CN115160240A - Organic electroluminescent compound and preparation method and application thereof - Google Patents

Organic electroluminescent compound and preparation method and application thereof Download PDF

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CN115160240A
CN115160240A CN202210827958.2A CN202210827958A CN115160240A CN 115160240 A CN115160240 A CN 115160240A CN 202210827958 A CN202210827958 A CN 202210827958A CN 115160240 A CN115160240 A CN 115160240A
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organic electroluminescent
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李明
姜永吉
卢振阳
郎兴旺
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention disclosesAn organic electroluminescent compound, a preparation method and an application thereof, which belong to the field of organic photoelectric materials, wherein the molecular structural general formula is represented by a formula A:
Figure DDA0003744724790000011
wherein, in the formula A, R is 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, and the like; the R is 4 Is monosubstituted, independently on an Ar1, ar2, ar3 ring, R 4 Substituted and unsubstituted triazine, pyrimidine, pyrazine, pyridazine electron transport groups, where the substituents are C1-C6 alkyl and the like. The invention provides an organic electroluminescent compound with good film forming property, high efficiency, low driving voltage and long service life.

Description

Organic electroluminescent compound and preparation method and application thereof
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to an organic electroluminescent compound and a preparation method and application thereof.
Background
The organic electroluminescent device has the characteristics of self luminescence, wide viewing angle, high contrast, short response time, low driving voltage, soft manufacture 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 on the market in batches and applied to high-end electronic products. Illumination sources will also be industrialized due to their absolute advantages. The electroluminescent device has an all-solid-state structure, and the organic electroluminescent material is the core and the foundation of the device. The development of new materials is a source power for promoting continuous progress of an electroluminescence technology, and the original material preparation and device optimization are also research hotspots of the current organic electroluminescence industry.
Therefore, the need to provide organic electroluminescent materials with long service life, high efficiency and low cost is a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, an object of the present invention is to provide an organic electroluminescent compound having good film-forming properties, high efficiency, low driving voltage, and long service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic electroluminescent compound having a general molecular structural formula represented by formula a:
Figure BDA0003744724780000021
wherein, in the formula A, 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 fused ring group;
the R is 4 Is monosubstituted, independently on the Ar1, ar2, ar3 ring, R 4 Is substituted and unsubstituted triazine, pyrimidine, pyrazine, pyridazine 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.
Preferably, said R is 4 A triazine is selected.
Preferably, the alkyl group is selected from the group consisting of a straight-chain alkyl group, a branched-chain alkyl group, a cyclic alkyl group, a straight-chain alkyl group substituted with 1 or several substituents, a branched-chain alkyl group substituted with 1 or several substituents, and a cyclic alkyl group substituted with 1 or several substituents; wherein the substituents are independently selected from halogen, deuterium, cyano, hydroxy.
Preferably, the aryl group is selected from unsubstituted aryl groups, aryl groups substituted with 1 or several substituents; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy.
Preferably, the aromatic heterocyclic group is selected from 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, hydroxyl.
Preferably, said R is 1 、R 2 、R 3 The substitution position is any position of the ring.
Preferably, said R is 1 、R 2 、R 3 Can be independent of each otherAnd mutually 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, 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 substituents on the aliphatic ring, the aromatic heterocycle and the spirocycle are 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 spirocycle; the aromatic heterocyclic ring contains one or more heteroatoms selected from B, N, O, S, si and P.
Preferably, said R 4 The position of (a) is represented by the following structural formula:
Figure BDA0003744724780000031
preferably, the specific structural formula of the organic electroluminescent compound can also be represented by the following structure:
Figure BDA0003744724780000032
Figure BDA0003744724780000041
Figure BDA0003744724780000051
Figure BDA0003744724780000061
Figure BDA0003744724780000071
Figure BDA0003744724780000081
Figure BDA0003744724780000091
Figure BDA0003744724780000101
preferably, the synthetic route of the parent core compound for preparing the organic electroluminescent compound is as follows:
Figure BDA0003744724780000111
preferably, the synthesis route of the parent nucleus compound is as follows:
s1, adding 1-bromo-2-naphthalene methyl benzoate, o-bromobenzoic acid, tetrakis (triphenylphosphine) palladium, 100ml of potassium carbonate purified water and 300ml of tetrahydrofuran into a three-opening 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 a first intermediate.
S2: adding the first intermediate, 2-aminophenylboronic acid pinacol ester, tetrakis (triphenylphosphine) palladium, potassium carbonate, purified water and dioxane into a three-opening reaction bottle, heating to 120 ℃ under the protection of nitrogen, reacting for 10 hours, extracting with dichloromethane after the reaction is finished, and concentrating and performing chromatography (PE/EA = 5/1) to obtain a second intermediate.
S3: and adding the second intermediate, acetic acid and sulfuric acid into a three-mouth reaction bottle, cooling to 0 ℃, slowly dropwise adding a sodium nitrite aqueous solution, slowly pouring the reaction solution into water after the reaction is finished, filtering, and performing filter cake column chromatography purification to obtain a third intermediate.
S4: and (3) adding the third intermediate and polyphosphoric acid to 100 ℃, reacting for 3 hours, monitoring the reaction, slowly pouring the reaction liquid into water, extracting with dichloromethane, concentrating, and purifying by column chromatography to obtain a fourth intermediate.
S5: adding 2-bromo-4-chloro-1,1-biphenyl into tetrahydrofuran, cooling to-78 ℃, dropwise adding n-butyllithium, keeping for 0.5h after dropwise adding is finished, quickly dropwise adding a tetrahydrofuran solution dissolved with a fourth intermediate into a reaction solution, carrying out heat preservation reaction for 2h, recovering room temperature for reaction for 2h, adding water for quenching, and extracting and concentrating ethyl acetate to obtain a fifth intermediate.
S6: and adding the fifth intermediate and dichloromethane into a three-opening reaction bottle, cooling to 0 ℃, dropwise adding methanesulfonic acid, reacting at room temperature for 3 hours after the dropwise adding is finished, adding water, and extracting and concentrating with dichloromethane to obtain a sixth intermediate.
S7: the sixth intermediate and Pd 2 (dba) 3 AcOK, DMF, and nitrogen protection at 170 ℃ for 12h, adding water after the reaction is finished, filtering, and carrying out column chromatography purification on the solid to obtain the mother nucleus compound.
Preferably, the synthetic route for preparing the organic electroluminescent compounds is as follows:
Figure BDA0003744724780000121
wherein R is 4 Is a boronic acid pinacol ester group.
The application of the organic electroluminescent compound in an organic electroluminescent device comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the organic layer comprises a luminescent layer, and the raw material of the luminescent layer comprises a doping material and the organic luminescent material; the mass ratio of the organic luminescent material to the doping material is (90-99.5) to (0.5-10).
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 intermolecular charge transition capability is facilitated, and meanwhile, the R4 position of the compound structural formula is connected with a substituent group, so that the intermolecular crystallization and aggregation are not easy to occur, and the material has higher photo-thermal stability. Therefore, by using the organic electroluminescent compounds of the present invention as host in the light-emitting layer, we found through research that the effect achieved by substituting this mother core with triazine electron transport groups at different positions is different, which may be related to homo/lumo distribution, and tested that the efficiency and lifetime effect of the organic electroluminescent device is better at the specific positions defined in the present invention.
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.
Preparation of intermediate L:
Figure BDA0003744724780000131
step 1: adding 1-bromo-2-naphthalene methyl benzoate (200 mmol), o-bromobenzoic acid (200 mmol), tetrakis (triphenylphosphine) palladium (2 mmol), potassium carbonate (300 mmol), purified water (100 ml) and tetrahydrofuran (300 ml) into a three-mouth reaction bottle, heating to 80 ℃ under the protection of nitrogen, reacting for 8 hours, extracting with dichloromethane after the reaction is finished, and concentrating an organic phase to obtain an intermediate L-1.
And 2, step: adding 50ml of purified water containing L-1 (100 mmol), 2-aminobenzeneboronic acid pinacol ester (100 mmol), tetrakis (triphenylphosphine) palladium (1 mmol), potassium carbonate (150 mmol) and 50ml of purified water containing 300ml of dioxane into a three-mouth reaction bottle, heating to 120 ℃ under the protection of nitrogen, reacting for 10 hours, extracting with dichloromethane after the reaction is finished, and concentrating the solution to obtain an intermediate L-2 through chromatography (PE/EA = 5/1).
And step 3: adding 100ml of L-2 (40 mmol) acetic acid and 15ml of sulfuric acid into a three-mouth reaction bottle, cooling to 0 ℃, slowly dripping aqueous solution of sodium nitrite (50 mmol), after the reaction is finished, slowly pouring the reaction solution into water, filtering, and performing column chromatography purification on a filter cake to obtain an intermediate L-3.
And 4, step 4: adding L-3 (50 mmol) 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 (30 mmol) into tetrahydrofuran, cooling to-78 ℃, dropwise adding n-butyllithium (36 mmol), keeping for 0.5h after dropwise adding is finished, quickly dropwise adding a tetrahydrofuran solution dissolved with L-4 (30 mmol) into a reaction solution, keeping the temperature for reaction for 2h, recovering the room temperature for reaction for 2h, adding water for quenching, and extracting and concentrating ethyl acetate to obtain an intermediate L-5.
And 6: adding L-5 (30 mmol) and dichloromethane 150ml into a three-mouth reaction bottle, cooling to 0 ℃, dropwise adding methanesulfonic acid (40 ml), reacting at room temperature for 3h, adding water, extracting with dichloromethane, and concentrating to obtain an intermediate L-6.
And 7: mixing L-6 (50 mmol) and Pd 2 (dba) 3 (1 mmol), acOK (90 mmol) and DMF120ml, reacting for 12h at 170 ℃ under the protection of nitrogen, adding water after the reaction is finished, filtering, and carrying out column chromatography purification on the solid 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 an intermediate M:
Figure BDA0003744724780000151
and (3) synthesizing the intermediate N by only replacing 2-bromo-4-chloro-1,1-biphenyl in the step 5 for synthesizing the intermediate L with 2-bromo-5-chloro-1,1-biphenyl, and carrying out the other steps.
Synthesis of intermediate N
Figure BDA0003744724780000152
And (3) synthesizing the intermediate P 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 above.
And (3) synthesizing an intermediate P:
Figure BDA0003744724780000153
and (3) synthesizing the intermediate P 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.
Example 1: preparation of Compound A1
Figure BDA0003744724780000161
Under a nitrogen protection system, L (31.1g, 55mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.3g, 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. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 21.8g of a pale yellow solid with a yield of 65%. H-NMR (CDCl 3) δ (ppm) =8.52-8.57 (4H); δ (ppm) =7.89-7.92 (1H); δ (ppm) =7.82-7.85 (1H); δ (ppm) =7.64-7.78 (8H); δ (ppm) =7.54-7.58 (1H); δ (ppm) =7.43-7.53 (8H); δ (ppm) =7.26-7.4 (4H); δ (ppm) =7.14-7.17 (1H); δ (ppm) =6.85-6.88 (1H).
Mass spectrum: calculated as 671.79; the test value was 671.89. Elemental analysis: calculated values are C:89.39 percent; h:4.35 percent; n:6.25% test value C:89.66%; h:4.30 percent; n:6.04 percent.
Figure BDA0003744724780000162
Under a nitrogen protection system, L (31.1g, 55mmol), 2- (2-bromophenyl) -4,6-diphenyl-1,3,5-triazine (19.4g, 50mmol) and potassium carbonate (13.8g, 100mmol) are put into a three-neck reaction flask, 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 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 23.3g of a pale yellow solid with a yield of 62.5%.
Mass spectrum: calculated as 747.88; the test value was 747.33. Elemental analysis: calculated values are C:89.93%; h:4.45 percent; n:5.62% test value C:89.73%; h:4.38 percent; n:5.89 percent.
Example 3: preparation of Compound A16
Figure BDA0003744724780000171
Under a nitrogen protection system, L (31.1g, 55mmol), 2-chloro-4- (2-dibenzofuranyl) -6- (2-dibenzothiophenyl) -1,3,5-triazine (23.1g, 50mmol) and potassium carbonate (13.8g, 100mmol) are placed in a three-neck reaction flask, and 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 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 15.4g of a pale yellow solid with a yield of 35.7%.
Mass spectrum: calculated as 868.01; the test value was 867.92. Elemental analysis: calculated values are C:85.79%; h:3.83 percent; n:4.84 percent; 1.84 percent of O; s:3.69% test value C:85.72%; h:3.67 percent; n:4.79 percent; 1.81 percent of O; s:4.01 percent.
Example 4: preparation of Compound A20
Figure BDA0003744724780000181
M (31.1g, 55mmol), 2-chloro-4- (biphenyl-4-yl) -6-phenyl-1,3,5-triazine (17.1g, 50mmol) and potassium carbonate (13.8g, 100mmol) were placed in a three-neck reaction flask under nitrogen protection, followed by addition of 200mL of tetrahydrofuran and 50mL of purified water, heating to 80 ℃, stirring and reacting for 24h. 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 ℃ to obtain light yellow powder. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) is used as a solvent, column chromatography separation is carried out, and the filtrate is concentrated to obtain 21g of light yellow solid with the yield of 56.4%.
Mass spectrum: calculated as 747.88; the test value was 747.44. Elemental analysis: the calculated values are C:89.93%; h:4.45 percent; n:5.62% test value C:89.76%; h:4.35 percent; n:5.89 percent.
Example 5: preparation of Compound A27
Figure BDA0003744724780000182
M (31.1g, 55mmol), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (19.4g, 50mmol) and potassium carbonate (13.8g, 100mmol) were put into a three-necked reaction flask under a nitrogen atmosphere, and then 200mL of tetrahydrofuran and 50mL of purified water were added to 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 ℃ to obtain light yellow powder. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 26.3g of a pale yellow solid with a yield of 70.4%.
Mass spectrum: calculated as 747.88; the test value was 747.38. Elemental analysis: the calculated values are C:89.93%; h:4.45 percent; n:5.62% test value C:89.66%; h:4.41 percent; n:5.93 percent.
Example 6: preparation of Compound A33
Figure BDA0003744724780000191
N (31.1g, 55mmol), 2-chloro-4- (2-naphthyl) -6-phenyl-1,3,5-triazine (15.8g, 50mmol) and potassium carbonate (13.8g, 100mmol) were placed in a three-neck reaction flask under a nitrogen atmosphere, and 200mL of tetrahydrofuran and 50mL of purified water were added to the reaction flask, 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. A mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 17.1g of a pale yellow solid with a yield of 47.6%.
Mass spectrum: calculated as 721.84; the test value was 721.43. Elemental analysis: calculated values are C:89.85%; h:4.33 percent; n:5.82% test value C:89.78%; h:4.42 percent; n:5.80 percent.
Example 7: preparation of Compound A40
Figure BDA0003744724780000201
P (31.1g, 55mmol), 2,4-bis ([ 1,1-biphenyl ] -4-yl) chloro-4- (2-naphthyl) -6-phenyl-1,3,5-triazine (21g, 50mmol), and potassium carbonate (13.8g, 100mmol) were placed in a three-neck reaction flask under nitrogen protection, followed by addition of 200mL of tetrahydrofuran, 50mL of purified water, heating to 80 ℃, stirring, and reacting 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 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 15.8g of a pale yellow solid with a yield of 38.4%.
Mass spectrum: calculated as 823.98; the test value was 823.64. Elemental analysis: calculated values are C:90.37%; h:4.53 percent; n:5.10% test value C:90.28 percent; h:4.45 percent; n:5.27 percent.
Example 19: preparation of Compound A53
Figure BDA0003744724780000202
L (31.1g, 55mmol), 4- (biphenyl-4-yl) -6- (4-bromophenyl) 2-phenylpyrimidine (23.1g, 50mmol), and potassium carbonate (13.8g, 100mmol) were put into a three-necked reaction flask under a nitrogen atmosphere, and then 200mL of tetrahydrofuran and 50mL of purified water were added to 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 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 21.9g of a pale yellow solid, with a yield of 58.7%.
Mass spectrum: calculated as 746.89; the test value was 746.63. Elemental analysis: calculated values are C:91.66 percent; h:4.59 percent; n:3.75% test value is C:91.68 percent; h:4.48 percent; n:3.82 percent.
Example 20: preparation of Compound A73
Figure BDA0003744724780000211
Under a nitrogen protection system, L (31.1g, 55mmol), 2-chloro-3-phenylbenzo [ F ] quinoxaline (14.5g, 50mmol) and potassium carbonate (13.8g, 100mmol) are placed into a three-mouth reaction bottle, 200mL of tetrahydrofuran and 50mL of purified water are added into the reaction system, the mixture is 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 ℃ to obtain light yellow powder. The mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether = 1:5) was used as a solvent, column chromatography was performed, and the filtrate was concentrated to obtain 14.7g of a pale yellow solid with a yield of 42.3%.
Mass spectrum: calculated as 694.82; the test value was 694.63. Elemental analysis: calculated values are C:91.62%; h:4.35 percent; n:4.03% test value is C:91.41 percent; h:4.48 percent; n:3.11 percent.
Other examples test data are shown in table 1:
TABLE 1
Figure BDA0003744724780000212
Figure BDA0003744724780000221
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; the light-emitting layer was prepared from the organic electroluminescent compound A1 prepared in example 1 and the dopant material E.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
an ITO anode: coating with a thickness of
Figure BDA0003744724780000222
The ITO (indium tin oxide) glass substrate is cleaned in distilled water for 2 times, ultrasonically cleaned for 30min, repeatedly cleaned with distilled water for 2 times, ultrasonically cleaned for 10min, and after the cleaning is finished, ultrasonically cleaned with methanol, acetone and isopropanol in sequence (each time for 5 min), dried, and then transferred into a plasma cleaning machine for cleaning for 5min to obtain the ITO anode.
HIL (hole injection layer): in the vapor deposition machine, I2-TNATA (i.e., N1- (2-naphthyl) -N4, N4-bis (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenylbenzene-1,4-diamine) was vacuum evaporated onto the TO anode
Figure BDA0003744724780000223
A hole injection layer is formed.
HTL (hole transport layer): NPB (i.e., N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4,4' -diamine) is then vacuum evaporated on the hole injection layer
Figure BDA0003744724780000224
A hole transport layer is formed.
EML (light-emitting layer): a mixed material of the host material and the dopant material E of the compound A1 produced in example 1 was vacuum-evaporated as a light-emitting layer on the hole transport layer, wherein the weight ratio of the host material to the dopant material was 90
Figure BDA0003744724780000231
Wherein the structural formula of the doping material E is as follows;
Figure BDA0003744724780000232
HBL (hole blocking layer): vacuum evaporating bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BALq) on the luminescent layer
Figure BDA0003744724780000233
And forming a hole blocking layer.
ETL (electron transport layer): vacuum evaporation of 8-hydroxyquinoline aluminum (Alq 3) onto the hole-blocking layer
Figure BDA0003744724780000234
An electron transport layer is formed.
EIL (electron injection layer): vacuum evaporation of LiF on the electron transport layer
Figure BDA0003744724780000235
An electron injection layer is formed.
Cathode: vapor plating Al on the electron injection layer
Figure BDA0003744724780000236
And forming a cathode to obtain the organic electroluminescent device.
Referring to the organic electroluminescent device and the method for manufacturing the same provided in example 1, organic electroluminescent compounds A7, A9, a11, a13, a16, a19, a21, a22, a27, a29, a30, a33, a36, a38, a40, a41, a44, a53, a57, a62, a71, and a73 were selected respectively for replacement of the organic electroluminescent compound A1 provided in example 1, and host materials were deposited to prepare organic electroluminescent devices of the corresponding compounds, examples 2 to 23 respectively.
Comparative example 1: referring to the organic electroluminescent device and the method for manufacturing the same provided in example 1, the organic electroluminescent compound A1 was replaced with the host material RH-1, and evaporation of the host material was performed to prepare an organic electroluminescent device of a corresponding compound, that is, comparative example 1. Wherein the structural formula of the main material RH-1 is as follows:
Figure BDA0003744724780000241
comparative example 2: RH-1 in the above comparative example 1 was replaced with RH-2, and other conditions were not changed
Figure BDA0003744724780000242
Performance detection
The organic electroluminescent devices obtained in examples 1 to 18 and comparative examples 1 and 2 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 BDA0003744724780000243
Figure BDA0003744724780000251
Figure BDA0003744724780000261
As can be seen from table 2, compared with comparative examples 1 and 2, the organic electroluminescent devices provided in practical examples 1 to 23 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 have a luminous efficiency of more than 5% and a lifetime of more than 15% higher than that of the comparative examples, so that it can be seen that the organic electroluminescent devices prepared using the organic electroluminescent compounds provided in the present invention as the luminescent layer material have significantly reduced driving voltage and significantly improved luminous efficiency and lifetime compared with the organic electroluminescent devices prepared using the comparative examples as the luminescent layer material.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
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 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 (10)

1. An organic electroluminescent compound characterized by having a general molecular structural formula represented by formula a:
Figure FDA0003744724770000011
wherein, in the formula A, R 1 、R 2 And R 3 Is a mono-or polysubstituted radical; 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 fused ring group;
said R is 4 Is monosubstituted, independently on the Ar1, ar2, ar3 ring, R 4 Is substituted and unsubstituted triazine, pyrimidine, pyrazine, pyridazine 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.
2. An organic electroluminescent compound according to claim 1, wherein the alkyl group is selected from the group consisting of a straight-chain alkyl group, a branched-chain alkyl group, a cyclic alkyl group, a straight-chain alkyl group substituted with 1 or several substituents, a branched-chain alkyl group substituted with 1 or several substituents, and a cyclic alkyl group substituted with 1 or several substituents; wherein the substituents are independently selected from halogen, deuterium, cyano, hydroxy.
3. An organic electroluminescent compound according to claim 1, wherein the aryl group is selected from the group consisting of an unsubstituted aryl group, an aryl group substituted with 1 or more substituents; wherein, the substituent groups are independently selected from halogen, deuterium, amino, cyano, nitro and hydroxyl.
4. An organic electroluminescent compound according to claim 1, wherein the aromatic heterocyclic group is selected from an unsubstituted heteroaryl group and 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, hydroxyl.
5. The organic electroluminescent compound according to claim 1, wherein R is 1 、R 2 、R 3 Can 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 respectively and independently; 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 substituents on the aliphatic ring, aromatic heterocycle, spiro ring are selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclyl, substituted or unsubstituted C5-C60 spiro ring; the aromatic heterocyclic ring contains one or more heteroatoms selected from B, N, O, S, si and P.
6. The organic electroluminescent compound according to claim 1, wherein R is 4 The position of (a) is represented by the following structural formula:
Figure FDA0003744724770000021
7. the organic electroluminescent compound according to claim 1, wherein the synthesis route of the parent compound for preparing the organic electroluminescent compound is as follows:
Figure FDA0003744724770000022
8. the organic electroluminescent compound according to claim 1, wherein the synthetic route for preparing the organic electroluminescent compound is as follows:
Figure FDA0003744724770000031
wherein R is 4 Is a boronic acid pinacol ester group.
9. Use of an organic electroluminescent compound in an organic electroluminescent device, wherein the organic electroluminescent device comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and the raw material of the light-emitting layer comprises a dopant material and the organic light-emitting material according to any one of claims 1 to 6; the mass ratio of the organic luminescent material to the doping material is (90-99.5) to (0.5-10).
10. The application of the organic electroluminescent compound in an organic electroluminescent device is characterized in that the organic layer further comprises 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.
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CN115108919A (en) * 2022-06-20 2022-09-27 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and organic electroluminescent device

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CN115108919A (en) * 2022-06-20 2022-09-27 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and organic electroluminescent device

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