IP Library › Granted Patent US 9,923,152
Granted Patent B2
US 9,923,152 · App. 14/007,182 · Granted Mar 20, 2018

Organic ionic functional materials

Inventors: Junyou Pan (Frankfurt am Main, DE); Amir Hossain Parham (Frankfurt am Main, DE)
Assignee: Merck Patent GmbH
H01L51/0072A61N5/0616H01L51/007H01L51/0067A61N2005/0653A61N2005/0656H01L51/0003H01L51/004H01L51/0052H01L51/0085H01L51/5032Y02E10/549
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Quick Facts
Patent No.
US 9,923,152
App. No.
14/007,182
Granted
Mar 20, 2018
Kind
B2
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.

Claims (19)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2013
From: PAN, JUNYOU; PARHAM, AMIR HOSSAIN
To: MERCK PATENT GMBH
Reel/Frame 031269/0844 →
Priority Claims (1)
EP 11002481 · Mar 24, 2011 · regional
Continuity (1)
Related Publication 20140014885A1 · Jan 16, 2014