Organic light-emitting material with xanthene spirothioxanthene oxide as parent nucleus and application thereof

An electroluminescent material, spirothiaxanthene technology, applied in the direction of luminescent materials, organic chemistry, circuits, etc., can solve the problems of increasing the difficulty of high-efficiency TADF main materials, quenching, low device performance, etc., and achieve good industrialization prospects , enhanced stability, and good photoelectric performance

Active Publication Date: 2017-08-18
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In OLEDs devices, the TADF material is usually used as a guest and doped into the host as the light-emitting layer to overcome the low performance of the device due to concentration quenching.
Since TADF materials and their host materials are

Method used

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  • Organic light-emitting material with xanthene spirothioxanthene oxide as parent nucleus and application thereof
  • Organic light-emitting material with xanthene spirothioxanthene oxide as parent nucleus and application thereof
  • Organic light-emitting material with xanthene spirothioxanthene oxide as parent nucleus and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of compound C03

[0031]

[0032] Under nitrogen protection, raw material A-1 (1.62g, 2.5mmol), raw material B-1 (1.41g, 5.5mmol), 80mL toluene and 20mL water were added to a 250mL three-necked flask, and then the catalyst tetrakis(triphenylphosphine ) palladium (0.029g, 0.025mmol), acid-binding agent potassium carbonate (1.04g, 7.5mmol). The temperature of the system was raised to reflux for 8 hours, and the temperature was naturally lowered to 20-25° C., the liquid was separated, the solvent was removed, and the crude product was crystallized with toluene to obtain 1.62 g of target C03 with a yield of 86.6%.

[0033] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 53 h 32 o 3 S, theoretical value 748.207, test value 748.206. Elemental analysis (C 53 h 32 o 3 S), theoretical value C: 85.00, H: 4.31, O: 6.41, S: 4.28, measured value C: 80.01, H: 4.30, O: 6.40, S: 4.29.

Embodiment 2

[0034] Embodiment 2: the preparation of compound C10

[0035]

[0036] The synthesis method refers to the preparation method of C03, and the total yield is 76.8%.

[0037] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 37 h 22 o 4 S, theoretical value 562.124, test value 562.123. Elemental analysis (C 37 h 22 o 4 S), theoretical value C: 78.99, H: 3.94, O: 11.37, S: 5.70, measured value C: 78.10, H: 3.93, O: 11.37, S: 5.70.

Embodiment 3

[0038] Embodiment 3: the preparation of compound C11

[0039]

[0040] The synthesis method refers to the preparation method of C03, and the total yield is 77.1%.

[0041] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 40 h 28 o 3 S, theoretical value 588.176, test value 588.177. Elemental analysis (C 40 h 28 o 3 S), theoretical value C: 81.61, H: 4.79, O: 8.15, S: 5.45, measured value C: 81.61, H: 4.79, O: 8.15, S: 5.45.

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Abstract

The invention relates to an organic light-emitting material with xanthene spirothioxanthene oxide as a parent nucleus and application thereof. Xanthene spirothioxanthene oxide has a molecular formula as shown in formula I (as shown in the description), wherein Ar<1> and Ar<2> independently represent any of hydrogen, an aromatic group containing 6-60 carbon atoms or an arylamine group. According to the compound, xanthene spirothioxanthene oxide is taken as the parent nucleus, spirane structures have a high spatial stereoscopic effect, and highly twisted configuration can effectively inhibit all intermolecular interactions among guests, among hosts and among hosts and guests in doped thin film, so that a quenching effect caused by a collision is inhibited to the utmost extent. A xanthene ring is connected with a thioxanthene oxide ring through spirane carbon, so that the conjugation degree of the xanthene ring and the thioxanthene oxide ring is effectively reduced, and the xanthene ring and the thioxanthene oxide ring have appropriate HOMO and LUMO energy levels.

Description

technical field [0001] The invention relates to an organic electroluminescence material, in particular to an organic electroluminescence material with xanthene spirothiaxanthene oxide as a parent nucleus and an application thereof, belonging to the field of organic electroluminescence. Background technique [0002] Since 1987, Organic Light-Emitting Diodes (OLEDs for short) have gradually become the industry-recognized next-generation flat panel display technology. Traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light. The internal quantum efficiency of the device is low (up to 25%), and the external quantum efficiency is generally lower than 5%, which is far from the efficiency of phosphorescent devices. big gap. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit coupling at the center of heavy atoms, the singlet and triplet excitons formed by electrical exci...

Claims

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Application Information

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IPC IPC(8): C07D495/10C09K11/06H01L51/54
CPCC09K11/06C07D495/10C09K2211/1092C09K2211/1088C09K2211/1029H10K85/624H10K85/653H10K85/655
Inventor 张成新高自良盛磊胡葆华李韶涛李健
Owner VALIANT CO LTD
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