JP6900457B2 - 遅延蛍光化合物と、それを含む有機発光ダイオードおよび有機発光表示装置 - Google Patents
遅延蛍光化合物と、それを含む有機発光ダイオードおよび有機発光表示装置 Download PDFInfo
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- JP6900457B2 JP6900457B2 JP2019220169A JP2019220169A JP6900457B2 JP 6900457 B2 JP6900457 B2 JP 6900457B2 JP 2019220169 A JP2019220169 A JP 2019220169A JP 2019220169 A JP2019220169 A JP 2019220169A JP 6900457 B2 JP6900457 B2 JP 6900457B2
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- light emitting
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- organic light
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Description
1.化合物1−1の合成
(1)化合物A−2
(1)化合物B−1
陽極(ITO)上に、正孔注入層(HATCN、化学式4、7nm)、正孔輸送層(NPB、化学式5、55nm)、電子遮断層(m−CBP、化学式6、10nm)、発光物質層(35nm)、正孔遮断層(B3PYMPM、化学式7、10nm)、電子輸送層(TPBi、化学式8、20nm)、電子注入層(LiF)、陰極(Al)を順次積層した。
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式9の化合物(30重量%)を用いて発光物質層を形成した。
(2)比較例2
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式10の化合物(30重量%)を用いて発光物質層を形成した。
(3)実験例1
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式2の化合物1−1(30重量%)を用いて発光物質層を形成した。
(4)実験例2
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式2の化合物1−2(30重量%)を用いて発光物質層を形成した。
(5)実験例3
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式2の化合物1−6(30重量%)を用いて発光物質層を形成した。
(6)実験例4
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式2の化合物2−2(30重量%)を用いて発光物質層を形成した。
(7)実験例5
ホストに化学式3の化合物H−1(70重量%)を用いて、ドーパントに化学式2の化合物3−2(30重量%)を用いて発光物質層を形成した。
すなわち、遅延蛍光化合物において、逆系間交差により、遅延蛍光化合物の三重項エネルギーが遅延蛍光化合物の一重項エネルギーに変換され、遅延蛍光化合物の一重項エネルギーが蛍光化合物の一重項エネルギーへ伝達される。このとき、遅延蛍光化合物は、三重項エネルギーと一重項エネルギーとの差が0.3eVより小さい。それにより、遅延蛍光化合物の三重項エネルギーが遅延蛍光化合物の一重項エネルギーへ変換される逆系間交差(Reverse Inter System Crossing;RISC)が起こる。
第1層442は、本発明の遅延蛍光化合物をドーパントとして含み、第2層444と第3層446のそれぞれは、蛍光化合物をドーパントとして含む。第2層444と第3層446の蛍光化合物は、同じであってもよく、異なってもよい。遅延蛍光化合物の一重項エネルギーは、蛍光化合物の一重項エネルギーより大きい。
Claims (17)
- 第1電極と、
前記第1電極と対向する第2電極と、
前記第1電極と前記第2電極の間に位置する第1発光物質層とを備え、
前記第1発光物質層は、請求項1または2に記載の遅延蛍光化合物を含む有機発光ダイオード。 - 前記遅延蛍光化合物は、第1ドーパントとして用いられ、
前記第1発光物質層は、第1ホストをさらに含むことを特徴とする、請求項3に記載の有機発光ダイオード。 - 前記第1ホストの最高被占軌道レベル(HOMOHost)と前記第1ドーパントの最高被占軌道レベル(HOMODopant)との差(│HOMOHost−HOMODopant│)、または前記第1ホストの最低空軌道レベル(LUMOHost)と前記第1ドーパントの最低空軌道レベル(LUMODopant)との差(│LUMOHost−LUMODopant│)は、0.5eV以下であることを特徴とする、請求項4に記載の有機発光ダイオード。
- 前記第1発光物質層は、第2ドーパントをさらに含み、
前記第1ドーパントの一重項エネルギーは、第2ドーパントの一重項エネルギーより大きいことを特徴とする、請求項4に記載の有機発光ダイオード。 - 前記第1ドーパントの三重項エネルギーは、前記第1ホストの三重項エネルギーより小さく、前記第2ドーパントの三重項エネルギーより大きいことを特徴とする、請求項7に記載の有機発光ダイオード。
- 第2ホストと第1蛍光ドーパントとを含み、前記第1電極と前記第1発光物質層との間に位置する第2発光物質層をさらに含むことを特徴とする、請求項4に記載の有機発光ダイオード。
- 前記第1電極と前記第2発光物質層との間に位置する電子遮断層をさらに含み、前記第2ホストは、前記電子遮断層の物質と同じであることを特徴とする、請求項9に記載の有機発光ダイオード。
- 第3ホストと第2蛍光ドーパントとを含み、前記第1発光物質層と前記第2電極との間に位置する第3発光物質層をさらに含むことを特徴とする、請求項9に記載の有機発光ダイオード。
- 前記第2電極と前記第3発光物質層との間に位置する正孔遮断層をさらに含み、前記第3ホストは、前記正孔遮断層の物質と同じであることを特徴とする、請求項11に記載の有機発光ダイオード。
- 前記第1ドーパントの一重項エネルギーは、前記第1蛍光ドーパントおよび前記第2蛍光ドーパントの一重項エネルギーより大きいことを特徴とする、請求項11に記載の有機発光ダイオード。
- 前記第1ホストの一重項エネルギーと三重項エネルギーのそれぞれは、前記第1ドーパントの一重項エネルギーと三重項エネルギーより大きく、
前記第2ホストの一重項エネルギーは、前記第1蛍光ドーパントの一重項エネルギーより大きく、
前記第3ホストの一重項エネルギーは、前記第2蛍光ドーパントの一重項エネルギーより大きいことを特徴とする、請求項11に記載の有機発光ダイオード。 - 前記第1ドーパントの一重項エネルギーは、前記第1蛍光ドーパントの一重項エネルギーより大きいことを特徴とする、請求項9に記載の有機発光ダイオード。
- 前記第1ホストの一重項エネルギーと三重項エネルギーのそれぞれは、前記第1ドーパントの一重項エネルギーと三重項エネルギーより大きく、前記第2ホストの一重項エネルギーは、前記第1蛍光ドーパントの一重項エネルギーより大きいことを特徴とする、請求項9に記載の有機発光ダイオード。
- 基板と、
前記基板の上に位置する請求項3ないし請求項16のうち、いずれか1項に記載の有機発光ダイオードとを備える有機発光表示装置。
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