CN117651433A

CN117651433A - Organic electroluminescent device

Info

Publication number: CN117651433A
Application number: CN202410020288.2A
Authority: CN
Inventors: 董秀芹; 周雯庭; 韩春雪; 刘喜庆
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2024-01-05
Filing date: 2024-01-05
Publication date: 2024-03-05

Abstract

The invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescent devices. The organic electroluminescent device comprises an anode, an organic layer and a cathode, wherein the organic layer is arranged between the anode and the cathode, the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, the hole transmission region is arranged between the anode and the luminescent layer, the electron transmission region is arranged between the luminescent layer and the cathode, the hole transmission region contains a compound shown in a formula 1, and the electron transmission region contains a compound shown in a formula 2. The compound in the formula 1 in the hole transmission area and the compound in the formula 2 in the electron transmission area of the organic electroluminescent device have matched energy levels, good thermal stability and film forming property, are favorable for realizing charge balance in the device, promote efficient recombination of holes and electrons in the luminescent layer, improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device.

Description

Organic electroluminescent device

Technical Field

The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.

Background

An organic electroluminescent device (OLED) is a technology for directly converting electric energy into light energy using an organic material. The organic electroluminescent device has the advantages of light and thin body, wide visual angle, quick response, wide use temperature range, low energy consumption, high efficiency, good color purity and high definition, can realize flexible display, and is widely used in electronic products such as mobile phones, computers, televisions, wearable equipment and the like.

The working principle of the organic electroluminescent device is that proper voltage is applied to two ends of an electrode, holes and electrons are generated at the two ends of the electrode, the electric field is driven to enable the holes and the electrons to be respectively injected into an organic functional layer from the two ends of the electrode, the holes and the electrons are transmitted through the organic functional layer, finally the holes and the electrons reach a light-emitting layer to be combined into high-energy excitons, and then the excitons decline and radiate photons to emit light. Nowadays, organic electroluminescent devices mostly adopt sandwich structures, i.e. organic functional layers are arranged between the cathode and the anode on both sides of the device. The organic functional layer may include a hole transport region including a hole injection layer, a hole transport layer, an electron blocking layer, etc., an emission layer, an electron transport region including an electron injection layer, an electron transport layer, a hole blocking layer, etc.

With the development of organic electroluminescent devices, the luminous efficiency and the service life of the organic electroluminescent devices are important problems that need to be solved at present. However, in order to further improve the light emitting efficiency of the organic electroluminescent device and to extend the service life of the organic electroluminescent device, it is necessary to obtain a material having a balance between hole and electron transport and to control the holes and electrons to be efficiently recombined in the light emitting layer. The key point is that the energy levels of the functional layers and the properties of the materials are matched with each other, and the performance of the organic electroluminescent device can be truly improved only if the optimal combination of the organic layers is realized. Therefore, it is necessary to develop a hole transport region material and an electron transport region material which have good thermal stability and film forming property, energy level matching, and can realize charge balance of the device, improve the light emitting efficiency of the organic electroluminescent device, and prolong the service life of the organic electroluminescent device.

Disclosure of Invention

Aiming at the problems in the prior art, the invention provides an organic electroluminescent device.

The invention provides an organic electroluminescent device, comprising an anode, an organic layer and a cathode, wherein the organic layer is arranged between the anode and the cathode, the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, the hole transmission region is arranged between the anode and the luminescent layer, the electron transmission region is arranged between the luminescent layer and the cathode, the hole transmission region contains a compound shown in a formula 1, the electron transmission region contains a compound shown in a formula 2,

In formula 1, the Ar ₁ One or a combination of substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted alicyclic of C3-C20 and condensed ring group of aromatic ring of C6-C30;

the R is ₀ One selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups;

the R is ₁ The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or adjacent two R ₁ Bonded to each other to form a substituted or unsubstituted ring;

said Z is selected from O, S, CR _a R _b Or NR (NR) _c ；

The R is _a 、R _b The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, one of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring condensed ring group, or adjacent R _a 、R _b Bonded to each other to form a substituted or unsubstituted ring;

the R is _c One selected from a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C20 alicyclic ring, and a condensed ring group of a C6-C30 aromatic ring;

the R is ₂ The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or adjacent two R ₂ Bonded to each other to form a substituted or unsubstituted ring;

the a ₁ Selected from 0, 1, 2, 3 or 4; said b ₁ Selected from 0, 1, 2, 3 or 4; said b ₂ Selected from 0, 1, 2 or 3;

the L is ₀ 、L ₁ 、L ₂ Independently selected from one or a combination of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted alicyclic of C3-C20 and sub-condensed ring group of aromatic ring of C6-C30;

in formula 2, x is the same or different and is selected from CH or N, and at least one is selected from N, when x is bonded with other groups, the x is selected from C atoms;

The Ar is as follows ₃ 、Ar ₄ 、Ar ₅ The same or different aryl groups selected from substituted or unsubstituted C6-C30, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic rings and one or a combination of condensed ring groups of the aromatic rings of C6-C30;

the L is ₃ 、L ₄ 、L ₅ Independently selected from one or a combination of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30, substituted or unsubstituted alicyclic of C3-C20 and condensed ring-subunit of aromatic ring of C6-C30;

wherein the Ar is ₃ 、Ar ₄ 、Ar ₅ 、L ₃ 、L ₄ 、L ₅ At least one group of (C) is substituted with one or more Si (R ₄ ) ₃ Substitution;

the R is ₄ The same or different one selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

the R is ₃ One selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

The c ₁ Selected from 0, 1 or 2.

The beneficial effects are that: the hole transmission region of the organic electroluminescent device provided by the invention comprises the compound shown in the formula 1, and the electron transmission region comprises the compound shown in the formula 2, so that the hole transmission region and the electron transmission region have matched energy levels, good thermal stability and film forming property, are favorable for realizing charge balance in the device, promote the recombination efficiency of holes and electrons in a luminescent layer, improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device.

Detailed Description

The present invention is further illustrated below in conjunction with specific embodiments, it being understood that these embodiments are meant to be illustrative of the invention and not limiting the scope of the invention, and that modifications of the invention, which are all within the scope of the invention as claimed by those skilled in the art after reading the present invention.

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

The halogen in the invention comprises fluorine, chlorine, bromine and iodine.

In the present invention, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding selectable positions of the ring.

For example, the number of the cells to be processed,can indicate-> Can indicate-> Can indicate-> And so on.

In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to any of the two or more rings, in particular to any of the corresponding selectable sites of the rings. For example, e.g.Can indicate->And so on.

In the present invention, "adjacent two groups are bonded to form a ring" means that a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring is formed by bonding adjacent groups to each other and optionally aromatizing. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may include aliphatic or aromatic heterocycles. The aliphatic hydrocarbon ring may be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring may be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may be a single ring or a polycyclic group. As exemplified below:

in addition, a ring formed by bonding adjacent groups may be linked to another ring to form a spiro structure. As exemplified below:

in the present invention, the ring formed by the connection may be a three-membered ring, four-membered ring, five-membered ring, six-membered ring, seven-membered ring, eight-membered ring, condensed ring, spiro ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but is not limited thereto.

In the present invention, "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not substituted with a substituent. For example, "unsubstituted aryl" in "substituted or unsubstituted C6-C60 aryl" means that the hydrogen atom of the "aryl" is not replaced by a substituent. And so on.

In the present invention, "CXX to CYY" in the "substituted or unsubstituted CXX to CYY ZZ group" means the number of carbon atoms in the unsubstituted "ZZ group", and when the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C6 to C30" in the "substituted or unsubstituted C6 to C30 aryl" represents the number of carbon atoms in the unsubstituted "aryl", and when the "aryl" has a substituent, the number of carbon atoms in the substituent is not included. "C3 to C20" in the "fused ring group of a substituted or unsubstituted C3 to C20 alicyclic ring and a C6 to C30 aromatic ring" means the number of carbon atoms in the unsubstituted "alicyclic ring", and when the "alicyclic ring" has a substituent, the number of carbon atoms of the substituent is not included; "C6-C30" represents the number of carbon atoms in an unsubstituted "aromatic ring", and when the "aromatic ring" has a substituent, the number of carbon atoms in the substituent is not included. And so on.

"substituted" in "substituted or unsubstituted" as used herein means that at least one hydrogen atom on the group is replaced with a substituent. When a plurality of hydrogens are replaced with a plurality of substituents, the plurality of substituents may be the same or different. The position of the hydrogen substituted with the substituent may be any position. The substituents represented by "substitution" in the above "substituted or unsubstituted" include the following groups, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C15 alkoxy, substituted or unsubstituted C6 to C20 aryloxy, substituted or unsubstituted C2 to C15 heterocyclic group, substituted or unsubstituted C1 to C15 alkyl, substituted or unsubstituted C3 to C15 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heteroaryl, fused ring group of substituted or unsubstituted C3 to C15 alicyclic ring and C6 to C20 aromatic ring, fused ring group of substituted or unsubstituted C3 to C15 alicyclic ring and C2 to C20 heteroaromatic ring, and the like. The following groups are preferred: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphene, isobornyl, fenchyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, anthracenyl, pyrenyl, Radicals, fluoranthene radicals, benzocyclopropane radicals, benzoringsButyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl, fluorenyl, spirobifluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the like. Further, each of the above substituents may be substituted or unsubstituted. Two adjacent substituents may be bonded to form a ring.

The alkyl refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group may be a straight chain alkyl group or a branched chain alkyl group. When the number of carbon atoms of the chain alkyl group is three or more, the present invention includes isomers thereof, for example, propyl group includes n-propyl group and isopropyl group; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and the like. The number of carbon atoms of the alkyl group is from C1 to C20, preferably from C1 to C15, and more preferably from C1 to C10.

The silyl group according to the present invention means-Si (R _k ) ₃ A group wherein each R _k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring. Preferably, each R _k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The number of carbon atoms of the alkyl group is preferably C1 to C20, more preferably C1 to C15, still more preferably C1 to C10, and most preferably C1 to C8. The cycloalkyl groupThe number of carbon atoms of (C) is preferably from C3 to C20, more preferably from C3 to C15, still more preferably from C3 to C10, most preferably from C3 to C7. Preferably, each R _k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. Preferred substituted silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like.

The cycloalkyl refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloparaffin molecule. The cycloalkyl group includes monocyclic cycloalkyl, polycyclic cycloalkyl, bridged cycloalkyl. Examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphene, fenchyl, isobornyl, and the like. The cycloalkyl group has a carbon number of 3 to 20, preferably 3 to 15, more preferably 3 to 10.

The aryl refers to the generic term that monovalent groups remain after one hydrogen atom is removed from the aromatic nucleus carbon of an aromatic compound molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused ring aryl groups, or combinations thereof. Examples of the aryl group include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, triphenylenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, spiroanthracrenyl, pyrenyl, and the like,A radical, a fluoranthenyl radical, etc., but is not limited thereto. The number of carbon atoms of the aryl group is from C6 to C30, preferably from C6 to C25, and more preferably from C6 to C20.

Heteroaryl as used herein refers to a monovalent group in which at least one carbon atom of the aryl group is replaced with a heteroatom. The hetero atom is selected from O, S, N, si, B, P and the like, but is not limited thereto. Examples of heteroaryl groups include, but are not limited to, benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothienyl, naphthothienyl, phenanthrothienyl, dibenzothienyl, benzodibenzothienyl, indolyl, naphtalindolyl, carbazolyl, benzocarbazolyl, spirofluorenoxaanthracenyl, spirofluorenthiaanthracenyl, spirofluorenazaanthracenyl, spirofluorensilaanthracenyl, benzodioxanyl, benzodisulfide, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothienyl, dihydroisobenzothienyl, phenoxazinyl, phenothiazinyl, dihydroacridinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the like. The heteroaryl group may have a carbon number of from 2 to 30, preferably from 2 to 25, and more preferably from 3 to 20.

The arylene group refers to the general term that divalent groups remain after two hydrogen atoms are removed from the aromatic nucleus carbon of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a fused ring arylene group, or a combination thereof. Examples of the arylene group include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthylene fluorenylene, spirobifluorenylene, and the like, but are not limited thereto. The arylene group has a carbon number of from C6 to C30, preferably from C6 to C25, more preferably from C6 to C20, and still more preferably from C6 to C18.

Heteroaryl-ene as used herein refers to a divalent group in which at least one carbon atom of the arylene group is replaced with a heteroatom. The hetero atom is selected from O, S, N, si, B, P and the like, but is not limited thereto. The heteroarylene includes a monocyclic heteroarylene, a polycyclic heteroarylene, a fused ring heteroarylene, or a combination thereof. Examples of the heteroarylene group include, but are not limited to, a pyridyl group, a pyrimidylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, a quinazolinylene group, a naphthyridinyl group, and the like. The heteroarylene group has a carbon number of from 2 to 30, preferably from 2 to 25, and more preferably from 2 to 20.

The fused ring radical of the alicyclic ring and the aromatic ring refers to the general term that two hydrogen atoms are reduced after the alicyclic ring and the aromatic ring are fused together, and divalent groups are remained. The fused ring of the alicyclic ring and the aromatic ring includes, but is not limited to, indanylene, indenylene, tetrahydronaphthalylene, dihydronaphthalylene, benzocyclopropylene, benzocyclobutylene, benzocycloheptylene, benzocyclobutenyl, naphthocyclopentylene, and the like. The alicyclic ring has 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, and more preferably 3 to 8 carbon atoms. The number of carbon atoms of the aromatic ring is 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 10.

The term "at least one" in the present invention includes one, two, three, four, five or more, under the allowable conditions.

The term "one or more" in the present invention includes one, two, three, four, five, six, seven, eight, nine, ten or more, where permitted.

In the organic electroluminescent device according to the present invention, each functional layer may be formed of a single layer or two or more thin films, and each thin film may be formed of one material or two or more materials, however, the structure of the organic electroluminescent device is not limited thereto.

The material of each layer of thin film in the organic electroluminescent device is not particularly limited, and materials known in the art can be used.

The invention provides an organic electroluminescent device, which comprises an anode, an organic layer and a cathode, wherein the organic layer is arranged between the anode and the cathode, the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, the hole transmission region is arranged between the anode and the luminescent layer, the electron transmission region is arranged between the luminescent layer and the cathode, the hole transmission region contains a compound shown in a formula 1, and the electron transmission region contains a compound shown in a formula 2.

Hereinafter, the structure of an organic electroluminescent device including the compound of formula 1 as a hole transport region material and the compound of formula 2 as an electron transport region material will be described in more detail.

The anode according to the present invention is preferably a material having a high work function so that holes smoothly enter the organic layer. Conductive metal oxide films, semitransparent metal thin films, and the like are often used, but are not limited thereto. Specific examples of the anode material may include gold (Au), platinum (Pt), aluminum (Al), magnesium-silver (Mg-Ag), indium Zinc Oxide (IZO), indium Tin Oxide (ITO), zinc oxide (ZnO), tin dioxide (SnO) ₂ ) Indium tin oxide/silver/indium tin oxide (ITO/Ag/ITO), polyaniline, and the like, but is not limited thereto.

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

Preferably, the hole transport region according to the present invention includes a hole injection layer, a hole transport layer, and an electron blocking layer;

preferably, the hole transport region according to the present invention includes a hole injection layer and a hole transport layer;

preferably, the hole transport region according to the present invention includes a hole injection layer and an electron blocking layer;

preferably, the hole transport region according to the present invention includes a hole transport layer and an electron blocking layer;

preferably, the hole transport region according to the present invention includes a hole injection layer;

preferably, the hole transport region according to the present invention includes an electron blocking layer;

preferably, the hole transport region according to the present invention includes a hole transport layer;

preferably, the hole transport region according to the present invention includes at least one of a first hole transport layer, a second hole transport layer, and a third hole transport layer;

preferably, the hole transport layer of the present invention is located between the anode and the light emitting layer;

Preferably, the hole transport layer of the present invention is located between the hole injection layer and the light emitting layer.

The hole transport region according to the present invention contains a compound represented by formula 1,

Said Z is selected from O, S, CR _a R _b Or NR (NR) _c ；

The R is _a 、R _b The same or different aryl groups selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, and substituted or unsubstituted C6-C30 arylOne of the radicals, substituted or unsubstituted C3-C20-alicyclic and C6-C30-aromatic condensed ring radicals, or adjacent R _a 、R _b Bonded to each other to form a substituted or unsubstituted ring;

preferably, the Ar ₁ One or a combination of the following groups,

the R is ₅ The same or different one or combination of condensed ring groups selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ringOr adjacent two R ₅ Bonded to each other to form a substituted or unsubstituted ring;

the R is _d The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl and substituted or unsubstituted C6-C30 aryl;

the m is ₁ Selected from 0, 1, 2, 3, 4 or 5; the m is ₂ Selected from 0, 1, 2, 3 or 4; the m is ₃ Selected from 0, 1, 2 or 3; the m is ₄ Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m is ₅ Selected from 0, 1, 2, 3, 4, 5 or 6; the m is ₆ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m is ₇ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

the r is ₁ Selected from 0, 1 or 2; the r is ₂ Selected from 0, 1, 2, 3 or 4; the r is ₃ Selected from 0, 1, 2, 3, 4, 5 or 6; the r is ₄ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

Preferably, said R ₅ The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptyl, or two adjacent R ₅ Are bonded to each other to form a substituted or unsubstituted benzene ring.

Preferably, said R _d The same or different radicals selected from hydrogen, deuterium, tritium, cyano, halogen, or substituted by one or more deuterium, C1-C6 alkyl radicalsUnsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptyl.

Preferably, the saidSelected from one of the groups shown below,

said b ₁ Selected from 0, 1, 2, 3 or 4; said b ₂ Selected from 0, 1, 2 or 3; said b ₃ Selected from 0, 1, 2, 3, 4, 5 or 6; said b ₄ Selected from 0, 1, 2, 3, 4 or 5; said b ₅ Selected from 0, 1, 2, 3, 4, 5, 6 or 7.

Preferably, said R ₂ The same or different are selected from hydrogen, deuterium, tritium, cyanogenA group, halogen, or any of the following substituted or unsubstituted with one or more deuterium, C1 to C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptyl.

Preferably, the L ₀ 、L ₁ 、L ₂ Independently selected from a single bond or one or a combination of the groups shown below,

The R is ₆ The same or different is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or adjacent two R ₆ Bonded to each other to form a substituted or unsubstituted ring;

said n ₁ Selected from 0, 1, 2, 3 or 4; said n ₂ Selected from 0, 1, 2, 3, 4, 5 or 6; said n ₃ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said n ₄ Selected from 0, 1, 2, 3, 4 or 5; said n ₅ Selected from 0, 1 or 2.

Preferably, said R ₆ The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-Butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentyl, benzocyclohexenyl, benzocyclopentenyl or benzocyclohexenyl.

Preferably, the formula 1 is selected from any one of the compounds shown below,

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the hole transport region of the present invention is exemplified above as containing some specific chemical structures of the compound of formula 1, but the present invention is not limited to these chemical structures listed, and substituents are included as defined above, whenever the structure shown in formula 1 is used as a basis.

The hole injection layer is preferably a material with good hole injection capability. The hole injection material includes, but is not limited to, silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, and other metal oxides, phthalocyanine compounds, biphenylamine compounds, phenazine compounds, and other materials. Specific examples of the hole injection material may include copper phthalocyanine (CuPc), N '-bis [ 4-di (m-tolyl) aminophenyl ] -N, N' -diphenyl benzidine (DNTPD), 4',4 "-tris (N- (1-naphthyl) -N-phenylamino) triphenylamine (1-TNATA), 4' -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), and the like, but are not limited thereto. Preferred are compounds of formula 1 according to the invention.

The hole transport layer of the present invention is preferably a material having good hole transport properties. The hole transport material includes, but is not limited to, carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, and the like. Specific examples of the hole transport material may include, but are not limited to, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N4' -bis (biphenyl-4-yl) -N4, N4' -diphenyl biphenyl-4, 4' -diamine (TPD-10), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 1,3, 5-tris (9-carbazolyl) benzene (TCB), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), polyvinylcarbazole (PVC), and the like. Preferred are compounds of formula 1 according to the invention.

The electron blocking layer is preferably a material with better hole transmission capability and electron blocking capability. The electron blocking material includes, but is not limited to, an aromatic amine derivative, a carbazole derivative, and the like. Specific examples of the electron blocking material may include N, N '-bis (naphthalen-1-yl) -N, N' -diphenyl-benzidine (NPD), N-bis ([ 1,1 '-biphenyl ] -4-) - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-amine, and the like, but are not limited thereto. Preferred are compounds of formula 1 according to the invention.

Preferably, at least one of the hole injection layer, the hole transport layer, and the electron blocking layer contains the compound of formula 1.

Preferably, the hole injection layer contains a compound of formula 1.

Preferably, the hole transport layer contains a compound of formula 1.

Preferably, the electron blocking layer comprises a compound of formula 1.

The light-emitting layer comprises a host material and a doping material. The light-emitting layer can be a single light-emitting layer or can be a composite light-emitting layer which is transversely or longitudinally overlapped. The doping ratio of the host material and the doping material may be determined according to the material used, and the doping ratio of the doping material is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%. The host material of the light emitting layer needs to have bipolar charge transport properties and also needs to have an appropriate energy level to efficiently transfer excitation energy to the guest light emitting material. The host material includes, but is not limited to, heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, and the like. Specific examples may include 4,4' -bis (carbazol-9-yl) biphenyl (CBP), 1, 3-bis (N-carbazolyl) benzene (MCP), 1,3, 5-tris (carbazol-9-yl) benzene (TCP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), tris (8-hydroxyquinoline) aluminum (Alq ₃ ) Etc., but is not limited thereto. The doping material can be a red light emitting material, a green light emitting material and a blue light emitting material. The dopant includes, but is not limited to, heavy metal complexes, phosphorescent rare earth metal complexes, and the like. Specific examples may include tris (2-phenylpyridine) iridium (Ir (ppy) ₃ ) Ir (ppy) iridium bis (2-phenylpyridine) (acetylacetonate) ₂ (acac)), bis (1-phenyl-isoquinoline) (acetylacetonate) iridium (Ir (piq) ₂ (acac)), tris (1-benzeneIr (piq) iridium (base-isoquinoline) ₃ ) And 2,5,8, 11-tetra-t-butylperylene (TBPe), etc., but are not limited thereto.

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

Preferably, the electron transport region according to the present invention includes an electron injection layer, an electron transport layer, and a hole blocking layer;

preferably, the electron transport region according to the present invention includes an electron injection layer and an electron transport layer;

preferably, the electron transport region of the present invention includes an electron injection layer and a hole blocking layer;

preferably, the electron transport region according to the present invention includes an electron transport layer and a hole blocking layer;

preferably, the electron transport region according to the present invention includes an electron injection layer;

Preferably, the electron transport region according to the present invention includes an electron transport layer;

preferably, the electron transport region according to the present invention includes a hole blocking layer.

The electron transport region according to the present invention contains a compound represented by formula 2,

the L is ₃ 、L ₄ 、L ₅ Independently selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroaryleneAryl, one or a combination of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring sub-condensed ring radicals;

the c ₁ Selected from 0, 1 or 2.

Preferably, x is the same or different and is selected from CH or N, and at least one is selected from N, meaning that one, two or three of the x are selected from N atoms.

Preferably, said R ₃ Any one selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, naphthyridine.

Preferably, the Ar ₃ 、Ar ₄ 、Ar ₅ One or a combination of the following groups,

the v is the same or different and is selected from CR ₇ Or N, when v is bonded to the other group, said v is selected from a C atom;

said W, X being identical or different and being selected from O, S, CR _h R _i Or NR (NR) _j One of the following;

y is selected from CH or N;

the R is ₇ One or a combination of condensed ring groups selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent two R ₇ Bonded to each other to form a substituted or unsubstituted ring;

the R is _h 、R _i The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and condensed ring group of C6-C30 aromatic ring, or adjacent R _h 、R _i Bonded to each other to form a substituted or unsubstituted ring;

the R is _j One selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring.

the R is ₇ The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following;

the R is _e The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following;

the R is _h 、R _i The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following;

the R is _h 、R _i Can be bonded to each other to form one of the groups shown below,

the R is _k The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinylOne of the bases;

the R is _j Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following;

the R is ₇ 、R _e 、R _h 、R _i 、R _j May be substituted with one or more substituents which may be the same or different selected from deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following; when two or more substituents are present, the two or more substituents may be the same or different from each other;

the i is ₁ Selected from 0, 1, 2, 3 or 4; the i is ₂ Selected from 0, 1, 2. 3, 4, 5 or 6; the i is ₃ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the i is ₄ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the i is ₅ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the i is ₆ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; the i is ₇ Selected from 0, 1, 2, 3, 4 or 5;

the p is ₁ Selected from 0, 1, 2, 3, 4 or 5; the p is ₂ Selected from 0, 1, 2, 3 or 4; the p is ₃ Selected from 0, 1, 2 or 3; the p is ₄ Selected from 0, 1, 2, 3, 4, 5, 6 or 7; p is p ₅ Selected from 0, 1, 2, 3, 4, 5 or 6; p is p ₆ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the p is ₇ Selected from 0, 1 or 2; the p is ₈ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the p is ₉ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the p is ₁₀ Selected from 0 or 1;

the q is ₁ Selected from 0, 1 or 2; the q is ₂ Selected from 0, 1, 2, 3 or 4; the q is ₃ Selected from 0, 1, 2, 3, 4, 5 or 6; the q is ₄ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

Preferably, the L ₃ 、L ₄ 、L ₅ Independently selected from a single bond or one or a combination of the groups shown below,

the R is _f The same or different is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, two R _f Bonded to each other to form a substituted or unsubstituted ring;

the R is _g The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

the t is ₁ Selected from 0, 1, 2, 3 or 4; the t is ₂ Selected from 0, 1, 2, 3, 4, 5 or 6; the t is ₃ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t is ₄ Selected from 0, 1, 2 or 3; the t is ₅ Selected from 0, 1 or 2; the t is ₆ Selected from 0 or 1; the t is ₇ Selected from 0, 1, 2, 3, 4 or 5; the t is ₈ Selected from 0, 1, 2, 3, 4, 5, 6 or 7;

the s is ₁ Selected from 0, 1 or 2; the s is ₂ Selected from 0, 1, 2, 3 or 4; the s is ₃ Selected from 0, 1, 2, 3, 4, 5 or 6; the s is ₄ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the s is ₅ Selected from 0 or 1.

Preferably, said R _f The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, si (R) ₄ ) ₃ Or any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, benzocyclopentyl, benzocyclohexenyl, benzocycloheptyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, or benzothienyl.

Preferably, said R _g The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantylNorbornyl, phenyl, biphenyl, terphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuranyl, or benzothienyl.

Preferably, the Ar ₃ 、Ar ₄ 、Ar ₅ 、L ₃ 、L ₄ 、L ₅ At least one group of (C) is substituted with one or more Si (R ₄ ) ₃ Substitution, comprising: ar (Ar) ₃ -Ar ₅ 、L ₃ -L ₅ Is bonded to one or more Si (R ₄ ) ₃ Substituted, particularly Ar ₃ 、Ar ₄ 、Ar ₅ 、L ₃ 、L ₄ Or L ₅ Is formed by one or more Si (R ₄ ) ₃ Substitution; ar (Ar) ₃ -Ar ₅ 、L ₃ -L ₅ Each of the two groups in (2) is substituted with one or more Si (R ₄ ) ₃ Substituted, particularly Ar ₃ And Ar is a group ₄ 、Ar ₃ And Ar is a group ₅ 、Ar ₄ And Ar is a group ₅ 、L ₃ And L ₄ 、L ₃ And L ₅ 、L ₄ And L ₅ 、Ar ₃ And L ₃ 、Ar ₄ And L ₄ 、Ar ₅ And L ₅ 、Ar ₃ And L ₄ 、Ar ₃ And L ₅ 、Ar ₄ And L ₃ 、Ar ₄ And L ₅ 、Ar ₅ And L ₃ 、Ar ₅ And L ₄ Each group of (C) is substituted with one or more Si (R ₄ ) ₃ Substitution; ar (Ar) ₃ -Ar ₅ 、L ₃ -L ₅ Each of the three groups in (a) is substituted with one or more Si (R) ₄ ) ₃ Substituted, particularly Ar ₃ 、Ar ₄ And Ar is a group ₅ ，L ₃ 、L ₄ And L ₅ ，Ar ₃ 、Ar ₄ And L ₃ ，Ar ₃ 、Ar ₄ And L ₄ ，Ar ₃ 、Ar ₄ And L ₅ ，Ar ₃ 、Ar ₅ And L ₃ ，Ar ₃ 、Ar ₅ And L ₄ ，Ar ₃ 、Ar ₅ And L ₅ ，Ar ₅ 、Ar ₄ And L ₃ ，Ar ₅ 、Ar ₄ And L ₄ ，Ar ₅ 、Ar ₄ And L ₅ ，L ₃ 、L ₄ And Ar is a group ₃ ，L ₃ 、L ₄ And Ar is a group ₄ ，L ₃ 、L ₄ And Ar is a group ₅ ，L ₃ 、L ₅ And Ar is a group ₃ ，L ₃ 、L ₅ And Ar is a group ₄ ，L ₃ 、L ₅ And Ar is a group ₅ ，L ₄ 、L ₅ And Ar is a group ₃ ，L ₄ 、L ₅ And Ar is a group ₄ ，L ₄ 、L ₅ And Ar is a group ₅ Each group of (C) is substituted with one or more Si (R ₄ ) ₃ Substitution; ar (Ar) ₃ -Ar ₅ 、L ₃ -L ₅ Each of the four groups in (2) is substituted with one or more Si (R) ₄ ) ₃ Substituted, particularly Ar ₃ 、Ar ₄ 、Ar ₅ And L ₃ ，Ar ₃ 、Ar ₄ 、Ar ₅ And L ₄ ，Ar ₃ 、Ar ₄ 、Ar ₅ And L ₅ ，L ₃ 、L ₄ 、L ₅ And Ar is a group ₃ ，L ₃ 、L ₄ 、L ₅ And Ar is a group ₄ ，L ₃ 、L ₄ 、L ₅ And Ar is a group ₅ ，Ar ₃ 、Ar ₄ 、L ₄ And L ₃ ，Ar ₃ 、Ar ₅ 、L ₅ And L ₃ ，Ar ₅ 、Ar ₄ 、L ₄ And L ₅ Each group of (C) is substituted with one or more Si (R ₄ ) ₃ Substitution; ar (Ar) ₃ -Ar ₅ 、L ₃ -L ₅ Is substituted with one or more Si (R ₃ ) ₃ Substituted, particularly Ar ₃ 、Ar ₄ 、L ₄ 、L ₃ And L ₅ ，Ar ₃ 、Ar ₄ 、L ₄ 、L ₃ And Ar is a group ₅ ，Ar ₃ 、Ar ₅ 、L ₅ 、L ₃ And L ₄ ，Ar ₃ 、Ar ₅ 、L ₅ 、L ₃ And Ar is a group ₄ ，Ar ₄ 、Ar ₅ 、L ₅ 、L ₄ And L ₃ ，Ar ₄ 、Ar ₅ 、L ₅ 、L ₄ And Ar is a group ₃ Each group of (C) is substituted with one or more Si (R ₄ ) ₃ Substitution; ar (Ar) ₃ -Ar ₅ 、L ₃ -L ₅ Is composed of one or more Si (R ₄ ) ₃ Substituted, particularly Ar ₃ 、Ar ₄ 、Ar ₅ 、L ₃ 、L ₄ And L ₅ Each group of (C) is substituted with one or more Si (R ₄ ) ₃ And (3) substitution.

Preferably, the compound of formula 2 contains one, two, three, four or more Si (R) ₄ ) ₃ 。

Preferably Ar ₃ Comprising one, two, three or more Si (R ₄ ) ₃ 。

Preferably Ar ₄ Comprising one, two, three or more Si (R ₄ ) ₃ 。

Preferably Ar ₅ Comprising one, two, three or more Si (R ₄ ) ₃ 。

Preferably Ar ₃ 、Ar ₄ 、Ar ₅ Together comprising one, two, three, four or more Si (R ₄ ) ₃ 。

Preferably, the Si (R ₄ ) ₃ Selected from one of the groups shown below,

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

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the electron transport region of the present invention has been exemplified above as containing some specific chemical structures of the compound of formula 2, but the present invention is not limited to these chemical structures listed, and substituents are included as defined above, whenever the structure shown in formula 2 is used as a basis.

The hole blocking layer is preferably a material with better electron transmission capability and hole blocking capability. The hole blocking material includes, but is not limited to, a metal complex, a heteroaromatic compound, and the like. Specific examples may include bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), and the like, but are not limited thereto. Preferred are compounds of formula 2 according to the present invention.

The electron transport layer is preferably a material with better stability and higher electron mobility. The electron transport material includes, but is not limited to, aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, high molecular compounds, and the like. Specific examples may include aluminum 8-hydroxyquinoline (Alq ₃ ) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq ₂ ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 2- (4-biphenyl) -5-phenyloxadi-NOxazole (PBD), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4' -bis (4, 6-diphenyl-1, 3, 5-triazin-2-yl) biphenyl (BTB), and the like, but are not limited thereto. Preferred are compounds of formula 2 according to the present invention.

The electron injection layer according to the present invention is preferably a material having a small potential difference from a potential barrier of an adjacent organic transport material, host material, or the like, and has an effect of injecting electrons from the cathode. The electron injection layer material includes a metal, a metal compound, a metal oxide, and the like, but is not limited thereto. Specific examples may include ytterbium (Yb), lithium fluoride (LiF), magnesium fluoride (MgF) ₂ ) Lithium 8-hydroxyquinoline (LiQ), cesium carbonate (Cs) ₂ CO ₃ ) Rubidium acetate (CH) ₃ COORb), etc., but is not limited thereto. Preferred are compounds of formula 2 according to the present invention.

Preferably, at least one of the electron injection layer, the electron transport layer, and the hole blocking layer contains the compound of formula 2.

Preferably, the electron injection layer contains a compound of formula 2.

Preferably, the electron transport layer comprises a compound of formula 2.

Preferably, the hole blocking layer comprises a compound of formula 2.

The cathode according to the invention is preferably a material having a relatively low work function. The cathode material includes, but is not limited to, a metal alloy, and the like. Specific examples of the cathode material may include aluminum (Al), silver (Ag), gold (Au), lithium (Li), magnesium (Mg), magnesium silver alloy (Mg: ag), lithium aluminum alloy (Li: al), and the like, but are not limited thereto.

The cover material of the present invention has the effect of coupling out light trapped within the device. The capping layer material includes an aromatic amine derivative, a metal compound, a carbazole derivative, and the like, but is not limited thereto. Specific examples may include tris (8-hydroxyquinoline) aluminum (Alq ₃ ) 4,4' -bis (carbazol-9-yl) biphenyl (CBP), and the like, but is not limited thereto.

The organic electroluminescent device according to the present invention may further include a substrate, and the substrate according to the present invention preferably uses a material that does not change when forming electrodes and other functional layers, and specific examples of the substrate material that can be used in the present invention may include glass, quartz, plastic, polymer film, silicon, etc., but are not limited thereto. The substrate may remain in a light emitting device or an electronic apparatus using the organic electroluminescent device of the present invention, or may serve as a support only in a manufacturing process of the organic electroluminescent device without remaining in a final product.

However, the structure of the organic electroluminescent device according to the present invention 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 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 light-emitting type of the organic electroluminescent device can be a top-emitting device or a bottom-emitting device, and the difference between the two is that the light-emitting direction of the device is the direction of emitting light through the substrate or deviating from the substrate. For a bottom emission device, the light emitting direction of the device is through the substrate emission; for top-emitting devices, the light exiting direction of the device is the direction away from the substrate.

The method for producing the thin films of each layer in the organic electroluminescent device of the present invention is not particularly limited, and vacuum deposition, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

The organic electroluminescent device is mainly applied to the technical field of information display, the lighting field and the plane light source field, and is widely applied to various information displays in the aspect of information display, such as mobile phones, tablet computers, flat televisions, intelligent watches, VR, vehicle-mounted systems, digital cameras, wearable devices 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.

Synthetic examples

Raw materials and reagents: the starting materials or reagents used in the following synthetic examples are not particularly limited and may be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and the reagents used in the invention are all reagent pure.

Instrument: g2—si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk); vario EL cube organic element analyzer (Elementar, germany).

The method for producing the compounds represented by the formulas 1 and 2 of the present invention is not particularly limited, and conventional methods known to those skilled in the art can be employed. For example, the compounds represented by the formulas 1 and 2 of the present invention can be prepared by the synthetic routes shown below.

The synthetic route of formula 1:

The synthetic route of formula 2:

the Xn is halogen, for example, xn is the same or different and is selected from Cl, br and I.

The Ar is as follows ₁ 、Ar ₃ ～Ar ₅ 、L ₀ 、L ₁ ～L ₅ 、R ₁ 、R ₂ 、R ₃ 、x、a ₁ 、b ₁ 、b ₂ 、c ₁ The limitations are the same as those described above.

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.

Synthesis example 1: preparation of Compounds 1-60

Synthesis of intermediate A-1-60: a-1-60 (14.27 g,50.00 mmol), c-1-60 (19.87 g,50.00 mmol), sodium t-butoxide (9.61 g,100.00 mmol), toluene (500 ml), palladium acetate (0.11 g,0.50 mmol), tri-t-butylphosphine (0.10 g,0.50 mmol) were added to the flask under nitrogen protection, and reacted under reflux for 7.5 hours. After the reaction was completed, cooled to room temperature, water was added, extraction was performed with methylene chloride, the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purification was performed by silica gel column chromatography (methylene chloride: n-hexane=1:5) to give intermediate a-1-60 (23.77 g, yield 79%); the HPLC purity is more than or equal to 99.84 percent. Mass spectrum m/z:601.2780 (theory: 601.2770).

Synthesis of Compounds 1-60: a-1-60 (18.05 g,30.00 mmol), b-1-60 (9.70 g,30.00 mmol), sodium t-butoxide (5.77 g,60.00 mmol), toluene (300 ml), dibenzylideneacetone dipalladium (0.55 g,0.60 mmol), and tri-t-butylphosphine (0.12 g,0.60 mmol) were added to the flask under nitrogen, and reacted under reflux for 9 hours. After the reaction was completed, cooled to room temperature, water was added, extraction was performed with methylene chloride, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to give compounds 1 to 60 (19.24 g, yield 76%); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:843.3513 (theory: 843.3501). Theoretical element content (%) C ₆₄ H ₄₅ NO: c,91.07; h,5.37; n,1.66. Measured element content (%): c,91.10; h,5.41; n,1.61.

Synthesis example 2: preparation of Compounds 1-82

According to the same manner as that of Compound 1-60 in Synthesis example 1, a-1-60, c-1-60, b-1-60 were replaced with equimolar amounts of a-1-82, c-1-82, b-1-82, respectively, to give the Compound1-82 (19.80 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:891.3517 (theory: 891.3501). Theoretical element content (%) C ₆₈ H ₄₅ NO: c,91.55; h,5.08; n,1.57. Measured element content (%): c,91.53; h,5.12; n,1.54.

Synthesis example 3: preparation of Compounds 1-92

Synthesis of intermediate c-1-92: d-1-92 (26.82 g,80.00 mmol), e-1-92 (12.51 g,80.00 mmol), na under nitrogen ₂ CO ₃ (16.96 g,160.00 mmol) was added to 600ml tetrahydrofuran and 150ml distilled water, pd (PPh) was added with stirring ₃ ) ₄ (0.92 g,0.80 mmol) and the mixture of the above reactants was heated under reflux for 4h. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by reduced pressure distillation, cooling for crystallization, suction filtering, and recrystallizing the obtained solid with toluene to obtain an intermediate c-1-92 (22.89 g, 78%), wherein the HPLC purity is not less than 99.80%. Mass spectrum m/z:366.1166 (theory: 366.1175).

Synthesis of Compounds 1-92: according to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar a-1-82, c-1-92, b-1-82, respectively, to give compound 1-92 (18.68 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:829.3330 (theory: 829.3345). Theoretical element content (%) C ₆₃ H ₄₃ NO: c,91.16; h,5.22; n,1.69. Measured element content (%): c,91.20; h,5.19; n,1.71.

Synthesis example 4: preparation of Compounds 1-107

According to the same manner as that for preparing Compound 1-60 in Synthesis example 1, a-1-60, c-1-60 and b-1-60 are replaced with equimolar ones, respectivelyA-1-107, c-1-107, b-1-107 to give compound 1-107 (16.85 g); HPLC purity is more than or equal to 99.98%. Mass spectrum m/z:779.4118 (theory: 779.4127). Theoretical element content (%) C ₅₈ H ₅₃ NO: c,89.30; h,6.85; n,1.80. Measured element content (%): c,89.26; h,6.89; n,1.78.

Synthesis example 5: preparation of Compounds 1-112

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar a-1-112, c-1-112, b-1-112, respectively, to give compound 1-112 (16.63 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:791.3168 (theory: 791.3188). Theoretical element content (%) C ₆₀ H ₄₁ NO: c,90.99; h,5.22; n,1.77. Measured element content (%): c,90.97; h,5.19; n,1.82.

Synthesis example 6: preparation of Compounds 1-115

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar amounts of a-1-115, c-1-115, b-1-115, respectively, to give compound 1-115 (17.08 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:801.3043 (theory: 801.3032). Theoretical element content (%) C ₆₁ H ₃₉ NO: c,91.36; h,4.90; n,1.75. Measured element content (%): c,91.40; h,4.88; n,1.72.

Synthesis example 7: preparation of Compounds 1-242

According to the same manner as that for preparing compound 1-60 in synthetic example 1, a-1-60, b-1-60 are replaced respectivelyEquimolar amounts of a-1-242 and b-1-242, to give compound 1-242 (17.62 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:733.3723 (theory: 733.3709). Theoretical element content (%) C ₅₆ H ₄₇ N: c,91.64; h,6.45; n,1.91. Measured element content (%): c,91.68; h,6.42; n,1.89.

Synthesis example 8: preparation of Compounds 1-247

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, b-1-60 are replaced with equimolar a-1-247, b-1-247, respectively, to give compound 1-247 (16.85 g); the HPLC purity is more than or equal to 99.97 percent. Mass spectrum m/z:684.3512 (theory: 684.3522). Theoretical element content (%) C ₅₂ H ₃₂ D ₇ N: c,91.19; h,6.77; n,2.05. Measured element content (%): c,91.22; h,6.75; n,2.08.

Synthesis example 9: preparation of Compounds 1-281

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, b-1-60 are replaced with equimolar amounts of a-1-281, b-1-281, respectively, to give compound 1-281 (17.25 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:727.3224 (theory: 727.3239). Theoretical element content (%) C ₅₆ H ₄₁ N: c,92.40; h,5.68; n,1.92. Measured element content (%): c,92.37; h,5.70; n,1.95.

Synthesis example 10: preparation of Compounds 1-302

According to the same manner as that for preparing compound 1-60 in Synthesis example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar a-1, respectively-302, c-1-302, b-1-302, giving compound 1-302 (17.51 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:767.3560 (theory: 767.3552). Theoretical element content (%) C ₅₉ H ₄₅ N: c,92.27; h,5.91; n,1.82. Measured element content (%): c,92.31; h,5.89; n,1.78.

Synthesis example 11: preparation of Compounds 1-309

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, b-1-60 are replaced with equimolar amounts of a-1-309, b-1-302, respectively, to give compound 1-309 (17.57 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:731.3565 (theory: 731.3552). Theoretical element content (%) C ₅₆ H ₄₅ N: c,91.89; h,6.20; n,1.91. Measured element content (%): c,91.91; h,6.16; n,1.89.

Synthesis example 12: preparation of Compounds 1-318

Following the same procedure as for the preparation of compound 1-60 in Synthesis example 1, a-1-60, c-1-60 and b-1-60 were replaced with equimolar amounts of a-1-318, c-1-318 and b-1-242, respectively, to compound 1-318 (19.18 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:829.3726 (theory: 829.3709). Theoretical element content (%) C ₆₄ H ₄₇ N: c,92.61; h,5.71; n,1.69. Measured element content (%): c,92.57; h,5.68; n,1.74.

Synthesis example 13: preparation of Compounds 1-329

According to the same manner as that for preparing compound 1-60 in Synthesis example 1, a-1-60 and b-1-60 are replaced with equimolar a-1-329 and b-1-3, respectively29, to give compounds 1-329 (17.25 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:727.3221 (theory: 727.3239). Theoretical element content (%) C ₅₆ H ₄₁ N: c,92.40; h,5.68; n,1.92. Measured element content (%): c,92.44; h,5.65; n,1.89.

Synthesis example 14: preparation of Compounds 1-383

Synthesis of intermediate c-1-383: according to the method for producing intermediate c-1-60 in Synthesis example 3, d-1-92, e-1-92 were replaced with equimolar amounts of c-1-60, e-1-383, respectively, to give intermediate c-1-383 (26.33 g); the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z:432.1591 (theory: 432.1583).

Synthesis of Compounds 1-383: according to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 were replaced with equimolar amounts of a-1-383, c-1-383, b-1-383, respectively, to give compound 1-383 (19.52 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:890.4513 (theory: 890.4524). Theoretical element content (%) C ₆₈ H ₃₄ D ₁₃ N: c,91.64; h,6.78; n,1.57. Measured element content (%): c,91.61; h,6.80; n,1.60.

Synthesis example 15: preparation of Compounds 1-385

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar amounts of a-1-281, c-1-385, b-1-385, respectively, to give compound 1-385 (19.49 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:877.3719 (theory: 877.3709). Theoretical element content (%) C ₆₈ H ₄₇ N: c,93.01; h,5.40; n,1.60. Measured element content (%): c,93.05; h,5.36; n,1.58.

Synthesis example 16: preparation of Compounds 1-458

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60 and b-1-60 are replaced with equimolar a-1-458 and b-1-458, respectively, to give compound 1-458 (19.15 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:839.3535 (theory: 839.3552). Theoretical element content (%) C ₆₅ H ₄₅ N: c,92.93; h,5.40; n,1.67. Measured element content (%): c,92.89; h,5.38; n,1.72.

Synthesis example 17: preparation of Compounds 1-492

According to the same manner as that for preparing compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar amounts of a-1-492, c-1-492, b-1-492 to compound 1-492 (19.08 g), respectively; HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:882.4970 (theory: 882.4961). Theoretical element content (%) C ₆₇ H ₅₄ D ₅ N: c,91.11; h,7.30; n,1.59. Measured element content (%): c,91.09; h,7.27; n,1.63.

Synthesis example 18: preparation of Compounds 1-493

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar amounts of a-1-493, c-1-493, b-1-493, respectively, to give compound 1-493 (19.34 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:961.4480 (theory: 961.4493). Theoretical element content (%) C ₇₄ H ₃₉ D ₁₀ N: c,92.37; h,6.18; n,1.46. Measured element content (%): c,92.40; h,6.20; n,1.42.

Synthesis example 19: preparation of Compounds 1-502

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, b-1-60 are replaced with equimolar a-1-502, b-1-302, respectively, to give compound 1-502 (17.78 g); HPLC purity is more than or equal to 99.98%. Mass spectrum m/z:749.3490 (theory: 749.3478). Theoretical element content (%) C ₅₅ H ₄₇ NSi: c,88.07; h,6.32; n,1.87. Measured element content (%): c,88.10; h,6.27; n,1.83.

Synthesis example 20: preparation of Compounds 1-511

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar amounts of a-1-511, c-1-511, b-1-511, respectively, to give compound 1-511 (18.66 g); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:875.3931 (theory: 875.3947). Theoretical element content (%) C ₆₅ H ₅₃ NSi: c,89.10; h,6.10; n,1.60. Measured element content (%): c,89.13; h,6.08; n,1.57.

Synthesis example 21: preparation of Compounds 1-535

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 were replaced with equimolar amounts of a-1-535, c-1-535, b-1-535, respectively, to give compound 1-535 (19.19 g); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:875.4437 (theory: 875.4429). Theoretical element content (%) C ₆₇ H ₄₉ D ₄ N: c,91.84; h,6.56; n,1.60. Measured element content (%): c,91.88; h,6.54; n,1.57.

Synthesis example 22: preparation of Compounds 1-537

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, b-1-60 are replaced with equimolar a-1-247, b-1-537, respectively, to give compound 1-537 (18.68 g); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:829.3722 (theory: 829.3709). Theoretical element content (%) C ₆₄ H ₄₇ N: c,92.61; h,5.71; n,1.69. Measured element content (%): c,92.65; h,5.68; n,1.71.

Synthesis example 23: preparation of Compounds 1-540

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar a-1-540, c-1-540, b-1-540, respectively, to give compound 1-540 (19.96 g); HPLC purity is more than or equal to 99.94%. Mass spectrum m/z:977.4407 (theory: 977.4417). Theoretical element content (%) C ₇₃ H ₅₉ NSi: c,89.62; h,6.08; n,1.43. Measured element content (%): c,89.58; h,6.11; n,1.46.

Synthesis example 24: preparation of Compounds 1-591

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar amounts of a-1-281, c-1-591, b-1-591 to compound 1-591 (18.34 g), respectively; HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:825.4351 (theory: 825.4335). Theoretical element content (%) C ₆₃ H ₅₅ N: c,91.59; h,6.71; n,1.70. Measured element content (%): c,91.63; h,6.56; n,1.67.

Synthesis example 25: preparation of Compounds 1-642

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar a-1-642, c-1-642, b-1-642, respectively, to give compound 1-642 (18.24 g); HPLC purity is more than or equal to 99.96%. Mass spectrum m/z:855.3846 (theory: 855.3865). Theoretical element content (%) C ₆₆ H ₄₉ N: c,92.59; h,5.77; n,1.64. Measured element content (%): c,92.61; h,5.74; n,1.68.

Synthesis example 26: preparation of Compounds 1-700

According to the same production method as that of compound 1-60 in synthetic example 1, a-1-60, c-1-60, b-1-60 are replaced with equimolar a-1-700, c-1-92, b-1-700, respectively, to give compound 1-700 (18.00 g); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:856.3825 (theory: 856.3817). Theoretical element content (%) C ₆₅ H ₄₈ N ₂ : c,91.09; h,5.64; n,3.27. Measured element content (%): c,91.05; h,5.67; n,3.29.

Synthesis example 27: preparation of intermediate B-2-251

Step 1: 50mL of anhydrous tetrahydrofuran solvent was added to magnesium turnings (2.02 g,84.00 mmol) under nitrogen protection, then three pieces of iodine were added, and b-2-251 (18.34 g,80.00 mmol) of tetrahydrofuran solution (100 mL) was slowly added dropwise to initiate a format reaction, after the dropwise addition was completed, the reaction was carried out at room temperature for 7 hours, and after the reaction was completed, the mixture was cooled to room temperature.

Step 2: under the protection of nitrogen, a-2-251 (14.75 g,80.00 mmol) is added into a reaction bottle, then 200mL of tetrahydrofuran solvent is added, the system temperature is reduced to minus 5 ℃, then the format reagent prepared in the step 1 is slowly dripped for 2-3 hours, the reaction is carried out at minus 5 ℃ for 6 hours after the dripping is finished, after the reaction is finished, the reaction solution is poured into 12% dilute hydrochloric acid, after the reaction is fully stirred for 30 minutes, dichloromethane is used for extraction (300 mL multiplied by 3 times), the organic phase is separated, the organic phase is dried by anhydrous magnesium sulfate, the solvent is concentrated by reduced pressure distillation, and the solvent is recrystallized by tetrahydrofuran after suction filtration, thus obtaining an intermediate A-2-251 (17.18 g, yield 72%) with HPLC purity of not less than 99.80%. Mass spectrum m/z:297.0235 (theory: 297.0256).

Step 3: to the reaction flask was added intermediate A-2-251 (14.91 g,50.00 mmol), c-2-251 (12.71 g,50.00 mmol), anhydrous potassium carbonate (13.82 g,100.00 mmol), then 350mL of toluene solution, 3 times replaced with nitrogen, and tetrakis (triphenylphosphine) palladium (0.58 g,0.50 mmol) was added thereto under stirring and heating for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the solvent was concentrated by distillation under reduced pressure, the filter cake was then washed with ethanol, and the obtained filter cake was recrystallized from toluene to give intermediate B-2-251 (15.81 g, 67% yield) with an HPLC purity of 99.75%. Mass spectrum m/z:471.0963 (theory: 471.0983).

Synthesis example 28: preparation of intermediate B-2-276

According to the same manner as that for intermediate B-2-251 in Synthesis example 27, c-2-251 was replaced with equimolar c-2-276 to obtain intermediate B-2-251 (13.11 g), and the purity of the solid was not less than 99.80% as measured by HPLC. Mass spectrum m/z:379.0919 (theory: 379.0908).

Synthesis example 29: preparation of intermediate B-2-393

According to the same manner as that for intermediate B-2-251 in Synthesis example 27, c-2-251 was replaced with equimolar c-2-293 to obtain intermediate B-2-293 (14.26 g), and the purity of the solid was not less than 99.84% as measured by HPLC. Mass spectrum m/z:395.1565 (theory: 395.1585).

Synthesis example 30: preparation of intermediate B-2-511

According to the same manner as that for intermediate B-2-251 in Synthesis example 27, c-2-251 was replaced with equimolar c-2-511 to obtain intermediate B-2-511 (13.88 g), and the purity of the solid was not less than 99.79% as measured by HPLC. Mass spectrum m/z:390.1081 (theory: 390.1068).

Synthesis example 31: preparation of intermediate B-2-533

According to the same manner as that used for preparing intermediate B-2-251 in Synthesis example 27, c-2-251 was replaced with equimolar c-2-533 to obtain intermediate B-2-533 (14.31 g), and the purity of the solid was not less than 99.81% as measured by HPLC. Mass spectrum m/z:420.1572 (theory: 420.1585).

Synthesis example 32: preparation of Compound 2-1

Synthesis of intermediate F-2-1: d-2-1 (24.69 g,80.00 mmol), E-2-1 (24.42 g,80.00 mmol), potassium carbonate (20.73 g,150.00 mmol) and then 450mL of toluene/ethanol/water mixture (vtoluene: vethanol: vwater=2:1:1) were added under nitrogen protection, then tetrakis (triphenylphosphine) palladium (0.92 g,0.80 mmol) was added to the flask and reacted under stirring and refluxing for 3 hours, after the completion of the reaction, the reaction was cooled to room temperature, distilled water was added, the mixture was left to stand to separate, the separated organic phase was concentrated in solvent by distillation under reduced pressure, suction filtration was performed, the filter cake was rinsed with ethanol, and the obtained filter cake was recrystallized from toluene/ethanol (vtoluene: vethanol=10:1) to give F-2-1 (28.17 g, 72%), HPLC purity was not less than 99.75%, mass spectrum m/z:488.1743 (theory: 488.1727).

Synthesis of intermediate G-2-1: f-2-1 (24.46 g,50.00 mmol), pinacol ester of diboronic acid (12.70 g,50.00 mmol), KOAc (14.72 g,150.00 mmol) and then 300mL of 1, 4-dioxane were added under nitrogen, after 3 changes of air with nitrogen, pd (dppf) Cl was added ₂ (0.37G, 0.50 mmol) under heating, stirring, cooling the reaction to room temperature after the completion of the reaction, adding distilled water, extracting with dichloromethane (700 mL. Times.3), separating the organic phase, drying the organic phase with anhydrous magnesium sulfate, and recrystallizing the obtained solid with toluene to give G-2-1 (23.23G, 80%), HPLC purity > 99.87%, mass spectrum m/z:580.2957 (theory: 580.2969).

Synthesis of Compound 2-1: g-2-1 (17.42G, 30.00 mmol), B-2-1 (8.00G, 30.00 mmol), potassium carbonate (8.29G, 60.00 mmol) and then 300mL of toluene/ethanol/water mixture (vtoluene: vethanol: vwater=2:1:1) and then Pd were added under nitrogen protection ₂ (dba) ₃ (0.27 g,0.30 mmol), (1.2 mL,0.60 mmol) P (t-Bu) ₃ (0.5M toluene solution), heating and stirring for reaction for 6.5 hours, cooling the reactant to room temperature after the reaction is finished, adding distilled water, standing for liquid separation, concentrating a solvent by reduced pressure distillation of a separated organic phase, suction-filtering, flushing a filter cake with ethanol and distilled water, and recrystallizing the obtained filter cake with toluene to obtain a compound 2-1 (14.18 g, 69%), wherein the HPLC purity is not less than 99.96%, and the mass spectrum M/z:684.2950 (theory: 684.2961). Theoretical element content (%) C ₄₉ H ₄₀ N ₂ Si: c,85.92; h,5.89; n,4.09. Measured element content (%): c,85.90; h,5.92; n,4.11.

Synthesis example 33: preparation of Compounds 2-17

Following the same procedure as in synthesis example 32 for preparation of compound 2-1,f-2-1 and B-2-1 are respectively replaced by F-2-17 and B-2-17 with equal mole to obtain compound 2-17 (14.02 g), and the purity of the solid detected by HPLC is more than or equal to 99.93%. Mass spectrum m/z:648.2950 (theory: 648.2961). Theoretical element content (%) C ₄₆ H ₄₀ N ₂ Si: c,85.14; h,6.21; n,4.32. Measured element content (%): c,85.10; h,6.25; n,4.35.

Synthesis example 34: preparation of Compounds 2-28

According to the same manner as that of Compound 2-1 in Synthesis example 32, B-2-1 was replaced with equimolar B-2-28 to give Compound 2-28 (13.99 g), whose purity by HPLC was not less than 99.95%. Mass spectrum m/z:685.2930 (theory: 685.2913). Theoretical element content (%) C ₄₈ H ₃₉ N ₃ Si: c,85.05; h,5.73; n,6.13. Measured element content (%): c,85.01; h,5.71; n,6.16.

Synthesis example 35: preparation of Compounds 2-42

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According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, F-2-17 and B-2-42, respectively, to give Compound 2-42 (15.23 g), and the purity of the solid as measured by HPLC was not less than 99.91%. Mass spectrum m/z:780.3353 (theory: 780.3333). Theoretical element content (%) C ₄₈ H ₃₉ N ₃ Si: c,83.04; h,5.94; n,5.38. Measured element content (%): c,83.08; h,5.92; n,5.36.

Synthesis example 36: preparation of Compounds 2-46

According to the same as that of Compound 2-1 in Synthesis example 32The preparation method is characterized in that D-2-1, E-2-1 and B-2-1 are respectively replaced by equimolar D-2-42, E-2-46 and B-2-46, so that the compound 2-46 (15.92 g) is obtained, and the purity of the solid detected by HPLC is more than or equal to 99.95%. Mass spectrum m/z:757.3328 (theory: 757.3309). Theoretical element content (%) C ₅₁ H ₄₇ N ₃ Si ₂ : c,80.80; h,6.25; n,5.54. Measured element content (%): c,80.77; h,5.24; n,5.56.

Synthesis example 37: preparation of Compounds 2-65

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-65 and B-2-28, respectively, to give Compound 2-65 (11.69 g), and the purity of the solid as measured by HPLC was not less than 99.98%. Mass spectrum m/z:533.2255 (theory: 533.2287). Theoretical element content (%) C ₃₆ H ₃₁ N ₃ Si: c,81.01; h,5.85; n,7.87. Measured element content (%): c,81.03; h,5.86; n,7.86.

Synthesis example 38: preparation of Compounds 2-67

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-67, E-2-67 and B-2-67, respectively, to give Compound 2-67 (15.29 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z:727.3370 (theory: 727.3383). Theoretical element content (%) C ₅₁ H ₄₅ N ₃ Si: c,84.14; h,6.23; n,5.77. Measured element content (%): c,84.11; h,6.28; n,5.79.

Synthesis example 39: preparation of Compounds 2-118

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According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-118 and B-2-118, respectively, to give Compound 2-118 (12.59 g), and the purity of the solid as measured by HPLC was not less than 99.91%. Mass spectrum m/z:590.2856 (theory: 590.2883). Theoretical element content (%) C ₄₀ H ₂₆ D ₇ N ₃ Si: c,81.31; h,6.82; n,7.11. Measured element content (%): c,81.30; h,6.83; n,7.10.

Synthesis example 40: preparation of Compounds 2-119

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-65 and B-2-119, respectively, to give Compound 2-119 (14.28 g), whose purity by HPLC was not less than 99.93%. Mass spectrum m/z:639.2139 (theory: 639.2164). Theoretical element content (%) C ₄₂ H ₃₃ N ₃ SSi: c,78.84; h,5.20; n,6.57. Measured element content (%): c,78.86; h,5.18; n,6.57.

Synthesis example 41: preparation of Compounds 2-126

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-126, E-2-126 and B-2-126, respectively, to give Compound 2-126 (11.99 g), and the purity of the solid as measured by HPLC was not less than 99.91%. Mass spectrum m/z:532.2309 (theory: 532.2335). Theoretical element content (%) C ₃₇ H ₃₂ N ₂ Si: c,83.42; h,6.05; n,5.26. Measured element content (%): c,83.40; h,6.09; n,5.25.

Synthesis example 42: preparation of Compounds 2-159

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-159, E-2-126 and B-2-28, respectively, to give Compound 2-159 (13.17 g), whose purity as measured by HPLC was not less than 99.96%. Mass spectrum m/z:609.2619 (theory: 609.2600). Theoretical element content (%) C ₄₂ H ₃₅ N ₃ Si: c,82.72; h,5.79; n,6.89. Measured element content (%): c,82.77; h,5.77; n,6.95.

Synthesis example 43: preparation of Compounds 2-217

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-217, E-2-217 and B-2-217, respectively, to give Compound 2-217 (14.17 g), and the purity of the solid as measured by HPLC was not less than 99.90%. Mass spectrum m/z:704.2926 (theory: 704.2909). Theoretical element content (%) C ₄₇ H ₃₂ D ₄ N ₄ OSi: c,80.08; h,5.72; n,7.95. Measured element content (%): c,80.10; h,5.71; n,7.94.

Synthesis example 44: preparation of Compounds 2-241

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42 and B-2-241, respectively, to give Compound 2-241 (14.70 g), which was found to have a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:709.2934 (theory: 709.2913). Theoretical element content (%) C ₅₀ H ₃₉ N ₃ Si: c,84.59; h,5.54; n,5.92. Measured element content (%): c,84.60; h,5.52; n,5.89.

Synthesis example 45: preparation of Compounds 2-251

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-251, E-2-251 and B-2-251, respectively, to give Compound 2-251 (14.71 g), and the purity of the solid as measured by HPLC was not less than 99.92%. Mass spectrum m/z:742.2557 (theory: 742.2586). Theoretical element content (%) C ₄₉ H ₃₈ N ₄ SSi: c,79.21; h,5.16; n,7.54. Measured element content (%): c,79.26; h,5.13; n,7.52.

Synthesis example 46: preparation of Compounds 2-269

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-269, E-2-269 and B-2-28, respectively, to give Compound 2-269 (13.31 g), and the purity of the solid as measured by HPLC was not less than 99.93%. Mass spectrum m/z:633.2621 (theory: 633.2600). Theoretical element content (%) C ₄₄ H ₃₅ N ₃ Si: c,83.37; h,5.57; n,6.63. Measured element content (%): c,83.34; h,5.60; n,6.65.

Synthesis example 47: preparation of Compounds 2-276

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-276, E-2-276 and B-2-276, respectively, to give Compound 2-276 (14.77 g), and the purity of the solid as measured by HPLC was not less than 99.90%. Mass spectrum m/z:723.2733 (theory: 723.2706). Theoretical element content (%) C ₅₀ H ₃₇ N ₃ OSi: c,82.95; h,5.15; n,5.80. Measured element content (%): c,82.91; h,5.19; n,5.82。

Synthesis example 48: preparation of Compounds 2-279

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-279, E-2-279 and B-2-279, respectively, to obtain Compound 2-279 (14.23 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:649.2940 (theory: 649.2913). Theoretical element content (%) C ₄₅ H ₃₉ N ₃ Si: c,83.16; h,6.05; n,6.47. Measured element content (%): c,83.19; h,6.03; n,6.44.

Synthesis example 49: preparation of Compounds 2-287

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-279, E-2-287 and B-2-287, respectively, to give Compound 2-287 (17.34 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z:849.3519 (theory: 849.3539). Theoretical element content (%) C ₆₁ H ₄₇ N ₃ Si: c,86.18; h,5.57; n,4.94. Measured element content (%): c,86.14; h,5.60; n,4.96.

Synthesis example 50: preparation of Compound 2-289

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-279, E-2-289 and B-2-28, respectively, to give Compound 2-289 (15.08 g), which was found to have a solid purity of not less than 99.91% by HPLC. Mass spectrum m/z:697.2927 (theory: 697.2913). Theoretical element content (%) C ₄₉ H ₃₉ N ₃ Si: c,84.32; h,5.63; n,6.02. Measured element content (%): c,84.29; h,5.66; n,6.03.

Synthesis example 51: preparation of Compounds 2-330

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-330 and B-2-28, respectively, to give Compound 2-330 (16.97 g), and the purity of the solid as measured by HPLC was not less than 99.97%. Mass spectrum m/z:843.3437 (theory: 843.3465). Theoretical element content (%) C ₅₈ H ₄₉ N ₃ Si ₂ : c,82.52; h,5.85; n,4.98. Measured element content (%): c,82.55; h,5.82n,4.95.

Synthesis example 52: preparation of Compounds 2-342

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-279, E-2-342 and B-2-342, respectively, to give Compound 2-342 (12.57 g), and the purity of the solid as measured by HPLC was not less than 99.95%. Mass spectrum m/z:573.2619 (theory: 573.2600). Theoretical element content (%) C ₃₉ H ₃₅ N ₃ Si: c,81.63; h,6.15; n,7.32. Measured element content (%): c,81.65; h,6.12; n,7.36.

Synthesis example 53: preparation of Compounds 2-393

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-393 and B-2-393, respectively, to give Compound 2-393 (15.25 g), whose purity of solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z: 705.3549 (theory: 705.3539). Theoretical element content (%) C ₄₉ H ₄₇ N ₃ Si: c,83.36; h,6.71; n,5.95. Measured element content (%): c,83.39h,6.73; n,5.93.

Synthesis example 54: preparation of Compounds 2-401

According to the same manner as that of Compound 2-1 in Synthesis example 32, F-2-1 and B-2-1 were replaced with equimolar F-2-401 and B-2-46, respectively, to give Compound 2-401 (16.40 g), whose purity by HPLC was not less than 99.96%. Mass spectrum m/z:769.3320 (theory: 769.3309). Theoretical element content (%) C ₅₂ H ₄₇ N ₃ Si ₂ : c,81.10; h,6.15; n,5.46. Measured element content (%): c,81.07; h,6.12; n,5.48.

Synthesis example 55: preparation of Compounds 2-442

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-279, E-2-442 and B-2-442, respectively, to give Compound 2-442 (16.85 g), and the purity of the solid as measured by HPLC was not less than 99.90%. Mass spectrum m/z:813.4292 (theory: 813.4275). Theoretical element content (%) C ₅₆ H ₄₇ D ₅ N ₄ Si: c,82.61; h,7.06; n,6.88. Measured element content (%): c,82.59; h,7.09; n,6.91.

Synthesis example 56: preparation of Compounds 2-453

According to the same manner as that for preparing compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 are replaced with equimolar amounts of D-2-279 and E-2-342, respectively, B-2-453 to give compound 2-453 (16.76 g), the purity of the solid was not less than 99.94% by HPLC. Mass spectrum m/z:797.3648 (theory: 797.3622). Theoretical element content (%) C ₅₄ H ₅₁ N ₃ Si ₂ : c,81.26; h,6.44; n,5.26. Measured element content (%): c,81.23; h,6.41; n,5.30.

Synthesis example 57: preparation of Compound 2-488

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-488, E-2-342 and B-2-342, respectively, to give Compound 2-488 (14.70 g), and the purity of the solid as measured by HPLC was not less than 99.96%. Mass spectrum m/z:689.3245 (theory: 689.3226). Theoretical element content (%) C48H43N3Si: c,83.56; h,6.28; n,6.09. Measured element content (%): c,83.53; h,6.24; n,6.13.

Synthesis example 58: preparation of Compounds 2-510

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-510, E-2-510 and B-2-342, respectively, to give Compound 2-510 (14.23 g), and the purity of the solid as measured by HPLC was not less than 99.94%. Mass spectrum m/z:649.2928 (theory: 649.2913). Theoretical element content (%) C ₄₅ H ₃₉ N ₃ Si: c,83.16; h,6.05; n,6.47. Measured element content (%): c,83.17; h,6.09; n,6.50.

Synthesis example 59: preparation of Compounds 2-511

According to the same manner as that for preparing compound 2-1 in Synthesis example 32, D-2-1, E-2-1, B-2-1 are replaced by equimolar D-2-511, E-2-511, B-2-511 respectively to obtain compound 2-511 (14.17 g), and the purity of the solid detected by HPLC is more than or equal to 99.93%. Mass spectrum m/z:674.2516 (theory: 674.2502). Theoretical element content (%) C ₄₅ H ₃₄ N ₄ OSi: c,80.09; h,5.08; n,8.30. Measured element content (%): c,80.13; h,5.10; n,8.27.

Synthesis example 60: preparation of Compounds 2-516

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-516 and B-2-516, respectively, to give Compound 2-516 (15.50 g), and the purity of the solid as measured by HPLC was not less than 99.91%. Mass spectrum m/z:759.3052 (theory: 759.3070). Theoretical element content (%) C ₅₄ H ₄₁ N ₃ Si: c,85.34; h,5.44; n,5.53. Measured element content (%): c,85.37; h,5.41; n,5.49.

Synthesis example 61: preparation of Compounds 2-517

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-517 and B-2-342, respectively, to give Compound 2-517 (15.32 g), and the purity of the solid as measured by HPLC was not less than 99.90%. Mass spectrum m/z:739.3010 (theory: 739.3019). Theoretical element content (%) C ₅₁ H ₄₁ N ₃ OSi: c,82.78; h,5.58; n,5.68. Measured element content (%): c,82.80; h,5.61; n,5.64.

Synthesis example 62: preparation of Compounds 2-530

According to the same manner as that of Compound 2-1 in Synthesis example 32, E-2-1 and B-2-1 were replaced with E-2-65 and B-2-46 in equimolar amounts, respectively, to give Compound 2-530 (15.61 g), which was found to have a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:753.3377 (theory: 753.3391). Theoretical element content (%) C ₄₈ H ₅₁ N ₃ Si ₃ : c,76.44; h,6.82; n,5.57. Measured element content (%): c,76.47; h,6.79; n,5.60.

Synthesis example 63: preparation of Compound 2-533

According to the same manner as that of Compound 2-1 in Synthesis example 32, D-2-1, E-2-1 and B-2-1 were replaced with equimolar amounts of D-2-42, E-2-533 and B-2-533, respectively, to give Compound 2-533 (14.80 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:704.3036 (theory: 704.3020). Theoretical element content (%) C ₄₈ H ₃₂ D ₅ N ₃ OSi: c,81.78; h,6.00; n,5.96. Measured element content (%): c,81.80; h,6.03; n,5.95.

Device embodiment

In the invention, the ITO glass substrate and the ITO/Ag/ITO glass substrate are ultrasonically cleaned by 5% glass cleaning liquid for 2 times, 20 minutes each time, and then ultrasonically cleaned by deionized water for 2 times, 10 minutes each time. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. The organic materials are sublimated, and the purity is over 99.99 percent.

Test software, a computer, a K2400 digital source list manufactured by Keithley company in U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company in U.S. are combined into a combined IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates 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.

Example 1: preparation of organic electroluminescent device 1

Vacuum evaporating HI-1 on the ITO anode to form a hole injection layer with the thickness of 15nm; vacuum evaporating the compounds 1-61 as hole transport layers on the hole injection layer, wherein the thickness of the hole transport layers is 110nm; vacuum evaporating a main material RH-1 and a doping material RD-1 on the hole transport layer, wherein the main material RH-1, the doping material RD-1 and the doping material are doped in a ratio of RH-1:RD-1=98:2 (wt%) to form a light emitting layer, and the thickness is 22nm; vacuum evaporating compounds 2-159 on the light-emitting layer as hole blocking layer material, wherein the thickness is 40nm; vacuum evaporating ET-1:Liq=1:1 (wt%) as an electron transport layer on the hole blocking layer, wherein the thickness is 27nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.1nm; al is vacuum evaporated on the electron injection layer as a cathode, and the thickness is 105nm.

Examples 2 to 20: preparation of organic electroluminescent devices 2 to 20

Changing the compound 1-61 in the hole transport layer of example 1 to the compound 1-121, the compound 1-181, the compound 1-208, the compound 1-242, the compound 1-247, the compound 1-254, the compound 1-309, the compound 1-318, the compound 1-329, the compound 1-356, the compound 1-383, the compound 1-397, the compound 1-400, the compound 1-464, the compound 1-492, the compound 1-502, the compound 1-537, the compound 1-535, and the compound 1-664, respectively; the hole blocking layer is prepared by changing the compound 2-159 into the compound 2-126, the compound 2-251, the compound 2-401, the compound 2-46, the compound 2-530, the compound 2-289, the compound 2-28, the compound 2-1, the compound 2-119, the compound 2-393, the compound 2-287, the compound 2-118, the compound 2-279, the compound 2-269, the compound 2-217, the compound 2-453, the compound 2-533, the compound 2-65 and the compound 2-42, respectively, and the other steps are the same.

Comparative example 1: preparation of comparative organic electroluminescent device 1

Vacuum evaporating HI-1 on the ITO anode to form a hole injection layer with the thickness of 15nm; vacuum evaporating the compounds 1-121 as hole transport layers on the hole injection layer, wherein the thickness is 110nm; vacuum evaporating a main material RH-1 and a doping material RD-1 on the hole transport layer, wherein the main material RH-1, the doping material RD-1 and the doping material are doped in a ratio of RH-1:RD-1=98:2 (wt%) to form a light emitting layer, and the thickness is 22nm; vacuum evaporating ET-1:Liq=1:1 (wt%) on the luminescent layer as an electron transport layer, wherein the thickness is 67nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.1nm; al is vacuum evaporated on the electron injection layer as a cathode, and the thickness is 105nm.

Comparative examples 2 to 5: preparation of comparative organic electroluminescent devices 2 to 5

The compounds 1 to 121 in the hole transport layer of comparative example 1 were changed to the compounds 1 to 309, the compounds 1 to 356, the compounds 1 to 400, and the compounds 1 to 537, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 2 to 5.

Comparative examples 6 to 10: preparation of comparative organic electroluminescent devices 6 to 10

The comparative organic electroluminescent devices 6 to 10 were obtained by changing the compounds 2 to 159, 2 to 287, 2 to 401, 2 to 287, 2 to 217, and 2 to 42 in the hole blocking layers of example 1, example 4, example 12, example 16, and example 20 to R-2 in the same manner.

The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 1 to 20 of the present invention and comparative examples 1 to 10 are shown in table 1.

Table 1 light emission characteristic test data of organic electroluminescent device

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As can be seen from table 1, compared with the comparative devices 1 to 10, the organic electroluminescent device using the structure of formula 1 according to the present invention as a hole transport layer and the structure of formula 2 as a hole blocking layer has lower driving voltage, higher luminous efficiency and longer service life, and the device performance is more excellent.

Example 21: preparation of organic electroluminescent device 21

Vacuum evaporating HI-2 on the ITO anode to form a hole injection layer with the thickness of 12nm; vacuum evaporating HT-1 on the hole injection layer to form a first hole transport layer with the thickness of 65nm; vacuum evaporating the compounds 1-60 of the invention on the first hole transport layer to form a second hole transport layer with the thickness of 45nm; vacuum evaporating a main material GH-1 and a doping material GD-1 on the second hole transmission layer, wherein the main material GH-1 and the doping material GD-1 are doped in a ratio of GH-1:GD-1=92:8 (wt%) to form a light-emitting layer, and the thickness is 25nm; vacuum evaporating compound 2-279 on the luminescent layer as hole blocking layer material with thickness of 32nm; vacuum evaporating ET-2:Liq=1:1 (wt%) as an electron transport layer on the hole blocking layer, wherein the thickness is 25nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as a cathode, and the thickness is 110nm.

Examples 22 to 40: preparation of organic electroluminescent devices 22-40

Changing the compound 1-60 in the second hole transport layer of example 21 to the compound 1-82, the compound 1-92, the compound 1-218, the compound 1-233, the compound 1-234, the compound 1-281, the compound 1-302, the compound 1-303, the compound 1-363, the compound 1-385, the compound 1-428, the compound 1-448, the compound 1-458, the compound 1-511, the compound 1-535, the compound 1-580, the compound 1-591, the compound 1-664, and the compound 1-700, respectively; the hole blocking layer is prepared by changing the compound 2-279 into the compound 2-118, the compound 2-442, the compound 2-453, the compound 2-46, the compound 2-530, the compound 2-510, the compound 2-251, the compound 2-516, the compound 2-401, the compound 2-119, the compound 2-330, the compound 2-287, the compound 2-65, the compound 2-241, the compound 2-393, the compound 2-289, the compound 2-511, the compound 2-533 and the compound 2-67, respectively, and the other steps are the same.

Comparative example 11: preparation of comparative organic electroluminescent device 11

Vacuum evaporating HI-2 on the ITO anode to form a hole injection layer with the thickness of 12nm; vacuum evaporating HT-1 on the hole injection layer to form a first hole transport layer with the thickness of 65nm; vacuum evaporating the compounds 1-60 of the invention on the first hole transport layer to form a second hole transport layer with the thickness of 45nm; vacuum evaporating a main material GH-1 and a doping material GD-1 on the second hole transmission layer, wherein the main material GH-1 and the doping material GD-1 are doped in a ratio of GH-1:GD-1=92:8 (wt%) to form a light-emitting layer, and the thickness is 25nm; vacuum evaporating ET-2:Liq=1:1 (wt%) as electron transport layer on the luminescent layer, the thickness is 57nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as a cathode, and the thickness is 110nm.

Comparative examples 12 to 14: preparation of comparative organic electroluminescent devices 12 to 14

The compounds 1 to 60 in the second hole transport layer of comparative example 11 were changed to the compounds 1 to 281, the compounds 1 to 428, and the compounds 1 to 700, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 12 to 14.

Comparative example 15: preparation of contrast organic electroluminescent device 15

Vacuum evaporating HI-2 on the ITO anode to form a hole injection layer with the thickness of 12nm; vacuum evaporating HT-1 on the hole injection layer as a first hole transport layer, wherein the thickness is 110nm; vacuum evaporating a main material GH-1 and a doping material GD-1 on the first hole transmission layer, wherein the main material GH-1 and the doping material GD-1 are doped in a ratio of GH-1:GD-1=92:8 (wt%) to form a light-emitting layer, and the thickness is 25nm; vacuum evaporating compound 2-119 on the luminescent layer as hole blocking layer material, with thickness of 32nm; vacuum evaporating ET-2:Liq=1:1 (wt%) as an electron transport layer on the hole blocking layer, wherein the thickness is 25nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as a cathode, and the thickness is 110nm.

Comparative examples 16 to 18: preparation of contrast organic electroluminescent devices 16-18

And respectively changing the compounds 2-119 in the hole blocking layer of the comparative example 15 into the compounds 2-442, the compounds 2-530 and the compounds 2-533, and obtaining the comparative organic electroluminescent devices 16-18 in the same steps.

Comparative examples 19 to 22: preparation of contrast organic electroluminescent devices 19 to 22

The compounds 1 to 302, 1 to 303, 1 to 458, and 1 to 580 in the hole transport layers of examples 28, 29, 34, and 37 were changed to R-3, and the other steps were the same, to obtain comparative organic electroluminescent devices 19 to 22.

Comparative examples 23 to 26: preparation of comparative organic electroluminescent devices 23 to 26

The comparative organic electroluminescent devices 23 to 26 were obtained by replacing the compounds 2 to 118, 2 to 453, 2 to 287 and 2 to 511 in the hole blocking layers of examples 22, 24, 33 and 39 with R-4 in the same manner.

The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 21 to 40 of the present invention and comparative examples 11 to 26 are shown in table 2.

Table 2 light emission characteristic test data of organic electroluminescent device

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As can be seen from table 2, compared with the comparative devices 11 to 26, the organic electroluminescent device using the formula 1 structure of the present invention as the second hole transport layer and the formula 2 structure as the hole blocking layer has lower driving voltage, higher luminous efficiency and longer service life, and the device performance is more excellent.

Example 41: preparation of organic electroluminescent device 41

Vacuum evaporating HI-3 on the ITO anode to form a hole injection layer with the thickness of 60nm; vacuum evaporating HT-1 on the hole injection layer as a first hole transport layer, wherein the thickness is 35nm; vacuum evaporating HT-2 on the first hole transport layer to serve as a second hole transport layer, wherein the thickness of the second hole transport layer is 40nm; vacuum evaporating the compounds 1-67 of the invention on the second hole transport layer to form a third hole transport layer with the thickness of 35nm; vacuum evaporating a main material GH-1 and a doping material GD-1 on the third hole transmission layer, wherein the main material GH-1 and the doping material GD-1 are doped in a ratio of GH-1:GD-1=92:8 (wt%) to form a light-emitting layer, and the thickness is 22nm; vacuum evaporating compound 2-530 on the luminescent layer as hole blocking layer material with thickness of 30nm; vacuum evaporating ET-3 on the hole blocking layer as an electron transport layer, wherein the thickness is 23nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as a cathode, and the thickness is 110nm.

Examples 42 to 60: preparation of organic electroluminescent devices 42-60

Changing the compound 1-67 in the third hole-transporting layer of example 41 to the compound 1-82, the compound 1-107, the compound 1-112, the compound 1-115, the compound 1-218, the compound 1-223, the compound 1-244, the compound 1-281, the compound 1-303, the compound 1-363, the compound 1-385, the compound 1-458, the compound 1-493, the compound 1-511, the compound 1-540, the compound 1-591, the compound 1-642, the compound 1-664, and the compound 1-700, respectively; the hole blocking layer is prepared by changing the compound 2-530 into the compound 2-533, the compound 2-46, the compound 2-119, the compound 2-442, the compound 2-453, the compound 2-401, the compound 2-28, the compound 2-1, the compound 2-287, the compound 2-393, the compound 2-65, the compound 2-342, the compound 2-517, the compound 2-251, the compound 2-276, the compound 2-279, the compound 2-17, the compound 2-289 and the compound 2-118, and the other steps are the same.

Comparative example 27: preparation of comparative organic electroluminescent device 27

Vacuum evaporating HI-3 on the ITO anode to form a hole injection layer with the thickness of 60nm; vacuum evaporating HT-1 on the hole injection layer as a first hole transport layer, wherein the thickness is 35nm; vacuum evaporating HT-2 on the first hole transport layer to serve as a second hole transport layer, wherein the thickness of the second hole transport layer is 40nm; vacuum evaporating the compounds 1-112 of the invention on the second hole transport layer to form a third hole transport layer with the thickness of 35nm; vacuum evaporating a main material GH-1 and a doping material GD-1 on the third hole transmission layer, wherein the main material GH-1 and the doping material GD-1 are doped in a ratio of GH-1:GD-1=92:8 (wt%) to form a light-emitting layer, and the thickness is 22nm; vacuum evaporating ET-3 on the luminous layer as an electron transport layer, wherein the thickness is 53nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as a cathode, and the thickness is 110nm.

Comparative examples 28 to 30: preparation of comparative organic electroluminescent devices 28 to 30

The compounds 1 to 112 in the third hole transport layer of comparative example 27 were changed to the compounds 1 to 363, the compounds 1 to 540, and the compounds 1 to 591, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 28 to 30.

Comparative example 31: preparation of comparative organic electroluminescent device 31

Vacuum evaporating HI-3 on the ITO anode to form a hole injection layer with the thickness of 60nm; vacuum evaporating HT-1 on the hole injection layer as a first hole transport layer, wherein the thickness is 60nm; vacuum evaporating HT-2 on the first hole transport layer to serve as a second hole transport layer, wherein the thickness of the second hole transport layer is 50nm; vacuum evaporating a main material GH-1 and a doping material GD-1 on the second hole transmission layer, wherein the main material GH-1 and the doping material GD-1 are doped in a ratio of GH-1:GD-1=92:8 (wt%) to form a light-emitting layer, and the thickness is 22nm; vacuum evaporating compound 2-1 on the luminescent layer as hole blocking layer material with thickness of 30nm; vacuum evaporating ET-3 on the hole blocking layer as an electron transport layer, wherein the thickness is 23nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1.0nm; al is evaporated on the electron injection layer in vacuum as a cathode, and the thickness is 110nm.

Comparative examples 32 to 34: preparation of comparative organic electroluminescent devices 32-34

The compound 2-1 in the hole blocking layer of comparative example 31 was changed to compound 2-17, compound 2-342, and compound 2-453, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 32 to 34.

Comparative examples 35 to 38: preparation of comparative organic electroluminescent devices 35 to 38

The comparative organic electroluminescent devices 35 to 38 were obtained by replacing the compounds 1 to 107, 1 to 493, 1 to 511, and 1 to 664 in the hole transport layers of examples 43, 54, 55, and 59 with R-5 in the same manner.

Comparative examples 39 to 42: preparation of comparative organic electroluminescent devices 39-42

The comparative organic electroluminescent devices 39 to 42 were obtained by changing the compounds 2 to 533, 2 to 442, 2 to 401, and 2 to 65 in the hole blocking layers of examples 42, 45, 47, and 52 to R-6 in the same manner.

The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 41 to 60 and comparative examples 27 to 42 according to the present invention are shown in table 3.

Table 3 light emission characteristics test data of organic electroluminescent device

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As can be seen from table 3, compared with the comparative devices 27 to 42, the organic electroluminescent device using the formula 1 structure of the present invention as the third hole transport layer and the formula 2 structure as the hole blocking layer has lower driving voltage, higher luminous efficiency and longer service life, and the device performance is more excellent.

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. An organic electroluminescent device comprising an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises a hole transport region, a luminescent layer and an electron transport region, the hole transport region is positioned between the anode and the luminescent layer, and the electron transport region is positioned between the luminescent layer and the cathode, characterized in that the hole transport region contains a compound shown in formula 1, the electron transport region contains a compound shown in formula 2,

said Z is selected from O, S, CR _a R _b Or NR (NR) _c ；

The R is _a 、R _b The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groups, or adjacent R _a 、R _b Bonded to each other to form a substituted or unsubstituted ring;

the Ar is as follows ₃ 、Ar ₄ 、Ar ₅ The same or different condensed rings selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ringsOne of the bases or a combination thereof;

the c ₁ Selected from 0, 1 or 2.

2. The organic electroluminescent device of claim 1, wherein the Ar ₁ One or a combination of the following groups,

the R is ₅ The same or different one or more selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring condensed ring groupsA combination thereof, or two adjacent R ₅ Bonded to each other to form a substituted or unsubstituted ring;

3. The organic electroluminescent device of claim 1, wherein the organic electroluminescent device comprisesSelected from one of the groups shown below,

the R is ₂ The same or different aryl groups selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, and substituted or unsubstituted C6-C30 arylOne of the condensed ring groups of the substituted or unsubstituted C3-C20 alicyclic ring and the C6-C30 aromatic ring, or two adjacent R ₂ Bonded to each other to form a substituted or unsubstituted ring;

4. The organic electroluminescent device of claim 1, wherein the L ₀ 、L ₁ 、L ₂ Independently selected from a single bond or one or a combination of the groups shown below,

5. The organic electroluminescent device as claimed in claim 1, wherein the formula 1 is selected from any one of the compounds shown below,

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6. the organic electroluminescent device of claim 1, wherein the Ar ₃ 、Ar ₄ 、Ar ₅ One or a combination of the following groups,

y is selected from CH or N;

the R is _j Selected from the group consisting of substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groupsA group, a substituted or unsubstituted aryl group of C6 to C30, a substituted or unsubstituted heteroaryl group of C2 to C30, a substituted or unsubstituted alicyclic ring of C3 to C20, and a condensed cyclic group of an aromatic ring of C6 to C30.

7. The organic electroluminescent device of claim 1, wherein the Ar ₃ 、Ar ₄ 、Ar ₅ One or a combination of the following groups,

the R is _e The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl,trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothienyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following;

the R is _k The same or different radicals are selected from hydrogen, deuterium, tritium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenylOne of biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclopentenyl, benzofuranyl, benzothienyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;

the R is ₇ 、R _e 、R _h 、R _i 、R _j May be substituted with one or more substituents which may be the same or different and are selected from deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, ethyldimethylsilyl, t-butyldimethylsilyl,benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentene, benzocyclohexene, benzofuranyl, benzothienyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, si (R) ₄ ) ₃ One of the following; when two or more substituents are present, the two or more substituents may be the same or different from each other;

the i is ₁ Selected from 0, 1, 2, 3 or 4; the i is ₂ Selected from 0, 1, 2, 3, 4, 5 or 6; the i is ₃ Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the i is ₄ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the i is ₅ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the i is ₆ Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; the i is ₇ Selected from 0, 1, 2, 3, 4 or 5;

8. The organic electroluminescent device of claim 1, wherein the L ₃ 、L ₄ 、L ₅ Independently selected from a single bond or one or a combination of the groups shown below,

9. The organic electroluminescent device according to claim 1, wherein the Si (R ₄ ) ₃ Selected from one of the groups shown below,

10. the organic electroluminescent device according to claim 1, wherein the formula 2 is selected from any one of the compounds shown below,

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