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Aromatic compound and organic light-emitting display device

A technology of aromatic compounds and heteroaryl groups, applied in the field of organic electroluminescent materials, to achieve the effect of improving solution processability, improving solubility, and small FWHM

Active Publication Date: 2018-12-14
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few TADF materials have been found so far, so it is urgent to develop new TADF materials that can be used in OLED devices.

Method used

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  • Aromatic compound and organic light-emitting display device
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  • Aromatic compound and organic light-emitting display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Synthesis of intermediate S2

[0105]

[0106] At room temperature, add 20ml of concentrated sulfuric acid to a 50ml single-necked flask, then add 6mL of bromobenzene S1 (57mmol), stir at room temperature for half an hour to obtain a white turbid liquid, then add 1.0g of mercaptosalicylic acid (6.5 mmol). Stir at room temperature for 24 hours, then heat at 100°C for 2-3 hours, after cooling to room temperature, carefully pour into ice water, filter with suction to obtain a solid, then add 20% NaOH aqueous solution, stir for 2 hours, filter with suction, wash with water until neutral, and get Yellow solid S2 (5.2 mmol, 80%).

[0107] 1 H NMR (400MHz, CDCl 3 , ppm): 7.70-7.90 (s, 2H), 7.40-7.60 (m, 4H), 7.30 (m, 1H). MALDI-TOF MS: m / z calcd for C 13 h 7 BrOS: 289.9; found: 290.0

[0108] Synthesis of intermediate S3

[0109]

[0110] At room temperature, add 40mL glacial acetic acid and 20mL dichloromethane to a 50mL single-necked flask, add raw material int...

Embodiment 2

[0124]

[0125] Under the condition of nitrogen protection, weigh S8 (20mmol), add 60mL of acetic acid, and add 24mmol of liquid bromine dropwise under the condition of stirring, and stir the resulting mixed solution at 80°C for 5h. Use NaHSO 3 The excess bromine element was quenched with aqueous solution, extracted with dichloromethane (100mL×3), the organic phase was collected, and washed with anhydrous Na 2 SO 4 Dry processing. After filtration, the solvent was distilled off under reduced pressure with a rotary evaporator to obtain a crude product. The crude product was purified by gradient elution of silica gel column chromatography, and finally purified by recrystallization from n-hexane to obtain solid powder S9 (16.8 mmol, 84%).

[0126] MALDI-TOF MS: m / z calcd for C 12 h 7 BrS 2 :293.9; found: 293.8

[0127]

[0128] At room temperature, add 40mL glacial acetic acid and 20mL dichloromethane into a 50mL single-necked flask, add raw material intermediate S9 ...

Embodiment 3

[0142]

[0143] S13 (8mmol), S7 (10.5mmol), (dibenzylideneacetone) dipalladium (0) (0.05mmol), sodium tert-butoxide (14mmol), 4,5-bisdiphenylphosphine-9,9 - Dimethylxanthene (0.2 mmol) was put into a 50 mL three-necked flask, and while stirring, degassing and nitrogen replacement were repeated three times rapidly, and 20 mL of toluene was added through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain intermediate S14 (5.3 mmol, 66%).

[0144] MALDI-TOF MS: m / z calcd for C 33 h 38 BrN: 527.2; found: 527.5

[0145]

[0146] In a 250ml three-necked flask, first mix S14 (30mmol), pinacol diborate (36mmol), (1,1'-bis(diphenylphosphino)ferrocene)dichl...

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Abstract

The invention relates to an aromatic compound having thermally activated delayed fluorescence (TADF) properties. The aromatic compound has a structure of formula (I), wherein D is an electron donor; Ais an electron acceptor; R10 and R20 each is cycloalkyl; m and n are respectively the number of electron donors D and electron acceptors A attached to formula (I); d and e are respectively the numberof substituents R10 and R20; f is the number of parent nuclear phenyls; f is 1 or 2; d and e are respectively 1 or 2; m and n are respectively 1, 2 or 3; when f = 1, m + n + d + e is less than or equal to 6; and when f = 2, m + n + d + e is less than or equal to 10. The aromatic compound provided by the invention has a light-emitting mechanism of TADF, has high light-emitting efficiency, can increase the light-emitting efficiency of an organic light-emitting display device when the aromatic compound is as a light-emitting material, a light-emitting subject material or object material appliedto the organic light-emitting display device, and has the advantages of relatively low cost and longer service life. The invention also provides the organic light-emitting display device.

Description

technical field [0001] The invention relates to the field of organic electroluminescence materials, in particular to a cycloalkyl-containing aromatic compound material with thermally activated delayed fluorescence (TADF) performance and the application of the material in organic light-emitting display devices. Background technique [0002] With the development of electronic display technology, OLED is widely used in various display devices, and the research and application of OLED light-emitting materials are also increasing. [0003] According to the light-emitting mechanism, there are four main types of OLED light-emitting layer materials: [0004] (1) fluorescent material; (2) phosphorescent material; (3) triplet-triplet annihilation (TTA) material 0; (4) thermally activated delayed fluorescence (TADF) material. [0005] For fluorescent materials, according to spin statistics, the ratio of singlet and triplet excitons in excitons is 1:3, so the maximum internal quantum y...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C07D219/02C07D409/10H01L51/54
CPCC09K11/06C07D219/02C07D409/10C07F5/027C09K2211/1092C09K2211/1029C09K2211/1007C09K2211/1014H10K85/6576H10K85/6572
Inventor 高威王湘成张磊牛晶华刘营邓东阳罗学强安平黄高军
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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