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A kind of fused ring compound and its preparation method and application

A compound and fused ring technology, which is applied in the field of fused ring compounds and their preparation, can solve the problems of low luminous efficiency and luminous performance of devices, inefficient energy transfer of host materials, and low triplet energy level, so as to improve performance and luminous efficiency , high thermal stability and morphological stability, and the effect of reducing the injection barrier

Active Publication Date: 2021-04-20
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Therefore, the technical problem to be solved by the present invention is to overcome the low triplet energy level and easy crystallization of the host material of the light-emitting layer in the prior art, and the energy of the host material cannot be efficiently transferred to the guest material, resulting in low luminous efficiency and luminous performance of the device. Defects

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  • A kind of fused ring compound and its preparation method and application
  • A kind of fused ring compound and its preparation method and application
  • A kind of fused ring compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0071] This embodiment provides a condensed ring compound, which has the structure shown in the following formula D-1:

[0072]

[0073] The synthetic route of the condensed ring compound shown in formula D-1 is as follows:

[0074]

[0075] The preparation method of the condensed ring compound shown in formula D-1 specifically comprises the following steps:

[0076] (1) Synthesis of intermediate 1-1

[0077] Under nitrogen protection, into a 1L three-necked flask, add 13.8g (50mmol) of the compound represented by formula (A-1), 500mL of tetrahydrofuran, and add 110mL (1M) of methylmagnesium bromide solution at -20°C, Mix well, react at room temperature for 6 hours, add water to quench the reaction, extract three times with dichloromethane, remove the solvent by rotary evaporation, transfer the obtained solid to a 1L three-necked flask, add 600mL toluene, 5g p-toluenesulfonic acid, and heat to reflux After reacting for 2 hours, cool to room temperature, extract with to...

Embodiment 2

[0086] This embodiment provides a condensed ring compound, which has the structure shown in the following formula D-11:

[0087]

[0088] The synthetic route of the condensed ring compound shown in formula D-11 is as follows:

[0089]

[0090] The preparation method of the condensed ring compound shown in formula D-11 specifically comprises the following steps:

[0091] (1) Synthesis of intermediate 3-1

[0092] Under nitrogen protection, into a 1L three-necked flask, add 13.8g (50mmol) of the compound represented by formula (C-1), 500mL of tetrahydrofuran, and add 110mL (1M) of methylmagnesium bromide solution at -20°C, Mix well, react at room temperature for 6 hours, add water to quench the reaction, extract three times with dichloromethane, remove the solvent by rotary evaporation, transfer the obtained solid to a 1L three-necked flask, add 600mL toluene, 5g p-toluenesulfonic acid, and heat to reflux After reacting for 2 hours, cool to room temperature, extract with...

Embodiment 3

[0101] This embodiment provides a condensed ring compound, which has the structure shown in the following formula D-5:

[0102]

[0103] The synthetic route of the condensed ring compound shown in formula D-5 is as follows:

[0104]

[0105] The preparation method of the condensed ring compound shown in formula D-5 specifically includes the following contents:

[0106] Using the compound represented by formula (A-2) as a starting material, the fused ring compound represented by formula D-5 was prepared according to the synthesis steps and reaction conditions of step (1) to step (4) in Example 1.

[0107] Elemental analysis: (C41H27N3O2) theoretical value: C, 82.95; H, 4.58; N, 7.08; O, 5.39; measured value: C, 82.91; H, 4.62; N, 7.07; z(M+): theoretical value: 593.21; measured value: 593.37.

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Abstract

The invention discloses a condensed ring compound, which has the structure shown in formula (I) or formula (II). The above-mentioned condensed ring compounds have high triplet energy level and glass transition temperature. As the host material of the light-emitting layer, it can ensure the efficient transfer of energy to the guest material, and is not easy to crystallize, which is conducive to improving the luminous efficiency of the device. The substituent group of the fused ring compound is adjusted so that it has both electron transport and hole transport properties, reduces the energy level difference between its singlet state and triplet state, broadens the recombination area of ​​carriers, and prevents the annihilation of triplet excitons. The invention also discloses an organic electroluminescent device, at least one functional layer contains the above-mentioned condensed ring compound, and the condensed ring compound is used as the host material of the light-emitting layer to match the energy level of the adjacent carrier transport layer. While improving the luminous efficiency of the device, the driving voltage of the device is reduced, which is beneficial to realizing the long-term use of the organic electroluminescent device.

Description

technical field [0001] The invention belongs to the field of display technology, and specifically relates to a condensed ring compound and its preparation method and application. Background technique [0002] Pope et al. first discovered the electroluminescent properties of single crystal anthracene in 1965, which is the first electroluminescent phenomenon of organic compounds; in 1987, Tang et al. from Kodak Company of the United States successfully developed low-voltage, High-brightness organic light-emitting diode (Organic Light-Emitting Diode, OLED). As a new type of display technology, Organic Light-Emitting Diode (OLED) has many advantages such as self-illumination, wide viewing angle, low energy consumption, rich colors, fast response speed, wide applicable temperature range and flexible display. , has great application prospects in the fields of display and lighting, and has been paid more and more attention by people. [0003] Most OLEDs use a sandwich structure, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C09K11/06H01L51/54
CPCC09K11/06C07D491/052C09K2211/1059C09K2211/1044C09K2211/1088H10K85/654H10K85/6574H10K85/6572
Inventor 孙华陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD