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Terpyridyl derivative with electroluminescent and electrochromic characteristics and complex thereof

An electrochromic and terpyridine technology, applied in the field of organic electronics, can solve the problems of low device service life, limited practical application, poor thermal stability, etc., and achieve the effect of sensitive electrochromic characteristics

Inactive Publication Date: 2012-07-04
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor thermal stability of traditional organic electroluminescent device materials and organic electrochromic materials leads to low device lifetime and limits their practical application.
The terpyridine triphenylamine branched structure provided by the present invention endows the material with good thermal stability, which can overcome the shortcomings of poor stability commonly found in current organic photoelectric materials; With the report of electrochromic properties, the electrochromic-electroluminescent bifunctional organic material reported by the present invention has potential application value in the field of flexible organic electronics

Method used

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  • Terpyridyl derivative with electroluminescent and electrochromic characteristics and complex thereof
  • Terpyridyl derivative with electroluminescent and electrochromic characteristics and complex thereof
  • Terpyridyl derivative with electroluminescent and electrochromic characteristics and complex thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0071] Embodiment 1: the synthesis of 4-(4'-nitro)-phenyl terpyridine

[0072]

[0073] [1] Synthesis of Intermediate 1: Add 10.8 mmol p-nitrobenzaldehyde to 100 mL MeOH, then add equimolar 2-acetylpyridine (10.8 mmol) and NaOH (2%, 0.44 g, 22 mL) and stir for 2 hours, A solid powder precipitated out. Rinse with water and methanol, filter and dry to obtain solid powder with a yield of 89.3%.

[0074] [2] Synthesis of Intermediate 2: Dissolve elemental iodine 5.06g (20mmol) in hot pyridine (30mL), add 2-acylpyridine (2.42g, 20.0mmol) under argon protection, and stir at 80°C 4h. After cooling, the solid product was filtered and rinsed 3 times with pyridine. The solid product was then decolorized by boiling 2 L of ethanol containing activated carbon. Filtrate while hot to obtain a yellow-green solid, and dry to obtain 4.38 g of a yellow-green solid with metallic luster, with a yield of 67.2%. Melting point: 227-228°C.

[0075] [3] Synthesis of 4-(4'-nitro)-phenyl terpyri...

Embodiment 2

[0076] Embodiment 2: the synthesis of 4-(4'-formyl)-phenyl terpyridine

[0077] Using a method similar to that in Example 1, only 4-nitrobenzaldehyde in step 1 was changed to 1,4-terephthalaldehyde according to the obtained compound, and the yield was 42.3%. Mass spectrum: m / z (EI) 337.12 (M + , 100%). 1 H NMR (CDCl 3 ; 400MHz; TMS): δ, ppm 7.12 (m, 2H, Ar-H), 7.66 (m, 4H, Ar-H), 7.87 (d, 2H, Ar-H), 8.46 (m, 4H, pyr- H), 8.59 (d, 2H, o-pyr-H), 9.87 (s, 1H, CHO).

[0078] The molecular formula of the compound obtained in this embodiment is,

[0079]

Embodiment 3

[0080] Embodiment 3: the synthesis of 4-(4'-carboxy)-phenyl terpyridine

[0081] Put 1g of the compound obtained in Example 2 into a three-necked flask, add 20mL of methanol and a small amount of tetrabutylammonium bromide, stir, and then dropwise add KMnO 4 Aqueous solution (2g KMnO 4 ), the dropwise addition was completed and the reaction was continued for 24 hours, then the reaction solution was suction filtered until clarified, and the pH value of the filtrate was adjusted until solids were precipitated, then filtered and dried. 0.76 g of product was obtained, a 72% yield. Mass spectrum: m / z (EI) 353.14 (100%, M + ). 1 H NMR (CDCl 3 ; 400MHz; TMS): δ, ppm 7.12 (m, 2H, o-pyr-H), 7.69-7.66 (m, 4H, Ar-H), 8.19 (d, 2H, o-benzoic acid), 8.46 (m , 4H, pyr-H), 8.59 (d, 2H, o-pyr-H). The molecular formula of the compound obtained in this embodiment is,

[0082]

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Abstract

The invention discloses a derivative with electroluminescent and electrochromic characteristics and a complex thereof. Specifically, a series of mono-branched and poly-branched structures are obtained by taking 4-phenyl terpyridyl as a terminal group and connecting electron-attracting groups (such as nitro, aldehyde group and carboxyl group) or push donor groups (such as hydroxyl, a diphenylamine derivative and a triphenylamine derivative). A general formula is shown in the specifications. The triple pyridine derivative disclosed by the invention has superior light stability, superior thermal stability and remarkable electroluminescent characteristic; a metal complex of the derivative has remarkable triplet luminous characteristic, and can be applied to an OLED (Organic Light Emitting Diode) luminous material; and more importantly, the metal complex has superior electrochromic characteristic, and is suitable to be taken as a smart off-color material.

Description

technical field [0001] The invention belongs to the field of organic electronics, and in particular relates to a class of derivatives containing terpyridine, which has good organic electroluminescent properties, and its metal complexes have excellent electrochromic properties. Background technique [0002] As a relatively rare tridentate organic ligand, terpyridine is widely used in the construction of molecular devices, supramolecular assemblies, colorimetric determination of metal ions and research on coordination chemistry. [0003] The planar structure of the terpyridine group and its strong ability to accept electrons will effectively expand the range of electron delocalization when it is connected with a conjugated system such as a triphenylamine group; The delocalization on the ring can form triphenylammonium cation radicals (holes) during oxidation, and show obvious hole migration characteristics under the action of an electric field. Therefore, the terpyridine is co...

Claims

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Application Information

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IPC IPC(8): C07D213/26C07D213/48C07D213/55C07D213/38C07F15/00C07F15/02C07F15/06C09K11/06C09K9/02
Inventor 王筱梅范丛斌陈志刚叶常青罗建芳王晓宏梁小龙
Owner SUZHOU UNIV OF SCI & TECH
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