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US 2017/0250347 A1Published application
Organic semiconductor composition comprising a liquid medium
AssigneeBASF SE
InventorsIlja VLADIMIROV, Jochen BRILL, Dieter FREYBERG, Thomas WEITZ, Thomas MUSIOL, Silke Annika KOEHLER
Life of this patent
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Abstract
Disclosed are a novel semiconductor composition comprising at least one organic semiconductor in a liquid medium and the use thereof the production of organic semiconductor devices, in particular organic field effect transistors, organic solar cells, light-emitting diodes and sensors.
Claims21
1:
- A composition comprising
- A) at least one organic semiconductor selected from
- rylene compounds of the general formula (I.a)
- wherein
- n is 1, 2, 3 or 4,
- Ra and Rb are independently of one another selected from hydrogen and in each case unsubstituted or substituted alkyl, alkenyl, alkadienyl, alkynyl, cycloalkyl, bicycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl,
- the Rn1, Rn2, Rn3 and Rn4 radicals are independently of one another selected from hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, formyl, acyl, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, alkylsulfonyl, arylsulfonyl, amidino, NE1E2, where E1 and E2 are each independently selected from hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl,
- in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, (monoalkyl)amino, (dialkyl)amino, cycloalkyl, cycloalkoxy, cycloalkylthio, (monocycloalkyl)amino, (dicycloalkyl)amino, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylthio, (monoheterocycloalkyl)amino, (diheterocycloalkyl)amino, aryl, aryloxy, arylthio, (monoaryl)amino, (diaryl)amino, hetaryl, hetaryloxy, hetarylthio, (monohetaryl)amino and (dihetaryl)amino,
- compounds of the formula (I.b)
- wherein
- R1b and R2b are independently selected from hydrogen and in each case unsubstituted or substituted linear C1-C30-alkyl, branched C3-C30-alkyl, linear C2-C30-alkenyl, branched C3-C30-alkenyl, linear C2-C30-alkinyl, branched C4-C30-alkinyl, cycloalkyl, aryl and hetaryl,
- Y1b and Y2b are independently selected from O, S, Se and NR3b, where R3b is selected from hydrogen and in each case unsubstituted or substituted alkyl, cycloalkyl and aryl,
- compounds of the formula (I.c)
- wherein
- R1c and R2c are independently selected from hydrogen and in each case unsubstituted or substituted linear C1-C30-alkyl, branched C3-C30-alkyl, linear C2-C30-alkenyl, branched C3-C30-alkenyl, linear C2-C30-alkinyl, branched C4-C30-alkinyl, cycloalkyl, aryl and hetaryl,
- Y1c, Y2c and Y3c are independently selected from O, S, Se and NR3c, where R3c is selected from hydrogen and in each case unsubstituted or substituted alkyl, cycloalkyl and aryl,
- compounds of the formula (I.d)
- wherein
- R1d and R2d are independently selected from hydrogen and in each case unsubstituted or substituted linear C1-C30-alkyl, branched C3-C30-alkyl, linear C2-C30-alkenyl, branched C3-C30-alkenyl, linear C2-C30-alkinyl, branched C4-C30-alkinyl, cycloalkyl, aryl and hetaryl,
- Y1d, Y2d, Y3d and Y4d are independently selected from O, S, Se and NR3d, where R3d is selected from hydrogen and in each case unsubstituted or substituted alkyl, cycloalkyl and aryl,
- compounds of the formula (I.e)
- wherein
- R1e and R2e are independently selected from hydrogen and in each case unsubstituted or substituted linear C1-C30-alkyl, branched C3-C30-alkyl, linear C2-C30-alkenyl, branched C3-C30-alkenyl, linear C2-C30-alkinyl, branched C4-C30-alkinyl, cycloalkyl, aryl and hetaryl,
- Y1e and Y2e are independently selected from O, S, Se and NR3e, where R3e is selected from hydrogen and in each case unsubstituted or substituted alkyl, cycloalkyl and aryl,
- B) at least one compound that is liquid at 20° C. and 1013 mbar, selected from compounds of the formula (II)
- Rc—X1-A-X2—Rd (II)
- wherein
- A is a 5- to 8-membered unsubstituted or substituted, aliphatic or aromatic carbocycle or heterocycle,
- X1 and X2 are independently selected from *—(C═O)—O—, *—(CH2)m—O— or *—(CH2)m—O—(C═O)—, where * is the point of linkage to the aliphatic or aromatic carbocycle or heterocycle, and m has the value 0, 1, or 2;
- and
- Rc and Rd are independently selected from unbranched and branched C1-C12-alkyl and C2-C12-alkenyl.
28 more elements
2:
- A composition according to claim 1, wherein Ra and Rb are independently of one another selected from hydrogen, linear C1-C30-alkyl, branched C3-C30-alkyl, perfluoro-C1-C30-alkyl, 1H,1H-perfluoro-C2-C30-alkyl, 1H,1H,2H,2H-perfluoro-C3-C30-alkyl, a radical of the formula G.1, a radical of the formula G.2 and a radical of the formula G.3
- where
- # represents the bonding side to a nitrogen atom,
- B where present, is a C1-C10-alkylene group which may be interrupted by one or more nonadjacent groups which are selected from —O— and —S—,
- y is 0 or 1,
- Rm is independently of one another selected from C1-C30-alkyl, C1-C30-fluoroalkyl, fluorine, chlorine, bromine, NE3E4, nitro and cyano, where E3 and E4, independently of one another, are hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl,
- Rn is independently of one another selected from C1-C30-alkyl,
- x in formulae G.2 and G.3 is 1, 2, 3, 4 or 5.
5 more elements
3:
- A composition according to claim 1, wherein Ra and Rb are selected from radicals of the general formulae (III.1), (III.2) and (III.3)
- wherein
- # is a bonding site, and
- in the formula (III.1) Re and Rf are independently selected from C1- to C27-alkyl, where the sum of the carbon atoms of the Re and Rf radicals is an integer from 2 to 28, in the formula (III.2) Rg and Rh are independently selected from C1- to C28-alkyl, where the sum of the carbon atoms of the Rg and Rh radicals is an integer from 2 to 29, in the formula (III.3) Ri, Rk and Rl are independently selected from C1- to C27-alkyl, where the sum of the carbon atoms of the Ri, Rk and Rl radicals is an integer from 3 to 29.
1 more element
4:
- A composition according to claim 1, wherein Ra and Rb have the same meaning.
5:
- A composition according to claim 1, wherein the component A) is selected from compounds of the general formula (I.a1)
- wherein
- Ra and Rb are defined as above,
- R12 and R23 are independently selected from F, Cl, Br, CN, and
- R11, R13, R14, R21, R22 and R24 are hydrogen.
2 more elements
6:
- A composition according to claim 1, wherein the compounds of the general formula (II) are characterized by at least one of the following parameters:
- a Hansen solubility parameter (delta D) in the range of from 15 to 20, more preferably 16 to 19 mPa1/2,
- a Hansen solubility parameter (delta P) in the range of from 7 to 12, more preferably 8 to 11 mPa1/2,
- a Hansen solubility parameter (delta H) in the range of from 3.5 to 5.5, more preferably 4 to 5 mPa1/2,
- a boiling point at 1013.25 mbar of at least 100° C., more preferably of at least 150° C., in particular of at least 200° C.
2 more elements
7:
- A composition according to claim 1, wherein the compound of the general formula (II) is selected from compounds of the formulae (II.1), (II.2), (II.3), (II.4) and (II.5)
- wherein
- X1 and X2 are independently selected from *—(C═O)—O—, *—(CH2)m—O— or *—CH2)m—O—(C═O)—, where * is the point of linkage to the aliphatic or aromatic carbocycle or heterocycle, and m has the value 0, 1, or 2;
- and
- Rc and Rd are independently selected from unbranched and branched C1-C12-alkyl and C2-C12-alkenyl.
2 more elements
8:
- A composition according to claim 7, where in the compounds of the formulae (II), (II.1), (II.2), (II.3), (II.4) and (II.5) Rc and Rd are independently selected methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, tert.-butyl, isobutyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, isononyl, isodecyl, 2-propylheptyl, n-undecyl and isoundecyl.
9:
- A composition according to claim 7, where in the compounds of the formulae (II), (II.1), (II.2), (II.3), (II.4) and (II.5) the groups X1 and X2 are both
- *—(C═O)—O—.
10:
- A composition according to claim 1, wherein the compound of the formula II is selected from dimethylphthalate, diethylphthalate, di(n-propyl)phthalate, di(n-butyl)phthalate, diallylphthalate and mixtures thereof.
11:
- A composition according to claim 1, wherein the organic semiconductor A) has a solubility in component B) at 20° C. of at least 0.01 mg/ml, preferably of at least 0.05 mg/ml.
12:
- A composition according to claim 1, comprising a cosolvent C) selected from organic solvents different from component B) and mixtures of organic solvents different from component B).
13:
- A composition according to claim 12, wherein the cosolvent C) is selected from
- aliphatic, cycloaliphatic and aromatic hydrocarbons,
- aromatic ethers,
- open chain aliphatic ethers, polyethers, ether alcohols and cyclic ethers,
- ketones,
- esters,
- aliphatic and cycloaliphatic alcohols,
- benzene based alcohols,
- halogenated aromatic compounds,
- thiophenols and alkylthio-substituted benzenes,
- aromatic compounds comprising a phenyl group fused to a 5-, 6-, or 7-membered cycloheteroalkyl group,
- 5-membered heteroaryl compounds and benzo-fused 5-membered heteroaryl compounds,
- aromatic carboxylic acids,
- aromatic aldehydes,
- trifluoromethyl-substituted benzene compounds,
- cyano-substituted or isocyano-substituted benzene compounds,
- nitro-substituted benzene compounds,
- phenyl sulfones,
- 6-membered heteroaryl compounds and benzofused 6-membered heteroaryl compounds,
- 5-membered heteroaryl compounds and benzofused 5-membered heteroaryl compounds,
- aprotic polar solvents and
- mixtures thereof.
19 more elements
14:
- A composition according to claim 12 in which the organic semiconductor A) has a solubility in the mixture of components B) and C) at 20° C. of at least 0.01 mg/ml, preferably of at least 0.1 mg/ml.
15:
- A composition according to claim 1 that contains a viscosity-modifying additive, preferably selected from dielectric polymers or semiconductive polymers, in particular polystyrene.
(canceled)
17:
- A process for the preparation of an electronic device, optical device, optoelectronic device or sensor, comprising:
- (a) providing a composition comprising A) at least one organic semiconductor and B) at least one compound that is liquid at 20° C. and 1013 mbar, as defined in claim 1,
- (b) applying the composition provided in step (a) to at least a portion of the surface of a substrate to allow deposition of the at least one organic semiconductor on the substrate.
18:
- The process according to claim 17, wherein in step (b) the application of the composition provided in step (a) to at least a portion of the surface of the substrate is performed by printing.
19:
- The process according to claim 17, wherein the surface of the substrate that is employed for the application of the semiconductor composition provided in step (a) is coated with a dielectric.
20:
- The process according to claim 17, wherein the surface of the substrate or, if present, the dielectric coating on the substrate, is subjected to a surface modification prior to the application of the semiconductor composition provided in step (a), wherein the compound used for the surface modification is selected from silanes, phosphonic acids, carboxylic acids, hydroxamic acids, amines, phosphines, sulfur-comprising compounds and mixtures thereof.
21:
- The process according to claim 17, wherein the device is selected from organic field-effect transistors, electroluminescent arrangements, organic solar cells and photodetectors.
Dependencies are inferred from the claim text.