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Donor-acceptor type based organic electroluminescent material

An electroluminescent material and donor-acceptor-type technology, which is applied in the fields of luminescent materials, organic chemistry, preparation of organic compounds, etc., can solve problems such as limiting molecular design, and achieve fewer synthesis steps, simple methods, and simple and easy purification methods. effective effect

Inactive Publication Date: 2013-07-10
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This long-term "consensus" greatly limits the molecular design of acceptor-type luminescent materials

Method used

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  • Donor-acceptor type based organic electroluminescent material
  • Donor-acceptor type based organic electroluminescent material
  • Donor-acceptor type based organic electroluminescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add malononitrile (1.87 g, 28.3 mmol) and isophorone (3.90 g, 28.3 mmol) to a mixed solution consisting of 28 μl acetic acid, 18 μl acetic anhydride, 380 μl piperidine and 8 ml N,N-dimethylformamide Stir at room temperature for 1 hour, then raise the temperature to 78°C and stir for 1 hour, then add 3.4526g of salicylaldehyde, stir at 78°C for 1 hour, pour the reactant into 200ml of 3% hydrochloric acid solution heated to 60°C while hot , stirred to produce a brick red precipitate.

[0039] The precipitate was collected, vacuum filtered, and the precipitate was washed with 100 ml of deionized water for 3 times. Recrystallize with a mixed solution of chloroform and ethyl acetate at a volume ratio of 3:1, use 50 ml of the mixed solution each time, and recrystallize 5 times to obtain purified 3-dinitrile methylene-5,5-dimethyl- 1-(2-Hydroxystyrene)cyclohexene (DCD(2-OH)SC), 65% yield.

[0040] Characterize the chemical structure of the purified DCD(2-OH)SC:

[0041] 1. ...

Embodiment 2

[0055] Add 1.84 g of malononitrile and 4.05 g of isophorone to a mixed solution consisting of 30 μl of acetic acid, 19 μl of acetic anhydride, 407 μl of piperidine and 8.6 ml of N,N-dimethylformamide, stir at room temperature for 60 min, and then Raise the temperature to 80°C and stir for 1 hour, then add 3.74g of 3-hydroxybenzaldehyde, stir and react at 80°C for 1 hour, pour the reactant into 200ml of 3.25% hot hydrochloric acid solution heated to 60°C while it is still hot, and stir to produce brick red Precipitate.

[0056] Recrystallize according to the method of Example 1 to obtain brick red solid 3-dinitrile methylene-5,5-dimethyl-1-(3-hydroxystyrene) cyclohexene (DCD(3-OH)SC) Yield 84%.

[0057] 1. Elemental analysis:

[0058] The molecular formula of DCD(3-OH)SC is C 19 h 18 N 2 O, molecular weight 290.35, its elemental analysis (%) result is as follows:

[0059] Calculated: C, 78.52; H, 6.20; N, 9.64;

[0060] Measured values: C, 78.47; H, 6.17; N, 9.60.

[00...

Embodiment 3

[0066] Add 1.79 g of malononitrile and 3.80 g of isophorone to a mixed solution consisting of 26 μl of acetic acid, 17 μl of acetic anhydride, 359 μl of piperidine and 7.56 ml of N,N-dimethylformamide, stir at room temperature for 1 h, and then Raise the temperature to 75°C and stir for 1 hour, then add 3.4526g of 4-hydroxybenzaldehyde, stir and react at 80°C for 1 hour, pour the reactant into 200ml of 3.2% hot hydrochloric acid solution heated to 60°C while it is still hot, and stir to produce a brick-red precipitate thing.

[0067] Recrystallize according to the method of Example 1 to obtain brick red solid 3-dinitrile methylene-5,5-dimethyl-1-(4-hydroxystyrene) cyclohexene (DCD(4-OH)SC) , yield 93.4%.

[0068] 1. Elemental analysis:

[0069] The molecular formula of DCD(4-OH)SC is C 19 h 18 N 2 O, molecular weight 290.35, its elemental analysis (%) result is as follows:

[0070] Calculated: C, 78.52; H, 6.20; N, 9.64;

[0071] Measured values: C, 78.40; H, 6.17; N, 9...

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Abstract

The invention relates to a donor-acceptor type based organic electroluminescent material expressed by the general formula (I). In the formula, R represents a hydroxyl group, an alkyl group of C1-3, an alkoxyl group of C1-3, one or more halogen atom substituted alkyl groups of C1-3 or a halogen atom. In the invention, an aromatic aldehyde derivative, malononitrile and isophorone are used as raw materials of the organic electroluminescent material, and the raw materials react in a mixed solution of acetic acid, acetic anhydride, piperidine and N,N-dimethylformamide; the organic electroluminescent material is an intramolecular charge transfer compound with an electron donor-electron acceptor structural unit; and proved by a property testing result, the intramolecular charge transfer compoundhas better film forming property and good luminescent property and can be used as an organic electroluminescent material.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and relates to an organic electroluminescence material, in particular to an organic electroluminescence material based on a donor-acceptor type. Background technique [0002] 4-(Dinitrilemethylene)-2-methyl-6-(4-dimethylamino-styrene)-4H-pyran (DCM) is a very effective arylene laser dye. Since Tang et al first reported organic light-emitting diodes (OLEDs) made of DCM as a fluorescent dye in 1989, many organic light-emitting compounds with DCM skeletons have been synthesized and exhibited good light-emitting properties. At present, devices made of red light-doped materials represented by Kodak's classic doped red light-emitting material DCJTB have received extensive attention due to their excellent comprehensive performance, but their preparation methods are cumbersome and require more than five steps of organic reactions. , easy to produce by-products with symmetrical struct...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/36C07C255/32C07C255/37C07C255/35C07C253/30C07C253/34C09K11/06
Inventor 陈柳青刘旭光许并社许慧侠陶鹏王华郝玉英周禾丰高志翔徐阳张存
Owner TAIYUAN UNIV OF TECH
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