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Fused ring compound as well as preparation method and application thereof

A compound and condensed ring technology, applied in the field of condensed ring compounds and their preparation, can solve the problems of inefficient energy transfer of host materials, unsatisfactory light-emitting area, and low light-emitting efficiency and light-emitting performance of devices

Active Publication Date: 2018-12-14
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

[0074] The present embodiment provides a fused ring compound having the structure shown in the following formula D-2:

[0075]

[0076] The synthetic route of the fused ring compound represented by formula D-2 is as follows:

[0077]

[0078] The preparation method of the fused ring compound shown in formula D-2 specifically comprises the following steps:

[0079] (1) Synthesis of Intermediate 1-1

[0080] Under nitrogen protection, into a 500mL three-necked flask, add 9.1g (50mmol) of the compound represented by formula (A-1), 7.8g (25mmol) of 2,2'-dibromobiphenyl (formula (B-1) the compound shown), 200 mL of tetradioxane, 48 mg of cuprous iodide (0.25 mmol), 3.5 g of sodium tert-butoxide (36 mmol), 0.3 mL of cis-1,2-cyclohexanediamine, 100°C After the reaction was performed for 12 hours, after extraction with chloroform three times, the solvent was removed by rotary evaporation, and passed through a silica gel column to obtain 6.2 g of solid intermediate 1-1 (yield: ...

Embodiment 2

[0087] The present embodiment provides a fused ring compound having the structure shown in the following formula D-1:

[0088]

[0089] The synthetic route of the fused ring compound represented by formula D-1 is as follows:

[0090]

[0091] The preparation method of the fused ring compound represented by formula D-1 specifically comprises the following steps:

[0092] (1) with the synthetic method shown in embodiment 1, synthesize intermediate 2-1;

[0093] (2) Synthesis of fused ring compound D-1

[0094] Under nitrogen protection, add 1.7g compound 1-2 (5mmol), 0.03g palladium acetate (0.15mmol), 0.1g tri-tert-butylphosphine (0.55mmol), 2g compound (5.1mmol), 1.41g of sodium tert-butoxide, 750mL 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 2.6g of solid compound C-16 (yield 81%) ).

[0095] Elemental analysis: (C45H29N5) Theoret...

Embodiment 3

[0097] The present embodiment provides a fused ring compound having the structure shown in the following formula D-7:

[0098]

[0099] The synthetic route of the fused ring compound represented by formula D-7 is as follows:

[0100]

[0101] The preparation method of the fused ring compound represented by formula D-7 specifically includes the following content:

[0102] (1) Synthesis of intermediate 3-1

[0103] Under nitrogen protection, into a 500mL three-necked flask, add 5.6g of the compound (20mmol) of formula (C-1), 3.5g of 3-chloro-2-fluoronitrobenzene (compound of formula (E-1)) (20mmol) ), 7.8g of cesium carbonate (24mmol), 80mL of dimethyl sulfoxide, reacted for 15 hours, extracted with toluene, evaporated to remove the solvent, passed through a silica gel column to obtain 6.5g of solid intermediate 3-1 (yield 75%);

[0104] (2) Synthesis of intermediate 4-1

[0105] Under nitrogen protection, 4.3 g of intermediate 3-1 (10 mmol), 0.2 g of palladium acetate ...

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Abstract

The invention discloses a fused ring compound. The fused ring compound has the structure as shown in a formula (I) or a formula (II). The fused ring compound is favorable for balancing electronic transmission property while improving the cavitation performance by controlling effective conjugation of an aromatic ring and a heterocyclic ring; and the compound has high three linear energy level and vitreous transition temperature, the material molecules are not liable to crystallization, and the compound serving as a main body material of a light-emitting layer can guarantee that the energy is efficiently transmitted to an object material. The substituent group of the fusing ring compound is adjusted, so that the transmission performance of electrons and cavities is further improved, single linear and three linear energy level difference is reduced, the composite area of a current carrier is widened and three linear exciton annihilation is avoided. The invention also discloses an organicelectroluminescence device; at least one functional layer comprises the fused ring compound; the fused ring compound serves as the main body material of the light-emitting layer and is matched with the energy level of the adjacent current carrier transmission layer; and the driving voltage of the device is reduced while the light-emitting efficiency of the device is improved.

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): C07D471/22C07D487/06C07D487/16C07D487/22C09K11/06H01L51/54
CPCC09K11/06C07D471/22C07D487/06C07D487/16C07D487/22C09K2211/1029C09K2211/1007C09K2211/1059C09K2211/1044H10K85/654H10K85/6574H10K85/6572H10K50/11H10K2101/40H10K50/15C07D487/04H10K50/12C09K2211/1018H10K2101/10H10K2101/30
Inventor 孙华陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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