CN111072666A - Organic electroluminescent material and application thereof - Google Patents

Organic electroluminescent material and application thereof Download PDF

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CN111072666A
CN111072666A CN201811218432.4A CN201811218432A CN111072666A CN 111072666 A CN111072666 A CN 111072666A CN 201811218432 A CN201811218432 A CN 201811218432A CN 111072666 A CN111072666 A CN 111072666A
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黄鑫鑫
邢其锋
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Beijing Eternal Material Technology Co Ltd
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Abstract

The present invention discloses compounds of the general formula (1):
Figure DDA0001834140670000011
wherein: y is1～Y8Each independently selected from C, CH or N; x1、X2Each independently selected from a single bond or N, and when one is a single bond, the other is N; r1～R3Each independently selected from the group consisting of: H. c1～C12Alkyl of (C)1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl,Amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C5～C30Heteroarylamino group of (a), substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C5～C30The heteroaryl group of (a); r4Is H, C6～C30Aryl of (C)5～C30One of the heteroaryl groups of (a); a and c are respectively independent integers from 0 to 4, and b is an integer from 0 to 2; l is selected from a single bond or substituted or unsubstituted C6～C30Aryl group of (1). The compound of the present invention shows excellent device performance and stability when used as a light emitting material in an OLED device. The invention also protects the organic electroluminescent device adopting the compound with the general formula.

Description

Organic electroluminescent material and application thereof
Technical Field
The invention relates to an organic electroluminescent material and application of the compound in an organic electroluminescent device.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage direct current drive, full curing, wide viewing angle, light weight, simple composition and process and the like, and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle, low power, 1000 times of response speed of the liquid crystal display, and lower manufacturing cost than the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research of efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The phosphorescent host materials used at present have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts.
Disclosure of Invention
The invention provides a novel general formula compound which can be used as a bipolar compound to be used as a main material of a light-emitting layer, is beneficial to charge balance and realizes high light-emitting efficiency aiming at the problems in the prior art.
The compound of the present invention is represented by the following general formula (1):
Figure BDA0001834140660000021
wherein:
Y1～Y8each independently selected from C, CH or N;
X1、X2each independently selected from a single bond or N, and when one isOne is N;
R1～R3each independently selected from the group consisting of: H. c1～C12Alkyl of (C)1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C5～C30Heteroarylamino group of (a), substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C5～C30One of the heteroaryl groups of (1), R1～R3Two adjacent of the two can be connected to form a ring, or R1～R3Each independently may be fused to the attached aryl or heteroaryl group to form a ring;
R4is H, C6～C30Aryl of (C)5～C30One of the heteroaryl groups of (a);
a and c are respectively independent integers from 0 to 4, and b is an integer from 0 to 2;
l is selected from a single bond or substituted or unsubstituted C6～C30Aryl of (a); n is …
A is a structure represented by the following formula (2):
Figure BDA0001834140660000022
wherein Z is1～Z6Each independently selected from CR 'or N, R' is H, C6～C30Aryl of (C)5～C30And Z is one of the heteroaryl groups of1～Z6At least one of which is N.
When the above groups have substituents, the substituents are respectively and independently selected from halogen, cyano, C1～C10Alkyl or cycloalkyl of, C2～C6Alkenyl or cycloalkenyl of1～C6Alkoxy or thioalkoxy of C6～C30Aryl of (C)3～C30One of the heteroaryl groups of (a).
Further preferably, the compound of the above general formula (1) is represented by the following general formula (1-1) to formula (1-2):
Figure BDA0001834140660000031
among formulae (1-1) to (1-2), A, Y1～Y8、X1、X2、R1～R3、R4L and a, b and c are the same as defined in the general formula (1).
Further preferably, the compound of the above general formula (1) is represented by the following general formulae (1-3) to (1-6):
Figure BDA0001834140660000032
a, Y in formulae (1-3) to (1-6)1～Y8、R1～R3、R4L and a, b and c are the same as defined in the general formula (1).
Still more preferably, in the general formula (1), the general formula (1-1), and the formula (1-2), the general formula (1-3) to the formula (1-6), A is a structure represented by the following formulae (2-1) to (2-4):
Figure BDA0001834140660000041
wherein R is5Is H, C6～C30Aryl of (C)5～C30One of the heteroaryl groups of (a).
Even more preferably, R1～R3Each independently selected from the group consisting of: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
Figure BDA0001834140660000043
Aryl, furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienylOne of isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl;
R4selected from the following groups: hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthyl, triphenylenyl, pyrenyl, perylenyl,
Figure BDA0001834140660000044
One of a group, furyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group and carbazolyl group.
Even more preferably, R5Selected from the following groups: hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthyl, triphenylenyl, pyrenyl, perylenyl,
Figure BDA0001834140660000045
One of a group, furyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group and carbazolyl group.
Further, in the general formula (1) of the present invention, the following specific structural compounds P1 to P81 can be preferably selected, and these compounds are merely representative.
Figure BDA0001834140660000042
Figure BDA0001834140660000051
Figure BDA0001834140660000061
Figure BDA0001834140660000071
Figure BDA0001834140660000081
Figure BDA0001834140660000091
Figure BDA0001834140660000101
Figure BDA0001834140660000111
Figure BDA0001834140660000121
Figure BDA0001834140660000131
Figure BDA0001834140660000141
The invention also provides, as another aspect thereof, the use of a compound as described above in an organic electroluminescent device. The compounds of the invention are preferably used as light-emitting host materials in organic electroluminescent devices.
As still another aspect of the present invention, the present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer comprising at least one light-emitting layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains a compound represented by the above-mentioned general formula (1) or includes at least one compound represented by the above-mentioned general formulae (1-1) to (1-2) or the above-mentioned general formulae (1-3) to (1-6).
The present inventors have found that the compounds of the above general formula of the present invention have good film-forming properties and are suitable for use as a light-emitting host material, and the principle thereof is not clear, and it is presumed that the following reasons may be considered:
the quinazoline is introduced into one end N atom of the indolocarbazole serving as the parent nucleus structure, and the nitrogen-containing heterocycle is introduced into the other end N atom of the indolocarbazole, so that the quinazoline can be used as a bipolar material, and the migration of electrons and holes in the material can be effectively balanced, so that the luminous efficiency is improved.
The introduction of electron-withdrawing moieties (such as pyridine, pyrimidine, triazine, etc.) as substituent groups can make the LUMO value of the compound shallow, which is beneficial to charge injection, thereby achieving the effect of reducing voltage. Meanwhile, the introduction of the electron-withdrawing fragment can effectively improve the charge transfer rate of the material and improve the luminous efficiency of the material.
The compound can be used as a bipolar compound, and is beneficial to the charge balance in a device when being used as a main material of a light-emitting layer of an organic electroluminescent device, so that high light-emitting efficiency can be realized.
The compound of the invention has simple synthesis and easy operation of process, and is suitable for industrial production.
Detailed Description
The present invention will be described in further detail below with reference to specific embodiments in order to make the present invention better understood by those skilled in the art. Compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially.
Synthetic examples
Representative synthetic route 1:
Figure BDA0001834140660000151
representative synthetic route 2:
Figure BDA0001834140660000161
different target compounds can be obtained by substituting different substituents. The above-described synthesis method is not limited to the method of coupling a substituent to an indolocarbazole ring using Suzuki coupling, and one skilled in the art may select other methods such as, but not limited to, Stille coupling, grignard reagent, Kumada-Tamao, and the like, and any equivalent synthesis method may be selected as needed to achieve the purpose of coupling a substituent to an indolocarbazole ring.
Synthesis of intermediate M1:
Figure BDA0001834140660000162
2, 4-dichloroquinazoline (20g, 100mmol), dibenzothiophene-4-boronic acid (22.8g, 100mmol), tetrakis (triphenylphosphine) palladium (1.15g, 1mmol), potassium carbonate (27.6g, 200mmol), 1, 4-dioxane (300 ml) and distilled water (100 ml) were placed in a 1L reaction vessel under a nitrogen atmosphere, and reacted at 100 ℃ for 12 hours under reflux. Cool to room temperature and combine the concentrated organic phases. Separation by column chromatography gave intermediate M125.7g. M is 346.8.
Synthesis of intermediate M2:
Figure BDA0001834140660000163
2, 4-dichloroquinazoline (20g, 100mmol), 2-naphthylboronic acid (17.2g, 100mmol), tetrakis (triphenylphosphine) palladium (1.15g, 1mmol), potassium carbonate (27.6g, 200mmol), 300ml of 1, 4-dioxane, and 100ml of distilled water were placed in a 1L reaction vessel under a nitrogen atmosphere, and reacted at 100 ℃ for 12 hours under reflux. Cool to room temperature and combine the concentrated organic phases. Isolation by column chromatography gave intermediate M224.3g. 290.7.
More specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthesis example 1: synthesis of P1
Figure BDA0001834140660000171
5, 12-indolino [3,2-A ] carbazole (10g, 39.1mmol), 2-chloro-4-phenylquinazoline (11.3g, 46.9mmol), potassium carbonate (10.8g, 78.2mmol) and 200ml of DMF were placed in a 1L reaction vessel under a nitrogen atmosphere, and reacted at 120 ℃ under reflux for 12 hours. Cooled to room temperature, filtered and the filter cake retained. Separation by column chromatography gave 1-a14.5g of intermediate. And M is 460.5.
Figure BDA0001834140660000172
Under a nitrogen atmosphere, intermediate 1-a (14g, 30.4mmol), 5-bromo-2-phenylpyridine (8.5g, 36.5mmol), Pd2(dba)3(0.3g，0.3mmol)、(t-Bu)3HBF4(0.2g, 0.6mmol), t-BuONa (5.8g, 60.8mmol) and 200ml of toluene were placed in a 1L reaction vessel and reacted at 110 ℃ under reflux for 12 hours. Cool to room temperature and combine the concentrated organic phases. The extract was separated by column chromatography to obtain P111.1g. 613.7.
Synthesis example 2: synthesis of P13
Substitution of the 2-chloro-4-phenylquinazoline in synthesis example 1 for intermediate M1, with the others unchanged, gave P13. M: 719.9.
synthesis example 3: synthesis of P46
Substitution of 5, 12-indolino [3,2-a ] carbazole for 11, 12-indolino [2,3-a ] carbazole and 2-chloro-4-phenylquinazoline for intermediate M1 in synthesis example 1, and the others were unchanged to give P46. M: 719.9.
synthesis example 3: synthesis of P52
Substitution of 5, 12-indolino [3,2-a ] carbazole for 5, 7-indolino [2,3-B ] carbazole and 2-chloro-4-phenylquinazoline for intermediate M2 in synthesis example 1, and leaving the others unchanged gave P52. M: 663.8.
synthesis example 5: synthesis of P57
Substitution of 5, 12-indolino [3,2-a ] carbazole in synthesis example 1 with 5, 8-indolino [2,3-C ] carbazole, the others being unchanged, gave P57. M: 613.7.
synthesis example 6: synthesis of P62
Substitution of 5, 12-indolino [3,2-a ] carbazole in synthesis example 1 with 5, 11-indolino [2,3-B ] carbazole, and the others were unchanged gave P62. M: 613.7.
synthesis example 7: synthesis of P66
Figure BDA0001834140660000181
Under nitrogen atmosphere, 5, 12-indolino [3,2-A ] is reacted]Carbazole (10g, 39.1mmol), 5-bromo-2-phenylpyridine (9.2g, 39.1mmol), Pd2(dba)3(0.37g，0.4mmol)、(t-Bu)3HBF4(0.23g, 0.8mmol), t-BuONa (7.5g, 78.2mmol) and 200ml of toluene were placed in a 1L reaction vessel and reacted at 110 ℃ under reflux for 12 hours. Cool to room temperature and combine the concentrated organic phases. The intermediate 2-a13.4g was isolated by column chromatography. And M is 490.5.
Figure BDA0001834140660000182
Under nitrogen atmosphere, intermediate 2-a (10g, 20.4mmol), 2-chloro-4-phenylquinazoline (4.9g, 20.4mmol), Pd2(dba)3(0.18g, 0.2mmol), s-phos (0.16g, 0.4mmol), t-BuONa (3.9g, 40.8mmol) and 200ml of toluene were placed in a 1L reaction vessel and reacted at 110 ℃ under reflux for 12 hours. Cool to room temperature and combine the concentrated organic phases. Separation by column chromatography gave P66. 48 g. M: 613.7.
device embodiments
The specific implementation mode is as follows:
the OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn 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, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. 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 a combination 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).
The material of the hole transport region may be selected from, but is 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 compounds shown below in HT-1 to HT-34; or any combination thereof.
Figure BDA0001834140660000191
Figure BDA0001834140660000201
Figure BDA0001834140660000211
The hole injection layer is located between the anode and the hole transport layer. 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 compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
Figure BDA0001834140660000212
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 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.
Figure BDA0001834140660000221
Figure BDA0001834140660000231
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.
Figure BDA0001834140660000232
Figure BDA0001834140660000241
Figure BDA0001834140660000251
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The following structural compound R-1 is a compound selected from the prior art as a comparative material in the device examples of the present invention.
Figure BDA0001834140660000261
The preparation process of the organic electroluminescent device in the embodiment is as follows:
example 1
The glass plate coated with the ITO transparent conductive layer 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 × 10-5～9×10-3Pa, 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;
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;
a luminescent layer of the device is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material P1 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is set in a proportion of 3%, and the total film thickness of evaporation is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material ET-1 of the device on the light emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness 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.
Example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with P6.
Example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with P13.
Example 4
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with P27.
Example 5
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with P33.
Example 6
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with P66.
Example 7
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with P45.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound P1 was replaced with the compound R-1 of the prior art.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples 1 to 6 and comparative example 1 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 results of the performance tests of the organic electroluminescent devices prepared above are detailed in table 1 below.
Table 1:
example numbering Compound numbering Require a brightness cd-m2 Voltage V Current efficiency cd/A LT95
Comparative example 1 R-1 5000.00 5.2 14.5 80
Example 1 P1 5000.00 3.8 22.9 107
Example 2 P6 5000.00 3.6 21.7 110
Example 3 P13 5000.00 4.1 21.1 90
Example 4 P27 5000.00 4.3 20.7 99
Example 5 P34 5000.00 4.4 20.2 94
Example 6 P67 5000.00 3.9 22.3 106
Example 7 P46 5000.00 4.5 19.8 88
As can be seen from the data in Table 1, the novel organic material of the present invention is used for the organic electroluminescent device, can effectively reduce the rise-fall voltage and improve the current efficiency, and is a red light host material with good performance.
As can be seen from a comparison of examples 1-6 with comparative example 1, the synthesized compounds of the present invention, when used as host materials in OLED devices, are superior in performance, both in terms of turn-on voltage, current efficiency and lifetime, to known OLED devices prepared using prior art materials.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.

Claims (10)

1. A compound of the formula (1):
Figure FDA0001834140650000011
in formula (1):
Y1～Y8each independently selected from C, CH or N;
X1、X2each independently selected from a single bond or N, and when one is a single bond, the other is N;
R1～R3each independently selected from the group consisting of: H. c1～C12Alkyl of (C)1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C5～C30Heteroarylamino group of (a), substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C5～C30One of the heteroaryl groups of (1), R1～R3Two adjacent of the two can be connected to form a ring, or R1～R3Each independently may be fused to the attached aryl or heteroaryl group to form a ring;
R4is H, C6～C30Aryl of (C)5～C30One of the heteroaryl groups of (a);
a and c are respectively independent integers from 0 to 4, and b is an integer from 0 to 2;
l is selected from a single bond or substituted or unsubstituted C6～C30Aryl of (a);
a is a structure represented by the following formula (2):
Figure FDA0001834140650000012
wherein，Z1～Z6Each independently selected from CR 'or N, R' is H, C6～C30Aryl of (C)5～C30And Z is one of the heteroaryl groups of1～Z6At least one of which is N.
When the above groups have substituents, the substituents are respectively and independently selected from halogen, cyano, C1～C10Alkyl or cycloalkyl of, C2～C6Alkenyl or cycloalkenyl of1～C6Alkoxy or thioalkoxy of C6～C30Aryl of (C)3～C30One of the heteroaryl groups of (a).
2. The general formula compound according to claim 1, wherein the compound of formula (1) is represented by the following formula (1-1) or formula (1-2):
Figure FDA0001834140650000021
among formulae (1-1) to (1-2), A, Y1～Y8、X1、X2、R1～R3、R4L and a, b and c are the same as defined in the general formula (1).
3. The general formula compound according to claim 1, wherein the compound of formula (1) is represented by any one of the following general formulae (1-3) to (1-6):
Figure FDA0001834140650000022
a, Y in formulae (1-3) to (1-6)1～Y8、R1～R3、R4L and a, b and c are the same as defined in the general formula (1).
4. A compound of general formula (la) according to any one of claims 1 to 3, wherein in formula (1), formula (1-1) to formula (1-2), formula (1-3) to formula (1-6), a is a structure represented by the following formulae (2-1) to (2-4):
Figure FDA0001834140650000031
wherein R is5Is H, C6～C30Aryl of (C)5～C30One of the heteroaryl groups of (a).
5. A compound of general formula according to any one of claims 1 to 3, wherein in formula (1), formulae (1-1) to (1-2), formulae (1-3) to (1-6):
R1～R3each independently selected from the group consisting of: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
Figure FDA0001834140650000033
One of a group, furyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group;
R4selected from the following groups: hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthyl, triphenylenyl, pyrenyl, perylenyl,
Figure FDA0001834140650000034
One of a group, furyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group and carbazolyl group.
6. A compound of formula (la) according to claim 4, wherein in formulae (2-1) to (2-4), R5Selected from the following groups: hydrogen, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthyl, triphenylenePhenyl, pyrenyl, perylenyl,
Figure FDA0001834140650000035
One of a group, furyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group and carbazolyl group.
7. A compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
Figure FDA0001834140650000032
Figure FDA0001834140650000041
Figure FDA0001834140650000051
Figure FDA0001834140650000061
Figure FDA0001834140650000071
Figure FDA0001834140650000081
Figure FDA0001834140650000091
Figure FDA0001834140650000101
Figure FDA0001834140650000111
Figure FDA0001834140650000121
Figure FDA0001834140650000131
8. use of a compound of formula (la) according to claim 1, 2 or 3 as a light-emitting host material in an organic electroluminescent device.
9. Use of the structural compound according to claim 7 as a light-emitting host material in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound according to any one of claims 1, 2,3 or 7.
CN201811218432.4A 2018-10-19 2018-10-19 Organic electroluminescent material and application thereof Pending CN111072666A (en)

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