Carbazolyl-based organic electroluminescence compound

A compound and luminescent technology, applied in organic chemistry, luminescent materials, circuits, etc., can solve the problems of reduced probability of electron and hole recombination, poor carrier transport performance, and reduced device luminous efficiency, so as to improve luminescence Efficiency and life, satisfying the effect of high preparation efficiency and good electron transport performance

Inactive Publication Date: 2013-05-08
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The main reasons for this situation are: on the one hand, the triplet state energy level of the blue phosphorescent host material is not high enough, which causes the energy return from the guest to the host, thereby reducing the luminous efficiency of the device; on the other hand, the dark blue phosphorescent host material Poor carrier transport performance reduces electron and hole recombination probability and reduces device efficiency

Method used

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  • Carbazolyl-based organic electroluminescence compound
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  • Carbazolyl-based organic electroluminescence compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Dissolve 10.032g of carbazole and 7.3191g of 1,6-dibromohexane in 90ml of tetrahydrofuran in turn, add 0.192g of catalyst tetrabutylammonium bromide under nitrogen protection, stir and mix evenly, add 16mol / L of potassium hydroxide The solution was 40ml, warmed up to reflux, and reacted for 12h. After the reaction, extract the organic layer with dichloromethane, dry over magnesium sulfate, concentrate the solution by rotary evaporation, apply to a silica gel chromatography column, rinse with petroleum ether, evaporate the eluent, and recrystallize and purify with ethanol to obtain white needles 1, 6-dicarbazolylhexane (hCP) crystals.

[0046]

[0047] [0040] by 1 The structures of the obtained compounds were characterized by HNMR and FT-IR, figure 1 middle 1 HNMR (CDCl 3 , 600MHz)δ: 1.3881(m, 4H), 1.8309(m, 4H), 4.2439(td, 4H), 7.2194(ts, 4H), 7.32665(d, 4H), 7.4194(td, 4H), 8.0934(d , 4H); figure 2 Medium FT-IR (KBr): 3445, 2926, 2852, 2360, 1626, 1456, 75...

Embodiment 2

[0065] Dissolve 11.72g of 3,6-dimethylcarbazole and 7.3191g of 1,6-dibromohexane in sequence in 90ml of tetrahydrofuran, add 0.192g of catalyst tetrabutylammonium bromide under nitrogen protection, stir and mix evenly, add 40ml of 16mol / L potassium hydroxide solution was heated to reflux and reacted for 12h. After the reaction, extract the organic layer with dichloromethane, dry over magnesium sulfate, concentrate the solution by rotary evaporation, apply to a silica gel chromatography column, rinse with petroleum ether, evaporate the eluent, and recrystallize and purify with ethanol to obtain white needles 1, 6-bis(4,7-dimethylcarbazolyl)hexane (mhCP) crystals.

[0066]

[0067] The mhCP obtained by the reaction was dissolved in a mixed solution of dichloromethane and petroleum ether with a volume ratio of 1:2, and left for 48 hours to obtain a white needle-like transparent single crystal.

Embodiment 3

[0069] Dissolve 13.39g of 3,6-diethylcarbazole and 7.3191g of 1,6-dibromohexane in sequence in 90ml of tetrahydrofuran, add 0.192g of tetrabutylammonium bromide, stir and mix well, then add 16mol / L of hydrogen Potassium oxide solution 40ml, reflux reaction 12h, above-mentioned operations are all carried out under nitrogen protection. After the reaction, extract the organic layer with dichloromethane, dry over magnesium sulfate, concentrate the solution by rotary evaporation, apply to a silica gel chromatography column, rinse with petroleum ether, evaporate the eluent, and recrystallize and purify with ethanol to obtain white needles 1, 6-bis(4,7-diethylcarbazolyl)hexane (ehCP) crystals.

[0070]

[0071] [0056] The ehCP obtained by the reaction was dissolved in a mixed solution of dichloromethane and petroleum ether with a volume ratio of 1:2, and left for 48 hours to obtain a white needle-like transparent single crystal.

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Abstract

The invention discloses a carbazolyl-based organic electroluminescence compound which has the structural general formula shown by formula (I), wherein R is H, CH3 or CH2CH3. The organic electroluminescence compound disclosed by the invention is used as phosphorescent host material in an organic electrophosphorescent device, and has good electronic transmission characteristic and thermal stability; and meanwhile, the host material has relatively high triplet state energy level and can effectively prevent back transfer of triplet state energy so as to improve the luminous efficiency and prolong the service life of the organic electrophosphorescent device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and relates to a carbazole-based organic electroluminescent material. The invention also relates to an organic electroluminescence device made by using the compound. Background technique [0002] Phosphorescent organic-light emitting device (PhOLED: Phosphorescent organic-light emitting device) can capture triplet and singlet excitons at the same time, so its internal quantum efficiency breaks the theoretical limit of 25% of traditional fluorescent OLEDs, making 100% internal quantum efficiency become possible. In PhOLED, due to the quenching effect of the guest material—the phosphorescence emitting material, it can only be doped in the host material as the emitting layer. Compared with other materials, the lack of deep blue phosphorescent host materials has seriously restricted the development of OLEDs and has become a bottleneck for the industrialization of OLEDs....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/54
Inventor 许并社杨婷婷许慧侠王华苗艳勤武钰铃杜晓刚景姝
Owner TAIYUAN UNIV OF TECH
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