Red organic electroluminescent materials containing naphthylamine group and method for preparing same

A naphthylamine group, electroluminescence technology, applied in the field of red light-emitting materials and preparation thereof, can solve the problems of difficulty in large-scale production and application, shift of light-emitting wavelength, cumbersome preparation method, etc., and achieves reduction of self-quenching phenomenon and simple method. , the effect of good carrier transport characteristics

Inactive Publication Date: 2007-08-22
未名光电盐城有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently used red organic electroluminescent materials are DCM derivatives containing pyran groups. Due to the high polarity of the molecules, the clustering effect between molecules will cause concentration quenching, so these materials can only emit light as guests. Materials, doped in the host light-emitting material to make light-emitting devices, and slight changes in doping concentration will cause the light-emitting wavelength to shift, which makes it difficult to make light-emitting devices with stable performance
Introducing a group with a large steric hindrance in the molecule can reduce the clustering effect between molecules and improve the luminescent performance of the red luminescent material. The widely used red luminescent material DCJTB is a DCM derivative modified according to this idea (C.H.Chen, C.W.Tang, J.Shi and K.P.Klubek.Macromol.Symp., 1997,125:49-58), but its preparation method is very loaded down with trivial details, needs organic reaction through more than five steps, and raw material is rare, and cost is high, and large-scale production and Difficulty applying

Method used

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  • Red organic electroluminescent materials containing naphthylamine group and method for preparing same
  • Red organic electroluminescent materials containing naphthylamine group and method for preparing same
  • Red organic electroluminescent materials containing naphthylamine group and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1, the preparation of 4-(bis(1-naphthyl)amino)benzaldehyde (III-1): add 7.0g (20mmol) bis(1-naphthyl)aniline, 2.3ml (30mmol ) DMF and 30 ml 1,2-dichloroethane. The reaction flask was placed in an ice-water bath, and 2.8ml (30mmol) POCl was added dropwise under stirring 3 . After the addition, reflux in an oil bath at 95°C for 20 hours, pour into 300ml of ice water while hot, and adjust the pH of the solution to 7 with 1M NaOH solution. Extract with ethyl acetate, dry, and remove the solvent on a rotary evaporator. Purified by column chromatography (eluent: toluene) to obtain 2.70 g of light yellow product (36.2% yield).

[0044] IR (KBr, cm -1 ): 3045, 2922, 2851, 1689, 1597, 1569, 1504, 1392, 1164, 797, 774. 1 HNMR (500Hz, CDCl 3 ): δ9.76 (s, 1H), 8.0 (d, J = 8.5Hz, 2H), 7.93 (d, J = 8.3Hz, 2H), 7.81-7.79 (m, 2H), 7.59 (d, J = 8.7Hz, 2H), 7.52(t, J=7.5Hz, 2H), 7.43-7.40(m, 6H), 6.60(s(br), 2H).

Embodiment 2

[0045]Embodiment 2, the preparation of DNP-2CN: in 50ml round bottom flask, add 1.10g (8.0mmol) isophorone and 0.53g (8.0mmol) malononitrile, 0.27ml glacial acetic acid and 0.17ml acetic anhydride are dissolved in 20ml DMF, take 2.1ml and add to the reaction bottle; dissolve 1.66ml piperidine in 10ml DMF, take 2.3ml and add to the reaction bottle. Stir at room temperature for 0.5 hours, heat up to 100°C and stir for 0.5 hours, add 2.70 g (7.24 mmol) of 4-(di(1-naphthyl)amino)benzaldehyde (III-1, Example 1), and continue stirring for 0.5 hours , pour it into 200ml (containing 6ml concentrated HCl) hot water and stir while it is hot, separate the solid, stir in a mixed solution of 40ml isopropanol and 5ml water, collect the precipitated solid by suction filtration, recrystallize in acetonitrile to obtain a red crystal product 2.50 g (63.8% yield). Melting point: 250°C.

[0046] IR (KBr, cm -1 ): 3035, 2924, 2853, 2217, 1687, 1602, 1586, 1554, 1521, 1502, 1392, 1304, 1290, 117...

Embodiment 3

[0051] Embodiment 3, the preparation of 4-(phenyl (1-naphthyl) amino) benzaldehyde (III-2): add 4.56g (15.5mmol) (1-naphthyl) diphenylamine, 1.8ml in 100ml eggplant-shaped bottle (23mmol) DMF and 40ml 1,2-dichloroethane. The reaction flask was placed in an ice-water bath, and 2.1ml (23 mmol) POCl was added dropwise under stirring 3 . After the addition, reflux in an oil bath at 95°C for 1 hour, pour into 200ml of ice water while hot, and adjust the pH of the solution to 7 with 1M NaOH. Extract with ethyl acetate, dry, and remove the solvent on a rotary evaporator. Purification by column chromatography (eluent: toluene / petroleum ether (60-90° C.) = 1 / 1) gave 3.26 g of a light yellow product (65.1% yield).

[0052] IR (KBr, cm -1 ): 3035, 2851, 1687, 1602, 1586, 1504, 1491, 1391, 1249, 1223, 1163, 774, 752, 695.

[0053] 1 H NMR (500Hz, CDCl 3 ): δ9.78(s, 1H), 7.92(d, J=8.2Hz, 1H), 7.86(t, J=8.2Hz, 2H), 7.64(d, J=8.7Hz, 2H), 7.53-7.48 (d+d, 2H), 7.43-7.38(d+d, 2H), 7.31(...

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Abstract

The invention discloses a red organic electroluminescent materials containing naphthylamine group and method for preparing same, wherein the material has the basic frame of triarylamine, whose extensibility on the three dimensional space and the large rigidity and molecular dimension of the naphthyl can reduce the clustering between the molecules.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence materials, in particular to a red light-emitting material for organic electroluminescence and a preparation method thereof. technical background [0002] Organic electroluminescence has the characteristics of low-voltage DC drive, high brightness, and wide viewing angle, and is considered to be one of the most promising flat-panel display technologies for the next generation (C.W.Tang and S.A.VanSlyke.Appl.Phys.Lett., 1987, 51(12 ): 913-915). Since the luminous efficiency and lifespan of red organic electroluminescent devices are far behind those of green and blue light emitting devices, it has become the key to restricting organic electroluminescence to achieve color display. Most of the currently used red organic electroluminescent materials are DCM derivatives containing pyran groups. Due to the high polarity of the molecules, the clustering effect between molecules will ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06H05B33/00
Inventor 肖斐付慧英徐吉翔詹义强
Owner 未名光电盐城有限公司
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