Compound taking ketone and fluorene as cores, and preparation method and application thereof

A compound, unsubstituted technology, used in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve problems such as different performance, achieve stable three-dimensional structure, improve luminous efficiency, and large steric hindrance.

Pending Publication Date: 2020-04-07
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

Method used

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  • Compound taking ketone and fluorene as cores, and preparation method and application thereof
  • Compound taking ketone and fluorene as cores, and preparation method and application thereof
  • Compound taking ketone and fluorene as cores, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0073] Preparation of Intermediate A

[0074]

[0075] Under a nitrogen atmosphere, weigh raw material B and dissolve it in tetrahydrofuran (THF), then bis(pinacolyl)diboron, (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium ( II) Add potassium acetate, stir the mixture, heat the mixed solution of the above reactants to reflux at a reaction temperature of 70-90° C. for 5-10 hours; after the reaction is completed, add water to cool, and filter the mixture and dry it in a vacuum oven. The obtained residue was separated and purified through a silica gel column to obtain intermediate A;

[0076] Take the synthesis of intermediate A1 as an example:

[0077]

[0078] In a 250mL three-neck flask, blow nitrogen gas, add 0.02mol of raw material B1 and dissolve it in 150ml of tetrahydrofuran, then add 0.024mol of bis(pinacol radical) diboron, 0.0002mol of (1,1'-bis(diphenylphosphine) Ferrocene) dichloropalladium (II) and 0.05mol potassium acetate were added, the mixture wa...

Embodiment 1

[0084] Embodiment 1: the preparation of compound 1

[0085]

[0086] In a 250ml three-neck flask, add 0.01mol of raw material 1 and 0.015mol of intermediate A1, and dissolve in a mixed solvent of toluene, ethanol and water with a volume ratio of 2:1:1; under an inert atmosphere, add 0.02mol of Na 2 CO 3 Aqueous solution (2M), 0.0001mol Pd(PPh 3 ) 4 The mixed solution of the above reactants was reacted at a reaction temperature of 100°C for 15 hours, cooled and filtered the reaction solution, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a HPLC purity of 99.90% and a yield of 76.8%. Elemental analysis structure (molecular formula C 44 h 28 o 2 ): Theoretical: C, 89.77; H, 4.79; O, 5.44; Tested: C, 89.77; H, 4.78; O, 5.43. HPLC-MS: The molecular weight of the material is 588.71, and the measured molecular weight is 588.70.

Embodiment 2

[0087] Embodiment 2: the preparation of compound 11

[0088]

[0089] The preparation method of compound 11 is the same as that in Example 1, except that raw material 2 is used to replace raw material 1, and intermediate A1 is replaced by intermediate A2. Elemental analysis structure (molecular formula C 44 h 28 o 2 ): Theoretical: C, 89.77; H, 4.79; O, 5.44; Tested: C, 89.78; H, 4.77; O, 5.43. HPLC-MS: The molecular weight of the material is 588.71, and the measured molecular weight is 588.74.

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Abstract

The invention discloses a compound taking ketone and fluorene as cores, and a preparation method and an application thereof, and belongs to the technical field of semiconductors. The compound providedby the invention has the structure represented by a general formula (I) defined in the specification. The invention also discloses the preparation method and the application of the compound. The structure of the compound is formed by connecting ketone and fluorene structures, and the compound has a high triplet state energy level (T1); the chemical stability is improved, and the compound has relatively high glass transition temperature and molecular thermal stability. In addition, HOMO and LUMO distribution positions of the compound are separated from each other, so that the compound has appropriate HOMO and LUMO energy levels. Therefore, after the compound is applied to an OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Description

technical field [0001] The invention relates to a compound with ketone and fluorene as the core, a preparation method and application thereof, and belongs to the technical field of semiconductors. 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 negative charges in the organic layer fun...

Claims

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Application Information

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IPC IPC(8): C07C49/675C07D219/06C07D311/86C07D335/16C07D405/10C07D407/04C07D407/10C07D409/10C09K11/06H01L51/54
CPCC07D311/86C07D407/10C07D409/10C07D405/10C07D407/04C07D335/16C07C49/675C07D219/06C09K11/06C09K2211/1088C09K2211/1011C09K2211/1092C09K2211/1029C07C2603/18C07C2603/24H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572
Inventor 李崇吴秀芹王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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