Hole transport material

Patent metadata

Field	Value
Publication number	US-2016254449-A1
Application number	US-201415026776-A
Country	US
Kind code	A1
Filing date	Sep 16, 2014
Priority date	Oct 2, 2013
Publication date	Sep 1, 2016
Grant date	—

Abstract

The invention relates to 2,2′,7,7′-tetrakis-(N,N′-di-4-methoxy-3-methylphenylamine)-9,9′-spirofluorene, to a process for its preparation, and to its use as hole transport material for electronic or optoelectronic devices, especially for solid-state dye-sensitized solar cells.

First claim

1 . A compound of formula (I)

2 . A process for the preparation of the compound according to claim 1 comprising reacting 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene in a Buchwald-Hartwig amination with bis(4-methoxy-3-methylphenylamine).

3 . A process according to claim 2 in which the reaction is carried out at temperatures between 100° C. and 140° C.

4 . Preparation comprising the compound of formula (I) according to claim 1 and at least one solvent.

5 . (canceled)

6 . Electronic or optoelectronic device comprising the compound of formula (I) according to claim 1 .

7 . Device according to claim 6 which is an organic electroluminescent device, an organically integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, a solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell or an organic laser diode, an organic plasmon emitting device, an electrophotography device or a wave converter.

8 . Device according to claim 6 which is a solid-state dye-sensitized solar cell or a perovskite containing solar cell

9 . Device according to claim 6 , characterized in that the compound of formula (I) is employed as hole transport material.

10 . Charge transport layer comprising a compound of formula (I) according to claim 1 .

11 . A layer according to claim 10 which is a photosensitized nanoparticle layer comprising a sensitizing dye or perovskite and the compound of formula (I).

12 . A layer according to claim 10 further comprising an insulator.

13 . A layer according to claim 10 comprising semiconductor oxide nanoparticles.

14 . Device according to claim 8 comprising a charge transport layer comprising a compound of formula I.

15 . A module comprising a device according to claim 6 .

16 . The compound bis(4-methoxy-3-methylphenylamine).

17 . A process for the preparation of bis(4-methoxy-3-methylphenylamine) comprising reacting 5-bromo-2-methoxy-1,3-dimethylbenzene in a Buchwald-Hartwig amination with 4-methoxy-3,5-dimethylphenylaniline.

Assignees

• Merck Patent Gmbh

Inventors

• Shinohara Hiromi
• Sawada Atsushi
• Montenegro Elvira
• Becker Heinrich

Classifications

• H10F77/311

  for photovoltaic cells · CPC title

• H01L51/006 Primary

  Electricity · mapped topic

• C07C213/02 Primary

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• H01G9/2031

  comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence) · CPC title

• H01G9/2059

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title