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A kind of phosphorescent ptm3 heterotetranuclear complex and its preparation method and use

A complex, phosphorescence technology, applied in chemical instruments and methods, luminescent materials, semiconductor/solid-state device manufacturing, etc., can solve the problems of incomplete chromaticity, high price, shortage of iridium resources, etc., and achieve excellent performance and high conversion efficiency. Effect

Active Publication Date: 2020-02-21
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are challenging problems such as high price, incomplete chromaticity (lack of blue phosphorescent materials), shortage of iridium resources, and difficulty in preparing large-scale devices.

Method used

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  • A kind of phosphorescent ptm3 heterotetranuclear complex and its preparation method and use
  • A kind of phosphorescent ptm3 heterotetranuclear complex and its preparation method and use
  • A kind of phosphorescent ptm3 heterotetranuclear complex and its preparation method and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1: the preparation of complex 1

[0065] Dissolved Pt(PPh 3 ) 2 (C≡C-4-C 6 h 4 Carb-9) 2 (62.6mg, 0.05mmol) in dichloromethane solution was added (Ph 2 PCH 2 ) 3 P(62.8mg, 0.1mmol), Au(tht)Cl(48mg, 0.15mmol), NH 4 ClO 4(18 mg, 0.15 mmol). The reaction solution turned light yellow after being stirred at room temperature for 8 hours. The product was purified by silica gel column chromatography using CH 2 Cl 2 / MeOH (V / V=10:0.5) was used as the eluent to collect the main product. Yield: 68%. 1 H NMR (CDCl 3 ,ppm):8.18(d,4H,J=7.72Hz), 7.93-7.97(m,16H),7.72(d,8H,J=6.88Hz),7.50-7.54(m,16H),7.39-7.42( m, 14H), 7.31-7.34(m, 10H), 7.16(t, 8H, J=7.52Hz), 6.90(d, 4H, J=8.36Hz), 5.70(d, 4H, J=8.32Hz), 4.17(br,4H),3.67(br,8H). 31 P NMR (CDCl 3 ,ppm):30.4(t, 4P,J P-P =31.5Hz), 22.7(m,2P,J P-P =25.0Hz), 4.2(t,2P,J P-P =25.1Hz,J Pt-P = 2676Hz).HRMS(ESI): According to C 118 h 96 Au 3 ClN 2 P 8 Pt[M-2ClO 4 ] 2+ Calculated value: 1305.1880; Measured...

Embodiment 2

[0066] Embodiment 2: the preparation of complex 2

[0067] Preparation method is identical with method in embodiment 1, only is to use Pt(PPh 3 ) 2 (C≡C-C 6 h 4 Bu t -4) 2 Instead of Pt(PPh 3 ) 2 (C≡C-4-C 6 h 4 Carb-9) 2 , Yield: 72%. 1 H NMR (CDCl 3 ,ppm): 7.89-7.93(m,8H),7.74-7.77(m,8H,7.66-7.70(m,8H),7.49-7.52(m,14H), 7.31-7.34(m,14H),7.02- 7.05(m,8H,6.54(d,4H,J=8.04Hz),5.41(d,4H,J=8.04Hz),4.08(br,4H),3.85(br,4H),3.54(br,4H) 0.98-1.2(m,18H). 31 P NMR (CDCl 3 ,ppm):29.1(t,4P,J P-P =32.6Hz), 17.8(m,2P,J P-P =30.0Hz),4.8(t,2P,J P-P =27.1Hz,J Pt-P =2694Hz).HRMS(ESI):according to C 102 h 98 Au 3 ClN 2 P 8 Pt[M-2ClO 4 ] 2+ Calculated value: 1196.1927; Measured value: 1196.1976.IR(KBr,cm -1 ):2105w(C≡C), 1100s(ClO 4 - ).

Embodiment 3

[0068] Embodiment 3: the preparation of complex 3

[0069] Preparation method is identical with method in embodiment 1, only is to use Pt(PPh 3 ) 2 (C≡C-2-PhCarb-9) 2 Instead of Pt(PPh 3 ) 2 (C≡C-4-C 6 h 4 Carb-9) 2 . Yield: 70%. 1 H NMR (CDCl 3 ,ppm): 8.01-8.03(m,8H),7.74-7.77(m,10H),7.66-7.69(m,10H),7.51-7.55(m,12H), 7.43-7.49(m,12H),7.37 -7.41(m,16H),6.95(m,10H),6.78(d,2H,J=8.4Hz), 6.02(s,2H),5.78(d,2H,J=8.4Hz),4.13(br, 4H), 4.03(br,4H), 3.65(br,4H). 31 P NMR (CDCl 3 ,ppm):29.6(t,4P,J P-P =32.0Hz), 18.1(m,2P,J P-P =30.6Hz), 6.2(t,2P,J P-P =30.0Hz,J Pt-P =2726Hz).HRMS(ESI):according to C 118 h 96 Au 3 ClN 2 P 8 Pt[M-2ClO 4 ] 2+ Calculated value: 1305.1880; Measured value: 1305.1909.IR (KBr, cm -1 ):2099w(C≡C),1100s(ClO 4 - ).

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Abstract

The present invention relates to an ionic phosphorescent metal complex and its preparation method and application. The structure of the complex is: [PtM 3 {(PPh 2 CH 2 ) 3 P}(C≡CR)}(C≡CR’)(μ‑Cl)] 2+ A n‑ 2 / n ; wherein, M is selected from Au (I) or Ag (I); R, R' the same or different, independently selected from: alkyl, alkenyl, alkynyl, aryl, heteroaryl; the alkyl Base, alkenyl, alkynyl, aryl, heteroaryl can be substituted by one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, amino, halogen, haloalkane radical, aryl, heteroaryl; said substituent is optionally further substituted by one or more of the following groups: alkyl, alkoxyl, amino, halogen, haloalkyl, aryl, heteroaryl; A n‑ is a monovalent or divalent anion, n is 1 or 2; μ‑represents a bridge. The organic light-emitting diode prepared by using the complex as the dopant of the light-emitting layer has an external quantum efficiency greater than 10%, and can be applied in the fields of flat panel display and daily lighting.

Description

technical field [0001] The invention belongs to the field of phosphorescent materials and organic light-emitting diodes, in particular to a phosphorescent PtM 3 Heterotetranuclear organometallic alkyne complex and its preparation method and use. Background technique [0002] Organic light-emitting diode (OLED) is a thin-film light-emitting device with a sandwich structure, which can convert electrical energy into light energy under the action of a low voltage of 3-12V, that is, electroluminescence, which has a very wide application in the field of flat panel display and lighting . The core of organic light-emitting diodes is the light-emitting material. At present, most of the commercial phosphorescent materials are electrically neutral cyclometallic iridium (III) complexes, which are doped into the organic host material to form the light-emitting layer. The biggest advantage is that it is convenient for vacuum thermal evaporation. Plating makes an ideal thin film light em...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C09K11/06H01L51/50H01L51/54H01L51/56
CPCC09K11/06C07F19/00C09K2211/185C09K2211/188H10K85/361H10K85/371H10K50/12H10K85/6565H10K85/346H10K50/11H10K2101/10H10K2101/90H10K50/156H10K50/166
Inventor 陈忠宁施林熙王金云
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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