A 1,2,4-oxadiazole small molecule host material and its preparation method and application

A technology of oxadiazole small molecule and host material, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc. Structured novel effect

Inactive Publication Date: 2016-05-04
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A 1,2,4-oxadiazole small molecule host material and its preparation method and application
  • A 1,2,4-oxadiazole small molecule host material and its preparation method and application
  • A 1,2,4-oxadiazole small molecule host material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0069]

[0070] Under ice bath conditions, sodium carbonate (Na 2 CO 3 ) (8.48 g, 80.0 mmol) was slowly added to a solution of hydroxylamine hydrochloride (5.65 g, 81.3 mmol) in water (27 mL), followed by pouring the above mixture into a solution of isophthalonitrile (2.56 g, 20.0 mmol). In anhydrous ethanol (30 mL), the reaction was refluxed for 14 h. After cooling to room temperature, the mixture was placed in a refrigerator (2-4° C.) for 12 h. After suction filtration, the obtained solid was washed with water and ethanol, and recrystallized with absolute ethanol to obtain a white solid (2.84 g, 14.6 mmol). The yield was 73.3%. 1 HNMR (300MHz, MeOD), δ (ppm): 7.92 (m, 1H), 7.71 (d, 1H), 7.68 (d, 1H), 7.42 (t, 1H). 13 CNMR (MeOD, 75MHz), δ (ppm): 153.59, 133.11, 128.22, 127.09, 123.81.Anal.Calcd.forC 8 H 10 N 4 O 2 : C, 49.48; H, 5.19; N, 28.85. Found: C, 48.84; H, 5.39; N, 28.78.

[0071] Step 2:...

Embodiment 2

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

[0080]

[0081] Under ice bath conditions, sodium carbonate (Na 2 CO 3 ) (5.30 g, 50.0 mmol) was slowly added to a solution of hydroxylamine hydrochloride (3.48 g, 50.0 mmol) in water (14 mL), then the above mixture was poured into a solution of 3-bromoxynil (4.56 g, 25.0 mmol) in anhydrous ethanol (25 mL), refluxed for 14 h. After cooling to room temperature, the mixture was placed in a refrigerator (2-4° C.) for 12 h. After suction filtration, the obtained solid was washed with water and ethanol, and recrystallized from absolute ethanol to obtain a white solid (5.03 g, 23.4 mmol). The yield was 93.5%. 1 HNMR (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,...

Embodiment 3

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

[0090]

[0091] Under a nitrogen atmosphere, 3-bromobenzoyl chloride (3.0 ml, 22.8 mmol) was added to 53 ml of anhydrous pyridine in which 3-bromo-N-hydroxy-benzamidine (4.35 g, 20.2 mmol) was dissolved in one portion with a syringe, Stir in an oil bath at 120°C for 2 days. After cooling to room temperature, the mixture was poured into 300 mL of deionized water. After suction filtration, the obtained solid was washed with water and ethanol, and recrystallized with absolute ethanol to obtain a white solid (5.43 g, 14.3 mmol). The yield was 70.7%. 1 HNMR (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 CNMR (CDCl 3 , 75MHz), δ(ppm): 174.61, 167.96, 135.87, 134.32, 131.08, 130.72, 130.54, 130.46, 128.62, 126.66, 126.02, 125.85, 123.21, 122.99.CalcdC 14 H 8 N 2 OBr 2 380.3, APCI + -MS(m / z): 380.9(M + ).

[0092] Step 2: Pre...

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Abstract

The invention discloses a 1,2,4-oxadiazole small molecule host material, which contains one or more electrophilic 1,2,4-oxadiazoles as electron acceptor units. The end is connected with the electron donor unit. The invention also discloses a preparation method of the above-mentioned small molecule host material, using m-bromoxynil as a reaction raw material to prepare a dibromo-substituted intermediate 1,2,4-oxadiazole compound, and then through the Suzuki coupling reaction to convert the electron The donor unit is attached to the bisbromo-substituted intermediate 1,2,4-oxadiazole compound. The invention also discloses the application of the above-mentioned small molecule host material. The small molecule host material of the present invention has better solubility and film-forming property, stronger electrophilicity, lower LUMO energy level and higher electron 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 a preparation method and application thereof. 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 OLEDs have the advantages of self-luminescence, fast response time, wide viewing angle, high contrast ratio and light weight, they show very attractive application prospects in next-generation flat panel displays and white lighting. In recent years, research based on OLEDs has mainly focused on the high efficiency and long lifetime of the devices. According to the theory of spin quantum statistics, the ratio of singlet and triplet excitons formed is roughly 1:3 under electric field excitation, so the efficiency of conventional fluorescent OLEDs is limited to 25%. How...

Claims

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Application Information

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Patent Type & Authority Patents(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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