JP2018531232A - アミン化合物およびこれを含む有機発光素子 - Google Patents
アミン化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP2018531232A JP2018531232A JP2018515253A JP2018515253A JP2018531232A JP 2018531232 A JP2018531232 A JP 2018531232A JP 2018515253 A JP2018515253 A JP 2018515253A JP 2018515253 A JP2018515253 A JP 2018515253A JP 2018531232 A JP2018531232 A JP 2018531232A
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- light emitting
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- -1 Amine compound Chemical class 0.000 title claims abstract description 55
- 239000010410 layer Substances 0.000 claims description 211
- 150000001875 compounds Chemical class 0.000 claims description 92
- 238000002347 injection Methods 0.000 claims description 64
- 239000007924 injection Substances 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 46
- 230000005525 hole transport Effects 0.000 claims description 44
- 239000012044 organic layer Substances 0.000 claims description 32
- 239000011368 organic material Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 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 7
- 125000001624 naphthyl group Chemical group 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000005581 pyrene group Chemical group 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000005578 chrysene group Chemical group 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 230000032258 transport Effects 0.000 description 39
- 239000000463 material Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 229940126214 compound 3 Drugs 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 150000001716 carbazoles Chemical group 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- 125000005264 aryl amine 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
- 238000000576 coating method Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 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
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 2
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 230000000903 blocking effect Effects 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
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000003003 spiro group Chemical group 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
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-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
- 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
- ZZLQHXCRRMUGQJ-UHFFFAOYSA-N 2'-Hydroxyflavone Natural products OC1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 ZZLQHXCRRMUGQJ-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
- 125000005916 2-methylpentyl group Chemical group 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
- RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 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
- 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
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-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
- 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
- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000011248 coating agent Substances 0.000 description 1
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- 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
- 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
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- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical compound O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
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- 125000005842 heteroatom Chemical group 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
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 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
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
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- 239000011133 lead Substances 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
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- 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
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- JWTJIFMXLBCLPV-UHFFFAOYSA-N n,9,9-triphenylfluoren-2-amine Chemical compound C=1C=C2C3=CC=CC=C3C(C=3C=CC=CC=3)(C=3C=CC=CC=3)C2=CC=1NC1=CC=CC=C1 JWTJIFMXLBCLPV-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- 230000003472 neutralizing effect Effects 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
- 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
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- 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
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
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- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 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
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-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
- 238000010992 reflux Methods 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring 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
- 230000002194 synthesizing effect Effects 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
- 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
- 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
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
[化学式1]
Ar1〜Ar4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リール基または置換もしくは非置換のヘテロ環基であるか、Ar1とAr2がE1によって互いに連結されるか、Ar3とAr4がE2によって互いに連結され、
E1およびE2は、互いに同一または異なり、それぞれ独立に、直接結合、CRR'、NR、O、またはS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、直接結合であるか、置換もしくは非置換のアリーレンまたは置換もしくは非置換のヘテロアリーレンであり、nおよびmは、互いに同一または異なり、それぞれ0〜3の整数であり、nおよびmがそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なり、
R1、R2、RおよびR'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;ニトリル基;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シクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルアルキル基;置換もしくは非置換のアルアルケニル基;置換もしくは非置換のアルキルアリール基;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環基であり、pおよびqは、互いに同一または異なり、それぞれ0〜7の整数であり、pおよびqがそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なる。
2:陽極
3:発光層
4:陰極
5:正孔注入層
6:正孔輸送層
7:電子輸送層
[化学式2]
[化学式A−1]
wは、1以上の整数であり、
Ar5は、置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L3は、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、
Ar6およびAr7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リール基;置換もしくは非置換のシリル基;置換もしくは非置換のゲルマニウム基;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アルキル基;または置換もしくは非置換のヘテロアリール基であるか、互いに結合して置換もしくは非置換の環を形成してもよいし、
wが2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
[化学式A−2]
Ar8およびAr9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単環のアリール基;または置換もしくは非置換の多環のアリール基であり、
G1〜G8は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基である。
1−ブロモ−2−ヨードベンゼン(30g、106mmol)と(2−クロロフェニル)ボロン酸(16.9g、108.6mmol)をジオキサン(300ml)に添加した後、2Mポタシウムカーボネート水溶液(100ml)を添加し、テトラキストリフェニル−ホスフィノパラジウム(2.45g、2mol%)を入れた後、4時間加熱撹拌した。常温に温度を下げて反応を終了した後、ポタシウムカーボネート溶液を除去して層分離した。溶媒除去後、ヘキサンでカラムして、前記化合物A1、白色固体(25.3g、90%)を製造した。
MS[M+H]+=266.95
化合物A1(20g、75.2mmol)をTHF(250ml)に溶解した後、温度を−78℃に下げた後、2.5M n−BuLi(39ml)を滴加し、30分後、2−ブロモ−9H−フルオレ−9−オン(19.3、75.2mmol)を入れて、常温に温度を上げた後、1時間撹拌した。1N HCl(300ml)を入れて30分間撹拌した後、層分離して、溶媒除去後、エチルアセテートで洗い落として、化合物A2(28.5g、85%)を製造した。
MS[M+H]+=447.01
化合物A2(20g、44.84mmol)を酢酸(250ml)に入れた後、硫酸2mlを滴加して撹拌還流した。常温に温度を下げて水で中和した後、濾過した固体をエチルアセテートで再結晶して、化合物A3(13.43g、70%)を製造した。
MS[M+H]+=429.00
MS[M+H]+=803.33
MS[M+H]+=879.37
MS[M+H]+=843.37
MS[M+H]+=891.37
MS[M+H]+=751.30
MS[M+H]+=727.92
MS[M+H]+=804.02
ITO(インジウムスズ酸化物)が1,000Å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。
前記実施例1において、正孔輸送層として製造例2で合成した化合物3の代わりに化合物4を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例1において、正孔輸送層として製造例2で合成した化合物3の代わりに化合物5を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例1において、正孔輸送層として製造例2で合成した化合物3の代わりにHT1を、正孔調節層としてHT2の代わりに化合物1を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例4において、正孔調節層として製造例2で合成した化合物1の代わりに化合物2を用いたことを除けば、同様に有機発光素子を製造した。
実施例1のように用意されたITO透明電極上に、化合物3を50Åの厚さに熱真空蒸着して正孔注入層(100Å)を形成するが、A2を5%のドーピング濃度にドーピングし、その上に、正孔を輸送する物質である前記化合物3(1100Å)を真空蒸着した後、次に、前記正孔輸送層上に、HT2を膜厚さ(600Å)に真空蒸着して正孔調節層を形成した。発光層としてホストH1とドーパントD1の化合物(2%)を300Åの厚さに真空蒸着した。次に、E1化合物をLiQと1:1(350Å)で電子輸送層として形成した後、順次に、10Åの厚さのリチウムフルオライド(LiF)と、1000Åの厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
前記実施例6において、正孔注入層および正孔輸送層として製造例2で合成した化合物3の代わりに化合物5を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例6において、正孔注入層および正孔輸送層として化合物3の代わりにHT1を、正孔調節層としてHT2の代わりに化合物1を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例8において、正孔調節層として製造例2で合成した化合物1の代わりに化合物2を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例1において、正孔輸送層として製造例2で合成した化合物3の代わりに化合物6を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例8において、正孔調節層として製造例2で合成した化合物1の代わりに化合物7を用いたことを除けば、同様に有機発光素子を製造した。
前記実施例1において、正孔輸送層として製造例2で合成した化合物3の代わりにHT1を用いたことを除けば、同様に実験した。
前記実施例6において、正孔注入層および正孔輸送層として化合物3の代わりにHT1を用いたことを除けば、同様に実験した。
用意されたITO透明電極上に、前述のA1を50Åの厚さに熱真空蒸着して正孔注入層を形成した。その上に、正孔を輸送する物質である化合物3(800Å)を真空蒸着して正孔輸送層を形成し、その上に、HT2(100Å)を正孔調節層として形成させた後、順次に、ホストH2とドーパントD2(4重量%)を300Åの厚さに真空蒸着した。次に、E1化合物をLiQと1:1(300Å)で電子輸送層として形成した後、順次に、10Åの厚さのリチウムフルオライド(LiF)と、800Åの厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
前記実施例12において、正孔輸送層として製造例2で合成した化合物3の代わりに化合物4を用いたことを除けば、同様に実験した。
前記実施例12において、正孔輸送層として製造例2で合成した化合物3の代わりに化合物5を用いたことを除けば、同様に実験した。
実施例1のように用意されたITO透明電極上に、化合物3を50Åの厚さに熱真空蒸着して正孔注入層を形成するが、化合物A1を10%のドーピング濃度にドーピングし、正孔輸送層として化合物3(800Å)を真空蒸着して形成し、その上に、HT2(100Å)を正孔調節層として形成させた後、順次に、ホストH2とドーパントD2(4重量%)を300Åの厚さに真空蒸着した。次に、E1化合物をLiQと1:1(300Å)で電子輸送層として形成した後、順次に、10Åの厚さのリチウムフルオライド(LiF)と、800Åの厚さのアルミニウムを蒸着して陰極を形成し、有機発光素子を製造した。
前記実施例15において、正孔注入層および正孔輸送層として化合物3の代わりに化合物5を用いたことを除けば、同様に実験した。
前記実施例13において、正孔注入層および正孔輸送層として化合物3の代わりにHT1を、正孔調節層としてHT2の代わりに化合物1を用いたことを除けば、同様に実験した。
前記実施例12において、正孔輸送層として製造例2で合成した化合物3の代わりにHT1を用いたことを除けば、同様に実験した。
前記実施例15において、正孔注入層および正孔輸送層として化合物3の代わりにHT1を用いたことを除けば、同様に実験した。
前記実施例12において、正孔輸送層として製造例2で合成した化合物3の代わりにHT3を用いたことを除けば、同様に実験した。
前記実施例12において、正孔輸送層として製造例2で合成した化合物3の代わりにHT4を用いたことを除けば、同様に実験した。
前記実施例15において、正孔注入層および正孔輸送層として化合物3の代わりにHT3を用いたことを除けば、同様に実験した。
前記実施例15において、正孔注入層および正孔輸送層として化合物3の代わりにHT4を用いたことを除けば、同様に実験した。
Claims (15)
- 下記化学式1の化合物:
[化学式1]
Ar1〜Ar4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リール基または置換もしくは非置換のヘテロ環基であるか、Ar1とAr2がE1によって互いに連結されるか、Ar3とAr4がE2によって互いに連結され、
E1およびE2は、互いに同一または異なり、それぞれ独立に、直接結合、CRR'、NR、O、またはS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、直接結合であるか、置換もしくは非置換のアリーレンまたは置換もしくは非置換のヘテロアリーレンであり、nおよびmは、互いに同一または異なり、それぞれ0〜3の整数であり、
R1、R2、RおよびR'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;ニトリル基;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シクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルアルキル基;置換もしくは非置換のアルアルケニル基;置換もしくは非置換のアルキルアリール基;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環基であり、pおよびqは、互いに同一または異なり、それぞれ0〜7の整数である。 - 前記化学式1は、下記化学式2で表されるものである、
請求項1に記載の化合物:
[化学式2]
- Ar1〜Ar4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フェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のターフェニル基、置換もしくは非置換のクォーターフェニル基、置換もしくは非置換のナフチル基、置換もしくは非置換のフェナントリル基、置換もしくは非置換のトリフェニレン基、置換もしくは非置換のフルオレニル基、置換もしくは非置換のスピロビフルオレニル基、置換もしくは非置換のジベンゾチオフェン基、置換もしくは非置換のジベンゾフラン基、または置換もしくは非置換のカルバゾール基である、
請求項1または2に記載の化合物。 - Ar1とAr2またはAr3とAr4は、CRR'、NR、S、またはOを介して互いに結合し、
RおよびR'の定義は、化学式1に記載した通りである、
請求項1から3のいずれか1項に記載の化合物。 - 前記化学式1は、下記構造式から選択されるものである、
請求項1に記載の化合物:
- 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発光素子であって、
前記有機物層のうちの1層以上は、請求項1〜5のいずれか1項に記載の化合物を含むものである
有機発光素子。 - 前記有機物層は、正孔輸送層を含み、
前記正孔輸送層は、前記化合物を含むものである、
請求項6に記載の有機発光素子。 - 前記有機物層は、正孔注入層を含み、
前記正孔注入層は、前記化合物を含むものである、
請求項6または7に記載の有機発光素子。 - 前記有機物層は、正孔調節層を含み、
前記正孔調節層は、前記化合物を含むものである、
請求項6から8のいずれか1項に記載の有機発光素子。 - 前記有機物層は、正孔注入および正孔輸送を同時に行う層を含み、
前記正孔注入および正孔輸送を同時に行う層は、前記化合物を含むものである、
請求項6から9のいずれか1項に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、下記化学式A−1で表される化合物を含むものである、
請求項6から10のいずれか1項に記載の有機発光素子:
[化学式A−1]
wは、1以上の整数であり、
Ar5は、置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L3は、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、
Ar6およびAr7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リール基;置換もしくは非置換のシリル基;置換もしくは非置換のゲルマニウム基;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アルキル基;または置換もしくは非置換のヘテロアリール基であるか、互いに結合して置換もしくは非置換の環を形成してもよいし、
wが2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。 - 前記L3は、直接結合であり、
前記Ar5は、2価のピレン基であり、
前記Ar6および前記Ar7は、互いに同一または異なり、それぞれ独立に、メチル基で置換もしくは非置換のフェニル基;またはtert−ブチル基で置換もしくは非置換のジベンゾフラン基であり、
wは、2である、
請求項11に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、下記化学式A−2で表される化合物を含むものである、
請求項6から10のいずれか1項に記載の有機発光素子:
[化学式A−2]
Ar8およびAr9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単環のアリール基;または置換もしくは非置換の多環のアリール基であり、
G1〜G8は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基である。 - 前記Ar8は、1−ナフチル基であり、
前記Ar9は、2−ナフチル基である、
請求項13に記載の有機発光素子。 - 前記発光層は、下記化学式A−2で表される化合物を含むものである、
請求項11または12に記載の有機発光素子:
[化学式A−2]
Ar8およびAr9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単環のアリール基;または置換もしくは非置換の多環のアリール基であり、
G1〜G8は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基である。
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