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Preparation and application of 3-substituted-N-hexyl phenothiazine derivative

A phenothiazine derivative, phenothiazine technology, applied in electrical components, electrical solid devices, circuits, etc., to achieve the effect of good electroluminescence performance

Inactive Publication Date: 2009-12-16
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research on the three primary color materials in the display field finds that although the luminous lifetime of the materials ge

Method used

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  • Preparation and application of 3-substituted-N-hexyl phenothiazine derivative
  • Preparation and application of 3-substituted-N-hexyl phenothiazine derivative
  • Preparation and application of 3-substituted-N-hexyl phenothiazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Compound 1 Preparation:

[0072]

[0073] 3-Formyl-N-hexylphenothiazine (0.33 g, 1.1 mmol) and malononitrile (80.1 mg, 1.2 mmol) were added to a round bottom flask, and 15 mL of pyridine was added, and refluxed for 1 hour. The reaction mixture was cooled and poured into water, extracted with chloroform, washed with brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain a reddish-brown crude product; the crude product was purified with a 300-400 mesh silica gel column, eluent: petroleum ether : acetone=15:1 (volume ratio), the red product-compound 1 (0.34 g, yield 87%) was obtained.

[0074] Compound 1:

[0075] Elemental analysis: measured value C% 73.31 H% 5.70 N% 12.03 S% 8.96;

[0076] Calculated value C% 73.54 H% 5.85 N% 11.70 S% 8.91

[0077] IR (cm -1 ) 2217 (CN), 960 (C=C).

[0078] 1 HNMR (CDCl 3 , 400MHz) δ: 0.88(t, 3H, CH 3 ), 1.32 (d, 4H, CH 2 ), 1.43(t, 2H, CH 2 ), 1.80(t,...

Embodiment 2

[0081] Compound 2 Preparation:

[0082]

[0083] Add 3-formyl-N-hexylphenothiazine (0.87g, 2.8mmol) in a 50mL round-bottomed flask equipped with a reflux condenser, and add n-butanol (27mL) and 3 drops of catalytic amount of piperidine, heat up Reflux, 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-methanesulfonic acid (0.30g, 1.3mmol) was added to the reaction flask in four times, and the addition was completed. After reacting for 72 hours, n-butanol was distilled off under reduced pressure, purified by 300-400 mesh silica gel chromatography column, eluent: petroleum ether: ethyl acetate = 15:1 (volume ratio), and the first color band was collected to obtain purple Black product - compound 2 (190.3 mg, 19% yield).

[0084] Compound 2

[0085] Elemental analysis: measured value C% 67.87 H% 5.72 N% 10.39 S% 12.21;

[0086] Calculated C% 67.95 H% 5.95 N% 10.34 S% 11.83.

[0087] IR (cm -1 ) 1660, 937 (C=C), 1335, 1165 (SO 2 )

[0088] 1 HNMR (CDCl 3 , 400MH...

Embodiment 3

[0091] Compound 3 preparation:

[0092]

[0093] Add 3-formyl-N-hexyl phenothiazine (0.87g, 2.8mmol) in a 50mL round-bottomed flask equipped with a reflux condenser, and add n-butanol (27mL) and 4 drops of catalytic amount of piperidine, heat up Reflux, 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-methanesulfonic acid (0.30g, 1.3mmol) was added to the reaction flask in four times, and the addition was completed. After reacting for 72 hours, n-butanol was distilled off under reduced pressure, purified by using a 300-400 mesh silica gel chromatography column, eluent: petroleum ether: ethyl acetate=15:1 (volume ratio), and the second color band was collected to obtain orange Yellow solid product-compound 3 (277.0 mg, yield 42%).

[0094] Compound 3

[0095] Elemental analysis: measured value C% 62.45 H% 5.67 N% 13.50 S% 12.16;

[0096] Calculated C% 62.40 H% 5.62 N% 13.48 S% 12.34.

[0097] IR (cm -1 ) 936 (C=C), 1333, 1163 (SO 2 ).

[0098] 1 HNMR (CDCl 3...

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Abstract

The invention discloses preparation and application of a 3-substituted-N-hexyl phenothiazine derivative shown in a general formula (I). In the formula, R is malononitrile group, 1, 2, 4-triazolo [1, 5-a] pyrimidyl, spiropyranyl, 3-dicyanomethylene-1, 5, 5-trimethylcyclohexenyl, 1, 3-diethyl-2-thiobarbituric acidyl, N, N-dimethylaminophenyl, p-nitrobenzophenone or 2, 4, 6-trimethyl-3, 5-dicyanopyridyl. All the compounds have fine solubility and thermostability and can be applied to flat-panel displays as red electroluminescent materials.

Description

technical field [0001] The invention belongs to the technical field of electroluminescence, and specifically relates to the preparation and application of a class of 3-substituted-N-hexylphenothiazine derivatives with excellent electron injection and hole transport capabilities. This type of compound has good solubility and thermal stability, and can be used as a red electroluminescent material in flat panel displays. Background technique [0002] Phenothiazine, also known as sulfurized diphenylamine or thiazaxanthene, is a three-membered heterocyclic compound with sulfur and nitrogen heteroatoms. Since it was first synthesized in 1883 [1], it has been used in dye chemistry, medicinal chemistry, photoelectrochemistry, etc. The field has a wide range of applications. For example, compounds such as Lowe's violet, methylene blue, and thiamine blue containing phenothiazine structural units have strong absorption of visible light and are widely used as dyes; phenothiazine has a ...

Claims

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Application Information

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IPC IPC(8): C07D279/22C07D487/04C07D417/14C07D417/06C09K11/06H01L27/32
Inventor 王宏里徐文远张彬肖文精
Owner HUAZHONG NORMAL UNIV
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