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Arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof

A metal platinum and aromatic amine technology, applied in the field of near-infrared electroluminescent materials, can solve the problems of restricting the development of organocyclic metal platinum complexes, difficult to satisfy, low photoluminescence quantum efficiency, etc., and improve carrier transport. ability, improve energy conversion efficiency, and improve the effect of photoelectric conversion efficiency

Active Publication Date: 2016-04-13
XIANGTAN UNIV
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are some problems in these cyclometal platinum complex near-infrared luminescent materials and their electroluminescent devices, which are mainly reflected in: 1)d 8 The electronic structure of platinum cyclometal complexes has good planarity, and the molecules are easy to aggregate, resulting in low photoluminescence quantum efficiency; The need for near-infrared electroluminescent devices that emit light efficiently; 3) At high current densities, the luminescence is easily quenched, and the efficiency of the device rolls off seriously
These problems seriously restrict the development of organic cyclometal platinum complexes in the field of near-infrared electroluminescence

Method used

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  • Arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof
  • Arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof
  • Arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Cyclometallic Platinum Complex TPA-2q-PtCl 2 Synthesis

[0048]

[0049] 1.1 Synthesis of Intermediate 1

[0050] In a 100mL single-necked bottle, add 4-tert-butylaniline (537mg, 3.6mmol), 1,3-dibromobenzene (2.50g, 10.8mmol), sodium tert-butoxide (1.04g, 10.8mmol), three ( Dibenzylideneacetone)dipalladium (166mg, 0.29mmol), 1,1'-bis(diphenylphosphino)ferrocene (160mg, 0.29mmol) and toluene (40mL). Stir and heat to 120°C under nitrogen atmosphere, react for 18h, and cool to room temperature. Add 50 mL of ethyl acetate and continue stirring for 30 min. Suction filtration, the filtrate was collected, the solvent was distilled off under reduced pressure, and the mixed solution of n-hexane / ethyl acetate with a volume ratio of 20:1 was used as the eluent for column chromatography to obtain 785 mg of the product with a yield of 47.5%. 1 HNMR (400MHz, CDCl 3 )δ: 7.30 (d, J = 8.5Hz, 2H), 7.16 (d, J = 16.4Hz, 2H), 7.10 (q, J = 8.1Hz, 4H), 6.98 (t, J = 8.2Hz, 4H) ,1.33(s...

Embodiment 2

[0056] Cyclometallic Platinum Complex 3TPA-2q-PtCl 2 Synthesis

[0057]

[0058] 2.1 Synthesis of intermediate 3

[0059] The synthesis of Intermediate 3 in Example 2 is similar to the synthesis of Intermediate 1 in Example 1. A white solid was obtained with a yield of 36%. 1 HNMR (400MHz, CDCl 3 )δ:7.33(s,2H),7.31(s,4H),7.28(d,J=5.3Hz,6H),7.25(s,4H),7.19(s,2H),7.13(s,2H), 7.05(d,J=5.4Hz,10H),7.02(s,4H),1.33(s,9H),1.31(s,36H).MALDI-MS(m / z):1169.521for[M + ]. 13 CNMR (100MHz, CDCl 3 )δ: 31.46, 34.34, 120.68, 122.50, 123.23, 124.01, 124.30, 124.50, 126.14, 126.55, 127.56, 132.12, 143.67, 143.81, 144.74, 146.08, 148.23, 149.17

[0060] 2.2 Synthesis of Intermediate 4

[0061] The synthesis of Intermediate 4 in Example 2 is similar to the synthesis of Intermediate 2 in Example 1. A white solid was obtained with a yield of 32%. 1 HNMR (400MHz, CDCl 3 )δ: 8.57 (d, J = 5.3Hz, 2H), 8.04 (d, J = 8.1Hz, 2H), 7.83 (d, J = 7.9Hz, 2H), 7.57 (dd, J = 19.8, 11.9Hz, 8H),7.47–7....

Embodiment 3

[0065] Characterization of arylamine-based tetradentate cyclometal platinum complexes and their fabrication and luminescent properties of single-emitting layer polymer electroluminescent devices

[0066] Arylamine Tetradentate Cyclometallic Platinum Complexes 1 The HNMR spectrum was measured by BrukerDex-400NMR instrument, the UV-visible absorption spectrum was measured by CARY100 UV-visible spectrometer, and the photoluminescence spectrum was measured by Perkin-ElmerLS-50 fluorescence spectrometer.

[0067] Single-emitting layer polymer electroluminescent devices based on arylamine tetradentate cyclometal platinum complex phosphorescent materials include: indium tin oxide (ITO) conductive glass, polydioxyethylthiophene (PEDOT) electron blocking layer, light-emitting layer ,cathode. The light-emitting layer is composed of a host material and a dopant material. The host material is PVK, the dopant is an aromatic amine tetradentate cyclometal platinum complex phosphorescent ma...

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Abstract

The invention discloses arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof. The cyclometalated platinum complexes contain ligands comprising dual donor units (triphenylamine fluorene or carbazole) and dual C^N tetradentate coordination structures; the donor units in cyclometalated complex molecules can further enlarge a conjugated system of the complexes, red shift of the emission spectra of the complexes is realized, and the complexes have a near-infrared emission characteristic. Efficient near-infrared emission can be realized when the cyclometalated platinum complexes are applied to preparation of polymer electroluminescent devices.

Description

technical field [0001] The invention relates to a near-infrared electroluminescence material of an aromatic amine tetradentate ring metal platinum complex, a synthesis method thereof, and an application of the near-infrared electroluminescence material in a polymer electroluminescence device; it belongs to a near-infrared electroluminescence material field. Background technique [0002] With the popularization of today's network technology and digital multimedia technology, information light source, as an indispensable part of large-capacity and high-speed optical communication, optical storage and photoelectric display technology, is playing an increasingly important role, and has aroused great interest from scientists. big interest. [0003] As one of the important sources of information light sources, organic near-infrared luminescent materials have been widely used in night vision technology, biological probes, and optical fiber communications in recent years ([1].G.Qia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0006C09K2211/185H10K85/346C09B57/008C09B57/10H10K85/141H10K85/6572H10K50/11H10K2101/10
Inventor 朱卫国张友明谭华王亚飞刘煜
Owner XIANGTAN UNIV
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