CN112110895B - Compound and application thereof, and organic electroluminescent device using compound - Google Patents

Compound and application thereof, and organic electroluminescent device using compound Download PDF

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CN112110895B
CN112110895B CN201910529822.1A CN201910529822A CN112110895B CN 112110895 B CN112110895 B CN 112110895B CN 201910529822 A CN201910529822 A CN 201910529822A CN 112110895 B CN112110895 B CN 112110895B
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CN112110895A (en
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李之洋
黄鑫鑫
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention relates to a novel organic compound, which has the structure shown in the following formula (1): X is O, S or NR 3,R3 is selected from one of substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl; ar 1 is selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl containing N; y 1～Y4 is independently selected from CR 4 or CR 5, and at least one of them is CR 5;R5 selected from substituted or unsubstituted C6-C30 aryl. The compounds of the present invention exhibit excellent device performance and stability when used as light emitting materials in OLED devices. The invention also protects an organic electroluminescent device adopting the compound of the general formula.

Description

Compound and application thereof, and organic electroluminescent device using compound
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel compound and application thereof, and an organic electroluminescent device containing the compound.
Background
Optoelectronic devices based on organic materials have become increasingly popular in recent years. The inherent flexibility of organic materials makes them very suitable for fabrication on flexible substrates, which can be designed to produce aesthetically pleasing and cool optoelectronic products, as desired, with no comparable advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like.
The OLED device core is a thin film structure containing a plurality of organic functional materials. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.
Various organic materials have been developed, and various peculiar device structures are combined, so that carrier mobility can be improved, carrier balance can be regulated, electroluminescent efficiency can be broken through, and device attenuation can be delayed. For quantum mechanical reasons, common fluorescent emitters emit light mainly by singlet excitons generated when electrons and air are combined, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property, and sensitizes the luminophor in an energy transfer mode, so that higher luminous efficiency can be realized.
As OLED products continue to enter the market, there is an increasing demand for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifetime, cost, etc. The researchers of the present invention have discovered a smart molecular design through careful thought and continuous experimentation and are described in detail below. Surprisingly, the disclosed compounds are well suited for application to OLEDs and to enhance the performance of the device.
Although the compound reported by KR1020160041768A solves some problems, the voltage, efficiency and service life are improved, the performance of the compound can not meet the market demand along with the update iteration of the material, and the compound of the invention has a further breakthrough in comprehensive performance by continuously developing the material with better performance.
Disclosure of Invention
Aiming at the defects of the prior art scheme, the invention provides a new compound for an organic electroluminescent device by integrating the stability of a molecular structure and the balance transmission of carriers so as to meet the requirement of continuously improving the photoelectric property and the service life of the OLED device.
The present invention proposes a novel compound represented by the following formula (1):
wherein: x is O, S or NR 3,R3 is selected from one of substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C3-C18 heteroaryl;
Ar 1 is selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl containing N;
Y 1～Y4 are each independently selected from CR 4 or CR 5, and at least one of which is CR 5;
R 4 is selected from one of hydrogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C3-C30 heteroaryl;
r 5 is selected from substituted or unsubstituted aryl of C6-C30;
R 1 and R 2 each independently represent a single substituent to the maximum permissible substituent and are each independently selected from one of H, deuterium, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
When substituents are present on the above groups, the substituents are selected from one or a combination of at least two of hydrogen, halogen, C1-C10 alkyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon, C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon.
Further preferably, in the general formula (1), 1 or 2 of Y 1～Y4 are defined as CR 5,R5 and are the same as those in the general formula (1).
Preferably, the above formula (1) of the present invention is represented by the following formula (2):
In formula (2), X, ar 1、R1、R2、R5 and Y 1、Y2 and Y 4 are as defined in formula (1).
Further preferably, in formula (2), Y 1、Y2 and Y 4 are defined as CR 4,R4 as in formula (1).
Preferably, the above formula (1) of the present invention is represented by the following formula (1-a) or formula (1-b):
In the formula (1-a) or the formula (1-b), X, ar 1、R1、R2、R5 and Y 1～Y4 are the same as those defined in the formula (1).
Further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), ar 1 is selected from substituted or unsubstituted C3-C30 and contains at least two electron-deficient groups of N;
Still further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), ar 1 is selected from structures shown in any one of the following formulas (3-1) to (3-2):
In formula (3-1), Z 1、Z2、Z3、Z4 and Z 5 are each independently selected from CR 6 or an N atom, and at least one of Z 1、Z2、Z3、Z4 and Z 5 is an N atom;
In formula (3-2), Z 6、Z7、Z8、Z9、Z10、Z11、Z12 and Z 13 are each independently selected from CR 6 or an N atom, and at least one of Z 6、Z7、Z8、Z9、Z10、Z11、Z12 and Z 13 is an N atom;
wherein R 6 is selected from one of hydrogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
Still further preferably, in the formula (3-1), at least two of Z 1、Z2、Z3、Z4 and Z 5 are N atoms;
In formula (3-2), at least two of Z 6、Z7、Z8、Z9、Z10、Z11、Z12 and Z 13 are N atoms.
Further preferred, in formula (1), formula (2), formula (1-a) or formula (1-b), ar 1 is selected from one of the following substituted or unsubstituted groups: quinazolinyl, triazinyl, pyrimidinyl, and quinoxalinyl.
Further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), ar 1 is selected from one of substituted or unsubstituted groups represented by the following formulas A1 to A14:
further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-B), ar 1 is one selected from the groups represented by the following B1-B19:
Preferably, in formula (1), formula (2), formula (1-a) or formula (1-b), R 5 is selected from substituted or unsubstituted C 6～C18 aryl; preferably, R 5 is selected from the following groups, substituted or unsubstituted: phenyl, naphthyl, biphenyl.
Preferably, in formula (1), formula (2), formula (1-a) or formula (1-b), R 1 and R 2 are hydrogen.
Preferably, in formula (1), formula (2), formula (1-a) or formula (1-b), R 4 when any one of Y 1～Y4 is independently selected from CR 4 is hydrogen.
Further, among the compounds of the general formula of the present invention, the following specific structural compounds are preferable:
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As another aspect of the present invention, the compounds of the above general formula of the present invention are useful as materials for light-emitting hosts in organic electroluminescent devices.
As still another aspect of the present invention, there is also provided an organic electroluminescent device including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer containing at least one compound represented by the general formula as described above. Preferably, the light-emitting layer included in the organic layer contains any one or a combination of at least two of the compounds represented by the general formula described above.
The specific reasons for the excellent properties of the above-described compounds of the present invention for use as a light-emitting host material in an organic electroluminescent device are not clear, and it is presumed that the following reasons are possible:
The general formula compound is designed in the structure to be connected with the power supply parent nucleus by adopting a specific electricity-absorbing group, wherein the electricity-absorbing group has good electron transmission performance, the LUMO energy level is matched with a functional layer, the transmission barrier is smaller, the transmission of electrons is facilitated, and the parent nucleus structure of the naphthocarbazole provides a stable carrier for the transmission of holes, so that the compound realizes the balanced transmission of electrons and holes, and brings low-voltage and high-efficiency photoelectric performance. Therefore, the organic electroluminescent device prepared by adopting the compound disclosed by the invention as a luminescent material has the advantages of low voltage, high efficiency and long service life.
The compound provided by the invention is used in an organic electroluminescent device, so that the organic electroluminescent device has the effects of low starting voltage, high luminous efficiency and long service life, the starting voltage is less than or equal to 4.7V, the current efficiency is more than or equal to 15cd/A, and the LT95 service life is more than or equal to 68h.
Detailed Description
In order that those skilled in the art will better understand the present invention, the present invention will be described in further detail with reference to specific embodiments.
All compounds of the synthesis process not mentioned in the present invention are commercially available starting products. The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, quinazoline, triazine, quinoxaline and the like, may be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai Pichia pharmaceutical company, carboline reagent company and the like. In addition, the person skilled in the art can synthesize the compounds by known methods.
The method for synthesizing the compound of the present invention will be briefly described.
The synthetic route of the compounds of formula (1) of the present invention:
Different target compounds can be obtained by replacing different substituents. One of Y1 to Y4 is halogen and is coupled to R 5 -B (OH), and the above synthetic method uses Buchwald-Hartwig coupling to link the substituent Ar 1 to the parent nucleus, but the synthetic method is not limited to this coupling method, and one skilled in the art may select other methods, for example, known methods such as the ullmann coupling method, the grignard reagent method, the SUZUKI method, etc., but not limited to these methods, and any equivalent synthetic method may be used to achieve the purpose of linking the substituent Ar to the parent nucleus, and may be selected according to the need.
Synthetic examples
Synthesis example 1:
synthesis of Compound P1
10-Bromo-7H-benzocarbazole (100 mmol), phenylboronic acid (110 mmol), potassium carbonate (150 mmol), dioxane (300 ml), water 50ml, tetrakis (triphenylphosphine) palladium 0.5g were added to the reaction flask, heated to reflux for 5H, TLC monitored for completion of the reaction, and the reaction solution was poured into water and concentrated P1-A was extracted with dichloromethane.
P1-A (80 mmol), 3-bromo-5-chlorofluorobenzene (100 mmol), potassium carbonate (150 mmol) and DMF (300 ml) were added to a reaction flask, heated to reflux for 5h, TLC monitored the completion of the reaction, the reaction solution was poured into water and filtered, and the filter cake was washed with ethanol to give intermediate P1-B.
P1-B (50 mmol), dibenzothiophene 4-boric acid (50 mmol), potassium carbonate (60 mmol), dioxane (200 ml), water (40 ml) and tetrakis (triphenylphosphine) palladium (0.3 g) were added to a reaction flask, heated to reflux for 5h, TLC monitored for completion of the reaction, and the reaction mixture was poured into water and concentrated P1-C was extracted with dichloromethane.
P1-C (50 mmol), pinacol diboronate (100 mmol), potassium acetate (100 mmol), dioxane (200 ml), pd 2(dba)3 0.4.4 g, S-Phos0.4g were added to the reaction flask, heated to reflux for 5h, TLC monitored for completion of the reaction, and the reaction mixture was poured into water and concentrated P1-D was extracted with dichloromethane.
P1-D (30 mmol), 2-chloro-4-phenylquinazoline (35 mmol), potassium carbonate (50 mmol), dioxane (200 ml), water (30 ml) and tetrakis (triphenylphosphine) palladium (0.4 g) were added to a reaction flask, heated to reflux for 5h, TLC monitored for completion of the reaction, and the reaction mixture was poured into water and concentrated P1 was extracted with dichloromethane.
1H NMR(500MHz,Chloroform)δ8.55(ddd,J＝14.6,4.9,3.2Hz,2H),8.49–8.40(m,2H),8.37–8.25(m,4H),8.13(dd,J＝15.0,3.1Hz,1H),8.04–7.93(m,2H),7.91–7.71(m,8H),7.71–7.36(m,13H),7.31(td,J＝15.0,3.0Hz,1H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 2:
Synthesis of Compound P12
The procedure is as in Synthesis example 1, except that 2-chloro-4-phenylquinazoline is replaced with an equivalent amount of 2-phenyl-3-chloroquinoxaline to give a compound P12.1H NMR(500MHz,Chloroform)δ8.87(t,J＝3.0Hz,1H),8.55(ddd,J＝14.6,4.9,3.2Hz,2H),8.48–8.38(m,3H),8.38–8.29(m,2H),8.10–7.93(m,3H),7.91–7.24(m,21H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 3:
Synthesis of Compound P21
The procedure is as in synthesis example 1, except that 2-chloro-4-phenylquinazoline is replaced with an equivalent of 2-chloro-4, 6-diphenyl (1, 3, 5) triazine to give compound P21.
1H NMR(500MHz,Chloroform)δ8.55(ddd,J＝14.6,4.9,3.2Hz,2H),8.45(dd,J＝14.4,3.1Hz,2H),8.42–8.25(m,8H),7.99(dt,J＝14.6,3.2Hz,1H),7.87(ddd,J＝15.0,5.5,3.1Hz,2H),7.80–7.67(m,3H),7.66–7.36(m,14H),7.31(td,J＝15.0,3.0Hz,1H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 4:
synthesis of Compound P27
The same procedure was followed except for the substitution of 2-chloro-4-phenylquinazoline to equivalent amounts of 2-chloro-4, 6-diphenylpyrimidine to give the compound P27.1H NMR(500MHz,Chloroform)δ8.55(ddd,J＝14.6,4.9,3.2Hz,2H),8.49–8.41(m,2H),8.36–8.26(m,4H),8.23(s,1H),8.02–7.82(m,7H),7.79–7.66(m,3H),7.66–7.36(m,14H),7.31(td,J＝15.0,3.0Hz,1H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 5:
Synthesis of Compound P46
Synthesis example 1 was repeated except that dibenzothiophene-4-boronic acid was replaced with an equivalent amount of dibenzofuran-4-boronic acid to give compound P46.
1H NMR(500MHz,Chloroform)δ8.55(ddd,J＝14.6,4.9,3.2Hz,2H),8.49–8.40(m,2H),8.37–8.25(m,4H),8.13(dd,J＝15.0,3.1Hz,1H),8.04–7.93(m,2H),7.91–7.71(m,8H),7.71–7.36(m,13H),7.31(td,J＝15.0,3.0Hz,1H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 6:
synthesis of Compound P57
Synthesis example 5, except that 2-chloro-4-phenylquinazoline was replaced with an equivalent of 2-phenyl-3-chloroquinoxaline to give compound P57.
1H NMR(500MHz,Chloroform)δ8.87(t,J＝3.0Hz,1H),8.55(ddd,J＝14.6,4.9,3.2Hz,2H),8.48–8.38(m,3H),8.38–8.29(m,2H),8.10–7.93(m,3H),7.91–7.24(m,21H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 7:
Synthesis of Compound P94
Synthesis example 1, except that 10-bromo-7H-benzocarbazole was replaced with an equivalent amount of 11-bromo-7H-benzocarbazole to give a compound P94.1H NMR(500MHz,Chloroform)δ8.54(dd,J＝13.8,3.1Hz,2H),8.45(dd,J＝14.9,3.0Hz,1H),8.35–8.24(m,4H),8.23–8.09(m,3H),8.04–7.91(m,3H),7.90–7.70(m,7H),7.70–7.36(m,11H),7.31(td,J＝15.0,3.0Hz,1H),7.16(dd,J＝14.9,3.0Hz,1H).
Synthesis example 8:
Synthesis of Compound P100
Synthesis example 1, dibenzothiophene-4-boronic acid was replaced with 2-cyanodibenzothiophene-8-boronic acid to give Compound P100.
1H NMR(500MHz,Chloroform)δ8.61–8.43(m,4H),8.39–8.26(m,3H),8.13(ddd,J＝15.0,4.4,3.0Hz,2H),8.07–7.94(m,4H),7.87(dd,J＝15.0,3.1Hz,1H),7.84–7.36(m,17H),7.16(dd,J＝14.9,3.0Hz,1H).
Device embodiment
The specific embodiment is as follows:
The OLED includes a first electrode and a second electrode, 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 particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. 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 serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and 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 compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have 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 conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-34; or any combination thereof.
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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 of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-34 may also be used to dope one or more of HI-1-HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (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 plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together 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 simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
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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, combinations of one or more of ET-1 through ET-57 listed below.
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An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The structural formula of the comparative compound used in the comparative example in the examples of the present invention is shown below:
the preparation process of the organic electroluminescent device in this embodiment is as follows:
Device example 1
The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam; placing the glass substrate with the anode in a vacuum cavity, vacuumizing to <1×10 -5 Pa, sequentially vacuum evaporating 10nm of HT-4:HI-3 (97/3,w/w) mixture as a hole injection layer, 60nm of compound HT-4 as a hole transport layer, 40nm of compound P1:RPD-8 (100:3, w/w) binary mixture as a light-emitting layer, 25nm of compound ET-46:ET-57 (50/50, w/w) mixture as an electron transport layer, 1nm of LiF as an electron injection layer and 150nm of metallic aluminum as a cathode on the anode layer. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Device example 2
Device example 2 was fabricated in the same manner as device example 1, except that P1 in the light-emitting layer was replaced with P12.
Device example 3
Device example 3 was fabricated in the same manner as device example 1, except that P1 in the light-emitting layer was replaced with P21.
Device example 4
Device example 4 was fabricated in the same manner as device example 1, except that P1 in the light-emitting layer was replaced with P27.
Device example 5
Device example 5 was fabricated in the same manner as device example 1, except that P1 in the light-emitting layer was replaced with P46.
Device example 6
Device example 6 was fabricated in the same manner as device example 1, except that P1 in the light-emitting layer was replaced with P57.
Device example 7
Device example 7 was fabricated in the same manner as device example 1, except that P1 in the light-emitting layer was replaced with P94.
Device example 8
Device example 8 was fabricated in the same manner as in device example 1, except that P1 in the light-emitting layer was replaced with P101.
Comparative example 1
Comparative example 1 was produced in the same manner as in device example 1 except that P1 in the light-emitting layer was replaced with compound C1.
Comparative example 2
Comparative example 2 was prepared in the same manner as in device example 1 except that P1 in the light-emitting layer was replaced with compound C2.
Method for testing a device (including apparatus and test conditions):
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
The driving voltage and current efficiency and the lifetime of the organic electroluminescent devices manufactured in examples 1 to 8 and comparative examples 1 to 2 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was increased at a rate of 0.1V per second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent device reached 3000cd/m 2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: the time for the luminance of the organic electroluminescent device to drop to 9500cd/m 2 was measured in hours using a luminance meter maintaining a constant current at 10000cd/m 2 luminance.
The organic electroluminescent device performance is shown in the following table:
Numbering of compounds The required brightness cd/m 2 Voltage V Current efficiency cd/a T95h(10000nit)
Comparative example 1 3000.00 4.1 14.2 45
Comparative example 2 3000.00 4.3 13.5 43
Device example 1 3000.00 3.8 18.3 62
Device example 2 3000.00 3.7 17.6 61
Device example 3 3000.00 3.7 18.2 60
Device example 4 3000.00 3.8 17.9 58
Device example 5 3000.00 3.8 18.4 64
Device example 6 3000.00 3.6 17.1 60
Device example 7 3000.00 3.6 17.5 58
Device example 8 3000.00 3.7 18.1 57
The result shows that the novel organic material is used for an organic electroluminescent device, can effectively reduce the voltage at take off and land, improves the current efficiency, and is a red light main body material with good performance.
Compared with comparative example 1, the invention is different from C1 in the electricity absorbing group, the benzo [ H ] quinazoline in C1 is shown by experimental comparison to have inferior comprehensive performance as the material of the invention, and the reason for this is analyzed that we guess that one possible substituent group such as quinazoline in the invention has inferior electron transmission performance as the benzo [ H ] quinazoline. The LUMO value of the material is shallower than that of C1, and the transmission barrier of electrons is small. Furthermore, the invention introduces aryl substitution on the carbazole mother nucleus, and replaces the active site of the molecule with stable aryl group, thereby increasing the stability of the molecule in electrochemical environment and showing longer service life.
Compared with comparative example 2, the C2 compound introduces an aza atom into the parent nucleus, which makes HOMO of the molecule deep, unfavorable for hole transport, and makes it impossible to match with electron transport, and carrier balance cannot be achieved.
While the invention has been described in connection with the embodiments, it is not limited to the above embodiments, but it should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.

Claims (14)

1. A compound of the general formula (1) as shown below:
Wherein: x is selected from O or S;
Ar 1 is selected from the structures shown in any one of the following formulas (3-1) - (3-2):
In the formula (3-1), Z 1、Z2、Z3、Z4 and Z 5 are each independently selected from CR 6 or an N atom, and at least two of Z 1、Z2、Z3、Z4 and Z 5 are N atoms, at least one of Z 1、Z2、Z3、Z4 and Z 5 is selected from CR 6, and R 6 is a substituted or unsubstituted C6-C30 aryl group;
In the formula (3-2), Z 6、Z7、Z8、Z9、Z10、Z11、Z12 and Z 13 are each independently selected from CR 6 or an N atom, and at least two of Z 6、Z7、Z8、Z9、Z10、Z11、Z12 and Z 13 are N atoms, at least one of Z 6、Z7、Z8、Z9、Z10、Z11、Z12 and Z 13 is selected from CR 6, and R 6 is a substituted or unsubstituted C6-C30 aryl group;
wherein R 6 is selected from one of hydrogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
Y 1～Y4 are each independently selected from CR 4 or CR 5, and 1 or 2 of Y 1～Y4 are CR 5;
R 4 is selected from one of hydrogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C3-C30 heteroaryl;
r 5 is selected from substituted or unsubstituted aryl of C6-C30;
R 1 and R 2 each independently represent a single substituent to the maximum permissible substituent and are each independently selected from one of H, deuterium, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
When substituents are present on the above groups, the substituents are selected from one or a combination of at least two of halogen, C1-C10 alkyl or C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic or fused ring aromatic hydrocarbon, C3-C30 monocyclic heteroaromatic or fused ring heteroaromatic hydrocarbon.
2. The compound of the general formula according to claim 1, wherein the general formula (1) is represented by the following formula (2):
In formula (2), X, ar 1、R1、R2、R5 and Y 1、Y2 and Y 4 are as defined in formula (1).
3. A compound of formula (la) according to claim 2, wherein in formula (2) Y 1、Y2 and Y 4 are both CR 4,R4 as defined in formula (1).
4. The compound of formula (la) according to claim 1, wherein formula (1) is represented by the following formula (1-a) or formula (1-b):
In the formula (1-a) or the formula (1-b), X, ar 1、R1、R2 and Y 1～Y4 are the same as those defined in the formula (1).
5. A compound of general formula (la) according to any one of claims 1,2 or 4, formula (1), formula (2), formula (1-a) or formula (1-b), wherein Ar 1 is selected from one of the following substituted groups: quinazolinyl, triazinyl, pyrimidinyl, and quinoxalinyl.
6. The compound of the general formula according to any one of claims 1, 2 or 4, wherein Ar 1 is selected from one of substituted or unsubstituted groups represented by the following formulae A1 to a14 in formula (1), formula (2), formula (1-a) or formula (1-b):
7. The compound of the general formula (la), formula (1), formula (2), formula (1-a) or formula (1-B) according to any one of claims 1,2 or 4, wherein Ar 1 is one of the groups represented by the following B1-B19:
8. The compound of formula (la), formula (lb), formula (la), formula (1-a), or formula (1-b) according to any one of claims 1,2, or 4, wherein R 5 is selected from substituted or unsubstituted C 6～C18 aryl.
9. The compound of formula (la), formula (lb), formula (la), formula (1-a), or formula (1-b) according to any one of claims 1,2, or 4, wherein R 5 is selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl.
10. The compound of formula (la), formula (1), formula (2), formula (1-a) or formula (1-b) according to any one of claims 1,2 or 4, wherein R 1 and R 2 are hydrogen.
11. The compound of general formula (la), formula (1), formula (2), formula (1-a), or formula (1-b) according to any one of claims 1,2, or 4, wherein when any one of Y 1～Y4 is independently selected from CR 4, the R 4 is hydrogen.
12. A compound of the general formula according to claim 1, selected from the following specific structural compounds:
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13. Use of a compound according to any one of claims 1-12 as a light-emitting host material in an organic electroluminescent device.
14. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, characterized in that the organic layer comprises at least one compound according to any one of claims 1 to 12.
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