JP2020113557A

JP2020113557A - アザカルバゾール構造を有する化合物および有機エレクトロルミネッセンス素子

アザカルバゾール構造を有する化合物および有機エレクトロルミネッセンス素子 Download PDF

Info

Publication number: JP2020113557A
Authority: JP; Japan
Prior art keywords: group; substituted; unsubstituted; atom; aromatic
Prior art date: 2017-03-28
Legal status : Pending

Application number

JP2017062155A

Other languages

English (en)

Japanese (ja)

Inventor

安達　千波矢

Chihaya Adachi

千波矢安達

卓也上原

Takuya Uehara

卓也上原

Current Assignee

Kyushu University NUC

Hodogaya Chemical Co Ltd

Original Assignee

Kyushu University NUC

Hodogaya Chemical Co Ltd

Priority date

2017-03-28

Filing date

2017-03-28

Publication date

2020-07-27

2017-03-28 Application filed by Kyushu University NUC, Hodogaya Chemical Co Ltd filed Critical Kyushu University NUC

2017-03-28 Priority to JP2017062155A priority Critical patent/JP2020113557A/ja

2018-03-27 Priority to PCT/JP2018/012526 priority patent/WO2018181370A1/fr

2020-07-27 Publication of JP2020113557A publication Critical patent/JP2020113557A/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 135
BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 title claims abstract description 27
239000000463 material Substances 0.000 claims abstract description 61
239000000470 constituent Substances 0.000 claims abstract description 4
239000010410 layer Substances 0.000 claims description 133
125000004432 carbon atom Chemical group C* 0.000 claims description 97
-1 di-substituted amino group Chemical group 0.000 claims description 85
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 57
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 55
125000001424 substituent group Chemical group 0.000 claims description 53
229910052757 nitrogen Inorganic materials 0.000 claims description 36
125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
229910052799 carbon Inorganic materials 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
125000004434 sulfur atom Chemical group 0.000 claims description 19
125000004430 oxygen atom Chemical group O* 0.000 claims description 18
125000004104 aryloxy group Chemical group 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
125000001309 chloro group Chemical group Cl* 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 17
125000001153 fluoro group Chemical group F* 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 14
229910052805 deuterium Inorganic materials 0.000 claims description 14
125000004431 deuterium atom Chemical group 0.000 claims description 14
125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 10
238000005401 electroluminescence Methods 0.000 claims description 6
239000012044 organic layer Substances 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 4
239000010409 thin film Substances 0.000 abstract description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
238000007740 vapor deposition Methods 0.000 description 36
239000010408 film Substances 0.000 description 34
238000000034 method Methods 0.000 description 28
238000002347 injection Methods 0.000 description 19
239000007924 injection Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
239000000203 mixture Substances 0.000 description 18
239000002356 single layer Substances 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
230000000903 blocking effect Effects 0.000 description 15
239000000758 substrate Substances 0.000 description 14
230000005525 hole transport Effects 0.000 description 13
238000005160 1H NMR spectroscopy Methods 0.000 description 12
238000002156 mixing Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000011521 glass Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
229940125782 compound 2 Drugs 0.000 description 8
229940125898 compound 5 Drugs 0.000 description 8
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
239000000843 powder Substances 0.000 description 8
VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 7
UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 7
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
229940125904 compound 1 Drugs 0.000 description 7
238000005259 measurement Methods 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
239000000243 solution Substances 0.000 description 7
ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 6
RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
230000009477 glass transition Effects 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
238000001296 phosphorescence spectrum Methods 0.000 description 6
238000004528 spin coating Methods 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 5
101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 5
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 5
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 5
125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 5
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
125000002541 furyl group Chemical group 0.000 description 5
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
125000001041 indolyl group Chemical group 0.000 description 5
125000005956 isoquinolyl group Chemical group 0.000 description 5
125000001624 naphthyl group Chemical group 0.000 description 5
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 5
125000003226 pyrazolyl group Chemical group 0.000 description 5
125000001725 pyrenyl group Chemical group 0.000 description 5
125000004076 pyridyl group Chemical group 0.000 description 5
125000000714 pyrimidinyl group Chemical group 0.000 description 5
125000000168 pyrrolyl group Chemical group 0.000 description 5
125000005493 quinolyl group Chemical group 0.000 description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
125000001544 thienyl group Chemical group 0.000 description 5
125000004306 triazinyl group Chemical group 0.000 description 5
125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
YRTQWABQLUPBDW-UHFFFAOYSA-N 5-(4-bromophenyl)pyrido[4,3-b]indole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=NC=C2C2=CC=CC=C21 YRTQWABQLUPBDW-UHFFFAOYSA-N 0.000 description 4
CZZLHOWUECFBMS-UHFFFAOYSA-N 8-bromo-5-phenylpyrido[4,3-b]indole Chemical compound C12=CC=NC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 CZZLHOWUECFBMS-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010992 reflux Methods 0.000 description 4
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
FHJJVSJWFYYPAC-UHFFFAOYSA-N 3-carbazol-9-yl-9h-carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C2NC3=CC=CC=C3C2=C1 FHJJVSJWFYYPAC-UHFFFAOYSA-N 0.000 description 3
NTEHSMCNSXIYEW-UHFFFAOYSA-N 5-phenylpyrido[4,3-b]indole Chemical compound C1=CC=CC=C1N1C2=CC=NC=C2C2=CC=CC=C21 NTEHSMCNSXIYEW-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
125000002102 aryl alkyloxo group Chemical group 0.000 description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
150000001716 carbazoles Chemical class 0.000 description 3
125000000000 cycloalkoxy group Chemical group 0.000 description 3
238000000151 deposition Methods 0.000 description 3
230000008021 deposition Effects 0.000 description 3
239000007772 electrode material Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
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 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
238000000746 purification Methods 0.000 description 3
150000004322 quinolinols Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
LKGNNDAICZOLMY-UHFFFAOYSA-N 5-[4-(3-carbazol-9-ylcarbazol-9-yl)phenyl]pyrido[4,3-b]indole Chemical compound C1=CC=C2C(=C1)N(C1=CC=NC=C21)C1=CC=C(N2C3=C(C4=C2C=CC=C4)C=C(N2C4=C(C5=C2C=CC=C5)C=CC=C4)C=C3)C=C1 LKGNNDAICZOLMY-UHFFFAOYSA-N 0.000 description 2
WUIJXGYSOLXBBG-UHFFFAOYSA-N 8-(3-carbazol-9-ylcarbazol-9-yl)-5-phenylpyrido[4,3-b]indole Chemical compound C1=C2C3=CC(N4C5=C(C6=CC=CC=C46)C=CC=C5)=CC=C3N(C2=CC=C1)C1=CC=C2N(C3=CC=NC=C3C2=C1)C1=CC=CC=C1 WUIJXGYSOLXBBG-UHFFFAOYSA-N 0.000 description 2
HWTHOPMRUCFPBX-UHFFFAOYSA-N 9,9-diphenyl-10h-acridine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 HWTHOPMRUCFPBX-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
238000006887 Ullmann reaction Methods 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
125000002252 acyl 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
229910052786 argon Inorganic materials 0.000 description 2
125000003609 aryl vinyl group Chemical group 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
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 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000002019 doping agent Substances 0.000 description 2
230000005284 excitation Effects 0.000 description 2
230000005281 excited state Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000006872 improvement Effects 0.000 description 2
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
229910052741 iridium Inorganic materials 0.000 description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
230000001678 irradiating effect Effects 0.000 description 2
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
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 2
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
150000007978 oxazole derivatives Chemical class 0.000 description 2
125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010926 purge Methods 0.000 description 2
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238000004519 manufacturing process Methods 0.000 description 1
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ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
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YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
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NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical class C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
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XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical group N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
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150000003220 pyrenes Chemical class 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
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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
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