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Platinum complex of ONCN tetradentate ligand containing carbazole

A technology of platinum complexes and tetradentate ligands, which is applied in the field of OLED materials to achieve high-efficiency conversion, simple synthesis steps, and reduced aggregation effects

Pending Publication Date: 2022-06-03
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, in terms of performance, such as luminous efficiency and service life, it still needs to be further improved.

Method used

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  • Platinum complex of ONCN tetradentate ligand containing carbazole
  • Platinum complex of ONCN tetradentate ligand containing carbazole
  • Platinum complex of ONCN tetradentate ligand containing carbazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of Intermediate G

[0036]

[0037] Synthesis of Intermediate C

[0038] Take a 1000ml three-necked bottle and put in A (10.0g, 40mmol, 1.0eq.), B (11.7g, 50mmol, 1.25eq.), Pd 132 (280mg, 0.4mmol, 1%eq.), K 2 CO 3 (13.8g, 100mmol, 2.5eq.) and toluene / ethanol / H 2 O (200 / 200 / 50ml), under nitrogen protection, the reaction was stirred at 90°C for 12h. After the reaction, most of the reaction solution was spin-dried, deionized water was added, extracted with dichloromethane three times, and the mixture was spin-dried and mixed with silica gel to pass through the column (Hex:EA=10:1). Finally, 21.0 g of a brown solid was obtained (yield 94.2%). The hydrogen spectrum data are as follows:

[0039] 1 H NMR (400MHz, CDCl 3 )δ8.52(s, 1H), 8.31(d, J=5.2Hz, 1H), 8.16–8.07(m, 2H), 7.46(dd, J=9.1, 2.6Hz, 3H), 7.31(s, 1H) ), 7.28(s, 1H), 7.20(dd, J=5.3, 1.4Hz, 1H), 7.08(s, 1H), 4.03(s, 3H).

[0040] Synthesis of Intermediate D

[0041] Take 250ml sing...

Embodiment 2

[0048] Example 2: Synthesis of Complex 2

[0049]

[0050] Synthesis of Intermediate 2b

[0051] In a 250ml three-necked flask, add G (5.0g, 1.0eq), 2-iodonaphthalene (5.50g, 3.0eq), Cu (230mg, 0.5eq), CuI (688mg, 0.5eq), 1,10-Philo Linen (1.30g, 1.0eq) and cesium carbonate (7.06g, 3.0eq), 100ml of anhydrous xylene as the reaction solvent, nitrogen protection, oil bath temperature 160 ℃ for 3d reaction, cooled to room temperature, the reaction solution was rinsed with EA The agent was directly filtered to remove inorganic salts, and then stirred with silica gel column chromatography (chromatographic liquid hex:EA=8:1), and 3.8 g of yellow fluorescent product spots were collected. The hydrogen spectrum data is as follows 1 H NMR (400MHz, CDCl 3 )δ8.30(dd,J=5.9,3.1Hz,1H),8.24(d,J=8.2Hz,2H),8.18(s,2H),8.07(d,J=4.1Hz,2H),7.89( s, 1H), 7.59(t, J=5.1Hz, 6H), 7.48(d, J=8.6Hz, 2H), 7.45–7.30(m, 8H), 7.29(s, 1H), 7.17(s, 2H ), 7.06(dd, J=8.7, 5.1Hz, 3H), 3.91(s, 3H), 1.43(s, 18...

Embodiment 3

[0055] Example 3: Synthesis of complex 19

[0056] Synthesis of complex 19

[0057]

[0058] Synthesis of Intermediate 19b

[0059] Get 250ml there-necked flask, drop into intermediate G ((2.5g, 3.61mmol), 20a (2.02g, 7.22mmol), Cu (115mg, 1.81mmol), CuI (345mg, 1.81mmol), CsCO 3 (3.53 g, 10.83 mmol), o-phenanthroline (651 mg, 3.61 mmol) and xylene (50 ml), under nitrogen protection, the reaction was stirred at 160° C. for 30 h. After the reaction, it was directly filtered with suction, rinsed with EA, and spin-dried to obtain a brown solid, which was then passed through a silica gel column with (Hex:EA=5:1) to obtain 2.2 g of a white solid. The hydrogen spectrum data are as follows:

[0060] 1H NMR (400MHz, CDCl3) δ 8.49 (s, 1H), 8.42 (d, J=4.9Hz, 1H), 8.27 (dd, J=5.5, 3.5Hz, 1H), 8.19 (dd, J=14.2, 7.7Hz, 2H), 8.01 (d, J=6.4Hz, 2H), 7.90 (d, J=7.7Hz, 1H), 7.84 (d, J=1.1Hz, 1H), 7.57–7.47 (m, 4H) ,7.46(s,1H),7.38(ddd,J=22.4,10.0,5.3Hz,5H),7.28(d,J=8.1Hz,1H),7.22–7.07(m...

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Abstract

The invention relates to a platinum complex of an ONCN tetradentate ligand containing carbazole. The structure of the 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. And meanwhile, the platinum complex molecule of the ONCN tetradentate ligand has the advantages of simple synthesis steps and more modifiable sites. 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 platinum complex containing a carbazole-containing ONCN tetradentate ligand. Background technique [0002] Organic Light-Emitting Diode (OLED) was discovered in the laboratory by Chinese-American professor Ching W.Tang in 1979, because of its self-luminescence, wide viewing angle, almost infinitely high contrast ratio, high contrast ratio, and high contrast ratio. The advantages of low power consumption, extremely high reaction speed, and potential flexibility and foldability have attracted extensive attention and research. In the field of OLED materials, phosphorescent OLED light-emitting layer doping materials have developed rapidly and maturely, which are mainly based on some heavy metal organic complexes. Phosphorescent materials can make full use of the energy of singlet and triplet excitons in the process of luminescence, so theoretically their quantum efficiency can reach ...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC07F15/0086C09K11/06C09K2211/185H10K85/346H10K50/11H10K50/12H10K85/00H10K2101/10C07D401/14C09K2211/1044
Inventor 吴信蔚李慧杨戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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