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Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative and application thereof

A technology of ethyl sulfide and derivatives, applied in semiconductor/solid-state device manufacturing, electrical components, circuits, etc., to achieve good photoluminescence and electroluminescence performance effects

Inactive Publication Date: 2009-10-21
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although organic electroluminescence has achieved remarkable development, many high-performance electroluminescent materials have been developed, and commercialized organic EL display devices are also emerging, but in order to have high efficiency, low cost, and high stability , the advantages of long life, there are still many difficulties

Method used

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  • Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative and application thereof
  • Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative and application thereof
  • Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of compound 1a:

[0035]

[0036]Add 0.2g 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl sulfide and 2.1 mole For ferrocene monoaldehyde, add 20 mL of n-propanol to dissolve, add 10 drops of piperidine, and heat, stir and reflux for 2 days. After it was cooled, the solvent was distilled off under reduced pressure, dried, dissolved in chloroform, and purified by silica gel (300-400 mesh) chromatographic column (eluent: chloroform:ethyl acetate=1:1 (volume ratio)) . The second color band is purple-red solid compound 1a (0.28 g, yield 78%), m.p.178-179°C.

[0037] Elemental analysis: measured value C% 59.41 H% 4.98 N% 13.86 S% 7.93;

[0038] Calculated for C% 59.53 H% 4.87 N% 13.58 S% 8.09.

[0039] IR (cm -1 ) 1657 (C=C), 956 (C=C).

[0040] 1 HNMR (CDCl 3 , 400MHz) δ: 7.96 (d, 1H, J=15.0HZ, -CH=CH-), 7.08 (d, 1H, J=15.0HZ, -CH=CH-), 6.94 (s, 1H, Py), 4.65(s, 2H, Ar), 4.52(s, 2H, Ar), 4.20(s, 5H, Ar), 3.35(m, 2H, J=4.8HZ, S-CH 2 ),...

Embodiment 2

[0042] Preparation of compound 1b:

[0043]

[0044] Add 0.2g 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl sulfide and 2.1 mole For 3-formyl-N-hexylcarbazole, add 20 mL of n-propanol to dissolve, add 10 drops of piperidine, and heat, stir and reflux for 2 days. After it was cooled, the crude product was evaporated to dryness under reduced pressure, dissolved in chloroform and purified on a silica gel (300-400 mesh) chromatographic column (eluent: chloroform:ethyl acetate=15:1 (volume ratio)) . The second color band is yellow solid compound 1b (0.11 g, yield 26%), m.p.158-160°C.

[0045] Elemental analysis: measured value C% 71.61 H% 6.65 N% 14.86 S% 6.51;

[0046] Calculated C% 71.35 H% 6.74 N% 14.91 S% 6.83.

[0047] IR (cm -1 ) 1632 (C=C), 958 (C=C).

[0048] 1 HNMR (CDCl 3 , 400MHz) δ: 8.16 (m, 2H, -CH=CH-and Ar), 7.78 (d, 1H, J=8.8Hz, Ar), 7.56 (d, 1H, J=16.4Hz, -CH=CH- ), 7.43 (m, 4H, Ar), 7.04 (s, 1H, Py-H), 6.70 (s, 1H, Ar), 4.29 (m, 2H, J=7.2Hz, N-C...

Embodiment 3

[0051] Preparation of compound 1c:

[0052]

[0053] Add 0.2g 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl sulfide and 2.1 mole For 6-bromo-3-formyl-N-hexylcarbazole, add 20 mL of n-propanol to dissolve, add 10 drops of piperidine dropwise, and heat, stir and reflux for 2 days. After it was cooled, the crude product was evaporated to dryness under reduced pressure, dissolved in chloroform and purified on a silica gel (300-400 mesh) chromatographic column (eluent: chloroform:ethyl acetate=15:1 (volume ratio)) . The second color band is yellow solid compound 1c (0.19 g, yield 36%), m.p.147-149°C.

[0054] Elemental analysis: measured value C% 61.31 H% 5.51 N% 12.77 S% 5.85;

[0055] Calculated for C% 61.29 H% 5.72 N% 12.65 S% 5.54.

[0056] IR (cm -1 ) 1631 (C=C), 958 (C=C).

[0057] 1 HNMR (CDCl 3 , 400MHz) δ: 8.28 (m, 3H, -CH=CH-and Ar), 7.83 (d, 1H, J=8.4Hz, Ar-H), 7.55 (t, 2H, Py-H and Ar), 7.44 (d, 1H, J=6.0Hz, Ar-H), 7.30 (d, 1H, J=7.2Hz, Ar-H...

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Abstract

The invention discloses preparation for a 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative with a general formula (1) and application thereof. In the formula, Ar is ferrocenyl, triphenylamine, N-hexyl carbazyl, 6-bromine-N-hexyl carbazyl, 4-(N,N-bis p-bromine diphenyl)aminophenyl or N,N-dimethylamino benzyl. The compound has good solubility and thermal stability, can be used as a blue, green or red electroluminescent material, and can be applied to a flat-panel display.

Description

technical field [0001] The invention belongs to the technical field of photoluminescence and electroluminescence, and specifically relates to the preparation of a class of 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl sulfide monosubstituted derivatives and their use as Application of photoluminescent and electroluminescent materials in organic flat panel displays. This type of compound has good solubility and thermal stability, and can be used as blue or green photoluminescent and electroluminescent materials in flat panel displays. Background technique [0002] Triazolopyrimidine heterocyclic derivatives have a wide range of biological activities due to their molecular structure containing two important active structural units, triazole and pyrimidine [1], and have been widely used in the fields of pesticides and medicine. The application of pesticides [1] is a hot field in the research and development of new pesticides. For example, Berecz et al. reported that 7-chloro-5,6-cy...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07F17/02C09K11/06H01L51/54
Inventor 王宏里张彬徐文远肖文精
Owner HUAZHONG NORMAL UNIV