JP6506534B2 - 有機電界発光素子用材料及びこれを用いた有機電界発光素子 - Google Patents
有機電界発光素子用材料及びこれを用いた有機電界発光素子 Download PDFInfo
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- JP6506534B2 JP6506534B2 JP2014227220A JP2014227220A JP6506534B2 JP 6506534 B2 JP6506534 B2 JP 6506534B2 JP 2014227220 A JP2014227220 A JP 2014227220A JP 2014227220 A JP2014227220 A JP 2014227220A JP 6506534 B2 JP6506534 B2 JP 6506534B2
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- 239000000463 material Substances 0.000 title claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 53
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- 230000005525 hole transport Effects 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- -1 naphthylphenyl group Chemical group 0.000 claims description 12
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
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- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
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- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-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
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- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
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- 125000003710 aryl alkyl group Chemical group 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- YVVVSJAMVJMZRF-UHFFFAOYSA-N c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 Chemical group c1cncc(c1)-c1cccc(c1)-c1cccc(c1)-c1nc(nc(n1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1)-c1cccc(c1)-c1cccc(c1)-c1cccnc1 YVVVSJAMVJMZRF-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005283 ground state Effects 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GQCUGWCIKIYVOY-UHFFFAOYSA-M lithium;quinoline-8-carboxylate Chemical compound [Li+].C1=CN=C2C(C(=O)[O-])=CC=CC2=C1 GQCUGWCIKIYVOY-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl 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])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
- 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
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 238000002360 preparation method 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
- 125000005412 pyrazyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007704 transition Effects 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
- 150000003852 triazoles Chemical class 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Description
R1、R2はそれぞれ独立に水素原子、ハロゲン原子、炭素数1〜15のアルキル基、置換もしくは無置換の環形成炭素数6〜30のアリール基、または置換もしくは無置換の環形成炭素数1〜30のヘテロアリール基であり、n、mは1〜4の整数である。
本発明者は、有機電界発光素子の発光寿命を改善することができる有機電界発光素子用材料について鋭意検討した結果、本実施形態に係る有機電界発光素子用材料に想到した。この有機電界発光素子用材料は、特に正孔輸送材料として用いた場合に、有機電界発光素子の発光寿命を改善することができる。そこで、まず、本実施形態に係る有機電界発光素子用材料の構成について説明する。本実施形態に係る有機電界発光素子用材料は、以下の化学式I〜IIIのいずれかで示されるモノアミン化合物のうち、少なくとも1種を含む。
アリール基及びヘテロアリール基の置換基は、Arを構成するアリール基の置換基と同様である。
次に、図1を参照しながら、本実施形態に係る有機電界発光素子用材料を利用した有機電界発光素子について、簡単に説明する。図1は、本発明の実施形態に係る有機電界発光素子の一例を示す概略断面図である。
、ナフチル基、フェニルナフチル基、ナフチルフェニル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、アセトナフテニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、フラニル基、ピラニル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、およびジベンゾチエニル基などを挙げることができる。好ましくは、フェニル基、ビフェニル基、ターフェニル基、フルオレニル基、カルバゾリル基、ジベンゾフラニル基などを挙げることができる。
化合物C(化学式IIIで示されるモノアミンの例)を、以下の合成スキームに沿って合成した。
アルゴン(argon)雰囲気下、500mLの三つ口フラスコ(flask)に、化合物A 15.00g、酸化第一銅0.85g、アンモニア(ammonia)水20ml、NMP70mlを加え、25時間110℃で加熱した。空冷後、水を加え、有機層を分取し、溶媒留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィー(silica gel column chromatography)(ヘキサン/酢酸エチル)(hexane/ethyl acetate)で精製し、白色固体の化合物Bを7.4 g(収率66%)得た。得られた化合物Bの分子量をFAB−MS測定したところ、測定値193(C14H11N)という値を得た。
アルゴン雰囲気下、500mLの三つ口フラスコに、化合物B 1.00g、1−ブロモジベンゾフラン2.81g、ビス(ジベンジリデンアセトン)パラジウム(0)(bis−(dibenxylideneacetone)palladium(0))0.27 g、トリ−tert−ブチルホスフィン(tri−tert−butylphosphine)0.088g、ナトリウムtert−ブトキシド(sodium tert−butoxide)3.98gを加えて、200mLのトルエン溶媒中で7時間加熱還流した。空冷後、水を加えて有機層を分取し溶媒留去した。得られた粗生成物をシリカゲルカラムクロマトグラフィー(トルエン/ヘキサン)(toluene/hexane)で精製し、白色固体の化合物Cを1.90g(収率70%)得た。得られた化合物Cの分子量をFAB−MS測定したところ、525(C38H23NO2)という値を得た。また、化合物Cのガラス転移点を日立ハイテク社製、示差走査熱量計DSC7020を用いて測定したところ、120℃という値を得た。
化合物D(化合物IIで示されるモノアミン化合物の例)を、以下の合成スキーム(scheme)に沿って合成した。
化合物E(化学式Iで示されるモノアミン化合物の例)を、以下の合成スキーム(scheme)に沿って合成した。
以下の化合物C3を比較例として用意した。化合物C3は先行文献2に開示された化合物である。この化合物C3のガラス転移点を日立ハイテク社製、示差走査熱量計DSC7020を用いて測定したところ、100℃であった。化合物C、D、Eのガラス転移点と化合物C3のガラス転移点とを比較すると、これらの化合物の分子量はほぼ同じであるにもかかわらず、化合物C、D、Eのガラス転移点は化合物C3のガラス転移点よりも特異的に高くなった。この結果、Arにフェナントレニル基を含めることで、ガラス転移点が高くなることが確認できた。したがって、化合物C、D、Eを正孔輸送層または発光層に含めた有機電界発光素子は、熱安定性が向上することが期待される。
つぎに、有機電界発光素子を以下の製法により作製した。まず、予めパターニング(patterning)して洗浄処理を施したITO−ガラス基板に、紫外線オゾン(O3)による表面処理を行った。なお、かかるITO膜(第1電極)の膜厚は、150nmであった。オゾン処理後、基板を洗浄した。洗浄済基板を有機層成膜用ガラスベルジャー型蒸着機にセットし、真空度10−4〜10−5Pa下で、正孔注入層、HTL(正孔輸送層)、発光層、電子輸送層の順に蒸着を行った。正孔注入層の材料は2−TNATAとし、厚さは60nmとした。HTLの材料は表1に示されるものとし、厚さは30nmとした。
次に、作成された有機電界発光素子の駆動電圧、発光寿命について測定した。なお、作製した有機EL素子200の発光特性の評価には、浜松ホトニクス製C9920−11輝度配向特性測定装置を用いた。また、電流密度は10mA/cm2にて測定し、半減寿命は1000cd/m2にて測定した。結果を表1に示す。
110 基板
120 第1電極
130 正孔注入層
140 正孔輸送層
150 発光層
160 電子輸送層
170 電子注入層
180 第2電極
Claims (6)
- 以下の化学式I〜IIIのいずれかで示されるモノアミン化合物のうち、少なくとも1種を含むことを特徴とする有機電界発光素子用材料。
R1、R2はそれぞれ独立に水素原子、ハロゲン原子、炭素数1〜15のアルキル基、置換もしくは無置換の環形成炭素数6〜30のアリール基、または置換もしくは無置換の環形成炭素数1〜30のヘテロアリール基であり、
n、mは1〜4の整数である。
但し、前記Arが、置換もしくは無置換のピレニル基である場合、及び、置換もしくは無置換の2−ビフェニル含有基である場合を除く。
また、前記Arが、置換のフェニル基である場合に、置換もしくは無置換のアントラセニル基によって置換されたもの、及び、置換もしくは無置換のピレニル基によって置換されたものを除く。 - 前記Arは、置換もしくは無置換のフェニル基、ナフチル基、アントラセニル基、フェナントレニル基、ペリレニル基、テトラセニル基、ビフェニル基、ターフェニル基、ナフチルフェニル基、ビフェニレン基、インデニル基、フルオランテニル基、及びフルオレニル基から選択されることを特徴とする、請求項1記載の有機電界発光素子用材料。
- 前記Arは、置換もしくは無置換のフェナントレニル基、ターフェニル基、またはナフチルフェニル基であることを特徴とする、請求項1または2記載の有機電界発光素子用材料。
- 前記Arは、置換もしくは無置換のフェナントレニル基を含むことを特徴とする、請求項3記載の有機電界発光素子用材料。
- 請求項1〜4のいずれか1項に記載の有機電界発光素子用材料を含むことを特徴とする、有機電界発光素子。
- 前記有機電界発光素子用材料は、正孔輸送層に含まれることを特徴とする、請求項5記載の有機電界発光素子。
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JP2014227220A JP6506534B2 (ja) | 2014-11-07 | 2014-11-07 | 有機電界発光素子用材料及びこれを用いた有機電界発光素子 |
KR1020150078685A KR102471097B1 (ko) | 2014-11-07 | 2015-06-03 | 유기 전계 발광 소자용 재료 및 이것을 사용한 유기 전계 발광 소자 |
US14/925,960 US10347844B2 (en) | 2014-11-07 | 2015-10-28 | Material for organic electroluminescent device and organic electroluminescent device using the same |
US16/433,965 US10937969B2 (en) | 2014-11-07 | 2019-06-06 | Material for organic electroluminescent device and organic electroluminescent device using the same |
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US10937969B2 (en) | 2021-03-02 |
US20160133849A1 (en) | 2016-05-12 |
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