CN110950852A - Organic electron transport material, preparation method thereof and electroluminescent device thereof - Google Patents

Organic electron transport material, preparation method thereof and electroluminescent device thereof Download PDF

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CN110950852A
CN110950852A CN201911375885.2A CN201911375885A CN110950852A CN 110950852 A CN110950852 A CN 110950852A CN 201911375885 A CN201911375885 A CN 201911375885A CN 110950852 A CN110950852 A CN 110950852A
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compound
electron transport
organic
transport material
toluene
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CN110950852B (en
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王辉
陈剑锋
赵贺
李明
陈明
姜志远
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses an organic electron transport material which is characterized in that the general structural formula is shown in the specification; the preparation method comprises the following steps: (1) under the protection of nitrogen, mixing the compound A, the compound B and potassium carbonate, adding the mixture into a mixed solvent, adding tetrakis (triphenylphosphine) palladium, heating, refluxing, cooling, extracting and separating liquid to obtain an intermediate product C; (2) weighing intermediate product C, compound D and potassium carbonate, mixing, adding into a mixed solvent, adding palladium tetrakis (triphenylphosphine), heating and refluxing, leaching, drying, dissolving and separating out, leaching and drying to obtain the final product. The organic electron transport material is used for organic electroluminescent devices and has the advantages of good electron transport performance, high luminous efficiency and the like.

Description

Organic electron transport material, preparation method thereof and electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic electron transport material, a preparation method thereof and an electroluminescent device thereof.
Background
With the development of information technology, display devices have been widely used in various aspects of information science. Among them, the light emitting technology of the flat panel display is a research focus at present, and an Organic Light Emitting Diode (OLED) is gradually becoming a research focus of those skilled in the art as a display device with low voltage, low power, high brightness, wide viewing angle, full curing, full color display, light weight, and low price.
The electron transport materials currently used in the market, bathophenantholine (BPhen) and Bathocuproine (BCP), can basically meet the market demand of organic electroluminescent panels, but the efficiency and stability of the materials still need to be further improved. The symmetric structure of BPhen and BCP, analyzed from the molecular structure of BPhen and BCP, makes the molecules tend to be regularly stacked, but easily form crystals after time, once the electron transport material is crystallized, the charge transition mechanism between molecules becomes different from the amorphous film mechanism in normal operation, resulting in the change of electron transport property. If the material with the BPhen symmetrical molecular structure is used in an organic electroluminescent device, the conductivity of the whole device is changed after time, the mobility of electron and hole charges is unbalanced, the efficiency of the device is reduced, local short circuit can be generated in the device, the stability of the device is influenced, and the device even fails.
Therefore, the problem to be solved by those skilled in the art is how to develop an organic electron transport material with high electron transport rate, good electron transport performance and high light emitting efficiency.
Disclosure of Invention
In view of the above, the present invention provides an organic electron transport material, a method for preparing the same, and an electroluminescent device thereof, which have the advantages of high electron transport rate, good electron transport performance, high light emitting efficiency, and the like.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic electron transport material having the formula:
Figure BDA0002340941790000021
wherein A and Ar1、Ar2、Ar3Each independently selected from at least one of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
further, A is selected from substituted or unsubstituted C6-C18 aryl;
further, Ar mentioned above1、Ar2And Ar3Each independently selected from at least one of substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C12-C18 heteroaryl;
further, the substituents in the above substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl include deuterium, alkyl, cyano, halogen; further, halogen is fluorine.
Preferably, the organic light emitting material of the present invention is any one of the following structures:
Figure BDA0002340941790000031
Figure BDA0002340941790000041
Figure BDA0002340941790000051
Figure BDA0002340941790000061
Figure BDA0002340941790000071
Figure BDA0002340941790000081
Figure BDA0002340941790000091
Figure BDA0002340941790000101
Figure BDA0002340941790000111
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 substituted groups and substituted positions thereof, which is not described in detail herein.
The invention also provides a preparation method of the organic electron transport material, which comprises the following steps:
(1) under the protection of nitrogen, compound A
Figure BDA0002340941790000112
Compound B
Figure BDA0002340941790000113
Mixing with potassium carbonate, adding the mixture into a mixed solvent of toluene, ethanol and water, adding palladium tetrakis (triphenylphosphine), heating the mixture to reflux reaction for 20-30 h, cooling the mixture, and adding waterExtracting and separating the mixed solution with ethyl acetate, collecting an organic phase, performing silica gel column chromatography, and spin-drying to obtain an intermediate product C
Figure BDA0002340941790000121
(2) Weighing the intermediate product C and the compound D obtained in the step (1)
Figure BDA0002340941790000122
Mixing with potassium carbonate, adding the mixture into a mixed solvent of toluene, ethanol and water, adding palladium tetrakis (triphenylphosphine), heating the mixture until reflux reaction lasts for 20-30 h, carrying out suction filtration, sequentially leaching the mixture with toluene, acetone and purified water, drying the mixture, dissolving the mixture with toluene, cooling the dissolved mixture to separate out, carrying out suction filtration, leaching the mixture with toluene, and drying the dissolved mixture to obtain the organic electron transport material.
Further, in the compound a, X is halogen; in the compound B, Y is boric acid.
Further, in the step (1), the molar ratio of the compound A to the compound B to the potassium carbonate is 1:1: 5-10; preferably 1:1: 8;
the volume usage ratio of the mixed solvent of toluene, ethanol and water is 2:1:1, wherein the usage amount of toluene is 15-20 times of the mass of the compound A, the usage amount of ethanol is 5-10 times of the mass of the compound A, and the usage amount of water is 5-10 times of the mass of the compound A; preferably, the amount of toluene is 18 times of the mass of the compound A, the amount of ethanol is 9 times of the mass of the compound A, and the amount of water is 9 times of the mass of the compound A;
the dosage of the tetrakis (triphenylphosphine) palladium is 1 to 5 percent of the molar dosage of the compound A; preferably 2%;
the using amount of the mixed solution of water and ethyl acetate is 20-40 times of the mass of the compound A, wherein the using amount of water is 15-20 times of the mass of the compound A, and the using amount of ethyl acetate is 15-20 times of the mass of the compound A; preferably, the amount of the water and the ethyl acetate are both 20 times of the mass of the compound A;
further, in the step (2), the molar ratio of the intermediate product C, the compound D and potassium carbonate is 1:1.5: 2;
the volume usage ratio of the mixed solvent of toluene, ethanol and water is 2:2:1, wherein the usage amount of toluene is 8-12 times of the mass of the intermediate product C, the usage amount of ethanol is 8-12 times of the mass of the intermediate product C, and the usage amount of water is 4-6 times of the mass of the intermediate product C; preferably, the amount of the toluene is 10 times of the mass of the intermediate product C, the amount of the ethanol is 10 times of the mass of the intermediate product C, and the amount of the water is 5 times of the mass of the intermediate product C;
the dosage of the tetrakis (triphenylphosphine) palladium is 1 to 5 percent of the molar dosage of the intermediate product C. Preferably 2%, in the step (4), the silica gel column is 200-300 meshes, and the developing agent is dichloromethane and petroleum ether.
The synthetic route is as follows:
Figure BDA0002340941790000131
the invention has the beneficial effects that: the preparation method is simple and feasible, and the product purity is high.
The invention also provides an organic electroluminescent device containing the organic electron transport material, which comprises: the organic electron transport material comprises a first electrode (anode), a second electrode (cathode), and one or more electron transport layers arranged between the first electrode and the second electrode, wherein the electron transport layers are the organic electron transport material.
The application of the organic electron transport material in preparing organic electroluminescent device products.
An organic electroluminescent device containing the organic electron transport material is applied to the preparation of organic solar cells, electronic paper, organic photoreceptors or organic thin film transistors.
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.
Example 1
The organic electron transport material T001 has a structural formula:
Figure BDA0002340941790000141
the specific synthesis steps are as follows:
(1) weighing A01(37.85mmo1, 20g), B01(37..85mmo1, 10.06g) and potassium carbonate (302mmo1, 41.8g) in a nitrogen protection system, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (757 mu mo1, 875mg) in a refluxing reaction at 90 ℃ for 24 hours under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating, collecting an organic phase, carrying out spin drying on the organic phase, carrying out dry loading, carrying out silica gel column chromatography, using dichloromethane and petroleum ether as developing agents (DCM: PE ═ 1: 2), collecting a solution with the product, and carrying out spin drying to obtain C01(14.3g, wherein the yield is 56.4%); theoretical MW value: 669.2, test value: 669.5, respectively;
(2) weighing intermediate C01(20.9mmol, 14g), adding D01(31.73mmol, 7.72g), adding 5.78g of potassium carbonate into the system, adding a mixed solution of 140mL of toluene, 140mL of ethanol and 70mL of purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (536 mu mo1, 620mg) under the protection of nitrogen, stirring for 24 hours at 90 ℃, carrying out suction filtration, carrying out drip washing on a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, then cooling to 20 ℃ for precipitation, carrying out suction filtration, carrying out drip washing on the toluene, and drying to obtain T001(8.5g, the yield is 51.4%).
The process flow is as follows:
Figure BDA0002340941790000151
the compound T001 was analyzed, and the specific results were as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated value 790.27, test value 790.93;
elemental analysis:
calculated value C: 86.56 percent; h: 4.33 percent; n: 7.08 percent; o: 2.02 percent;
test value C: 86.57 percent; h: 4.34 percent; n: 7.07 percent; o: 2.03 percent.
Example 2
The organic electron transport material T010 has a structural formula:
Figure BDA0002340941790000161
the specific synthesis steps are as follows:
weighing A10(51.5mmo1, 20g), B10(51.5mmo1, 13.7g) and potassium carbonate (412mmo1, 57g) into a reaction system under the protection of nitrogen, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (1030 mu mo1, 1190mg) into the reaction system under the protection of nitrogen, refluxing at 90 ℃ for 24 hours, cooling the system to room temperature after the reaction is stopped, adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating, collecting an organic phase, spin-drying the organic phase, dry-loading, performing column chromatography on silica gel, using dichloromethane and petroleum ether as developing agents (DCM: PE ═ 1: 6), collecting a solution with the product, and spin-drying to obtain C10(18.2g, the yield being 66.74%), and the theoretical value of MW: 529.19, test value: 529.39, respectively;
(2) weighing intermediate C10(34mmol, 18g), adding D10(51mmol, 12.6g), adding 9.4g of potassium carbonate into the system, adding a mixed solution of 180mL of toluene, 180mL of ethanol and 90mL of purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (680 mu mo1, 785mg) under the protection of nitrogen, stirring at 90 ℃ for 24 hours, carrying out suction filtration, leaching a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, cooling to 20 ℃ for precipitation, carrying out suction filtration, leaching toluene, and drying to obtain T010(12g, the yield is 54.2%).
The process flow is as follows:
Figure BDA0002340941790000171
the compound T010 is detected and analyzed, and the specific results are as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated value 651.23, test value 651.77;
elemental analysis:
calculated value C: 86.61 percent; h: 4.49 percent; n: 6.45 percent; o: 2.45 percent;
test value C: 86.62 percent; h: 4.51 percent; n: 6.44 percent; o: 2.46 percent.
Example 3
Organic electron transport material T023, the structural formula is as follows:
Figure BDA0002340941790000172
the specific synthesis steps are as follows:
the method comprises the following steps: weighing A23(40.62mmo1, 20g), B23(40.62mmo1, 10.8g) and potassium carbonate (324.95mmo1, 45g) into a reaction system under the protection of nitrogen, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (812 mu mo1, 939mg) under the protection of nitrogen, refluxing at 90 ℃ for 24 hours, cooling the system to room temperature after the reaction is stopped, adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating, collecting an organic phase, spin-drying the organic phase, carrying out dry column chromatography, using silica gel as a developing agent, namely dichloromethane and petroleum ether (DCM: PE ═ 1: 5), collecting a solution with the product, and spin-drying to obtain C23(17.6g, wherein the yield is 68.4%); theoretical MW value: 633.2, test value: 633.5, respectively;
step 2: weighing intermediate C23(26.84mmol, 17g), adding D23(40.25mmol, 9.95g), adding 7.42g of potassium carbonate into the system, adding a mixed solution of 170mL of toluene, 170mL of ethanol and 85mL of purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (536 mu mo1, 620mg) under the protection of nitrogen, stirring for 24 hours at 90 ℃, carrying out suction filtration, carrying out drip washing on a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, then cooling to 20 ℃ for precipitation, carrying out suction filtration, carrying out drip washing on toluene, and drying to obtain T023(11.5g, the yield is 56.7%).
The process flow is as follows:
Figure BDA0002340941790000181
the compound T023 is subjected to detection analysis, and the specific results are as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated value 755.26, test value 755.88;
elemental analysis:
calculated value C: 85.81 percent; h: 4.40 percent; n: 5.56 percent; o: 4.23 percent;
test value C: 85.82 percent; h: 4.41 percent; n: 5.57 percent; o: 4.24 percent.
Example 4
The organic electron transport material T047 has a structural formula as follows:
Figure BDA0002340941790000191
the specific synthesis steps are as follows:
weighing A47(41.81mmo1, 20g), B47(41.81mmo1, 11.12g) and potassium carbonate (334.49mmo1, 46.23g) into a reaction system under the protection of nitrogen, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (836.23 mu mo1, 966.31mg) into the reaction system under the protection of nitrogen and refluxing at 90 ℃ for 24 hours, cooling the system to room temperature after the reaction is stopped, adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating liquid, collecting an organic phase, carrying out spin-drying on the organic phase, carrying out dry-method sample loading on the silica gel column chromatography, using dichloromethane and petroleum ether as developing agents (DCM: PE ═ 1: 2), collecting the solution with the product, carrying out spin-drying to obtain C47(17.7g, the yield is 68.34%), and the theoretical MW value is.2: the test value is: 619.4;
(2) weighing intermediate C47(28.25mmol, 17.5g), adding D47(42.37mmol, 7.7g), adding 7.8g of potassium carbonate into the system, adding a mixed solution of 180mL of toluene, 180mL of ethanol and 90mL of purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (566 mu mo1, 652.9mg) under the protection of nitrogen, stirring for 24 hours at 90 ℃, carrying out suction filtration, carrying out drip washing on a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, cooling to 20 ℃ for precipitation, carrying out suction filtration, carrying out drip washing on the toluene, and drying to obtain T047(10.2g, yield 53.35%).
The process flow is as follows:
Figure BDA0002340941790000201
the compound T047 is detected and analyzed, and the specific results are as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated value 676.2, test value 676.7;
elemental analysis:
calculated value C: 85.19 percent; h: 4.17 percent; n: 8.28 percent; o: 2.36 percent;
test value C: 85.21 percent; h: 4.16 percent; n: 8.29 percent; o: 2.37 percent.
Example 5
The organic electron transport material T055 has a structural formula:
Figure BDA0002340941790000211
the specific synthesis steps are as follows:
(1) weighing A55(37.85mmo1, 20g), B55(37..85mmo1, 10.06g) and potassium carbonate (302mmo1, 41.8g) in a nitrogen protection system, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (757 mu mo1, 875mg) in a refluxing reaction at 90 ℃ for 24 hours under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating, collecting an organic phase, carrying out spin drying on the organic phase, carrying out dry loading, carrying out silica gel column chromatography, using dichloromethane and petroleum ether as developing agents (DCM: PE ═ 1: 3), collecting a solution with the product, and carrying out spin drying to obtain C55(14.3g, wherein the yield is 56.4%); theoretical MW value: 669.2, test value: 669.5, respectively;
(2) weighing intermediate C55(20.9mmol, 14g), adding D55(31.4mmol, 4.96g), adding 5.78g potassium carbonate into the system, adding a mixed solution of 140mL toluene, 140mL ethanol and 70mL purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (418 mu mo1, 483mg) under the protection of nitrogen, stirring for 24 hours at 90 ℃, carrying out suction filtration, carrying out drip washing on a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, then cooling to 20 ℃ for precipitation, carrying out suction filtration, carrying out drip washing on toluene, and drying to obtain T055(8.4g, yield 57.2%).
The process flow is as follows:
Figure BDA0002340941790000221
the compound T055 was analyzed by detection, and the specific results were as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated 701.3 and test 701.8;
elemental analysis:
calculated value C: 85.45 percent; h: 4.3 percent; n: 7.97 percent; o: 2.28 percent;
test value C: 85.46 percent; h: 4.3 percent; n: 7.96 percent; o: 2.29 percent; .
Example 6
An organic electron transport material T081, structural formula is:
Figure BDA0002340941790000222
the specific synthesis steps are as follows:
(1) weighing A81(40.9mmo1, 20g), B55(40.9mmo1, 10.9g) and potassium carbonate (327.6mmo1, 45.3g) under a nitrogen protection system, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (819 mu mo1, 946mg) under the protection of nitrogen, refluxing at 90 ℃ for 24 hours, cooling the system to room temperature after the reaction is stopped, adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating, collecting an organic phase, carrying out spin drying on the organic phase, carrying out dry sample loading, carrying out silica gel column chromatography, using dichloromethane and petroleum ether as developing agents (DCM: PE is 1: 7), collecting a solution with the product, and carrying out spin drying to obtain C81(17.1g, wherein the yield is 61.5%); theoretical MW value: 679.2, test value: 679.5, respectively;
(2) weighing intermediate C81(27mmol, 17g), adding D81(40.5mmol, 6.36g), adding 7.46g of potassium carbonate into the system, adding a mixed solution of 170mL of toluene, 170mL of ethanol and 85mL of purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (540 mu mo1, 624mg) under the protection of nitrogen, stirring at 90 ℃ for 24 hours, carrying out suction filtration, carrying out drip washing on a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, then cooling to 20 ℃ to precipitate, carrying out suction filtration, carrying out drip washing on the toluene, and drying to obtain T081(9.2g, yield 51.5%).
The process flow is as follows:
Figure BDA0002340941790000231
compound T081 was assayed and the results are as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated value 661.2, test value 661.7;
elemental analysis:
calculated value C: 88.93 percent; h: 4.72 percent; n: 6.35 percent;
test value C: 88.94 percent; h: 4.73%; n: 6.34 percent.
Example 7
The organic electron transport material T100 has a structural formula as follows:
Figure BDA0002340941790000241
the specific synthesis steps are as follows:
(1) weighing A100(41.8mmo1, 20g), B100(41.8mmo1, 11.12g) and potassium carbonate (334.5mmo1, 46.23g) into a reaction system under the protection of nitrogen, adding a mixed solution of 360mL of toluene, 180mL of ethanol and 180mL of purified water, adding tetrakis (triphenylphosphine) palladium (836.23 mu mo1, 966.3mg) into the mixed solution, carrying out reflux reaction at 90 ℃ for 24 hours, and cooling the system to room temperature after the reaction is stopped; adding a mixed solution of 400mL of purified water and 400mL of ethyl acetate, extracting and separating, collecting an organic phase, spin-drying the organic phase, loading the organic phase by a dry method, performing silica gel column chromatography, using dichloromethane and petroleum ether (DCM: PE ═ 1: 4) as developing agents, collecting a solution with a product, and spin-drying to obtain C100(16.4g, the yield is 63.32%); theoretical MW value: 619.2, test value: 619.4;
(2) weighing intermediate C100(25.8mmol, 16g), adding D100(38.74mmol, 9.57g), adding 14g of potassium carbonate into the system, adding a mixed solution of 160mL of toluene, 160mL of ethanol and 80mL of purified water under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (516.57 mu mo1, 596mg) under the protection of nitrogen, stirring at 90 ℃ for 24 hours, carrying out suction filtration, carrying out drip washing on a small amount of toluene, acetone and purified water, drying, selecting toluene as a recrystallization solvent, dissolving at 110 ℃, then cooling to 20 ℃ to precipitate, carrying out suction filtration, carrying out drip washing on the toluene, and drying to obtain T100(10.3g, yield 53.7%).
The process flow is as follows:
Figure BDA0002340941790000251
the compound T100 is detected and analyzed, and the specific results are as follows:
HPLC purity: greater than 99.9%;
mass spectrum: calculated value 741.24, test value 741.85;
elemental analysis:
calculated value C: 85.81 percent; h: 4.21 percent; n: 5.66 percent; o: 4.31 percent;
test value C: 85.82 percent; h: 4.23 percent; n: 5.67 percent; o: 4.32 percent.
Since the synthesis methods of other compounds are the same as those of the 7 examples listed above, they are not exhaustive, and 15 compounds are selected as examples in the present invention, and the molecular formula and mass spectrum are shown in table 1.
TABLE 1 molecular formulae and Mass spectra of Compounds of other examples of the invention
Compound (I) Molecular formula Calculated mass spectrum Mass spectrometric test values
T006 C59H37N3O 803.29 803.94
T014 C51H31N3O 701.24 701.81
T024 C53H26D5N3O2 746.20 746.80
T054 C51H26D5N3O 706.27 706.84
T057 C60H34D5N3O 822.00 822.30
T060 C64H39N3 849.30 850.00
T064 C51H41N3 695.33 695.81
T065 C51H35N3 689.28 689.84
T073 C55H35N3 737.28 737.88
T078 C41H27N3 561.22 561.67
T079 C47H29N3O 651.23 651.75
T083 C59H39N3 789.31 789.96
T088 C51H33N3 687.26 687.82
T095 C53H31N3O2 741.24 741.83
T101 C47H28FN3O 669.23 669.72
The device of the invention can be used for an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
In order to further describe the present invention, more specific examples are set forth below.
Device example 1
The preparation of the organic electroluminescent device (electron transport layer) comprises the following steps:
an ITO glass substrate with a Fisher company coating thickness of 150nm is placed in distilled water to be cleaned for 2 times, ultrasonic cleaning is carried out for 30 minutes, then the ITO glass substrate is repeatedly cleaned for 2 times and 10 minutes by distilled water, after the cleaning by distilled water is finished, the ITO glass substrate is sequentially subjected to ultrasonic cleaning by isopropanol, acetone and methanol, then the ITO glass substrate is dried and transferred to a plasma cleaning machine, the substrate is cleaned for 5 minutes, and then the substrate is sent to an evaporation machine. Organic matter evaporation speed maintenance in the above process
Figure BDA0002340941790000261
The deposition rate of LiF is
Figure BDA0002340941790000262
The deposition rate of Al is
Figure BDA0002340941790000263
Figure BDA0002340941790000264
The organic electroluminescent device includes an anode, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, an auxiliary material layer, and a cathode. Wherein, the anode is indium tin oxide; the hole injection layer is 60nm thick (HAT-CN); the hole transport layer was [ di- [4- (N, N-xylyl-amino) -phenyl ] cyclohexane (TAPC) with a thickness of 30 nm; the organic light emitting layer was 10nm thick, and comprised 90% of 4, 4' -bis (carbazol-9-yl) -biphenyl, CBP) as the light emitting host material, and a light emitting material doped with 10% bis (1-phenyl-isoquinoline) (acetylacetonato) iridium (III) (ir (ppy)2 (acac)); the electron transport layer is one of 22 compounds with the thickness of 50nm or the compound of the formula (1); the auxiliary material layer is LiF with the thickness of 1 nm; and the cathode is aluminum.
Comparative example 1
Organic electroluminescent devices were prepared in the same manner as in the above experimental examples, except that the following compounds were used instead of the compounds of the present invention as the electron transport layer material.
Figure BDA0002340941790000271
Comparative example 2
Organic electroluminescent devices were prepared in the same manner as in the above experimental examples, except that the following compounds were used instead of the compounds of the present invention as the electron transport layer material.
Figure BDA0002340941790000272
Comparative example 3
Organic electroluminescent devices were prepared in the same manner as in the above experimental examples, except that the following compounds were used instead of the compounds of the present invention as the electron transport layer material.
Figure BDA0002340941790000281
Performance detection
1. The organic electroluminescent devices obtained in examples and comparative examples were subjected to a test for their emission characteristics, subjected to a forward bias voltage, measured for their emission characteristics using PR-650 photometric equipment from Photoresearch, and measured at 5000cd/m2The life of T95 was measured using a life measuring device manufactured by McScience, and the test results are shown in Table 2.
Table 2 organic electroluminescent device performance luminescence characteristic test results
Figure BDA0002340941790000282
Figure BDA0002340941790000291
As can be seen from table 2, the compound of the present invention used as an electron transport layer in an organic electroluminescent device (OLED) has lower driving voltage and higher efficiency than the organic electroluminescent device prepared in comparative example 1; comparing the organic electroluminescent devices prepared in comparative examples 2 and 3, it can be seen that when the compound of the present invention was used, the devices required lower driving voltage and were significantly improved in both yield and lifetime. The above experiments show that the compounds of the present invention maintain the charge balance of holes and electrons better in the light emitting layer than in comparative examples 2 and 3.
2. The organic electroluminescent devices obtained in examples and comparative examples were subjected to a luminescence life test using an LTS-1004AC life test apparatus 3000nit of ENCTECHNOLOGY, and the test time reached 97%, and the test results are shown in Table 3.
TABLE 3 organic electroluminescent device Performance luminescence Life test results
Figure BDA0002340941790000292
Figure BDA0002340941790000301
As can be seen from table 3, the organic electroluminescent devices obtained in the examples according to the present invention have better life characteristics than the comparative examples.
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 electron transport material is characterized by having a general structural formula:
Figure FDA0002340941780000011
wherein A and Ar1、Ar2、Ar3Are independently selected from at least one of substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.
2. The organic electron transport material of claim 1, wherein Ar is selected from the group consisting of1、Ar2And Ar3Each independently selected from at least one of substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C12-C18 heteroaryl.
3. The organic electron transport material of claim 1, wherein a is selected from substituted or unsubstituted C6-C18 aryl groups.
4. The organic electron transport material of any of claims 1 to 3, wherein the substituents of the substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl groups comprise deuterium, alkyl, cyano, halogen.
5. The method for preparing the organic electron transport material according to claim 1, comprising the following steps:
(1) under the protection of nitrogen, compound A
Figure FDA0002340941780000012
Compound B
Figure FDA0002340941780000013
Mixing with potassium carbonate, adding the mixture into a mixed solvent of toluene, ethanol and water, adding palladium tetrakis (triphenylphosphine), heating the mixture to reflux reaction for 20-30 h, cooling the mixture, adding a mixed solution of water and ethyl acetate, extracting and separating the liquid, collecting an organic phase, performing silica gel column chromatography, and spin-drying the organic phase to obtain an intermediate product C
Figure FDA0002340941780000021
(2) Weighing the intermediate product C and the compound D obtained in the step (1)
Figure FDA0002340941780000022
And mixing with potassium carbonate, adding the mixture into a mixed solvent of toluene, ethanol and water, adding palladium tetrakis (triphenylphosphine), heating the mixture until reflux reaction is carried out for 20-30 h, carrying out suction filtration, leaching, drying, carrying out suction filtration again, leaching and drying to obtain the organic electron transport material.
6. The method according to claim 5, wherein in the compound A, X is a halogen; in the compound B, Y is boric acid.
7. The method for preparing the organic electron transport material according to claim 5, wherein in the step (1), the molar ratio of the compound A to the compound B to the potassium carbonate is 1:1: 5-10;
the volume usage ratio of the mixed solvent of the toluene, the ethanol and the water is 2:1:1, wherein the usage amount of the toluene is 15-20 times of the mass of the compound A, the usage amount of the ethanol is 5-10 times of the mass of the compound A, and the usage amount of the water is 5-10 times of the mass of the compound A;
the molar usage of the tetrakis (triphenylphosphine) palladium is 1-5% of the compound A;
the amount of the mixed solution of water and ethyl acetate is 20-40 times of the mass of the compound A, wherein the amount of water is 15-20 times of the mass of the compound A, and the amount of ethyl acetate is 15-20 times of the mass of the compound A;
in the step (2), the molar ratio of the intermediate product C, the compound D and the potassium carbonate is 1:1.5: 2;
the volume usage ratio of the mixed solvent of the toluene, the ethanol and the water is 2:2:1, wherein the usage amount of the toluene is 8-12 times of the mass of the intermediate product C, the usage amount of the ethanol is 8-12 times of the mass of the intermediate product C, and the usage amount of the water is 4-6 times of the mass of the intermediate product C;
the molar usage of the tetrakis (triphenylphosphine) palladium is 1-5% of that of the intermediate product C.
8. An organic electroluminescent device comprising an organic electron transport material, comprising: a first electrode, a second electrode, one or more electron transport layers disposed between the first electrode and the second electrode;
the electron transport layer is the organic electron transport material of claim 1.
9. Use of the organic electron transport material according to any of claims 1 to 4 for the preparation of an organic electroluminescent device.
10. Use of an organic electroluminescent device comprising an organic electron transport material according to claim 8 for the preparation of an organic solar cell, an electronic paper, an organic photoreceptor or an organic thin film transistor.
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