JP6626047B2 - ホウ素含有化合物、有機発光ダイオードの発光層及び有機発光ダイオード装置 - Google Patents
ホウ素含有化合物、有機発光ダイオードの発光層及び有機発光ダイオード装置 Download PDFInfo
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- JP6626047B2 JP6626047B2 JP2017135281A JP2017135281A JP6626047B2 JP 6626047 B2 JP6626047 B2 JP 6626047B2 JP 2017135281 A JP2017135281 A JP 2017135281A JP 2017135281 A JP2017135281 A JP 2017135281A JP 6626047 B2 JP6626047 B2 JP 6626047B2
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- light emitting
- formula
- boron
- organic light
- emitting diode
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- 150000001875 compounds Chemical class 0.000 title claims description 55
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 53
- 229910052796 boron Inorganic materials 0.000 title claims description 53
- 239000000463 material Substances 0.000 claims description 44
- 239000002019 doping agent Substances 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 14
- 230000003111 delayed effect Effects 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000243 solution Substances 0.000 description 64
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 42
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000010586 diagram Methods 0.000 description 17
- 238000004896 high resolution mass spectrometry Methods 0.000 description 17
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 10
- 238000005424 photoluminescence Methods 0.000 description 10
- 230000005281 excited state Effects 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 7
- 238000004770 highest occupied molecular orbital Methods 0.000 description 7
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 6
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 6
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
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- NYWMKMGQYATDFJ-UHFFFAOYSA-N BrC1=C(C=C(C=C1C)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)OC)OC)C Chemical compound BrC1=C(C=C(C=C1C)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)OC)OC)C NYWMKMGQYATDFJ-UHFFFAOYSA-N 0.000 description 3
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
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- 239000010931 gold Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzothiophene Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3SC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- FFPUWZLVEGMKAR-UHFFFAOYSA-N 9-(4-bromo-3,5-dimethylphenyl)-3,6-ditert-butylcarbazole Chemical compound BrC1=C(C=C(C=C1C)N1C2=CC=C(C=C2C=2C=C(C=CC1=2)C(C)(C)C)C(C)(C)C)C FFPUWZLVEGMKAR-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
- YDUMUFRPWMBLFH-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)sulfonylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1S(=O)(=O)C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 YDUMUFRPWMBLFH-UHFFFAOYSA-N 0.000 description 1
- QBKVPXLLGMSPNX-UHFFFAOYSA-N 9-[4-[(4-carbazol-9-ylphenyl)-phenylphosphoryl]phenyl]carbazole Chemical compound C=1C=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1P(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)(=O)C1=CC=CC=C1 QBKVPXLLGMSPNX-UHFFFAOYSA-N 0.000 description 1
- MAGWCQAALJWICA-UHFFFAOYSA-N BrC1=C(C=C(C=C1C)N1C2=CC=CC=C2C=2C=CC=CC12)C.BrC1=C(C=C(C=C1C)N1C2=CC=CC=C2C=2C=CC=CC12)C Chemical compound BrC1=C(C=C(C=C1C)N1C2=CC=CC=C2C=2C=CC=CC12)C.BrC1=C(C=C(C=C1C)N1C2=CC=CC=C2C=2C=CC=CC12)C MAGWCQAALJWICA-UHFFFAOYSA-N 0.000 description 1
- CUWNNSIUGLUEAH-UHFFFAOYSA-N BrC1=C(C=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1C)C.BrC1=C(C=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1C)C Chemical compound BrC1=C(C=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1C)C.BrC1=C(C=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1C)C CUWNNSIUGLUEAH-UHFFFAOYSA-N 0.000 description 1
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
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- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
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- 230000007812 deficiency Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group 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
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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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
- H10K85/30—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H—ELECTRICITY
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- 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
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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Description
図1を参照する。図1は、本発明の一実施形態による有機発光ダイオードの発光層140を示す断面模式図である。図1において、発光層140は、本体材料141及びドーパント142を含む。ドーパント142は、式(I)に示す構造を有するホウ素含有化合物である。これにより、この発光層140を含むOLEDに、高効率、低コストであると共に広い光調色性能を提供する等の利点を持たせることができる。式(I)に示す構造を有するホウ素含有化合物について上記を参照し、ここで繰り返して説明しない。
有機発光ダイオードの発光層を含む有機発光ダイオード装置である。これにより、この発光層を含むOLED装置に、高効率、低コストであると共に広い光調色性能を提供する等の利点を持たせることができる。
1H NMR、13C NMR及びHRMSの測定結果から分かるように、実施例1の生成物は、確実に式(I−1−1)に示すホウ素含有化合物であった。
1H NMR(400MHz,CDCl3):δ 8.18(d,J=7.6 Hz,4H),7.77(dd,J=3.6,5.2 Hz,4H),7.63−7.59(m,8H),7.49−7.45(m,4H),7.33−7.29(m,8H),2.22(s,12H);
13C NMR(100MHz,CDCl3):δ141.1,139.7,139.0,134.0,125.8,124.5,124.5,123.3,120.3,119.7. 110.1,22.8;
HRMS Calcd for C52H40B2N2:714.3378. Found:714.3386)
1H NMR(400MHz,CDCl3):δ 8.16(d,J=1.4 Hz,4H),7.76(dd,J=3.2,5.2 Hz,4H),7.60−7.50(m,12H),7.29(s,4H),2.20(s,12H),1.48(s,36H);
13C NMR(100MHz,CDCl3):δ142.6,139.5,139.5,139.5,139.0,133.9,124.1,123.4,123.3,116.2,109.5,34.7,32.1,22.7;
HRMS Calcd for C68H72B2N2:938.5882. Found:938.5884)。
1H NMR(400MHz,CDCl3):δ 7.75(dd,J=3.2,5.2 Hz,4H),7.60−7.58(m,8H),7.52(d,J=8.8,4H),7.27(s,4H),7.10(dd,J=2.4,8.8 Hz,4H),3.97(s,12H),2.20(s,12H);
13C NMR(100MHz,CDCl3):δ153.9,139.6,139.0,137.4,136.5,133.9,124.1,123.5,115.2,111.1,102.8,56.2,22.8;
HRMS Calcd for C56H48B2N2O4:834.3800. Found:834.3778)
1H NMR(400MHz,CDCl3):δ7.68(dd,J=3.2,5.6 Hz,4H),7.51(dd,J=3.2,5.2 Hz,4H),7.30−7.26(m,8H),7.19−7.16(m,8H),7.02−6.98(m,4H),6.81(s,4H),1.97(s,12H);
13C NMR(100MHz,CDCl3):δ 148.2,139.0,138.8,133.5,129.1,124.1,124.1,122.3,122.1,22.7;
HRMS Calcd for C52H44B2N2:718.3691. Found:718.3687)。
図7A〜図7Dを参照する。図7Aは、実施例1の瞬間光ルミネセンス図である。図7Bは、実施例2の瞬間光ルミネセンス図である。図7Cは、実施例3の瞬間光ルミネセンス図である。図7Dは、実施例4の瞬間光ルミネセンス図である。図7A〜図7Dは、実施例1〜4のホウ素含有化合物をトルエンに溶解し、10-5Mの溶液に調製して、300K、真空条件で測定を行う結果であった。図7Aから分かるように、実施例1の蛍光ライフサイクル(τ1)は91.84nsであり、遅延蛍光ライフサイクル(τ2)は3.66・sであった。図7Bから分かるように、実施例2の蛍光ライフサイクルは108.75nsであり、遅延蛍光ライフサイクルは2.68・sであった。図7Cから分かるように、実施例3の蛍光ライフサイクルは103.37nsであり、遅延蛍光ライフサイクルは1.15・sであった。図7Dから分かるように、実施例4の蛍光ライフサイクルは35.04nsであり、遅延蛍光ライフサイクルは1.29・sであった。図7A〜図7Dの測定結果から分かるように、実施例1〜4のホウ素含有化合物は、TADF材料特性を有する。
実施例1〜実施例4のホウ素含有化合物を、合成した後大気環境に置いて、ほぼ5ヶ月以上経過し、更にその1H−NMRスペクトログラムをそれぞれ測定し、実施例1〜実施例4のホウ素含有化合物は大気環境で構造が改変するかどうかを観察した。同時に図3Aと図3Dを参照する。図3Aは、実施例1の1H−NMRスペクトログラムであり、2016年1月3日の測定結果である。図3Dは、実施例1の別の1H−NMRスペクトログラムであり、2016年6月20日の測定結果である。図3Aと図3Dから分かるように、実施例1のホウ素含有化合物を大気環境で5ヶ月以上置いて、その構造が改変しないので、空気/水気安定性を有する。
OLED装置A:実施例1のホウ素含有化合物(I−1−1)を発光層のドーパントとし、ドーピング濃度は10%(重量%)であった。OLED装置Aは、順に陽極、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層及び陰極を含み、OLED装置Aの構造について図2を参照する。OLED装置Aの材質組成及び厚さは、以下のとおりである。ITO(130nm)/NPB(40nm)/TCTA(10nm)/CBP:ホウ素含有化合物(I−1−1)(10%)(30nm)/TmPyPb(60nm)/LiF(1nm)/Al(100nm)。
110:陽極
120:正孔注入層
130:正孔輸送層
140:発光層
141:本体材料
142:ドーパント
150:電子輸送層
160:電子注入層
170:陰極
Claims (7)
- 前記ドーパントの前記発光層におけるドーピング濃度は、5%〜30%である請求項3に記載の有機発光ダイオードの発光層。
- 請求項3〜6のいずれか一項に記載の有機発光ダイオードの発光層を含む有機発光ダイオード装置。
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