JP2019537574A - 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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- JP2019537574A JP2019537574A JP2019520849A JP2019520849A JP2019537574A JP 2019537574 A JP2019537574 A JP 2019537574A JP 2019520849 A JP2019520849 A JP 2019520849A JP 2019520849 A JP2019520849 A JP 2019520849A JP 2019537574 A JP2019537574 A JP 2019537574A
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- Prior art keywords
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- substituted
- unsubstituted
- coating composition
- fluorene
- Prior art date
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims abstract description 130
- 150000001875 compounds Chemical class 0.000 title claims abstract description 114
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 41
- 239000008199 coating composition Substances 0.000 claims abstract description 87
- 239000000126 substance Substances 0.000 claims abstract description 54
- 239000010410 layer Substances 0.000 claims description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- -1 fluorene compound Chemical class 0.000 claims description 55
- 239000012044 organic layer Substances 0.000 claims description 50
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 49
- 229910052805 deuterium Inorganic materials 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 47
- 239000000463 material Substances 0.000 claims description 46
- 238000002347 injection Methods 0.000 claims description 43
- 239000007924 injection Substances 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 239000010409 thin film Substances 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 239000011368 organic material Substances 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 20
- 229920001187 thermosetting polymer Polymers 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 230000014759 maintenance of location Effects 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 3
- 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 2
- DBDNZCBRIPTLJF-UHFFFAOYSA-N boron(1-) monohydride Chemical compound [BH-] DBDNZCBRIPTLJF-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 109
- 230000015572 biosynthetic process Effects 0.000 description 46
- 238000003786 synthesis reaction Methods 0.000 description 45
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- 229940126062 Compound A Drugs 0.000 description 23
- 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 23
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 239000003960 organic solvent Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 230000032258 transport Effects 0.000 description 21
- 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 20
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000000376 reactant Substances 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229940093499 ethyl acetate Drugs 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000004982 aromatic amines Chemical class 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 125000006267 biphenyl group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000001624 naphthyl group Chemical group 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 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- SZDXPEWZZGNIBB-UHFFFAOYSA-N n-[4-[4-(naphthalen-1-ylamino)phenyl]phenyl]naphthalen-1-amine Chemical compound C1=CC=C2C(NC=3C=CC(=CC=3)C=3C=CC(NC=4C5=CC=CC=C5C=CC=4)=CC=3)=CC=CC2=C1 SZDXPEWZZGNIBB-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 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 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 101150103861 HINT3 gene Proteins 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 150000001502 aryl halides Chemical class 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229920005596 polymer binder Polymers 0.000 description 3
- 239000002491 polymer binding agent Substances 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- OZZSXAWYZYTWQD-UHFFFAOYSA-N 2,2'-dibromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=C(Br)C=C2C21C1=CC=CC=C1C1=CC=C(Br)C=C12 OZZSXAWYZYTWQD-UHFFFAOYSA-N 0.000 description 2
- MTCARZDHUIEYMB-UHFFFAOYSA-N 2-bromofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C2=C1 MTCARZDHUIEYMB-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 101150078517 Hint1 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- 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
- 230000002747 voluntary effect Effects 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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Abstract
Description
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り、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;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0または1である。
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り、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;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0または1である。
前記フルオレニル基が置換される場合、
本明細書において、前記アルキレン基は、2価の基のものを除き、前述したアルキル基の例示の中から選択されてもよい。
X12は、S、SO、CRuRv、SiRwRx、またはNRyであり、
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る。
R1〜R6、n1〜n6、m1、m2、Ar1、Ar2、X1およびX2の定義は、前記化学式1におけるものと同じであり、
R101〜R121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〜s5、s8、s16およびs19は、それぞれ0〜4の整数であり、
s6、s7およびs9は、それぞれ0〜6の整数であり、
s12、s13、s17およびs18は、それぞれ0〜3の整数であり、
s20およびs21は、それぞれ0〜7の整数であり、
s1〜s9、s12、s13およびs16〜s21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。
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。
前記発熱ピークと発熱ピーク前の吸熱ピークとの間の温度差が20℃〜200℃であってもよい。
硬化性基が結合したフルオレン系化合物は、次の方法で合成できる。
1.硬化性基が結合したフルオレンの合成方法1(FS1−製造例1、2)
下記表1に記載の化合物を用いてF4P、F5P、およびF6Pを合成した。
製造例9.
下記表2に記載の化合物を用いてF1PBPAおよびF8PBPAを合成した。
製造例12.化合物Aの合成
1H NMR:δ7.71(d,2H),7.65(d,2H),7.42(d,4H),7.35(d,4H),7.27−7.20(m,18H),7.17−7.13(m,4H),7.11−7.06(m,14H),7.03(t,2H),6.70−6.64(dd,2H),5.69(d,2H),5.19(d,2H).
1H NMR:δ7.70(d,2H),7.63(d,2H),7.43(d,4H),7.37(t,2H),7.30−7.20(m,14H),7.15−7.05(m,14H),7.02(t,2H),6.93(s,4H),6.86(s,2H),6.71−6.65(dd,2H),5.70(d,2H),5.20(d,2H),2.15(s,6H),1.57(s,6H).
1H NMR:δ7.51−7.46(m,6H),7.44(d,2H),7.40−7.36(m,2H),7.31−7.23(m,16H),7.23−7.17(m,2H),7.14(d,2H),7.13−7.09(m,8H),7.05−7.01(m,4H),6.97−6.92(m,4H),6.57−6.49(m,2H),6.49(d,4H),5.58(dd,2H),5.10(dt,2H),3.85(d,2H),3.63(d,2H).
1H NMR:δ7.74−7.69(m,4H),7.68−7.63(m,2H),7.62−7.56(m,2H),7.39(td,2H),7.33(ddddd,4H),7.26(tdd,6H),7.19−7.04(m,12H),7.04−6.90(m,14H),6.85(d,2H),6.76−6.68(m,4H),6.65−6.55(m,2H),5.78−5.70(m,2H),5.25(dq,2H),2.16(s,6H),1.57(s,6H).
1H NMR:δ7.73(d,2H),7.69(d,2H),7.59(d,4H),7.48(t,8H),7.43(t,4H),7.38−7.30(m,8H),7.28−7.11(m,30H),6.71−6.65(dd,2H),5.69(d,2H),5.20(d,2H).
1H NMR:δ7.73(d,2H),7.68(d,2H),7.58(d,4H),7.47(t,8H),7.43(t,4H),7.38−7.21(m,18H),7.17−7.05(m,18H),6.71−6.65(dd,2H),5.69(d,2H),5.20(d,2H),1.35(S,18H).
1H NMR:δ7.82−7.73(m,6H),7.68−7.62(m,18H),7.55−7.34(m,10H),7.34−7.05(m,30H),6.58−6.50(m,2H),6.49(d,4H),5.57(dd,2H),5.11(dt,2H),3.84(d,2H),3.63(d,2H),1.35(s,18).
1H NMR(H):δ7.77(s,2H),7.51−7.46(m,6H),7.44(d,2H),7.40−7.37(m,4H),7.32−7.18(m,22H),7.15−7.08(m,14H),7.06−7.01(m,6H),6.57−6.49(m,2H),6.49(d,4H),5.58(dd,2H),5.10(dt,2H),3.85(d,2H),3.63(d,2H),2.80−2.77(m,4H),1.54−1.46(m,4H),1.39−1.27(m,12H),0.90−0.87(m,6H).
1H NMR:δ7.91−7.89(m,2H),7.86(dd,2H),7.80−7.77(m,2H),7.66(dt,2H),7.58(dd,2H),7.50−7.44(m,4H),7.36−7.29(m,12H),7.22−7.11(m,14H),7.09−7.04(m,4H),7.03−6.96(m,10H),6.65(dd,2H),5.68(dd,2H),5.19(dd,2H).
1H NMR:δ7.90−7.88(m,2H),7.87(dd,2H),7.79−7.75(m,2H),7.64(dt,2H),7.59(dd,2H),7.49−7.41(m,4H),7.37−7.30(m,12H),7.22−7.11(m,8H),7.09−7.03(m,4H),7.02−6.96(m,6H),6.64(dd,2H),5.67(dd,2H),5.18(dd,2H).
1H NMR:δ7.92−7.90(m,2H),7.89(dd,2H),7.80−7.77(m,2H),7.64(dt,2H),7.59(dd,2H),7.49−7.41(m,4H),7.37−7.30(m,12H),7.22−7.12(m,8H),7.09−7.03(m,4H),7.03−6.98(m,6H),6.65(dd,2H),5.67(dd,2H),5.18(dd,2H).
1H NMR:δ7.73−7.67(m,3H),7.62(d,1H),7.59(d,2H),7.49−7.21(m,26H),7.19−7.02(m,17H),6.93(s,2H),6.86(s,1H),6.71−6.65(m,2H),5.71−5.66(m,2H),5.21−5.17(m,2H),2.14(s,3H),1.56(s,3H)
実験例1.薄膜保持率の測定
下記化合物Aと下記化学式9−2との重量比(化合物A:化学式9−2)を8:2で含む2wt%トルエンコーティング組成物、比較化合物1と化学式9−2の2wt%トルエンコーティング組成物をガラスにスピンコーティングして薄膜を形成した。それぞれの薄膜を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)に10分間浸漬した後、乾燥後にUVを測定した。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確認することができた。
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輸送させた。
ITO透明電極上に化合物Aと化学式9−2との重量比(化合物A:化学式9−2)を8:2で含む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し、220℃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α−NPD(N,N−ジ(1−ナフチル)−N,N−ジフェニル−(1,1’−ビフェニル)−4,4’−ジアミン)の2wt%トルエン(toluene)インクをスピンコーティングして正孔輸送層を40nmの厚さに形成した。この後、真空蒸着機に搬送した後、前記正孔輸送層上にADNとDPAVBiとの重量比(ADN:DPAVBi)を20:1として20nmの厚さに真空蒸着して発光層を形成した。前記発光層上にBCP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。
前記素子例1において、化合物Aの代わりに化合物Bを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Cを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Dを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Eを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Fを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Gを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Hを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Iを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Jを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Kを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに化合物Lを用いたことを除けば、前記素子例1と同様の方法で有機発光素子を製造した。
前記素子例1において、化合物Aの代わりに下記比較化合物2を用いたことを除けば、前記素子例1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 (14)
- 下記化学式1で表されるフルオレン系化合物:
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り、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;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0または1である。 - X1およびX2の定義のうち、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つである、請求項1に記載のフルオレン系化合物:
- 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に記載のフルオレン系化合物。
- 前記化学式1は、下記化合物のうちのいずれか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1〜5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6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7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むものである、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、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6または7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6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11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、請求項6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13に記載の有機発光素子の製造方法。
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CN109863133B (zh) | 2022-12-23 |
EP3514140A1 (en) | 2019-07-24 |
CN109843850A (zh) | 2019-06-04 |
WO2018159933A1 (ko) | 2018-09-07 |
EP3514139A4 (en) | 2019-11-06 |
EP3514140B1 (en) | 2024-03-06 |
JP6749675B2 (ja) | 2020-09-02 |
KR20180092270A (ko) | 2018-08-17 |
CN109843850B (zh) | 2022-12-16 |
US20200028083A1 (en) | 2020-01-23 |
KR20180099446A (ko) | 2018-09-05 |
CN109863133A (zh) | 2019-06-07 |
KR102056524B1 (ko) | 2019-12-17 |
EP3514140A4 (en) | 2019-11-06 |
JP6820055B2 (ja) | 2021-01-27 |
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