Organic electroluminescence material comprising 4,5-diazaspiro thioxanthone structure, application of organic electroluminescence material, and device

An electroluminescent material, diazaspiro technology, applied in luminescent materials, electric solid devices, electrical components, etc., can solve the problems of unbalanced OLED turn-on voltage and life, single carrier transport properties, high turn-on voltage, etc. , to achieve the effect of improving external quantum efficiency, high glass transition temperature and thermal decomposition temperature, and low turn-on voltage

Active Publication Date: 2017-01-25
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional host materials usually only have a single carrier transport property, and this unbalanced carrier transport property has been shown to be detrimental to the turn-on voltage and lifetime of OLEDs.
The development of new host materials must have good bipolar carrier (hole and electron) injection and transport properties to avoid the accumulation of carriers between the light-emitting layer and the charge-transport layer, causing the exciplexes at the interface to emit light , resulting in low external quantum efficiency, power efficiency, current efficiency and other main parameters of the device, high turn-on voltage, and spectral instability.

Method used

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  • Organic electroluminescence material comprising 4,5-diazaspiro thioxanthone structure, application of organic electroluminescence material, and device
  • Organic electroluminescence material comprising 4,5-diazaspiro thioxanthone structure, application of organic electroluminescence material, and device
  • Organic electroluminescence material comprising 4,5-diazaspiro thioxanthone structure, application of organic electroluminescence material, and device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of intermediate M1

[0036]

[0037] Under nitrogen protection, diphenylsulfone (10.9 g, 0.05 mol) and tetrahydrofuran (109 mL) were added into a 500 mL three-necked flask. The bath temperature was set at -85°C, and the temperature was lowered with stirring. When the internal temperature dropped to -80°C, a solution of n-butyllithium in n-hexane (24 mL, 2.5M) was added dropwise, and the dropping rate was controlled to keep the internal temperature below -80°C. After the dropwise addition, keep the reaction for 3h, move to room temperature at 25°C and stir for 2h. A solution of methyl 5-bromo-[2,2'-bipyridine]-3-carboxylate (14.6 g, 0.05 mol) in tetrahydrofuran (100 mL) was added dropwise. After the dropwise addition was completed, the mixture was stirred for 10 h at room temperature at 25°C. 100mL of saturated ammonium chloride aqueous solution was used to quench the reaction, and hydrolyzed to generate corresponding alcohol intermedi...

Embodiment 2

[0041] Embodiment 2: the preparation of intermediate M2

[0042]

[0043] Using a method similar to Example 1, using an equivalent amount of 6-bromo-[2,2'-bipyridine]-3-methyl carboxylate instead of 5-bromo-[2,2'-bipyridine]-3- Methyl formate, with other conditions unchanged, intermediate M2 was obtained, 5.3 g of off-white solid, yield 23%.

[0044] Mass spectrum MS (m / e), molecular formula C 23 h 13 BrN 2 o 2 S, theoretical value 459.9, test value 459.6.

[0045] Elemental analysis (C 23 h 13 BrN 2 o 2 S), theoretical value C: 59.88%, H: 2.84%, Br: 17.32, O: 6.94%, N: 6.07%, S: 6.95%; measured value C: 59.87%, H: 2.79%, Br: 17.40, O: 6.99%, N: 6.10%, S: 6.85%.

Embodiment 3

[0046] Embodiment 3: the preparation of intermediate M3

[0047]

[0048] Using a method similar to Example 1, using an equivalent amount of 5,5'-dibromo-[2,2'-bipyridine]-3-methyl carboxylate instead of 5-bromo-[2,2'-bipyridine ]-3-Methyl carboxylate, other conditions remained unchanged, to obtain intermediate M3, off-white solid 11.3g, yield 42%.

[0049] Mass spectrum MS (m / e), molecular formula C 23 h 12 Br 2 N 2 o 2 S, theoretical value 537.9, test value 538.1.

[0050] Elemental analysis (C 23 h 12 Br 2 N 2 o 2 S), theoretical value C: 51.14%, H: 2.24%, Br: 29.58, O: 5.92%, N: 5.19%, S: 5.94%; measured value C: 51.22%, H: 2.25%, Br: 29.47, O: 5.95%, N: 5.20%, S: 5.91%.

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Abstract

The invention belongs to the field of organic electroluminescence materials, and particularly relates to an organic electroluminescence material comprising a 4,5-diazaspiro thioxanthone structure, application of the organic electroluminescence material, and a device; the organic electroluminescence material can be used for OLEDs (Organic Light Emitting Diodes), has very good bipolar transmission property and can be used as a main material. A structural formula is as shown in the description, wherein Ar1 and Ar2 are independently selected from hydrogen atoms, substitutive or non-substitutive carbazole groups of C3 to C30, substitutive or non-substitutive arylamine groups of C3 to C30, substitutive or non-substitutive phenothiazine groups of C3 to C30, substitutive or non-substitutive phenoxazine groups of C3 to C30, substitutive or non-substitutive phenazine groups of C3 to C30 and substitutive or non-substitutive acridine groups of C3 to C30, and Ar1 and Ar2 are not hydrogen at the same time. The invention also relates to the device comprising at least one layer of bipolar compound as a main body, and a method for manufacturing the device.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and in particular relates to an organic electroluminescent material containing a 4,5-diazaspirothioxanthene structure and its application and device. Background technique [0002] Phosphorescent materials can make full use of the triplet excitons produced by electron-hole recombination in electroluminescent devices, which account for 75% of the ratio. Sub utilization can even reach 100%. Phosphorescent materials are usually doped as guest materials in the host material. An effective host material should have an ideal band gap for efficient energy transfer to the guest, and good carrier transport properties for balanced recombination of carriers in the emissive layer. , energy level matching with adjacent layers for efficient charge injection, and sufficient thermal and morphological stability for extended device lifetime, so the development of host materials is extremely impor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/20C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D495/20C07D519/00C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1029C09K2211/1011H10K85/6576H10K85/657H10K85/6572
Inventor 李庆张成新巴玲玲石宇刘英瑞高自良
Owner VALIANT CO LTD
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