in the general formula (A), R1 is an aromatic hydrocarbon group having 10 to 16 ring-forming carbon atoms, and R2 and R3 are aromatic heterocyclic groups having 8 to 15 ring-forming carbon atoms.

Further, R1 is selected from one of biphenyl, terphenyl, naphthyl, anthryl, dimethylfluorenyl, pyrenyl or phenanthryl, R2 and R3 are independently selected from benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl or

diphenyl

1,3,5 triazinyl, wherein R2 and R3 are the same or different.

Further, the specific structural formula of the compound is as follows:

the invention also discloses a material for an OLED electroluminescent device, which is characterized by comprising the organic compound which takes carbazole and pyrimidine as cores and is disclosed by any one ofclaims 1 to 3.

The invention further discloses an electroluminescent device which comprises a transparent substrate layer, a transparent electrode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode reflection electrode layer, and is characterized in that at least one of the light-emitting layer and the electron transport layer contains the organic compound which takes carbazole and pyrimidine as cores and is disclosed in any one of claims 1-3, and the electroluminescent device can be applied to an OLED light-emitting display or a lighting device.

The beneficial technical effects of the invention are as follows:

1. under the action of an electric field, the generated electroluminescent color of the OLED device prepared by the compound can display single specific color light such as red, blue, green and the like or combined light of a plurality of different colors;

2. the OLED device prepared by the compound can be applied to the fields of passive matrix OLED display (namely PM-OLED), active matrix OLED display (namely AM-OLED) or OLED lighting devices.

Drawings

FIG. 1 is a schematic structural diagram of an OLED device according to the present invention.

Wherein, 1 is a transparent substrate layer, 2 is a transparent electrode layer, 3 is a hole injection layer (HIM), 4 is a Hole Transport Layer (HTL), 5 is an emission layer (EML), 6 is an Electron Transport Layer (ETL), 7 is an electron injection layer, and 8 is a cathode reflective electrode layer.

Detailed Description

The present invention will be described in detail with reference to the drawings and examples.

Example 1, synthesis ofcompound 1 in claim 3:

specific synthetic route forcompound 1

Under the protection of nitrogen, 47.9g of compound a (100mmol), 26.2g of compound B (120mmol), 1.2g of dmap (10mmol) and 500g of dichloromethane were added to a 500ml three-necked flask, the mixture was stirred at room temperature for 3 hours, TLC was followed until no compound a was present, 50g of water was added to quench the reaction, the organic phase was washed with 200g of water to pH 7, the solvent was removed under reduced pressure after drying and filtration with sodium sulfate, the filtrate was removed under reduced pressure, a mixed solution of 250g of tetrahydrofuran and 250g of ethanol was added after the removal of the solvent to recrystallize once, 52.5g of compound C was obtained after drying, yield: 91%, HPLC: 99.2 percent.

HPLC-MS: the theoretical molecular weight of the compound C is 579.0, and the molecular weight is 579.3 in actual detection.

Under nitrogen protection, 57.9g of Compound C (100mmol), 34.0g of Compound D (210mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 21.2g of sodium carbonate (200mmol), 84.8g of water, and 300g of toluene were added to a 500ml three-necked flask, followed by heating under reflux for 8 hours and TLC until no Compound C was present. After the reaction, the temperature was reduced to 30 ℃ and the layers were separated, the lower aqueous phase was separated, the organic phase was washed with water at 200 g.3 to pH 7, dried and passed through a silica gel column at normal pressure. After the column chromatography is finished, 100ml of toluene and 2 are used for eluting the silica gel column, after the elution is finished, the eluent and the column chromatography liquid are combined and decompressed to remove the solvent, 325g of tetrahydrofuran is added into the solvent to be recrystallized twice after the solvent is removed, and 52.9g of compound E is obtained after drying, the yield is as follows: 81%, HPLC: 99.5 percent.

HPLC-MS: the theoretical molecular weight of the compound E is 653.2, and the molecular weight is 653.7 in actual detection.

Under the protection of nitrogen, 65.3g of compound E (100mmol) and 300g of dichloromethane are added into a 500mL three-neck flask, 73.5mL of trifluoroacetic acid is added dropwise at room temperature, after the dropwise addition, the temperature is kept for 6 hours at room temperature, and TLC is carried out until no compound E is obtained. After the reaction, the solvent was removed under reduced pressure, 500g of ethyl acetate was added after the removal of the solvent, 200g of x 3 was washed with saturated aqueous sodium carbonate until pH 7, the solvent was removed under reduced pressure after the washing with water, 330g of tetrahydrofuran was added to recrystallize once, 49.8g of compound F after drying, yield 90%, HPLC: 99.3 percent.

HPLC-MS: the theoretical molecular weight of the compound F is 553.1, and the molecular weight is 553.5 in actual detection.

Under a nitrogen atmosphere, 55.3G of Compound F (100mmol), 25.5G of Compound G (110mmol), 3.8G of cuprous iodide (20mmol), 42.4G of tripotassium phosphate (200mmol), and 300G of xylene were charged into a 500ml three-necked flask, and the mixture was refluxed for 6 hours and TLC was carried out until no Compound F was present. After the reaction, the temperature was reduced to 30 ℃, the reaction mixture was filtered, 50ml of xylene was rinsed with 3, the filtrate was rinsed with 200g of 3 until the pH was 7, and the filtrate was dried and passed through a silica gel column under normal pressure. After column chromatography, eluting the silica gel column by 50ml of xylene by 2, merging eluent and column chromatography liquid, decompressing and removing solvent, adding mixed solution of 280g of tetrahydrofuran and 280g of ethanol for recrystallization twice after solvent removal, and drying to obtain 32.9g of acompound 1, wherein the yield is as follows: 46.7, HPLC: 99.5 percent.

HPLC-MS: the theoretical molecular weight of thecompound 1 is 705.2, and the molecular weight is 705.8 according to actual detection results.

Example 2, Synthesis ofCompound 3 inclaim 3

Synthetic route tocompound 3

Under nitrogen protection, 57.9g of Compound C (100mmol), 37.4g of Compound H (210mmol), 0.58g of Tetratriphenylphosphine palladium (0.5mmol), 21.2g of sodium carbonate (200mmol), 84.8g of water, and 300g of toluene were added to a 500ml three-necked flask, followed by heating under reflux for 8 hours and TLC until no Compound C was present. After the reaction, the temperature was reduced to 30 ℃ and the layers were separated, the lower aqueous phase was separated, the organic phase was washed with water at 200 g.3 to pH 7, dried and passed through a silica gel column at normal pressure. After the column chromatography is finished, 100ml of toluene and 2 are used for eluting the silica gel column, after the elution is finished, the eluent and the column chromatography liquid are combined and decompressed to remove the solvent, 345g of toluene is added after the solvent removal is finished to recrystallize for three times, and after drying, 45.9g of the compound I is obtained, and the yield is as follows: 67%, HPLC: 99.1 percent.

HPLC-MS: the theoretical molecular weight of the compound I is 685.2, and the molecular weight is 685.7 in actual detection.

Under the protection of nitrogen, 68.5g of compound I (100mmol) and 300g of dichloromethane are added into a 500mL three-neck flask, 75.4mL of trifluoroacetic acid is added dropwise at room temperature, after the dropwise addition, the temperature is kept for 6 hours at room temperature, and TLC is used for tracking till no compound I exists. After the reaction, the solvent was removed under reduced pressure, 500g of ethyl acetate was added after the removal of the solvent, 200g of x 3 was washed with saturated aqueous sodium carbonate until the pH became 7, the solvent was removed under reduced pressure after the washing with water, 351g of a mixed solution of tetrahydrofuran and 351g of petroleum ether was added to recrystallize once, 49.7g of compound J after drying was obtained, yield was 85%, HPLC: 99.4 percent.

HPLC-MS: the theoretical molecular weight of the compound J is 585.1, and the molecular weight is 585.7 in actual detection.

Under a nitrogen atmosphere, 58.5G of Compound J (100mmol), 25.5G of Compound G (110mmol), 3.8G of cuprous iodide (20mmol), 42.4G of tripotassium phosphate (200mmol) and 300G of xylene were added to a 500ml three-necked flask, and the mixture was refluxed for 6 hours and TLC was carried out until the compound J was eliminated. After the reaction, the temperature was reduced to 30 ℃, the reaction mixture was filtered, 50ml of xylene was rinsed with 3, the filtrate was rinsed with 200g of 3 until the pH was 7, and the filtrate was dried and passed through a silica gel column under normal pressure. After column chromatography, eluting the silica gel column by 50ml of xylene by 2, merging eluent and column chromatography liquid, decompressing and removing solvent, adding mixed solution of 400g of chloroform and 200g of ethanol for recrystallization twice after solvent removal, and drying to obtain 35g of acompound 3, wherein the yield is as follows: 47.5%, HPLC: 99.5 percent.

HPLC-MS: the theoretical molecular weight of thecompound 3 is 737.2, and the molecular weight is 737.9 in actual detection.

EXAMPLE 3 Synthesis of Compound 59 inclaim 3

Synthetic route to compound 59

Under nitrogen protection, 57.9g of Compound C (100mmol), 44.5g of Compound K (210mmol), 1.16g of tetrakistriphenylphosphine palladium (1mmol), 21.2g of sodium carbonate (200mmol), 84.8g of water, and 300g of toluene were added to a 500ml three-necked flask, followed by refluxing for 8 hours and TLC until no Compound C was present. After the reaction, the temperature was reduced to 30 ℃ and the layers were separated, the lower aqueous phase was separated, the organic phase was washed with water at 200 g.3 to pH 7, dried and passed through a silica gel column at normal pressure. After column chromatography, 100ml oftoluene 2 is used for eluting the silica gel column, after elution, the eluent and the column chromatography liquid are combined and decompressed to remove the solvent, after solvent removal, 300g of toluene is added for recrystallization twice, and after drying, 45.2g of compound L is obtained, and the yield is as follows: 60%, HPLC: 98.5 percent.

HPLC-MS: the theoretical molecular weight of the compound L is 753.3, and the molecular weight is 753.7 in actual detection.

Under the protection of nitrogen, 75.3g of compound L (100mmol) and 300g of dichloromethane are added to a 500mL three-necked flask, 82.8mL of trifluoroacetic acid is added dropwise at room temperature, and after the addition, the mixture is kept at room temperature for 6 hours, and TLC is carried out until no compound L exists. After the reaction, the solvent was removed under reduced pressure, 600g of ethyl acetate was added after the removal of the solvent, 200g of x 3 was washed with saturated aqueous sodium carbonate until pH 7, the solvent was removed under reduced pressure after the washing with water, 260g of tetrahydrofuran was added to recrystallize once, 60.1g of compound M after drying, yield 92%, HPLC: 98.7 percent.

HPLC-MS: the theoretical molecular weight of the compound M is 653.2, and the molecular weight is 653.7 in actual detection.

Under a nitrogen atmosphere, 65.3g of Compound M (100mmol), 28.2g of Compound N (110mmol), 3.8g of cuprous iodide (20mmol), 42.4g of tripotassium phosphate (200mmol), and 300g of xylene were charged into a 500ml three-necked flask, and the mixture was refluxed for 6 hours and TLC was carried out until the compound M was removed. After the reaction, the temperature was reduced to 30 ℃, the reaction mixture was filtered, 50ml of xylene was rinsed with 3, the filtrate was rinsed with 200g of 3 until the pH was 7, and the filtrate was dried and passed through a silica gel column under normal pressure. After the column chromatography is finished, eluting the silica gel column by 50ml of xylene and 2, merging eluent and the column chromatography liquid, decompressing and removing the solvent, adding 400g of chloroform and 400g of normal hexane for recrystallization twice after the solvent removal is finished, and drying to obtain 40g of a compound 59, wherein the yield is as follows: 48.3%, HPLC: 99.3 percent.

HPLC-MS: the theoretical molecular weight of the compound 59 is 829.3, and the molecular weight is 829.5 in actual detection.

EXAMPLE 4 Synthesis of Compound 45 inclaim 3

Synthetic route to compound 45

Under nitrogen protection, 57.9g of Compound C (100mmol), 58.2g of Compound O (210mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 21.2g of sodium carbonate (200mmol), 84.8g of water, and 300g of toluene were added to a 500ml three-necked flask, followed by heating under reflux for 8 hours and TLC until no Compound C was present. After the reaction, the temperature was reduced to 30 ℃ and the layers were separated, the lower aqueous phase was separated, the organic phase was washed with water at 200 g.3 to pH 7, dried and passed through a silica gel column at normal pressure. After column passing, 100ml oftoluene 2 is used for eluting the silica gel column, after elution, the eluent and the column passing liquid are combined and decompressed to remove the solvent, after solvent removal, 600g of toluene is added for recrystallization twice, and after drying, 53g of compound P is obtained, the yield is as follows: 60%, HPLC: 99.0 percent.

HPLC-MS: the theoretical molecular weight of the compound P is 883.3, and the molecular weight is 883.9 in actual detection.

Under the protection of nitrogen, 88.3g of compound P (100mmol) and 300g of dichloromethane are added to a 500mL three-necked flask, 97.1mL of trifluoroacetic acid is added dropwise at room temperature, and after the addition, the mixture is kept at room temperature for 6 hours, and TLC is carried out until no compound P is obtained. After the reaction, the solvent was removed under reduced pressure, 700g of ethyl acetate was added after the removal of the solvent, 200g ofx 3 was washed with saturated aqueous sodium carbonate until the pH was 7, the solvent was removed under reduced pressure after the washing with water, 400g of tetrahydrofuran was added to recrystallize once, 70.5g of compound Q after drying, yield 90%, HPLC: 98.8 percent.

HPLC-MS: the theoretical molecular weight of the compound Q is 783.3, and the molecular weight is 783.9 in actual detection.

78.3g of Compound Q (100mmol), 30.3g of Compound R (110mmol), 7.6g of cuprous iodide (40mmol), 42.4g of tripotassium phosphate (200mmol) and 300g of xylene were added to a 500ml three-necked flask under a nitrogen atmosphere, and the mixture was refluxed for 6 hours and TLC was carried out until no Compound Q was present. After the reaction, the temperature was reduced to 30 ℃, the reaction mixture was filtered, 50ml of xylene was rinsed with 3, the filtrate was rinsed with 200g of 3 until the pH was 7, and the filtrate was dried and passed through a silica gel column under normal pressure. After column chromatography, eluting the silica gel column by 50ml of xylene by 2, merging eluent and the column chromatography liquid, decompressing and removing the solvent, adding 400g of chloroform and 400g of normal hexane for recrystallization for three times after solvent removal, and drying to obtain 41.5g of a compound 45, wherein the yield is as follows: 42.5%, HPLC: 99.5 percent.

HPLC-MS: the theoretical molecular weight of the compound 45 is 977.4, and the molecular weight is 977.9 in actual detection.

EXAMPLE 5 Synthesis of Compound 76 inclaim 3

Synthetic route to compound 76

Under nitrogen protection, 57.9g of Compound C (100mmol), 16.9g of Compound H (95mmol), 0.29g of Tetratriphenylphosphine palladium (0.25mmol), 21.2g of sodium carbonate (200mmol), 84.8g of water, and 300g of toluene were added to a 500ml three-necked flask, followed by heating under reflux for 8 hours and TLC until no Compound H was present. After the reaction, the temperature was reduced to 30 ℃ and the layers were separated, the lower aqueous phase was separated, the organic phase was washed with water at 200 g.3 to pH 7, dried and passed through a silica gel column at normal pressure. After the column chromatography is finished, 100ml of toluene and 2 are used for eluting the silica gel column, after the elution is finished, the eluent and the column chromatography liquid are combined and decompressed to remove the solvent, 480g of toluene is added for recrystallization twice after the solvent removal is finished, and 46.6g of compound S is obtained after drying, wherein the yield is as follows: 77.7%, HPLC: 99.2 percent.

HPLC-MS: the theoretical molecular weight of the compound S is 631.1, and the molecular weight is 632.0 according to actual detection results.

63.1g of Compound S (100mmol), 17.0g of Compound D (105mmol), 0.29g of tetrakistriphenylphosphine palladium (0.25mmol), 21.2g of sodium carbonate (200mmol), 84.8g of water and 300g of toluene were added to a 500ml three-necked flask under nitrogen protection, and the mixture was refluxed for 8 hours and TLC was continued until no Compound S was present. After the reaction, the temperature was reduced to 30 ℃ and the layers were separated, the lower aqueous phase was separated, the organic phase was washed with water at 200 g.3 to pH 7, dried and passed through a silica gel column at normal pressure. After the column chromatography is finished, 100ml of toluene and 2 are used for eluting the silica gel column, after the elution is finished, the eluent and the column chromatography liquid are combined and decompressed to remove the solvent, after the solvent removal is finished, 350 tetrahydrofuran is added for recrystallization twice, and 53.5g of compound T is obtained after drying, the yield is: 80%, HPLC: 99.5 percent.

HPLC-MS: the theoretical molecular weight of the compound T is 669.2, and the molecular weight is 669.7 according to actual detection results.

Under the protection of nitrogen, 66.9g of compound T (100mmol) and 300g of dichloromethane are added into a 500mL three-neck flask, 73.6mL of trifluoroacetic acid is added dropwise at room temperature, after the dropwise addition, the temperature is kept for 6 hours at room temperature, and TLC tracks that no compound T exists. After the reaction, the solvent was removed under reduced pressure, 800g of ethyl acetate was added after the removal of the solvent, 200g ofx 3 was washed with saturated aqueous sodium carbonate until the pH was 7, the solvent was removed under reduced pressure after the washing with water, 300g of tetrahydrofuran was added to recrystallize once, 51.8g of compound U after drying, yield 91%, HPLC: 98.5 percent.

HPLC-MS: the theoretical molecular weight of the compound U is 569.2, and the molecular weight is 569.9 in actual detection.

56.9g of Compound U (100mmol), 30.3g of Compound V (110mmol), 7.6g of cuprous iodide (40mmol), 42.4g of tripotassium phosphate (200mmol) and 300g of xylene were added to a 500ml three-necked flask under a nitrogen atmosphere, and the mixture was refluxed for 6 hours and TLC was carried out until no Compound U was contained. After the reaction, the temperature was reduced to 30 ℃, the reaction mixture was filtered, 50ml of xylene was rinsed with 3, the filtrate was rinsed with 200g of 3 until the pH was 7, and the filtrate was dried and passed through a silica gel column under normal pressure. After the column chromatography is finished, eluting the silica gel column by 50ml of xylene and 2, merging eluent and the column chromatography liquid, decompressing and removing the solvent, adding 500g of tetrahydrofuran and 200g of normal hexane after the solvent removal is finished, recrystallizing for three times, and drying to obtain 30.7g of a compound 76, wherein the yield is as follows: 40.0%, HPLC: 99.6 percent.

HPLC-MS: compound 76 has a theoretical molecular weight of 769.2 and a molecular weight of 769.9 as determined by actual testing.

The application effect of the synthesized compound of the present invention to an OLED device is described in detail by using examples 1 to 5.

Comparative example 1

Comparative example 1 atransparent electrode layer 2 having a transparent substrate layer 1 (the thickness of thetransparent electrode layer 2 was 215nm) was subjected to photolithography and etching to form a regular pattern of thetransparent electrode layer 2, and the transparentglass substrate layer 1 was subjected to alkali washing, high-purity water washing, drying, and then UV-ozone washing of the surface of thetransparent electrode layer 2 to remove organic residues. After washing, the anode of thetransparent substrate layer 1 was evaporated (molybdenum crucible, evaporation rate 0.1nm/s, vacuum degree about 5.0 x 10)^-5Pa) to form ahole injection layer 3 having a film thickness of 60nm by vapor deposition of an organic compound represented by the following structural formula (1):

on thehole injection layer 3, the layer was deposited by a vacuum deposition apparatus (molybdenum crucible, deposition rate 0.1nm/s, degree of vacuum of about 5.0 x 10)^-5Pa) of 10nm thick, and depositing an organic compound of the formula (2) as thehole transport layer 4

The light-emittinglayer 5 of the device was formed by vapor deposition of a compound of formula (3) onto the hole-transporting layer 4 (molybdenum crucible, vapor deposition rate 0.1nm/s, vacuum degree about 5.0 x 10^-5Pa)

The electron transport layer 6 was formed on thelight emitting layer 5 by a deposition apparatus (molybdenum crucible, deposition rate 0.1nm/s, vacuum degree of about 5.0 x 10)^-5Pa) using a compound of the formula (4) as an electronThe transmission material is evaporated on the luminescent layer to manufacture an electron transmission layer with the thickness of 25 nm;

the electron injection layer 7 was a 1nm thick layer of lithium fluoride (LiF) and passed through a vacuum evaporation apparatus (molybdenum crucible, evaporation rate 0.1nm/s, vacuum degree about 5.0 x 10^-5Pa) vapor deposition preparation;

thereflective electrode layer 8 was an aluminum (Al) layer having a film thickness of 140nm, and the layer was passed through a vacuum deposition apparatus (BN crucible, deposition rate 0.1nm/s, degree of vacuum of about 5.0 x 10^-5Pa) vapor deposition preparation.

After the device was produced, the anode and the cathode were connected by a known drive circuit, and the luminous efficiency, the luminous spectrum, and the current-voltage characteristics of the device were measured by a luminance measuring instrument (product name BM7, TOPCON corporation).

The manufacturing processes of the devices of application examples 1 to 5 of the present invention are completely the same, the devices use the same substrate and electrode material, the thickness of the electrode material is ensured to be the same, only the luminescent layer or the electron transport material is replaced by the material of the present invention, and the compounds used in the main structural layers of the devices of comparative example 1 and application examples 1 to 5 are shown in table 1

TABLE 1

The results of comparative example 1 and the OLED light-emitting devices manufactured in application examples 1 to 5 are shown in table 2.

TABLE 2

Examples	Luminous efficiency (cd/A)	Color(s)	CIE coordinates (x, y)
				Comparative example 1	8	Blue light	0.13，0.15
Application example 1	8.3	Blue light	0.13，0.12
				Application example 2	8.7	Blue light	0.13，0.14
Application example 3	8.5	Blue light	0.13，0.15
				Application example 4	9.1	Blue light	0.13，0.14
Application example 5	9.0	Blue light	0.13，0.16

The analysis of table 2 shows that the luminescent device prepared by using the organic compound of the present invention as the OLED luminescent material has greater advantages in terms of luminescent efficiency and color purity performance than the currently used OLED luminescent device, and has good industrialization prospects.

Claims

1. An organic compound with carbazole and pyrimidine as core is characterized in that the compound takes carbazole and pyrimidine structure as main body, and the general formula of the molecular structure is shown as general formula (A):

in formula (A), R1 is selected from:

one of (1);

r2 and R3 are independently selected from:

wherein R2 and R3 are the same or different.

2. A carbazole and pyrimidine core organic compound according to claim 1, wherein the compound has the following specific formula:

3. a material for an OLED electroluminescent device, characterized by comprising an organic compound having carbazole and pyrimidine as a core according to any one of claims 1 to 2.

4. An electroluminescent device comprising a transparent substrate layer, a transparent electrode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode reflection electrode layer, wherein at least one of the light emitting layer and the electron transport layer contains the carbazole-pyrimidine-centered organic compound according to any one of claims 1 to 2.