JP6749675B2 - フルオレン系化合物、これを用いた有機発光素子およびその製造方法 - Google Patents
フルオレン系化合物、これを用いた有機発光素子およびその製造方法 Download PDFInfo
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- JP6749675B2 JP6749675B2 JP2019519247A JP2019519247A JP6749675B2 JP 6749675 B2 JP6749675 B2 JP 6749675B2 JP 2019519247 A JP2019519247 A JP 2019519247A JP 2019519247 A JP2019519247 A JP 2019519247A JP 6749675 B2 JP6749675 B2 JP 6749675B2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims description 86
- -1 Fluorene compound Chemical class 0.000 title claims description 62
- 238000000034 method Methods 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 239000010410 layer Substances 0.000 claims description 151
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 239000008199 coating composition Substances 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 230000015572 biosynthetic process Effects 0.000 claims description 53
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 50
- 229910052805 deuterium Inorganic materials 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 49
- 239000011368 organic material Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 41
- 239000007924 injection Substances 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 239000010409 thin film Substances 0.000 claims description 33
- 230000005525 hole transport Effects 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- 229920001187 thermosetting polymer Polymers 0.000 claims description 16
- 230000014759 maintenance of location Effects 0.000 claims description 15
- 125000005549 heteroarylene group Chemical group 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 claims description 3
- DBDNZCBRIPTLJF-UHFFFAOYSA-N boron(1-) monohydride Chemical compound [BH-] DBDNZCBRIPTLJF-UHFFFAOYSA-N 0.000 claims description 2
- DCGQVDFBDSTUML-AWEZNQCLSA-N 2-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidine-1-carbonyl]chromen-4-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1OC2=CC=CC=C2C(C=1)=O DCGQVDFBDSTUML-AWEZNQCLSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 132
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 103
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 238000003786 synthesis reaction Methods 0.000 description 46
- 239000000203 mixture Substances 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000003960 organic solvent Substances 0.000 description 22
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 230000008569 process Effects 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000032258 transport Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 125000001624 naphthyl group Chemical group 0.000 description 15
- 125000006267 biphenyl group Chemical group 0.000 description 13
- 229940125904 compound 1 Drugs 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 229940126062 Compound A Drugs 0.000 description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 9
- NOJDQJYQJQZCGS-UHFFFAOYSA-N 2-bromo-9-phenyl-9h-fluorene Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1C2C1=CC=CC=C1 NOJDQJYQJQZCGS-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 150000004982 aromatic amines Chemical class 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 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 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- RGSXRPAZIFLLPK-UHFFFAOYSA-N 2-bromo-9-[6-(4-ethenylphenoxy)hexyl]-9-phenylfluorene Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(CCCCCCOC1=CC=C(C=C1)C=C)C1=CC=CC=C1 RGSXRPAZIFLLPK-UHFFFAOYSA-N 0.000 description 7
- CWFALOFIVBAZFV-UHFFFAOYSA-N 4-(6-bromohexoxy)benzaldehyde Chemical compound BrCCCCCCOC1=CC=C(C=O)C=C1 CWFALOFIVBAZFV-UHFFFAOYSA-N 0.000 description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- OGUHBBPKPSQTHB-UHFFFAOYSA-N 2-bromo-9-(4-ethenylphenyl)-9-phenylfluorene Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(C1=CC=C(C=C1)C=C)C1=CC=CC=C1 OGUHBBPKPSQTHB-UHFFFAOYSA-N 0.000 description 6
- IQJFYDIYRBKMKE-UHFFFAOYSA-N 4-(2-bromo-9-hydroxyfluoren-9-yl)benzaldehyde Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(O)C1=CC=C(C=O)C=C1 IQJFYDIYRBKMKE-UHFFFAOYSA-N 0.000 description 6
- NSDOEOWTTXZPFG-UHFFFAOYSA-N 4-(4-bromobutoxy)benzaldehyde Chemical compound BrCCCCOC1=CC=C(C=O)C=C1 NSDOEOWTTXZPFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 5
- GBLYKAYFSRNIBE-UHFFFAOYSA-N 1-bromo-4-(6-bromohexyl)benzene Chemical compound BrCCCCCCC1=CC=C(Br)C=C1 GBLYKAYFSRNIBE-UHFFFAOYSA-N 0.000 description 5
- PMQYJJBYTDKRNF-UHFFFAOYSA-N 2-bromo-9-[4-(4-ethenylphenoxy)butyl]-9-phenylfluorene Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(CCCCOC1=CC=C(C=C1)C=C)C1=CC=CC=C1 PMQYJJBYTDKRNF-UHFFFAOYSA-N 0.000 description 5
- MAKUNMAGEXSECN-UHFFFAOYSA-N 4-[2-bromo-9-(2,5-dimethylphenyl)fluoren-9-yl]benzaldehyde Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(C1=C(C=CC(=C1)C)C)C1=CC=C(C=O)C=C1 MAKUNMAGEXSECN-UHFFFAOYSA-N 0.000 description 5
- 229940127007 Compound 39 Drugs 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- 229940127204 compound 29 Drugs 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 4
- HKRCCUWLVOOAIH-UHFFFAOYSA-N 1-(6-bromohexyl)-4-ethenylbenzene Chemical compound BrCCCCCCC1=CC=C(C=C)C=C1 HKRCCUWLVOOAIH-UHFFFAOYSA-N 0.000 description 4
- ILNHMTIDILBCFT-UHFFFAOYSA-N 4-(2-bromo-9-phenylfluoren-9-yl)benzaldehyde Chemical compound C1=CC=CC2=C1C(C1=CC=C(C=O)C=C1)(C1=CC=CC=C1)C1=CC(Br)=CC=C21 ILNHMTIDILBCFT-UHFFFAOYSA-N 0.000 description 4
- LZRKOLCDCPTAFG-UHFFFAOYSA-N 4-[4-(2-bromo-9-phenylfluoren-9-yl)butoxy]benzaldehyde Chemical compound BrC1=CC=2C(C3=CC=CC=C3C=2C=C1)(C1=CC=CC=C1)CCCCOC1=CC=C(C=O)C=C1 LZRKOLCDCPTAFG-UHFFFAOYSA-N 0.000 description 4
- WMZSBQFUEJWRKJ-UHFFFAOYSA-N 4-phenyl-n-[4-[4-(4-phenylanilino)phenyl]phenyl]aniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC(=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 WMZSBQFUEJWRKJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- 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 3
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ABFRAZBKBONXKO-UHFFFAOYSA-N 2-bromo-9-(2,5-dimethylphenyl)-9-(4-ethenylphenyl)fluorene Chemical compound C1=CC=C2C(=C1)C(C1=CC=C(C=C)C=C1)(C1=CC(C)=CC=C1C)C1=CC(Br)=CC=C21 ABFRAZBKBONXKO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Description
L1およびL2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキレン基;置換もしくは非置換のシクロアルキレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Lは、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
R1〜R6は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であるか、隣接した基は、互いに結合して置換もしくは非置換の炭化水素環を形成してもよく、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
X1およびX2は、互いに同一または異なり、それぞれ独立に、光硬化性基または熱硬化性基であり、
n1およびn4は、それぞれ独立に、0〜5の整数であり、
n2およびn6は、それぞれ独立に、0〜4の整数であり、
n3およびn5は、それぞれ独立に、0〜3の整数であり、
n1〜n6がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なり、
m1およびm2は、それぞれ独立に、2〜12の整数であり、
m1およびm2がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なる。
L1およびL2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキレン基;置換もしくは非置換のシクロアルキレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Lは、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
R1〜R6は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であるか、隣接した基は、互いに結合して置換もしくは非置換の炭化水素環を形成してもよく、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
X1およびX2は、互いに同一または異なり、それぞれ独立に、光硬化性基または熱硬化性基であり、
n1およびn4は、それぞれ独立に、0〜5の整数であり、
n2およびn6は、それぞれ独立に、0〜4の整数であり、
n3およびn5は、それぞれ独立に、0〜3の整数であり、
n1〜n6がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なり、
m1およびm2は、それぞれ独立に、2〜12の整数であり、
m1およびm2がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なる。
A1〜A3は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数1〜6のアルキル基である。
X1〜X11は、互いに同一または異なり、それぞれ独立に、O、S、SiR’R”、またはNRであり、
R11〜R25、Rs、Rt、Ru、Rv、Rw、Rx、Ry、R、R’およびR”は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
s1は、0〜4の整数である。
Wは、O、S、NRa、CRbRc、またはSiRdReであり、
R31〜R41、Ra、Rb、Rc、RdおよびReは、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
p1は、0〜7の整数であり、
p2、p4およびp5は、それぞれ0〜4の整数であり、
p3およびp6は、それぞれ0〜5の整数であり、
p1〜p6がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なる。
例えば、前記化学式1のフルオレン系化合物は、下記反応式1のようなコア構造が製造される。置換基は、当技術分野で知られている方法によって結合可能であり、置換基の種類、位置または個数は、当技術分野で知られている技術によって変更可能である。
製造例1.化合物1の合成
(1)中間体3の合成
化合物1のNMR測定値:1H NMR(500MHz,CD2Cl2)δ7.70(d,2H),7.68(d,2H),7.57(d,4H),7.48(t,8H),7.41(t,4H),7.34−7.26(m,8H),7.23−7.10(m,26H),6.76(d,4H),6.64−6.58(dd,2H),5.56(d,2H),5.07(d,2H),3.85(t,4H),2.46−2.36(m,4H),1.67−1.61(m,4H)1.35−1.23(m,8H),0.92−0.73(m 4H)
(1)中間体10の合成
(1)中間体12の合成
(1)中間体19の合成
(1)中間体22の合成
(1)中間体20の合成
(1)比較化合物Cの合成
実験例1.DSC試料分析
30℃で開始して1分あたり10℃ずつ300℃まで上げた後、30分間維持した。再び1分あたり10℃ずつ30℃まで下げた後、再び1分あたり10℃ずつ300℃まで上げて、DSC資料を得た。得られたTg、Tmおよび硬化点を表1に示した。
化合物1および比較化合物Aの2wt%トルエン(toluene)溶液でガラスにスピンコーティングして薄膜を形成した。窒素雰囲気内で化合物1で形成された薄膜の場合に200℃で、比較化合物Aで形成された薄膜の場合に220℃で30分間熱処理し、各薄膜のUV吸収を測定した。再びその薄膜をトルエン(toluene)およびシクロヘキサノン(CHON、cyclohexanone)に10分間浸漬した後、乾燥後にUVを測定した。トルエン(Toluene)およびシクロヘキサノン(CHON、cyclohexanone)に浸漬する前後のUV吸収の最大ピーク(peak)の大きさの比較で薄膜保持率を測定した。
ITO基板の準備
ITO(indium tin oxide)が1,500Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行させた。
蒸留水洗浄が終わった後、イソプロピルアルコール、アセトンの溶剤で超音波洗浄をし乾燥させた後、前記基板を5分間洗浄した後、グローブボックスに基板を移した。
ITO透明電極上にHT−1:TB(8:2)の1.5wt%トルエン(toluene)インクをITO表面上にスピンコーティング(4000rpm)し、230℃で30分間熱処理(硬化)して30nmの厚さに正孔注入層を形成した。前記形成された正孔注入層上に化合物1の2wt%トルエン(toluene)インクをスピンコーティング(3000rpm)し、200℃で30分間熱処理(硬化)して正孔輸送層を40nmの厚さに形成した。形成された正孔輸送層上にEM−1の1wt%トルエン(toluene)インクを用いてスピンコーティング(3000rpm)し、熱処理して20nmの厚さに発光層を成膜した。この後、真空蒸着機に搬送した後、前記発光層上にET−1を35nmの厚さに真空蒸着して電子注入および輸送層を形成した。前記電子注入および輸送層上に、順次に、1nmの厚さにLiFと100nmの厚さにアルミニウムを蒸着してカソードを形成した。
素子例1の作製過程において、正孔注入層の成膜時、HT−1:TB(8:2)1.5wt%トルエン(toluene)インクの代わりに化合物1:TB(8:2)の1.5wt%トルエン(toluene)インクを用いたことを除けば、素子例1の過程と同様の方法で有機発光素子を製造した。
素子例1の作製過程において、正孔輸送層の成膜時、化合物1 2wt%トルエン(toluene)インクの代わりに化合物29 2wt%トルエン(toluene)インクを用いたことを除けば、素子例1の過程と同様の方法で有機発光素子を製造した。
素子例1の作製過程において、正孔輸送層の成膜時、化合物1 2wt%トルエン(toluene)インクの代わりに化合物39 2wt%トルエン(toluene)インクを用いたことを除けば、素子例1の過程と同様の方法で有機発光素子を製造した。
素子例1の作製過程において、正孔輸送層の成膜時、化合物1 2wt%トルエン(toluene)インクの代わりに化合物43 2wt%トルエン(toluene)インクを用いたことを除けば、素子例1の過程と同様の方法で有機発光素子を製造した。
素子例1の作製過程において、正孔輸送層の成膜時、化合物1の2wt%トルエン(toluene)インクの代わりにVNPBの2wt%トルエン(toluene)インクを用いたことを除けば、素子例1の過程と同様の方法で有機発光素子を製造した。
201:アノード
301:正孔注入層
401:正孔輸送層
501:発光層
601:電子注入および電子輸送を同時に行う層
701:カソード
Claims (13)
- 下記化学式1で表されるフルオレン系化合物:
L1およびL2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキレン基;置換もしくは非置換のシクロアルキレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Lは、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
R1〜R6は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であるか、隣接した基は、互いに結合して置換もしくは非置換の炭化水素環を形成してもよく、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
X1およびX2は、互いに同一または異なり、それぞれ独立に、光硬化性基または熱硬化性基であり、光硬化性基または熱硬化性基は、下記構造:
のうちのいずれか1つであり、
n1およびn4は、それぞれ独立に、0〜5の整数であり、
n2およびn6は、それぞれ独立に、0〜4の整数であり、
n3およびn5は、それぞれ独立に、0〜3の整数であり、
n1〜n6がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なり、
m1およびm2は、それぞれ独立に、2〜12の整数であり、
m1およびm2がそれぞれ2以上の場合、括弧内の置換基は、互いに同一または異なる。 - 前記Lは、置換もしくは非置換の炭素数6〜30のアリーレン基;または置換もしくは非置換の炭素数2〜30のヘテロアリーレン基である、請求項1に記載のフルオレン系化合物。
- 前記Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数6〜30のアリール基;または置換もしくは非置換の炭素数2〜30のヘテロアリーレン基である、請求項1又は2に記載のフルオレン系化合物。
- 下記化合物1〜48のうちのいずれか1つである、請求項1に記載のフルオレン系化合物:
- 請求項1〜4のいずれか1項に記載のフルオレン系化合物を含むコーティング組成物。
- 前記コーティング組成物は、pドーピング物質をさらに含むものである、請求項5に記載のコーティング組成物。
- 前記pドーピング物質は、F4TCNQ;またはホウ素陰イオンを含む化合物である、請求項6に記載のコーティング組成物。
- 前記コーティング組成物は、熱硬化性基または光硬化性基を含む単分子;または熱によるポリマー形成が可能な末端基を含む単分子をさらに含み、熱硬化性基または光硬化性基が、
下記構造:
から選択される、請求項5に記載のコーティング組成物。 - 前記コーティング組成物は、250℃以下の熱処理後、薄膜保持試験で薄膜保持率が95%以上である、請求項5に記載のコーティング組成物。
- 第1電極と、
第2電極と、
前記第1電極と前記第2電極との間に備えられる1層以上の有機物層とを含み、
前記有機物層のうちの1層以上は、請求項5に記載のコーティング組成物またはその硬化物を含み、
前記コーティング組成物の硬化物は、前記コーティング組成物を熱処理または光処理によって硬化した状態のものである有機発光素子。 - 前記コーティング組成物またはその硬化物を含む有機物層は、正孔輸送層、正孔注入層、または正孔輸送および正孔注入を同時に行う層である、請求項10に記載の有機発光素子。
- 基板を準備するステップと、
前記基板上に第1電極を形成するステップと、
前記第1電極上に1層以上の有機物層を形成するステップと、
前記有機物層上に第2電極を形成するステップとを含み、
前記有機物層を形成するステップは、前記請求項5に記載のコーティング組成物を用いて1層以上の有機物層を形成するステップを含むものである有機発光素子の製造方法。 - 前記コーティング組成物を用いて形成された有機物層を形成するステップは、
前記第1電極上に前記コーティング組成物をコーティングするステップと、
前記コーティングされたコーティング組成物を熱処理または光処理するステップとを含むものである、請求項12に記載の有機発光素子の製造方法。
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