Bipolar body organic electroluminescent material and application thereof

An electroluminescent material, bipolar technology, applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of unbalanced OLED turn-on voltage and life, high turn-on voltage, disadvantage, etc., to improve external quantum efficiency, Effects of high stability, high glass transition temperature and thermal decomposition temperature

Active Publication Date: 2016-10-12
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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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  • Bipolar body organic electroluminescent material and application thereof
  • Bipolar body organic electroluminescent material and application thereof
  • Bipolar body organic electroluminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Embodiment 1: Preparation of intermediate 1,8-diazadibenzothiophene sulfone

[0080]

[0081] Preparation of intermediate 1,8-diazadibenzothiophene sulfone: Add 1,8-diazadibenzothiophene (18.6 g, 0.1 mol) and AcOH (300 mL) into a 2 L three-necked flask. At room temperature, a mass fraction of 30% H was added dropwise 2 o 2 (1200mL), the dropwise addition was completed within 1 hour. Under nitrogen protection, stir at reflux for 18h. Room temperature 25°C, suction filtration under reduced pressure to obtain a white powdery solid, rinse the filter cake with water until neutral. Add 200 mL of diethyl ether to the obtained white solid, stir at room temperature for 1 h, and filter with suction to obtain 18.7 g of white powdery solid product, yield: 86%.

[0082] Mass spectrum MS (m / e), molecular formula C 10 h 6 N 2 o 2 S, theoretical value 218.0, test value 219.0.

[0083] Elemental analysis (C 10 h 6 N 2 o 2 S), theoretical value C: 55.04%, H: 2.77%, O: 14....

Embodiment 2

[0084] Embodiment 2: the preparation of intermediate M1

[0085]

[0086] 1) Preparation of Intermediate M1-A

[0087] In a 250mL three-necked flask, 1,8-diazadibenzothiophene sulfone (4.36g, 0.02mol), 2,7-dibromo-9H-xanthene (11.6g, 0.034mol), dioxane ring (100 mL). Nitrogen strictly replaces the air in the reaction system, and maintains the nitrogen environment of the system. At room temperature of 25°C, KN(SiMe 3 ) 2 Toluene solution (0.5M, 120mL, 0.06mol), the dropwise addition was completed within 50min. The bath temperature was set at 100°C, the reaction was kept for 12 hours, and the temperature was lowered to room temperature 25°C. Pour 100 mL of saturated NH into the reaction system 4 Cl aqueous solution was used to quench the reaction system. Extract twice with 100 mL of ethyl acetate, combine the organic phases, wash the organic phase with 100 mL*2 water until the organic phase is neutral, dry the organic phase with anhydrous sodium sulfate, filter under re...

Embodiment 3

[0098] Embodiment 3: the preparation of intermediate M2

[0099]

[0100] Using a method similar to Example 2, using equimolar equivalents of 2,7-dibromo-9H-thioxanthene instead of 2,7-dibromo-9H-oxanthene, and other conditions unchanged, intermediate M2 was obtained , off-white solid 3.7g, yield 35%.

[0101] Mass spectrum MS (m / e), molecular formula C 35 h 20 N 4 S, theoretical value 528.1, test value 529.1.

[0102] Elemental analysis (C 35 h 20 N 4 S), theoretical value C: 79.52%, H: 3.81%, N: 10.60%, S: 6.07%; measured value C: 79.54%, H: 3.80%, N: 10.63%, S: 6.03%.

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Abstract

The invention relates to a bipolar body organic electroluminescent material. The formula of the bipolar body organic electroluminescent material is as shown in formula (1), wherein X is optional one of O, S and CMe2; R1 and R2 are identical or different, and R1 and R2 are independently selected from C1-C10 aliphatic linear chain or branch chain alkyl containing substituent group or unsubstituted group, C6-C30 aryl containing substituent group or unsubstituted group and C3-C30 heteroatom-containing aryl containing substituent group or unsubstituted group; R3-R10 are independently selected from hydrogen atom, C1-C10 aliphatic linear chain or branch chain alkyl and C6-C30 aryl containing substituent group or unsubstituted group, or the two adjacent groups of the R3-R10 are connected into a ring. The bipolar body organic electroluminescent material which can be used as the blue light and green light body material is good in thermodynamic stability, good in film forming performance, appropriate in triplet state energy level, and the like.

Description

technical field [0001] The invention relates to a bipolar organic electroluminescent material and its application, belonging to the field of organic electroluminescent materials. 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%. [0003] The exciton utilization efficiency of phosphorescent devices 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 important for high-efficiency elec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22C07D495/22C07D471/22C09K11/06H01L51/54
CPCC09K11/06C07D471/22C07D491/22C07D495/22C09K2211/1059C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1029H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 李庆石宇张学衡刘英瑞张成新高自良
Owner VALIANT CO LTD
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