KR20200048218A - Ink composition for organic light emitting device - Google Patents
Ink composition for organic light emitting device Download PDFInfo
- Publication number
- KR20200048218A KR20200048218A KR1020180130046A KR20180130046A KR20200048218A KR 20200048218 A KR20200048218 A KR 20200048218A KR 1020180130046 A KR1020180130046 A KR 1020180130046A KR 20180130046 A KR20180130046 A KR 20180130046A KR 20200048218 A KR20200048218 A KR 20200048218A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- unsubstituted
- substituted
- ink composition
- compound
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000002904 solvent Substances 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000000126 substance Substances 0.000 claims abstract description 10
- -1 biphenylyl Chemical group 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 6
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 claims description 6
- CHWNEIVBYREQRF-UHFFFAOYSA-N 4-Ethyl-2-methoxyphenol Chemical compound CCC1=CC=C(O)C(OC)=C1 CHWNEIVBYREQRF-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 6
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 claims description 4
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 claims description 4
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 claims description 4
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 claims description 4
- LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 claims description 4
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 claims description 4
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims description 4
- CDIKGISJRLTLRA-UHFFFAOYSA-N 4-Methyl-2-phenyl-1,3-dioxolane Chemical compound O1C(C)COC1C1=CC=CC=C1 CDIKGISJRLTLRA-UHFFFAOYSA-N 0.000 claims description 3
- SUFDFKRJYKNTFH-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=CC(OC)=CC=C21 SUFDFKRJYKNTFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 2
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 claims description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 claims description 2
- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 claims description 2
- PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 claims description 2
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims description 2
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 claims description 2
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 claims description 2
- BBUPBICWUURTNP-UHFFFAOYSA-N 2,4-dimethyl-1-nitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C(C)=C1 BBUPBICWUURTNP-UHFFFAOYSA-N 0.000 claims description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 claims description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 2
- RUGISKODRCWQNE-UHFFFAOYSA-N 2-(2-methylphenyl)ethanol Chemical compound CC1=CC=CC=C1CCO RUGISKODRCWQNE-UHFFFAOYSA-N 0.000 claims description 2
- UOBQDYFTAJKQAL-UHFFFAOYSA-N 2-cyclohexylcyclohexan-1-one Chemical compound O=C1CCCCC1C1CCCCC1 UOBQDYFTAJKQAL-UHFFFAOYSA-N 0.000 claims description 2
- QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 claims description 2
- CWZGKTMWPFTJCS-UHFFFAOYSA-N 2-cyclopentylcyclopentan-1-one Chemical compound O=C1CCCC1C1CCCC1 CWZGKTMWPFTJCS-UHFFFAOYSA-N 0.000 claims description 2
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 claims description 2
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical group COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 claims description 2
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical group CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 claims description 2
- BOHCMQZJWOGWTA-UHFFFAOYSA-N 3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1 BOHCMQZJWOGWTA-UHFFFAOYSA-N 0.000 claims description 2
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 claims description 2
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 claims description 2
- 229940077398 4-methyl anisole Drugs 0.000 claims description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims description 2
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 claims description 2
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 claims description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims description 2
- DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 claims description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 2
- NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- PLZZPPHAMDJOSR-UHFFFAOYSA-N nonanenitrile Chemical compound CCCCCCCCC#N PLZZPPHAMDJOSR-UHFFFAOYSA-N 0.000 claims description 2
- 229960002446 octanoic acid Drugs 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 claims 1
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 claims 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical group CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 claims 1
- NDDFBEOUDFSIHZ-UHFFFAOYSA-N 3-(1-hydroxyethyl)benzene-1,2-diol Chemical compound CC(O)C1=CC=CC(O)=C1O NDDFBEOUDFSIHZ-UHFFFAOYSA-N 0.000 claims 1
- 0 *c1c(*)c(*)c(C2(Cc3ccc(C=C)cc3)c3cc(N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c4c(*)c(*)c(*)c(*)c4*)ccc3-c3ccccc23)c(*)c1* Chemical compound *c1c(*)c(*)c(C2(Cc3ccc(C=C)cc3)c3cc(N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c4c(*)c(*)c(*)c(*)c4*)ccc3-c3ccccc23)c(*)c1* 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229940125904 compound 1 Drugs 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002346 layers by function Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XKWSWANXMRXDES-UHFFFAOYSA-N 3-methylbutyl octanoate Chemical compound CCCCCCCC(=O)OCCC(C)C XKWSWANXMRXDES-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- YWSNHSLHRJLFFH-UHFFFAOYSA-N C(C1)C(C2)C1=CC=C2Oc1ccc(C2(c(cc(cc3)N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc4C5(c(cc6)ccc6OC6=CC=CCC6)c(cc6)ccc6Oc6ccc(CC7)c7c6)ccc4-c4c5cccc4)c3-c3ccccc23)c(cc2)ccc2Oc2ccccc2)cc1 Chemical compound C(C1)C(C2)C1=CC=C2Oc1ccc(C2(c(cc(cc3)N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc4C5(c(cc6)ccc6OC6=CC=CCC6)c(cc6)ccc6Oc6ccc(CC7)c7c6)ccc4-c4c5cccc4)c3-c3ccccc23)c(cc2)ccc2Oc2ccccc2)cc1 YWSNHSLHRJLFFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000005137 deposition process Methods 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000006467 substitution reaction Methods 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
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- DSXKDTZEIWTHRO-UHFFFAOYSA-N 1,2,3,9-tetrahydrocarbazol-4-one Chemical compound N1C2=CC=CC=C2C2=C1CCCC2=O DSXKDTZEIWTHRO-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
- 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
- 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
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-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
- 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- JVNCFFFHVBWVBR-UHFFFAOYSA-N 2-(1-hydroxyethyl)phenol Chemical compound CC(O)C1=CC=CC=C1O JVNCFFFHVBWVBR-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NJRNORJLPQYHHY-UHFFFAOYSA-N 2-bromo-9-phenylfluoren-9-ol Chemical compound C12=CC=CC=C2C2=CC=C(Br)C=C2C1(O)C1=CC=CC=C1 NJRNORJLPQYHHY-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
- VJJZJBUCDWKPLC-UHFFFAOYSA-N 3-methoxyapigenin Chemical compound O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C=C1 VJJZJBUCDWKPLC-UHFFFAOYSA-N 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
- SZCUTTWWJLTJTK-UHFFFAOYSA-N 4-[2-bromo-9-(4-methylphenyl)fluoren-9-yl]phenol Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(C1=CC=C(C=C1)C)C1=CC=C(C=C1)O SZCUTTWWJLTJTK-UHFFFAOYSA-N 0.000 description 1
- PGJKRGODHQXPHT-UHFFFAOYSA-N 4-[2-bromo-9-(4-tert-butylphenyl)fluoren-9-yl]phenol Chemical compound C1=CC(C(C)(C)C)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(Br)=CC=C2C2=CC=CC=C21 PGJKRGODHQXPHT-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
- 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
- CIPNASZLMQSHNV-UHFFFAOYSA-N C=CCSc1ccc(C(C2C=CC=CC22)(c3c2ccc(N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)C(C=CC2c4ccccc44)=CC2C4(c(cc2)ccc2F)c(cc2)ccc2SCC=C)c3)c(cc2)ccc2F)cc1 Chemical compound C=CCSc1ccc(C(C2C=CC=CC22)(c3c2ccc(N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)C(C=CC2c4ccccc44)=CC2C4(c(cc2)ccc2F)c(cc2)ccc2SCC=C)c3)c(cc2)ccc2F)cc1 CIPNASZLMQSHNV-UHFFFAOYSA-N 0.000 description 1
- WXRTXRAOUFORDF-UHFFFAOYSA-N C=Cc(cc1)ccc1Sc1ccc(C2(c(cc(cc3)N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc4)cc5c4-c4ccccc4C5(c(cc4)ccc4F)c(cc4)ccc4Sc4ccc(C=C)cc4)c3-c3ccccc23)c(cc2)ccc2F)cc1 Chemical compound C=Cc(cc1)ccc1Sc1ccc(C2(c(cc(cc3)N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc4)cc5c4-c4ccccc4C5(c(cc4)ccc4F)c(cc4)ccc4Sc4ccc(C=C)cc4)c3-c3ccccc23)c(cc2)ccc2F)cc1 WXRTXRAOUFORDF-UHFFFAOYSA-N 0.000 description 1
- SYCJCWYROQSNRX-UHFFFAOYSA-N C=Cc1ccc(CC2(c(cc(cc3)N(c(cc4)ccc4-c4ccccc4)c(cc45)ccc4-c4ccccc4C54c(cc(cc5)N(c(cc6)ccc6-c6ccccc6)c(cc6)cc7c6-c6ccccc6C7(Cc6ccc(C=C)cc6)c(c(F)c(c(F)c6F)F)c6F)c5-c5ccccc45)c3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 Chemical compound C=Cc1ccc(CC2(c(cc(cc3)N(c(cc4)ccc4-c4ccccc4)c(cc45)ccc4-c4ccccc4C54c(cc(cc5)N(c(cc6)ccc6-c6ccccc6)c(cc6)cc7c6-c6ccccc6C7(Cc6ccc(C=C)cc6)c(c(F)c(c(F)c6F)F)c6F)c5-c5ccccc45)c3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 SYCJCWYROQSNRX-UHFFFAOYSA-N 0.000 description 1
- LIQVMQSZEJNGPB-UHFFFAOYSA-N C=Cc1ccc(CC2(c3cc(N(c(cc4)ccc4-c4ccccc4)c(cc4)c(cccc5)c5c4-c(c4c5cccc4)ccc5N(c(cc4)ccc4-c4ccccc4)c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c(c(F)c(c(F)c4F)F)c4F)ccc3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 Chemical compound C=Cc1ccc(CC2(c3cc(N(c(cc4)ccc4-c4ccccc4)c(cc4)c(cccc5)c5c4-c(c4c5cccc4)ccc5N(c(cc4)ccc4-c4ccccc4)c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c(c(F)c(c(F)c4F)F)c4F)ccc3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 LIQVMQSZEJNGPB-UHFFFAOYSA-N 0.000 description 1
- LYUMJYNJOBAIHC-UHFFFAOYSA-N C=Cc1ccc(CC2(c3cc(N(c(cc4)ccc4-c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c(cc4)ccc4-c4ccccc4)c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c(c(F)c(c(F)c4F)F)c4F)ccc3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 Chemical compound C=Cc1ccc(CC2(c3cc(N(c(cc4)ccc4-c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c(cc4)ccc4-c4ccccc4)c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c(c(F)c(c(F)c4F)F)c4F)ccc3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 LYUMJYNJOBAIHC-UHFFFAOYSA-N 0.000 description 1
- OTGLNFLRJKEFTC-UHFFFAOYSA-N C=Cc1ccc(CC2(c3cc(N(c4c(cccc5)c5ccc4)c(c4c5cccc4)ccc5-c(cc4)c(cccc5)c5c4N(c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c(c(F)c(c(F)c4F)F)c4F)c4cccc5c4cccc5)ccc3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 Chemical compound C=Cc1ccc(CC2(c3cc(N(c4c(cccc5)c5ccc4)c(c4c5cccc4)ccc5-c(cc4)c(cccc5)c5c4N(c(cc45)ccc4-c4ccccc4C5(Cc4ccc(C=C)cc4)c(c(F)c(c(F)c4F)F)c4F)c4cccc5c4cccc5)ccc3-c3c2cccc3)c(c(F)c(c(F)c2F)F)c2F)cc1 OTGLNFLRJKEFTC-UHFFFAOYSA-N 0.000 description 1
- YIBLSGXWEOIOEF-UHFFFAOYSA-N C=Cc1ccc(CSc2ccc(C3(c(cc(cc4)N(c5ccccc5)c(cc5)ccc5-c(cc5)ccc5N(c5ccccc5)c(cc5)cc6c5-c5ccccc5C6(c(cc5)ccc5F)c(cc5)ccc5SCc5ccc(C=C)cc5)c4-c4ccccc34)c(cc3)ccc3F)cc2)cc1 Chemical compound C=Cc1ccc(CSc2ccc(C3(c(cc(cc4)N(c5ccccc5)c(cc5)ccc5-c(cc5)ccc5N(c5ccccc5)c(cc5)cc6c5-c5ccccc5C6(c(cc5)ccc5F)c(cc5)ccc5SCc5ccc(C=C)cc5)c4-c4ccccc34)c(cc3)ccc3F)cc2)cc1 YIBLSGXWEOIOEF-UHFFFAOYSA-N 0.000 description 1
- QSVCYAUEKKEFNU-UHFFFAOYSA-N CC(C)(C)c1ccc(C2(c3cc(C(F)(F)F)ccc3-c3ccccc23)c(cc2)ccc2Oc2ccc(C=O)cc2)cc1 Chemical compound CC(C)(C)c1ccc(C2(c3cc(C(F)(F)F)ccc3-c3ccccc23)c(cc2)ccc2Oc2ccc(C=O)cc2)cc1 QSVCYAUEKKEFNU-UHFFFAOYSA-N 0.000 description 1
- KYMHFDLNQVYAKM-UHFFFAOYSA-N CC(CC(Nc1ccccc1)=CC1)C1c(cc1)ccc1Nc1ccccc1 Chemical compound CC(CC(Nc1ccccc1)=CC1)C1c(cc1)ccc1Nc1ccccc1 KYMHFDLNQVYAKM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- KBMAQKIHSJOMEL-UHFFFAOYSA-N Fc1ccc(C2(c(cc(cc3)N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc4)cc5c4-c4ccccc4C5(c(cc4)ccc4F)c(cc4)ccc4Sc4ccc(CC5)c5c4)c3-c3ccccc23)c(cc2)ccc2Sc2cc(CC3)c3cc2)cc1 Chemical compound Fc1ccc(C2(c(cc(cc3)N(c4ccccc4)c(cc4)ccc4-c(cc4)ccc4N(c4ccccc4)c(cc4)cc5c4-c4ccccc4C5(c(cc4)ccc4F)c(cc4)ccc4Sc4ccc(CC5)c5c4)c3-c3ccccc23)c(cc2)ccc2Sc2cc(CC3)c3cc2)cc1 KBMAQKIHSJOMEL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 125000001246 bromo group Chemical group Br* 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000006165 cyclic alkyl 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
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- TUEYHEWXYWCDHA-UHFFFAOYSA-N ethyl 5-methylthiadiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=NSC=1C TUEYHEWXYWCDHA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 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
- 125000005549 heteroarylene group 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 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
- 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- H01L51/0007—
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
Abstract
Description
본 발명은 잉크젯 공정에 적용할 수 있는 유기 발광 소자용 잉크 조성물에 관한 것이다. The present invention relates to an ink composition for an organic light emitting device that can be applied to an inkjet process.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layered structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.
한편, 최근에는 공정 비용 절감을 위하여 기존의 증착 공정 대신 용액 공정, 특히 잉크젯 공정을 이용한 유기 발광 소자가 개발되고 있다. 초창기에는 모든 유기 발광 소자 층을 용액 공정으로 코팅하여 유기 발광 소자를 개발하려 하였으나 현재 기술로는 한계가 있어, 정구조 형태에서 HIL, HTL, EML만을 용액 공정으로 진행하고 추후 공정은 기존의 증착 공정을 활용하는 하이브리드(hybrid) 공정이 연구 중이다. Meanwhile, an organic light emitting device using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process to reduce process cost. In the early days, all organic light-emitting device layers were coated with a solution process to develop an organic light-emitting device, but there are limitations in current technology, so only HIL, HTL, and EML are used as a solution process in the form of a regular structure, and the subsequent process is an existing deposition process. A hybrid process that utilizes is being studied.
잉크젯 공정을 이용하여 유기 발광 소자의 기능층을 형성하는 경우, 정밀도를 위하여 잉크가 헤드의 노즐에서 안정하게 토출되어야 하며, 도포된 후 건조되는 과정에서 균일하면서도 평탄한 막을 형성하여야 한다. 예를 들어, 격벽으로 둘러싸인 기능층 형성 영역에 잉크를 도포한 후 건조시키면, 잉크 막이 불균일하게 고화되는 경우에는 막 편탕성을 확보하기 어려운데, 특히 중심부의 막 두께가 격벽측 보다 두꺼워지거나(볼록한 모양), 중심부보다 격벽측 막두께가 두꺼워지는 현상(오목한 모양)이 발생하는 경우가 많다.In the case of forming the functional layer of the organic light emitting device using the inkjet process, the ink must be stably discharged from the nozzle of the head for precision, and a uniform and flat film should be formed in the process of drying after application. For example, when ink is applied to a functional layer forming region surrounded by a partition wall and then dried, it is difficult to secure film flatness when the ink film is solidified non-uniformly. In particular, the film thickness of the central portion becomes thicker than the partition wall side (convex shape) ), A phenomenon in which the thickness of the partition wall side becomes thicker than the center (concave shape) is often generated.
따라서, 잉크젯 공정을 적용함에 있어, 상기의 문제를 해결할 수 있는 유기 발광 소자용 잉크 조성물의 개발이 요구된다. Therefore, in applying the inkjet process, there is a need to develop an ink composition for an organic light emitting device that can solve the above problems.
본 발명은 잉크젯 공정에 적용할 수 있는 유기 발광 소자용 잉크 조성물을 제공하기 위한 것이다. The present invention is to provide an ink composition for an organic light emitting device that can be applied to an inkjet process.
상기 과제를 해결하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물, 및 용매를 포함하는 유기 발광 소자용 잉크 조성물에 있어서, 상기 용매는, log P가 1.5 이상이고, 분자 부피가 190 cm3/mole 이하인, 잉크 조성물을 제공한다:In order to solve the above problems, the present invention in the ink composition for an organic light emitting device comprising a compound represented by the formula (1), and a solvent, the solvent, log P is 1.5 or more, molecular volume is 190 cm 3 / Provides an ink composition that is less than mole:
[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
L 및 L1 내지 L4는 각각 독립적으로 치환 또는 비치환된 C1-60 알킬렌; 치환 또는 비치환된 C6-60 아릴렌이고,L and L 1 to L 4 are each independently substituted or unsubstituted C 1-60 alkylene; Substituted or unsubstituted C 6-60 arylene,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
R1 내지 R4는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1-60 알킬, 치환 또는 비치환된 C1-60 알콕시, 치환 또는 비치환된 C6-60 아릴, 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,R 1 to R 4 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 1-60 alkoxy, substituted or unsubstituted C 6-60 aryl, or N, O And C 2-60 heteroaryl comprising any one or more heteroatoms selected from the group consisting of S,
Y1 내지 Y4는 각각 독립적으로 수소, 또는 -X-A이되, 단 Y1 내지 Y4 중 2 이상이 -X-A이며,Y 1 to Y 4 are each independently hydrogen, or -XA, provided that 2 or more of Y 1 to Y 4 are -XA,
X는 단일 결합, O, 또는 S이고,X is a single bond, O, or S,
A는 열 또는 광에 의하여 가교 가능한 작용기이고,A is a functional group capable of crosslinking by heat or light,
n1 및 n4는 각각 0 내지 4의 정수이고,n1 and n4 are each an integer from 0 to 4,
n2 및 n3는 각각 0 내지 3의 정수이다.n2 and n3 are each an integer of 0-3.
본 발명에 따른 유기 발광 소자 형성용 잉크 조성물은, 잉크젯 공정으로 잉크막 형성 후 건조하였을 때 표면이 매끄러우면서 평탄한 막을 형성할 수 있다. The ink composition for forming an organic light emitting device according to the present invention can form a smooth and flat film when dried after forming an ink film by an inkjet process.
도 1은, 본 발명의 실험예에 따라 막 평탄도를 측정하는 방법을 도식적으로 나타낸 것이다.
도 2는, 본 발명의 실험예에 따라 막이미지가 X로 평가된 것의 예들을 나타낸다.
도 3은, 본 발명의 실험예에 따라 막이미지가 O로 평가된 것의 예를 나타낸다. 1 schematically shows a method for measuring film flatness according to an experimental example of the present invention.
2 shows examples of membrane images evaluated as X according to an experimental example of the present invention.
3 shows an example in which the membrane image is evaluated as O according to the experimental example of the present invention.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail in order to help the understanding of the present invention.
용어의 정의Definition of Terms
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, styrenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isooxazolyl group, tiadiia A sleepy group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
화학식 1로 표시되는 화합물Compound represented by Formula 1
상기 화학식 1로 표시되는 화합물은, 유기 발광 소자 내의 기능층을 구성하는 물질이다. 또한, 용매와의 친화성이 높아 용매 선택성(orthogonality)을 가지며, 상기 화합물을 포함하는 유기물층 외에 다른 층을 용액 공정으로 형성할 시 사용하는 용매에 대하여 내성을 가져, 다른 층으로 이동을 방지할 수 있다. 또한, 이를 포함하는 유기 발광 소자는 낮은 구동전압, 높은 발광효율 및 높은 수명 특성을 가질 수 있다.The compound represented by Formula 1 is a material constituting the functional layer in the organic light emitting device. In addition, it has a high affinity for the solvent, has solvent selectivity (orthogonality), and has resistance to the solvent used when forming another layer in a solution process in addition to the organic layer containing the compound, so that migration to another layer can be prevented. have. In addition, the organic light emitting device including the same may have low driving voltage, high luminous efficiency, and high lifespan characteristics.
바람직하게는, A는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, A is any one selected from the group consisting of:
상기에서, In the above,
T1은 수소; 또는 치환 또는 비치환된 C1-6 알킬이고,T 1 is hydrogen; Or substituted or unsubstituted C 1-6 alkyl,
T2 내지 T4는 각각 독립적으로 치환 또는 비치환된 C1-6 알킬이다. T 2 to T 4 are each independently substituted or unsubstituted C 1-6 alkyl.
바람직하게는, L은 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, L is any one selected from the group consisting of:
상기에서, In the above,
R은 각각 독립적으로 수소, 또는 C1-10 알킬이다. Each R is independently hydrogen or C 1-10 alkyl.
바람직하게는, L1 내지 L4는 각각 독립적으로 C1-10 알킬렌, 또는 하기 화학식 1-A 또는 1-B이다:Preferably, L 1 to L 4 are each independently C 1-10 alkylene, or the following formulas 1-A or 1-B:
[화학식 1-A][Formula 1-A]
[화학식 1-B][Formula 1-B]
상기 화학식 1-A 및 1-B에 있어서,In Chemical Formulas 1-A and 1-B,
R11 내지 R13은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C1-60 알콕시; 치환 또는 비치환된 C6-60 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,R 11 to R 13 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl comprising any one or more heteroatoms selected from the group consisting of N, O and S,
m1 내지 m3는 각각 0 내지 4의 정수이다.m1 to m3 are each an integer of 0-4.
바람직하게는, Ar1 및 Ar2는 서로 동일하고, 페닐, 비페닐릴, 나프틸, 페난쓰레닐, 디메틸플루오레닐, 또는 디페닐플루오레닐이다. Preferably, Ar 1 and Ar 2 are the same as each other and are phenyl, biphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, or diphenylfluorenyl.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 하기와 같다:Representative examples of the compound represented by Formula 1 are as follows:
한편, 상기 화학식 1로 표시되는 화합물은 하기 반응식 1과 같은 방법으로 제조할 수 있다.Meanwhile, the compound represented by Chemical Formula 1 may be prepared in the same manner as in Scheme 1 below.
[반응식 1][Scheme 1]
상기 반응식 1에서, Y'를 제외한 나머지 정의는 앞서 정의한 바와 같으며, Y'는 할로겐이고, 바람직하게는 브로모, 또는 클로로이다. 상기 반응식 1은 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. In Reaction Scheme 1, definitions other than Y 'are as defined above, and Y' is halogen, preferably bromo, or chloro. Reaction Scheme 1 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be modified as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.
바람직하게는, 본 발명에 따른 잉크 조성물에서, 상기 화학식 1로 표시되는 화합물은 0.1 내지 10 wt%로 포함되고, 보다 바람직하게는 0.1 내지 5 wt%, 0.1 내지 2 wt%로 포함된다. Preferably, in the ink composition according to the present invention, the compound represented by Formula 1 is included in 0.1 to 10 wt%, more preferably 0.1 to 5 wt%, and 0.1 to 2 wt%.
한편, 본 발명에 따른 잉크 조성물은, 상기 화학식 1로 표시되는 화합물 외에 p 도핑 물질을 추가로 포함한다. 상기 p 도핑 물질이란, 호스트 물질을 p 반도체 특성을 갖도록 하는 물질을 의미한다. p 반도체 특성이란 HOMO(highest occupied molecular orbital) 에너지 준위로 정공을 주입받거나 수송하는 특성 즉, 정공의 전도도가 큰 물질의 특성을 의미한다.Meanwhile, the ink composition according to the present invention further includes a p-doped material in addition to the compound represented by Formula 1 above. The p-doped material means a material that makes the host material have p-semiconductor properties. The p-semiconductor property means a property in which holes are injected or transported at a HOMO (highest occupied molecular orbital) energy level, that is, a property of a material having high hole conductivity.
바람직하게는, 상기 p 도핑 물질은 하기 화학식 A 내지 F 중 어느 하나로 표시될 수 있다. Preferably, the p-doped material may be represented by any one of the following formulas A to F.
[화학식 A][Formula A]
[화학식 B][Formula B]
[화학식 C][Formula C]
[화학식 D][Formula D]
[화학식 E][Formula E]
[화학식 F][Formula F]
바람직하게는, 상기 p 도핑 물질의 함량은 상기 화학식 1로 표시되는 화합물 대비 0 중량% 내지 50 중량%이다.Preferably, the content of the p-doped material is 0% to 50% by weight relative to the compound represented by Chemical Formula 1.
용매menstruum
상기 화학식 1로 표시되는 화합물을 용액 공정으로 기능층을 형성할 수 있는데, 최근에는 용액 공정 중에서도 잉크젯 프린팅(inkjet printing) 공정이 가장 많이 검토되고 있다. 잉크젯 프린팅 공정은 미세 drop을 토출하기 때문에, 재료의 소모량을 최소화할 수 있을 뿐만 아니라 정밀 패턴이 가능하다는 이점이 있다. The compound represented by Chemical Formula 1 may form a functional layer through a solution process. Recently, among the solution processes, an inkjet printing process has been most frequently studied. Since the inkjet printing process discharges a fine drop, it has the advantage of not only minimizing the consumption of material but also enabling a precise pattern.
용액 공정으로 평탄한 기능층을 제조하기 위해서는 기본적으로 잉크의 공정성과 막 표면 이미지, 막 평탄성을 동시에 확보해야 한다. 잉크 조성물은 대부분 용매로 이루어져 있으며(최소 90%, 최대 99.9%), 용매에 의해 잉크 물성이 결정되기 때문에 용매의 선택이 무엇보다 중요하다.In order to manufacture a flat functional layer by a solution process, it is necessary to secure the processability of the ink, the film surface image, and the film flatness at the same time. The ink composition is mostly composed of a solvent (min 90%, max 99.9%), and the choice of the solvent is most important because the ink properties are determined by the solvent.
잉크의 공정성은 잉크젯 장비의 노즐에서 잉크가 마르는 현상 없이 안정적으로 토출될 수 있는 특성이며, 이를 위해서는 증기압이 충분히 낮은 고비점 특성을 갖는 용매를 선택해야 한다. 잉크 막 이미지는 기능층 제조 과정에서 건조 과정을 거칠 때, 석출/상분리 없이 표면이 균일한 막 이미지를 형성하는 특성이며, 이를 위해서는 기능층의 재료를 충분히 용해할 수 있는 높은 용해도 특성과 진공 건조에 적합한 건조 특성을 갖는 용매를 선택해야 한다. 또한, 막 이미지와 동시에 요구되는 특성은 막 평탄성이다. 기능층은 여러 개의 적층 구조로 형성되기 때문에 각 기능층이 평탄하게 형성되어야, 완성된 유기 발광 소자에서 안정적인 발광 특성을 낼 수 있다. 따라서, 잉크 조성물에서 잉크 공정성, 막 이미지, 및 막 평탄성을 동시에 확보할 수 있는 용매 선택이 중요하다. 이에 본 발명에서는 상술한 용매를 사용함으로써, 상기의 특성을 구현할 수 있다. The fairness of the ink is a characteristic that the ink can be stably discharged from the nozzle of the inkjet equipment without drying, and for this, it is necessary to select a solvent having a high boiling point characteristic with a sufficiently low vapor pressure. The ink film image is a characteristic of forming a film image with a uniform surface without precipitation / phase separation when undergoing a drying process in the process of manufacturing a functional layer, and for this purpose, it has high solubility characteristics and vacuum drying to sufficiently dissolve the material of the functional layer. Solvents with suitable drying properties should be selected. In addition, a characteristic required at the same time as the film image is film flatness. Since the functional layer is formed of a plurality of stacked structures, each functional layer must be formed flat, so that stable light emission characteristics can be obtained in the completed organic light emitting device. Therefore, it is important to select a solvent capable of simultaneously securing ink fairness, film image, and film flatness in the ink composition. Therefore, in the present invention, the above-described characteristics can be realized by using the above-described solvent.
본 발명에서 사용되는 용매는 log P가 1.5 이상이고, 분자 부피가 190 cm3/mole 이하라는 특징이 있다. The solvent used in the present invention has a characteristic that the log P is 1.5 or more and the molecular volume is 190 cm 3 / mole or less.
상기 "log P"란, 물과 옥탄올의 분배계수를 의미하는 것으로, 실험적으로 측정하거나 또는 이론적으로 예측 가능하며, 각 용매의 고유 물성이다. 상기 용매의 log P가 1.5 미만인 경우에는, 잉크 조성물을 건조하는 과정에서 앞서 설명한 화학식 1로 표시되는 화합물이 결정으로 석출되는 문제가 있다. 한편, 상기 용매의 log P의 상한은 특별히 제한되지 않으나, 바람직하게는 11.5 이하, 11.0 이하, 10.5 이하, 또는 10.0 이하이다. The "log P" means a partition coefficient of water and octanol, which can be experimentally measured or theoretically predicted, and is the intrinsic physical property of each solvent. When the log P of the solvent is less than 1.5, there is a problem in that the compound represented by Formula 1 described above is precipitated as crystals in the process of drying the ink composition. On the other hand, the upper limit of the log P of the solvent is not particularly limited, but is preferably 11.5 or less, 11.0 or less, 10.5 or less, or 10.0 or less.
상기 "분자 부피"란, 분자 1몰이 차지하는 부피를 의미하는 것으로, 본 발명에서는 상온(25℃) 및 상압(1 기압)에서 측정한 값을 의미하며, 각 용매의 고유 물성이다. 상기 용매의 분자 부피가 190 cm3/mole 초과인 경우에는, 잉크 조성물을 건조하는 과정에서 용매의 확산 속도가 낮기 때문에, 앞서 설명한 화학식 1로 표시되는 화합물이 석출되는 문제가 있다. 한편, 상기 용매의 분자 부피의 하한은 특별히 제한되지 않으나, 바람직하게는 100 cm3/mole 이상, 105 cm3/mole 이상, 또는 100 cm3/mole 이상이다. The "molecular volume" means a volume occupied by one mole of a molecule, and in the present invention, means a value measured at room temperature (25 ° C) and normal pressure (1 atm), and is an intrinsic property of each solvent. When the molecular volume of the solvent is more than 190 cm 3 / mole, the diffusion rate of the solvent is low in the process of drying the ink composition, and thus there is a problem that the compound represented by Chemical Formula 1 is precipitated. Meanwhile, the lower limit of the molecular volume of the solvent is not particularly limited, but is preferably 100 cm 3 / mole or more, 105 cm 3 / mole or more, or 100 cm 3 / mole or more.
또한, 본 발명에 따른 용매는 단일 용매일 수 있으며, 혼합 용매일 수 있다. 혼합 용매인 경우에는, 2종 이상의 용매가 이하 수학식 1 및 2의 방법으로 계산된 Log P 및 분자 부피가 상술한 범위를 만족하는 것을 의미한다. Further, the solvent according to the present invention may be a single solvent or a mixed solvent. In the case of a mixed solvent, it means that two or more solvents satisfy the above-described range of the log P and the molecular volume calculated by the methods of Equations 1 and 2 below.
[수학식 1][Equation 1]
상기 수학식 1에서, In Equation 1,
wi는 i번째 용매의 질량비이고,w i is the mass ratio of the i th solvent,
logPi는 i번째 용매의 logP이고,logP i is logP of the i-th solvent,
[수학식 2][Equation 2]
상기 수학식 2에서, In Equation 2,
wi는 i번째 용매의 질량비이고,w i is the mass ratio of the i th solvent,
MolVoli는 i번째 용매의 분자부피이다. MolVol i is the molecular volume of the i-th solvent.
바람직하게는, 상기 용매는, 1-메톡시-2-니트로벤젠, (페녹시메틸)-옥시란, 2-(2-메틸페닐)에탄올(Peomosa), n-헥사노익애시드, 2,3-크실리딘, 2,6-크실리딘, 3,5-크실리딘, 2-헥실옥시에탄올, 벤젠프로판올, m-디메톡시벤젠, 3-하이드록시톨루엔, 1,2-디메톡시벤젠, 1-(2-하이드록시페닐)에탄올, 벤조싸이아졸, a,a-디메틸벤젠에탄올, 페닐아세트알데하이드디메틸아세탈, 4-메틸벤즈알데하이드, 3-메틸벤조니트릴, 4-메틸-2-페닐-1,3-디옥솔란, n-에틸아닐린, p-아니스알데하이드디메틸아세탈, 4-에틸-2-메톡시페놀, 2-사이클로펜틸사이클로펜타논, 2,3-디하이드로-2,2-디메틸-7-하이드록시벤조퓨란, 1,2,3,4-테트라하이드로퀴놀린, n-헵타노익애시드, 2,4-디메틸페놀, 사이클로헥산에탄올, 2-에틸페놀, m-에틸페놀, 1-메틸-1h-인돌, 6-메틸퀴놀린, 4-메틸아니솔, o-이소프로필페놀, 1,2-디메틸-3-니트로벤젠, 4-니트로-m-크실렌, 카프릴릭애시드, 2-에틸니트로벤젠, 3-페녹시벤질알코올, 2-(1-사이클로헥실)사이클로헥사논, o-t-부틸페놀, 노나노니트릴, 2-메틸-5-(1-메틸에틸)페놀, 1-메톡시나프탈렌, 노나노익애시드, 1-노나놀, 6-메톡시-1,2,3,4-테트라하이드로나프탈렌, 테트랄린, 1-메틸나프탈렌, 1,2,3,4-테트라메틸벤젠, 디페닐에테르, 디페닐설파이드, 3-페녹시톨루엔, 사이클로헥실벤젠, 사이클로데칸, 에틸 4-에톡시벤조에이트, 이소부틸 살리실레이트, 벤조익 애시드 부틸 에스터, 에틸 4-메톡시벤조에이트, b-페닐에틸아세테이트, 에틸 페닐아세테이트, 에틸 p-톨루에이트, 에틸 벤조에이트, 아세틱 애시드 페닐메틸 에스터, 2-하이드록시-벤조익 애시드 메틸 에스터, 3,4-디하이드로-2h-1-벤조피란-2-온, 및 이의 혼합 용매이다. Preferably, the solvent is 1-methoxy-2-nitrobenzene, (phenoxymethyl) -oxirane, 2- (2-methylphenyl) ethanol (Peomosa), n-hexanoic acid, 2,3-x Silydine, 2,6-xylidine, 3,5-xylidine, 2-hexyloxyethanol, benzenepropanol, m-dimethoxybenzene, 3-hydroxytoluene, 1,2-dimethoxybenzene, 1- (2-hydroxyphenyl) ethanol, benzothiazole, a, a-dimethylbenzeneethanol, phenylacetaldehydedimethylacetal, 4-methylbenzaldehyde, 3-methylbenzonitrile, 4-methyl-2-phenyl-1,3 -Dioxolane, n-ethylaniline, p-anisaldehydedimethylacetal, 4-ethyl-2-methoxyphenol, 2-cyclopentylcyclopentanone, 2,3-dihydro-2,2-dimethyl-7-hydride Roxybenzofuran, 1,2,3,4-tetrahydroquinoline, n-heptanoic acid, 2,4-dimethylphenol, cyclohexaneethanol, 2-ethylphenol, m-ethylphenol, 1-methyl-1h-indole , 6-methylquinoline, 4-methylanisole, o-isopropylphenol, 1,2- Methyl-3-nitrobenzene, 4-nitro-m-xylene, caprylic acid, 2-ethylnitrobenzene, 3-phenoxybenzyl alcohol, 2- (1-cyclohexyl) cyclohexanone, ot-butylphenol, Nonanonitrile, 2-methyl-5- (1-methylethyl) phenol, 1-methoxynaphthalene, nonanoic acid, 1-nonanol, 6-methoxy-1,2,3,4-tetrahydronaphthalene , Tetralin, 1-methylnaphthalene, 1,2,3,4-tetramethylbenzene, diphenyl ether, diphenylsulfide, 3-phenoxytoluene, cyclohexylbenzene, cyclodecane, ethyl 4-ethoxybenzoate , Isobutyl salicylate, benzoic acid butyl ester, ethyl 4-methoxybenzoate, b-phenylethyl acetate, ethyl phenylacetate, ethyl p-toluate, ethyl benzoate, acetic acid phenylmethyl ester, 2- Hydroxy-benzoic acid methyl ester, 3,4-dihydro-2h-1-benzopyran-2-one, and mixed solvents thereof.
잉크 조성물Ink composition
상술한 본 발명에 따른 잉크 조성물은 유기 발광 소자의 기능층 제조에 사용할 수 있다. 상기 잉크 조성물을 이용하여 용액 공정으로 유기 발광 소자의 기능층 제조에 사용할 수 있으며, 특히 잉크젯 공정을 적용할 수 있다. The ink composition according to the present invention described above can be used for manufacturing a functional layer of an organic light emitting device. The ink composition may be used to prepare a functional layer of an organic light emitting device by a solution process, and in particular, an inkjet process may be applied.
상기 잉크젯 공정은 상술한 본 발명에 따른 잉크 조성물을 사용하는 것을 제외하고는 당업계에 사용되는 방법을 사용할 수 있다. 일례로, 상기 잉크 조성물을 토출하여 잉크막을 형성하는 단계; 및 상기 잉크막을 건조하는 단계를 포함할 수 있다. 또한, 상술한 화학식 1로 표시되는 화합물은 열 또는 광에 의하여 가교 가능한 작용기를 포함하고 있기 때문에, 상기 단계 이후에 열처리 또는 광처리하는 단계를 추가로 포함할 수 있다. The inkjet process may use a method used in the art, except for using the ink composition according to the present invention described above. In one example, discharging the ink composition to form an ink film; And drying the ink film. In addition, since the compound represented by Chemical Formula 1 includes a functional group capable of crosslinking by heat or light, it may further include a step of heat treatment or light treatment after the step.
한편, 상기 잉크 조성물로 형성할 수 있는 기능층은 유기 발광 소자의 정공주입층, 정공수송층 및 발광층일 수 있다. 또한, 상기 기능층을 제외하고는 당업계에서 사용되는 유기 발광 소자의 구성 및 제조 방법을 적용할 수 있기 때문에, 본 명세서에서는 상세한 설명을 생략한다. Meanwhile, the functional layer that can be formed from the ink composition may be a hole injection layer, a hole transport layer, and a light emitting layer of an organic light emitting device. In addition, since the configuration and manufacturing method of the organic light emitting device used in the art can be applied except for the functional layer, a detailed description is omitted herein.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐, 이에 의해 본 발명의 내용이 한정되는 것은 아니다.Hereinafter, preferred embodiments are provided to help understanding of the present invention. However, the following examples are only provided to more easily understand the present invention, and the contents of the present invention are not limited thereby.
[[ 제조예Manufacturing example ]]
제조예Manufacturing example 1: 화합물 3의 제조 1: Preparation of compound 3
상기 화합물 3-1(1.58 g, 3.74 mmol), N4,N4'-디페닐-[1,1'-비페닐]-4,4'-디아민(572 mg, 1.7 mmol), 및 소듐 t-부톡사이드(980 mg, 10.2 mmol)이 든 플라스크에 톨루엔을 넣었다. 90℃ 오일 배쓰에 플라스크를 담근 뒤, Pd(PtBu3)2(43 mg, 0.085 mmol)를 넣고 1시간 동안 반응시켰다. 물을 넣어 반응을 중지시키고 디클로로메탄으로 추출한 다음, MgSO4로 유기층을 건조시켰다. 유기 용매를 진공 회전 농축기를 사용하여 제거한 후, 잔여물을 컬럼 크로마토그라피로 정제하여 상기 화합물 3(수율 55%)을 얻었다. Compound 3-1 (1.58 g, 3.74 mmol), N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (572 mg, 1.7 mmol), and sodium t-butok Toluene was added to the flask containing the side (980 mg, 10.2 mmol). After soaking the flask in a 90 ° C oil bath, Pd (PtBu 3 ) 2 (43 mg, 0.085 mmol) was added and reacted for 1 hour. The reaction was stopped by adding water, extracted with dichloromethane, and then the organic layer was dried over MgSO 4 . After removing the organic solvent using a vacuum rotary concentrator, the residue was purified by column chromatography to obtain the compound 3 (yield 55%).
MS[M+H]+= 1022MS [M + H] + = 1022
제조예Manufacturing example 2: 화합물 1의 제조 2: Preparation of compound 1
화합물 3-1 대신 화합물 1-1을 사용하고, N4,N4'-디페닐-[1,1'-비페닐]-4,4'-디아민 대신 N4,N4'-디(비페닐-4-일)비페닐-4,4'-디아민을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법으로 화합물 1을 제조하였다. Compound 1-1 is used instead of compound 3-1, and N4, N4'-di (biphenyl-4-) is used instead of N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine. 1) Compound 1 was prepared in the same manner as in Preparation Example 1, except that biphenyl-4,4'-diamine was used.
MS[M+H]+= 1374MS [M + H] + = 1374
제조예Manufacturing example 3: 화합물 2의 제조 3: Preparation of compound 2
화합물 3-1 대신 화합물 2-1을 사용하고, N4,N4'-디페닐-[1,1'-비페닐]-4,4'-디아민 대신 N4,N4'-디(비페닐-4-일)비페닐-4,4'-디아민을 사용한 것을 제외하고는, 상기 제조예 1과 동일한 방법으로 화합물 2를 제조하였다. Compound 2-1 is used instead of compound 3-1, and N4, N4'-di (biphenyl-4-) is used instead of N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine. 1) Compound 2 was prepared in the same manner as in Production Example 1, except that biphenyl-4,4'-diamine was used.
MS[M+H]+= 1342MS [M + H] + = 1342
제조예Manufacturing example 4: 화합물 4의 제조 4: Preparation of compound 4
1) 중간체 4-1의 제조1) Preparation of Intermediate 4-1
500 ml 둥근 플라스크에 2-브로모-9-페닐-9H-플루오렌-9-올(50 g, 148.3 mmol, 1.0 eq)과 페놀(41.8 g, 444.9 mmol, 3.0 eq)을 넣고 메탄술폰산(200 ml, 0.74 M)에 녹였다. 환류 하에서 밤새 교반시켰다. 이후 포화 NaHCO3 수용액으로 반응을 중지시키고 에틸아세테이트로 유기층을 추출하였다. 황산마그네슘으로 유기층을 건조시킨 뒤 용매를 제거하고 컬럼 크로마토그래피로 정제하여 중간체 화합물 4-1을 얻었다.2-bromo-9-phenyl-9H-fluorene-9-ol (50 g, 148.3 mmol, 1.0 eq) and phenol (41.8 g, 444.9 mmol, 3.0 eq) were added to a 500 ml round flask and methanesulfonic acid (200 ml, 0.74 M). It was stirred under reflux overnight. Then, the reaction was stopped with an aqueous saturated NaHCO 3 solution, and the organic layer was extracted with ethyl acetate. After drying the organic layer with magnesium sulfate, the solvent was removed and purified by column chromatography to obtain intermediate compound 4-1.
2) 중간체 4-2의 제조2) Preparation of Intermediate 4-2
500 ml 둥근 플라스크에 중간체 4-1(30 g, 63.9 mmol, 1.0 eq)과 세슘 카보네이트(41.6 g, 127.8 mmol, 2.0 eq)을 DMF(120 ml, 0.5 M)에 녹인 후 50℃로 승온하여 교반시켰다. 이후 4-비닐벤질클로라이드(9.15 ml, 9.75 g, 1.0 eq)를 넣고 60℃에서 교반하였다. 상온까지 식힌 후 물을 넣어 반응을 중단시킨 후 에틸 아세테이트를 이용하여 유기층을 추출하였다. 유기층을 분리하여 황산 마그네슘으로 건조시킨 뒤 용매를 제거하고 컬럼 크로마토그래피로 정제하여 중간체 화합물 4-2를 얻었다.In a 500 ml round flask, intermediate 4-1 (30 g, 63.9 mmol, 1.0 eq) and cesium carbonate (41.6 g, 127.8 mmol, 2.0 eq) were dissolved in DMF (120 ml, 0.5 M), heated to 50 ° C. and stirred. Ordered. Then 4-vinyl benzyl chloride (9.15 ml, 9.75 g, 1.0 eq) was added and stirred at 60 ° C. After cooling to room temperature, water was added to stop the reaction, and then an organic layer was extracted using ethyl acetate. The organic layer was separated, dried over magnesium sulfate, and the solvent was removed and purified by column chromatography to obtain intermediate compound 4-2.
3) 화합물 4의 제조3) Preparation of compound 4
250 ml 둥근 플라스크에 중간체 4-2(12.0 g, 20.49 mmol, 2.05 eq), N4,N4'-디페닐-[1,1'-비페닐]-4,4'-디아민(3.36 g, 10.0 mmol, 1.0 eq), NaOtBu(3.36 g, 34.99 mmol, 3.5 eq), Pd(PtBu3)2(255 mg, 0.5 mmol, 0.05 eq)를 톨루엔(100 ml)에 녹인 후 교반하여 질소 분위기 하에 교반하여 반응시켰다. 이후 반응이 종결되면 물과 에틸아세테이트로 work-up하고, 유기층을 분리하여 건조시킨 뒤 필터하였다. 이후 용매를 회전 감압증발기로 제거하였다. 얻어진 crude 물질을 칼럼 크로마토그래피로 정제하고 용매를 제거하여 화합물 4(흰색 고체)을 수득하였다.Intermediate 4-2 (12.0 g, 20.49 mmol, 2.05 eq), N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (3.36 g, 10.0 mmol) in a 250 ml round flask , 1.0 eq), NaOtBu (3.36 g, 34.99 mmol, 3.5 eq), Pd (PtBu 3 ) 2 (255 mg, 0.5 mmol, 0.05 eq) was dissolved in toluene (100 ml), stirred and stirred under nitrogen atmosphere for reaction Ordered. Then, when the reaction was completed, work-up was performed with water and ethyl acetate, and the organic layer was separated and dried before filtering. Thereafter, the solvent was removed using a rotary vacuum evaporator. The crude material obtained was purified by column chromatography and the solvent was removed to obtain compound 4 (white solid).
MS[M+H]+= 1234MS [M + H] + = 1234
제조예Manufacturing example 5: 화합물 5의 제조 5: Preparation of compound 5
1) 중간체 5-1의 제조1) Preparation of Intermediate 5-1
500 ml 둥근 플라스크에 4-(2-브로모-9-(4-(tert-부틸)페닐)-9H-플루오렌-9-일)페놀(50 g, 106.50 mmol, 1.0 eq), 4-브로모벤즈알데하이드(23.6 g, 127.8 mmol, 1.2 eq), 포타슘 카보네이트(44.2 g, 319.50 mmol, 3.0 eq)을 넣고 드라이 피리딘(200 ml, 0.5 M)에 녹였다. 이후 산화구리(II)(17.0 g, 213.0 mmol, 2 eq)를 천천히 첨가하고 120℃로 승온하여 환류 하에서 반응을 진행시켰다. 반응이 끝나면 포화 NaHCO3 수용액으로 반응을 중지시키고 에틸 아세테이트로 유기층을 추출하였다. 황산마그네슘으로 유기층을 건조시킨 뒤 용매를 제거하여 얻은 crude를 디클로로메탄에 녹여 에탄올에 침전을 잡음으로써 고체인 중간체 화합물 5-1을 얻었다.4- (2-bromo-9- (4- (tert-butyl) phenyl) -9H-fluoren-9-yl) phenol (50 g, 106.50 mmol, 1.0 eq), 4-bro in a 500 ml round flask Mobenzaldehyde (23.6 g, 127.8 mmol, 1.2 eq) and potassium carbonate (44.2 g, 319.50 mmol, 3.0 eq) were added and dissolved in dry pyridine (200 ml, 0.5 M). After that, copper (II) oxide (17.0 g, 213.0 mmol, 2 eq) was slowly added and heated to 120 ° C to proceed the reaction under reflux. When the reaction was over, the reaction was stopped with saturated aqueous NaHCO 3 solution, and the organic layer was extracted with ethyl acetate. After drying the organic layer with magnesium sulfate, the crude obtained by removing the solvent was dissolved in dichloromethane and precipitated in ethanol to obtain a solid intermediate compound 5-1.
2) 중간체 5-2의 제조2) Preparation of Intermediate 5-2
메틸트리페닐포스포늄 브로마이드(12.46 g, 34.87 mmol, 2.0 eq)가 담긴 둥근 플라스크에 무수 테트라하이드로퓨란(50 ml, 0.2 M)을 넣고 아이스 배쓰에 둥근 플라스크를 담궜다. 포타슘 tert-부톡사이드(3.9 g, 34.87 mmol, 2.0 eq)를 한번에 넣고 아이스 배쓰에서 20분간 교반시켰다. 중간체 화합물 5-1(10.0 g, 17.44 mmol, 1.0 eq)를 테트라하이드로퓨란(30 ml)에 녹인 후 적하 깔때기를 이용하여 점차적으로 혼합물에 첨가하였다. 이후 테트라하이드로퓨란(10 ml)으로 둥근 플라스크와 깔때기를 씻어주며 마저 넣어주었다. 물(50 ml)을 넣어 반응을 종료시키고, 에틸 아세테이트로 유기층을 추출하였다. 황산 마그네슘으로 유기층을 건조시킨 뒤 용매를 제거하고 컬럼 크로마토그래피로 정제하여, 화합물 5-2를 얻었다.Methyl triphenylphosphonium bromide (12.46 g, 34.87 mmol, 2.0 eq) was placed in anhydrous tetrahydrofuran (50 ml, 0.2 M) in a round flask and the round flask was immersed in an ice bath. Potassium tert-butoxide (3.9 g, 34.87 mmol, 2.0 eq) was added at once and stirred in an ice bath for 20 minutes. Intermediate compound 5-1 (10.0 g, 17.44 mmol, 1.0 eq) was dissolved in tetrahydrofuran (30 ml) and gradually added to the mixture using a dropping funnel. Afterwards, a round flask and a funnel were washed with tetrahydrofuran (10 ml) and even put. The reaction was terminated by adding water (50 ml), and the organic layer was extracted with ethyl acetate. After drying the organic layer with magnesium sulfate, the solvent was removed and purified by column chromatography to obtain compound 5-2.
3) 화합물 5의 제조3) Preparation of compound 5
250 ml 둥근 플라스크에 중간체 화합물 5-2(10.0 g, 17.50 mmol, 2.05 eq), N4,N4'-디페닐-[1,1'-비페닐]-4,4'-디아민(2.87 g, 8.53 mmol, 1.0 eq), NaOtBu(2.87 g, 29.86 mmol, 3.5 eq), Pd(PtBu3)2(218.0 mg, 0.43 mmol, 0.05 eq)를 톨루엔(90 ml)에 녹인 후 교반하여 질소 분위기 하에 교반하여 반응시켰다. 이후 반응이 종결되면 물과 에틸 아세테이트로 work-up하고, 유기층을 분리하여 건조시킨 뒤 필터하였다. 이후 용매를 회전 감압증발기로 제거하였다. 얻어진 crude 물질을 컬럼 크로마토그래피로 정제하고 용매를 제거하여 화합물 5(흰색 고체)을 수득하였다.Intermediate compound 5-2 (10.0 g, 17.50 mmol, 2.05 eq), N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (2.87 g, 8.53) in a 250 ml round flask mmol, 1.0 eq), NaOtBu (2.87 g, 29.86 mmol, 3.5 eq), Pd (PtBu 3 ) 2 (218.0 mg, 0.43 mmol, 0.05 eq) was dissolved in toluene (90 ml), stirred and stirred under a nitrogen atmosphere. To react. Then, when the reaction was completed, work-up was performed with water and ethyl acetate, and the organic layer was separated and dried before filtering. Thereafter, the solvent was removed using a rotary vacuum evaporator. The crude material obtained was purified by column chromatography and the solvent was removed to obtain compound 5 (white solid).
MS[M+H]+= 1318MS [M + H] + = 1318
제조예Manufacturing example 6: 화합물 6의 제조 6: Preparation of compound 6
1) 중간체 6-1의 제조1) Preparation of Intermediate 6-1
250 ml 둥근 플라스크에 4-(2-브로모-9-(p-톨릴)-9H-플루오렌-9-일)페놀(15 g, 35.1 mmol, 1.0 eq), 포타슘 카보네이트(14.6 g, 105.3 mmol, 3 eq), 요오드화 구리(I)(334.3 mg, 1.76 mmol, 0.05 eq), 1-부틸이미다졸(4.4 g, 35.1 mmol, 1.0 eq)를 넣고 톨루엔(175 ml)에 녹였다. 환류 장치를 설치한 뒤 120℃로 가열하여 교반하며 반응을 진행시켰다. 반응이 종결되면 포화 NaHCO3 수용액으로 반응을 중지시키고 물과 에틸 아세테이트로 work-up하였다. 유기층을 분리하여 MgSO4를 통해 건조시킨 뒤 필터하였다. 이후 용매를 회전 감압증발기로 제거하고, 얻어진 crude 물질을 컬럼 크로마토그래피로 정제하여 중간체 화합물 6-1을 얻었다.4- (2-bromo-9- (p-tolyl) -9H-fluoren-9-yl) phenol (15 g, 35.1 mmol, 1.0 eq), potassium carbonate (14.6 g, 105.3 mmol) in a 250 ml round flask , 3 eq), copper (I) iodide (334.3 mg, 1.76 mmol, 0.05 eq), 1-butylimidazole (4.4 g, 35.1 mmol, 1.0 eq) was added and dissolved in toluene (175 ml). After installing the reflux device, the reaction was carried out by heating to 120 ° C. and stirring. When the reaction was completed, the reaction was stopped with saturated aqueous NaHCO 3 solution, and work-up was performed with water and ethyl acetate. The organic layer was separated, dried over MgSO 4 and filtered. Thereafter, the solvent was removed by a rotary evaporator, and the crude material obtained was purified by column chromatography to obtain Intermediate Compound 6-1.
2) 화합물 6의 제조2) Preparation of compound 6
250 ml 둥근 플라스크에 중간체 화합물 6-1(10.0 g ,18.89 mmol, 2.05 eq), N4,N4'-디페닐-[1,1'-비페닐]-4,4'-디아민(3.10 g, 9.21 mmol, 1.0 eq), NaOtBu(3.10 g, 32.24 mmol, 3.5 eq), Pd(PtBu3)2(235.1 mg, 0.46 mmol, 0.05 eq)를 톨루엔(120 ml)에 녹인 후 질소 분위기 하에 교반하여 반응시켰다. 이후 반응이 종결되면 물과 에틸아세테이트로 work-up하고, 유기층을 분리하여 건조시킨 뒤 필터하였다. 이후 용매를 회전 감압증발기로 제거하였다. 얻어진 crude 물질을 컬럼 크로마토그래피로 정제하고 용매를 제거하여 화합물 6(흰색 고체)을 수득하였다.Intermediate compound 6-1 (10.0 g, 18.89 mmol, 2.05 eq), N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (3.10 g, 9.21) in a 250 ml round flask mmol, 1.0 eq), NaOtBu (3.10 g, 32.24 mmol, 3.5 eq), Pd (PtBu 3 ) 2 (235.1 mg, 0.46 mmol, 0.05 eq) was dissolved in toluene (120 ml) and stirred under nitrogen atmosphere to react. . Then, when the reaction was completed, work-up was performed with water and ethyl acetate, and the organic layer was separated and dried before filtering. Thereafter, the solvent was removed using a rotary vacuum evaporator. The crude material obtained was purified by column chromatography and the solvent was removed to obtain compound 6 (white solid).
MS[M+H]+= 1234MS [M + H] + = 1234
실시예Example 및 And 비교예Comparative example
하기 표 1과 같이, 기능층 물질로서 앞서 제조한 화합물 1, 및 p-도핑 물질로서 하기 화합물 B가 각각 1.6 wt% 및 0.4 wt%가 되도록 각 용매에 용해시켜 잉크 조성물을 제조하였다. As shown in Table 1 below, compound 1 prepared as a functional layer material and compound B as a p-doped material were dissolved in each solvent so as to be 1.6 wt% and 0.4 wt%, respectively, to prepare an ink composition.
[화합물 B][Compound B]
상기 제조한 잉크 조성물을 Dimatix Materials Cartridge(Fujifilm사)의 head에 주입하고, 각 픽셀에 9 방울씩 잉크 방울을 토출하였다(도 1 참조). 이어 진공 건조 및 열처리하여 용매를 제거하였고, 최종 잉크 막을 형성하였다. 제조된 잉크막에 대하여 막이미지(Optical microscope로 확인), 및 profile(optical profiler로 확인, Zygo 장비 사용)을 관찰하여 이하와 같이 평가하였다. The prepared ink composition was injected into the head of a Dimatix Materials Cartridge (Fujifilm), and 9 drops of ink were discharged to each pixel (see FIG. 1). Then, the solvent was removed by vacuum drying and heat treatment, and a final ink film was formed. The prepared ink film was evaluated as follows by observing the film image (checked with an optical microscope) and profile (checked with an optical profiler, using Zygo equipment).
X: 픽셀 내에 알갱이 같은 이물이나, 반짝거리는 점, 흰점 등이 관찰되는 경우(도 2 참조) X: When foreign matter such as granules, twinkling dots, white dots, etc. are observed in the pixel (see FIG. 2).
O: 상기의 경우가 관찰되지 않는 경우(도 3 참조)O: When the above case was not observed (see Fig. 3)
물질Functional layer
matter
물질p-doping
matter
Claims (8)
상기 용매는, log P가 1.5 이상이고, 분자 부피가 190 cm3/mole 이하인,
잉크 조성물:
[화학식 1]
상기 화학식 1에서,
L 및 L1 내지 L4는 각각 독립적으로 치환 또는 비치환된 C1-60 알킬렌; 치환 또는 비치환된 C6-60 아릴렌이고,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
R1 내지 R4는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1-60 알킬, 치환 또는 비치환된 C1-60 알콕시, 치환 또는 비치환된 C6-60 아릴, 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
Y1 내지 Y4는 각각 독립적으로 수소, 또는 -X-A이되, 단 Y1 내지 Y4 중 2 이상이 -X-A이며,
X는 단일 결합, O, 또는 S이고,
A는 열 또는 광에 의하여 가교 가능한 작용기이고,
n1 및 n4는 각각 0 내지 4의 정수이고,
n2 및 n3는 각각 0 내지 3의 정수이다.
In the ink composition for an organic light emitting device comprising a compound represented by the formula (1), and a solvent,
The solvent has a log P of 1.5 or more and a molecular volume of 190 cm 3 / mole or less,
Ink composition:
[Formula 1]
In Chemical Formula 1,
L and L 1 to L 4 are each independently substituted or unsubstituted C 1-60 alkylene; Substituted or unsubstituted C 6-60 arylene,
Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
R 1 to R 4 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 1-60 alkoxy, substituted or unsubstituted C 6-60 aryl, or N, O And C 2-60 heteroaryl comprising any one or more heteroatoms selected from the group consisting of S,
Y 1 to Y 4 are each independently hydrogen, or -XA, provided that 2 or more of Y 1 to Y 4 are -XA,
X is a single bond, O, or S,
A is a functional group capable of crosslinking by heat or light,
n1 and n4 are each an integer from 0 to 4,
n2 and n3 are each an integer of 0-3.
A는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
잉크 조성물:
상기에서,
T1은 수소; 또는 치환 또는 비치환된 C1-6 알킬이고,
T2 내지 T4는 각각 독립적으로 치환 또는 비치환된 C1-6 알킬이다.
According to claim 1,
A is any one selected from the group consisting of,
Ink composition:
In the above,
T 1 is hydrogen; Or substituted or unsubstituted C 1-6 alkyl,
T 2 to T 4 are each independently substituted or unsubstituted C 1-6 alkyl.
L은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
잉크 조성물:
상기에서,
R은 각각 독립적으로 수소, 또는 C1-10 알킬이다.
According to claim 1,
L is any one selected from the group consisting of,
Ink composition:
In the above,
Each R is independently hydrogen or C 1-10 alkyl.
L1 내지 L4는 각각 독립적으로 C1-10 알킬렌, 또는 하기 화학식 1-A 또는 1-B인,
잉크 조성물:
[화학식 1-A]
[화학식 1-B]
상기 화학식 1-A 및 1-B에 있어서,
R11 내지 R13은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C1-60 알콕시; 치환 또는 비치환된 C6-60 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
m1 내지 m3는 각각 0 내지 4의 정수이다.
According to claim 1,
L 1 to L 4 are each independently C 1-10 alkylene, or Formula 1-A or 1-B,
Ink composition:
[Formula 1-A]
[Formula 1-B]
In Chemical Formulas 1-A and 1-B,
R 11 to R 13 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl comprising any one or more heteroatoms selected from the group consisting of N, O and S,
m1 to m3 are each an integer of 0-4.
Ar1 및 Ar2는 서로 동일하고, 페닐, 비페닐릴, 나프틸, 페난쓰레닐, 디메틸플루오레닐, 또는 디페닐플루오레닐인,
잉크 조성물.
According to claim 1,
Ar 1 and Ar 2 are the same as each other, and are phenyl, biphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, or diphenylfluorenyl,
Ink composition.
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
잉크 조성물:
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
Ink composition:
상기 용매는 비점이 200℃ 이상인,
잉크 조성물.
According to claim 1,
The solvent has a boiling point of 200 ° C or higher,
Ink composition.
상기 용매는, 1-메톡시-2-니트로벤젠, (페녹시메틸)-옥시란, 2-(2-메틸페닐)에탄올(Peomosa), n-헥사노익애시드, 2,3-크실리딘, 2,6-크실리딘, 3,5-크실리딘, 2-헥실옥시에탄올, 벤젠프로판올, m-디메톡시벤젠, 3-하이드록시톨루엔, 1,2-디메톡시벤젠, 1-(2-하이드록시페닐)에탄올, 벤조싸이아졸, a,a-디메틸벤젠에탄올, 페닐아세트알데하이드디메틸아세탈, 4-메틸벤즈알데하이드, 3-메틸벤조니트릴, 4-메틸-2-페닐-1,3-디옥솔란, n-에틸아닐린, p-아니스알데하이드디메틸아세탈, 4-에틸-2-메톡시페놀, 2-사이클로펜틸사이클로펜타논, 2,3-디하이드로-2,2-디메틸-7-하이드록시벤조퓨란, 1,2,3,4-테트라하이드로퀴놀린, n-헵타노익애시드, 2,4-디메틸페놀, 사이클로헥산에탄올, 2-에틸페놀, m-에틸페놀, 1-메틸-1h-인돌, 6-메틸퀴놀린, 4-메틸아니솔, o-이소프로필페놀, 1,2-디메틸-3-니트로벤젠, 4-니트로-m-크실렌, 카프릴릭애시드, 2-에틸니트로벤젠, 3-페녹시벤질알코올, 2-(1-사이클로헥실)사이클로헥사논, o-t-부틸페놀, 노나노니트릴, 2-메틸-5-(1-메틸에틸)페놀, 1-메톡시나프탈렌, 노나노익애시드, 1-노나놀, 6-메톡시-1,2,3,4-테트라하이드로나프탈렌, 테트랄린, 1-메틸나프탈렌, 1,2,3,4-테트라메틸벤젠, 디페닐에테르, 디페닐설파이드, 3-페녹시톨루엔, 사이클로헥실벤젠, 사이클로데칸, 에틸 4-에톡시벤조에이트, 이소부틸 살리실레이트, 벤조익 애시드 부틸 에스터, 에틸 4-메톡시벤조에이트, b-페닐에틸아세테이트, 에틸 페닐아세테이트, 에틸 p-톨루에이트, 에틸 벤조에이트, 아세틱 애시드 페닐메틸 에스터, 2-하이드록시-벤조익 애시드 메틸 에스터, 3,4-디하이드로-2h-1-벤조피란-2-온, 및 이의 혼합 용매인,
잉크 조성물.The method of claim 7,
The solvent is 1-methoxy-2-nitrobenzene, (phenoxymethyl) -oxirane, 2- (2-methylphenyl) ethanol (Peomosa), n-hexanoic acid, 2,3-xylidine, 2 , 6-Xylidine, 3,5-Xylidine, 2-hexyloxyethanol, benzenepropanol, m-dimethoxybenzene, 3-hydroxytoluene, 1,2-dimethoxybenzene, 1- (2-hydroxy Hydroxyphenyl) ethanol, benzothiazole, a, a-dimethylbenzeneethanol, phenylacetaldehydedimethylacetal, 4-methylbenzaldehyde, 3-methylbenzonitrile, 4-methyl-2-phenyl-1,3-dioxolane, n-ethylaniline, p-anisaldehydedimethylacetal, 4-ethyl-2-methoxyphenol, 2-cyclopentylcyclopentanone, 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran, 1,2,3,4-tetrahydroquinoline, n-heptanoic acid, 2,4-dimethylphenol, cyclohexaneethanol, 2-ethylphenol, m-ethylphenol, 1-methyl-1h-indole, 6-methyl Quinoline, 4-methylanisole, o-isopropylphenol, 1,2-dimethyl-3-nitro Benzene, 4-nitro-m-xylene, caprylic acid, 2-ethylnitrobenzene, 3-phenoxybenzyl alcohol, 2- (1-cyclohexyl) cyclohexanone, ot-butylphenol, nonanonitrile, 2 -Methyl-5- (1-methylethyl) phenol, 1-methoxynaphthalene, nonanoic acid, 1-nonanol, 6-methoxy-1,2,3,4-tetrahydronaphthalene, tetralin, 1-methylnaphthalene, 1,2,3,4-tetramethylbenzene, diphenyl ether, diphenylsulfide, 3-phenoxytoluene, cyclohexylbenzene, cyclodecane, ethyl 4-ethoxybenzoate, isobutyl salicyl Rate, benzoic acid butyl ester, ethyl 4-methoxybenzoate, b-phenylethyl acetate, ethyl phenylacetate, ethyl p-toluate, ethyl benzoate, acetic acid phenylmethyl ester, 2-hydroxy-benzoic Acid methyl ester, 3,4-dihydro-2h-1-benzopyran-2-one, and mixed solvents thereof,
Ink composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020180130046A KR102651100B1 (en) | 2018-10-29 | 2018-10-29 | Ink composition for organic light emitting device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020180130046A KR102651100B1 (en) | 2018-10-29 | 2018-10-29 | Ink composition for organic light emitting device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20200048218A true KR20200048218A (en) | 2020-05-08 |
| KR102651100B1 KR102651100B1 (en) | 2024-03-22 |
Family
ID=70677512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020180130046A KR102651100B1 (en) | 2018-10-29 | 2018-10-29 | Ink composition for organic light emitting device |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR102651100B1 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| KR20120096075A (en) * | 2005-02-15 | 2012-08-29 | 미쓰비시 가가꾸 가부시키가이샤 | Film forming composition and organic electroluminescent device |
| KR20150093995A (en) * | 2014-02-10 | 2015-08-19 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20170108054A (en) * | 2015-01-26 | 2017-09-26 | 스미또모 가가꾸 가부시키가이샤 | Composition and light emitting device using the same |
| KR101799137B1 (en) * | 2010-12-21 | 2017-11-17 | 스미또모 가가꾸 가부시키가이샤 | High-molecular compound and light-emitting element using same |
| KR20180099446A (en) * | 2017-02-28 | 2018-09-05 | 주식회사 엘지화학 | Fluorene-based compound, organic light emitting device using the same and method of manufacturing the same |
-
2018
- 2018-10-29 KR KR1020180130046A patent/KR102651100B1/en active IP Right Grant
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| KR20120096075A (en) * | 2005-02-15 | 2012-08-29 | 미쓰비시 가가꾸 가부시키가이샤 | Film forming composition and organic electroluminescent device |
| KR101799137B1 (en) * | 2010-12-21 | 2017-11-17 | 스미또모 가가꾸 가부시키가이샤 | High-molecular compound and light-emitting element using same |
| KR20150093995A (en) * | 2014-02-10 | 2015-08-19 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20170108054A (en) * | 2015-01-26 | 2017-09-26 | 스미또모 가가꾸 가부시키가이샤 | Composition and light emitting device using the same |
| KR20180099446A (en) * | 2017-02-28 | 2018-09-05 | 주식회사 엘지화학 | Fluorene-based compound, organic light emitting device using the same and method of manufacturing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102651100B1 (en) | 2024-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3336159B1 (en) | Organic light-emitting element | |
| CN112771033B (en) | Novel compound and organic light emitting device comprising the same | |
| KR102134382B1 (en) | Novel compound and organic light emitting device comprising the same | |
| CN110267942B (en) | Novel heterocyclic compound and organic light-emitting device using same | |
| KR102469107B1 (en) | Organic light emitting device | |
| JP6801162B2 (en) | New heterocyclic compounds and organic light emitting devices using them | |
| CN108779392B (en) | Organic light emitting device | |
| CN112424191B (en) | Compound and organic light emitting device comprising the same | |
| KR102465732B1 (en) | Novel compound and organic light emitting device comprising the same | |
| TWI707924B (en) | Ink composition for organic light emitting device | |
| KR102175712B1 (en) | Novel hetero-cyclic compound and organic light emitting device comprising the same | |
| KR102166850B1 (en) | Novel compound and organic light emitting device comprising the same | |
| KR102651100B1 (en) | Ink composition for organic light emitting device | |
| KR102495828B1 (en) | Novel compound and organic light emitting device comprising the same | |
| KR102413612B1 (en) | Ink composition for organic light emitting device | |
| KR20210026941A (en) | Organic light emitting device | |
| KR20210023254A (en) | Novel compound and organic light emitting device comprising the same | |
| KR20210048334A (en) | Novel compound and organic light emitting device comprising the same | |
| CN111868053B (en) | Novel compound and organic light emitting device comprising the same | |
| KR102218558B1 (en) | Novel polymer and organic light emitting device comprising the same | |
| CN112689639B (en) | Compound and organic light emitting device comprising the same | |
| CN112368277B (en) | Novel compound and organic light emitting device comprising the same | |
| KR20210125839A (en) | Novel compound and organic light emitting device comprising the same | |
| KR20230096213A (en) | Novel compound and organic light emitting device comprising the same | |
| KR20220032906A (en) | Novel compound and organic light emitting device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant |