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Fused ring compound as well as preparation method and purpose thereof

A compound and fused ring technology, applied in the field of fused ring compounds and their preparation, can solve the problems of unsatisfactory light-emitting region, inefficient energy transfer of host materials, and easy crystallization.

Active Publication Date: 2018-11-23
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 in 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; Efficient transfer to the guest material, leading to the defect of low luminous efficiency and luminous performance of the device

Method used

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  • Fused ring compound as well as preparation method and purpose thereof
  • Fused ring compound as well as preparation method and purpose thereof
  • Fused ring compound as well as preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
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, weigh 10g of compound (33mmol) shown in formula (A-1), 6.7g 1-bromo-2-nitrobenzene (33mmol) (compound shown in formula (B-1)), 0.2g palladium acetate (1.0mmol), 0.66g tri-tert-butylphosphine (3.5mmol), 9.3g sodium tert-butoxide, 1000mL toluene, reacted at 110°C for 12 hours, cooled to room temperature, extracted with chloroform, rotary evaporated to remove the solvent, and passed through a silica gel column to obtain 11.0 g solid intermediate 1-1 (yield 85%);

[0078] (2) Synthesis of Intermediate 2-1

[0079] Under the protection of n...

Embodiment 2

[0084] This embodiment provides a condensed ring compound, which has the structure shown in the following formula D-2:

[0085]

[0086] The synthetic route of the condensed ring compound shown in formula D-2 is as follows:

[0087]

[0088] The preparation method of the condensed ring compound shown in formula D-2 specifically comprises the following steps:

[0089] (1) Using the compound shown in formula (A-2) and the compound shown in formula (B-1) as starting materials, according to the synthetic method in Example 1, synthesize intermediate 2-2;

[0090] (2) Synthesis of condensed ring compound D-2

[0091] Under nitrogen protection, add 3.8g intermediate 2-2 (10mmol), 3.2g compound (12mmol), 3.4g cesium carbonate (10mmol), 0.6g 4-dimethylaminopyridine (5mmol), dimethyl sulfoxide 40mL, 100 ℃ reaction 3 hours, after cooling to room temperature, toluene extraction, rotary evaporation removes solvent, Pass through a silica gel column to obtain 5.0 g of solid condens...

Embodiment 3

[0094] This embodiment provides a condensed ring compound, which has the structure shown in the following formula D-8:

[0095]

[0096] The synthetic route of the condensed ring compound shown in formula D-8 is as follows:

[0097]

[0098] The preparation method of the condensed ring compound shown in formula D-8 specifically comprises the following steps:

[0099] (1) Synthesize intermediate 2-2 with the synthetic method in Example 2;

[0100] (2) Under nitrogen protection, add 3.8g intermediate 2-2 (10mmol), 0.09g palladium acetate (0.4mmol), 0.29g tri-tert-butylphosphine (1.42mmol), 4.5g (12mmol), 4.2g sodium tert-butoxide, 250mL toluene, reacted at 110°C for 12 hours, cooled to room temperature, extracted with chloroform, and removed the solvent by rotary evaporation, and passed through a silica gel column to obtain 5.7g solid condensed ring compound D-8 (yield: 82 %).

[0101] Elemental analysis: (C49H31N5) Theoretical value: C, 85.32; H, 4.53; N, 10.15; Found...

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Abstract

The invention discloses a fused ring compound, which has a structure shown as a formula (I) or a formula (II). The effective conjugation of aromatic rings and heterocyclic rings is controlled in the fused ring compound; the hole performance is improved; meanwhile, the electronic transmission performance is favorably balanced; the compound has high triplet state energy level and glass transition temperature; material molecules cannot easily crystallize; when the fused ring compound is used as a luminescent layer host material, the efficient transfer of energy to guest materials can be guaranteed. The substituent group of the fused ring compound is regulated, so that the electron and hole transmission performance is further improved; the singlet state and triplet state energy level difference is reduced; the compound region of carriers is expanded; the triplet state exciton annihilation is prevented. The invention also discloses an organic electroluminescence device; at least one function layer contains the fused ring compound; the fused ring compound is used as the host material of the luminescent layer and is matched with the adjacent carrier transmission layer energy level; the luminous efficiency of the device is improved; meanwhile, the driving voltage of the device is reduced.

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, low-voltage, High-brightness organic light-emitting diode (Organic Light-Emitting Diode, OLED). Organic Light-Emitting Diode (OLED), as a new type of display technology, has many advantages such as self-illumination, wide viewing angle, low energy consumption, rich colors, fast response, 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 sandwic...

Claims

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Application Information

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IPC IPC(8): C07D487/06C07D487/16C07D487/22C07D471/22C07D471/16C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/16C07D471/22C07D487/06C07D487/16C07D487/22C09K2211/1088C09K2211/1044C09K2211/1059C09K2211/1007C09K2211/1029H10K85/6574H10K85/6572H10K50/12
Inventor 孙华陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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