Novel compounds
AssigneesOxford University Innovation Limited, King Abdullah University of Science and Technology (KAUST), Flexenable Technology Limited
InventorsIain MCCULLOCH, Hu CHEN, Helen BRISTOW, Yoann PORTE, Patrick TOO
Life of this patent
Estimating the term…
Abstract
Novel compounds comprising x-conjugated moicties are disclosed, as well as their uses as semiconducting materials. The novel compounds comprise adjacent x-electron rich and x-electron deficient moieties. The novel compounds exhibit improved charge mobility and are particularly suited to use in electronic devices and components, such as organic thin film transistors.
Claims25
A compound comprising a unit of formula (I):
- wherein
- D is a collinear, π-electron rich group of formula (II)
- wherein:
- X is a polycyclic, π-conjugated, ring system;
- and
- A is a collinear, π-electron deficient group of formula (III):
- wherein:
- Q is selenium or tellurium;
- and
- Y is a monocyclic or polycyclic, π-conjugated, ring system:
The compound of any one of the preceding claims, wherein A is a collinear, π-electron deficient group of formula (IIIa-i), (IIIa-ii), (IIIa-iii), (IIIa-iv), (IIIa-v), (IIIa-vi) or (IIIa-vii):
- wherein Q has any of those definitions recited in any preceding claim.
The compound of any one of the preceding claims, wherein A is
- wherein Q has any of those definitions recited in any preceding claim.
The compound of any one of the preceding claims, wherein X comprises a plurality of fused, 5-and/or 6-membered, π-conjugated rings.
The compound of any one of the preceding claims, wherein D is a collinear, π-electron rich group of formula (IIa):
- wherein:
- X1 is a monocyclic or polycyclic π-conjugated ring system;
- Each RY is independently selected from the group consisting of hydroxy, cyano, halo, alkyl, alkenyl and alkynyl, optionally wherein one or more carbon atom in the alkyl, alkenyl and alkynyl group is replaced by a heteroatom;
- v is 0, 1, 2, 3, 4, 5 or 6;
- and
- L is sulfur, oxygen, nitrogen or selenium.
The compound of any one of the preceding claims, wherein D is a collinear, π-electron rich group of formula (IIb):
- wherein:
- X2 is absent, or is a monocyclic or polycyclic π-conjugated ring system;
- each RY is independently selected from the group consisting of hydroxy, cyano, halo, alkyl, alkenyl and alkynyl, optionally wherein one or more carbon atom in the alkyl, alkenyl and alkynyl group is replaced by a heteroatom;
- v is 0, 1, 2, 3, 4, 5 or 6;
- and
- each L is independently sulfur, oxygen, nitrogen or selenium.
The compound of any one of the preceding claims, wherein D is a collinear, π-electron rich group selected from the group consisting of thioenothiophene (TT), thieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene (TTTT), indacenodithiophene (IDT), indacenodithieno[3,2-b]dithiophene (IDTT), indacenodithieno[3,2-b:2′,3′-d]thiophene (IDTTT), indacenodithieno[3,2-b]dibenzo[1,2-b:4,5-b′]thiophene (TBIDT), indacenodithienodinaphtho [2,3-b:6,7-b′]thiophene (TNIDT), indacenodithienodibenzo[b]thieno[2,3-d]thiophene (TTBIDT), indacenodithienodithieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene (IDTTTT), indacenodithienodithieno[2,3-d]benzo[1,2-b:4,5-b′]thiophene (TBTIDT), dithieno[3,2-b]indenofluorene (TIF);
- dithieno[2,3-d]thienoindenofluorene (TTIF), dithienobenzo[1,2-b:4,5-b′]indenofluorene (TBIF), dithienonaphtho [1,2-b:4,5-b′]indenofluorene (TBBIF), dithieno[2,3-d]thienodibenzo[1,2-b:4,5-b′]indenofluorene (TTBIF), dithienodithieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thienoindenofluorene (TTTIF) and dithieno[2,3-d]benzo[1,2-b:4,5-b′]thienoindenofluorene (TBTTIF), any one of which is optionally substituted with one or more RY.
The compound of any one of the preceding claims, wherein D is a collinear, π-electron rich group selected from the group consisting of indacenodithiophene (IDT), dithieno[3,2-b]indenofluorene (TIF), indacenodithieno[3,2-b]dibenzo[1,2-b:4,5-b′]thiophene (TBIDT) and dithieno[2,3-d]thienoindenofluorene (TTIF), any one of which is optionally substituted with one or more RY.
The compound of any one of the preceding claims, wherein D is indacenodithiophene (IDT) optionally substituted with one or more RY.
The compound of any one of the preceding claims, wherein A is:
- and D is indacenodithiophene (IDT) optionally substituted with one or more RY as defined any preceding statement.
The compound of any one of the preceding claims, wherein the compound comprises a plurality of units of formula (I).
The compound of any one of the preceding claims, wherein the compound is a polymer or an oligomer.
The compound of any one of the preceding claims, wherein the compound is semiconductive.
An electronic device or component comprising a compound or polymer of any one of the preceding claims.
Use of a compound as defined in any one of the preceding claims as a semiconducting material.
Dependencies are inferred from the claim text.