Organic ionic functional materials

Patent metadata

Field	Value
Publication number	US-9923152-B2
Application number	US-201214007182-A
Country	US
Kind code	B2
Filing date	Feb 28, 2012
Priority date	Mar 24, 2011
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The present invention relates to a novel non-polymeric organic ionic compound comprising one ion having a functional organic group, such as a matrix group, a hole injection group, a hole transport group, an electron injection group and an electron transport group, and comprising another ion preferably being so small that it may act as a mobile ion in films containing the organic ionic compound. Furthermore, the present invention relates to a composition containing the novel organic ionic compound and another functional compound. The novel organic ionic compound or the composition may be used in organic devices as functional materials, such as matrix materials or for materials charge transport. The resulting organic devices are also object of the present invention.

First claim

The invention claimed is:

1. A composition comprising a non-polymeric organic ionic compound having the following Formula (1):
( M ) +/− ( N ) −/+   Formula (1),

wherein the symbols have the following meanings:
M is a mono-charged organic anionic compound comprising a functional group acting as a matrix group, a hole injection group, a hole transport group, an electron injection group or an electron transport group;
N is an alkali or an alkaline earth metal group,
wherein M and N are counter ions, and a functional organic compound selected from the group consisting of a matrix material, a fluorescent or phosphorescent emitter, a dye, a hole injection material, a hole transport material, an electron injection material and an electron transport material.

2. The composition according to claim 1 , wherein the function of the functional organic group of M is different from the function of the functional organic compound.

3. The composition according to claim 1 , further comprising a matrix compound and a fluorescent or phosphorescent emitter compound.

4. The composition according to claim 1 , further comprising an ion conductor compound.

5. The composition according to claim 1 , further comprising a matrix compound and a dye.

6. An electronic device comprising the composition according to claim 1 .

7. The device according to claim 6 , wherein the device is an organic light emitting diode, a polymer light emitting diode, an organic light emitting transistor, an organic light emitting electrochemical cell, an organic light emitting electrochemical transistor, an organic field effect transistor, a thin film transistor, an organic solar cell, an organic laser diode, an organic integrated circuit, a radio frequency identification tag, a photodetector, sensor, a logic circuit, a memory element, a capacitor, a charge injection layer, a Schottky diode, a planarizing layer, an antistatic film, a conducting substrate or a pattern, a photoconductor, an electrophotographic element, an organic solar concentrator, an organic spintronic device, or an organic plasmon emitting device.

8. The device according to claim 6 , wherein the device is an organic light emitting electrochemical cell or an organic solar cell.

9. The device according to claim 6 , wherein the device is for use for phototherapy in medicine.

10. The device according to claim 6 , wherein the device is for use phototherapy in the field of cosmetics.

11. The composition according to claim 1 , wherein M is selected from the group consisting of arylamine, styrylamine, fluorescein, perynone, phthaloperynone, naphthaloperynone, diphenylbutadiene, tetraphenylbutadiene, cyclopentadienes, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, coumarine, oxadiazole, bisbenzoxazoline, oxazone, pyridine, pyrazine, imine, benzothiazole, benz-oxazole, benzimidazole, aldazines, stilbene, styrylarylene derivatives, distyrylarylene derivatives, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, diketopyrrolopyrrole, mellocyanine, acridone, quinacridone, and cinnamic acid esters.

12. The composition according to claim 1 , wherein M is an anion of formula (28) to (42), (64) to (93), (116) to (124) or (148)-(153)

wherein X is CR or N, and
R can be the same or different in each occurrence and is selected from H, CN, linear and branched alkyl rest with 1 to 20 C-atoms, linear or branched alkenyl radical with 2 to 20 C-atoms and one or more non conjugated double bonds, linear or branched alkinyl rest with 2 to 20 C-atoms and one or more non conjugated triple bonds, partly or completely non saturated cycloalkyl rest with 3 to 7 C-atoms which can be substituted with alkyl rests with 1 to 6 C-atoms, saturated and partly or completely non saturated heteroaryls, heteroaryl-C 1 -C 6 -alkyl, or alkyl-C 1 -C 6 -alkyl, wherein different R together can form a ring, wherein one or more of the substituents R can partly or completely be substituted with halogen, particularly with —F and/or —Cl, and —OR′, —CN, —C(O)OH, —C(O)NR′ 2 , —SO 2 NR′ 2 , —C(O)Y, —SO 2 OH, —SO 2 Y, —NO 2 , wherein the substituents R are not substituted with halogen at the same time, wherein one or two carbon atoms of the substituents R, which are non adjacent or bound to an heteroatom, can be substituted by a group selected from —O—, —S—, —S(O)—, —SO 2 —, —N + R′ 2 —, —C(O)NR′—, —SO 2 NR′—, and —P(O)R′— wherein R′═H, unsubstituted, partly or completely with —F substituted alkyl with 1 to 6 C-atoms, cycloalkyl with 3 to 7 C-atoms, unsubstituted or substituted phenyl and Y=halogen.

Assignees

• Pan Junyou
• Parham Amir Hossain
• Merck Patent Gmbh

Inventors

• Pan Junyou
• Parham Amir Hossain

Classifications

• A61N5/0616 Primary

  Skin treatment other than tanning · CPC title

• A61N2005/0656

  Chemical light sources · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61N2005/0653

  Organic light emitting diodes · CPC title

• Y02E10/549

  Organic PV cells · CPC title