Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether disubstituted 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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  • Abstract
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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 ...

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of compound 1a:

[0034]

[0035] 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 with a small amount of chloroform, and purified by silica gel (300-400 mesh) chromatographic column (eluent: chloroform:ethyl acetate=1:1 (volume ratio) ). The first color band is purple-red solid compound 1a (0.03 g, yield 5%), m.p.242-244°C.

[0036] Compound 1a:

[0037]Elemental analysis: measured value C% 62.01 H% 4.70 N% 9.33 S% 5.34;

[0038] Calculated C% 62.45 H% 4.67 N% 9.02 S% 5.21.

[0039] IR (cm -1 ) 1632 (C=C), 966 (C=C).

[0040] 1 HNMR (CDCl 3 , 400MHz) δ: 8.00 (d, 1H, J=16.0Hz, -CH=CH-), 7.90 (d, 1H, J=15.6Hz, -CH=CH-), 7.09 (d, 1H, J=16.4 Hz, -CH=CH-), 6.97(s, 1H, Py-H), 6.73(d, 1H, ...

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, and after dissolving a small amount of chloroform, it was purified by silica gel (300-400 mesh) chromatographic column (eluent: chloroform:ethyl acetate=15:1 (volume ratio)) . The first color band is yellow solid compound 1b (0.12 g, yield 17%), m.p. 204-206°C.

[0045] Compound 1b:

[0046] Elemental analysis: measured value C% 77.22 H% 6.89 N% 11.50 S% 4.39;

[0047] Calculated C% 76.96 H% 6.77 N% 11.68 S% 4.54.

[0048] IR (cm -1 ) 1625 (C=C), 956 (C=C).

[0049] 1 HNMR (CDCl 3 , 400MHz) δ: 8.29 (m, 2H, Ar), 8.15 (m, 3H, Ar and-CH=CH-), 7.65 (dd, J=8.4Hz, 2H, Ar), 7.36 (m, 9H, Ar and-CH=CH-), 7.05 (...

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 solvent was distilled off under reduced pressure, dried, dissolved with a small amount of chloroform, and purified by silica gel (300-400 mesh) chromatographic column (eluent: chloroform:ethyl acetate=15:1 (volume ratio) ). The first color band is yellow solid compound 1c (0.09 g, yield 11%), m.p.189-191°C.

[0054] Compound 1c:

[0055] Elemental analysis: measured value C% 63.51 H% 5.44 N% 9.46 S% 3.61;

[0056] Calculated C% 63.70 H% 5.19 N% 9.53 S% 3.70.

[0057] IR (cm -1 ) 1632 (C=C), 962 (C=C).

[0058] 1 HNMR (CDCl 3 , 400MHz) δ: 8.25(m, 4H, -CH=CH-and Ar), 7.80(m, 2H, Ar), 7.55(m, 3H, -CH=CH-and Py-H), 7.3(m, 8H, -CH=CH-and Ar), 4.28(t, 4H...

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Abstract

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

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
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