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Conjugated compound containing 9,9-diimidazolyl thiaxanthene and preparation and application thereof

A technology of conjugated compound and diimidazole, which is applied in the field of electroluminescent materials to achieve the effects of improving physical properties, good reproducibility and improving device performance

Inactive Publication Date: 2019-01-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Up to now, most of the evaporation molecules used in organic optoelectronic devices have skeletons of sulfoxyfluorene, phosphorus oxide, triphenylamine and other units as the core, while organic light-emitting small molecules with 9,9-diimidazolyl thioxanthene as the core Molecules are rarely reported

Method used

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  • Conjugated compound containing 9,9-diimidazolyl thiaxanthene and preparation and application thereof
  • Conjugated compound containing 9,9-diimidazolyl thiaxanthene and preparation and application thereof
  • Conjugated compound containing 9,9-diimidazolyl thiaxanthene and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Dissolve 2-bromophenylphenylsulfide (11mmol, 2.93g) in 60ml of anhydrous THF, cool to -78°C, add n-BuLi (14.36mmol) dropwise, keep warm for 1 hour, and mix N,N '-Carbonyldiimidazole (10mmol, 3.38g) was dissolved in 30ml THF and added dropwise to the reaction system overnight. Extract with dichloromethane, dry, and pass through a silica gel column to obtain a white solid. The obtained product was directly added to glacial acetic acid, heated to reflux, and 15 ml of concentrated hydrochloric acid was added to form a solid precipitate, which was filtered by suction to obtain the white solid product M1 (2.7 g, yield 50%). 1 HNMR: 7.43-7.45 (d, 2H), 7.37-7.40 (d, 4H), 7.17-7.23 (m, 6H), 6.87-6.90 (d, 4H), 6.62-6.65 (d, 2H).

[0030] (2) Dissolve M1 (2.7g, 7.7mmol) in 50mL of glacial acetic acid and heat to reflux. Add 2 times molar equivalent of liquid bromine and react overnight. It was extracted with dichloromethane, washed with water, dried, and the solvent was rem...

Embodiment 2

[0035] (1) M2 (1.5mmol, 0.81g), carbazole (3.3ml, 0.57g), CuI (0.23g), K 2 CO 3 (0.55g), C 18 o 6 (0.1g) was dissolved in DMPU, heated at 180°C overnight, extracted with dichloromethane, dried, extracted, and passed through the column to obtain 0.83g of conjugated compound P1 containing 9,9-diimidazolylthioxanthene, yield 82% . 1HNMR:8.33-8.34(d,2H),8.14-8.16(d,4H),7.65-7.67(d,4H),7.56-7.58(d,4H),5.49-5.51(d,4H),7.41-7.44 (d, 4H), 7.29-7.31 (m, 6H), 7.17-7.18 (d, 4H).

[0036] (2) M3 (1.5mmol, 0.81g), carbazole (3.3ml, 0.57g), CuI (0.23g), K 2 CO 3 (0.55g), C 18 o 6 (0.1g) was dissolved in DMPU, heated at 180°C overnight, extracted with dichloromethane, dried, extracted, and passed through the column to obtain 0.83g of conjugated compound P2 containing 9,9-diimidazolylthioxanthene, yield 80% . 1 HNMR:8.85-8.84(d,2H),8.14-8.16(d,4H),7.65-7.67(d,4H),7.56-7.58(d,4H),5.49-5.51(d,4H),7.41-7.44 (d, 4H), 7.29-7.31 (m, 6H), 7.17-7.18 (d, 4H).

[0037] The reaction process ...

Embodiment 3

[0040] (1) M2 (1.5mmol, 0.81g), tert-butylcarbazole (3.3ml, 0.92g), CuI (0.23g), K 2 CO 3 (0.55g), C 18 o 6 (0.1g) was dissolved in DMPU, heated at 180°C overnight, extracted with dichloromethane, dried, extracted, and passed through the column to obtain 0.83g of conjugated compound P3 containing 9,9-diimidazolylthioxanthene, yield 82% .

[0041] (2) M3 (1.5mmol, 0.81g), carbazole (3.3ml, 0.57g), CuI (0.23g), K 2 CO 3 (0.55g), C 18 o 6 (0.1g) was dissolved in DMPU, heated at 180°C overnight, extracted with dichloromethane, dried, extracted, and passed through the column to obtain 0.83g of conjugated compound P4 containing 9,9-diimidazolylthioxanthene, yield 80% . 1 HNMR:8.85-8.84(d,2H),8.14-8.16(d,4H),7.65-7.67(d,4H),7.56-7.58(d,4H),5.49-5.51(d,4H),7.41-7.44 (d, 4H), 7.29-7.31 (m, 4H), 7.17-7.18 (d, 4H), 1.43 (d, 18H).

[0042] The reaction process of this embodiment is shown in the following formula:

[0043]

[0044]

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Abstract

The invention belongs to the technical field of electroluminescent materials and discloses a conjugated compound containing 9,9-diimidazolyl thiaxanthene and preparation and an application thereof. The conjugated compound containing 9,9-diphenyl thiaxanthene has a structural formula as shown in a formula 1 or a formula 2, wherein R1 and R2 are same or different aromatic rings formed by vinylene bases, ethynylene bases and carbon and hydrogen atoms with donor giving properties, aromatic rings formed by carbon, silicon and hydrogen atoms, C1-C24 alkyl, alkyl substituted conjugated units, alkoxylsubstituted conjugated units or alkyl and alkoxyl simultaneously substituted conjugate units. The compound has a fluorescent property, and can improve the external quantum efficiency of an apparatusobviously as an organic electroluminescent dioxide. The formula is as shown in the description.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a conjugated compound containing 9,9-diimidazolylthioxanthene and its preparation and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the OLED device developed by the 10V DC voltage drive had a luminous brightness of 1000cd / m 2 , so that OLED has achieved an epoch-making development. Over the past two decades, OLED devices employing novel emitters, especially organic-heavy metal complex phosphorescent emitters, have achieved considerable success. However, due to the difficult...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C07D413/14C07D417/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D409/14C07D413/14C07D417/14C09K2211/1044C09K2211/1092H10K85/636H10K85/631H10K85/654H10K85/6576H10K85/657H10K85/6572
Inventor 苏仕健刘坤坤彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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