CN110642724A - Blue light electroluminescent material and application thereof - Google Patents

Blue light electroluminescent material and application thereof Download PDF

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CN110642724A
CN110642724A CN201910978417.8A CN201910978417A CN110642724A CN 110642724 A CN110642724 A CN 110642724A CN 201910978417 A CN201910978417 A CN 201910978417A CN 110642724 A CN110642724 A CN 110642724A
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reaction vessel
electroluminescent material
added
substituted
nitrogen
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王辉
刘志远
李建行
段伟伟
李猛
张思铭
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention relates to a blue light electroluminescent material and application thereof, wherein the structural formula of the blue light electroluminescent material is shown as the following chemical formula 1:

Description

Blue light electroluminescent material and application thereof
Technical Field
The invention relates to the field of organic luminescent materials, in particular to a blue light electroluminescent material and application thereof.
Background
In the early 60 s of the 20 th century, organic electroluminescence was observed. In 1963, Pope et al, university of New York, USA, developed a crystal study on organic aromatic anthraceneAt present, when hundreds of volts are applied to the anthracene crystal, the crystal can be observed to have weak blue light emission, and thus, a research and development way for photoelectric materials is opened up. However, this finding has not been considered to be important because the required driving voltage is too high and the light emission efficiency is low. In 1987, doctor Deng Qingyun reported an electroluminescent diode technology based on organic luminescent materials, and mainly adopts a vacuum evaporation mode to prepare a double-layer device with a transmission layer and a luminescent layer, so that the quantum efficiency is improved to 1%, and the quantum efficiency can reach 1000cd/m under the working voltage lower than 10V2The brightness of the organic electroluminescent device is attracted by the wide attention of scientific enthusiasts in the world, and the organic electroluminescent technology is pushed to move to the practical stage.
With the continuous development of Organic Light-Emitting diode technology, Organic Light-Emitting devices (OLEDs for short) are widely used in the fields of information display and illumination by virtue of their advantages of self-luminescence, wide Light-Emitting viewing angle, thinness, low driving voltage, fast response speed, flexibility, folding, and the like. The light emitting layer is an important component of OLEDs and is composed of three organic electroluminescent materials, i.e., red, green and blue, among which a blue light emitting material is particularly important because it can provide blue light required for illumination and display, and can obtain red light and green light by energy transfer. Although the organic electroluminescent material is the earliest discovered organic electroluminescent material, the properties of the red light material and the green light material which are disclosed in the prior art can meet the requirements and applications of large-scale production, and the blue light material has a wider energy gap and is difficult to provide higher luminous efficiency under low voltage, so that the search for the blue light organic electroluminescent material with high performance and good stability becomes a key and difficult problem for making a major breakthrough in the field of OLEDs.
Disclosure of Invention
The blue light electroluminescent material provided by the invention has the advantages of high luminous efficiency, high color saturation, good film-forming property, good thermal stability and the like.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
the invention provides a blue light electroluminescent material, the structural formula of which is shown as the following chemical formula 1:
Figure BDA0002234414390000021
wherein R is1～R8The same or different, each independently represents H, deuterium, an alkyl group, an oxyalkyl group, an aryl group, an aryloxy group, a diarylamino group, a siloxane, or a silyl group;
l represents a bond, a substituted or unsubstituted C6-C60 aryl, or a substituted or unsubstituted C3-C60 heteroaryl;
Ar1、Ar2each independently represents deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, alkylamino, arylamine, heteroarylamine, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C1-C60 aliphatic, substituted or unsubstituted C1-C60 alkoxy, or substituted or unsubstituted C3-C60 heteroaryl.
In the above technical scheme, R1～R8Deuterium is preferred.
In the above technical scheme, Ar1And Ar2Identical or different and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl.
In the above technical scheme, Ar1、Ar2And adjacent substituents are joined to form a single ring or multiple rings, specifically a C3-C60 aliphatic or aromatic ring.
In the above technical scheme, when Ar is1、Ar2When linked to an adjacent substituent to form a monocyclic or polycyclic ring, the carbon atom is substituted with at least one nitrogen, oxygen or sulfur atom.
In the above technical solution, Ar is1And Ar2The substituent on it is preferably deuterium.
The above "substituted or unsubstituted" means: the substituent is deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C1-C60 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkyl, C3-C60 cycloalkenyl, C1-C60 alkylsilyl, or C6-C60 arylsilyl; preferably deuterium;
the above-mentioned "hydrocarbon group" includes straight chain, branched chain and cyclic hydrocarbon groups, and carbon atoms on the cyclic hydrocarbon group may be substituted by hetero atoms of oxygen, nitrogen and sulfur; the "hydrocarbon group" mentioned above includes alkyl, alkenyl, alkynyl; the "hydrocarbon group" is preferably a C1-C60 alkyl group, C3-C60 cycloalkyl group, C3-C60 cycloalkenyl group, or C3-C60 heterocycloalkyl group.
In the above technical solution, the blue electroluminescent material is selected from any one of the following structures:
Figure BDA0002234414390000031
Figure BDA0002234414390000041
Figure BDA0002234414390000051
Figure BDA0002234414390000061
Figure BDA0002234414390000071
the invention also provides application of the blue light electroluminescent material in preparing an organic light-emitting device.
The organic light emitting device includes: a first electrode, an organic material layer, and a second electrode; wherein the organic material layer includes the blue electroluminescent material represented by chemical formula 1 of the present invention.
In the above technical solution, the organic material layer includes at least one of a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer.
The invention has the beneficial effects that:
the blue light electroluminescent material provided by the invention has the advantages of high luminous efficiency, high color saturation, good film forming property, good thermal stability and the like.
Compared with the conventional blue host material, the blue electroluminescent material provided by the invention has the characteristics of high luminous efficiency and long service life of the prepared device.
The invention also finds that the characteristic of the deuterium element is utilized, the deuterium element is introduced into the material structure, the quantum efficiency, the color saturation, the service life and the like can be improved, and meanwhile, the material has higher tolerance when a device is prepared.
Detailed Description
The blue light electroluminescent material provided by the invention can be prepared by the following preparation method:
method 1
Step 1, fully reacting a raw material A-a with a raw material B-a to prepare an intermediate C-a;
step 2, fully reacting the intermediate C-a with the raw material D-a to obtain an intermediate E-a;
step 3, fully reacting the intermediate E-a with the raw material F-a to obtain an intermediate G-a;
step 4, fully reacting the intermediate G-a with the raw material H-a to obtain an intermediate I-a;
and step 5, fully reacting the intermediate I-a with the raw material J-a to obtain the compound of the chemical formula 1-a.
Scheme 1: ar (Ar)1And Ar2All substituted by deuterium
Figure BDA0002234414390000081
Method 2
Step 1, fully reacting a raw material A-B with a raw material B-B to prepare an intermediate C-B;
step 2, fully reacting the intermediate C-b with the raw material D-b to obtain an intermediate E-b;
step 3, fully reacting the intermediate E-b with the raw material F-b to obtain an intermediate G-b;
step 4, fully reacting the intermediate G-b with the raw material H-b to obtain a compound of a chemical formula 1-b;
scheme 2: ar (Ar)1When substituted by deuterium
Figure BDA0002234414390000091
Method 3
Step 1, fully reacting a raw material A-C with a raw material B-C to prepare an intermediate C-C;
step 2, fully reacting the intermediate C-C with the raw material D-C to obtain an intermediate E-C;
step 3, fully reacting the intermediate E-c with the raw material F-c to obtain an intermediate G-c;
step 4, fully reacting the intermediate G-c with the raw material H-c to obtain a compound of a chemical formula 1-c;
scheme 3: ar (Ar)2When substituted by deuterium
Figure BDA0002234414390000092
In the above substituents, Hal represents halogen, Ar1-D represents Ar1The substituent is deuterium, Ar2-D represents Ar2The substituents above are deuterium, and the other substituents are each in the same range as described in chemical formula 1.
The invention relates to a blue light electroluminescent material, which comprises the following specific embodiments:
example 1: preparation of Compound No. F002
Figure BDA0002234414390000101
Preparation of intermediate C-2:
a reaction vessel was purged with nitrogen, and to the reaction vessel were added raw material A-2(85.6mmol, 14.72g), raw material B-2(77.82mmol, 20g) and potassium carbonate (3.2g) under a nitrogen atmosphere, and to the reaction vessel, toluene (400mL), ethanol (200mL) and water (200mL) were added under a nitrogen atmosphere, and the reaction vessel was stirred uniformly, and to the reaction vessel, tetrakis (triphenylphosphine) palladium (0.9g) was added under a nitrogen atmosphere, and the reaction was carried out at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate C-221.3 g (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 305.21.
Preparation of intermediate E-2:
the reaction vessel was purged with nitrogen, and intermediate C-2(66.93mmol, 20.37g), starting material D-2(80.31mmol, 14.3g) and methylene chloride (300mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was reacted for 16 hours under stirring in the nitrogen purge reactor, and Na was added to the reaction system2CO3The organic phase was washed (10%, 100mL), and after separating the organic phase, the organic phase was washed with water three times, separated, dried over anhydrous sodium sulfate, filtered, added to silica gel, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate E-223.3 g (yield 91%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 384.35.
Preparation of intermediate G-2:
the reaction vessel was replaced with nitrogen, and intermediate E-2(60mmol, 22.99g), starting material F-2(120mmol, 30.5g) and potassium acetate (14.72g) were added to the reaction vessel under a nitrogen atmosphere, and 1, 4-dioxane (200mL) was added under a nitrogen atmosphere, the reaction vessel was replaced with nitrogen, and the mixture was stirred uniformly, and tris (dibenzylideneacetone) dipalladium (0.55g) was added under a nitrogen atmosphere, and reacted at 100 ℃ for 16 hours. Cooling to room temperature, adding 200mL of water into the reaction system, carrying out suction filtration to obtain a white-like solid, leaching with 50mL of ethanol and 50mL of petroleum ether, and drying. The solid was dissolved in methylene chloride, filtered, the filtrate was concentrated to 60mL, 60mL of ethanol was added dropwise to the filtrate, and the mixture was filtered by suction to obtain G-215.49G (yield: 60%) as a solid intermediate, which was 99.5% pure by HPLC. The mass spectrum detection value was 431.42.
Preparation of intermediate I-2:
the reaction vessel was replaced with nitrogen, and intermediate G-2(34.2mmol, 14.7G), raw material H-2(28.5mmol, 5.9G) and potassium carbonate (11.8G) were added to the reaction vessel under a nitrogen atmosphere, and toluene (300mL), ethanol (150mL) and water (150mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.3G) was added to the reaction vessel under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate I-212g (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 471.51.
Preparing a compound F002;
the reaction vessel was purged with nitrogen, and intermediate I-2(26.3mmol, 12.37g) and benzene-D6 (J-2) (200mL) were added to the reaction vessel under a nitrogen atmosphere, the reaction vessel was purged with nitrogen, stirred at room temperature for 18 hours, and D was added2O (100 mL). The aqueous phase was washed with dichloromethane (60mL), combined with the organic phase and dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to give F00211.66g (yield 90%) as a solid compound having a purity of 99.9% by HPLC. The mass spectrum detection value was 493.61.
Example 2: preparation of Compound No. F004
Figure BDA0002234414390000121
Preparation of intermediate C-4:
a reaction vessel was purged with nitrogen, and to the reaction vessel were added raw material A-4(85.6mmol, 14.72g), raw material B-4(77.82mmol, 20g) and potassium carbonate (3.2g) under a nitrogen atmosphere, and to the reaction vessel, toluene (400mL), ethanol (200mL) and water (200mL) were added under a nitrogen atmosphere, and the reaction vessel was stirred uniformly, and to the reaction vessel, tetrakis (triphenylphosphine) palladium (0.9g) was added under a nitrogen atmosphere, and the reaction was carried out at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate C-421.3 g (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 305.25.
Preparation of intermediate E-4:
the reaction vessel was purged with nitrogen, and intermediate C-4(66.93mmol, 20.37g), starting material D-4(80.31mmol, 14.3g) and methylene chloride (300mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was reacted for 16 hours while stirring in the nitrogen purged reactor, and Na was added to the reaction system2CO3The organic phase was washed (10%, 100mL), and after separating the organic phase, the organic phase was washed with water three times, separated, dried over anhydrous sodium sulfate, filtered, added to silica gel, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate E-423.3 g (yield 91%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 384.41.
Preparation of intermediate G-4:
the reaction vessel was purged with nitrogen, and intermediate E-4(60mmol, 22.99g), starting material F-4(120mmol, 30.5g) and potassium acetate (14.72g) were added to the reaction vessel under a nitrogen atmosphere, and 1, 4-dioxane (200mL) was added under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred uniformly, and tris (dibenzylideneacetone) dipalladium (0.55g) was added under a nitrogen atmosphere, and reacted at 100 ℃ for 16 hours. Cooling to room temperature, adding 200mL of water into the reaction system, carrying out suction filtration to obtain a white-like solid, leaching with 50mL of ethanol and 50mL of petroleum ether, and drying. The solid was dissolved in methylene chloride, filtered, the filtrate was concentrated to 60mL, 60mL of ethanol was added dropwise to the filtrate, and the mixture was filtered by suction to obtain G-415.49G (yield: 60%) as a solid intermediate, which was 99.5% pure by HPLC. The mass spectrum detection value was 431.47.
Preparation of intermediate I-4:
the reaction vessel was replaced with nitrogen, and intermediate G-4(34.2mmol, 14.7G), raw material H-4(28.5mmol, 7.49G) and potassium carbonate (11.8G) were added to the reaction vessel under a nitrogen atmosphere, and toluene (300mL), ethanol (150mL) and water (150mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.3G) was added to the reaction vessel under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate I-412.48 g (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 487.52.
Preparation of compound F004;
the reaction vessel was purged with nitrogen, and intermediate I-4(26.3mmol, 12.79g) and benzene-D6 (J-4) (200mL) were added to the reaction vessel under a nitrogen atmosphere, the reaction vessel was purged with nitrogen, stirred at room temperature for 18 hours, and D was added2O (100 mL). The aqueous phase was washed with dichloromethane (60mL), combined with the organic phase and dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to give F00413.38g as a solid compound (yield 90%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 508.49.
Example 3: preparation of Compound No. F013
Figure BDA0002234414390000151
Preparation of intermediate C-13:
the reaction vessel was purged with nitrogen, and to the reaction vessel were added raw material A-13(85.6mmol, 16.95g), raw material B-13(77.82mmol, 20g), and potassium carbonate (32g) under nitrogen, and the reaction vessel was purged with nitrogen, and to the reaction vessel, toluene (400mL), ethanol (200mL), and water (200mL) were added under nitrogen, and the reaction vessel was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.9g) was added under nitrogen, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate C-1323.1 g (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 331.25.
Preparation of intermediate E-13:
the reaction vessel was purged with nitrogen, and intermediate C-13(66.93mmol, 22.1g), starting material D-13(80.31mmol, 14.3g) and methylene chloride (300mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was reacted for 16 hours under stirring in the nitrogen purge reactor, and Na was added to the reaction system2CO3The organic phase was washed (10%, 100mL), and after separating the organic phase, the organic phase was washed with water three times, separated, dried over anhydrous sodium sulfate, filtered, added to silica gel, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate E-1324.7 g (yield 90%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 410.52.
Preparation of intermediate G-13:
the reaction vessel was purged with nitrogen, and intermediate E-13(60mmol, 24.6g), starting material F-13(120mmol, 30.5g) and potassium acetate (14.72g) were added to the reaction vessel under a nitrogen atmosphere, and 1, 4-dioxane (200mL) was added under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred uniformly, and tris (dibenzylideneacetone) dipalladium (0.55g) was added under a nitrogen atmosphere, and reacted at 100 ℃ for 16 hours. Cooling to room temperature, adding 200mL of water into the reaction system, carrying out suction filtration to obtain a white-like solid, leaching with 50mL of ethanol and 50mL of petroleum ether, and drying. The solid was dissolved in methylene chloride, filtered, the filtrate was concentrated to 60mL, 60mL of ethanol was added dropwise to the filtrate, and the resulting solution was filtered under suction to obtain 1316.4G (yield: 60%) of a solid intermediate G, which was 99.2% pure by HPLC. The mass spectrum detection value was 457.25.
Preparation of intermediate I-13:
the reaction vessel was replaced with nitrogen, and intermediate G-13(34.2mmol, 15.6G), raw material H-13(28.5mmol, 7G) and potassium carbonate (11.8G) were added to the reaction vessel under a nitrogen atmosphere, and toluene (300mL), ethanol (150mL) and water (150mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.3G) was added to the reaction vessel under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate I-1311.3 g (yield 80%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 497.53.
Preparation of compound F013:
displacing the reaction vessel with nitrogen, adding intermediate I-13(20.14mmol, 10g) and benzene-D6 (J-13) (200mL) into the reaction vessel under nitrogen atmosphere, displacing the reaction vessel with nitrogen, stirring at room temperature for 18h, and adding D2O (100 mL). The aqueous phase was washed with dichloromethane (60mL), combined with the organic phase and dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to give F0139.4 g (yield 90%) as a solid compound with a purity of 99.9% by HPLC. The mass spectrum detection value was 521.54.
Example 4: preparation of Compound No. F021
Figure BDA0002234414390000171
Preparation of intermediate C-21:
the reaction vessel was purged with nitrogen, and to the reaction vessel were added raw material A-21(85.6mmol, 16.92g), raw material B-21(77.82mmol, 20g), and potassium carbonate (32g) under a nitrogen atmosphere, and to the reaction vessel, toluene (400mL), ethanol (200mL), and water (200mL) were added under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.9g) was added under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain C-2123 g (yield 90%) as a solid intermediate with a purity of 99.9% by HPLC. The mass spectrum detection value was 331.27.
Preparation of intermediate E-21:
the reaction vessel was purged with nitrogen, and intermediate C-21(66.93mmol, 22.1g), starting material D-21(80.31mmol, 14.3g) and methylene chloride (300mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was reacted for 16 hours under stirring in the nitrogen purge reactor, and Na was added to the reaction system2CO3The organic phase was washed (10%, 100mL), and after separating the organic phase, the organic phase was washed with water three times, separated, dried over anhydrous sodium sulfate, filtered, added to silica gel, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate E-2124.7 g (yield 90%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 410.63.
Preparation of intermediate G-21:
the reaction vessel was purged with nitrogen, and intermediate E-21(60mmol, 24.6g), starting material F-21(120mmol, 30.5g) and potassium acetate (14.72g) were added to the reaction vessel under a nitrogen atmosphere, and 1, 4-dioxane (200mL) was added under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred uniformly, and tris (dibenzylideneacetone) dipalladium (0.55g) was added under a nitrogen atmosphere, and reacted at 100 ℃ for 16 hours. Cooling to room temperature, adding 200mL of water into the reaction system, carrying out suction filtration to obtain a white-like solid, leaching with 50mL of ethanol and 50mL of petroleum ether, and drying. The solid was dissolved in methylene chloride, filtered, the filtrate was concentrated to 60mL, 60mL of ethanol was added dropwise to the filtrate, and the mixture was filtered by suction to obtain G-2116.4G (yield: 60%) as a solid intermediate, which was 99.2% pure by HPLC. The mass spectrum detection value was 457.21.
Preparation of intermediate I-21:
the reaction vessel was replaced with nitrogen, and intermediate G-21(34.2mmol, 15.6G), raw material H-21(28.5mmol, 7.5G) and potassium carbonate (11.8G) were added to the reaction vessel under a nitrogen atmosphere, and toluene (300mL), ethanol (150mL) and water (150mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.3G) was added to the reaction vessel under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate I-2111.7 g (yield 80%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 513.32.
Preparation of compound F021:
displacing the reaction vessel with nitrogen, adding intermediate I-21(19.5mmol, 10g) and benzene-D6 (J-21) (200mL) into the reaction vessel under nitrogen atmosphere, displacing the reaction vessel with nitrogen, stirring at room temperature for 18h, and adding D2O (100 mL). The aqueous phase was washed with dichloromethane (60mL), combined with the organic phase and dried over anhydrous sodium sulfate, and after concentration, column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain f0219.5 g (yield 90%) as a solid compound, and HPLC showed 99.9% purity. The mass spectrum detection value was 537.77.
Example 5: preparation of Compound No. F049
Figure BDA0002234414390000201
Preparation of intermediate C-49:
the reaction vessel was purged with nitrogen, and to the reaction vessel were added raw material A-49(85.6mmol, 16.95g), raw material B-49(77.82mmol, 20g) and potassium carbonate (32g) under a nitrogen atmosphere, and to the reaction vessel, toluene (400mL), ethanol (200mL) and water (200mL) were added under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.9g) was added under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate C-4923.1 g (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 331.28.
Preparation of intermediate E-49:
the reaction vessel was purged with nitrogen, and intermediate C-49(66.93mmol, 22.1g), starting material D-49(80.31mmol, 14.3g) and methylene chloride (300mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was reacted for 16 hours under stirring in the nitrogen-purged reaction vessel, and Na was added to the reaction system2CO3The organic phase was washed (10%, 100mL), and after separating the organic phase, the organic phase was washed with water three times, separated, dried over anhydrous sodium sulfate, filtered, added to silica gel, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate E-4924.6 g (yield 90%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 410.27.
Preparation of intermediate G-49:
the reaction vessel was purged with nitrogen, and intermediate E-49(60mmol, 24.5g), starting material F-49(120mmol, 30.5g) and potassium acetate (14.72g) were added to the reaction vessel under a nitrogen atmosphere, and 1, 4-dioxane (200mL) was added under a nitrogen atmosphere to the reaction vessel, and the reaction vessel was purged with nitrogen, stirred uniformly, and tris (dibenzylideneacetone) dipalladium (0.55g) was added under a nitrogen atmosphere to react at 100 ℃ for 16 hours. Cooling to room temperature, adding 200mL of water into the reaction system, carrying out suction filtration to obtain a white-like solid, leaching with 50mL of ethanol and 50mL of petroleum ether, and drying. The solid was dissolved in methylene chloride, filtered, the filtrate was concentrated to 60mL, 60mL of ethanol was added dropwise to the filtrate, and the mixture was filtered by suction to obtain G-4916.5G (yield: 60%) as a solid intermediate, which was 99.6% pure by HPLC. The mass spectrum detection value was 457.35.
Preparation of intermediate I-49:
the reaction vessel was replaced with nitrogen, and intermediate G-49(34.2mmol, 15.6G), raw material H-49(28.5mmol, 8.5G) and potassium carbonate (11.8G) were added to the reaction vessel under a nitrogen atmosphere, and toluene (300mL), ethanol (150mL) and water (150mL) were added to the reaction vessel under a nitrogen atmosphere, and the mixture was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.3G) was added to the reaction vessel under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate I-4912.5 g (yield 80%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 547.66.
Preparation of compound F049:
the reaction vessel was purged with nitrogen, and to the reaction vessel were added the intermediate I-49(18.29mmol, 10g) and benzene-D6 (J-49) (200mL) under a nitrogen atmosphere, the reaction vessel was purged with nitrogen, stirred at room temperature for 18 hours, and D was added2O (100 mL). The aqueous phase was washed with dichloromethane (60mL), combined with the organic phase and dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to give F0499.4 g (yield 90%) as a solid compound with a purity of 99.9% by HPLC. The mass spectrum detection value was 573.62.
Example 6: preparation of Compound No. F061
Preparation of intermediate C-61:
the reaction vessel was purged with nitrogen, and intermediate A-61(60.00mmol, 15.79g), raw material B-61(77.82mmol, 19.7g) and potassium acetate (14.72g) were added to the reaction vessel under a nitrogen atmosphere, and 1, 4-dioxane (200mL) was added under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred uniformly, and tris (dibenzylideneacetone) dipalladium (0.55g) was added under a nitrogen atmosphere, and reacted at 100 ℃ for 16 hours. Cooling to room temperature, adding 200mL of water into the reaction system, carrying out suction filtration to obtain a white-like solid, leaching with 50mL of ethanol and 50mL of petroleum ether, and drying. The solid was dissolved in methylene chloride, filtered, the filtrate was concentrated to 60mL, 60mL of ethanol was added dropwise to the filtrate, and the mixture was filtered by suction to obtain C-6111.18 g (yield: 60%) as a solid intermediate, which was 99.6% pure by HPLC. The mass spectrum detection value was 311.25.
Preparation of intermediate E-61:
a reaction vessel was purged with nitrogen, and to the reaction vessel were added raw material C-61(34.12mmol, 11g), raw material D-61(37.53mmol, 9.6g) and potassium carbonate (14.12g) under a nitrogen atmosphere, and to the reaction vessel, toluene (200mL), ethanol (100mL) and water (100mL) were added under a nitrogen atmosphere, and the reaction vessel was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.39g) was added under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain intermediate E-6111.10 g (yield 90%) as a solid with a purity of 99.9% by HPLC. The mass spectrum detection value was 362.42.
Preparation of intermediate G-61:
the reaction vessel was purged with nitrogen, and intermediate E-61(85.6mmol, 11g), benzene-D6 (F-61) (77.82mmol, 20g) and potassium carbonate (32g) were added to the reaction vessel under a nitrogen atmosphere, and toluene (400mL), ethanol (200mL) and water (200mL) were added to the reaction vessel under a nitrogen atmosphere, and the reaction vessel was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.9g) was added to the reaction vessel under a nitrogen atmosphere, followed by reaction at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (200mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate G-6123.1G (yield 90%) with a purity of 99.9% by HPLC. The mass spectrum detection value was 378.56.
Preparing an intermediate I-61;
the reaction vessel was purged with nitrogen, and then, the intermediates G-61(30.43mmol, 10G) and H-61(200mL) were added to the reaction vessel under a nitrogen atmosphere, and the reaction vessel was purged with nitrogen, stirred at room temperature for 18 hours, and then, D was added2O (100 mL). The aqueous phase was washed with dichloromethane (60m), combined with the organic phase and dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid intermediate I-6111.49 g (yield 90%), which was 99.9% pure by HPLC. The mass spectrum detection value is 456.44.
Preparation of compound F061:
a reaction vessel was replaced with nitrogen, and to the reaction vessel were added raw material I-61(24.15mmol, 16.95g), J-61(21.95mmol, 3.77g) and potassium carbonate (6.05g) under a nitrogen atmosphere, and to the reaction vessel were replaced with nitrogen, toluene (200mL), ethanol (100mL) and water (100mL) under a nitrogen atmosphere, and the reaction vessel was stirred uniformly, and tetrakis (triphenylphosphine) palladium (0.25g) was added under a nitrogen atmosphere, and reacted at 90 ℃ for 16 hours. Cooling to room temperature, separating to obtain an organic phase, extracting an aqueous phase with dichloromethane (100mL), combining the separated liquid and the organic phase, drying with anhydrous sodium sulfate, filtering, concentrating to 50mL, pouring into 50mL of methanol, and filtering to obtain a solid. The solid was dissolved in dichloromethane, silica gel was added, concentrated and dried, and column chromatography was performed using a mixed solvent of dichloromethane and petroleum ether as an eluent to obtain solid compound F0619.91g (yield 90%), which showed a purity of 99.9% by HPLC. The mass spectrum detection value was 502.65.
The synthesis methods of other compounds are the same as those described above, and are not repeated herein, and the mass spectrum or molecular formula of other synthesis examples is shown as follows:
compound (I) Molecular formula Calculated mass spectrum Mass spectrometric test values
F065 C34H7D13N2O 485.63 486.66
F069 C38D2S2 564.85 565.31
F071 C42D24S2 616.92 617.25
F077 C45D27N3O 652.90 653.87
Manufacturing an OLED using the blue electroluminescent material of chemical formula 1 according to the present invention;
example 7:
coating thickness of Fisher company of
Figure BDA0002234414390000241
The ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. 4,4' -tri [ 2-naphthyl phenylamino ] with the thickness of 50nm is evaporated on the prepared ITO transparent electrode]Triphenylamine (2-TNATA) as a hole injection layer.N-bis (1-naphthyl) -N, N ' -diphenyl- (1,1' -biphenyl) -4,4' -diamine (NPB) having a thickness of 30nm was vacuum-evaporated on the formed hole injection layer as a hole transport layer. Then, 4' -bis [4- (di-p-tolylamino) styryl group as a host material and a dopant material was vapor-deposited on the above hole transport layer with the compound F002 of the present invention having a thickness of 30nm]Biphenyl (DPAVBi). The weight ratio of host material to dopant material was 97: 3. Then, bis (2-methyl-8-hydroxyquinoline-N1, 08) - (1,1' -biphenyl-4-hydroxy) aluminum (BALq) as a hole-blocking layer was vacuum-evaporated on the above light-emitting layer to a thickness of 10 nm. Tris (8-hydroxyquinoline) aluminum (III) Alq3 was vacuum-deposited on the hole-blocking layer to a thickness of 40nm as an electron-transporting layer. Lithium fluoride (LiF) was vacuum-deposited on the electron transport layer to a thickness of 0.5nm as an electron injection layer. And finally, evaporating aluminum with the thickness of 150nm as a cathode, thereby completing the preparation of the organic electroluminescent device.
Figure BDA0002234414390000251
Referring to the above method, compounds F004, F013, F021, F049, F061, F065, F069, F071 and F077 were used in place of compound F002 to prepare organic electroluminescent devices of the corresponding compounds.
Comparative example 1:
an organic electroluminescent device was produced in the same manner as in example 7, except that compound 9, 10-bis- (1-naphthyl) Anthracene (ADN) was used instead of compound 2.
Electroluminescent properties of OLEDs in the above technology:
the efficiency (flow density: 10 mA/cm) of each of the organic electroluminescent devices manufactured in examples and comparative example 1 was evaluated2) And life (10 mA/cm)2T90 at current density).
Figure BDA0002234414390000262
From the above table, it is understood that the compound of the present invention can be used as a high-efficiency blue electroluminescent material. Furthermore, the device to which the compound of the present invention was applied as a host material showed a significant improvement in color purity. The improvement in both lifetime and luminous efficiency demonstrates the excellent properties of the materials of the present invention.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (10)

1. A blue electroluminescent material, characterized in that its structural formula is shown in chemical formula 1:
Figure FDA0002234414380000011
wherein R is1～R8The same or different, each independently represents H, deuterium, an alkyl group, an oxyalkyl group, an aryl group, an aryloxy group, a diarylamino group, a siloxane, or a silyl group;
l represents a bond, a substituted or unsubstituted C6-C60 aryl, or a substituted or unsubstituted C3-C60 heteroaryl;
Ar1、Ar2each independently represents deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, alkylamino, arylamine, heteroarylamine, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C1-C60 aliphatic, substituted or unsubstituted C1-C60 alkoxy, or substituted or unsubstituted C3-C60 heteroaryl.
2. The blue electroluminescent material according to claim 1, wherein R is1～R8Is deuterium.
3. The blue electroluminescent material according to claim 1, wherein Ar is Ar1And Ar2Identical or different and at least one is selected from substituted or unsubstituted C3-C60 heteroaryl.
4. The blue electroluminescent material according to claim 1, wherein Ar is Ar1、Ar2And adjacent substituents are joined to form a single ring or multiple rings, specifically a C3-C60 aliphatic or aromatic ring.
5. The blue electroluminescent material according to claim 4, wherein Ar is Ar1、Ar2When linked to an adjacent substituent to form a monocyclic or polycyclic ring, the carbon atom is substituted with at least one nitrogen, oxygen or sulfur atom.
6. The blue electroluminescent material of claim 1, wherein Ar is selected from the group consisting of1And Ar2Wherein the substituent is deuterium.
7. The blue electroluminescent material according to claim 1, wherein the blue electroluminescent material is selected from any one of the following structures:
Figure FDA0002234414380000021
Figure FDA0002234414380000041
Figure FDA0002234414380000051
Figure FDA0002234414380000061
8. use of the blue electroluminescent material according to any one of claims 1 to 7 for the production of organic light-emitting devices.
9. Use according to claim 8, wherein the organic light emitting device comprises: a first electrode, an organic material layer, and a second electrode; wherein the organic material layer comprises the blue electroluminescent material according to any one of claims 1 to 7.
10. The use according to claim 9, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer.
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