阅读说明：本技术 化合物、其应用及包含其的有机电致发光器件 (Compound, application thereof and organic electroluminescent device comprising compound ) 是由 黄金华 曾礼昌 于 2019-09-04 设计创作，主要内容包括：本发明提供了一种化合物、其应用及包含其的有机电致发光器件。该化合物具有结构式,L为单键、取代或未取代的C_6～C_(30)的亚芳基、C_3～C_(30)的杂亚芳基；Ar为取代或未取代的C_6～C_(30)的芳基、C_3～C_(30)的杂芳基,m为1～6中的任意一个整数；R~1、R~2各自独立地选自取代或未取代的C_1～C_(20)的烷基、C_1～C_(12)的烷氧基、C_3～C_(20)的环烷基、C_1～C_6的醚基、C_6～C_(30)的芳基、C_2～C_(30)杂环烷基、C_3～C_(30)的杂芳基,且R~1、R~2以单键的方式连接在母核上,n1和n2为0～4中的任意一个整数；G为C_6～C_(60)的多环亚环烷基,多环亚环烷基与式I中位于其两侧的两个苯基连接,且连接位为一个季碳原子。(The invention provides a compound, application thereof and an organic electroluminescent device comprising the compound. The compound has Structural formula, L is a single bond, substituted or unsubstituted C 6 ～C 30 Arylene of, C 3 ～C 30 The heteroarylene group of (a); ar is substituted or unsubstituted C 6 ～C 30 Aryl of (C) 3 ～C 30 M is any integer of 1-6; r 1 、R 2 Each independently selected from substituted or unsubstituted C 1 ～C 20 Alkyl of (C) 1 ～C 12 Alkoxy group of (C) 3 ～C 20 Cycloalkyl of, C 1 ～C 6 Ether group of (C) 6 ～C 30 Aryl of (C) 2 ～C 30 Heterocycloalkyl radical, C 3 ～C 30 And R is heteroaryl of 1 、R 2 The single bond is connected to the mother nucleus, and n1 and n2 are any integer of 0-4; g is C 6 ～C 60 The polycyclic cycloalkylene group of (a) is bonded to the two phenyl groups on both sides thereof in formula I, and the bonding position is a quaternary carbon atom.)

1. A compound having the structure shown in formula I:

wherein L is a single bond, substituted or unsubstituted C₆～C₃₀Arylene of (a), substituted or unsubstituted C₃～C₃₀The heteroarylene group of (a);

ar is substituted or unsubstituted C₆～C₃₀Aryl, substituted or unsubstituted C₃～C₃₀M is any integer of 1-6;

R¹、R²each independently selected from substituted or unsubstituted C₁～C₂₀Alkyl, substituted or unsubstituted C₁～C₁₂Alkoxy, substituted or unsubstituted C₃～C₂₀Cycloalkyl, substituted or unsubstituted C₁～C₆Ether group of (A), substituted or unsubstituted C₆～C₃₀Aryl, substituted or unsubstituted C₂～C₃₀Heterocycloalkyl, substituted or unsubstituted C₃～C₃₀And R is heteroaryl of¹、R²The single bond is connected to the mother nucleus, and n1 and n2 are any integer of 0-4;

g is C₆～C₆₀Said polycyclic cycloalkylene being linked to the two phenyl groups on either side of said formula I, and the linking position being a quaternary carbon atom;

when substituents are present in each of the above groups, thenThe substituents are respectively and independently selected from halogen and C₁～C₁₀Alkyl of (C)₃～C₁₀Cycloalkyl of, C₁～C₆Alkoxy group of (C)₁～C₆Thioalkoxy of, C₆～C₃₀Aryl of (C)₃～C₃₀One or more of the heteroaryl groups may be,

in formula I, the expression of the "-" underlined loop structure means that the linking site is located at any position on the loop structure capable of forming a bond.

2. The compound of claim 1, wherein G is C₆～C₂₀Preferably said G is bridged polycyclic cycloalkylene, further preferably said G is selected from one of the following polycyclic cycloalkylene groups:

wherein ". sup." represents the position of access of the group.

3. A compound according to claim 1 or 2, wherein Ar is substituted or unsubstituted C₆～C₂₀Aryl, substituted or unsubstituted C₅～C₂₀The heteroaryl group of (a).

4. A compound according to any one of claims 1 to 3, wherein R is¹、R²Each independently selected from substituted or unsubstituted C₁～C₁₀Alkyl, substituted or unsubstituted C₃～C₆Ether group of (A), substituted or unsubstituted C₃～C₁₀Cycloalkyl, substituted or unsubstituted C₆～C₂₀Aryl, substituted or unsubstituted C₅～C₂₀Any one of the heteroaryl groups of (a).

5. According to claim 3 or 4The compound of (1), wherein C is₆～C₂₀The aryl group of (A) is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,Any one group of the group consisting of phenyl and tetracenyl, preferably the biphenyl group comprises 2-biphenyl, 3-biphenyl and 4-biphenyl, preferably the terphenyl group comprises p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; preferably, the naphthyl group includes 1-naphthyl and 2-naphthyl; preferably the anthracenyl group includes 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group comprises 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; preferably the fluorenyl derivative group includes 9,9 '-dimethylfluorenyl, 9' -spirobifluorenyl and benzofluorenyl; preferably, the pyrenyl groups include 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; preferably the tetracenyl group includes 1-tetracenyl, 2-tetracenyl and 9-tetracenyl;

preferably said C₅～C₂₀The heteroaryl group is any one of the group consisting of furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, preferably the carbazolyl derivative comprises 9-phenylcarbazolyl, 9-naphthylcarbazole benzocarbazolyl, dibenzocarbazolyl and indolocarbazolyl.

6. A compound according to any one of claims 1 to 5, wherein when a substituent is present in each of the above groups, the substituents are each independently selected from C₁～C₅Alkyl of (C)₁～C₅Alkoxy group of (C)₆～C₂₀Non-condensed ring aryl of, C₅～C₂₀Preferably, the substituents are each independently selected from fluoro, chloro, bromo, methyl, ethyl, n-heteroarylAny one of propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, tetrahydrofuran, pyrrolidine, tetrahydrothiophene, phenyl, biphenyl, terphenyl, 2-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl.

7. A compound according to any one of claims 1 to 3, wherein R is¹、R²Each independently is any one of phenyl, biphenyl, naphthyl, pyrenyl, 9' -dimethylfluorenyl, benzofluorenyl, dibenzofuranyl, dibenzothienyl and 9-phenylcarbazolyl, and preferably R is₁、R₂Each independently is any one of phenyl, biphenyl, 9' -dimethylfluorenyl, dibenzofuranyl, dibenzothienyl and 9-phenylcarbazolyl.

8. A compound according to claim 1 or 4 or 7, wherein Ar is selected from any one of the following groups:

wherein, the expression of the "-" crossed loop structure indicates that the connecting site is at any position on the loop structure capable of forming a bond, and the "-" represents the access position of the group.

9. The compound of claim 1, wherein the compound has a structure represented by any one of the following structural formulae P1-P248:

10. use of a compound according to any one of claims 1 to 9 as a hole transport material in an organic electroluminescent device.

11. An organic electroluminescent device comprising an anode and a cathode and a plurality of organic layers arranged between the anode and the cathode, at least one of the organic layers having a compound disposed therein, characterized in that at least one of the compounds is a compound according to any one of claims 1 to 9.

12. The organic electroluminescent device according to claim 11, characterized in that the organic layer comprises a hole transport layer and/or an electron blocking layer, in which the compound according to any one of claims 1 to 9 is disposed.

Technical Field

The invention relates to the technical field of organic light-emitting materials, in particular to a compound, application thereof and an organic electroluminescent device comprising the compound.

Background

Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.

With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.

In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.

So far, the development of the existing OLED photoelectric functional material is far behind the requirements of panel manufacturing enterprises on the OLED material, so it is very urgent to develop an organic functional material with better performance to meet the development requirements of the current industry.

Disclosure of Invention

The invention mainly aims to provide a compound, application thereof and an organic electroluminescent device comprising the compound, so as to solve the problems of high starting voltage and low luminous efficiency of an organic photoelectric functional material in the prior art.

In order to achieve the above object, according to one aspect of the present invention, there is provided a compound having a structure represented by formula I below:

wherein L is a single bond, substituted or unsubstituted C₆～C₃₀Arylene of (a), substituted or unsubstituted C₃～C₃₀The heteroarylene group of (a); ar is substituted or unsubstituted C₆～C₃₀Aryl, substituted or unsubstituted C₃～C₃₀M is any integer of 1-6; r¹、R²Each independently selected from substituted or unsubstituted C₁～C₂₀Alkyl, substituted or unsubstituted C₁～C₁₂Alkoxy, substituted or unsubstituted C₃～C₂₀Cycloalkyl, substituted or unsubstituted C₁～C₆Ether group of (A), substituted or unsubstituted C₆～C₃₀Aryl, substituted or unsubstituted C₂～C₃₀Heterocycloalkyl, substituted or unsubstituted C₃～C₃₀And R is heteroaryl of¹、R²Singly bound to the parent nucleus, n1 andn2 is any integer of 0-4; g is C₆～C₆₀The polycyclic cycloalkylene group of (a) is linked to the two phenyl groups on both sides thereof in formula I, and the linking position is a quaternary carbon atom; when the above groups have substituents, the substituents are respectively and independently selected from halogen and C₁～C₁₀Alkyl of (C)₃～C₁₀Cycloalkyl of, C₁～C₆Alkoxy group of (C)₁～C₆Thioalkoxy of, C₆～C₃₀Aryl of (C)₃～C₃₀The expression of a "-" underlined ring structure in formula I denotes a linking site at any position on the ring structure capable of bonding.

According to another aspect of the present invention there is provided a use of a compound according to any one of the above as a hole transport material in an organic electroluminescent device.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising an anode and a cathode and a plurality of organic layers disposed between the anode and the cathode, at least one of the organic layers having a compound disposed therein, at least one of the compounds being a compound of any one of the above.

When the technical scheme of the invention is applied and the compound is used as a hole transport layer or an electron blocking layer of an organic electroluminescent device, compared with the prior art, the driving voltage can be further reduced, the luminous efficiency can be improved, and the service life can be prolonged. Specifically, when the compound is applied to a device, the performance improvement may be attributed to specific rearrangement of triarylamine intermolecular arrangement in the structure caused by occupation of polycyclic cycloalkyl groups on methylene, and the hole transport performance and stability of an amorphous film based on the arrangement are greatly improved.

Detailed Description

It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail with reference to examples.

As is conventional in the art for expression,the expression of the "-" underlined ring structure in the following structural formula means that the linking site is located at any position on the ring structure capable of forming a bond; "" denotes the position of access of the group. In the present invention, C₆～C₃₀Substituted or unsubstituted arylene of and C₆～C₃₀C in substituted or unsubstituted aryl₆～C₃₀Represents the number of carbon atoms in the group, preferably the number of carbon atoms is 3,5, 8, 10, 12, 15, 18, 20, 23, 25, 28 or 30; preferably C₃～C₃₀Substituted or unsubstituted heteroarylene of (1) and C₃～C₃₀The number of carbon atoms in the substituted or unsubstituted heteroaryl group is 3,5, 8, 10, 12, 15, 18, 20, 23, 25, 28, or 30; preferably C₁～C₂₀Has 1, 3,5, 8, 10, 12, 15, 18 or 20 carbon atoms. Also, the definition of other ranges of carbon numbers indicates that the number of carbon atoms in the group may take any integer within the numerical range. Unless otherwise specified, generally the number of carbon atoms does not include the number of carbon atoms of the substituent. In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium". The heteroatom of the present invention is generally selected from N, O, S.

As analyzed in the background of the present application, the organic photoelectric functional material of the prior art has the problems of high starting voltage and low luminous efficiency, and in order to solve the problems, the present application provides a compound having the structure shown in formula I below:

wherein L is a single bond, substituted or unsubstituted C₆～C₃₀Arylene of (a), substituted or unsubstituted C₃～C₃₀The heteroarylene group of (a); ar is substituted or unsubstituted C₆～C₃₀Aryl, substituted or unsubstituted C₃～C₃₀M is any integer of 1-6; r¹、R²Each independently selected from substituted or unsubstituted C₁～C₂₀Alkyl, substituted or unsubstituted C₁～C₁₂Alkoxy, substituted or unsubstituted C₃～C₂₀Cycloalkyl, substituted or unsubstituted C₁～C₆Ether group of (A), substituted or unsubstituted C₆～C₃₀Aryl, substituted or unsubstituted C₂～C₃₀Heterocycloalkyl, substituted or unsubstituted C₃～C₃₀And R is heteroaryl of¹、R²The single bond is connected to the mother nucleus, and n1 and n2 are any integer of 0-4; g is C₆～C₆₀And said polycyclic cycloalkylene is linked to the two phenyl groups on both sides of said polycyclic cycloalkylene of formula I, and the linking position is a quaternary carbon atom, and when substituents are present for each of the above groups, the substituents are each independently selected from C₁～C₁₀Alkyl of (C)₃～C₁₀Cycloalkyl of, C₁～C₆Alkoxy group of (C)₁～C₆Thioalkoxy of, C₆～C₃₀Aryl of (C)₃～C₃₀The expression of a "-" underlined ring structure in formula I denotes a linking site at any position on the ring structure capable of bonding.

When the compound is used as a hole transport layer or an electron blocking layer of an organic electroluminescent device, compared with the prior art, the compound can further reduce the driving voltage, improve the luminous efficiency and prolong the service life. Specifically, when the compound is applied to a device, the performance improvement may be attributed to specific rearrangement of triarylamine intermolecular arrangement in the structure caused by occupation of polycyclic cycloalkyl groups on methylene, and the hole transport performance and stability of an amorphous film based on the arrangement are greatly improved.

In one embodiment, G in formula I is preferably C₆～C₂₀Preferably said G is bridged polycyclic cycloalkylene, further preferably G is selected from one of the following polycyclic cycloalkylene groups:

wherein ". x" represents the access position of the group.

Preferably, Ar is substituted or unsubstituted C₆～C₂₀Aryl, substituted or unsubstituted C₅～C₂₀The heteroaryl group of (a).

In another embodiment, the above R is preferred¹、R²Each independently selected from substituted or unsubstituted C₁～C₁₀Alkyl, substituted or unsubstituted C₃～C₆Ether group of (A), substituted or unsubstituted C₃～C₁₀Cycloalkyl, substituted or unsubstituted C₆～C₂₀Aryl, substituted or unsubstituted C₅～C₂₀Any one of the heteroaryl groups of (a).

The above-mentioned substituted or unsubstituted C₁～C₂₀The alkyl group in the alkyl group is preferably C₁～C₁₀More preferably C₁～C₆The alkyl group of (3) is more preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a n-hexyl group, a n-octyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group or a cyclohexyl group. Substituted or unsubstituted C₃～C₃₀Cycloalkyl in cycloalkyl is C₃～C₁₀Cycloalkyl of (b) is preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

In Ar or R¹、R²In, C₆～C₂₀The aryl group of (A) is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,Any one group of the group consisting of a radical and a tetracenyl radical, preferably a bisPhenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl, preferably terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; preferred naphthyl groups include 1-naphthyl and 2-naphthyl; preferred anthracenyl groups include 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; preferred fluorenyl derivative groups include 9,9 '-dimethylfluorenyl, 9' -spirobifluorenyl, and benzofluorenyl; the preferred pyrenyl groups include 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; preferred tetracenyl groups include 1-tetracenyl, 2-tetracenyl and 9-tetracenyl; preferably C₅～C₂₀The heteroaryl group is any one of the group consisting of furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, and preferably the carbazolyl derivative comprises 9-phenylcarbazolyl, 9-naphthylcarbazole benzocarbazolyl, dibenzocarbazolyl and indolocarbazolyl.

In one embodiment, the substituents are each independently selected from C₁～C₅Alkyl of (C)₁～C₅Alkoxy group of (C)₆～C₂₀Non-condensed ring aryl of, C₅～C₂₀One or more of non-fused ring heteroaryl groups. The non-condensed ring aryl or the non-condensed ring heteroaryl is selected as a substituent, so that the conjugation degree of the aromatic ring can be reduced, and the triplet state energy level of the material can be improved. Preferably, the above substituents are each independently selected from any one of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, tetrahydrofuran, pyrrolidine, tetrahydrothiophene, phenyl, biphenyl, terphenyl, 2-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl.

R is as defined above¹、R²Each independently is phenyl, biphenylAny one of naphthyl, pyrenyl, 9' -dimethylfluorenyl, benzofluorenyl, dibenzofuranyl, dibenzothienyl and 9-phenylcarbazolyl, and R is preferably R₁、R₂Each independently is any one of phenyl, biphenyl, 9' -dimethylfluorenyl, dibenzofuranyl, dibenzothienyl and 9-phenylcarbazolyl.

Further, it is preferable that each of n1 and n2 is 0, 1 or 2 independently.

More preferably, Ar is selected from any one of the following groups:

wherein, the expression of the "-" crossed loop structure indicates that the connecting site is at any position on the loop structure capable of forming a bond, and the "-" represents the access position of the group.

The number of m may be selected from any one integer of 1 to 6, preferably 1.

Further, L is preferably a single bond.

Through experiments, the compound preferably has a structure shown in a formula II:formula II, in one embodiment, L in formula II is preferably a single bond.

More preferably, the compound has a structure represented by any one of the following structural formulae P1 to P248:

the synthetic route of the organic photoelectric compound of the present application can refer to the following synthetic route:

based on the synthetic route and thought of the above compounds, the person skilled in the art can obtain the compound shown in formula I with the substituent Ar.

In another exemplary embodiment of the present application, there is provided a use of the compound of any one of the above as a hole transport material in an organic electroluminescent device.

The compound of the present invention can be applied to a hole transport layer or an electron blocking layer in an organic electronic device, and examples of the organic electronic device include an organic electroluminescent device, a lighting device, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a large-area sensor such as a sheet scanner, an electronic paper, an organic EL panel, and the like.

In another exemplary embodiment of the present application, there is also provided an organic electroluminescent device including an anode and a cathode, and a plurality of organic layers disposed between the anode and the cathode, at least one of the organic layers having an organic photoelectric compound disposed therein, at least one of the organic photoelectric compounds being a compound of any one of the above. When the compound is applied to an organic electroluminescent device, the turn-on voltage of the device can be reduced, the photoelectric efficiency can be improved, and the service life of the device can be prolonged.

In one embodiment, the organic layer includes a hole transport layer and/or an electron blocking layer, and the compound of the present application is disposed in the hole transport layer and/or the electron blocking layer.

In addition, the organic functional material layer may further include a hole transport layer, a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer, which are sequentially disposed away from the anode.

Next, the organic electroluminescent device will be explained in detail.

The organic electroluminescent device includes first and second electrodes, and an organic material layer between the electrodes. The organic material layer may be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.

In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.

The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used₂) Transparent conductive oxide materials such as zinc oxide (ZnO), and the like, and their useAny combination of (a). When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.

The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and combinations thereof.

The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).

When the hole transport layer of the hole transport region is selected from one of the above-mentioned compounds or any combination thereof, the electron blocking layer of the hole transport region may be absent, may be present, and is selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenyleneethylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below as HT-1 to HT-34; or any combination thereof. When the hole transport layer of the hole transport region is selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below as HT-1 to HT-34, or any combination thereof; the electron blocking layer of the hole transport region is selected from one or any combination of the compounds described above.

The materials for the hole transport region and the hole injection region may be selected from, but not limited to, the compounds of the present invention and the above-mentioned compounds; or any combination thereof. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds of the present invention described above, or employ one or more of the compounds of HI1-HI3 described below; one or more of the compounds may also be used to dope one or more of the compounds described below as HI1-HI 3.

The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.

According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.

In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.

In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.

Wherein D is deuterium.

In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.

In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1-YPD-11 listed below.

The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).

In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.

An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li₂O、Cs₂CO₃BaO, Na, Li and Ca.

The technical solution of the present invention is further illustrated by the following specific examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.

The solvents and reagents used in the following synthetic examples of the present invention, such as aryl bromide, 2-bromo-9, 9 '-dimethylfluorene, 2-bromodibenzofuran, 2-bromodibenzothiophene, 4-bromobiphenyl, [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, tris (dibenzylideneacetone) dipalladium, toluene, petroleum ether, n-hexane, methylene chloride, acetone, sodium sulfate, ethyl acetate, ethanol, tritylphosphine, potassium/sodium tert-butoxide and the like, are commercially available or customized from domestic chemical product markets, such as from national drug group reagents, Sigma-Aldrich, and Bailingwei reagents, and intermediate M is supplied by Nakagaku, Bailingo. In addition, they can be synthesized by a known method by those skilled in the art.

Synthesis example 1: synthesis of Compound P1

In a 500ml single-neck flask, 15g (50mmol) of M1, 7.8g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P1, wherein the theoretical value of M/Z is 377, and the actual value of M/Z is 378.

Synthesis example 2: synthesis of Compound P2

In a 500ml single-mouth bottle,15g (50mmol) of M1, 10.5g (50mmol) of 1-bromonaphthalene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P2, wherein the theoretical value of M/Z is 427, and the actual value of M/Z is 428.

Synthetic example 3: synthesis of Compound P3

In a 500ml single-necked flask, 15g (50mmol) of M1, 10.5g (50mmol) of 2-bromonaphthalene, and 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P3, wherein the theoretical value of M/Z is 427, and the actual value of M/Z is 428.

Synthetic example 4: synthesis of Compound P6

In a 500ml single-neck flask, 15g (50mmol) of M1, 11.5g (50mmol) of 3-bromobiphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5h, and reactingAnd stopping the reaction to obtain a reaction solution. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P6, wherein the theoretical value of M/Z is 453, and the actual value of M/Z is 454.

Synthesis example 5: synthesis of Compound P9

In a 500ml single neck flask, 15g (50mmol) of M1, 15.4g (50mmol) of 3, 5-diphenylbromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P9, wherein the theoretical value of M/Z is 529, and the actual value of M/Z is 530.

Synthetic example 6: synthesis of Compound P17

In a 500ml single-neck flask, 15g (50mmol) of M1, 13.1g (50mmol) of 2-bromodibenzothiophene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P17, wherein the theoretical value of M/Z is 483, and the actual value of M/Z is 484.

Synthetic example 7: synthesis of Compound P18

In a 500ml single-neck flask, 15g (50mmol) of M1, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P18, wherein the theoretical value of M/Z is 468, and the actual value of M/Z is 469.

Synthesis example 8: synthesis of Compound P19

In a 500ml single-neck flask, 15g (50mmol) of M1, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P19, wherein the theoretical value of M/Z is 493, and the actual value of M/Z is 494.

Synthetic example 9: synthesis of Compound P25

In a 500ml single-neck flask, 15g (50mmol) of M1, 13.1g (50mmol) of 4-bromodibenzothiophene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P25, wherein the theoretical value of M/Z is 483, and the actual value of M/Z is 484.

Synthetic example 10: synthesis of Compound P26

In a 500ml single-neck flask, 15g (50mmol) of M1, 12.3g (50mmol) of 4-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P26, wherein the theoretical value of M/Z is 468, and the actual value of M/Z is 469.

Synthetic example 11: synthesis of Compound P45

In a 500ml single-neck flask, 16g (50mmol) of M2, 7.8g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu)And-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for 5 hours, and stopping the reaction after the reaction is finished to obtain a reaction solution. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P45, wherein the theoretical value of M/Z is 393, and the actual value of M/Z is 394.

Synthetic example 12: synthesis of Compound P50

In a 500ml single-necked flask, 16g (50mmol) of M2, 11.5g (50mmol) of 3-bromobiphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene), 714.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5h, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P50, wherein the theoretical value of M/Z is 469, and the actual value of M/Z is 470.

Synthetic example 13: synthesis of Compound P53

In a 500ml single neck flask, 16g (50mmol) of M2, 15.4g (50mmol) of 3, 5-diphenylbromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and vacuum filtering to obtain light yellow powder shown as structural formula P53The theoretical value of M/Z was 545, and the observed value of M/Z was 546.

Synthesis example 14: synthesis of Compound P61

In a 500ml single-neck flask, 16g (50mmol) of M2, 13.1g (50mmol) of 2-bromodibenzothiophene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P61, wherein the theoretical value of M/Z is 499, and the actual value of M/Z is 500.

Synthetic example 15: synthesis of Compound P62

In a 500ml single-neck flask, 16g (50mmol) of M2, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P62, wherein the theoretical value of M/Z is 483, and the actual value of M/Z is 484.

Synthetic example 16: synthesis of Compound P105

In a 500ml single-neck flask, 11.5g (50mmol) of M3, 13.1g (50mmol) of 2-bromodibenzothiophene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P105, wherein the theoretical value of M/Z is 416, and the actual value of M/Z is 417.

Synthetic example 17: synthesis of Compound P106

In a 500ml single-neck flask, 11.5g (50mmol) of M3, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P106, wherein the theoretical value of M/Z is 399, and the actual value of M/Z is 400.

Synthetic example 18: synthesis of Compound P149

In a 500ml single-neck flask, 13.8g (50mmol) of M4, 13.1g (50mmol) of 2-bromodibenzothiophene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL tritidineRadical phosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P149, wherein the theoretical value of M/Z is 458, and the actual value of M/Z is 459.

Synthetic example 19: synthesis of Compound P150

In a 500ml single-neck flask, 13.8g (50mmol) of M4, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P150, wherein the theoretical value of M/Z is 442, and the actual value of M/Z is 443.

Synthesis example 20: synthesis of Compound P177

In a 500ml single-neck flask, 15g (50mmol) of M5, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, and concentrating the organic phaseAdding methanol into the concentrated organic phase, stirring for 1h, and vacuum filtering to obtain light yellow powder, which is a compound shown as a structural formula P177, wherein the theoretical value of M/Z is 469, and the actual value of M/Z is 470.

Synthetic example 21: synthesis of compound P178

In a 500ml single-neck flask, 12.3g (50mmol) of M6, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P178, wherein the theoretical value of M/Z is 416, and the actual value of M/Z is 417.

Synthetic example 22: synthesis of Compound P179

In a 500ml single-neck flask, 15g (50mmol) of M7, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P179, wherein the theoretical value of M/Z is 469, and the actual value of M/Z is 470.

Synthetic example 23: synthesis of Compound P180

In a 500ml single-neck flask, 13g (50mmol) of M8, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P180, wherein the theoretical value of M/Z is 428, and the actual value of M/Z is 429.

Synthetic example 24: synthesis of Compound P181

In a 500ml single-neck flask, 16g (50mmol) of M9, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P181, wherein the theoretical value of M/Z is 483, and the actual value of M/Z is 484.

Synthetic example 25: synthesis of Compound P182

In a 500ml single-neck flask, 13g (50mmol) of M10 and 12.3g (50mmol) of 2-bromobiphenyl were addedAnd furan, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P182, wherein the theoretical value of M/Z is 427, and the actual value of M/Z is 428.

Synthetic example 26: synthesis of Compound P183

In a 500ml single-neck flask, 15g (50mmol) of M11, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P183, wherein the theoretical value of M/Z is 497, and the actual value of M/Z is 498.

Synthetic example 27: synthesis of compound P184

In a 500ml single-neck flask, 15g (50mmol) of M12, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5h, and finishing the reactionAfter that, the reaction was stopped to obtain a reaction solution. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P184, wherein the theoretical value of M/Z is 469, and the actual value of M/Z is 470.

Synthetic example 28: synthesis of Compound P185

In a 500ml single-neck flask, 13.5g (50mmol) of M13, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P185, wherein the theoretical value of M/Z is 441, and the actual value of M/Z is 442.

Synthetic example 29: synthesis of Compound P186

In a 500ml single-neck flask, 13.5g (50mmol) of M14, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P186, wherein the theoretical value of M/Z is 441, and the actual value of M/Z is 442.

Synthetic example 30: synthesis of compound P187

In a 500ml single-neck flask, 14.4g (50mmol) of M15, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P187, wherein the theoretical value of M/Z is 455, and the actual value of M/Z is 456.

Synthetic example 31: synthesis of Compound P188

In a 500ml single-neck flask, 14.4g (50mmol) of M16, 12.3g (50mmol) of 2-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P188, wherein the theoretical value of M/Z is 455, and the actual value of M/Z is 456.

Synthetic example 32: synthesis of Compound P189

In a 500ml single-necked flask, 18.5g (50mmol) of M17, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P189, wherein the theoretical value of M/Z is 569, and the actual value of M/Z is 570.

Synthetic example 33: synthesis of Compound P190

In a 500ml single-neck flask, 22.5g (50mmol) of M18, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. And cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating an organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P190, wherein the theoretical value of M/Z is 645, and the actual value of M/Z is 646.

Synthesis example 34: synthesis of Compound P191

In a 500ml single-necked flask, 26.5g (50mmol) of M19, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of toluene(Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P191, wherein the theoretical value of M/Z is 721, and the actual value of M/Z is 722.

Synthetic example 35: synthesis of compound P192

In a 500ml single-necked flask, 18.5g (50mmol) of M20, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P192, wherein the theoretical value of M/Z is 586, and the actual value of M/Z is 587.

Synthetic example 36: synthesis of Compound P193

In a 500ml single-necked flask, 23.5g (50mmol) of M21, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, and adding the concentrated organic phaseStirring the methanol for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P193, wherein the theoretical value of M/Z is 661, and the actual value of M/Z is 662.

Synthetic example 37: synthesis of Compound P194

In a 500ml single-necked flask, 27.2g (50mmol) of M22, 13.6g (50mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P194, wherein the theoretical value of M/Z is 737, and the actual value of M/Z is 738.

Synthetic example 38: synthesis of Compound P12

In a 500ml single-necked flask, 15g (50mmol) of M1, 18g (50mmol) of 1-bromo-2- (1-naphthyl) biphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and filtering to obtain light yellow powder which is a compound shown as a structural formula P12, wherein the theoretical value of M/Z is 579, and the actual value of M/Z is 580.

Synthetic example 39: synthesis of Compound P38

In a 500ml single-necked flask, 15g (50mmol) of M1, 16g (50mmol) of 4-bromo-9-phenyl-carbazole, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P38, wherein the theoretical value of M/Z is 542, and the actual value of M/Z is 543.

Synthetic example 40: synthesis of Compound P128

In a 500ml single-necked flask, 12.3g (50mmol) of M6, 15g (50mmol) of 2-bromobenzonaphthofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P128, wherein the theoretical value of M/Z is 449, and the actual value of M/Z is 450.

Synthesis example 41: synthesis of Compound P213

In a 500ml single-neck flask, 15g (50mmol) of M1, 21.8g (50mmol) of Z1, 0.9g (1mmol) of tris (dibenzylideneacetone) were charged) Dipalladium (i.e. Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain light yellow powder which is a compound shown as a structural formula P213, wherein the theoretical value of M/Z is 633, and the actual value of M/Z is 634.

Synthesis example 42: synthesis of compound P218

In a 500ml single-neck flask, 30g (100mmol) of M1, 13g (50mmol) of Z2, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P218, wherein the theoretical value of M/Z is 701, and the actual value of M/Z is 702.

Synthetic example 43: synthesis of Compound P224

In a 500ml single-neck flask, 30g (100mmol) of M1, 16.5g (50mmol) of Z3, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction solution to room temperature, and separating the reaction solutionConcentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and vacuum filtering to obtain light yellow powder which is a compound shown as a structural formula P224, wherein the theoretical value of M/Z is 777, and the measured value of M/Z is 778.

Synthetic example 44: synthesis of Compound P241

In a 500ml single-neck flask, 32g (100mmol) of M2, 18g (50mmol) of Z4, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating an organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P241, wherein the theoretical value of M/Z is 834, and the actual value of M/Z is 835.

Synthetic example 45: synthesis of Compound P245

In a 500ml single-neck flask, 15.8g (50mmol) of M2, 10.3g (50mmol) of Z5, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)₂(dba)₃) 0.5mL of tributylphosphine ((t-Bu)₃P), 300ml of Toluene (Toluene) and 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, heating the reaction to 110 ℃ for reaction for 5 hours, and stopping the reaction after the reaction is finished to obtain reaction liquid. Cooling the reaction liquid to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol into the concentrated organic phase, stirring for 1h, and performing suction filtration to obtain a light yellow powder which is a compound shown as a structural formula P245, wherein the theoretical value of M/Z is 443, and the actual value of M/Z is 444.

Device example 1

The preparation process of the organic electroluminescent device in the embodiment is as follows:

the glass plate coated with the ITO transparent conductive layer (as anode) was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;

placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10^-5Pa, performing vacuum evaporation on the anode layer film to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;

the compound P1 prepared in example 1 was vacuum-evaporated on the hole injection layer at an evaporation rate of 0.1nm/s and a total film thickness of 80nm as a hole transport layer of the device;

on the hole transport layer, vacuum evaporation plating HT-14 as an electron barrier layer of the device, wherein the evaporation plating rate is 0.1nm/s, and the total film thickness of the evaporation plating is 80 nm;

a luminescent layer of the device is vacuum evaporated on the electron blocking layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material GPH-59 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-8 is 3% of the evaporation rate of the main material, the proportion is set, and the total evaporation film thickness is 30 nm;

vacuum evaporating electron transport layer materials ET-46 and ET-57 of the device on the light emitting layer, wherein the mass ratio of the two materials is 1:1, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;

LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.

Device examples 2 to 7

The organic electroluminescent device in each device example was produced in the same manner as in device example 1 except that compound P1 was replaced with the corresponding compound in table 1 as the hole transport layer material.

Device comparative example 1

In this comparative example, the organic electroluminescent device was prepared in the same manner as in example 1 except that compound P1 was replaced with a compound having the following structure III as a hole transporting material:

the following performance measurements were made for the organic electroluminescent devices prepared in device examples 1 to 7 and device comparative example 1:

the driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1 to 7 and device comparative example 1 and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 5000cd/m²The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m²The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance²Time in hours. The measurement results are shown in table 1.

TABLE 1

As can be seen from the results in Table 1, when the compound of the present invention is used as a hole transport material for an organic electroluminescent device, the luminance of the device reaches 5000cd/m²When the hole transport material is used, the driving voltage is low below 8.9V, the current efficiency is as high as more than 13cd/A, LT95 is more than 16h, the driving voltage can be effectively reduced, the current efficiency is improved, the service life of the device is prolonged, and the hole transport material is good in performance.

In contrast to the compound P3 in example 3, the compound III in comparative example 1, which is different from the compound P3 in example 3 in that only the cyclohexyl group of the alkyl moiety is changed to a polycyclic group, when it is used as a hole transport material for an organic electroluminescent device, has a device driving voltage of 10.5V, a current efficiency of 8.5cd/a, and a LT95 lifetime of 6h, and the data are inferior to those in example 3, which may be attributed to the fact that the compound P3 has better intermolecular stacking and thus better hole transport properties.

Device example 8

The organic electroluminescent device preparation in this example differs from the device example 1 described above in that:

evaporating HT-4 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm; vacuum evaporating a compound P2 on the hole transport layer to be used as an electron blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 5 nm; a luminescent layer of the device is vacuum evaporated on the electron barrier layer, the luminescent layer comprises a main material and a dye material, BFH-2 is adjusted to be used as the main material by utilizing a multi-source co-evaporation method, the evaporation rate is 0.1nm/s, the evaporation rate of dye BFD-4 is set in a proportion of 3%, and the total evaporation film thickness is 30 nm; forming an electron transport layer by vacuum evaporation of an electron transport layer material ET46 of the device on the light emitting layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm; LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.

Device examples 9-15 differ from device example 8 only in that the hole transport material compound P2 was replaced with another compound, as specified in table 2. Device comparative example 2

In this comparative example, an organic electroluminescent device was produced in the same manner as in device example 8 except that compound P2 was replaced with a compound having the following structure III as an electron blocking material:

the following performance measurements were made on the organic electroluminescent devices prepared by the procedures of the above device examples 8 to 15 and device comparative example 2:

the driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 8 to 15 and device comparative example 2 and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 5000cd/m²The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m²The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance²The time (d) is in hours, and the measurement results are shown in Table 2.

TABLE 2

As can be seen from the data in Table 2, when the compound of the invention is used as an electron barrier material of an organic electroluminescent device, the luminance of the device reaches 5000cd/m²When the material is used, the driving voltage is low below 8.5V, the current efficiency is as high as more than 11cd/A, LT95 is more than 17h, the driving voltage can be effectively reduced, the current efficiency is improved, the service life of the device is prolonged, and the material is an electron barrier material with good performance.

Compared with the compound P3 in the device example 9, the difference between the compound III in the device comparative example 2 and the compound P3 in the device example 9 is that only the cyclohexyl of the alkyl part is changed into the polycyclic group, when the compound is used as a hole transport material of an organic electroluminescent device, the driving voltage of the device is 9.8V, the current efficiency is 10.8cd/A, the service life of LT95 is 12h, and all data are poor compared with the device example 9, which may be attributed to the fact that the compound P3 has better intermolecular accumulation and thus has better hole transport performance.

Device example 16

The preparation process of the organic electroluminescent device in the embodiment is as follows:

the glass plate coated with the ITO (50nm) transparent conductive layer is subjected to ultrasonic treatment in a commercial cleaning agent, washed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent (volume ratio is 1: 1), baked in a clean environment until the moisture is completely removed, cleaned by ultraviolet light and ozone, and the surface is bombarded by low-energy cation beams.

Placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10^-5Vacuum evaporating 2-TNATA (4,4' -tris [ N, N- (2-naphthyl) -phenylamino ] group on the anode layer film]Triphenylamine) to form a hole injection layer having a thickness of 60 nm; a compound NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 20nm at a deposition rate of 0.1 nm/s.

Forming an electroluminescent layer on the hole transport layer, and specifically operating as follows: the compound TDH1 as a light-emitting layer host was placed in a cell of a vacuum vapor deposition apparatus, the compound P213 as a dopant was placed in another cell of the vacuum vapor deposition apparatus, and the two materials were simultaneously evaporated at different rates, the concentration of the compound P213 was 20 wt%, and the total film thickness by evaporation was 30 nm.

Bphen was vacuum evaporated on the light emitting layer to form an electron transport layer with a thick film of 20nm at an evaporation rate of 0.1 nm/s.

And (3) performing vacuum evaporation on the electron transport layer to form a LiF layer with the thickness of 0.5nm as an electron injection layer and an Al layer with the thickness of 150nm as a cathode of the device.

Device examples 17 to 20 differ from device example 16 only in that the hole transport material compound P213 was replaced with another compound, as specified in table 3.

Device comparative example 3

In this comparative example, an organic electroluminescent device was produced in the same manner as in device example 16 except that compound P213 was replaced with a compound having the following structure IV as a light-emitting dopant:

the organic electroluminescent devices obtained in device examples 16 to 20 and device comparative example 3 were subjected to the performance test described above, and the test results are shown in table 3.

TABLE 3

	Electron barrier material	Required luminance (cd/m)2)	Voltage (V)	Current efficiency (cd/A)
					Comparative example 3	IV	1000.00	7.2	9.1
Example 16	P213	1000.00	6.5	9.9
					Example 17	P218	1000.00	5.8	11.2
Example 18	P224	1000.00	6.2	10.8
					Example 19	P241	1000.00	5.2	11
Example 20	P245	1000.00	6.8	10.6

As can be seen from the data in Table 3, when the compound of the present invention is used as an electron blocking layer material of an organic electroluminescent device, the luminance of the device reaches 1000cd/m²When the driving voltage is lower than 6.8V, the current efficiency is higher than 9.9cd/A, and compared with a device prepared from a comparative compound, the blue light-emitting diode can realize more blue light emission.

Compared with the compound P245 in the device example 20, the compound IV in the device comparative example 3 is different in that only the cyclohexyl group of the alkyl part is changed into a polycyclic group, when the compound is used as a dopant of an organic electroluminescent device, the driving voltage of the device is 7.2V, the current efficiency is 9.1cd/A, and each item of data is worse compared with the device example 20, which is probably due to the fact that the compound P245 has a higher triplet state (the triplet state energy levels of the Gaussian calculation comparison column and the P245 are respectively 2.52eV and 2.67eV), and the better intermolecular distance can effectively reduce the luminescent molecule quenching and the refractive index of the material with better linear arrangement of the molecules so as to improve the light extraction rate of the device.

The present invention is illustrated by the above examples of the compounds of the present invention and their application in OLED devices, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention has to be implemented by means of the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.