KR20240163623A

KR20240163623A - 폴리머 및 그 이용

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Publication number: KR20240163623A
Authority: KR; South Korea
Prior art keywords: group; carbon atoms; charge; polymer; formula
Prior art date: 2022-03-28
Legal status : Pending

Application number

KR1020247029616A

Other languages

English (en)

Korean (ko)

Inventor

요스케 구라타

케이스케 슈토

Original Assignee

닛산 가가쿠 가부시키가이샤

Priority date

2022-03-28

Filing date

2023-03-10

Publication date

2024-11-19

2023-03-10 Application filed by 닛산 가가쿠 가부시키가이샤 filed Critical 닛산 가가쿠 가부시키가이샤

2024-11-19 Publication of KR20240163623A publication Critical patent/KR20240163623A/ko

Status Pending legal-status Critical Current

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229920000642 polymer Polymers 0.000 title claims abstract description 78
239000010409 thin film Substances 0.000 claims abstract description 74
-1 trifluorovinyl group Chemical group 0.000 claims description 305
125000004432 carbon atom Chemical group C* 0.000 claims description 204
125000000217 alkyl group Chemical group 0.000 claims description 77
239000002966 varnish Substances 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 65
239000000463 material Substances 0.000 claims description 61
125000003118 aryl group Chemical group 0.000 claims description 57
238000002347 injection Methods 0.000 claims description 53
239000007924 injection Substances 0.000 claims description 53
239000002904 solvent Substances 0.000 claims description 52
125000005843 halogen group Chemical group 0.000 claims description 36
239000002096 quantum dot Substances 0.000 claims description 33
230000005525 hole transport Effects 0.000 claims description 28
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000000732 arylene group Chemical group 0.000 claims description 14
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
150000002430 hydrocarbons Chemical group 0.000 claims description 13
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000003700 epoxy group Chemical group 0.000 claims description 9
125000003566 oxetanyl group Chemical group 0.000 claims description 9
150000004982 aromatic amines Chemical class 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
125000001033 ether group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
238000005401 electroluminescence Methods 0.000 claims description 5
150000003577 thiophenes Chemical class 0.000 claims description 5
125000005549 heteroarylene group Chemical group 0.000 claims description 4
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
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230000000052 comparative effect Effects 0.000 description 20
239000002019 doping agent Substances 0.000 description 20
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 20
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229910052751 metal Inorganic materials 0.000 description 18
239000002184 metal Substances 0.000 description 18
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238000004519 manufacturing process Methods 0.000 description 15
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230000015572 biosynthetic process Effects 0.000 description 12
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230000008569 process Effects 0.000 description 12
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 12
125000003342 alkenyl group Chemical group 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 11
230000009467 reduction Effects 0.000 description 11
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 10
229960001826 dimethylphthalate Drugs 0.000 description 10
125000003709 fluoroalkyl group Chemical group 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 9
125000002947 alkylene group Chemical group 0.000 description 9
125000000304 alkynyl group Chemical group 0.000 description 9
230000000903 blocking effect Effects 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
238000007654 immersion Methods 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
150000001448 anilines Chemical class 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
125000004122 cyclic group Chemical group 0.000 description 8
238000000151 deposition Methods 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
125000001072 heteroaryl group Chemical group 0.000 description 8
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 7
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125000003710 aryl alkyl group Chemical group 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
150000002739 metals Chemical class 0.000 description 7
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125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 7
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150000003254 radicals Chemical class 0.000 description 7
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 6
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 6
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 6
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
229910052782 aluminium Inorganic materials 0.000 description 6
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
230000008021 deposition Effects 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
238000010304 firing Methods 0.000 description 6
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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 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
239000002798 polar solvent Substances 0.000 description 6
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238000007789 sealing Methods 0.000 description 6
238000000926 separation method Methods 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
125000005309 thioalkoxy group Chemical group 0.000 description 6
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125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
229910004298 SiO 2 Inorganic materials 0.000 description 5
125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
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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 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
238000005227 gel permeation chromatography Methods 0.000 description 5
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
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 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
239000002994 raw material Substances 0.000 description 5
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125000002130 sulfonic acid ester group Chemical group 0.000 description 5
239000010936 titanium Substances 0.000 description 5
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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125000001309 chloro group Chemical group Cl* 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
229940126214 compound 3 Drugs 0.000 description 4
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 4
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
238000005516 engineering process Methods 0.000 description 4
229910052732 germanium Inorganic materials 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000003999 initiator Substances 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
239000002346 layers by function Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
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 4
239000010955 niobium Substances 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000007870 radical polymerization initiator Substances 0.000 description 4
229910052710 silicon Inorganic materials 0.000 description 4
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 4
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
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JBAWUBIVHLJCMP-UHFFFAOYSA-N ditert-butyl 4-(4-tert-butylperoxycarbonylbenzoyl)benzene-1,2-dicarboperoxoate Chemical compound C1=CC(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 JBAWUBIVHLJCMP-UHFFFAOYSA-N 0.000 description 1
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LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
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KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
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MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
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BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
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QTRRAHGRSMFAKW-UHFFFAOYSA-N iridium(3+);1-phenylpyrazole Chemical compound [Ir+3].C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1 QTRRAHGRSMFAKW-UHFFFAOYSA-N 0.000 description 1
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USSPHSVODLAWSA-UHFFFAOYSA-N n,n-dimethylbutan-2-amine Chemical compound CCC(C)N(C)C USSPHSVODLAWSA-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
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