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Ladder compound, and organic electroluminescent element using same

A technology for electroluminescent elements and compounds, applied in electroluminescent light sources, electrical components, organic semiconductor devices, etc., can solve problems such as inability to obtain high performance, and achieve high efficiency.

Active Publication Date: 2015-06-17
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As for the phosphorescent organic EL element, it is known from its luminescent characteristics that it is impossible to obtain a high-performance element simply by transferring the technology of the fluorescent element

Method used

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  • Ladder compound, and organic electroluminescent element using same
  • Ladder compound, and organic electroluminescent element using same
  • Ladder compound, and organic electroluminescent element using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0251] Embodiment 1 (synthesis of compound (7))

[0252] (1) Synthesis of compound (7-a)

[0253] [chem 28]

[0254]

[0255] 20.0 g (80.9 mmol) of dibenzofuran and 200 ml of dehydrated tetrahydrofuran were added to the three-necked flask, and the reactor was cooled to -70° C. under a nitrogen atmosphere. 53 ml (88.9 mmol) of a 1.68M sec-butyllithium hexane solution was added dropwise to the reactor, followed by stirring at -70°C for 1 hour. 37.3 ml (162 mmol) of triisopropyl borate was further added thereto, followed by stirring at room temperature for 6 hours. After completion of the reaction, 100 ml of 1N HCl aqueous solution was added and stirred for 30 minutes, then the sample solution was transferred to a separatory funnel, and extracted several times with dichloromethane. This was dried over anhydrous magnesium sulfate, filtered, and concentrated. This was dispersed and washed with hexane to obtain compound (7-a) as a white solid.

[0256] The harvested amount w...

Embodiment 2

[0284] A glass substrate with an ITO electrode line with a film thickness of 130 nm (manufactured by Gioma Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then to UV ozone cleaning for 30 minutes.

[0285] Install the washed glass substrate with ITO electrode wires on the substrate holder of the vacuum evaporation device, and first, resistively heat and vapor-deposit the compound (HI1) on the surface of the side where the ITO electrode wires are formed to cover the ITO electrode wires. Then, the compound (HT1) was resistively heated and vapor-deposited to a thickness of 20 nm, and thin films were sequentially formed. The film formation rate is These thin films function as a hole injection layer and a hole transport layer, respectively.

[0286] Next, the compound (7) and the compound (BD1) were vapor-deposited by resistance heating at the same time on the hole injection / transport layer to form a thin film with a film thickness of 50 nm...

Embodiment 3

[0305] Embodiment 3 (synthesis of compound (40))

[0306] (1) Synthesis of compound (40-a)

[0307] [chem 35]

[0308]

[0309] Add compound (7-c) 34.6g (100mmol), 2-bromodibenzofuran 24.7g (100mmоl), copper iodide 19.0g (100mmol), tripotassium phosphate 21.2g (100mmol), cyclohexane 5.9 g (50 mmol) of alkanediamine and 500 mL of dehydrated 1,4-dioxane were refluxed for 48 hours under an argon atmosphere.

[0310] After the reaction, the reactant was filtered through diatomaceous earth, moved to a separatory funnel, and extracted several times with toluene. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. This was purified by silica gel chromatography (hexane:toluene=10:1 to 5:1 to 2:1) to obtain compound (40-a) as a white solid.

[0311] The harvested amount was 11.8 g, and the yield was 23%.

[0312] (2) Synthesis of compound (40)

[0313] [chem 36]

[0314]

[0315] Add compound (40-a) 3.5g (10mmol), 2-bromodiben...

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PUM

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Abstract

A compound represented by formula (1), formula (2), or formula (3), a hole transport material for an organic electroluminescent element, and an organic electroluminescent element having the same. (In formula (1)-(3), X is O, S, or N-Ra, Y1-Y12 are N or C-Ra.　In formula (1), Ar1 and Ar2 are a heteroaryl group or an aryl group and can be the same or different, but if they are the same, none of the following can be the same group as each other: Y1 and Y12; Y2 and Y11; Y3 and Y10; Y4 and Y9; Y5 and Y8; and Y6 and Y7.　In formula (2), both Ar3 are the same heteroaryl group, and all of the following are the same group as each other: Y1 and Y12; Y2 and Y11; Y3 and Y10; Y4 and Y9; Y5 and Y8; and Y6 and Y7.　In formula (3), both Ar4 are the same aryl group, and all of the following are the same group as each other: Y1 and Y12; Y2 and Y11; Y3 and Y10; Y4 and Y9; Y5 and Y8; and Y6 and Y7.)

Description

technical field [0001] The present invention relates to a novel ladder compound, a material for an organic electroluminescent device using the ladder compound, and an organic electroluminescent device. Background technique [0002] Among organic electroluminescent (EL) elements, there are fluorescent and phosphorescent types, and the optimal element design has been studied according to each light-emitting mechanism. As for the phosphorescent organic EL element, it is known from the light emission characteristics that a high-performance element cannot be obtained simply by transferring the technology of the fluorescent element. [0003] Phosphorescence is emission using triplet excitons, and therefore, the energy gap of the compound used in the light emitting layer has to be large. This is due to the following reasons, that is, the value of the energy gap (hereinafter also referred to as singlet energy) of a certain compound is generally higher than the value of the triplet ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14C07D491/147C07D495/14C09K11/06H01L51/50H10K99/00
CPCC07D487/14C07D491/147C07D491/22C07D495/14C07D495/22C07D519/00C09K11/06C09K2211/1029C09K2211/1033C09K2211/1048C09K2211/1059C09K2211/1062H10K85/657H10K85/6572H10K2102/00C07D491/14H05B33/20C09K2211/1007C09K2211/1088C09K2211/1092H10K85/631H10K85/6576H10K85/6574H10K85/342H10K50/15H10K50/11H10K50/17H10K50/81H10K50/82H10K50/171H10K2101/10H10K2102/103
Inventor 中野裕基桥本亮平吉田圭
Owner IDEMITSU KOSAN CO LTD
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