Micromolecular host material based on D-R-A as well as preparation method and applications thereof

A host material and small molecule technology, applied in the field of D-R-A-based small molecule host material and its preparation, can solve the problems of device performance degradation and annihilation

Inactive Publication Date: 2014-07-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While typical phosphorescent emitters have long lifetimes and can diffuse over longer distances, resulting in potential concentration quenching and triplet-triplet (T 1 -T 1 ) annihilation, which eventually leads to the performance degradation of the device

Method used

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  • Micromolecular host material based on D-R-A as well as preparation method and applications thereof
  • Micromolecular host material based on D-R-A as well as preparation method and applications thereof
  • Micromolecular host material based on D-R-A as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Step 1: Preparation of 2-(3,6-dibromocarbazol-9-yl)ethanol (a1)

[0059]

[0060] Under nitrogen atmosphere, add potassium hydroxide (KOH) (10.52g, 187.5mmol), 60ml DMF, 3,6-dibromocarbazole (9.76g, 30.0mmol) into a 250ml three-necked flask, stir for 30min, and use a syringe 2-Bromoethanol (2.4ml, 31.5mmol) was added dropwise, the mixture was heated to 155°C and reacted overnight. After cooling to room temperature, add an appropriate amount of water to quench the reaction, dilute with dichloromethane (DCM), separate the liquids to obtain an organic phase, extract the water phase with DCM 3 times, combine the organic phases, and wash the organic layer 3 times with saturated brine . Dry over anhydrous magnesium sulfate, filter with suction, remove the solvent from the obtained filtrate under reduced pressure; column separation (9.15g, 24.8mmol) white solid. Yield 82.7%. 1 H NMR (300MHz, CDCl 3 ), (ppm):8.14(s,2H),7.57-7.54(d,2H),7.35-7.32(d,2H),4.42(t,2H),4.03(t,...

Embodiment 2

[0068] Step 1: Preparation of 6-(3,6-dibromocarbazol-9-yl)-hexan-1-ol (b1)

[0069]

[0070] Under a nitrogen atmosphere, add KOH (10.5g, 187.5mmol), 60mlDMF, 3,6-dibromocarbazole (9.75g, 30.0mmol) into a 250ml three-necked flask, stir for 30min, and add 6- Chlorohex-1-ol (4.4ml, 31.5mmol), the mixture was heated to 155°C and reacted overnight. After cooling to room temperature, an appropriate amount of water was added to quench the reaction, diluted with DCM, and separated to obtain an organic phase. The aqueous phase was extracted three times with DCM, the organic phases were combined, and the organic layer was washed three times with saturated brine. Dry over anhydrous magnesium sulfate, filter with suction, remove the solvent from the filtrate under reduced pressure; column separation (6.36g, 15.0mmol) white solid. Yield 50.0%. 1 H NMR (300MHz, CDCl 3 ), (ppm):8.14(s,2H),7.55(d,2H),7.28-7.25(d,2H),4.25(t,2H),3.62(t,2H),1.90-1.80(m,2H), 1.60-1.50(m,2H),1.40(m,4H). ...

Embodiment 3

[0078] Step 1: Preparation of 3,6-dibromo-9-(6-bromohexyl)-9H-carbazole (C1)

[0079]

[0080] Under a nitrogen atmosphere, sodium hydride (NaH) (1.44 g, 60 mmol) was added to a three-necked flask equipped with 80 ml of anhydrous THF, and then 3,6-dibromocarbazole (9.75 g, 30.0 mmol) was slowly added, and again Add 1,6-dibromohexane (22.0 g, 90.0 mmol) gradually, heat the mixture to reflux, and react overnight. After cooling to room temperature, it was poured into water, diluted with DCM, and separated to obtain an organic phase. The aqueous phase was extracted 3 times with DCM, the organic phases were combined, and the organic layer was washed 3 times with saturated brine. Dry over anhydrous magnesium sulfate, filter with suction, remove the solvent from the filtrate under reduced pressure; column separation (4.63g, 9.49mmol) white solid. Yield 31.6%. 1 H NMR (300MHz, CDCl 3 ), (ppm):8.14(s,2H),7.55(d,2H),7.28-7.25(d,2H),4.26(t,2H),3.36(t,2H),1.91-1.76(m,4H), 1.50-1....

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Abstract

The invention discloses a micromolecular host material based on D-R-A. According to the micromolecular host material, an electrophilic diphenylphosphine oxide group serves as an electron acceptor unit, carbazole or triphenylamine serves as an electron donor unit, and the electron acceptor unit and the electron donor unit are isolated from each other by an insulating alkyl chain. The invention also discloses a preparation method and applications of the micromolecular host material based on D-R-A. The micromolecular host material based on D-R-A has excellent bipolar transmission performance, very good solubility and film-forming performance, and has great potential when serving as a host material of a light emitting layer.

Description

technical field [0001] The invention relates to a D-R-A type organic small molecule material, in particular to a D-R-A-based small molecule host material and its preparation method and application. Background technique [0002] Since OLEDs were first reported by Dr. Qingyun Deng et al. in 1987, there have been more than 20 years of research and development in the field of organic optoelectronics. Because of the advantages of self-luminescence, fast response time, wide viewing angle, high contrast ratio and light weight of OLEDs, OLEDs show very attractive application prospects in the next generation of flat panel displays and white lighting. In recent years, researches based on OLEDs have mainly focused on high efficiency and long lifetime of the devices. According to the spin quantum statistical theory, under electric field excitation, the ratio of singlet and triplet exciton formation is roughly 1:3, so the efficiency of conventional fluorescent OLEDs is limited to 25%. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558H01L51/54
Inventor 苏仕健叶华周凯锋曹镛
Owner SOUTH CHINA UNIV OF TECH
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