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Novel compound, charge transport material, and organic device

A compound and bonding technology, which is applied in the direction of electric solid-state devices, electric components, luminescent materials, etc., can solve the problems of unrecorded production of dimers of triphenylamine derivatives, and achieve the effect of suppressing power consumption

Inactive Publication Date: 2014-01-08
KYUSHU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no description in this document on the production of dimers of triphenylamine derivatives.

Method used

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  • Novel compound, charge transport material, and organic device
  • Novel compound, charge transport material, and organic device
  • Novel compound, charge transport material, and organic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0297] Compound 1 was synthesized according to the following scheme.

[0298] [chemical formula 27]

[0299]

[0300] Compound 21a (19.8g, 84.6mmol), compound 23a (7.74g, 37.2mmol), K 2 CO 3 (21.5g, 156mmol), and Cu (7.82g, 123mmol) were dissolved in o-dichlorobenzene [ODCB] (100ml) and heated at 180°C for 110 hours. The reaction mixture was filtered, and the insoluble matter was washed three times with chloroform (100 ml). The filtrate was washed with water and then washed with MgSO 4Dry, filter, and concentrate under reduced pressure. Furthermore, the obtained black solid was washed with hexane to obtain Compound 24a (10.6 g, 25.4 mmol) as a white powder with a yield of 68%.

[0301] Mp: 157.5-158.5°C.

[0302] 1 H NMR (300MHz, CDCl 3 , ppm) δ7.10-6.94 (m, 4H), 6.94-6.81 (m, 6H), 3.60 (s, 6H).

[0303] 13 C NMR (75MHz, CDCl 3 , ppm): δ158.24 (dd, 1 J(C,F)=252.4, 3 J(C,F)=6.9Hz), 153.25, 136.12, 124.61, 121.10, 115.29 (dd, 2 J(C,F)=17.8, 4 J(C,F)=9.2Hz), 114...

Embodiment 2

[0321] Compound 2 was synthesized according to the following scheme.

[0322] [chemical formula 28]

[0323]

[0324] Compound 21b (20.4g, 77.2mmol), compound 23b (6.86g, 33.0mmol), K 2 CO 3 (18.2g, 132mmol), and Cu (6.80g, 107mmol) were dissolved in o-dichlorobenzene [ODCB] (90ml) and heated at 180°C for 150 hours. The insoluble material was removed by filtration with CH 2 Cl 2 (100ml) was washed three times, and the filtrate was washed with water. The obtained organic phase was washed with MgSO 4 Dry, filter, and concentrate under reduced pressure. Then utilize silica gel column chromatography (developing solvent: hexane / CH 2 Cl 2 (1 / 3), Rf=0.56) to obtain compound 24b (9.63 g, 20.1 mmol) as a white solid in 61% yield.

[0325] Mp: 96.4-97.3°C.

[0326] 1 H NMR (300MHz, CDCl 3 , ppm) δ7.05-6.90 (m, 2H), 6.83 (d, 3 J(H,H)=8.4Hz,2H), 6.46(d, 4 J(H,H)=2.7Hz,2H), 6.38(dd, 3 J(H,H)=8.7, 4 J(H, H)=2.7Hz, 2H), 3.78(s, 6H), 3.60(s, 6H).

[0327] 13 C NMR (75MHz,...

Embodiment 3

[0342] Compound 24 was synthesized according to the following scheme.

[0343] [chemical formula 29]

[0344]

[0345] Compound 21c (11.7g, 49.9mmol), compound 23c (9.19g, 44.2mmol), Pd 2 (dba) 3 · CHCl 3 (0.799g, 0.765mmol), sodium tert-butoxide (4.38g, 45.6mmol), tri-tert-butylphosphine (0.920g, 4.55mmol) were dissolved in anhydrous toluene (100ml), and stirred at 100°C for 26 hours. The insoluble matter was filtered and washed with toluene (60ml). Then, water was added to the filtrate, and extracted with toluene (50ml×3). The organic layer was washed with Na 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure. The obtained solid was subjected to silica gel column chromatography (CH 2 Cl 2 :hexane=1:5, R f =0.30) to afford compound 24c-pre (7.73 g, 24.6 mmol) as a white solid in 50% yield.

[0346] Mp: 71.2-72.2°C.

[0347] 1 H NMR (300MHz, CDCl 3 , ppm) δ7.20-7.11 (m, 2H), 6.91-6.80ppm (m, 3H), 6.57 (td, 3 J(H,H)=8.7Hz, 4 J(H, H)=2.7Hz...

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Abstract

A compound represented by the general formula below has high thermal stability and has excellent characteristics as a charge transport material. (Ar1 denotes a single bond, a benzene ring or the like; X1 denotes a linking group linked via an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom or a silicon atom; one of L1 and L2 or L3 and L4 bond together to form a linking group linked via an oxygen atom, a sulfur atom, a carbon atom, a nitrogen atom, a phosphorus atom or a silicon atom and the other of L1 and L2 or L3 and L4 are hydrogen atoms or substituent groups; Y1 denotes a linking group linked via a nitrogen atom, a boron atom or a phosphorus atom; R1, R2, R5 to R7 and R10 to R12 are hydrogen atoms or substituent groups, and n1 is an integer of 2 or higher.)

Description

technical field [0001] The present invention relates to a novel compound and a charge transport material formed from the novel compound. In addition, the present invention also relates to organic devices (organic devices) such as organic electroluminescence elements and organic thin-film solar cells using the novel compound. Background technique [0002] Organic devices such as organic electroluminescent elements and organic thin film solar cells require charge transport materials with high charge mobility. Thus, various charge-transporting materials have been proposed so far, and it is known that compounds having a triphenylamine structure exhibit high charge mobility in particular. [0003] As a compound having a triphenylamine structure, for example, like N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4 having the structure shown below ,4'-diamine[TDP], N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine[α- NPD] Such a triphenylamine dimer is widely kno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K11/06H01L51/42H01L51/50
CPCH01L51/0071H01L51/5088Y02E10/549C07D519/00H10K85/657H10K50/17H10K50/15H10K85/6572H10K50/155H10K50/165
Inventor 若宫淳志西村秀隆村田靖次郎福岛达也梶弘典
Owner KYUSHU UNIV
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