发明名称 Diketopyrrolopyrrole polymers and small molecules
摘要 The present invention relates to polymers, comprising a repeating unit of the formula (I), and compounds of formula (II), wherein Y, Y15, Y16 and Y17 are independently of each other a group of formula (a) characterized in that the polymers and compounds comprise silicon-containing solubilizing side chains and their use as organic semiconductor in organic devices, especially in organic photovoltaics and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers and compounds according to the invention can have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers and compounds according to the invention are used in organic field effect transistors, organic photovoltaics and photodiodes.;
申请公布号 US9293718(B2) 申请公布日期 2016.03.22
申请号 US201314386123 申请日期 2013.04.02
申请人 BASF SE 发明人 Hayoz Pascal
分类号 C08G75/00;H01L51/00;C09K11/06;C08G73/06;C08G61/12;C07D487/04;C09B57/00;C09B67/22;C09B69/00;C09B69/10;H05B33/10;C07F7/08;H01L51/05;H01L51/42;H01L51/50 主分类号 C08G75/00
代理机构 Oblon, McClelland, Maier & Neustadt, L.L.P. 代理人 Oblon, McClelland, Maier & Neustadt, L.L.P.
主权项 1. A polymer comprising a repeating unit of the formulawherein a is 0, 1, 2, or 3, a′ is 0, 1, 2, or 3; b is 0, 1, 2, or 3; b′ is 0, 1, 2, or 3; c is 0, 1, 2, or 3; c′ is 0, 1, 2, or 3; R1 and R2 may be the same or different and are selected from the group consisting of a C1-C100alkyl group, which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; and/or can optionally be interrupted by —O—, —S—, —NR39—, —COO—, —CO—, —OCO—, C6-C24arylene, C2-C20heteroarylene, C3-C12cycloalkylene, or DSi, a C2-C100alkenyl group, which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; and/or can optionally be interrupted by —O—, —S—, —NR39—, —COO—, —CO—, —OCO—, C6-C24arylene, C2-C20heteroarylene, C3-C12cycloalkylene, or DSi, a C3-C100alkinyl group, which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; and/or can optionally be interrupted by —O—, —S—, —NR39—, —COO—, —CO—, —OCO—, C6-C24arylene, C2-C20heteroarylene, C3-C12cycloalkylene, or DSi, a C3-C12cycloalkyl group, which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; and/or can optionally be interrupted by —O—, —S—, —NR39—, —COO—, —CO—, —OCO—, C6-C24arylene, C2-C20heteroarylene, C3-C12cycloalkylene, or DSi, a C6-C24aryl group, which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; a C2-C20heteroaryl group, which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; and —CO—C1-C18alkyl, —CO—C5-C12cycloalkyl, —COO—C1-C18alkyl which can optionally be substituted one or more times with C1-C12alkyl, C1-C12alkoxy, halogen, C5-C12cycloalkyl, nitro, cyano, vinyl, allyl, C6-C24aryl, C2-C20heteroaryl, or ESi; and/or can optionally be interrupted by —O—, —S—, —NR39—, —COO—, —CO—, —OCO—, C6-C24arylene, C2-C20heteroarylene, C3-C12cycloalkylene, or DSi; wherein ESi is —SiR161R162R163 or —O—SiR161R162R163, DSi is —SiR161R162—, —SiR161R162—(O—SiR161R162)d— or —O—SiR161R162—, R161, R162 and R163 are independently of each other hydrogen, C1-C25alkyl, C3-C12cycloalkyl, which might optionally be substituted with C1-C4alkyl, C1-C25haloalkyl, C2-C25alkenyl, —O—SiR164R165R166, —(O—SiR164R165)d—R166, C1-C25alkoxy, C3-C24(hetero)aryloxy, NR167R168, halogen, C1-C25acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C1-C24alkyl, halogen, cyano or C1-C25alkoxy; R164, R165 and R166 are independently of each other hydrogen, C1-C25alkyl, C3-C12cycloalkyl, which might optionally be substituted with C1-C4alkyl, C1-C25haloalkyl, C2-C25alkenyl, —O—SiR169R170R171, —(O—SiR169R170)d—R171, C1-C25alkoxy, C3-C24(hetero)aryloxy, NR167R168, halogen, C1-C25acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C1-C24alkyl, halogen, cyano or C1-C25alkoxy; R169, R170 and R171 are independently of each other hydrogen, C1-C25alkyl, C3-C12cycloalkyl, which might optionally be substituted with C1-C4alkyl, C1-C25haloalkyl, C2-C25alkenyl, —O—Si(CH3)3, C1-C25alkoxy, C3-C24(hetero)aryloxy, NR167R168, halogen, C1-C25acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C1-C24alkyl, halogen, cyano or C1-C25alkoxy; R167 and R168 are independently of each other hydrogen, C6-C18aryl, C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy, or C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or C7-C25arylalkyl; d is an integer from 1 to 50; R39 is hydrogen, C1-C18alkyl, C1-C18haloalkyl, C7-C25arylalkyl, or C1-C18alkanoyl, Ar1, Ar1′, Ar2, Ar2′, Ar3 and Ar3′ are independently of each otherwherein X is —O—, —S—, —NR8—, —Si(R11)(R11′)—, —Ge(R11)(R11′)—, —C(R7)(R7′)—, —C(═O)—, —C(═CR104R104′)—, R3 and R3′ are independently of each other hydrogen, halogen, ESi, halogenated C1-C25alkyl, cyano, C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C7-C25arylalkyl, C1-C25alkyl substituted with one or more ESi, or C1-C25alkoxy; R4, R4′, R5, R5′, R6, and R6′ are independently of each other hydrogen, halogen, ESi, halogenated C1-C25alkyl, cyano, C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C7-C25arylalkyl, C1-C25alkyl substituted with one or more ESi, or C1-C25alkoxy; R7, R7′, R9 and R9′ are independently of each other hydrogen, C1-C25alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C1-C25alkyl substituted with one or more ESi, or C7-C25arylalkyl, or R7 and R7′, or R9 and R9′ are together ═CR104R104′; R8 and R8′ are independently of each other hydrogen, C6-C18aryl; C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy, C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C1-C25alkyl substituted with one or more ESi, or C7-C25arylalkyl, R11 and R11′ are independently of each other C1-C25alkyl group, C7-C25arylalkyl, or a phenyl group, which can be substituted one to three times with C1-C8alkyl and/or C1-C8alkoxy; R12 and R12′ are independently of each other hydrogen, halogen, cyano, C1-C25alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C1-C25alkoxy, C7-C25arylalkyl, or —≡—R13, wherein R13 is a C1-C10alkyl group, or a tri(C1-C8alkyl)silyl group; Ar1, Ar1′, Ar2, Ar2′, Ar3 and Ar3′ are independently of each other wherein X1′ is S, O, NR107—, —Si(R117)(R117′)—, —Ge(R117)(R117′)—, —C(R108)(R109)—, —C(═O)—, —C(═CR104R104′)—, R104 and R104′ are independently of each other hydrogen, cyano, COOR103, a C1-C25alkyl group, a C6-C24aryl or C2-C20heteroaryl; R103 is C1-C25alkyl, C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or is C7-C25arylalkyl; R105, R105′, R106 and R106′ are independently of each other hydrogen, halogen, cyano, C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C7-C25arylalkyl, or C1-C18alkoxy, R107 is hydrogen, C7-C25arylalkyl, C6-C18aryl, C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy, C1-C18perfluoroalkyl, C1-C25alkyl, which may be interrupted by —O—, or —S—; or —COOR103; R108 and R109 are independently of each other H, C1-C25alkyl, C1-C25alkyl which is substituted by E and/or interrupted by D, C7-C25arylalkyl, C6-C24aryl, C6-C24aryl which is substituted by G, C2-C20heteroaryl, C2-C20heteroaryl which is substituted by G, C2-C18alkenyl, C2-C18alkynyl, C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D, or C7-C25aralkyl, or R108 and R109 together form a group of formula ═CR110R111, wherein R110 and R111 are independently of each other H, C1-C18alkyl, C1-C18alkyl which is substituted by E and/or interrupted by D, C6-C24aryl, C6-C24aryl which is substituted by G, or C2-C20heteroaryl, or C2-C20heteroaryl which is substituted by G, or R108 and R109 together form a five or six membered ring, which optionally can be substituted by C1-C18alkyl, C1-C18alkyl which is substituted by E and/or interrupted by D, C6-C24aryl, C6-C24aryl which is substituted by G, C2-C20heteroaryl, C2-C20heteroaryl which is substituted by G, C2-C18alkenyl, C2-C18alkynyl, C1-C18alkoxy, C1-C18alkoxy which is substituted by E and/or interrupted by D, or C7-C25aralkyl, D is —CO—, —COO—, —S—, —O—, or —NR112—, E is C1-C8thioalkoxy, C1-C8alkoxy, CN, —NR112R113, —CONR112R113, or halogen, G is E, or C1-C18alkyl, and R112 and R113 are independently of each other H, C6-C18aryl, C6-C18aryl which is substituted by C1-C18alkyl or C1-C18alkoxy, C1-C18alkyl, or C1-C18alkyl which is interrupted by —O—, R114 is C1-C25alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, R115 and R115′ are independently of each other hydrogen, halogen, cyano, C1-C25alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C1-C25alkoxy, C7-C25arylalkyl, or —≡—R116, wherein R116 is a C1-C10alkyl group, or a tri(C1-C8alkyl)silyl group; R117 and R117′ are independently of each other C1-C25alkyl group, C7-C25arylalkyl, or a phenyl group, which can be substituted one to three times with C1-C8alkyl and/or C1-C8alkoxy; R118, R119, R120 and R121 are independently of each other hydrogen, halogen, halogenated C1-C25alkyl, cyano, C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C7-C25arylalkyl, or C1-C25alkoxy; R122 and R122′ are independently of each other hydrogen, C6-C18aryl, C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy, or C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, or C7-C25arylalkyl, with the proviso that at least one of the groups R1, R2, R3, R3′, R4, R4′, R5, R5′, R6, R6′, R7, R7′, R8, R8′, R9 and R9′ comprise ESi and/or DSi; and wherein the polymer comprises at least one unit of the formula Ia to Ie, wherein R1 and R2 may be the same or different and are selected from C1-C8alkyl which is substituted with ESi, ESi is —SiR161R162R163; R161, R162 and R163 are independently of each other C1-C8alkyl, C5-C6cycloalkyl, which might optionally be substituted with C1-C4alkyl, C1-C8haloalkyl, C2-C8alkenyl, —O—SiR164R165R166, —(O—SiR164R165)d—R166, or phenyl; R164, R165, R166 are independently of each other C1-C8alkyl, C1-C8haloalkyl, C2-C8alkenyl, —O—SiR169R170R171, —(O—SiR169R170)d—R171, or phenyl; R169, R170, R171 are independently of each other C1-C8alkyl, C1-C8haloalkyl, C2-C8alkenyl, —O—Si(CH3)3, or phenyl; d is an integer from 1 to 10; R3 and R3′ are independently of each other hydrogen, or C1-C25alkyl; and R8 and R8′ are independently of each other hydrogen, or C1-C25alkyl.
地址 Ludwigshafen DE