Compound taking dibenzo five-membered heterocyclic ring as core and application thereof

A five-membered heterocycle and compound technology, applied in the field of semiconductors, can solve the problems of device efficiency and lifespan to be improved, short lifespan, inability to balance electron transport and hole transport in the light-emitting layer, etc.

Active Publication Date: 2021-01-05
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The internal electron transport and hole transport of the light-emitting layer material itself need to reach a proper balance to effectively prevent light emission at the interface. If the hole-type material and the electron-type material in the double host are not well matched, the device will be at the interf

Method used

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  • Compound taking dibenzo five-membered heterocyclic ring as core and application thereof
  • Compound taking dibenzo five-membered heterocyclic ring as core and application thereof
  • Compound taking dibenzo five-membered heterocyclic ring as core and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Embodiment 1. Preparation of compound 1:

[0090]

[0091] (1) In a three-necked flask, under the protection of nitrogen, weigh 0.01mol of raw material A-1 and dissolve it in tetrahydrofuran, cool to -78°C, and then add 8ml of 1.6mol / L n-butyllithium tetrahydrofuran solution to the reaction system , after reacting for 3 hours at -78°C, add 0.013mol triisopropyl borate, react for 2h, then raise the reaction system to 0°C, add 10ml 2mol / L hydrochloric acid solution, stir for 3h, the reaction is complete, add ether to extract, the extract Add anhydrous magnesium sulfate to dry, spin evaporate, and recrystallize with ethanol solvent to obtain intermediate I-1;

[0092] (2) In the three-necked flask, under the protection of nitrogen, add 0.01mol intermediate I-1, 0.012mol raw material B-1, dissolve with mixed solvent (90ml toluene, 45ml ethanol), and then add 1×10 -4 mol Pd(PPh 3 ) 4 , 0.03molK 2 CO 3 Aqueous solution (2M), heating and reflux reaction for 15 hours, s...

Embodiment 4

[0094] Example 4. Preparation of compound 33:

[0095]

[0096] (1) In a three-necked flask, under the protection of nitrogen, weigh 0.01mol of raw material A-2 and dissolve it in tetrahydrofuran, cool to -78°C, and then add 8ml of 1.6mol / L n-butyllithium tetrahydrofuran solution to the reaction system , after reacting for 3 hours at -78°C, add 0.013mol triisopropyl borate, react for 2h, then raise the reaction system to 0°C, add 10ml 2mol / L hydrochloric acid solution, stir for 3h, the reaction is complete, add ether to extract, the extract Add anhydrous magnesium sulfate to dry, spin evaporate, and recrystallize with ethanol solvent to obtain intermediate I-2;

[0097] (2) In the three-neck flask, under the protection of nitrogen, add 0.01mol intermediate I-2, 0.012mol raw material B-1, dissolve with mixed solvent (90ml toluene, 45ml ethanol), and then add 1×10 -4 mol Pd(PPh 3 ) 4 , 0.03molK 2 CO 3 Aqueous solution (2M), heating and reflux reaction for 15 hours, sampl...

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PUM

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Abstract

The invention discloses a compound taking a dibenzo five-membered heterocyclic ring as a core and an application thereof, and belongs to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (1) or a general formula (2), the compound provided by the invention contains a dibenzo five-membered heterocyclic parent nucleus structure, and has appropriate HOMO and LUMO energy levels, a relatively high triplet state energy level (T1) and a relatively low dipole moment. After the compound is applied to an OLED device, the luminousefficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Description

technical field [0001] The invention relates to a compound with a dibenzo five-membered heterocycle as the core and an application thereof, belonging to the technical field of semiconductors. Background technique [0002] When an organic electroluminescent device includes an anode, a cathode, and an organic functional layer arranged between the anode and the cathode, the organic functional layer is a general term for all layers between the cathode and the anode. The organic functional layer comprises an emitting layer, there may be a hole-transporting region between the anode and the emitting layer, and there may be an electron-transporting region between the emitting layer and the cathode. Holes from the anode can migrate to the light emitting layer through the hole transport region, and electrons from the cathode can migrate to the light emitting layer through the electron transport region. Carriers (holes and electrons) recombine in the light-emitting layer to generate e...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D409/14C07D209/86C07D401/14C07D403/14C07D491/048C07D519/00C07D487/04C07D495/04C09K11/06H01L51/50H01L51/54
CPCC07D405/14C07D409/14C07D209/86C07D401/14C07D403/14C07D491/048C07D519/00C07D487/04C07D495/04C09K11/06C09K2211/1029C09K2211/1088C09K2211/1011C09K2211/1007C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1092H10K85/622H10K85/615H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K50/11
Inventor 陈海峰殷梦轩李崇崔明
Owner JIANGSU SUNERA TECH CO LTD
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