Pt- or pd-carbene complexes for use in organic light emitting diodes

A complex of the general formula (I) or (II)

• wherein M, A1, A2, R1, R2, R3, R4, R5, R6, R7 and R10 are each defined as follows:
• M is Pt or Pd,
• A1 is N or CR8,
• A2 is N or CR9,
• R1 and R2
• are independently of each other a C1-C18alkyl group, which can optionally be substituted by at least one substituent E;
• a C3-C12cycloalkyl group, which can optionally be substituted by at least one substituent E;
• a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR65 and/or substituted by at least one substituent E;
• a C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR65;
• a C1-C18haloalkyl group;
• or CN;
• R3
• is hydrogen;
• a C1-C18alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D;
• a C3-C12cycloalkyl group, which can optionally be substituted by at least one substituent E;
• a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR65 and/or substituted by at least one substituent E;
• a C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a —O—C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR65;
• a halogen atom;
• a C1-C18haloalkyl group;
• or CN;
• or
• R1 and R3 or R2 and R3 together form a group of formula
• wherein X′ is present in the position of R3 and is selected from O, S, NR75 and CR73R74;
• Rf, Rg, Rh, Ri, Rj and Rk are independently of each other H, a C1-C5alkyl group, a fluoroC1-C4alkyl group, or a C3-C6cycloalkyl group;
• n is 0 or 1;
• wherein the group of formula (III) comprises 0, 1 or 2 double bonds;
• in the case that 1 or 2 double bonds are present in the group of formula (III), the carbon atoms connected with the double bonds are each substituted by only one residue Rf, Rj and/or—in the case that n is 1—Rh;
• R5 and R6
• are independently of each other hydrogen;
• a C1-C18alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D;
• a C3-C12cycloalkyl group, which can optionally be substituted by at least one substituent E;
• a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR65 and/or substituted by at least one substituent E;
• a C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a —NR65—C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR65;
• a halogen atom;
• a C1-C18haloalkyl group;
• CN;
• or SiR80R81R82;
• or
• R5 and R6 together form a group of formula
• wherein X is O, S, NR75 or CR73R74;
• R′″ is C1-C8alkyl and a is 0, 1 or 2;
• R4 and R7
• are independently of each other hydrogen;
• a C1-C18alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D;
• a C3-C12cycloalkyl group, which can optionally be substituted by at least one substituent E;
• a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR65 and/or substituted by at least one substituent E;
• a C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR65 a halogen atom;
• a C1-C18haloalkyl group;
• CN;
• or SiR80R81R82;
• or
• R6 and R7 together form a group of formula
• wherein X is O, S, NR75 or CR73R74;
• R′″ is C1-C8alkyl and a is 0, 1 or 2;
• R8 and R9
• are independently of each other hydrogen;
• a C1-C18alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D;
• a C3-C12cycloalkyl group, which can optionally be substituted by at least one substituent E;
• a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR65 and/or substituted by at least one substituent E;
• a C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a —O—C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR65;
• a halogen atom;
• a C1-C18haloalkyl group;
• or CN;
• or
• R8 and R9 together form a group of formula
• wherein Y is N or CRn;
• Z is N or CRo;
• Rl, Rm, Rn and Ro are independently of each other H, a C1-C5alkyl group, a fluoroC1-C4alkyl group, or a C3-C6cycloalkyl group;
• R10
• is a C1-C18alkyl group, which can optionally be substituted by at least one substituent E;
• a C3-C12cycloalkyl group, which can optionally be substituted by at least one substituent E;
• a heterocycloalkyl group comprising 3 to 6 ring atoms, interrupted by at least one of O, S and NR65 and/or substituted by at least one substituent E;
• a C6-C14aryl group, which can optionally be substituted by at least one substituent G;
• a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by at least one substituent G, interrupted by at least one of O, S, N and NR65;
• D is —CO—, —COO—, —S—, —SO—, —SO2—, —O—, —NR65—, —SiR70R71—, —POR72—, —CR63═CR64—, or —C≡C;
• E is —OR69, —SR69, —NR65R66, —COR68, —COOR67, —CONR65R66, —CN, halogen, or a C1-C18alkyl group, which can optionally be substituted by at least one substituent E and/or interrupted by D;
• G is E;
• or an unsubstituted C6-C14aryl group;
• a C6-C14aryl group, which is substituted by F, C1-C18alkyl, or C1-C18alkyl, which is substituted by F and/or interrupted by O;
• an unsubstituted heteroaryl group comprising 5 to 11 ring atoms, interrupted by at least one of O, S, N and NR65;
• or a heteroaryl group comprising 5 to 11 ring atoms, interrupted by at least one of O, S, N and NR65, which is substituted by F, unsubstituted C1-C18alkyl, SiR80R81R82, or C1-C18alkyl which is substituted by F and/or interrupted by O;
• R63 and R64 are independently of each other H;
• unsubstituted C6-C18aryl;
• C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• unsubstituted C1-C18alkyl;
• or C1-C18alkyl which is interrupted by —O—;
• R65 and R66 are independently of each other H, an unsubstituted C6-C18aryl group;
• a C6-C18aryl group which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• an unsubstituted C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• or R65 and R66 together form a five or six membered ring;
• R67 is H, an unsubstituted C6-C18aryl group;
• a C6-C18aryl group, which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• an unsubstituted C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R68 is H;
• an unsubstituted C6-C18aryl group;
• a C6-C18aryl group, which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• an unsubstituted C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R69 is H, an unsubstituted C6-C18aryl;
• a C6-C18aryl, which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• an unsubstituted C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R70 and R71 are independently of each other an unsubstituted C1-C18alkyl group;
• an unsubstituted C6-C18aryl group;
• or a C6-C18aryl group, which is substituted by C1-C18alkyl;
• R72 is an unsubstituted C1-C18alkyl group;
• an unsubstituted C6-C18aryl group, or a C6-C18aryl group, which is substituted by C1-C18alkyl;
• R73 and R74 are independently of each other H;
• unsubstituted C6-C18aryl;
• C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• unsubstituted C1-C18alkyl;
• or C1-C18alkyl which is interrupted by —O;
• R75 is a C6-C18aryl group;
• a C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R80, R81 and R82 are independently of each other a C1-C25alkyl group, which can optionally be interrupted by O;
• a C6-C14aryl group, which can optionally be substituted by C1-C18alkyl;
• or a heteroaryl group comprising 5 to 11 ring atoms, which can optionally be substituted by C1-C18alkyl.