KR102141284B1 - 다환 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
다환 화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
- Publication number
- KR102141284B1 KR102141284B1 KR1020180135223A KR20180135223A KR102141284B1 KR 102141284 B1 KR102141284 B1 KR 102141284B1 KR 1020180135223 A KR1020180135223 A KR 1020180135223A KR 20180135223 A KR20180135223 A KR 20180135223A KR 102141284 B1 KR102141284 B1 KR 102141284B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- substituted
- unsubstituted
- formula
- same
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 64
- 239000000126 substance Substances 0.000 claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 220
- 239000010410 layer Substances 0.000 claims description 170
- 125000003118 aryl group Chemical group 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 239000011368 organic material Substances 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 238000002347 injection Methods 0.000 claims description 34
- 239000007924 injection Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 26
- 125000005264 aryl amine group Chemical group 0.000 claims description 22
- 239000012044 organic layer Substances 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 18
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
- 229910052711 selenium Inorganic materials 0.000 claims description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 101000831940 Homo sapiens Stathmin Proteins 0.000 claims description 5
- 102100024237 Stathmin Human genes 0.000 claims description 5
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 82
- 239000000463 material Substances 0.000 description 57
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
- -1 3-methylcyclopentyl Chemical group 0.000 description 34
- 125000000623 heterocyclic group Chemical group 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229910052805 deuterium Inorganic materials 0.000 description 23
- 125000001624 naphthyl group Chemical group 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 125000006267 biphenyl group Chemical group 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 18
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- 125000004665 trialkylsilyl group Chemical group 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 13
- 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 13
- 239000002904 solvent Substances 0.000 description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 0 CC(C)(C)c(cccc1)c1N(c1c2c(N(c3c(C(C)(C)*4)cccc3)c3c(C5(C)C=CC=CC5O5)c5c5-c6ccccc6)cc4c1)c1c4-c6ccccc6*c4c(-c4ccccc4)c4c1B2c3c5N4c1ccccc1 Chemical compound CC(C)(C)c(cccc1)c1N(c1c2c(N(c3c(C(C)(C)*4)cccc3)c3c(C5(C)C=CC=CC5O5)c5c5-c6ccccc6)cc4c1)c1c4-c6ccccc6*c4c(-c4ccccc4)c4c1B2c3c5N4c1ccccc1 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 125000003367 polycyclic group Chemical group 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000005580 triphenylene group Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 150000001716 carbazoles Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical group C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 description 6
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 6
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000005577 anthracene group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 6
- 125000005956 isoquinolyl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 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 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 6
- 125000005493 quinolyl group Chemical group 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- QJTQKPNNQVLHHO-UHFFFAOYSA-N 9h-carbazole;1h-indole Chemical compound C1=CC=C2NC=CC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 QJTQKPNNQVLHHO-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005566 carbazolylene group Chemical group 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004957 naphthylene group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 4
- 125000005560 phenanthrenylene group Chemical group 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 125000006836 terphenylene group Chemical group 0.000 description 4
- 125000005730 thiophenylene group Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WYLIRYQDDKDHLT-UHFFFAOYSA-N CC1=CC=CC=C1C.CC1=CC=CC=C1C Chemical compound CC1=CC=CC=C1C.CC1=CC=CC=C1C WYLIRYQDDKDHLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910003813 NRa Inorganic materials 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000002987 phenanthrenes Chemical group 0.000 description 3
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000003974 aralkylamines Chemical group 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000460 chlorine Substances 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
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical group 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000007774 positive electrode material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-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
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 1
- MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-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
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- AJUHJMMNWVKCER-UHFFFAOYSA-N 2-(2-phenylphenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 AJUHJMMNWVKCER-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 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
- 125000006027 3-methyl-1-butenyl group Chemical group 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RXAFXHRAUBYNMP-UHFFFAOYSA-N C(C)(C)(C)C1=NC(=CC=C1)C(C)(C)C.C(C)(C)(C)C1=NC(=CC=C1)C(C)(C)C Chemical compound C(C)(C)(C)C1=NC(=CC=C1)C(C)(C)C.C(C)(C)(C)C1=NC(=CC=C1)C(C)(C)C RXAFXHRAUBYNMP-UHFFFAOYSA-N 0.000 description 1
- KHPWDBWPFQFUKV-UHFFFAOYSA-N C(C1)C=CC=C1c1cc(-c2ccccc2)c2N(c3ccccc3)c3c4[o]c(cccc5)c5c4cc(O4)c3B3c2c1N(c1ccccc1)c1cc([o]c2ccccc22)c2c4c31 Chemical compound C(C1)C=CC=C1c1cc(-c2ccccc2)c2N(c3ccccc3)c3c4[o]c(cccc5)c5c4cc(O4)c3B3c2c1N(c1ccccc1)c1cc([o]c2ccccc22)c2c4c31 KHPWDBWPFQFUKV-UHFFFAOYSA-N 0.000 description 1
- POUNBOJRWBDHCG-VBHTVASYSA-N CC(C(C=C1)c2ccccc2)c2c1[o]c1c2c(N(c2ccccc2)c2c(B3c(c(N4c5ccccc5)cc(C)c5)c5N5c6ccccc6)c5c([C@]5(C)C=CC=CC5O5)c5c2)c3c4c1 Chemical compound CC(C(C=C1)c2ccccc2)c2c1[o]c1c2c(N(c2ccccc2)c2c(B3c(c(N4c5ccccc5)cc(C)c5)c5N5c6ccccc6)c5c([C@]5(C)C=CC=CC5O5)c5c2)c3c4c1 POUNBOJRWBDHCG-VBHTVASYSA-N 0.000 description 1
- AQXONGXNKJIASO-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(C(C)(C12)C=C(C)C=C1N(c1ccc(C(C)(C)C)cc1)c1cc(c3ccc4)c5[o]c3c4[SiH-](C)(C)C)c3c(C4C=CC=CC4O4)c4cc4c3B2c1c5S4 Chemical compound CC(C)(C)c(cc1)ccc1N(C(C)(C12)C=C(C)C=C1N(c1ccc(C(C)(C)C)cc1)c1cc(c3ccc4)c5[o]c3c4[SiH-](C)(C)C)c3c(C4C=CC=CC4O4)c4cc4c3B2c1c5S4 AQXONGXNKJIASO-UHFFFAOYSA-N 0.000 description 1
- JCSJBNTZDSTFHZ-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c(c(B12)c3Oc4c1c(N1c5ccc(C(C)(C)C)cc5)c(c5ccccc5[o]5)c5c4)cc4c3[o]c3c4cccc3)c3c2c1cc(C)c3 Chemical compound CC(C)(C)c(cc1)ccc1N(c(c(B12)c3Oc4c1c(N1c5ccc(C(C)(C)C)cc5)c(c5ccccc5[o]5)c5c4)cc4c3[o]c3c4cccc3)c3c2c1cc(C)c3 JCSJBNTZDSTFHZ-UHFFFAOYSA-N 0.000 description 1
- OIMFRLPKUMZUOJ-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c1c(B23)c(N4c5ccc(C(C)(C)C)cc5)cc(C)c1)C(C=C1c(cc(C(C)(C)C)cc5)c5O[C]11)=C2C1=P(c1ccccc1)c1c3c4c(c2ccccc2[o]2)c2c1 Chemical compound CC(C)(C)c(cc1)ccc1N(c1c(B23)c(N4c5ccc(C(C)(C)C)cc5)cc(C)c1)C(C=C1c(cc(C(C)(C)C)cc5)c5O[C]11)=C2C1=P(c1ccccc1)c1c3c4c(c2ccccc2[o]2)c2c1 OIMFRLPKUMZUOJ-UHFFFAOYSA-N 0.000 description 1
- CGAAHBWPJYFMKN-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c1c(B2c(c(N3c4ccc(C(C)(C)C)cc4)c4[s]c(cccc5)c5c4c4)c4Sc4c22)c3cc(C)c1)c2cc-1c4SCc2c-1cccc2 Chemical compound CC(C)(C)c(cc1)ccc1N(c1c(B2c(c(N3c4ccc(C(C)(C)C)cc4)c4[s]c(cccc5)c5c4c4)c4Sc4c22)c3cc(C)c1)c2cc-1c4SCc2c-1cccc2 CGAAHBWPJYFMKN-UHFFFAOYSA-N 0.000 description 1
- OEYRDNYFBPIVOI-QHEHZHCGSA-N CC(C)(C)c(cc1)ccc1N(c1cc(C)cc(N2c3ccc(C(C)(C)C)cc3)c1B13)C(C=C4c(cccc5)c5O[C]44)=C1C4=P(c1ccccc1)c1c3c2c(C2C=CC=C[C@H]2O2)c2c1 Chemical compound CC(C)(C)c(cc1)ccc1N(c1cc(C)cc(N2c3ccc(C(C)(C)C)cc3)c1B13)C(C=C4c(cccc5)c5O[C]44)=C1C4=P(c1ccccc1)c1c3c2c(C2C=CC=C[C@H]2O2)c2c1 OEYRDNYFBPIVOI-QHEHZHCGSA-N 0.000 description 1
- XSNYXPLVXAEVQY-UHFFFAOYSA-N CC(C)(C)c(cccc1)c1N(C(C1B23)=C(c4ccccc4O4)C4=C(C4CCCCC4)C1N(c1ccccc1)c1c2c(N2c4c(C(C)(C)C)cccc4)c(c(cccc4)c4[o]4)c4c1C1CCCCC1)c1c3c2cc(C)c1 Chemical compound CC(C)(C)c(cccc1)c1N(C(C1B23)=C(c4ccccc4O4)C4=C(C4CCCCC4)C1N(c1ccccc1)c1c2c(N2c4c(C(C)(C)C)cccc4)c(c(cccc4)c4[o]4)c4c1C1CCCCC1)c1c3c2cc(C)c1 XSNYXPLVXAEVQY-UHFFFAOYSA-N 0.000 description 1
- NHJWQAOCKQTKMJ-UHFFFAOYSA-N CC(C)(C)c1cc(N(c2c(C(C)(C)C)cccc2)c2c(B3C(C(C)(C(c4cc(C5CCCCC5)ccc4O4)C4=C4)P5c6ccccc6)=C4N4c6c(C(C)(C)C)cccc6)c5cc5c2c2ccccc2[o]5)c3c4c1 Chemical compound CC(C)(C)c1cc(N(c2c(C(C)(C)C)cccc2)c2c(B3C(C(C)(C(c4cc(C5CCCCC5)ccc4O4)C4=C4)P5c6ccccc6)=C4N4c6c(C(C)(C)C)cccc6)c5cc5c2c2ccccc2[o]5)c3c4c1 NHJWQAOCKQTKMJ-UHFFFAOYSA-N 0.000 description 1
- QPCCKDXJFPMVAX-UHFFFAOYSA-N CC(C)(C)c1cc(N(c2c(C(C)(C)C)cccc2)c2c3c(cccc4)c4[o]c3cc3c2B2c(c(N4c5c(C(C)(C)C)cccc5)cc5c6c(cc(C7CCCCC7)cc7)c7[o]5)c6O3)c2c4c1 Chemical compound CC(C)(C)c1cc(N(c2c(C(C)(C)C)cccc2)c2c3c(cccc4)c4[o]c3cc3c2B2c(c(N4c5c(C(C)(C)C)cccc5)cc5c6c(cc(C7CCCCC7)cc7)c7[o]5)c6O3)c2c4c1 QPCCKDXJFPMVAX-UHFFFAOYSA-N 0.000 description 1
- LXUBTTJTLZDJAQ-UHFFFAOYSA-N CC(C)(C)c1cc(N(c2cccc3c2cccc3)C(c2c([CH]3)c(cccc4)c4[o]2)=C(B24)C3=P(c3ccccc3)c3c2c(N2c5c(cccc6)c6ccc5)nc5c3c3ccccc3[o]5)c4c2c1 Chemical compound CC(C)(C)c1cc(N(c2cccc3c2cccc3)C(c2c([CH]3)c(cccc4)c4[o]2)=C(B24)C3=P(c3ccccc3)c3c2c(N2c5c(cccc6)c6ccc5)nc5c3c3ccccc3[o]5)c4c2c1 LXUBTTJTLZDJAQ-UHFFFAOYSA-N 0.000 description 1
- VCKRUTJFDXJBHT-UHFFFAOYSA-N CC(C)(C)c1cc(N(c2ccccc2)c2cc([o]c(c3ccc4)c4N(c4ccccc4)c4ccccc4)c3c3c2B2c(c(N4c5ccccc5)c(c(cccc5)c5[o]5)c5c5)c5N3c3ccccc3)c2c4c1 Chemical compound CC(C)(C)c1cc(N(c2ccccc2)c2cc([o]c(c3ccc4)c4N(c4ccccc4)c4ccccc4)c3c3c2B2c(c(N4c5ccccc5)c(c(cccc5)c5[o]5)c5c5)c5N3c3ccccc3)c2c4c1 VCKRUTJFDXJBHT-UHFFFAOYSA-N 0.000 description 1
- POHAITQYKFVSRJ-ICUBTYBPSA-N CC(C)(C)c1cc(N(c2ccccc2)c2cc([o]c3c4C=CC[C@]3(C)N(c3ccccc3)c3ccccc3)c4c3c2B2c(c(N4c5ccccc5)c(C5(C)C=CC=CC5O5)c5c5)c5O3)c2c4c1 Chemical compound CC(C)(C)c1cc(N(c2ccccc2)c2cc([o]c3c4C=CC[C@]3(C)N(c3ccccc3)c3ccccc3)c4c3c2B2c(c(N4c5ccccc5)c(C5(C)C=CC=CC5O5)c5c5)c5O3)c2c4c1 POHAITQYKFVSRJ-ICUBTYBPSA-N 0.000 description 1
- XHTNSNMCGHRPMW-UHFFFAOYSA-N CC(C)(C)c1ccccc1N(c1c2c(N(C3=C(C(C)(C)C)C=CCC3)C3=CC(C)(C45)Oc6c4cccc6)cc(C4CCCCC4)c1)c1c(c(cccc4)c4[o]4)c4cc4c1B2C3=C5S4 Chemical compound CC(C)(C)c1ccccc1N(c1c2c(N(C3=C(C(C)(C)C)C=CCC3)C3=CC(C)(C45)Oc6c4cccc6)cc(C4CCCCC4)c1)c1c(c(cccc4)c4[o]4)c4cc4c1B2C3=C5S4 XHTNSNMCGHRPMW-UHFFFAOYSA-N 0.000 description 1
- TZJSNAYAYSWLRF-UHFFFAOYSA-N CC(C1)C=Cc2c1c(C=C1N(c3ccccc3)c3cccc(N(c4ccccc4)c4c(c5ccccc5[o]5)c5c5)c3B3c4c5OC4C13)c4[o]2 Chemical compound CC(C1)C=Cc2c1c(C=C1N(c3ccccc3)c3cccc(N(c4ccccc4)c4c(c5ccccc5[o]5)c5c5)c3B3c4c5OC4C13)c4[o]2 TZJSNAYAYSWLRF-UHFFFAOYSA-N 0.000 description 1
- WDNMJPIUAJDYPR-UHFFFAOYSA-N CC(C1)C=Cc2c1c(cc(c(B13)c4Oc5c1c(N1c6cccc7c6cccc7)c(c(cccc6)c6[o]6)c6c5)N(c5c(cccc6)c6ccc5)c5c3c1cc(-c1ccccc1)c5)c4[o]2 Chemical compound CC(C1)C=Cc2c1c(cc(c(B13)c4Oc5c1c(N1c6cccc7c6cccc7)c(c(cccc6)c6[o]6)c6c5)N(c5c(cccc6)c6ccc5)c5c3c1cc(-c1ccccc1)c5)c4[o]2 WDNMJPIUAJDYPR-UHFFFAOYSA-N 0.000 description 1
- HVWSSOCASFRXIO-UHFFFAOYSA-N CC(C1)C=Cc2c1c(cc1N(c3ccccc3)C(C=CC3C4=CCC=CCC4C)=C4C3N(c3ccccc3)c3c5[o]c(cccc6)c6c5cc5c3B4c1c1N5C3=CC=CCC3)c1[o]2 Chemical compound CC(C1)C=Cc2c1c(cc1N(c3ccccc3)C(C=CC3C4=CCC=CCC4C)=C4C3N(c3ccccc3)c3c5[o]c(cccc6)c6c5cc5c3B4c1c1N5C3=CC=CCC3)c1[o]2 HVWSSOCASFRXIO-UHFFFAOYSA-N 0.000 description 1
- ACWBZRGNQYTVHH-UHFFFAOYSA-N CC(C1)C=Cc2c1c1cc(N(C3=C(B4c(c(N5c6cc(-c7ccccc7)ccc6)c6[o]c(cccc7)c7c6c6)c6S6)C5=CC(C)C3)c3cc(-c5ccccc5)ccc3)c4c6c1[n]2-c1ccccc1 Chemical compound CC(C1)C=Cc2c1c1cc(N(C3=C(B4c(c(N5c6cc(-c7ccccc7)ccc6)c6[o]c(cccc7)c7c6c6)c6S6)C5=CC(C)C3)c3cc(-c5ccccc5)ccc3)c4c6c1[n]2-c1ccccc1 ACWBZRGNQYTVHH-UHFFFAOYSA-N 0.000 description 1
- DKEPQWYHNCWECY-UHFFFAOYSA-N CC(CC=C1)C=C1N(c(c1c2N(c3ccc(C(C)(C)C)cc3)c3cc(C)cc(N4c5ccc(C(C)(C)C)cc5)c3B11)cc3c2[o]c2c3cccc2)c2c1c4nc1c2[o]c2ccccc12 Chemical compound CC(CC=C1)C=C1N(c(c1c2N(c3ccc(C(C)(C)C)cc3)c3cc(C)cc(N4c5ccc(C(C)(C)C)cc5)c3B11)cc3c2[o]c2c3cccc2)c2c1c4nc1c2[o]c2ccccc12 DKEPQWYHNCWECY-UHFFFAOYSA-N 0.000 description 1
- LPRDPFOMHPRZSN-UHFFFAOYSA-N CC(CC=C1)c([o]c2c3)c1c2c1Oc2cc([o]c4ccccc44)c4c(N4C5(C)C(C(C)(C)C)=CC=CC5)c2B2c1c3N(c1c(C(C)(C)C)cccc1)c1cc(C3CCCCC3)cc4c21 Chemical compound CC(CC=C1)c([o]c2c3)c1c2c1Oc2cc([o]c4ccccc44)c4c(N4C5(C)C(C(C)(C)C)=CC=CC5)c2B2c1c3N(c1c(C(C)(C)C)cccc1)c1cc(C3CCCCC3)cc4c21 LPRDPFOMHPRZSN-UHFFFAOYSA-N 0.000 description 1
- PUYKWTZDSZKBSK-UHFFFAOYSA-N CC(CC=C1)c([o]c2c3)c1c2c1SC(C24C)=CC(OC5(C)C=CC=CC55)=C5C2N(c2cc(-c5ccccc5)ccc2)c2cc(C)cc5c2B4c1c3N5c1cc(-c2ccccc2)ccc1 Chemical compound CC(CC=C1)c([o]c2c3)c1c2c1SC(C24C)=CC(OC5(C)C=CC=CC55)=C5C2N(c2cc(-c5ccccc5)ccc2)c2cc(C)cc5c2B4c1c3N5c1cc(-c2ccccc2)ccc1 PUYKWTZDSZKBSK-UHFFFAOYSA-N 0.000 description 1
- BSKDRUOKLHJCLK-IOXNKQMXSA-N CC1(C=CC=CC1)c(ccc(N(c1c(C)cccc1)c1c(c2ccccc2[o]2)c2c2)c3B4c1c2N1c2ccccc2)c3N(c2c(C)cccc2)c2c4c1cc1c2c(C#C)c(/C=C\C)[o]1 Chemical compound CC1(C=CC=CC1)c(ccc(N(c1c(C)cccc1)c1c(c2ccccc2[o]2)c2c2)c3B4c1c2N1c2ccccc2)c3N(c2c(C)cccc2)c2c4c1cc1c2c(C#C)c(/C=C\C)[o]1 BSKDRUOKLHJCLK-IOXNKQMXSA-N 0.000 description 1
- SHUSJLFSKVHMHW-UHFFFAOYSA-N CC1(C=CC=CC1Oc1c2)c1c1N(c3ccccc3)c3cccc(N4C5=CC=CCC5)c3B3c1c2Sc1c3c4cc2c1OC1(C)C=CC=CC21 Chemical compound CC1(C=CC=CC1Oc1c2)c1c1N(c3ccccc3)c3cccc(N4C5=CC=CCC5)c3B3c1c2Sc1c3c4cc2c1OC1(C)C=CC=CC21 SHUSJLFSKVHMHW-UHFFFAOYSA-N 0.000 description 1
- PFDIZMFVRRAHAU-UHFFFAOYSA-N CC1(C=CC=CC1Oc1cc2c3B4c(c(N5C6(C)C=CC=CC6)c(c(cccc6)c6[o]6)c6c6)c6N2c2ccccc2)c1c3N(c1ccccc1)c(c(-c1ccccc1)c1)c4c5c1-c1ccccc1 Chemical compound CC1(C=CC=CC1Oc1cc2c3B4c(c(N5C6(C)C=CC=CC6)c(c(cccc6)c6[o]6)c6c6)c6N2c2ccccc2)c1c3N(c1ccccc1)c(c(-c1ccccc1)c1)c4c5c1-c1ccccc1 PFDIZMFVRRAHAU-UHFFFAOYSA-N 0.000 description 1
- KLNCDBYZKDQONW-UHFFFAOYSA-N CC1(C=CC=CC1Oc1cc2c3B4c(c(N5c6cccc(-c7ccccc7)c6)cc6c7c8ccccc8[o]6)c7O2)c1c3N(c1cc(-c2ccccc2)ccc1)c1c4c5cc(C)c1 Chemical compound CC1(C=CC=CC1Oc1cc2c3B4c(c(N5c6cccc(-c7ccccc7)c6)cc6c7c8ccccc8[o]6)c7O2)c1c3N(c1cc(-c2ccccc2)ccc1)c1c4c5cc(C)c1 KLNCDBYZKDQONW-UHFFFAOYSA-N 0.000 description 1
- KAJJOKJGTSOKTD-UHFFFAOYSA-N CC1(C=CC=CC1Oc1cc2c3B4c(c(N5c6ccccc6C)c(c(cccc6)c6[o]6)c6c6)c6N2c2ccccc2)c1c3N(c1ccccc1C)c1c4c5cc(-[n]2c(C=CCC3)c3c3ccccc23)c1 Chemical compound CC1(C=CC=CC1Oc1cc2c3B4c(c(N5c6ccccc6C)c(c(cccc6)c6[o]6)c6c6)c6N2c2ccccc2)c1c3N(c1ccccc1C)c1c4c5cc(-[n]2c(C=CCC3)c3c3ccccc23)c1 KAJJOKJGTSOKTD-UHFFFAOYSA-N 0.000 description 1
- SPFBJLXKEPUJKI-UHFFFAOYSA-N CC1(c(cccc2)c2N2c3cc(N(C(C(B45)(C)C(C6)P(c7ccccc7)c7c4c(N4c8ccccc8C)cc8c7c(cccc7)c7[o]8)c7c6c(cccc6)c6[o]7)c6ccccc6C)c5c4c3)C2=CC=CC1 Chemical compound CC1(c(cccc2)c2N2c3cc(N(C(C(B45)(C)C(C6)P(c7ccccc7)c7c4c(N4c8ccccc8C)cc8c7c(cccc7)c7[o]8)c7c6c(cccc6)c6[o]7)c6ccccc6C)c5c4c3)C2=CC=CC1 SPFBJLXKEPUJKI-UHFFFAOYSA-N 0.000 description 1
- BECGYMCQBLXKHH-UHFFFAOYSA-N CC1(c2ccccc2C=CC1)N(c1c2c(N(c3c(cccc4)c4ccc3)c3cc4c5[o]c6c4cccc6)cc(-c4ccccc4)c1)c1c(c(cccc4)c4[o]4)c4cc4c1B2c3c5N4c1ccccc1 Chemical compound CC1(c2ccccc2C=CC1)N(c1c2c(N(c3c(cccc4)c4ccc3)c3cc4c5[o]c6c4cccc6)cc(-c4ccccc4)c1)c1c(c(cccc4)c4[o]4)c4cc4c1B2c3c5N4c1ccccc1 BECGYMCQBLXKHH-UHFFFAOYSA-N 0.000 description 1
- ZXOGUNPSGJAPNT-UHFFFAOYSA-N CC1C(C2(C(C3C4=C5B6[C]7C(N8C9=CCC(C(C)(C)C)C=C9)=C9Sc(cccc%10)c%10C9=CC7=P4c4ccccc4)C=C5N(c4ccc(C(C)(C)C)cc4)c4c6c8cc(C)c4)c(cccc4)c4-c4c2cccc4)=C3C=CC1 Chemical compound CC1C(C2(C(C3C4=C5B6[C]7C(N8C9=CCC(C(C)(C)C)C=C9)=C9Sc(cccc%10)c%10C9=CC7=P4c4ccccc4)C=C5N(c4ccc(C(C)(C)C)cc4)c4c6c8cc(C)c4)c(cccc4)c4-c4c2cccc4)=C3C=CC1 ZXOGUNPSGJAPNT-UHFFFAOYSA-N 0.000 description 1
- DBSSFTLOQIQGJY-UHFFFAOYSA-N CC1C(c(cccc23)c2[o]c2c3c(Oc3c(B4C(C(N5c6ccccc6)=CCC(C)=C6)=C6N6c7ccccc7)c5c(c5ccccc5[o]5)c5c3)c4c6c2)=CC=CC1 Chemical compound CC1C(c(cccc23)c2[o]c2c3c(Oc3c(B4C(C(N5c6ccccc6)=CCC(C)=C6)=C6N6c7ccccc7)c5c(c5ccccc5[o]5)c5c3)c4c6c2)=CC=CC1 DBSSFTLOQIQGJY-UHFFFAOYSA-N 0.000 description 1
- VUSUKCAGSXMYTD-UHFFFAOYSA-N CC1C=CC(N(c2c3c(P(c4cc5c6c7ccccc7[o]5)=C5C=CC=C[C]5C5=CCC7)c8c5c7[o]c8c2)c2cc(N(c5ccc(C(C)(C)C)cc5)c5ccc(C(C)(C)C)cc5)cc5c2B3c4c6N5c2ccccc2C)=C(C)C1 Chemical compound CC1C=CC(N(c2c3c(P(c4cc5c6c7ccccc7[o]5)=C5C=CC=C[C]5C5=CCC7)c8c5c7[o]c8c2)c2cc(N(c5ccc(C(C)(C)C)cc5)c5ccc(C(C)(C)C)cc5)cc5c2B3c4c6N5c2ccccc2C)=C(C)C1 VUSUKCAGSXMYTD-UHFFFAOYSA-N 0.000 description 1
- UQZPLLHBCFTMKJ-PKMYLGHKSA-N C[C@@]12c(c(N(c3c(cccc4)c4ccc3)c3c(B4c(c(N5c6ccccc6)c(c6c7c8ccccc8[o]6)-c6ccccc6)c7N6c7cccc8c7cccc8)c6cc(-c6c(C)cccc6)c3)c4c5c3-c4ccccc4)c3OC1C=CC=C2 Chemical compound C[C@@]12c(c(N(c3c(cccc4)c4ccc3)c3c(B4c(c(N5c6ccccc6)c(c6c7c8ccccc8[o]6)-c6ccccc6)c7N6c7cccc8c7cccc8)c6cc(-c6c(C)cccc6)c3)c4c5c3-c4ccccc4)c3OC1C=CC=C2 UQZPLLHBCFTMKJ-PKMYLGHKSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UNIGQHXNADRYAT-UHFFFAOYSA-N Cc(cc1C)c2N(c3ccccc3)c3c(c(cccc4)c4[o]4)c4cc(N4c5ccccc5)c3B3c2c1N(c1ccccc1)c1c(c2ccccc2[o]2)c2cc4c31 Chemical compound Cc(cc1C)c2N(c3ccccc3)c3c(c(cccc4)c4[o]4)c4cc(N4c5ccccc5)c3B3c2c1N(c1ccccc1)c1c(c2ccccc2[o]2)c2cc4c31 UNIGQHXNADRYAT-UHFFFAOYSA-N 0.000 description 1
- JOGFZRLYADUVBF-UHFFFAOYSA-N Cc(cccc1)c1N(c1c(B2c(c(N3c4ccccc4)cc4c5c6ccccc6[o]4)c5N4c5ccccc5C)c4cc(N(c4ccccc4)c4ccccc4)c1)c(c1c4OC5C=CC=CC15)c2c3c4-c1ccccc1 Chemical compound Cc(cccc1)c1N(c1c(B2c(c(N3c4ccccc4)cc4c5c6ccccc6[o]4)c5N4c5ccccc5C)c4cc(N(c4ccccc4)c4ccccc4)c1)c(c1c4OC5C=CC=CC15)c2c3c4-c1ccccc1 JOGFZRLYADUVBF-UHFFFAOYSA-N 0.000 description 1
- ZDPZQCSCOWRBPA-UHFFFAOYSA-N Cc(cccc1)c1N1c2cc(-[n]3c4ccccc4c4c3cccc4)cc(N(c3ccccc3C)c3c(c(cccc4)c4[o]4)c4c4)c2B2c3c4Sc3c2c1cc1c3c(cccc2)c2[o]1 Chemical compound Cc(cccc1)c1N1c2cc(-[n]3c4ccccc4c4c3cccc4)cc(N(c3ccccc3C)c3c(c(cccc4)c4[o]4)c4c4)c2B2c3c4Sc3c2c1cc1c3c(cccc2)c2[o]1 ZDPZQCSCOWRBPA-UHFFFAOYSA-N 0.000 description 1
- FEVKBTYPBYTLOO-UHFFFAOYSA-N Cc1cc(N(c2cccc(-c3ccccc3)c2)c2nc([o]c3ccccc33)c3c3c2B2c(c(N4)c5[o]c(cccc6)c6c5c5)c5S3)c2c4c1 Chemical compound Cc1cc(N(c2cccc(-c3ccccc3)c2)c2nc([o]c3ccccc33)c3c3c2B2c(c(N4)c5[o]c(cccc6)c6c5c5)c5S3)c2c4c1 FEVKBTYPBYTLOO-UHFFFAOYSA-N 0.000 description 1
- ZDLZRAZBGARGID-UHFFFAOYSA-N Cc1cc(N(c2ccccc2)c(c(B23)c4N(c5ccccc5)c5c2c(N2C6=CC=CCC6)c(c6ccccc6[o]6)c6c5-[n]5c(cccc6)c6c6c5CCC=C6)c(c(cccc5)c5[o]5)c5c4-[n]4c5ccccc5c5c4cccc5)c3c2c1 Chemical compound Cc1cc(N(c2ccccc2)c(c(B23)c4N(c5ccccc5)c5c2c(N2C6=CC=CCC6)c(c6ccccc6[o]6)c6c5-[n]5c(cccc6)c6c6c5CCC=C6)c(c(cccc5)c5[o]5)c5c4-[n]4c5ccccc5c5c4cccc5)c3c2c1 ZDLZRAZBGARGID-UHFFFAOYSA-N 0.000 description 1
- CLXIAQPHNCLDTJ-UHFFFAOYSA-N Cc1cc(N(c2ccccc2)c2c(B3c(c(N4c5ccccc5)nc5c6c7ccccc7[o]5)c6N5c6ccccc6)c4cc4c2c2ccccc2[o]4)c3c5c1 Chemical compound Cc1cc(N(c2ccccc2)c2c(B3c(c(N4c5ccccc5)nc5c6c7ccccc7[o]5)c6N5c6ccccc6)c4cc4c2c2ccccc2[o]4)c3c5c1 CLXIAQPHNCLDTJ-UHFFFAOYSA-N 0.000 description 1
- REFZFAHPXLJFBA-UHFFFAOYSA-N Cc1cc(N(c2ccccc2)c2cc(SC3C=CC=CC33)c3c3c2B2c(c(N4c5ccccc5)cc(-c(cccc5)c5S)c5)c5S3)c2c4c1 Chemical compound Cc1cc(N(c2ccccc2)c2cc(SC3C=CC=CC33)c3c3c2B2c(c(N4c5ccccc5)cc(-c(cccc5)c5S)c5)c5S3)c2c4c1 REFZFAHPXLJFBA-UHFFFAOYSA-N 0.000 description 1
- QOLAVPJIQDXLRX-UHFFFAOYSA-N Cc1cc(N(c2ccccc2)c2cc([o]c(c3ccc4)c4-c4ccccc4)c3c3c2B2c(c(N4c5ccccc5)c(c5ccccc5[o]5)c5c5)c5S3)c2c4c1 Chemical compound Cc1cc(N(c2ccccc2)c2cc([o]c(c3ccc4)c4-c4ccccc4)c3c3c2B2c(c(N4c5ccccc5)c(c5ccccc5[o]5)c5c5)c5S3)c2c4c1 QOLAVPJIQDXLRX-UHFFFAOYSA-N 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
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NFTRAGGUIJBGHD-UHFFFAOYSA-N N-(9H-fluoren-1-yl)phenanthren-1-amine Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC1=2)NC1=CC=CC=2C3=CC=CC=C3CC1=2 NFTRAGGUIJBGHD-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- ACYWVHCCUGTDEW-UHFFFAOYSA-N N-naphthalen-1-yl-9H-fluoren-1-amine Chemical group C1(=CC=CC2=CC=CC=C12)NC1=CC=CC=2C3=CC=CC=C3CC12 ACYWVHCCUGTDEW-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- GGLALOILOBJLRX-UHFFFAOYSA-N [Li]C(C)(C)C.CCCCC Chemical compound [Li]C(C)(C)C.CCCCC GGLALOILOBJLRX-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 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 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 239000012267 brine Substances 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
- OIKVGTJLVXINCP-UHFFFAOYSA-N c(cc1)ccc1-c1cc(N(c2ccccc2)c2c(c(cccc3)c3[o]3)c3nc(N3c4ccccc4)c2B2c4c3nc3[o]c(cccc5)c5c3c4N3c4ccccc4)c2c3c1 Chemical compound c(cc1)ccc1-c1cc(N(c2ccccc2)c2c(c(cccc3)c3[o]3)c3nc(N3c4ccccc4)c2B2c4c3nc3[o]c(cccc5)c5c3c4N3c4ccccc4)c2c3c1 OIKVGTJLVXINCP-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium 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
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 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
- 238000005137 deposition process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 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
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- NJVSFOMTEFOHMI-UHFFFAOYSA-N n,2-diphenylaniline Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1NC1=CC=CC=C1 NJVSFOMTEFOHMI-UHFFFAOYSA-N 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
- 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
- HCISEFFYVMEPNF-UHFFFAOYSA-N n-phenyl-9h-fluoren-1-amine Chemical group C=12CC3=CC=CC=C3C2=CC=CC=1NC1=CC=CC=C1 HCISEFFYVMEPNF-UHFFFAOYSA-N 0.000 description 1
- UMGBMWFOGBJCJA-UHFFFAOYSA-N n-phenylphenanthren-1-amine Chemical group C=1C=CC(C2=CC=CC=C2C=C2)=C2C=1NC1=CC=CC=C1 UMGBMWFOGBJCJA-UHFFFAOYSA-N 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
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000003226 pyrazolyl 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
- 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-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
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001544 thienyl 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
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- 238000007740 vapor deposition Methods 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
- 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/008—
-
- H01L51/5012—
-
- H01L51/5056—
-
- H01L51/5072—
-
- H01L51/5096—
-
- 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
-
- 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
- H10K50/16—Electron transporting layers
-
- 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
- C09K2211/1018—Heterocyclic compounds
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/18—Carrier blocking layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20170146798 | 2017-11-06 | ||
| KR1020170146798 | 2017-11-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20190051867A KR20190051867A (ko) | 2019-05-15 |
| KR102141284B1 true KR102141284B1 (ko) | 2020-08-05 |
Family
ID=66332645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020180135223A KR102141284B1 (ko) | 2017-11-06 | 2018-11-06 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR102141284B1 (zh) |
| CN (1) | CN111094302B (zh) |
| WO (1) | WO2019088799A1 (zh) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101876763B1 (ko) * | 2017-05-22 | 2018-07-11 | 머티어리얼사이언스 주식회사 | 유기화합물 및 이를 포함하는 유기전계발광소자 |
| KR102353148B1 (ko) * | 2019-01-18 | 2022-01-19 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20200119453A (ko) * | 2019-04-09 | 2020-10-20 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
| KR20220019714A (ko) * | 2019-06-11 | 2022-02-17 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 |
| JPWO2020251049A1 (zh) * | 2019-06-14 | 2020-12-17 | ||
| KR102381641B1 (ko) * | 2019-07-31 | 2022-04-01 | 주식회사 엘지화학 | 유기 발광 소자 |
| WO2021049889A1 (ko) * | 2019-09-10 | 2021-03-18 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| CN110981899B (zh) * | 2019-11-20 | 2023-02-03 | 苏州久显新材料有限公司 | 多环有机硼衍生物和电子器件 |
| CN110903311B (zh) * | 2019-11-20 | 2022-11-22 | 苏州久显新材料有限公司 | 多环有机硼衍生物和电子器件 |
| WO2021107744A1 (ko) * | 2019-11-29 | 2021-06-03 | 주식회사 엘지화학 | 유기 발광 소자 |
| US20230104248A1 (en) | 2019-12-19 | 2023-04-06 | Merck Patent Gmbh | Polycyclic compounds for organic electroluminescent devices |
| CN113666951B (zh) * | 2020-05-14 | 2022-12-20 | 季华实验室 | 一种硼氮化合物、有机电致发光组合物及包含其的有机电致发光器件 |
| CN111647010B (zh) * | 2020-06-02 | 2023-04-07 | 苏州久显新材料有限公司 | 多环含硼化合物及其电子器件 |
| CN113801151B (zh) * | 2020-07-14 | 2023-09-19 | 北京八亿时空液晶科技股份有限公司 | 一种稠环芳香族化合物及其应用 |
| CN114106021A (zh) * | 2020-08-25 | 2022-03-01 | 北京鼎材科技有限公司 | 一种化合物及其应用 |
| KR20220051823A (ko) * | 2020-10-19 | 2022-04-26 | 에스에프씨 주식회사 | 유기발광소자 |
| KR20220064474A (ko) | 2020-11-11 | 2022-05-19 | 삼성디스플레이 주식회사 | 발광 소자 |
| EP4380338A1 (en) * | 2021-07-27 | 2024-06-05 | Lordin Co., Ltd | Organic light-emitting diode |
| CN113416206B (zh) * | 2021-08-23 | 2022-03-15 | 浙江华显光电科技有限公司 | 螺环化合物、制剂、有机电致发光二极管及显示装置 |
| KR20240019321A (ko) * | 2021-09-20 | 2024-02-14 | 삼성디스플레이 주식회사 | 광전자 소자용 유기 분자 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266484A (zh) * | 2017-07-14 | 2017-10-20 | 瑞声科技（南京）有限公司 | 有机电致发光材料及其发光器件 |
| US20180069182A1 (en) | 2016-09-07 | 2018-03-08 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101317511B1 (ko) * | 2009-04-30 | 2013-10-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
| KR102524531B1 (ko) * | 2015-11-03 | 2023-04-24 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| JP6634838B2 (ja) * | 2016-01-12 | 2020-01-22 | コニカミノルタ株式会社 | 電子デバイス材料、有機エレクトロルミネッセンス素子、表示装置、及び、照明装置 |
| KR102100008B1 (ko) * | 2016-04-12 | 2020-04-10 | 주식회사 엘지화학 | 안트라센계 화합물 및 이를 포함하는 유기 발광 소자 |
-
2018
- 2018-11-06 KR KR1020180135223A patent/KR102141284B1/ko active IP Right Grant
- 2018-11-06 WO PCT/KR2018/013380 patent/WO2019088799A1/ko active Application Filing
- 2018-11-06 CN CN201880055634.3A patent/CN111094302B/zh active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180069182A1 (en) | 2016-09-07 | 2018-03-08 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
| CN107266484A (zh) * | 2017-07-14 | 2017-10-20 | 瑞声科技（南京）有限公司 | 有机电致发光材料及其发光器件 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2019088799A1 (ko) | 2019-05-09 |
| CN111094302A (zh) | 2020-05-01 |
| KR20190051867A (ko) | 2019-05-15 |
| CN111094302B (zh) | 2022-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102141284B1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| JP7251711B2 (ja) | 有機発光素子 | |
| KR20210042873A (ko) | 유기발광소자 | |
| KR20200081302A (ko) | 화합물 및 이를 포함하는 유기발광소자 | |
| KR102117765B1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20200087717A (ko) | 화합물 및 이를 포함하는 유기발광소자 | |
| KR20180099564A (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR102132536B1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20200090123A (ko) | 유기 발광 소자 | |
| KR20200107855A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR102618829B1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR102256782B1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20180042944A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
| KR20200078156A (ko) | 신규한 화합물 및 이를 포함하는 유기발광 소자 | |
| KR20180042967A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
| KR102560366B1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20190129509A (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR102364567B1 (ko) | 화합물 및 이를 포함하는 유기발광소자 | |
| KR102176862B1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR102238900B1 (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20210010407A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20200090122A (ko) | 유기 발광 소자 | |
| KR20200075777A (ko) | 다환 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR102578743B1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
| KR20230018103A (ko) | 화합물 및 이를 포함하는 유기 발광 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 | ||
| GRNT | Written decision to grant |