Specifically substituted benzofuro- and benzothienoquinolines for organic light emitting diodes

An organic electronic device, comprising a heterocyclic derivative of formula (1a) or (1b)

• wherein
• X is O or S;
• B1 is CR1;
• B2 is CH;
• B3 is CR3;
• B4 is CR4;
• B5 is CR5;
• B6 is CR6;
• B7 is CR7;
• B8 is CR8;
• R1, R3, R4, R5, R6, R7, and R8 are independently of each other H;
• E;
• a group of formula -(A1)o-(A2)p-(A3)q-(A4)r-R20;
• or a C1-C25alkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by D;
• wherein o is 0 or 1, p is 0 or 1, q is 0 or 1, r is 0 or 1 in the formula -(A1)o-(A2)p-(A3)q-(A4)r-R20 for R1, R3, R4, R5, R6, R7, and R8;
• RA1 is a group of formula -(A1)o-(A2)p-(A3)q-(A4)r-R20, wherein o is 1, p is 0 or 1, q is 0 or 1, r is 0 or 1 in the formula -(A1)o-(A2)p-(A3)q-(A4)r-R20 for RA1;
• RA2 is selected from group consisting of
• A1, A2, A3, and A4 are independently of each other a C6-C24 arylene group which is unsubstituted or substituted by G, a C1-C24 heteroarylene group which is unsubstituted or substituted by G;
• R20 is H;
• E;
• a C6-C60 aryl group which is unsubstituted or substituted by G, a C1-C60 heteroaryl group which is unsubstituted or substituted by G, a C1-C25alkyl group, which is unsubstituted or substituted by at least one group G and/or interrupted by D;
• D is —CO—, —COO—, —S—, —SO—, —SO2—, —CR63═CR64—, —NR65—, —SiR70R71—, —POR73—, or —C≡C—;
• E is —SR69, —COR68, —COOR67, —CONR65R66, —CN, —SiR70R71R72, or —POR74R75;
• G is E;
• or a C1-C24alkyl group;
• a C1-C24alkyl group, which is interrupted by O;
• a C6-C60aryl group, a C6-C60aryl group, which is substituted by F, —CF3, —CF2CF3, —CF2CF2CF3, —CF(CF3)2, —(CF2)3CF3, —C(CF3)3, a C1-C24alkyl or a C1-C24alkyl which is interrupted by O;
• a C2-C60heteroaryl group;
• or a C2-C60heteroaryl group, which is substituted by F, —CF3, —CF2CF3, —CF2CF2CF3, —CF(CF3)2, —(CF2)3CF3, —C(CF3)3, a C1-C24alkyl or a C1-C24alkyl which is interrupted by O;
• R63 and R64 are independently of each other a C6-C18aryl;
• a C6-C18aryl which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a C1-C18alkyl;
• or a C1-C18alkyl which is interrupted by —O—;
• H;
• R65 and R66 are independently of each other a C6-C18aryl group;
• a C6-C18aryl which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a 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, which can be substituted or benzanullated;
• R67 is a C6-C18aryl group;
• a C6-C18aryl group, which is substituted by a C1-C18alkyl, or a C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R68 is H;
• a C6-C18aryl group;
• a C6-C18aryl group, which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R69 is a C6-C18aryl;
• a C6-C18aryl, which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R70, R71 and R72 are independently of each other a C1-C18alkyl group, a C6-C18aryl group, or a C6-C18aryl group, which is substituted by a C1-C18alkyl;
• and
• R73, R74, and R75 is a C1-C18alkyl group, a C6-C18aryl group, or a C6-C18aryl group, which is substituted by a C1-C18 alkyl;
• wherein in the case of formula (1b) B3 is CH and o, p, q and r in the definition of R6 and R7 are 0.

An organic electroluminescence device, comprising

• a first electron transport layer and a second electron transport layer, wherein the second electron transport layer comprises a heterocyclic derivative of formula (1):
• wherein
• X is O or S;
• A1 is N or CRA1;
• A2 is N or CRA2;
• wherein one of A1 and A2 is N;
• B1 is CR1;
• B2 is CH;
• B3 is CR3;
• B4 is CR4;
• B5 is CR5;
• B6 is CR6;
• B7 is CR7;
• B8 is CR8;
• R1, R3, R4, R5, R6, R7, and R8 are independently of each other H;
• E;
• a group of formula -(A1)o-(A2)p-(A3)q-(A4)r-R20;
• or a C1-C25alkyl group, which is unsubstituted or substituted by at least one group E and/or interrupted by D;
• wherein o is 0 or 1, p is 0 or 1, q is 0 or 1, r is 0 or 1 in the formula -(A1)o-(A2)p-(A3)q-(A4)r-R20 for R1, R3, R4, R5, R6, R7, and R8;
• RA1 is selected from the group consisting of
• RA2 is selected from group consisting of
• A1, A2, A3, and A4 are independently of each other a C6-C24 arylene group which is unsubstituted or substituted by G, a C1-C24 heteroarylene group which is unsubstituted or substituted by G;
• R20 is H;
• E;
• a C6-C60 aryl group which is unsubstituted or substituted by G, a C1-C60 heteroaryl group which is unsubstituted or substituted by G, a C1-C25alkyl group, which is unsubstituted or substituted by at least one group G and/or interrupted by D;
• D is —CO—, —COO—, —S—, —SO—, —SO2—, —CR63═CR64—, —NR65—, —SiR70R71—, —POR73—, or —C≡C—;
• E is —SR69, —COR68, —COOR67, —CONR65R66, —CN, —SiR70R71R72, or —POR74R75;
• G is E;
• or a C1-C24alkyl group;
• a C1-C24alkyl group, which is interrupted by O;
• a C6-C60aryl group, a C6-C60aryl group, which is substituted by F, —CF3, —CF2CF3, —CF2CF2CF3, —CF(CF3)2, —(CF2)3CF3, —C(CF3)3, a C1-C24alkyl or a C1-C24alkyl which is interrupted by O;
• a C2-C60heteroaryl group;
• or a C2-C60heteroaryl group, which is substituted by F, —CF3, —CF2CF3, —CF2CF2CF3, —CF(CF3)2, —(CF2)3CF3, —C(CF3)3, a C1-C24alkyl or a C1-C24alkyl which is interrupted by O;
• R63 and R64 are independently of each other a C6-C18aryl;
• a C6-C18aryl which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a C1-C18alkyl;
• or a C1-C18alkyl which is interrupted by —O—;
• H;
• R65 and R66 are independently of each other a C6-C18aryl group;
• a C6-C18aryl which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a 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, which can be substituted or benzanullated;
• R67 is a C6-C18aryl group;
• a C6-C18aryl group, which is substituted by a C1-C18alkyl, or a C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R68 is H;
• a C6-C18aryl group;
• a C6-C18aryl group, which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R69 is a C6-C18aryl;
• a C6-C18aryl, which is substituted by a C1-C18alkyl or a C1-C18alkoxy;
• a C1-C18alkyl group;
• or a C1-C18alkyl group, which is interrupted by —O—;
• R70, R71 and R72 are independently of each other a C1-C18alkyl group, a C6-C18aryl group, or a C6-C18aryl group, which is substituted by a C1-C18alkyl;
• and
• R73, R74, and R75 is a C1-C18alkyl group, a C6-C18aryl group, or a C6-C18aryl group, which is substituted by a C1-C18 alkyl;
• wherein in the case that A1 is CRA1 and A2 is N, B3 is CH and o, p, q and r in the definition of R6 and R7 are 0.