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2,2'-bibenzo[d]imidazolidene compound having condensed rings at the 1-, 1'-, 3- and 3'-positions, and organic light-emitting element, display device, image information processing apparatus, lighting device, image forming apparatus and exposure unit, each containing the same

一种有机发光元件、有机化合物的技术，应用在2领域，能够解决元件稳定性和寿命劣化等问题

Active Publication Date: 2017-08-01
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If any of these compounds is used in an organic electronic element such as an organic light-emitting element, the element deteriorates in terms of stability and lifetime

Method used

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  • 2,2'-bibenzo[d]imidazolidene compound having condensed rings at the 1-, 1'-, 3- and 3'-positions, and organic light-emitting element, display device, image information processing apparatus, lighting device, image forming apparatus and exposure unit, each containing the same
  • 2,2'-bibenzo[d]imidazolidene compound having condensed rings at the 1-, 1'-, 3- and 3'-positions, and organic light-emitting element, display device, image information processing apparatus, lighting device, image forming apparatus and exposure unit, each containing the same
  • 2,2'-bibenzo[d]imidazolidene compound having condensed rings at the 1-, 1'-, 3- and 3'-positions, and organic light-emitting element, display device, image information processing apparatus, lighting device, image forming apparatus and exposure unit, each containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0189] Synthesis of Exemplary Compound A2

[0190] (1) Synthesis of Compound E3

[0191]

[0192] The following compounds and solvents were added to a 100 mL recovery flask:

[0193] E11: 1.36g (10.0mmol)

[0194] E15: 4.35g (21.0mmol)

[0195] Tris(dibenzylideneacetone)dipalladium(0): 274mg(0.3mmol)

[0196] 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl: 333mg (0.7mmol)

[0197] Sodium tert-butoxide: 2.31g (24.0mmol)

[0198] Toluene: 50mL

[0199] A mixture of these materials was heated to reflux with stirring for 8 hours. After completion of the reaction, the reaction mixture was filtered through Celite and then separated by adding water. The isolated reaction product was purified by silica gel column chromatography (eluent: heptane / chloroform=3 / 1 to 2 / 1) to obtain 2.53 g of Compound E3 (yield: 65%).

[0200] (2) Synthesis of Compound E4

[0201]

[0202] The following compounds and solvents were added to a 100 mL recovery flask:

[0203] E27: 1.94g ...

Embodiment 2

[0217] Synthesis of Exemplified Compound A4

[0218] Exemplary compound A4 was synthesized in the same manner as in operation (1) of Example 1, except that compound E5 shown below was used instead of compound E1.

[0219]

[0220] The resulting compounds were identified as described below.

[0221] The resulting compound was subjected to matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF-MS) using Autoflex LRF manufactured by Bruker.

[0222] Measured value: m / z = 852.33; Calculated value: 852.42

[0223] The oxidation potential measured using an electrochemical analyzer Model 660C manufactured by ALS was -0.95V.

Embodiment 3

[0225] Synthesis of Exemplified Compound A7

[0226] Exemplary compound A7 was synthesized in the same manner as in operation (1) of Example 1, except that compound E6 shown below was used instead of compound E1.

[0227]

[0228] The resulting compounds were identified as described below.

[0229] The resulting compound was subjected to matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF-MS) using Autoflex LRF manufactured by Bruker.

[0230] Measured value: m / z = 892.55; Calculated value: 892.36

[0231] The oxidation potential measured using an electrochemical analyzer Model 660C manufactured by ALS was -0.92V.

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Abstract

A stable 2,2'-bibenzo[d]imidazolidene compound is provided. The 2,2'-bibenzo[d]imidazolidene compound is expressed by the following General Formula (1). In General Formula (1), Ar1 to Ar8 each represent a substituted or unsubstituted condensed ring. R1 to R8 each represent a hydrogen atom or a substituent.

Description

technical field [0001] The present invention relates to 2,2'-bibenzo[d]imidazolylene compounds having condensed rings at 1-, 1'-, 3- and 3'-positions, and organic light-emitting elements, display devices, Image information processing device, lighting equipment, image forming device and exposure unit. Background technique [0002] An organic light emitting element includes an anode and a cathode and an organic compound layer between the anode and the cathode. This organic light-emitting element emits light by recombination of holes injected from an anode and electrons injected from a cathode in a light-emitting layer that is one type of organic compound layer. Recent remarkable progress in the development of organic light-emitting elements has realized thin, lightweight light-emitting devices capable of emitting various emission wavelengths at low driving voltages and responding rapidly. [0003] In order to lower the driving voltage of the organic light emitting element, i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20C07D235/30C07D409/14C09K11/06H01L51/50H05B33/08H10K99/00H05B44/00
CPCC07D235/20C07D409/14C09B23/102C09B57/00C07D401/14H10K85/626H10K85/6572H10K85/6576H10K50/171H10K59/8051H10K59/8052H10K59/8794H05B45/60H10K59/1213H10K50/11H10K50/81H10K50/82H10K50/87G03G15/04036H01L27/1225H01L29/7869
Inventor 镰谷淳西出洋祐宫下广和山田直树
Owner CANON KK