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-2:HT-2 (mass ratio 3:97) was evaporated on the anode to form a layer with a thickness of HT-2 is evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer. The compound 13 of the present invention is evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is deposited on the second hole transport layer. The light-emitting layer is formed by evaporating BH-2 as the main material of the light-emitting layer and doping 4wt% of BD-2 to form a thickness of ET-2 is evaporated on the luminescent layer to form a luminescent layer with a thickness of The electron transport layer is formed by evaporating LiF on the electron transport layer to form a layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0310]
[0311] [Examples 37 to 70]
[0312] Compound 37, compound 53, compound 68, compound 86, compound 97, compound 108, compound 111, compound 131, compound 140, compound 148, compound 167, compound 177, compound 181, compound 195, compound 203, compound 208, compound 277, compound 288, compound 300, compound 328, compound 332, compound 365, compound 433, compound 460, compound 465, compound 479, compound 498, compound 501, compound 514, compound 532, compound 588, compound 652, compound 654, and compound 707 of the present invention were used to replace compound 13 in Example 36 as the second hole transport layer material, except that an organic electroluminescent device was prepared by the same preparation method as Example 36.
[0313] [Comparative Examples 4 to 6]
[0314] Organic electroluminescent devices were prepared by the same preparation method as in Example 36 except that Compound P-4, Compound P-5 and Compound P-6 were used to replace Compound 13 in Example 36 as the second hole transport layer material.
[0315] The test environment is an atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments 36 to 70 of the present invention and the comparative embodiments 4 to 6 are shown in Table 2 below.
[0316] Table 2:
[0317]
[0318]
[0319] It can be seen from the results in Table 2 that when the aromatic amine compound described in the present invention is applied to the second hole transport layer of the organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-4 to P-6. The compound of the present invention is a second hole transport layer material with good performance.
[0320] [Example 71]
[0321] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, it was transferred to a plasma cleaning machine, and after washing, the substrate was transferred to an evaporator. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-2:HT-3 (mass ratio 2:98) was evaporated on the anode to form a layer with a thickness of HT-3 is evaporated on the hole injection layer to form a hole injection layer with a thickness of A light-emitting layer was evaporated on the hole transport layer, with RH-3: the compound 13 of the present invention (mass ratio 1:1) as the main material of the light-emitting layer and 3 wt% of RD-3 doped to form a layer with a thickness of HB-3 is evaporated on the luminescent layer to form a light-emitting layer with a thickness of ET-3:LiQ (mass ratio 1:1) was evaporated on the hole blocking layer to form a layer with a thickness of The electron transport layer is formed by evaporating LiF on the electron transport layer to form a layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0322]
[0323] [Examples 72 to 105]
[0324] Compound 37, compound 53, compound 68, compound 86, compound 97, compound 108, compound 111, compound 131, compound 140, compound 148, compound 167, compound 177, compound 181, compound 195, compound 203, compound 208, compound 277, compound 288, compound 300, compound 328, compound 332, compound 365, compound 433, compound 460, compound 465, compound 479, compound 498, compound 501, compound 514, compound 532, compound 588, compound 652, compound 654 and compound 707 of the present invention are used to replace compound 13 in Example 71 as the main material of the light-emitting layer. Except for this, an organic electroluminescent device is prepared by the same preparation method as Example 71.
[0325] [Comparative Examples 7 to 8]
[0326] An organic electroluminescent device was prepared by the same preparation method as in Example 71, except that Compound P-7 and Compound P-8 were used to replace Compound 13 in Example 71 as the main materials of the light-emitting layer.
[0327] The test environment is an atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments of the present invention 71-105 and comparative examples 7-8 are shown in Table 3 below.
[0328] Table 3:
[0329]
[0330]
[0331] The results in Table 3 show that when the aromatic amine compound of the present invention is applied to the light-emitting layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-7 to P-8. The compound of the present invention is a main material for the light-emitting layer with good performance.
[0332] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.
Claims
1. An aromatic amine compound, characterized in that The aromatic amine compound has a structure represented by Formula I: Wherein, the x is independently selected from any one of CH and N; The Ar1 and Ar2 are independently selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a fused ring group of a C6-C30 aromatic ring, a substituted or unsubstituted C1-C25 heterocycloalkane and a fused ring group of a C6-C30 aromatic ring, and a substituted or unsubstituted C3-C25 alicyclic ring and a fused ring group of a C2-C30 heteroaromatic ring; The L is selected from any one of the following groups or a combination of two or more of the following groups: The z is independently selected from any one of CH and N; The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings; The Y a , Y b , Y c independently selected from O, S, N(R s ) The Y d , Y e independently selected from O, S, C(R p R q )、N(R t ) The R b , R b 'Independently selected from any one of fluorine, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl; The R p , R q is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p , R q are connected to form a substituted or unsubstituted ring; The R s , R t Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; b1 is selected from 0, 1, 2, 3 or 4; b2 is selected from 0, 1, 2, 3, 4, 5 or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; b4 is selected from 0, 1 or 2; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; the b'1 is selected from 0, 1 or 2; when there are two or more R b ', two or more R b ' are the same or different from each other; wherein at least one of b1, b2, b3, b4, b'1 is not selected from 0; The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic group and C6-C30 aromatic ring condensed group, and a substituted or unsubstituted C3-C25 alicyclic group and C2-C30 heteroaromatic ring condensed group; The R1 and R2 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group; At least one of Ar1, Ar2, L1, L2, R1, and R2 contains one or more -Si(R n )3; The R n Any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group; The n1 is selected from 0, 1, 2, 3 or 4; when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring; The n2 is selected from 0, 1, 2, 3 or 4; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring.
2. An aromatic amine compound according to claim 1, characterized in that: The Ar1 and Ar2 are independently selected from any one of the following groups: The v is independently selected from any one of CH and N; The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring; Said X1 and X2 are independently selected from O, S, N (R v ) The X3, X4, and X5 are independently selected from O, S, C(R x R y )、N(R z ) The R a , R a ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3. any one of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C1-C25 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, a substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group; The R x , R y independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3, any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R x , R y are connected to form a substituted or unsubstituted ring; The R v , R z independently selected from hydrogen, deuterium, tritium, -Si(R n )3. any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a5 is selected from 0, 1 or 2; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a7 is selected from 0, 1, 2 or 3; when two or more R a When two or more R a The same or different from each other, or two adjacent R a are connected to each other to form a substituted or unsubstituted ring; a'0 is selected from 0 or 1; a'1 is selected from 0, 1 or 2; when there are two or more R a ', two or more R a ' are the same as or different from each other.
3. An aromatic amine compound according to claim 1, characterized in that: The Ar1 and Ar2 are independently selected from any one of the following groups: The R a , R a ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3. Substituted or unsubstituted groups as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorene any one of benzofuranyl, fluorantheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl; The R x , R y independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3. substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The R v , R z independently selected from hydrogen, deuterium, tritium, -Si(R n )3. substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The L' is selected from the following groups: single bond, substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, pyrenylene, perylene, fluoranthenylene, pyridylene, pyrimidylene, triazineylene, furanylene, thienylene, carbazolylene, benzofuranylene, benzothiophenylene, benzocarbazolylene, dibenzofuranylene, dibenzothiophenylene, dibenzo Any one of carbazolyl, benzodibenzofuranyl, benzodibenzothiophenylene, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzoxazolyl, dibenzothiazolyl, dibenzimidazolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, bipyridyl, bipyrimidyl, phenylpyridyl, and phenylpyrimidyl; a'0 is selected from 0 or 1; a'1 is selected from 0, 1 or 2; a'2 is selected from 0, 1, 2, 3 or 4; a'3 is selected from 0, 1, 2, 3, 4, 5 or 6; a'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R a ', two or more R a ' are the same as or different from each other.
4. An aromatic amine compound according to claim 1, characterized in that: The L is selected from any one of the following groups or a combination of two or more of the following groups: The R b , R b 'Independently selected from fluorine, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl; The R p , R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro ... The R s , R t independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; b'1 is selected from 0, 1 or 2; b'2 is selected from 0, 1, 2, 3 or 4; b'3 is selected from 0, 1, 2, 3, 4, 5 or 6; b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R b ', two or more R b ' are the same or different from each other; wherein at least one of said b1, b2, b3, b4, b'1, b'2, b'3, b'4, b'5 is not selected from 0.
5. An aromatic amine compound according to claim 1, characterized in that: The L1 and L2 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The u is independently selected from any one of CH and N; The ring C is selected from a substituted or unsubstituted C3-C10 alicyclic ring; Said Y1 and Y2 are independently selected from O, S, N (R m ) The Y3, Y4, and Y5 are independently selected from O, S, C(R i R j )、N(R k ) The R c , R c ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3. any one of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C1-C25 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, a substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group; The R i , R j independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3, any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R i , R j are connected to form a substituted or unsubstituted ring; The R m , R k independently selected from hydrogen, deuterium, tritium, -Si(R n )3. any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said p is selected from 1, 2, 3 or 4; The c1 is selected from 0, 1, 2, 3 or 4; the c2 is selected from 0, 1, 2, 3, 4, 5 or 6; the c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c4 is selected from 0, 1 or 2; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring; The c'1 is selected from 0, 1 or 2; when there are two or more R c ', two or more R c ' are the same as or different from each other.
6. An aromatic amine compound according to claim 1, characterized in that: The L1 and L2 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The R c , R c ' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3. Substituted or unsubstituted groups as follows: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorene any one of benzofuranyl, fluorantheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl; The R i , R j independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, -Si(R n )3. substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The R m , R k independently selected from hydrogen, deuterium, tritium, -Si(R n )3. substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R c ', two or more R c ' are the same as or different from each other.
7. An aromatic amine compound according to claim 1, characterized in that: The formula I is selected from any one of the following structures:
8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or located on a side of the cathode away from the anode, characterized in that: The organic layer contains at least one of the aromatic amine compounds according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, wherein: The organic layer comprises at least one of a hole transport layer and a light-emitting layer, wherein the hole transport layer is located between the anode and the cathode, and the light-emitting layer is located between the hole transport layer and the cathode, and at least one of the hole transport layer and the light-emitting layer comprises at least one of the aromatic amine compounds described in any one of claims 1 to 7.
10. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, wherein: The organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generation layer comprises at least one of the aromatic amine compounds described in any one of claims 1 to 7.