General formula compound and organic light-emitting device

A compound and general formula technology, applied in the field of organic electroluminescent devices, can solve the problems of dependence on global resources and high material costs

Active 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, phosphorescent materials generally contain rare metals such as Ir and Pt, which are costly and rely on limited global resources

Method used

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  • General formula compound and organic light-emitting device
  • General formula compound and organic light-emitting device
  • General formula compound and organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0075] Synthesis Example 1: Synthesis of Compound P1

[0076]

[0077] Add 8.79g (35mmol) of isopropylcarbazole into a 250ml three-neck flask, add 100ml of N,N-dimethylformamide as a reaction solvent, and stir on a magnetic stirrer for 10min under ice-bath conditions. 0.72g (30mmol) NaH was added to the reaction flask in batches, and the stirring was continued for 1h. Dissolve 2.07g (10mmol) of 2,4,6-trichloro-5-cyanopyrimidine in 40ml of N,N-dimethylformamide solution and add it dropwise to the reaction system. Under reaction 24h. After the reaction, the reaction solution was poured into 200ml concentration of 10% dilute hydrochloric acid to quench, after vacuum filtration, washed with water, dried, the crude product obtained was washed with sherwood oil and dichloromethane (PE:DCM=10: 1) Pass the column as the mobile phase. 5.56 g of white solid powder was obtained with a yield of 65.2%. (1HNMR(δ,CDCl3):7.40(6H,s),7.28(6H,s),6.71-6.68(6H,d),3.08-3.01(6H,m),1.19-1.10(1...

Synthetic example 2

[0078] Synthesis Example 2: Synthesis of Compound P2

[0079]

[0080] Add 8.79g (35mmol) of isopropylcarbazole into a 250ml three-neck flask, add 100ml of N,N-dimethylformamide as a reaction solvent, and stir on a magnetic stirrer for 10min under ice-bath conditions. 0.72g (30mmol) NaH was added to the reaction flask in batches, and the stirring was continued for 1h. Dissolve 2.83g (10mmol) of 2,4,6-trichloro-5-cyanophenylpyrimidine in 40ml of N,N-dimethylformamide solution and add it dropwise to the reaction system. Reaction at room temperature for 24h. After the reaction, the reaction solution was poured into 200ml concentration of 10% dilute hydrochloric acid to quench, after vacuum filtration, washed with water, dried, the crude product obtained was washed with sherwood oil and dichloromethane (PE:DCM=10: 1) Pass the column as the mobile phase. 4.99 g of white solid powder was obtained with a yield of 53.7%.

[0081] (1HNMR(δ,CDCl3):7.60-7.56(4H,d),7.38(6H,s),7.30(6H...

Synthetic example 3

[0082] Synthesis Example 3: Synthesis of Compound P5

[0083]

[0084] Under nitrogen protection, 6.28g (25mmol) isopropylcarbazole, 2.83g (10mmol) 2,4,6-trichloro-5-cyanopyrimidine, 1.92g (20mmol) NaOBu-t, 1.92g (0.2 mmol)(t-Bu) 3 HBF 4 , 0.09g (0.1mmol) Pd 2 (dba) 3 Add it into a 250ml three-neck flask, add 100ml of toluene as a reaction solvent, heat up to reflux temperature, and stir overnight on a magnetic stirrer. After the reaction, the reaction solution was spin-dried, and the obtained crude product was passed through the column with petroleum ether and dichloromethane (PE:DCM=5:1) as the mobile phase. Intermediate 1 was obtained as white solid powder, weighing 4.70 g, and the yield was 73.7%.

[0085] 1.56g (7.5mmol) 9,9-Dimethylacridine Add to a 250ml three-neck flask, add 50ml of N,N-dimethylformamide as a reaction solvent, and stir on a magnetic stirrer for 10min under ice-bath conditions. 0.36g (15mmol) NaH was added to the reaction flask in batches, an...

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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), A4 is selected from cyano or benzene cyano. A1, A2 and A3 are each independently represented by the formula (II) or (III) shown in the specification. In the formula (II) and formula (III), R1-R8 and R9-R16 are each independently selected from hydrogen, a C1-C10 alkyl group, asubstituted or unsubstituted C6-C30 aryl or fused ring aromatic hydrocarbon group, a substituted or unsubstituted C3-C30 heteroaryl or fused heterocyclic aromatic hydrocarbon group; and any adjacent two of the R1-R8 are optionally joined to a cyclic structure, any adjacent two of the R9-R16 are optionally joined to a cyclic structure; and when A1 is selected from the formula (II), at least one ofR1 to R8 in the formula (II) is hydrogen; when the A1 is selected from the formula (III), at least one of R9 to R16 in the formula (III) is hydrogen; in the formula (III), X is selected from the groupconsisting of oxygen, sulfur, imino, methylene, and silicylene. The invention further relates to an organic electroluminescent device employing the compound of the formula (I).

Description

technical field [0001] The invention relates to a novel general formula compound and an organic electroluminescent device using the compound. Background technique [0002] Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal display, organic electroluminescent display is not It needs a backlight source, has a large viewing angle, low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufacturing cost is lower than that of a liquid crystal display with the same resolution. Therefore, organic electroluminescent devices have broad application prospects. [0003] With the continuous advancement of OLED technology in the two major fields of lighting and display, people pay more attention to the research of high-efficiency organic mater...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C07D413/14C07D417/14C07F7/08C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D403/14C07D413/14C07D417/14C07F7/0816C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1029C09K2211/1007H10K85/657H10K85/6572H10K85/40H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171
Inventor 高文正黄鑫鑫任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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