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Organic electroluminescent material and application thereof

A carbon atom, selected technology, applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of difficulty in implementation, inability to make proper evaluation of compound performance, and lack of data on light-emitting devices

Active Publication Date: 2011-03-23
TSINGHUA UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

International Patent Application Publication (WO2007123254) discloses another dibenzo[a,c]anthracene derivative used in organic EL devices, but the patent does not have device evaluation data, so it cannot be used as a luminescent material for these appropriate evaluation of compound properties
Japanese Patent Application Publication Hei 12(2000)-178548 discloses a luminescent material 1,2-benzo[a]anthracene derivative with high heat resistance, but the material is limited to C-H aryl substitution 1, 2-Benzo[a]anthracene derivatives or alkoxy-substituted aryl-substituted 1,2-benzo[a]anthracene derivatives containing only C-H, and there is also no data on light-emitting devices, and it is also impossible to analyze these Evaluation of the Luminescent Properties of Compounds Used as Luminescent Materials
In addition, International Patent Application Publication (WO2008145239) mentions a 1,2-benzo[a]anthracene derivative containing a nitrogen atom, which involves a single secondary amino group or N at the 2-, 4-, 5-, or 6-position -carbazolyl monosubstituted 1,2-benzo[a]anthracene derivatives, but in fact the most active chemical substitution position of 1,2-benzo[a]anthracene is the 7th position, which needs to be functionally substituted or used as an electronic material Protection can be better used; or it is 7, 12 or 6, 12 secondary amine or bis (N-carbazolyl) disubstituted 1,2-benzo [a] anthracene derivatives, but in 7, 12 It is too difficult or even impossible to implement due to too much steric hindrance when connecting with a secondary amine or bis(N-carbazolyl)
The patent does not explicitly mention derivatives substituted by a single secondary amine or N-carbazolyl at the 7-position of 1,2-benzo[a]anthracene, nor the above-mentioned 1,2-benzo[a]anthracene series Derivative-related material luminescence performance data

Method used

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  • Organic electroluminescent material and application thereof
  • Organic electroluminescent material and application thereof
  • Organic electroluminescent material and application thereof

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Effect test

preparation example Construction

[0090] Preparation of some intermediates:

[0091] (1) Preparation of 7-bromo-1,2-benzo[a]anthracene (M1)

[0092]

[0093] In a 1000ml three-necked flask, 35 grams (147.4mmol) of 1,2-benzo[a]anthracene was dissolved in 550ml of N,N-dimethylsulfoxide (DMF), and another 32.8 grams (184.4mmol) of N-bromo Succinimide (NBS) was dissolved in 140ml DMF. Under room temperature and magnetic stirring, the NBS solution was added dropwise into the reaction flask through a constant pressure dropping funnel, and the addition was completed in about 30 minutes. The reaction was continued for 2 hours, and the end point of the reaction was monitored by TLC. The reaction solution was transferred to a beaker, and under rapid stirring, 400ml of water was added dropwise. After fully stirring, the precipitated yellow precipitate was filtered by suction, rinsed with water and absolute ethanol successively, and dried to obtain 35.8 grams of light orange-yellow solid. The yield : 78%.

[0094] ...

Embodiment 1

[0160] The synthesis of embodiment one compound V3

[0161]

[0162] Under the protection of argon, add 1.22 g (5 mmol) M2, 1.44 g (15 mmol) sodium tert-butoxide, 2.22 g (12 mmol) 2,4-dimethylbromobenzene, 0.029 g (0.05 mmol) di (Dibenzylideneacetone)palladium(0)(Pd(dba) 2 ), 0.20 grams (0.1 mmol) of tri-tert-butylphosphine (10% mass toluene solution) and 30 ml of dry toluene, magnetically stirred and refluxed for 5 hours, and TLC monitored the reaction end point. Cool, wash with water, separate the liquids, evaporate the solution by rotary evaporation, separate and purify by silica gel column chromatography, and elute with ethyl acetate:petroleum ether=1:12 (volume ratio) to obtain 1.65 g of a yellow solid with a yield of 73%.

[0163] Product FD-MS (m / z): 451.0, corresponding to: C 34 h 29 N=451.6, elemental analysis: C 34 h 29 N, theoretical value: C, 90.43; H, 6.47; N, 3.10; experimental value: C, 90.38; H, 6.40; N, 3.11; prove that the compound is the target produ...

Embodiment 2

[0164] The synthesis of embodiment two compound V8

[0165]

[0166] Under the protection of argon, add 1.84 g (5 mmol) M1, 1.44 g (15 mmol) sodium tert-butoxide, 1.47 g (6 mmol) N-p-biphenylaniline (M11), 0.029 g (0.05 mmol) (Dibenzylideneacetone)palladium(0)(Pd(dba) 2 ), 0.20 grams (0.1 mmol) of tri-tert-butylphosphine (10% mass toluene solution) and 35 ml of dry toluene, magnetically stirred and refluxed for 2 hours, and TLC monitored the reaction end point. Cool, wash with water, separate the liquid, evaporate the solution by rotary evaporation, separate and purify by silica gel column chromatography, and elute with ethyl acetate:petroleum ether=1:15 (volume ratio) to obtain 2.12 g of a yellow solid, with a yield of 90%.

[0167] Product FD-MS (m / z): 471.1, corresponding to: C 36 h 25 N=471.59, elemental analysis: C 36 h 25 N, theoretical value: C, 91.69; H, 5.34; N, 2.97; experimental value: C, 91.60; H, 5.27; N, 2.91; prove that the compound is the target product...

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Abstract

The invention relates to a 1,2-benzo[a]anthracene derivative and an organic electroluminescent device containing the compound. The general structural formula of the compound is shown in a structural general formula (1), wherein A1 and A2 are independently selected from aromatic groups with 6 to 25 nuclear carbon atoms respectively, or selected from substituent groups represented by the general formulae (1) to (4). The material of the invention can be preferably used as a luminous body, and simultaneously can be used as a transmission material. The electroluminescent device manufactured by the material of the invention has the high performances of low drive voltage, high luminescent efficiency and the like.

Description

technical field [0001] The invention relates to a novel organic compound and belongs to the field of photoelectric materials. Background technique [0002] Organic light-emitting device (Organic light-emitting device, hereinafter referred to as OLED) and corresponding research began as early as the 1960s. In 1963, p.pope and others first discovered the electroluminescence phenomenon of organic single crystal anthracene, but due to the limitation of technical conditions, its driving voltage was as high as 400V, which failed to attract widespread attention. In 1987, C.W.Tang et al. of Kodak Corporation of the United States used vapor-deposited tri(8-hydroxyquinolinium) aluminum (Alq 3 ) and HTM-2 made an amorphous film type device, and the driving voltage was reduced to within 20V, and OLED attracted the attention of the world (US4356429). Due to the advantages of high brightness, wide viewing angle, fast photoelectric response, low voltage, low power consumption, rich color...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D209/88C07D209/86C09K11/06H01L51/50H01L51/54
Inventor 邱勇李建仁李银奎
Owner TSINGHUA UNIV
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