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Organic photoelectric material containing C60 condensed ring, preparation method and application thereof

A technology of organic photoelectric materials and condensed rings, which is applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of high cost, poor stability, and many steps of axenic compounds, and achieve improved film-forming performance and electrical conductivity. The effect of increasing the efficiency and improving the hole injection efficiency

Pending Publication Date: 2020-10-27
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, in the prior art, most of the materials of the doped hole injection layer are Lewis acid metal complexes, halogens, axenene and quinone compounds, and the metal complexes and halogens have poor stability during device processing. problems, and axenic compounds have more steps in the synthesis, and the cost is higher

Method used

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  • Organic photoelectric material containing C60 condensed ring, preparation method and application thereof
  • Organic photoelectric material containing C60 condensed ring, preparation method and application thereof
  • Organic photoelectric material containing C60 condensed ring, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0048] This embodiment provides an organic optoelectronic material compound 1 containing a C60 fused ring, its structural formula is as follows The reaction formula for preparing compound 1 is:

[0049]

[0050] Concrete preparation method comprises the following steps:

[0051] Add 0.49g of fullerene C60 (1mmol), 0.40g of compound 1a (2mmol), 0.16g of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene into the reaction flask , and reacted at 120°C for 10 hours; filtered and concentrated to obtain a crude product; then separated and purified with a 200-300 mesh silica gel column to obtain the product compound 1.

[0052] Characterization data: mass spectrum MS: 887;

[0053] NMR 1 H-NMR (400 MHz, CDCl 3 ): δ1.52(d,2H), 2.85(s,3H), 2.99(m,1H), 3.32(d,1H), 3.37(t,1H).

Embodiment 2

[0055] This embodiment provides an organic photoelectric material compound 2 containing a C60 fused ring, its structural formula is as follows The reaction formula for preparing compound 2 is:

[0056]

[0057] Concrete preparation method comprises the following steps:

[0058] Add 0.49g of fullerene C60 (1mmol), 0.82g of compound 2a (2mmol), 0.16g of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene into the reaction flask , and reacted at 120°C for 10 hours; filtered and concentrated to obtain a crude product; then separated and purified with a 200-300 mesh silica gel column to obtain the product compound 2.

[0059] Characterization data: mass spectrum MS: 901;

[0060] NMR 1 H-NMR (400 MHz, CDCl 3 ): δ1.52(d,2H), 2.85(s,3H), 2.99(m,1H), 3.36(d,1H), 3.40(t,1H).

Embodiment 3

[0062] This embodiment provides an organic photoelectric material compound 3 containing a C60 fused ring, its structural formula is as follows The reaction formula for preparing compound 3 is:

[0063]

[0064] Concrete preparation method comprises the following steps:

[0065] Add 0.49g of fullerene C60 (1mmol), 1.10g of compound 3a (2mmol), 0.16g of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, 0.7mmol) and 5mL of chlorobenzene into the reaction flask , and reacted at 120°C for 10 hours; filtered and concentrated to obtain a crude product; then separated and purified with a 200-300 mesh silica gel column to obtain the product compound 3.

[0066] Characterization data: mass spectrum MS: 1039;

[0067] NMR 1 H-NMR (400 MHz, CDCl 3 ): δ1.52(d,2H), 2.99(m,1H), 3.32(d,1H), 3.37(t,1H).

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Abstract

The invention provides an organic photoelectric material containing a C60 condensed ring, wherein the organic photoelectric material containing the C60 condensed ring has a structure represented by aformula I. According to the invention, the organic photoelectric material has a C60 condensed ring skeleton, so that the organic photoelectric material has good thermal stability, and the film-formingproperty in the later processing and using process is favorably improved; the C60 condensed ring in the organic photoelectric material cooperates with substituent groups with strong electron withdrawing performance, such as halogen, cyano and the like, so that molecules are endowed with strong reduction potential, and the organic photoelectric material can be used as an object material to improvethe hole injection performance; and the organic photoelectric material containing the C60 condensed ring serves as a hole injection layer object material of an OLED device, so that charge injection can be effectively increased, the driving voltage of the OLED device is reduced, the overall efficiency of the device is improved, and the service life of the device is prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to an organic photoelectric material and its preparation method and application. Background technique [0002] The research on organic electroluminescent devices began in 1963. The device uses organic anthracene crystals as light-emitting materials, but its driving voltage is as high as 400 V, and the efficiency and life of the device are not as good as inorganic electroluminescent devices, so it has not attracted people's attention. Pay attention to. Until 1987, Tang et al. used the vacuum deposition coating method to use the arylamine derivative HTM1 as the hole transport layer and 8-hydroxyquinoline aluminum as the light-emitting layer for the first time, and achieved a brightness of 1000cd / m at a driving voltage of 10 V. 2 green light emission. So far, organic electroluminescent devices have become a research hotspot due to their advantages of sm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/94C09K11/06H01L51/50H01L51/54
CPCC07D209/94C09K11/06C09K2211/1007C09K2211/1029H10K85/6572H10K50/17
Inventor 俞云海谭奇张晓龙
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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