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Organic electrofluorescent iridium complex material

A technology of phosphorescent materials and iridium complexes, which is applied in the field of iridium complex-based organic electrophosphorescent materials and their synthesis, can solve the problems of reduced lifetime and stability of light-emitting devices, concentration quenching, etc., and achieve reduced phosphorescent lifetime and reduced interaction role, reduce the effect of phase separation

Inactive Publication Date: 2009-08-26
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, organic electrophosphorescent metal complex materials are usually doped with a certain concentration in the host material to make light-emitting devices. Since the light-emitting device will generate Joule heat during operation, the original uniformly dispersed small molecule light-emitting materials will be produced. Aggregation and crystallization, resulting in phase separation and quenching of the concentration of phosphorescent materials, resulting in reduced lifetime and stability of light-emitting devices

Method used

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  • Organic electrofluorescent iridium complex material

Examples

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Embodiment 1

[0024] The organic electrophosphorescent material in this embodiment is an orange-red phosphorescent material, and the purpose of increasing the molecular volume is achieved by introducing a tert-butyl group to the para-position of the 2-phenyl group of the 2-phenylbenzothiazole ligand. Its structural formula is as follows:

[0025]

[0026] In the above structural formula, X is S, R is C(CH 3 ) 3 .

[0027] The preparation process is:

[0028] 1, Preparation of 2-p-tert-butylphenylbenzothiazole (referred to as ligand 1)

[0029] at room temperature, N 2 Under protection, add 0.1mol o-aminothiophenol and 60ml 1-methyl-2-pyrrolidone to a 100ml three-necked flask equipped with a tail gas absorption and condenser tube, then add 0.1mol p-tert-butylbenzene dropwise with a constant pressure funnel Acyl chloride, after the dropwise addition, heated to 100°C for 1 hour to react, the color of the solution changed from yellow to brown, cooled to room temperature, poured the solu...

Embodiment 2

[0034] The organic electrophosphorescent material in this embodiment is an orange-red phosphorescent material, and the purpose of increasing the molecular volume is achieved by introducing an isopropyl group to the para-position of the 2-phenyl group of the 2-phenylbenzothiazole ligand. Its structural formula is as follows:

[0035]

[0036] In the above structural formula, X is S, R is CH(CH 3 ) 2 .

[0037] The preparation process is:

[0038] 1, Preparation of 2-p-isopropylphenylbenzothiazole (referred to as ligand 2)

[0039] Process flow and relevant parameter are identical with embodiment 1, and raw material is substantially identical with embodiment 1, and difference with embodiment 1 is that p-tert-butylbenzoyl chloride in raw material is changed to p-isopropylbenzoyl chloride. The p-cymenoyl chloride used was prepared by refluxing p-cymenic acid with excess thionyl chloride.

[0040] 2. Preparation of complex organic electrophosphorescent material acetylaceton...

Embodiment 3

[0044] The organic electrophosphorescent material in this embodiment is a green phosphorescent material, which is obtained by introducing a tert-butyl group to the para-position of the 2-position phenyl of the 1,2-diphenyl-1H-benzo[d]imidazole ligand. To achieve the purpose of increasing the molecular volume. Its structural formula is as follows:

[0045]

[0046] In the above structural formula, X is ph-N, R is C(CH 3 ) 3 .

[0047] The preparation process is:

[0048] 1. Preparation of 1-phenyl-2-(p-tert-butylphenyl)-1H-benzo[d]imidazole (ligand 3 for short)

[0049] Add 110mmol of o-nitro-N-phenylaniline, 15mmol of zinc chloride, 100ml of benzene and 100mol of p-tert-butylbenzoyl chloride into a 250ml three-necked flask at room temperature, and then heat to reflux for 3 hours. After the reaction is complete, cool to room temperature and filter with suction. The filtrate was evaporated to dryness, and the obtained solid was recrystallized from ethanol to obtain pure...

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Abstract

The iridium complex organic electrophosphorescent material provided by the present invention introduces a group R with large steric hindrance on the ligand, and the structural formula is as follows: in the above structural formula, R is tert-butyl or isopropyl, and X is A sulfur atom or a nitrogen atom to which a phenyl substituent is attached. The combination of R and X has four forms: or X is an S atom, R is a tert-butyl group; or X is an S atom, and R is an isopropyl group; or X is an N atom with a phenyl substituent, and R is tert-butyl; or X is an N atom with a phenyl substituent, and R is an isopropyl group. The phosphorescence material can reduce the influence of phosphorescence quenching caused by phase separation on the luminous efficiency of the device, and the phosphorescence lifetime is reduced by about one time compared with the existing similar materials.

Description

technical field [0001] The invention belongs to the field of organic electrophosphorescent materials, in particular to an iridium complex organic electrophosphorescent material and a synthesis method thereof. Background technique [0002] Organic electrophosphorescent materials have attracted extensive attention because they can effectively utilize triplet excitons and greatly improve luminous efficiency. In 1999, Professor Thompson of the University of Southern California and Professor Forrest of Princeton University introduced three (2-phenylpyridine) iridium (III) [abbreviated as Ir (ppy) 3 ] doped into 4,4'-N, N-dicarbazole biphenyl (abbreviated as BCP) to make a green photoluminescence phosphorescent device, and its highest external quantum efficiency reaches 8.0% [see Baldo M A, Lamansky S, BurrowsP E , Thompson M E, Forrest S R, Appl. Phys. Lett. 1999, 11, 3709]. Subsequently, Thompson et al. reported a series of cyclometallic ligands (C^N) and monoanionic bidentate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06
Inventor 黄荣魏孝强卢志云谢明贵
Owner SICHUAN UNIV
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