KR102639496B1 - Heterocyclic compound and organic electronic device comprising the same - Google Patents
Heterocyclic compound and organic electronic device comprising the same Download PDFInfo
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- KR102639496B1 KR102639496B1 KR1020190041389A KR20190041389A KR102639496B1 KR 102639496 B1 KR102639496 B1 KR 102639496B1 KR 1020190041389 A KR1020190041389 A KR 1020190041389A KR 20190041389 A KR20190041389 A KR 20190041389A KR 102639496 B1 KR102639496 B1 KR 102639496B1
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- South Korea
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- compound
- organic
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- ylidene
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 29
- 239000010410 layer Substances 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 description 113
- 238000002360 preparation method Methods 0.000 description 85
- 239000000463 material Substances 0.000 description 42
- -1 fullerene compound Chemical class 0.000 description 32
- 238000000034 method Methods 0.000 description 29
- 239000000758 substrate Substances 0.000 description 19
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 18
- 239000000370 acceptor Substances 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011368 organic material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 8
- QNVKZKOSAXYVFZ-UHFFFAOYSA-N 2-(3-oxoinden-1-ylidene)propanedinitrile Chemical compound C1=CC=C2C(=O)CC(=C(C#N)C#N)C2=C1 QNVKZKOSAXYVFZ-UHFFFAOYSA-N 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- UYSZYWIPEGBWIR-UHFFFAOYSA-N 2-(3-oxocyclopenta[b]naphthalen-1-ylidene)propanedinitrile Chemical compound O=C1CC(C2=CC3=CC=CC=C3C=C21)=C(C#N)C#N UYSZYWIPEGBWIR-UHFFFAOYSA-N 0.000 description 6
- FKMLTPDJPCYVHT-UHFFFAOYSA-N 2-(5,6-difluoro-3-oxoinden-1-ylidene)propanedinitrile Chemical compound FC=1C=C2C(CC(C2=CC=1F)=C(C#N)C#N)=O FKMLTPDJPCYVHT-UHFFFAOYSA-N 0.000 description 6
- ZWYYFFSHJKUYHA-UHFFFAOYSA-N 2-(5,6-dimethyl-3-oxoinden-1-ylidene)propanedinitrile Chemical compound Cc1cc2C(=O)CC(=C(C#N)C#N)c2cc1C ZWYYFFSHJKUYHA-UHFFFAOYSA-N 0.000 description 6
- MABYCDQSGPPWTM-UHFFFAOYSA-N 2-(5-chloro-3-oxoinden-1-ylidene)propanedinitrile Chemical compound ClC=1C=C2C(CC(C2=CC=1)=C(C#N)C#N)=O MABYCDQSGPPWTM-UHFFFAOYSA-N 0.000 description 6
- HLAQKJZRTQNBDB-UHFFFAOYSA-N 2-(6-bromo-3-oxoinden-1-ylidene)propanedinitrile Chemical compound BrC1=CC=C2C(=O)CC(=C(C#N)C#N)C2=C1 HLAQKJZRTQNBDB-UHFFFAOYSA-N 0.000 description 6
- HSXULKAPILMKHA-UHFFFAOYSA-N 2-(6-fluoro-3-oxoinden-1-ylidene)propanedinitrile Chemical compound FC1=CC=C2C(=O)CC(=C(C#N)C#N)C2=C1 HSXULKAPILMKHA-UHFFFAOYSA-N 0.000 description 6
- NXFDCVXZHNVIRH-UHFFFAOYSA-N 2-(6-methyl-3-oxoinden-1-ylidene)propanedinitrile Chemical compound CC1=CC=C2C(=O)CC(=C(C#N)C#N)C2=C1 NXFDCVXZHNVIRH-UHFFFAOYSA-N 0.000 description 6
- HDHQGIWTIHTYRM-UHFFFAOYSA-N 2-(6-oxocyclopenta[b]thiophen-4-ylidene)propanedinitrile Chemical compound O=C1CC(=C(C#N)C#N)c2ccsc12 HDHQGIWTIHTYRM-UHFFFAOYSA-N 0.000 description 6
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 6
- GBBRGVXKTMQPSL-UHFFFAOYSA-N O=C1CC(C=2C1=CSC=2)=C(C#N)C#N Chemical compound O=C1CC(C=2C1=CSC=2)=C(C#N)C#N GBBRGVXKTMQPSL-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000005605 benzo group Chemical group 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- MXHOLIARBWJKCR-UHFFFAOYSA-N 1-bromo-4-hexylbenzene Chemical compound CCCCCCC1=CC=C(Br)C=C1 MXHOLIARBWJKCR-UHFFFAOYSA-N 0.000 description 5
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- UKHQRARQNZOXRL-UHFFFAOYSA-N trimethyltin Chemical compound C[SnH](C)C UKHQRARQNZOXRL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- 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 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
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- 238000007650 screen-printing Methods 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- MKDLYSABBHXXSV-UHFFFAOYSA-N 1-iodo-4-(4-propylphenyl)benzene Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(I)C=C1 MKDLYSABBHXXSV-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 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
- 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 1
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- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HQOWCDPFDSRYRO-CDKVKFQUSA-N CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 Chemical compound CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 HQOWCDPFDSRYRO-CDKVKFQUSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000005224 alkoxybenzenes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- PDYDQPWWVZTVQD-UHFFFAOYSA-N ethyl 2-bromothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1Br PDYDQPWWVZTVQD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 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
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 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 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-M thiophene-3-carboxylate Chemical compound [O-]C(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-M 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- H—ELECTRICITY
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Abstract
본 명세서는 화학식 1로 표시되는 헤테로환 화합물, 상기 헤테로환 화합물을 유기활성층에 포함하는 유기 전자 소자 및 상기 헤테로환 화합물을 이용한 유기 전자 소자의 제조 방법에 관한 것이다.This specification relates to a heterocyclic compound represented by Formula 1, an organic electronic device including the heterocyclic compound in an organic active layer, and a method of manufacturing an organic electronic device using the heterocyclic compound.
Description
본 명세서는 헤테로환 화합물, 이를 포함하는 유기 전자 소자의 유기활성층 형성용 조성물 및 유기 전자 소자에 관한 것이다.This specification relates to heterocyclic compounds, compositions containing the same for forming an organic active layer of an organic electronic device, and organic electronic devices.
본 명세서에서, 유기 전자 소자란 유기 반도체 물질을 이용한 전자 소자로서, 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다. 유기 전자 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 전자 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 전자 소자이다.In this specification, an organic electronic device is an electronic device using an organic semiconductor material and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic electronic devices can be broadly divided into two categories according to their operating principles as follows. First, excitons are formed in the organic layer by photons flowing into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as current sources (voltage sources). It is a type of electronic device. The second is an electronic device that applies voltage or current to two or more electrodes to inject holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes, and operates by the injected electrons and holes.
유기 전자 소자의 예로는 유기 태양 전지, 유기 광전 소자, 유기 발광 소자, 유기 감광체(OPC) 및 유기 트랜지스터 등이 있으며, 이들은 모두 소자의 구동을 위하여 전자/정공 주입 물질, 전자/정공 추출 물질, 전자/정공 수송 물질 또는 발광 물질을 필요로 한다. 이하에서는 주로 유기 태양 전지에 대하여 구체적으로 설명하지만, 상기 유기 전자 소자들에서는 전자/정공 주입 물질, 전자/정공 추출 물질, 전자/정공 수송 물질 또는 발광 물질이 모두 유사한 원리로 작용한다.Examples of organic electronic devices include organic solar cells, organic photovoltaic devices, organic light-emitting devices, organic photoreceptors (OPCs), and organic transistors, which all use electron/hole injection materials, electron/hole extraction materials, and electrons to drive the devices. /Requires hole transport material or light emitting material. Hereinafter, organic solar cells will be mainly described in detail, but in the organic electronic devices, electron/hole injection materials, electron/hole extraction materials, electron/hole transport materials, or light-emitting materials all operate on similar principles.
태양 전지는 태양 빛으로부터 직접 전기적 에너지를 변화시키는 전지로, 화석 에너지의 고갈과 이의 사용에 의한 지구 환경적인 문제를 해결하기 위한 청정한 대체 에너지원이기 때문에 연구가 활발히 진행되고 있다. 여기서 태양 전지란 태양빛으로부터 광 에너지를 흡수하여 전자와 정공이 발생하는 광기전 효과를 이용하여 전류-전압을 생성하는 전지를 의미한다.Solar cells are batteries that change electrical energy directly from sunlight, and research is actively underway because they are a clean alternative energy source to solve global environmental problems caused by the depletion of fossil energy and its use. Here, a solar cell refers to a battery that absorbs light energy from sunlight and generates current-voltage using the photovoltaic effect, which generates electrons and holes.
태양 전지는 광기전력효과(photovoltaic effect)를 응용함으로써 태양에너지를 직접 전기에너지로 변환할 수 있는 소자이다. 태양 전지는 박막을 구성하는 물질에 따라 무기 태양 전지와 유기 태양 전지로 나뉠 수 있다.A solar cell is a device that can directly convert solar energy into electrical energy by applying the photovoltaic effect. Solar cells can be divided into inorganic solar cells and organic solar cells depending on the materials that make up the thin film.
태양 전지의 설계에 따른 다양한 층 및 전극의 변화를 통하여, 에너지 변환 효율을 높이기 위한 많은 연구가 진행되고 있다.Much research is being conducted to increase energy conversion efficiency through changes in various layers and electrodes according to the design of solar cells.
본 발명은 헤테로환 화합물, 이를 포함하는 유기 전자 소자의 유기활성층 형성용 조성물 및 유기 전자 소자를 제공하는 것을 목적으로 한다.The purpose of the present invention is to provide a heterocyclic compound, a composition containing the same for forming an organic active layer of an organic electronic device, and an organic electronic device.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 헤테로환 화합물을 제공한다.An exemplary embodiment of the present specification provides a heterocyclic compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
L1 내지 L4는 서로 같거나 상이하며 각각 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 to L4 are the same or different from each other and are each a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
L5 및 L6는 서로 같거나 상이하며 각각 치환 또는 비치환된 아릴렌기이고,L5 and L6 are the same or different from each other and are each a substituted or unsubstituted arylene group,
R1 내지 R8은 서로 같거나 상이하며 각각 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 또는 치환 또는 비치환된 알킬티오기이고,R1 to R8 are the same or different from each other and are each hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkylthio group,
R9 및 R10은 서로 같거나 상이하며 각각 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 알킬티오기이며,R9 and R10 are the same or different from each other and are each a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted alkylthio group,
Ar1 및 Ar2는 서로 같거나 상이하며 각각 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are the same or different from each other and are each a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Y1 및 Y2는 서로 같거나 상이하며 각각 수소; 할로겐기; 또는 치환 또는 비치환된 알킬기이고,Y1 and Y2 are the same or different and are each hydrogen; halogen group; Or a substituted or unsubstituted alkyl group,
n 및 m은 서로 같거나 상이하며 각각 0 내지 6의 정수이다.n and m are the same as or different from each other and are each integers from 0 to 6.
또한, 본 명세서의 일 실시상태는In addition, one embodiment of the present specification is
상기 헤테로환 화합물을 포함하는 유기 전자 소자의 유기활성층 형성용 조성물을 제공한다.Provided is a composition for forming an organic active layer of an organic electronic device containing the heterocyclic compound.
또한, 본 명세서의 일 실시상태는 In addition, one embodiment of the present specification is
제1 전극; first electrode;
상기 제1 전극과 대향하여 구비되는 제2 전극; 및 a second electrode provided opposite the first electrode; and
상기 제1 전극과 제2 전극 사이에 구비되고, 유기활성층을 포함하는 1층 이상의 유기물층을 포함하며, It is provided between the first electrode and the second electrode, and includes one or more organic layers including an organic active layer,
상기 유기활성층은 상기 헤테로환 화합물을 포함하는 것인 유기 전자 소자를 제공한다.The organic active layer provides an organic electronic device including the heterocyclic compound.
본 명세서의 일 실시상태에 헤테로환 화합물은 알콕시 벤젠의 도입으로 용해도 문제를 개선하여 유기 태양 전지의 성능에 유리한 유기 박막 형성이 가능해져, 상기 헤테로환 화합물을 유기 전자 소자의 유기활성층에 사용하였을 때, 높은 수준의 광-전 변환 효율을 얻을 수 있다.In one embodiment of the present specification, the heterocyclic compound improves the solubility problem by introducing alkoxy benzene, making it possible to form an organic thin film that is advantageous to the performance of an organic solar cell, and when the heterocyclic compound is used in the organic active layer of an organic electronic device , a high level of photo-electric conversion efficiency can be achieved.
도 1은 본 명세서의 일 실시상태에 따르는 유기 태양 전지를 나타낸 도이다.
도 2 내지 도 61은 각각 화합물 1 내지 60의 필름상태의 UV-Vis 흡수 스펙트럼(UV-vis-absorption spectrum) 을 나타낸 도이다.1 is a diagram showing an organic solar cell according to an exemplary embodiment of the present specification.
Figures 2 to 61 show the UV-vis absorption spectra of compounds 1 to 60 in a film state, respectively.
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this specification will be described in more detail.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 헤테로환 화합물을 제공한다.An exemplary embodiment of the present specification provides a heterocyclic compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
L1 내지 L4는 서로 같거나 상이하며 각각 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 to L4 are the same or different from each other and are each a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
L5 및 L6는 서로 같거나 상이하며 각각 치환 또는 비치환된 아릴렌기이고,L5 and L6 are the same or different from each other and are each a substituted or unsubstituted arylene group,
R1 내지 R8은 서로 같거나 상이하며 각각 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 또는 치환 또는 비치환된 알킬티오기이고,R1 to R8 are the same or different from each other and are each hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkylthio group,
R9 및 R10은 서로 같거나 상이하며 각각 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 알킬티오기이며,R9 and R10 are the same or different from each other and are each a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted alkylthio group,
Ar1 및 Ar2는 서로 같거나 상이하며 각각 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are the same or different from each other and are each a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Y1 및 Y2는 서로 같거나 상이하며 각각 수소; 할로겐기; 또는 치환 또는 비치환된 알킬기이고,Y1 and Y2 are the same or different and are each hydrogen; halogen group; Or a substituted or unsubstituted alkyl group,
n 및 m은 서로 같거나 상이하며 각각 0 내지 6의 정수이다..n and m are the same or different from each other and are each integers from 0 to 6.
종래의 유기 전자 소자에 대한 연구는 유기활성층의 전자 받개가 PCBM과 같은 플러렌 화합물일 때 고효율을 내는 전자 주개 물질을 찾는데 집중되었다, 그러나, 플러렌 화합물을 포함하는 유기 전자 소자는 흡수 영역, 개방 전압 및 소자 수명 등의 성능에서 한계에 부딪히고 있기 때문에 ITIC와 같은 비플러렌계 화합물을 전자 받개로 활용하는 연구가 증가하고 있다. Conventional research on organic electronic devices has focused on finding electron donor materials that produce high efficiency when the electron acceptor of the organic active layer is a fullerene compound such as PCBM. However, organic electronic devices containing fullerene compounds have low absorption area, open-circuit voltage, and Because limitations are being encountered in performance such as device lifespan, research on using non-fullerene compounds such as ITIC as electron acceptors is increasing.
비플러렌계 화합물은 대부분 EWG(electron withdrawing group)-EDG(electron donating group)-EWG(electron withdrawing group) 형태로 이루어져 있다. 본 발명의 발명자들은 상기 EDG의 side chain으로 알콕시 페닐기를 도입하였고, 이를 통해 향상된 용해도에 의해 전자 주개 물질과의 섞임성이 우수해져 유기 태양 전지의 소자 특성이 개선됨을 확인하였다. 이는 EDG 그룹에 도입된 side chain 인 페닐기가 기존에 일반적으로 사용되어 온 티오펜 또는 알콕시기에 비해 용이하게 free rotation 이 가능하고 전자 주개 능력이 티오펜인 경우에 비해낮아져 낮은 HOMO/높은 LUMO 에너지 레벨을 유발하기 때문이다. 또한 페닐기의 para- 또는 meta- 위치에 알콕시기를 도입함으로써 용해도 조절과 에너지 레벨 조절 또한 가능해졌다. Most non-fullerene compounds are in the form of EWG (electron withdrawing group)-EDG (electron donating group)-EWG (electron withdrawing group). The inventors of the present invention introduced an alkoxy phenyl group into the side chain of EDG, and confirmed that this improved solubility and excellent miscibility with electron donor materials, thereby improving device characteristics of organic solar cells. This is because the phenyl group, which is a side chain introduced into the EDG group, can easily free rotate compared to the thiophene or alkoxy group that has been commonly used, and its electron donating ability is lower than that of thiophene, resulting in low HOMO/high LUMO energy levels. Because it causes it. In addition, by introducing an alkoxy group at the para- or meta- position of the phenyl group, solubility control and energy level control were also possible.
본 명세서에서 어떤 부분이 어떤 구성요소를 '포함' 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part 'includes' a certain component, this means that it may further include other components rather than excluding other components unless specifically stated to the contrary.
본 명세서에서 어떤 부재가 다른 부재 '상에' 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is said to be located 'on' another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
본 명세서에 있어서, 에너지 준위는 에너지의 크기를 의미하는 것이다. 따라서, 진공준위로부터 마이너스(-) 방향으로 에너지 준위가 표시되는 경우에도, 에너지 준위는 해당 에너지 값의 절대값을 의미하는 것으로 해석된다. 예컨대, HOMO 에너지 준위란 진공준위로부터 최고 점유 분자 오비탈(highest occupied molecular orbital)까지의 거리를 의미한다. 또한, LUMO 에너지 준위란 진공준위로부터 최저 비점유 분자 오비탈(lowest unoccupied molecular orbital)까지의 거리를 의미한다. In this specification, energy level refers to the amount of energy. Therefore, even when the energy level is displayed in the minus (-) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, the HOMO energy level means the distance from the vacuum level to the highest occupied molecular orbital. Additionally, the LUMO energy level refers to the distance from the vacuum level to the lowest unoccupied molecular orbital.
본 명세서에 있어서, '치환'이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 같거나 상이할 수 있다.In this specification, the term 'substitution' means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, 2 In the case of more than one substitution, two or more substituents may be the same or different from each other.
본 명세서에서 '치환 또는 비치환된'이라는 용어는 중수소; 할로겐기; 히드록시기; 알킬기; 시클로알킬기; 알콕시기; 아릴옥시기; 알케닐기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. In this specification, the term 'substituted or unsubstituted' refers to deuterium; halogen group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; alkenyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
본 명세서에 있어서, 분지쇄를 갖는 치환기의 탄소수는 상기 분지쇄의 탄소수를 포함한다. 예를 들어, '하나 이상의 메틸기를 분지쇄로 갖는 탄소수 3 내지 20의 알킬기'에서 상기 '3 내지 20'은 상기 '하나 이상의 메틸기'의 탄소수를 포함하는 수치이다.In the present specification, the number of carbon atoms of a substituent having a branched chain includes the number of carbon atoms of the branched chain. For example, in 'an alkyl group having 3 to 20 carbon atoms having one or more methyl groups as a branch', '3 to 20' is a number including the number of carbon atoms of the 'one or more methyl groups'.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸부틸, 1-에틸부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸헥실, 4-메틸헥실 및 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl , 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, Examples include, but are not limited to, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylhexyl, 4-methylhexyl, and 5-methylhexyl.
본 명세서에 있어서, 상기 알킬티오기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알킬티오기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메틸티오, 에틸티오, n-프로필티오, 이소프로필티오, i-프로필티오, n-부틸티오, 이소부틸티오, tert-부틸티오, sec-부틸티오, n-펜틸티오, 네오펜틸티오, 이소펜틸티오, n-헥실티오, 3,3-디메틸부틸티오, 2-에틸부틸티오, n-옥틸티오, n-노닐티오, n-데실티오, 벤질티오 및 p-메틸벤질티오 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkylthio group may be straight chain, branched chain, or cyclic chain. The number of carbon atoms of the alkylthio group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methylthio, ethylthio, n-propylthio, isopropylthio, i-propylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio. , isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and p-methylbenzylthio. , but is not limited to this.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, (3,3-디메틸부틸)옥시, (2-에틸부틸)옥시, (2-헥실데실)옥시, n-옥틸옥시, n-노닐옥시 및 n-데실옥시 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, (3,3-dimethylbutyl)oxy, (2-ethylbutyl)oxy, (2-hexyldecyl)oxy, n-octyloxy, n-nonyloxy and n-decyloxy. Poetry, etc., but is not limited to this.
본 명세서에 있어서, 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group may be monocyclic or polycyclic.
본 명세서에서 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기 및 터페닐기 등이 있으나, 이에 한정되는 것은 아니다. In this specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, monocyclic aryl groups include phenyl groups, biphenyl groups, and terphenyl groups, but are not limited thereto.
본 명세서에서 상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기 및 플루오레닐기 등이 있으나, 이에 한정되는 것은 아니다. 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다.In this specification, when the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms. Specifically, polycyclic aryl groups include, but are not limited to, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, and fluorenyl group. The fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 헤테로고리기의 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로 고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린(phenanthroline)기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and a heteroatom. Specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group , benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzo. furanyl groups, etc., but are not limited to these.
상기 헤테로고리기는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있다.The heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description regarding the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group.
상기 Ar1 및 Ar2에 위치하는 방향족 탄화수소고리 및 헤테로고리는 1가기인 것을 제외하며, 예컨대, 2가 이상의 아릴 또는 2가 이상의 헤테로고리일 수 있다.The aromatic hydrocarbon ring and heterocycle located at Ar1 and Ar2 are excluded from being monovalent groups, and may be, for example, a divalent or higher aryl group or a divalent or higher heterocyclic ring.
본 명세서의 일 실시상태에 있어서, 상기 L5 및 L6는 페닐렌기이다.In one embodiment of the present specification, L5 and L6 are phenylene groups.
본 명세서의 일 실시상태에 있어서, 상기 -OR9 및 -OR10는 각각 페닐렌기의 meta 위치 또는 para 위치에 치환될 수 있다. 즉, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시되는 것이다.In an exemplary embodiment of the present specification, -OR9 and -OR10 may each be substituted at the meta or para position of the phenylene group. That is, the above Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 화학식 1-1 및 1-2에서,In Formulas 1-1 and 1-2,
R1 내지 R10, L1 내지 L4, Ar1, Ar2, Y1, Y2, n 및 m은 상기 화학식 1에서 정의한 것과 동일하다.R1 to R10, L1 to L4, Ar1, Ar2, Y1, Y2, n and m are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 화학식 1-1로 표시된다. 상기 화학식 1이 화학식 1-2로 표시되는 경우(-OR9 및 -OR10가 para 위치에 치환되는 경우), 전자의 흐름이 분자 전체에 영향을 주어 HOMO 가 상대적으로 up-shift 되고 LUMO 는 down-shift 되는 경향이 있다. 반면 화학식 1이 화학식 1-1로 표시되는 경우(-OR9 및 -OR10가 meta 위치에 치환되는 경우), 이를 개선할 수 있는데, 이 경우 전자의 흐름이 분자 전체에 영향을 주지 않으므로 상대적으로 높은 LUMO 에너지 레벨을 가질 수 있으며, 이에 따라 개방전압이 높게 나타날 수 있다. In one embodiment of the present specification, Formula 1 is represented by Formula 1-1. When the above formula 1 is expressed as formula 1-2 (when -OR9 and -OR10 are substituted at the para position), the flow of electrons affects the entire molecule, causing HOMO to relatively up-shift and LUMO to down-shift. tends to be On the other hand, if Formula 1 is expressed as Formula 1-1 (-OR9 and -OR10 are substituted at the meta position), this can be improved. In this case, the flow of electrons does not affect the entire molecule, resulting in a relatively high LUMO. It may have an energy level, and accordingly, the open-circuit voltage may appear high.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L4는 각각 단환 또는 다환의 아릴렌기이다.In an exemplary embodiment of the present specification, L1 to L4 are each a monocyclic or polycyclic arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L4는 각각 탄소수 6 내지 10의 아릴렌기이다.In an exemplary embodiment of the present specification, L1 to L4 are each an arylene group having 6 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L4는 각각 페닐렌(phenylene)기이다.In an exemplary embodiment of the present specification, L1 to L4 are each a phenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L4는 각각 S 또는 Se를 포함하는 2가의 헤테로고리기이다.In an exemplary embodiment of the present specification, L1 to L4 are each divalent heterocyclic group containing S or Se.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L4는 각각 2가의 티오펜(thiophene)기이다.In an exemplary embodiment of the present specification, L1 to L4 each represent a divalent thiophene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L4는 각각 2가의 셀레노펜(selenophene)기이다.In an exemplary embodiment of the present specification, L1 to L4 each represent a divalent selenophene group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 2-1 또는 2-2로 표시되는 것이다.In one embodiment of the present specification, Formula 1 is represented by the following Formula 2-1 or 2-2.
[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
상기 화학식 2-1 및 2-2에서,In Formulas 2-1 and 2-2,
L5, L6, R1 내지 R10, Ar1, Ar2, Y1, Y2, n 및 m은 상기 화학식 1에서 정의한 것과 동일하고,L5, L6, R1 to R10, Ar1, Ar2, Y1, Y2, n and m are the same as defined in Formula 1 above,
Q1 내지 Q4는 서로 같거나 상이하며 각각 S 또는 Se이다.Q1 to Q4 are the same or different from each other and are S or Se, respectively.
본 명세서의 일 실시상태에 있어서, 상기 L5 및 L6는 각각 단환 또는 다환의 아릴렌기이다.In an exemplary embodiment of the present specification, L5 and L6 are each a monocyclic or polycyclic arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L5 및 L6는 탄소수 6 내지 10의 아릴렌기이다.In one embodiment of the present specification, L5 and L6 are arylene groups having 6 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L5 및 L6는 페닐렌기이다.In one embodiment of the present specification, L5 and L6 are phenylene groups.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 3-1 또는 3-2로 표시되는 것이다.In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 3-1 or 3-2.
[화학식 3-1][Formula 3-1]
[화학식 3-2][Formula 3-2]
상기 화학식 3-1 및 3-2에서,In Formulas 3-1 and 3-2,
R1 내지 R10, Y1, Y2, Ar1, Ar2, n 및 m은 상기 화학식 1에서 정의한 것과 동일하고, Q1 내지 Q4는 서로 같거나 상이하며 각각 S 또는 Se이다.R1 to R10, Y1, Y2, Ar1, Ar2, n and m are the same as defined in Formula 1 above, and Q1 to Q4 are the same or different from each other and are S or Se, respectively.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 단환 또는 다환의 방향족 탄화수소고리이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are monocyclic or polycyclic aromatic hydrocarbon rings.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 치환 또는 비치환된 벤젠고리이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are substituted or unsubstituted benzene rings.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 치환 또는 비치환된 나프탈렌고리이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are substituted or unsubstituted naphthalene rings.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 치환 또는 비치환된 티오펜이다.In one embodiment of the present specification, Ar1 and Ar2 are substituted or unsubstituted thiophene.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 4-1 내지 4-4 중 어느 하나로 표시되는 것이다.In one embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 4-1 to 4-4.
[화학식 4-1][Formula 4-1]
[화학식 4-2][Formula 4-2]
[화학식 4-3][Formula 4-3]
[화학식 4-4][Formula 4-4]
상기 화학식 4-1 내지 4-4에서,In Formulas 4-1 to 4-4,
R1 내지 R10, L1 내지 L4, Y1, Y2, n 및 m은 상기 화학식 1에서 정의한 것과 동일하고,R1 to R10, L1 to L4, Y1, Y2, n and m are the same as defined in Formula 1 above,
R15 내지 R22은 서로 같거나 상이하며 각각 수소; 또는 치환 또는 비치환된 알킬기이다.R15 to R22 are the same or different from each other and are each hydrogen; Or it is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 5-1 내지 5-8 중 어느 하나로 표시되는 것이다.In one embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 5-1 to 5-8.
[화학식 5-1][Formula 5-1]
[화학식 5-2][Formula 5-2]
[화학식 5-3][Formula 5-3]
[화학식 5-4][Formula 5-4]
[화학식 5-5][Formula 5-5]
[화학식 5-6][Formula 5-6]
[화학식 5-7][Formula 5-7]
[화학식 5-8][Formula 5-8]
상기 화학식 5-1 내지 5-8에서,In Formulas 5-1 to 5-8,
R1 내지 R10, Y1, Y2, n 및 m은 상기 화학식 1에서 정의한 것과 동일하고,R1 to R10, Y1, Y2, n and m are the same as defined in Formula 1 above,
R15 내지 R22은 서로 같거나 상이하며 각각 수소; 또는 치환 또는 비치환된 알킬기이며,R15 to R22 are the same or different from each other and are each hydrogen; Or a substituted or unsubstituted alkyl group,
Q1 내지 Q4는 서로 같거나 상이하며 각각 S 또는 Se이다.Q1 to Q4 are the same or different from each other and are S or Se, respectively.
본 명세서의 일 실시상태에 있어서, 상기 Q1 내지 Q4는 각각 S이다.In an exemplary embodiment of the present specification, Q1 to Q4 are each S.
본 명세서의 일 실시상태에 있어서, 상기 Y1 및 Y2는 각각 수소이다.In an exemplary embodiment of the present specification, Y1 and Y2 are each hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 Y1 및 Y2는 각각 탄소수 1 내지 10의 직쇄의 알킬기이다.In one embodiment of the present specification, Y1 and Y2 are each a straight-chain alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Y1 및 Y2는 각각 메틸기이다.In an exemplary embodiment of the present specification, Y1 and Y2 are each a methyl group.
본 명세서의 일 실시상태에 있어서, 상기 Y1 및 Y2는 각각 불소, 염소 또는 브롬이다.In an exemplary embodiment of the present specification, Y1 and Y2 are each fluorine, chlorine, or bromine.
본 명세서의 일 실시상태에 있어서, 상기 Y1 및 Y2는 각각 불소이다.In an exemplary embodiment of the present specification, Y1 and Y2 are each fluorine.
본 명세서의 일 실시상태에 있어서, 상기 Y1 및 Y2는 각각 염소이다.In an exemplary embodiment of the present specification, Y1 and Y2 are each chlorine.
본 명세서의 일 실시상태에 있어서, 상기 n 및 m은 각각 0 내지 4의 정수이다.In an exemplary embodiment of the present specification, n and m are each integers from 0 to 4.
본 명세서의 일 실시상태에 있어서, 상기 n 및 m은 각각 0 내지 2의 정수이다.In an exemplary embodiment of the present specification, n and m are each integers from 0 to 2.
본 명세서의 일 실시상태에 있어서, 상기 n 및 m은 각각 1이다.In an exemplary embodiment of the present specification, n and m are each 1.
본 명세서의 일 실시상태에 있어서, 상기 n 및 m은 각각 2이다.In an exemplary embodiment of the present specification, n and m are each 2.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 각각 치환 또는 비치환된 알킬기이다.In an exemplary embodiment of the present specification, R1 to R4 are each a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 각각 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.In an exemplary embodiment of the present specification, R1 to R4 are each a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 각각 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기이다.In one embodiment of the present specification, R1 to R4 are each a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 각각 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기이다.In an exemplary embodiment of the present specification, R1 to R4 are each a straight-chain or branched alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 각각 탄소수 1 내지 10의 직쇄의 알킬기이다.In an exemplary embodiment of the present specification, R1 to R4 are each a straight-chain alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R4는 각각 헥실기이다.In one embodiment of the present specification, R1 to R4 are each a hexyl group.
본 명세서의 일 실시상태에 있어서, 상기 R5 내지 R8은 각각 수소이다.In one embodiment of the present specification, R5 to R8 are each hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 탄소수 1내지 30의 직쇄 또는 분지쇄의 알킬기 이다. In an exemplary embodiment of the present specification, R9 and R10 are each a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 탄소수 3 내지 15의 직쇄 또는 분지쇄의 알킬기이다.In an exemplary embodiment of the present specification, R9 and R10 are each a straight-chain or branched alkyl group having 3 to 15 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 탄소수 5 내지 10의 직쇄 또는 분지쇄의 알킬기이다.In an exemplary embodiment of the present specification, R9 and R10 are each a straight-chain or branched alkyl group having 5 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 탄소수 5 내지 10의 분지쇄의 알킬기이다.In an exemplary embodiment of the present specification, R9 and R10 are each a branched alkyl group having 5 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 에틸헥실 (ethylhexyl) 이다.In an exemplary embodiment of the present specification, R9 and R10 are each ethylhexyl.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 단환 또는 다환의 아릴기이다.In an exemplary embodiment of the present specification, R9 and R10 are each a monocyclic or polycyclic aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 탄소수 6 내지 10의 아릴기이다.In an exemplary embodiment of the present specification, R9 and R10 are each an aryl group having 6 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R9 및 R10은 각각 페닐기이다.In an exemplary embodiment of the present specification, R9 and R10 are each a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R15 내지 R22는 각각 수소이다.In an exemplary embodiment of the present specification, R15 to R22 are each hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R15 및 R17은 각각 탄소수 1 내지 10의 직쇄의 알킬기이다.In one embodiment of the present specification, R15 and R17 are each a straight-chain alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R15 및 R17은 각각 메틸기이다.In an exemplary embodiment of the present specification, R15 and R17 are each a methyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 6-1 내지 6-60 중 선택된 어느 하나이다.In an exemplary embodiment of the present specification, Formula 1 is any one selected from Formulas 6-1 to 6-60 below.
[화학식 6-1][Formula 6-1]
[화학식 6-2][Formula 6-2]
[화학식 6-3][Formula 6-3]
[화학식 6-4][Formula 6-4]
[화학식 6-5][Formula 6-5]
[화학식 6-6][Formula 6-6]
[화학식 6-7][Formula 6-7]
[화학식 6-8][Formula 6-8]
[화학식 6-9][Formula 6-9]
[화학식 6-10][Formula 6-10]
[화학식 6-11][Formula 6-11]
[화학식 6-12][Formula 6-12]
[화학식 6-13][Formula 6-13]
[화학식 6-14][Formula 6-14]
[화학식 6-15][Formula 6-15]
[화학식 6-16][Formula 6-16]
[화학식 6-17][Formula 6-17]
[화학식 6-18][Formula 6-18]
[화학식 6-19][Formula 6-19]
[화학식 6-20][Formula 6-20]
[화학식 6-21][Formula 6-21]
[화학식 6-22][Formula 6-22]
[화학식 6-23][Formula 6-23]
[화학식 6-24][Formula 6-24]
[화학식 6-25][Formula 6-25]
[화학식 6-26][Formula 6-26]
[화학식 6-27][Formula 6-27]
[화학식 6-28][Formula 6-28]
[화학식 6-29][Formula 6-29]
[화학식 6-30][Formula 6-30]
[화학식 6-31][Formula 6-31]
[화학식 6-32][Formula 6-32]
[화학식 6-33][Formula 6-33]
[화학식 6-34][Formula 6-34]
[화학식 6-35][Formula 6-35]
[화학식 6-36][Formula 6-36]
[화학식 6-37][Formula 6-37]
[화학식 6-38][Formula 6-38]
[화학식 6-39][Formula 6-39]
[화학식 6-40][Formula 6-40]
[화학식 6-41][Formula 6-41]
[화학식 6-42][Formula 6-42]
[화학식 6-43][Formula 6-43]
[화학식 6-44][Formula 6-44]
[화학식 6-45][Formula 6-45]
[화학식 6-46][Formula 6-46]
[화학식 6-47][Formula 6-47]
[화학식 6-48][Formula 6-48]
[화학식 6-49][Formula 6-49]
[화학식 6-50][Formula 6-50]
[화학식 6-51][Formula 6-51]
[화학식 6-52][Formula 6-52]
[화학식 6-53][Formula 6-53]
[화학식 6-54][Formula 6-54]
[화학식 6-55][Formula 6-55]
[화학식 6-56][Formula 6-56]
[화학식 6-57][Formula 6-57]
[화학식 6-58][Formula 6-58]
[화학식 6-59][Formula 6-59]
[화학식 6-60][Formula 6-60]
상기 화학식 6-1 내지 6-60에서, 와 같이 표시된 구조를 포함하는 경우, Y1이 5번 위치에 치환된 화합물과 6번 위치에 치환된 화합물이 혼합되어 있음을 의미하며, Y1이 5번 위치에 치환된 화합물과 Y1이 6번 위치에 치환된 화합물의 질량비는 1:9 내지 9:1, 구체적으로 7:3일 수 있다.In Formulas 6-1 to 6-60, If it contains a structure shown as, it means that a compound with Y1 substituted at position 5 and a compound with Y1 substituted at position 6 are mixed, and a compound with Y1 substituted at position 5 and a compound with Y1 substituted at position 6 The mass ratio of the substituted compound may be 1:9 to 9:1, specifically 7:3.
본 명세서의 일 실시상태에 있어서, 상기 헤테로환 화합물은 300nm 내지 900nm의 흡수 영역을 나타내고, 바람직하게는 700nm 내지 900nm에서 최대 흡수 파장을 가진다.In one embodiment of the present specification, the heterocyclic compound exhibits an absorption region of 300 nm to 900 nm, and preferably has a maximum absorption wavelength of 700 nm to 900 nm.
이에 따라, 유기 전자 소자에 적용시 전자 주개의 흡수 영역(300nm 내지 700nm)과 상보적인 흡수를 나타내어 유기 전자 소자에 적용시 높은 단락전류를 나타낼 수 있다.Accordingly, when applied to an organic electronic device, it exhibits complementary absorption to the absorption region (300 nm to 700 nm) of the electron donor, and thus can exhibit a high short-circuit current when applied to an organic electronic device.
본 명세서의 일 실시상태에 있어서, 상기 헤테로환 화합물은 가시광선 전파장 영역의 광 흡수가 가능하며, 적외선 영역의 광도 흡수할 수 있다. 이에 따라, 소자의 흡수 파장 범위가 넓은 효과를 나타낼 수 있다.In one embodiment of the present specification, the heterocyclic compound is capable of absorbing light in the visible light full-wave range and can also absorb light in the infrared range. Accordingly, the effect of having a wide absorption wavelength range of the device can be achieved.
본 명세서의 일 실시상태는 상기 헤테로환 화합물을 포함하는 유기 전자 소자의 유기활성층 형성용 조성물을 제공한다.An exemplary embodiment of the present specification provides a composition for forming an organic active layer of an organic electronic device containing the heterocyclic compound.
본 명세서의 일 실시상태에 있어서, 상기 헤테로환 화합물은 상기 조성물 100wt%를 기준으로 0.5wt% 내지 3wt%, 바람직하게는 1wt% 내지 1.5wt%의 함량으로 포함된다.In one embodiment of the present specification, the heterocyclic compound is included in an amount of 0.5 wt% to 3 wt%, preferably 1 wt% to 1.5 wt%, based on 100 wt% of the composition.
중합체의 함량이 3wt%를 초과할 경우, 용해도 문제로 인해 깨끗한 박막 형성이 어려운 단점이 있다.When the polymer content exceeds 3 wt%, there is a disadvantage in that it is difficult to form a clean thin film due to solubility problems.
본 명세서의 일 실시상태에 있어서, 상기 조성물은 후술하는 전자 주개 물질을 더 포함할 수 있으며, 상기 조성물 100wt%를 기준으로 상기 전자 주개 물질의 함량은 1wt% 내지 3wt%이다. In one embodiment of the present specification, the composition may further include an electron donor material to be described later, and the content of the electron donor material is 1 wt% to 3 wt% based on 100 wt% of the composition.
본 명세서의 일 실시상태에 있어서, 상기 조성물은 용매로서 톨루엔(toluene) 및 자일렌(xylene) 중 선택되는 1종 이상을 더 포함할 수 있으나 이에 한정되는 것은 아니며, 상기 조성물 중 상기 헤테로환 화합물 및 전자 주개 물질을 제외한 잔부는 모두 용매이다.In an exemplary embodiment of the present specification, the composition may further include, but is not limited to, one or more solvents selected from toluene and xylene, and the heterocyclic compound and Everything remaining except the electron donor material is the solvent.
본 명세서의 일 실시상태는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비되고, 유기활성층을 포함하는 1층 이상의 유기물층을 포함하며, 상기 유기활성층은 상기 헤테로환 화합물을 포함하는 것인 유기 전자 소자를 제공한다.An exemplary embodiment of the present specification includes a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode and including an organic active layer, wherein the organic active layer includes the heterocyclic compound.
또한, 본 명세서의 일 실시상태는 기판 상에 제1 전극을 형성하는 단계; 상기 제1 전극 상에 유기활성층을 포함하는 1층 이상의 유기물층을 형성하는 단계; 및 상기 유기물층 상에 제2 전극을 형성하는 단계를 포함하고, 상기 유기활성층은 상기 헤테로환 화합물을 포함하는 것인 유기 전자 소자의 제조 방법을 제공한다.Additionally, an exemplary embodiment of the present specification includes forming a first electrode on a substrate; forming one or more organic layers including an organic active layer on the first electrode; and forming a second electrode on the organic material layer, wherein the organic active layer includes the heterocyclic compound.
본 명세서의 일 실시상태에 있어서, 상기 유기 전자 소자의 제조 방법은 상기 제1 전극 상에 전자수송층을 형성하는 단계를 더 포함할 수 있다.In one embodiment of the present specification, the method of manufacturing the organic electronic device may further include forming an electron transport layer on the first electrode.
본 명세서의 일 실시상태에 있어서, 상기 유기물층을 형성하는 단계는 스핀-코팅(spin-coating), 슬롯다이, 블레이드 코팅 또는 롤투롤 코팅 방식으로 수행되며, 상기 스핀-코팅 속도는 700rpm 내지 1,300rpm일 수 있다.In one embodiment of the present specification, the step of forming the organic material layer is performed by spin-coating, slot die, blade coating, or roll-to-roll coating, and the spin-coating speed is 700 rpm to 1,300 rpm. You can.
스핀-코팅의 속도가 상기 범위에 있을 때, 유기활성층의 두께가 100nm 내외로 형성되어 유기 전자 소자의 성능이 향상될 수 있다.When the spin-coating speed is within the above range, the thickness of the organic active layer can be formed to be about 100 nm, thereby improving the performance of the organic electronic device.
본 발명의 유기 전자 소자는 상기 화학식 1로 표시되는 헤테로환 화합물이 유기활성층에 포함되는 것을 제외하고는, 통상의 유기 전자 소자의 제조 방법 및 재료에 의하여 제조될 수 있다.The organic electronic device of the present invention can be manufactured by conventional organic electronic device manufacturing methods and materials, except that the heterocyclic compound represented by Formula 1 is included in the organic active layer.
본 명세서의 일 실시상태에 있어서, 상기 유기활성층은 전자 주개 및 전자 받개를 포함하며, 상기 전자 받개는 상기 헤테로환 화합물을 포함한다.In one embodiment of the present specification, the organic active layer includes an electron donor and an electron acceptor, and the electron acceptor includes the heterocyclic compound.
본 명세서에 있어서, 유기활성층은 광활성층 또는 발광층일 수 있다.In this specification, the organic active layer may be a photoactive layer or a light-emitting layer.
본 명세서에 있어서, 상기 유기 전자 소자는 유기 태양 전지, 유기 광전 소자, 유기 발광 소자, 유기 감광체(OPC) 또는 유기 트랜지스터일 수 있다. In the present specification, the organic electronic device may be an organic solar cell, an organic photoelectric device, an organic light-emitting device, an organic photoreceptor (OPC), or an organic transistor.
이하에서는, 유기 태양 전지에 대하여 예시한다. 상기 유기 태양 전지에서 유기활성층은 광활성층이며, 전술한 유기 전자 소자는 후술하는 유기 태양 전지에 대한 설명을 인용할 수 있다.Below, organic solar cells will be exemplified. In the organic solar cell, the organic active layer is a photoactive layer, and the above-mentioned organic electronic device can be referred to the description of the organic solar cell described later.
본 명세서의 일 실시상태는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비되고, 광활성층을 포함하는 1층 이상의 유기물층을 포함하며, 상기 광활성층은 상기 헤테로환 화합물을 포함하는 것인 유기 태양 전지를 제공한다.An exemplary embodiment of the present specification includes a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode and including a photoactive layer, wherein the photoactive layer includes the heterocyclic compound.
상기 유기 태양 전지는 기판, 정공수송층, 정공주입층, 전자주입층 및/또는 전자수송층을 더 포함할 수 있다.The organic solar cell may further include a substrate, a hole transport layer, a hole injection layer, an electron injection layer, and/or an electron transport layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 부가적인 유기물층을 더 포함할 수 있다. 상기 유기 태양 전지는 여러 기능을 동시에 갖는 유기물을 사용하여 유기물층의 수를 감소시킬 수 있다.In one embodiment of the present specification, the organic solar cell may further include an additional organic material layer. The organic solar cell can reduce the number of organic material layers by using organic materials that have multiple functions simultaneously.
본 명세서의 일 실시상태에 있어서, 상기 광활성층은 전자 주개 및 전자 받개를 포함하고, 상기 전자 받개는 상기 헤테로환 화합물을 포함한다.In one embodiment of the present specification, the photoactive layer includes an electron donor and an electron acceptor, and the electron acceptor includes the heterocyclic compound.
본 명세서의 일 실시상태에 있어서, 상기 전자 주개는 당 기술 분야에서 적용되는 물질을 사용할 수 있으며, 예컨대, 폴리 3-헥실 티오펜(P3HT: poly 3-hexyl thiophene), PCDTBT(poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4'-7'-di-2-thienyl-2',1',3'-benzothiadiazole)]), PCPDTBT(poly[2,6-(4,4-bis-(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)]), PFO-DBT(poly[2,7-(9,9-dioctylfluorene)-alt-5,5-(4,7-bis(thiophene-2-yl)benzo-2,1,3-thiadiazole)]), PTB7(Poly[[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl][3-fluoro-2-[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl]]), PSiF-DBT(Poly[2,7-(9,9-dioctyl-dibenzosilole)-alt-4,7-bis(thiophen-2-yl)benzo-2,1,3-thiadiazole]), PTB7-Th(Poly[4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b;4,5-b']dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene-)-2-carboxylate-2-6-diyl)]) 및 PBDB-T(poly(benzodithiophene-benzotriazole)로 이루어진 군에서 선택되는 1종 이상의 물질을 포함할 수 있다.In one embodiment of the present specification, the electron donor may use a material applied in the art, for example, poly 3-hexyl thiophene (P3HT), poly[N-9 (PCDTBT) '-heptadecanyl-2,7-carbazole-alt-5,5-(4'-7'-di-2-thienyl-2',1',3'-benzothiadiazole)]), PCPDTBT(poly[2,6 -(4,4-bis-(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] ), PFO-DBT(poly[2,7-(9,9-dioctylfluorene)-alt-5,5-(4,7-bis(thiophene-2-yl)benzo-2,1,3-thiadiazole)] ), PTB7 (Poly[[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl][3-fluoro-2- [(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl]]), PSiF-DBT(Poly[2,7-(9,9-dioctyl-dibenzosilole)-alt-4,7-bis(thiophen -2-yl)benzo-2,1,3-thiadiazole]), PTB7-Th(Poly[4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b; 4,5-b']dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene-)-2-carboxylate-2-6-diyl) ]) and PBDB-T (poly(benzodithiophene-benzotriazole)).
본 명세서의 일 실시상태에 있어서, 상기 전자 주개는 PBDB-T이다. 상기 전자 주개와 상기 전자 받개의 질량비는 1:2 내지 2:1 일 수 있으며, 바람직하게는 1:1.5 내지 1.5:1, 더욱 바람직하게는 1:1이다.In one embodiment of the present specification, the electron donor is PBDB-T. The mass ratio of the electron donor and the electron acceptor may be 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.
본 명세서의 일 실시상태에 있어서, 상기 전자 주개 및 전자 받개는 벌크 헤테로 정션(BHJ)을 구성할 수 있다. 벌크 헤테로 정션이란 광활성층에서 전자 주개 물질과 전자 받개 물질이 서로 섞여 있는 것을 의미한다.In one embodiment of the present specification, the electron donor and electron acceptor may form a bulk heterojunction (BHJ). Bulk heterojunction means that electron donor materials and electron acceptor materials are mixed together in the photoactive layer.
본 명세서의 일 실시상태에 있어서, 상기 전자 주개는 p형 유기물층이고, 상기 전자 받개는 n형 유기물층이다.In one embodiment of the present specification, the electron donor is a p-type organic material layer, and the electron acceptor is an n-type organic material layer.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 애노드이고, 상기 제2 전극은 캐소드이다. 또 하나의 실시상태에 있어서, 상기 제1 전극은 캐소드이고, 상기 제2 전극은 애노드이다. In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode. In another embodiment, the first electrode is a cathode and the second electrode is an anode.
또 하나의 실시상태에 있어서, 상기 유기 태양 전지는 애노드, 정공수송층, 광활성층, 전자수송층 및 캐소드 순으로 배열될 수도 있고, 캐소드, 전자수송층, 광활성층, 정공수송층 및 애노드 순으로 배열될 수도 있으나, 이에 한정되지 않는다.In another embodiment, the organic solar cell may be arranged in the following order: an anode, hole transport layer, photoactive layer, electron transport layer, and cathode, or may be arranged in the order of cathode, electron transport layer, photoactive layer, hole transport layer, and anode. , but is not limited to this.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 노멀(Normal)구조이다. 상기 노멀구조에서는 기판, 제1 전극, 정공수송층, 광활성층을 포함하는 유기물층, 전자수송층 및 제2 전극의 순서로 적층될 수 있다. In one embodiment of the present specification, the organic solar cell has a normal structure. In the normal structure, a substrate, a first electrode, a hole transport layer, an organic material layer including a photoactive layer, an electron transport layer, and a second electrode may be stacked in that order.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 인버티드(Inverted) 구조이다. 상기 인버티드 구조에서는 기판, 제1 전극, 전자수송층, 광활성층을 포함하는 유기물층, 정공수송층 및 제2 전극의 순서로 적층될 수 있다. In one embodiment of the present specification, the organic solar cell has an inverted structure. In the inverted structure, a substrate, a first electrode, an electron transport layer, an organic material layer including a photoactive layer, a hole transport layer, and a second electrode may be stacked in that order.
도 1은 본 명세서의 일 실시상태에 따른 유기 태양 전지를 나타낸 도이다. 도 1에 따르면, 유기 태양 전지는 제1 전극(100) 및/또는 제2 전극(300) 측으로부터 빛이 입사되어 광활성층(200)이 전 파장 영역의 빛을 흡수하면 내부에서 엑시톤이 생성될 수 있다. 엑시톤은 광활성층(200)에서 정공과 전자로 분리되고, 분리된 정공은 제1 전극(100)과 제2 전극(300) 중 하나인 애노드 측으로 이동하고 분리된 전자는 제1 전극(100)과 제2 전극(300) 중 다른 하나인 캐소드 측으로 이동하여 유기 태양 전지에 전류가 흐를 수 있게 된다.1 is a diagram showing an organic solar cell according to an exemplary embodiment of the present specification. According to FIG. 1, when light is incident from the first electrode 100 and/or the second electrode 300 and the photoactive layer 200 absorbs light in the entire wavelength range, an exciton is generated inside the organic solar cell. You can. Exciton is separated into holes and electrons in the photoactive layer 200, the separated holes move to the anode side, which is one of the first electrode 100 and the second electrode 300, and the separated electrons move to the first electrode 100 and the anode. It moves to the cathode side, which is the other one of the second electrodes 300, so that current can flow through the organic solar cell.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 탠덤(tandem)구조이다. 이 경우 상기 유기 태양 전지는 2 층 이상의 광활성층을 포함할 수 있다. In one embodiment of the present specification, the organic solar cell has a tandem structure. In this case, the organic solar cell may include two or more photoactive layers.
본 명세서의 일 실시상태에 따른 유기 태양 전지는 광활성층이 1층 또는 2층 이상일 수 있다.The organic solar cell according to an exemplary embodiment of the present specification may have one or two or more layers of photoactive layers.
또 하나의 일 실시상태에 있어서, 버퍼층이 광활성층과 정공수송층 사이 또는 광활성층과 전자수송층 사이에 구비될 수 있다. 이때, 정공주입층이 애노드와 정공수송층 사이에 더 구비될 수 있다. 또한, 전자주입층이 캐소드와 전자수송층 사이에 더 구비될 수 있다.In another embodiment, a buffer layer may be provided between the photoactive layer and the hole transport layer or between the photoactive layer and the electron transport layer. At this time, a hole injection layer may be further provided between the anode and the hole transport layer. Additionally, an electron injection layer may be further provided between the cathode and the electron transport layer.
본 명세서의 일 실시상태에 있어서, 상기 기판은 투명성, 표면평활성, 취급용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 될 수 있으나, 이에 한정되지 않으며, 유기 태양 전지에 통상적으로 사용되는 기판이면 제한되지 않는다. 구체적으로 유리, PET(polyethylene terephthalate), PEN(polyethylene naphthalate), PP(polypropylene), PI(polyimide) 및 TAC(triacetyl cellulose) 등이 있으나. 이에 한정되는 것은 아니다. In one embodiment of the present specification, the substrate may be a glass substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto, and is limited to any substrate commonly used in organic solar cells. It doesn't work. Specifically, there are glass, PET (polyethylene terephthalate), PEN (polyethylene naphthalate), PP (polypropylene), PI (polyimide), and TAC (triacetyl cellulose). It is not limited to this.
상기 제1 전극의 재료는 투명하고 전도성이 우수한 물질이 될 수 있으나, 이에 한정되지 않는다. 예컨대, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 및 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The material of the first electrode may be a transparent and highly conductive material, but is not limited thereto. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited to these. .
상기 제1 전극의 형성 방법은 특별히 한정되지 않으나, 예컨대 스퍼터링, E-빔, 열증착, 스핀코팅, 스크린 프린팅, 잉크젯 프린팅, 닥터 블레이드 또는 그라비아 프린팅법을 사용할 수 있다.The method of forming the first electrode is not particularly limited, but for example, sputtering, E-beam, thermal evaporation, spin coating, screen printing, inkjet printing, doctor blade, or gravure printing can be used.
상기 제1 전극을 기판 상에 형성하는 경우, 이는 세정, 수분제거 및 친수성 개질 과정을 거칠 수 있다.When forming the first electrode on a substrate, it may undergo cleaning, moisture removal, and hydrophilic modification processes.
예컨대, 패터닝된 ITO 기판을 세정제, 아세톤, 이소프로필 알코올(IPA)로 순차적으로 세정한 다음, 수분 제거를 위해 가열판에서 100℃ 내지 150℃에서 1분 내지 30분간, 바람직하게는 120℃에서 10분간 건조하고, 기판이 완전히 세정되면 기판 표면을 친수성으로 개질한다.For example, the patterned ITO substrate was sequentially cleaned with a detergent, acetone, and isopropyl alcohol (IPA), and then washed on a heating plate at 100°C to 150°C for 1 minute to 30 minutes, preferably at 120°C for 10 minutes to remove moisture. After drying and completely cleaning the substrate, the surface of the substrate is modified to be hydrophilic.
상기와 같은 표면 개질을 통해 접합 표면 전위를 광활성층의 표면 전위에 적합한 수준으로 유지할 수 있다. 또한, 개질 시 제1 전극 위에 고분자 박막의 형성이 용이해지고, 박막의 품질이 향상될 수도 있다. Through the surface modification described above, the bonding surface potential can be maintained at a level suitable for the surface potential of the photoactive layer. Additionally, during modification, the formation of a polymer thin film on the first electrode may become easier and the quality of the thin film may be improved.
제1 전극의 전 처리 기술로는 a) 평행 평판형 방전을 이용한 표면 산화법, b) 진공상태에서 UV 자외선을 이용하여 생성된 오존을 통해 표면을 산화하는 방법, 및 c) 플라즈마에 의해 생성된 산소 라디칼을 이용하여 산화하는 방법 등이 있다.Pretreatment technologies for the first electrode include a) a surface oxidation method using parallel plate discharge, b) a method of oxidizing the surface through ozone generated using UV ultraviolet rays in a vacuum, and c) oxygen generated by plasma. There is a method of oxidation using radicals.
제1 전극 또는 기판의 상태에 따라 상기 방법 중 한가지를 선택할 수 있다. 다만, 어느 방법을 이용하든지 공통적으로 제1 전극 또는 기판 표면의 산소이탈을 방지하고 수분 및 유기물의 잔류를 최대한 억제하는 것이 바람직하다. 이 때, 전 처리의 실질적인 효과를 극대화할 수 있다. One of the above methods can be selected depending on the state of the first electrode or substrate. However, whichever method is used, it is generally desirable to prevent oxygen escape from the surface of the first electrode or substrate and to suppress the remaining moisture and organic matter as much as possible. At this time, the practical effect of pre-processing can be maximized.
구체적인 예로서, UV를 이용하여 생성된 오존을 통해 표면을 산화하는 방법을 사용할 수 있다. 이 때, 초음파 세정 후 패터닝된 ITO 기판을 가열판(hot plate)에서 베이킹(baking)하여 잘 건조시킨 다음, 챔버에 투입하고, UV 램프를 작용시켜 산소 가스가 UV 광과 반응하여 발생하는 오존에 의하여 패터닝된 ITO 기판을 세정할 수 있다. As a specific example, a method of oxidizing the surface through ozone generated using UV light can be used. At this time, after ultrasonic cleaning, the patterned ITO substrate is baked on a hot plate and dried well, then placed in a chamber, and a UV lamp is applied to produce ozone generated when oxygen gas reacts with UV light. The patterned ITO substrate can be cleaned.
그러나, 본 명세서에 있어서의 패터닝된 ITO 기판의 표면 개질 방법은 특별히 한정시킬 필요는 없으며, 기판을 산화시키는 방법이라면 어떠한 방법도 무방하다.However, the method for modifying the surface of the patterned ITO substrate in this specification does not need to be particularly limited, and any method may be used as long as it oxidizes the substrate.
상기 제2 전극은 일함수가 작은 금속이 될 수 있으나, 이에 한정되지 않는다. 구체적으로 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; 또는 LiF/Al, LiO2/Al, LiF/Fe, Al:Li, Al:BaF2, Al:BaF2:Ba와 같은 다층 구조의 물질이 될 수 있으나, 이에 한정되는 것은 아니다. The second electrode may be a metal with a low work function, but is not limited thereto. Specifically, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; Alternatively, it may be a multi-layered material such as LiF/Al, LiO 2 /Al, LiF/Fe, Al:Li, Al:BaF 2 , Al:BaF 2 :Ba, but is not limited thereto.
상기 제2 전극은 5 ×10-7torr 이하의 진공도를 보이는 열증착기 내부에서 증착되어 형성될 수 있으나, 이 방법에만 한정되는 것은 아니다.The second electrode may be formed by depositing inside a thermal evaporator with a vacuum of 5 × 10 -7 torr or less, but the method is not limited to this method.
상기 정공수송층 및/또는 전자수송층 물질은 광활성층에서 분리된 전자와 정공을 전극으로 효율적으로 전달시키는 역할을 담당하며, 물질을 특별히 제한하지는 않는다. The hole transport layer and/or electron transport layer material serves to efficiently transfer electrons and holes separated from the photoactive layer to the electrode, and the material is not particularly limited.
상기 정공수송층 물질은 PEDOT:PSS(Poly(3,4-ethylenediocythiophene) doped with poly(styrenesulfonic acid)), 몰리브데늄 산화물(MoOx); 바나듐 산화물(V2O5); 니켈 산화물(NiO); 및 텅스텐 산화물(WOx) 등이 될 수 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer material includes PEDOT:PSS (Poly(3,4-ethylenediocythiophene) doped with poly(styrenesulfonic acid)), molybdenum oxide (MoO x ); vanadium oxide (V 2 O 5 ); Nickel oxide (NiO); and tungsten oxide (WO x ), but is not limited to these.
상기 전자수송층 물질은 BCP(bathocuproine) 또는 전자추출금속 산화물(electron-extracting metal oxides)이 될 수 있으며, 구체적으로 BCP(bathocuproine), 8-히드록시퀴놀린의 금속착물; Alq3를 포함한 착물; Liq를 포함한 금속착물; LiF; Ca; 티타늄 산화물(TiOx); 아연 산화물(ZnO); 및 세슘 카보네이트(Cs2CO3) 등이 될 수 있으나, 이들에만 한정되는 것은 아니다.The electron transport layer material may be BCP (bathocuproine) or electron-extracting metal oxides, and specifically, BCP (bathocuproine), a metal complex of 8-hydroxyquinoline; Complex containing Alq 3 ; Metal complexes containing Liq; LIF; Ca; Titanium oxide (TiO x ); zinc oxide (ZnO); and cesium carbonate (Cs 2 CO 3 ), but is not limited to these.
본 명세서의 일 실시상태에 있어서, 상기 광활성층을 형성하는 방법으로는 진공 증착법 또는 용액 도포법을 사용할 수 있으며, 용액 도포법이라 함은 전자공여체 및/또는 전자수용체와 같은 광활성 물질을 유기용매에 용해시킨 후 용액을 스핀 코팅, 딥코팅, 스크린 프린팅, 스프레이 코팅, 닥터 블레이드 및 브러쉬 페인팅 등의 방법으로 도포하는 방법을 의미하나, 이들 방법에만 한정되는 것은 아니다.In one embodiment of the present specification, a vacuum deposition method or a solution application method may be used as a method of forming the photoactive layer, and the solution application method refers to adding a photoactive material such as an electron donor and/or an electron acceptor in an organic solvent. This refers to a method of dissolving and then applying the solution using methods such as spin coating, dip coating, screen printing, spray coating, doctor blade, and brush painting, but is not limited to these methods.
본 명세서의 일 실시상태에 따른 화합물은 후술하는 제조 방법으로 제조될 수 있다. 후술하는 제조예들에서는 대표적인 예시들을 기재하지만, 필요에 따라, 치환기를 추가하거나 제외할 수 있으며, 치환기의 위치를 변경할 수 있다. 또한, 당 기술분야에 알려져 있는 기술을 기초로, 출발물질, 반응물질 및 반응 조건 등을 변경할 수 있다.A compound according to an exemplary embodiment of the present specification may be produced by a production method described later. Representative examples are described in the production examples described below, but as needed, substituents can be added or excluded, and the positions of the substituents can be changed. Additionally, starting materials, reactants, reaction conditions, etc. can be changed based on techniques known in the art.
또한, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세히 설명한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지는 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.In addition, in order to explain the present specification in detail, examples will be given in detail. However, the embodiments according to the present specification may be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described in detail below. The embodiments of this specification are provided to more completely explain the present specification to those with average knowledge in the art.
<제조예 : 화합물 1 내지 60의 합성><Preparation example: Synthesis of compounds 1 to 60>
제조예 1. 화합물 1 내지 10의 제조Preparation Example 1. Preparation of compounds 1 to 10
(1) 화합물 A의 제조(1) Preparation of Compound A
콘덴서가 장착된 둥근 플라스크에 (4,8-bis(4-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) 10g 을 Pd2(dba)3 0.43g 및 트리(o-톨릴)포스핀(Tri(o-tolyl)phosphine) 0.57g와 함께 톨루엔 150mL에 녹인 후 환류시켰다. 온도가 100℃가 되었을 때 에틸 2-브로모티오펜-3-카복실레이트(ethyl 2-bromothiophene-3-carboxylate) 5.15g(2.5eq)을 톨루엔 5mL 에 녹여 천천히 주입한 후 12시간 동안 환류시켰다. 반응이 종료된 후, 컬럼크로마토크래피를 통해 상기 화합물 A(diethyl 2,2'-(4,8-bis(4-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(thiophene-3-carboxylate))를 수득하였다.(4,8-bis(4-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis in a round flask equipped with a condenser. (trimethylstannane) 10g was dissolved in 150mL of toluene along with 0.43g of Pd 2 (dba) 3 and 0.57g of tri(o-tolyl)phosphine and then refluxed. When the temperature reached 100°C, 5.15 g (2.5 eq) of ethyl 2-bromothiophene-3-carboxylate was dissolved in 5 mL of toluene, slowly injected, and refluxed for 12 hours. After the reaction was completed, the compound A (diethyl 2,2'-(4,8-bis(4-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4) was obtained through column chromatography. ,5-b']dithiophene-2,6-diyl)bis(thiophene-3-carboxylate)) was obtained.
(2) 화합물 B의 제조(2) Preparation of Compound B
둥근 플라스크에서 1-브로모-4-헥실벤젠(1-bromo-4-hexylbenzene) 8.16g (5.3eq)을 THF 200mL에 녹인 후 -78℃에서 n-BuLi 13.5mL를 천천히 주입한 후 1시간 동안 같은 온도에서 교반시켰다. (1)에서 제조한 화합물 A를 THF 50mL에 녹인 후 교반 중인 둥근 플라스크에 천천히 주입한 후 상온에서 12시간 동안 교반시켰다. 클로로포름을 통해 유기층을 추출한 후 용매를 제거하고, 옥탄 100mL, 아세트산(acetic acid) 10mL 및 황산 1mL에 녹인 후 65℃에서 4시간 동안 환류시켰다. 증류수를 통해 반응을 종료하고 컬럼크로마토크래피를 통해 상기 화합물 B를 수득하였다. Dissolve 8.16g (5.3eq) of 1-bromo-4-hexylbenzene in 200mL of THF in a round flask, then slowly inject 13.5mL of n-BuLi at -78°C for 1 hour. It was stirred at the same temperature. Compound A prepared in (1) was dissolved in 50 mL of THF, then slowly injected into a stirring round flask and stirred at room temperature for 12 hours. After extracting the organic layer with chloroform, the solvent was removed, dissolved in 100 mL of octane, 10 mL of acetic acid, and 1 mL of sulfuric acid, and refluxed at 65°C for 4 hours. The reaction was terminated with distilled water, and the compound B was obtained through column chromatography.
(3) 화합물 C의 제조(3) Preparation of Compound C
둥근플라스크에서 상기 (2)에서 제조한 화합물 B 1g을 THF 100mL에 녹인 다음 -78℃에서 n-BuLi 0.76mL을 천천히 주입하였다. 1시간 동안 같은 온도에서 교반한 후 DMF 0.5mL을 천천히 주입하고 12시간 동안 교반하였다. 증류수를 통해 반응을 종료한 후 유기층을 추출한 뒤 컬럼크로마토크래피를 통해 화합물 C를 수득하였다.In a round flask, 1 g of Compound B prepared in (2) above was dissolved in 100 mL of THF, and then 0.76 mL of n-BuLi was slowly injected at -78°C. After stirring at the same temperature for 1 hour, 0.5 mL of DMF was slowly injected and stirred for 12 hours. After the reaction was terminated with distilled water, the organic layer was extracted and Compound C was obtained through column chromatography.
(4) 화합물 1의 제조(4) Preparation of Compound 1
콘덴서가 장착된 둥근 플라스크에서 상기 (3)에서 제조한 화합물 C 1g 및 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 0.7g을 클로로포름 10mL에 녹이고 피리딘 1mL를 주입한 후 60℃에서 12시간 동안 환류시켰다. 메탄올을 통해 여과 후 컬럼크로마토크래피를 통해 화합물 1을 수득하였다. In a round flask equipped with a condenser, 1 g of compound C prepared in (3) above and 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3- 0.7 g of oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile) was dissolved in 10 mL of chloroform, 1 mL of pyridine was added, and the mixture was refluxed at 60°C for 12 hours. Compound 1 was obtained through column chromatography after filtration through methanol.
(5) 화합물 2 내지 10의 제조(5) Preparation of compounds 2 to 10
상기 (4)에서 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 대신 각각 하기 표 1의 재료를 사용한 것을 제외하고는 상기 (4)와 동일한 과정을 진행하여 하기 화합물 2 내지 10을 제조하였다.In (4) above, 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3-oxo-2,3-dihydro-1H-inden-1 The following compounds 2 to 10 were prepared by following the same process as (4), except that the materials in Table 1 below were used instead of -ylidene) malononitrile).
[화합물 2][Compound 2]
[화합물 3][Compound 3]
[화합물 4][Compound 4]
[화합물 5][Compound 5]
[화합물 6][Compound 6]
[화합물 7][Compound 7]
[화합물 8][Compound 8]
[화합물 9][Compound 9]
[화합물 10][Compound 10]
제조예 2. 화합물 11 내지 20의 제조Preparation Example 2. Preparation of compounds 11 to 20
(1) 화합물 B2의 제조(1) Preparation of compound B2
상기 제조예 1의 (2)에서 1-브로모-4-헥실벤젠(1-bromo-4-hexylbenzene) 대신 1-브로모-3-헥실벤젠(1-bromo-3-hexylbenzene) 을 사용한 것을 제외하고는 제조예 1의 (2)와 동일한 과정으로 상기 화합물 B2를 제조하였다.In (2) of Preparation Example 1, except that 1-bromo-3-hexylbenzene was used instead of 1-bromo-4-hexylbenzene. Then, the compound B2 was prepared in the same process as (2) of Preparation Example 1.
(2) 화합물 C2의 제조(2) Preparation of compound C2
상기 제조예 1의 (3)에서 화합물 B 대신 상기 화합물 B2를 사용한 것을 제외하고는 제조예 1의 (3)와 동일한 과정으로 상기 화합물 C2를 제조하였다.Compound C2 was prepared through the same process as Preparation Example 1 (3), except that Compound B2 was used instead of Compound B in Preparation Example 1 (3).
(3) 화합물 11의 제조(3) Preparation of compound 11
상기 제조예 1의 (4)에서 화합물 C 대신 상기 화합물 C2를 사용한 것을 제외하고는 제조예 1의 (4)와 동일한 과정으로 상기 화합물 11을 제조하였다. Compound 11 was prepared in the same manner as Preparation Example 1 (4), except that Compound C2 was used instead of Compound C in Preparation Example 1 (4).
(4) 화합물 12 내지 20의 제조(4) Preparation of compounds 12 to 20
상기 제조예 2의 (3)에서 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 대신 각각 하기 표 2의 재료를 사용한 것을 제외하고는 상기 제조예 2 의 (3)와 동일한 과정을 진행하여 하기 화합물 12 내지 20을 제조하였다.In (3) of Preparation Example 2, 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3-oxo-2,3-dihydro-1H The following compounds 12 to 20 were prepared by following the same process as (3) of Preparation Example 2, except that the materials in Table 2 below were used instead of -inden-1-ylidene)malononitrile).
[화합물 12][Compound 12]
[화합물 13][Compound 13]
[화합물 14][Compound 14]
[화합물 15][Compound 15]
[화합물 16][Compound 16]
[화합물 17][Compound 17]
[화합물 18][Compound 18]
[화합물 19][Compound 19]
[화합물 20][Compound 20]
제조예 3. 화합물 21 내지 30의 제조Preparation Example 3. Preparation of compounds 21 to 30
(1) 화합물 B3의 제조(1) Preparation of compound B3
상기 제조예 1의 (2)에서 1-브로모-4-헥실벤젠(1-bromo-4-hexylbenzene) 대신 2-헥실티오펜(2-hexylthiophene) 을 사용한 것을 제외하고는 제조예 1의 (2)와 동일한 과정으로 상기 화합물 B3를 제조하였다.(2) of Preparation Example 1, except that 2-hexylthiophene was used instead of 1-bromo-4-hexylbenzene in (2) of Preparation Example 1. ) Compound B3 was prepared in the same manner as above.
(2) 화합물 C3의 제조(2) Preparation of compound C3
상기 제조예 1의 (3)에서 화합물 B 대신 상기 화합물 B3를 사용한 것을 제외하고는 제조예 1의 (3)와 동일한 과정으로 상기 화합물 C3를 제조하였다.Compound C3 was prepared in the same manner as Preparation Example 1 (3), except that Compound B3 was used instead of Compound B in Preparation Example 1 (3).
(3) 화합물 21의 제조(3) Preparation of compound 21
상기 제조예 1의 (4)에서 화합물 C 대신 상기 화합물 C3를 사용한 것을 제외하고는 제조예 1의 (4)와 동일한 과정으로 상기 화합물 21을 제조하였다. Compound 21 was prepared in the same manner as Preparation Example 1 (4), except that Compound C3 was used instead of Compound C in Preparation Example 1 (4).
(4) 화합물 22 내지 30의 제조(4) Preparation of compounds 22 to 30
상기 제조예 3 의 (3)에서 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 대신 각각 하기 표 3의 재료를 사용한 것을 제외하고는 상기 제조예 3의 (3)과 동일한 과정을 진행하여 하기 화합물 22 내지 30를 제조하였다.In (3) of Preparation Example 3, 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3-oxo-2,3-dihydro-1H The following compounds 22 to 30 were prepared by following the same process as (3) in Preparation Example 3, except that the materials in Table 3 below were used instead of -inden-1-ylidene)malononitrile).
[화합물 22][Compound 22]
[화합물 23][Compound 23]
[화합물 24][Compound 24]
[화합물 25][Compound 25]
[화합물 26][Compound 26]
[화합물 27][Compound 27]
[화합물 28][Compound 28]
[화합물 29][Compound 29]
[화합물 30][Compound 30]
제조예 4. 화합물 31 내지 40의 제조Preparation Example 4. Preparation of compounds 31 to 40
(1) 화합물 D의 제조(1) Preparation of Compound D
상기 제조예 1의 (1)에서 (4,8-bis(4-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) 대신 (4,8-bis(3-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) 를 사용한 것을 제외하고는 제조예 1의 (1)과 동일한 과정으로 상기 화합물 D를 제조하였다.In (1) of Preparation Example 1, (4,8-bis(4-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl ) instead of bis(trimethylstannane) (4,8-bis(3-((2-ethylhexyl)oxy)phenyl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis( Compound D was prepared in the same manner as in Preparation Example 1 (1), except that trimethylstannane) was used.
(2) 화합물 E의 제조(2) Preparation of Compound E
상기 제조예 1의 (2)에서 사용된 화합물 A 대신 상기 제조예 4의 (1)에서합성된 화합물 D를 사용한 것을 제외하고는 제조예 1의 (2)과 동일한 과정으로 상기 화합물 E를 제조하였다.Compound E was prepared in the same manner as Preparation Example 1 (2), except that Compound D synthesized in Preparation Example 4 (1) was used instead of Compound A used in Preparation Example 1 (2). .
(3) 화합물 F의 제조(3) Preparation of Compound F
상기 제조예 1의 (3)에서 사용된 화합물 B 대신 상기 제조예 4의 (2)에서합성된 화합물 E를 사용한 것을 제외하고는 제조예 1의 (3)과 동일한 과정으로 상기 화합물 F를 제조하였다.Compound F was prepared in the same manner as Preparation Example 1 (3), except that Compound E synthesized in Preparation Example 4 (2) was used instead of Compound B used in Preparation Example 1 (3). .
(4) 화합물 31의 제조(4) Preparation of compound 31
상기 제조예 1의 (4)에서 사용된 화합물 C 대신 상기 제조예 4의 (3)에서 합성된 화합물 F를 사용한 것을 제외하고는 제조예 1의 (4)과 동일한 과정으로 상기 화합물 31를 제조하였다.Compound 31 was prepared in the same manner as Preparation Example 1 (4), except that Compound F synthesized in Preparation Example 4 (3) was used instead of Compound C used in Preparation Example 1 (4). .
(5) 화합물 32 내지 40의 제조(5) Preparation of compounds 32 to 40
상기 제조예 4의 (4)에서 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 대신 각각 하기 표 4의 재료를 사용한 것을 제외하고는 상기 제조예 4의 (4)와 동일한 과정을 진행하여 하기 화합물 32 내지 40를 제조하였다.In (4) of Preparation Example 4, 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3-oxo-2,3-dihydro-1H Compounds 32 to 40 below were prepared in the same manner as (4) in Preparation Example 4, except that the materials shown in Table 4 below were used instead of -inden-1-ylidene)malononitrile).
[화합물 32][Compound 32]
[화합물 33][Compound 33]
[화합물 34][Compound 34]
[화합물 35][Compound 35]
[화합물 36][Compound 36]
[화합물 37][Compound 37]
[화합물 38][Compound 38]
[화합물 39][Compound 39]
[화합물 40][Compound 40]
제조예 5. 화합물 41 내지 50의 제조Preparation Example 5. Preparation of compounds 41 to 50
(1) 화합물 E2의 제조(1) Preparation of compound E2
상기 제조예 4의 (2)에서 1-브로모-4-헥실벤젠(1-bromo-4-hexylbenzene) 대신 1-브로모-3-헥실벤젠(1-bromo-3-hexylbenzene) 을 사용한 것을 제외하고는 제조예 4의 (2)와 동일한 과정으로 상기 화합물 E2를 제조하였다.In (2) of Preparation Example 4, except that 1-bromo-3-hexylbenzene was used instead of 1-bromo-4-hexylbenzene. Then, the compound E2 was prepared in the same process as (2) in Preparation Example 4.
(2) 화합물 F2의 제조(2) Preparation of compound F2
상기 제조예 4의 (3)에서 화합물 E 대신 상기 화합물 E2를 사용한 것을 제외하고는 제조예 4의 (3)와 동일한 과정으로 상기 화합물 F2를 제조하였다.Compound F2 was prepared in the same manner as (3) in Preparation Example 4, except that Compound E2 was used instead of Compound E in (3) of Preparation Example 4.
(3) 화합물 41의 제조(3) Preparation of compound 41
상기 제조예 4의 (4)에서 화합물 F 대신 상기 화합물 F2를 사용한 것을 제외하고는 제조예 4의 (4)와 동일한 과정으로 상기 화합물 41을 제조하였다. Compound 41 was prepared in the same manner as Preparation Example 4 (4), except that Compound F2 was used instead of Compound F in Preparation Example 4 (4).
(4) 화합물 42 내지 50의 제조(4) Preparation of compounds 42 to 50
상기 제조예 5의 (3)에서 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 대신 각각 하기 표 5의 재료를 사용한 것을 제외하고는 상기 제조예 5의 (3)와 동일한 과정을 진행하여 하기 화합물 42 내지 50를 제조하였다.In (3) of Preparation Example 5, 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3-oxo-2,3-dihydro-1H Compounds 42 to 50 below were prepared in the same process as (3) of Preparation Example 5, except that the materials shown in Table 5 below were used instead of -inden-1-ylidene)malononitrile).
[화합물 42][Compound 42]
[화합물 43][Compound 43]
[화합물 44][Compound 44]
[화합물 45][Compound 45]
[화합물 46][Compound 46]
[화합물 47][Compound 47]
[화합물 48][Compound 48]
[화합물 49][Compound 49]
[화합물 50][Compound 50]
제조예 6. 화합물 51 내지 60의 제조Preparation Example 6. Preparation of compounds 51 to 60
(1) 화합물 E3의 제조(1) Preparation of compound E3
상기 제조예 4의 (2)에서 1-브로모-4-헥실벤젠(1-bromo-4-hexylbenzene) 대신 2-헥실티오펜(2-hexylthiophene)을 사용한 것을 제외하고는 제조예 4의 (2)와 동일한 과정으로 상기 화합물 E3를 제조하였다.(2) of Preparation Example 4, except that 2-hexylthiophene was used instead of 1-bromo-4-hexylbenzene in (2) of Preparation Example 4. ) Compound E3 was prepared in the same manner as above.
(2) 화합물 F3의 제조(2) Preparation of compound F3
상기 제조예 4의 (3)에서 화합물 E 대신 상기 화합물 E3를 사용한 것을 제외하고는 제조예 4의 (3)와 동일한 과정으로 상기 화합물 F3를 제조하였다.Compound F3 was prepared in the same manner as (3) in Preparation Example 4, except that Compound E3 was used instead of Compound E in (3) of Preparation Example 4.
(3) 화합물 51의 제조(3) Preparation of compound 51
상기 제조예 4의 (4)에서 화합물 F 대신 상기 화합물 F3를 사용한 것을 제외하고는 제조예 4의 (4)와 동일한 과정으로 상기 화합물 51을 제조하였다. Compound 51 was prepared in the same manner as Preparation Example 4 (4), except that Compound F3 was used instead of Compound F in Preparation Example 4 (4).
(4) 화합물 52 내지 60의 제조(4) Preparation of compounds 52 to 60
상기 제조예 6의 (3)에서 2-(3-옥소-2,3-디하이드로-1H-인덴-1-일리덴)말로노니트릴(2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile) 대신 각각 하기 표 6의 재료를 사용한 것을 제외하고는 상기 제조예 6의 (3)과 동일한 과정을 진행하여 하기 화합물 52 내지 60을 제조하였다.In (3) of Preparation Example 6, 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2-(3-oxo-2,3-dihydro-1H The following compounds 52 to 60 were prepared by following the same process as (3) of Preparation Example 6, except that the materials in Table 6 below were used instead of -inden-1-ylidene)malononitrile).
제조된 화합물 1 내지 60의 필름상태의 UV-Vis 스펙트럼을 도 2 내지 도 61에 각각 나타내었다.The UV-Vis spectra of the prepared compounds 1 to 60 in the film state are shown in Figures 2 to 61, respectively.
[화합물 52][Compound 52]
[화합물 53][Compound 53]
[화합물 54][Compound 54]
[화합물 55][Compound 55]
[화합물 56][Compound 56]
[화합물 57][Compound 57]
[화합물 58][Compound 58]
[화합물 59][Compound 59]
[화합물 60][Compound 60]
<실시예 : 유기 태양 전지의 제조><Example: Manufacturing of organic solar cell>
실시예 1.Example 1.
(1) 복합 용액의 제조(1) Preparation of composite solution
하기 화합물 폴리[(2,6-(4,8-비스(5-(2-에틸헥실)티오펜-2-일)-벤조[1,2-b:4,5-b']디티오펜))-알트-(5,5-(1',3'-디-2-티에닐-5',7'-비스(2-에틸헥실)벤조[1',2'-c:4',5'-c']디티오펜-4,8-다이온))](poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)- benzo[1,2-b:4,5-b']dithiophene))-alt-(5,5-(1',3'-di-2-thienyl-5',7'- bis(2-ethylhexyl)benzo[1',2'-c:4',5'-c']dithiophene-4,8-dione))], PBDB-T)(Mn: 25,000g/mol, Solarmer 社)를 전자 주개 물질로, 상기 제조예에서 합성된 화합물 1을 전자 받개 물질로 하여 1:1의 질량비로 클로로벤젠(Chlorobenzene, CB)에 녹여 전자주개+전자받개의 농도가 2wt% 농도인 복합 용액(composite solution)을 제조하였다. The following compound poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b']dithiophene) )-alt-(5,5-(1',3'-di-2-thienyl-5',7'-bis(2-ethylhexyl)benzo[1',2'-c:4',5 '-c']dithiophen-4,8-dione))](poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1, 2-b:4,5-b']dithiophene))-alt-(5,5-(1',3'-di-2-thienyl-5',7'- bis(2-ethylhexyl)benzo[1 ',2'-c:4',5'-c']dithiophene-4,8-dione))], PBDB-T) (Mn: 25,000 g/mol, Solarmer) as an electron donor material, prepared above Compound 1 synthesized in the example was dissolved in chlorobenzene (CB) at a mass ratio of 1:1 using the electron acceptor material to prepare a composite solution with an electron donor + electron acceptor concentration of 2 wt%.
(2) 유기 태양 전지의 제조 (2) Manufacturing of organic solar cells
ITO가 1.5×1.5cm2의 바타입(bar type)으로 코팅된 유리 기판(11.5Ω/□)을 증류수, 아세톤 및 2-프로판올을 이용하여 초음파 세척하고, ITO 표면을 10분 동안 오존 처리하여 제1 전극을 형성하였다. A glass substrate (11.5Ω/□) coated with ITO in a 1.5×1.5cm 2 bar type was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was treated with ozone for 10 minutes. 1 Electrode was formed.
상기 제1 전극 상에 ZnO 나노입자 용액(N-10, Nanograde Ltd, 2.5wt% in 1-butanol, 0.45㎛ PTFE에 필터링)을 4,000rpm으로 40초 동안 스핀-코팅(spin-coating)한 후, 80℃에서 10분간 열처리하여 남아있는 용매를 제거함으로써 전자수송층을 형성하였다.After spin-coating a ZnO nanoparticle solution (N-10, Nanograde Ltd, 2.5wt% in 1-butanol, filtered through 0.45㎛ PTFE) on the first electrode at 4,000rpm for 40 seconds, An electron transport layer was formed by heat treatment at 80°C for 10 minutes to remove the remaining solvent.
이후, 상기 (1)에서 제조한 복합 용액을 상기 전자수송층 상에 70℃에서 900rpm으로 25초간 스핀-코팅하여 광활성층을 형성하고, 상기 광활성층 상에 MoO3를 0.2Å/s의 속도 및 10-7torr 진공 하에서 10nm의 두께로 열 증착하여 정공수송층을 형성하였다.Thereafter, the composite solution prepared in (1) was spin-coated on the electron transport layer at 70°C at 900 rpm for 25 seconds to form a photoactive layer, and MoO 3 was applied on the photoactive layer at a speed of 0.2 Å/s and 10 A hole transport layer was formed by thermal deposition to a thickness of 10 nm under -7 torr vacuum.
이후 열 증착기 내부에서 Ag를 1Å/s의 속도에서 100nm 두께로 증착하여 제2 전극을 형성함으로써, 인버티드(inverted) 구조의 유기 태양 전지를 제조하였다.Afterwards, Ag was deposited to a thickness of 100 nm at a speed of 1 Å/s inside a thermal evaporator to form a second electrode, thereby manufacturing an organic solar cell with an inverted structure.
실시예 2 내지 실시예 60.Examples 2 to 60.
상기 실시예 1에서 복합 용액 제조시, 화합물 1 대신 상기 화합물 2 내지 60을 각각 사용한 것을 제외하고는 상기 실시예 1과 동일한 과정으로 실시예 2 내지 60의 유기 태양 전지를 제조하였다. Organic solar cells of Examples 2 to 60 were prepared in the same process as Example 1, except that Compounds 2 to 60 were used instead of Compound 1 when preparing the composite solution in Example 1.
비교예 1.Comparative Example 1.
상기 실시예 1에서 복합 용액 제조시, 화합물 1 대신 하기 비교 화합물 1을 사용한 것을 제외하고는 상기 실시예 1과 동일한 과정으로 유기 태양 전지를 제조하였다.An organic solar cell was prepared in the same manner as in Example 1, except that Comparative Compound 1 below was used instead of Compound 1 when preparing the composite solution in Example 1.
[비교 화합물 1][Comparative Compound 1]
상기 실시예 1 내지 60 및 비교예 1 에서 제조된 유기 태양 전지의 광전변환특성을 100mW/cm2 (AM 1.5) 조건에서 측정하고, 하기 표 7에 그 결과를 나타내었다.The photoelectric conversion characteristics of the organic solar cells prepared in Examples 1 to 60 and Comparative Example 1 were measured under 100 mW/cm 2 (AM 1.5) conditions, and the results are shown in Table 7 below.
(V) V oc
(V)
(mA/cm2) J sc
(mA/ cm2 )
(%) η
(%)
상기 표 7에서, 상기 Spin-speed는 전자수송층 상에 복합 용액을 스핀-코팅하여 광활성층을 형성할 때 장비의 회전 속도를, VOC는 개방전압을, JSC는 단락전류를, FF는 충전율(Fill factor)을, η는 에너지 변환 효율을 의미한다. 개방전압과 단락전류는 각각 전압-전류 밀도 곡선의 4사분면에서 X축과 Y축 절편이며, 이 두 값이 높을수록 태양 전지의 효율은 바람직하게 높아진다. 또한 충전율(Fill factor)은 곡선 내부에 그릴 수 있는 직사각형의 넓이를 단락전류와 개방전압의 곱으로 나눈 값이다. 에너지 변환 효율(η)은 상기 개방전압(Voc), 단락전류(Jsc) 및 충전율(FF)의 곱을 입사된 빛의 세기(Pin)로 나누면 구할 수 있으며, 이 값이 높을수록 바람직하다.In Table 7, Spin-speed is the rotation speed of the equipment when forming a photoactive layer by spin-coating the composite solution on the electron transport layer, V OC is the open-circuit voltage, J SC is the short-circuit current, and FF is the charging rate. (Fill factor) and η means energy conversion efficiency. The open-circuit voltage and short-circuit current are the X-axis and Y-axis intercepts in the fourth quadrant of the voltage-current density curve, respectively, and the higher these two values, the higher the efficiency of the solar cell. Additionally, the fill factor is the area of the rectangle that can be drawn inside the curve divided by the product of the short-circuit current and the open-circuit voltage. Energy conversion efficiency (η) can be obtained by dividing the product of the open-circuit voltage (V oc ), short-circuit current (J sc ), and charging rate (FF) by the intensity of incident light (P in ), and the higher this value, the more preferable. .
상기 표 7의 결과를 살펴보면, 본 명세서의 일 실시상태에 따른 화합물 1 내지 60을 전자 받개로 사용한 실시예 1 내지 60의 유기 태양 전지는 알콕시페닐을 포함하지 않는 비교 화합물을 사용한 비교예 1의 유기 태양 전지에 비해 개방 전압이 높고, 충전율 등의 소자 효율이 우수하며, 에너지 변환 효율이 우수한 것을 알 수 있다. 이는 알콕시페닐이 티오펜에 비해 낮은 HOMO/높은 LUMO 에너지 레벨을 유발하므로, 개방전압이 높아지기 때문이다.Looking at the results in Table 7, the organic solar cells of Examples 1 to 60 using Compounds 1 to 60 according to an exemplary embodiment of the present specification as electron acceptors are the organic solar cells of Comparative Example 1 using a comparative compound not containing alkoxyphenyl. It can be seen that compared to solar cells, the open-circuit voltage is high, the device efficiency such as charging rate is excellent, and the energy conversion efficiency is excellent. This is because alkoxyphenyl causes lower HOMO/higher LUMO energy levels compared to thiophene, resulting in higher open-circuit voltage.
또한, 알콕시기가 벤젠고리의 meta 위치에 치환된 화합물 31 내지 60을 사용한 실시예 31 내지 60의 개방전압이 para 위치에 치환된 화합물 1 내지 30을 사용한 실시예 1 내지 30에 비해 대체적으로 개방전압이 더 높고, 이에 따라 에너지 변환 효율도 대부분 더 우수한 것을 확인 할 수 있다. 이는 para 위치에 치환된 알콕시기에 비해 meta 위치에 치환된 알콕시기가 상대적으로 높은 LUMO 에너지 레벨을 형성하기 때문이다.In addition, the open-circuit voltages of Examples 31 to 60 using Compounds 31 to 60 in which the alkoxy group was substituted in the meta position of the benzene ring were generally lower than those in Examples 1 to 30 using Compounds 1 to 30 in which the alkoxy group was substituted in the para position. It can be seen that it is higher, and thus the energy conversion efficiency is also mostly superior. This is because the alkoxy group substituted at the meta position forms a relatively higher LUMO energy level than the alkoxy group substituted at the para position.
100: 제1 전극
200: 광활성층
300: 제2 전극100: first electrode
200: Photoactive layer
300: second electrode
Claims (12)
[화학식 5-1]
[화학식 5-2]
[화학식 5-3]
[화학식 5-4]
[화학식 5-5]
[화학식 5-6]
[화학식 5-7]
[화학식 5-8]
상기 화학식 5-1 내지 5-8에서,
R1 내지 R4는 서로 같거나 상이하며 각각 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이고,
R5 내지 R8은 수소이고,
R9 및 R10은 서로 같거나 상이하며 각각 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 6 내지 10의 아릴기이며,
Y1 및 Y2는 서로 같거나 상이하며 각각 할로겐기; 또는 탄소수 1 내지 10의 직쇄의 알킬기이고,
n 및 m은 서로 같거나 상이하며 각각 0 내지 6의 정수이고,
R15 내지 R22은 서로 같거나 상이하며 각각 수소; 또는 탄소수 1 내지 10의 직쇄의 알킬기이며,
Q1 내지 Q4는 서로 같거나 상이하며 각각 S 또는 Se이다.Heterocyclic compounds represented by any of the following formulas 5-1 to 5-8:
[Formula 5-1]
[Formula 5-2]
[Formula 5-3]
[Formula 5-4]
[Formula 5-5]
[Formula 5-6]
[Formula 5-7]
[Formula 5-8]
In Formulas 5-1 to 5-8,
R1 to R4 are the same or different from each other and are each a straight-chain or branched alkyl group having 1 to 30 carbon atoms,
R5 to R8 are hydrogen,
R9 and R10 are the same or different from each other and are each a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or an aryl group having 6 to 10 carbon atoms,
Y1 and Y2 are the same or different from each other and are each a halogen group; or a straight-chain alkyl group having 1 to 10 carbon atoms,
n and m are the same or different from each other and are each integers from 0 to 6,
R15 to R22 are the same or different and are each hydrogen; or a straight-chain alkyl group having 1 to 10 carbon atoms,
Q1 to Q4 are the same or different from each other and are S or Se, respectively.
상기 헤테로환 화합물은 하기 화학식 6-1 내지 6-60 중 선택된 어느 하나인 것인 헤테로환 화합물:
[화학식 6-1]
[화학식 6-2]
[화학식 6-3]
[화학식 6-4]
[화학식 6-5]
[화학식 6-6]
[화학식 6-7]
[화학식 6-8]
[화학식 6-9]
[화학식 6-10]
[화학식 6-11]
[화학식 6-12]
[화학식 6-13]
[화학식 6-14]
[화학식 6-15]
[화학식 6-16]
[화학식 6-17]
[화학식 6-18]
[화학식 6-19]
[화학식 6-20]
[화학식 6-21]
[화학식 6-22]
[화학식 6-23]
[화학식 6-24]
[화학식 6-25]
[화학식 6-26]
[화학식 6-27]
[화학식 6-28]
[화학식 6-29]
[화학식 6-30]
[화학식 6-31]
[화학식 6-32]
[화학식 6-33]
[화학식 6-34]
[화학식 6-35]
[화학식 6-36]
[화학식 6-37]
[화학식 6-38]
[화학식 6-39]
[화학식 6-40]
[화학식 6-41]
[화학식 6-42]
[화학식 6-43]
[화학식 6-44]
[화학식 6-45]
[화학식 6-46]
[화학식 6-47]
[화학식 6-48]
[화학식 6-49]
[화학식 6-50]
[화학식 6-51]
[화학식 6-52]
[화학식 6-53]
[화학식 6-54]
[화학식 6-55]
[화학식 6-56]
[화학식 6-57]
[화학식 6-58]
[화학식 6-59]
[화학식 6-60]
In claim 1,
The heterocyclic compound is any one selected from the following formulas 6-1 to 6-60:
[Formula 6-1]
[Formula 6-2]
[Formula 6-3]
[Formula 6-4]
[Formula 6-5]
[Formula 6-6]
[Formula 6-7]
[Formula 6-8]
[Formula 6-9]
[Formula 6-10]
[Formula 6-11]
[Formula 6-12]
[Formula 6-13]
[Formula 6-14]
[Formula 6-15]
[Formula 6-16]
[Formula 6-17]
[Formula 6-18]
[Formula 6-19]
[Formula 6-20]
[Formula 6-21]
[Formula 6-22]
[Formula 6-23]
[Formula 6-24]
[Formula 6-25]
[Formula 6-26]
[Formula 6-27]
[Formula 6-28]
[Formula 6-29]
[Formula 6-30]
[Formula 6-31]
[Formula 6-32]
[Formula 6-33]
[Formula 6-34]
[Formula 6-35]
[Formula 6-36]
[Formula 6-37]
[Formula 6-38]
[Formula 6-39]
[Formula 6-40]
[Formula 6-41]
[Formula 6-42]
[Formula 6-43]
[Formula 6-44]
[Formula 6-45]
[Formula 6-46]
[Formula 6-47]
[Formula 6-48]
[Formula 6-49]
[Formula 6-50]
[Formula 6-51]
[Formula 6-52]
[Formula 6-53]
[Formula 6-54]
[Formula 6-55]
[Formula 6-56]
[Formula 6-57]
[Formula 6-58]
[Formula 6-59]
[Formula 6-60]
상기 헤테로환 화합물의 함량은 상기 조성물 100wt%를 기준으로 0.5wt% 내지 3wt% 인 것인 유기 전자 소자의 유기활성층 형성용 조성물.In claim 8,
A composition for forming an organic active layer of an organic electronic device, wherein the content of the heterocyclic compound is 0.5 wt% to 3 wt% based on 100 wt% of the composition.
상기 제1 전극과 대향하여 구비되는 제2 전극; 및
상기 제1 전극과 제2 전극 사이에 구비되고, 유기활성층을 포함하는 1층 이상의 유기물층을 포함하며,
상기 유기활성층은 청구항 1 또는 7에 따른 헤테로환 화합물을 포함하는 것인 유기 전자 소자.first electrode;
a second electrode provided opposite the first electrode; and
It is provided between the first electrode and the second electrode, and includes one or more organic layers including an organic active layer,
An organic electronic device wherein the organic active layer includes the heterocyclic compound according to claim 1 or 7.
상기 유기활성층은 전자 주개 및 전자 받개를 포함하며,
상기 전자 받개는 상기 헤테로환 화합물을 포함하는 것인 유기 전자 소자.In claim 10,
The organic active layer includes an electron donor and an electron acceptor,
An organic electronic device wherein the electron acceptor includes the heterocyclic compound.
상기 유기 전자 소자는 유기 태양 전지, 유기 광전 소자, 유기 발광 소자, 유기 감광체 또는 유기 트랜지스터인 것인 유기 전자 소자.In claim 10,
The organic electronic device is an organic solar cell, an organic photoelectric device, an organic light-emitting device, an organic photoreceptor, or an organic transistor.
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