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Iridium complex with main ligand containing carbazolyl and application

A technology of iridium complexes and alkyl groups, which is applied in the direction of indium organic compounds, platinum group organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problems of increasing the non-radiative transition rate of molecules and unfavorable luminescent processes , to achieve the effect of improving device efficiency, high external quantum efficiency, and excellent device performance

Pending Publication Date: 2021-02-09
马鞍山南大高新技术研究院有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The structure of the previously reported carbazole-based iridium complex is not restricted due to the free relaxation of the group attached to the carbazole nitrogen, which will increase the non-radiative transition rate of the molecule, which is not conducive to the luminescence process

Method used

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  • Iridium complex with main ligand containing carbazolyl and application
  • Iridium complex with main ligand containing carbazolyl and application
  • Iridium complex with main ligand containing carbazolyl and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 prepares the iridium complex AG02 of the present invention

[0035]

[0036] Preparation of compound L1-1 in the above route: 1-bromo-9H-carbazole (3.00g, 12.24mmol), iodobenzene (3.00g, 14.71mmo), K 2 CO 3 (2.53g, 18.36mmol) and DMPU (10 drops) were added into a sealed pressure-resistant tube, and heated at 200°C for 18h. After cooling to ambient temperature, the mixture was filtered, washing with dichloromethane. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (pure PE eluent) to obtain 3.50 g of compound L1-1 (89% yield).

[0037] Preparation of compound L1-2 in the above route: add n-BuLi (4.78mL, 12.00mmol, 2.50M hexane solution) dropwise to L1-1 (3.50g, 10.90mmol, 1.00equiv.) in anhydrous tetrahydrofuran (60mL ) solution, a pale yellow solution was obtained at -78°C. After stirring for 1 h, trimethyl borate (1.70 g, 16.35 mmol, 1.50 equiv.) was added. The resulting solution was stirred at -78°C f...

Embodiment 2

[0043] Embodiment 2 prepares the iridium complex AG26 of the present invention

[0044]

[0045] Similarly, referring to the synthesis scheme of Example 1 above, the iridium complex AG26 can be prepared by replacing the corresponding raw materials and following a certain mass ratio of the substances. 1 H NMR (500MHz, CD 2 Cl 2 )δ8.52(d, J=5.9Hz, 2H), 7.96(d, J=7.6Hz, 2H), 7.71(s, 2H), 7.62(d, J=8.2Hz, 4H), 7.57–7.49( m,5H),7.36(dd,J=8.8,5.5Hz,6H),7.28(t,J=7.3Hz,3H),7.14(d,J=5.8Hz,2H),6.09(d,J=7.9 Hz,2H),5.68(s,1H),1.04(s,18H). 13 C NMR (126MHz, CD 2 Cl 2 )δ195.19,167.47,154.22,148.29,142.16,141.94,140.02,137.36,137.09,129.96,128.91,126.85,126.57,125.51,125.09,122.01,121.37,121.32,118.85,118.00,115.58,110.79,90.14,53.88,53.67 ,53.45,53.23,53.02,41.15,27.96.HRMS(MALDI-TOF,m / z):[M] + calcd for C59H47F6IrN4O2, 1050.323; found, 1050.666.

Embodiment 3

[0046] Embodiment 3 prepares the iridium complex AG50 of the present invention

[0047]

[0048] Similarly, referring to the synthesis schemes of the above-mentioned examples 1 and 2, the iridium complex AG50 can be prepared by replacing the corresponding raw materials and following a certain mass ratio of the substances. 1 H NMR (500MHz, CD 2 Cl 2 )δ8.32(d, J=5.4Hz, 2H), 7.94(d, J=7.5Hz, 2H), 7.70–7.58(m, 7H), 7.45(d, J=7.8Hz, 6H), 7.29( ddd, J=23.4, 15.4, 7.3Hz, 7H), 7.06(d, J=5.2Hz, 2H), 6.10(d, J=7.8Hz, 2H), 5.66(s, 1H), 1.06(s, 18H ),0.25(s,18H). 13 C NMR (126MHz, CD 2 Cl 2 )δ194.39,164.77,153.59,150.11,146.12,142.48,142.21,139.15,130.76,129.64,127.08,126.93,126.19,124.91,124.69,124.62,121.67,121.16,119.65,118.67,110.75,89.75,53.88,53.67,53.45 ,53.24,53.02,41.13,28.03,-1.69.HRMS(MALDI-TOF,m / z):[M] + calcd for C 63 h 65 IrN 4 o 2 Si 2 , 1058.424; found, 1059.346.

[0049] The iridium complexes AG02, AG26, AG50 thermal analysis spectrum of the present invent...

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Abstract

The invention belongs to the technical field of electroluminescent materials, and relates to a novel iridium complex with a main ligand containing carbazolyl, in the structure, pyridine and derivatives thereof are introduced into the 1-site of carbazole to realize steric hindrance and limit the free relaxation of a benzene ring at the 9-site of carbazole, so that the non-radiative transition process of molecules can be inhibited. The iridium complex disclosed by the invention has very high photoluminescence quantum yield and short excited state service life. A device prepared from the iridiumcomplex is excellent in performance, has high external quantum efficiency, low starting voltage and low efficiency roll-off, and has potential application value in the field of OLED illumination and display.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent devices (OLEDs), in particular to a class of iridium complexes containing carbazole groups as main ligands and their application as luminescent materials in organic electroluminescent devices. Background technique [0002] High-performance phosphorescent emitters for organic light-emitting diodes (OLEDs) have been developed rapidly in the past decades. In particular, OLEDs based on iridium(III) complexes have attracted extensive attention due to their superior quantum efficiency, short triplet excited state lifetime, excellent coordination ability, and tunable color range. Such an advantage is due to the strong spin-orbit coupling caused by the heavy iridium atoms, which accelerates the intersystem cross-acceleration of the singlet excited state to the strongly emitting triplet excited state, so that both singlet and triplet excitons can be captured simultaneously. Therefore, I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54B01J31/22
CPCC07F15/0033C09K11/06B01J31/2295C09K2211/185B01J2531/827H10K85/342H10K50/11B01J35/39
Inventor 郑佑轩张锋罗旭峰曲忠泽杨楠王毅吕宝源潘毅
Owner 马鞍山南大高新技术研究院有限公司
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