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Cyclic metallic platinum compounding agent electrofluor scence material containing triaryl amine functional redical

A phosphorescent material and electrophosphorescence technology, applied in luminescent materials, electroluminescence light sources, electric light sources, etc., can solve the problems of difficulty in improving luminous efficiency and achieve good carrier injection and excellent recombination performance

Inactive Publication Date: 2006-06-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Since organic cyclometal platinum complexes have a longer phosphorescence lifetime (30-50 μs) than cyclometal iridium complexes, and their structure is a planar structure, it is generally believed that organic cyclometal platinum complexes are prone to phosphorescence quenching, and the luminous efficiency is difficult. improve

Method used

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  • Cyclic metallic platinum compounding agent electrofluor scence material containing triaryl amine functional redical
  • Cyclic metallic platinum compounding agent electrofluor scence material containing triaryl amine functional redical
  • Cyclic metallic platinum compounding agent electrofluor scence material containing triaryl amine functional redical

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of 2-(4-aminophenyl)pyridine

[0027]

[0028] In a 100mL three-necked flask, add 4.0g (20mmol) 2-(4-nitrophenyl)pyridine and 40mL ethanol, heat to 50°C, add 0.2g 5% Pd-C, and then add 4mL 80 % hydrazine hydrate and 0.2g 5% Pd-C, reflux reaction 4hr. After most of the ethanol was evaporated, 15 mL of water was added to precipitate a white solid, which was filtered by suction, washed with water, and dried in vacuum to obtain 3.4 g of white crystals with a yield of 98.8%. Melting point (m.p). 96-97°C (literature value [9] 97-98°C). Infrared spectrum (IR) (KBr, cm -1 ): 3452, 3306 (N-H), 3190 (Ar-NH2 combination peak), 1631, 1606, 1522, 1470 (aromatic ring skeleton), 836 (1,4-disubstituted benzene). Proton nuclear magnetic spectrum (1HNMR) (400MHz, CDCl 3 ) δppm: 8.62 (d, 1H), 7.83 (d, 2H), 7.70 ~ 7.61 (m, 2H), 7.14 ~ 7.09 (t, 1H), 6.76 (d, 2H), 3.81 (s, 2H).

Embodiment 2

[0030] Synthesis of N,N-bis(4-tert-butylphenyl)-4-(2'-pyridyl)aniline (BuPhNPPy)

[0031]

[0032] 1.0g (5.9mmol) 2-(4-aminophenyl) pyridine, 3.8g (14.6mmol) 4-tert-butyl iodobenzene, 6.6g anhydrous potassium carbonate, 1.5g activated copper powder, 0.4g dibenzo -18-Crown-6 and 20mL of o-dichlorobenzene were added to a 100mL three-neck flask, under the protection of nitrogen, heated to reflux for 21hr, cooled, suction filtered, and o-dichlorobenzene was recovered by vacuum distillation, and the residue was washed with 200-300 mesh silica gel As the stationary phase, dichloromethane was used as the eluent, and separated by column chromatography to obtain 1.2 g of white solid with a yield of 46.8%. m.p.228~230℃. 1HNMR (400MHz, CDCl3 ) δppm: 8.54 (d, 1H), 7.85 (d, 2H), 7.64 ~ 7.70 (m, 2H), 7.28 (d, 4H), 7.04 ~ 7.17 (m, 7H), 1.32 (s, 18H).

Embodiment 3

[0034] Synthesis of N, N-diphenyl-4-(2'-pyridyl)aniline (PhNPPy)

[0035]

[0036] 1.5g (8.9mmol) 2-(4-aminophenyl) pyridine, 2.5mL (21.9mmol) iodobenzene, 9.9g (71.7mmol) anhydrous potassium carbonate, 2.3g activated copper powder, 0.6g dibenzo- Add 18-crown-6 and 30mL o-dichlorobenzene into a 100mL three-necked flask, heat and reflux for 24hrs under the protection of nitrogen, cool, filter with suction, and recover o-dichlorobenzene by distillation under reduced pressure. As the stationary phase, dichloromethane was used as the eluent and separated by column chromatography to obtain 1.5 g of white solid with a yield of 51.7%. m.p.178-179°C. 1HNMR (400MHz, CDCl 3 )δppm: 8.73~8.62(d, 1H), 7.88~7.86(d, 2H), 7.73~7.65(m, 2H), 7.29~7.25(t, 4H), 7.18~7.05(m, 7H), 7.06~ 7.02(t, 2H).

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Abstract

The invention relates to ring metal platinum complexes electro phosphorescence material containing tri-fragrant amine function group. Its manufacturing includes the following steps: linkage of pyridine heterocyclic compound and tri-fragrant amine to form CN bi-tooth ligand; further reacting with platinum ion and OO anion auxiliary ligand to gain the new type single ring metal platinum complexes electro phosphorescence material. The invention mixes ring metal platinum complexes with PFO and PVK to form polymer electro phosphorescence device. It can adjudge electronic structure, hole-injection, and transmission performance to renovate electroluminescence of the device. The invention can be applied to organic electroluminescence field, especially used to manufacture high performance organic electroluminescence device.

Description

technical field [0001] The invention relates to an organic electrophosphorescent material, in particular to an electrophosphorescent material of a ring metal platinum complex containing a triarylamine functional group. Background technique [0002] In 1998, the Forrest group of Princeton University in the United States reported for the first time that octaethyl porphyrin platinum (II) complex (PtOEt) was doped in 8-hydroxyquinoline aluminum (Alq 3 ), obtained an electrophosphorescent device with an internal quantum efficiency of 23% and an external quantum efficiency of 4% (M.A.Baldo, D.F.O'Brien, Y.You, et al.Nature, 1998, 395, 151), which immediately caused It has aroused great interest in electrophosphorescent materials and their devices. Subsequently, organic iridium (Ir) (Appl.Phys.Lett.2001, 78, 1622.Adv.Funct.Mater.2005, 15, 1451), platinum (Pt) (Appl.Phys.Lett.2005, 86, 153505, Adv.Funct.Mater.2005, 15, 223), osmium (Os) (Chem.Mater.2005, 17, 3532), ruthenium (Ru) ...

Claims

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Application Information

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IPC IPC(8): C09K11/06H05B33/14
Inventor 朱卫国刘坚罗翠萍胡峥勇刘煜朱美香
Owner XIANGTAN UNIV
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