JP7456757B2 - 有機電界発光素子及び有機電界発光素子用多環化合物 - Google Patents
有機電界発光素子及び有機電界発光素子用多環化合物 Download PDFInfo
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- JP7456757B2 JP7456757B2 JP2019215631A JP2019215631A JP7456757B2 JP 7456757 B2 JP7456757 B2 JP 7456757B2 JP 2019215631 A JP2019215631 A JP 2019215631A JP 2019215631 A JP2019215631 A JP 2019215631A JP 7456757 B2 JP7456757 B2 JP 7456757B2
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- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- SKRQCHDXFSWTHN-UHFFFAOYSA-N 4-methyl-n-[4-[2-[4-[1-(4-methyl-n-(4-methylphenyl)anilino)-2-phenylethenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C(C=1C=CC(C=CC=2C=CC(=CC=2)N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=CC=1)=CC1=CC=CC=C1 SKRQCHDXFSWTHN-UHFFFAOYSA-N 0.000 description 1
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- BJWISAZIWBYQRE-UHFFFAOYSA-N 9-(3-bromo-5-chlorophenyl)carbazole Chemical compound Clc1cc(Br)cc(c1)-n1c2ccccc2c2ccccc12 BJWISAZIWBYQRE-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000005104 aryl silyl group Chemical group 0.000 description 1
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- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
- 229940125904 compound 1 Drugs 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 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
- 230000007423 decrease Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229930195733 hydrocarbon Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004219 molecular orbital method Methods 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- NRKQPQQULQMWBV-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-yl]ethenyl]aniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 NRKQPQQULQMWBV-MBALSZOMSA-N 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000000059 patterning Methods 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 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
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical group S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000001308 synthesis method Methods 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
- 238000001931 thermography Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 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
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/04—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Description
化学式1において、XはS、O、C(=O)、NRa、またはBRbであり、R1及びR2はそれぞれ重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基であり、Ra及びRbはそれぞれ独立して、水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基である。R1、R2、Ra及びRbは隣接する基と互いに結合して環を形成するか、または結合しない。m及びnはそれぞれ独立して0以上3以下の整数であり、Ar1~Ar3はそれぞれ独立して、環形成炭素数5以上60以下の炭化水素環基、または環形成原子であって、窒素原子を含まない環形成炭素数5以上60以下のヘテロ環基であり、Ar4及びAr5はそれぞれ独立して、下記化学式2で表される。
前記化学式2において、pは0または1であり、pが1であれば、Yは単結合またはCRcRdであり、Ar6及びAr7はそれぞれ独立して、環形成炭素数5以上60以下の炭化水素環基、または環形成原子であって、窒素原子を含まない環形成炭素数5以上60以下のヘテロ環基である。R3、R4、Rc及びRdはそれぞれ独立して、水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基であり、隣接する基と結合して環を形成するか、または結合しない。a及びbはそれぞれ独立して0以上4以下の整数である。
前記化学式1-1において、X、Ar1~Ar5、R1、R2、m、及びnは、前記化学式1で定義した通りである。
前記化学式1-2A及び化学式1-2Bにおいて、X、Ar2~Ar5、R1、R2、m、及びnは、前記化学式1で定義した通りである。
前記化学式1-3A及び化学式1-3Bにおいて、X、及びAr1~Ar5は前記化学式1で定義した通りである。
前記化学式2-1及び化学式2-2において、Ar6、Ar7、R3、R4、a及びbは前記化学式2で定義した通りである。
[第1化合物群]
1.多環化合物の合成
まず、本実施形態に係る多環化合物の合成方法について、化合物A-5、A-3、A-22、及びA-24の合成方法を例示して詳しく説明する。また、以下で説明する多環化合物の合成法は一例であって、本発明の実施形態に係る多環化合物の合成法は下記実施例に限らない。
多環化合物A-5は、例えば、下記反応式1によって合成される。
[反応式1]
ジメチルフェニルボロナート(1eq)と9-(3-ブロモ-5-クロロフェニル)-9H-カルバゾール(2.1eq)を500mlのトルエンに溶解させた。Pd(PPh3)4(0.02eq)を添加し、更にトルエン400ml及び2MのK2CO3飽和溶液70mlを添加した後、5時間還流撹拌した。反応終結後、MC(メチレンクロライド)400mlと蒸留水150mlで洗浄及び抽出してから、溶媒を除した後、生成された固体をカラムクロマトグラフィで精製して所望の中間体1-1(収率55.4%)を得た。質量分析器で測定した結果、分子量から、中間体1-1であることを確認した。(HRMS for C42H27BCl2N2 [M]+:calcd:641、found:640)
中間体1-1(1eq)とN1,N2-ジフェニルベンゼン-1,2-ジアミン(1eq)を入れたフラスコに、Pd(dba)3(0.03eq)、(t-Bu)3P(0.06eq)及びトルエン(0.1M、1eq試薬基準)を添加した後、8時間還流撹拌した。常温で冷却した後、MCで抽出し、蒸留水で洗浄した。MgSO4で乾燥させ、減圧蒸留した後、残渣をカラムで分離して化合物A-5(収率78.87%)を得た。質量分析器で測定した分子量から、化合物A-5であることを確認した。(HRMS for C60H41BN4 [M]+:calcd:828、found:827)
多環化合物A-3は、例えば、下記反応式2によって合成される。
[反応式2]
ベンゼン-1,2-ジアミン(1eq)とビス(3-ブロモ-5-クロロフェニル)スルファン(1eq)を入れ、Pd(dba)3(0.03eq)、(t-Bu)3P(0.06eq)及びトルエン(0.1M、1eq試薬基準)を添加した後、8時間還流撹拌した。常温で冷却した後、MCで抽出し、蒸留水で洗浄した。MgSO4で乾燥させ、減圧蒸留した後、残渣をカラムで分離して化合物2-1(収率78.87%)を得た。質量分析器で測定した結果、分子量から、中間体2-1であることを確認した。(HRMS for C18H12BCl2N2S[M]+:calcd:359、found:358)
中間体2.2(1eq)とブロモベンゼン(2.2eq)を入れ、Pd(dba)3(0.03eq)、(t-Bu)3P(0.06eq)及びトルエン(0.1M、1eq試薬基準)を添加した後、8時間還流撹拌した。常温で冷却した後、MCで抽出し、蒸留水で洗浄した。MgSO4で乾燥させ、減圧蒸留した後、残渣をカラムで分離して化合物2-2(収率87%)を得た。質量分析器で測定した結果、分子量から、中間体2-2であることを確認した。(HRMS for C30H20Cl2N2S [M]+:calcd:512、found:511)
中間体2-2(1eq)とカルバゾール(2.2eq)を入れたフラスコに、Pd(dba)3(0.03eq)、(t-Bu)3P(0.06eq)及びトルエン(0.1M、1eq試薬基準)を添加した後、8時間還流撹拌した。常温で冷却した後、MCで抽出し、蒸留水で洗浄した。MgSO4で乾燥させ、減圧蒸留した後、残渣をカラムで分離して化合物A-3(収率88.44%)を得た。質量分析器で測定した結果、分子量から、化合物A-3であることを確認した。(HRMS for C54H36N4S [M]+:calcd:772、found:771)
一実施例による多環化合物A-22は、例えば、下記反応式3によって合成される。
[反応式3]
N1,N3-ジフェニルベンゼン-1,3-ジアミン(1eq)と1-ブロモ-3-クロロ-5-ヨードベンゼン(2.1eq)を入れ、Pd(dba)3(0.03eq)、(t-Bu)3P(0.06eq)及びトルエン(0.1M、1eq試薬基準)を添加した後、3時間120℃温度で撹拌した。常温で冷却し、MCで抽出し、蒸留水で洗浄した。MgSO4で乾燥させ、減圧蒸留した後、残渣をカラムで分離して化合物3-1(収率81.7%)を得た。質量分析器で測定した結果、分子量から、中間体3-1であることを確認した。(HRMS for C30H20Br2Cl2N2 [M]+:calcd:639、found:638)
中間体3-1(1eq)とジメチルフェニルボロナート(1eq)を500mlのトルエンに溶解させた。次に、Pd(PPh3)4(0.02eq)を添加した。更にトルエン400ml及び2MのK2CO3飽和溶液70mlを添加した後、5時間還流撹拌させた。反応終結後、MC400mlと蒸留水150mlで洗浄及び抽出してから、溶媒を除した後、生成された固体をカラムクロマトグラフィで精製して所望の中間体3-2(収率66.7%)を得た。質量分析器で測定した結果、分子量から、中間体3-2であることを確認した。(HRMS for C36H25BCl2N2 [M]+:calcd:567、found:566)
中間体3-2(1eq)とカルバゾール(2.2eq)を入れたフラスコに、Pd(dba)3(0.03eq)、(t-Bu)3P(0.06eq)及びトルエン(0.1M、1eq試薬基準)を添加した後、8時間還流撹拌した。常温で冷却し、MCで抽出した後、蒸留水で洗浄した。MgSO4で乾燥させ、減圧蒸留した後、残渣をカラムで分離して化合物A-22(収率85.6%)を得た。質量分析器で測定した結果、分子量から、化合物A-22であることを確認した。(HRMS for C60H41BN4 [M]+:calcd:828、found:827)
化合物A-5の合成方法から、N1,N2-ジフェニルベンゼン-1,2-ジアミン に代わってN1,N3-ジフェニルベンゼン-1,3-ジアミンを使用したことを除いては、化合物A-5の合成方法と同じ方法で化合物A-24を合成した。質量分析器で測定した結果、分子量から、化合物A-24であることを確認した。(HRMS for C60H41BN4 [M]+:calcd:828、found:827)
下記表1は、実施例化合物である化合物A-5、化合物A-3、A-22、及び化合物A-24のHOMOエネルギー準位、LUMOエネルギー準位、最低一重項励起エネルギー準位(S1 level)、最低三重項励起エネルギー準位(T1 level)、及びΔEST値を示している。
(有機電界発光素子の製作)
一実施形態に係る多環化合物を発光層に含む、一実施形態に係る有機電界発光素子を下記方法で製造した。上述した化合物A-5、化合物A-3、化合物A-22、及び化合物A-24の多環化合物を発光層のドーパント材料として使用し、実施例1~実施例4の有機電界発光素子を作製した。
表3は、実施例1~実施例4、及び比較例1~比較例2に対する有機電界発光素子の評価結果を示している。表2は、製作された有機電界発光素子の駆動電圧、発光効率及び外部量子効率(EOE)を比較して示している。表3に示した実施例及び比較例に対する特性評価結果において、発光効率は電流密度10mA/cm2に対する電流効率値を示す。
EL2:第2電極 HTR:正孔輸送領域
EML:発光層 ETR:電子輸送領域
Claims (10)
- 下記化学式1-2A、化学式1-2Bまたは化学式1-3Bで表される多環化合物。
(前記化学式1-2Aおよび前記化学式1-2Bにおいて、
XはC(=O)またはBRbであり、
R1及びR2はそれぞれ独立して、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基であり、
R b は、水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基であり、
m及びnはそれぞれ独立して0以上3以下の整数であり、
前記化学式1-3Bにおいて、
XはS、O、C(=O)、NR a 、またはBR b であり、
R a 及びR b はそれぞれ独立して、水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基であり、
前記化学式1-2A、前記化学式1-2Bまたは前記化学式1-3Bにおいて、
Ar1 ~Ar3はそれぞれ独立して、環形成炭素数5以上60以下の炭化水素環基、または環形成原子であって、窒素原子を含まない環形成炭素数5以上60以下のヘテロ環基であり、
Ar4及びAr5はそれぞれ独立して、下記化学式2で表され、
前記化学式2において、
pは0または1であり、
pが1であれば、Yは単結合またはCRcRdであり、
Ar6及びAr7はそれぞれ独立して、環形成炭素数5以上60以下の炭化水素環基、または環形成原子であって、窒素原子を含まない環形成炭素数5以上60以下のヘテロ環基であり、
R3、R4、Rc及びRdはそれぞれ独立して、水素原子、重水素原子、ハロゲン原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基であり、
a及びbはそれぞれ独立して0以上4以下の整数である。) - 前記化学式2は、下記化学式2-1または2-2で表される請求項1に記載の多環化合物。
- Ar2及びAr3は置換若しくは無置換のフェニル基である請求項1に記載の多環化合物。
- Ar4及びAr5は同じである請求項1に記載の多環化合物。
- 前記下記化学式1-2A、化学式1-2Bまたは化学式1-3Bで表される多環化合物は、熱活性遅延蛍光発光材料である請求項1に記載の多環化合物。
- 前記下記化学式1-2A、化学式1-2Bまたは化学式1-3Bで表される多環化合物は、下記第1化合物群に示した化合物のうちからいずれか一つである請求項1に記載の多環化合物。
[第1化合物群]
- 第1電極と、
前記第1電極の上に配置される正孔輸送領域と、
前記正孔輸送領域の上に配置され、請求項1乃至請求項6のうちいずれか一つである多環化合物を含む発光層と、
前記発光層の上に配置される電子輸送領域と、
前記電子輸送領域の上に配置される第2電極と、を含み、
前記第1電極及び前記第2電極はそれぞれ独立して、Ag,Mg,Cu,Al,Pt,Pd,Au,Ni,Nd,Ir,Cr,Li,Ca,LiF/Ca,LiF/Al,Mo,Ti,In,Sn及びZnからなる群から選択される一つ、これらの中から選択される複数を含む化合物、これらの中から選択される複数を含む混合物、又はこれらの中から選択される1つ以上の酸化物を含む、有機電界発光素子。 - 前記発光層は、遅延蛍光を放出する請求項7に記載の有機電界発光素子。
- 前記発光層はホスト及びドーパントを含む遅延蛍光発光層であり、
前記ドーパントは前記化学式1で表される多環化合物を含む請求項7に記載の有機電界発光素子。 - 前記発光層は、青色光を放出する請求項7に記載の有機電界発光素子。
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