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Compounds using fluorene as core, preparation method of compounds and application of compounds in organic light emission diode device

A compound, organic technology, applied in the application of organic electroluminescent devices, the field of organic compounds, can solve the problems of different performance and so on

Active Publication Date: 2019-09-24
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compounds using fluorene as core, preparation method of compounds and application of compounds in organic light emission diode device
  • Compounds using fluorene as core, preparation method of compounds and application of compounds in organic light emission diode device
  • Compounds using fluorene as core, preparation method of compounds and application of compounds in organic light emission diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] The preparation of embodiment 1 intermediate

[0086] The preparation of embodiment 1-1 intermediate I1

[0087]

[0088] Step 1: In a 250mL three-necked flask, blow nitrogen gas, add 0.05mol raw material U1, 0.06molMg powder, dissolve with 60mL dry tetrahydrofuran, add 0.0004mol elemental I 2 , heated to 40°C and stirred until the solution changed from yellow to colorless, heated the above mixed solution to 80°C, and stirred for 4 hours. At this time, no magnesium powder remained, indicating that the reaction was complete, and Grignard reagent intermediate V1 was generated without purification. Go directly to the next step;

[0089] Step 2: In a 250mL three-neck flask, blow nitrogen, add 0.03mol 9-fluorenone, dissolve in 40mL dry tetrahydrofuran, slowly add the above-mentioned Grignard reagent intermediate V1 solution dropwise, heat and reflux for 15h, a large amount of white precipitate is formed, and then cool to room temperature, add saturated NHCl 4 Convert t...

Embodiment 2

[0114]Embodiment 2 takes fluorene as the preparation of the compound of core

Embodiment 2-1

[0115] The preparation of embodiment 2-1 compound 6

[0116]

[0117] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol intermediate I4 and 0.015mol intermediate II1 were added, dissolved in a mixed solvent of toluene and ethanol (90mL of toluene, 45mL of ethanol), and then 0.03mol of Na 2 CO 3 Aqueous solution (2M), stirred with nitrogen for 1h, then added 0.0001mol Pd(PPh 3 ) 4 , Heated to reflux for 15h, sampled and plated, the reaction was complete. After natural cooling, filtration, rotary evaporation of the filtrate, and passing the residue through a silica gel column, the target product was obtained with a purity of 97.8% and a yield of 73.5%. Elemental analysis structure (molecular formula C 43 h 27 NO): Theoretical C, 90.03; H, 4.74; N, 2.44; O, 2.79; Tested: C, 90.04; H, 4.73; N, 2.44; ESI-MS(m / z)(M + ): The theoretical value is 573.21, and the measured value is 573.33.

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Abstract

The invention relates to organic compounds using fluorene as a core, a preparation method of the compounds and an application of the compounds in an organic light emission diode (OLED) device. The compounds have a following structure: the fluorene is connected with a dibenzo five-membered ring and ring structure through a carbon-carbon bond, the carbon-carbon bond connection not only improves the chemical stability of the material, but also avoids exposure of active positions of a branched chain group, and the whole molecule is a larger rigid structure and has a higher triplet state energy level (T1); the compounds have large steric hindrance, are not easy to rotate, and have a more stable stereoscopic space structure, so that the compounds have a higher glass transition temperature and molecular thermal stability; in addition, HOMO and LUMO distribution positions of the compounds are separated from each other, so that the compounds have suitable HOMO and LUMO energy levels; therefore, the compounds can effectively improve the luminous efficiency and the service life of the device after being applied to the OLED device.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with fluorene as the core, its preparation method and its application in organic electroluminescent devices. Background technique [0002] Organic Light Emission Diodes (OLED) device technology can be used not only to manufacture new display products, but also to make new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive and negat...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D495/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC07D491/048C07D495/04C07D519/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1088C09K2211/1092H10K85/622H10K85/626H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/18H10K50/11
Inventor 庞羽佳唐丹丹张兆超李崇王芳
Owner JIANGSU SUNERA TECH CO LTD
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