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

A technology of spirofluoranthrone and compounds, which is applied in the application field of organic electroluminescent devices, and can solve problems such as performance differences

Inactive Publication Date: 2020-02-28
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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  • 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
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Effect test

preparation example Construction

[0089] Preparation of Intermediate II-1

[0090]

[0091] (1) In a 250mL three-neck flask, under the protection of nitrogen, add 0.01mol raw material M1, 0.012mol raw material N1, 150mL mixed solvent of toluene and ethanol (toluene 100mL, ethanol 50mL) and stir to mix, then add 0.02mol K 2 CO 3 , 1×10 -4 mol Pd(PPh 3 ) 4 , heated to 120°C, reflux reaction for 24h, sampling plate, showing no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C), and the residue was over neutral Silica gel column to obtain intermediate a1;

[0092] (2) Weigh 0.01mol of intermediate a1 and dissolve it in 100mL of o-dichlorobenzene, add 1×10 -4 mol triphenylphosphine, reacted at 180°C for 12 hours, cooled to room temperature after the reaction, filtered, the filtrate was rotary evaporated, and the residue was passed through a silica gel column to obtain intermediate II-1; ...

Embodiment 1

[0120] The preparation of embodiment 1 compound H1

[0121]

[0122] In a 250ml three-neck flask, add 0.01 mol of intermediate material I-1 and 0.015 mol of intermediate III-1, and dissolve in a mixed solvent of toluene and ethanol with a volume ratio of 2:1; under an inert atmosphere, add 0.02 mol 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 99.85% and a yield of 75.4%. Elemental analysis structure (molecular formula C 53 h 35 NO): Theoretical: C, 90.70; H, 5.03; N, 2.00; O, 2.28; Tested: C, 90.71; H, 5.03; N, 2.00; O, 2.27. HPLC-MS: The molecular weight of the material is 701.87, and the measured molecular weight is 701.85.

Embodiment 2

[0123] The preparation of embodiment 2 compound H24

[0124]

[0125] In a 250ml three-neck flask, under nitrogen protection, add 0.01mol raw material I-2, 0.012mol intermediate II-1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , the target product was obtained, the HPLC purity was 99.77%, and the yield was 76.3%. Elemental analysis structure (molecular formula C 44 h 25 NO 2 ): theoretical value: C, 88.13; H, 4.20; N, 2.34; O, 5.34; test value: C, 88.12; H, 4.21; N, 2.34; HPLC-MS: The molecular weight of the material is 599.69, and the measured molecular weight is 599.66.

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Abstract

The invention relates to a compound taking spirofluorene anthrone as a core, a preparation method and applications thereof, wherein the structure of the compound is formed by linking spirofluorene anthrone to a five-membered ring fused ring structure, and the whole molecule is a large rigid structure and has a high triplet state energy level (T1). According to the invention, 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 the application 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 the technical field of semiconductors, in particular to an organic compound with a spirofluoranthrone structure as the core and a five-membered ring structure and its application in an organic electroluminescent device. 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 bo...

Claims

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Application Information

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IPC IPC(8): C07D209/80C07D491/048C07D487/04C07D491/147C07D401/04C07D471/10C07D519/00C07D209/88C07D209/86C07D491/153C07D495/04C07D405/14C09K11/06H01L51/50H01L51/54
CPCC07D209/80C07D491/048C07D487/04C07D491/147C07D401/04C07D471/10C07D519/00C07D209/88C07D209/86C07D491/153C07D495/04C07D405/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/624H10K85/653H10K85/615H10K85/631H10K85/636H10K85/657H10K85/6572H10K85/6574H10K50/12H10K50/18H10K50/15
Inventor 李崇吴秀芹王芳徐浩杰
Owner JIANGSU SUNERA TECH CO LTD
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