Organic semiconductor formulation

Patent metadata

Field	Value
Publication number	US-12245492-B2
Application number	US-202017593921-A
Country	US
Kind code	B2
Filing date	Mar 25, 2020
Priority date	Mar 28, 2019
Publication date	Mar 4, 2025
Grant date	Mar 4, 2025

Abstract

The invention relates to novel organic semiconductor (OSC) formulations, to their use for the preparation of OSC layers or OSC patterns in organic electronic (OE) devices, especially organic photovoltaic (OPV) devices, perovskite-based solar cell (PSC) devices, organic photo-detectors (OPD), organic field effect transistors (OFET) and organic light emitting diodes (OLED), and to OE, OPV, PSC, OPD, OFET and OLED devices comprising an OSC layer or OSC pattern prepared from these OSC formulations.

First claim

The invention claimed is:

1. A formulation comprising a p-type organic semiconductor (OSC) and an n-type OSC, the formulation further comprising a first solvent selected from terpenes or terpenoids and a second solvent selected from aromatic, heteroaromatic, or partially unsaturated alicyclic or heterocyclic solvents, wherein the first solvent is selected from the group consisting of β-caryophyllene, vetiveryl acetate, carvacrol, valencene, D-carvone, citral diethyl acetal, verbenone, nerol, menthone, citral, derivatives of the aforementioned, and any combination of the aforementioned, and the p-type OSC is a conjugated polymer having a molecular weight Mn>5000 g/mol.

2. The formulation according to claim 1 , characterized in that the first solvent is selected from the group consisisting of β-caryophyllene, vetiveryl acetate and carvacrol.

3. The formulation according to claim 2 , characterized in that the first solvent is β-caryophyllene.

4. The formulation according to claim 1 , characterized in that the second solvent is selected from the group consisting of alkylated benzene, alkoxylated benzene, indane, alkylated indane, alkoxylated indane, tetralin, alkylated tetralin, naphthalene, alkylated naphthalene, anisole and alkylated anisole.

5. The formulation according to claim 4 , characterized in that the second solvent is selected from the group consisting of 1,5-dimethyltetralin, 1-methylnaphthalene, 1-ethylnaphthalene, 2-ethylnaphthalene, 1,2-dimethylnaphthalene, 1,3-dimethylnaphthalene, 1,4-dimethylnaphthalene, 2,6-dimethylnaphthalene, 2,7-diisopropylnaphthalene and dimethylanisole.

6. The formulation according to claim 5 , characterized in that the second solvent is selected from the group consisting of 1,5-dimethyltetralin, 1-methylnaphthalene and dimethylanisole.

7. The formulation according to claim 1 , characterized in that the concentration of the first solvent is from 2 to 30%, and the concentration of the second solvent is from 50 to 90%.

8. The formulation according to claim 7 , characterized in that the concentration of the p-type OSC is from 1 to 5%, and the concentration of the n-type OSC is from 1 to 5%.

9. The formulation according to claim 1 , characterized in that the formulation does, except for the n-type and p-type OSC, only contain volatile organic compounds.

10. The formulation according to claim 1 , characterized in that the total concentration of all solids is ≤6%.

11. The formulation according to claim 1 , characterized in that the p-type OSC is a conjugated polymer having a molecular weight Mn>5000 g/mol and comprising at least one electron donating unit D and at least one electron accepting unit A, and optionally at least one spacer unit Sp separating a donor unit from an acceptor unit, wherein each donor and acceptor units is directly connected to another donor or acceptor unit or to a spacer unit, and wherein the spacer units, if present, are located between the donor and acceptor units such that a donor unit and an acceptor unit are not directly connected to each other,
and wherein all of the donor, acceptor and spacer units are each independently selected from arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L or R 1 , wherein
R 1 is H, F, Cl, CN, -Sp-R C , or straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more CH 2 groups are each optionally replaced by —O—, —S—, —C(═O)—, —C(═S)—, —C(═O)—O—, —O—C(═O)—, —NR 0 —, —SiR 0 R 00 —, —CF 2 —, —CR 0 ═CR 00 , —CY 1 ═CY 2 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, and in which one or more H atoms are each optionally replaced by F, Cl, Br, I or CN, or aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxy or heteroaryloxy, wherein each of the aforementioned cyclic groups has 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
L is F, Cl, —NO 2 , —CN, —NC, —NCO, —NCS, —OCN, —SCN, R 0 , OR 0 , SR 0 , —C(═O)X 0 , —C(═O)R 0 , —C(═O)—OR 0 , —O—C(═O)—R 0 , —NH 2 , —NHR 0 , —NR 0 R 00 , —C(═O)NHR 0 , —C(═O)NR 0 R 00 , —SO 3 R 0 , —SO 2 R 0 , —OH, —CF 3 , —SF 5 , or optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 30 C atoms that is optionally substituted and optionally comprises one or more hetero atoms,
R 0 , R 00 denote H or straight-chain or branched alkyl with 1 to 20 C atoms that is optionally fluorinated,
X 0 is halogen.

12. The formulation according to claim 11 , characterized in that the p-type OSC is a conjugated polymer selected from the following formulae

wherein w, x, y and z are each, independently of one another, a non-integer>0 and <1, with x+y=1, and x+y+w+Z=1, n is an integer>1,
R 11-19 are H, F, Cl, CN, -Sp-R C , or straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more CH 2 groups are each optionally replaced by —O—, —S—, —C(═O)—, —C(═S)—, —C(═O)—O—, —O—C(═O)—, —NR 0 —, —SiR 0 R 00 —, —CF 2 —, —CR 0 —CR 00 , —CY 1 ═CY 2 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, and in which one or more H atoms are each optionally replaced by F, Cl, Br, I or CN, or aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxy or heteroaryloxy, wherein each of the aforementioned cyclic groups has 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
L is F, Cl, —NO 2 , —CN, —NC, —NCO, —NCS, —OCN, —SCN, R 0 , OR 0 , SR 0 , —C(═O)X 0 , —C(═O)R 0 , —C(═O)—OR 0 , —O—C(═O)—R 0 , —NH 2 , —NHR 0 , —NR 0 R 00 , —C(═O)NHR 0 , —C(═O) NR 0 R 00 , —SO 3 R 0 , —SO 2 R 0 , —OH, —CF 3 , —SF 5 , or optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 30 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, —CN, R 0 , —OR 0 , —SR 0 , —C(═O)—R 0 , —C(═O)—OR 0 , —O—C(═O)—R 0 , —O—C(═O)—OR 0 , —C(═O)—NHR 0 , or —C(═O)—NR 0 R 00 ,
R 0 , R 00 denote H or straight-chain or branched alkyl with 1 to 20 C atoms that is optionally fluorinated,
X 0 is halogen,

and X 1 , X 2 , X 3 and X 4 denote H, F or Cl.

13. The formulation according to claim 1 , characterized in that the n-type OSC is a small molecule.

14. The formulation according to claim 1 , characterized in that the n-type OSC is a fullerene or a substituted fullerene.

15. The formulation according to claim 14 , characterized in that the n-type OSC is selected from PCBM-C60, PCBM-C70, bis-PCBM-C60, bis-PCBM-C70, ICMA-c60 (1′,4′-dihydro-naphtho [2′,3′: 1,2] [5,6]fullerene-C60), ICBA, oQDM-C60 (1′,4′-dihydro-naphtho [2′,3′: 1,9] [5,6]fullerene-C60-Ih), and bis-oQDM-C60.

16. A method of preparing an organ

Assignees

• Raynergy Tek Inc

Inventors

• Malandraki Andromachi
• Chen Lichun
• May Philip Edward
• Miskiewicz Pawel

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H10K71/13

  using printing techniques, e.g. ink-jet printing or screen printing · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K85/215

  comprising substituents, e.g. PCBM · CPC title

• H10K85/211

  Fullerenes, e.g. C60 · CPC title