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A kind of fused polycyclic compound and its preparation method and use

A technology of fused polycyclic compounds, applied in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problem of low luminous efficiency and luminous performance of devices, inefficient energy transfer of host materials, and triplet energy levels. Low-level problems, to achieve the effect of improving performance and luminous efficiency, high thermal stability and morphological stability, and improved matching

Active Publication Date: 2020-04-21
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 polycyclic compound and its preparation method and use
  • A kind of fused polycyclic compound and its preparation method and use
  • A kind of fused polycyclic compound and its preparation method and use

Examples

Experimental program
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Embodiment 1

[0056] This embodiment provides a fused polycyclic compound having the structure shown in the following formula D-1:

[0057]

[0058] The synthetic route of the fused polycyclic compound shown in formula D-1 is as follows:

[0059]

[0060] The preparation method of the fused polycyclic compound shown in formula D-1 specifically comprises the following steps:

[0061] (1) Synthesis of intermediate 1-1

[0062] 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, and mix well , After reacting 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 resulting solid to a 1L three-necked flask, add 600mL toluene, 5g p-toluenesulfonic acid, and heat to reflux for reaction 2 After 1 hour, it was cooled to room t...

Embodiment 2

[0071] This embodiment provides a fused polycyclic compound having the structure shown in the following formula D-5:

[0072]

[0073] The synthetic route of fused polycyclic compound shown in formula D-5 is as follows:

[0074]

[0075] The preparation method of the fused polycyclic compound shown in formula D-5 specifically comprises the following steps:

[0076] (1) By the synthesis method shown in Example 1, intermediate 3-1 was synthesized.

[0077] (2) Synthesis of fused polycyclic compound D-5

[0078] Under nitrogen protection, add 5g intermediate 3-1 (16.7mmol), 5.3g compound (22mmol), 5.5g cesium carbonate (16.7mmol), 1g 4-dimethylaminopyridine (8.2mmol), 90mL dimethyl sulfoxide, mix well, react at 100°C for 3 hours, after cooling to room temperature, extract with toluene, spin The solvent was evaporated and passed through a silica gel column to obtain 6.7 g of solid condensed polycyclic compound D-5 (yield 81%).

[0079]Elemental analysis: (C35H25N3O) the...

Embodiment 3

[0081] This embodiment provides a fused polycyclic compound having the structure shown in the following formula D-9:

[0082]

[0083] The synthetic route of condensed polycyclic compound shown in formula D-9 is as follows:

[0084]

[0085] The preparation method of the fused polycyclic compound shown in formula D-9 specifically comprises the following steps:

[0086] (1) By the synthesis method shown in Example 1, intermediate 3-1 was synthesized.

[0087] (2) Synthesis of fused polycyclic compound D-9

[0088] Under nitrogen protection, add 5g intermediate 3-1 (16.7mmol), 5.3g compound (22mmol), 5.5g cesium carbonate (16.7mmol), 1g 4-dimethylaminopyridine (8.2mmol), 90mL dimethyl sulfoxide, mix well, react at 100°C for 3 hours, after cooling to room temperature, extract with toluene, spin The solvent was evaporated and passed through a silica gel column to obtain 7.1 g of fused polycyclic compound D-9 (yield 82%).

[0089] Elemental analysis: (C36H26N4O) theoreti...

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Abstract

The invention discloses a condensed polycyclic compound, which has the structure shown in formula (I) or formula (II). The above-mentioned fused polycyclic compound has 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. Adjust the substituent group of the fused polycyclic compound 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 fused polycyclic compound, the fused polycyclic compound is used as the main material of the light-emitting layer, and the adjacent carrier transport layer can Level matching, while improving the luminous efficiency of the device, reduces the driving voltage of the device, which is beneficial to the long-term use of the organic electroluminescent device.

Description

technical field [0001] The invention belongs to the field of display technology, and in particular relates to a condensed polycyclic 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. Advantages, it has great application prospects in the field of display and lighting, and more and more people pay attention to it. [0003] Most OLEDs use a sandwich...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D491/052C07D519/00C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/631H10K85/654H10K85/6576H10K85/657H10K85/6572H10K50/11
Inventor 孙华陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD