Organic photoelectric material based on nitrogen-heterocyclic molecules substituted by carbazole derivatives and preparation method and application of organic photoelectric material

A technology of organic optoelectronic materials and carbazole derivatives, which can be used in organic chemistry, circuits, electrical components, etc., and can solve the problems of ineffective use of triplet exciton energy, low exciton radiation deactivation rate, and weak coupling effect. , to achieve the effect of simple structure, strong electrochemical stability and stable performance

Inactive Publication Date: 2019-04-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The spin-orbit coupling of most organic light-emitting materials is weak, making T 1 The radiative deactivation rate of excitons is very low, making exciton quenching prone to loss of luminescence
For traditional fluorescent materials, the energy of the 75% triplet excitons cannot be effectively utilized, resulting in a theoretical external quantum efficiency of only about 5%.

Method used

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  • Organic photoelectric material based on nitrogen-heterocyclic molecules substituted by carbazole derivatives and preparation method and application of organic photoelectric material
  • Organic photoelectric material based on nitrogen-heterocyclic molecules substituted by carbazole derivatives and preparation method and application of organic photoelectric material
  • Organic photoelectric material based on nitrogen-heterocyclic molecules substituted by carbazole derivatives and preparation method and application of organic photoelectric material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] In this embodiment, intermediate a is first prepared, and the specific synthesis steps are shown in the following formula:

[0046]

[0047] in N 2 Atmosphere and a low temperature environment of -78°C, in a 100mL three-necked flask, 2.03g (10mmol) of 5-bromo-2-fluoro-1,3-dimethylbenzene was dissolved in 60mL of anhydrous tetrahydrofuran THF, and then 6.0 mL of 2.5 mol / L n-butyllithium (n-hexane as solvent) was added dropwise, and the system was kept at -78°C and stirred for 1 h. Afterwards, 4.1 mL (20 mmol) of isopropanol pinacol borate was slowly added to the reaction system, and the reaction was continued to be stirred at -78°C for 1 h, and then the system was returned to room temperature for overnight reaction. After the reaction was completed, THF was removed by rotary evaporation, extracted several times with dichloromethane DCM and water, the organic phase was taken out, excess DCM was removed by rotary evaporation, and 1.75 g of intermediate a was obtained b...

Embodiment 2

[0055] The organic photoelectric material P2 based on nitrogen heterocyclic molecules substituted by carbazole derivatives, the specific synthesis steps are shown in the following formula:

[0056]

[0057] The 3,6-di-tert-butylcarbazole used in the preparation of P1 in Example 1 was replaced with 999.94 mg (4.4 mmol) of equivalent 3,6-dimethoxycarbazole, and the rest of the raw materials and steps were the same as in Example 1. Likewise, 1.22 g of product P2 can be obtained with a yield of 75%. Molecular formula: C 54 h 46 N 4 o 4 ; M / Z=814.35; m / s=814.35 (100.0%), 815.36 (58.4%), 816.36 (16.7%), 817.36 (2.3%); Elemental analysis: C, 79.58; H, 5.69; N, 6.87; O, 7.85.

Embodiment 3

[0059] Firstly, intermediate B is prepared, and the specific synthesis steps are shown in the following formula:

[0060]

[0061] The 4,6-dichloro-2-phenylpyrimidine used in the preparation of A intermediate in Example 1 was replaced by an equivalent of 2,4-dichloro-6-phenyl-1,3,5-triazine 565.15mg (2.5mmol), all the other raw materials and steps are the same as in Example 1, and 883mg of intermediate B can be obtained with a yield of 88%. Molecular formula: C 25 h 21 f 2 N 3 ; M / Z=401.17; m / s=401.17 (100.0%), 402.17 (27.0%), 403.18 (2.7%), 402.17 (1.1%); Elemental analysis: C, 74.80; H, 5.27; F, 9.46; N, 10.47.

[0062] The organic photoelectric material P3 based on nitrogen heterocyclic molecules substituted by carbazole derivatives, the specific synthesis steps are shown in the following formula:

[0063]

[0064] The A intermediate used in the preparation of P1 in Example 1 was replaced by an equivalent of 802.92 mg (2 mmol) of B intermediate, and the rest of ...

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Abstract

The invention discloses an organic photoelectric material based on nitrogen-heterocyclic molecules substituted by carbazole derivatives. A nitrogen heterocyclic ring is taken as a receptor unit, different kinds of carbazole derivative groups are connected at different positions, luminescent molecules with different molecular structures are obtained, and an alkyl group or an alkoxy group is introduced into the joint between a benzene ring and a donor. The invention further discloses a preparation method and application of the organic photoelectric material. The organic photoelectric material has the advantages that the molecular weight is determined, the structure is single, the decomposition temperature is higher, the electrochemical stability is higher, it can be ensured that the materialhas a high enough T1 energy level, which is very beneficial for the stability of the luminescence performance of electrically driven devices such as an organic light-emitting diode under the condition of high brightness, and the organic photoelectric material can be effectively applied in the organic light emitting diodes.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to an organic photoelectric material based on nitrogen heterocyclic molecules substituted by carbazole derivatives and its preparation method and application. Background technique [0002] Since the beginning of the 21st century, OLED display technology has been gradually promoted and applied to commercial fields such as mobile phones and tablets, as well as TVs, digital cameras, and portable devices, gradually accumulating competitive advantages that can compete with the LCD industry. In OLEDs devices, it is predicted based on simple data statistics: only 25% of the injected charges can generate singlet excitons (S 1 ), leading to the generation of fluorescence (S 1 →S 0 ), while the remaining 75% of the injected charges generate triplet excitons (T 1 ), which can be used to generate phosphorescence (T 1 →S 0 ). The spin-orbit coupling of most organic li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D403/14H01L51/54
CPCC07D403/10C07D403/14H10K85/654H10K85/6572
Inventor 苏仕健蔡成松李彬彬
Owner SOUTH CHINA UNIV OF TECH
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