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General formula compound and organic electroluminescent device

A general formula compound, organic technology, applied in the field of organic compounds, can solve the problems of high driving voltage, unfavorable carrier injection and transport balance, lack of host materials, etc.

Inactive Publication Date: 2019-04-02
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, high-efficiency red light-emitting devices are rare, mainly due to the lack of suitable host materials.
[0004] At present, the host material widely used in red phosphorescent devices is CBP, but it requires a higher driving voltage, Tg=62°C, and is easy to crystallize
In addition, CBP is a p-type material, and the hole mobility is much higher than the electron mobility, which is not conducive to the balance of carrier injection and transport.
[0005] However, there is still much room for improvement in the luminescence performance of existing organic electroluminescent materials, and the industry urgently needs to develop new organic electroluminescent materials

Method used

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  • General formula compound and organic electroluminescent device
  • General formula compound and organic electroluminescent device
  • General formula compound and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0060] Synthesis Example 1: Synthesis of Intermediate M1

[0061]

[0062] In a 250ml three-necked flask, add 1.0g of compound A, 1.2g of compound B, Pd 2 (dba) 3 0.04g, 0.75g of sodium tert-butoxide, 0.02g of tri-tert-butylphosphine tetrafluoroborate and 30ml of xylene, pump nitrogen gas three times, heat up to reflux temperature under the protection of nitrogen gas, and cool down to room temperature after reacting overnight. Diluted with toluene, passed through a silica gel column, and recrystallized with toluene to obtain 1.4 g of a yellow solid with a yield of 80%. MS (m / e): 456, 1 H NMR (300MHz, CDCl 3 ): 8.56(1H), 8.43(2H), 8.11(2H), 8.13(1H), 8.00(2H), 7.95(1H), 7.90(1H), 7.64(2H), 7.61(2H), 7.57(1H ), 7.34(1H), 7.32(1H), 7.30(1H), 7.28(1H), elemental analysis: C(89.5%), N(6.2%), H(4.3%).

Synthetic example 2

[0063] Synthesis Example 2: Synthesis of Compound P1

[0064]

[0065] Into a 250ml three-necked flask, add 1.0g of compound M1, 0.58g of compound C, 0.91g of potassium carbonate and 30ml of DMF, pump nitrogen three times, raise the temperature to 130°C under the protection of nitrogen, and react overnight, then cool down to room temperature, and the reaction solution Pour into water to precipitate a precipitate, filter the precipitate, dissolve the filter cake in toluene, pass through a silica gel column, and recrystallize with toluene to obtain 1.2 g of a bright yellow solid, MS (m / e): 660, yield 80%. MS (m / e): 456, 1 H NMR (300MHz, CDCl 3 ): 8.56(2H), 8.43(2H), 8.16(1H), 8.11(2H), 8.06(2H), 7.95(4H), 7.80(4H), 7.64(1H), 7.61(2H), 7.52(2H ), 7.42(1H), 7.34(2H), 7.32(1H), 7.28(2H), elemental analysis: C(87.3%), N(8.5%), H(4.2%).

Synthetic example 3

[0066] Synthesis Example 3: Synthesis of Compound P11

[0067]

[0068] The preparation method was the same as P1, except that compound C was replaced by compound D to obtain 1.0 g of a bright yellow solid product with a yield of 81%. MS(m / s): 584, 1 H NMR (300MHz, CDCl 3 ): 9.75(1H), 8.56(2H), 8.43(2H), 8.16(1H), 8.11(2H), 8.06(2H), 7.95(4H), 7.80(2H), 7.64(1H), 7.61(2H ), 7.34(2H), 7.32(1H), 7.28(2H), elemental analysis: C(86.3%), N(9.6%), H(4.1%).

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PUM

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Abstract

The present invention relates to a compound represented by the formula (I) shown in the specification. In the formula (I), R is selected from the formula (II) or (III) shown in the specification, in the formula (II), P and Q are each independently selected from C or N, and at least one of P and Q is N; Ra represents mono-, di-, tri-, tetra-or non-substituted, and any two adjacent Ra are optionallyjoined, and R1 is optionally bonded to an adjacent Ra; Ra and R1 are each independently selected from hydrogen, C1-C10 alkyl group, C6-C30 arylamine group, substituted or unsubstituted C6-C30 aryl group or fused ring aromatic hydrocarbon group, and substituted or unsubstituted C3 to C30 heteroaryl or fused heterocyclic aromatic hydrocarbon group. In formula (III), X, Y and Z are each independently selected from C or N, wherein at least one of the X, Y and Z is N; and R2 and R3 are each independently selected from hydrogen, C1-C10 alkyl, halogen, C6-C30 arylamine group, substituted or unsubstituted C6-C30 aryl group or fused ring aromatic hydrocarbon group, and substituted or unsubstituted C3 to C30 heteroaryl or fused heterocyclic aromatic hydrocarbon group. The invention further relatesto an organic electroluminescent device employing the compound of the formula (I).

Description

technical field [0001] The invention relates to an organic compound, which can be used as a host material for a light-emitting layer of an organic electroluminescent device; the invention also relates to the application of the compound in an organic electroluminescent device. Background technique [0002] At present, with the continuous advancement of OLED technology in the two major fields of lighting and display, people are paying more attention to the research on its core materials. An organic electroluminescent device with high efficiency and long life is usually the result of an optimized combination of device structure and various organic materials. As a result, this provides great opportunities and challenges for chemists to design and develop functionalized materials with various structures. Common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D487/04C07D519/00C09K2211/1088C09K2211/1092C09K2211/1059C09K2211/1044C09K2211/1029H10K85/622H10K85/631H10K85/626H10K85/654H10K85/657H10K85/6576H10K85/6572H10K85/6574
Inventor 高文正张春雨任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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