Organic blue fluorescent material and preparation method and application thereof

Abstract

The invention relates to an organic blue fluorescent material and a preparation method and application thereof. The material adopts a delta bond as a bridge chain to connect two anthracene molecule luminescence units and regulate the conjugation state of organic molecules; meanwhile, a steric hindrance group is introduced onto the delta bond to inhibit a pi-pi accumulation effect among the organicmolecules, and correspondingly the organic blue fluorescent material is prepared and has high thermal stability and high luminous quantum efficiency. The specific preparation method and application mainly include the steps of adopting 9-benzanthracene-10 borate and 4,4'-dibromo diphenyl bis-substituted methane for conducting a Suzuki coupling reaction to prepare the organic blue fluorescent material. The material is adopted as a luminous layer and achieves a non-doped deep blue OLED device with high performance.

Description

Technical field

[0001] The invention belongs to the field of organic electroluminescent diodes, and in particular relates to an organic blue fluorescent material and its preparation method and application.

Background technique

[0002] Since 1987, Organic Light-Emitting Diodes (OLEDs for short) have gradually become the industry-recognized next-generation flat panel display technology. Because of its advantages of active luminescence, low driving voltage, light and thin, wide luminous viewing angle, fast response, bendable and foldable, simple preparation process, low cost, and large-area production, it has great potential in the fields of full-color flat panel display and solid-state lighting. application prospects. At present, compared with the existing red and green organic electroluminescent materials and devices, blue organic electroluminescent materials and devices are always scarce. Relatively speaking, blue light materials have a wide energy gap, so it is diffi...

Examples

Embodiment 1

[0056] ①Add 2.60g of 9-bromoanthracene, 1.83g of phenylboronic acid, 13.82g of potassium carbonate (add 30mL of distilled water to make a 2.0M solution), 100mL of toluene, and 30mL of ethanol into the reaction flask, then add 0.58g of tetrakis(triphenylphosphine )palladium. Then vacuumize the system, and reflux at 100° C. for 12 hours under the protection of nitrogen. After the reaction, the product was obtained by toluene extraction, rotary evaporation, column chromatography (eluent: n-hexane), and recrystallization (n-hexane / toluene=4:1). Yield 86%.

[0057] ②Bromination of 9-benzoanthracene: Add 2.15g of 9-benzoanthracene, 100mL of DMF, and 1.80g of NBS into the reaction flask, then vacuumize the system, and react under nitrogen protection at 85°C for 1 hour. After the reaction, the product was washed with methanol and suction filtered to obtain the product 9-bromo-10-benzanthracene. Yield 85%.

[0058] ③9-Bromo-10-Benzanthracene Boronate: Add 1.40g of 9-Bromo-10-Benzan...

Embodiment 2

[0062] ① Add 3.50g of 9-bromoanthracene, 2.52g of phenylboronic acid, 18.82g of potassium carbonate (add 45mL of water to form a solution), 136mL of toluene, and 45mL of ethanol into the reaction flask, and finally add 0.82g of tetrakis(triphenylphosphine) palladium. The system was evacuated and refluxed at 105° C. for 18 hours under nitrogen protection. After the reaction, the product was obtained by toluene extraction, rotary evaporation, column chromatography (eluent: n-hexane), and recrystallization (n-hexane / toluene=4:1). Yield 86%. ②9-Benzanthracene bromination: Add 3.50 g of 9-Benzanthracene, 130 mL of DMF, and 2.94 g of NBS into the reaction flask, then vacuumize the system, and react at 88°C for 1.5 h under the protection of nitrogen. After the reaction, the product was washed with methanol and filtered with suction to obtain the product 9-bromo-10-benzanthracene with a yield of 87%. ③Boronization of 9-bromo-10-benzanthracene: Add 2 g of 9-bromo-10-benzanthracene, ...

Embodiment 3

[0064] ①Add 5.14g of 9-bromoanthracene, 3.66g of phenylboronic acid, 27.64g of potassium carbonate (add 60mL of water to form a solution), 200mL of toluene, and 60mL of ethanol into the reaction flask, and finally add 1.16g of tetrakis(triphenylphosphine)palladium . Then the system was evacuated and refluxed at 110° C. for 24 hours under the protection of argon. After the reaction, the product was obtained by toluene extraction, rotary evaporation, column chromatography (eluent: n-hexane), and recrystallization (n-hexane / toluene=4:1). Yield 86%. ②9-Benzanthracene bromination: Add 4.29g of 9-benzanthracene, 200mL of DMF, and 3.6g of NBS into the reaction flask, then vacuumize the system, and react at 90°C for 2 hours under the protection of argon. After the reaction was completed, the product was washed with methanol and suction filtered to obtain the product 9-bromo-10-benzanthracene with a yield of 77%. ③9-Bromo-10-benzoanthracene boronate: Add 2.80g of 9-bromo-10-benzoant...

Technical field

[0001] The invention belongs to the field of organic electroluminescent diodes, and in particular relates to an organic blue fluorescent material and its preparation method and application.

Background technique

[0002] Since 1987, Organic Light-Emitting Diodes (OLEDs for short) have gradually become the industry-recognized next-generation flat panel display technology. Because of its advantages of active luminescence, low driving voltage, light and thin, wide luminous viewing angle, fast response, bendable and foldable, simple preparation process, low cost, and large-area production, it has great potential in the fields of full-color flat panel display and solid-state lighting. application prospects. At present, compared with the existing red and green organic electroluminescent materials and devices, blue organic electroluminescent materials and devices are always scarce. Relatively speaking, blue light materials have a wide energy gap, so it is diffi...

Examples

Embodiment 1

[0056] ①Add 2.60g of 9-bromoanthracene, 1.83g of phenylboronic acid, 13.82g of potassium carbonate (add 30mL of distilled water to make a 2.0M solution), 100mL of toluene, and 30mL of ethanol into the reaction flask, then add 0.58g of tetrakis(triphenylphosphine )palladium. Then vacuumize the system, and reflux at 100° C. for 12 hours under the protection of nitrogen. After the reaction, the product was obtained by toluene extraction, rotary evaporation, column chromatography (eluent: n-hexane), and recrystallization (n-hexane / toluene=4:1). Yield 86%.

[0057] ②Bromination of 9-benzoanthracene: Add 2.15g of 9-benzoanthracene, 100mL of DMF, and 1.80g of NBS into the reaction flask, then vacuumize the system, and react under nitrogen protection at 85°C for 1 hour. After the reaction, the product was washed with methanol and suction filtered to obtain the product 9-bromo-10-benzanthracene. Yield 85%.

[0058] ③9-Bromo-10-Benzanthracene Boronate: Add 1.40g of 9-Bromo-10-Benzan...

Embodiment 2

[0062] ① Add 3.50g of 9-bromoanthracene, 2.52g of phenylboronic acid, 18.82g of potassium carbonate (add 45mL of water to form a solution), 136mL of toluene, and 45mL of ethanol into the reaction flask, and finally add 0.82g of tetrakis(triphenylphosphine) palladium. The system was evacuated and refluxed at 105° C. for 18 hours under nitrogen protection. After the reaction, the product was obtained by toluene extraction, rotary evaporation, column chromatography (eluent: n-hexane), and recrystallization (n-hexane / toluene=4:1). Yield 86%. ②9-Benzanthracene bromination: Add 3.50 g of 9-Benzanthracene, 130 mL of DMF, and 2.94 g of NBS into the reaction flask, then vacuumize the system, and react at 88°C for 1.5 h under the protection of nitrogen. After the reaction, the product was washed with methanol and filtered with suction to obtain the product 9-bromo-10-benzanthracene with a yield of 87%. ③Boronization of 9-bromo-10-benzanthracene: Add 2 g of 9-bromo-10-benzanthracene, ...

Embodiment 3

[0064] ①Add 5.14g of 9-bromoanthracene, 3.66g of phenylboronic acid, 27.64g of potassium carbonate (add 60mL of water to form a solution), 200mL of toluene, and 60mL of ethanol into the reaction flask, and finally add 1.16g of tetrakis(triphenylphosphine)palladium . Then the system was evacuated and refluxed at 110° C. for 24 hours under the protection of argon. After the reaction, the product was obtained by toluene extraction, rotary evaporation, column chromatography (eluent: n-hexane), and recrystallization (n-hexane / toluene=4:1). Yield 86%. ②9-Benzanthracene bromination: Add 4.29g of 9-benzanthracene, 200mL of DMF, and 3.6g of NBS into the reaction flask, then vacuumize the system, and react at 90°C for 2 hours under the protection of argon. After the reaction was completed, the product was washed with methanol and suction filtered to obtain the product 9-bromo-10-benzanthracene with a yield of 77%. ③9-Bromo-10-benzoanthracene boronate: Add 2.80g of 9-bromo-10-benzoant...

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