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Naphtho-five-membered ring-benzofused heterocyclic organic compounds and application thereof

A technology of organic compounds and five-membered rings, applied in the field of organic optoelectronic materials, can solve problems such as unbalanced carrier transport, mismatch between electrons and holes, shortened lifespan, etc., achieve simple preparation process and reduce turn-on voltage , the effect of improving life expectancy

Pending Publication Date: 2020-06-09
YANTAI XIANHUA CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently used phosphorescent host materials often have a single carrier transport capability, such as hole transport hosts and electron transport hosts. However, a single carrier transport capability will cause a mismatch between electrons and holes in the light-emitting layer. , resulting in severe efficiency roll-off and shortened life
[0005] Although CN108290875A discloses the main structure of a class of condensed thiophene, it can only be used as a double-host material due to the unbalanced carrier transport

Method used

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  • Naphtho-five-membered ring-benzofused heterocyclic organic compounds and application thereof
  • Naphtho-five-membered ring-benzofused heterocyclic organic compounds and application thereof
  • Naphtho-five-membered ring-benzofused heterocyclic organic compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of compound A1, the reaction equation is as follows:

[0028]

[0029] The synthesis method is as follows:

[0030] (1) Add (100mmol) 5-bromonaphthobenzothiophene, (110mmol) o-hydroxyphenylboronic acid, (1%) Pd(PPh 3 ) 4 , sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, and the reaction was completed; the reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain a yellow solid M1;

[0031] (2) Add (100mmol) intermediate M1 to 1000mL DMF solution, add (300mmol) copper oxide and (300mmol) potassium carbonate, heat to reflux, react for 12h, and the reaction is complete; evaporate the solvent, silica gel column chromatography, separate, Intermediate M2 was obtained;

[0032](3) Dissolve (100mmol) M2 in 500mL THF, add (120mmol) butyllithium at -78°C, stir under temperature control, react for 1h, add dibromoethane (120mmol) dropwise, react for 12h; A...

Embodiment 2

[0038] The synthesis of compound A5, reaction equation is as follows:

[0039]

[0040] The synthesis method is as follows:

[0041] (1) Add (100mmol) 5-bromonaphthobenzothiophene, (110mmol) o-nitrophenylboronic acid, (1%) Pd(PPh 3 ) 4 , sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, and the reaction was completed; the reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain a yellow solid M1;

[0042] (2) Add (100mmol) intermediate M1 to 1000ml o-dichlorobenzene solution, add (300mmol) triphenylphosphine, heat to reflux, react for 12h, and the reaction is complete; evaporate the solvent, perform silica gel column chromatography, and separate to obtain Intermediate M2;

[0043] (3) In the reaction flask, add (100mmol) M2, (110mmol) iodobenzene, (1%) Pd (dba), (1%) S-Phos, sodium tert-butoxide 40g (300mmol) and xylene 800mL, heat To reflux, react for 8h, and the r...

Embodiment 3

[0050] The synthesis of compound A10, the reaction equation is as follows:

[0051]

[0052] The synthesis method is as follows:

[0053] (1) Add (100mmol) 5-bromonaphthobenzofuran, (110mmol) o-nitrophenylboronic acid, (1%) Pd(PPh 3 ) 4 , sodium carbonate 40g (300mmol), toluene 800mL, ethanol 200mL and water 200mL, heated to reflux, reacted for 8h, and the reaction was completed; the reaction solution was extracted with ethyl acetate, and the organic phase was concentrated to obtain a yellow solid M1;

[0054] (2) Add (100mmol) intermediate M1 to 1000ml o-dichlorobenzene solution, add (300mmol) triphenylphosphine, heat to reflux, react for 12h, and the reaction is complete; evaporate the solvent, perform silica gel column chromatography, and separate to obtain Intermediate M2;

[0055] (3) In the reaction flask, add (100mmol) M2, (110mmol) iodobenzene, (1%) Pd (dba), (1%) S-Phos, sodium tert-butoxide 40g (300mmol) and xylene 800mL, heat To reflux, react for 8h, and the ...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to naphtha-five-membered ring-benzofused heterocycle organic compounds and application thereof. The organic compounds disclosed by the invention have a parent structure of naphtho-five-membered ring-benzofused heterocycle, are high in interatomic bond energy, present good thermal stability, are beneficial for intermolecular solid accumulation, and can be used as luminescent layer materials to effectively prolong the service life of materials. The compounds provided by the invention are derivatives of large conjugated fused heterocycles, are applied to light emitting layers, have proper energy levels matched with adjacent layers, facilitate injection of holes and electrons, can effectively reduce turn-on voltage, and can realize good light emitting efficiency in a device due to a relatively high exciton migration rate. The compounds disclosed by the invention have relatively large conjugate planes, are beneficial for molecular accumulation, show good thermodynamic stability and present long service life in devices. A preparation process of the derivatives is simple and feasible,raw materials are easy to obtain, and the derivatives are suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a naphthopentacyclic acene-fused heterocyclic organic compound and its application. Background technique [0002] Electroluminescence (EL) refers to the phenomenon that luminescent materials are excited by electric current and electric field to emit light under the action of electric field. It is a luminescence process that directly converts electrical energy into light energy. Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal display, organic electroluminescent display is not It requires a backlight source, has a large viewing angle and low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D487/04C07D491/048C07D491/147C07D491/153C07D495/04C07D495/14C07D498/04C07D498/14H01L51/54H01L51/50
CPCC07D495/14C07D495/04C07D491/153C07D491/048C07D491/147C07D498/14C07D498/04C07D403/04C07D487/04H10K85/615H10K85/654H10K85/657H10K85/6572H10K50/12
Inventor 邢其锋丰佩川刘子彦胡灵峰陈跃陈义丽
Owner YANTAI XIANHUA CHEM TECH CO LTD
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