Use of a Metal Complex as an N-Dopant for an Organic Semiconducting Matrix Material, Organic of Semiconducting Material and Electronic Component, and also a Dopant and Ligand and Process for Producing same

A dopant for doping an organic semiconducting matrix material having the

• following structure:
• wherein a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8— and e=—CR9R10—, where R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are, at the same time or independently of one another, H, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably R1, R3, R5, R7, R9=H and R2, R4, R6, R8, R10,=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, or optionally, a or b or e or d can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, or at c, C is replaced by Si;
• wherein the bonds b-d and c-e or b-d and a-c can, at the same time or independently of one another, be unsaturated,
• wherein the bonds b-d, a-c and c-e can, at the same time or independently of one another, be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn,
• wherein the bonds b-d, a-c and c-e can, at the same time or independently of one another be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the atom E is an element from the main group, preferably selected from the group N, P, As, Sb, though without being limited to these,
• wherein the structural element a-E-b can be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, or
• the structural element a-E-b can be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is a transition metal, preferably W or Mo;
• wherein the structural elements a-f can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8—, e=—CR9R10— and f=CR11R12, where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are hydrogen, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably R1, R3, R5, R7, R9, R11=H and R2, R4, R6, R8, R10, R12=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, the structure 65b with R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12=H being excluded from this, or in the structural elements c and/or d, C can be replaced by Si, wherein
• a or b or e or f can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and f or b and e can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl,
• wherein the bonds a-c, b-d, c-e and d-f, but not simultaneously a-c and c-e and not simultaneously b-d and d-f can be unsaturated,
• wherein the bonds a-c, b-d, c-e and d-f can be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the bonds a-c, b-d, c-e and d-f can be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the atom E is an element from the main group, selected from the group N, P, As, Sb, though without being limited to these,
• wherein the structural element a-E-b can be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the structural element a-E-b can be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is one of W, Mo, and a transition metal,
• wherein the structural elements a-f can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8—, e=—CR9R10— and f=CR11R12, where R1, R2, R3, 4, R5, 6, R7, R8, R9, R10, R11 and R12 can, at the same time or independently from one another, be H, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably R1, R3, R5, R7, R9, R11=H and R2, R4, R6, R8, R10, R12=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, wherein
• at c or e, C can be replaced by Si, wherein
• a or b or d or f can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and d or band f can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl,
• wherein the bonds a-c, c-e, e-f and b-d, but not simultaneously a-c, c-e and e-f and not simultaneously a-c and c-e and not simultaneously c-e and e-f can be unsaturated,
• wherein the bonds a-c, c-e, e-f and b-d can be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the bonds a-c, c-e, e-f and b-d can be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the atom E is an element from the main group, preferably selected from the group N, P, As, Sb, though without being limited to these,
• wherein the structural element a-E-b can optionally be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the structural element a-E-b can optionally be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is a transition metal, preferably W or Mo;
• or
• wherein the structural elements a-g can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8—, e=—CR9R10—, f=CR11R12 and g=CR13R14, where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 can, at the same time or independently from one another, be H, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably, R1, R3, R5, R7, R9, R11, R13=H and R2, R4, R6, R8, R10, R12, R14=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, or
• at c, d and f, though not d and f simultaneously, C can be replaced by Si, wherein
• a or b or e or g can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and g or b and e can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl,
• wherein the bonds a-c, c-e, b-d, d-f and f-g, but not simultaneously a-c and c-e, and not simultaneously b-d, d-f and f-g, and not simultaneously b-d and d-f, and not simultaneously d-f and f-g, can be unsaturated,
• wherein the bonds a-c, c-e, b-d, d-f and f-g can be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the bonds a-c, c-e, b-d, d-f and f-g can be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the atom E is an element from the main group, preferably selected from the group N, P, As, Sb, though without being limited to these,
• wherein the structural element a-E-b can optionally be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the structural element a-E-b can be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N
• wherein the metal M is a transition metal, preferably W or Mo.

A ligand for a metal complex, selected from the group consisting of

• wherein the structural elements a-e can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8— and e=—CR9R10—, where R1, R2, R3, R4, R5, R6, R7, Rx, R9 and R10 are, at the same time or independently of one another, H, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably R1, R3, R5, R7, R9=H and R2, R4, R6, R8, R10=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, where the structure 65a′ with R1 to R10=H is excluded from this, where the structure 65a′ with R1 and R2=aryl is excluded from this, where in the structure 65a′ R1 and R10 are always H, wherein
• a or b or e or d can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and d or b and e can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• at c, C is replaced by Si,
• wherein the bonds b-d and c-e or b-d and a-c can, at the same time or independently of one another, be unsaturated, wherein the bonds b-d, a-c and c-e can, at the same time or independently of one another, be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, where the ligand with c-e=cyclohexyl and cyclohexenyl is excluded from this, or
• wherein the bonds b-d, a-c and c-e can, at the same time or independently of one another be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N, where the ligand in which b-d, a-c and c-e are components of benzene is excluded from this,
• wherein the atom E is an element from the main group, preferably selected from the group consisting of N, P, As, Sb, though without being limited to these,
• wherein the structural element a-E-b can be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, or
• the structural element a-E-b can optionally be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is a transition metal, preferably W or Mo;
• wherein the structural elements a-f can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8—, e=—CR9R10— and f=CR11R12, where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are hydrogen, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably R1, R3, R5, R7, R9, R11=H and R2, R4, R6, R8, R10, R12=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, the structure 65b with R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12=H being excluded from this, the ligand with R9, R10, R11 and R12=phenyl, methyl, allyl, RSCH2— and ROCH2— being excluded from this, the ligand with R9=phenyl, R10=H, R11=phenyl, R12=H being excluded from this, the ligand with R1=phenyl being excluded from this, the ligand with R5, R6, R7, R8=phenoxy being excluded from this, wherein
• in the structural elements c and/or d, C can be replaced by Si, wherein
• a or b or e or f can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and f or b and e can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl,
• wherein the bonds a-c, b-d, c-e and d-f, but not simultaneously a-c and c-e and not simultaneously b-d and d-f can be unsaturated,
• wherein the bonds a-c, b-d, c-e and d-f can be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the bonds a-c, b-d, c-e and d-f can be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N, the ligand in which a-c, b-d, c-e and d-f are components of benzene being excluded from this,
• wherein the atom E is an element from the main group, preferably selected from the group N, P, As, Sb, though without being limited to these,
• wherein the structural element a-E-b can be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, excluding from this the ligand with a-E-b=component of cyclopentyl and pyranyl with R9 to R12=alkyl, wherein
• the structural element a-E-b can optionally be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is a transition metal, preferably W or Mo;
• wherein the structural elements a-f can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8—, e=—CR9R10— and f=CR11R12, where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 can, at the same time or independently from one another, be H, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably R1, R3, R5, R7, R9, R11=H and R2, R4, R6, R8, R10, R12=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, the ligand with R11 to R12=H being excluded from this, or
• at c or e, C can be replaced by Si, wherein
• a or b or d or f can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and d or band f can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl,
• wherein the bonds a-c, c-e, e-f and b-d, but not simultaneously a-c, c-e and e-f and not simultaneously a-c and c-e and not simultaneously c-e and e-f can be unsaturated,
• wherein the bonds a-c, c-e, e-f and b-d can be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the bonds a-c, c-e, e-f and b-d can be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N, the ligand with E=N and simultaneously e-f and/or b-d as part of benzene or naphthalene being excluded from this, the ligand with E=N and simultaneously R7=R8=phenyl being excluded from this, the ligand with E=N and R3=phenyl, benzyl being excluded from this
• wherein the atom E is an element from the main group, preferably selected from the group N, P, As, Sb, though without being limited to these, the ligand with E=N and simultaneously the seven-membered ring with more than one unsaturated bond being excluded from this
• wherein the structural element a-E-b can optionally be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the structural element a-E-b can optionally be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is a transition metal, preferably W or Mo;
• wherein the structural elements a-g can mean:
• a=—CR1R2—, b=—CR3R4—, c=—CR5R6—, d=—CR7R8—, e=—CR9R10—, f=CR11R12 and g=CR13R14, where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 can, at the same time or independently from one another, be H, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, preferably, R1, R3, R5, R7, R9, R11, R13=H and R2, R4, R6, R8, R10, R12, R14=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, —NR2 or —OR, or
• at c, d and f, though not d and f simultaneously, C can be replaced by Si, wherein
• a or b or e or g can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl, wherein
• a and g or b and e can be NR with R=C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkenyl, C1-C20 alkinyl, aryl, heteroaryl,
• wherein the bonds a-c, c-e, b-d, d-f and f-g, but not simultaneously a-c and c-e, and not simultaneously b-d, d-f and f-g, and not simultaneously b-d and d-f, and not simultaneously d-f and f-g, can be unsaturated, the ligand in which b-d and f-g are simultaneously unsaturated being excluded from this,
• wherein the bonds a-c, c-e, b-d, d-f and f-g can be part of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the bonds a-c, c-e, b-d, d-f and f-g can be part of an aromatic or condensed aromatic ring system which can also contain the heteroelements O, S, Se, N, the ligand in which c-e and f-g are simultaneously part of a benzene ring being excluded from this,
• wherein the atom E is an element from the main group, preferably selected from the group B, C, N, O, Si, P, S, As, Se, Sb, Te, particularly preferably selected from the group S, Se, N, P, though without being limited to these,
• wherein the structural element a-E-b can optionally be a component of a saturated or unsaturated ring system which can also contain the heteroelements O, S, Se, N, P, Si, Ge, Sn, wherein
• the structural element a-E-b can optionally be a component of an aromatic ring system which can also contain the heteroelements O, S, Se, N,
• wherein the metal M is a transition metal, preferably W or Mo.