KR20200021075A - 전자 디바이스용 재료 - Google Patents
전자 디바이스용 재료 Download PDFInfo
- Publication number
- KR20200021075A KR20200021075A KR1020207001204A KR20207001204A KR20200021075A KR 20200021075 A KR20200021075 A KR 20200021075A KR 1020207001204 A KR1020207001204 A KR 1020207001204A KR 20207001204 A KR20207001204 A KR 20207001204A KR 20200021075 A KR20200021075 A KR 20200021075A
- Authority
- KR
- South Korea
- Prior art keywords
- groups
- aromatic ring
- polymer
- group
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000463 material Substances 0.000 title claims description 41
- 229920000642 polymer Polymers 0.000 claims abstract description 148
- 125000003118 aryl group Chemical group 0.000 claims description 127
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 150000003254 radicals Chemical class 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 33
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000004132 cross linking Methods 0.000 claims description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 230000000903 blocking effect Effects 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 5
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 106
- 150000001875 compounds Chemical class 0.000 description 37
- -1 benzoti Offen Chemical compound 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000005859 coupling reaction Methods 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 229920006037 cross link polymer Polymers 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 229920000547 conjugated polymer Polymers 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 238000007239 Wittig reaction Methods 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 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 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Chemical group 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical compound C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- UTBZAFJTSSNRNN-UHFFFAOYSA-N 2H-diazaphosphole Chemical class C1=CP=NN1 UTBZAFJTSSNRNN-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
Description
Claims (18)
- 하기 식 (I) 의 적어도 하나의 구조 단위를 함유하는 폴리머로서,
식 중, 발생하는 변수들은 다음과 같다:
U 는 각 경우에 동일하거나 상이하며 C(R1)2, CR1=CR1, Si(R1)2, O 또는 S 이고, CR1=CR1, O 및 S 으로부터 선택된 기들은 서로 직접 결합하지 않는다;
Z 는 각 경우에 동일하거나 상이하고, 이에 기가 결합되지 않는 경우 N 또는 CR2 이고, 이에 기가 결합되는 경우 C 이다;
Ar1, Ar2, Ar3, Ar4 및 Ar5 는 동일하거나 상이하고, 5 내지 40 개의 방향족 고리 원자를 갖고 하나 이상의 R3 라디칼로 치환될 수도 있는 헤테로방향족 고리 시스템으로부터, 그리고 6 내지 40 개의 방향족 고리 원자를 갖고 하나 이상의 R3 라디칼로 치환될 수도 있는 방향족 고리 시스템으로부터 선택된다;
R1 은 각 경우에 동일하거나 상이하고, H, D, F, C(=O)R4, CN, Si(R4)3, N(R4)2, P(=O)(R4)2, OR4, S(=O)R4, S(=O)2R4, 1 내지 20 개의 탄소 원자를 갖는 직쇄 알킬 또는 알콕시기, 3 내지 20 개의 탄소 원자를 갖는 분지형 또는 환형 알킬 또는 알콕시기, 2 내지 20 개의 탄소 원자를 갖는 알케닐 또는 알키닐기, 6 내지 40 개의 방향족 고리 원자를 갖는 방향족 고리 시스템, 및 5 내지 40 개의 방향족 고리 원자를 갖는 헤테로방향족 고리 시스템으로부터 선택되고; 둘 이상의 R1 또는 R2 또는 R3 라디칼은 서로 연결될 수도 있고 고리를 형성할 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기 및 상기 방향족 고리 시스템 및 헤테로방향족 고리 시스템은 하나 이상의 R4 라디칼에 의해 각각 치환될 수 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기에서의 하나 이상의 CH2 기는 -R4C=CR4-, -C≡C-, Si(R4)2, C=O, C=NR4, -C(=O)O-, -C(=O)NR4-, NR4, P(=O)(R4), -O-, -S-, SO 또는 SO2 에 의해 대체될 수도 있다;
R2, R3 은 각 경우에 동일하거나 상이하고, H, D, F, C(=O)R4, CN, Si(R4)3, N(R4)2, P(=O)(R4)2, OR4, S(=O)R4, S(=O)2R4, 1 내지 20 개의 탄소 원자를 갖는 직쇄 알킬 또는 알콕시기, 3 내지 20 개의 탄소 원자를 갖는 분지형 또는 환형 알킬 또는 알콕시기, 2 내지 20 개의 탄소 원자를 갖는 알케닐 또는 알키닐기, 6 내지 40 개의 방향족 고리 원자를 갖는 방향족 고리 시스템, 및 5 내지 40 개의 방향족 고리 원자를 갖는 헤테로방향족 고리 시스템으로부터 선택되고; 둘 이상의 R1 또는 R2 또는 R3 라디칼은 서로 연결될 수도 있고 고리를 형성할 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기 및 상기 방향족 고리 시스템 및 헤테로방향족 고리 시스템은 하나 이상의 R4 라디칼에 의해 각각 치환될 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기에서의 하나 이상의 CH2 기는 -R4C=CR4-, -C≡C-, Si(R4)2, C=O, C=NR4, -C(=O)O-, -C(=O)NR4-, NR4, P(=O)(R4), -O-, -S-, SO 또는 SO2 에 의해 대체될 수도 있다;
R4 는 각 경우에 동일 또는 상이하고, H, D, F, C(=O)R5, CN, Si(R5)3, N(R5)2, P(=O)(R5)2, OR5, S(=O)R5, S(=O)2R5, 1 내지 20 개의 탄소 원자를 갖는 직쇄 알킬 또는 알콕시기, 3 내지 20 개의 탄소 원자를 갖는 분지형 또는 환형 알킬 또는 알콕시기, 2 내지 20 개의 탄소 원자를 갖는 알케닐 또는 알키닐기, 6 내지 40 개의 방향족 고리 원자를 갖는 방향족 고리 시스템, 및 5 내지 40 개의 방향족 고리 원자를 갖는 헤테로방향족 고리 시스템으로부터 선택되고; 2개 이상의 R4 라디칼은 서로 연결될 수도 있고 고리를 형성할 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기 및 상기 방향족 고리 시스템 및 헤테로방향족 고리 시스템은 각각 하나 이상의 R5 라디칼에 의해 치환될 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기에서 하나 이상의 CH2 기는 -R5C=CR5-, -C≡C-, Si(R5)2, C=O, C=NR5, -C(=O)O-, -C(=O)NR5-, NR5, P(=O)(R5), -O-, -S-, SO 또는 SO2 에 의해 대체될 수도 있다;
R5 는 각 경우에 동일하거나 상이하며, H, D, F, CN, 1 내지 20 개의 탄소 원자를 갖는 알킬 또는 알콕시 기, 2 내지 20 개의 탄소 원자를 갖는 알케닐 또는 알키닐 기, 6 내지 40 개의 방향족 고리 원자를 갖는 방향족 고리 시스템 및 5 내지 40 개의 방향족 고리 원자를 갖는 헤테로방향족 고리 시스템로부터 선택되고; 2개 이상의 R5 라디칼은 서로 연결될 수도 있고 고리를 형성할 수도 있고; 그리고 상기 알킬, 알콕시, 알케닐 및 알키닐 기, 방향족 고리 시스템 및 헤테로방향족 고리 시스템은 F 또는 CN 으로 치환될 수도 있다;
p 가 1 인 경우 r 은 1, 2 또는 3 이고, p 가 0 인 경우 r 은 1 이다;
q 가 1 인 경우 s 은 0, 1, 2 또는 3 이고, q 가 0 인 경우 s 는 1 이다;
p 는 0 또는 1 이며; 여기서, p 가 0 일 때, 지수 p 를 갖는 대괄호 사이에서 단위에 결합된 기들은 서로 직접 결합된다;
q 는 0 또는 1 이며; 여기서, q 가 0 일 때, 지수 q 를 갖는 대괄호 사이에서 단위에 결합된 기들은 서로 직접 결합된다;
n 는 0 또는 1 이며, 여기서, n 가 0 일 때, 지수 n 를 갖는 대괄호 사이에서 단위에 결합된 기들은 서로 직접 결합된다;
m 는 0 또는 1 이며, 여기서, m 가 0 일 때, 지수 m 를 갖는 대괄호 사이에서 단위에 결합된 기들은 서로 직접 결합된다;
o 는 0 또는 1 이며, 여기서, o 가 0 일 때, 지수 o 를 갖는 대괄호 사이에서 단위에 결합된 기들은 서로 직접 결합된다;
i 은 각 경우에 동일하거나 상이하고, 1, 2, 3, 4, 5, 6, 7 또는 8 이다;
여기서 1 내지 20 개의 탄소 원자를 갖는 직쇄형 알킬 또는 알콕시기, 3 내지 20 개의 탄소 원자를 갖는 분지형 또는 환형 알킬 또는 알콕시기, 2 내지 20 개의 탄소 원자를 갖는 알케닐 또는 알키닐기, 6 내지 40 개의 방향족 고리 원자를 갖는 방향족 고리 시스템, 및 5 내지 40 개의 방향족 고리 원자를 갖는 헤테로방향족 고리 시스템에서 선택되는 하나 이상의 R1 기들을 함유하는 적어도 하나의 U 기가 존재하고; 둘 이상의 R1 또는 R2 또는 R3 라디칼은 서로 연결될 수도 있으며 고리를 형성할 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기, 및 상기 방향족 고리 시스템 및 헤테로방향족 고리 시스템은 각각 하나 이상의 R4 라디칼에 의해 치환될 수도 있고; 상기 알킬, 알콕시, 알케닐 및 알키닐기에서의 하나 이상의 CH2 기는-R4C=CR4-, -C≡C-, Si(R4)2, C=O, C=NR4, -C(=O)O-, -C(=O)NR4-, NR4, P(=O)(R4), -O-, -S-, SO 또는 SO2 에 의해 대체될 수도 있는, 폴리머. - 제 1 항에 있어서,
Ar1, Ar2, Ar3, Ar4 및 Ar5 는 각 경우에 동일 또는 상이하며, 각각이 하나 이상의 R1 라디칼로 치환될 수도 있는, 벤젠, 바이페닐, 테르페닐, 플루오렌, 나프탈렌, 페난트렌, 인데노플루오렌, 스피로바이플루오렌, 디벤조푸란, 디벤조티오펜, 카르바졸, 인데노카르바졸 및 인돌로카르바졸로부터 선택되는 것을 특징으로 하는 폴리머. - 제 1 항 또는 제 2 항에 있어서,
R1 은 각 경우에 동일하거나 상이하며 H, D, F, 1 내지 10 개의 탄소 원자를 갖는 직쇄 알킬 기, 및 3 내지 10 개의 탄소 원자를 갖는 분지형 알킬 기로부터 선택되는 것을 특징으로 하는 폴리머. - 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,
다리목 탄소 원자에 바로 인접한 그러한 2개의 U 기들은, F, CN, Si(R4)3, OR4, 1 내지 10 개의 탄소 원자를 갖는 직쇄 알킬 및 알콕시 기, 3 내지 10 개의 탄소 원자를 갖는 분지형 알킬 및 알콕시 기, 및 6 내지 20 개의 방향족 고리 원자를 갖는 방향족 고리 시스템으로부터 선택된 R1 라디칼들을 지니고, 2개 이상의 R1 또는 R2 또는 R3 라디칼은 서로 연결될 수도 있고 고리를 형성할 수도 있으며; 그리고 상기 알킬 및 알콕시 기 및 상기 방향족 고리 시스템은 각각 하나 이상의 R4 라디칼로 치환될 수도 있는 것을 특징으로 하는 폴리머. - 제 1 항 내지 제 7 항 중 어느 한 항에 있어서,
상기 폴리머에서 상기 식 (I) 의 구조 단위의 비율은 상기 폴리머에서 구조 단위로서 존재하는 모든 공중합성 모노머의 100 몰 %를 기준으로 하여 30 내지 70 몰% 범위인 것을 특징으로 하는 폴리머. - 제 1 항 내지 제 8 항 중 어느 한 항에 있어서,
상기 폴리머는 가교성 Q기를 함유하는 적어도 하나의 구조 단위를 함유하는 것을 특징으로 하는 폴리머. - 제 9 항에 있어서,
상기 가교성 Q 기는 하기 식으로부터 선택되고
식 중 R11, R12, R13 및 R14 는 각 경우에 동일하거나 상이하고 H 및 1 내지 6 개의 탄소 원자를 갖는 직쇄 또는 분지형 알킬 기로부터 선택되고, s = 0 내지 8, t = 1 내지 8 이고, Ar10 은, 6 내지 40 개의 방향족 고리 원자를 갖고 하나 이상의 R11 로 치환될 수도 있는 방향족 고리 시스템으로부터, 그리고 5 내지 40 개의 방향족 고리 원자를 갖고 하나 이상의 R11 로 치환될 수도 있는 헤테로방향족 고리 시스템으로부터 선택되고, 점선 결합은 상기 식의 나머지에 대한 결합을 나타내는 것을 특징으로 하는 폴리머. - 제 9 항 또는 제 10 항에 기재된 폴리머의 가교 반응에 의해 수득 가능한 폴리머.
- 제 1 항 내지 제 11 항 중 어느 한 항에 기재된 하나 이상의 폴리머 및 하나 이상의 추가 중합체성, 올리고머성, 수지상 및/또는 저분자량 물질을 포함하는 혼합물.
- 제 1 항 내지 제 11 항 중 어느 한 항에 기재된 하나 이상의 폴리머 및 하나 이상의 용매들을 포함하는 용액.
- 전자 디바이스에서의, 제 1 항 내지 제 11 항 중 어느 한 항에 기재된 폴리머의 용도.
- 제 1 항 내지 제 11 항 중 어느 한 항에 기재된 적어도 하나의 폴리머를 포함하는 전자 디바이스.
- 제 15 항에 있어서,
제 1 항 내지 제 11 항 중 어느 한 항에 기재된 폴리머는 정공 수송 층, 정공 주입 층, 전자 차단 층 및 방출 층으로부터 선택된 층에 존재하는 것을 특징으로 하는 전자 디바이스. - 제 1 항 내지 제 11 항 중 어느 한 항에 기재된 폴리머의 제조 방법으로서,
Suzuki 중합, Yamamoto 중합, Stille 중합, Heck 중합, Negishi 중합, Sonogashira 중합, Hiyama 중합 및 Hartwig-Buchwald 중합으로부터 선택된 중합이 수행되는 것을 특징으로 하는 폴리머의 제조 방법.
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EP3642258B1 (de) | 2024-04-03 |
JP7262404B2 (ja) | 2023-04-21 |
KR102548554B1 (ko) | 2023-06-28 |
CN110770277A (zh) | 2020-02-07 |
EP3642258A1 (de) | 2020-04-29 |
US11407854B2 (en) | 2022-08-09 |
JP2020524737A (ja) | 2020-08-20 |
TW201920343A (zh) | 2019-06-01 |
US20200216605A1 (en) | 2020-07-09 |
WO2018234220A1 (de) | 2018-12-27 |
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