CN115108919A - Organic electroluminescent compound and organic electroluminescent device - Google Patents

Organic electroluminescent compound and organic electroluminescent device Download PDF

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CN115108919A
CN115108919A CN202210698948.3A CN202210698948A CN115108919A CN 115108919 A CN115108919 A CN 115108919A CN 202210698948 A CN202210698948 A CN 202210698948A CN 115108919 A CN115108919 A CN 115108919A
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organic electroluminescent
ring
group
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李明
段伟伟
李猛
王辉
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses an organic electroluminescent compound and an organic electroluminescent device, the provided organic electroluminescent compound is favorable for intermolecular charge transition capacity due to a rigid ring structure consisting of a polycyclic ring and a spiro ring, and meanwhile, the R4 position of the compound structural formula is connected with a substituent group, so that the intermolecular is not easy to crystallize and aggregate, and the material has higher photo-thermal stability. Therefore, the organic electroluminescent compound provided by the invention is used as a hole transport material in an organic electroluminescent device, and the applicant finds that the effect achieved by substituting triarylamine at different positions of the parent nucleus of the organic electroluminescent compound is different, which may be the reason of the change of the relation between the Highest Occupied Molecular Orbital (HOMO) and the work function of the anode material. Tests prove that the specific position defined by the invention has better efficiency and service life effect of the organic electroluminescent device.

Description

Organic electroluminescent compound and organic electroluminescent device
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic electroluminescent compound and an organic electroluminescent device.
Background
The organic electroluminescent diode (OLED) has the characteristics of self luminescence, wide viewing angle, high contrast, short response time, low driving voltage, wide temperature adaptation range, capability of being manufactured into soft and the like, can realize a full-color OLED display through three organic electroluminescent materials (red, green and blue), is a new generation of flat panel display technology, can be used for flat panel displays and illumination light sources, and is currently commercialized flat panel displays which are put into the market in batches and applied to high-end electronic products.
The organic electroluminescent element is a self-luminous element utilizing the following principle: by applying an electric field, the fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode. It has the following structure: an anode, a cathode, and an organic material layer therebetween. In order to improve efficiency and stability of the organic electroluminescent element, the organic material layer generally includes a plurality of layers having different materials, such as a hole injection layer HIL), a hole transport layer HTL), a light emitting layer, an electron transport layer ETL), and an electron injection layer EIL). In such an organic light emitting element, when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode are injected into an organic material layer, and the generated excitons generate light having a specific wavelength while shifting to a ground state. Wherein the hole transport layer can change hole transport efficiency, light emitting efficiency, lifetime, etc. of holes to the light emitting layer.
4,4 ' -bis [ N-1-naphthyl-N-phenylamino ] biphenyl NPB, N ' -diphenyl-N, N ' -bis 3-methylphenyl-1, 1 ' -biphenyl-4, 4 ' -diamine TPD and the like are currently used as hole transport materials. Although organic electroluminescent elements using these materials have improved hole transport efficiency, light emission efficiency, lifetime, and the like; however, it is still not very desirable in terms of service life.
Therefore, the development of a hole transport material with a novel structure to improve the long service life of an electroluminescent device is a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the defects of the prior art, the invention provides an organic electroluminescent material with good film forming property, high efficiency, low driving voltage and long service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides an organic electroluminescent compound, which has a structure shown in the following chemical formula A:
Figure BDA0003703208340000021
R 1 、R 2 and R 3 Is a mono-or polysubstituent; each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, substituted or unsubstitutedUnsubstituted C8-C16 condensed ring group;
r is monosubstituted and independently positioned on Ar1, Ar2 and Ar3 rings, R4 is substituted or unsubstituted triarylamine electron transport group, wherein the substituent is C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, substituted or unsubstituted C8-C16 condensed ring group
Wherein the alkyl is a straight-chain alkyl, a branched-chain alkyl, a cyclic alkyl, a straight-chain alkyl substituted by at least 1 substituent, a branched-chain alkyl substituted by at least 1 substituent, or a cyclic alkyl substituted by at least 1 substituent; wherein, the substituent is one or more of halogen, deuterium, cyano and hydroxyl independently.
The aryl group is preferably an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein, the substituents are independently selected from halogen, deuterium, amino, cyano, nitro and hydroxyl;
the heteroaromatic heterocyclic group is preferably an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro and hydroxyl;
R 1 、R 2 and R 3 The substitution position is any position of the ring;
R 1 、R 2 and R 3 Independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle and a substituted or unsubstituted C5-C60 spiro ring with other substituents on the ring;
R 1 、R 2 、R 3 substituted or unsubstituted C3-C30 aliphatic ring, substituted or unsubstituted C6-C60 aromatic ring, substituted or unsubstituted C2-C60 aromatic heterocycle, substituted or unsubstituted C5-C60 spiro ring;
the substituent on the aliphatic ring, the aromatic heterocyclic ring and the spiro ring is at least one selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group and substituted or unsubstituted C5-C60 spiro ring;
the heteroaromatic ring contains at least one heteroatom selected from B, N, O, S, Si and P.
The synthetic route of the organic electroluminescent compound provided by the invention is as follows:
Figure BDA0003703208340000031
wherein R is 4 Is a boronic acid pinacol ester group
In the present invention, the R4 position is selected from the following positions:
Figure BDA0003703208340000032
further, the organic electroluminescent compound is selected from any one of the compounds represented by the following structural formula (including but not limited to the compounds described below);
Figure BDA0003703208340000033
Figure BDA0003703208340000041
Figure BDA0003703208340000051
Figure BDA0003703208340000061
Figure BDA0003703208340000071
Figure BDA0003703208340000081
Figure BDA0003703208340000091
Figure BDA0003703208340000101
Figure BDA0003703208340000111
Figure BDA0003703208340000121
Figure BDA0003703208340000131
Figure BDA0003703208340000141
Figure BDA0003703208340000151
Figure BDA0003703208340000161
Figure BDA0003703208340000171
Figure BDA0003703208340000181
some specific structural forms are listed above, but the series of compounds are not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of the groups and the substitution positions thereof, which is not repeated herein
The invention provides an organic electroluminescent compound, and also provides a method for synthesizing a main body structure of the organic electroluminescent compound, which comprises the following steps:
Figure BDA0003703208340000191
it is still another object of the present invention to provide an organic electroluminescent device prepared by the aforementioned organic electroluminescent compounds;
preferably, the organic electroluminescent device comprises an anode, a cathode and at least one organic layer arranged between the anode and the cathode, wherein the organic layer comprises the organic electroluminescent compound;
preferably, the organic layer includes a light emitting layer; wherein, the raw material for forming the luminescent layer comprises a doping material and the organic electroluminescent compound;
preferably, the organic layer further includes a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
According to the technical scheme, compared with the prior art, the invention has the following beneficial effects: the organic electroluminescent compound provided by the embodiment of the invention has a rigid ring structure consisting of a polycyclic ring and a spiro ring, so that the organic electroluminescent compound is favorable for intermolecular charge transition capacity, and meanwhile, R in the structural formula of the compound 4 The position is connected with a substituent group, so that the intermolecular is not easy to crystallize and aggregate, and the material has higher photo-thermal stability. Thus, using the organic electroluminescent compounds of the present invention as hole transport materials in the light-emitting layer, the applicants have found that the effect achieved by the triarylamine substitution at different positions of the parent nucleus of the organic electroluminescent compounds is not the same, which may be the highest occupied fractionThe reason for the change in the relationship of the sub-orbital (HOMO) to the work function of the anode material. Tests prove that the specific position defined by the invention has better efficiency and service life effect of the organic electroluminescent device.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Synthesis of intermediate L
Figure BDA0003703208340000201
Step 1: adding 1-bromo-2-naphthalene methyl benzoate (200mmol), o-bromobenzoic acid (200mmol), tetrakis (triphenylphosphine) palladium (2mmol), potassium carbonate (300mmol) and purified water (100 ml) and tetrahydrofuran (300 ml) into a three-port reaction bottle, heating to 80 ℃ under the protection of nitrogen for reacting for 8 hours, extracting by using dichloromethane after the reaction is finished, and concentrating an organic phase to obtain an intermediate L-1.
Step 2: adding L-1(100mmol), 2-aminophenylboronic acid pinacol ester (100mmol), tetrakis (triphenylphosphine) palladium (1mmol), potassium carbonate (150mmol), 50ml purified water and 300ml dioxane into a three-port reaction bottle, heating to 120 ℃ under the protection of nitrogen, reacting for 10 hours, extracting with dichloromethane after the reaction is finished, and concentrating to perform chromatography (PE/EA is 5/1) to obtain an intermediate L-2.
And 3, step 3: adding 100ml of L-2(40mmol) acetic acid and 15ml of sulfuric acid into a three-mouth reaction bottle, cooling to 0 ℃, slowly dropwise adding an aqueous solution of sodium nitrite (50mmol), slowly pouring a reaction solution into water after the reaction is finished, filtering, and purifying a filter cake column chromatography to obtain an intermediate L-3.
And 4, step 4: adding L-3(50mmol) and polyphosphoric acid 150ml to 100 ℃, reacting for 3h, monitoring the reaction, slowly pouring the reaction liquid into water, extracting with dichloromethane, concentrating, and purifying by column chromatography to obtain an intermediate L-4.
And 5: adding 2-bromo-4-chloro-1, 1-biphenyl (30mmol) into tetrahydrofuran, cooling to-78 ℃, dropwise adding n-butyllithium (36mmol), keeping for 0.5h after dropwise adding, quickly dropwise adding a tetrahydrofuran solution dissolved with L-4(30mmol) into a reaction solution, carrying out heat preservation reaction for 2h, recovering to room temperature for reaction for 2h, adding water for quenching, and extracting and concentrating ethyl acetate to obtain an intermediate L-5.
Step 6: adding L-5(30mmol) and 150ml of dichloromethane into a three-mouth reaction bottle, cooling to 0 ℃, dropwise adding methanesulfonic acid (40ml), reacting at room temperature for 3 hours after dropwise adding, adding water, and extracting and concentrating with dichloromethane to obtain an intermediate L-6.
And 7: mixing L-6(50mmol) and Pd 2 (dba) 3 (1mmol), AcOK (90mmol) and DMF120ml, reacting for 12h at 170 ℃ under the protection of nitrogen, adding water after the reaction is finished, filtering, and purifying the solid by column chromatography to obtain an intermediate L. H-NMR (CDCl) 3 )δ(ppm)＝7.82-7.85(1H)；δ(ppm)＝7.78-7.82(1H)；δ(ppm)＝7.65-7.75(6H)；δ(ppm)＝7.52-7.57(2H)；δ(ppm)＝7.43-7.47(1H)；δ(ppm)＝7.28-7.42(6H)；δ(ppm)＝7.13-7.16(1H)；δ(ppm)＝6.85-6.9(1H)；δ(ppm)＝1.2-1.28(12H)
Synthesis of intermediate M
Figure BDA0003703208340000211
And (3) synthesizing the intermediate M by only replacing the o-bromobenzoic acid in the step 1 for synthesizing the intermediate L with 2-bromo-3-chlorobenzeneboronic acid, wherein the rest steps are the same as the above steps.
Synthesis of intermediate N
Figure BDA0003703208340000221
And (3) synthesizing the intermediate N by only replacing the 2-aminophenylboronic acid pinacol ester in the step 2 for synthesizing the intermediate L with the 2-amino-4-chlorophenylboronic acid pinacol ester, wherein the rest steps are as above.
In the following examples, each of Z-2 to Z-9 was synthesized from a base material without specifying the synthesis process.
Example 1: preparation of Compound A1
Figure BDA0003703208340000222
Under a nitrogen protection system, L (31.1g,55mmol), Z-1(16.2g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 24.6g of a white solid with a yield of 72.1%. 1HNMR (500MHz, Chloroform-d) delta 8.14-8.07 (1H), 8.07-8.03 (3H), 7.95-7.92 (1H),7.85-7.71(6H), 7.63-7.57 (3H), 7.54-7.52 (1H), 7.47-7.42 (6H),7.33-7.3(2H), 7.27-
7.22(4H),7.10-7.0,6(4H)，7.02-6.97(2H).
Mass spectrum: calculated value 683.84; the test value was 683.89. Elemental analysis: calculated values are C: 93.09%; h: 4.86 percent; n: 2.05% test value is C: 93.13 percent; h: 4.92 percent; n: 1.95 percent
Example 2: preparation of Compound A3
Figure BDA0003703208340000231
Under a nitrogen protection system, L (31.1g,55mmol), Z-2(25.8g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 22.9g of a white solid with a yield of 52.5%.
Mass spectrum: calculated value 876.09; the test value was 876.24. Elemental analysis: calculated values are C: 93.22 percent; h: 5.18 percent; n: 1.60% test value is C: 93.44 percent; h: 4.90 percent; n: 1.66 percent
Example 3: preparation of Compound A18
Figure BDA0003703208340000232
Under a nitrogen protection system, L (31.1g,55mmol), Z-3(21g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, carrying out suction filtration after precipitation is separated out, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃ to obtain light yellow powder. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to give 16.5g of a pale yellow solid with a yield of 40.1%.
Mass spectrum: calculated value 823.97; the test value was 823.81. Elemental analysis: calculated values are C: 91.83 percent; h: 4.53 percent; n: 1.7 percent; o: 1.94% test value C: 91.92 percent; h: 4.49 percent; n: 1.68 percent; o is 1.91 percent
Example 4: preparation of Compound A58
Figure BDA0003703208340000241
M (31.1g,55mmol), Z-4(19.1g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle under a nitrogen protection system, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to give 15.5g of a white solid in 39.4% yield.
Mass spectrum: calculated value 787.98; the test value was 787.88. Elemental analysis: calculated values are C: 92.98 percent; h: 5.24 percent; n: 1.78% test value is C: 92.76 percent; h: 5.30 percent; n: 1.94 percent
Example 5: preparation of Compound A63
Figure BDA0003703208340000242
M (31.1g,55mmol), Z-5(24.1g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle under a nitrogen protection system, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 24.2g of a white solid with a yield of 54.7%.
Mass spectrum: calculated value 886.09; the test value was 886.21. Elemental analysis: calculated values are C: 93.53%; h: 4.89%; n: 1.58% test value is C: 93.42 percent; h: 4.95 percent; n: 1.63 percent
Example 6: preparation of Compound A81
Figure BDA0003703208340000251
M (31.1g,55mmol), Z-6(24.1g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle under a nitrogen protection system, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. Column chromatography was performed using a mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 1:6) as a solvent, and the filtrate was concentrated to give 17.4g of a white solid with a yield of 39.3%.
Mass spectrum: calculated value 886.09; the test value was 886.23. Elemental analysis: calculated values are C: 93.53 percent; h: 4.89%; n: 1.58% test value C: 93.39 percent; h: 4.95 percent; n: 1.66 percent
Example 7: preparation of Compound A92
Figure BDA0003703208340000252
N (31.1g,55mmol), Z-7(17.8g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-neck reaction flask under a nitrogen protection system, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to give 13.4g of a white solid in 35.4% yield.
Mass spectrum: the calculated value is 759.93; the test value was 759.76. Elemental analysis: calculated values are C: 93.25 percent; h: 4.91 percent; n: 1.84% test value C: 93.28 percent; h: 4.85 percent; n: 1.87 percent
Example 8: preparation of Compound A96
Figure BDA0003703208340000261
N (31.1g,55mmol), Z-8(19g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-mouth reaction bottle under a nitrogen protection system, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. The mixture of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 20.1g of a white solid in 51.4% yield.
Mass spectrum: calculated value 783.95; the test value was 783.63. Elemental analysis: calculated values are C: 93.46 percent; h: 4.76 percent; n: 1.79% test value is C: 93.58 percent; h: 4.68 percent; n: 1.74 percent
Example 9: preparation of Compound A108
Figure BDA0003703208340000271
N (31.1g,55mmol), Z-9(28.6g,50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-neck reaction flask under a nitrogen protection system, and then 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, heated to 80 ℃, stirred uniformly and reacted for 24 hours. Cooling to room temperature of 25 ℃ after the reaction is stopped, leaching after precipitation, washing with absolute ethyl alcohol, and drying at the temperature of 80 ℃. Column chromatography was performed using a mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 1:6) as a solvent, and the filtrate was concentrated to obtain 17.4g of a white solid in a yield of 35.7%.
Mass spectrum: calculated value 976.17; the test value was 976.28. Elemental analysis: calculated values are C: 92.28%; h: 4.65 percent; n: 1.43 percent; o: 1.64% test value is C: 92.14%; h: 4.58 percent; n: 1.47 percent; o: 1.67 percent
Example 10: preparation of Compound A114
Figure BDA0003703208340000272
Under a nitrogen protection system, adding L-6(23.7g,50mmol), Z-10(19.8g,55mmol) and sodium tert-butoxide (9.6g,100mmol) into a reaction bottle, replacing with nitrogen for 3 times, adding toluene (160ml) under nitrogen protection, replacing with nitrogen for 3 times, adding tris (dibenzylideneacetone) dipalladium (0.915g,1mmol) and 50% tri-tert-butylphosphine (0.81g,2mmol) under nitrogen protection, replacing with nitrogen for 3 times, heating to 120 ℃, and stirring for 12 hours. Cooling to room temperature, adding 160ml of water, stirring for 30min, performing suction filtration to obtain a solid, drying, performing column chromatography separation by using a mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) as a solvent, and concentrating the filtrate to obtain 30.8g of a white solid with the yield of 77%.
Mass spectrum: calculated value is 800.0; the test value was 800.5. Elemental analysis: calculated values are C: 93.08 percent; h: 5.17 percent; n: 1.75%, test value C: 92.96%; h: 5.19 percent; n: 1.85 percent
Example 11: preparation of Compound A131
Figure BDA0003703208340000281
Under a nitrogen protection system, adding L-6(23.7g,50mmol), Z-11(18.4g,55mmol) and sodium tert-butoxide (9.6g,100mmol) into a reaction bottle, replacing with nitrogen for 3 times, adding toluene (160ml) under nitrogen protection, replacing with nitrogen for 3 times, adding tris (dibenzylideneacetone) dipalladium (0.915g,1mmol) and 50% tri-tert-butylphosphine (0.81g,2mmol) under nitrogen protection, replacing with nitrogen for 3 times, heating to 120 ℃, and stirring for 12 hours. Cooling to room temperature, adding 160ml of water, stirring for 30min, performing suction filtration to obtain a solid, drying, performing column chromatography separation by using a mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether: 1:6) as a solvent, and concentrating the filtrate to obtain a white solid 20.4g, wherein the yield is 52.7%.
Mass spectrum: calculated value 773.92; the test value was 773.76. Elemental analysis: calculated values are C: 91.56 percent; h: 4.56 percent; n: 1.81 percent; o: 2.07, test value C: 91.65 percent; h: 4.49 percent; n: 1.75 percent; o: 2.11
Other examples test data are shown in Table 1
TABLE 1
Figure BDA0003703208340000282
Figure BDA0003703208340000291
The embodiment provides an organic electroluminescent device, which comprises a first electrode, and a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer and a second electrode which are sequentially arranged on the first electrode. Wherein the first electrode is an ITO anode; the second electrode is a cathode;
device example 1: the hole transport material of the invention is used for preparing red light phosphorescence doped organic electroluminescent devices (OLED)
The structure of the prepared OLED device is as follows: ITO anode/HIL/HTL/EML/ETL/EIL/cathode
a. An ITO anode: coating with a thickness of
Figure BDA0003703208340000292
The ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate is cleaned in distilled water for 2 times, ultrasonically cleaned for 30min, then repeatedly cleaned for 2 times by distilled water, ultrasonically cleaned for 10min, and after the cleaning is finished, ultrasonically cleaned by methanol, acetone and isopropanol in sequence (each time for 5min), dried, then transferred into a plasma cleaning machine for cleaning for 5min, and then sent into an evaporation machine, and other functional layers are evaporated on the substrate by taking the substrate as an anode in sequence.
b. HIL (hole injection layer): a hole injection layer was formed by evaporation of 2-TNATA (N1- (2-naphthyl) -N4, N4-bis (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenylbenzene-1, 4-diamine) at 10 nm.
c. HTL (hole transport layer): the compound a115nm prepared in example 1 was evaporated to form a hole-transporting layer.
d. EML (light-emitting layer): the host material EMH-1 and the doping material EMD-1 are mixed and evaporated by weight ratio of 97: 3 for 40nm to form a luminescent layer. Wherein the structural formulas of the host material EMH-1 and the doping material EMD-1 are as follows;
f. ETL (electron transport layer): and evaporating ET-1 and Liq 40nm to form an electron transport layer. Wherein the weight ratio of ET-1 to Liq is 60:40, wherein the structural formula of ET-1 is as follows
g. EIL (electron injection layer): and evaporating Yb to 1.0nm to form an electron injection layer.
h. Cathode: and (4) evaporating and plating magnesium and silver at 18nm in a weight ratio of 1:9 to obtain the OLED device.
Figure BDA0003703208340000293
Referring to the method provided by device example 1, compounds A3, a18, a22, a34, a48, a58, a60, a63, a71, a78, a81, a92, a96, a97, a101, a105, a108, a114, a124, a131, and a133 in the present example were selected instead of compound A1, and evaporation of a hole transport layer was performed to prepare corresponding organic electroluminescent devices, which are denoted as device examples 2 to 22, respectively.
Device comparative example 1:
the comparative example provides an organic electroluminescent device, and the only difference between the preparation method of the organic electroluminescent device and the device example 1 is that the organic electroluminescent device is prepared by adopting the existing comparative compound NPB to replace the hole transport material (compound A1) in the device example 1 for evaporation, and the corresponding organic electroluminescent device is marked as device comparative example 1. Wherein the chemical structural formula of the comparative compound NPB is:
Figure BDA0003703208340000301
device comparative example 2:
and (3) carrying out evaporation on the compound NPB in the comparative example 1 instead of HT-1 to prepare a corresponding organic electroluminescent device, wherein the chemical structural formula of the comparative compound HT-1 is as follows:
Figure BDA0003703208340000302
device comparative example 3:
the compound NPB in the comparative example 1 replaces HT-2 to carry out evaporation coating to prepare a corresponding organic electroluminescent device, and the chemical structural formula of the comparative compound HT-2 is as follows:
Figure BDA0003703208340000303
device comparative example 4:
the compound NPB in the comparative example 1 replaces HT-3 to carry out evaporation coating to prepare a corresponding organic electroluminescent device, and the chemical structural formula of the comparative compound HT-3 is as follows:
Figure BDA0003703208340000311
performance detection
The organic electroluminescent devices obtained in examples 1 to 18 and comparative example 1 were characterized at a luminance of 6000(nits) for driving voltage, luminous efficiency and lifetime, and the test results are shown in table 2 below.
TABLE 2
Figure BDA0003703208340000312
Figure BDA0003703208340000321
As can be seen from table 2, compared with comparative examples 1 to 4, the organic electroluminescent devices provided in examples 1 to 22 of the present invention have a driving voltage of 3.3V to 3.6V, which is significantly lower than that of the comparative examples, and also have a luminous efficiency of more than 10% and a lifetime of more than 5% higher than that of the comparative examples, and thus it is known that the organic electroluminescent devices prepared using the organic electroluminescent compounds provided in the present invention as hole transport materials have significantly reduced driving voltage and significantly improved luminous efficiency and lifetime, as compared with the organic electroluminescent devices prepared using the comparative examples as hole transport materials.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (7)

1. An organic electroluminescent compound, characterized by having a structure represented by formula A:
Figure FDA0003703208330000011
wherein in the above formula, R 1 、R 2 And R 3 Is a mono-or polysubstituent; each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, substituted or unsubstituted C8-C16 condensed ring group;
r is monosubstituted and independently positioned on an Ar1, Ar2 or Ar3 ring, and R is a substituted or unsubstituted triarylamine electron transport group, wherein the substituent is C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, and substituted or unsubstituted C8-C16 condensed ring group.
2. An organic electroluminescent compound according to claim 1, wherein the alkyl group is a straight-chain alkyl group, a branched-chain alkyl group, a cyclic alkyl group, a straight-chain alkyl group substituted with at least 1 substituent, a branched-chain alkyl group substituted with at least 1 substituent, or a cyclic alkyl group substituted with at least 1 substituent; wherein, the substituent is selected from one or more of halogen, deuterium, cyano and hydroxyl;
the aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein, the substituent independently selects one or more of halogen, deuterium, amino, cyano, nitro and hydroxyl;
the heteroaromatic heterocyclic group is an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituent is one or more of halogen, deuterium, amino, cyano, nitro and hydroxyl.
3. The organic electroluminescent compound according to claim 1, wherein R is 1 、R 2 And R 3 The substitution position is any position of the ring;
R 1 、R 2 and R 3 Independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle and a substituted or unsubstituted C5-C60 spiro ring with other substituents on the ring;
or the like, or, alternatively,
R 1 、R 2 and R 3 Substituted or unsubstituted C3-C30 aliphatic ring, substituted or unsubstituted C6-C60 aromatic ring, substituted or unsubstituted C2-C60 aromatic heterocycle, substituted or unsubstituted C5-C60 spiro ring;
wherein, the substituent on the aliphatic ring, the aromatic heterocyclic ring and the spiro ring is at least one selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group and substituted or unsubstituted C5-C60 spiro ring;
the aromatic heterocycle contains at least one heteroatom selected from B, N, O, S, Si and P.
4. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is synthesized by the following steps:
Figure FDA0003703208330000021
wherein the content of the first and second substances,R 4 is a boronic acid pinacol ester group.
5. An organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound comprises the following structure:
Figure FDA0003703208330000022
Figure FDA0003703208330000031
Figure FDA0003703208330000041
Figure FDA0003703208330000051
Figure FDA0003703208330000061
Figure FDA0003703208330000071
Figure FDA0003703208330000081
Figure FDA0003703208330000091
Figure FDA0003703208330000101
Figure FDA0003703208330000111
Figure FDA0003703208330000121
Figure FDA0003703208330000131
Figure FDA0003703208330000141
Figure FDA0003703208330000151
Figure FDA0003703208330000161
Figure FDA0003703208330000171
6. an organic electroluminescent device comprising an anode, a cathode and at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises the organic electroluminescent compound according to any one of claims 1 to 5.
7. An organic electroluminescent device according to claim 6, wherein the organic layer comprises a light-emitting layer comprising the organic electroluminescent compound according to any one of claims 1 to 5 and a dopant material.
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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN115160240A (en) * 2022-07-13 2022-10-11 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115160240A (en) * 2022-07-13 2022-10-11 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and preparation method and application thereof

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