Heteroaromatic compounds for organic electronics
The present invention provides compounds of formula (I) wherein X is O, S or NR 10 , wherein R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(0)-OR 11 , R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl, and an electronic device comprising the compounds as semiconducting material.
1. A compound of formula (1):
wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(O)—OR 11 ,
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl, substituted S—C 1-30 -alkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen,
or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 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 C 1-30 -alkyl, substituted C 2-30 -alkenyl, substituted C 2-30 -alkynyl, substituted O—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, at each occurrence, are C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, O—C 1-30 -alkyl, respectively, S—C 1-30 -alkyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 6-14 -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 C 6-14 -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 C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ,
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, can be replaced by a linking group selected from the group consisting of O, S, NR 12 , CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR 12 —C(O), C(O)—NR 12 , OC(O)—NR 12 and NR 12 —C(O)—O,
R 12 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(O)—OR d , and
R a , R b , R c and R d are independently from each other and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, and 5 to 12 membered heteroaryl.
2. The compound of claim 1 , wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, or C(O)—OR 11 ,
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl, substituted S—C 1-30 -alkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen, or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 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 C 1-30 -alkyl, substituted C 2-30 -alkenyl, substituted O—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, at each occurrence, are C 1-30 -alkyl, C 2-30 -alkenyl, O—C 1-30 -alkyl, respectively, S—C 1-30 -alkyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 6-14 -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 C 6-14 -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 C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ,
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, can be replaced by a linking group selected from the group consisting of O, S, NR 12 , CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR 12 —C(O), C(O)—NR 12 , OC(O)—NR 12 and NR 12 —C(O)—O,
R 12 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, or C(O)—OR d , and
R a , R b , R c and R d are independently from each other and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, and 5 to 12 membered heteroaryl.
3. The compound of claim 1 , wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl or C(O)—OR 11 ,
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen, or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 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 C 1-30 -alkyl, substituted C 2-30 -alkenyl, at each occurrence, are C 1-30 -alkyl, respectively, C 2-30 -alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 6-14 -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 C 6-14 -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 C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ,
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl can be replaced by a linking group selected from the group consisting of O, S, NR 12 , CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR 12 —C(O), C(O)—NR 12 , OC(O)—NR 12 and NR 12 —C(O)—O,
R 12 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, or C(O)—OR d ,
R a , R b , R c and R d are independently from each other and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, and 5 to 12 membered heteroaryl.
4. The compound of claim 1 , wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl or C(O)—OR 11 ,
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl and substituted 5 to 15 membered heteroaryl; or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 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 C 1-30 -alkyl, substituted C 2-30 -alkenyl, at each occurrence, are C 1-30 -alkyl, respectively, C 2-30 -alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl,
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl;
substituted C 6-14 -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 C 6-14 -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 C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl;
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl can be replaced by a linking group selected from the group consisting of O, S, NR 12 ,
R 12 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl or C(O)—OR d , and
R d is at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, and 5 to 12 membered heteroaryl.
5. The compound of claim 1 , wherein:
X is S,
R 1 is selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 6-10 -aryl, substituted C 6-10 -aryl, 5 to 12 membered heteroaryl, and substituted 5 to 12 membered heteroaryl; or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 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 C 1-30 -alkyl and substituted C 2-30 -alkenyl, at each occurrence, are C 1-30 -alkyl, respectively, C 2-30 -alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, phenyl and 5 to 9 membered heteroaryl,
substituted C 5-8 -cycloalkyl and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -cycloalkyl, phenyl and 5 to 9 membered heteroaryl,
substituted C 6-10 -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 C 6-10 -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 C 1-20 -alkyl, C 5-6 -cycloalkyl, phenyl, 5 to 9 membered heteroaryl, and
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 5-8 -cycloalkyl and substituted C 5-8 -cycloalkyl, can be replaced by the linking group O.
6. The compound of claim 1 , wherein:
X is S,
R 1 is selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl,
substituted C 1-30 -alkyl and substituted C 2-30 -alkenyl, at each occurrence, are C 1-30 -alkyl, respectively, C 2-30 -alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, phenyl and 5 to 9 membered heteroaryl, and
substituted C 5-8 -cycloalkyl and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -cycloalkyl, phenyl and 5 to 9 membered heteroaryl.
7. The compound of claim 1 , wherein:
X is S,
R 1 is selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl and substituted C 5-8 -cycloalkenyl,
R 2 , R 4 , R 5 , R 6 , R 7 and R 9 are H,
R 3 and R 8 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 5-8 -cycloalkyl and substituted C 5-8 -cycloalkyl,
substituted C 1-30 -alkyl and substituted C 2-30 -alkenyl, at each occurrence, are C 1-30 -alkyl, respectively, C 2-30 -alkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl and phenyl, and
substituted C 5-8 -cycloalkyl and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -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:
R 1 O—C(O)-LG
to obtain the compound of formula (1):
wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(O)—OR 11 ;
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl;
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl, substituted S—C 1-30 -alkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen,
or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 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 C 1-30 -alkyl, substituted C 2-30 -alkenyl, substituted C 2-30 -alkynyl, substituted O—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, at each occurrence, are C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, O—C 1-30 -alkyl, respectively, S—C 1-30 -alkyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 6-14 -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 C 6-14 -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 C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, can be replaced by a linking group selected from the group consisting of O, S, NR 12 , CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR 12 —C(O), C(O)—NR 12 , OC(O)—NR 12 and NR 12 —C(O)—O;
R 12 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(O)—OR d ;
R a , R b , R c and R d are independently from each other and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, and 5 to 12 membered heteroaryl; and
LG is a leaving group.
9. An electronic device, comprising the compound of claim 1 , wherein said electronic device is an organic photovoltaic device (OPV), an organic field-effect transistor (OFET), an organic light emitting diode (OLED), or an organic photodiode (OPD).
10. The electronic device of claim 9 , wherein the electronic device is an organic field effect transistor (OFET).
11. A semiconducting material, comprising the compound of claim 1 .