JP6707805B2 - 化合物およびこれを含む有機電子素子 - Google Patents
化合物およびこれを含む有機電子素子 Download PDFInfo
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- JP6707805B2 JP6707805B2 JP2018524782A JP2018524782A JP6707805B2 JP 6707805 B2 JP6707805 B2 JP 6707805B2 JP 2018524782 A JP2018524782 A JP 2018524782A JP 2018524782 A JP2018524782 A JP 2018524782A JP 6707805 B2 JP6707805 B2 JP 6707805B2
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- 150000001875 compounds Chemical class 0.000 title claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 239000000126 substance Substances 0.000 claims description 44
- 238000002347 injection Methods 0.000 claims description 41
- 239000007924 injection Substances 0.000 claims description 41
- 239000011368 organic material Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 7
- 125000005580 triphenylene group Chemical group 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 162
- -1 1-methylpentyl Chemical group 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 32
- 230000032258 transport Effects 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 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 21
- 229940125904 compound 1 Drugs 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 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 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000005416 organic matter Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 238000004506 ultrasonic cleaning Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005549 heteroarylene group Chemical group 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 125000003277 amino group Chemical group 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 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
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000005406 washing Methods 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
- RUETVLNXAGWCDS-UHFFFAOYSA-N (4-chlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RUETVLNXAGWCDS-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 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
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 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
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- 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
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Description
Qは、炭素数10〜30の縮合多環芳香族基;または単環もしくは多環のヘテロ環基であり、
L1およびL2は、互いに同一または異なり、それぞれ独立に、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R1〜R3は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;シアノ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
aは、1〜4の整数であり、
bは、1〜4の整数であり、
cは、1〜4の整数であり、
aが2以上の場合、2以上のR1は、互いに同一または異なり、
bが2以上の場合、2以上のR2は、互いに同一または異なり、
cが2以上の場合、2以上のR3は、互いに同一または異なる。
Q、L1、L2、Ar2、R1〜R3、およびa〜cに関する定義は、前記化学式1で定義したものと同じであり、
X1〜X3のうちの少なくとも1つは、Nであり、残りは、互いに同一または異なり、それぞれ独立に、NまたはCRであり、
X4〜X6のうちの少なくとも1つは、Nであり、残りは、互いに同一または異なり、それぞれ独立に、NまたはCRであり、
Ar3〜Ar6は、互いに同一または異なり、それぞれ独立に、水素;重水素;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基である。
L1、L2、Ar1、Ar2、R1〜R3、およびa〜cに関する定義は、前記化学式1で定義したものと同じであり、
R4およびR5は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;シアノ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
dは、1〜6の整数であり、
eは、1〜8の整数であり、
dが2以上の場合、2以上のR4は、互いに同一または異なり、
eが2以上の場合、2以上のR5は、互いに同一または異なる。
窒素雰囲気下、(4−クロロフェニル)(4−ヒドロキシフェニル)メタノン(化合物1A、100.0g、429.81mmol)をアセトニトリル1000mlに添加し、撹拌しながら、ポタシウムカーボネート(118.8g、859.62mmol)を水500mlに混合して添加した。この後、水浴で加熱しながら1−ブタンスルホニルフルオライド(194.8g、644.72mmol)をゆっくり添加した。この後、約1時間反応進行後に反応を終了した。反応終了後、常温に温度を下げた後、水層と有機層とを分離した後、有機層を減圧蒸留して、化合物1B(210g、95%)を製造した。
窒素雰囲気下、前記化合物1B(210.2g、408.36mmol)、ビス(ピナコラト)ジボロン(103.7g、408.36mmol)、および酢酸カリウム(120.2g、1225.08mmol)を混合し、テトラヒドロフラン(THF)1000mlに添加し、撹拌しながら加熱した。還流する状態で、[1,1'−ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(II)(1.8g、2.45mmol)を入れて、24時間加熱撹拌した。反応終了後、常温に温度を下げた後、濾過した。濾液に水を注いでクロロホルムで抽出し、有機層を無水硫酸マグネシウムで乾燥した。減圧蒸留後、エタノールで再結晶して、化合物1C(100.0g、72%)を製造した。
窒素雰囲気下、前記化合物1C(39.0g、145.67mmol)と2−クロロ−4,6−ジフェニル−1,3,5−トリアジン(化合物1D、50.0g、145.67mmol)をテトラヒドロフラン300mlに入れて、撹拌および還流した。この後、ポタシウムカーボネート(60.4g、437.02mmol)を200mlの水に溶かして投入した後、十分に撹拌後、テトラキストリフェニル−ホスフィノパラジウム(5.0g、4.37mmol)を投入した。12時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、中間体1(52.2g、80%)を製造した。
ITO(インジウムスズ酸化物)が1000Åの厚さに薄膜コーティングされたガラス基板(corning 7059 glass)を、分散剤を溶かした蒸留水に入れて超音波洗浄した。洗剤はFischer Co.の製品を使用し、蒸留水はMillipore Co.製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノール溶剤の順に超音波洗浄をし乾燥させた。
前記実験例1−1における電子輸送層として化合物1の代わりに化合物2を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における電子輸送層として化合物1の代わりに化合物3を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における電子輸送層として化合物1の代わりに化合物4を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における電子輸送層として化合物1の代わりに化合物5を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
ITO(indium tin oxide)が1,500Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
前記実験例2−1における発光層として化合物1の代わりに化合物2を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例2−1における発光層として化合物1の代わりに化合物3を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例2−1における発光層として化合物1の代わりに化合物4を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例2−1における発光層として化合物1の代わりに化合物5を用いたことを除けば、実験例2−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における化合物1の代わりに下記ET5の化合物を用いたことを除けば、前記実験例1−1と同様の方法で有機発光素子を作製した。
また、本願明細書の化合物を発光層物質として用いて製造された有機発光素子も、比較例2−1〜2−4の物質に比べて、特に寿命において優れた特性を示すことが分かる。
20:基板
30:第1電極
40:発光層
50:第2電極
60:正孔注入層
70:正孔輸送層
80:電子阻止層
90:電子輸送層
100:電子注入層
Claims (11)
- 下記化学式1で表される化合物:
Qは、ナフチレン;アントラセン;またはフェナントレンであり、
L1およびL2は、互いに同一または異なり、それぞれ独立に、直接結合;フェニレン基;またはビフェニレン基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、アリール基で置換されたトリアジン基、アリール基で置換されたピリミジン基、アリール基で置換されたピリジン基、トリフェニレン基、またはカルバゾール基であり(ただし、Ar1およびAr2の両方がカルバゾール基である場合を除く)、
R1〜R3は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;シアノ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
aは、1〜4の整数であり、
bは、1〜4の整数であり、
cは、1〜4の整数であり、
aが2以上の場合、2以上のR1は、互いに同一または異なり、
bが2以上の場合、2以上のR2は、互いに同一または異なり、
cが2以上の場合、2以上のR3は、互いに同一または異なる。 - 前記化学式1は、下記化学式1−Aまたは1−Bで表される、請求項1に記載の化合物:
Q、L1、L2、R1〜R3、Ar2およびa〜cに関する定義は、前記化学式1で定義したものと同じであり、
X1〜X3のうちの少なくとも1つは、Nであり、残りは、互いに同一または異なり、それぞれ独立に、NまたはCRであり、
X4〜X6のうちの少なくとも1つは、Nであり、残りは、互いに同一または異なり、それぞれ独立に、NまたはCRであり、
Rは、水素;重水素;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
Ar3〜Ar6は、互いに同一または異なり、それぞれ独立に、水素;重水素;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;また置換もしくは非置換のヘテロアリール基である。 - 前記化学式1は、下記化学式2〜5のうちのいずれか1つで表される、請求項1に記載の化合物:
L1、L2、Ar1、Ar2、R1〜R3、およびa〜cに関する定義は、前記化学式1で定義したものと同じであり、
R4およびR5は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;シアノ基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
dは、1〜6の整数であり、
eは、1〜8の整数であり、
dが2以上の場合、2以上のR4は、互いに同一または異なり、
eが2以上の場合、2以上のR5は、互いに同一または異なる。 - 第1電極と、前記第1電極に対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含む有機電子素子であって、前記有機物層のうちの1層以上は、請求項1〜4のいずれか1項に記載の化合物を含むものである有機電子素子。
- 前記有機物層は、発光層を含み、前記発光層は、前記化合物を含むものである、請求項5に記載の有機電子素子。
- 前記有機物層は、正孔注入層または正孔輸送層を含み、前記正孔注入層または正孔輸送層は、前記化合物を含むものである、請求項5に記載の有機電子素子。
- 前記有機物層は、電子注入層または電子輸送層を含み、前記電子輸送層または電子注入層は、前記化合物を含むものである、請求項5に記載の有機電子素子。
- 前記有機物層は、電子阻止層または正孔阻止層を含み、前記電子阻止層または正孔阻止層は、前記化合物を含むものである、請求項5に記載の有機電子素子。
- 前記有機電子素子は、正孔注入層、正孔輸送層、電子注入層、電子輸送層、電子阻止層、および正孔阻止層からなる群より選択される1層または2層以上をさらに含むものである、請求項5に記載の有機電子素子。
- 前記有機電子素子は、有機発光素子、有機燐光素子、有機太陽電池、有機感光体(OPC)、および有機トランジスタからなる群より選択される、請求項5に記載の有機電子素子。
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