KR101950855B1 - 신규 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
신규 화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
- Publication number
- KR101950855B1 KR101950855B1 KR1020160121649A KR20160121649A KR101950855B1 KR 101950855 B1 KR101950855 B1 KR 101950855B1 KR 1020160121649 A KR1020160121649 A KR 1020160121649A KR 20160121649 A KR20160121649 A KR 20160121649A KR 101950855 B1 KR101950855 B1 KR 101950855B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- substituted
- unsubstituted
- layer
- light emitting
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 142
- 239000010410 layer Substances 0.000 claims description 281
- 125000003118 aryl group Chemical group 0.000 claims description 120
- 125000002560 nitrile group Chemical group 0.000 claims description 71
- 238000002347 injection Methods 0.000 claims description 58
- 239000007924 injection Substances 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- -1 (8H-cyclopenta [a] acenaphthylene-8-ylidene) malonitrile group Chemical group 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000011368 organic material Substances 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 239000000872 buffer Substances 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000005578 chrysene group Chemical group 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 229910052732 germanium Inorganic materials 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000463 material Substances 0.000 description 54
- 239000007787 solid Substances 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 125000000623 heterocyclic group Chemical group 0.000 description 25
- 230000005525 hole transport Effects 0.000 description 25
- 238000001819 mass spectrum Methods 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 238000005259 measurement Methods 0.000 description 23
- 125000003710 aryl alkyl group Chemical group 0.000 description 20
- 238000001816 cooling Methods 0.000 description 19
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- 230000032258 transport Effects 0.000 description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 125000002877 alkyl aryl group Chemical group 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 15
- 238000000926 separation method Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 12
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000003974 aralkylamines Chemical group 0.000 description 8
- 125000005264 aryl amine group Chemical group 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 239000010406 cathode material Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical group C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 6
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910052727 yttrium Inorganic materials 0.000 description 5
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 4
- DQQKEYDDVSREIE-UHFFFAOYSA-N 1,3-bis(4-bromophenyl)propan-2-one Chemical compound C1=CC(Br)=CC=C1CC(=O)CC1=CC=C(Br)C=C1 DQQKEYDDVSREIE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- KSVMTHKYDGMXFJ-UHFFFAOYSA-N n,n'-bis(trimethylsilyl)methanediimine Chemical compound C[Si](C)(C)N=C=N[Si](C)(C)C KSVMTHKYDGMXFJ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- NYCBYBDDECLFPE-UHFFFAOYSA-N 1,2-bis(4-bromophenyl)ethane-1,2-dione Chemical compound C1=CC(Br)=CC=C1C(=O)C(=O)C1=CC=C(Br)C=C1 NYCBYBDDECLFPE-UHFFFAOYSA-N 0.000 description 3
- BPARIXKHXBXFHU-UHFFFAOYSA-N 1,3-bis(4-fluorophenyl)propan-2-one Chemical compound C1=CC(F)=CC=C1CC(=O)CC1=CC=C(F)C=C1 BPARIXKHXBXFHU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000005266 diarylamine group Chemical group 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- 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 2
- HNWFFTUWRIGBNM-UHFFFAOYSA-N 2-methyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C)=CC=C21 HNWFFTUWRIGBNM-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QTDJJWDSZNIADG-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C1c2c3)c(cccc4)c4-c2ccc3C#N)c(cc2)ccc2F)C1c(cc1)ccc1F Chemical compound N#CC(C#N)=C(C(C(C1c2c3)c(cccc4)c4-c2ccc3C#N)c(cc2)ccc2F)C1c(cc1)ccc1F QTDJJWDSZNIADG-UHFFFAOYSA-N 0.000 description 2
- QWHSOGHGURZEKZ-UHFFFAOYSA-N N#CC(C#N)=C(C(C1c2c3)c4ccccc4)C(c4ccccc4)=C1c(cccc1)c1-c2ccc3C#N Chemical compound N#CC(C#N)=C(C(C1c2c3)c4ccccc4)C(c4ccccc4)=C1c(cccc1)c1-c2ccc3C#N QWHSOGHGURZEKZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000005165 aryl thioxy group Chemical group 0.000 description 2
- 125000003609 aryl vinyl group Chemical group 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 239000007773 negative electrode material Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- 0 *C1=C(c2ccc(*)c3c2c2ccc3*)C2=C(*)C1=IN Chemical compound *C1=C(c2ccc(*)c3c2c2ccc3*)C2=C(*)C1=IN 0.000 description 1
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 1
- BRKULQOUSCHDGS-UHFFFAOYSA-N 1,2-bis(4-fluorophenyl)ethane-1,2-dione Chemical compound C1=CC(F)=CC=C1C(=O)C(=O)C1=CC=C(F)C=C1 BRKULQOUSCHDGS-UHFFFAOYSA-N 0.000 description 1
- WHTKSZOXPDAVMH-UHFFFAOYSA-N 1,2-bis[4-(trifluoromethyl)phenyl]ethane-1,2-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)C(=O)C1=CC=C(C(F)(F)F)C=C1 WHTKSZOXPDAVMH-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- QYAPROVUZGLSLI-UHFFFAOYSA-N 5,6-difluoroacenaphthylene-1,2-dione Chemical compound FC1=CC=C2C(C(C=3C=CC(=C1C=32)F)=O)=O QYAPROVUZGLSLI-UHFFFAOYSA-N 0.000 description 1
- PHPQHHFMRUWUJG-UHFFFAOYSA-N 5-bromoacenaphthylene-1,2-dione Chemical compound C1=CC=C2C(Br)=CC=C3C(=O)C(=O)C1=C23 PHPQHHFMRUWUJG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- 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
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 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
- LHTGTTQXCORLLV-RKMIRMFUSA-N N#C/N=C(/C(C(C12)c3cccc4c(C(F)(F)F)ccc1c34)c1ccc(C(F)(F)F)cc1)\C2c1ccc(C(F)(F)F)cc1 Chemical compound N#C/N=C(/C(C(C12)c3cccc4c(C(F)(F)F)ccc1c34)c1ccc(C(F)(F)F)cc1)\C2c1ccc(C(F)(F)F)cc1 LHTGTTQXCORLLV-RKMIRMFUSA-N 0.000 description 1
- JJRFUXLBYRALKK-HOKWUGLCSA-N N#C/N=C(\C(C12)c3ccc(C(F)(F)F)cc3)/C(c3ccc(C(F)(F)F)cc3)=C1c1ccc(C(F)(F)F)c3c(C(F)(F)F)ccc2c13 Chemical compound N#C/N=C(\C(C12)c3ccc(C(F)(F)F)cc3)/C(c3ccc(C(F)(F)F)cc3)=C1c1ccc(C(F)(F)F)c3c(C(F)(F)F)ccc2c13 JJRFUXLBYRALKK-HOKWUGLCSA-N 0.000 description 1
- PMSVVWMEABUWFS-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C12)C(C34)=CC=CC3=CC=C3C4=C1C=CC3)c(cc1)ccc1F)C2c(cc1)ccc1F Chemical compound N#CC(C#N)=C(C(C(C12)C(C34)=CC=CC3=CC=C3C4=C1C=CC3)c(cc1)ccc1F)C2c(cc1)ccc1F PMSVVWMEABUWFS-UHFFFAOYSA-N 0.000 description 1
- LUCSRUPTBFIECO-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C12)C(C34)=CC=CC3=CC=C3C4=C1C=CC3)c1ccccc1)C2c1ccccc1 Chemical compound N#CC(C#N)=C(C(C(C12)C(C34)=CC=CC3=CC=C3C4=C1C=CC3)c1ccccc1)C2c1ccccc1 LUCSRUPTBFIECO-UHFFFAOYSA-N 0.000 description 1
- QZCGGFOGTMORKK-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C12)c(cccc3)c3-c(cc3)c1cc3C#N)c(cc1)ccc1C#N)C2c(cc1)ccc1C#N Chemical compound N#CC(C#N)=C(C(C(C12)c(cccc3)c3-c(cc3)c1cc3C#N)c(cc1)ccc1C#N)C2c(cc1)ccc1C#N QZCGGFOGTMORKK-UHFFFAOYSA-N 0.000 description 1
- LMBGEBPEDZHMAD-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C12)c3c4-c5c1cccc5Cc4ccc3)c(cc1)ccc1C#N)C2c(cc1)ccc1C#N Chemical compound N#CC(C#N)=C(C(C(C12)c3c4-c5c1cccc5Cc4ccc3)c(cc1)ccc1C#N)C2c(cc1)ccc1C#N LMBGEBPEDZHMAD-UHFFFAOYSA-N 0.000 description 1
- LWLVDPYJQTYTHP-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C12)c3cccc4cc5ccccc5c1c34)c1ccccc1)C2c1ccccc1 Chemical compound N#CC(C#N)=C(C(C(C12)c3cccc4cc5ccccc5c1c34)c1ccccc1)C2c1ccccc1 LWLVDPYJQTYTHP-UHFFFAOYSA-N 0.000 description 1
- MRQBSHMBGKPMCZ-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C1c(cc2)c34)c3cccc4c2C#N)c(cc2)ccc2OC(F)(F)F)C1c(cc1)ccc1OC(F)(F)F Chemical compound N#CC(C#N)=C(C(C(C1c(cc2)c34)c3cccc4c2C#N)c(cc2)ccc2OC(F)(F)F)C1c(cc1)ccc1OC(F)(F)F MRQBSHMBGKPMCZ-UHFFFAOYSA-N 0.000 description 1
- DBNTVPVSHZGQPZ-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C1c(cc2)c34)c3cccc4c2F)c(cc2)ccc2OC(F)(F)F)C1c(cc1)ccc1OC(F)(F)F Chemical compound N#CC(C#N)=C(C(C(C1c(cc2)c34)c3cccc4c2F)c(cc2)ccc2OC(F)(F)F)C1c(cc1)ccc1OC(F)(F)F DBNTVPVSHZGQPZ-UHFFFAOYSA-N 0.000 description 1
- MKNUKIXJYOQPAH-UHFFFAOYSA-N N#CC(C#N)=C(C(C(C1c2c3)c4ccccc4-c2ccc3C#N)c2ccccc2)C1c1ccccc1 Chemical compound N#CC(C#N)=C(C(C(C1c2c3)c4ccccc4-c2ccc3C#N)c2ccccc2)C1c1ccccc1 MKNUKIXJYOQPAH-UHFFFAOYSA-N 0.000 description 1
- VFKYMFOTBQFVIU-UHFFFAOYSA-N N#CC(C#N)=C(C(C12)C3C=CC(C#N)=CC3)C(c(cc3)ccc3C#N)=C1c1c3c4c2cccc4ccc3ccc1 Chemical compound N#CC(C#N)=C(C(C12)C3C=CC(C#N)=CC3)C(c(cc3)ccc3C#N)=C1c1c3c4c2cccc4ccc3ccc1 VFKYMFOTBQFVIU-UHFFFAOYSA-N 0.000 description 1
- PDPPZBARKQBERC-UHFFFAOYSA-N N#CC(C#N)=C(C(C12)c(cc3)ccc3C#N)C(c(cc3)ccc3C#N)=C1c1cccc3cc(cccc4)c4c2c13 Chemical compound N#CC(C#N)=C(C(C12)c(cc3)ccc3C#N)C(c(cc3)ccc3C#N)=C1c1cccc3cc(cccc4)c4c2c13 PDPPZBARKQBERC-UHFFFAOYSA-N 0.000 description 1
- MJHJVYIHBNXBIH-UHFFFAOYSA-N N#CC(C#N)=C(C(C12)c(cc3)ccc3OC(F)(F)F)C(c(cc3)ccc3OC(F)(F)F)=C1c1cccc3cccc2c13 Chemical compound N#CC(C#N)=C(C(C12)c(cc3)ccc3OC(F)(F)F)C(c(cc3)ccc3OC(F)(F)F)=C1c1cccc3cccc2c13 MJHJVYIHBNXBIH-UHFFFAOYSA-N 0.000 description 1
- XUUYEVCRTSGHQL-UHFFFAOYSA-N N#CC(C#N)=C(C(C12)c3ccc(C(F)(F)F)cc3)C(c3ccc(C(F)(F)F)cc3)=C1c(cccc1)c1-c(cc1)c2cc1C#N Chemical compound N#CC(C#N)=C(C(C12)c3ccc(C(F)(F)F)cc3)C(c3ccc(C(F)(F)F)cc3)=C1c(cccc1)c1-c(cc1)c2cc1C#N XUUYEVCRTSGHQL-UHFFFAOYSA-N 0.000 description 1
- VTOHJKYXWHNXKL-UHFFFAOYSA-N N#CC(C#N)=C(C(C1C=CC(C#N)=CC1)=C1c2c3)C(c(cc4)ccc4C#N)=C1c1ccccc1-c2ccc3C#N Chemical compound N#CC(C#N)=C(C(C1C=CC(C#N)=CC1)=C1c2c3)C(c(cc4)ccc4C#N)=C1c1ccccc1-c2ccc3C#N VTOHJKYXWHNXKL-UHFFFAOYSA-N 0.000 description 1
- XYMIKMPZUYNTCS-UHFFFAOYSA-N N#CC(C#N)=C(C(C1c(cc2)c3c4c2C#N)c(cc2)ccc2OC(F)(F)F)C(c(cc2)ccc2OC(F)(F)F)=C1c3ccc4C#N Chemical compound N#CC(C#N)=C(C(C1c(cc2)c3c4c2C#N)c(cc2)ccc2OC(F)(F)F)C(c(cc2)ccc2OC(F)(F)F)=C1c3ccc4C#N XYMIKMPZUYNTCS-UHFFFAOYSA-N 0.000 description 1
- DDKSZIMDDPXOLK-UHFFFAOYSA-N N#CC(C#N)=C(C(C1c(cc2)c3c4c2F)c(cc2)ccc2OC(F)(F)F)C(c(cc2)ccc2OC(F)(F)F)=C1c3ccc4F Chemical compound N#CC(C#N)=C(C(C1c(cc2)c3c4c2F)c(cc2)ccc2OC(F)(F)F)C(c(cc2)ccc2OC(F)(F)F)=C1c3ccc4F DDKSZIMDDPXOLK-UHFFFAOYSA-N 0.000 description 1
- PQNKCYQUYPWGFA-UHFFFAOYSA-N N#CC(C#N)=C(C(C1c2ccc3-c(cc4)ccc4C#N)c(cc4)ccc4OC(F)(F)F)C(c(cc4)ccc4OC(F)(F)F)=C1c(cc1)c2c3c1-c(cc1)ccc1C#N Chemical compound N#CC(C#N)=C(C(C1c2ccc3-c(cc4)ccc4C#N)c(cc4)ccc4OC(F)(F)F)C(c(cc4)ccc4OC(F)(F)F)=C1c(cc1)c2c3c1-c(cc1)ccc1C#N PQNKCYQUYPWGFA-UHFFFAOYSA-N 0.000 description 1
- VOOLEEFBFWSWOY-UHFFFAOYSA-N N#CC(C#N)=C(C(C1c2ccc3-c4ccc(C(F)(F)F)cc4)c(cc4)ccc4F)C(c(cc4)ccc4F)=C1c(cc1)c2c3c1-c1ccc(C(F)(F)F)cc1 Chemical compound N#CC(C#N)=C(C(C1c2ccc3-c4ccc(C(F)(F)F)cc4)c(cc4)ccc4F)C(c(cc4)ccc4F)=C1c(cc1)c2c3c1-c1ccc(C(F)(F)F)cc1 VOOLEEFBFWSWOY-UHFFFAOYSA-N 0.000 description 1
- WWZZUUZXUGLKLV-UHFFFAOYSA-N N#CC(C#N)=C(C(C1c2ccccc2-c2cc(C(F)(F)F)ccc2C11)c2ccccc2)C1c1ccccc1 Chemical compound N#CC(C#N)=C(C(C1c2ccccc2-c2cc(C(F)(F)F)ccc2C11)c2ccccc2)C1c1ccccc1 WWZZUUZXUGLKLV-UHFFFAOYSA-N 0.000 description 1
- KWLACBLNLNYOAZ-UHFFFAOYSA-N N#CC(C#N)=C(C(c1ccccc1)=C12)C(c3ccccc3)=C1C1=C3C4C2=CC=CC4CC3CC=C1 Chemical compound N#CC(C#N)=C(C(c1ccccc1)=C12)C(c3ccccc3)=C1C1=C3C4C2=CC=CC4CC3CC=C1 KWLACBLNLNYOAZ-UHFFFAOYSA-N 0.000 description 1
- JXRNKOSICSJHNZ-UHFFFAOYSA-N N#CC(C#N)=C1C(c(cc2)ccc2C#N)=C(c(c2c3cc4)ccc(-c(cc5)ccc5F)c2c4-c(cc2)ccc2F)C3=C1c(cc1)ccc1C#N Chemical compound N#CC(C#N)=C1C(c(cc2)ccc2C#N)=C(c(c2c3cc4)ccc(-c(cc5)ccc5F)c2c4-c(cc2)ccc2F)C3=C1c(cc1)ccc1C#N JXRNKOSICSJHNZ-UHFFFAOYSA-N 0.000 description 1
- SEVIJTHOALQPTE-UHFFFAOYSA-N N#CC(C#N)=C1C(c(cc2)ccc2F)=C2c3cc(C#N)ccc3-c3ccccc3C2C1c(cc1)ccc1F Chemical compound N#CC(C#N)=C1C(c(cc2)ccc2F)=C2c3cc(C#N)ccc3-c3ccccc3C2C1c(cc1)ccc1F SEVIJTHOALQPTE-UHFFFAOYSA-N 0.000 description 1
- LWIHRDLQFSFIQT-UHFFFAOYSA-N N#CC(C#N)=C1C(c2ccc(C(F)(F)F)cc2)=C2C(C=CC3)=C(C45)C3=CC=C4C=CC=C5C2=C1c1ccc(C(F)(F)F)cc1 Chemical compound N#CC(C#N)=C1C(c2ccc(C(F)(F)F)cc2)=C2C(C=CC3)=C(C45)C3=CC=C4C=CC=C5C2=C1c1ccc(C(F)(F)F)cc1 LWIHRDLQFSFIQT-UHFFFAOYSA-N 0.000 description 1
- PWNGMJNLVRIJEX-UHFFFAOYSA-N N#CC(C#N)=C1c(cc(cc2)-c3ccccc3)c2-c(cc2)c1cc2-c1ccccc1 Chemical compound N#CC(C#N)=C1c(cc(cc2)-c3ccccc3)c2-c(cc2)c1cc2-c1ccccc1 PWNGMJNLVRIJEX-UHFFFAOYSA-N 0.000 description 1
- XPFJJNCKXOPETM-UHFFFAOYSA-N N#Cc(cc1)ccc1-c(cc1)ccc1C(C1=NC#N)=C(c(cc2)c(c3ccc4F)c4c2F)C3=C1c(cc1)ccc1-c(cc1)ccc1C#N Chemical compound N#Cc(cc1)ccc1-c(cc1)ccc1C(C1=NC#N)=C(c(cc2)c(c3ccc4F)c4c2F)C3=C1c(cc1)ccc1-c(cc1)ccc1C#N XPFJJNCKXOPETM-UHFFFAOYSA-N 0.000 description 1
- CHPWFYRXPUPIGG-MIDJFWNWSA-N N#Cc1c(cccc2C(C3C(/C4=N\C#N)c5ccc(C(F)(F)F)cc5)=C4c4ccc(C(F)(F)F)cc4)c2c3cc1 Chemical compound N#Cc1c(cccc2C(C3C(/C4=N\C#N)c5ccc(C(F)(F)F)cc5)=C4c4ccc(C(F)(F)F)cc4)c2c3cc1 CHPWFYRXPUPIGG-MIDJFWNWSA-N 0.000 description 1
- OIOOOOWICGXEAF-OJZPPULMSA-N N#Cc1c2c(C#N)ccc(C(C3C(/C4=N\C#N)c5ccc(C(F)(F)F)cc5)=C4c4ccc(C(F)(F)F)cc4)c2c3cc1 Chemical compound N#Cc1c2c(C#N)ccc(C(C3C(/C4=N\C#N)c5ccc(C(F)(F)F)cc5)=C4c4ccc(C(F)(F)F)cc4)c2c3cc1 OIOOOOWICGXEAF-OJZPPULMSA-N 0.000 description 1
- MLHWWAZVNGNKOP-UHFFFAOYSA-N N=C(C(C(C1c(cc2)c34)c3cccc4c2-c2ccc(C(F)(F)F)cc2)c(cc2)ccc2C#N)C1c(cc1)ccc1C#N Chemical compound N=C(C(C(C1c(cc2)c34)c3cccc4c2-c2ccc(C(F)(F)F)cc2)c(cc2)ccc2C#N)C1c(cc1)ccc1C#N MLHWWAZVNGNKOP-UHFFFAOYSA-N 0.000 description 1
- IUXIMDVTDKBKGV-UHFFFAOYSA-N N=C(C(C1c(cc2)c34)c(cc5)ccc5-c(cc5)ccc5F)C(c(cc5)ccc5-c(cc5)ccc5F)=C1c3cccc4c2C#N Chemical compound N=C(C(C1c(cc2)c34)c(cc5)ccc5-c(cc5)ccc5F)C(c(cc5)ccc5-c(cc5)ccc5F)=C1c3cccc4c2C#N IUXIMDVTDKBKGV-UHFFFAOYSA-N 0.000 description 1
- FZHGOPFWTYPWIQ-UHFFFAOYSA-N N=C(C(C1c(cc2)c34)c(cc5)ccc5F)C(c(cc5)ccc5F)=C1c3cccc4c2-c(cc1)ccc1C#N Chemical compound N=C(C(C1c(cc2)c34)c(cc5)ccc5F)C(c(cc5)ccc5F)=C1c3cccc4c2-c(cc1)ccc1C#N FZHGOPFWTYPWIQ-UHFFFAOYSA-N 0.000 description 1
- XKWKSKVZPPQIRA-UHFFFAOYSA-N N=C(C(C1c(cc2)c34)c5ccccc5)C(c5ccccc5)=C1c3cccc4c2-c(cc1)ccc1C#N Chemical compound N=C(C(C1c(cc2)c34)c5ccccc5)C(c5ccccc5)=C1c3cccc4c2-c(cc1)ccc1C#N XKWKSKVZPPQIRA-UHFFFAOYSA-N 0.000 description 1
- UZBLJCYRKCGJQD-UHFFFAOYSA-N N=C(C(C1c(cc2)c3c4c2F)c(cc2)ccc2-c2ccccc2)C(c(cc2)ccc2-c2ccccc2)=C1c3ccc4F Chemical compound N=C(C(C1c(cc2)c3c4c2F)c(cc2)ccc2-c2ccccc2)C(c(cc2)ccc2-c2ccccc2)=C1c3ccc4F UZBLJCYRKCGJQD-UHFFFAOYSA-N 0.000 description 1
- WYVKBTUKZXHRMS-UHFFFAOYSA-N N=C1C(c(cc2)ccc2-c(cc2)ccc2F)=C(c(c2c3ccc(F)c22)ccc2F)C3=C1c(cc1)ccc1-c(cc1)ccc1F Chemical compound N=C1C(c(cc2)ccc2-c(cc2)ccc2F)=C(c(c2c3ccc(F)c22)ccc2F)C3=C1c(cc1)ccc1-c(cc1)ccc1F WYVKBTUKZXHRMS-UHFFFAOYSA-N 0.000 description 1
- FQLVEKNAZWIDMC-UHFFFAOYSA-N N=C1C(c(cc2)ccc2C#N)=C(c(cc2)c(c3ccc4)c4c2-c(cc2)ccc2C#N)C3=C1c(cc1)ccc1C#N Chemical compound N=C1C(c(cc2)ccc2C#N)=C(c(cc2)c(c3ccc4)c4c2-c(cc2)ccc2C#N)C3=C1c(cc1)ccc1C#N FQLVEKNAZWIDMC-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 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
- 239000010405 anode material Substances 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 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
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 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
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 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
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)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
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- YTIFDAAZLZVHIX-UHFFFAOYSA-N naphtho[1,2-g][1]benzofuran Chemical group C1=CC=C2C3=CC=C4C=COC4=C3C=CC2=C1 YTIFDAAZLZVHIX-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N perylene Chemical compound C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 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
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ILIAWFGIVGTZJI-UHFFFAOYSA-J pyridine;tetrachlorotitanium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ti+4].C1=CC=NC=C1 ILIAWFGIVGTZJI-UHFFFAOYSA-J 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl 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
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical group O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/50—
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20150133837 | 2015-09-22 | ||
KR1020150133837 | 2015-09-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20170035344A KR20170035344A (ko) | 2017-03-30 |
KR101950855B1 true KR101950855B1 (ko) | 2019-02-22 |
Family
ID=58386438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020160121649A KR101950855B1 (ko) | 2015-09-22 | 2016-09-22 | 신규 화합물 및 이를 포함하는 유기 발광 소자 |
Country Status (4)
Country | Link |
---|---|
KR (1) | KR101950855B1 (zh) |
CN (1) | CN107406350B (zh) |
TW (1) | TWI638798B (zh) |
WO (1) | WO2017052221A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107235858A (zh) * | 2017-07-13 | 2017-10-10 | 长春海谱润斯科技有限公司 | 一种具有电子传输效应的有机电致发光材料及其有机发光器件 |
CN112552246A (zh) * | 2019-09-26 | 2021-03-26 | 广州华睿光电材料有限公司 | 环戊二烯并吡嗪类有机化合物及其应用 |
CN112552304B (zh) * | 2019-09-26 | 2022-06-07 | 广州华睿光电材料有限公司 | 芳环并芘醌类化合物及其应用 |
CN112778081B (zh) * | 2020-12-28 | 2022-11-25 | 上海和辉光电股份有限公司 | 一种用于有机发光的化合物及其应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5700614A (en) * | 1994-03-03 | 1997-12-23 | Ricoh Company, Ltd. | cyclopentadiene derivative compounds and electrophotographic photoconductor comprising one cyclopentadiene derivative compound |
JPH09319110A (ja) * | 1996-05-27 | 1997-12-12 | Konica Corp | 電子写真感光体 |
JP5242917B2 (ja) | 2004-03-19 | 2013-07-24 | エルジー・ケム・リミテッド | 新規な正孔注入または輸送用物質及びこれを用いた有機発光素子 |
KR100809481B1 (ko) * | 2006-04-17 | 2008-03-03 | 네오뷰코오롱 주식회사 | 적색 유기 발광 화합물 및 이를 포함하는 유기 발광다이오드 |
CN101558507A (zh) * | 2006-12-15 | 2009-10-14 | 出光兴产株式会社 | 有机电致发光元件用材料以及有机电致发光元件 |
KR20150010016A (ko) * | 2013-07-17 | 2015-01-28 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
-
2016
- 2016-09-22 WO PCT/KR2016/010574 patent/WO2017052221A1/ko active Application Filing
- 2016-09-22 TW TW105130634A patent/TWI638798B/zh active
- 2016-09-22 KR KR1020160121649A patent/KR101950855B1/ko active IP Right Grant
- 2016-09-22 CN CN201680014648.1A patent/CN107406350B/zh active Active
Non-Patent Citations (1)
Title |
---|
Chemistry A European Journal, Vol.21, pp.8168-8176, 2015. |
Also Published As
Publication number | Publication date |
---|---|
CN107406350A (zh) | 2017-11-28 |
TW201722889A (zh) | 2017-07-01 |
TWI638798B (zh) | 2018-10-21 |
KR20170035344A (ko) | 2017-03-30 |
WO2017052221A1 (ko) | 2017-03-30 |
CN107406350B (zh) | 2021-04-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101781739B1 (ko) | 신규 화합물 및 이를 포함하는 유기 발광 소자 | |
KR102087487B1 (ko) | 신규 화합물 및 이를 포함하는 유기 발광 소자 | |
KR101980730B1 (ko) | 니트릴계 화합물 및 이를 포함하는 유기 발광 소자 | |
KR102000171B1 (ko) | 스피로형 화합물 및 이를 포함하는 유기 발광 소자 | |
KR101878544B1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
KR102465732B1 (ko) | 신규한 화합물 및 이를 포함하는 유기 발광 소자 | |
KR20200129993A (ko) | 유기 발광 소자 | |
KR101968213B1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
KR101950855B1 (ko) | 신규 화합물 및 이를 포함하는 유기 발광 소자 | |
KR20200129989A (ko) | 유기 발광 소자 | |
KR102175713B1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 | |
KR102322872B1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
KR102235477B1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자 | |
KR102235479B1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 | |
KR102280866B1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
KR20200115159A (ko) | 신규한 화합물 및 이를 포함하는 유기발광 소자 | |
KR20200105388A (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
KR101961342B1 (ko) | 헤테로환 화합물 및 이를 포함하는 유기 발광 소자 | |
KR102311640B1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
KR102171941B1 (ko) | 신규한 화합물 및 이를 포함하는 유기 발광 소자 | |
KR101951378B1 (ko) | 아민계 화합물 및 이를 포함하는 유기 발광 소자 | |
KR20200117257A (ko) | 신규한 화합물 및 이를 포함하는 유기발광 소자 | |
KR102246975B1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
KR102238703B1 (ko) | 유기 발광 소자 | |
KR102246983B1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right |