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Dendritic iridium coordination compound with double-carrier transport property, application and prepared organic electrophosphorescent device

A technology of transmission properties and iridium complexes, which is applied in the field of organic electrophosphorescent devices and dendritic iridium complexes, can solve the problems of difficult to obtain red electrophosphorescent materials with color purity, increased synthesis difficulty, and poor color purity. Achieve the effect of good development prospects, short reaction time and simple structure

Inactive Publication Date: 2014-03-19
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the large steric hindrance of the coordinated nucleus itself, the red light material is connected to the branch, the steric hindrance is greater, and the synthesis difficulty is also increased.
At the same time, after the branches are added, the spectrum will be red-shifted, and the color purity will become poor. It is difficult to obtain red electrophosphorescent materials with good color purity.

Method used

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  • Dendritic iridium coordination compound with double-carrier transport property, application and prepared organic electrophosphorescent device
  • Dendritic iridium coordination compound with double-carrier transport property, application and prepared organic electrophosphorescent device
  • Dendritic iridium coordination compound with double-carrier transport property, application and prepared organic electrophosphorescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] Synthesis of 1-(3-(9-carbazole)biphenyl)-3,4-dihydroisoquinoline (1) 6.50g (22.7mmol) 1-(3'-bromophenyl)-3,4 - dihydroisoquinoline and 9.22 g (25.0 mmol) N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborinyl)phenyl)carbazole, 12.6mL of 2M sodium carbonate solution, 70ml of toluene, and 35ml of ethanol were put into a 200ml three-necked flask, and Pd(PPh 3 ) 4 0.578g, reflux reaction for 24 hours, extracted with dichloromethane, washed with water several times, dried over anhydrous magnesium sulfate, rotovaped the solvent, passed the column with ethyl acetate:dichloromethane (1:9), and obtained a light yellow solid 4.46 g, yield 83.2%. GC-MS: m / z, 447.2, [M-1] + .1H NMR (300MHz, CDCl 3 ), (ppm): 8.17-8.14 (d, 2H), 7.96 (s, 1H), 7.88-7.85 (m, 2H), 7.81-7.78 (m, 1H), 7.66-7.55 (m, 4H), 7.48 -7.40(m, 6H), 7.36-7.27(m, 4H), 3.94-3.89(m, 2H), 2.89-2.85(t, 2H).

Embodiment 2

[0058]

[0059] Synthesis of 1-(3-(4-N-carbazolyl))biphenylisoquinoline (2) Weigh 3.52g (7.86mmol) 1-(3-(9-carbazole)biphenyl)- 3,4-dihydroisoquinoline (1) was dissolved in 20mL of 1,3,5-trimethylbenzene, light yellow solution, after argon gas was passed in for 30 minutes, 0.45g of 10% Pd / C was added, and the temperature was raised to 190°C. Reacted for 5h, filtered, washed with dichloromethane, evaporated the solvent, and passed through the column with ethyl acetate:dichloromethane (1:9) to obtain a white solid (3.09g, 88.2%). GC-MS: m / z, 445.2, [M-1] + . 1 H NMR (300MHz, CDCl 3 )(ppm): 8.68-8.67(m, 1H), 8.22-8.14(m, 3H), 8.04(s, 1H), 7.96-8.83(m, 4H), 7.83-7.58(m, 7H), 7.49- 7.39(m, 4H), 7.32-7.27(m, 2H).

Embodiment 3

[0061]

[0062] Synthesis of 1-(3-(4-N-(3,6-dibromocarbazolyl))biphenylisoquinoline (3) 1-(3-(4-N-carbazolyl))biphenyl Base isoquinoline (2) was dissolved in 20mL of dichloromethane, 1.98g (11.12mmol) N-bromosuccinimide was added, and the reaction was stirred at room temperature for 3h. The solvent was evaporated, and the volume ratio was 2:1 Dichloromethane and petroleum ether were used as eluents, and silica gel column chromatography gave white powder (2.83g, 85.8%). ESI-MS: m / z, 605.0, [M+1] + . 1 H NMR (300MHz, CDCl 3 ), (ppm): 8.67-8.65 (d, 1H), 8.20-8.18 (d, 3H), 8.02 (s, 1H), 7.94-7.88 (m, 3H), 7.85-7.62 (m, 4H), 7.58 -7.50(m, 5H), 7.32-7.26(m, 2H).

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Abstract

The invention relates to a dendritic iridium coordination compound with a double-carrier transport property, application and a prepared organic electrophosphorescent device. A cyclic metal ligand contained by the heterocyclic iridium coordination compound contains a carbazolyl group with a hole transport property and an auxiliary ligand contains a triazolyl group with an electron transport property. A prepared luminescent material has a good dissolubility in high-boiling-point solvent and a luminescent device can be prepared in a spin coating way. By using solution to produce the luminescent device and by using the red dendritic phosphorescent material with the double-carrier transport property as an independent luminescent layer, the energy level matching and the compatibility of various materials are not required to be considered, a hole transport layer is not required, the production technology of the device is simple and the efficiency of the device is high. The application prospect in the aspect of large-area high-efficiency luminescent devices is good.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence. In particular, it relates to a dendritic iridium complex with dual carrier transport properties, the application of the complex in organic electroluminescent devices, and the prepared organic electroluminescent device. Background technique [0002] Since C.W.Tang published a high-efficiency, high-brightness double-layer structure device, the research of organic electroluminescence has become a hot spot in the field of display (C.W.Tang, S.A.Vanslyke, Appl.Phys.Lett, 1987, 51, 913-915) . Among them, the phosphorescent material breaks through the theoretical limit of the internal quantum efficiency of not more than 25%, and its internal quantum efficiency can reach 100% theoretically, making a major breakthrough in the luminous efficiency of organic light-emitting diodes. Organic / polymer electrophosphorescence (O / PLEDs) has attracted the attention of researchers all over the w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 梁波
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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