WO2012095796A1 - Organic photovoltaic device and manufacturing method thereof - Google Patents
Organic photovoltaic device and manufacturing method thereof Download PDFInfo
- Publication number
- WO2012095796A1 WO2012095796A1 PCT/IB2012/050132 IB2012050132W WO2012095796A1 WO 2012095796 A1 WO2012095796 A1 WO 2012095796A1 IB 2012050132 W IB2012050132 W IB 2012050132W WO 2012095796 A1 WO2012095796 A1 WO 2012095796A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- carbon atoms
- group
- phenyl
- formula
- Prior art date
Links
- 238000013086 organic photovoltaic Methods 0.000 title claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 163
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 78
- 239000003381 stabilizer Substances 0.000 claims abstract description 71
- 239000006096 absorbing agent Substances 0.000 claims abstract description 49
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 45
- 230000002225 anti-radical effect Effects 0.000 claims abstract description 41
- 230000015556 catabolic process Effects 0.000 claims abstract description 15
- 238000006731 degradation reaction Methods 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 211
- -1 cycloalkyl radical Chemical class 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 105
- 239000001257 hydrogen Substances 0.000 claims description 100
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 49
- 150000003254 radicals Chemical class 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- 230000007704 transition Effects 0.000 claims description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 238000009499 grossing Methods 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 22
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 18
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 11
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 claims description 7
- HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 6
- 238000007646 gravure printing Methods 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- RXELBMYKBFKHSM-UHFFFAOYSA-N 2-phenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC=N1 RXELBMYKBFKHSM-UHFFFAOYSA-N 0.000 claims description 4
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 238000007647 flexography Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 238000007756 gravure coating Methods 0.000 claims description 4
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 3
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- NQKXXZJNWGZAAQ-UHFFFAOYSA-N 4-[2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenoxy]hexan-2-ol Chemical compound CC(O)CC(CC)OC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 NQKXXZJNWGZAAQ-UHFFFAOYSA-N 0.000 claims description 3
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 238000001125 extrusion Methods 0.000 claims description 3
- 238000005227 gel permeation chromatography Methods 0.000 claims description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- UUINYPIVWRZHAG-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 UUINYPIVWRZHAG-UHFFFAOYSA-N 0.000 claims description 2
- OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 claims description 2
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 claims description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 claims description 2
- PXXWRCVMDNLZOS-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2-phenylpropan-2-yl)-6-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)CC(C)(C)C)=CC=1C(C)(C)C1=CC=CC=C1 PXXWRCVMDNLZOS-UHFFFAOYSA-N 0.000 claims description 2
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 claims description 2
- ITLDHFORLZTRJI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1N1N=C2C=CC=CC2=N1 ITLDHFORLZTRJI-UHFFFAOYSA-N 0.000 claims description 2
- UZUNCLSDTUBVCN-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C(O)C=1C(C)(C)C1=CC=CC=C1 UZUNCLSDTUBVCN-UHFFFAOYSA-N 0.000 claims description 2
- RTNVDKBRTXEWQE-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O RTNVDKBRTXEWQE-UHFFFAOYSA-N 0.000 claims description 2
- VQMHSKWEJGIXGA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-dodecyl-4-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O VQMHSKWEJGIXGA-UHFFFAOYSA-N 0.000 claims description 2
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 claims description 2
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 claims description 2
- DBYBHKQEHCYBQV-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-dodecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 DBYBHKQEHCYBQV-UHFFFAOYSA-N 0.000 claims description 2
- LSNNLZXIHSJCIE-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-tridecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 LSNNLZXIHSJCIE-UHFFFAOYSA-N 0.000 claims description 2
- WPMUMRCRKFBYIH-UHFFFAOYSA-N 2-[4,6-bis(2-hydroxy-4-octoxyphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=N1 WPMUMRCRKFBYIH-UHFFFAOYSA-N 0.000 claims description 2
- NPUPWUDXQCOMBF-UHFFFAOYSA-N 2-[4,6-bis(4-methylphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C=CC(C)=CC=2)=NC(C=2C=CC(C)=CC=2)=N1 NPUPWUDXQCOMBF-UHFFFAOYSA-N 0.000 claims description 2
- PIGBIZGGEUNVCV-UHFFFAOYSA-N 2-[4,6-bis[4-(3-butoxy-2-hydroxypropoxy)-2-hydroxyphenyl]-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=N1 PIGBIZGGEUNVCV-UHFFFAOYSA-N 0.000 claims description 2
- HHIVRACNDKRDTF-UHFFFAOYSA-N 2-[4-(2,4-dimethylphenyl)-6-(2-hydroxy-4-propoxyphenyl)-1,3,5-triazin-2-yl]-5-propoxyphenol Chemical compound OC1=CC(OCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(OCCC)=CC=2)O)=N1 HHIVRACNDKRDTF-UHFFFAOYSA-N 0.000 claims description 2
- PQJZHMCWDKOPQG-UHFFFAOYSA-N 2-anilino-2-oxoacetic acid Chemical class OC(=O)C(=O)NC1=CC=CC=C1 PQJZHMCWDKOPQG-UHFFFAOYSA-N 0.000 claims description 2
- LHHLLQVLJAUUDT-UHFFFAOYSA-N 2-ethylhexyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCC(CC)CCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O LHHLLQVLJAUUDT-UHFFFAOYSA-N 0.000 claims description 2
- AWEVLIFGIMIQHY-UHFFFAOYSA-N 2-ethylhexyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCC(CC)CCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O AWEVLIFGIMIQHY-UHFFFAOYSA-N 0.000 claims description 2
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 claims description 2
- BVNWQSXXRMNYKH-UHFFFAOYSA-N 4-phenyl-2h-benzotriazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NN=N2 BVNWQSXXRMNYKH-UHFFFAOYSA-N 0.000 claims description 2
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 claims description 2
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 claims description 2
- VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 claims description 2
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 claims description 2
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 claims description 2
- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229940068886 polyethylene glycol 300 Drugs 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 150000003235 pyrrolidines Chemical class 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- CBVFXTMAKVQDQY-UHFFFAOYSA-N octyl 4-[4,6-bis(3-ethoxy-2-hydroxy-4-octoxycarbonylphenyl)-1,3,5-triazin-2-yl]-2-ethoxy-3-hydroxybenzoate Chemical compound C(CCCCCCC)OC(=O)C1=C(C(=C(C=C1)C1=NC(=NC(=N1)C1=C(C(=C(C=C1)C(=O)OCCCCCCCC)OCC)O)C1=C(C(=C(C=C1)C(=O)OCCCCCCCC)OCC)O)O)OCC CBVFXTMAKVQDQY-UHFFFAOYSA-N 0.000 claims 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 1
- NEAHJFGPHPHWND-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C=1C(C)(C)C1=CC=CC=C1 NEAHJFGPHPHWND-UHFFFAOYSA-N 0.000 claims 1
- FESJNIGBEZWAIB-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(2-hydroxy-3-octoxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 FESJNIGBEZWAIB-UHFFFAOYSA-N 0.000 claims 1
- BZQCIHBFVOTXRU-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-butoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 BZQCIHBFVOTXRU-UHFFFAOYSA-N 0.000 claims 1
- CWVUGNSYIROMGD-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-6-[2-hydroxy-4-(2-hydroxyethoxy)phenyl]-1,3,5-triazin-2-yl]-5-(2-hydroxyethoxy)phenol Chemical compound OC1=CC(OCCO)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=NC(C=2C(=CC(OCCO)=CC=2)O)=N1 CWVUGNSYIROMGD-UHFFFAOYSA-N 0.000 claims 1
- DRXGKQPTFWTTJW-UHFFFAOYSA-N 5-butoxy-2-[4-(4-butoxy-2-hydroxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazin-2-yl]phenol Chemical compound OC1=CC(OCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCC)=CC=2)OCCCC)=N1 DRXGKQPTFWTTJW-UHFFFAOYSA-N 0.000 claims 1
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 claims 1
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 claims 1
- ZDOGYJHWBOXMHB-UHFFFAOYSA-N octyl 4-[4-(2,4-dihydroxyphenyl)-6-(3-ethoxy-2-hydroxy-4-octoxycarbonylphenyl)-1,3,5-triazin-2-yl]-2-ethoxy-3-hydroxybenzoate Chemical compound C(CCCCCCC)OC(=O)C1=C(C(=C(C=C1)C1=NC(=NC(=N1)C1=C(C(=C(C=C1)C(=O)OCCCCCCCC)OCC)O)C1=C(C=C(C=C1)O)O)O)OCC ZDOGYJHWBOXMHB-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 134
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002184 metal Substances 0.000 description 24
- 0 CC(C)(C)Cc(cc(*)cc1-[n]2nc(cccc3)c3n2)c1O Chemical compound CC(C)(C)Cc(cc(*)cc1-[n]2nc(cccc3)c3n2)c1O 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 14
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 229910003472 fullerene Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- AZSFNTBGCTUQFX-UHFFFAOYSA-N C12=C3C(C4=C5C=6C7=C8C9=C(C%10=6)C6=C%11C=%12C%13=C%14C%11=C9C9=C8C8=C%11C%15=C%16C=%17C(C=%18C%19=C4C7=C8C%15=%18)=C4C7=C8C%15=C%18C%20=C(C=%178)C%16=C8C%11=C9C%14=C8C%20=C%13C%18=C8C9=%12)=C%19C4=C2C7=C2C%15=C8C=4C2=C1C12C3=C5C%10=C3C6=C9C=4C32C1(CCCC(=O)OC)C1=CC=CC=C1 Chemical compound C12=C3C(C4=C5C=6C7=C8C9=C(C%10=6)C6=C%11C=%12C%13=C%14C%11=C9C9=C8C8=C%11C%15=C%16C=%17C(C=%18C%19=C4C7=C8C%15=%18)=C4C7=C8C%15=C%18C%20=C(C=%178)C%16=C8C%11=C9C%14=C8C%20=C%13C%18=C8C9=%12)=C%19C4=C2C7=C2C%15=C8C=4C2=C1C12C3=C5C%10=C3C6=C9C=4C32C1(CCCC(=O)OC)C1=CC=CC=C1 AZSFNTBGCTUQFX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000007539 photo-oxidation reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002041 carbon nanotube Substances 0.000 description 3
- 229910021393 carbon nanotube Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000010954 inorganic particle Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000002096 quantum dot Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229940044613 1-propanol Drugs 0.000 description 1
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
- VARDNKCBWBOEBW-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]phenol Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC=CC=2)O)=N1 VARDNKCBWBOEBW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
- GARHCDOTUULBOQ-PKNBQFBNSA-N 4-{(1e)-3-oxo-3-[(2-phenylethyl)amino]prop-1-en-1-yl}-1,2-phenylene diacetate Chemical compound C1=C(OC(C)=O)C(OC(=O)C)=CC=C1\C=C\C(=O)NCCC1=CC=CC=C1 GARHCDOTUULBOQ-PKNBQFBNSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BAMPVSWRQZNDQC-UHFFFAOYSA-N Cc1c(C)[s]c(C)n1 Chemical compound Cc1c(C)[s]c(C)n1 BAMPVSWRQZNDQC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- 238000006716 Hiyama reaction Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MXZNUGFCDVAXLG-CHWSQXEVSA-N [(2S)-1-[(2R)-3-methyl-2-(pyridine-4-carbonylamino)butanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@@H](NC(=O)c1ccncc1)C(=O)N1CCC[C@@H]1B(O)O MXZNUGFCDVAXLG-CHWSQXEVSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000002908 as-indacenyl group Chemical group C1(=CC=C2C=CC3=CC=CC3=C12)* 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- GOJOVSYIGHASEI-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)NC(C)(C)C1 GOJOVSYIGHASEI-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004623 carbolinyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000003790 chinazolinyl group Chemical group 0.000 description 1
- 125000003787 chinoxalinyl group Chemical group 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- CPELXLSAUQHCOX-DYCDLGHISA-N deuterium bromide Chemical compound [2H]Br CPELXLSAUQHCOX-DYCDLGHISA-N 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DVVDGSKDQGMLPW-UHFFFAOYSA-N ditert-butyl-(1-phenylpyrrol-2-yl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CN1C1=CC=CC=C1 DVVDGSKDQGMLPW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000006342 heptafluoro i-propyl group Chemical group FC(F)(F)C(F)(*)C(F)(F)F 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- HRHKULZDDYWVBE-UHFFFAOYSA-N indium;oxozinc;tin Chemical compound [In].[Sn].[Zn]=O HRHKULZDDYWVBE-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002891 organic anions Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007649 pad printing Methods 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229920006296 quaterpolymer Polymers 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to an organic photovoltaic (OPV) device comprising at least one photovoltaic layer, said layer comprising a mixture which comprises at least one
- DPP diketopyrrolopyrrole
- the stabilizing agent is preferably selected from the group consisting of a UV absorbing agent and an anti- radical agent; and further relates to the use of a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one DPP polymer for increasing the product life of an OPV device containing the mixture in at least one photovoltaic layer, or to the use of a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one DPP polymer for preventing the at least one DPP polymer from degradation during production of an OPV device containing the mixture in at least one photovoltaic layer.
- DPP diketopyrrolopyrrole
- OLED organic photovoltaic
- semiconductor layer as photovoltaic layer is the degradation of said layer due to, for example, the direct contact with oxygen and/or (sun)light (e.g. Neugebauer et al., Solar Energy Mat. & Solar Cells 61 [2000] 35).
- unsun unsun
- the conditions under which such protecting material are applied onto such organic semiconductor layer are often times very harsh, and there is a considerable risk to damage the organic semiconductor material during application of the protecting material and thus to loose at least partially the semiconducting properties of the organic material.
- DPP polymers exhibit excellent characteristics such as high efficiency in energy conversion, field effect mobility, good on/off current ratios, and stability. Moreover, these polymers have an excellent solubility in organic solvents and also excellent film-forming properties. Certain DPP polymers are described, for example, in WO 2008/000664 A1 , WO 2010/049321 A1 , or WO 2010/049323 A1 . In particular, WO 2008/000664 A1 discloses the use of DPP polymers in OPV devices; however, this document is silent on OPV devices comprising specific stabilizing agents to prevent the DPP polymers from degradation.
- a photovoltaic layer comprising or consisting of DPP polymer and a corresponding photovoltaic cell or device containing such a layer, surprisingly may be protected against degradation by radiation and/or oxidation in that at least one stabilizing agent is admixed to the photoactive layer comprising the DPP polymer while photoelectric activity is retained.
- a mixture of at least one stabilizing agent and at least one polymer can be used at least as component of a photovoltaic layer of an OPV device.
- the present invention relates to an organic photovoltaic (OPV) device comprising at least one photovoltaic layer, said layer comprising a mixture which comprises at least one diketopyrrolopyrrole (DPP) polymer and at least one stabilizing agent. Further, the present invention relates to a process for the production of an organic photovoltaic (OPV) device, said process comprising
- aa providing at least one diketopyrrolopyrrole (DPP) polymer, at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and preferably at least one electron acceptor material;
- DPP diketopyrrolopyrrole
- the present invention relates to the use of a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one diketopyrrolopyrrole (DPP) polymer for increasing the product life of an organic photovoltaic (OPV) device containing the mixture in at least one photovoltaic layer.
- at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent
- DPP diketopyrrolopyrrole
- the present invention relates to the use of a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one diketopyrrolopyrrole (DPP) polymer for preventing the at least one DPP polymer from degradation during production of an OPV device containing the mixture in at least one photovoltaic layer.
- at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent
- DPP diketopyrrolopyrrole
- the stabilizing agent is the stabilizing agent
- stabilizing agent has the meaning commonly known in the field of organic polymer technology and generally stands for an agent providing protection against degradation by irradiation and/or oxidation; see chapters “antioxidants” and “light stabilizers” in Plastics Additives Handbook, H. Zweifel (ed), 5 th edition, Hanser 2001 .
- the stabilizing agent itself generally has no conducting, semiconducting, photoelectric properties.
- the stabilizing agents often are classified as UV absorbers (i.e. UV absorbing agents) or anti-radical agents.
- UV absorbers generally possess a high extinction coefficient (usually higher than the one of the material to be protected) and are not degraded during their action since the absorbed radiation energy is transformed into heat.
- Anti-radical agents commonly are either radical-trapping agents (radical scavengers) or antioxidants.
- Antioxidants such as hindered phenols, mainly act as reducing agents (H-donors), which get oxidized themselves during their activity.
- Radical-trapping agents such as hindered amine light stabilizers (HALS) show further effects; alike UV absorbers, HALS generally retain their activity over several cycles.
- Conceivable stabilizing agents thus are, for example, UV absorbers and anti-radical agents such as hindered phenols or HALS.
- Hindered amines such as hindered amine light stabilizer (HALS), hindered nitroxyl compounds or hindered hydroxylamine compounds or salts thereof generally conform to the structures
- R is H or an organic residue such as alkyl or alkoxy (e.g. of 1 to 20 carbon atoms);
- A-i and A 2 are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene, Z-i and Z 2 are, for example, each methyl, or Z-i and Z 2 together form a linking moiety which may additionally be substituted by an ester, ether, hydroxy, oxo, cyanohydrin, amide, amino, carboxy or urethane group,
- h is the number of positive charges and j is the number of negative charges
- X is an inorganic or organic anion, and where the total charge of cations h is equal to the total charge of anions j.
- anti-radical agents are benzofuranone compounds, e.g. of the structure
- d is hydrogen; CrC 22 alkyl; CrC 22 alkylthio; C 2 -C 22 alkylthioalkyl; C 5 - C 7 cycloalkyl; phenyl; C 7 -C 9 phenylalkyl; or S0 3 M;
- G 2 is Ci-C 22 alkyl; C 5 -C 7 cycloalkyl; phenyl; or C 7 -C 9 phenylalkyl;
- G 4 and G 5 are each independently of the other hydrogen; or Ci-C 22 alkyl; and a is 0, 1 , or 2.
- Useful UV absorbing agents are, for example, suitable benzophenone derivatives like 2- hydroxybenzophenone derivatives, suitable benzotriazole derivatives like 2-hydroxyphenyl benzotriazole derivatives, or suitable hydroxyphenyltriazine derivatives like 2- hydroxyphenyltriazine derivatives.
- the stabilizing agent is selected from the group consisting of a UV absorbing agent and an anti-radical agent. More preferably, the anti-radical agent is a hindered phenol.
- the mixture comprising at least one diketopyrrolopyrrole (DPP) polymer and at least one stabilizing agent is free of a hindered amine light stabilizer (HALS), preferably free of a hindered amine, said mixture being comprised in the at least one photovoltaic layer comprised in the organic photovoltaic (OPV) device.
- UV absorbing agent is selected from the group consisting of a UV absorbing agent and an anti-radical agent. More preferably, the anti-radical agent is a hindered phenol.
- the mixture comprising at least one diketopyrrolopyrrole (DPP) polymer and at least one stabilizing agent is free of a hindered amine light stabilizer (HALS), preferably free of a hindered amine, said mixture being comprised in the at least one
- Preferred UV absorbing agents used according to the present invention are selected from the group consisting of hydroxybenzophenone derivatives, hydroxyphenyl benzotriazole derivatives, oxalic acid anilide derivatives, hydroxyphenyl triazine derivatives, and mixtures of two or more thereof. More preferably, the UV absorbing agents used according to the present invention are selected from the group consisting of hydroxybenzophenone derivatives, hydroxyphenyl benzotriazole derivatives, hydroxyphenyl triazine derivatives, and mixtures of two or more thereof.
- the UV absorbing agents used according to the present invention are selected from the group consisting of 2-hydroxybenzophenone derivatives, 2-hydroxyphenyl benzotriazole derivatives, 2- hydroxyphenyl triazine derivatives, and mixtures of two or more thereof.
- the present invention relates to above-described OPV device wherein the UV absorbing agent is
- a 2-hydroxyphenyltriazine is of formula
- v is an integer from 1 to 3 and w is 1 or 2 and the substituents Z independently of one another are hydrogen, halogen, hydroxyl or alkoxy having 1 to 12 carbon atoms; in the compounds of the formula (lla),
- Ri is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyi having 1 to 4 carbon atoms in the alkyl moiety, cycloalkyl having 5 to 8 carbon atoms or a radical of the formula
- R 4 and R 5 independently of one another are alkyl having in each case 1 to 5 carbon atoms, or R 4 , together with the radical C n H 2n+1-m , forms a cycloalkyl radical having 5 to 12 carbon atoms, m is 1 or 2, n is an integer from 2 to 20 and
- M is a radical of the formula -COOR 6 in which
- R 6 is hydrogen, alkyl having 1 to 12 carbon atoms, alkoxyalkyl having in each case 1 to 20 carbon atoms in the alkyl moiety and in the alkoxy moiety or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
- R 2 is hydrogen, halogen, alkyl having 1 to 18 carbon atoms, and phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and
- R 3 is hydrogen, chlorine, alkyl or alkoxy having in each case 1 to 4 carbon atoms or -COOR 6 in which R 6 is as defined above, at least one of the radicals Ri and R 2 being other than hydrogen; in the compounds of the formula (lib),
- T is hydrogen or alkyl having 1 to 6 carbon atoms
- T-i is hydrogen, chlorine or alkyl or alkoxy having in each case 1 to 4 carbon atoms, n is 1 or 2 and,
- T 2 is chlorine or a radical of the formula -OT 3 or — and
- T 5 if n is 2, T 2 is a radical of the formula 10 ⁇ or -0-T 9 -0-; in which
- T 3 is hydrogen, alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups or by -OCOT 6 , alkyl which has 3 to 18 carbon atoms, is interrupted once or several times by -O- or -NT 6 - and is unsubstituted or substituted by hydroxyl or -OCOT 6 , cycloalkyl which has 5 to 12 carbon atoms and is unsubstituted or substituted by hydroxyl and/or alkyl having 1 to 4 carbon atoms, alkenyl which has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula
- T 4 and T 5 independently of one another are hydrogen, alkyl having 1 to 18 carbon atoms, alkyl which has 3 to 18 carbon atoms and is interrupted once or several times by -O- or
- cycloalkyl having 5 to 12 carbon atoms phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 8 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety or hydroxyalkyl having 2 to 4 carbon atoms,
- T 6 is hydrogen, alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, alkenyl having 3 to 8 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
- T 7 is hydrogen, alkyl having 1 to 18 carbon atoms, phenyl which is unsubstituted or substituted by hydroxyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or -CH 2 OT 8 ,
- T 8 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 8 carbon atoms, cycloalkyi having 5 to 10 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
- T 9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, alkynylene having 4 carbon atoms, cyclohexylene, alkylene which has 2 to 8 carbon atoms and is interrupted once or several times by -0-, or a radical of the formula - CH 2 CH(OH)CH 2 OTiiOCH2CH(OH)CH2- or -CH 2 -C(CH 2 OH) 2 -CH 2 -,
- T-io is alkylene which has 2 to 20 carbon atoms and can be interrupted once or several times by -0-, or cyclohexylene,
- T-i-i is alkylene having 2 to 8 carbon atoms, alkylene which has 2 to 18 carbon atoms and is interrupted once or several times by -0-, 1 ,3-cyclohexylene, 1 ,4-cyclohexylene, 1 ,3-phenylene or 1 ,4-phenylene, or
- T-io and T 6 together with the two nitrogen atoms, are a piperazine ring; in the compounds of formula (lie),
- R' 2 is Ci-Ci 2 alkyl and k is a number from 1 to 4; in the compounds of the formula (III),
- u is 1 or 2 and r is an integer from 1 to 3, the substituents
- Y 2 is alkyl having 1 to 18 carbon atoms, phenyl which is unsubstituted or substituted by hydroxyl, halogen, alkyl or alkoxy having 1 to 18 carbon atoms;
- alkyl which has 1 to 12 carbon atoms and is substituted by -COOH, -COOY 8 , -CONH 2 , -
- CONHY 9 , -CONY 9 Y 10 , -NH 2 , -NHY 9 , -NY 9 Y 10 , -NHCOYn, -CN and/or -OCOYn;
- alkyl which has 4 to 20 carbon atoms, is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms, alkenyl having 3 to 6 carbon atoms, glycidyl, cyclohexyl which is unsubstituted or substituted by hydroxyl, alkyl having 1 to 4 carbon atoms and/or -OCOYn, phenylalkyl which has 1 to 5 carbon atoms in the alkyl moiety and is unsubstituted or substituted by hydroxyl, chlorine and/or methyl, -COYi 2 or - if u is 2,
- Y 2 is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylylene, alkylene which has 3 to 20 carbon atoms, is interrupted by one or more -O- atoms and/or is substituted by hydroxyl, -CH 2 CH(OH)CH 2 -0-Yi 5 -OCH 2 CH(OH)CH 2 , -CO-Yi 6 -CO-, -CO-NH-Y 17 - NH-CO- or -(CH 2 ) m -C0 2 -Yi 8 -OCO-(CH 2 ) m , in which m is 1 , 2 or 3,
- Y 8 is alkyi having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyi which has 3 to 20 carbon atoms, is interrupted by one or more oxygen or sulfur atoms or -NT 6 - and/or is substituted by hydroxyl, alkyi which has 1 to 4 carbon atoms and is substituted by -P(0)(OYi 4 ) 2 , -NYgY-io or -OCOY 11 and/or hydroxyl, alkenyl having 3 to 18 carbon atoms, glycidyl, or phenylalkyl having 1 to 5 carbon atoms in the alkyi moiety,
- Y 9 and Y 10 independently of one another are alkyi having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cyclohexyl having 5 to 12 carbon atoms, or Y 9 and Y 10 together are alkylene, oxaalkylene or azaalkylene having in each case 3 to 9 carbon atoms,
- Y 11 is alkyi having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl
- Y 12 is alkyi having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino
- Y-I3 is alkyi having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyi radical
- Yi 4 is alkyi having 1 to 12 carbon atoms or phenyl
- Y-I5 is alkylene having 2 to 10 carbon atoms, phenylene or a group -phenylene-M-phenylene- in which M is -0-, -S-, -S0 2 -, -CH 2 - or -C(CH 3 ) 2 -,
- Yi 6 is alkylene, oxaalkylene or thiaalkylene having in each case 2 to 10 carbon atoms, phenylene or alkenylene having 2 to 6 carbon atoms,
- Y-I7 is alkylene having 2 to 10 carbon atoms, phenylene or alkylphenylene having 1 to 1 1 carbon atoms in the alkyi moiety, and
- Y18 is alkylene having 2 to 10 carbon atoms or alkylene which has 4 to 20 carbon atoms and is interrupted once or several times by oxygen;
- x is an integer from 1 to 3 and the substituents L independently of one another are hydrogen, alkyi, alkoxy or alkylthio having in each case 1 to 22 carbon atoms, phenoxy or phenylthio.
- CrCi 8 alkyl may be linear or branched.
- alkyi having up to 18 carbon atoms are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1 -methylpentyl, 1 ,3-dimethylbutyl, n-hexyl, 1 -methylhexyl, n-heptyl, isoheptyl, 1 , 1 ,3,3- tetramethylbutyl, 1 -methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1 , 1 ,3-trimethylhexyl, 1 , 1 ,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1 -
- R-i can be hydrogen or alkyi having 1 to 24 carbon atoms, such as methyl, ethyl, propyl, butyl, hexyl, octyl, nonyl, dodecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl and eicosyl and also corresponding branched isomers.
- R-i can also be cycloalkyl having 5 to 8 carbon atoms, for example cyclopentyl, cyclohexyl and R 4
- cyclooctyl or a radical of the formula —
- M is a radical of the formula -COOR 6 in which R 6 is not only hydrogen but also alkyl having 1 to 12 carbon atoms or alkoxyalkyl having 1 to 20 carbon atoms in each of the alkyl and alkoxy moieties.
- Suitable alkyl radicals R 6 are those enumerated for R- ⁇ .
- suitable alkoxyalkyl groups are -C2H 4 OC 2 H5, -C2H 4 OC 8 H 17 and -C 4 H 8 OC 4 H 9 .
- R 6 is, for example, benzyl, cumyl, alpha-methylbenzyl or phenylbutyl.
- R 2 can also be alkyl having 1 to 18 carbon atoms. Examples of such alkyl radicals are indicated in the definitions of Ri .
- R 2 can also be phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, for example benzyl, alpha-methylbenzyl and cumyl.
- Halogen as a substituent means in all cases fluorine, chlorine, bromine or iodine, preferably chlorine or bromine and more preferably chlorine.
- At least one of the radicals Ri and R 2 must be other than hydrogen.
- R 3 is also alkyl or alkoxy having in each case 1 to 4 carbon atoms, for example methyl, butyl, methoxy and ethoxy, and also -COOR 6 .
- T is hydrogen or alkyl having 1 to 6 carbon atoms, such as methyl and butyl
- ⁇ is not only hydrogen or chlorine, but also alkyl or alkoxy having in each case 1 to 4 carbon atoms, for example methyl, methoxy and butoxy
- T 2 is chlorine or a radical of the formula -OT 3 or -NT 4 T 5
- T 3 is here hydrogen or alkyl having 1 to 18 carbon atoms (cf. the definition of R-i). These alkyl radicals can be substituted by 1 to 3 hydroxyl groups or by a radical -OCOT 6 .
- T 3 can be alkyl having 3 to 18 carbon atoms (cf.
- R-i which is interrupted once or several times by -O- or -NT 6 - and is unsubstituted or substituted by hydroxyl or -OCOT 6 .
- T 3 as cycloalkyl are cyclopentyl, cyclohexyl or cyclooctyl.
- T 3 can also be alkenyl having 2 to 18 carbon atoms. Suitable alkenyl radicals are derived from the alkyl radicals enumerated in the definitions of Ri . These alkenyl radicals can be substituted by hydroxyl.
- T 3 examples are benzyl, phenylethyl, cumyl, alpha- methylbenzyl or benzyl.
- T 3 can also be a radical of the formula -CH 2 CH(OH)-T 7 or
- T 4 and T 5 can, independently of one another, be not only hydrogen but also alkyl having 1 to 18 carbon atoms or alkyl which has 3 to 18 carbon atoms and is interrupted once or several times by -O- or -NT 6 -.
- T 4 and T 5 can also be cycloalkyl having 5 to 12 carbon atoms, for example cyclopentyl, cyclohexyl and cydooctyl.
- T 4 and T 5 as alkenyl groups can be found in the illustrations of T 3 .
- T 4 and T 5 as phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety are benzyl or phenylbutyl.
- substituents can also be
- hydroxyalkyl having 1 to 3 carbon atoms.
- T 2 is a divalent radical of the formula or -O-T9-O-.
- T 6 is alkyl, cycloalkyl, alkenyl, aryl or phenylalkyl; examples of such radicals have already been given above.
- T 7 can be phenyl or hydroxyphenyl and also -CH 2 OT 8 in which T 8 can be one of the alkyl, alkenyl, cycloalkyl, aryl or phenylalkyl radicals enumerated.
- the divalent radical T 9 can be alkylene having 2 to 8 carbon atoms, and such radicals can also be branched. This also applies to the alkenylene and alkynylene radicals T 9 . As well as cyclohexylene, T 9 can also be a radical of the formula -CH 2 CH(OH)CH20TiiOCH2CH(OH)CH 2 - or -CH 2 -C(CH 2 OH) 2 -CH 2 -.
- T-io is a divalent radical and, in addition to cyclohexylene, is also alkylene which has 2 to 20 carbon atoms and which can be interrupted once or several times by -0-.
- Suitable alkylene radicals are derived from the alkyl radicals mentioned in the definitions of Ri.
- T-i-i is also an alkylene radical. It contains 2 to 8 carbon atoms or, if it is interrupted once or several times by -0-, 4 to 10 carbon atoms.
- Tn is also 1 ,3-cyclohexylene, 1 ,4-cyclohexylene, 1 ,3-phenylene or 1 ,4-phenylene.
- T 6 and T 10 can also be a piperazine ring.
- alkyl, alkoxy, phenylalkyl, alkylene, alkenylene, alkoxyalkyl and cycloalkyl radicals and also alkylthio, oxaalkylene or azoalkylene radicals in the compounds of the formulae (I), (I la), (lib), (lie), (III) and IV) can be deduced from the above statements.
- the compounds of formulae (I la), (lib), and (lie) as well as (III) are preferred.
- those according to formula (I la) are in general preferred.
- the UV absorbers of the formulae (I), (I la), (lib), (lie), (III) and (IV) are known per se and are described, together with their preparation in, for example, WO 96/28431 A1 , EP 0 323 408 A1 , EP 0 057 160 A1 , US 5,736,597, EP 0 434 608 A1 , US 4,619,956, DE 31 35 810 A1 , GB 1 336 391 A.
- Preferred meanings of substituents and individual compounds can be deduced from the documents mentioned.
- the present invention relates to above- described device wherein the 2-hydroxybenzophenone is selected from group consisting of the 4-hydroxy, 4-methoxy, 4- octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, and 2'-hydroxy-4,4'-dimethoxy derivative of the hydroxybenzophenone;
- the 2-hydroxyphenylbenzotriazole is selected from the group consisting of 2-(2'-hydroxy-5'- methylphenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert- butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1 ,1 ,3,3-tetramethylbutyl)phenyl)benzo- triazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphen
- R 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2- ylphenyl, 2-[2'-hydroxy-3'-(alpha,alpha-dimethylbenzyl)-5'-(1 ,1 ,3,3-tetramethylbutyl)-phenyl]- benzotriazole; and 2-[2'-hydroxy-3'-(1 ,1 ,3,3-tetramethylbutyl)-5'-(alpha,alpha-dimethylbenzyl)- phenyl]benzotriazole;
- the 2-hydroxyphenyltriazine is selected from the group consisting of 2,4,6-tris(2-hydroxy-4- octyloxyphenyl)-1 ,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)- 1 ,3,
- a preferred 2-hydroxybenzophenone is the com ound of formula
- 2-hydroxyphenylbenzotriazole is the compound of formula
- An especially preferred 2-hydroxyphenyltriazine is the compound of formula
- UV absorbing agents are merocyanines such as disclosed in US- 201 1/200540 and further references cited therein; see especially sections [0015] - [0047], [0072] - [0078], [0079] - [0084], compounds of table 1 in section [0085], sections [0247] - [0256] (example A1 ), which passages of US-201 1/200540 are hereby incorporated by reference.
- merocyanines useful in the present invention include compounds of the formula V
- Qi and Q 2 independently of each other are hydrogen; CrC 2 2alkyl; C 2 -C 2 2 alkenyl, C 2 -C 2 2alkinyl, C 3 -Ci 2 cycloalkyl, C 3 -Ci 2 cycloalkenyl, C 7 -C 20 aralkyl, CrC 20 heteroalkyl, C 3 -Ci 2 cycloheteroalkyl, C 5 -Cnheteroaralkyl, C 6 -C 20 aryl, C4-C 9 heteroaryl, COQ1 3 or CONQ 13 Q 14 ;
- Q 3 is CN; -COOQ 5 ; -CONHQ 5 ; -COQ 5 ; -S0 2 Q 5 ; -CONQ 5 Q 6; C 6 -C 20 aryl; or C 4 -C 9 heteroaryl;
- Q 4 is CN; -COOQ 7 ; -CONHQ 7 ; -COQ 7 ; -S0 2 Q 7 ; -CONQ 7 Q 8 ; C C 22 alkyl; C 2 - C 22 alkenyl; C 2 -C 22 alkinyl; C 3 -Ci 2 cycloalkyl; C 3 -Ci 2 cycloalkenyl; C 7 -C 20 aralkyl; d- C 20 heteroalkyl; C 3 -Ci 2 cycloheteroalkyl; C 5 -Cn heteroaralkyl; C 6 -C 20 aryl; or C 4 -C 9 heteroaryl;
- Q 5 , ⁇ 3 ⁇ 4, Q 7 and Q 8 independently of each other are hydrogen; Ci-C 22 alkyl; C 2 -C 22 alkenyl; C 2 -C 22 alkinyl; C 3 -Ci 2 cycloalkyl; C 3 -Ci 2 cycloalkenyl; C 7 -C 20 aralkyl; CrC 20 heteroalkyl, C 3 -Ci 2 cycloheteroalkyl; C 5 -Cnheteroaralkyl; C 6 -C 20 aryl; C 4 -C 9 heteroaryl; S1Q15Q16Q17; Si(OQi 5 )(OQi6)(OQi 7 ); SiQi5(OQi6)(OQi 7 ); SiQi 5 Qi6(OQi 7 ); or a radical -XS;
- Li, L 2 or L 3 independently of each other are hydrogen, Ci-C 22 alkyl; C 2 -C 22 alkenyl, C 2 - C 22 alkinyl; C 3 -Ci 2 cycloalkyl; C 3 -Ci 2 cycloalkenyl; C 7 -C 20 aralkyl; CrC 20 heteroalkyl; C 3 - Ci 2 cycloheteroalkyl; C 5 -Cn heteroaralkyl; C 6 -C 20 aryl; C 4 -C 9 heteroaryl; CN; OH; OQ 9 ; or COOQ 9 ;
- Q 9 is hydrogen; Ci-C 22 alkyl; C 2 -C 22 alkenyl; C 2 -C 22 alkinyl; C 3 -Ci 2 cycloalkyl; C 3 - Ci 2 cycloalkenyl; C 7 -C 20 aralkyl; CrC 20 heteroalkyl; C 3 -Ci 2 cycloheteroalkyl; C 5 -Cnhetero- aralkyl; C 6 -C 20 aryl; or C 4 -C 9 heteroaryl;
- U and L 2 , U and L 3 , L 2 and L 3 , U and Q 4 , L 2 and Q 4 , U and Qi, L 2 and Qi, L 3 and Qi, L 3 and Q 5 , Q 3 and Q 4 , Qi and Q 2 , Q 7 and Q 8 , Q5 and Q 6 may be linked together to form 1 , 2, 3 or 4 carbocyclic or N, O and/or S-heterocyclic rings, which may be further fused with other aromatic rings;
- Q10 represents Q i3 ; COQ i3 ; COOQ i3 ; CONH 2 ; CONHQ 13 ; or CONQ 13 Q 14 ;
- On represents halogen; OH; NH 2 ; NHQ 15 ; NQ 15 Qi 6 ; NQ 15 OQi 6 ; 0-Q i5 ; 0-CO-Qi 5 ; S- Q i5 ; CO-Q15; oxo; thiono; CN; COOH; CONH 2 ; COOQi 5 ; CONHQ 15 ; CONQ 15 Qi 6 ; S0 2 NH 2 ; S0 2 NHQ 15 ; S0 2 NQ 15 Q 16 ; S0 2 Qi 5 ; S0 3 Qi 5 ; S1Q15Q16Q17; SiOQi 5 (OQi 6 )(OQi 7 );
- Q i2 represents halogen, CN, SH, OH, CHO, Q i8 ; OQ i8 ; SQi 8 ;
- Ci-C 22 alkyl C 3 -Ci 2 cycloalkyl
- Ci-Ci 2 alkenyl C 3 -Ci 2 cycloalkenyl
- Qi 3 , On, Qi5, Qi6, Qi7, Qi8, Qi9 and Q 20 independently of each other are Ci-C 22 alkyl; C 3 -Ci 2 cycloalkyl; C 2 -Ci 2 alkenyl; C 3 -Ci 2 cycloalkenyl; C 6 -Ci 4 aryl; C 4 -Ci 2 heteroaryl;
- Qi 3 and Q14, Q15 and Qi 6 , Q16 and Q17 and/or Q 18 and Qi 9 may be linked together to form unsubstituted or with d-C 4 alkyl substituted pyrrolidine, piperidine, piperazine or morpholine;
- X represents a linker
- S signifies a silane-, oligosiloxane- or polysiloxane-moiety
- n has a value of 0, 1 or 2
- o has a value of 3, 2 or 1 ; and m + o have a value of 3 or refers to groups of the general formula (1 a) ; or
- A represents a bond to the linker X
- s has a value of 4 to 250;
- t has a value of 5 to 250
- q has a value of 1 to 30;
- n 1 or integer
- n is from 1 to 6;
- Qi, Q 5 or Q 4 is a bivalent alkyl group; or Q-i and Q 2 together with the 2 nitrogen atoms linking them form a unsubstituted or alkyl-substituted
- v is from 1 to 4
- w is from 1 to 4;
- Preferred anti-radical agents used according to the present invention are hindered phenols. More preferably, an anti-radical agent used according to the present invention is a compound of formula (1 )
- Gi is hydrogen; CrC 22 alkyl; CrC 22 alkylthio; C 2 -C 22 alkylthioalkyl; C 5 -C 7 cycloalkyl; phenyl; C 7 -C 9 phenylalkyl; or S0 3 M;
- G 2 is Ci-C 22 alkyl; C 5 -C 7 cycloalkyl; phenyl; or C 7 -C 9 phenylalkyl;
- Q is -C m H 2m -; -CH- ; -C m H 2m -NH; a radical of formula
- T is -C n H 2n -; -(CH 2 ) n -0-CH 2 -; phenylene; -C n H 2n — NH— C— ; or a radical of
- V is -O-; or -NH-;
- a is 0; 1 ; or 2;
- d and g are each independently of one another 0; or 1 ;
- e is an integer from 1 to 4.
- f is an integer from 1 to 3;
- n and p are each independently of one another an integer from 1 to 3;
- G 3 is propyl substituted by OH and/or by C 2 -C 22 alkanoyloxy;
- M is alkali; ammonium; H;
- each of b and c independently is selected from 0 and 1 ;
- G 3 is the radical of formula (1 g) AA
- each of b and c independently is selected from 0 and 1 ;
- G 3 is — C— ;
- G 4 are each independently of the other hydrogen; or C1 -C22alkyl; or a compound of the formulae (16), (18), (20), (21 ), (22), (23)
- Preferred anti-radical agents include compounds listed in the following Table 1: Table 1 : Preferred anti-radical agents compound of
- An especially preferred compound is the compound of formula (23)
- DPP polymer used as component of the photovoltaic layer according to the present invention is concerned, no specific restrictions exist with the proviso that the DPP polymer is suitable for use as semiconductor material in an OPV device.
- DPP polymers are generally characterized in containing one or more DPP skeletons, as
- R 1 and R 2 are the same or different from each other and are selected from trhe group consisting of hydrogen; a C1-C100 alkyl group; -COOR 106 ; a C1-C100 alkyl group which is substituted by one or more halogen atoms, hydroxyl groups, nitro groups, -CN, or C 6 -Ci 8 aryl groups and/or interrupted by - 0-, -COO-, -OCO-, or -S-; a C7-C100 arylalkyl group; a carbamoyl group; a C5-C12 cycloalkyl group which can be substituted one to three times with a Ci-C 8 alkyl group and/or a Ci-C 8 alkoxy group; a C 6 -C 2 4 aryl group, in particular phenyl or 1 - or 2-naphthyl which can be substituted one to three times with
- DPP polymers and their synthesis are, for example, described in US6451459B1 , WO05/049695, WO2008/000664, WO2010/049321 , WO2010/049323, WO2010/108873, WO2010/1 15767, WO2010/136353, PCT/EP201 1/060283, WO2010/136352; and especially PCT/EP201 1/057878.
- the DPP polymer usually stands for a polymer comprising at least one diketo-pyrrolopyrrole repeating unit of the formula
- R 1 and R 2 independently are selected from hydrogen, a Ci-Ciooalkyl group, such as a C 6 - C 24 alkyl group; said alkyl group which is substituted by one or more halogen atoms, hydroxyl groups, nitro groups, -CN, C 6 -Ci 8 aryl groups and/or is interrupted by -0-, -COO-, -OCO-, or -S-; COO-CrC 5 oalkyl; a C 7 -Ci 0 oarylalkyl group; a carbamoyl group; C 5 -Ci 2 cycloalkyl which can be substituted one to three times with Ci-C 8 alkyl and/or Ci-C 8 alkoxy; C 6 -C2 4 aryl, in particular phenyl or 1 - or 2-naphthyl which can be substituted one to three times with CrC 8 alkyl, d- C 8 thioalkoxy, and/
- R b is hydrogen, CrCi 8 alkyl, or Ci-Ci 8 alkoxy, and R 32 is methyl, CI, or methoxy.
- R 1 and R 2 preferably are optionally branched C 8 -C 36 alkyl groups in the DPP polymers used according to the invention.
- Ar independently stands for a divalent residue selected from 2,5-thienylene and 2,5-furylene, each of which may be unsubstituted or bstituted by R 3 ', or for a divalent thiophene or thiazole moiety of the formula
- R 3 ' independently stands for halogen such as fluoro, or a CrC 25 alkyl group, C 7 -C 25 arylalkyl, or CrC 25 alkoxy, especially for a C 4 -C 25 alkyl group, which may optionally be interrupted by one or more oxygen or sulphur atoms;
- R 104 and R 104 independently are hydrogen or are as defined for R 3 ';
- R 116 is hydrogen, C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, Ci-Ci 8 perfluoroalkyl, or Ci-Ci 8 alkoxy; CrC 25 alkyl or COO-CrC 25 alkyl each of which is unsubstituted or substituted in its alkyl part by CN, halogen, C 6 -Ci 8 aryl, and/or, in case that its alkyl part comprises 2 or more carbon atoms, may be interrupted by -CO-, -COO-, -CONR 112 -, -0-, -NR 112 -, or -S-; where R 112 is H; C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, or Ci-Ci 8 alkoxy; CrCi 8 alkyl; or C 2 - Ci 8 alkyl which is interrupted
- DPP polymers for use in the present photovoltaic layers and for combination with the stabilizing agent in accordance with the present invention are those disclosed in the patent application No. PCT/EP201 1 /057878.
- the DPP polymer used according to the present invention includes a polymer comprising one or more (repeating) unit(s) of the formula
- Ar 23 is a group of formula or
- Ar 30 is a group of formula , or
- R 26 and R 26 are independently of each other a C 4 -Ci 8 alkyl group, especially a C 4 -Ci 8 alkyl group, A is a group of formula
- a is 0, or an integer of 1 , or 2
- b is 0, or an integer of 1 , or 2
- p is 0, or an integer of 1 , or 2
- y is 0, or 1 ,
- q is 0, or an integer of 1 , or 2, s is 0, or 1 ,
- u is an integer of 1 , or 2
- t is 0, or 1 ,
- v is an integer of 1 , or 2
- w is 0, or 1
- Ar 21 , Ar 21' , Ar 24 , Ar 24' , Ar 25 , Ar 27 , Ar 29 , Ar 31 , Ar 31' , Ar 38 , Ar 34 , Ar 36 , Ar 39 , Ar 1 and Ar 1' are
- Ar 3 and Ar 3 independently of each other have the meaning of Ar 1 , or are a group of formula
- Ar 2 , Ar 2' , Ar 26 , Ar 28 , Ar 33 , Ar 35 , Ar 37 , Ar 32 , Ar 32' , Ar 22 and Ar 22' are independently of each other a group of formula or x-— x 4 one of X 1 and X 2 is N and the other is CH,
- one of X 3 and X 4 is N and the other is CR 3 ,
- R 1 , R 2 , R 24 and R 25 may be the same or different and are selected from hydrogen, a Ci-Ciooalkyl group, especially a C 6 -C 24 alkyl group, a C 6 -C 24 aryl, in particular phenyl or 1 - or 2-naphthyl which can be substituted one to three times with CrC 8 alkyl, CrC 8 thioalkoxy, and/or CrC 8 alkoxy, or pentafluorophenyl,
- R 3 and R 3 are independently of each other a C C 25 alkyl group, especially a C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms, and B, D and E are independently of each other a group of formula
- I is 0, or 1 ,
- r 0, or 1 ,
- Ar 4 , Ar 5 , Ar 6 and Ar 7 are independently of each other a group of formula or wherein one of X 5 and X 6 is N and the other is CR
- c is an integer of 1 , 2, or 3,
- d is an integer of 1 , 2, or 3,
- Ar 8 and Ar 8 are independently of each other a group of formula
- R 1 and R 2 may be the same or different and are selected from hydrogen, a CrC 36 alkyl group, especially a C 6 -C 24 alkyl group, a C 6 -C 24 aryl, in particular phenyl or 1- or 2-naphthyl which can be substituted one to three times with CrC 8 alkyl, CrC 8 thioalkoxy, and/or CrC 8 alkoxy, or pentafluorophenyl,
- R 14 , R 14 , R 17 and R" are independently of each other H, or a C C 25 alkyl group, especially a C 6 C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms.
- the polymers of the present invention are preferably prepared (are obtainable) by (Suzuki) polymerisation of a dihalogenide, such as a dibromide or dichloride, especially a dibromide of formula Br A Br and Br B Br with an (equimolar) amount of a diboronic acid or
- X 11 is as defined below, is reacted with an (equimolar) amount of a dihalogenide, such as a dibromide or dichloride, especially a dibromide of formula Br D Br and optionally Br— E— Br .
- a dihalogenide such as a dibromide or dichloride, especially a dibromide of formula Br D Br and optionally Br— E— Br .
- the polymers of the present invention are copolymers.
- a copolymer is a polymer derived from more than one species of monomer, e.g. bipolymer, terpolymer, quaterpolymer, etc.
- the term polymer comprises oligomers as well as polymers.
- the oligomers of this invention have a weight average molecular weight of ⁇ 4,000 Daltons.
- the polymers of this invention preferably have a weight average molecular weight of 4,000 Daltons or greater, especially 4,000 to 2,000,000 Daltons, more preferably 10,000 to 1 ,000,000 and most preferably 10,000 to 100,000 Daltons.
- Molecular weights are determined according to high-temperature gel permeation chromatography (HT-GPC) using polystyrene standards.
- the polymers of this invention preferably have a polydispersibility of 1 .01 to 10, more preferably 1 .1 to 3.0, most preferred 1.5 to 2.5. Polymers are more preferred than oligomers.
- R 1 and R 2 can be hydrogen, but are preferably different from hydrogen.
- R 1 and R 2 can be different, but are preferably the same.
- R 1 and R 2 independently from each other stand for Ci-Ciooalkyl, C 5 -Ci 2 cycloalkyl, which can be substituted one to three times with CrC 8 alkyl and/or CrC 8 alkoxy, phenyl or 1 - or 2-naphthyl which can be substituted one to three times with C C 8 alkyl and/or C C 8 alkoxy, or -CR 301 R 302 -(CH 2 ) u -A 3 , wherein R 301 and R 302 stand for hydrogen, or CrC 4 alkyl, A 3 stands for phenyl or 1 - or 2-naphthyl, which can be substituted one to three times with Ci-C 8 alkyl and/or CrC 8 alkoxy, and u stands for 0, 1 , 2 or 3.
- R 1 and R 2 are more preferably a CrC 36 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert. -butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, 1 ,1 ,3,3- tetramethylpentyl, n-hexyl, 1 -methylhexyl, 1 ,1 ,3,3,5, 5-hexamethylhexyl, n-heptyl, isoheptyl,
- a CrC 36 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert. -butyl, n-pentyl, 2-pentyl, 3-
- R 1 and R 2 are a 2-hexyldecyl
- Chiral side chains, such as R 1 and R 2 can either be homochiral, or racemic, which can influence the morphology of the polymers.
- Ar 21 and Ar 21' , Ar 24 and Ar 24' , Ar 31 and Ar 31' , Ar 8 and Ar 8' , Ar 1 and Ar 1' can be the same and can be different, but are preferably the same.
- Ar 36 , Ar 39 , Ar 8 , Ar 8' , 1 and Ar 1' can be a group of formula s , or s , wherein a group of formula is preferred.
- Ar 3 and Ar 3 have preferably the meaning of Ar 1 .
- Ar 2 and Ar 2 , Ar 32 and Ar 32 , Ar 22 and Ar 22 can be the same and can be different, but are preferably , Ar 33 , Ar 35 , Ar 37 , Ar 32 , Ar 32' , Ar 22 and Ar 22' can be a group
- Ar 2 can be composed o can, for example, be a group of formula
- the group can be attached to the DPP basic unit, or arranged in the polymer chain
- R 24 and R 25 , R 1 and R 2 can be different, but are preferably the same.
- R 24 , R 25 , R 1 and R 2 can be linear, but are preferably branched.
- R 24 , R 25 , R 1 and R 2 are preferably a C 8 -C 36 alkyl group, especially a Ci 2 -C 2 4alkyl group, such as n-dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethyl-hexyl, 2-butyl-hexyl, 2-butyl-octyl, 2-hexyldecyl, 2-decyl-tetradecyl, heptadecyl, octadecyl, eicosyl, heneicosyl, docosyl, or tetracosyl.
- the C 8 -C 36 alkyl and Ci 2 -C 2 4alkyl group can be linear, or branched, but are preferably branched.
- R 24 , R 25 , R 1 and R 2 are a 2-hexyldecyl or 2-decyl-tetradecyl group.
- R 24 , R 25 , R 1 and R 2 can be represented by formula
- Chiral side chains such as R 24 , R 25 , R 1 and R 2 , can either be homochiral, or racemic, which can influence the morphology of the polymers.
- R 1 and R 2 may be the same or different and are selected from hydrogen, a CrC 36 alkyl group, especially a C 6 -C 24 alkyl group.
- R 3 and R 3 are independently of each other a CrC 25 alkyl group.
- R 3 and R 3 can be branched, but are preferably linear.
- R 3 and R 3 are especially a linear C 4 -C 25 alkyl group, very especially n- hexyl.
- groups R 15 and R 3 are present in a polymer of the presence invention, they are preferably identical. In addition, polymers are preferred, wherein at least 5 thiophenes are present between two DPP
- A is preferably a group of formula I, wherein Ar 3 and Ar 3 have the meaning of Ar 1 .
- A is preferably a group of formula
- B, D and E are independently of each other a group of formula N and the other is CR , or CH,
- R 15 , R 15 , R 17 and R 17 are independently of each other H, or a C C 25 alkyl group, especially a C 6 - C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms, and R 14 is a C C 25 alkyl group, especially a C 6 -C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms.
- B, D and E are more preferably a group of formula
- R 14 , R 15 , R 15' and R 17 are independently of each other a C 6 -C 25 alkyl.
- B, D and E are a group of formula they are preferably a group of
- the head to tail arrangement of R is important to introduce more solubility.
- B is preferably a group of formula
- X 1 , X 2 , R 1 and R 2 are as defined above.
- B is a group of formula la, lb, Ic, Id, le, If, Ig, or Ih, provided that B is different from A.
- R 1 and R 2 are a C 8 -C 35 alkyl group
- R 3 is a CrCi 8 alkyl group
- R is a C 4 -Ci 8 alkyl grou
- the polymers comprise repeating units
- A is a group of formula la, lb, lc, Id, le, If, Ig, or Ih,
- R 1 and R 2 are a C 8 -C 35 alkyl group
- R 3 is a C 4 -Ci 8 alkyl group
- B is a group of formula Va, lib, lie, lid, Me, llf, llg, llh, or Mi, or a group of formula la, lb, lc, Id, le, If, or Ig, with the proviso that B is different from A,
- R 1 and R 2 are a C 8 -C 35 alkyl group
- one of X 1 and X 2 is N and the other is CH,
- A is a group of formula I and B is a group of formula II x is preferably 0.2 to 0.8 and y is preferably 0.8 to 0.2. If A and B are both a group of formula II x is preferably 0.99 to 0.3 and y preferably 0.01 to 0.7.
- the DPP polymer is a polymer comprising repeating units of the formula
- R 1 and R 2 are a C 8 -C 35 alkyl group
- R 3 is a Ci-Ci 8 alkyl group
- R 15 is a C 4 -Ci 8 alkyl grou D is a group of formula and
- x 0.995 to 0.005
- y 0.005 to 0.995
- especially x 0.4 to 0.9
- y 0.6 to 0.1
- x + y 1 .
- R 1 and R 1" are a C 8 -C 38 alkyl group
- R 5 , R 15 , and R 3 are a C C 18 alkyl group, especially a C 4 -d 8 alkyl group, R 1 , is C 8 -C 36 alkyl,
- R 3 ' is Ci-Ci 8 alkyl, especially a C 4 -Ci 8 alkyl group, R 1 ⁇ R 1 ' and/or R 3 ⁇ R 3 ',
- x is 0.005 to 0.995, preferably 0.01 to 0.99
- y is 0.995 to 0.005, preferably 0.99 to 0.01.
- A is a group of formula (IV), wherein a' is an integer of 1 , or 2,
- b is an integer of 1 , or 2
- c is 0, or an integer of 1 , or 2
- d is 0, or an integer of 1 , or 2,
- e is 0, or an integer of 1 , or 2
- f is 0, or an integer of 1 , or 2
- R 1 and R 2 may be the same or different and are selected from hydrogen, a Ci-Ciooalkyl group, - COOR 203 , a C Ciooalkyl group which is substituted by one or more halogen atoms, hydroxyl groups, nitro groups, -CN, or C 6 -Ci 8 aryl groups and/or interrupted by -0-, -COO-, -OCO-, or -S-; a C 7 -Ciooarylalkyl group, a carbamoyl group, a C 5 -Ci 2 cycloalkyl group, which can be substituted one to three times with CrC 8 alkyl and/or CrC 8 alkoxy, a C 6 -C2 4 aryl group, in particular phenyl or 1 - or 2-naphthyl which can be substituted one to three times with CrC 8 alkyl, CrC 8 thioalkoxy, and/or Ci-C 8 alkoxy
- R 99 , R 104 and R 104 are independently of each other hydrogen, halogen, especially F, or a d- C 25 alkyl group, especially a C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C2 5 arylalkyl, or a CrC 25 alkoxy group,
- R 105 , R 105' , R 106 and R 106' are independently of each other hydrogen, halogen, Ci-C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; C 7 -C2 5 arylalkyl, or d- Ci 8 alkoxy,
- R 107 is C 7 -C2 5 arylalkyl, C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, d- Ci 8 perfluoroalkyl, or CrCi 8 alkoxy; CrC 25 alkyl; C C 25 alkyl which is interrupted by -O-, or -S-; or -COOR 119 ;
- R 116 is hydrogen, C 7 -C2 5 arylalkyl, C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, d- Ci 8 perfluoroalkyl, or CrCi 8 alkoxy; CrC 25 alkyl; C C 25 alkyl which is interrupted by -O-, or -S-; or -COOR 119 ;
- R 119 is CrC 25 alkyl, CrC 25 alkyl which is substituted by E' and/or interrupted by D',
- R 108 and R 109 together form a five or six membered ring, which optionally can be substituted by CrCi 8 alkyl, CrCi 8 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 2 oheteroaryl, C 2 -C 2 oheteroaryl which is substituted by G, C 2 - Ci 8 alkenyl, C 2 -Ci 8 alkynyl, CrCi 8 alkoxy, Ci-Ci 8 alkoxy which is substituted by E' and/or interrupted by D', or C 7 -C 25 aralkyl,
- D' is -CO-, -COO-, -S-, -0-, or -NR 112 -,
- E' is Ci-C 8 thioalkoxy, C C 8 alkoxy, CN, -NR 112 R 113 , -CONR 112 R 113 , or halogen,
- G is E', or Ci-Ci 8 alkyl
- R 112 and R 113 are independently of each other H; C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; Ci-Ci 8 alkyl; or Ci-Ci 8 alkyl which is interrupted by -0-,
- I is 0, or 1 ,
- r 0, or 1 ,
- z is 0, or 1 ,
- a is an integer of 1 to 5, especially 1 to 3,
- g is an integer of 1 , or 2
- h is an integer of 1 , or 2
- i 0, or an integer of 1 , or 2
- j is 0, or an integer of 1 , or 2
- k is 0, or an integer of 1 , or 2
- I is 0, or an integer of 1 , or 2
- R 1 and R 2 have independently of each other the meaning of R 1 ,
- Ar 8 , Ar 8' , Ar 9 , Ar 9' , Ar 10 and Ar 10 have independently of each other the meaning of Ar 2 ,
- Ar 4 , Ar 5 , Ar 6 and Ar 7 are independently of each other a group of formula
- Ar 20 is an arylene group, or a heteroarylene group, each of which may optionally be substituted, R 118 has the meaning of R 116 , R 12 and R 12 are independently of each other hydrogen, halogen, CrC 25 alkyl, especially C 4 - C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, d-
- R 13 is a Ci-Ci 0 alkyl group, or a tri(CrC 8 alkyl)silyl group,
- R 14 , R 14' , R 15 , R 15' , R 17 and R 17' are independently of each other H, or a Ci-C 25 alkyl group, especially a C 6 -C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms; R 18 and R 18 independently of each other hydrogen, halogen, d-C 25 alkyl, especially C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 -C 25 aralkyl, or CrC 25 alkoxy;
- R 19 is hydrogen, C 7 -C 25 aralkyl, C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, or d- Ci 8 alkoxy; or CrC 25 alkyl, especially C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms;
- R 20 and R 20 are independently of each other hydrogen, C 7 -C 25 aralkyl, CrC 25 alkyl, especially C 4 - C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms,
- R 100 and R 100 are independently of each other H, F, CrCi 8 alkyl, Ci-Ci 8 alkyl which is interrupted by O, Ci-Ci 8 alkoxy, Ci-Ci 8 alkoxy which is interrupted by O, Ci-Ci 8 perfluoroalkyl, C 6 -C 24 aryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or CrC 8 alkoxy, C 2 - C 20 heteroaryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or d- C 8 alkoxy;
- R 303 , R 304 , R 305 and R 306 are independently of each other H, F, C Ci 8 alkyl, C Ci 8 alkyl which is interrupted by O, Ci-Ci 8 alkoxy, Ci-Ci 8 alkoxy which is interrupted by O, Ci-Ci 8 perfluoroalkyl, C 6 - C 24 aryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or d- C 8 alkoxy, d-doheteroaryl, which may optionally be substituted one to three times with d- dalkyl and/or d-dalkoxy;
- R 307 and R 308 are independently of each other H, or d-dsalkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms;
- R 309 , R 310 , R 311 and R 312 are independently of each other H, d-dsalkoxy, or d-dsalkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms;
- R 101 and R 101 are independently of each other H, F, CrCi 8 alkyl, CrCi 8 alkyl which is interrupted by O, CrCi 8 alkoxy, CrCi 8 alkoxy which is interrupted by O, Ci-Ci 8 perfluoroalkyl, C 6 -C24aryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or CrC 8 alkoxy, C 2 - C 2 oheteroaryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or d- C 8 alkoxy;
- R 102 and R 102 are independently of each other H, halogen, CrC 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; C 7 -C2 5 arylalkyl, or CrC 25 alkoxy;
- R 103 and R 103 are independently of each other hydrogen, halogen, CrC 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; C6-C 24 aryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or Ci-C 8 alkoxy; C 7 -C 25 arylalkyl, CN, or CrC 25 alkoxy; or
- R 103 and R 103' together form a ring
- R 115 and R 115 are independently of each other hydrogen, C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by Ci-Ci 8 alkyl, or Ci-Ci 8 alkoxy; CrC 25 alkyl, especially C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; or C 7 -C 25 arylalkyl,
- R 117 and R 117 are independently of each other CrC 35 alkyl group, C 7 -C 25 arylalkyl, or a phenyl group, which optionally can be substituted one to three times with Ci-C 8 alkyl and/or Ci- Csalkoxy,
- R 120 and R 120 are independently of each other hydrogen, Ci-C 35 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms; or C 7 -C 25 arylalkyl,
- R 121 is H, CrCi 8 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, Ci-C-isperfluoroalkyl, C 6 -C 24 aryl, which may optionally be substituted one to three times with CrC 8 alkyl and/or CrC 8 alkoxy; C 2 -C 20 heteroaryl, which may optionally be substituted one to three times with Ci-C 8 alkyl and/or Ci-C 8 alkoxy; or CN,
- ⁇ represents the bond to the DPP skeleton. That is, the group 0 is most preferred.
- the polymer comprises (repeating) unit(s) of the formula ( ⁇ '), wherein A is a d D is a group of formula
- X 7 is preferably different from -S-, and -C(R 1 I 2 U 0) ⁇ (/R120')-.
- X' is preferably -0-, -NR -,
- X 7 is preferably -0-, -S-, -NR" 3 -, -C(R I U )(R )-, -
- DPP polymers wherein R 1 and R 2 are an optionally branched C 8 -C 36 alkyl group.
- the aryl moiety in direct vicinity to the DPP skeleton i.e. Ar, or Ar 1 and Ar 1 , in the above formulae
- Ar, or Ar 1 and Ar 1 are independently of each other .
- Ar, or Ar 1 and Ar 1 are independently of each other , wherein and s " are most preferred
- Ar groups such as Ar 1 and Ar 1 can be different, but are preferably the same.
- the present invention is directed to olymers, wherein Ar 1 and Ar 1
- X 3 is CH and X 4 is N, or X 3 is N and X 4 is CH, and R 116 is as defined above. R 116 is preferably different from H.
- A is preferably a group of formula
- R 1 and R 2 are independently of each other a CrC 36 alkyl group, especially a C 8 - C 36 alkyl group,
- R 104 is a C C 25 alkyl group, especially a C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, and
- R 116 is H, or CrC 25 alkyl; or C C 25 alkyl which is interrupted by -O-, or -S-.
- A is more preferably a group of formula IVa', IVc', IVe', IVg', IVh', IVi' and IVk'.
- Groups of formula IVa', IVc', IVe', IVg', IVh' and IVi' are especially preferred.
- B, D and E are independently of each other a group of formula
- R 120 and R 120 are as defined in claim 1 , a is an integer of 1 to 5, especially 1 to 3, one of X 1 and X 2 is N and the other is CH , one of X 5 and X 6 is N and the other is CR 1 20 is an arylene group, which may optionally be substituted, such as
- R 114 and R 114 are independently of each other hydrogen, or CrCi 8 alkyl,
- R 116 is H, or CrC 25 alkyl, R 117 is d-C 25 alkyl,
- R 12 and R 12 are independently of each other hydrogen, halogen, CrC 25 alkyl, especially C 4 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, C
- R 13 is a Ci-Ci 0 alkyl group, or a tri(C 1 -C 8 alkyl)silyl group,
- R 15 , R 15 , R 17 and R 17 are independently of each other H, or a CrC 25 alkyl group, especially a C 6 -C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms,
- R 14 is a CrC 25 alkyl group, especially a C 6 -C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms,
- R 18 and R 18 independently of each other hydrogen, halogen, CrC 25 alkyl, especially C 4 - C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, C 7 - C 25 aralkyl, or CrC 25 alkoxy;
- R 19 is hydrogen, C 7 -C 25 aralkyl, C 6 -Ci 8 aryl; C 6 -Ci 8 aryl which is substituted by CrCi 8 alkyl, or Ci-Ci 8 alkoxy; or CrC 25 alkyl, especially C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; and
- R 20 and R 20 are independently of each other hydrogen, C 7 -C 25 aralkyl, CrC 25 alkyl, especially C 4 -C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms.
- B, D and E are independently of each other a group of formula Va', Vb', Vc', Ve', Vf , Vh', Vi', Vj', Vk', VL', Vm', Vn', Vo', Vp', Vq', Vr', Vs', Vu', Vv', Vw', Vx', Vy, Vz.
- Groups of formula Va', Vc', Vf, Vh', Vi', Vk', Vo', Vp', Vq', Vr', Vs', Vu', Vw', Vx' and Va" are most preferred.
- groups of formula Vx' a group of formula Vx" is most preferred.
- the group of formula (Vb') is preferably a group of formula
- R 309 and R 310 are independently of each other CrC 25 alkoxy.
- the present invention is directed to polymers comprising (repeating) unit(s) of the formula I', especially la', or polymers of formula II', or III', wherein A is a group of
- R 309 and R 310 are independently of each other d-
- the group of formula (Vc') is preferably a group of formula
- the group of formula (Vd') is preferably a group of formula
- the present invention is directed to polymers, comprising repeating
- A is a group of formula IVa', IVc', IVe', IVg', IVh', IVi', IVj', or IVk',
- R 1 and R 2 are a C C 35 alkyl group, especially a C 8 -C 35 alkyl group,
- R 104 is a C C 25 alkyl group, especially a C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms, D is a gro
- polymers of the formula (la') are more preferred, wherein n is 4 (especially 10) to 1000, especially 4 to 200, very especially 5
- polymers where A is a group of formula IVa' and D is a roup of formula Vx', especially Vx", such as, for example, uch a polymer is a polymer of formula
- n is 4 (especially 10) to 1000, especially 4 to 200, very especially 5 (especially 20) to 100 and R 1 is a C C 35 alkyl group, especially a C 8 -C 35 alkyl group.
- Said polymers show high efficiency of energy conversion, when used in solar cells.
- the present invention is directed to polymers of formula I', especially of
- the DPP polymer is a polymer of structure
- x is 0.01 to 0.99, especially 0.8 to 0.4 and y is 0.99 to 0.01 , especially 0.2 to 0.6,
- R 1 is a C 8 -C 36 alkyl group, especially hexyl-decyl, and
- R 3 and R 15 are a CrCi 8 alkyl group, especially n-hexyl.
- the DPP polymer is a polymer of structure
- R 1 , R 2 , R 1' and R 2 are independently of each other a CrC 36 alkyl group, especially a C 8 - C 36 alkyl group,
- R 104 is a CrC 25 alkyl group, especially a C 4 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms
- R 15 , R 15 , R 17 and R 17 are independently of each other H, or a C C 25 alkyl group, especially a C 6 - C 25 alkyl, which may optionally be interrupted by one or more oxygen atoms,
- R 20 and R 20 are independently of each other hydrogen, C 7 -C 25 aralkyl, CrC 25 alkyl, especially C 4 - C 25 alkyl, which may optionally be interrupted by one, or more oxygen, or sulphur atoms, R 100 and R 100' are H,
- R 101 and R 101 are H, a CrC 25 alkyl group, or a CrC 25 alkoxy group,
- R 102 and R 102' are H, or a C C 25 alkyl group
- R 103 and R 103' are H, or a C C 25 alkyl group
- R 116 is H, or a C C 25 alkyl group
- R 120 and R 120 are a Ci-C 35 alkyl group
- n 4 to 1000, especially 4 to 200, very especially 5 to 100, and
- DPP copolymers can be obtained, for example, by the Suzuki reaction.
- the condensation reaction of an aromatic boronate and a halogenide, especially a bromide, commonly referred to as the "Suzuki reaction" is tolerant of the presence of a variety of organic functional groups as reported by N. Miyaura and A. Suzuki in Chemical Reviews, Vol. 95, pp. 457-2483 (1995).
- Preferred catalysts are 2-dicyclohexylphosphino-2',6'-di-alkoxybiphenyl/palladium(ll)acetates, tri-alykl-phosphonium salts/palladium (0) derivatives and tri-alkylphosphine/palladium (0) derivatives.
- Especially preferred catalysts are 2-dicyclohexylphosphino-2',6'-di-methoxybiphenyl (sPhos)/palladium(ll)acetate and, tri-tert-butylphosphonium tetrafluoroborate ((t-Bu) 3 P *
- a dihalogenide such as a dibromide or dichloride, especially a dibromide corresponding to formula Br A Br and Br B Br is reacted with an (equimolar) amount of a diboronic acid or diboronate corresponding to formula
- X is independently in each occurrence -B(OH) 2 , -B(OY ) 2 , is independently in each occurrence a CrCi 0 alkyl group and Y 2 is independently in each occurrence a C 2 -Ci 0 alkylene group, such as - CY 3 Y 4 -CY 5 Y 6 -, or -CY 7 Y 8 -CY 9 Y 10 - CY 11 Y 12 -, wherein Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 and Y 12 are independently of each other hydrogen, or a CrCi 0 alkyl group, especially -C(CH 3 ) 2 C(CH 3 ) 2 -, -CH 2 C(CH 3 ) 2 CH 2 -, or -C(CH 3 ) 2 CH 2 C(CH 3 ) 2 -, and Y 13 and Y 14
- the reaction is typically conducted at about 0 °C to 180 °C in an aromatic hydrocarbon solvent such as toluene, xylene.
- aromatic hydrocarbon solvent such as toluene, xylene.
- Other solvents such as dimethylformamide, dioxane, dimethoxyethan and tetrahydrofuran can also be used alone, or in mixtures with an aromatic hydrocarbon.
- An aqueous base preferably sodium carbonate or bicarbonate, potassium phosphate, potassium carbonate or bicarbonate is used as activation agent for the boronic acid, boronate and as the HBr scavenger.
- a polymerization reaction may take 0.2 to 100 hours.
- Organic bases such as, for example, tetraalkylammonium hydroxide, and phase transfer catalysts, such as, for example TBAB, can promote the activity of the boron (see, for example, Leadbeater & Marco; Angew. Chem. Int. Ed. Eng. 42 (2003) 1407 and references cited therein).
- phase transfer catalysts such as, for example TBAB
- Other variations of reaction conditions are given by T. I. Wallow and B. M. Novak in J. Org. Chem. 59 (1994) 5034-5037; and M. Remmers, M. Schulze, and G. Wegner in Macromol. Rapid Commun. 17 (1996) 239- 252. Controll of molecular weight is possible by using either an excess of dibromide, diboronic acid, or diboronate, or a chain terminator.
- a monofunctional aryl halide or aryl boronate may be used as a chain-terminator such reactions, which will result in the formation of a terminal aryl group.
- the polymers of the present invention can also be sythesized by the Stille coupling (see, for example, Babudri et al, J. Mater. Chem., 2004, 14, 1 1 -34; J. K. Stille, Angew. Chemie Int. Ed. Engl. 1986, 25, 508).
- a dihalogenide such as a dibromide or dichloride, especially a dibromide corresponding to formula and , wherein X is a group -
- the tin compounds and the halogen compounds are preferably introduced into one or more inert organic solvents and stirred at a temperature of from 0 to 200°C, preferably from 30 to 170°C for a period of from 1 hour to 200 hours, preferably from 5 hours to 150 hours.
- the crude product can be purified by methods known to the person skilled in the art and appropriate for the respective polymer, for example repeated re-precipitation or even by dialysis.
- Suitable organic solvents for the process described are, for example, ethers, for example diethyl ether, dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran, dioxane, dioxolane, diisopropyl ether and tert-butyl methyl ether, hydrocarbons, for example hexane, isohexane, heptane, cyclohexane, benzene, toluene and xylene, alcohols, for example methanol, ethanol, 1 -propanol, 2-propanol, ethylene glycol, 1-butanol, 2-butanol and tert-butanol, ketones, for example acetone, ethyl methyl ketone and isobutyl methyl ketone, amides, for example dimethylformamide (DMF), dimethylacetamide and N-methylpyrrolidone, nitriles, for
- the palladium and phosphine components should be selected analogously to the description for the Suzuki variant.
- the polymers of the present invention can also be synthesized by the Negishi reaction using zinc reagents A-(ZnX 22 ) 2 and B-(ZnX 22 ) 2 , wherein X 22 is halogen and halides, and D-(X 23 ) 2 , wherein X 23 is halogen or triflate, or using A-(X 22 ) 2 , B-(X 22 ) 2 , and D-(ZnX 23 ) 2 .
- A-(ZnX 22 ) 2 and B-(ZnX 22 ) 2 wherein X 22 is halogen and halides
- D-(X 23 ) 2 wherein X 23 is halogen or triflate
- the polymers of the present invention can also be synthesized by the Hiyama reaction using organosilicon reagents A-(SiR 210 R 211 R 212 ) 2 and B-(SiR 210 R 211 R 212 ) 2 , wherein R 210 , R 211 and R 212 are identical or different and are halogen, CrC 6 alkyl and D-(X 23 ) 2 , wherein X 23 is halogen or triflate, or using A-(X 22 ) 2 , B-(X 22 ) 2 , and D-(SiR 210 R 211 R 212 ) 2 .
- organosilicon reagents A-(SiR 210 R 211 R 212 ) 2 and B-(SiR 210 R 211 R 212 ) 2 , wherein R 210 , R 211 and R 212 are identical or different and are halogen, CrC 6 alkyl and D-(X 23 ) 2 , wherein X 23
- the polymers, wherein R 1 and/or R 2 are hydrogen can be obtained by using a protecting group which can be removed after polymerization (see, for example, EP-A-0 648 770, EP-A-0 648 817, EP-A-0 742 255, EP-A-0 761 772, WO98/32802, W098/45757, WO98/58027, WO99/0151 1 , WO00/17275, WO00/39221 , WO00/63297 and EP-A-1 086 984).
- Conversion of the pigment precursor into its pigmentary form is carried out by means of fragmentation under known conditions, for example thermally, optionally in the presence of an additional catalyst, for example the catalysts described in WO00/36210.
- L is preferably a group of formula
- Z 4 and Z 8 are independently of each other CrC 6 alkyl, CrC 6 alkyl interrupted by oxygen, sulfur or N(Z 12 ) 2 , or unsubstituted or CrC 6 alkyl-, CrC 6 alkoxy-, halo-, cyano- or nitro-substituted phenyl or biphenyl,
- Z 5 , Z 6 and Z 7 are independently of each other hydrogen or CrC 6 alkyl
- Z is hydrogen, d-C 6 alkyl or a group of formula or
- Z 10 and Z 11 are each independently of the other hydrogen, CrC 6 alkyl, CrC 6 alkoxy, halogen, cyano, nitro, N(Z 12 ) 2 , or unsubstituted or halo-, cyano-, nitro-, CrC 6 alkyl- or CrC 6 alkoxy- substituted phenyl,
- Z 12 and Z 13 are CrC 6 alkyl
- Z 14 is hydrogen or CrC 6 alkyl
- Z 15 is hydrogen, CrC 6 alkyl, or unsubstituted or CrC 6 alkyl-substituted phenyl
- Q is p,q-C 2 -C 6 alkylene unsubstituted or mono- or poly-substituted by CrC 6 alkoxy, CrC 6 alkylthio or C 2 -Ci 2 dialkylamino, wherein p and q are different position numbers,
- X is a hetero atom selected from the group consisting of nitrogen, oxygen and sulfur, m' being the number 0 when X is oxygen or sulfur and m being the number 1 when X is nitrogen, and L 1 and L 2 are independently of each other unsubstituted or mono- or poly-Ci-Ci 2 alkoxy-, -Ci-Ci 2 alkylthio-, -C 2 -C 24 dialkylamino-, -C 6 -Ci 2 aryloxy-, -C 6 -Ci 2 arylthio-, -C 7 -C 24 alkylarylamino- or -Ci2-C 24 diarylamino-substituted CrC 6 alkyl or [-(p',q'-C2-C 6 alkylene)-Z-] n '-Ci-C 6 alkyl , n' being a number from 1 to 1000, p' and q' being different position numbers, each Z
- C 2 -C 6 alkylene in the repeating [-C 2 -C 6 alkylene-Z-] units independently of any others being a hetero atom oxygen, sulfur or Ci-Ci 2 alkyl-substituted nitrogen, and it being possible for C 2 -C 6 alkylene in the repeating [-C 2 -C 6 alkylene-Z-] units to be the same or different,
- Most preferred L is a group of formula O CH
- Halogen is fluoro, chloro, bromo or iodo, preferably fluoro.
- CrC 25 alkyl (CrCi 8 alkyl) is typically linear or branched, where possible. Examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2- dimethylpropyl, 1 ,1 ,3,3-tetramethylpentyl, n-hexyl, 1 -methylhexyl, 1 ,1 ,3,3,5,5-hexamethylhexyl, n-heptyl, isoheptyl, 1 ,1 ,3,3-tetramethylbutyl, 1 -methylheptyl, 3-methylheptyl, n-octyl, 1 ,1 ,3,3- tetramethylbutyl and 2-ethylhexyl, n-non
- CrC 8 alkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethyl-propyl, n-hexyl, n-heptyl, n-octyl, 1 , 1 ,3,3- tetramethylbutyl and 2-ethylhexyl.
- CrC 4 alkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.
- C 2 -Ci 8 alkenyl groups are straight-chain or branched alkenyl groups, such as e.g. vinyl, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl.
- C 2- i 8 alkynyl is straight-chain or branched and preferably C 2 - 8 alkynyl, which may be unsubstituted or substituted, such as, for example, ethynyl, 1-propyn-3-yl, 1 -butyn-4-yl, 1 -pentyn-5-yl, 2-methyl-3-butyn-2-yl, 1 ,4-pentadiyn-3-yl, 1 ,3-pentadiyn-5-yl, 1 -hexyn-6-yl, cis-3-methyl-2- penten-4-yn-1 -yl, trans-3-methyl-2-penten-4-yn-1 -yl, 1 ,3-hexadiyn-5-yl, 1 -octyn-8-yl, 1 -nonyn-9- yl, 1 -decyn-10-yl, or 1 -tetracosyn-24-y
- CrC 25 alkoxy groups are straight-chain or branched alkoxy groups, e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy.
- CrC 8 alkoxy examples are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, 2-pentoxy, 3-pentoxy, 2,2-dimethylpropoxy, n-hexoxy, n-heptoxy, n- octoxy, 1 ,1 ,3,3-tetramethylbutoxy and 2-ethylhexoxy, preferably CrC 4 alkoxy such as typically methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy.
- alkylthio group means the same groups as the alkoxy groups, except that the oxygen atom of the ether linkage is replaced by a sulfur atom.
- d-Cisperfluoroalkyl especially Ci-C 4 perfluoroalkyl, is a branched or unbranched radical such as for example -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3, -CF(CF 3 ) 2, -(CF 2 ) 3 CF 3 , and -C(CF 3 ) 3 .
- carbamoyl group is typically a Ci-i 8 carbamoyl radical, preferably Ci -8 carbamoyl radical, which may be unsubstituted or substituted, such as, for example, carbamoyl, methylcarbamoyl, ethylcarbamoyl, n-butylcarbamoyl, tert-butylcarbamoyl,
- C 5 -Ci 2 cycloalkyl is typically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, preferably cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, which may be unsubstituted or substituted.
- the cycloalkyl group in particular a cyclohexyl group, can be condensed one or two times by phenyl which can be substituted one to three times with CrC 4 -alkyl, halogen and cyano. Examples of such condensed
- R 156 are independently of each other CrC 8 -alkyl, CrC 8 -alkoxy, halogen and cyano, in particular hydrogen.
- C 6 -C 24 aryl (C 6 -Ci 8 aryl) is typically phenyl, indenyl, azulenyl, naphthyl, biphenyl, as-indacenyl, s- indacenyl, acenaphthylenyl, fluorenyl, phenanthryl, fluoranthenyl, triphenlenyl, chrysenyl, naphthacen, picenyl, perylenyl, pentaphenyl, hexacenyl, pyrenyl, or anthracenyl, preferably phenyl, 1 -naphthyl, 2-naphthyl, 4-biphenyl, 9-phenanthryl, 2- or 9-fluorenyl, 3- or 4-biphenyl, which may be unsubstituted or substituted.
- Examples of C 6 -Ci 2 aryl are phen
- C 7 -C 25 aralkyl is typically benzyl, 2-benzyl-2-propyl, ⁇ -phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, co-phenyl-butyl, ⁇ , ⁇ -dimethyl-co-phenyl-butyl, co-phenyl-dodecyl, co-phenyl-octadecyl, co-phenyl- eicosyl or co-phenyl-docosyl, preferably C 7 -Ci 8 aralkyl such as benzyl, 2-benzyl-2-propyl, ⁇ - phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ , ⁇ -dimethyl-co-phenyl-butyl, co-phenyl- dodecyl or co-phenyl-octadecyl, and particularly preferred C 7 -Ci
- Heteroaryl is typically C 2 -C 20 heteroaryl, i.e. a ring with five to seven ring atoms or a condensed ring system, wherein nitrogen, oxygen or sulfur are the possible hetero atoms, and is typically an unsaturated heterocyclic group with five to 30 atoms having at least six conjugated ⁇ -electrons such as thienyl, benzo[b]thienyl, dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl, 2H- pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, phenoxythienyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl
- Possible substituents of the above-mentioned groups are CrC 8 alkyl, a hydroxyl group, a mercapto group, CrC 8 alkoxy, CrC 8 alkylthio, halogen, halo-CrC 8 alkyl, a cyano group, a carbamoyl group, a nitro group or a silyl group, especially Ci-C 8 alkyl, Ci-C 8 alkoxy, d- C 8 alkylthio, halogen, halo-Ci-C 8 alkyl, or a cyano group.
- CrCi 8 alkyl interrupted by one or more O is, for example, (CH2CH 2 0)i-9-R x , where R x is H or d- Ci 0 alkyl, CH2-CH(OR y ')-CH 2 -0-R y , where R y is C Ci 8 alkyl, and R y ' embraces the same definitions as R y or is H.
- a substituent such as, for example R 18 , occurs more than one time in a group, it can be different in each occurrence.
- substituted by G means that one, or more, especially one to three substituents G might be present.
- the aforementioned groups may be substituted by E' and/or, if desired, interrupted by D'. Interruptions are of course possible only in the case of groups containing at least 2 carbon atoms connected to one another by single bonds; C 6 -Ci 8 aryl is not interrupted; interrupted arylalkyl contains the unit D' in the alkyl moiety.
- Ci-Ci 8 alkyl substituted by one or more E' and/or interrupted by one or more units D' is, for example, (CH2CH 2 0)i-9-R x , where R x is H or d-Cioalkyl or C 2 -Ci 0 alkanoyl (e.g.
- a mixture containing a polymer of the present invention results in a semi-conducting layer comprising a polymer of the present invention (typically 5% to 99.9999% by weight, especially 20 to 85 % by weight) and at least another material.
- the other material can be, but is not restricted to a fraction of the same polymer of the present invention with different molecular weight, another polymer of the present invention, a semi-conducting polymer, organic small molecules, carbon nanotubes, a fullerene derivative, inorganic particles (quantum dots, quantum rods, quantum tripods, Ti0 2 , ZnO etc.), conductive particles (Au, Ag etc.), insulator materials like the ones described for the gate dielectric (PET, PS etc.).
- the present DPP polymers can be blended with small molecules described, for example, in European patent application no. 09155919.5, WO09/047104, US-6690029, WO2007082584, WO2008107089.
- the photovoltaic layer of the present OPV device comprises a mixture which comprises the at least one diketopyrrolopyrrole (DPP) polymer and the at least one stabilizing agent.
- DPP diketopyrrolopyrrole
- said mixture may comprise one or more of above- described DPP polymers and one or more of above-described stabilizing agents.
- the mixture may comprise one or more DPP polymers and one or more UV absorbing agents and no anti-radical agent.
- the mixture may comprise one or more DPP polymers and no UV absorbing agent and one or more anti-radical agents.
- the mixture may comprise one or more DPP polymers and one or more UV absorbing agent and one or more anti-radical agents.
- the mixture comprises one or more DPP polymers, more preferably one DPP polymer, more preferably one DPP polymer of structure (VII), even more preferably of a structure
- UV absorbing agent and one or more anti-radical agents preferably one anti-radical agent, more preferably one hindered phenol, more preferably one hindered phenol of structure (23)
- the mixture comprises one or more DPP polymers, more preferably one DPP polymer, more preferably one DPP polymer of structure (VII), even more preferably of structure (Vllb) or (lc")
- UV absorbing agents preferably one UV absorbing agent, more preferably a UV absorbing agent of formula (lla), (lib), (lie) or (III), as described above, more preferably a UV absorbing agent of formula (lla), and no anti-radical agents.
- UV absorbing agents are compounds of structures
- the mixture comprising the at least one DPP polymer and the at least one stabilizing agent, the weight ratio of stabilizing agent relative to the DPP polymer is in the range of from 0.0005:1 to 0.1 :1 to, preferably from 0.001 :1 to less than 0.05:1 , more preferably from 0.005:1 to 0.025:1 .
- the term "stabilizing agent” relates to the sum of all stabilizing agents contained in the mixture
- the "DPP polymer” relates to the sum of all DPP polymers contained in the mixture.
- the stabilizing agent selected from hindered phenols and/or HALS is contained in the mixture in a weight ratio stabilizing agent : DPP polymer ranging from
- 0.0001 :1 to 0.01 :1 preferably from 0.0005:1 to 0.005:1 , more preferably from 0.0005:1 to 0.002:1 .
- the stabilizing agent selected from UV absorbers is contained in the mixture in a weight ratio stabilizing agent : DPP polymer ranging from 0.0005:1 to 0.1 :1 , preferably from 0.001 :1 to less than 0.1 :1.
- the photovoltaic layer of the present invention comprising the inventive mixture of at least one DPP polymer and at least one stabilizing agent contains the DPP polymer usually as electron donor.
- the photovoltaic layer of the present invention comprising the mixture of the present invention comprising the at least one DPP polymer and the at least one stabilizing agent additionally comprises at least one suitable electron acceptor material.
- suitable electron acceptor material there are no specific restrictions as far as the chemical nature of the at least one suitable electron acceptor material is concerned.
- the acceptor material can be a material selected from the group consisting of a suitable organic polymer such as a suitable DPP polymer or a suitable semiconducting polymer provided that the polymers retain acceptor- type and electron mobility characteristics, suitable organic small molecule, carbon nanotubes, inorganic particles such as quantum dots, quantum rods, quantum tripods, Ti0 2 , ZnO and the like.
- a fullerene in particular a suitably modified such a suitably functionalized fullerene is employed as an electron acceptor.
- Fullerenes useful in this invention may have a broad range of sizes (number of carbon atoms per molecule).
- fullerene as used herein includes various cage-like molecules of pure carbon, including Buckminsterfullerene (C60) and the related "spherical" fullerenes as well as carbon nanotubes.
- Fullerenes may be selected from those known in the art ranging from, for example, C20-C1000-
- the fullerene is selected from the range of C60 to C96.
- the compound [70]PCBM has the following structure:
- the present invention also relates to above-described device wherein the electron acceptor material is an optionally suitably modified fullerene, preferably having from 60 to 96 carbon atoms.
- the weight ratio of the electron acceptor material relative to the DPP polymer is in the range of from 0.1 :1 to 10:1 , preferably from 0.5:1 to 3:1 , more preferably from 0.8:1 to 2:1.
- the term "electron acceptor material” relates to the sum of all electron acceptor materials contained in the mixture
- the "DPP polymer” relates to the sum of all DPP polymers contained in the mixture.
- the photovoltaic layer consists of the inventive mixture comprising the at least one DPP polymer and the at least one stabilizing agent, and optionally the at least one electron acceptor material.
- the photovoltaic layer consists of the inventive mixture which consists of the at least one DPP polymer and the at least one stabilizing agent, and optionally the at least one electron acceptor material.
- OLED device The Organic Photovoltaic Device
- an OPV device of the present invention comprising the inventive mixture generally can be designed according to the respective needs.
- an OPV device of the present invention comprises, most preferably in this order,
- the photovoltaic layer (c) is the photovoltaic layer of the present invention which comprises the at least one DPP polymer and the at least one stabilizing agent according to the present invention.
- the electrodes, the cathode (a) and the anode (j), are preferably composed of metals or metal substitutes.
- metal includes both materials composed of an elementally pure metal, for example Mg, and also metal alloys which are materials composed of two or more elementally pure metals, for example Mg and Ag together, denoted Mg:Ag.
- metal substitute refers to a material that is not a metal within the normal definition, but which has the metal-like properties that are desired in the present OPV device application.
- metal substitutes for electrodes and charge transfer layers would include doped wide-bandgap semiconductors, for example, transparent conducting oxides such as indium tin oxide (ITO), gallium indium tin oxide (GITO), and zinc indium tin oxide (ZITO).
- ITO indium tin oxide
- GITO gallium indium tin oxide
- ZITO zinc indium tin oxide
- Another suitable metal substitute is the transparent conductive polymer polyanaline (PANI) and its chemical relatives, or PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate)).
- Metal substitutes may be further selected from a wide range of non-metallic materials, wherein the term "non- metallic" as used in this context of the present invention includes a wide range of materials provided that the material is free of metal in its chemically uncombined form.
- Highly transparent, non-metallic, low resistance cathodes or highly efficient, low resistance metallic/non-metallic compound cathodes are, for example, disclosed in US 6,420,031 B1 and US 5,703,436 B1.
- the substrate can be, for example, a plastic (flexible substrate), or glass substrate.
- a smoothing layer is located between the anode and the photovoltaic layer.
- a preferred material for this smoothing layer comprises a film of 3,4- polyethylenedioxythiophene (PEDOT), or PEDOT:PSS).
- the OPV device of the present invention can also be processed on a fiber as described, for example, in US 20070079867 A1 and US 20060013549 A1.
- the OPV device comprises, as described for example, in US 6,933,436 B1 , a transparent glass carrier as substrate (k), onto which an electrode layer made of indium/tin oxide (ITO) is applied as anode (j).
- This electrode layer generally has a comparatively rough surface structure, so that it is covered with a smoothing layer (d) made of a suitable polymer, typically PEDOT, which is made electrically conductive through suitable doping.
- the photovoltaic layer (c) has a layer thickness of, for example, 100 nm to a few micrometers depending on the specific OPV device design, and is applied onto the smoothing layer (d).
- the photovoltaic layer is made of the mixture comprising the at least one DPP polymer and the at least one stabilizing agent, the DPP polymer preferably acting as an electron donor, and a suitable electron acceptor material, preferably a fullerene, more preferably a functionalized fullerene PCBM.
- a preferably thin transition layer is optionally applied, which must be electrically insulating, and has, for example, a layer thickness of 0.6 nm.
- this transition layer is made of an alkali halogenide, more preferably lithium fluoride. If, for example, ITO is used as a hole-collecting electrode, aluminum, which is preferably vapor deposited onto the electrically insulating transition layer (d), is used as an electron-collecting electrode.
- the electric insulation properties of the transition layer obviously prevent influences which hinder the crossing of the charge carrier from being effective, particularly in the transition region from the photovoltaic layer to the transition layer.
- the OPV device of the present invention can also consist of multiple junction solar cells that are processed on top of each other in order to absorb more of the solar spectrum.
- Such structures are, for example, described in App. Phys. Let. 90, 143512 (2007), Adv. Funct. Mater. 16, 1897- 1903 (2006), and WO 2004/1 12161 .
- the present invention also relates to above-described OPV device, wherein the transition layer (b) is an alkali halogenide, preferably lithium fluoride; the cathode (a) is a metal or a metal substitute; the anode (j) is a metal or a metal substitute; and the substrate (k) is a plastic or glass substrate.
- the transition layer (b) is an alkali halogenide, preferably lithium fluoride
- the cathode (a) is a metal or a metal substitute
- the anode (j) is a metal or a metal substitute
- the substrate (k) is a plastic or glass substrate.
- the device in addition to the layers described above, further comprises
- the OPV device comprises, in this order,
- the middle electrode (e) comprises, preferably consists of a metal or a metal substitute, preferably of a metal such as Au or Al, or other suitable materials such as ZnO, Ti oxides such as ⁇ 02, or the like.
- the optional further electrode (f) comprises, preferably consists of a metal or a metal substitute.
- the optionally transition layer (g) reference is made to the description of the transition layer (b) hereinabove wherein the transition layer (g) may be comprised of the same material(s) as the transition layer (b), or may be different from the transition layer (b).
- the present invention also relates to above-described OPV device, wherein the middle electrode (e) is a metal or a metal substitute; the further electrode (f) is a metal or a metal substitute; the transition layer (g) is an alkali halogenide, preferably lithium fluoride.
- the present invention relates to such process for the production of an organic photovoltaic (OPV) device as described above, said process comprising
- aa providing at least one diketopyrrolopyrrole (DPP) polymer, at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and preferably at least one electron acceptor material;
- DPP diketopyrrolopyrrole
- Step (dd) According to (cc), the two, preferably the three components are mixed with at least one suitable solvent and applied, according to (dd), as a solution onto the anode, optionally onto the smoothing layer applied onto the anode, by a suitable method.
- application according to (dd) is carried out via either at least one suitable coating technique and/or at least one suitable printing technique. Therefore, the present invention also relates to above-described process, wherein applying in (dd) is performed via coating and/or printing, preferably coating or printing.
- Suitable coating techniques which can be used according to the present invention are, for example, spin-coating, slot-die coating (also called as extrusion coating), curtain coating, reverse gravure coating, blade coating, spray coating, and dip coating.
- Preferred coating techniques are, for example, slot-die (extrusion) coating or reverse gravure coating.
- Suitable printing techniques which can be used according to the present invention are, for example, inkjet printing, flexography printing, (forward) gravure printing, screen printing, pad printing, offset printing, and reverse offset printing.
- Preferred printing techniques are, for example, flexography printing or (forward) gravure printing.
- the present invention also relates to above-described process, wherein applying in (dd) is performed via via coating, preferably slot-die (extrusion) coating or reverse gravure coating, or printing, preferably flexography printing or (forward) gravure printing.
- step (dd) the inventive photovoltaic layer is obtained, being located on the anode, optionally on the smoothing layer. Therefore, the present invention also relates to above- described process comprising
- a photovoltaic layer comprising a mixture which comprises at least one diketopyrrolopyrrole (DPP) polymer and at least one stabilizing agent wherein the stabilizing agent is preferably selected from the group consisting of a UV absorbing agent and an anti-radical agent.
- DPP diketopyrrolopyrrole
- At least one suitable solvent is employed.
- suitable solvents for preparing the mixtures according to the present application are all common solvents in which the DPP polymer and stabilizing agents have satisfactory solubility.
- common organic solvents include, but are not limited to,
- aromatic hydrocarbons such as benzene, chlorobenzene, dichlorobenzene, preferably 1 ,2-dichlorobenzene, trichlorobenzene, cyclohexylbenzene, toluene, anisole, xylene, naphthalene, chloronaphtalene, tetraline, indene, indane, cyclooctadiene, styrene, decaline and mesitylene;
- aromatic hydrocarbons such as benzene, chlorobenzene, dichlorobenzene, preferably 1 ,2-dichlorobenzene, trichlorobenzene, cyclohexylbenzene, toluene, anisole, xylene, naphthalene, chloronaphtalene, tetraline, indene, indane, cyclooctadiene, styrene, decaline and me
- halogenated aliphatic hydrocarbons such as dichloromethane, chloroform and ethylenechloride
- ethers such as dioxane and dioxolane
- ketones such as cyclopentanone and cyclohexanone
- aliphatic hydrocarbons such as hexanes and cyclohexanes
- solvents are dichlorobenzene, toluene, xylene, tetraline, chloroform, mesitylene and mixtures of two or more thereof. Therefore, the present invention also relates to above- described process, wherein in (cc), dichlorobenzene, preferably 1 ,2-dichlorobenzene,l toluene, xylene, tetraline, chloroform, mesitylene and mixtures of two or more thereof is used as solvent.
- Usual concentrations of the compounds according to (cc) in the solvent are generally in the range of from 0.01 to 90% by weight, based on the weight of the solvent.
- an OPV device as described above comprising, most preferably in this order, (a) a cathode;
- a transition layer and a cathode are applied onto the photovoltaic layer.
- this transition layer is made of an alkali halogenide, most preferably lithium fluoride.
- the alkali halogenide, most preferably lithium fluoride is vapor deposited in a suitable vacuum such as 2 x 10 "6 torr at a suitable rate such as 0.2 nm/minute.
- the electric insulation properties of the transition layer obviously prevent influences which hinder the crossing of the charge carrier from being effective, particularly in the transition region from the photovoltaic layer to the transition layer.
- a suitable cathode (a) is applied. While there are no specific restrictions as far as the respective application method is concerned, it is preferred, for example, to apply the cathode (a) by vapor deposition.
- the present invention also relates to above-described process comprising steps (aa) to (dd), further optionally comprising the step (ee) and further comprising (ff) of
- one or more of the layers may be treated with plasma prior to depositing the next layer. It is particularly advantageous that the smoothing layer, preferably the smoothing layer comprising PEDOT:PSS be subject to a mild plasma treatment prior to deposition of the next layer.
- a photovoltaic layer comprising a DPP polymer
- a further layer which protects the photovoltaic layer and, therefore, the OPV device in total from degradation during using the OPV device
- HALS hindered amine light stabilizer
- the present invention also relates to the of a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one diketopyrrolopyrrole (DPP) polymer for increasing the product life of an organic photovoltaic (OPV) device containing the mixture in at least one photovoltaic layer.
- at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent
- DPP diketopyrrolopyrrole
- the present invention also relates to a method of increasing the product life of an organic photovoltaic (OPV) device by using a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one
- OCV organic photovoltaic
- DPP diketopyrrolopyrrole
- the present invention also relates to the use of a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and at least one diketopyrrolopyrrole (DPP) polymer for preventing the at least one DPP polymer from degradation during production of an OPV device containing the mixture in at least one photovoltaic layer.
- at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent
- DPP diketopyrrolopyrrole
- the present invention also relates to a method of preventing at least one DPP polymer from degradation during production of an OPV device containing said at least one DPP polymer by using a mixture comprising at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent, and said at least one diketopyrrolopyrrole (DPP) polymer, the OPV device containing said mixture in at least one photovoltaic layer.
- at least one stabilizing agent which is preferably a UV absorbing agent or an anti-radical agent
- DPP diketopyrrolopyrrole
- Fig. 1 shows the absorbance at a wavelength of 690 nm of the film prepared according to
- Fig. 1 the followings symbols stand for:
- Fig. 2 shows the absorbance at a wavelength of 690 nm of the film prepared according to
- Fig. 2 the followings symbols stand for:
- Fig. 3 shows the absorbance at a wavelength of 690 nm of the film prepared according to
- Example 2 with Chimassorb® 81 as stabilizing agent dependent on the duration (in days) of exposure of the film to light of said wavelength.
- Fig. 3 the followings symbols stand for:
- the polymer is purified by Soxhlet extraction using different solvents: tetrahydrofurane, chloroform and ortho-dichlorobenzene. 720 mg of the ortho-dichlorobenzene fraction contains the above polymer 8 of Mw of 100 ⁇ 00 and a polydispersity of 2.59 (measured by high temperature GPC).
- Random copolymer 7 is prepared according to WO 2010/049323 A1 (Example 1 , page 45, line 24 to age 47, line 9):
- Example 1 Polymer based bulk heterojunction solar cells Structure of the solar cells
- the solar cells used have the following structures (in brackets: layer thickness):
- transition layer LiF layer (1 nm)
- photovoltaic layer organic layer, comprising as DPP polymer the random copolymer 7 - described in WO 2010/049323 A1 ; and [70]PCBM (95%, Solene BV) with or without stabilizing additives according to the table hereinunder;
- PSS poly(styrenesulfonic acid)
- (k) substrate glass substrate (1.1 mm)
- the solar cells are made by spin coating a layer of the PEDOT-PSS on a pre-patterned ITO on the glass substrate. Then, a 1 :1 .5:"X" mixture of the random copolymer 7 (1 % by weight) :
- PCBM stabilizing additive is spin coated from o-dichlorobenzene (organic layer). Samples containing no stabilizing agent are used as reference. As to the amount of stabilizing agent ("X”), reference is made to the tables hereinunder.
- the solar cell is measured under a solar light simulator. Then, with the External Quantum Efficiency (EQE) graph, the current is estimated under AM1 .5 conditions. This leads to a values reported in the tables below.
- the abbreviations stand for: short current density (Jsc); open circuit voltages (Voc); fill factor (FF); maximum power point (MPP).
- Tinuvin® 312 1 14.6 0.61 55.9 5.0
- Tinuvin® 622 1 0.5 0.1 1 18.7 0
- Tinuvin® 234 2-(2H-benzotriazol-2- l)-4,6-bis(1 -methyl-1 -phenylethyl)phenol
- Tinuvin® 1577 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1 ,3,5-triazine
- Tinuvin® 120 2',4'-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate
- Tinuvin® 780 bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate
- Tinuvin® 312 2-ethoxy-2'-ethyl-oxanilide:
- Tinuvin® 622 is a polymer with the repeating unit:
- the films are made by spin-coating (600 rpm, 2 min.) the DPP polymer (1 % by weight) in o- dichlorobenzene onto glass substrates (50x50x1 mm microscope slides), together with the specified amount "X" of stabilizing agent (wt% with respect to the weight of the DPP polymer).
- Stabilizing agents are as identified in below Tables d and e (see also Figure 3).
- a protective layer of poly(methyl methacrylate) (PMMA, 4 % by weight in butylacetate) is spin-coated (1000 rpm, 30 s) on top.
- PMMA poly(methyl methacrylate)
- the sample films are left in air and normal atmosphere and the degradation of the films is followed by UV-VIS spectroscopy
- Photooxidation is determined numerically by measuring the absorbance of the DPP polymer at 690 nm. The absorption peak decreases upon exposure to oxidation. Results are shown in the below Tables d and e for exposure times of 1 15 days and 56 days, respectively. UV-absorbers provide good protection against photo-oxidation. An effect is further achieved by addition of phenolic antioxidant (Tinuvin® 120) or hindered amine light stabilizer (HALS; Tinuvin® 780), especially in low concentration.
- phenolic antioxidant Tinuvin® 120
- HALS hindered amine light stabilizer
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/978,260 US20130306151A1 (en) | 2011-01-13 | 2012-01-11 | Organic photovoltaic device and manufacturing method thereof |
EP12734624.5A EP2663595A1 (en) | 2011-01-13 | 2012-01-11 | Organic photovoltaic device and manufacturing method thereof |
CN201280004514.3A CN103282421B (en) | 2011-01-13 | 2012-01-11 | Organic photovoltaic device and manufacturing method thereof |
KR1020137021018A KR20140044287A (en) | 2011-01-13 | 2012-01-11 | Organic photovoltaic device and process for its procution |
JP2013548918A JP2014508196A (en) | 2011-01-13 | 2012-01-11 | Organic photovoltaic device and manufacturing method thereof |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161432204P | 2011-01-13 | 2011-01-13 | |
EP11150782 | 2011-01-13 | ||
US61/432,204 | 2011-01-13 | ||
EP11150782.8 | 2011-01-13 | ||
EP11156218 | 2011-02-28 | ||
EP11156218.7 | 2011-02-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012095796A1 true WO2012095796A1 (en) | 2012-07-19 |
Family
ID=46506809
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2012/050132 WO2012095796A1 (en) | 2011-01-13 | 2012-01-11 | Organic photovoltaic device and manufacturing method thereof |
Country Status (7)
Country | Link |
---|---|
US (1) | US20130306151A1 (en) |
EP (1) | EP2663595A1 (en) |
JP (1) | JP2014508196A (en) |
KR (1) | KR20140044287A (en) |
CN (1) | CN103282421B (en) |
TW (1) | TW201233707A (en) |
WO (1) | WO2012095796A1 (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014202184A1 (en) | 2013-06-21 | 2014-12-24 | Merck Patent Gmbh | Conjugated polymers |
WO2015036075A1 (en) | 2013-09-11 | 2015-03-19 | Merck Patent Gmbh | Cyclohexadiene fullerene derivatives |
WO2015067336A2 (en) | 2013-11-06 | 2015-05-14 | Merck Patent Gmbh | Conjugated polymers |
WO2015139802A1 (en) | 2014-03-17 | 2015-09-24 | Merck Patent Gmbh | Organic semiconducting compounds |
WO2015192942A1 (en) | 2014-06-17 | 2015-12-23 | Merck Patent Gmbh | Fullerene derivatives |
CN105439971A (en) * | 2015-12-31 | 2016-03-30 | 华东师范大学 | Synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine |
EP3029749A4 (en) * | 2013-07-31 | 2016-08-31 | Fujifilm Corp | Organic semiconductor composition, organic thin film transistor, electronic paper and display device |
EP3070756A1 (en) | 2015-03-18 | 2016-09-21 | Merck Patent GmbH | Semiconductor mixtures comprising nanoparticles |
US9543521B2 (en) | 2011-11-15 | 2017-01-10 | Basf Se | Organic semiconductor device and process for its production |
US9608219B2 (en) | 2010-12-22 | 2017-03-28 | Basf Se | Semiconductor structure and method for its production |
EP3173435A1 (en) | 2015-11-26 | 2017-05-31 | Merck Patent GmbH | Semiconducting mixtures |
WO2017157504A1 (en) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Organic semiconductors |
WO2017157782A1 (en) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Organic semiconductors |
US20170346018A1 (en) * | 2015-03-13 | 2017-11-30 | Fujifilm Corporation | Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device |
WO2018007431A1 (en) | 2016-07-08 | 2018-01-11 | Merck Patent Gmbh | Fused dithienothiophene derivatives and their use as organic semiconductors |
WO2018041768A1 (en) | 2016-08-29 | 2018-03-08 | Merck Patent Gmbh | 1,3-dithiolo[5,6-f]benzo-2,1,3-thiadiazole or 1,3-dithiolo[6,7-g]quinoxaline based organic semiconductors |
WO2020187867A1 (en) | 2019-03-19 | 2020-09-24 | Raynergy Tek Inc. | Organic semiconductors |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8440043B1 (en) | 2012-03-30 | 2013-05-14 | The Procter & Gamble Company | Absorbent article process and apparatus for intermittently deactivating elastics in elastic laminates |
US9039855B2 (en) | 2012-03-30 | 2015-05-26 | The Procter & Gamble Company | Apparatuses and methods for making absorbent articles |
US9050213B2 (en) | 2012-03-30 | 2015-06-09 | The Procter & Gamble Company | Apparatuses and methods for making absorbent articles |
US9028632B2 (en) | 2012-03-30 | 2015-05-12 | The Procter & Gamble Company | Apparatuses and methods for making absorbent articles |
US20130255861A1 (en) | 2012-03-30 | 2013-10-03 | Uwe Schneider | Apparatuses and Methods for Making Absorbent Articles |
KR20160033392A (en) * | 2014-09-18 | 2016-03-28 | 한국과학기술연구원 | Light stabilizer, organic photovoltaic cell comprising the same, and the preparation method thereof |
CN104409638A (en) * | 2014-11-13 | 2015-03-11 | 无锡中洁能源技术有限公司 | Cathode-anode interface modified layer film material of solar cell and preparation method of cathode-anode interface modified layer film material |
CN104409640A (en) * | 2014-11-13 | 2015-03-11 | 无锡中洁能源技术有限公司 | Broad spectrum solar cell material and preparation method thereof |
CN104377305A (en) * | 2014-11-13 | 2015-02-25 | 无锡中洁能源技术有限公司 | Degradable photoelectric material and preparing method for degradable photoelectric material |
CN106117983A (en) * | 2016-07-25 | 2016-11-16 | 广西南宁胜祺安科技开发有限公司 | A kind of novel solar battery degradable environment-friendly type photoelectric material |
CN106084673A (en) * | 2016-07-25 | 2016-11-09 | 广西南宁胜祺安科技开发有限公司 | A kind of degradable photoelectric material |
CN106117984A (en) * | 2016-07-25 | 2016-11-16 | 广西南宁胜祺安科技开发有限公司 | A kind of novel degradable photoelectric material |
DE102020131756A1 (en) * | 2020-12-01 | 2022-06-02 | Heliatek Gmbh | Layer system for an organic electronic component |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010049323A1 (en) * | 2008-10-31 | 2010-05-06 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
WO2010108873A1 (en) * | 2009-03-23 | 2010-09-30 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5789298B2 (en) * | 2010-07-09 | 2015-10-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | Semiconducting polymer |
-
2012
- 2012-01-11 US US13/978,260 patent/US20130306151A1/en not_active Abandoned
- 2012-01-11 EP EP12734624.5A patent/EP2663595A1/en not_active Withdrawn
- 2012-01-11 CN CN201280004514.3A patent/CN103282421B/en not_active Expired - Fee Related
- 2012-01-11 WO PCT/IB2012/050132 patent/WO2012095796A1/en active Application Filing
- 2012-01-11 KR KR1020137021018A patent/KR20140044287A/en not_active Application Discontinuation
- 2012-01-11 JP JP2013548918A patent/JP2014508196A/en not_active Withdrawn
- 2012-01-12 TW TW101101285A patent/TW201233707A/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010049323A1 (en) * | 2008-10-31 | 2010-05-06 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
WO2010108873A1 (en) * | 2009-03-23 | 2010-09-30 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9608219B2 (en) | 2010-12-22 | 2017-03-28 | Basf Se | Semiconductor structure and method for its production |
US9543521B2 (en) | 2011-11-15 | 2017-01-10 | Basf Se | Organic semiconductor device and process for its production |
WO2014202184A1 (en) | 2013-06-21 | 2014-12-24 | Merck Patent Gmbh | Conjugated polymers |
EP3029749A4 (en) * | 2013-07-31 | 2016-08-31 | Fujifilm Corp | Organic semiconductor composition, organic thin film transistor, electronic paper and display device |
US10008682B2 (en) | 2013-07-31 | 2018-06-26 | Fujifilm Corporation | Organic semiconductor composition, organic thin film transistor, electronic paper and display device |
WO2015036075A1 (en) | 2013-09-11 | 2015-03-19 | Merck Patent Gmbh | Cyclohexadiene fullerene derivatives |
WO2015067336A2 (en) | 2013-11-06 | 2015-05-14 | Merck Patent Gmbh | Conjugated polymers |
WO2015139802A1 (en) | 2014-03-17 | 2015-09-24 | Merck Patent Gmbh | Organic semiconducting compounds |
WO2015192942A1 (en) | 2014-06-17 | 2015-12-23 | Merck Patent Gmbh | Fullerene derivatives |
EP4008708A1 (en) | 2014-06-17 | 2022-06-08 | Nano-C, Inc. | Fullerene derivatives for organic semiconductors |
US10510965B2 (en) * | 2015-03-13 | 2019-12-17 | Fujifilm Corporation | Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device |
US20170346018A1 (en) * | 2015-03-13 | 2017-11-30 | Fujifilm Corporation | Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device |
EP3070756A1 (en) | 2015-03-18 | 2016-09-21 | Merck Patent GmbH | Semiconductor mixtures comprising nanoparticles |
EP3173435A1 (en) | 2015-11-26 | 2017-05-31 | Merck Patent GmbH | Semiconducting mixtures |
WO2017088955A1 (en) | 2015-11-26 | 2017-06-01 | Merck Patent Gmbh | Semiconducting mixtures |
CN105439971A (en) * | 2015-12-31 | 2016-03-30 | 华东师范大学 | Synthetic method of 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine |
WO2017157782A1 (en) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Organic semiconductors |
WO2017157504A1 (en) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Organic semiconductors |
WO2018007431A1 (en) | 2016-07-08 | 2018-01-11 | Merck Patent Gmbh | Fused dithienothiophene derivatives and their use as organic semiconductors |
WO2018041768A1 (en) | 2016-08-29 | 2018-03-08 | Merck Patent Gmbh | 1,3-dithiolo[5,6-f]benzo-2,1,3-thiadiazole or 1,3-dithiolo[6,7-g]quinoxaline based organic semiconductors |
WO2020187867A1 (en) | 2019-03-19 | 2020-09-24 | Raynergy Tek Inc. | Organic semiconductors |
Also Published As
Publication number | Publication date |
---|---|
TW201233707A (en) | 2012-08-16 |
CN103282421B (en) | 2015-05-27 |
KR20140044287A (en) | 2014-04-14 |
EP2663595A1 (en) | 2013-11-20 |
US20130306151A1 (en) | 2013-11-21 |
CN103282421A (en) | 2013-09-04 |
JP2014508196A (en) | 2014-04-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2012095796A1 (en) | Organic photovoltaic device and manufacturing method thereof | |
EP2035428B1 (en) | Diketopyrrolopyrrole polymers as organic semiconductors | |
EP2571919B1 (en) | Diketopyrrolopyrrole polymers for use in organic semiconductor devices | |
EP2834284B1 (en) | Phenanthro[9,10-b]furan polymers and small molecules for electronic applications | |
EP2411986B1 (en) | Diketopyrrolopyrrole polymers for use in organic semiconductor devices | |
EP2928940B1 (en) | Functionalized benzodithiophene polymers for electronic application | |
EP2764034B1 (en) | Polymers based on benzodiones | |
EP2834286B1 (en) | Diketopyrrolopyrrole polymers and small molecules | |
EP2818493A1 (en) | Near infrared absorbing polymers for electronic applications | |
WO2014016219A1 (en) | Dithienobenzofuran polymers and small molecules for electronic application | |
EP2780409A1 (en) | Organic semiconductor device and manufacturing method thereof | |
Istanbulluoglu et al. | Synthesis of a benzotriazole bearing alternating copolymer for organic photovoltaic applications | |
EP2917304B1 (en) | Polymers based on naphthodiones |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 12734624 Country of ref document: EP Kind code of ref document: A1 |
|
REEP | Request for entry into the european phase |
Ref document number: 2012734624 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012734624 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13978260 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2013548918 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20137021018 Country of ref document: KR Kind code of ref document: A |