Organic compound taking fluorene as core and application of organic compound

An organic compound, an organic technology, applied to the application of organic electroluminescent devices, in the field of organic compounds, can solve problems such as performance differences, achieve three-dimensional structure stability, improve material stability, and improve current efficiency and life.

Inactive Publication Date: 2017-12-01
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Organic compound taking fluorene as core and application of organic compound
  • Organic compound taking fluorene as core and application of organic compound
  • Organic compound taking fluorene as core and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of intermediate I and intermediate II

[0047] a. Synthesis of Intermediate I:

[0048]

[0049] (1) Weigh raw material U and Mg powder, dissolve with dry tetrahydrofuran (THF); under inert atmosphere, add catalyst amount I 2 , heated to 40°C and stirred until the solution changed from yellow to colorless, then heated the above mixed solution to 60-90°C, stirred and reacted for 3-5 hours, no magnesium powder remained, the reaction was complete, and Grignard reagent intermediate V was generated; The mol ratio of described raw material U and Mg is 1:1.0~1.2; I 2 The molar ratio with raw material U is 0.006~0.02:1;

[0050] (2) Weigh 9-fluorenone and dissolve it in dry THF; under an inert atmosphere, add the above-mentioned Grignard reagent intermediate V dropwise, and stir the resulting mixed solution at 60-90°C for 10-24 hours to generate a large amount of white Precipitate, then cool to room temperature, add saturated NHCl4 to convert G...

Embodiment 2

[0075] Embodiment 2: the synthesis of compound 5:

[0076]

[0077] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol of intermediate M1, 0.015mol of intermediate O1, dissolve in a mixed solvent (90ml of toluene, 45ml of ethanol), and then add 0.03mol of Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.5% and a yield of 76.4%. Elemental analysis structure (molecular formula C 46 h 32 O): Theoretical value C, 91.97; H, 5.37; O, 2.66; Test value: C, 91.96; H, 5.36; O, 2.68. ESI-MS(m / z)(M + ): The theoretical value is 600.25, and the measured value is 600.41.

Embodiment 3

[0078] Embodiment 3: the synthesis of compound 9:

[0079]

[0080] In a 250ml three-neck flask, under an atmosphere of nitrogen gas, add 0.01mol intermediate M1, 0.015mol intermediate O2, dissolve with a mixed solvent (90ml toluene, 45ml ethanol), and then add 0.03mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0001mol Pd(PPh 3 ) 4 , heating to reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.3% and a yield of 68.5%. Elemental analysis structure (molecular formula C 46 h 32S): theoretical value C, 89.57; H, 5.23; S, 5.20; test value: C, 89.55; H, 5.24; S, 5.21. ESI-MS(m / z)(M + ): The theoretical value is 616.22, and the measured value is 616.47.

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Abstract

The invention relates to an organic compound taking fluorene as a core and application of the organic compound in an OLED (Organic Light Emission Diodes) device. The compound is of a structure that the fluorene is connected with a dibenzo five-membered ring combination structure by a carbon-carbon bond; by carbon-carbon bond connection, not only is the chemical stability of a material improved, but also an active position of a branch chain group is prevented from being exposed, and moreover, a whole molecule is of a bigger rigid structure and has a high triplet state energy level (T1); in addition, steric hindrance is great, rotation is not easy, and a three-dimensional space structure is more stable, so the compound has higher glass-transition temperature and molecular heat stability; besides, distribution positions of HOMO and LUMO of the compound are separated from each other, so that the compound has proper HOMO and LUMO energy levels; therefore, after the compound is applied to the OLED device, the luminous efficiency and the service life of the device can be effectively improved and prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with fluorene as the core and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/66C07C13/62C07D307/77C07D333/78C07D333/08C07D209/94C07D405/04C07D409/04C07D401/10C07D403/14C07D409/10C07D403/10C07C1/32H01L51/54
CPCC07C13/62C07C13/66C07D209/94C07D307/77C07D333/08C07D333/78C07D401/10C07D403/10C07D403/14C07D405/04C07D409/04C07D409/10H10K85/653H10K85/655H10K85/626H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572
Inventor 唐丹丹李崇张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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