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Phenylcarbazole spiro derivative and application thereof, organic electronic device, display device or lighting device

An organic electronic device, a technology of phenylcarbazole spiro, which is applied in the field of organic optoelectronic materials, can solve the problems affecting the application of organic electrophosphorescent devices, the efficiency roll-off of phosphorescent devices, and the reduction of external quantum efficiency, so as to improve device performance or efficiency. , Improved efficiency roll-off, excellent film formation and thermal stability

Pending Publication Date: 2022-07-01
维思普新材料(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current commercialized organic electroluminescent materials are divided into traditional fluorescent materials and phosphorescent materials, in which fluorescent materials can only use 25% of singlet excitons, and the remaining 75% of triplet excitons are lost through heat or other non-radiative means, while Phosphorescent materials can utilize 100% of excitons due to the heavy atom effect. Although the luminous efficiency is much higher than that of traditional fluorescent materials, most phosphorescent devices have a serious efficiency roll-off, that is, at lower brightness or lower current density. With the maximum efficiency, as the brightness or current density increases, the external quantum efficiency of the device generally decreases severely and is restricted by the price of precious metals
This undoubtedly increases the cost of the device and affects the application of organic electrophosphorescent devices in lighting and full-color display.

Method used

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  • Phenylcarbazole spiro derivative and application thereof, organic electronic device, display device or lighting device
  • Phenylcarbazole spiro derivative and application thereof, organic electronic device, display device or lighting device
  • Phenylcarbazole spiro derivative and application thereof, organic electronic device, display device or lighting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of Compound 1-1

[0032] The structural formula and synthetic route of compound 1-1 are shown in the following figure:

[0033]

[0034] The preparation method of the compound of formula M1 is as follows: 2.8g (16.8mmol) of carbazole, 11.6g (67.2mmol) of 1-bromo-2-fluorobenzene, 10.9g (33.5mmol) of cesium carbonate and 120mL of N are successively added to a 250mL two-necked flask, N-dimethylformamide was heated to 150°C with stirring for 24 hours. After the reaction was completed, the system was cooled to room temperature, poured into water, filtered under reduced pressure, and the filter residue was washed with a large amount of water. After separation and purification, 4.9 g of M1 was obtained with a yield of 90.8%. MS (ET): m / z 321.05 [M+]. Elemental analysis calculated value C 18 H 12 BrN (%): C, 67.10; H, 3.75; N, 4.35; found: C, 67.05; H, 3.70; N, 4.25.

[0035] The preparation method of compound 1-1 is as follows: under nitrogen prot...

Embodiment 2

[0036] Example 2: Synthesis of Compound 1-2

[0037] The structural formula and synthetic route of compound 1-2 are shown in the following figure:

[0038]

[0039] The preparation method of the compound of formula M2 is as follows: 2.3g (5.5mmol) 3,6-diiodocarbazole, 3.8g (22.0mmol) 1-bromo-2-fluorobenzene, 3.6g (11.0mmol) 3.6g (11.0mmol) are successively added to a 250mL two-necked flask ) Cesium carbonate and 120 mL of N,N-dimethylformamide were stirred and heated to 150° C. to react for 24 hours. After the reaction was completed, the system was cooled to room temperature, poured into water, filtered under reduced pressure, and the filter residue was washed with a large amount of water. After separation and purification, 2.9 g of M2 was obtained with a yield of 92.0%. MS (EI): m / z 572.75 [M+]. Elemental analysis calculated value C 18 H 10 BrI 2N (%): C, 37.67; H, 1.76; N, 2.44; found: C, 37.60; H, 1.75; N, 2.40.

[0040] The preparation method of the compound of f...

Embodiment 3

[0042] Example 3: Synthesis of Compounds 1-3

[0043] The structural formulas and synthetic routes of compounds 1-3 are shown in the following figure:

[0044]

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Abstract

The invention provides a phenylcarbazole spiro derivative, an organic electronic device, a display device or a lighting device, and the phenylcarbazole spiro derivative has excellent film-forming property, thermal stability and photoelectric property through a molecular configuration and molecular orbital characteristics formed by matching a parent nucleus overall structure and branched chains of the phenylcarbazole spiro derivative. The compound can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells. In addition, the phenylcarbazole spiro derivative can be used as a constituent material of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, a hole blocking layer and an electron transport layer of an electronic device, and can reduce driving voltage, improve efficiency, brightness, prolong the service life and the like. More importantly, the phenylcarbazole spiro compound can effectively isolate donor and acceptor groups, and is an ideal skeleton for constructing a thermally activated delayed fluorescent material. The preparation method of the phenylcarbazole spiro derivative is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The invention relates to a phenylcarbazole spiro ring derivative and its application, an organic electronic device, a display device or a photo device, and belongs to the technical field of organic optoelectronic materials. Background technique [0002] An organic light-emitting diode (OLED) is a self-luminous device. By applying a voltage, electrons injected from the cathode and holes injected from the anode recombine at the luminescent center to form molecular excitons, and the molecular excitons release energy when they return to the ground state. glow. Organic electroluminescent devices have the characteristics of low turn-on voltage, high brightness, wide color gamut, high color purity, wide viewing angle, fast response, good temperature adaptability, etc., and can be widely used in mobile phone, computer, MP3, TV and other electronic product displays. [0003] Currently commercial organic electroluminescent materials are divided into traditional...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10C09K11/06H01L51/30H01L51/46H01L51/54
CPCC07D471/10C09K11/06C09K2211/1029C09K2211/1007C09K2211/1014C09K2211/1033C09K2211/1037H10K85/636H10K85/657H10K85/6572
Inventor 朱向东袁晓冬陈华
Owner 维思普新材料(苏州)有限公司
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