CN110734446A - organic compound and application thereof - Google Patents

organic compound and application thereof Download PDF

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CN110734446A
CN110734446A CN201911044566.3A CN201911044566A CN110734446A CN 110734446 A CN110734446 A CN 110734446A CN 201911044566 A CN201911044566 A CN 201911044566A CN 110734446 A CN110734446 A CN 110734446A
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邢其锋
丰佩川
陈跃
胡灵峰
陈义丽
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YANTAI XIANHUA CHEM-TECH Co Ltd
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YANTAI XIANHUA CHEM-TECH Co Ltd
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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to organic compounds and application thereof.

Description

organic compound and application thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to organic compounds and application thereof.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has series advantages of self-luminescence, low-voltage direct current driving, full curing, wide viewing angle, light weight, simple composition and process, etc., 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 broad application prospect.
With the continuous advance of OLED technology in both lighting and display fields, people pay more attention to the research on high-efficiency organic materials affecting the performance of OLED devices, and organic electroluminescent devices with good efficiency and long service life are generally the result of optimized matching of device structures and various organic materials.
CN102558121A reports that carbazole fused ring aromatic amine compounds are used as hole transport materials, but the mobility of the materials is not high enough, the voltage of devices is high, and the service life is to be improved.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides an organic compound and application thereof.
The technical scheme for solving the technical problems is that organic compounds have the following structural formula:
Figure BDA0002253776430000021
wherein Ar is1、Ar2Each independently is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any of the heteroaromatic groups of (a);
R1-R6ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri are each independently hydrogen, deuterium, C1-C6Alkyl radical, C5-C20Cycloalkyl, spirocycloalkyl, C6-C30Aryl or C3-C30Any of the heteroaromatic groups of (a);
x, Y are each independently a bond, O, S, CR7R8Or NR9And at least are not chemical bonds;
wherein R is7、R8Each independently is C1-C6Alkyl radical, C5-C20Cycloalkyl radical, C6-C30Aryl or C3-C30Any kinds of heteroaromatic radical, R9Is C6-C30Aryl or C3-C30Any kinds of heteroaromatic groups.
Step , Ar1、Ar2Each independently is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
Step , R1-R6Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri are each independently hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
Step , R7、R8Each independently of the otherOr is methyl, ethyl, cyclohexyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl; r9Is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
Step , R1-R6And/or two groups which are arbitrarily adjacent to each other between Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh and Ri are connected to form a ring.
Further , the structural formula of the organic compound is preferably as follows:
Figure BDA0002253776430000031
Figure BDA0002253776430000041
the second object of the present invention is to provide the use of the above organic compounds in organic electroluminescent devices.
organic electroluminescent device comprises th electrode, second electrode and organic layer between th electrode and second electrode, wherein the organic layer contains the compound.
The invention has the beneficial effects that:
the compound has an ortho-aryl substituted triarylamine structure, the triarylamine structure has high migration efficiency to holes, meanwhile, the vapor deposition temperature of the ortho-aryl substituted compound is obviously reduced, the compound can keep good thermodynamic stability while the vapor deposition temperature is reduced, and the presence of an ortho-substituent can provide a protection effect on an arylamine center, so that the compound has a good effect on the service life of the material. The compounds of the present invention are suitable for use as hole transport layers in OLED devices.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
Synthesis of Compound A1, the reaction equation is as follows:
Figure BDA0002253776430000051
the synthesis method comprises the following steps:
(1) in a reaction flask, dibenzofuran-4-boronic acid (100mmol), 2-iodo-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) were added, and the mixture was reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M1;
(2) adding M1(100mmol), triphenylphosphine (100mmol) and 1000mL of o-dichlorobenzene in a reaction bottle, heating and refluxing, reacting for 12h, concentrating the reaction solution, performing column chromatography, and separating to obtain an intermediate M2;
(3) adding M2(100mmol), iodobenzene (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M3;
(4) into a reaction flask, M3(100mmol), (2-biphenylyl) -aniline (110mmol), 0.9g (0.785mmol, 0.5%) Pd2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain A1.
1H NMR(CDCl3,400MHz)δ8.04(dd,J＝12.0,7.2Hz,4H),7.60(t,J＝10.0Hz,4H),7.54(s,1H),7.53–7.33(m,10H),7.31(s,1H),7.24(s,2H),7.11(d,J＝10.0Hz,4H),7.00(s,1H),6.40(s,1H)。
Example 2
Synthesis of Compound A6, the reaction equation is as follows:
Figure BDA0002253776430000061
the synthesis method comprises the following steps:
(1) into a reaction flask, dibenzothiophene-1-boronic acid (100mmol), 2-iodo-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) were added, and the mixture was reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M1;
(2) adding M1(100mmol), triphenylphosphine (100mmol) and 1000mL of o-dichlorobenzene in a reaction bottle, heating and refluxing, reacting for 12h, concentrating the reaction solution, performing column chromatography, and separating to obtain an intermediate M2;
(3) adding M2(100mmol), iodobenzene (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M3;
(4) into a reaction flask, M3(100mmol), (1-dibenzofuranyl) -aniline (110mmol), 0.9g (0.785mmol, 0.5%) Pd was added2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain A6.
1H NMR(CDCl3,400MHz)δ8.45(s,1H),8.25(s,1H),7.97(d,J＝10.0Hz,2H),7.86(s,2H),7.78(s,1H),7.62(s,2H),7.60–7.52(m,4H),7.50(s,2H),7.39(s,1H),7.30(d,J＝7.6Hz,2H),7.24-7.00(m,8H),6.40(s,1H)。
Example 3
Synthesis of Compound A10, the reaction equation is as follows:
Figure BDA0002253776430000081
the synthesis method comprises the following steps:
(1) adding N-phenylcarbazole-4-boric acid (100mmol), 2-iodine-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) into a reaction bottle, and reacting at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M1;
(2) adding M1(100mmol), triphenylphosphine (100mmol) and 1000mL of o-dichlorobenzene in a reaction bottle, heating and refluxing, reacting for 12h, concentrating the reaction solution, performing column chromatography, and separating to obtain an intermediate M2;
(3) adding M2(100mmol), 4-iodobiphenyl (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M3;
(4) into a reaction flask, M3(100mmol), (2-biphenylyl) -aniline (110mmol), 0.9g (0.785mmol, 0.5%) Pd2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain A10.
1H NMR(CDCl3,400MHz)δ8.55(s,1H),7.93(t,J＝12.0Hz,4H),7.75(s,1H),7.81–7.56(m,6H),7.53(dd,J＝10.8,6.0Hz,2H),7.52–7.35(m,11H),7.24(s,2H),7.12(dd,J＝9.6,8.0Hz,8H),7.00(s,1H),6.40(s,1H)。
Example 4
Synthesis of Compound A17, the reaction equation is as follows:
Figure BDA0002253776430000091
the synthesis method comprises the following steps:
(1) into a reaction flask, dibenzothiophene-1-boronic acid (100mmol), 2-iodo-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) were added, and the mixture was reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M1;
(2) adding M1(100mmol), triphenylphosphine (100mmol) and 1000mL of o-dichlorobenzene in a reaction bottle, heating and refluxing, reacting for 12h, concentrating the reaction solution, performing column chromatography, and separating to obtain an intermediate M2;
(3) adding M2(100mmol), 4-iodobiphenyl (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M3;
(4) into a reaction flask, M3(100mmol), (2-biphenyl) - (2, 6-dimethyl-biphenyl) amine (110mmol), 0.9g (0.785mmol, 0.5%) Pd2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain A17.
1H NMR(CDCl3,400MHz)δ8.13(d,J＝12.4Hz,2H),7.75(s,2H),8.07–7.58(m,6H),7.77–7.58(m,7H),7.77–7.54(m,4H),7.52–7.35(m,5H),7.31-7.08(m,6H),2.13(s,6H)。
Example 5
Synthesis of Compound A30, the reaction equation is as follows:
the synthesis method comprises the following steps:
(1) in a reaction flask, naphthobenzofuran-6-boric acid (100mmol), 2-iodo-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water and 40g of potassium carbonate (300mmol) were added, and reaction was carried out at 100 ℃ for 8 h; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M1;
(2) adding M1(100mmol), triphenylphosphine (100mmol) and 1000mL of o-dichlorobenzene in a reaction bottle, heating and refluxing, reacting for 12h, concentrating the reaction solution, performing column chromatography, and separating to obtain an intermediate M2;
(3) adding M2(100mmol), 9-dimethylfluorene-2-iodine (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 hours; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M3;
(4) into a reaction flask, M3(100mmol), (1-dibenzofuranyl) -aniline (110mmol), 0.9g (0.785mmol, 0.5%) Pd was added2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain A30.
1H NMR(CDCl3,400MHz)δ8.51(s,2H),8.24(s,1H),7.98(dd,J＝12.0,8.4Hz,5H),7.92–7.75(m,3H),7.72(s,1H),7.69–7.48(m,3H),7.48–7.45(m,1H),7.39(s,2H),7.33(t,J＝10.0Hz,4H),7.24(d,J＝6.4Hz,4H),7.16(s,1H),7.08(s,2H),7.00(s,1H),6.40(s,1H),1.69(s,6H)。
Example 6
Synthesis of Compound A43, the reaction equation is as follows:
Figure BDA0002253776430000111
the synthesis method comprises the following steps:
(1) adding 4-bromophenoxaxine (100mmol), 4-iodobiphenyl (105mmol), CuI (1%), 1, 10-phenanthroline (1%), dimethylbenzene 800mL and potassium carbonate 40g (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M1;
(2) m1(100mmol), pinacol diborate (120mmol), 0.9g (0.785mmol, 0.5%) Pd were added to the reaction flask2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain M2;
(3) m2(100mmol), 2-iodo-5-bromonitrobenzene (100mmol), 0.9g (0.785mmol, 0.5%) of tetratriphenylphosphine palladium, 500mL of toluene, 200mL of ethanol, 200mL of water, and 40g of potassium carbonate (300mmol) were added to a reaction flask, and reacted at 100 ℃ for 8 hours; stopping the reaction after the reaction is finished; cooling to room temperature, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M3;
(4) adding M3(100mmol), triphenylphosphine (100mmol) and 1000mL of o-dichlorobenzene in a reaction bottle, heating and refluxing, reacting for 12h, concentrating the reaction solution, performing column chromatography, and separating to obtain an intermediate M4;
(5) adding M4(100mmol), iodobenzene (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M5;
(6) into a reaction flask, M5(100mmol), (2-biphenylyl) -aniline (110mmol), 0.9g (0.785mmol, 0.5%) Pd2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, performing silica gel column chromatography, and recrystallizing to obtain A43.
1H NMR(CDCl3,400MHz)δ8.03(d,J＝10.0Hz,2H),7.75(s,1H),7.60–7.52(m,4H),7.52–7.35(m,8H),7.31-7.14(m,7H),7.03–6.96(m,13H)。
Example 7
The synthesis of compound 31, the reaction equation is as follows:
Figure BDA0002253776430000131
the synthesis method comprises the following steps:
(1) into a reaction flask were added (100mmol) 1-bromo-2-hydroxynaphthalene, pinacol diboron (120mmol), 0.9g (0.785mmol, 0.5%) Pd2(dba)31500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting at 100 ℃ for 5 h; stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water and ethyl acetate for extraction, concentrating, carrying out organic phase column chromatography, and recrystallizing and purifying the obtained solid in toluene to obtain an intermediate M1;
(2) taking (100mmol) M1, (100mmol) 2-bromo-6-chloroFluorobenzene, (1%) Pd (PPh)3)4Heating 40g (300mmol) of sodium carbonate, toluene (800mL), ethanol (200mL) and water (200mL) to reflux, and reacting for 8 h; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M2;
(3) taking (100mmol) M2, (1%) Pd (OAc)2Heating 40g (300mmol) of sodium carbonate and DMF (500mL) to reflux, and reacting for 8 h; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M3;
(4) into a reaction flask, M3(100mmol), pinacol diborate (120mmol), 0.9g (0.785mmol, 0.5%) Pd2(dba)31500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting at 100 ℃ for 5 h; stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water and ethyl acetate for extraction, concentrating, carrying out organic phase column chromatography, and recrystallizing and purifying the obtained solid in toluene to obtain an intermediate M4;
(5) taking (100mmol) M4, 32.6g (100mmol) 2-iodo-5-bromonitrobenzene and (1%) Pd (PPh)3)4Heating 40g (300mmol) of sodium carbonate, toluene (800mL), ethanol (200mL) and water (200mL) to reflux, and reacting for 8 h; extracting the reaction liquid by ethyl acetate, and concentrating an organic phase to obtain a yellow solid M5;
(6) adding (100mmol) M5 and 1000mL o-dichlorobenzene solution into a reaction bottle to neutralize (300mmol) triphenylphosphine, heating to reflux, reacting for 12h, and finishing the reaction; evaporating to remove solvent, performing silica gel column chromatography, and separating to obtain intermediate M6;
(7) adding M6(100mmol), iodobenzene (105mmol), CuI (1%), 1, 10-phenanthroline (1%), xylene (800mL) and potassium carbonate (40 g) (300mmol) into a reaction bottle, and reacting at 140 ℃ for 12 h; stopping the reaction after the reaction is finished; cooling to room temperature, adding water, separating organic phase, concentrating, and performing silica gel column chromatography to obtain yellow powder M7;
(6) into a reaction flask, M7(100mmol), (2-methyl-6-phenylbenzene) -phenylamine (110mmol), and 0.9g (0.785mmol, 0.5%) Pd2(dba)3500mL of toluene and 40g (300mmol) of sodium tert-butoxide, and reacting for 8h at 100 ℃; stopping the reaction after the reaction is finished; cooling to room temperature, concentrating, and making silica gel columnChromatography and recrystallization gave a 31.
1H NMR(CDCl3,400MHz)δ8.34-8.24(m,3H),7.98(t,J＝10.0Hz,3H),7.56–7.39(m,8H),7.29(s,1H),7.24(d,J＝8.0Hz,3H),7.12-7.04(m,6H),6.90-6.76(m,5H),2.13(s,3H).
The other compounds of the present invention can be synthesized by selecting raw materials with suitable structures according to the above-mentioned ideas of examples 1-7, and the details are not repeated herein.
Device application example
An OLED includes th and second electrodes, and an organic layer between the electrodes, which in turn may be divided into a plurality of regions.
In a specific application example, a substrate may be used under the th electrode or over the second electrode, and the substrate may be made of glass or a polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency.
The th electrode may be formed by sputtering or depositing a material used as the th electrode on the substrate when the th electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) th electrode as a cathode can be made of a metal or 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.
The organic layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic layer may be small organic molecules, large organic molecules, and polymers, and combinations thereof.
The hole transport region may be a Hole Transport Layer (HTL) having a single layer structure including a single layer containing compounds only and a single layer containing a plurality of compounds, or a multi-layer structure including at least layers among 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.
For example, or more compounds of HT-1 to HT-34, or or more compounds of HI1-HI3, or or more compounds of HT-1 to HT-34 can be used to dope or more compounds of HI 1-3.
Figure BDA0002253776430000172
The light emitting layer may include light emitting dyes (i.e., dopants) that may emit different wavelength spectra and may also include a Host material (Host), the light emitting layer may be a single color light emitting layer that may emit a single color such as red, green, blue, etc., a plurality of single color light emitting layers of different colors may be arranged in a planar manner according to a pixel pattern or may be stacked at to form a color light emitting layer, when the light emitting layers of different colors are stacked at , they may be spaced apart from each other or may be connected to each other, the light emitting layer may also be a single color light emitting layer that may emit different colors such as red, green, blue, etc., simultaneously.
According to different technologies, different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermal activation delayed fluorescence luminescent materials and the like can be adopted as luminescent layer materials, in OLED devices, a single luminescent technology can be adopted, and a combination of a plurality of different luminescent technologies can be adopted.
The device light emitting layer may comprise a host material and a light emitting dye, wherein the host material includes, but is not limited to, or combinations of more of the conventional materials shown in GPH1-GPH80 below.
Figure BDA0002253776430000181
Figure BDA0002253776430000191
Figure BDA0002253776430000201
In aspects of the invention, the emissive layer employs phosphorescent electroluminescent technology, the emissive layer may have a phosphorescent dopant selected from, but not limited to, the combination of of RPD-1 through RPD-57 listed below.
Figure BDA0002253776430000202
The electron transport region may be a single-layer structure of an Electron Transport Layer (ETL), including a single-layer electron transport layer containing only compounds and a single-layer electron transport layer containing a plurality of compounds.
In the aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of or more of ET-1 through ET-57 listed below.
Figure BDA0002253776430000212
Figure BDA0002253776430000221
Figure BDA0002253776430000231
Figure BDA0002253776430000241
The device may further comprise an electron injection layer disposed between the electron transport layer and the cathode, the electron injection layer comprising a material selected from the group consisting of, but not limited to, or more selected from the group consisting of LiQ, LiF, NaCl, CsF, Li2O,Cs2CO3,BaO,Na,Li,Ca。
The effects of the compounds obtained in examples 1 to 7 of the present invention and comparative example R1 as a hole transport layer in a device are described in detail by performance tests below.
The preparation process of the organic electroluminescent device in the application example of the device is as follows:
the following compounds were used as controls:
Figure BDA0002253776430000242
(1) ultrasonically treating the glass plate coated with the ITO transparent conducting layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent, baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
(2) the above-mentioned belt is provided withPlacing the glass substrate of 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;
(3) the compounds of examples 1 to 7 and R1 were each vacuum-evaporated on a hole injection layer at a rate of 0.1nm/s and a total film thickness of 80nm as a hole transport layer of a device;
(4) a luminescent layer of the device is evaporated in vacuum on the hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material GPH-59 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, the proportion of 3% evaporation of the dye RPD-1 is set, and the total film thickness of evaporation is 30 nm;
(5) an electron transport layer of the device is vacuum evaporated on the light emitting layer, and the material ET-42 is selected, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
(6) 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.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the organic electroluminescent device obtained in the application example and the comparative example was measured for driving voltage, current efficiency and lifetime at the same luminance using a digital source meter and a luminance meter, specifically, for increasing the voltage at a rate of 0.1V per second, and it was measured 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 are shown in table 1 below.
TABLE 1
Figure BDA0002253776430000251
Figure BDA0002253776430000261
As can be seen from the data in Table 1, the novel organic material prepared by the invention is used for a hole transport layer of an organic electroluminescent device, can effectively reduce the take-off and landing voltage, improves the current efficiency, prolongs the service life of the device, and is a hole transport layer material with good performance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (8)

  1. An organic compound of class 1, , having the formula:
    wherein Ar is1、Ar2Each independently is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any of the heteroaromatic groups of (a);
    R1-R6ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri are each independently hydrogen, deuterium, C1-C6Alkyl radical, C5-C20Cycloalkyl, spirocycloalkyl, C6-C30Aryl or C3-C30Any of the heteroaromatic groups of (a);
    x, Y are each independently a bond, O, S, CR7R8Or NR9And at least are not chemical bonds;
    wherein R is7、R8Each independently is C1-C6Alkyl radical, C5-C20Cycloalkyl radical, C6-C30Aryl or C3-C30Any kinds of heteroaromatic radical, R9Is C6-C30Aryl or C3-C30Any kinds of heteroaromatic groups.
  2. 2. The organic compound of claim 1, wherein Ar is Ar1、Ar2Each independently is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
  3. 3. An organic compound according to claim 1, wherein R is1-R6Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri are each independently hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
  4. 4. An organic compound according to claim 1, wherein R is7、R8Each independently is methyl, ethyl, cyclohexyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl; r9Is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
  5. 5. An organic compound according to claim 1, wherein R is1-R6And/or two groups which are arbitrarily adjacent to each other between Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh and Ri are connected to form a ring.
  6. 6. An organic compound according to claim 1, having the formula:
    Figure FDA0002253776420000031
  7. use of organic compounds according to any one of claims 1 to 6 to in an organic electroluminescent device.
  8. An organic electroluminescent device, comprising a th electrode, a second electrode and an organic layer comprising at least light-emitting layers interposed between the th electrode and the second electrode, wherein the organic layer contains the compound of of any one of claims 1 to 6.
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