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Polysubstituted quinazine derivative funcional material, and preparing method and thereof

A technology for functional materials and derivatives, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of high price, unfavorable application, easy crystallization, etc., and achieve easy mass production, novel structural features, and low preparation costs. Effect

Inactive Publication Date: 2006-12-27
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although red, green, and blue are the three basic colors in a full-color display, some bright colors (such as light yellow, sky blue, etc.) are needed to enrich the variety of colors.
The most common yellow luminescent material is rubrene (Rubrene) ([3]Flora W.H., Hall H.K., Armstrong N.R.J.Phys.Chem.B, 2003, 107(5), 1142.), but it is expensive and easy to crystallize, Therefore, it is not conducive to practical application

Method used

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  • Polysubstituted quinazine derivative funcional material, and preparing method and thereof
  • Polysubstituted quinazine derivative funcional material, and preparing method and thereof
  • Polysubstituted quinazine derivative funcional material, and preparing method and thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1.68g (0.01mol) 1-phenylethylidene malononitrile, 1.06g (0.01mol) benzaldehyde and 20mL ethanol mixed solution, add 4mL 2M NaOH dropwise under stirring, stir at room temperature for 6h, heat to reflux for 6h, cool , filtered, and the crude product was recrystallized from ethanol to obtain a yellow solid. Yield 70%, m.p.299~300℃, UV-vis(solid)λ max : 336, 408nm; IR (KBr) v: 3452, 3345, 2216, 1633, 1560, 1495, 1414, 1368cm -1 ; 1 H NMR (DMSO-d 6 , 500MHz) δ: 6.94~7.74 (m, 18H, ArH+NH 2 ); 13 C NMR (DMSO-d 6 , 500MHz) δ: 98.8, 106.5, 116.1, 117.7, 118.3, 127.4, 127.7, 127.9, 128.2, 128.9, 129.2, 129.3, 129.4, 129.8, 130.1, 136.6, 137.8, 140.5, 1, 76.9, 147.2 .

Embodiment 2

[0053] 2.18g (0.01mol) 1-(2-naphthyl) ethylene malononitrile, 1.06g (0.01mol) benzaldehyde and 20mL ethanol mixed solution, and then add 4mL 2M NaOH dropwise under stirring, stir at room temperature for 6h, heat Reflux for 6h, cool, filter, the crude product is recrystallized from ethanol, yellow-green solid, yield: 61%; mp>300°C; UV-vis (solid, absorption) λ max 346, 408nm; IR (KBr) v3405, 3333 (NH 2 ), 2220(CN)cm -1 ; 1 H NMR (500MHz, DMSO-d 6 )δ6.55-8.34 (22H, m, ArH+NH 2 ); 13 C NMR (500MHz, DMSO-d 6 )δ98.9, 106.7, 116.1, 117.9, 118.7, 126.6, 126.7, 126.8, 127.0, 127.2, 127.3, 127.5, 127.6, 127.7, 127.8, 128.1, 128.3, 128.4, 128.7, 13, 128.9, 329.2 , 132.7, 133.1, 133.4, 134.0, 135.3, 140.5, 147.0, 149.5, 152.4, 157.2, 157.4. MS (EI) m / z 522 (M, 100).

Embodiment 3

[0055] 2.13g (0.01mol) 1-(4-nitrophenyl) ethylene malononitrile, 1.06g (0.01mol) benzaldehyde and 20mL ethanol mixed solution, add 4mL 2M NaOH dropwise under stirring, and stir at room temperature for 6h , heated to reflux for 6h, cooled, filtered, the crude product was recrystallized from ethanol, yellow solid, yield: 60%; mp>300°C; UV-vis (solid, absorption) λ max 340, 411nm; IR (KBr) v3475, 3357 (NH 2 ), 2219 (CN), 1348 (NO 2 )cm -1 ; 1 H NMR (500MHz, DMSO-d 6 )δ6.95-8.40 (16H, m, ArH+NH 2 ); 13 C NMR (500MHz, DMSO-d 6 )δ95.5, 99.3, 106.9, 115.5, 117.2, 118.7, 122.9, 124.2, 127.7, 128.0, 130.2, 130.7, 131.1, 131.9, 140.0, 143.3, 144.0, 146.7, 147.4, 148.4, 1551.9 (EI) m / z 512 (M, 100).

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Abstract

The invention relates to a preparation and application of 4, 5, 7-triaryl substituted 2- amino-3, 8-dicyano quinoline material, prepared of aromatic aldehyde and various 1-aryl ethylene methylene cyanides. It contains many aromatic substituting groups and amido and cyan compose a particular 'push-absorb' electronic structure, its melting point is above 300 deg.C, it has good stability and when it vacuum films, the film can permanently keep in a amorphous state. It can be used as the luminous layer of organic electroluminescent device and also doping material of the luminous layer to modulate luminous color. In addition, it is also used as the intermediate of organic synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic functional molecular materials and organic electroluminescent materials, and specifically relates to 4,5,7-triaryl-substituted 2-amino-3,8-dicyanoquinoline derivative functional materials and a preparation method thereof. and applications in organic electroluminescent devices. technical background [0002] Organic electroluminescence is a hot spot in the field of flat display technology ([1] Tang C.W., Van Slyke S.A. Appl. Phys. Lett., 1987, 51, 913; [2] Muller C.D., Falcou A., Reckefuss N.et al.. Nature, 2003, 421, 829.). Although red, green, and blue are the three basic colors in a full-color display, some bright colors (such as light yellow, sky blue, etc.) are needed to enrich the variety of colors. The most common yellow luminescent material is rubrene (Rubrene) ([3]Flora W.H., Hall H.K., Armstrong N.R.J.Phys.Chem.B, 2003, 107(5), 1142.), but it is expensive and easy to crystallize, Theref...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/58C09K11/06
Inventor 吕银祥周辉徐伟
Owner FUDAN UNIV
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