Heteroaromatic compounds for organic electronics

2:

• The compound of formula (1) of claim 1, wherein:
• X is O, S or NR,
• R10 is H, C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl or C(O)—OR11,
• R1 and R11 are independently from each other selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl,
• R2, R3, R4, R5, R6, R7, R8 and R9 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl, O—C1-30-alkyl, substituted O—C1-30-alkyl, S—C1-30-alkyl, substituted S—C1-30-alkyl, C6-14-aryl, substituted C6-14-aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen;
• or R2 and R3, R3 and R4, R4 and R5, R6 and R7, R7 and R8, or, R8 and R9 together with the C-atoms, to which they are connected, form a 6 to 10 membered aromatic ring system, substituted 6 to 10 membered aromatic ring system, 5 to 12 membered heteroaromatic ring system or a substituted 5 to 12 membered heteroaromatic ring system,
• substituted C1-30-alkyl, substituted C2-30-alkenyl, substituted O—C1-30-alkyl and substituted S—C1-30-alkyl, at each occurrence, are C1-30-alkyl, C2-30-alkenyl, O—C1-30-alkyl, respectively, S—C1-30-alkyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbRc, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbR, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• substituted C5-8-cycloalkyl and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbRc, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbR, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• substituted C6-14-aryl, substituted 5 to 15 membered heteroaryl, substituted 6 to 10 membered aromatic ring system and substituted 5 to 12 membered heteroaromatic ring system, at each occurrence, are C6-14-aryl, 5 to 15 membered heteroaryl, 6 to 10 membered aromatic ring system, respectively, 5 to 12 membered heteroaromatic ring system, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbR, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbRc, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2,
• at least one CH2-group, but not adjacent CH2-groups, of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl, O—C1-30-alkyl, substituted O—C1-30-alkyl, S—C1-30-alkyl and substituted S—C1-30-alkyl, can be replaced by a linking group selected from the group consisting of O, S, NR12, CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR12—C(O), C(O)—NR12, OC(O)—NR12 and NR12—C(O)—O,
• R12 is H, C1-30-alkyl, substituted C1-30-alkyl, or C(O)—ORd, and
• Ra, Rb, Rc and Rd are independently from each other and at each occurrence selected from the group consisting of H, C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, and 5 to 12 membered heteroaryl.

3:

• The compound of claim 1, wherein:
• X is O, S or NR10,
• R10 is H, C1-30-alkyl, substituted C1-30-alkyl or C(O)—OR11,
• R1 and R11 are independently from each other selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl,
• R2, R3, R4, R5, R6, R7, R8 and R9 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C6-14-aryl, substituted C6-14-aryl, 5 to 15 membered heteroaryl and substituted 5 to 15 membered heteroaryl;
• or R2 and R3, R3 and R4, R4 and R5, R6 and R7, R7 and R8, or, R8 and R9 together with the C-atoms, to which they are connected, form a 6 to 10 membered aromatic ring system, substituted 6 to 10 membered aromatic ring system, 5 to 12 membered heteroaromatic ring system or a substituted 5 to 12 membered heteroaromatic ring system,
• substituted C1-30-alkyl and substituted C2-30-alkenyl, at each occurrence, are C1-30-alkyl, respectively, C2-30-alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbRe, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbR, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbR, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• substituted C5-8-cycloalkyl and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbRc, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbR, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• substituted C6-14-aryl, substituted 5 to 15 membered heteroaryl, substituted 6 to 10 membered aromatic ring system, and substituted 5 to 12 membered heteroaromatic ring system, at each occurrence, are C6-14-aryl, 5 to 15 membered heteroaryl, 6 to 10 membered aromatic ring system, respectively, 5 to 12 membered heteroaromatic ring system, which are substituted with at least one substituent independently selected from the group consisting of C1-120-alkyl, C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbR, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbRc, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2,
• at least one CH2-group, but not adjacent CH2-groups, of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl can be replaced by a linking group selected from the group consisting of O, S, NR12, CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR12—C(O), C(O)—NR12, OC(O)—NR12 and NR12—C(O)—O,
• R12 is H, C1-30-alkyl, substituted C1-30-alkyl or C(O)—ORd,
• Ra, Rb, Rc and Rd are independently from each other and at each occurrence selected from the group consisting of H, C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, and 5 to 12 membered heteroaryl.

4:

• The compound of claim 1, wherein:
• X is O, S or NR10,
• R10 is H, C1-30-alkyl, substituted C1-30-alkyl or C(O)—OR11,
• R1 and R11 are independently from each other selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl,
• R2, R3, R4, R5, R6, R7, R8 and R9 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C6-14-aryl, substituted C6-14-aryl, 5 to 15 membered heteroaryl and substituted 5 to 15 membered heteroaryl;
• or R2 and R3, R3 and R4, R4 and R5, R6 and R7, R7 and R8, or, R8 and R9 together with the C-atoms, to which they are connected, form a 6 to 10 membered aromatic ring system, substituted 6 to 10 membered aromatic ring system, 5 to 12 membered heteroaromatic ring system or a substituted 5 to 12 membered heteroaromatic ring system,
• substituted C1-30-alkyl and substituted C2-30-alkenyl, at each occurrence, are C1-30-alkyl, respectively, C2-30-alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl, C6-10-aryl, and 5 to 12 membered heteroaryl,
• substituted C5-8-cycloalkyl and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, and 5 to 12 membered heteroaryl;
• substituted C6-14-aryl, substituted 5 to 15 membered heteroaryl, substituted 6 to 10 membered aromatic ring system, and substituted 5 to 12 membered heteroaromatic ring system, at each occurrence, are C6-14-aryl, 5 to 15 membered heteroaryl, 6 to 10 membered aromatic ring system, respectively, 5 to 12 membered heteroaromatic ring system, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl;
• wherein
• at least one CH2-group, but not adjacent CH2-groups, of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl can be replaced by a linking group selected from the group consisting of O, S, and NR12,
• R12 is H, C1-30-alkyl, substituted C1-30-alkyl or C(O)—ORd, and
• Rd is at each occurrence selected from the group consisting of H, C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-6-cycloalkyl, C5-6-cycloalkenyl, C6-10-aryl, and 5 to 12 membered heteroaryl.

5:

• The compound of claim 1, wherein:
• X is S,
• R1 is selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl,
• R2, R3, R4, R5, R6, R7, R8 and R9 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C6-10-aryl, substituted C6-10-aryl, 5 to 12 membered heteroaryl, and substituted 5 to 12 membered heteroaryl;
• or R2 and R3, R3 and R4, R4 and R5, R6 and R7, R7 and R8, or, R8 and R9 together with the C-atoms, to which they are connected, form a 6 membered aromatic ring system, substituted 6 membered aromatic ring system, 5 to 9 membered heteroaromatic ring system or a substituted 5 to 9 membered heteroaromatic ring system,
• substituted C1-30-alkyl and substituted C2-30-alkenyl, at each occurrence, are C1-30-alkyl, respectively, C2-30-alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl, phenyl and 5 to 9 membered heteroaryl,
• substituted C5-8-cycloalkyl and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, phenyl and 5 to 9 membered heteroaryl,
• substituted C6-10-aryl, substituted 5 to 12 membered heteroaryl, substituted 6 membered aromatic ring system, and substituted 5 to 9 membered heteroaromatic ring system, at each occurrence, are C6-10-aryl, 5 to 12 membered heteroaryl, 6 membered aromatic ring system, respectively, 5 to 9 membered heteroaromatic ring system, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, phenyl, 5 to 9 membered heteroaryl, and
• at least one CH2-group, but not adjacent CH2-groups, of C1-30-alkyl, substituted C1-30-alkyl, C5-8-cycloalkyl and substituted C5-8-cycloalkyl, can be replaced by the linking group O.

6:

• The compound of claim 1, wherein:
• X is S,
• R1 is selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl,
• R2, R3, R4, R5, R6, R7, R8 and R9 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C5-8-cycloalkyl, and substituted C5-8-cycloalkyl,
• substituted C1-30-alkyl and substituted C2-30-alkenyl, at each occurrence, are C1-30-alkyl, respectively, C2-30-alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl, phenyl and 5 to 9 membered heteroaryl, and
• substituted C5-8-cycloalkyl and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl, phenyl and 5 to 9 membered heteroaryl.

7:

• The compound of claim 1, wherein:
• X is S,
• R1 is selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl and substituted C5-8-cycloalkenyl,
• R2, R4, R5, R6, R7 and R9 are H,
• R3 and R8 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C5-8-cycloalkyl and substituted C5-8-cycloalkyl,
• substituted C1-30-alkyl and substituted C2-30-alkenyl, at each occurrence, are C1-30-alkyl, respectively, C2-30-alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl and phenyl, and
• substituted C5-8-cycloalkyl and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C5-6-cycloalkyl and phenyl.

8:

• A process for preparing the compound of claim 1,
• the process comprising treating a compound of formula (2):
• with a compound of formula:
• R1O—C(O)-LG,
• to obtain the compound of formula (1):
• wherein:
• X is O, S or NR10;
• R10 is H C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C2-30-alkynyl, substituted C1-30-alkynyl or C(O)—OR11;
• R1 and R11 are independently from each other selected from the group consisting of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C2-30-alkynyl, substituted C2-30-alkynyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl, and substituted C5-8-cycloalkenyl;
• R2, R3, R4, R5, R6, R7, R8 and R9 are independently from each other selected from the group consisting of H, C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C2-30-alkynyl, substituted C2-30-alkynyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl, substituted C5-8-cycloalkenyl, O—C1-30-alkyl, substituted O—C1-30-alkyl, S—C1-30-alkyl, substituted S—C1-30-alkyl, C6-14-aryl, substituted C6-14-aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen,
• or R2 and R3, R3 and R4, R4 and R5, R6 and R7, R7 and R8, or, R8 and R9 together with the C-atoms, to which they are connected, form a 6 to 10 membered aromatic ring system, substituted 6 to 10 membered aromatic ring system, 5 to 12 membered heteroaromatic ring system or a substituted 5 to 12 membered heteroaromatic ring system;
• substituted C1-30-alkyl, substituted C2-30-alkenyl, substituted C2-30-alkynyl, substituted O—C1-30-alkyl and substituted S—C1-30-alkyl, at each occurrence, are C1-30-alkyl, C1-30-alkenyl, C2-30-alkynyl, O—C1-30-alkyl, respectively, S—C1-30-alkyl, which are substituted with at least one substituent independently selected from the group consisting of C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbRc, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbR, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• substituted C5-8-cycloalkyl, and substituted C5-8-cycloalkenyl, at each occurrence, are C5-8-cycloalkyl, respectively, C5-8-cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C1-20-alkenyl, C2-20-alkynyl, C5-6-cycloalkyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbR, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb, NRa—NRbRc, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• substituted C6-14-aryl, substituted 5 to 15 membered heteroaryl, substituted 6 to 10 membered aromatic ring system, and substituted 5 to 12 membered heteroaromatic ring system, at each occurrence, are C6-14-aryl, 5 to 15 membered heteroaryl, 6 to 10 membered aromatic ring system, respectively, 5 to 12 membered heteroaromatic ring system, which are substituted with at least one substituent independently selected from the group consisting of C1-20-alkyl, C2-20-alkenyl, C2-20-alkynyl, C5-6-cycloalkyl, C5-6-cycloalkenyl, C6-10-aryl, 5 to 12 membered heteroaryl, ORa, OC(O)—Ra, OC(O)—ORa, OC(O)—NRaRb, C(O)—Ra, C(O)—ORa, C(O)—NRaRb, C(O)—NRa—NRbRc, C(O)—NRa—ORb, C(O)—NRa—C(O)—Rb, C(O)—NRa—C(O)—ORb, C(O)—SRa, NRaRb NRa—NRbR, NRa—C(O)Rb, NRa—C(O)—ORb, NRa—C(O)—NRbRc, SRa, S—C(O)—Ra, halogen, CN, and NO2;
• at least one CH2-group, but not adjacent CH2-groups, of C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C1-30-alkenyl, C2-30-alkynyl, substituted C2-30-alkynyl, C5-8-cycloalkyl, substituted C5-8-cycloalkyl, C5-8-cycloalkenyl, substituted C5-8-cycloalkenyl, O—C1-30-alkyl, substituted O—C1-30-alkyl, S—C1-30-alkyl and substituted S—C1-30-alkyl, can be replaced by a linking group selected from the group consisting of O, S, NR12, CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR12—C(O), C(O)—NR12, OC(O)—NR12 and NR12—C(O)—O;
• R12 is H, C1-30-alkyl, substituted C1-30-alkyl, C2-30-alkenyl, substituted C2-30-alkenyl, C2-30-alkynyl, substituted C1-30-alkynyl or C(O)—ORd;
• Ra, Rb, Re and Rd are independently from each other and at each occurrence selected from the group consisting of H, C1-20-alkyl, C1-20-alkenyl, C2-20-alkynyl, C5-6 cycloalkyl, C5-6-cycloalkenyl, C6-10-aryl, and 5 to 12 membered heteroaryl;
• and
• LG is a leaving group.