A triarylamine derivative and an organic electroluminescent device thereof

Abstract

The application provides a triarylamine derivative and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. In order to solve the problem of low device performance caused by the covering layer material in the prior art, the application provides a triarylamine derivative and an organic electroluminescent device thereof, which is applied to an organic electroluminescent device as a covering layer material to effectively improve the luminous efficiency and service life of the device. Since the triarylamine derivative has strong rigidity, a suitable glass transition temperature (Tg), good thermal stability and a high refractive index in the molecule, the coupling efficiency of light in the device is increased, the light extraction efficiency is improved, the generation of Joule heat is reduced, and the service performance of the device is improved.

Description

[0001] This application is a divisional application of the invention patent application filed on November 21, 2023, with application number 202311054758.9 and invention title "A triarylamine derivative and its organic electroluminescent device". Technical Field

[0002] This invention relates to the field of organic electroluminescent materials technology, specifically to a triarylamine derivative and its organic electroluminescent device. Background Technology

[0003] In the new era, the internet has brought about tremendous changes to humanity, accelerating technological development. To facilitate richer and more convenient information exchange, there is a need for displays with superior performance to meet human needs. Organic light-emitting diodes (OLEDs), as the next generation of displays, have quickly become a research hotspot and possess immense potential to replace LCD technology, becoming a star technology in the display field. Compared to traditional LCDs, OLED display technology offers advantages such as self-illumination, wide viewing angles, high resolution, lower power consumption, and extremely fast response times. It has broad application prospects in next-generation display and lighting products and has been a popular research area for the past decade or so.

[0004] In OLEDs, under the influence of an applied electric field, electrons from the cathode and holes from the anode recombine in the organic layer, releasing energy and transferring it to the organic light-emitting compound. This causes the compound to transition from its ground state to an excited state. The excited molecules then return to their ground state, releasing energy in the form of light, thus creating the luminescence phenomenon. OLEDs have a sandwich-like structure, typically consisting of an anode, a cathode, and an organic layer formed between these two electrodes. Currently, the organic layers involved in OLEDs include hole injection layers, hole transport layers, hole blocking layers, light-emitting layers, electron blocking layers, electron transport layers, electron injection layers, and capping layers. Although OLED manufacturing processes are constantly being innovated and reformed, large-scale commercial applications still face many challenges due to the current limitations of organic light-emitting materials.

[0005] With the increasing demands of the market, the performance requirements for OLED devices are constantly rising. However, the capping materials currently used in organic light-emitting diodes (OLEDs) have many drawbacks. Most conventional capping materials are inorganic, which presents several disadvantages. Firstly, the deposition of inorganic materials requires high temperatures, causing device deformation due to the high temperatures. Secondly, the internal light of the device exhibits plasmon resonance and total internal reflection, reducing the coupling efficiency of external light and increasing Joule heat generation during operation. Therefore, to improve the luminous efficiency and lifespan of organic light-emitting diodes, it is crucial to develop capping materials with low absorption in the visible light region, high refractive index, excellent thin-film stability, and good thermal stability. Summary of the Invention

[0006] To address the aforementioned problems, this invention provides a triarylamine derivative and its organic electroluminescent device, which significantly improves the luminous efficiency and lifespan of the device.

[0007] This invention provides a triarylamine derivative having the structure shown in Formula I.

[0008] In Formula I, the x atoms are the same or different from each other, are selected from CH or N atoms, and at least two x atoms are selected from N atoms. When x is bonded to other groups, the x atoms are selected from C atoms. The Y is selected from O or S; The Ar1 is selected from any one of the groups shown in Formula II-1 to Formula II-11;

[0009] The z may be the same as or different from each other, and are selected from CH or N atoms. When z is bonded to other groups, the z is selected from C atoms, and at least one z in each group of formulas II-1 to II-9 is selected from N atoms. The t is selected from any one of O, S, and N(R); the R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R can be directly bonded to L1; Q is selected from O, S, C(R) x R y ) or N(R z ); The R x R yThey may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring; or R x R y Either one can be directly bonded to L1, or R x R y They can be connected to each other to form a ring as shown below; ; The R4 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, or terphenyl. p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; and p7 is selected from 0, 1 or 2.

[0010] The R z Selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring; or R z It can be directly bonded to L1; The rings A and B may be the same or different from each other, and are selected from any one of the following: unsubstituted or substituted benzene rings, substituted or unsubstituted naphthalene rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted N-heterobenzene rings, and substituted or unsubstituted N-heteronaphthalene rings. The R1s may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C7 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a5 is selected from 0, 1, 2, 3 or 4; a6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a7 is selected from 0, 1, 2 or 3. When there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s can be connected to each other to form substituted or unsubstituted rings. The R a R b R c They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group; The m1 is selected from 0, 1, 2, 3, 4, 5, or 6, when there are two or more R a At that time, two or more R a Two Rs that are the same or different from each other, or adjacent to each other a They can connect with each other to form substituted or unsubstituted rings; The m2 is selected from 0, 1, 2, 3 or 4, when there are two or more R b At that time, two or more R b Two Rs that are the same or different from each other, or adjacent to each other b They can connect with each other to form substituted or unsubstituted rings; The m3 is selected from 0, 1, 2, 3, 4, or 5, when there are two or more R c At that time, two or more R c They are the same or different from each other; The L0 and L1 may be the same or different from each other, and are selected from any one of the following: single bond, substituted or unsubstituted C6~C30 arylene, substituted or unsubstituted C2~C30 heteroarylene, divalent substituted or unsubstituted C6~C30 aromatic ring and C3~C30 aliphatic ring fused ring group and combination thereof.

[0011] The present invention also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic layer comprises at least one or more of the triarylamine derivatives.

[0012] Beneficial effects: The triarylamine derivatives provided by this invention have strong intramolecular rigidity, suitable glass transition temperature (Tg), good thermal stability, and high refractive index, which promote uniform intermolecular arrangement and reduce intermolecular recrystallization. This is beneficial for forming a uniform and stable thin film during the device evaporation process. When used as a capping layer material in organic electroluminescent devices, it increases the coupling efficiency of light inside the device, improves the light extraction efficiency, and reduces the Joule heat generated during device operation, thereby improving the luminous efficiency and lifespan of the device. Detailed Implementation

[0013] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0014] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0015] In this specification, " "This refers to the portion that is connected to another substituent."

[0016] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0017] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent or ; Can represent , , And so on.

[0018] In this specification, when the position of the benzene ring on the ring is not fixed, it means that it can be attached to any two of the corresponding optional sites on the ring, for example... Can represent , , And so on.

[0019] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0020] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but are not limited thereto.

[0021] The alkenyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl or a branched alkenyl, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms. The alkenyl group can be substituted or unsubstituted. Specific examples may include vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, 3-methyl-1-butenyl, allyl, 1-phenylvinyl-1-yl, styryl, etc., but are not limited thereto.

[0022] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0023] The aryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.

[0024] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, and preferably have 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a] ... Phinyl, o-phenanthroline, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiaazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0025] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably with 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 7 carbon atoms. It can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0026] The fused ring of aromatic and aliphatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused ring of aromatic and aliphatic rings can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0027] The arylene group described in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, even more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the aforementioned arylene groups, monocyclic arylene groups can be phenylene, etc., but are not limited to these. The arylene group can be substituted or unsubstituted. Polycyclic arylene groups can be biphenylene, terphenylene, tetraphenylene, etc., but are not limited to these. Fused-ring arylene groups can be naphthylene, anthraceneene, phenanthrene, pyrene, fluorene, spirofluorene, triphenylene, perylene, fluorenyl, phenanthrene, etc., but are not limited to these.

[0028] The heteroaryl group described in this invention refers to the general term for a divalent group formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatoms can be one or more of N, O, S, Si, and P, and can be monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroaryl group can be substituted or unsubstituted. Examples may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, thiopheneyl, pyrroloyl, furanyl, pyranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, carbazolyl, benzocarbazolyl, acridineyl, imoxazanyl, thionazanyl, phenazinyl, phenthiazolyl, phenoxazinyl, indolyl, quinolinyl, isoquinolinyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, dibenzothiopheneyl, quinoxolinyl, quinoxolinyl, naphthinyl, purineyl, and phenanthrolineyl.

[0029] The fused ring groups of divalent aromatic and aliphatic rings described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linkage sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the fused ring groups of aromatic and aliphatic rings described above.

[0030] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.

[0031] The substituents described in the "substituted or unsubstituted" of this invention may be the same as or different from each other, and are selected from deuterium, cyano, nitro, trifluoromethyl, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted C6-C30... The aromatic ring and any one of the fused ring groups of C3-C30 aliphatic rings are preferred, including deuterium, cyano, halogen atom, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, and C2-C30 heteroaryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, and biphenyl. Triphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene, phenyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopentane The group includes, but is not limited to, alkyl, naphthocyclohexyl, naphthocycloheptyl, naphthocyclopentenyl, naphthocyclohexenyl, naphthocycloheptenyl, pyrroleyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc.

[0032] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0033] In this invention, the ring formed by the 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 the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0034] This invention provides a triarylamine derivative having the structure shown in Formula I.

[0035] In Formula I, the x atoms are the same or different from each other, are selected from CH or N atoms, and at least two x atoms are selected from N atoms. When x is bonded to other groups, the x atoms are selected from C atoms. The Y is selected from O or S; The Ar1 is selected from any one of the groups shown in Formula II-1 to Formula II-11;

[0036] The z may be the same as or different from each other, and are selected from CH or N atoms. When z is bonded to other groups, the z is selected from C atoms, and at least one z in each group of formulas II-1 to II-9 is selected from N atoms. The t is selected from any one of O, S, and N(R); the R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R can be directly bonded to L1; Q is selected from O, S, C(R) x R y ) or N(R z ); The R x R y They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring; or R x R y Either one can be directly bonded to L1, or R x R y They can be connected to each other to form a ring as shown below; ; The R4 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, or terphenyl. p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; and p7 is selected from 0, 1 or 2.

[0037] The R z Selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring; or R z It can be directly bonded to L1; The rings A and B may be the same or different from each other, and are selected from any one of the following: unsubstituted or substituted benzene rings, substituted or unsubstituted naphthalene rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted N-heterobenzene rings, and substituted or unsubstituted N-heteronaphthalene rings. The R1s may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C7 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a5 is selected from 0, 1, 2, 3 or 4; a6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a7 is selected from 0, 1, 2 or 3. When there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s can be connected to each other to form substituted or unsubstituted rings. The Ra R b R c They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group; The m1 is selected from 0, 1, 2, 3, 4, 5, or 6, when there are two or more R a At that time, two or more R a Two Rs that are the same or different from each other, or adjacent to each other a They can connect with each other to form substituted or unsubstituted rings; The m2 is selected from 0, 1, 2, 3 or 4, when there are two or more R b At that time, two or more R b Two Rs that are the same or different from each other, or adjacent to each other b They can connect with each other to form substituted or unsubstituted rings; The m3 is selected from 0, 1, 2, 3, 4, or 5, when there are two or more R c At that time, two or more R c They are the same or different from each other; The L0 and L1 may be the same or different from each other, and are selected from any one of the following: single bond, substituted or unsubstituted C6~C30 arylene, substituted or unsubstituted C2~C30 heteroarylene, divalent substituted or unsubstituted C6~C30 aromatic ring and C3~C30 aliphatic ring fused ring group and combination thereof.

[0038] Preferably, Formula I In this context, x may be the same or different from each other, are selected from CH or N atoms, and at least two x are selected from N atoms, including two, three, four, five, six or seven x selected from N atoms.

[0039] Preferably, in Formula I Choose from any of the structures shown below. ; The R cThe following groups are selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; b1 is selected from 0, 1, 2, 3, 4, or 5; b2 is selected from 0, 1, 2, 3, or 4; b3 is selected from 0, 1, 2, or 3; b4 is selected from 0, 1, or 2; b5 is selected from 0 or 1. When there are two or more R... c At that time, two or more R c They are the same or different from each other.

[0040] Preferably, in Formula I Choose from any of the structures shown below. ; c1 is selected from 1, 2, 3, 4 or 5, c2 is selected from 1, 2, 3 or 4, and c3 is selected from 1, 2 or 3.

[0041] Preferably, in Formula I Choose from any of the structures shown below. ; The R a R b They may be the same as or different from each other, selected from hydrogen, deuterium, cyano, nitro, halogen atom, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornel, adamantane, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9-methyl-9-phenylfluorene 9,9'-spirodifluorenyl, furanyl, dibenzofuranyl, thiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphridinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornelyl, methyl-substituted adamantyl, deuterium Deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated fluorenyl, deuterated furanyl, deuterated dibenzofuranyl, deuterated thiophene, deuterated dibenzothiophene, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted Any one of the following: substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated isopropyl-substituted phenyl, and deuterated tert-butyl-substituted phenyl; The n1 is selected from 0, 1, 2, 3, 4, 5, or 6; the n2 is selected from 0, 1, 2, or 3; the n3 is selected from 0, 1, 2, 3, 4, or 5; the n4 is selected from 0, 1, 2, 3, or 4; and the n5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8. When there are two or more R... a R b At that time, two or more R a R b They are the same or different from each other.

[0042] Preferably, the Ar1 is selected from any one of the following structures; ; The z atoms may be the same or different from each other, and are selected from CH or N atoms, with at least one z in each group being selected from N atoms; when z is bonded to other groups, the z atoms are selected from C atoms; The R1s may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, dibenzofuranyl, dibenzothiophenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12; the d4 is selected from 0, 1, 2, 3, 4, 5 or 6; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the d6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and the d9 is selected from 0, 1, 2 or 3. When there are two or more R1s, the two or more R1s are the same or different from each other.

[0043] Preferably, the Ar1 is selected from any one of the following structures; ; Q is selected from O, S, C(R) x R y) or N(R) z ); The R x R y They may be identical or different from each other, selected from any one of the following groups: hydrogen, deuterium, or substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; or R x R y Either one can be directly bonded to L1, or R x R y They can be connected to each other to form a ring as shown below; ; The R4 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, or terphenyl. p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; and p7 is selected from 0, 1 or 2.

[0044] The R z Selected from any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; or Rz It can be directly bonded to L1; The t is selected from any one of O, S, and N(R); The R is selected from any one of the following groups that are substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, dibenzofuranyl, dibenzothiophenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; or R can be directly bonded to L1.

[0045] Preferably, L0 and L1 are the same or different from each other, and are selected from single bonds or any of the structures shown below. ; The R2 may be the same as or different from each other, and is selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; The number e1 is selected from 0, 1, 2, 3 or 4; the number e2 is selected from 0, 1, 2 or 3; the number e3 is selected from 0, 1 or 2; the number e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the number e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the number e6 is selected from 0, 1, 2, 3, 4, 5 or 6; and the number e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12. When there are two or more R2s, the two or more R2s are the same as or different from each other.

[0046] Preferably, L0 and L1 are the same or different from each other, and are selected from single bonds or any of the structures shown below. ; The q is selected from 1, 2, 3 or 4.

[0047] Preferably, the triarylamine derivative is selected from any one of the following structures: .

[0048] The above lists some specific structural forms of triarylamine derivatives represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0049] The present invention also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic layer comprises at least one or more of the triarylamine derivatives described in the present invention.

[0050] Preferably, the organic layer is located outside either the anode or the cathode electrode, and the organic layer includes a capping layer, which contains at least one or more of the triarylamine derivatives described in this invention.

[0051] Preferably, the organic layer of the present invention is located between the anode and the cathode, and includes at least one of the hole transport region, the light-emitting layer, and the electron transport region.

[0052] Preferably, the hole transport region of the present invention comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0053] Preferably, the hole transport region of the present invention includes at least one of a hole injection layer and a hole transport layer, and more preferably, the hole transport region of the present invention includes a hole transport layer.

[0054] Preferably, the hole transport layer of the present invention includes a first hole transport layer and a second hole transport layer.

[0055] Preferably, the light-emitting layer of the present invention comprises a host material and a dopant material.

[0056] Preferably, the electron transport region of the present invention comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0057] The organic electroluminescent device of the present invention may have each functional layer composed of a single layer or two or more thin films, and each thin film may be composed of one material or two or more materials. However, the structure of the organic electroluminescent device is not limited to this.

[0058] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below: The anode material described in this invention preferably uses a material with a high energy function, which improves hole injection efficiency. The anode material that can be used in this invention is selected from the following: indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0059] The hole injection layer described in this invention preferably uses a material with good hole-accepting ability. Specific examples of materials that can be used in the hole injection layer of this invention may include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, and phenazine compounds, such as copper phthalocyanine (CuPc), titanium phthalocyanine, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), and N,N,N',N'-tetra(4-methoxyphenyl)biphenyl. Amines such as MeO-TPD, diquinoxolino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), and 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA) are available, but are not limited to these.

[0060] The hole transport layer material described in this invention is preferably a material with high hole mobility. It can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc. Examples of hole transport layer materials include, but are not limited to, materials such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), and N,N,N',N'-tetra(3-methylphenyl)-3,3'-dimethylbiphenyldiamine (HMTPD).

[0061] The light-emitting layer material of this invention includes a host material and a dopant material. The host material of the light-emitting layer needs to possess bipolar charge transport properties and have suitable energy levels, and is selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-AND), N,N'-bis-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3 ,5-tris(9-carbazolyl)benzene (TCP), etc. Besides the above materials and their combinations, the main material of the luminescent layer may also include other known materials suitable for the luminescent layer, but is not limited thereto. The luminescent layer doping materials of this invention are divided into blue luminescent materials, green luminescent materials, and red luminescent materials. The luminescent layer doping material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials, selected from (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine) (DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(2-hydroxyphenylpyridine)beryllium (Bepp2), bis(4,6-difluorophenylpyridine-C2) Examples of iridium(N)pyridinecarboxylate (FIrpic), tris(2-phenylpyridine)iridium(Ir(ppy)3), di(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), tris[1-phenylisoquinoline-C2,N]iridium(III)(Ir(piq)3), di(1-phenylisoquinoline)(acetylacetonate)iridium(Ir(piq)2(acac)), etc., but not limited to these.

[0062] The doping ratio of the host material and the guest material in the light-emitting layer of the present invention is determined according to the materials used. The amount of dopant material is preferably 0.1~70% by mass, more preferably 0.1~30% by mass, further preferably 1~30% by mass, even more preferably 1~20% by mass, and particularly preferably 1~10% by mass.

[0063] The hole blocking layer of this invention preferably uses a material with strong hole blocking capability and suitable HOMO / LUMO energy levels. The hole blocking layer material of this invention can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc., but is not limited thereto.

[0064] The electron transport layer material of the present invention is preferably a material with high electron mobility. It can be selected from any one or more of the following structures: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 8-hydroxyquinoline-lithium (Liq), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), and 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but is not limited thereto.

[0065] The electron injection layer material described in this invention is preferably a material with a small barrier difference to the adjacent organic layer material. Specific examples may include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, cesium 8-hydroxyquinoline, aluminum 8-hydroxyquinoline), organometallic salts (metal acetate, metal benzoate, or metal stearate), molybdenum trioxide, aluminum, etc., but are not limited to these.

[0066] The cathode material of this invention preferably uses a material with a low work function that can promote electron injection into the organic layer, thereby reducing the electron injection barrier. It can be selected from any one or more of the following materials: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0067] The capping layer of this invention is provided on the outside of either the anode or the cathode electrode, and preferably uses a material that can improve the internal optical coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., but is not limited thereto. The compound of formula I described in this invention is preferred.

[0068] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0069] The organic electroluminescent device of the present invention can be applied using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating.

[0070] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0071] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0072] Preparation and characterization of compounds

[0073] There are no particular limitations on the preparation method of the structure shown in Formula I of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. The structure shown in Formula I of the present invention can be prepared by the synthetic route shown below.

[0074] Preparation of intermediate A:

[0075] Preparation of intermediate C:

[0076] Preparation of compound I: Among them, X a X b They may be the same or different from each other, and are selected from any one of Cl, Br, and I; Ar1, L0, L1, R a ~R c The limitations of m1~m3, Y, and x are the same as those mentioned above.

[0077] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; they can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent purity.

[0078] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg. Synthesis Example 1: Preparation of Intermediate A-19:

[0079] Under nitrogen protection, a-19 (17.60 g, 100.00 mmol), b-19 (25.51 g, 100.00 mmol), K2CO3 (22.11 g, 160 mmol), and 420 mL of mixed solvent (toluene:ethanol:water = 2:1:1) were added sequentially to the reaction flask. The air was then purged with nitrogen three times. Pd(PPh3)4 (1.16 g, 1.00 mmol) was then added, and the mixture was stirred at reflux for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The resulting solid was recrystallized from toluene and dried to obtain intermediate A-19 (16.15 g, yield 72%); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 224.1239 (theoretical value: 224.1252).

[0080] By substituting the raw materials accordingly, intermediate A can be prepared according to the preparation method of intermediate A-19 in Synthesis Example 1. The raw materials are shown in the table below:

[0081] Synthesis Example 2: Preparation of Intermediate C-57:

[0082] Under nitrogen protection, c-57 (19.15 g, 100.00 mmol), b-57 (25.61 g, 100.00 mmol), K2CO3 (20.73 g, 150.00 mmol), and 540 mL of mixed solvent (toluene:ethanol:water = 2:1:1) were added sequentially to the reaction flask. After purging the air three times with nitrogen, Pd(PPh3)4 (1.21 g, 1.05 mmol) was added. The reaction was stirred at reflux for 3.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 15:2 to obtain intermediate C-57 (18.05 g, yield 75%) with HPLC purity ≥ 99.81%. Mass spectrometry m / z: 240.0468 (theoretical value: 240.0454).

[0083] By substituting the raw materials accordingly, intermediate C can be prepared according to the preparation method of intermediate C-57 in Synthesis Example 2. The raw materials are shown in the table below:

[0084] Synthesis Example 3: Preparation of Compound 5

[0085] Synthetic intermediate I-5

[0086] Under nitrogen protection, A-5 (13.62 g, 80.00 mmol), B-5 ​​(23.77 g, 80.00 mmol), and NaOt-Bu (12.49 g, 130.00 mmol) were dissolved in 650 mL of toluene. Pd(OAc)₂ (0.24 g, 1.09 mmol) and P(t-Bu)₃ (4.36 mL of 0.5 M toluene solution, 2.18 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, added distilled water, extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered. The resulting solid was recrystallized from toluene:methanol = 10:1 to give intermediate I-5 (23.81 g, yield 77%), with an HPLC purity ≥ 99.89%. Mass spectrometry m / z: 386.1429 (theoretical value: 386.1419).

[0087] Synthetic compound 5

[0088] Under nitrogen protection, intermediates I-5 (19.32 g, 50.00 mmol), C-5 (21.87 g, 50.00 mmol), and NaOt-Bu (8.46 g, 88.00 mmol) were dissolved in 440 mL of toluene. Pd2(dba)3 (0.69 g, 0.75 mmol) and X-Phos (0.72 g, 1.50 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 7 h. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and the layers were separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered. The resulting solid was recrystallized from toluene to give compound 5 (27.86 g, 75% yield), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 742.2718 (theoretical value: 742.2733). Theoretical element content (%) C 53 H 34 N4O: C, 85.69; H, 4.61; N, 7.54. Measured elemental content (%): C, 85.72; H, 4.59; N, 7.52.

[0089] Synthesis Example 4: Preparation of Compound 16

[0090] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-16, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-16, yielding compound 16 (27.64 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 717.2542 (theoretical value: 717.2529). Theoretical elemental content (%) C 50 H 31 N5O: C, 83.66; H, 4.35; N, 9.76. Measured elemental content (%): C, 83.70; H, 4.39; N, 9.78.

[0091] Synthesis Example 5: Preparation of Compound 19

[0092] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-19, B-5 ​​with an equimolar amount of B-19, and C-5 with an equimolar amount of C-19, yielding compound 19 (24.18 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 644.2530 (theoretical value: 644.2514). Theoretical elemental content (%) C 45 H 24 D4N4O: C, 83.83; H, 5.00; N, 8.69. Measured elemental content (%): C, 83.79; H, 5.02; N, 8.71.

[0093] Synthesis Example 6: Preparation of Compound 45

[0094] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-45, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-45, yielding compound 45 (30.57 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 793.2854 (theoretical value: 793.2842). Theoretical elemental content (%) C 56 H 35 N5O: C, 84.72; H, 4.44; N, 8.82. Measured elemental content (%): C, 84.69; H, 4.41; N, 8.85.

[0095] Synthesis Example 7: Preparation of Compound 57

[0096] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-57, B-5 ​​with an equimolar amount of B-57, and C-5 with an equimolar amount of C-57, yielding compound 57 (24.39 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 641.2228 (theoretical value: 641.2216). Theoretical elemental content (%) C 44 H 27 N5O: C, 82.35; H, 4.24; N, 10.91. Measured elemental content (%): C, 82.33; H, 4.22; N, 10.88.

[0097] Synthesis Example 8: Preparation of Compound 71

[0098] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-71, B-5 ​​with an equimolar amount of B-71, and C-5 with an equimolar amount of C-71, yielding compound 71 (24.71 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 641.2205 (theoretical value: 641.2216). Theoretical elemental content (%) C 44 H 27 N5O: C, 82.35; H, 4.24; N, 10.91. Measured elemental content (%): C, 82.37; H, 4.21; N, 10.87.

[0099] Synthesis Example 9: Preparation of Compound 82

[0100] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-82, B-5 ​​with an equimolar amount of B-82, and C-5 with an equimolar amount of C-82, yielding compound 82 (23.74 g) with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 641.2207 (theoretical value: 641.2216). Theoretical elemental content (%) C 44 H 27 N5O: C, 82.35; H, 4.24; N, 10.91. Measured elemental content (%): C, 82.38; H, 4.22; N, 10.88.

[0101] Synthesis Example 10: Preparation of Compound 84

[0102] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-84, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-84, yielding compound 84 (25.03 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 641.2206 (theoretical value: 641.2216). Theoretical elemental content (%) C 44 H 27 N5O: C, 82.35; H, 4.24; N, 10.91. Measured elemental content (%): C, 82.37; H, 4.20; N, 10.89.

[0103] Synthesis Example 11: Preparation of Compound 118

[0104] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-118, B-5 ​​with an equimolar amount of B-118, and C-5 with an equimolar amount of C-118, yielding compound 118 (27.45 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 741.2540 (theoretical value: 741.2529). Theoretical elemental content (%) C 52 H 31 N5O: C, 84.19; H, 4.21; N, 9.44. Measured elemental content (%): C, 84.21; H, 4.18; N, 9.47.

[0105] Synthesis Example 12: Preparation of Compound 132

[0106] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-132, B-5 ​​with an equimolar amount of B-132, and C-5 with an equimolar amount of C-132, yielding compound 132 (23.75) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 650.2766 (theoretical value: 650.2781). Theoretical elemental content (%) C 44 H 18 D9N5O: C, 81.21; H, 5.57; N, 10.76. Measured elemental content (%): C, 81.17; H, 5.60; N, 10.78.

[0107] Synthetic Example 13: Preparation of Compound 133

[0108] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-133, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-45, yielding compound 133 (27.73 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 729.2433 (theoretical value: 729.2416). Theoretical elemental content (%) C 52 H 31 N3O2: C, 85.58; H, 4.2s8; N, 5.76. Measured elemental content (%): C, 85.61; H, 4.30; N, 5.73.

[0109] Synthesis Example 14: Preparation of Compound 181

[0110] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-181, B-5 ​​with an equimolar amount of B-181, and C-5 with an equimolar amount of C-181, yielding compound 181 (26.27 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 729.2430 (theoretical value: 729.2416). Theoretical elemental content (%) C 52 H 31 N3O2: C, 85.58; H, 4.28; N, 5.76. Measured elemental content (%): C, 85.55; H, 4.30; N, 5.78.

[0111] Synthesis Example 15: Preparation of Compound 208

[0112] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-208, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-45, yielding compound 208 (26.17 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 679.2248 (theoretical value: 679.2260). Theoretical elemental content (%) C 48 H 29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured elemental content (%): C, 84.78; H, 4.26; N, 6.20.

[0113] Synthesis Example 16: Preparation of Compound 232

[0114] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-232, B-5 ​​with an equimolar amount of B-19, and C-5 with an equimolar amount of C-232, yielding compound 232 (22.46 g) with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 632.2225 (theoretical value: 632.2212). Theoretical elemental content (%) C 43 H 28 N4O2: C, 81.63; H, 4.46; N, 8.86. Measured elemental content (%): C, 81.59; H, 4.48; N, 8.90.

[0115] Synthesis Example 17: Preparation of Compound 237

[0116] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-237, B-5 ​​with an equimolar amount of B-57, and C-5 with an equimolar amount of C-237, yielding compound 237 (25.05 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 695.2042 (theoretical value: 695.2031). Theoretical elemental content (%) C 48 H 29 N3OS: C, 82.85; H, 4.20; N, 6.04. Measured elemental content (%): C, 82.80; H, 4.18; N, 6.06.

[0117] Synthesis Example 18: Preparation of Compound 252

[0118] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-252, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-45, yielding compound 252 (27.57 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 706.2353 (theoretical value: 706.2369). Theoretical elemental content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured elemental content (%): C, 83.30; H, 4.25; N, 7.88.

[0119] Synthesis Example 19: Preparation of Compound 289

[0120] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-289, B-5 ​​with an equimolar amount of B-289, and C-5 with an equimolar amount of C-289, yielding compound 289 (28.78 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 832.2850 (theoretical value: 832.2838). Theoretical elemental content (%) C 59 H 36 N4O2: C, 85.08; H, 4.36; N, 6.73. Measured elemental content (%): C, 85.11; H, 4.39; N, 6.69.

[0121] Synthesis Example 20: Preparation of Compound 299

[0122] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-299, B-5 ​​with an equimolar amount of B-16, and C-5 with an equimolar amount of C-45, yielding compound 299 (29.14 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 756.2511 (theoretical value: 756.2525). Theoretical elemental content (%) C 53 H 32 N4O2: C, 84.11; H, 4.26; N, 7.40. Measured elemental content (%): C, 84.08; H, 4.21; N, 7.37.

[0123] Synthesis Example 21: Preparation of Compound 339

[0124] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-339, B-5 ​​with an equimolar amount of B-339, and C-5 with an equimolar amount of C-339, yielding compound 339 (24.99 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 703.2423 (theoretical value: 703.2406). Theoretical elemental content (%) C 46 H 33 N5OS: C, 78.50; H, 4.73; N, 9.95. Measured elemental content (%): C, 78.45; H, 4.69; N, 9.98.

[0125] Synthesis Example 22: Preparation of Compound 367

[0126] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-367, B-5 ​​with an equimolar amount of B-367, and C-5 with an equimolar amount of C-367, yielding compound 367 (31.60 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 853.3611 (theoretical value: 853.3626). Theoretical elemental content (%) C 60 H 27 D 10 N5O: C, 84.38; H, 5.54; N, 8.20. Measured elemental content (%): C, 84.41; H, 5.49; N, 8.25.

[0127] Synthesis Example 23: Preparation of Compound 371

[0128] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-371, B-5 ​​with an equimolar amount of B-371, and C-5 with an equimolar amount of C-371, yielding compound 371 (24.21 g) with an HPLC purity ≥ 99.90%. Mass spectrometry m / z: 691.2359 (theoretical value: 691.2372). Theoretical elemental content (%) C 48 H 29 N5O: C, 83.34; H, 4.23; N, 10.12. Measured elemental content (%): C, 83.32; H, 4.25; N, 10.09.

[0129] Synthesis Example 24: Preparation of Compound 401

[0130] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-45, B-5 ​​with an equimolar amount of B-401, and C-5 with an equimolar amount of C-45, yielding compound 401 (30.78 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 809.2628 (theoretical value: 809.2613). Theoretical elemental content (%) C 56 H 35 N5S: C, 83.04; H, 4.36; N, 8.65. Measured elemental content (%): C, 83.07; H, 4.40; N, 8.62.

[0131] Synthesis Example 25: Preparation of Compound 423

[0132] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-423, B-5 ​​with an equimolar amount of B-423, and C-5 with an equimolar amount of C-423, yielding compound 423 (24.01 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 657.1969 (theoretical value: 657.1987). Theoretical elemental content (%) C 44 H 27 N5S: C, 80.34; H, 4.14; N, 10.65. Measured elemental content (%): C, 80.36; H, 4.09; N, 10.62.

[0133] Synthesis Example 26: Preparation of Compound 466

[0134] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-466, B-5 ​​with an equimolar amount of B-466, and C-5 with an equimolar amount of C-466, yielding compound 466 (26.48 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 745.2175 (theoretical value: 745.2188). Theoretical elemental content (%) C 52 H 31 N3OS: C, 83.73; H, 4.19; N, 5.63. Measured elemental content (%): C, 83.69; H, 4.21; N, 5.66.

[0135] Synthesis Example 27: Preparation of Compound 518

[0136] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-518, B-5 ​​with an equimolar amount of B-518, and C-5 with an equimolar amount of C-518, yielding compound 518 (24.29 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 647.1765 (theoretical value: 647.1780). Theoretical elemental content (%) C 42 H 25 N5OS: C, 77.88; H, 3.89; N, 10.81. Measured elemental content (%): C, 77.90; H, 3.86; N, 10.78.

[0137] Synthesis Example 28: Preparation of Compound 551

[0138] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-551, B-5 ​​with an equimolar amount of B-551, and C-5 with an equimolar amount of C-551, yielding compound 551 (27.30 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 802.2750 (theoretical value: 802.2733). Theoretical elemental content (%) C 58 H 34 N4O: C, 86.76; H, 4.27; N, 6.98. Measured elemental content (%): C, 86.80; H, 4.30; N, 6.96.

[0139] Synthesis Example 29: Preparation of Compound 555

[0140] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-555, B-5 ​​with an equimolar amount of B-555, and C-5 with an equimolar amount of C-555, yielding compound 555 (25.26 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 742.2752 (theoretical value: 742.2733). Theoretical elemental content (%) C 53 H 34 N4O: C, 85.69; H, 4.61; N, 7.54. Measured elemental content (%): C, 85.70; H, 4.59; N, 7.53.

[0141] Synthesis Example 30: Preparation of Compound 579

[0142] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-579, B-5 ​​with an equimolar amount of B-579, and C-5 with an equimolar amount of C-579, yielding compound 579 (26.72 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 785.3328 (theoretical value: 785.3344). Theoretical elemental content (%) C 57 H 35 D4N3O: C, 87.10; H, 5.51; N, 5.35. Measured elemental content (%): C, 87.09; H, 5.49; N, 5.38.

[0143] Synthesis Example 31: Preparation of Compound 593

[0144] Following the same preparation method as in Synthesis Example 3, A-5 was replaced with an equimolar amount of A-593, B-5 ​​with an equimolar amount of B-593, and C-5 with an equimolar amount of C-593, yielding compound 593 (29.22 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 846.2803 (theoretical value: 846.2817). Theoretical elemental content (%) C 60 H 38 N4S: C, 85.08; H, 4.52; N, 6.61. Measured elemental content (%): C, 85.10; H, 4.53; N, 6.59.

[0145] [Device Example 1]

[0146] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0147] Using vacuum evaporation, NPNPB with a thickness of 15 nm was deposited as a hole injection layer on a cleaned ITO / Ag / ITO substrate; 80 nm thick compound NPB was deposited as a hole transport layer on this hole injection layer; TcTa:Ir(piq)2(acac)=98:2 (mass ratio) was deposited as a light-emitting layer with a thickness of 40 nm on this hole transport layer; BAlq was deposited as a hole blocking layer with a thickness of 40 nm on this light-emitting layer; TPBi and Liq (doping mass ratio of 1:1) were deposited as an electron transport layer with a thickness of 30 nm on this hole blocking layer; LiF was deposited as an electron injection layer with a thickness of 1.0 nm on this electron transport layer; and Mg:Ag=1:9 was deposited on this electron injection layer. (Doping mass ratio 1:1) is used as the cathode, and the deposition thickness is 12nm. Then, compound 5 is deposited on the cathode as a capping layer with a deposition thickness of 70nm, thereby preparing an organic electroluminescent device.

[0148] ; [Device Examples 2-29] Compound 16, 19, 45, 57, 71, 82, 84, 118, 132, 133, 181, 208, 232, 237, 252, 289, 299, 339, 367, 371, 401, 423, 466, 518, 551, 555, 579, or 593 of the present invention were used to replace compound 5 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0149] [Comparative Device Examples 1-3]

[0150] The organic electroluminescent device was prepared by replacing compound 5 in device example 1 with comparative compound 1, comparative compound 2 or comparative compound 3 as the capping material, except that the organic electroluminescent device was prepared by the same preparation method as device example 1.

[0151] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0152] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 1 to 29 of the present invention and Comparative Examples 1 to 3 are shown in Table 1 below.

[0153]

[0154] As can be seen from the data results in Table 1, the triarylamine derivative of the present invention, when used as a coating material in organic electroluminescent devices, effectively reduces total internal reflection of light inside the device, increases light extraction efficiency, and thus improves the luminous efficiency and lifespan of the device.

[0155] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A triarylamine derivative, characterized in that, The triarylamine derivative has the structure shown in Formula I. In Formula I, the x atoms are the same or different from each other, are selected from CH or N atoms, and at least two x atoms are selected from N atoms. When x is bonded to other groups, the x atoms are selected from C atoms. The Y is selected from O or S; The Ar1 is selected from any one of the groups shown in Formula II-1 to Formula II-11; The z may be the same as or different from each other, and are selected from CH or N atoms. When z is bonded to other groups, the z is selected from C atoms, and at least one z in each group of formulas II-1 to II-9 is selected from N atoms. The t is selected from any one of O, S, and N(R); the R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R can be directly bonded to L1; Q is selected from O, S, C(R) x R y ) or N(R z ); The R x R y They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring; or R x R y Either one can be directly bonded to L1, or R x R y They can be connected to each other to form a ring as shown below; ； The R4 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, or terphenyl. p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; p7 is selected from 0, 1 or 2. The R z Selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring; or R z It can be directly bonded to L1; The rings A and B may be the same or different from each other, and are selected from any one of the following: unsubstituted or substituted benzene rings, substituted or unsubstituted naphthalene rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted N-heterobenzene rings, and substituted or unsubstituted N-heteronaphthalene rings. The R1s may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C7 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a5 is selected from 0, 1, 2, 3 or 4; a6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a7 is selected from 0, 1, 2 or 3. When there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s can be connected to each other to form substituted or unsubstituted rings. The R a R b R c They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group; The m1 is selected from 0, 1, 2, 3, 4, 5, or 6, when there are two or more R a At that time, two or more R a Two Rs that are the same or different from each other, or adjacent to each other a They can connect with each other to form substituted or unsubstituted rings; The m2 is selected from 0, 1, 2, 3 or 4, when there are two or more R b At that time, two or more R b Two Rs that are the same or different from each other, or adjacent to each other b They can connect with each other to form substituted or unsubstituted rings; The m3 is selected from 0, 1, 2, 3, 4, or 5, when there are two or more R c At that time, two or more R c They are the same or different from each other; The L0 and L1 may be the same or different from each other, and are selected from any one of the following: single bond, substituted or unsubstituted C6~C30 arylene, substituted or unsubstituted C2~C30 heteroarylene, divalent substituted or unsubstituted C6~C30 aromatic ring and C3~C30 aliphatic ring fused ring group and combination thereof.

2. The triarylamine derivative according to claim 1, characterized in that, In Equation I Choose from any of the structures shown below. ； The R c The following groups are selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; b1 is selected from 0, 1, 2, 3, 4, or 5; b2 is selected from 0, 1, 2, 3, or 4; b3 is selected from 0, 1, 2, or 3; b4 is selected from 0, 1, or 2; b5 is selected from 0 or 1. When there are two or more R... c At that time, two or more R c They are the same or different from each other.

3. A triarylamine derivative according to claim 1, characterized in that, In Equation I Choose from any of the structures shown below. ； c1 is selected from 1, 2, 3, 4 or 5, c2 is selected from 1, 2, 3 or 4, and c3 is selected from 1, 2 or 3.

4. A triarylamine derivative according to claim 1, characterized in that, In Equation I Choose from any of the structures shown below. ； The R a R b They may be the same as or different from each other, selected from hydrogen, deuterium, cyano, nitro, halogen atom, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornel, adamantane, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9-methyl-9-phenylfluorene 9,9'-spirodifluorenyl, furanyl, dibenzofuranyl, thiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphridinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornelyl, methyl-substituted adamantyl, deuterium Deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated fluorenyl, deuterated furanyl, deuterated dibenzofuranyl, deuterated thiophene, deuterated dibenzothiophene, fluorinated phenyl, fluorinated biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted Any one of the following: substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated isopropyl-substituted phenyl, and deuterated tert-butyl-substituted phenyl; The n1 is selected from 0, 1, 2, 3, 4, 5, or 6; the n2 is selected from 0, 1, 2, or 3; the n3 is selected from 0, 1, 2, 3, 4, or 5; the n4 is selected from 0, 1, 2, 3, or 4; and the n5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8. When there are two or more R... a R b At that time, two or more R a R b They are the same or different from each other.

5. A triarylamine derivative according to claim 1, characterized in that, Ar1 is selected from any of the following structures; ； The z atoms may be the same or different from each other, and are selected from CH or N atoms, with at least one z in each group being selected from N atoms; when z is bonded to other groups, the z atoms are selected from C atoms; The R1s may be the same as or different from each other, and are selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, dibenzofuranyl, dibenzothiophenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12; the d4 is selected from 0, 1, 2, 3, 4, 5 or 6; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the d6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and the d9 is selected from 0, 1, 2 or 3. When there are two or more R1s, the two or more R1s are the same or different from each other.

6. A triarylamine derivative according to claim 1, characterized in that, Ar1 is selected from any of the following structures; ； Q is selected from O, S, C(R) x R y) or N(R) z ); The R x R y They may be identical or different from each other, selected from any one of the following groups: hydrogen, deuterium, or substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; or R x R y Either one can be directly bonded to L1, or R x R y They can be connected to each other to form a ring as shown below; ； The R4 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, or terphenyl. p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; p7 is selected from 0, 1 or 2. The R z Selected from any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; or R z It can be directly bonded to L1; The t is selected from any one of O, S, and N(R); The R is selected from any one of the following groups that are substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, dibenzofuranyl, dibenzothiophenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; or R can be directly bonded to L1.

7. A triarylamine derivative according to claim 1, characterized in that, L0 and L1 may be the same or different from each other, and are selected from single bonds or any of the structures shown below. ； The R2 may be the same as or different from each other, and is selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, or C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, or benzocycloheptane; The number e1 is selected from 0, 1, 2, 3 or 4; the number e2 is selected from 0, 1, 2 or 3; the number e3 is selected from 0, 1 or 2; the number e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the number e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the number e6 is selected from 0, 1, 2, 3, 4, 5 or 6; and the number e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12. When there are two or more R2s, the two or more R2s are the same as or different from each other.

8. A triarylamine derivative according to claim 1, characterized in that, The triarylamine derivative is selected from any one of the following structures. 。 9. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, characterized in that, The organic layer comprises at least one or more of the triarylamine derivatives as described in any one of claims 1 to 8.

10. An organic electroluminescent device according to claim 9, wherein the organic layer is located outside either the anode or the cathode electrode, characterized in that, The organic layer includes a capping layer, which contains at least one or more of the triarylamine derivatives according to any one of claims 1 to 8.

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