Compound taking spirofluorene anthrone as core, preparation method and applications thereof

A technology of spirofluorenthrone and compound, applied in the field of semiconductor, can solve the problem of different performance, achieve the effect of stable three-dimensional structure, improve compound efficiency and not easy to rotate

Inactive Publication Date: 2020-02-28
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 spirofluorene anthrone as core, preparation method and applications thereof
  • Compound taking spirofluorene anthrone as core, preparation method and applications thereof
  • Compound taking spirofluorene anthrone as core, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0107] Preparation of intermediate Ⅱ-1

[0108]

[0109] (1) In a 250mL three-neck flask, under the protection of nitrogen, add 0.01mol of raw material C-1, 0.015mol of raw material D-1, dissolve with a mixed solvent of toluene and ethanol (90mL of toluene, 45mL of ethanol), and then add 0.03 mol 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. Cool naturally, filter, spin evaporate the filtrate, and pass the residue through a silica gel column to obtain intermediate S1-1; HPLC purity 98.4%, yield 82.6%;

[0110] Elemental analysis structure (molecular formula C 21 h 17 NO 4 ): theoretical value C, 72.61; H, 4.93; N, 4.03; 0, 18.42; test value: C, 72.62; ESI-MS (m / z) (M+): theoretical value 347.12, found value 347.34.

[0111] (2) In a 250mL three-neck flask, under the protection of nitrogen, add 0.02mol of intermediate S1-1, dissolve it with 1...

Embodiment 1

[0132] Embodiment 1: the preparation of compound H5

[0133]

[0134] In a 250mL three-neck flask, under the protection of nitrogen, add 0.01mol raw material I-1, 0.012mol intermediate III-1, 150mL toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 98.4%, yield 86.2%;

[0135] Elemental analysis structure (molecular formula C 46 h 30 N 2OS): Theoretical value C, 83.86; H, 4.59; N, 4.25; O, 2.43; S, 4.87; Test value: C, 83.87; HPLC-MS: The molecular weight of the material is 658.21, and the measured molecular weight is 658.34.

Embodiment 2

[0136] Embodiment 2: the preparation of compound H22

[0137]

[0138] The preparation method of compound H22 is the same as in Example 1, except that raw material I-2 is used to replace raw material I-1, and intermediate III-2 is used to replace intermediate III-1. Elemental analysis structure (molecular formula C 47 h 31 NO 2 ): theoretical value C, 87.96; H, 4.87; N, 2.18; 0, 4.99; test value: C, 87.98; HPLC-MS: The molecular weight of the material is 641.24, and the measured molecular weight is 641.35.

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Abstract

The invention discloses a compound taking spirofluorene anthrone as a core, a preparation method and applications thereof, and belongs to the technical field of semiconductors, wherein the structure of the compound is represented by a general formula (I). The invention further discloses a preparation method and applications of the compound. According to the invention, spirofluorene anthrone is linked to a six-membered ring fused ring derivative structure, and the whole molecule has a large rigid structure and has a high triplet state energy level (T1); the compound is high in structural stereoscopicity, large in steric hindrance and not easy to rotate, so the chemical stability of the material is improved, and the compound has high glass transition temperature and high molecular thermal stability; the HOMO distribution position and the LUMO distribution position of the compound are separated from each other, so that the compound has appropriate HOMO and LUMO energy levels; and with theapplication of the compound in an OLED device, the light emitting efficiency and the service life of the device can be effectively improved.

Description

technical field [0001] The invention relates to a compound with spirofluoranthrone as the core, a preparation method and an application thereof, belonging 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): C07D491/048C07D471/14C07D498/04C07D265/34C07D513/04C07D279/14C07D495/04C07D471/04C07D221/18C07D405/12C07D491/147C07D265/38C07D219/02C07D219/04C07D487/04C07D221/20C07D519/00C09K11/06H01L51/50H01L51/54
CPCC07D491/048C07D471/14C07D498/04C07D265/34C07D513/04C07D279/14C07D495/04C07D471/04C07D221/18C07D405/12C07D491/147C07D265/38C07D219/02C07D219/04C07D487/04C07D221/20C07D519/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092H10K85/624H10K85/626H10K85/636H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6572H10K85/657H10K50/15H10K50/18H10K50/11
Inventor 李崇庞羽佳王芳张兆超
Owner JIANGSU SUNERA TECH CO LTD
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