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Spiro compound and application thereof

A spiro compound and condensing technology, applied in the field of organic electroluminescent materials, can solve the problems of poor film formation and great influence on the long-term stability of the device, and achieve the effect of low turn-on voltage and high external quantum efficiency

Inactive Publication Date: 2019-05-24
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For blue fluorescent materials, after long-term efforts in industry and academia, great progress has been made in terms of color purity and thermal stability. However, the easy crystallization of blue materials leads to poor film formation, which affects the device Long-term stability is greatly affected

Method used

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  • Spiro compound and application thereof
  • Spiro compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Embodiment 1: the synthesis of compound TM1

[0111] step 1

[0112]

[0113] Compound C-1 (3.5g, 12.2mmol) was added to 50mL of tetrahydrofuran, and n-butyllithium (5.8mL, 14.6mmol) was added dropwise at a low temperature of -78°C. After the reaction system continued to stir for 1 hour, the temperature was maintained and slowly A 10 mL solution of compound C-2 (10.8 mmol) was added and stirred for another 2 hours, then raised to room temperature and stirred for 12 hours. The reaction system was extracted with ethyl acetate and recrystallized from diethyl ether to obtain an intermediate. Add the obtained intermediate to 30 mL of acetic acid, raise the temperature to 80°C, add 1 drop of concentrated hydrochloric acid, reflux for 2 hours, cool to room temperature, and filter to obtain compound C-3. Yield 59%.

[0114] step 2

[0115]

[0116] Compound C-3 (4.1g, 10mmol) was dissolved in 50mL DMF, then NBS (2.1g, 12mmol) was slowly added dropwise, and 50mL of dist...

Embodiment 2

[0122] Embodiment 2: the synthesis of compound TM2

[0123] step 1

[0124]

[0125] Compound C-3 (4.1g, 10mmol) was dissolved in 50mL DMF, then NBS (4.2g, 24mmol) was slowly added dropwise, and 50mL distilled water was added dropwise under stirring, and stirring was continued for 1 hour after the addition was completed, and the precipitate was filtered and used Recrystallize from n-hexane to obtain compound C-6. Yield 34%.

[0126] step 2

[0127]

[0128] Compound C-6 (5.7g, 10mmol) and compound C-7 (7.7g, 22mmol), tetrakistriphenylphosphine palladium (1.2g, 1mmol), potassium carbonate (5.6g, 120mmol), were added to 100mL toluene, In a mixed solvent of 100mL dioxane and 20mL water, reflux the reaction for 12 hours, extract with ethyl acetate, and carry out column chromatography to obtain the target compound TM2. Yield 27%.

[0129] Mass spectral data: [M+]=1012.

Embodiment 3

[0131] step 1

[0132]

[0133] Compound C-6 (5.7g, 10mmol) and compound C-5 (3.3g, 11mmol), tetrakis triphenylphosphine palladium (0.6g, 0.5mmol), potassium carbonate (2.8g, 60mmol), was added to 50mL toluene , 50 mL of dioxane, and 10 mL of water in a mixed solvent, refluxed for 12 hours, extracted with ethyl acetate, and carried out column chromatography to mention compound C-8. Yield 30%.

[0134] step 2

[0135]

[0136] Compound C-8 (7.9g, 10mmol) and compound C-9 (1.3g, 11mmol), tetrakis triphenylphosphine palladium (0.6g, 0.5mmol), potassium carbonate (2.8g, 60mmol), was added to 50mL toluene , 50mL dioxane, and 10mL water in a mixed solvent, reflux for 12 hours, extract with ethyl acetate, and carry out column chromatography to mention compound TM3. Yield 37%.

[0137] Mass spectral data: [M+]=786.

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Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a spiro compound and application thereof. The spiro compound has good thermal stability and device stability.The spiro compound serves as a main body material of a luminescent layer of an anelectroluminescent device, or an object material is doped in the luminescent layer of the electroluminescent device, the cut-in voltage of the device is significantly lowered, the luminous efficiency is improved, and the stability of the device is obviously improved.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a spiro compound and its application. Background technique [0002] Organic electroluminescent device is a device technology that realizes electroluminescence by introducing one or more layers of organic films on the cathode and anode. It can achieve ultra-thin, flexible and transparent performance, and is used in flat panel display and lighting industries. increase year by year. [0003] The organic electroluminescent device structure in the industry has various structures and methods in order to achieve different goals. For the light-emitting layer that emits a spectrum, one way is to use host-guest doping to improve efficiency and lifetime. The host material receives energy and transmits it to the guest, and the guest material emits a corresponding spectrum after receiving the energy. Different host and object materials can achieve different colors of lum...

Claims

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Application Information

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IPC IPC(8): C07C15/20C07C43/205C07B59/00C09K11/06H01L51/50H01L51/54
Inventor 黄达马腾达
Owner AAC TECH NANJING
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