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Bipolar fluorescent material based on benzo five-membered heterocycle, preparation method of bipolar fluorescent material and organic electroluminescent device

A technology of fluorescent material and five-membered heterocyclic ring, applied in the field of organic optoelectronics, can solve the problem of low luminous efficiency of devices, and achieve the effects of high luminous efficiency, improved unipolar characteristics, and balanced charge injection

Pending Publication Date: 2021-12-31
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a bipolar fluorescent material based on a benzo five-membered heterocyclic ring and its preparation method and an organic electroluminescent device, aiming at solving the problem that the existing luminescent material is a unipolar non-reactive materials, leading to the problem of low luminous efficiency of the device

Method used

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  • Bipolar fluorescent material based on benzo five-membered heterocycle, preparation method of bipolar fluorescent material and organic electroluminescent device
  • Bipolar fluorescent material based on benzo five-membered heterocycle, preparation method of bipolar fluorescent material and organic electroluminescent device
  • Bipolar fluorescent material based on benzo five-membered heterocycle, preparation method of bipolar fluorescent material and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] This example provides a bipolar fluorescent material based on a benzo five-membered heterocycle, which is compound 1, and the synthetic route of compound 1 is as follows:

[0073]

[0074] The synthetic method of compound 1 specifically comprises the following steps:

[0075] Synthesis of Intermediate 1: Take raw material 1 (1.73g, 10mmol), raw material 2 (2.36g, 12mmol), potassium carbonate (4.14g) and toluene (50mL) into a round bottom flask, react at 100°C for 12 hours, Add 50mL phosphoric acid aqueous solution, continue to stir for 2 hours, use chloroform to extract, the aqueous phase is extracted three times with 60mL ethyl acetate, combine organic phase, dry over anhydrous sodium sulfate, crude product is subjected to silica gel column chromatography (petroleum ether / ethyl acetate 6 / 1 (volume ratio)) to obtain Intermediate 1 (0.83 g, 42% yield).

[0076] Synthesis of Intermediate 2: Take a 200mL double-necked round-bottomed flask, connect it with a spherical c...

Embodiment 2

[0080] This example provides a bipolar fluorescent material based on a benzo five-membered heterocycle, which is compound 39. The synthetic route of compound 39 is as follows:

[0081]

[0082] The synthetic method of compound 39 specifically comprises the following steps:

[0083] Synthesis of intermediate 1: as described in compound 1, except that starting material 1 (2.36 g, 10 mmol) was used to obtain intermediate 1 (1.17 g, yield 45%).

[0084] Synthesis of Intermediate 2: Take a 200mL double-necked round-bottom flask, connect a spherical condenser to it, fill it with nitrogen after drying, add Intermediate 1 (3.62 g, 10 mmol), raw material 3 (5.57 g, 12 mmol), tetratriphenyl Palladium phosphine (183 mg, 0.2 mmol), 2 mol / L potassium carbonate aqueous solution (10 mL), toluene (100 mL). Heated to reflux for 24 hours, cooled to room temperature, the solution was poured into water, extracted with chloroform, the aqueous phase was extracted three times with ethyl acetate,...

Embodiment 3

[0088] This example provides a bipolar fluorescent material based on a benzo five-membered heterocycle, which is compound 48, and the synthetic route of compound 48 is as follows:

[0089]

[0090] The synthetic method of compound 48 specifically comprises the following steps:

[0091] Synthesis of intermediate 1: as described in compound 1, except that starting material 1 (1.73 g, 10 mmol) was used to obtain intermediate 1 (0.77 g, yield 39%).

[0092] Synthesis of intermediate 2: as described in compound 1, except that starting material 3 (2.51 g, 12 mmol) was used to obtain intermediate 2 (2.86 g, yield 88%).

[0093] Synthesis of intermediate 3: as described in compound 1, yield 98%.

[0094] Synthesis of Intermediate 4: Take Intermediate 3 (4.04g, 10mmol), raw material 4 (2.15g, 12mmol), potassium carbonate (4.14g) and DMF (50mL) into a round bottom flask, and react at 70°C for 12 hours , cooled to room temperature, the solution was poured into water, extracted with ...

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Abstract

The invention discloses a bipolar fluorescent material based on benzo five-membered heterocycle, a preparation method thereof and an organic electroluminescent device, the bipolar fluorescent material has the following structure: or in the structure, X and Y are independently selected from oxygen, sulfur, selenium, tellurium or nitrogen alkyl; R1-R4 are independently selected from hydrogen, deuterium or an alkyl chain; EG1-EG4 is an electrical group, and at least two of the EG1-EG4 are respectively selected from a fluorophore and an auxiliary group with polarity balanced with that of the fluorophore and are independently selected from hydrogen, deuterium or an alkyl chain. By introducing the auxiliary polar group, the unipolar characteristic of the material can be effectively improved, and charge injection is balanced. In addition, on the premise that the structure of a light-emitting area is not affected basically, the material structure is twisted, the material stacking effect is weakened, the aggregation quenching effect of a phosphor is reduced, the device stability and the adaptive doping concentration are improved, and regulation and control and yield improvement in the large-scale production process are facilitated.

Description

technical field [0001] The invention relates to the field of organic optoelectronics, in particular to a bipolar fluorescent material based on a benzo five-membered heterocycle, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] Compared with traditional inorganic light-emitting diodes, organic light-emitting diodes (Organic Light-Emitting Diode, OLED) have many advantages such as wide viewing angle, fast response speed, high color reproduction and flexible display. Organic light-emitting devices have a wide range of applications in automotive displays, smartphones, televisions, lighting, and wearable devices. [0003] Luminescent materials are OLED core materials that are focused on the development of academia and industry. The current luminescent materials are mainly low-efficiency ordinary fluorescent materials, phosphorescent materials using noble metals, and TADF materials with a short lifespan. [0004] Most of the c...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D413/14C07D417/14C07D409/14C07F5/02C07D421/14C07D495/04C07D517/04C09K11/06H01L51/54
CPCC07D405/14C07D413/14C07D417/14C07D409/14C07F5/02C07D421/14C07D495/04C07D517/04C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1055C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1096H10K85/654H10K85/657H10K85/6576H10K85/6574H10K85/6572
Inventor 孟鸿张鑫康王胧佩邹东文贺耀武闫朝一
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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