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An organic small molecule material based on spirothioxanthene and an organic photoelectric device using the material as a light-emitting layer

A technology of optoelectronic devices and small molecules, applied in the direction of electric solid devices, electrical components, luminescent materials, etc., can solve the problems of organic small molecule materials that are rarely reported, and achieve the effect of improving carrier transport characteristics and good solubility

Active Publication Date: 2017-04-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, although there have been many reports on organic small molecule materials used in organic electroluminescent devices, there are few reports on organic small molecule materials with a spirothioxanthene structure as the core.

Method used

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  • An organic small molecule material based on spirothioxanthene and an organic photoelectric device using the material as a light-emitting layer
  • An organic small molecule material based on spirothioxanthene and an organic photoelectric device using the material as a light-emitting layer
  • An organic small molecule material based on spirothioxanthene and an organic photoelectric device using the material as a light-emitting layer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of present embodiment intermediate 1 and 2:

[0034] Synthesis of 2-bromodiphenylsulfide: o-bromoiodobenzene (50mmol, 14.3g), diphenyldisulfide (16.625mmol, 3.40g), Cu 2 S(1.194g), Fe(1.05g), K 2 CO 3 (8.625g) was dissolved in 125ml of DMSO, heated to 120°C overnight to obtain 2-bromodiphenylsulfide (3.84g), yield 93%. 1H NMR: 7.55-7.59 (m, 1H), 7.36-7.48 (m, 5H), 7.13-7.18 (m, 1H), 7.01-7.07 (m, 1H), 6.92-6.96 (m, 1H). The reaction equation is as follows:

[0035]

[0036] Synthesis of Intermediates 1 and 2: Dissolve 2-bromodiphenylsulfide (11mmol, 2.93g) in 60ml of anhydrous THF, cool to -78°C, add n-BuLi (14.36mmol) dropwise, and keep warm for 1 hour , Dissolve 4,4'-dibromobenzophenone (10mmol, 3.38g) in 30ml THF, add to react overnight, extract with dichloromethane, and pass through a silica gel column. White solid a (2.35g) was obtained with a yield of 53%; the white solid a (4.46mmol, 2.35g) was directly added to glacial acetic acid, heated...

Embodiment 2

[0039] In this embodiment, the preparation of a spirothioxanthene-based organic small molecule material having the structural formula P5:

[0040] Intermediate 2 (1.5mmol, 0.81g) obtained in Example 1, carbazole (3.3mmol, 0.57g), CuI (0.23g), K2CO3 (0.55g), C18O6 (0.1g), were dissolved in 1,3 -Dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone (DMPU), heated to 180°C overnight, extracted with dichloromethane, passed through a silica gel column to obtain 0.78g P5, yield 90% . 1H NMR: 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).

[0041] The absorption and emission spectrograms of the P5 of the present embodiment in the thin film state are as follows figure 1 As shown, from the absorption edge wavelength λ=358nm of the film, according to the formula optical band gap Eg opt =1240 / λ learned, Eg opt = 3.46eV.

Embodiment 3

[0043] In this embodiment, the preparation of a spirothioxanthene-based organic small molecule material having the structural formula P6:

[0044]Intermediate 1 (1.5mmol, 0.81g) obtained in Example 1, carbazole (3.3ml, 0.57g), CuI (0.23g), K2CO3 (0.55g), C18O6 (0.1g), were dissolved in DMPU, Heated at 180°C overnight, extracted with dichloromethane, and passed through the column to obtain 0.83g of P6. The yield was 82%. 1H NMR: 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).

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Abstract

The invention belongs to the technical field of photoelectric materials, and in particular relates to an organic small molecule material based on spiro-thioxanthene and an organic photoelectric device using the material as a light-emitting layer. The small organic molecule material takes spirothioxanthene as a skeleton unit, and obtains the target compound through Friedel-Crafts reaction or Ullmann reaction. This type of material has a single structure, a certain molecular weight, and has good solubility and film-forming properties in common solvents; the spiral structure of the material of the present invention can adjust the packing mode between molecules, thereby effectively inhibiting the light emission of exciplexes. The development of high-efficiency devices has far-reaching significance; organic optoelectronic devices using this material as the light-emitting layer have good light-emitting properties and can be applied to organic small molecule light-emitting diodes.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to an organic small molecule material based on spiro-thioxanthene and an organic photoelectric device using the material as a light-emitting layer. Background technique [0002] In the past two decades, 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. [0003] Organic electroluminescence is mainly divided into fluorescence and phosphorescence, but according to the spin quantum st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/04C07D409/10C07D409/14C07F9/6553C09K11/06H01L51/54
CPCC07D409/04C07D409/10C07D409/14C07F9/655372C09K2211/1029C09K2211/1014C09K2211/1007C09K2211/1092H10K85/6576H10K85/6572
Inventor 苏仕健刘坤坤刘明彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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