WO2017142310A1 - 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 - Google Patents
헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 Download PDFInfo
- Publication number
- WO2017142310A1 WO2017142310A1 PCT/KR2017/001655 KR2017001655W WO2017142310A1 WO 2017142310 A1 WO2017142310 A1 WO 2017142310A1 KR 2017001655 W KR2017001655 W KR 2017001655W WO 2017142310 A1 WO2017142310 A1 WO 2017142310A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substituted
- unsubstituted
- compound
- heterocyclic
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 34
- -1 dibenzofuranyl group Chemical group 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 43
- 239000007924 injection Substances 0.000 claims description 43
- 239000011368 organic material Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 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 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 141
- 230000000052 comparative effect Effects 0.000 description 43
- 239000000463 material Substances 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 230000032258 transport Effects 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 0 C(C1C=CC=C2)C12c1ccc2-c3cccc(-c(cc4)ccc4N(c(cc4)ccc4-c4ccccc4)c(cc4)c5c6c4c4ccccc4[n]6c4c5cccc4)c3**c2c1 Chemical compound C(C1C=CC=C2)C12c1ccc2-c3cccc(-c(cc4)ccc4N(c(cc4)ccc4-c4ccccc4)c(cc4)c5c6c4c4ccccc4[n]6c4c5cccc4)c3**c2c1 0.000 description 17
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 239000010409 thin film Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000002514 liquid chromatography mass spectrum Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 239000010405 anode material Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 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
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SZLNOBJKCVERBJ-UHFFFAOYSA-N 1-azapentacyclo[10.6.1.02,7.08,19.013,18]nonadeca-2,4,6,8(19),9,11,13,15,17-nonaene Chemical compound C12=CC=CC=C2N2C3=CC=CC=C3C3=CC=CC1=C32 SZLNOBJKCVERBJ-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 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 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 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
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 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
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000007774 positive electrode material Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AELZBFQHFNMGJS-UHFFFAOYSA-N 1h-1-benzosilole Chemical group C1=CC=C2[SiH2]C=CC2=C1 AELZBFQHFNMGJS-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- JNVDPJAUWVJWAB-UHFFFAOYSA-N 4-bromo-1-chloro-2-iodobenzene Chemical compound ClC1=CC=C(Br)C=C1I JNVDPJAUWVJWAB-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 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
- NJXDAKUYTRAHCM-UHFFFAOYSA-N 9,9-dimethyl-n-(4-phenylphenyl)fluoren-3-amine Chemical compound C=1C=C2C(C)(C)C3=CC=CC=C3C2=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 NJXDAKUYTRAHCM-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PIVWLRRMOUDAAG-UHFFFAOYSA-N C(C1c2c(cc3)-c4ccccc14)Nc(cccc1)c1-c2c3N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1c(c(ccc(-c2ccccc2)c2)c2[s]2)c2ccc1 Chemical compound C(C1c2c(cc3)-c4ccccc14)Nc(cccc1)c1-c2c3N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1c(c(ccc(-c2ccccc2)c2)c2[s]2)c2ccc1 PIVWLRRMOUDAAG-UHFFFAOYSA-N 0.000 description 1
- SDRCBNQPVALHMS-UHFFFAOYSA-N C(Cc(cccc1)c1-c1c(cc2)N(c3ccc(c4ccccc4[n]4-c5ccccc5)c4c3)c(cc3)cc4c3c(cccc3)c3c3c4cccc3)C3c1c2-c1ccccc31 Chemical compound C(Cc(cccc1)c1-c1c(cc2)N(c3ccc(c4ccccc4[n]4-c5ccccc5)c4c3)c(cc3)cc4c3c(cccc3)c3c3c4cccc3)C3c1c2-c1ccccc31 SDRCBNQPVALHMS-UHFFFAOYSA-N 0.000 description 1
- XWWLOUOGOBXUNG-UHFFFAOYSA-N C(c(cccc1)c1-c1c2)c1ccc2N(c(cc1)ccc1-c(cc1)cc2c1[s]c1ccccc21)c(ccc-1c2C(C3)c4c-1cccc4)c2-c1c3cccc1 Chemical compound C(c(cccc1)c1-c1c2)c1ccc2N(c(cc1)ccc1-c(cc1)cc2c1[s]c1ccccc21)c(ccc-1c2C(C3)c4c-1cccc4)c2-c1c3cccc1 XWWLOUOGOBXUNG-UHFFFAOYSA-N 0.000 description 1
- UWMQTTCCEHAFBA-UHFFFAOYSA-N C(c1c(cc2)-c3ccccc33)N3c(cccc3)c3-c1c2N(c(cc1)ccc1-c1c2OCc(cccc3)c3-c2ccc1)c(cc1)cc2c1[s]c1ccccc21 Chemical compound C(c1c(cc2)-c3ccccc33)N3c(cccc3)c3-c1c2N(c(cc1)ccc1-c1c2OCc(cccc3)c3-c2ccc1)c(cc1)cc2c1[s]c1ccccc21 UWMQTTCCEHAFBA-UHFFFAOYSA-N 0.000 description 1
- PTZUDOSJFIYYIY-UHFFFAOYSA-N C1(=CC=C(C=C1)N(C1=CC=C(C=C1)B(O)O)C1=CC=C(C=C1)C1=CC=2C(C3=CC=CC=C3C=2C=C1)(C)C)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)N(C1=CC=C(C=C1)B(O)O)C1=CC=C(C=C1)C1=CC=2C(C3=CC=CC=C3C=2C=C1)(C)C)C1=CC=CC=C1 PTZUDOSJFIYYIY-UHFFFAOYSA-N 0.000 description 1
- XAPUETBVIRQWND-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 Chemical compound C1c(ccc(N(c(cc2)ccc2-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 XAPUETBVIRQWND-UHFFFAOYSA-N 0.000 description 1
- HBYRWPLYWWTUHV-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2[o]c2ccccc32)c(ccc-2c3C(CC4)c5c-2cccc5)c3-c2c4cccc2)c2)c2-c2c1cccc2 Chemical compound C1c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2[o]c2ccccc32)c(ccc-2c3C(CC4)c5c-2cccc5)c3-c2c4cccc2)c2)c2-c2c1cccc2 HBYRWPLYWWTUHV-UHFFFAOYSA-N 0.000 description 1
- ACRFAXQWSBAUNI-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2c(cccc2)c2[o]3)c(ccc-2c3C4c5c-2cccc5)c3-c2c4cccc2)c2)c2-c2c1cccc2 Chemical compound C1c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2c(cccc2)c2[o]3)c(ccc-2c3C4c5c-2cccc5)c3-c2c4cccc2)c2)c2-c2c1cccc2 ACRFAXQWSBAUNI-UHFFFAOYSA-N 0.000 description 1
- WGJCCNNYCQGNRT-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2c2ccccc2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 Chemical compound C1c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2c2ccccc2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 WGJCCNNYCQGNRT-UHFFFAOYSA-N 0.000 description 1
- AJRNUUSWQHKGSO-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c2ccc(c3ccccc3[s]3)c3c2)c(ccc-2c3C(CC4)c5c-2cccc5)c3-c2c4cccc2)c2)c2-c2c1cccc2 Chemical compound C1c(ccc(N(c(cc2)ccc2-c2ccc(c3ccccc3[s]3)c3c2)c(ccc-2c3C(CC4)c5c-2cccc5)c3-c2c4cccc2)c2)c2-c2c1cccc2 AJRNUUSWQHKGSO-UHFFFAOYSA-N 0.000 description 1
- OTYUUXYXAZJSNA-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c2cccc(c3ccccc33)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2c1cccc2 Chemical compound C1c(ccc(N(c(cc2)ccc2-c2cccc(c3ccccc33)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2c1cccc2 OTYUUXYXAZJSNA-UHFFFAOYSA-N 0.000 description 1
- OGYXGXODXBCSCO-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c2cccc3c2[s]c2c3cccc2)c(cc2)c3c4c2c2ccccc2[n]4c2c3cccc2)c2)c2-c2ccccc12 Chemical compound C1c(ccc(N(c(cc2)ccc2-c2cccc3c2[s]c2c3cccc2)c(cc2)c3c4c2c2ccccc2[n]4c2c3cccc2)c2)c2-c2ccccc12 OGYXGXODXBCSCO-UHFFFAOYSA-N 0.000 description 1
- NOWUZVLNNYCLDQ-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 Chemical compound C1c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 NOWUZVLNNYCLDQ-UHFFFAOYSA-N 0.000 description 1
- WXJWISUQUSTNSK-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[o]3)c(ccc(-c2c3cccc2)c2C3=CC3)c2-c2c3cccc2)c2)c2-c2c1cccc2 Chemical compound C1c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[o]3)c(ccc(-c2c3cccc2)c2C3=CC3)c2-c2c3cccc2)c2)c2-c2c1cccc2 WXJWISUQUSTNSK-UHFFFAOYSA-N 0.000 description 1
- FEUWYRGUMFSGBH-UHFFFAOYSA-N C1c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[s]3)c(cc2)c3c4c2c(cccc2)c2[n]4c2ccccc32)c2)c2-c2ccccc12 Chemical compound C1c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[s]3)c(cc2)c3c4c2c(cccc2)c2[n]4c2ccccc32)c2)c2-c2ccccc12 FEUWYRGUMFSGBH-UHFFFAOYSA-N 0.000 description 1
- TUNVDUSCLHBFKE-UHFFFAOYSA-N CC(C)(c(cccc1)c1-c1ccc2)c1c2-c(cc1)ccc1N(c1cc(-c2c(C3)cccc2)c3cc1)c(cc1)c2c3c1c1ccccc1[n]3c1c2cccc1 Chemical compound CC(C)(c(cccc1)c1-c1ccc2)c1c2-c(cc1)ccc1N(c1cc(-c2c(C3)cccc2)c3cc1)c(cc1)c2c3c1c1ccccc1[n]3c1c2cccc1 TUNVDUSCLHBFKE-UHFFFAOYSA-N 0.000 description 1
- UHXWCDJSOFDDKN-UHFFFAOYSA-N CC(C)(c1ccccc1-c1c2)c1ccc2N(c(cc1)ccc1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1)c(cc1)c2c3c1c(cccc1)c1[n]3c1c2cccc1 Chemical compound CC(C)(c1ccccc1-c1c2)c1ccc2N(c(cc1)ccc1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1)c(cc1)c2c3c1c(cccc1)c1[n]3c1c2cccc1 UHXWCDJSOFDDKN-UHFFFAOYSA-N 0.000 description 1
- SNWKTRDOYWOWAZ-UHFFFAOYSA-N CC(C)(c1ccccc1-c1ccc2)c1c2N(c(cc1)cc2c1c1ccccc1c1ccccc21)c(cc1)c2c3c1c1ccccc1[n]3c1c2cccc1 Chemical compound CC(C)(c1ccccc1-c1ccc2)c1c2N(c(cc1)cc2c1c1ccccc1c1ccccc21)c(cc1)c2c3c1c1ccccc1[n]3c1c2cccc1 SNWKTRDOYWOWAZ-UHFFFAOYSA-N 0.000 description 1
- DQDPGVMDBWPMSC-UHFFFAOYSA-N CC(CC=C1)c2c1[s]c(cc1)c2cc1N(C(C(C)C1)=CC=C1c1c2[s]c3ccccc3c2ccc1)C(C=CC1c2ccccc2NC11)=C1C1=C(C)C=CCC1C Chemical compound CC(CC=C1)c2c1[s]c(cc1)c2cc1N(C(C(C)C1)=CC=C1c1c2[s]c3ccccc3c2ccc1)C(C=CC1c2ccccc2NC11)=C1C1=C(C)C=CCC1C DQDPGVMDBWPMSC-UHFFFAOYSA-N 0.000 description 1
- MQNLQSAWQDODSS-UHFFFAOYSA-N CC1(C)c(cc(cc2)-c(cc3)ccc3N(c3cc(-c4ccccc4C4)c4cc3)c(cc3)c4c5c3c(cccc3)c3[n]5c3ccccc43)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)-c(cc3)ccc3N(c3cc(-c4ccccc4C4)c4cc3)c(cc3)c4c5c3c(cccc3)c3[n]5c3ccccc43)c2-c2c1cccc2 MQNLQSAWQDODSS-UHFFFAOYSA-N 0.000 description 1
- RKRGLSFTTHKYKU-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)cc4c3c3ccccc3c3ccccc43)c(cc3)c4c5c3c(cccc3)c3[n]5c3c4cccc3)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)cc4c3c3ccccc3c3ccccc43)c(cc3)c4c5c3c(cccc3)c3[n]5c3c4cccc3)c2-c2ccccc12 RKRGLSFTTHKYKU-UHFFFAOYSA-N 0.000 description 1
- OHMDBWGDPWNOBS-UHFFFAOYSA-N CC1(C)c(ccc(-c(cc2)ccc2N(c2cc(-c3ccccc3C3(C)C)c3cc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2c1cccc2 Chemical compound CC1(C)c(ccc(-c(cc2)ccc2N(c2cc(-c3ccccc3C3(C)C)c3cc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2c1cccc2 OHMDBWGDPWNOBS-UHFFFAOYSA-N 0.000 description 1
- UZQVRTNDQUPTPT-UHFFFAOYSA-N CC1(C)c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2[s]c2c3cccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2ccccc32)c2)c2-c2c1cccc2 Chemical compound CC1(C)c(ccc(N(c(cc2)ccc2-c(cc2)cc3c2[s]c2c3cccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2ccccc32)c2)c2-c2c1cccc2 UZQVRTNDQUPTPT-UHFFFAOYSA-N 0.000 description 1
- MFZWPWCOLBCQJJ-UHFFFAOYSA-N CC1(C)c(ccc(N(c(cc2)ccc2-c2c(C(C)(C)c3c-4cccc3)c-4ccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 Chemical compound CC1(C)c(ccc(N(c(cc2)ccc2-c2c(C(C)(C)c3c-4cccc3)c-4ccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2-c2ccccc12 MFZWPWCOLBCQJJ-UHFFFAOYSA-N 0.000 description 1
- ZRSVIALUWDHWOH-UHFFFAOYSA-N CC1(C)c(ccc(N(c(cc2)ccc2-c2c3[s]c4ccccc4c3ccc2)c(cc2)c3c4c2c2ccccc2[n]4c2c3cccc2)c2)c2-c2ccccc12 Chemical compound CC1(C)c(ccc(N(c(cc2)ccc2-c2c3[s]c4ccccc4c3ccc2)c(cc2)c3c4c2c2ccccc2[n]4c2c3cccc2)c2)c2-c2ccccc12 ZRSVIALUWDHWOH-UHFFFAOYSA-N 0.000 description 1
- UDJXLERXALFCSX-UHFFFAOYSA-N CC1(C)c(ccc(N(c(cc2)ccc2-c2cccc(c3ccccc33)c2[n]3-c2ccccc2)c(ccc-2c3C4(C5C4)c4c-2cccc4)c3-c2c5cccc2)c2)c2-c2ccccc12 Chemical compound CC1(C)c(ccc(N(c(cc2)ccc2-c2cccc(c3ccccc33)c2[n]3-c2ccccc2)c(ccc-2c3C4(C5C4)c4c-2cccc4)c3-c2c5cccc2)c2)c2-c2ccccc12 UDJXLERXALFCSX-UHFFFAOYSA-N 0.000 description 1
- FICPEFREMUAKEB-UHFFFAOYSA-N CC1(C)c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2ccccc32)c2)c2-c2ccccc12 Chemical compound CC1(C)c(ccc(N(c(cc2)ccc2-c2cccc3c2c(cccc2)c2[n]3-c2ccccc2)c(cc2)c3c4c2c(cccc2)c2[n]4c2ccccc32)c2)c2-c2ccccc12 FICPEFREMUAKEB-UHFFFAOYSA-N 0.000 description 1
- QCPQZIHSYQQYBV-UHFFFAOYSA-N CC1(C)c2cccc(-c(cc3)ccc3N(c3cc(-c4c(C5)cccc4)c5cc3)c(cc3)c4c5c3c3ccccc3[n]5c3c4cccc3)c2-c2c1cccc2 Chemical compound CC1(C)c2cccc(-c(cc3)ccc3N(c3cc(-c4c(C5)cccc4)c5cc3)c(cc3)c4c5c3c3ccccc3[n]5c3c4cccc3)c2-c2c1cccc2 QCPQZIHSYQQYBV-UHFFFAOYSA-N 0.000 description 1
- QMDZGMYYEVCZSA-UHFFFAOYSA-N CC1(C=C(c2ccccc2N2c3ccccc3)C2=CC1)C(CC1)=CC=C1N(c(cc1)cc2c1[s]c1ccccc21)c(cc1)c2-c(cccc3)c3N3c4ccccc4-c1c2C3 Chemical compound CC1(C=C(c2ccccc2N2c3ccccc3)C2=CC1)C(CC1)=CC=C1N(c(cc1)cc2c1[s]c1ccccc21)c(cc1)c2-c(cccc3)c3N3c4ccccc4-c1c2C3 QMDZGMYYEVCZSA-UHFFFAOYSA-N 0.000 description 1
- KOSOHFVXQGDEBP-UHFFFAOYSA-N CC1(C=CC=CC1Oc1c2)c1ccc2C(C=C1)=CCC1(C)N(c(cc1)cc2c1[s]c1ccccc21)c(cc1)c2-c(cccc3)c3NC3c2c1-c1c3cccc1 Chemical compound CC1(C=CC=CC1Oc1c2)c1ccc2C(C=C1)=CCC1(C)N(c(cc1)cc2c1[s]c1ccccc21)c(cc1)c2-c(cccc3)c3NC3c2c1-c1c3cccc1 KOSOHFVXQGDEBP-UHFFFAOYSA-N 0.000 description 1
- CKDFNUDBWCVCMQ-UHFFFAOYSA-N CCc(cccc1)c1-c(c(CC)c1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1[s]c1c2C(C)CC=C1)c(cc1)c2c3c1c(cccc1)c1[n]3c1c2cccc1 Chemical compound CCc(cccc1)c1-c(c(CC)c1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1[s]c1c2C(C)CC=C1)c(cc1)c2c3c1c(cccc1)c1[n]3c1c2cccc1 CKDFNUDBWCVCMQ-UHFFFAOYSA-N 0.000 description 1
- OARBEYGZUAGAEM-UHFFFAOYSA-N Cc(cc1)c2c3c1c(cccc1)c1[n]3c1ccccc21 Chemical compound Cc(cc1)c2c3c1c(cccc1)c1[n]3c1ccccc21 OARBEYGZUAGAEM-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YCAAVNFMPGCUTO-UHFFFAOYSA-N N-(4-dibenzothiophen-3-ylphenyl)-4-phenylaniline Chemical compound C1=CC(=CC=2SC3=C(C=21)C=CC=C3)C1=CC=C(C=C1)NC1=CC=C(C=C1)C1=CC=CC=C1 YCAAVNFMPGCUTO-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
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- SLMOVMMXPHLGON-UHFFFAOYSA-N [4-(4-dibenzothiophen-4-yl-N-triphenylen-2-ylanilino)phenyl]boronic acid Chemical compound C1=CC=C(C=2SC3=C(C=21)C=CC=C3)C1=CC=C(C=C1)N(C1=CC=C(C=C1)B(O)O)C1=CC=2C3=CC=CC=C3C3=CC=CC=C3C=2C=C1 SLMOVMMXPHLGON-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IPLWYBIUFZPRTM-UHFFFAOYSA-N c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c(cccc2)c2[o]4)c(cc2)cc4c2c2ccccc2c2c4cccc2)c3c2c1cccc2 Chemical compound c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c(cccc2)c2[o]4)c(cc2)cc4c2c2ccccc2c2c4cccc2)c3c2c1cccc2 IPLWYBIUFZPRTM-UHFFFAOYSA-N 0.000 description 1
- FTWIWIVOUYSAGH-UHFFFAOYSA-N c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c(cccc2)c2c2c4cccc2)c2cccc4c2[s]c2ccccc42)c3c2c1cccc2 Chemical compound c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c(cccc2)c2c2c4cccc2)c2cccc4c2[s]c2ccccc42)c3c2c1cccc2 FTWIWIVOUYSAGH-UHFFFAOYSA-N 0.000 description 1
- AYDNNOLECNZLQS-UHFFFAOYSA-N c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c(cccc2)c2c2ccccc42)c2c(c4ccccc4[o]4)c4ccc2)c3c2c1cccc2 Chemical compound c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c(cccc2)c2c2ccccc42)c2c(c4ccccc4[o]4)c4ccc2)c3c2c1cccc2 AYDNNOLECNZLQS-UHFFFAOYSA-N 0.000 description 1
- TUHRNILEQNKMJX-UHFFFAOYSA-N c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c2ccccc2c2c4cccc2)c2cccc4c2[o]c2c4cccc2)c3c2c1cccc2 Chemical compound c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)cc4c2c2ccccc2c2c4cccc2)c2cccc4c2[o]c2c4cccc2)c3c2c1cccc2 TUHRNILEQNKMJX-UHFFFAOYSA-N 0.000 description 1
- ICYLQIPGRUPAPX-UHFFFAOYSA-N c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)ccc2-c(cc2)cc4c2[s]c2c4cccc2)c(cc2)cc4c2[s]c2ccccc42)c3c2c1cccc2 Chemical compound c(cc1)cc2c1[n]1c3c2ccc(N(c(cc2)ccc2-c(cc2)cc4c2[s]c2c4cccc2)c(cc2)cc4c2[s]c2ccccc42)c3c2c1cccc2 ICYLQIPGRUPAPX-UHFFFAOYSA-N 0.000 description 1
- LLBYEVRWFCOVRH-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(c(N(c(cc2)cc3c2c(cccc2)c2c2c3cccc2)c2ccc3c4c2c(cccc2)c2[n]4c2ccccc32)ccc2)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(c(N(c(cc2)cc3c2c(cccc2)c2c2c3cccc2)c2ccc3c4c2c(cccc2)c2[n]4c2ccccc32)ccc2)c2c2ccccc12 LLBYEVRWFCOVRH-UHFFFAOYSA-N 0.000 description 1
- XNVUAHIIVMRGJF-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(ccc(N(c(cc2)cc3c2c2ccccc2c2ccccc32)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(ccc(N(c(cc2)cc3c2c2ccccc2c2ccccc32)c(cc2)c3c4c2c(cccc2)c2[n]4c2c3cccc2)c2)c2c2ccccc12 XNVUAHIIVMRGJF-UHFFFAOYSA-N 0.000 description 1
- RNMJCSFVQFMTDJ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)c2c3c1c(cccc1)c1[n]3c1ccccc21)c(cc1)ccc1-c1cccc2c1[s]c1ccccc21 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)c2c3c1c(cccc1)c1[n]3c1ccccc21)c(cc1)ccc1-c1cccc2c1[s]c1ccccc21 RNMJCSFVQFMTDJ-UHFFFAOYSA-N 0.000 description 1
- ITGHGHHTYHZLPT-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccc2[s]c(cc(cc3)-c4ccccc4)c3c2c1)c(cc1)c2c3c1c1ccccc1[n]3c1c2cccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccc2[s]c(cc(cc3)-c4ccccc4)c3c2c1)c(cc1)c2c3c1c1ccccc1[n]3c1c2cccc1 ITGHGHHTYHZLPT-UHFFFAOYSA-N 0.000 description 1
- LZPFYXANDKTHOE-UHFFFAOYSA-N c1ccc2[n](c(cccc3)c3c3c(cc4)N(c(cc5)cc6c5[s]c5ccccc65)c(cc5)cc6c5c5ccccc5c5c6cccc5)c3c4c2c1 Chemical compound c1ccc2[n](c(cccc3)c3c3c(cc4)N(c(cc5)cc6c5[s]c5ccccc65)c(cc5)cc6c5c5ccccc5c5c6cccc5)c3c4c2c1 LZPFYXANDKTHOE-UHFFFAOYSA-N 0.000 description 1
- NINRLGIDBRNJIC-UHFFFAOYSA-N c1ccc2[n](c(cccc3)c3c3c(cc4)N(c(cc5)cc6c5c5ccccc5[s]6)c5cc6c(cccc7)c7c(cccc7)c7c6cc5)c3c4c2c1 Chemical compound c1ccc2[n](c(cccc3)c3c3c(cc4)N(c(cc5)cc6c5c5ccccc5[s]6)c5cc6c(cccc7)c7c(cccc7)c7c6cc5)c3c4c2c1 NINRLGIDBRNJIC-UHFFFAOYSA-N 0.000 description 1
- BCYPZRKJTULRRJ-UHFFFAOYSA-N c1ccc2[n](c(cccc3)c3c3c(cc4)N(c(cc5)cc6c5c5ccccc5c5c6cccc5)c5c(c(cccc6)c6[s]6)c6ccc5)c3c4c2c1 Chemical compound c1ccc2[n](c(cccc3)c3c3c(cc4)N(c(cc5)cc6c5c5ccccc5c5c6cccc5)c5c(c(cccc6)c6[s]6)c6ccc5)c3c4c2c1 BCYPZRKJTULRRJ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000003618 dip coating Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002219 fluoranthenes Chemical class 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QLVJMUILAGEUOP-UHFFFAOYSA-N n-(4-dibenzofuran-4-ylphenyl)-4-phenylaniline Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 QLVJMUILAGEUOP-UHFFFAOYSA-N 0.000 description 1
- YAFZRDRWOQRUIP-UHFFFAOYSA-N n-[4-(9,9-dimethylfluoren-2-yl)phenyl]-4-phenylaniline Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1C(C=C1)=CC=C1NC(C=C1)=CC=C1C1=CC=CC=C1 YAFZRDRWOQRUIP-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
- 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
- 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- 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
Definitions
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
- the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound. do.
- FIG. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
- FIG. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
- L1 is a direct bond; Phenylene group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; Divalent fluorenyl group; Or a divalent dimethylfluorenyl group.
- L2 and L3 are the same as or different from each other, and each independently a direct bond or a phenylene group.
- the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
- the organic material layers may be formed of the same material or different materials.
- the organic EL device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
- an organic EL device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
- the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
- An organic electroluminescent device was manufactured in the same manner as in Comparative Example, except that the compound of H-6 was used instead of the compound EB in the comparative example.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201780011526.1A CN108699069B (zh) | 2016-02-15 | 2017-02-15 | 杂环化合物及包含其的有机电致发光元件 |
| JP2018539894A JP6705586B2 (ja) | 2016-02-15 | 2017-02-15 | ヘテロ環化合物およびこれを含む有機電界発光素子 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2016-0017271 | 2016-02-15 | ||
| KR20160017271 | 2016-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2017142310A1 true WO2017142310A1 (ko) | 2017-08-24 |
Family
ID=59625289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2017/001655 WO2017142310A1 (ko) | 2016-02-15 | 2017-02-15 | 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP6705586B2 (ja) |
| KR (1) | KR101919223B1 (ja) |
| CN (1) | CN108699069B (ja) |
| WO (1) | WO2017142310A1 (ja) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10249832B1 (en) | 2017-12-06 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10593889B1 (en) | 2018-09-26 | 2020-03-17 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
| WO2021160898A3 (de) * | 2020-05-27 | 2021-10-07 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
| US11608327B2 (en) | 2016-03-03 | 2023-03-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6743896B2 (ja) * | 2016-02-15 | 2020-08-19 | エルジー・ケム・リミテッド | ヘテロ環化合物およびこれを含む有機電界発光素子 |
| EP3502107B1 (en) * | 2017-12-20 | 2022-01-26 | Samsung Display Co., Ltd. | 1-aminodibenzofuran-based compound and organic light-emitting device including the same |
| KR102655912B1 (ko) * | 2019-01-25 | 2024-04-11 | 엘티소재주식회사 | 화합물, 유기 광전자 소자 및 표시 장치 |
| CN111004243B (zh) * | 2019-12-02 | 2021-08-03 | 武汉华星光电半导体显示技术有限公司 | 吲哚并[3,2,1-jk]咔唑衍生物、有机电致发光器件及显示面板 |
| KR102212689B1 (ko) * | 2020-08-25 | 2021-02-05 | 주식회사 이엘엠 | 유기 전기 발광 소자의 캐핑층용 조성물 및 이를 포함하는 유기 전기 발광 소자 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013147481A (ja) * | 2012-01-23 | 2013-08-01 | Udc Ireland Ltd | 合成法、その合成法を用いて合成された化合物および有機電界発光素子 |
| KR20150002219A (ko) * | 2013-06-28 | 2015-01-07 | 주식회사 이엘엠 | 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자 |
| KR20150073073A (ko) * | 2013-12-20 | 2015-06-30 | 삼성디스플레이 주식회사 | 유기 일렉트로루미네센스 소자용 재료 및 이를 포함하는 유기 일렉트로루미네센스 소자 |
| KR20150114905A (ko) * | 2014-04-02 | 2015-10-13 | 유니버셜 디스플레이 코포레이션 | 유기 전계발광 물질 및 소자 |
| KR20150131564A (ko) * | 2014-05-15 | 2015-11-25 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010005697A1 (de) * | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
| KR20130096334A (ko) * | 2011-06-24 | 2013-08-30 | 덕산하이메탈(주) | 유기전기소자, 및 유기전기소자용 화합물 |
| KR20130136359A (ko) * | 2012-06-04 | 2013-12-12 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
| JP2015122369A (ja) * | 2013-12-20 | 2015-07-02 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| JP2015122356A (ja) * | 2013-12-20 | 2015-07-02 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| JP2015122371A (ja) * | 2013-12-20 | 2015-07-02 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| JP6181116B2 (ja) * | 2014-07-24 | 2017-08-16 | ドク サン ネオルクス カンパニー リミテッド | 有機電子素子及びこれを含む電子装置 |
| JP6743896B2 (ja) * | 2016-02-15 | 2020-08-19 | エルジー・ケム・リミテッド | ヘテロ環化合物およびこれを含む有機電界発光素子 |
-
2017
- 2017-02-15 KR KR1020170020577A patent/KR101919223B1/ko active IP Right Grant
- 2017-02-15 JP JP2018539894A patent/JP6705586B2/ja active Active
- 2017-02-15 WO PCT/KR2017/001655 patent/WO2017142310A1/ko active Application Filing
- 2017-02-15 CN CN201780011526.1A patent/CN108699069B/zh active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013147481A (ja) * | 2012-01-23 | 2013-08-01 | Udc Ireland Ltd | 合成法、その合成法を用いて合成された化合物および有機電界発光素子 |
| KR20150002219A (ko) * | 2013-06-28 | 2015-01-07 | 주식회사 이엘엠 | 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자 |
| KR20150073073A (ko) * | 2013-12-20 | 2015-06-30 | 삼성디스플레이 주식회사 | 유기 일렉트로루미네센스 소자용 재료 및 이를 포함하는 유기 일렉트로루미네센스 소자 |
| KR20150114905A (ko) * | 2014-04-02 | 2015-10-13 | 유니버셜 디스플레이 코포레이션 | 유기 전계발광 물질 및 소자 |
| KR20150131564A (ko) * | 2014-05-15 | 2015-11-25 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11608327B2 (en) | 2016-03-03 | 2023-03-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| US12065431B2 (en) | 2016-03-03 | 2024-08-20 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| US10249832B1 (en) | 2017-12-06 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10658594B2 (en) | 2017-12-06 | 2020-05-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10672989B2 (en) | 2017-12-06 | 2020-06-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10680181B2 (en) | 2017-12-06 | 2020-06-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11557730B2 (en) | 2017-12-06 | 2023-01-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11569449B2 (en) | 2017-12-06 | 2023-01-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10593889B1 (en) | 2018-09-26 | 2020-03-17 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
| WO2021160898A3 (de) * | 2020-05-27 | 2021-10-07 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20170095755A (ko) | 2017-08-23 |
| KR101919223B1 (ko) | 2018-11-15 |
| CN108699069B (zh) | 2021-06-01 |
| JP2019507737A (ja) | 2019-03-22 |
| CN108699069A (zh) | 2018-10-23 |
| JP6705586B2 (ja) | 2020-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2019164331A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2020046049A1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
| WO2017142310A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| WO2020050623A1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
| WO2017142304A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| WO2015152650A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2021080368A1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
| WO2017138755A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기전계발광소자 | |
| WO2019172649A1 (ko) | 다중고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2017142308A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
| WO2020040514A1 (ko) | 유기 발광 소자 | |
| WO2020130511A1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2020149596A1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
| WO2019194616A1 (ko) | 아민 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2021091173A1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
| WO2020111586A1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
| WO2020111585A1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
| WO2020080729A1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 | |
| WO2020080720A1 (ko) | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 | |
| WO2019168378A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2020013572A1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2020013657A1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2019078700A1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| WO2020130327A1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
| WO2019240470A1 (ko) | 화합물 및 이를 포함하는 유기 발광 소자 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 17753471 Country of ref document: EP Kind code of ref document: A1 |
|
| ENP | Entry into the national phase |
Ref document number: 2018539894 Country of ref document: JP Kind code of ref document: A |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 17753471 Country of ref document: EP Kind code of ref document: A1 |