CN111187273A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN111187273A
CN111187273A CN202010118746.8A CN202010118746A CN111187273A CN 111187273 A CN111187273 A CN 111187273A CN 202010118746 A CN202010118746 A CN 202010118746A CN 111187273 A CN111187273 A CN 111187273A
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邢其锋
刘永祥
单宏斌
辛乐民
胡灵峰
陈跃
陈义丽
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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 an organic compound and application thereof. The compound has a triarylamine structure substituted by pyridine or pyridine derivatives, and the triarylamine structure has high migration efficiency for holes, and meanwhile, the compound substituted by pyridine or pyridine derivatives can properly reduce the HOMO energy level of the compound, improve the starting voltage under low brightness, and has an important effect on voltage collocation of red, green and blue devices. The compounds of the present invention are suitable for use as hole transport layers in OLED devices.

Description

Organic compound and application thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an organic compound and application thereof.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage direct current drive, full curing, wide viewing angle, light weight, simple composition and process and the like, and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle, low power, 1000 times of response speed of the liquid crystal display, and lower manufacturing cost than the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research of efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The currently applied hole transport layer material has room for improvement in hole mobility and evaporation temperature, and the industry also urgently hopes to obtain a material with higher hole mobility and lower evaporation temperature.
CN102558121A reports that a carbazole fused ring aromatic amine compound is used as a hole transport material, but the mobility of the material is not high enough, the voltage of a device is higher, 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 as follows: an organic compound having the following structural formula:
Figure BDA0002392302930000021
wherein Ar is1、Ar2Each independently is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
R1-R6each independently of the others is hydrogen, deuterium, C1-C6Alkyl radical, C5-C20Cycloalkyl, spirocycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
l is a bond, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
x, Y are each independently a bond, O, S, CR7R8Or NR9And X, Y at least one is not a bond;
wherein R is7、R8Each independently is C1-C6Alkyl radical, C5-C20Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups; r9Is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
Z1-Z5each independently is N or CRnAnd Z is1、Z2、Z3、Z4、Z5At least one of which is N;
wherein R isnRepresents a plurality of, each independently hydrogen, C1-C12Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of the heteroaromatic groups.
Further, Ar1、Ar2Each independently is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
Further, R1-R6Each independently hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
Further, L is a bond, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
Further, R7、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; rnIs hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothienyl, spirofluorenyl, dimethylfluorenyl or carbazolyl.
Further, R1-R6Any two adjacent groups between the two groups are connected to form a ring.
Further, R7、R8Are connected into a ring.
Further, RnAny two groups adjacent to each otherAre connected into a ring.
Further, the structural formula of the above organic compound is preferably as follows:
Figure BDA0002392302930000041
Figure BDA0002392302930000051
the second object of the present invention is to provide the use of the above organic compounds in organic electroluminescent devices.
An organic electroluminescent device comprises a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer contains the organic compound.
The invention has the beneficial effects that:
the compound has a triarylamine structure substituted by pyridine or pyridine derivatives, and the triarylamine structure has high migration efficiency for holes, and meanwhile, the compound substituted by pyridine or pyridine derivatives can properly reduce the HOMO energy level of the compound, improve the starting voltage under low brightness, and play an important role in voltage matching of red, green and blue devices. 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 BDA0002392302930000061
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-pyridin-2-phenyl) -2- (9, 9-dimethylfluorene) amine (110mmol), 0.9g (0.785mmol, 0.5%) Pd were 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 A1.
1H NMR(CDCl3,400MHz)δ9.31(s,1H),8.37(s,1H),8.07(d,J＝12.8Hz,2H),7.96(s,1H),7.88(d,J＝10.0Hz,2H),7.69–7.52(m,5H),7.50(s,1H),7.41–7.29(m,4H),7.25(d,J＝9.6Hz,2H),7.14-6.90(m,5H),6.40(s,1H),1.69(s,6H)。
Example 2
Synthesis of Compound A6, the reaction equation is as follows:
Figure BDA0002392302930000071
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), N-phenyl-3- (pyridin-2-yl) 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 A6.
1H NMR(CDCl3,400MHz)δ8.45(s,1H),8.39(s,1H),8.30(d,J＝12.4Hz,4H),8.06–7.51(m,8H),7.71–7.60(m,4H),7.71–7.51(m,6H),7.60–7.53(m,3H),7.50(s,1H),7.38(s,1H),7.31-7.18(m,4H),7.08(s,35H)-6.90(m,3H),6.40(s,1H)。
Example 3
Synthesis of Compound A10, the reaction equation is as follows:
Figure BDA0002392302930000081
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), 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) m3(100mmol), 9-phenyl-N- (4- (pyridin-2-yl) phenyl) -9H-carbazole-3-aniline (110mmol), 0.9g (0.785mmol, 0.5%) Pd were added to a 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 A10.
1H NMR(CDCl3,400MHz)δ8.55(s,1H),8.37(s,1H),8.04(d,J＝10.0Hz,2H),7.79(s,1H),7.66(d,J＝11.2Hz,4H),7.58(s,3H),7.51(d,J＝10.0Hz,5H),7.42–7.32(m,5H),7.12(dd,J＝27.5,12.5Hz,4H),6.90(s,1H),6.40(s,1H)。
Example 4
Synthesis of Compound A17, the reaction equation is as follows:
Figure BDA0002392302930000091
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) in a reaction flask, M3(100mmol), N- (2, 6-dimethyl-4- (pyridin-3-yl) phenyl) -9-phenyl-9H-carbazole-3-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 A17.
1H NMR(CDCl3,400MHz)δ9.24(s,1H),8.70(s,1H),8.55(s,2H),8.49–8.15(m,6H),7.91(d,J＝10.0Hz,2H),7.66–7.45(m,10H),7.36(d,J＝8.0Hz,2H),7.31-7.11(m,6H),6.40(s,2H),2.13(s,6H)。
Example 5
Synthesis of Compound A30, the reaction equation is as follows:
Figure BDA0002392302930000101
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) in a reaction flaskM3(100mmol), N- (4- (pyridin-2-yl) phenyl) dibenzofuranyl-2-amine (110mmol), 0.9g (0.785mmol, 0.5%) Pd were 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),8.37(s,2H),8.40–8.10(m,10H),8.04(s,2H),7.96(t,J＝9.6Hz,8H),7.90(s,2H),7.84(s,2H),7.77(s,1H),7.72(s,3H),7.54(d,J＝1.6Hz,6H),7.50–7.29(m,21H),7.24(s,1H),7.14(s,2H),6.90(s,2H),6.40(s,2H),1.69(s,12H)。
Example 6
The synthesis of compound 31, the reaction equation is as follows:
Figure BDA0002392302930000111
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 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 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 diboron (120mmol), and 0.9g (0.7 mmol) were charged85mmol，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, 1000mL o-dichlorobenzene solution and (300mmol) triphenylphosphine into a reaction bottle, 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;
(8) into a reaction flask, M7(100mmol), 2, 6-dimethyl-N- (3- (pyridin-3-yl) 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 A31.
1H NMR(CDCl3,400MHz)δ9.24(s,1H),8.70(s,1H),8.30(d,J＝13.6Hz,2H),7.97(d,J＝12.0Hz,2H),7.70(s,1H),7.56(ddd,J＝12.8,10.4,8.0Hz,8H),7.28(d,J＝10.0Hz,3H),7.23–7.12(m,3H),7.10(s,1H),6.40(s,1H),2.13(s,6H)。
Example 7
Synthesis of Compound A43, the reaction equation is as follows:
Figure BDA0002392302930000131
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), N, 6-diphenylpyridyl-2-amine (110mmol) and 0.9g (0.785mmol, 0.5%) of Pd were charged2(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)δ8.00(d,J＝10.0Hz,4H),7.75(s,1H),7.62(s,2H),7.72–7.52(m,8H),7.72–7.39(m,15H),7.37(s,2H),7.31(s,1H),7.28(d,J＝12.0Hz,3H),7.24(s,2H),7.31–7.06(m,7H),7.00(dd,J＝10.0,6.0Hz,4H),6.93(s,1H),6.83(s,1H),6.38(d,J＝10.0Hz,2H)。
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
The OLED includes first and second electrodes, and an organic layer between the electrodes. The organic layer may in turn be divided into a plurality of regions. For example, the organic layer may include a hole transport region, a light emitting layer, an electron transport region, and the like.
In a specific application example, 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, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. 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 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 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 BDA0002392302930000151
Figure BDA0002392302930000161
Figure BDA0002392302930000171
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
Figure BDA0002392302930000172
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.
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, one or more combinations of conventional materials as shown in GPH1-GPH80 below.
Figure BDA0002392302930000181
Figure BDA0002392302930000191
Figure BDA0002392302930000201
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 BDA0002392302930000202
Figure BDA0002392302930000211
The OLED organic layer may also 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 BDA0002392302930000212
Figure BDA0002392302930000221
Figure BDA0002392302930000231
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, combinations of one or more of the following: 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 the comparative product R1 as a hole transport layer in a device are described in detail by performance tests below.
The preparation processes of the organic electroluminescent devices described in application examples 1 to 7 and comparative example 1 of the present invention were as follows:
the following compounds were used as controls:
Figure BDA0002392302930000241
(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) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa，Vacuum evaporating HI-3 on the anode layer film to form 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 BDA0002392302930000251
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 (11)

1. An organic compound is characterized in that the structural formula is as follows:
Figure FDA0002392302920000011
wherein Ar is1、Ar2Each independently is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
R1-R6each independently of the others is hydrogen, deuterium, C1-C6Alkyl radical, C5-C20Cycloalkyl, spirocycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
l is a bond, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
x, Y are each independently a bond, O, S, CR7R8Or NR9And X, Y at least one is not a bond;
wherein R is7、R8Each independently is C1-C6Alkyl radical, C5-C20Cycloalkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups; r9Is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of heteroaromatic groups;
Z1-Z5each independently is N or CRnAnd Z is1、Z2、Z3、Z4、Z5At least one of which is N;
wherein R isnRepresents a plurality of, each independently hydrogen, C1-C12Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Any one of the heteroaromatic groups.
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. An organic compound according to claim 1, wherein R is1-R6Each independently hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
4. The organic compound of claim 1, wherein L is a bond, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
5. 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, dibenzothienyl, biphenyl,spirofluorenyl, dimethylfluorenyl, or carbazolyl; rnIs hydrogen, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, spirofluorenyl, dimethylfluorenyl, or carbazolyl.
6. An organic compound according to claim 1, wherein R is1-R6Any two adjacent groups between the two groups are connected to form a ring.
7. An organic compound according to claim 1, wherein R is7、R8Are connected into a ring.
8. An organic compound according to claim 1, wherein R isnAny two adjacent groups between the two groups are connected to form a ring.
9. An organic compound according to claim 1, having the formula:
Figure FDA0002392302920000031
Figure FDA0002392302920000041
10. use of an organic compound according to any one of claims 1 to 9 in an organic electroluminescent device.
11. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer comprising at least one light-emitting layer interposed between the first electrode and the second electrode, wherein the organic layer contains the organic compound according to any one of claims 1 to 9.
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