A class of blue organic semiconductor materials based on 2,6-di-tert-butylanthracene and its preparation method and application

An organic semiconductor, di-tert-butylanthracene technology, applied in the field of blue organic semiconductor materials and its preparation, can solve the problems of low fluorescence quantum yield, weakened fluorescence, poor stability, etc., and achieve excellent comprehensive performance and stable material structure , the effect of high yield

Active Publication Date: 2022-03-29
SOUTH CHINA UNIV OF TECH
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  • Description
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Problems solved by technology

Among the three primary colors, green and red high-efficiency materials have been developed successively and are gradually entering the commercial field. However, blue light materials, one of the three primary colors, have the characteristics of insufficient efficiency and poor stability.
However, due to its planar rigid structure, it is prone to strong interactions in the aggregated state, which weakens or severely quenches the fluorescence.
Consequently, blue emitters of many anthracene derivatives show low fluorescence quantum yields in thin films

Method used

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  • A class of blue organic semiconductor materials based on 2,6-di-tert-butylanthracene and its preparation method and application
  • A class of blue organic semiconductor materials based on 2,6-di-tert-butylanthracene and its preparation method and application
  • A class of blue organic semiconductor materials based on 2,6-di-tert-butylanthracene and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of Blue Light-emitting Organic Semiconductor Materials Based on 2,6-Di-tert-butylanthracene (DMAC-TABI)

[0043]

[0044] Reaction equation (1):

[0045]

[0046]

[0047] (1) Synthesis of Intermediate 2: In a reaction flask containing anthracene (4.45g, 25mmol), add 25mL of trifluoroacetic acid (TFA), and add tert-butanol (8.5ml, 88.8mmol) dropwise to the reaction In the bottle, after the dropwise addition, heat and reflux for 12 hours. After the reaction, pour the reaction solution into cold water to quench, stir and precipitate, then carry out suction filtration, then stir and reflux with ethanol and a small amount of n-hexane for recrystallization, and obtain the preliminary product by suction filtration Then recrystallize with ethanol twice to obtain a white solid product (intermediate 2), with a yield of 76%;

[0048] (2) Synthesis of Intermediate 3: Add Intermediate 2 (1.45g, 5mmol) into the reaction flask, dissolve it with dichloromethane (...

Embodiment 2

[0052] Preparation of Blue Light-emitting Organic Semiconductor Material (DPAC-TABI) Based on 2,6-Di-tert-butylanthracene

[0053]

[0054] Reaction equation (2):

[0055]

[0056] (1) with embodiment 1;

[0057] (2) with embodiment 1;

[0058] (3) with embodiment 1;

[0059] (4) Synthesis of DPAC-TABI: intermediate 5 (0.78g, 1mmol), intermediate 6 (0.60g, 1.5mmol), tetrakis(triphenylphosphine) palladium (0.12g, 0.1mmol), potassium carbonate ( Add 0.42g, 4mmol) into the reaction flask, replace the nitrogen three times, inject the solvent (toluene:ethanol:water=8:1:1 (volume ratio)) under the protection of nitrogen, heat and reflux at 110°C for 12h after the injection is completed, and the reaction is complete After extraction, concentration, powdering and column purification, a white solid product (DPAC-TABI) was obtained with a reaction yield of 78%. 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):8.03–7.90(m,2H),7.88–7.74(m,4H),7.65–7.44(m,15H),7.34(t,J=6.0Hz,4H),7.30( dd,...

Embodiment 3

[0061] Preparation of Blue Light-emitting Organic Semiconductor Materials Based on 2,6-Di-tert-butylanthracene (DMAC-TAPI)

[0062]

[0063] Reaction equation (3):

[0064]

[0065] (1) with embodiment 1;

[0066] (2) with embodiment 1;

[0067] (3) with embodiment 1;

[0068] (4) Synthesis of DMAC-TAPI: intermediate 5 (0.65g, 1mmol), intermediate 6 (0.75g, 1.5mmol), tetrakis(triphenylphosphine) palladium (0.12g, 0.1mmol), potassium carbonate ( Add 0.42g, 4mmol) into the reaction flask, replace the nitrogen three times, inject the solvent (toluene:ethanol:water=8:1:1 (volume ratio)) under the protection of nitrogen, heat and reflux at 110°C for 12h after the injection is completed, and the reaction is complete After extraction, concentration, powdering and column purification, a white solid product (DMAC-TAPI) was obtained with a reaction yield of 73%. 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):8.97(d,J=7.4Hz,1H),8.79(dd,J=31.6,8.5Hz,2H),7.87(d,J=9.8Hz,1H),7.85–7.77 (m,...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a blue-light organic semiconductor material based on 2,6-di-tert-butylanthracene, a preparation method and an application thereof. The organic semiconductor material based on 2,6-di-tert-butylanthracene has a specific structure such as: wherein, Ar 1 , Ar 2 As the control group, Ar 1 with Ar 2 Symmetrical or asymmetrical modifications can be made. The invention mainly adjusts the light-emitting physical properties and energy level characteristics of anthracene derivatives by connecting different modification groups on the 9 and 10 positions of anthracene. The luminescent material prepared by the present invention has efficient blue or deep blue emission in solid state; the energy level structure of the material has good control characteristics, thereby adjusting the electron / hole injection performance of the material, which is beneficial to the simplification of the device structure; all materials Both have good stability and film-forming properties, and can be formed into non-doped or doped devices by vacuum evaporation, and the device preparation process is flexible.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a class of blue organic semiconductor materials based on 2,6-di-tert-butylanthracene, a preparation method and application thereof. Background technique [0002] Organic light emitting diode (OLED) is widely used in the field of display and lighting due to its excellent characteristics such as low driving voltage, fast response speed, high luminous efficiency, wide color gamut, light weight and thin, and flexible folding. All show great application potential. After nearly 30 years of development of OLED, scientists have made great breakthroughs in material preparation, device optimization and theoretical research; and organic light-emitting materials, as the core technology of OLED, have always been the focus of scientific research in the display field. Among the three primary colors, green and red high-efficiency materials have been developed ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/50C07D209/86C07D401/10C09K11/06H01L51/54
CPCC07D401/10C07D209/86C07C255/50C09K11/06C09K2211/1029C09K2211/1044C09K2211/1007C09K2211/1011H10K85/615H10K85/6572
Inventor 唐本忠赵祖金邬子龙朱翔宇秦安军胡蓉蓉王志明
Owner SOUTH CHINA UNIV OF TECH
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