Divalent platinum complexes

A platinum complex, unsubstituted technology, used in the field of OLED materials, can solve the problems of high price of rare earth metal Ir, hinder application, and large pollution, and achieve the improvement of heavy atom effect, molecular spatial configuration, and low quenching constant. Effect

Pending Publication Date: 2022-06-21
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the rare earth metal Ir is expensive and polluting, hindering their application in mass production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Divalent platinum complexes
  • Divalent platinum complexes
  • Divalent platinum complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of the compound of structure 1 (1a, refer to CN110872325A, 1d is the ordered material)

[0036]

[0037] Synthesis of Intermediate 1c

[0038] Take a 2L three-necked flask, put in 1a (60.0g, 101mmol), 1b (30.0g, 202mmol), Pd (PPh) 3 ) 4 (5.90g, 5mmol), NaOH (8.2mg, 202mmol) and dioxane / water (1.2L / 240ml), under nitrogen protection, the reaction was stirred at 55°C for 12h. After the reaction, most of the solvent was spin-dried, water was added, extracted twice with DCM, mixed with silica gel and spin-dried (Hex:EA=10:1) and passed through a silica gel column. 58 g of white solid were obtained. The hydrogen spectrum data are as follows:

[0039] 1 H NMR (400MHz, CDCl 3 )δ8.69(s,1H),8.61(d,J=5.3Hz,1H),8.23(d,J=7.8Hz,1H),8.12–8.01(m,3H),7.91(d,J=1.4 Hz,1H),7.85(d,J=1.7Hz,1H),7.62(s,1H),7.55(s,3H),7.47-7.39(m,1H),7.30-7.26(m,1H),7.16 (s, 1H), 7.06(d, J=8.1Hz, 1H), 3.92(s, 3H), 1.41(s, 18H).

[0040] Synthesis of Intermediate 1e

[0041] Take a 250ml sin...

Embodiment 2

[0050] Example 2: Synthesis of the compound of structure 26 (26a is the ordered material)

[0051]

[0052] Synthesis of Intermediate 26b

[0053] Take a 250ml single-necked bottle, put in 1c (8.0g, 19.9mmol), 26a (8.5g, 21.4mmol), Pd 132 (0.303g, 0.42mmol), K 2 CO 3 (5.9g, 42.7mmol), and THF / water (80ml / 16ml), under nitrogen protection, react at 70°C for 12h. After the reaction, most of the solvent was spin-dried, water was added, extracted twice with EA, mixed with silica gel and spin-dried, and passed through a silica gel column with (Hex:EA=6:1) to obtain 11.08g of white solid. The hydrogen spectrum data are as follows:

[0054] 1 H NMR (400MHz, Chloroform-d) δ8.67 (d, J=4.5Hz, 1H), 8.22–8.17 (m, 3H), 8.17–8.08 (m, 3H), 7.95–7.86 (m, 4H), 7.72(dd,J=6.8,2.4Hz,1H),7.69-7.59(m,2H),7.53-7.27(m,10H),7.15(ddd,J=8.7,7.5,1.2Hz,1H),6.90( dd,J=7.7,1.2Hz,1H),3.90(s,3H),1.35(s,36H).

[0055] Synthesis of Intermediate 26c

[0056] Take a 500ml single-neck bottle, put in 26b...

Embodiment 3

[0060] Example 3: Synthesis of the compound of structure 36 (36a is the ordered material)

[0061]

[0062] Synthesis of Intermediate 36c

[0063] 36a in a dry 500ml double-necked flask (14.7g, 50mmol), add 36b (11.8g, 50mmol), toluene (120mL), add ethanol (60mL) and 2mol / L potassium carbonate solution (60mL), first ultrasonic 5- After 10 minutes, the nitrogen gas was rapidly stirred for 5 minutes, the catalyst tetrakis(triphenylphosphine) palladium (1.8 g, 1.5 mmol) was rapidly added, and a large amount of nitrogen gas was passed for 10 minutes. It was heated to 100° C., stirred for 12 hours, extracted first during treatment, spin-dried, and chromatographed with petroleum ether and dichloromethane to obtain 14.5 g of a white solid product with a yield of 90%. The hydrogen spectrum data are as follows:

[0064] 1 H NMR (400MHz, Chloroform-d) δ 9.54 (s, 1H), 8.37 (dd, J=4.0, 2.2Hz, 1H), 8.17–8.10 (m, 2H), 7.94 (dd, J=7.5, 2.2 Hz,1H),7.56(s,1H),7.55–7.48(m,2H),7.46(dd,J=7...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The structure of the bivalent platinum complex is shown as a formula (I). The complex has bright green light emission wavelength and can be applied to the field of OLED (organic light emitting diode) materials. Through structural design, the heavy atom effect of the phosphorescent material can be improved, spin coupling can be enhanced, and T1-S0 efficient conversion can be realized, so that efficient luminous efficiency is obtained. Meanwhile, the platinum complex molecule of the ONCN tetradentate ligand has the advantages of being simple in synthesis step, easy to coordinate and the like, has more modifiable sites, and can be used for adjusting the PL light-emitting wavelength and the thermal stability. Due to steric hindrance increased by carbazole groups, the aggregation effect among molecules can be effectively reduced, exciplexes are prevented from being formed, and the color purity and the luminous efficiency are further improved.

Description

technical field [0001] The invention relates to the field of OLED materials, in particular to a class of carbazole-containing divalent platinum complexes. Background technique [0002] Organic Light-Emitting Diode (OLED) has the advantages of self-luminescence, wide viewing angle, almost infinitely high contrast ratio, low power consumption, extremely high response speed, and potential flexible and foldable. Follow and research. Since it was discovered in the laboratory by Chinese-American professor Ching W.Tang in 1979, in 1998 S.R.Forrest et al. found that organometallic complexes can achieve fast system due to their strong spin-orbit coupling (SOC). Interstitial Crossing (ISC) and long-lived phosphorescent decay. And studies have shown that phosphorescent materials can make full use of the energy of singlet and triplet excitons during the luminescence process, improve the luminous efficiency of the complexes, and theoretically achieve an internal quantum efficiency of 1...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC07F15/0086C09K11/06C09K2211/185C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1044H10K85/346H10K50/11C07D401/14H10K85/00H10K50/00C07D405/14C07D409/14H10K50/12
Inventor 吴信蔚李慧杨沈文渊檀笑风戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap