CN112110895A - Compound, application thereof and organic electroluminescent device adopting compound - Google Patents

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

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CN112110895A
CN112110895A CN201910529822.1A CN201910529822A CN112110895A CN 112110895 A CN112110895 A CN 112110895A CN 201910529822 A CN201910529822 A CN 201910529822A CN 112110895 A CN112110895 A CN 112110895A
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CN112110895B (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 present invention relates to a novel organic compound having a structure represented by the following formula (1):
Figure DDA0002099379790000011
x is selected from O, S or NR3，R3One selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; ar (Ar)1Selected from substituted or unsubstituted C3-C30N-containing electron-deficient heteroaromaticsA group; y is1～Y4Are each independently selected from CR4Or CR5And at least one of them is CR5；R5Is selected from substituted or unsubstituted aryl of C6-C30. 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

Compound, application thereof and organic electroluminescent device adopting compound
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel compound, application thereof and an organic electroluminescent device containing the compound.
Background
In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and crunchy optoelectronic products, with unparalleled 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, OLEDs have been developed particularly rapidly, and have been commercially successful in the field of information display. The OLED can provide three colors of red, green and blue with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of colorful, light, thin and soft color and the like.
The core of the OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light.
People have developed various organic materials, and the organic materials are combined with various peculiar device structures, so that the carrier mobility can be improved, the carrier balance can be regulated and controlled, the electroluminescent efficiency can be broken through, and the attenuation of the device can be delayed. For quantum mechanical reasons, common fluorescent luminophores mainly utilize singlet excitons generated when electrons and air are combined to emit light, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet excitons and singlet excitons, which are called phosphorescent emitters, and the energy conversion efficiency can be increased by up to four times as compared with conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. Thermal excitation sensitized fluorescence (TASF) technology also achieves higher luminous efficiency by sensitizing the emitter by energy transfer using TADF-like materials.
As OLED products gradually enter the market, there are increasingly higher requirements on the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, service life, cost and the like. The present inventors have discovered a clever molecular design through careful consideration and ongoing experimentation, and are described in detail below. Surprisingly, the compounds disclosed in the present invention are very suitable for application in OLEDs and improve the performance of the devices.
While the compound reported by KR1020160041768A has solved some problems and improved in voltage, efficiency and life, with the update iteration of the material, the performance of the compound can not meet the market demand, and the compound of the invention has further breakthrough in comprehensive performance.
Disclosure of Invention
Aiming at the defects of the prior art scheme, the invention provides a novel compound for an organic electroluminescent device by integrating the stability of a molecular structure and the balanced transmission of current carriers so as to meet the requirements of continuously improving the photoelectric property and the service life of an OLED device.
The present invention provides a novel compound represented by the following formula (1):
Figure BDA0002099379780000021
wherein: x is selected from O, S or NR3，R3One selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl;
Ar1selected from substituted or unsubstituted C3-C30N-containing electron-deficient heteroaryl;
Y1～Y4are each independently selected from CR4Or CR5And at least one of them is CR5；
R4Selected from hydrogen, 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, and substituted or unsubstituted C3-one of a C30 heteroaryl group;
R5is selected from substituted or unsubstituted aryl of C6-C30;
R1and R2Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from the group consisting of H, deuterium, 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;
when the above groups have substituents, 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 fused ring aromatic hydrocarbon, C3-C30 monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon.
Further preferably, in the formula (1), Y1～Y41 or 2 of them being CR5，R5Is the same as defined in formula (1).
Preferably, the above formula (1) of the present invention is represented by the following formula (2):
Figure BDA0002099379780000031
in formula (2), X, Ar1、R1、R2、R5And Y1、Y2And Y4The same as defined in formula (1).
More preferably, in the formula (2), Y1、Y2And Y4Is CR4，R4Is the same as defined in formula (1).
Preferably, the above formula (1) of the present invention is represented by the following formula (1-a) or formula (1-b):
Figure BDA0002099379780000032
x, Ar in the formula (1-a) or the formula (1-b)1、R1、R2、R5And Y1～Y4Are all as defined in formula (1).
Further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), Ar is1An electron-deficient group selected from substituted or unsubstituted C3 to C30 and containing at least two N's;
still more preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), Ar is1Selected from the structures represented by any one of the following formulae (3-1) to (3-2):
Figure BDA0002099379780000041
in the formula (3-1), Z1、Z2、Z3、Z4And Z5Each independently selected from CR6Or an N atom, and Z1、Z2、Z3、Z4And Z5At least one of which is an N atom;
in the formula (3-2), Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13Each independently selected from CR6Or an N atom, and Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least one of which is an N atom;
wherein R is6One selected from hydrogen, 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 and substituted or unsubstituted C3-C30 heteroaryl.
Still further preferably, in the formula (3-1), Z1、Z2、Z3、Z4And Z5At least two of which are N atoms;
formula (3-2)In (1), Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least two of which are N atoms.
Further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), Ar is1One selected from the following substituted or unsubstituted groups: quinazolinyl, triazinyl, pyrimidinyl, quinoxalinyl.
Further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), Ar is1One selected from the group consisting of substituted or unsubstituted groups represented by the following formulae A1-A14:
Figure BDA0002099379780000051
further preferably, in the formula (1), the formula (2), the formula (1-a) or the formula (1-b), Ar is1One selected from the following groups represented by B1-B19:
Figure BDA0002099379780000052
Figure BDA0002099379780000061
preferably, in formula (1), formula (2), formula (1-a) or formula (1-b), R5Selected from substituted or unsubstituted C6～C18An aryl group; preferably, R5Selected from the following substituted or unsubstituted groups: phenyl, naphthyl and biphenyl.
Preferably, in formula (1), formula (2), formula (1-a) or formula (1-b), R1And R2Is hydrogen.
Preferably, in formula (1), formula (2), formula (1-a) or formula (1-b), when Y is1～Y4Each independently selected from CR4R of (A) is4Is hydrogen.
Further, the compounds of the general formula of the present invention are preferably those of the following specific structures:
Figure BDA0002099379780000062
Figure BDA0002099379780000071
Figure BDA0002099379780000081
Figure BDA0002099379780000091
Figure BDA0002099379780000101
Figure BDA0002099379780000111
Figure BDA0002099379780000121
Figure BDA0002099379780000131
Figure BDA0002099379780000141
Figure BDA0002099379780000151
Figure BDA0002099379780000161
Figure BDA0002099379780000171
Figure BDA0002099379780000181
as another aspect of the present invention, the compounds of the above general formula according to the present invention are used as materials for light emitting hosts 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 between the first electrode and the second electrode, the organic layer containing at least one compound represented by the general formula 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 formulae described above.
The specific reason why the above-mentioned compound of the present invention is excellent in the performance as a light-emitting host material in an organic electroluminescent device is not clear, and the following reason is presumed:
the general formula compound adopts a specific electricity-absorbing group connected with a power supply parent nucleus in the structural design, wherein the electricity-absorbing group has good electron transmission performance, the LUMO energy level is matched with a functional layer, the transmission barrier is small, the electron transmission is facilitated, and the parent nucleus structure of naphthocarbazole provides a stable carrier for the hole transmission, 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 using the compound of 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 service life of LT95 is more than or equal to 68 h.
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. 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, can be purchased from domestic chemical product markets, such as from national drug group reagent company, TCI company, Shanghai Bidi medicine company, Bailingwei reagent company and the like. In addition, they can be synthesized by a known method by those skilled in the art.
The synthesis of the compounds of the present invention is briefly described below.
The synthetic route for the compounds of formula (1) according to the invention:
Figure BDA0002099379780000191
different target compounds can be obtained by substituting different substituents. Note that one of Y1-Y4 is halogen, and R is5(OH) phase coupling, the above synthetic method usingBuchwald–HartwigCoupling with substituent Ar1The linker may be attached to the parent nucleus by any method known to those skilled in the art, including, but not limited to, Ullmann's coupling, Grignard, SUZUKI, and the like, and any equivalent synthetic method may be used to attach the substituent Ar to the parent nucleusA selection is required.
Synthetic examples
Synthesis example 1:
synthesis of Compound P1
Figure BDA0002099379780000201
Adding 10-bromo-7H-benzocarbazole (100mmol), phenylboronic acid (110mmol), potassium carbonate (150mmol), dioxane (300ml), 50ml of water and 0.5g of tetrakis (triphenylphosphine) palladium into a reaction bottle, heating to reflux for 5 hours, monitoring by TLC to complete the reaction, and pouring the reaction solution into water to extract concentrated P1-A by dichloromethane.
Adding P1-A (80mmol), 3-bromo-5-chlorofluorobenzene (100mmol), potassium carbonate (150mmol) and DMF (300ml) into a reaction bottle, heating to reflux for 5h, monitoring by TLC to complete the reaction, pouring the reaction liquid into water, filtering, and washing a filter cake with ethanol to obtain an intermediate P1-B.
P1-B (50mmol), dibenzothiophene 4-boric acid (50mmol), potassium carbonate (60mmol), dioxane (200ml), water (40 ml) and tetrakis (triphenylphosphine) palladium (0.3 g) are added into a reaction bottle, the reaction is heated to reflux for 5h, TLC monitors the reaction completion, and the reaction solution is poured into water to extract concentrated P1-C by dichloromethane.
Mixing P1-C (50mmol), pinacol diboron (100mmol), potassium acetate (100mmol), dioxane (200ml) and Pd2(dba)30.4g of S-Phos0.4g is added into a reaction flask, the mixture is heated to reflux reaction for 5 hours, TLC monitors the reaction completion, and the reaction liquid is poured into water to extract concentrated P1-D by dichloromethane.
P1-D (30mmol), 2-chloro-4-phenylquinazoline (35mmol), potassium carbonate (50mmol), dioxane (200ml), 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 solution was poured into water and dichloromethane extracted to concentrated P1.
1H NMR(500MHz,Chloroform)8.55(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 method is the same as that of synthesis example 1, except that 2-chloro-4-phenylquinazoline is replaced by equivalent 2-phenyl-3-chloroquinoxaline to obtain a compound P12.1H NMR(500MHz,Chloroform)8.87(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 by an equivalent amount of 2-chloro-4, 6-diphenyl (1,3,5) triazine to give compound P21.
1H NMR(500MHz,Chloroform)8.55(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 method is the same as that of synthesis example 1, except that 2-chloro-4-phenylquinazoline is replaced by equivalent 2-chloro-4, 6-diphenylpyrimidine to obtain a compound P27.1H NMR(500MHz,Chloroform)8.55(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 conducted except that dibenzothiophene-4-boronic acid was replaced with an equivalent amount of dibenzofuran-4-boronic acid to obtain compound P46.
1H NMR(500MHz,Chloroform)8.55(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 by a method other than substituting 2-chloro-4-phenylquinazoline with an equivalent amount of 2-phenyl-3-chloroquinoxaline, Compound P57 was obtained.
1H NMR(500MHz,Chloroform)8.87(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
Method Synthesis example 1, except that 10-bromo-7H-benzocarbazole was replaced with an equivalent amount of 11-bromo-7H-benzocarbazole, Compound P94 was obtained.1H NMR(500MHz,Chloroform)8.54(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
Method Synthesis example 1 Dibenzothiophene-4-boronic acid was replaced with 2-cyanobenzothiophene-8-boronic acid to give compound P100.
1H NMR(500MHz,Chloroform)8.61–8.43(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 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 BDA0002099379780000231
Figure BDA0002099379780000241
Figure BDA0002099379780000251
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 HI-1-HI-3 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 HI-1-HI-3 described below.
Figure BDA0002099379780000252
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
Figure BDA0002099379780000261
Figure BDA0002099379780000271
Figure BDA0002099379780000281
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 BDA0002099379780000282
Figure BDA0002099379780000291
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 BDA0002099379780000292
Figure BDA0002099379780000301
Figure BDA0002099379780000311
Figure BDA0002099379780000321
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 comparative examples in the examples of the invention employ comparative compounds having the following structural formula:
Figure BDA0002099379780000322
the preparation process of the organic electroluminescent device in the embodiment is as follows:
device 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<1×10-5Pa, performing vacuum thermal evaporation on the anode layer film in sequence to obtain a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer, a 60nm compound HT-4 as a hole transport layer, and a 40nm compound P1: RPD-8(100:3, w/w) binary mixture as a light-emitting layerAn optical layer, a mixture of compounds ET-46: ET-57(50/50, w/w) at 25nm as an electron transport layer, LiF at 1nm as an electron injection layer, and metallic aluminum at 150nm as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
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 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 produced in the same manner as in device example 1 except that P1 in the light-emitting layer was replaced with Compound C2.
Method of testing the device (including equipment and test conditions):
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 8 and comparative examples 1 to 2 and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 3000cd/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 10000cd/m2The luminance drop of the organic electroluminescent device was measured to be 9500cd/m by maintaining a constant current at luminance2Time in hours.
The organic electroluminescent device properties are given in the following table:
compound numbering Required luminance cd/m2 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 results show that the novel organic material provided by the invention is used for an organic electroluminescent device, can effectively reduce the take-off and landing voltage and improve 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, namely benzo [ H ] quinazoline in C1, and experimental comparison shows that the comprehensive performance of the invention is inferior to that of the material of the invention, and the reason for analyzing the invention is that the electron transport performance of benzo [ H ] quinazoline is probably inferior to that of substituent groups such as quinazoline in the invention. Specifically, the LUMO value of the material of the present invention is shallow compared to that of C1, and the barrier for electron transport is small. In addition, aryl substitution is introduced on the carbazole parent nucleus, and the active site of the molecule is substituted by stable aryl group, so that the stability of the molecule in an electrochemical environment is improved, and the longer service life is shown.
Compared with comparative example 2, the C2 compound introduces nitrogen heteroatom into the parent nucleus, so that HOMO of the molecule becomes deep, which is not beneficial to hole transmission, and cannot match with electron transmission, and carrier balance cannot be achieved.
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.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (15)

1. A compound of the formula (1):
Figure FDA0002099379770000011
wherein: x is selected from O, S or NR3，R3One selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl;
Ar1selected from substituted or unsubstituted C3-C30N-containing electron-deficient heteroaryl;
Y1～Y4are each independently selected from CR4Or CR5And at least one of them is CR5；
R4One selected from hydrogen, 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 and substituted or unsubstituted C3-C30 heteroaryl;
R5is selected from substituted or unsubstituted aryl of C6-C30;
R1and R2Each independently represents a single substituent to the maximum permissible substituent, and each independently is selected from H, deuterium, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxy, silyl, aminoOne of a group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
when the above groups have substituents, 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 hydrocarbon or fused ring aromatic hydrocarbon group, C3-C30 monocyclic heteroaromatic hydrocarbon group or fused ring heteroaromatic hydrocarbon group.
2. A compound of formula (1) as claimed in claim 1, wherein Y is1～Y41 or 2 of them being CR5，R5Is the same as defined in the general formula (1).
3. The general formula compound according to claim 1 or 2, wherein general formula (1) is represented by the following formula (2):
Figure FDA0002099379770000021
in formula (2), X, Ar1、R1、R2、R5And Y1、Y2And Y4The same as defined in formula (1);
preferably, in the formula (2), Y1、Y2And Y4Are all CR4，R4Is the same as defined in formula (1).
4. The general formula compound according to claim 1 or 2, wherein formula (1) is represented by the following formula (1-a) or formula (1-b):
Figure FDA0002099379770000022
x, Ar in the formula (1-a) or the formula (1-b)1、R1、R2AndY1～Y4are all as defined in formula (1).
5. A compound of formula (1), formula (2), formula (1-a) or formula (1-b) according to any one of claims 1,3 or 4, wherein Ar is Ar1An electron deficient heteroaryl group selected from substituted or unsubstituted C3 to C30 containing at least two N's.
6. A compound of formula (1), formula (2), formula (1-a) or formula (1-b) according to any one of claims 1,3 or 4, wherein Ar is Ar1Selected from the structures represented by any one of the following formulae (3-1) to (3-2):
Figure FDA0002099379770000031
in the formula (3-1), Z1、Z2、Z3、Z4And Z5Each independently selected from CR6Or an N atom, and Z1、Z2、Z3、Z4And Z5At least one of which is an N atom;
in the formula (3-2), Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13Each independently selected from CR6Or an N atom, and Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least one of which is an N atom;
wherein R is6One selected from hydrogen, 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 and substituted or unsubstituted C3-C30 heteroaryl.
7. A compound of formula (la) according to claim 6, wherein:
in the formula (3-1), the Z1、Z2、Z3、Z4And Z5At least two of which are N atoms;
in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least two of which are N atoms.
8. A compound of formula (1), formula (2), formula (1-a) or formula (1-b) according to any one of claims 1,3 or 4, wherein Ar is Ar1One selected from the following substituted or unsubstituted groups: quinazolinyl, triazinyl, pyrimidinyl, quinoxalinyl.
9. A compound of formula (1), formula (2), formula (1-a) or formula (1-b) according to any one of claims 1,3 or 4, wherein Ar is Ar1One selected from the group consisting of substituted or unsubstituted groups represented by the following formulae A1-A14:
Figure FDA0002099379770000041
preferably, Ar is1One selected from the following groups represented by B1-B19:
Figure FDA0002099379770000042
Figure FDA0002099379770000051
10. a compound of formula (I) according to any one of claims 1,3 or 4, wherein R is a member of formula (1), formula (2), formula (1-a) or formula (1-b)5Selected from substituted or unsubstituted C6～C18An aryl group;
preferably, R5Selected from substituted or unsubstitutedThe following groups: phenyl, naphthyl and biphenyl.
11. A compound of formula (I) according to any one of claims 1,3 or 4, wherein R is a member of formula (1), formula (2), formula (1-a) or formula (1-b)1And R2Is hydrogen.
12. A compound of formula (la), formula (1), formula (2), formula (1-a) or formula (1-b) according to any one of claims 1,3, 4, 10 or 11, wherein when Y is1～Y4Each of which is independently selected from CR4When R is in the above-mentioned range4Is hydrogen.
13. A compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
Figure FDA0002099379770000052
Figure FDA0002099379770000061
Figure FDA0002099379770000071
Figure FDA0002099379770000081
Figure FDA0002099379770000091
Figure FDA0002099379770000101
Figure FDA0002099379770000111
Figure FDA0002099379770000121
Figure FDA0002099379770000131
Figure FDA0002099379770000141
Figure FDA0002099379770000151
Figure FDA0002099379770000161
Figure FDA0002099379770000171
14. use of a compound as claimed in any one of claims 1 to 13 as a light-emitting host material in an organic electroluminescent device.
15. 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 to 13.
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