CN114907217B

CN114907217B - Triamine compound and organic electroluminescent device thereof

Info

Publication number: CN114907217B
Application number: CN202210273518.7A
Authority: CN
Inventors: 郭建华; 韩春雪; 孙月; 苗玉鹤
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2022-03-18
Filing date: 2022-03-18
Publication date: 2023-10-27
Anticipated expiration: 2042-03-18
Also published as: CN114907217A

Abstract

The invention provides a triamine compound and an organic electroluminescent device thereof, belonging to the technical field of organic electroluminescent. The triamine compound provided by the invention effectively reduces the movement of molecules in space, inhibits the crystallization trend of the molecules, thereby improving the thermal stability and film forming property of the material, simultaneously enhancing the mobility of electrons in the molecules, effectively improving the HOMO energy level of the triamine compound, reducing the electron energy, simultaneously increasing the contact opportunity between adjacent molecules, greatly improving the hole mobility of the material, and greatly improving the luminous efficiency and the service life of the device when the triamine compound is used as a hole transport layer/luminous auxiliary layer material. The benzidine derivative and the organic electroluminescent device thereof have good application effect and industrialization prospect.

Description

Triamine compound and organic electroluminescent device thereof

Technical Field

The invention relates to the technical field of organic electroluminescence, in particular to a triamine compound and an organic electroluminescent device thereof.

Background

An Organic Light-Emitting Diode (OLED) refers to a device in which an Organic semiconductor material and a Light-Emitting material are driven by an electric field through carrier injection and recombination. Compared to LCDs, OLEDs have the following irreplaceable advantages: (1) The self-luminous device has low power consumption and good contrast ratio in bright environment; (2) fast response (3 orders of magnitude faster than LCD); (3) wide viewing angle since the OLED is a self-luminous device. The image picture of the device is not distorted in a large range; (4) the light weight and the thinness are easy to realize, and the earthquake resistance is good; (5) broad temperature characteristics; (6) High brightness and high contrast, and is easy to realize color display; (7) the production can be performed on materials such as plastics and resins. The OLED has the advantages, so that the OLED is a hot spot for research in recent years and has excellent commercial and market prospects.

In order to improve the brightness, efficiency and lifetime of an organic electroluminescent device, a multi-layered structure of a sandwich structure is generally formed in the device using various materials, and mainly includes an electron, hole transport layer (carrier layer) and a light emitting layer. The hole transport layer serves as a connecting layer between the anode and the light emitting layer, and mainly plays two roles: firstly, holes injected from an anode are better transported to a light-emitting layer, and electrons are prevented from diffusing from the light-emitting layer to a hole transport layer to a certain extent, so that the electrons are better limited in the light-emitting layer, and the maximum recombination of carriers is realized; and secondly, the energy barrier of holes in the injection process is reduced, and the injection efficiency of the holes is improved, so that the brightness, the efficiency and the service life of the device are improved.

For the hole transport material, the following points are to be satisfied: (1) being capable of forming a uniform amorphous film free of pinholes; (2) The formed amorphous film has good thermal stability; (3) Has proper HOMO orbit energy level to ensure the effective injection and transmission of holes between the electrode/organic layer and the organic layer/organic layer interface; (4) has very high hole mobility. One of the important issues that hole transport layers need to be studied is their poor hole mobility, resulting in low device efficiency. The thermal stability is also an important aspect of research on hole transport materials, the hole transport materials generally exist in an amorphous glass state on a device, if Tg is low, the temperature of the material can easily reach or exceed Tg due to the exothermic effect of the photoelectric device, and when the device is stopped to be used and the temperature slowly drops, the material can easily crystallize, so that the service performance of the device can be seriously affected, and the service life is shortened.

Disclosure of Invention

At present, the crystallization of a hole transport material can be caused by the exothermic effect of the device, the service life of the device is influenced, and the reduction of the luminous efficiency of the device can be caused by the lower hole mobility of the material. The triamine compound provided by the invention has good hole mobility and thermal stability, and can be used as a hole transport material to be applied to an organic electroluminescent device, so that the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

The invention provides a triamine compound, which has a structure shown in a chemical formula 1,

wherein the Ar is ₁ ～Ar ₆ At least one of the structures shown in chemical formula 2, and the rest is the same or different and is selected from any one of the structures shown in the following,

the R is ₅ The same or different is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring condensed ring group, substituted or unsubstituted C1-C25 heterocycloalkyl group and C6-C30 aromatic ring condensed ring group;

Said b ₁ Selected from 0, 1, 2, 3, 4 or 5; said b ₂ The same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b ₃ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; when two or more R's are present ₅ When two or more R' s ₅ Are the same as or different from each other;

in chemical formula 2, the ring A is a substituted or unsubstituted C3-C10 alicyclic ring;

the R is ₄ The same or different is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring condensed ring group, substituted or unsubstituted C1-C25 heterocycloalkyl group and C6-C30 aromatic ring condensed ring group;

said a is selected from 0, 1, 2, 3 or 4; when a is greater than 1, two or more R ₄ Are identical or different from each other, or adjacent two R ₄ Are connected with each other to form a substituted or unsubstituted ring;

the L is ₁ ～L ₆ The same or different one selected from single bond, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring condensed ring group;

The R is ₁ 、R ₂ 、R ₃ The same or different is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring condensed ring group, substituted or unsubstituted C1-C25 heterocycloalkyl ring and C6-C30 aromatic ring condensed ring group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 heteroaromatic ring condensed ring group;

provided that the triamine compound is not

The invention also provides an organic electroluminescent device, which comprises an anode, a cathode, an organic layer between the anode and the cathode and outside the anode, wherein the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, and the hole transmission region contains one or more than one of the triamine compounds.

The invention has the beneficial effects that:

the triamine compound provided by the invention can form larger steric hindrance, reduce the planeness of molecules, effectively reduce the movement of molecules in space, inhibit the crystallization trend of molecules, thereby improving the thermal stability and film forming property of the material, and when the triamine compound is used as a hole transport material to be evaporated to a device, an amorphous glassy film can be formed, thus avoiding crystallization of the material due to the exothermic effect of the device, seriously affecting the service performance of the device and shortening the service life of the device; meanwhile, the triamine compound enlarges the delocalized range of electrons, enhances the mobility of electrons in molecules, effectively improves the HOMO energy level of the triamine compound, reduces the electron energy, simultaneously increases the contact opportunity between adjacent molecules, greatly improves the hole mobility of the material, and can block excitons in a luminescent layer while effectively transmitting holes when being used as a hole transmission material to be evaporated into a device, thereby greatly improving the luminous efficiency of the device.

Detailed Description

The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.

In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance.

In the present description of the invention,meaning to another substituentIs a part of the same.

In the present specification, "-" means a moiety attached to another substituent.

In this specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, the number of the cells to be processed,can indicate->And so on.

The alkyl group according to the present invention means a monovalent group having at least one hydrogen atom in an alkane molecule, and may be a straight chain alkyl group, a branched chain alkyl group, preferably having 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms, and examples may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

The alicyclic group according to the present invention means a monovalent group having one hydrogen atom at a small amount in the alicyclic hydrocarbon molecule, and may be a cycloalkyl group, a cycloalkenyl group, or the like, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and preferably 3 to 7 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, or the like, but are not limited thereto.

Cycloalkyl as used herein refers to a monovalent group of a cyclic alkane molecule having at least one hydrogen atom, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 7 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like, but are not limited thereto.

Cycloalkenyl as used herein refers to a monovalent group of a cyclic olefin molecule with at least one hydrogen atom, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 7 carbon atoms, and examples may include, but are not limited to, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like.

The heterocycloalkyl group refers to a monovalent group formed by removing one hydrogen atom in a heterocycloalkyl molecule, and the heteroatom can be one or more of N, O, S, si, P. Preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 7 carbon atoms, and examples may include azetidinyl, tetrahydropyrrolyl, piperidinyl, azepanyl, homopiperidinyl, morpholinyl, thiomorpholinyl, tetrahydrofuranyl, tetrahydrothienyl, dioxane, and the like, but are not limited thereto.

The aryl group according to the present invention means a monovalent group obtained by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group, a polycyclic aryl group or a condensed ring aryl group, preferably having 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and examples may include phenyl, biphenyl, terphenyl, naphthyl, indenyl, indanyl, dihydronaphthyl, tetrahydronaphthyl, anthracenyl, phenanthryl, pyrenyl, triphenylenyl, perylene, and the like, but are not limited thereto.

The fused ring group of the alicyclic ring and the aromatic ring refers to the general term that after the alicyclic ring and the aromatic ring are fused together, one hydrogen atom is removed, and a monovalent group is left. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.

The fused ring group of the heterocycloalkyl ring and the aromatic ring in the present invention means a generic term for the monovalent group remaining after the heterocycloalkyl ring and the aromatic ring are fused together to remove one hydrogen atom. Preferably having 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, examples may include benzoazetidinyl, benzotetrahydropyranyl, benzopiperidinyl, benzoazepanyl, naphthasprings tetrahydropyranyl, naphthasprings piperidinyl, phenanthrlocks piperidinyl, etc., but are not limited thereto.

Heteroaryl as used herein refers to the generic term for a monovalent radical that is formed by removing a hydrogen atom from the core atom of an aromatic heterocycle comprising carbon and a heteroatom. The heteroatom may be one or more of N, O, S, si, P, and may be a monocyclic heteroaryl group or a condensed ring heteroaryl group, preferably having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 3 to 12 carbon atoms, most preferably 3 to 8 carbon atoms, and examples may include pyrrolyl, pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, indolyl, quinolinyl, isoquinolinyl, oxazolyl, thiazolyl, imidazolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridooxazolyl, pyridothiazolyl, pyridoimidazolyl, pyrimidothiazolyl, dibenzofuranyl, dibenzothienyl, quinoxalinyl, quinazolinyl, quinoxazolyl, quinolizinyl, quinoimidazoimidazolyl, purinyl, 2-purinyl, N-imidazolyl, and the like, but are not limited thereto.

The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the general term that after the alicyclic ring and the heteroaromatic ring are fused together, one hydrogen atom is removed, and a monovalent group is left. Preferably having 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, examples may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidbenzocycloheptyl, dibenzofuran-benzocyclopropyl, dibenzofuran-benzocyclobutyl, dibenzofuran-benzocyclopentyl, dibenzofuran-benzocyclohexyl, dibenzofuran-benzocycloheptyl, dibenzothiophene-cyclopropyl, dibenzothiophene-benzocyclobutyl, dibenzothiophene-benzocyclopentyl, dibenzothiophene-benzocyclohexyl, dibenzothiophene-benzocycloheptyl, carbazolo-cyclopropyl, carbazolo-cyclobutyl, carbazolo-cyclopentyl, carbazolo-cyclohexyl, carbazolo-cycloheptyl, and the like, but are not limited thereto.

The arylene group according to the present invention means a generic term for divalent groups remaining after two hydrogen atoms are removed from the aromatic nucleus of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, still more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, and examples may include phenylene group, biphenylene group, terphenylene group, naphthylene group, anthrylene group, phenanthrylene group, pyrenylene group, triphenylene group, perylene group, and the like, but are not limited thereto.

The alicyclic group of the present invention means a divalent group obtained by removing two hydrogen atoms from an alicyclic hydrocarbon molecule, and may be a cycloalkylene group, a cycloalkenylene group or the like, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and preferably 3 to 7 carbon atoms, and examples may include, but are not limited to, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, an adamantylene group, a norbornylene group, a cyclopropylene group, a cyclobutenyl group, a cyclopentylene group, a cyclohexenylene group, a cycloheptylene group or the like.

The term "fused ring group" as used herein refers to a generic term for alicyclic and aromatic rings wherein two hydrogen atoms are removed after the alicyclic and aromatic rings are fused together, leaving a divalent group. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, examples may include, but are not limited to, benzobicyclopropyl, benzobicyclobutyl, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, benzocyclopentylene, benzocyclohexenylene, benzocycloheptylene, naphthocyclopropyl, naphthocyclobutylene, naphthocyclopentyl, naphthocyclohexyl, and the like.

"substituted" as used herein means that a hydrogen atom in a compound group is replaced with another atom or group, and the position of substitution is not limited.

The term "substituted or unsubstituted" as used herein means that it is unsubstituted or is selected from the group consisting ofOne or more substituents of the group: protium, deuterium, tritium, cyano, halogen atom, amino, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C30 alicyclic, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused ring group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C6-C30 aryloxy group, preferably protium, deuterium, tritium, halogen atom, cyano, C1-C12 alkyl, C3-C18 alicyclic, C6-C25 aryl, C2-C25 heteroaryl, specific examples may include protium, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, phenyl, tolyl, mesityl, pentadeutero-phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, benzophenanthryl, pyrenyl, triphenylenyl, A group, perylene group, fluoranthenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, carbazolyl group, 9-phenylcarbazolyl group, spirobifluorenyl group, carbazoloindolyl group, pyrrolyl group, furanyl group, thienyl group, indolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, oxazolyl group, thiazolyl group, imidazolyl group, benzoxazolyl group, benzothiazolyl group, benzotriazolyl group, benzimidazolyl group, pyridooxazolyl group, pyridothiazolyl group, pyridoimidazolyl group, pyrimidothiazolyl group, pyrimidoimidazolyl group, quinolino oxazolyl group, quinophthiazolyl group,Quinolinoimidazolyl, phenothiazinyl, phenoxazinyl, acridinyl, and the like, but is not limited thereto. Or when the substituents are two or more, adjacent substituents may be bonded to form a ring; when the substituents are two or more, the substituents are the same or different from each other.

The linkage described herein to form a substituted or unsubstituted ring means that the two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:

In the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, and examples may include benzene, pyridine, pyrimidine, naphthalene, cyclopentene, cyclohexene, cyclopentane, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

the R is ₅ The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring, substituted or unsubstituted C1-C25 heterocycloalkyl andany one of condensed ring groups of aromatic rings of C6-C30;

The R is ₁ 、R ₂ 、R ₃ The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ringAny one of a fused ring group of a substituted or unsubstituted C1 to C25 heterocycloalkyl ring and a C6 to C30 aromatic ring, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C25 alicyclic ring and a C2 to C30 heteroaromatic ring;

provided that the triamine compound is not

Preferably, the substituent in the "substituted or unsubstituted C3-C10 alicyclic ring" is any one of deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring condensed ring group, substituted or unsubstituted C1-C25 heterocycloalkyl group and C6-C30 aromatic ring condensed ring group.

Preferably Ar ₁ ～Ar ₆ At least one selected from the structures shown in chemical formula 2, including Ar ₁ Selected from the structure shown in chemical formula 2, or Ar ₂ Selected from the structure shown in chemical formula 2, or Ar ₃ Selected from the structure shown in chemical formula 2, or Ar ₄ Selected from the structure shown in chemical formula 2, or Ar ₅ Selected from the structure shown in chemical formula 2, or Ar ₆ Selected from the structure shown in chemical formula 2, or Ar ₁ And Ar is a group ₂ Selected from the structure shown in chemical formula 2, or Ar ₁ And Ar is a group ₃ Selected from the structure shown in chemical formula 2, or Ar ₁ And Ar is a group ₅ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₃ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₅ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₃ 、Ar ₅ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₃ 、Ar ₄ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₃ 、Ar ₅ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₅ 、Ar ₆ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₃ 、Ar ₄ 、Ar ₅ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₃ 、Ar ₅ 、Ar ₆ Selected from the structure shown in chemical formula 2, or Ar ₁ 、Ar ₂ 、Ar ₃ 、Ar ₄ 、Ar ₅ 、Ar ₆ Selected from the structures shown in chemical formula 2.

Preferably, the triamine compound is selected from any one of chemical formulas 1-1 to 1-3,

preferably, R is as described in the present invention ₁ 、R ₂ 、R ₃ Any one of the same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, azetidinyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, azepanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, fluorenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclooctyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl, naphthocyclohexyl, dibenzofuranyl, dibenzothienyl, carbazolyl;

The R is ₁ ～R ₃ May be substituted or unsubstituted with one or more substituents selected from deuterium, tritium, cyano, halogen, C1-C6 alkyl, C3-C12 alicyclic, C3-C8 heterocycloalkyl, C6-C18 aryl, C3-C12 alicyclic and C6-C18 aromatic fused ring groups.

Preferably, the chemical formula 2 is selected from any one of the structures shown below,

the R is ₄ 、R ₀ The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic, and C6-C30 aromatic ring condensed ring groups;

the a are the same or different and are selected from 0, 1, 2, 3 or 4; when a is greater than 1, two or more R ₄ Are identical or different from each other, or adjacent two R ₄ Are connected with each other to form a substituted or unsubstituted ring;

the c ₁ The same or different is selected from 0, 1, 2, 3 or 4; the c ₂ The same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the c ₃ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c ₄ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c ₅ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; when two or more R's are present ₀ When two or more R' s ₀ Are identical or different from each other, or adjacent two R ₀ Are linked to each other to form a substituted or unsubstituted ring.

the R is ₄ 、R ₀ 、R ₆ 、R ₇ The same or different one selected from hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, azetidinyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, azepanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclooctyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl, naphthocyclohexyl;

The R is ₄ 、R ₀ 、R ₆ 、R ₇ May be substituted or unsubstituted with one or more substituents selected from any of deuterium, tritium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl, naphthocyclohexyl;

the a ₁ The same or different is selected from 0, 1, 2, 3 or 4; the a ₂ The same or different is selected from 0, 1, 2 or 3; the a ₃ The same or different is selected from 0, 1 or 2; when two or more R's are present ₄ When two or more R' s ₄ Are the same as or different from each other;

the c ₁ The same or different is selected from 0, 1, 2, 3 or 4; the c ₂ The same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the c ₃ Identical or differentAnd is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 9; the c ₄ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c ₅ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the c ₆ The same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c ₇ The same or different is selected from 0, 1, 2 or 3; the c ₈ The same or different is selected from 0, 1 or 2; when two or more R's are present ₀ When two or more R' s ₀ Are the same as or different from each other; when two or more R's are present ₆ When two or more R' s ₆ Are the same as or different from each other; when two or more R's are present ₇ When two or more R' s ₇ Are the same as or different from each other.

the R is ₄ 、R ₀ 、R ₆ 、R ₇ The same or different one is selected from any one of hydrogen, deuterium, tritium, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, azetidinyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, azepanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl and naphthocyclohexyl;

The R is ₄ 、R ₀ 、R ₆ 、R ₇ May be substituted or unsubstituted with one or more substituents selected from deuterium, tritium, methyl, ethyl, isopropyl, t-butyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutyl, and benzocyclopentylAny one of benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl, and naphthocyclohexyl;

the p is ₁ The same or different is selected from 0, 1, 2 or 3; the p is ₂ The same or different is selected from 0, 1, 2, 3 or 4; the p is ₃ The same or different is selected from 0, 1 or 2; the q is ₁ The same or different is selected from 0, 1, 2, 3 or 4; the q is ₂ The same or different is selected from 0, 1, 2 or 3; the q is ₃ The same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the q is ₄ The same or different is selected from 0, 1, 2, 3, 4 or 5; the q is ₅ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q is ₆ The same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the q is ₇ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the q is ₈ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the q is ₉ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the q is ₁₀ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the q is ₁₁ The same or different are selected from 0, 1 or 2.

Preferably, the Ar ₁ ～Ar ₆ At least one of the structures shown in chemical formula 2, and the rest is the same or different and is selected from any one of the structures shown in the following,

the R is ₅ The same or different radicals are selected from hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, azetidinyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, azepanyl, goldAny one of an alkyl group, a norbornyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a benzocyclopropyl group, a benzocyclobutyl group, a benzocyclopentyl group, a benzocyclohexyl group, a benzocycloheptyl group, a benzocyclooctyl group, a benzocyclopentenyl group, a benzocyclohexenyl group, a benzopiperidinyl group, a naphthocyclopentyl group, and a naphthocyclohexyl group;

The R is ₅ May be substituted or unsubstituted with one or more substituents selected from deuterium, tritium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl, naphthocyclohexyl.

Preferably, the L ₁ ～L ₆ The same or different is selected from single bond or any one of the structures shown below,

the Ra, rb and Rc are the same or different and are selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring groups;

The m is ₁ The same or different is selected from 0, 1, 2, 3 or 4; the m is ₂ The same or different are selected from 0, 1, 2, 34, 5 or 6; the m is ₃ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m is ₄ The same or different is selected from 0, 1 or 2; the m is ₅ The same or different is selected from 0 or 1; the m is ₆ The same or different is selected from 0, 1, 2 or 3; the m is ₇ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more Ra are present, the two or more Ra are the same or different from each other; when two or more Rb are present, the two or more Rb are the same or different from each other; when two or more Rc are present, the two or more Rc are the same or different from each other.

the Ra, rb, rc are the same or different and are selected from any one of hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, azetidinyl, tetrahydropyrrolyl, piperidinyl, homopiperidinyl, azepanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclooctyl, benzocyclopentenyl, benzocyclohexenyl, benzopiperidinyl, naphthocyclopentyl and naphthocyclohexyl;

The Ra, rb, rc may be substituted or unsubstituted with one or more substituents selected from protium, deuterium, tritium, C1-C6 alkyl, C3-C12 alicyclic group, C3-C8 heterocycloalkyl group, C6-C18 aryl group, C3-C12 alicyclic ring, and C6-C18 condensed ring group.

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preferably, the triamine compound is selected from any one of the structures shown below,

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the invention also provides a preparation method of the triamine compound,

xa is the same or different and is selected from I, br and Cl;

Ar ₁ -Ar ₆ 、L ₁ -L ₆ 、R ₁ 、R ₂ 、R ₃ the definitions are the same as those described above;

the reaction types related to the triamine compound are Buchwald reaction and Suzuki reaction.

The present invention may bond the above substituents by a method known in the art, and the kind and position of substituents or the number of substituents may be changed according to a technique known in the art.

The invention provides an organic electroluminescent device, which comprises an anode, a cathode, an organic layer between the anode and the cathode and outside the anode, wherein the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, and the hole transmission region contains one or more than one of the triamine compounds.

The hole transport region comprises at least one layer of a hole injection layer, a hole transport layer and a light emitting auxiliary layer.

Preferably, the hole transport region includes a hole injection layer containing one or more of the triamine compounds of the present invention.

Preferably, the hole transport region includes a hole transport layer containing one or more of the triamine compounds of the present invention.

Preferably, the hole transport region includes a light-emitting auxiliary layer containing one or more of the triamine compounds of the present invention.

The electron transport region comprises at least one of an electron injection layer, an electron transport layer and a hole blocking layer.

The organic layer of the present invention may further comprise a cover layer, an encapsulation layer, etc. However, the structure of the organic electroluminescent device of the present invention is not limited to the above-described structure, and if necessary, a plurality of organic layers may be omitted or simultaneously provided, and an organic layer having the same function may be formed in a laminated structure of two or more layers.

The light-emitting layer according to the present invention may include a host material, a dopant material, or the like, and may be formed of a single-layer structure or a multilayer structure in which the above layers are stacked.

The organic electroluminescent device of the invention has the structure that:

a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;

a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;

a substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

a substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;

a substrate/anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

a substrate/anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;

a substrate/anode/hole injection layer/hole transport layer/light emitting auxiliary layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;

a substrate/anode/hole injection layer/hole transport layer/light emitting auxiliary layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;

However, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the device parameter requirement and the material characteristics, partial organic layers can be added or omitted, and the organic layers with the same function can be made into a laminated structure with more than two layers.

The organic electroluminescent device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed.

In the organic electroluminescent device according to the present invention, the anode material preferably uses a high work function material capable of promoting injection of holes into the organic layer. Specific examples of the anode material that can be used in the present invention may include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO); combinations of metals and oxides, such as ITO-Ag-ITO; conductive polymers such as poly (3-methylthiophene), polypyrrole, polyaniline, poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), and the like, but are not limited thereto. Preferably, the anode material of the present invention is selected from ITO, ITO-Ag-ITO, and the like.

In the organic electroluminescent device of the present invention, the hole injection material is preferably a material having a good hole accepting ability. Specific examples of the hole injecting material that can be used in the present invention may include: silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, other metal oxides, phthalocyanine compounds, biphenylamine compounds, phenazine compounds, other materials, such as copper phthalocyanine (CuPc), titanyl phthalocyanine, N ' -diphenyl-N, N ' -di- [4- (N, N-diphenylamine) phenyl ] benzidine (NPNPB), N ' -tetra (4-methoxyphenyl) benzidine (MeO-TPD), and bisquinoxalino [2,3-a:2',3' -c ] phenazine (HATNA), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like, but are not limited thereto. Preferably, the hole injection material of the present invention is selected from copper phthalocyanine (CuPc), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like.

In the organic electroluminescent device according to the present invention, the hole transporting material is preferably a material having excellent hole transporting property and HOMO level matching with the corresponding anode material. Specific examples of the hole transporting material that can be used in the present invention may include materials such as diphenylamines, triphenylamines, fluorenes, and carbazoles, such as N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -di (naphthalen-1-yl) -N, N ' -di (phenyl) -2,2' -dimethylbenzidine (α -NPD), N ' -diphenyl-N, N ' -di (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), 4- [1- [4- [ di (4-methylphenyl) amino ] phenyl ] cyclohexyl ] -N- (3-methylphenyl) -N- (4-methylphenyl) aniline (TAPC), the triamine compounds described in the present invention, and the like, but are not limited thereto. Preferably, the hole transport material is selected from one or more of the triamine compounds.

In the organic electroluminescent device, the luminescent auxiliary layer is preferably a material with good hole transmission performance and electron blocking performance. Specific examples of the light-emitting auxiliary material that can be used in the present invention may include triarylamine derivatives, spirofluorene derivatives, furan derivatives, and the like, such as TPD, NPB, N, N4-bis ([ 1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1,1':4',1 "-terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4 '-diamine, N- ([ 1,1' -diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9 '-spirobifluorene-2-amine, N-bis ([ 1,1' -biphenyl ] -4-yl) -3'- (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, triamine compounds described herein, and the like, but are not limited thereto. Preferably, the material of the light-emitting auxiliary layer is selected from one or more than one of the triamine compounds.

In the organic electroluminescent device of the present invention, the luminescent layer material comprises a luminescent layer host material and a luminescent layer doping material, and the luminescent layer host material may be selected from 4,4 '-bis (9-Carbazolyl) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -ADN), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4', 1':4', 1' -tetrabiphenyl ]-4, 4' -diamine (4 PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), etc., but is not limited thereto. Preferably, the host material of the light emitting layer of the present invention is selected from 9, 10-bis (2-naphthyl) Anthracene (ADN), 9'- (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), AND the like. The light-emitting layer doping material can be selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4' -di [4- (diphenylamino) styryl)]Biphenyl (BDAVBi), 4' -di [4- (di-p-tolylamino) styryl]Diphenyl (DPAVBi), bis (2-hydroxyphenylpyridine) beryllium (Bepp 2), bis (4, 6-difluorophenylpyridine-C2, N) iridium picolinate (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy) ₃ ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) ₂ (acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq) ₃ ) Ir (piq) iridium bis (1-phenylisoquinoline) (acetylacetonate) ₂ (acac)) and the like, but is not limited thereto. Preferably, the light-emitting layer object of the present invention is selected from 4,4' -bis [4- (two-pair) Tolylamino) styryl]Biphenyl (DPAVBi), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 9, 10-di [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like.

The doping ratio of the host material for the light-emitting layer and the doping material for the light-emitting layer may be varied depending on the materials used, and is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

In the organic electroluminescent device according to the present invention, the hole blocking material has a strong hole blocking ability and suitable HOMO and LUMO energy levels, and specific examples of the hole blocking material that can be used in the present invention may include imidazoles, triazoles, phenanthroline derivatives, etc., such as 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-t-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), etc., but are not limited thereto. Preferably, the hole blocking material according to the present invention is selected from 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), etc.

In the organic electroluminescent device according to the present invention, the electron transport material is preferably a material having a strong electron withdrawing ability and low HOMO and LUMO energy levels, and specific examples of the electron transport material usable in the present invention may include imidazoles, triazoles, phenanthroline derivatives, quinolines, etc., such as 2,9- (dimethyl) -4, 7-biphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris [ (3-pyridyl) -phenyl]Benzene (TmPyPB), 4' -bis (4, 6-diphenyl-1, 3, 5-triazinyl) biphenyl (BTB), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 2- (naphthalen-2-yl) -4,7- (diphenyl) -1, 10-phenanthroline (hnephen), 8-hydroxyquinoline-lithium, and the Like (LiQ), and the like, but are not limited thereto. Preferably, the electron transport material of the present invention is selected from 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq) ₃ ) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxy)Quinoline) (4-phenylphenol) aluminum (III) (BAlq) and the like, but is not limited thereto.

In the organic electroluminescent device according to the present invention, the electron injection material preferably has a small potential barrier difference from an adjacent organic transport material, host material, or the like, and at the same time has an effect of injecting electrons from the cathode. Examples of electron injection materials that can be used in the present invention include: alkali metal salts (e.g., liF, csF), alkaline earth metal salts (e.g., mgF) ₂ ) Metal oxides (such as Al ₂ O ₃ 、MoO ₃ ) But is not limited thereto. Preferably, the electron injection material of the present invention is selected from lithium fluoride (LiF), 8-hydroxyquinoline-lithium (Liq), and the like.

In the organic electroluminescent device according to the present invention, the cathode material preferably uses a low work function material capable of promoting electron injection into the organic layer. Specific examples of the cathode material that can be used in the present invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metallic materials, e.g. LiF/Al, mg/Ag, li/Al, liO ₂ /Al、BaF ₂ Al, etc., but is not limited thereto. Preferably, the cathode according to the invention is selected from a semitransparent cathode, such as Ag or Mg-Ag alloy or thin Al.

In the organic electroluminescent device according to the present invention, the material for the cover layer is preferably a material for improving optical coupling. Specific examples of the capping layer material that can be used in the present invention may include, but are not limited to, arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, and the like. The coating layer may be formed at the same time on the outer side of the anode and the outer side of the cathode, or may be disposed on the outer side of the anode or the outer side of the cathode, and preferably, the coating layer according to the present invention is disposed on the outer side of the cathode.

The thickness of each organic layer of the organic electroluminescent device is not particularly limited, and may be any thickness commonly used in the art.

The organic electroluminescent device of the present invention may be any one of a vacuum evaporation method, a spin coating method, a vapor deposition method, a blade coating method, a laser thermal transfer method, an electrospray coating method, a slit coating method, and a dip coating method, and in the present invention, a vacuum evaporation method is preferably used.

The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, indication boards, signal lamps and the like.

The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.

Preparation and characterization of the Compounds

Description of the starting materials, reagents and characterization equipment:

the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.

The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;

the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;

synthesis example 1: preparation of intermediate A-1

A-1 (28.46 g,120 mmol), g-1 (16.98 g,124 mmol), potassium carbonate (23.06 g,240 mmol), pd (PPh) were added to the flask under nitrogen ₃ ) ₄ (1.38 g,1.20 mmol) was added 400mL of toluene/ethanol/water (3:1:1) mixed solvent, and the mixture was stirred and the above reactant system was heated at reflux for 10 hours. After the reaction, cooling to room temperature, adding toluene, separating each phase, washing toluene phase with distilled water three times, drying with anhydrous magnesium sulfate, rotary evaporating to concentrate solvent, cooling to crystallize, suction filtering, and collecting solidBenzene was recrystallized to give intermediate a-1 (23.34 g, 78% yield) with purity of > 99.34% by HPLC. Mass spectrum m/z:249.1529 (theory: 249.1517).

Synthesis example 2: preparation of intermediate A-48

The procedure was otherwise identical except for substituting an equimolar amount of B-40 for a-1 in Synthesis example 1 to give intermediate A-48 (21.32 g), which was found to have a solid purity of ≡ 99.47% by HPLC. Mass spectrum m/z:285.1532 (theory: 285.1517).

Synthesis example 3: preparation of intermediate A-53

Preparation of intermediate g-53:

q-53 (31.81 g,150.00 mmol), pinacol diboronate (41.90 g,165.00 mmol), pd (dppf) Cl were added to the flask under argon ₂ (1.10 g,1.50 mmol), KOAc (44.16 g,450.00 mmol), DMF (500 mL), heating for 5 hours, adding distilled water after the reaction, extracting with dichloromethane, separating liquid, washing the organic phase with distilled water three times, drying with anhydrous magnesium sulfate, rotary evaporating to concentrate the solvent, cooling to crystallize, suction filtering, recrystallizing the obtained solid with toluene to obtain intermediate g-53 (32.26 g, yield 83%), HPLC purity not less than 98.68%. Mass spectrum m/z:259.1729 (theory: 259.1744).

Preparation of intermediate A-53:

b-34 (23.65 g,120 mmol), g-53 (31.62 g,122 mmol), potassium carbonate (33.17 g,240 mmol), pd (PPh) were added to the flask under nitrogen ₃ ) ₄ (1.39 g,1.20 mmol) was added 400mL of toluene/ethanol/water (3:1:1) mixed solvent and the mixture was stirred and the above reactant system was heated at reflux for 10 hours. After the reaction was completed, the mixture was cooled to room temperature, toluene was added and the phases were separated, and the toluene phase was washed three times with distilled water, anhydrous sulfurDrying magnesium acid, rotary evaporating to concentrate solvent, cooling for crystallization, suction filtering, and recrystallizing the obtained solid with toluene to obtain intermediate A-53 (23.34 g, yield 78%), wherein the purity of the solid detected by HPLC is not less than 98.75%. Mass spectrum m/z:249.1526 (theory: 249.1517).

Synthesis example 4: preparation of intermediate A-100

The procedure was otherwise identical except for substituting equimolar amounts of D-16 for B-34 in Synthesis example 3 to give intermediate A-100 (20.57 g) with a purity of 98.78% as measured by HPLC. Mass spectrum m/z:214.1529 (theory: 214.1518).

Synthesis example 5: preparation of intermediate A-127

The procedure was otherwise identical except for substituting q-53 and B-34 in Synthesis example 3 with equimolar amounts of q-127 and a-127 to obtain intermediate A-127 (26.28 g), and the purity of the solid was ≡ 98.83% by HPLC. Mass spectrum m/z:281.2131 (theory: 281.2143).

Synthesis example 6: preparation of intermediate A-207

The procedure was otherwise identical except for substituting q-53 and B-34 in Synthesis example 3 with equimolar amounts of q-207 and a-207 to give intermediate A-207 (26.11 g), and the purity of the solid was ≡ 98.86% by HPLC. Mass spectrum m/z:275.1662 (theory: 275.1674).

Synthesis example 7: preparation of intermediate C-236

The procedure was otherwise identical except for substituting q-53 and B-34 in Synthesis example 3 with equimolar amounts of q-236 and B-56 to give intermediate C-236 (27.05 g), and the purity of the solid was not less than 98.87% by HPLC. Mass spectrum m/z:285.1529 (theory: 285.1517).

Synthesis example 8: preparation of intermediate A-337

The procedure was otherwise identical except for substituting B-34 in Synthesis example 3 with an equimolar amount of a-337 to give A-337 (31.74 g), and the purity of the solid was ≡98.79% by HPLC. Mass spectrum m/z:343.2316 (theory: 343.2300).

Synthesis example 9: preparation of intermediate A-371

The same procedure was repeated except for substituting q-53 and B-34 in Synthesis example 3 with equimolar amounts of q-236 and a-371 to obtain intermediate A-371 (27.67 g), and the purity of the solid was 98.85% or more by HPLC. Mass spectrum m/z:303.1972 (theory: 303.1987).

Synthesis example 10: preparation of intermediate A-637

The procedure was otherwise identical except for substituting a-1 in synthetic example 1 with an equimolar amount of a-637 to give intermediate A-637 (29.08 g) with a purity of 98.78% as measured by HPLC. Mass spectrum m/z:327.1964 (theory: 327.1987).

Synthesis example 11: preparation of Compound 1

Preparation of intermediate G-1:

b-1 (9.42 g,60 mmol), intermediate A-1 (15.96 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) was then dissolved by adding 300ml toluene and reacted under reflux with heating for 4 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give intermediate G-1 (16.20G, yield 83%), and the purity of the solid was not less than 99.47% as measured by HPLC. Mass spectrum m/z:325.1839 (theory: 325.1830).

Preparation of intermediate M-1:

toluene (600 mL), H-1 (15.46, 63 mmol), n-1 (8.11 g,30 mmol), pd (OAc) were added to the reaction flask under nitrogen ₂ (0.10 g,0.45 mmol), sodium t-butoxide (11.53 g,120 mmol) and x-phos (1.07 g,2.25 mmol) and reacted under reflux for 4 hours. After the reaction, methylene dichloride and distilled water are added into the reaction liquid to be stirred, and the mixture is extracted in a liquid-separated mode. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and purified by column chromatography (petroleum ether: dichloromethane=10:1 as eluent) to give intermediate M-1 (14.38 g, yield 80%) and the solid purity was ≡ 99.86% by HPLC. Mass spectrum m/z:598.2165 (theory: 598.2176).

Preparation of Compound 1:

toluene (100 mL), intermediate M-1 (5.99G, 10 mmol), intermediate G-1 (3.58G, 11 mmol), pd were added to the reaction flask under nitrogen ₂ (dba) ₃ (0.09 g,0.10 mmol), BINAP (0.19 g,0.30 mmol) and sodium tert-butoxide (1.92 g,20 mmol) were dissolved by stirring and reacted under reflux for 24 hours under the protection of nitrogen, after the reaction was completed, methylene chloride and distilled water were added to the reaction solution, stirred, and liquid-separated extraction was performed. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, and the obtained solid was recrystallized from toluene to obtain compound 1 (6.66 g, yield 75%) and purity of the solid was not less than 99.93% by HPLC. Mass spectrum m/z:887.4247 (theory: 887.4239). Theoretical element content (%) C ₆₆ H ₅₃ N ₃ ：C,89.25, a step of; h,6.02; n,4.73. Measured element content (%): c,89.31; h,5.98; n,4.69.

Synthesis example 12: preparation of Compound 7

Preparation of intermediate G-7:

b-7 (12.27 g,60 mmol), intermediate A-7 (10.83 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) was then dissolved by adding 300ml toluene and reacted under reflux with heating for 4.5 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give intermediate G-7 (14.73G, yield 82%), and the purity of the solid was not less than 99.74% by HPLC. Mass spectrum m/z:299.1687 (theory: 299.1674).

Preparation of intermediate H-7:

b-1 (9.42 g,60 mmol), intermediate C-7 (11.73 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) was then dissolved by adding 300ml toluene and reacted under reflux with heating for 4 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give intermediate H-7 (12.92 g, yield 83%), and the purity of the solid was not less than 99.80% by HPLC. Mass spectrum m/z:259.1376 (theory: 259.1361).

Preparation of intermediate L-7:

toluene (350 mL), intermediate H-7 (11.93 g,46 mmol), n-7 (14, 42g,45 mmol), pd (OAc) were added to the flask under nitrogen ₂ (0.11 g,0.50 mmol), cesium carbonate (39.10 g,120 mmol) and tri-tert-butylphosphine (1.20 mL of a 0.50M toluene solution, 0.60 mmol) and reacted under reflux for 3 hours. After the reaction is completed, adding dichloromethane and distilled water into the reaction solution, stirring, and separating liquid for extraction. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and purified by column chromatography (n-hexane: dichloromethane=10:2 as eluent) to give intermediate L-7 (16.47 g, yield 81%), which was found to have a solid purity of ≡ 99.87% by HPLC. Mass spectrum m/z:450.0569 (theory: 450.0578).

Preparation of intermediate M-7:

toluene (300 mL), intermediate L-7 (13.55 g,30 mmol), K-7 (5.42 g,32 mmol), pd (OAc) were added to the reaction flask under nitrogen ₂ (0.10 g,0.45 mmol), sodium t-butoxide (5.77 g,60 mmol) and x-phos (1.07 g,2.25 mmol). And reacted under reflux for 4 hours. After the reaction, methylene dichloride and distilled water are added into the reaction liquid to be stirred, and the mixture is extracted in a liquid-separated mode. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and purified by column chromatography (n-hexane: ethyl acetate=10:3 as eluent) to give intermediate M-7 (12.64 g, yield 78%), which was found to have a solid purity of ≡ 99.93% by HPLC. Mass spectrum m/z:539.2218 (theory: 539.2208).

Preparation of compound 7:

toluene (100 mL), intermediate M-7 (5.40G, 10 mmol), intermediate G-7 (3.29G, 11 mmol), pd were added to the flask under nitrogen ₂ (dba) ₃ (0.09 g,0.10 mmol), BINAP (0.19 g,0.30 mmol) and sodium tert-butoxide (1.92 g,20 mmol) were dissolved by stirring and reacted under reflux for 24 hours under the protection of nitrogen, after the reaction was completed, methylene chloride and distilled water were added to the reaction solution, stirred, and liquid-separated extraction was performed. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, and the obtained solid was recrystallized from toluene to obtain compound 7 (6.10 g, yield 76%), the purity of the solid was not less than 99.99% by HPLC. Mass spectrum m/z:802.4102 (theory: 802.4115). Theoretical element content (%) C ₅₉ H ₄₆ D ₃ N ₃ : c,88.24; h,6.53; n,5.23. Measured element content (%): c,88.18; h,6.49; n,5.28.

Synthesis example 13: preparation of Compound 8

The procedure was otherwise identical except for substituting A-1 and B-1 in Synthesis example 11 with equimolar amounts of A-8 and B-8 to give Compound 8 (6.45 g), and the purity of the solid was ≡99.99% by HPLC detection. Mass spectrum m/z:847.3941 (theory: 847.3926). Theoretical element content (%) C ₆₃ H ₄₉ N ₃ : c,89.22; h,5.82; n,4.95. Measured element content (%): c,89.18; h,5.77; n,5.01.

Synthesis example 14: preparation of Compound 16

Preparation of intermediate G-16:

b-16 (15.55 g,60 mmol), intermediate A-7 (10.84 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) was then dissolved by adding 300ml toluene and reacted under reflux with heating for 5.5 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give intermediate G-16 (17.10G, yield 82%) which was found to have a solid purity of ≡ 99.72% by HPLC. Mass spectrum m/z:347.1690 (theory: 347.1674).

Preparation of intermediate H-16:

d-16 (9.72 g,60 mmol), intermediate C-16 (15.6 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) was then dissolved by adding 300ml toluene and reacted under reflux with heating for 3 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give intermediate H-16 (16.84 g, yield 86%), and the purity of the solid was not less than 99.79% by HPLC. Mass spectrum m/z:326.1849 (theory: 326.1831).

Preparation of intermediate M-16:

toluene (600 mL), H-16 (20.75 g,63 mmol), n-1 (8.11 g,30 mmol), pd (OAc) were added to the flask under nitrogen ₂ (0.10 g,0.45 mmol), sodium t-butoxide (11.53 g,120 mmol) and x-phos (1.07 g,2.25 mmol). And reacted under reflux for 5 hours. After the reaction, methylene dichloride and distilled water are added into the reaction liquid to be stirred, and the mixture is extracted in a liquid-separated mode. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and purified by column chromatography (petroleum ether: dichloromethane=10:3 as eluent) to give intermediate M-16 (18.50 g, yield 81%), which was found to have a solid purity of > 99.89% by HPLC. Mass spectrum m/z:760.3457 (theory: 760.3429).

Preparation of Compound 16:

toluene (100 mL), intermediate M-16 (7.61G, 10 mmol), intermediate G-16 (3.82G, 11 mmol), pd were added to the reaction flask under nitrogen ₂ (dba) ₃ (0.09 g,0.10 mmol), BINAP (0.19 g,0.30 mmol) and sodium tert-butoxide (1.92 g,20 mmol) were dissolved by stirring and reacted under reflux for 25 hours under the protection of nitrogen, after the reaction was completed, methylene chloride and distilled water were added to the reaction solution, stirred, and liquid-separated extraction was performed. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, and the obtained solid was recrystallized from toluene to obtain compound 16 (7.72 g, yield 72%), and the purity of the solid was not less than 99.94% by HPLC. Mass spectrum m/z:1071.5326 (theory: 1071.5337). Theoretical element content (%) C ₈₀ H ₄₉ D ₁₀ N ₃ : c,89.60; h,6.48; n,3.92. Measured element content (%): c,89.56; h,6.53; n,3.87.

Synthesis example 15: preparation of Compound 34

Preparation of intermediate G-34:

b-34 (11.82 g,60 mmol), intermediate A-34 (14.55 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) then dissolved by adding 300ml toluene and heatingThe reaction was refluxed for 3.5 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give intermediate G-34 (7.73G, yield 75%) which was found to have a solid purity of ≡ 99.72% by HPLC. Mass spectrum m/z:343.2318 (theory: 343.2300).

Preparation of compound 34:

toluene (200 mL), intermediate G-34 (11.34G, 33 mmol), n-34 (3.15G, 10 mmol), pd were charged to a reaction flask under nitrogen ₂ (dba) ₃ (0.09 g,0.10 mmol), BINAP (0.57 g,0.90 mmol) and sodium tert-butoxide (5.77 g,60 mmol) were dissolved by stirring, and the reaction was refluxed under the protection of nitrogen for 24 hours, after the completion of the reaction, methylene chloride and distilled water were added to the reaction solution, stirred, and then the solution was extracted by liquid separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and the obtained solid was recrystallized from toluene to obtain compound 34 (7.83 g, yield, 71%) which had a purity of not less than 99.93% by HPLC. Mass spectrum m/z:1101.6914 (theory: 1101.6900). Theoretical element content (%) C ₈₁ H ₈₇ N ₃ : c,88.24; h,7.95; n,3.81. Measured element content (%): c,88.27; h,7.98; n,3.77.

Synthesis example 16: preparation of Compound 40

A-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-40 and B-40, and the other steps were the same, to obtain Compound 40 (6.98 g), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:942.5511 (theory: 942.5494). Theoretical element content (%) C ₆₉ H ₄₂ D ₁₅ N ₃ : c,87.85; h,7.69; n,4.45. Measured element content (%): c,87.90; h,7.72; n,4.39.

Synthesis example 17: preparation of Compound 48

Preparation of compound 48:

a-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-48 and B-48, and the procedure was the same, except that compound 48 (8.12 g) was obtained, and the purity of the solid was not less than 99.92% by HPLC detection. Mass spectrum m/z:1158.5665 (theory: 1158.5680). Theoretical element content (%) C ₈₇ H ₆₆ D ₃ N ₃ : c,90.12; h,6.26; n,3.62. Measured element content (%): c,90.07; h,6.31; n,3.58.

Synthesis example 18: preparation of Compound 53

Preparation of Compound 53:

a-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-53 and B-1, and the procedure was the same, except that compound 53 (7.55 g) was obtained, and the purity of the solid was not less than 99.95% by HPLC detection. Mass spectrum m/z:1047.5479 (theory: 1047.5491). Theoretical element content (%) C ₇₈ H ₆₉ N ₃ : c,89.36; h,6.63; n,4.01. Measured element content (%): c,89.41; h,6.59; n,3.97.

Synthesis example 19: preparation of Compound 56

A-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-7 and B-56, and the other steps were the same, to obtain Compound 56 (6.87 g), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:927.4562 (theory: 927.4552). Theoretical element content (%) C ₆₉ H ₅₇ N ₃ : c,89.28; h,6.19; n,4.53. Measured element content (%): c,89.33; h,6.24; n,4.47.

Synthesis example 20: preparation of Compound 79

A-34 and B-34 in Synthesis example 15 were successively replaced with A-79 and B-79 in equimolar amounts, and the other steps were the same, to obtain compound 79 (7.33 g), and the purity of the solid was not less than 99.95% by HPLC detection. Mass spectrum m/z:1017.5949 (theory: 1017.5961). Theoretical element content (%) C ₇₅ H ₇₅ N ₃ : c,88.45; h,7.42; n,4.13. Measured element content (%): c,88.50; h,7.38; n,4.15.

Synthesis example 21: preparation of Compound 86

A-34 and B-34 in Synthesis example 15 were successively replaced with A-86 and B-86 in equimolar amounts, and the procedure was the same, except that compound 86 (7.40 g) was obtained, and the purity of the solid was not less than 99.94% by HPLC detection. Mass spectrum m/z:1026.6261 (theory: 1026.6247). Theoretical element content (%) C ₇₅ H ₃₀ D ₂₇ N ₃ : c,87.67; h,8.24; n,4.09. Measured element content (%): c,87.72; h,8.19; n,4.13.

Synthesis example 22: preparation of Compound 94

A-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-94 and B-40, and the other steps were the same, to obtain compound 94 (8.22 g), and the purity of the solid was not less than 99.92% by HPLC detection. Mass spectrum m/z:1176.6742 (theory: 1176.6757). Theoretical element content (%) C ₈₄ H ₈₄ N ₆ : c,85.67; h,7.19; n,7.14. Measured element content (%): c,85.68; h,7.13; n,7.08.

Synthesis example 23: preparation of Compound 100

Preparation of Compound 100:

the procedure was otherwise identical except for substituting A-34 and B-34 in Synthesis example 15 with equimolar amounts of A-100 and B-1 to give Compound 100 (6.98 g), with purity of solid ≡ 99.97% by HPLC detection. Mass spectrum m/z:942.5509 (theory: 942.5494). Theoretical element content (%) C ₆₉ H ₄₂ D ₁₅ N ₃ : c,87.85; h,7.69; n,4.45. Measured element content (%): c,87.90; h,7.71; n,4.41.

Synthesis example 24: preparation of Compound 127

Preparation of compound 127:

the procedure was otherwise as described except for substituting A-34 and B-34 in Synthesis example 15 with equimolar amounts of A-127 and B-1 to give compound 127 (8.01 g), which was found to have a solid purity of ≡ 99.92% by HPLC. Mass spectrum m/z:1143.7381 (theory: 1143.7370). Theoretical element content (%) C ₈₄ H ₉₃ N ₃ : c,88.14; h,8.19; n,3.67. Measured element content (%): c,88.09; h,8.22; n,3.71.

Synthesis example 15: preparation of Compound 139

A-34 and B-34 in the preparation of the compound 34 were successively replaced with equimolar amounts of A-139 and B-438, and the other steps were the same, to obtain a compound 139 (8.21 g), and the purity of the solid was not less than 99.93% by HPLC detection. Mass spectrum m/z:1155.5487 (theory: 1155.5491). Theoretical element content (%) C ₈₇ H ₆₉ N ₃ : c,90.35; h,6.01; n,3.63. Measured element content (%): c,90.39; h,6.02; n,3.58.

Synthesis example 26: preparation of Compound 173

A-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-173 and B-173, and the other steps were the same, to obtain compound 173 (6.76 g), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:912.5761 (theory: 912.5778). Theoretical element content (%) C ₆₆ H ₂₄ D ₂₇ N ₃ : c,86.80; h,8.60; n,4.60. Measured element content (%): c,86.76; h,8.65; n,4.57.

Synthesis example 27: preparation of Compound 196

A-1, B-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-196, B-40 and G-196, and the other steps were the same, to obtain compound 196 (7.04G), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:963.4541 (theory: 963.4552). Theoretical element content (%) C ₇₂ H ₅₇ N ₃ : c,89.68; h,5.96; n,4.36. Measured element content (%): c,89.72; h,5.91; n,4.41.

Synthesis example 28: preparation of Compound 207

A-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-207 and H-207, and the other steps were the same, to obtain compound 207 (7.38G), and the purity of the solid was not less than 99.95% by HPLC detection. Mass spectrum m/z:1023.5506 (theory: 1023.5491). Theoretical element content (%) C ₇₆ H ₆₉ N ₃ : c,89.11; h,6.79; n,4.10. Measured element content (%): c,89.08; h,6.83n,4.07.

Synthesis example 29: preparation of Compound 231

A-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-231 and H-231, and the other steps were the same, to obtain compound 231 (6.25G), and the purity of the solid was not less than 99.99% by HPLC detection. Mass spectrum m/z:821.4567 (theory: 821.4554). Theoretical element content (%) C ₆₀ H ₃₉ D ₁₀ N ₃ : c,87.66; h,7.23; n,5.11. Measured element content (%): c,87.71; h,7.19; n,5.13.

Synthesis example 30: preparation of Compound 236

The procedure was followed except for replacing B-16, D-16 and C-16 in Synthesis example 14 with equimolar amounts of B-34, B-1 and C-236, to give compound 236 (7.78 g), and the purity of the solid was ≡ 99.94% by HPLC. Mass spectrum m/z:1079.5195 (theory: 1079.5178). Theoretical element content (%) C ₈₁ H ₆₅ N ₃ : c,90.05; h,6.06; n,3.89. Measured element content (%): c,90.11; h,6.02; n,3.92.

Synthesis example 31: preparation of Compound 251

H-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of G-251 and H-251, and the other steps were the same, to obtain compound 251 (7.20G), and the purity of the solid was not less than 99.95% by HPLC detection. Mass spectrum m/z:999.5387 (theory: 999.5368). Theoretical element content (%) C ₇₄ H ₅₃ D ₈ N ₃ : c,88.85; h,6.95; n,4.20. Measured element content (%): c,88.81; h,7.01; n,4.16.

Synthesis example 32: preparation of Compound 282

H-1, n-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of G-282, n-282 and H-282, and the other steps were the same, to obtain compound 282 (6.88G), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:929.4697 (theory: 929.4709). Theoretical element content (%) C ₆₉ H ₅₉ N ₃ : c,89.09; h,6.39; n,4.52. Measured element content (%): c,89.12; h,6.44; n,4.49.

Synthesis example 33: preparation of Compound 293

A-1, B-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-7, B-293 and H-1, and the same procedure was repeated to obtain compound 293 (7.10G), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:971.5161 (theory: 971.5178). Theoretical element content (%) C ₇₂ H ₆₅ N ₃ : c,88.94; h,6.74; n,4.32. Measured element content (%): c,88.97; h,6.76; n,4.29.

Synthesis example 34: preparation of Compound 301

A-34 and B-34 in Synthesis example 15 were successively replaced with equimolar amounts of A-8 and B-301, and the other steps were the same, to obtain Compound 301 (6.89 g), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:930.4729 (theory: 930.4741). Theoretical element content (%) C ₆₉ H ₅₄ D ₃ N ₃ : c,88.99; h,6.49; n,4.51. Measured element content (%): c,89.03; h,6.51; n,4.47.

Synthesis example 35: preparation of Compound 316

A-1, B-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-8, B-316 and H-316, and the other steps were the same, to obtain compound 316 (6.66G), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:887.4231 (theory: 887.4239). Theoretical element content (%) C ₆₆ H ₅₃ N ₃ : c,89.25; h,6.02; n,4.73. Measured element content (%): c,89.29; h,6.08; n,4.68.

Synthesis example 36: preparation of Compound 337

The procedure was otherwise identical except for substituting A-34 and B-34 in Synthesis example 15 with equimolar amounts of A-337 and B-1 to give 337 (9.18 g), which was detected by HPLC to have a solid purity of ≡99.90%. Mass spectrum m/z:1329.7853 (theory: 1329.7839). Theoretical element content (%) C ₉₉ H ₉₉ N ₃ : c,89.34; h,7.50; n,3.16. Measured element content (%): c,89.29; h,7.47; n,3.21.

Synthesis example 37: preparation of Compound 367

A-1, B-1 and H-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-8, B-40 and H-367, and the other steps were the same, to obtain Compound 367 (6.50 g), and the purity of the solid was ≡ 99.98% by HPLC detection. Mass spectrum m/z:865.5069 (theory: 865.5056). Theoretical element content (%) C ₆₃ H ₃₁ D ₁₈ N ₃ : c,87.36; h,7.79; n,4.85. Measured element content (%): c,87.41; h,7.83N,4.79.

Synthesis example 38: preparation of Compound 371

A-7, B-16, C-16 and D-16 in Synthesis example 14 were successively replaced with A-8, D-371, A-371 and B-1, and the other steps were the same, to obtain Compound 371 (8.17 g), and the purity of the solid was ≡ 99.92% by HPLC detection. Mass spectrum m/z:1165.6262 (theory: 1165.6274). Theoretical element content (%) C ₈₇ H ₇₉ N ₃ : c,89.57; h,6.83; n,3.60. Measured element content (%): c,89.61; h,6.86; n,3.55.

Synthesis example 39: preparation of Compound 398

A-1, B-1 and H-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-40, B-398 and H-398, and the other steps were the same, to obtain compound 398 (6.47 g), and the purity of the solid was ≡ 99.98% by HPLC detection. Mass spectrum m/z:862.4851 (theory: 862.4868). Theoretical element content (%) C ₆₃ H ₃₄ D ₁₅ N ₃ : c,87.66; h,7.47; n,4.87. Measured element content (%): c,87.70; h,7.51; n,4.83.

Synthesis example 40: preparation of Compound 403

G-1 in Synthesis example 11 was replaced with an equimolar amount of G-367, and the procedure was the same, to give Compound 403 (6.45G), with a purity of the solid of ≡ 99.99% by HPLC detection. Mass spectrum m/z:847.3913 (theory: 847.3926). Theoretical element content (%) C ₆₃ H ₄₉ N ₃ : c,89.22; h,5.82; n,4.95. Measured element content (%): c,89.18; h,5.79; n,4.98.

Synthesis example 41: preparation of Compound 436

Preparation of intermediate L-436:

toluene (300 mL), G-236 (9.13G, 32 mmol), n-436 (13.14G, 30 mmol), pd (OAc) were added to the reaction flask under nitrogen ₂ (0.10 g,0.45 mmol), sodium t-butoxide (5.77 g,60 mmol), and X-PHOS (1.07 g,2.25 mmol). And reacted under reflux for 3 hours. After the reaction, methylene dichloride and distilled water are added into the reaction liquid to be stirred, and the mixture is extracted in a liquid-separated mode. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and purified by column chromatography (petroleum ether: ethyl acetate=10:2 as eluent) to give intermediate L-436 (14.29 g, yield 80%), which was found to have a solid purity of ≡ 99.79% by HPLC. Mass spectrum m/z:593.0339 (theory: 593.0354).

Preparation of intermediate G-436:

b-436 (9.54 g,60 mmol), intermediate A-7 (10.83 g,64 mmol), sodium tert-butoxide (8.64 g,90 mmol), pd (dppf) Cl were added to the flask under nitrogen ₂ (0.44 g,0.6 mmol) was then dissolved by adding 300ml toluene and reacted under reflux with heating for 5 hours. After the completion of the reaction, cooled to room temperature, water was added, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to give G-436 (6.31G, yield 85%), and the purity of the solid was not less than 99.88% by HPLC. Mass spectrum m/z:247.1302 (theory: 247.1287).

Preparation of compound 436:

toluene (100 mL), intermediate G-436 (5.44G, 22 mmol), intermediate L-436 (5.95G, 10 mmol), pd were added to a reaction flask under nitrogen ₂ (dba) ₃ (0.09 g,0.10 mmol), BINAP (0.19 g,0.30 mmol) and sodium tert-butoxide (3.84 g,40 mmol) were dissolved by stirring and reacted under reflux for 20 hours under the protection of nitrogen, after the reaction was completed, methylene chloride and distilled water were added to the reaction solution, stirred, and liquid-separated extraction was performed. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and the obtained solid was recrystallized from toluene to obtain compound 436 (13.74 g, yield 74%) and HPLC detected a solid purity of 99.97%. Mass spectrum m/z:927.4420 (theory: 927.4404). Theoretical element content (%) C ₆₉ H ₅₁ T ₂ N ₃ : c,89.28; h,6.19; n,4.53. Measured element content (%): c,89.33; h,6.21; n,4.49.

Synthesis example 42: preparation of Compound 438

A-1, B-1 and H-1 in Synthesis example 11 were successively replaced with equimolar amounts of A-8, B-438 and H-438, and the other steps were the same, to obtain compound 438 (6.72 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:895.3935 (theory: 895.3926). Theoretical element content (%) C ₆₇ H ₄₉ N ₃ : c,89.80; h,5.51; n,4.69. Measured element content (%): c,89.76; h,5.49; n,4.73.

Synthesis example 43: preparation of Compound 439

The procedure was followed except for sequentially substituting B-7, H-7, n-7 and K-7 in Synthesis example 12 into equimolar amounts of B-439, K-7, n-439 and K-439, to give Compound 439 (6.56 g), and the purity of the solid was ≡ 99.98% by HPLC detection. Mass spectrum m/z:873.4070 (theory: 873.4083). Theoretical element content (%) C ₆₅ H ₅₁ N ₃ : c,89.31; h,5.88; n,4.81. Measured element content (%): c,89.27; h,5.92; n,4.78.

Synthesis example 44: preparation of Compound 441

A-7, B-16, C-16 and D-16 in Synthesis example 14 were successively replaced with equimolar amounts of A-441, B-1, A-8 and D-441, and the other steps The same procedure is followed to give compound 441 (6.98 g) having a purity of > 99.96% as measured by HPLC. Mass spectrum m/z:961.5047 (theory: 961.5022). Theoretical element content (%) C ₆₉ H ₅₅ D ₄ N ₅ : c,86.12; h,6.60; n,7.28. Measured element content (%): c,86.16; h,6.58; n,7.26.

Synthesis example 45: preparation of Compound 506

H-1 and G-1 in Synthesis example 11 were successively replaced with equimolar amounts of G-40 and H-398, and the other steps were the same, to obtain Compound 506 (6.68G), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:902.5196 (theory: 902.5181). Theoretical element content (%) C ₆₆ H ₃₈ D ₁₅ N ₃ : c,87.76; h,7.59; n,4.65. Measured element content (%): c,87.71; h,7.63; n,4.68.

Synthesis example 46: preparation of Compound 545

The procedure was otherwise as described except for substituting A-34, B-34 and n-34 in Synthesis example 15 with equimolar amounts of A-86, B-545 and n-545 to give compound 545 (6.44 g) having a purity of > 99.98% as measured by HPLC. Mass spectrum m/z:858.4755 (theory: 858.4741). Theoretical element content (%) C ₆₃ H ₅₄ D ₃ N ₃ : c,88.07; h,7.04; n,4.89. Measured element content (%): c,88.11; h,6.99; n,4.92.

Synthesis example 47: preparation of Compound 603

A-7, B-16, C-16, D-16 and G-16 in Synthesis example 14 were successively replaced with equimolar amounts of A -603, B-603, A-8, c-603, G-603, the other steps being identical, giving compound 438 (6.77G), purity of the solid being ≡ 99.97% by HPLC. Mass spectrum m/z:913.5345 (theory: 913.5335). Theoretical element content (%) C ₆₇ H ₆₇ N ₃ : c,88.02; h,7.39; n,4.60. Measured element content (%): c,87.98; h,7.45; n,4.57.

Synthesis example 48: preparation of Compound 604

H-7, n-7, K-7 and G-7 in Synthesis example 12 were successively replaced with equimolar amounts of G-604, n-439, K-604 and H-251, and the other steps were the same, to obtain Compound 604 (6.17G), and the purity of the solid was ≡ 99.99% by HPLC detection. Mass spectrum m/z:811.4878 (theory: 811.4865). Theoretical element content (%) C ₅₉ H ₆₁ N ₃ : c,87.26; h,7.57; n,5.17. Measured element content (%): c,87.21; h,7.61; n,5.20.

Synthesis example 49: preparation of Compound 637

A-7, B-7, H-7, n-7 and K-7 in Synthesis example 12 were successively replaced with equimolar amounts of A-637, a-337, K-7, n-439 and H-637, and the other steps were the same, to obtain compound 637 (7.72 g), and the purity of the solid as measured by HPLC was ≡ 99.94%. Mass spectrum m/z:1071.5505 (theory: 1071.5491). Theoretical element content (%) C ₈₀ H ₆₉ N ₃ : c,89.60; h,6.49; n,3.92. Measured element content (%): c,89.56; h,6.53; n,3.95.

Synthesis example 50: preparation of Compound 664

In the synthesis example 11H-1 and G-1 were replaced with equimolar amounts of G-664 and H-664 in the same manner, and compound 664 (6.84G) was obtained in the same manner, and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:923.5164 (theory: 923.5178). Theoretical element content (%) C ₆₈ H ₆₅ N ₃ : c,88.37; h,7.09; n,4.55. Measured element content (%): c,88.42; h,7.13; n,4.51.

Device examples 1 to 18

The ITO glass substrate is ultrasonically cleaned by 5% glass cleaning liquid for 2 times each for 20 minutes, and then ultrasonically cleaned by deionized water for 2 times each for 10 minutes. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. Vacuum evaporating HI-1 serving as a hole injection layer on an ITO substrate to obtain an evaporation thickness of 15nm; vacuum evaporating the compound 16 as a hole transport layer on the hole injection layer, wherein the evaporation thickness is 80nm; vacuum evaporation BH-1:BD-1=96:4 (mass ratio) is adopted as a light-emitting layer on the hole transport layer, and the evaporation thickness is 20nm; vacuum evaporating ET-1 on the luminous layer as an electron transport layer, wherein the evaporating thickness is 30nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1nm; al is vacuum evaporated on the electron injection layer as a cathode, and the evaporation thickness is 70nm.

Device examples 2 to 18: an organic electroluminescent device was produced by the same procedure as in device example 1, except that the compound 16 according to the invention in device example 1 was replaced with the compound 34, 40, 48, 53, 56, 86, 100, 139, 196, 207, 367, 403, 441, 506, 603, 637, 664, respectively, as a hole transporting material.

Comparative examples 1 to 3: an organic electroluminescent device was produced by the same procedure as in device example 1, except that the compound 16 of the present invention in device example 1 was replaced with the comparative compound 1, comparative compound 2, and comparative compound 3, respectively, as a hole transport layer.

Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.

The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 1. Table 1 shows the results of the luminescence characteristics test of the organic electroluminescent devices prepared from the compounds prepared in the inventive examples and the comparative substances.

Device examples 19 to 47

The ITO glass substrate is ultrasonically cleaned by 5% glass cleaning liquid for 2 times each for 20 minutes, and then ultrasonically cleaned by deionized water for 2 times each for 10 minutes. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. Vacuum evaporating HI-1 serving as a hole injection layer on an ITO substrate to obtain an evaporation thickness of 15nm; vacuum evaporating HT-1 on the hole injection layer as a hole transport layer, wherein the evaporating thickness is 50nm; vacuum evaporating the compound 1 as a light-emitting auxiliary layer on the hole transport layer, wherein the evaporation thickness is 40nm, and vacuum evaporating BH-1:BD-1=96:4 (mass ratio) as a light-emitting layer on the light-emitting auxiliary layer, wherein the evaporation thickness is 20nm; vacuum evaporating ET-1 on the luminous layer as an electron transport layer, wherein the evaporating thickness is 30nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1nm; al is vacuum evaporated on the electron injection layer as a cathode, and the evaporation thickness is 70nm.

Device examples 20 to 47: an organic electroluminescent device was produced by the same procedure as in device example 19, except that the compound 1 of the present invention in device example 19 was used as a light-emitting auxiliary layer material, in place of the compound 1 of the present invention in device example 19, respectively, 7, 8, 34, 40, 56, 79, 94, 100, 127, 173, 231, 236, 251, 282, 293, 301, 316, 337, 367, 371, 398, 403, 436, 438, 439, 506, 545, 604.

Comparative examples 4 to 6: an organic electroluminescent device was produced by the same procedure as in device example 19, except that the compound 1 of the present invention in device example 19 was replaced with the comparative compound 1, comparative compound 2, and comparative compound 3, respectively, as a light-emitting auxiliary layer material.

The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 2. Table 2 shows the results of the test of the luminescence characteristics of the organic electroluminescent devices prepared from the compounds prepared in the inventive examples and the comparative substances.

As can be seen from tables 1 and 2, when the triamine compound of the present invention is used as a hole transport layer material and a light-emitting auxiliary layer material to be applied to an organic electroluminescent device, the light-emitting efficiency and the service life of the device are remarkably improved. The triamine compound disclosed by the invention has good hole mobility, can balance the carrier transmission in the device, improves the luminous efficiency of the device, has good thermal stability and film forming property, and can effectively prolong the service life of the device.

It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims

1. A triamine compound is characterized in that the triamine compound has a structure shown in a chemical formula 1,

the R is ₅₁ The same or different one is selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, cyclobutyl, cyclopentyl, cyclohexyl, piperidinyl, adamantyl and phenyl;

the R is ₅ The same or different hydrogen and deuterium;

when R is ₅₁ When selected from any one of methyl, ethyl, isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, piperidinyl, adamantyl and phenyl, R is the same as R ₅ May be substituted or unsubstituted with one or more substituents that are deuterium;

said b ₁ Selected from 0, 1, 2, 3, 4 or 5; said b ₂ The same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b ₃ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; when two or more R's are present ₅ When two or more R' s ₅ Are the same as or different from each other; when R is ₅₁ B is any one selected from methyl, ethyl, isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, piperidinyl, adamantyl and phenyl ₁ Selected from 1 or 2;

the chemical formula 2 is selected from any one of the structures shown below,

the R is ₄ The same or different one is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, adamantyl, norbornyl, phenyl and naphthyl; when said R is ₄ R is selected from any one of methyl, ethyl, isopropyl, tertiary butyl, adamantyl, norbornyl and naphthyl ₄ May be substituted or unsubstituted with one or more substituents that are deuterium; when said R is ₄ R is selected from phenyl ₄ May be substituted or unsubstituted with one or more deuterium, or may be substituted with an adamantyl group;

the R is ₁₀ The same or different hydrogen, deuterium, methyl or phenyl; when said R is ₁₀ R is selected from methyl and phenyl ₁₀ May be substituted or unsubstituted with one or more substituents that are deuterium;

The R is ₀ The same or different hydrogen, deuterium and methyl; when said R is ₀ When selected from methyl, R ₀ May be substituted or unsubstituted with one or more substituents that are deuterium;

the p is ₁ The same or different is selected from 0, 1, 2 or 3; the p is ₂ The same or different is selected from 0, 1, 2, 3 or 4; the q is ₁ The same or different is selected from 0, 1, 2, 3 or 4; the q is ₃ The same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the q is ₄ The same or different is selected from 0, 1, 2, 3, 4 or 5; the q is ₅ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q is ₇ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the q is ₉ The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12;

when R is ₄ Selected from methyl, ethyl, isopropyl, t-butyl, adamantyl, norbornyl, and naphthylAt any one of the above, p ₁ Selected from 1; the p is ₂ Selected from 1;

when R is ₁₀ When selected from phenyl, the q ₃ Selected from 1; the q is ₅ Selected from 1;

the L is ₁ ～L ₆ The same or different is selected from single bond or any one of the structures shown below,

the R is ₁ 、R ₂ 、R ₃ The same or different hydrogen, deuterium and methyl; when R is ₁ ～R ₃ When selected from methyl, the R ₁ ～R ₃ May be substituted or unsubstituted with one or more substituents that are deuterium;

provided that the triamine compound is not

2. A triamine compound according to claim 1, wherein the triamine compound is selected from any one of chemical formulas 1 to 3,

the R is ₁ 、R ₂ 、R ₃ The same or different hydrogen and deuterium.

3. A triamine compound is characterized in that the triamine compound is selected from any one of the structures shown in the specification,

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4. an organic electroluminescent device comprising an anode, a cathode, an organic layer between and beyond the anode and the cathode, the organic layer comprising a hole transport region, a light emitting layer, and an electron transport region, wherein the hole transport region contains one or more of the triamine compounds according to any of claims 1 to 3.

5. An organic electroluminescent device according to claim 4, wherein the hole transport region comprises a hole transport layer and/or a light-emitting auxiliary layer, the hole transport layer and/or the light-emitting auxiliary layer containing one or more of the triamine compounds according to any of claims 1 to 3.