Yellow electrochromic polymers (ECPs) are prepared that display a yellow neutral state and a highly transmissive oxidized state. The ECPs are copolymers where a dyad of dioxyhetereocyclic repeating unis alternate with a monad of an aromatic repeating unit. An alternate yellow ECP has an oxidation potential of 450 mV or less and is an alternating copolymer of an acyclic dioxythiophene (AcDOT) or a propylene dioxythiophene (ProDOT) with an aromatic repeating unit that has an electron donating substituent. The yellow ECPs can be processed from solution for electrochromic devices.

The invention relates to novel conjugated polymers containing one or more units based on dithieno[3,2-c;2′,3′-e]azepine-4,6-dione that is fused to further aromatic rings, to methods for their preparation and educts or intermediates used therein, to polymer blends, mixtures and formulations containing them, to the use of the polymers, polymer blends, mixtures and formulations as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising, or being prepared from, these polymers, polymer blends, mixtures or formulations.

Polymers comprising at least one unit of formulae

##STR00001##

and compounds of the formulae

##STR00002##

wherein, in formulae 1, 1′, 2 and 2′
n is 0, 1, 2, 3 or 4
m is 0, 1, 2, 3 or 4 M1 and M2 are independently of each other an aromatic or heteroaromatic monocyclic or bicyclic ring system;
X is at each occurrence selected from the group consisting of O, S, Se or Te,
Q is at each occurrence selected from the group consisting of C, Si or Ge
R is at each occurrence selected from the group consisting of hydrogen, C.sub.1-100-alkyl, C.sub.2-100-alkenyl, C.sub.2-100-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl, a 5 to 20 membered heteroaryl, C(O)—C.sub.1-100-alkyl, C(O)—C.sub.5-12-cycloalkyl and C(O)—OC.sub.1-100-alkyl.
R.sup.2, R.sup.2′, R.sup.2″, R* are at each occurrence independently selected from the group consisting of hydrogen, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-12-cycloalkyl, C.sub.6-18-aryl, 5 to 20 membered heteroaryl, OR.sup.21, OC(O)—R.sup.21, C(O)—OR.sup.21, C(O)—R.sup.21, NR.sup.21R.sup.22, NR.sup.21—C(O)R.sup.22, C(O)—NR.sup.21R.sup.22, N[C(O)R.sup.21][C(O)R.sup.22], SR.sup.21, halogen, CN, SiR.sup.SisR.sup.SitR.sup.Siu and OH,
L.sup.1 and L.sup.2 are independently from each other and at each occurrence selected from the group consisting of C.sub.6-30-arylene, 5 to 30 membered heteroarylene,

##STR00003##

The invention relates to novel organic semiconducting oligomers or polymers containing dithieno[2,3-d:2′,3′-d′]-s-indaceno[1,2-b:5,6-b′]dithiophene units, methods for their preparation and educts or intermediates used therein, polymers, blends, mixtures and formulations containing them, the use of the oligomers, polymers, blends, mixtures and formulations as semiconductor in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these oligomers, polymers, blends, mixtures or formulations.

A semiconductor composition for producing a semiconducting layer with consistently high mobility is disclosed. The semiconductor composition includes a diketopyrrolopyrrole-thiophene copolymer and an aromatic non-halogenated hydrocarbon solvent. The copolymer has a structure disclosed within. The aromatic non-halogenated aromatic hydrocarbon solvent contains sidechains having at least 2 carbon atoms and the aromatic ring contains at least 3 hydrogen atoms.

The invention relates to novel conjugated polymers containing one or more 5,6-difluoro-benzo[1,2,5]thiadiazole-4,7-diylunits (hereinafter referred to as “FF-BTZ” units) and two or more different bridged bithiophene units, to methods for their preparation and educts or intermediates used therein, to polymer blends, mixtures and formulations containing them, to the use of the polymers, polymer blends, mixtures and formulations as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising, or being prepared from, these polymers, polymer blends, mixtures or formulations.

An organic compound comprising: ##STR00001## In this organic compound, W is selected from the group consisting of: S, Se, O, and N-Q; and Q is selected from the group consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. Additionally, in this organic compound Ar.sub.1 and Ar.sub.2 are independently selected from the group selected from: H, an aryl group, and a heteroaryl group.

A method of forming a polymer, the method comprising combining 4-bromo-7-[5-bromo-4-(alkyl)thiophen-2-yl]-6-chloro-5-fluoro-2,1,3-benzothiadiazole, (3,3′-difluoro-[2,2′-bithiophene]-5,5′-diyl)bis(trimethylstannane), [4-(alkyl)-5-[5-(trimethylstannyl)thiophen-2-yl]thiophen-2-yl]trimethylstannane, tris(dibenzylideneacetone), and dipalladium P(o-tol).sub.3 tris(2-methylphenyl)phosphane to form the polymer: ##STR00001##
In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q. Additionally, Q is selected from the group consisting of: a straight-chain carbyl, silyl or hydrocarbyl, branched, cyclic alkyl with 1 to 30 atoms, and fused aromatic rings. Furthermore in this polymer, R.sub.1, and R.sub.4 are independently selected from the group consisting of: F, Cl, I, Br, CN, —NCO, —NCS, —OCN, —SCN, —OX, —SX, —NH.sub.2, —C(═O)X, —C(═O)—OX, —OX, —NHX, —NXX′, —C(═O)NHX, —C(═O)NXX′, —SO.sub.3X, —SO.sub.2X, —OH, —NO.sub.2, CF.sub.3, —SF.sub.5, a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. This polymer can also have R.sub.2 and R.sub.3 are independently selected from F, Cl, Br and I. Additionally, in this polymer, the fused aromatic rings can be independently fused with groups consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. Lastly, in this polymer, h+j is between 0.2 to 0.6 and i+k is between 0.4 and 0.8.

The present invention discloses a terpolymer based on 2,5-bis(2-thienyl)thiazolo[5,4-d]thiazolyl. In the invention, by introducing 2,5-bis(2-thienyl)thiazolo[5,4-d]thiazole units, the conjugated length of the polymers is enlarged and the aggregation in solution becomes weak. The introducing of 2,5-bis(2-thienyl)thiazolo[5,4-d]thiazole unit can easily tune the photophysical properties and the aggregation structure of the terploymers, and the terpolymers show excellent photovoltaic performance. The terpolymers have the following general formula:

##STR00001##

The present invention provides compounds comprising at least one unit of formula (1) or (1′) as well as a process for the preparation of the compounds, intermediates of this process, electronic devices comprising the compounds, and the use of the compounds as semiconducting materials.

##STR00001##