Phenanthro[9,10-B]furan polymers and small molecules for electronic applications
Phenanthro[9,10-b]furan polymers and small molecules for electronic applications. The present invention relates to polymers comprising a repeating unit of the formula (I), (II), (VIII), (IX) and compounds of formula (VIII), or (IX), wherein Y, Y 15 , Y 16 and Y 17 are independently of each other a group of formula (I), or (II), and their use as organic semiconductor in organic electronic devices, especially in organic photovoltaics and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers and compounds according to the invention can have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers and compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.
1. A polymer, comprising a repeating unit of formula (I) or formula (II):
where
R 1 and R 2 are each independently H, F, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E′ and/or interrupted by D′, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G′, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G′, or
R 1 and R 2 form together a group
R 205 , R 206 , R 206′ , R 207 , R 208 , R 208′ , R 209 , and R 210 are each independently H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E′ and/or interrupted by D′, alkoxy, or C 1 -C 18 alkoxy which is substituted by E′ and/or interrupted by D′, C 1 -C 18 fluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G′, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G′, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, C 7 -C 25 aralkyl which is substituted by G′; CN, or —CO—R 28 ,
D′ is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—,
E′ is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, CF 3 , or halogen,
G′ is E′, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by —O—,
R 28 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 63 and R 64 are each independently C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are each independently C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—; or
R 65 and R 66 together form a five or six membered ring,
R 67 is C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 68 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 69 is C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 70 and R 71 are each independently C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and
R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl.
2. The polymer according to claim 1 , wherein
R 1 and R 2 are each independently a group of formula
wherein R 400 , R 401 , R 402 , R 403 , R 404 and R 405 are each independently H, CN, F, CF 3 , C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—, or
R 1 and R 2 form together a group
3. The polymer according to claim 1 , wherein the polymer is a polymer of formula
or a polymer comprising repeating units of formulae
wherein
n is of 4 to 1000,
A is a repeating unit of the formula (I), or the formula (II), and
—COM 1 - is a repeating unit
wherein
k is 0, 1, 2, or 3; 1 is 1, 2, or 3; r is 0, 1, 2, or 3; z is 0, 1, 2, or 3;
Ar 4 , Ar 5 , Ar 6 and Ar 7 are each independently selected from the group consisting of the following formulae:
wherein X 1 is —O—, —S—, —NR 8 —, —Si(R 11 )(R 11′ )—, —Ge(R 11 )(R 11′ )—, —C(R 7 )(R 7′ )—, —C(═O)—, —C(═CR 104 R 104′ )—,
wherein X 1′ is S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 108 )(R 109 )—, —C(═O)—, —C(═CR 104 R 104′ )—,
R 3 and R 3′ are each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 104 and R 104′ are each independently hydrogen, cyano, COOR 103 , C 1 -C 25 alkyl, or C 6 -C 24 aryl or C 2 -C 20 heteroaryl,
R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 7 , R 7′ , R 9 and R 9′ are each independently hydrogen, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 8 and R 8′ are each independently hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; or C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 11 and R 11′ are each independently C 1 -C 25 alkyl, C 7 -C 25 arylalkyl, or a phenyl group, which is optionally substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 12 and R 12′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or
wherein R 13 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group; or
R 104 and R 104′ are each independently hydrogen, C 1 -C 18 alkyl, C 6 -C 10 aryl, which is optionally substituted by G, or C 2 -C 8 heteroaryl, which is optionally substituted by G,
R 105 , R 105′ , R 106 and R 106′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 18 alkoxy,
R 107 is hydrogen, C 7 -C 25 arylalkyl, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 perfluoroalkyl; C 1 -C 25 alkyl; which is optionally interrupted by —O—, or —S—; or —COOR 103 ;
R 108 and R 109 are each independently H, C 1 -C 25 alkyl, C 1 -C 25 alkyl which is substituted by E and/or interrupted by D, C 7 -C 25 arylalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
R 108 and R 109 together form a group of formula ═CR 110 R 111 , wherein
R 110 and R 111 are each independently H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 108 and R 109 together form a five or six membered ring, which is optionally substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl,
D is —CO—, —COO—, —S—, —O—, or —NR 112′ —,
E is C 1 -C 8 thioalkoxy, C 1 -C 8 alkoxy, CN, —NR 112′ R 113′ , —CONR 112′ R 113′ , or halogen,
G is E, or C 1 -C 18 alkyl, and
R 112′ and R 113′ are each independently H; C 6 -C 18 aryl; C 6 -C 18 aryl is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 115 and R 115′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or
wherein R 116 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group;
R 117 and R 117′ are each independently C 1 -C 25 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which is optionally substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 118 , R 119 , R 120 and R 121 each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 122 and R 122′ are each independently hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; or C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 201 is selected from the group consisting of hydrogen, a C 1 -C 100 alkyl group, —COOR 103 , a C 1 -C 100 alkyl group substituted by one or more halogen atoms, hydroxyl groups, nitro groups, —CN, or C 6 -C 18 aryl groups and/or interrupted by —O—, —COO—, —OCO— or —S—; a C 7 -C 25 arylalkyl group, a carbamoyl group, a C 5 -C 12 cycloalkyl group, which is optionally substituted one to three times with C 1 -C 100 alkyl and/or C 1 -C 100 alkoxy, a C 6 -C 24 aryl group, which is optionally substituted one to three times with C 1 -C 100 alkyl, C 1 -C 100 thioalkoxy, and/or C 1 -C 100 alkoxy; and pentafluorophenyl;
R 103 and R 114 are each independently C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms,
R 202 and R 203 are each independently selected from the group consisting of H, F, —CN, C 1 -C 100 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; and C 1 -C 100 alkoxy.
4. The polymer according to claim 1 , comprising at least one repeating unit of
wherein
A is a repeating unit of formula (I) or formula (II), and
—COM 1 - is a repeating unit of
wherein
R 3 , R 3′ , R 4 and R 4′ are each independently hydrogen or C 1 -C 25 alkyl;
R 8 and R 8′ are each independently hydrogen or C 1 -C 25 alkyl;
R 114 is a C 1 -C 38 alkyl group;
R 201 is a C 1 -C 38 alkyl group; and
R 202 and R 203 are each independently hydrogen or C 1 -C 25 alkyl.
5. The polymer according to claim 3 , wherein
A is a repeating unit of formula
wherein R 3 , R 3′ , R 4 and R 4′ are each independently hydrogen or C 1 -C 25 alkyl; and R 201 is a C 1 -C 38 alkyl group.
6. The polymer according to claim 4 , which is a polymer of formula
wherein
n is 4 to 1000,
R 3 , R 3′ , R 4 and R 4′ are each independently hydrogen or C 1 -C 25 alkyl; and
R 201 is a C 1 -C 38 alkyl group.
7. An organic semiconductor material, layer or component, comprising the polymer according to claim 1 .
8. An electronic device, comprising the polymer according to claim 1 .
9. The electronic device according to claim 8 , which is an organic light emitting diode, an organic photovoltaic device, a photodiode, or an organic field effect transistor.
10. The process for preparing an electronic device, the process comprising:
applying a solution and/or dispersion of the polymer according to claim 1 in an organic solvent to a suitable substrate, and
removing the solvent.
11. A polymer comprising a repeating unit of formula
wherein
A 1′ and A 2′ are each independently of formula
wherein a, b, and c are each independently 0, 1, 2, or 3,
Y, Y 15 , Y 16 and Y 17 are each independently
R 1 and R 2 are each independently H, F, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E′ and/or interrupted by D′, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G′, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G′, or
R 1 and R 2 form together a group
where
R 205 , R 206 , R 206′ , R 207 , R 208 , R 208′ , R 209 and R 210 are each independently H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E′ and/or interrupted by D′, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy which is substituted by E′ and/or interrupted by D′, C 1 -C 18 fluoroalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G′, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G′, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 7 -C 25 aralkyl, C 7 -C 25 aralkyl which is substituted by G′; CN, or —CO—R 28 ,
D′ is —CO—, —COO—, —S—, —SO—, —SO 2 —, —O—, —NR 65 —, —SiR 70 R 71 —, —POR 72 —, —CR 63 ═CR 64 —, or —C≡C—,
E′ is —OR 69 , —SR 69 , —NR 65 R 66 , —COR 68 , —COOR 67 , —CONR 65 R 66 , —CN, CF 3 , or halogen,
G′ is E′, C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by —O—,
R 28 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 63 and R 64 are each independently C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;
R 65 and R 66 are each independently C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—; or
R 65 and R 66 together form a five or six membered ring,
R 67 is C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 68 is H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 69 is C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 70 and R 71 are each independently C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and
R 72 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl;
p is 0 or 1;
q is 0 or 1;
A 1 and A 2 are each independently a group of formula
where a is 0, 1, 2, or 3; b is 0, 1, 2, or 3; c is 0, 1, 2, or 3; and R 10 is hydrogen, halogen, cyano, C 1 -C 25 alkyl, C 1 -C 25 alkyl which is substituted one or more times by E″ and/or interrupted one or more times by D″,
COO—C 1 -C 18 alkyl, C 4 -C 18 cycloalkyl group, C 4 -C 18 cycloalkyl group, which is substituted by G″, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 thioalkoxy, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E″ and/or interrupted by D″, C 7 -C 25 aralkyl, C 7 -C 25 aralkyl, which is substituted by G″, or a group of formulae IVa to IVm,
where
R 22 to R 26 and R 29 to R 58 each independently represent H, halogen, cyano, C 1 -C 25 alkyl, C 1 -C 25 alkyl which is substituted by E″ and/or interrupted by D″, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G″, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G″, a C 4 -C 18 cycloalkyl group, a C 4 -C 18 cycloalkyl group, which is substituted by G″, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E″ and/or interrupted by D″, C 7 -C 25 aralkyl, or C 7 -C 25 aralkyl, which is substituted by G″,
R 27 and R 28 are each independently hydrogen, C 1 -C 25 alkyl, halogen, cyano or C 7 -C 25 aralkyl, or R 27 and R 28 together represent alkylene or alkenylene which are optionally both bonded via oxygen and/or sulfur to the thienyl residue and which optionally both have up to 25 carbon atoms,
R 59 is hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; or C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
D″ is —CO—, —COO—, —S—, —O—, or —NR 112″ —,
E″ is C 1 -C 8 thioalkoxy, C 1 -C 8 alkoxy, CN, —NR 112″ R 113″ , —CONR 112″ R 113″ , or halogen,
G″ is E″, or C 1 -C 18 alkyl, and
R 112″ and R 113″ are each independently H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—;
R 214 and R 215 are each independently hydrogen, C 1 -C 18 alkyl, C 6 -C 24 aryl, C 2 -C 20 heteroaryl, —CN or COOR 216 ;
R 216 is C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, C 7 -C 25 arylalkyl, C 6 -C 24 aryl or C 2 -C 20 heteroaryl;
A 3 , A 4 , A 5 and A 5′ are each independently a group of formula -[Ar 4 ] k′ -[Ar 5 ] l -[Ar 6 ] r -[Ar 7 ] z -, where k′ is 0, 1, 2, or 3; 1 is 0, 1, 2, or 3; r is 0, 1, 2, or 3; and z is 0, 1, 2, or 3;
and
Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 are each independently selected from the group consisting of the following formulae:
where X 1 is —O—, —S—, —NR 8 —, —Si(R 11 )(R 11′ )—, —Ge(R 11 )(R 11′ )—, —C(R 7 )(R 7′ )—, —C(═O)—, —C(═CR 104 R 104′ )—,
where X 1′ is S, O, NR 107 —, —Si(R 117 )(R 117′ )—, —Ge(R 117 )(R 117′ )—, —C(R 108 )(R 109 )—, —C(═O)—, —C(═CR 104 R 104′ )—,
where
R 3 and R 3′ are each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 104 and R 104′ are each independently hydrogen, cyano, COOR 103 , C 1 -C 25 alkyl, or C 6 -C 24 aryl or C 2 -C 20 heteroaryl,
R 4 , R 4′ , R 5 , R 5′ , R 6 and R 6′ are each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 7 , R 7′ , R 9 and R 9′ are each independently hydrogen, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 1 -C 25 arylalkyl,
R 8 and R 8′ are each independently hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; or C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 11 and R 11″ are each independently C 1 -C 25 alkyl, C 7 -C 25 arylalkyl, or a phenyl group, which is optionally substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 12 and R 12′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 aryalkyl, or
wherein R 13 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group; or
R 104 and R 104′ are each independently hydrogen, C 1 -C 18 alkyl, C 6 -C 10 aryl, which is optionally substituted by G, or C 2 -C 8 heteroaryl, which is optionally substituted by G,
R 105 , R 105′ , R 106 and R 106′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1- C 18 alkoxy,
R 107 is hydrogen, C 7 -C 25 arylalkyl, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 perfluoroalkyl; C 1 -C 25 alkyl; which is optionally interrupted by —O—, or —S—; or —COOR 103 ;
R 108 and R 109 are each independently H, C 1 -C 25 alkyl, C 1 -C 25 alkyl which is substituted by E and/or interrupted by D, C 7 -C 25 arylalkyl, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl, or
R 108 and R 109 together form a group of formula ═CR 110 R 111 , wherein
R 110 and R 111 are each independently H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, or C 2 -C 20 heteroaryl, or C 2 -C 20 heteroaryl which is substituted by G, or
R 108 and R 109 together form a five or six membered ring, which is optionally substituted by C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E and/or interrupted by D, C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G, C 2 -C 20 heteroaryl, C 2 -C 20 heteroaryl which is substituted by G, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E and/or interrupted by D, or C 7 -C 25 aralkyl,
D is —CO—, —COO—, —S—, —O—, or —NR 112′ —,
E is C 1 -C 8 thioalkoxy, C 1 -C 8 alkoxy, CN, —NR 112′ R 113′ , —CONR 112′ R 113′ , or halogen,
G is E, or C 1 -C 18 alkyl, and
R 112′ and R 113′ are each independently H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by —O—,
R 115 and R 115′ are each independently hydrogen, halogen, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms, C 1 -C 25 alkoxy, C 7 -C 25 arylalkyl, or
wherein R 116 is a C 1 -C 10 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group;
R 117 and R 117′ are each independently C 1 -C 25 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which is optionally substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy;
R 118 , R 119 , R 120 and R 121 each independently hydrogen, halogen, halogenated C 1 -C 25 alkyl, cyano, C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; C 7 -C 25 arylalkyl, or C 1 -C 25 alkoxy;
R 122 and R 122′ are each independently hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; or C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
R 201 is selected from the group consisting of hydrogen, a C 1 -C 100 alkyl group, —COOR 103 , a C 1 -C 100 alkyl group substituted by one or more halogen atoms, hydroxyl groups, nitro groups, —CN, or C 6 -C 18 aryl groups and/or interrupted by —O—, —COO—, —OCO— or —S—; a C 7 -C 25 arylalkyl group, a carbamoyl group, a C 5 -C 12 cycloalkyl group, which is optionally substituted one to three times with C 1 -C 100 alkyl and/or C 1 -C 100 alkoxy, a C 6 -C 24 aryl group, which is optionally substituted one to three times with C 1 -C 100 alkyl, C 1 -C 100 thioalkoxy, and/or C 1 -C 100 alkoxy; and pentafluorophenyl;
R 103 and R 114 are each independently C 1 -C 25 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms,
R 202 and R 203 are each independently selected from the group consisting of H, F, —CN, C 1 -C 100 alkyl, which is optionally interrupted by one or more oxygen or sulphur atoms; and C 1 -C 100 alkoxy.