Triazine compound containing fluorene structure and organic luminous device thereof

A technology of organic light-emitting devices and triazine compounds, applied in the field of organic optoelectronic materials, can solve problems such as device performance degradation, and achieve the effects of low driving voltage, stable structure, and prevention of aggregation

Inactive Publication Date: 2018-09-28
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The hole mobility of the hole transport material in the device is generally much greater than the electron mobility of the electron transport material, which will cause a significant decrease in device performance

Method used

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  • Triazine compound containing fluorene structure and organic luminous device thereof
  • Triazine compound containing fluorene structure and organic luminous device thereof
  • Triazine compound containing fluorene structure and organic luminous device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] [Example 1] Synthesis of Compound A1

[0070]

[0071] Synthesis of intermediate a1-1

[0072] Take 3,5-dichlorobiphenyl (9.4g, 42.4mmol) into a three-necked flask, add 100mL of THF, protect it under nitrogen, stir at -78°C for 30 minutes, then add 21mL of n-butyllithium (2.5M), and react 1 After 1 hour, add 14 g of triisopropyl borate, react at low temperature for 1 hour, and gradually return to room temperature. In the post-treatment process, 2M hydrochloric acid was added to the system to make the pH of the solution 4-5, and the liquid separation was allowed to stand. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, and spin-dried to obtain intermediate a1-1 (8.2g, yield 80%).

[0073]Mass Spectrum m / z: 242.16 (calculated: 242.09). Theoretical element content (%)C 12 h 12 B 2 o 4 : C, 59.60; H, 5.00; B, 8.94; O, 26.46 The measured element content (%): C, 59.61; H, 5.02; B, 8.94; O, 26.43. The above results confirmed tha...

Embodiment 2

[0080] [Example 2] Synthesis of Compound A40

[0081]

[0082] The 2,4-dibromo-6-phenyl-1,3,5-triazine in Example 1 was replaced by an equimolar compound d, and the other steps were the same as in Example 1 to obtain the target product compound A40 . Mass Spectrum m / z: 936.26 (calculated: 936.15). Theoretical element content (%)C 69 h 49 N 3 O: C, 88.53; H, 5.28; N, 4.49; O, 1.71 Measured element content (%): C, 88.53; H, 5.26; N, 4.49; O, 1.73. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0083] [Example 3] Synthesis of Compound B1

[0084]

[0085] Synthesis of intermediate b1-1

[0086] After 4H-cyclopentaphenanthrene is replaced by iodomethane, react with liquid bromine to obtain 8-bromo-4,4-dimethylcyclopentaphenanthrene. Take 8-bromo-4,4-dimethylcyclopentaphenanthrene (12.6g, 42.4mmol) into a three-necked flask, add THF 100mL, protect with nitrogen, stir at -78°C for 30 minutes, then add n-butyllithium (2.5 M) 21 mL, reacted for 1 hour, then added 7 g of triisopropyl borate, reacted at low temperature for 1 hour, and gradually returned to room temperature. In the post-treatment process, 2M hydrochloric acid was added to the system to make the pH value of the solution 4-5, and the liquid separation was allowed to stand, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, and spin-dried to obtain intermediate b1-1 (8.3g, yield 75%).

[0087] Mass Spectrum m / z: 262.16 (calculated: 262.11). Theoretical element content (...

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Abstract

The invention discloses a triazine compound containing a fluorene structure and an organic luminous device thereof and relates to the technical field of organic optoelectronic materials. On the one hand, triazine group structures are stable and have high glass transition temperature, high electronic mobility and a low energy level, fluorene groups are three-dimensional spatial structures and can effectively prevent molecular aggregation and inhibit crystallization of molecules, and by means of the advantages of the fluorene groups that the fluorene groups are easy to modify and high in rigidness, the structure of the compound is stable. On the other hand, the triazine groups are combined with the fluorene groups and connected with the fluorene groups through benzene rings or biphenyl rings, conjugated systems are increased, continuous pi-conjugated systems bring great electronic mobility, and therefore high electronic mobility is achieved. Moreover, through the combination of the two kinds of groups, transmission of carriers is balanced. By applying the compound in the organic luminous device to serve as an electronic transmission layer or a cavity blocking layer for use, the device has the advantages that the driving voltage is low and the luminous efficiency is high, and is superior to existing frequently-used OLED devices.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triazine compound containing a fluorene 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 charge transport materials are a class of organic semiconductor materials that can achieve controllable directional and ordered ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/24C07D405/04C07D409/04C07D403/04C07D401/14C07D403/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D251/24C07D401/14C07D403/04C07D403/14C07D405/04C07D409/04C09K2211/1092C09K2211/1088C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1059C09K2211/1044H10K85/624H10K85/622H10K85/615H10K85/633H10K85/654H10K85/6576H10K85/6572H10K85/6574H10K50/16
Inventor 刘喜庆蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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