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Pyrene structure-containing compound, and organic luminescent device thereof

An organic light-emitting device and compound technology, which are applied in the field of pyrene-like structure-containing compounds and organic light-emitting devices to achieve the effects of not easy to crystallize, improved electron transport performance, and good industrialization prospects

Inactive Publication Date: 2019-01-11
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Organic electroluminescent materials have continuously achieved breakthroughs in recent years, and have made remarkable progress, posing a strong challenge to traditional display materials.

Method used

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  • Pyrene structure-containing compound, and organic luminescent device thereof
  • Pyrene structure-containing compound, and organic luminescent device thereof
  • Pyrene structure-containing compound, and organic luminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] [Example 1] Synthesis of Compound 1

[0091]

[0092] Synthesis of compound a1

[0093] Into a 250 mL two-necked flask was added 200 mL of DMF (dimethylformamide), followed by pentafluoropyridine (17.5 g, 103.5 mmol), potassium carbonate (17.2 g, 124.3 mmol) and ethyl cyanoacetate (11.7 g, 103.5 mmol) , stirred at room temperature for 48 hours. Distilled water and acetic acid were added dropwise to the mixture to terminate the reaction, and then extracted with dichloromethane, the organic phases were combined and dried, concentrated, and recrystallized to obtain compound a1 (24.4 g, yield 90%).

[0094] Mass Spectrum m / z: 262.12 (calculated: 262.16). Theoretical element content (%)C 10 h 6 f 4 N 2 o 2 : C, 45.81; H, 2.31; F, 28.99; N, 10.69; O, 12.21 The measured element content (%): C, 45.81; The above results confirmed that the obtained product was the target product.

[0095] Synthesis of compound b1

[0096] Compound a1 (26.7g, 102.4mmol), 50% acetic ac...

Embodiment 2

[0104] [Example 2] Synthesis of compound 13

[0105]

[0106] The pentafluoropyridine in Example 1 was replaced by equimolar cyanuric fluoride, and the other steps were the same as in Example 1 to obtain the target compound 13. Mass Spectrum m / z: 518.56 (calculated: 518.51). Theoretical element content (%)C 34 h 16 f 2 N 4 : C, 78.76; H, 3.11; F, 7.33; N, 10.81 Measured element content (%): C, 78.75; H, 3.11; F, 7.33; N, 10.82. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0107] [Example 3] Synthesis of compound 18

[0108]

[0109] The compound b1 in Example 1 was replaced with equimolar 2-(perfluorophenyl)acetonitrile, and the other steps were the same as in Example 1 to obtain the target compound 18. Mass Spectrum m / z: 569.56 (calculated: 569.52). Theoretical element content (%)C 37 h 16 f 5 N: C, 78.03; H, 2.83; F, 16.68; N, 2.46 Measured element content (%): C, 78.04; H, 2.84; F, 16.65; N, 2.47. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses a pyrene structure-containing compound, and an organic luminescent device thereof. The pyrene structure-containing compound is formed through combination of a pyrene ring structure with a fluorene alkenyl; on one hand, a foldable three dimensional structure is achieved, so that certain distortion of the pyrene structure-containing compound in the space three-dimensional structure is realized, and the film forming performance is improved; on the other hand, the pyrene structure possesses relatively high triplet state energy level and relatively wide energy gap, and excellent blue light performance, when the pyrene ring structure is connected with fluorene alkenyl with electron withdrawing performance, green light or red light is emitted after bathochromic shift. Thepyrene structure-containing compound possesses appropriate HOMO and LUMO values, is capable of blocking transmission from cavities to electron transmission layers, and improving effective luminescence. When the pyrene structure-containing compound is applied in organic luminescent devices, the pyrene structure-containing compound is taken as a luminescent layer or a cavity blocking layer, low driving voltage and high luminescent efficiency of the organic luminescent devices are achieved.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a compound containing a pyrene structure and an organic light-emitting device thereof. Background technique [0002] Organic light emitting diode (Organic Light Emitting Diode, OLED) is a light-emitting device prepared by using electrons and holes to recombine light in organic thin films. High, with high contrast, pure color, almost no problem of viewing angle; (3) ultra-thin, composed of very thin organic material coating and matrix material, small in size and suitable for portable products; (4) power consumption Very small, environmentally friendly and energy-saving; (5) fast response speed, one thousandth of that of LCD; (6) wide operating temperature range, and can still display normally at -40°C. [0003] Organic electroluminescent materials have continuously achieved breakthroughs in recent years, and have made remarkable progress, posing a strong c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D239/30C07D239/26C07D239/28C07D251/20C07D251/24C07C255/51C07C255/32C07C255/35C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C255/32C07C255/35C07C255/51C07D213/61C07D239/26C07D239/28C07D239/30C07D251/20C07D251/24C07C2603/50C07C2603/18C09K2211/1059C09K2211/1044C09K2211/1011C09K2211/1007C09K2211/1029H10K85/615H10K85/622H10K85/626H10K85/654H10K50/11
Inventor 刘喜庆蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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