Aromatic amine derivative organic electroluminescent material and device thereof

文档序号：1810290 发布日期：2021-11-09 浏览：18次中文

阅读说明：本技术 芳香族胺衍生物有机电致发光材料及其器件 (Aromatic amine derivative organic electroluminescent material and device thereof ) 是由张少博王峥毕欣夏传军邝志远于 2020-05-08 设计创作，主要内容包括：公开了芳香族胺衍生物有机电致发光材料及其器件。所述化合物为芳香族胺取代的芘类化合物,在其中芳胺的一个芳基N-邻位引入取代基且在N-对位引入含有邻位取代基的(杂)芳基,在另一个芳基的N-邻位引入取代基可以在增加分子共轭性和稳定性的同时减少分子各共轭体系的平面性。所述化合物可用作有机电致发光器件中发光材料。这些新型化合物能提供更好的器件性能,如器件寿命和外部量子效率。还公开了一种电致发光器件和化合物配方。(Disclosed are an aromatic amine derivative organic electroluminescent material and a device thereof. The compound is an aromatic amine substituted pyrene compound, wherein a substituent is introduced to the N-ortho position of one aryl of aromatic amine, a (hetero) aryl containing an ortho substituent is introduced to the N-para position, and the introduction of a substituent to the N-ortho position of the other aryl can increase the conjugation and stability of molecules and reduce the planarity of each conjugated system of the molecules. The compound can be used as a light-emitting material in an organic electroluminescent device. These novel compounds can provide better device performance such as device lifetime and external quantum efficiency. An electroluminescent device and compound formulation are also disclosed.)

1. A compound having the structure of formula 1:

wherein, in the formula 1,

substituent R₁-R₁₀Wherein at least one substituent has a structure represented by formula 2:

and the substituent R₁-R₁₀The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilane having 6 to 20 carbon atoms.A group, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

wherein, in the formula 2,

"' represents the position of the substituent with the structure of formula 2 connected with formula 1;

each occurrence of L is selected, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

X₁to X₄Selected from CR, identically or differently at each occurrence_x1Or N;

Y₁to Y₃Selected from CR, identically or differently at each occurrence_y1Or N;

Z₁to Z₄Selected from CR, identically or differently at each occurrence_z1Or N;

R_x1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms；

R_y1And R_z1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, mercapto, phosphino, and combinations thereof having 0-20 carbon atoms;

R_x，R_yand R_zEach occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.

2. The compound of claim 1, wherein substituent R₁To R₁₀At least two of which have a structure represented by formula 2; preferably, the substituent R₁-R₁₀Two of which have a structure represented by formula 2.

3. The compound of any one of claims 1-2, wherein substituent R₁And R₆Has a structure represented by formula 2.

4. A compound according to any one of claims 1 to 3, R₂，R₄-R₅，R₇And R₉-R₁₀Is hydrogen, a substituent R₃And R₈The same or different at each occurrence is selected from hydrogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

5. The compound of any one of claims 1-4, R_x1Each occurrence identically or differently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or combinations thereof;

more preferably, R_x1Each occurrence is selected from hydrogen, deuterium, fluoro, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, trifluoromethyl, cyano, trimethylsilyl, or a combination thereof.

6. A compound according to any one of claims 1 to 5, wherein the substituent R_y1Each occurrence identically or differently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or combinations thereof;

more preferably, wherein the substituent R_y1Each occurrence, the same or different, is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, phenyl, trimethylsilyl, or a combination thereof.

7. The compound of claim 1, formula 2 is further represented by formula 3, formula 4, or formula 5:

"' represents the position where the structure represented by formula 3, formula 4 and formula 5 is linked to formula 1;

L、R_x、R_y、R_Zand R_z1Have the same definitions as in claim 1.

8. The compound of any one of claims 1-7, wherein L, identically or differently on each occurrence, is selected from a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1-20 carbon atoms, a substituted or unsubstituted arylene group having 6-12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3-12 carbon atoms;

preferably, L is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group;

more preferably, L is a single bond.

9. A compound according to any one of claims 1 to 8, wherein the substituent R_z1Each occurrence identically or differently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or combinations thereof;

more preferably, wherein the substituent R_z1Each occurrence, identically or differently, is selected from the group consisting of methyl, ethyl, isopropyl, butyl, cyclopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclopentylHexyl, deuterated phenyl, deuterated methylphenyl, or a combination thereof.

10. The compound of any one of claims 1-9, wherein substituent R_x，R_y，R_zEach occurrence identically or differently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or combinations thereof;

preferably, R_x，R_y，R_zIdentical or different at each occurrence is selected from the group consisting of methyl, ethyl, isopropyl, butyl, isobutyl, tert-butyl, neopentyl, cyclopropyl, cyclopentyl, cyclohexyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl.

11. The compound of claim 1, wherein the compound is selected from the group consisting of:

wherein TMS represents trimethylsilyl.

12. An electroluminescent device, comprising:

an anode, a cathode, a anode and a cathode,

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of formula 1:

wherein, in the formula 1,

substituent R₁-R₁₀Wherein at least one substituent has a structure represented by formula 2;

and the substituent R₁-R₁₀The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

wherein, in the formula 2,

"' represents the position of the substituent with the structure of formula 2 connected with formula 1;

each occurrence of L is selected, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

X₁to X₄Selected from CR, identically or differently at each occurrence_x1Or N;

Y₁to Y₃Selected from CR, identically or differently at each occurrence_y1Or N;

Z₁to Z₄Selected from CR, identically or differently at each occurrence_Z1Or N;

R_y1and R_Z1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, mercapto, phosphino, and combinations thereof having 0-20 carbon atoms;

R_x，R_yand R_zEach occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstitutedCycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

13. The organic electroluminescent device as claimed in claim 12, wherein the organic layer comprises a light emitting layer, wherein the light emitting layer comprises a compound having formula 1.

14. The organic electroluminescent device of claim 13, wherein the light emitting layer further comprises a compound having formula 6:

wherein, in the formula 6,

R_g1to R_g8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

R_g9and R_g10Identical or different at each occurrenceSelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 6 to 30 carbon atoms.

15. A compound formulation comprising a compound as defined by any one of claims 1 to 11.

Technical Field

The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. And more particularly, to a pyrene compound substituted with an aromatic amine and an organic electroluminescent device and a compound formulation including the same.

Background

Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.

In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.

OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLED phosphorescent materials have been successfully commercialized. The existing phosphorescent blue OLED has the problems of short service life, difficulty in reaching deep blue, blue unsaturation, high working voltage and the like. The fluorescent blue OLED has a longer lifetime than the phosphorescent blue OLED, but has a low efficiency, and thus it is highly desirable to improve the efficiency and other properties of the fluorescent blue electroluminescent device.

KR1020110054192A discloses triarylamine compounds with pyrene as core, and its general formula isIn this application R₁-R₅At least one of which is a cyano substituent and at least one of which is a substituted or unsubstituted aryl group, most of the disclosed embodiments being aromatic amines in which the cyano substituent is located ortho to the N of one of the aryl substituents, andwithout further limitation of R₃Unlike the arylamine claimed in the present application, in which an ortho-substituted aryl group is further introduced into the N para position of the aryl substituent group, it is noted that the present invention is not concerned with the influence of the introduction of the ortho-substitution on the device performance.

KR1020140076170A discloses a study on triarylamine compounds with pyrene as core, and its general formula isThe compound must simultaneously contain an electron-withdrawing group and a deuterated aryl, wherein the electron-withdrawing substituent is halogenCyano and trifluoromethyl, the specific structure beingThe ortho substituents of the N-substituted aryl groups referred to in this application are electron withdrawing fluorine atoms and deuterated aryl groups and there is no disclosure or teaching that the presence of an N-ortho substituent on both aryl groups of an aromatic amine would improve device performance.

CN106170474A reports the research of triarylamine compounds with pyrene as a core, and the general formula of the triarylamine compounds isThe concrete structure is thatAlthough the application relates to a structure that two aryl groups of the arylamine have ortho-position substitution, the aryl group is further introduced into the N-para position of the arylamine to increase the conjugation property and stability of molecules so as to realize good luminous efficiency of a blue light device.

These documents disclose fluorescent light-emitting materials having an aromatic amine structure with pyrene as a core. Diarylamine substituted pyrene compounds have an important position in the field of fluorescent blue light, but fluorescent luminescent materials still need to be developed further to obtain higher device performance.

Disclosure of Invention

The invention aims to provide a series of novel pyrene compounds with aromatic amine structures to solve at least part of the problems. The compound can be used as a light-emitting material in an organic electroluminescent device. These novel compounds can provide better device performance such as external quantum efficiency and device lifetime.

According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:

wherein, in the formula 1,

R₁-R₁₀wherein at least one substituent has a structure represented by formula 2:

wherein, in the formula 2,

"' represents the position of the substituent with the structure of formula 2 connected with formula 1;

each occurrence of L is selected, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

X₁to X₄Selected from CR, identically or differently at each occurrence_x1Or N;

Y₁to Y₃Selected from CR, identically or differently at each occurrence_y1Or N;

Z₁to Z₄Selected from CR, identically or differently at each occurrence_z1Or N;

R_y1and R_z1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, mercapto, phosphino, and combinations thereof having 0-20 carbon atoms;

R_x，R_yand R_zAt each occurrenceThe same or different is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising the compound having the structure of formula 1. The specific structures of the compounds are described in the preceding examples.

According to another embodiment of the present invention, there is also disclosed a compound formulation comprising the compound having the structure of formula 1. Specific structures of the compounds are described in the preceding examples.

The pyrene compounds with a series of novel aromatic amine structures provided by the invention can be used as luminescent materials in organic electroluminescent devices. The novel compounds introduce an aryl group containing an ortho-position substituent at the N-para position of one aryl group of the arylamine, further have a substituent at the N-ortho position, and contain a substituent at the N-ortho position of the other aryl group of the arylamine, so that the conjugation property and the stability of molecules can be improved, and the planarity of each conjugated system of the molecules can be reduced. The novel compounds can provide better device performance such as external quantum efficiency, device life and the like when being applied to an organic electroluminescent device.

Drawings

FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.

Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.

Detailed Description

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:1₄TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.

In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.

Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.

The materials and structures described herein may also be used in other organic electronic devices as previously listed.

As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.

As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.

A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).

On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate a transition from a triplet state back to a singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of the backfill singlet excited state may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.

The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)_S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ E_S-T. These states may include CT states. In generalDonor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).

Definitions for substituent terms

Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.

Alkyl-comprises both straight and branched chain alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbons in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferable.

Cycloalkyl-as used herein, comprises a cyclic alkyl group. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.

Alkenyl-as used herein, encompasses both straight and branched chain olefinic groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group. In addition, alkenyl groups may be optionally substituted.

Alkynyl-as used herein, straight and branched alkynyl groups are contemplated. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chicory, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl.

Heterocyclyl or heterocyclic-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.

Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated which may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothienopyridine, thienobipyridine, benzothiophenopyridine, cinnolinopyrimidine, selenobenzodipyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.

Alkoxy-is represented by-O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.

Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.

Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-2-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable.

The term "aza" in azafluorene, azaspirobifluorene ring, azadibenzofuran, aza-dibenzothiophene, etc., means that one or more C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.

In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted with one or more members selected from deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having from 1 to 20 carbon atoms, an unsubstituted aralkyl group having from 7 to 30 carbon atoms, an unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted aryloxy group having from 6 to 30 carbon atoms, an unsubstituted alkenyl group having from 2 to 20 carbon atoms, an unsubstituted aryl group having from 6 to 30 carbon atoms or, preferably, an unsubstituted aryl group having from 6 to 12 carbon atoms, an unsubstituted heteroaryl group having from 3 to 30 carbon atoms or, preferably, an unsubstituted heteroaryl group having from 3 to 12 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.

In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device. In the compounds mentioned in the present disclosure, a deuterated substituent, such as deuterated methyl, means that at least one hydrogen atom in said substituent (methyl) is replaced by deuterium.

In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.

In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.

The expression that two adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

the expression that two adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

further, the expression that two adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:

according to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:

wherein, in the formula 1,

R₁-R₁₀wherein at least one substituent has a structure represented by formula 2:

wherein, in the formula 2,

"' represents the position of the substituent with the structure of formula 2 connected with formula 1;

l is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;

X₁to X₄Selected from CR, identically or differently at each occurrence_x1Or N;

Y₁to Y₃Selected from CR, identically or differently at each occurrence_y1Or N;

Z₁to Z₄Selected from CR, identically or differently at each occurrence_z1Or N;

R_y1and R_z1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryloxy groupOr unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, mercapto group, phosphino group, and combinations thereof;

In this example, the substituent R in formula 1₁To R₁₀Wherein at least one substituent has a structure represented by formula 2, and R₁To R₁₀The remainder of (a) are selected, identically or differently on each occurrence, from the group consisting of the substituents mentioned above. For example, when the substituent R₁Having a structure represented by formula 2, then R₁To R₁₀The remainder of (1), namely R₂To R₁₀Each occurrence is selected, identically or differently, from the group consisting of the substituents mentioned above. When the substituent R is₁And R₆Having a structure represented by formula 2, then R₁To R₁₀The remainder of (1), namely R₂To R₅And R₇To R₁₀Each occurrence is selected, identically or differently, from the group consisting of the substituents mentioned above. According to one embodiment of the invention, wherein the substituent R₁To R₁₀At least two of which have a structure represented by formula 2.

According to one embodiment of the invention, wherein the substituent R₁-R₁₀Two of which have a structure represented by formula 2.

According to one embodiment of the invention, wherein the substituent R₁And R₆Has a structure represented by formula 2.

According to one embodiment of the invention, R₂，R₄-R₅，R₇And R₉-R₁₀Is hydrogen, a substituent R₃And R₈Each occurrence, identically or differently, is selected from hydrogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

According to one embodiment of the invention, wherein the substituent R_x1Each occurrence is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or combinations thereof.

According to one embodiment of the invention, wherein the substituent R_x1Each occurrence, the same or different, is selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted silyl having 3 to 20 carbon atoms, or combinations thereof.

According to one embodiment of the invention, wherein R_x1Identically or differently at each occurrence is selected from hydrogen, deuterium, fluoro, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, trifluoromethyl, cyano, trimethylsilyl, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_y1Each occurrence, the same or different, is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_y1Is selected, identically or differently on each occurrence, from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 6 to 12An aryl group of carbon atoms, a substituted or unsubstituted alkylsilyl group of 3-20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_y1Identically or differently at each occurrence is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, phenyl, trimethylsilyl, or a combination thereof.

According to an embodiment of the present invention, formula 2 is further represented by formula 3, formula 4, or formula 5:

wherein, in formula 3, formula 4 and formula 5,

"' represents the position where the structure represented by formula 3, formula 4 and formula 5 is linked to formula 1;

each occurrence of L is selected, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

R_z1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atomsMercapto, phosphino, and combinations thereof;

According to one embodiment of the invention, wherein L is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms.

According to one embodiment of the invention, wherein L is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

According to one embodiment of the invention, wherein L is a single bond.

According to one embodiment of the invention, wherein the substituent R_z1Each occurrence, the same or different, is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_z1Each occurrence being the same or different and is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted aryl groups having 3 to 2A silane group of 0 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_z1Selected from, at each occurrence, methyl, ethyl, isopropyl, butyl, cyclopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, deuterated methylphenyl, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_x，R_y，R_zEach occurrence, the same or different, is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein the substituent R_x，R_y，R_zIdentical or different at each occurrence is selected from the group consisting of methyl, ethyl, isopropyl, butyl, isobutyl, tert-butyl, neopentyl, cyclopropyl, cyclopentyl, cyclohexyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl.

According to one embodiment of the present invention, the compound is selected from the group consisting of compound BD1 to compound BD622, and the specific structures of compound BD1 to compound BD622 are shown in claim 11.

According to an embodiment of the present invention, there is also disclosed an electroluminescent device, including:

an anode, a cathode, a anode and a cathode,

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of formula 1:

wherein, in the formula 1,

R₁-R₁₀each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

and, R₁-R₁₀Wherein at least one substituent has a structure represented by formula 2;

wherein, in the formula 2,

"' represents a position where a substituent having formula 2 is attached to formula 1;

each occurrence of L is selected, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

X₁to X₄Identical in each occurrence orAre differently selected from CR_x1Or N;

Y₁to Y₃Selected from CR, identically or differently at each occurrence_y1Or N;

Z₁to Z₄Selected from CR, identically or differently at each occurrence_z1Or N;

R_y1and R_z1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted with 0-20Amino, mercapto, phosphino, and combinations thereof, of carbon atoms;

R_x，R_yand R_zThe same or different at each occurrence is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.

According to one embodiment of the present invention, wherein the organic layer comprises a light emitting layer, wherein the light emitting layer comprises a compound having formula 1.

According to one embodiment of the present invention, wherein the light emitting layer further comprises a host material.

According to one embodiment of the present invention, wherein the light emitting layer further comprises a compound having formula 6:

wherein, in the formula 6,

R_g1to R_g8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted with 0-20 carbon atoms of an amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

R_g9and R_g10Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 6 to 30 carbon atoms.

According to one embodiment of the present invention, there is also disclosed a compound formulation comprising a compound having the structure of formula 1, the specific structure of which is shown in any of the preceding embodiments.

In combination with other materials

The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.

Materials synthesis example:

the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:

synthesis example 1: synthesis of Compound BD9

First step of

4-bromo-2-methylaniline (500g, 2687mmol), o-tolylboronic acid (40.0g, 295.6mmol), tetrakis (triphenylphosphine) palladium (9.3g, 8.1mmol) and potassium carbonate (93.0g, 671.8mmol) were added to tetrahydrofuran/water (3/1,1300.0mL) at room temperature in this order under a nitrogen atmosphere, and then the mixture was heated to 80 ℃ to react overnight, after completion of the reaction, celite was filtered while hot, the filtrate was concentrated and purified by column chromatography to give intermediate 1 as a clear oil (26.0g, 131.8mmol, 49% yield).

Second step of

Tris (dibenzylideneacetone) dipalladium (6.0g,6.6mmol),1,1 '-binaphthyl-2, 2' -bisdiphenylphosphine (8.0g,13.2mmol) was added to toluene (1000mL) at room temperature under nitrogen. Introducing N into the solution₂After 20 min, intermediate 2(41.0g, 158.2mmol), intermediate 1(26.0g, 131.8mmol), sodium tert-butoxide (31.0g, 330.0mmol) were added. Continuously introducing N₂After 10 minutes, the system was heated to 110 ℃ for 4 hours. The reaction solution was filtered, washed with toluene, the solvent removed by rotation and column chromatography to give intermediate 3(35.0g, 92.7mmol, 70% yield) as a white solid.

The third step

Palladium acetate (37.0mg,0.17mmol), tris (tert-butyl) phosphine tetrafluoroborate (97.0mg,0.33mmol) was added to xylene (40mL) at room temperature under nitrogen. Introducing N into the solution₂After 20 min, 1, 6-dibromopyrene (2.0g,5.56mmol), intermediate 3(5.2g, 13.89mmol), sodium tert-butoxide (1.7g,17.5mmol) were added successively. Continuously introducing N₂For 10 minutes, the system was heated to 90 ℃ until the reaction was complete. The reaction was filtered and washed with toluene, and recrystallized multiple times from toluene to give the desired product BD9 as a yellow-green solid (1.6g, 1.68mmol, 30% yield). The product was identified as the target product and had a molecular weight of 952.

Synthesis example 2: synthesis of compound BD549

Intermediate 3(10.7g,28.36mmol) and potassium tert-butoxide (5.7g,51mmol) were dissolved in deuterated dimethyl sulfoxide (25g) at room temperature under nitrogen protection and stirred at room temperature for 10 min. Slowly heating to 70 ℃, cooling to room temperature after 4H, extracting by a DCM/H2O system, and concentrating. Column chromatography eluting with PE/TOL (10:1) gave intermediate 4(yiled 90%).

Palladium acetate (37.0mg,0.17mmol), tris (tert-butyl) phosphine tetrafluoroborate (97.0mg,0.33mmol) was added to xylene (40mL) at room temperature under nitrogen. Introducing N into the solution₂After 20 min, 1, 6-dibromopyrene (2.0g,5.56mmol), intermediate 4(5.3g, 13.89mmol), sodium tert-butoxide (1.7g,17.5mmol) were added successively. Continuously introducing N₂For 10 minutes, the system was heated to 90 ℃ until the reaction was complete. The reaction was filtered and washed with toluene and recrystallized several times from toluene to give the desired product BD549 as a yellow-green solid (1.1g, 1.05mmol, 19% yield). The product was identified as the target product and had a molecular weight of 976.

Synthesis comparative example 1: synthesis of comparative Compound B

The first step is as follows:

tris (dibenzylideneacetone) dipalladium (6.0g,6.6mmol),1,1 '-binaphthyl-2, 2' -bisdiphenylphosphine (8.0g,13.2mmol) was added to toluene (1000mL) at room temperature under nitrogen. Introducing N into the solution₂After 20 min, 2-methyl-4-phenylbromide (36.9g, 150mmol), 2-methyl-4-phenylaniline (32.9g, 180mmol), sodium tert-butoxide (31.6g, 330.0mmol) were added successively. Continuously introducing N₂After 10 minutes, the system was heated to 110 ℃ for 4 hours. The reaction solution was filtered and washed with toluene, the solvent was removed and column chromatography gave intermediate 5 as a white solid (35.2g, 101mmol, 67% yield).

The second step is that:

palladium acetate (71.1mg,0.33mmol), tri-tert-butylphosphine tetrafluoroborate (194.0mg,0.66mmol) were added to xylene (40mL) at room temperature under nitrogen. Introducing N into the solution₂20 minutes1, 6-dibromopyrene (2.4g,6.76mmol), intermediate 5(5.2g, 14.89mmol), sodium tert-butoxide (1.7g,17.5mmol) were added successively. N was continued for 210 minutes and the system was heated to 90 ℃ until the reaction was complete. The reaction was filtered and washed with toluene and recrystallized multiple times from toluene to give the desired product compound B as a yellow-green solid (3.55g, 3.68mmol, 54.4% yield). The product was identified as the target product and had a molecular weight of 896.

Synthesis comparative example 2: synthesis of comparative Compound C

The first step is as follows:

palladium acetate (112.5mg,0.5mmol), tris (tert-butyl) phosphine tetrafluoroborate (289mg,1mmol) was added to xylene (100mL) at room temperature under nitrogen. Introducing N into the solution₂After 20 minutes, 1, 6-dibromopyrene (3.6g, 10mmol), bis (4-biphenylyl) amine (7.0g, 22mmol) and sodium tert-butoxide (2.13g,22.22mmol) were added successively. Continuously introducing N₂For 10 minutes, the system was heated to 90 ℃ until the reaction was complete. The reaction was filtered and washed with toluene, and recrystallized from toluene several times to obtain the objective compound C (2.4g,2.85mmol, yield 28.5%). The product was identified as the target product and had a molecular weight of 840.

It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.

Device embodiments

Device example 1

First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees^-8In the case of torr, the evaporation was performed by thermal vacuum evaporation at a rate of 0.2 to 2 angstroms/second in turn on an ITO anode. Compound HI as Hole Injection Layer (HIL)). The compound HT is used as a Hole Transport Layer (HTL). Compound EB was used as an Electron Blocking Layer (EBL). Then compound BD9 was doped in compound BH and co-evaporated to serve as the light emitting layer (EML). Compound HB was used as a Hole Blocking Layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.

Device example 2

Device comparative example 2 was carried out in the same manner as in device example 1 except that BD549 was used instead of compound BD9 in the light-emitting layer (EML).

Device comparative example 1

Device comparative example 1 was conducted in the same manner as in device example 1 except that compound a was used in place of compound BD9 in the light-emitting layer (EML).

Device comparative example 2

Device comparative example 2 was conducted in the same manner as in device example 1 except that the compound B was used in place of the compound BD9 in the light emitting layer (EML).

Device comparative example 3

Device comparative example 3 was conducted in the same manner as in device example 1 except that compound C was used in place of compound BD9 in the light-emitting layer (EML).

The detailed structure and thickness of the device layer portions are shown in table 1. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.

TABLE 1 device structures of device examples and comparative examples

The material structure used in the device is as follows:

the test lifetime LT97 and External Quantum Efficiency (EQE) data at 1000 nits are shown in table 2. LT97 represents the time for the lifetime of the device to decay to 97% of the initial brightness.

TABLE 2 device data

Device numbering	EQE(％)	LT97(hrs)
			Example 1	9.46	616
Example 2	9.56	827
			Comparative example 1	8.88	269
Comparative example 2	8.83	571
			Comparative example 3	7.90	256

Discussion:

compared with comparative example 3, the service life of the product in example 1 is improved by 140%, and the EQE is improved by nearly 20%. Example 2 compared to comparative example 3, the lifetime was improved by 223% and the EQE by 21%. In the same device structure, the fluorescent luminescent material is substituted at the N-ortho position while introducing the aryl containing ortho-substitution into the N-para position of the aryl in the arylamine, so that the service life and the EQE of the device are improved more compared with the fluorescent luminescent material without any ortho-substitution group to generate steric effect.

Example 1 and comparative example 1, the lifetime was improved by 129% and the EQE by 6%. Example 2 and comparative example 1, lifetime was improved by 207% and EQE by 7.6%. Therefore, in the same device structure, when pyrene compound fluorene containing ortho-substituted aryl is introduced into N-para position of arylamine as a fluorescent luminescent material, compared with pyrene compounds introducing aryl substituent into N-meta position, the molecular conjugation property and stability can be effectively improved, meanwhile, due to the steric effect of the ortho-substituted group, the planarity of a molecular conjugation system can be reduced, and finally, the service life and the efficiency of the device are improved.

Comparing example 1 with comparative example 2, the lifetime is improved by about 8% and the EQE is improved by 7%. Comparing example 2 with comparative example 2, the lifetime is improved by about 44.8% and the EQE is improved by 8.2%. It can be seen that in the same device structure, pyrene compounds with ortho-position substituent groups further introduced into N-para-position aryl of arylamine are used as fluorescent luminescent materials, and compared with pyrene compounds without ortho-position aryl substituent groups at N-para-position, the plane property of a molecular conjugated system can be reduced, and longer device service life and higher EQE can be obtained.

In conclusion, in the aromatic amine substituted pyrene compound, a (hetero) aryl group containing an ortho-position substituent is introduced into the N-para position of one aryl group of the arylamine and is substituted at the N-ortho position; the substituent is introduced at the N-ortho position of the other aryl group, and further contains the substituent at other positions, and the obtained compound is applied to a fluorescent luminescent material, so that better device efficiency, such as longer device life and EQE (electron quantum efficiency) can be obtained.

It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.

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