Ink composition for forming an organic layer of a semiconductor

Patent metadata

Field	Value
Publication number	US-11787965-B2
Application number	US-201816497879-A
Country	US
Kind code	B2
Filing date	Mar 29, 2018
Priority date	Mar 30, 2017
Publication date	Oct 17, 2023
Grant date	Oct 17, 2023

Abstract

The present invention is directed to an ink composition for forming an organic semiconductor layer, wherein the ink composition comprises: —at least one p-type dopant comprising electron withdrawing groups; —at least one first auxiliary compound, wherein the first auxiliary compound is an aromatic nitrile compound, wherein the aromatic nitrile compound has about ≥1 to about ≤3 nitrile groups and a melting point of about <100° C., wherein the first auxiliary compound is different from the p-type dopant; and wherein the electron withdrawing groups are fluorine, chlorine, bromine and/or nitrile.

First claim

The invention claimed is:

1. An ink composition for forming an organic semiconductor layer, wherein the ink composition comprises:
at least one p-type dopant comprising electron withdrawing groups;
at least one first auxiliary compound, wherein the first auxiliary compound is an aromatic nitrile compound, wherein the aromatic nitrile compound has about ≥1 to about ≤3 nitrile groups and a melting point of about ≤100° C., wherein the first auxiliary compound is different from the p-type dopant;

wherein the electron withdrawing groups are fluorine, chlorine, bromine and/or nitrile;
wherein the ink composition is a homogeneous solution in which the at least one p-type dopant is dissolved by the at least one first auxiliary compound; and
wherein the ink composition comprises about ≥0.00001 wt.-% to about ≤2 wt.-% of the at least one p-type dopant, based on the total weight of the ink composition.

2. The ink composition according to claim 1 , wherein the ink composition comprises:
at least one p-type dopant comprising electron withdrawing groups, and which is solid at about ≥100° C.;
at least one organic charge transport material, which is solid at about ≥100° C., and wherein the organic charge transport material is different from the p-type dopant;
at least one first auxiliary compound, wherein the first auxiliary compound is an aromatic nitrile compound, wherein the aromatic nitrile compound has about ≥1 to about ≤3 nitrile groups and a melting point of about <100° C., wherein the first auxiliary compound is different from the p-type dopant; and

wherein the electron withdrawing groups are fluorine, chlorine, bromine and/or nitrile.

3. An ink composition according to claim 1 , wherein the ink composition comprises:
at least one p-type dopant, having about ≥4 atoms and wherein the amount of electron withdrawing groups in the sum formula of the at least one p-type dopant is about ≥17 atomic percent to about ≤90 atomic percent;
at least one organic charge transport material, having about ≥4 atoms and wherein the amount of electron withdrawing groups in the sum formula of the at least one organic charge transport material is ≥0 to about <17 atomic percent and having a melting point of about ≥100° C.;
at least one first auxiliary compound, wherein the first auxiliary compound is an aromatic nitrile compound, wherein the aromatic nitrile compound has about ≥1 to about ≤3 nitrile groups and a melting point of about <100° C., wherein the first auxiliary compound is different from the p-type dopant; and

wherein the electron withdrawing groups are fluorine, chlorine, bromine and/or nitrile.

4. The ink composition according to claim 1 , wherein the at least one p-type dopant has about ≥3 to about ≤100 electron withdrawing groups.

5. The ink composition according to claim 1 , wherein the molecular mass of the p-type dopant is in the range of about ≥60 g/mol to about ≤5000 g/mol.

6. The ink composition according to claim 1 , wherein the ink composition comprises at least two organic charge transport materials, of at least a first organic charge transport material and of at least a second organic charge transport material, wherein the molecular mass of the first organic charge transport material is lower than the molecular mass of the second organic charge transport material.

7. The ink composition according to claim 6 , wherein
the average molecular mass of the first organic charge transport material is in the range of about ≥300 g/mol to about ≤1500 g/mol; and/or
the average molecular mass of the second organic charge transport material is in the range of ≥600 g/mol to about ≤2,000,000;

wherein the molecular mass of the first organic charge transport material is lower than the molecular mass of the second organic charge transport material.

8. The ink composition according to claim 1 , wherein the at least one first auxiliary compound is selected from the group comprising substituted or unsubstituted benzonitrile, alkylbenzonitrile, methylbenzonitrile, ortho-tolunitrile, 4-butyl-benzonitrile, and the substituents are selected from alkyl, aryl or halogen.

9. The ink composition according to claim 1 , wherein the molecular mass of the at least one first auxiliary compound is in the range of about ≥100 g/mol to about ≤500 g/mol.

10. The ink composition according to claim 1 , wherein the ink composition comprises in addition at least one second auxiliary compound, which is liquid at about 23° C., and wherein the at least one second auxiliary compound has a chemical structure that is different from the first auxiliary compound and is different from the p-type dopant.

11. The ink composition according to claim 10 , wherein the at least one second auxiliary compound is selected from the group comprising:
an alkane compound, such as nonane, decane, undecane, or dodecane;
an aliphatic alcohol compound, such as hexanol, heptanol, octanol, nonyl alcohol, or decyl alcohol;
an aliphatic ether compound, such as dibutyl ether, dipentyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl propyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, or tetraethylene glycol dimethyl ether;
an aliphatic nitrile compound such as acetonitrile, propionitrile, or butyronitrile;
an aromatic hydrocarbon compound, such as 1,3-diisopropylbenzene, 1,4-diisopropylbenzene, triisopropylbenzene, pentylbenzene, hexylbenzene, cyclohexylbenzene, heptylbenzene, octylbenzene, or nonylbenzene 3-phenoxy toluene, 2-isopropyl naphthalene, dibenzyl ether, isopropyl biphenyl, or bis dimethyl phenyl ethane
a fluorinated hydrocarbon compound, such as hydro-fluoro ethers or methoxy-nonafluorobutane.

12. The ink composition according to claim 1 , wherein the p-type dopant is selected from the group comprising:
hexaazatriphenylene substituted with at least four nitrile groups;
cyanobenzoquinone-dimethanes and/or cyanobenzoquinone-diimines, which are substituted with at least four electron withdrawing groups selected from the group comprising fluorine, chlorine, bromine and/or nitrile;
radialene compounds;
tris(1-(pyridin-2-yl)-1H-pyrazol)cobalt(III) tris(hexafluorophosphate);
Molybdenum tris-[1,2-bis(trifluoromethyl)ethane-1,2-dithiolene];
C 60 F 48 ;
charge neutral metal amide compounds, which are substituted with at least four electron withdrawing groups selected from the group comprising fluorine, chlorine, bromine and/or nitrile;
metal organic complex.

13. The ink composition according to claim 1 , wherein the p-type dopant has the following chemical formula (P1) to (P25):

wherein M + is a monovalent cation.

14. A method of forming an organic semiconductor layer of an organic electronic device, wherein the ink composition according to claim 1 is processed

Assignees

• Novaled Gmbh

Inventors

• Lederer Kay
• Runge Steffen
• Ganier Jerome
• Limbach Anke

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• C09D11/52 Primary

  Electrically conductive inks · CPC title

• H10K71/15 Primary

  characterised by the solvent used · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/611

  Charge transfer complexes · CPC title