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Fused ring compound as well as preparation method and application thereof

A compound and fused ring technology, applied in the field of fused ring compounds and their preparation, can solve the problems of unbalanced charge transport of host materials, unsatisfactory light-emitting area, and inefficient transfer of host material energy.

Active Publication Date: 2018-11-02
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 application thereof
  • Fused ring compound as well as preparation method and application thereof
  • Fused ring compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] The present embodiment provides a fused ring compound having the structure shown in the following formula D-3:

[0067]

[0068] The synthetic route of the fused ring compound represented by formula D-3 is as follows:

[0069]

[0070] The preparation method of the fused ring compound represented by formula D-3 specifically comprises the following steps:

[0071] (1) Synthesis of intermediate 3-1

[0072] Under nitrogen protection, in the 500mL three-necked flask, add the compound (50mmol) shown in 12.8g formula (C-1), 8.8g 3-chloro-2-fluoronitrobenzene (50mmol) (formula (E-1) The compound shown), 19.5g of cesium carbonate (60mmol), 200mL of dimethyl sulfoxide, reacted for 15 hours, extracted with toluene, evaporated to remove the solvent, passed through a silica gel column to obtain 14.8g of solid intermediate 3-1 (yield 72%) ;

[0073] (2) Synthesis of intermediate 4-1

[0074] Under nitrogen protection, into a 500mL three-necked flask, add 12.4g intermediat...

Embodiment 2

[0081] The present embodiment provides a fused ring compound having the structure shown in the following formula D-4:

[0082]

[0083] The synthetic route of the fused ring compound represented by formula D-4 is as follows:

[0084]

[0085] The preparation method of the fused ring compound represented by formula D-4 specifically comprises the following steps:

[0086] Using the compound represented by formula (C-2) and the compound represented by formula (E-1) as raw materials, according to the synthesis method provided in Example 1, the fused ring compound represented by formula (D-4) was obtained.

[0087] Elemental analysis: (C43H24N6) Theoretical value: C, 82.67; H, 3.87; N, 13.45; Found value: C, 82.61; H, 3.83; N, 13.49, HRMS(ESI) m / z(M+): Theoretical value: 624.21; Found: 624.19.

Embodiment 3

[0089] The present embodiment provides a fused ring compound having the structure shown in the following formula D-1:

[0090]

[0091] The synthetic route of the fused ring compound represented by formula D-1 is as follows:

[0092]

[0093] (1) Synthesis of Intermediate 1-1

[0094] Under nitrogen protection, weigh 8.7g of compound represented by formula (A-1) (30mmol), 6.7g of 1-bromo-2-nitrobenzene (33mmol), 0.2g of palladium acetate (1.0mmol), 0.66g of tri-tertiary Butylphosphine (3.5mmol), 9.3g of sodium tert-butoxide, 1000mL of toluene, reacted at 110°C for 12 hours, cooled to room temperature, extracted with chloroform, evaporated to remove the solvent, and passed through a silica gel column to obtain 10.5g of solid intermediate 1-1 ( Yield 85%);

[0095] (2) Synthetic intermediate 2-1

[0096] Under nitrogen protection, add 8.2g intermediate 1-1 (20mmol), 21.6g stannous chloride dihydrate (96mmol), 17mL hydrochloric acid, 250mL ethanol, react at 60 degrees Ce...

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Abstract

The invention discloses a fused ring compound comprising a structure shown as a formula (I) or (II). According to the fused ring compound, by controlling effective conjugation of aromatic rings and heterocyclic rings, the electron transport performance is balanced while the hole performance is improved. The compound has high triplet state energy level and glass transition temperature, is difficultin crystallization of material molecules, and is capable of ensuring high-efficiency transfer of energy to a guest material while serving as a host material of a luminous layer. The substituent groupof the fused ring compound is adjusted, the electron and hole transport performances are further improved, the singlet state and triplet state energy level difference is reduced, the compound area ofthe carrier is widened, and triplet state exciton annihilation is avoided. The invention further discloses an organic electroluminescence device. At least one functional layer contains the fused ringcompound, and the fused ring compound serves as the host material of the luminous layer and is matched with the energy level of an adjacent carrier transport layer. The luminous efficiency of the device is improved, and the driving voltage of the device is reduced.

Description

technical field [0001] The invention belongs to the technical field of display, and in particular relates to a condensed ring compound and a preparation method and application thereof. Background technique [0002] Pope et al. first discovered the electroluminescence properties of single crystal anthracene in 1965, which is the first electroluminescence phenomenon of organic compounds; in 1987, Tang et al. of Kodak Company in the United States successfully developed low-voltage, low-voltage, High-brightness organic light-emitting diodes (Organic Light-Emitting Diode, OLED). As a new type of display technology, Organic Light-Emitting Diode (OLED) has the advantages of self-luminescence, wide viewing angle, low energy consumption, rich colors, fast response speed, wide applicable temperature range and flexible display. It has great application prospects in the field of display and lighting, and has attracted more and more attention. [0003] OLEDs mostly use a sandwich struc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/16C07D487/16C07D491/22C07D487/22C07D495/22C07D471/16C07D471/22C07D487/06C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/16C07D471/22C07D487/06C07D487/16C07D487/22C07D491/16C07D491/22C07D495/22C09K2211/1092C09K2211/1088C09K2211/1059C09K2211/1044C09K2211/1029C09K2211/1011C09K2211/1007H10K85/654H10K85/6572H10K85/657H10K50/11H10K2101/30C07D493/12C07D487/04C07D487/12C07D493/22H10K50/12C09K2211/1018H10K50/121H10K2101/10
Inventor 孙华陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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