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1, 2, 4-oxadiazole micromolecule main body material as well as preparation method and application thereof

A technology of oxadiazole small molecules and host materials, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., and can solve the problems of device performance degradation and annihilation

Inactive Publication Date: 2014-07-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While typical phosphorescent emitters have long lifetimes and can diffuse over longer distances, resulting in potential concentration quenching and triplet-triplet (T 1 -T 1 ) annihilation, which eventually leads to the performance degradation of the device

Method used

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  • 1, 2, 4-oxadiazole micromolecule main body material as well as preparation method and application thereof
  • 1, 2, 4-oxadiazole micromolecule main body material as well as preparation method and application thereof
  • 1, 2, 4-oxadiazole micromolecule main body material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Step 1: Preparation of 1,3-bis-N-hydroxy-benzamidine (A1)

[0069]

[0070] In an ice bath, sodium carbonate (Na 2 CO 3 ) (8.48g, 80.0mmol) was slowly added to water (27mL) dissolved in hydroxylamine hydrochloride (5.65g, 81.3mmol), and subsequently, the above mixture was poured into a solution of isophthalonitrile (2.56g, 20.0mmol) In absolute ethanol (30mL), reflux for 14h. After cooling to room temperature, the mixture was placed in the refrigerator (2-4° C.) for 12 h. Suction filtration, the obtained solid was washed with water and ethanol, and recrystallized with absolute ethanol to obtain a white solid (2.84g, 14.6mmol). The yield was 73.3%. 1 H NMR (300MHz, MeOD), δ (ppm): 7.92 (m, 1H), 7.71 (d, 1H), 7.68 (d, 1H), 7.42 (t, 1H). 13 C NMR (MeOD, 75MHz), δ (ppm): 153.59, 133.11, 128.22, 127.09, 123.81.Anal.Calcd.for C 8 h 10 N 4 o 2 H, 5.19; N, 28.85. Found: C, 48.84; H, 5.39; N, 28.78.

[0071] Step 2: Preparation of 1,3-bis(5-(3-bromophenyl)-1,2,4-oxa...

Embodiment 2

[0079] Step 1: Preparation of 3-bromo-N-hydroxy-benzamidine (B1)

[0080]

[0081] In an ice bath, sodium carbonate (Na 2 CO 3 ) (5.30g, 50.0mmol) was slowly added into water (14mL) dissolved in hydroxylamine hydrochloride (3.48g, 50.0mmol), and subsequently, the above mixture was poured into 3-bromobenzonitrile (4.56g, 25.0mmol) In anhydrous ethanol (25mL), the reaction was refluxed for 14h. After cooling to room temperature, the mixture was placed in the refrigerator (2-4° C.) for 12 h. Suction filtration, the obtained solid was washed with water and ethanol, and recrystallized with absolute ethanol to obtain a white solid (5.03g, 23.4mmol). The yield was 93.5%. 1 H NMR (300MHz, MeOD), δ (ppm): 7.82 (t, 1H), 7.60 (m, 2H), 7.31 (t, 1H). 13 CNMR(MeOD,75MHz),δ(ppm):152.55,136.00,132.17,129.83,128.82,124.58,121.91.

[0082] Step 2: Preparation of 1,3-bis(3-(3-bromophenyl)-1,2,4-oxadiazol-5-yl)benzene (B2)

[0083]

[0084] Under a nitrogen atmosphere, isophthaloyl c...

Embodiment 3

[0089] Step 1: Preparation of 3,5-bis-(3-bromophenyl)-1,2,4-oxadiazole (C1)

[0090]

[0091] Under a nitrogen atmosphere, add 3-bromobenzoyl chloride (3.0ml, 22.8mmol) to 53ml of anhydrous pyridine dissolved in 3-bromo-N-hydroxy-benzamidine (4.35g, 20.2mmol) with a syringe, It was stirred for 2 days under the condition of an oil bath at 120°C. After cooling to room temperature, the mixture was poured into 300 mL of deionized water. Suction filtration, the obtained solid was washed with water and ethanol, and recrystallized with absolute ethanol to obtain a white solid (5.43g, 14.3mmol). The yield was 70.7%. 1 H NMR (300MHz, CDCl 3 ),δ(ppm):8.38(s,1H),8.33(s,1H),8.12(dd,2H),7.75(d,1H),7.67(d,1H),7.47-7.37(m,2H) . 13 C NMR (CDCl 3 C 14 h 8 N 2 OBr 2 380.3, APCI + -MS(m / z):380.9(M + ).

[0092] Step 2: Preparation of 3,5-bis(3'-(9H-carbazol-9-yl)biphenyl-3-yl)-1,2,4-oxadiazole (124OXD)

[0093]

[0094] Under argon atmosphere, add C1 (0.95g, 2.5mmol), 9-(3-(4...

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Abstract

The invention discloses a 1, 2, 4-oxadiazole micromolecule main body material. The 1, 2, 4-oxadiazole micromolecule main body material contains one or multiple electrophilic 1, 2, 4-oxadiazoles which serve as electron acceptor units, wherein the tail ends of molecules are connected to electron donor units. The invention also discloses a preparation method of the micromolecule main body material. The preparation method is characterized in that a dibromo substituted intermediate, namely a 1, 2, 4-oxadiazole compound is prepared by using bromobenzonitrile as a reaction raw material, and then electron donor units are connected to the dibromo substituted intermediate, namely the 1, 2, 4-oxadiazole compound through Suzuki coupling reaction. The invention also discloses an application of the 1, 2, 4-oxadiazole micromolecule main body material. The 1, 2, 4-oxadiazole micromolecule main body material has relatively good solubility and film-forming property, relatively strong eletrophilicity, relatively low LUMO (Lowest Unoccupied Molecular Orbital) energy level and relatively high electronic mobility.

Description

technical field [0001] The invention relates to an organic small molecule host material, in particular to a 1,2,4-oxadiazole small molecule host material and its preparation method and application. Background technique [0002] Since OLEDs were first reported by Dr. Qingyun Deng et al. in 1987, there have been more than 20 years of research and development in the field of organic optoelectronics. Because of the advantages of self-luminescence, fast response time, wide viewing angle, high contrast ratio and light weight of OLEDs, OLEDs show very attractive application prospects in the next generation of flat panel displays and white lighting. In recent years, researches based on OLEDs have mainly focused on high efficiency and long lifetime of the devices. According to the spin quantum statistical theory, under electric field excitation, the ratio of singlet and triplet exciton formation is roughly 1:3, so the efficiency of conventional fluorescent OLEDs is limited to 25%. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14H01L51/54
CPCC09K11/06C07D413/14C09K2211/1029C09K2211/1007C09K2211/1048H10K85/6565H10K85/6572
Inventor 苏仕健叶华周凯锋周世杰曹镛
Owner SOUTH CHINA UNIV OF TECH
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