WO2022131743A1 - 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 - Google Patents
유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 Download PDFInfo
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- WO2022131743A1 WO2022131743A1 PCT/KR2021/018963 KR2021018963W WO2022131743A1 WO 2022131743 A1 WO2022131743 A1 WO 2022131743A1 KR 2021018963 W KR2021018963 W KR 2021018963W WO 2022131743 A1 WO2022131743 A1 WO 2022131743A1
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- 239000003086 colorant Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 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 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 238000001771 vacuum deposition 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 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
Classifications
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- C07D403/02—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 two hetero rings
- C07D403/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- 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
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- 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
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- 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
- H10K50/16—Electron transporting layers
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- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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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
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Definitions
- the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent electron transport ability and an organic electric field having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including it in one or more organic material layers It relates to a light emitting device.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.
- the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing better natural colors according to the emission color.
- a host/dopant system may be used as a light emitting material.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB, BCP, Alq3, etc. are widely known as materials for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as materials for the light emitting layer.
- metal complex compounds containing Ir such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
- Patent Document 1 Republic of Korea Patent Publication KR2015-7027517
- Patent Document 2 There is a Republic of Korea Patent Publication KR2019-0061314.
- An object of the present invention is to provide a novel compound that can be applied to an organic electroluminescent device, and is excellent in both electron injection and transport ability, light emitting ability, etc. in addition to thermal stability.
- the present invention provides a compound represented by the following formula (1).
- Q 1 To Q 3 are the same as or different from each other, and are each independently a C6 to C10 aromatic ring,
- L is a single bond, or is selected from the group consisting of a C 6 ⁇ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
- R 1 To R 4 are the same as or different from each other, and each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group , C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group , C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group , C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 Monoarylphosphinyl group, C 6 ⁇ C 60 Diarylphosphinyl group, C 6
- A is a substituent represented by the following formula (a),
- Y is S or O
- X 1 to X 4 are the same as or different from each other, and each independently is CH or N, provided that at least two of X 1 to X 4 are N,
- Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl Boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphinyl group, C 6
- the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, wherein at least among the one or more organic material layers One provides an organic electroluminescent device including the compound represented by Formula 1 above.
- the compound according to the present invention has excellent thermal stability, electron injection/transport ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
- the organic electroluminescent device of the present invention comprising the compound in an organic material layer has greatly improved aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.
- the novel compound represented by Formula 1 has a structure in which a single or polycyclic aromatic ring such as a benzene ring and a naphthalene ring is condensed with a spiro structure (eg, fluorene-xanthene) as a core, and , As an electron withdrawing group (EWG) with high electron absorption in the core, a heterocyclic ring (eg, BTP (Benzo[4,5]thieno[3,2-d]pyrimidine), BFP (Benzofuro[3) ,2-d]pyrimidine)) is linked directly or through various linkers (L) as the basic backbone. Since the compound of Formula 1 has excellent electron injection and transport ability, it may exhibit excellent properties as an electron transport layer or an electron transport auxiliary layer material.
- a spiro structure eg, fluorene-xanthene
- EWG electron withdrawing group
- a heterocyclic ring eg, BTP (Benzo[4,5]thieno[3,2-
- the spiro structure basically has very excellent electrochemical stability, has a high glass transition temperature (Tg), has excellent carrier transport ability, and especially exhibits a characteristic that blue light emitting efficiency is increased due to very excellent electron mobility.
- Tg glass transition temperature
- the conjugation length is increased while maintaining the original characteristics of the spiro structure. Lifespan characteristics can be increased by enhancing the thermal stability of the device.
- the compound having a core including the spiro structure may reduce the packing of the core by forming more rings than the compound having fluorene as the core. Therefore, when used as a light emitting layer, the refractive index is increased, thereby improving the efficiency and lifespan of the device.
- a heterocyclic ring eg, Benzo[4,5]thieno[3,2-d]pyrimidine
- BFP having an electron withdrawing ability (EWG) superior to the azine series in the core of the spiro structure
- EWG electron withdrawing ability
- Patent Publication No. 2019-0061314 an organic compound used for an electron transport layer or a hole auxiliary layer, in which a core including a spiro structure is bonded to the 2nd position of a heterocyclic ring (eg, BTP, BFP) The compounds are disclosed.
- the core including the spiro structure is bonded to the 4th position of the heterocycle, and thus the core including the spiro structure is bonded to the 2nd position of the heterocycle.
- electrons are attracted appears stronger, and electron mobility may be improved, and thus the properties of ETL and aETL may be excellent.
- the compound of Formula 1 When the compound of Formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can accept electrons from the cathode well and thus smoothly transfer electrons to the light emitting layer, thereby lowering the driving voltage of the device and improving high efficiency and long lifespan can induce As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.
- the compound of Formula 1 can easily control HOMO and LUMO energy levels according to the direction or position of a substituent, electron mobility may be excellent. Accordingly, the organic electroluminescent device including this compound exhibits high efficiency.
- the compound represented by Formula 1 since the compound represented by Formula 1 has excellent electron transport ability and light emitting properties, it can be used as any one material of the organic material layer of the organic electroluminescent device, such as a light emitting layer, an electron transport layer, and an electron injection layer, preferably For example, it may be used as a material for a light emitting layer of blue phosphorescence, or as a material for an electron transport layer.
- the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (green, red, and blue phosphorescent host material), an electron transport layer/injection layer material, a light emitting auxiliary layer material, It can be used as an electron transport auxiliary layer material, more preferably a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material.
- the performance and lifespan characteristics of the organic electroluminescent device of the present invention including the compound of Formula 1 can be greatly improved, and the performance of a full color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.
- the novel compound represented by Formula 1 has a structure in which a single or polycyclic aromatic ring such as a benzene ring and a naphthalene ring is condensed with a spiro structure (eg, fluorene-xanthene) as a core, and , A structure in which a heterocycle (eg, BTP, BFP) is linked to the core directly or through various linkers (L) is the basic skeleton.
- a spiro structure eg, fluorene-xanthene
- L linkers
- Q 1 to Q 3 are the same as or different from each other, and each independently represent a C6 to C10 aromatic ring.
- Q 1 to Q 3 include a phenylene ring, a naphthalene ring, and the like.
- all of Q 1 to Q 3 may be a C6 aromatic ring, or any one of Q 1 to Q 3 may be a C10 aromatic ring and the rest may be a C6 aromatic ring.
- a to d are integers of 0 to 3.
- a to d when a to d are each 0, it means that hydrogen is not substituted with substituents R 1 to R 4 , respectively.
- a to d when a to d are not 0, specifically, when a to d are an integer of 1 to 3, a plurality of R 1 to R 4 are the same as or different from each other, and each independently, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 Aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40
- Q 1 to Q 3 is a heterocyclic ring bonded directly to the condensed core or through a separate linker (L), a substituent a having excellent electron transport ability as a type of electron withdrawing group (Electron Withdrawing Group, EWG) appears as A.
- Y is S or O
- X 1 to X 4 are the same as or different from each other, and are each independently CH or N, provided that X 1 to X 4 At least two are N. Since the substituent a exhibits stronger EWG than the azine series, it exhibits excellent electron absorption properties, which is advantageous for electron injection and transport.
- Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 Monoarylphosphinyl group, C 6 ⁇ C 60 Diarylphosphinyl group,
- the Ar 1 is selected from the group consisting of a C 6 ⁇ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and the aryl group and the heteroaryl group of A 1 are deuterium (D), halogen, Cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocyclo of 3 to 40 nuclear atoms Alkyl group, C 6 ⁇ C 60 Aryl group, nuclear atom number 5 to 60 heteroaryl group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkylsilyl Group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Arylphosphine
- D
- two of X 1 to X 4 may be N.
- the formula a may be embodied as the following formula a-1.
- the aforementioned substituent A may be directly bonded to the core or may be bonded through a separate linker (L).
- L a separate linker
- the linker (L) may be a linker of a conventional divalent group known in the art.
- L is a single bond or C 6 ⁇ C 18 It may be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms.
- n is an integer of 0 to 3, specifically 0 to 2.
- L is a single bond
- n is an integer of 1 to 3
- L is a divalent linker, a C 6 ⁇ C 18 arylene group and It may be selected from the group consisting of a heteroarylene group having 5 to 18 nuclear atoms.
- L may be further specified as a single bond or a linker selected from the following structural formula.
- * means a portion where a bond with Chemical Formula 1 is formed.
- the compound represented by Formula 1 may be more specific to a compound represented by any one of Formulas 2 to 5 below, depending on the type and position of a ring condensed on the core.
- the present invention is not limited thereto.
- Q 1 to Q 3 are each a C10 aromatic ring
- L, R 1 to R 4 , A, a to d, and n are each as defined in Formula 1.
- the compound represented by Formula 1 may be more specific to a compound represented by any one of Formulas 6 to 12 below, depending on the type and position of a ring condensed on the core.
- the present invention is not limited thereto.
- L, A, and n are each as defined in Formula 1.
- the compound represented by Formula 1 may be more specific to a compound represented by any one of Formulas 13 to 18 below depending on the position of the linker (L) bonded to the core.
- the present invention is not limited thereto.
- Q 1 to Q 3 , L, R 1 to R 4 , A, a to d, and n are each as defined in Formula 1.
- the electron mobility may be improved compared to the case where the substituent A is coupled to the top of the spiro compound.
- the compound represented by Formula 1 according to the present invention described above may be further embodied as the following exemplary compounds, for example, Compounds 1 to 361.
- the compound represented by Formula 1 of the present invention is not limited by those exemplified below.
- alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
- alkenyl refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
- alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined.
- two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms.
- one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
- R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure.
- R' means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
- arylamine refers to an amine substituted with an aryl having 6 to 40 carbon atoms.
- cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se.
- heterocycloalkyl include, but are not limited to, morpholine and piperazine.
- alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl refers to silyl substituted with aryl having 5 to 40 carbon atoms.
- condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
- the present invention provides an electron transport layer comprising the compound represented by the formula (1).
- the electron transport layer serves to move electrons injected from the cathode to an adjacent layer, specifically, the light emitting layer.
- the compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
- ETL electron transport layer
- the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
- the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compound, aluminum complex (eg, Alq 3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complex (eg, Gaq'2OPiv, Gaq) '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.
- the present invention provides an electron transport auxiliary layer comprising the compound represented by the formula (1).
- the electron transport layer is disposed between the emission layer and the electron transport layer, and serves to prevent the excitons or holes generated in the emission layer from diffusing into the electron transport layer.
- the compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
- the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
- the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a nitrogen-containing heterocyclic derivative, and the like.
- the compound of Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and may be appropriately adjusted within a range known in the art.
- another aspect of the present invention relates to an organic electroluminescent device (hereinafter, 'organic EL device') including the compound represented by the above-described formula (1).
- the organic electroluminescent device includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above.
- the compound may be used alone, or two or more may be used in combination.
- the at least one organic material layer may be any one or more of a light emitting layer, a light emission auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer, and at least one organic material layer is represented by Formula 1 compounds that become Specifically, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer, an electron transport layer, and an electron transport auxiliary layer.
- the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and in this case, the compound of Formula 1 may be included as the host material.
- the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.
- the compound represented by Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic electroluminescent device (luminous efficiency and power efficiency), lifespan, luminance, and driving voltage can be improved.
- the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a blue and/or green phosphorescent host, a fluorescent host, or a dopant material.
- the compound represented by Formula 1 of the present invention since the compound represented by Formula 1 of the present invention has excellent electron injection and transport ability, it is preferably an electron transport layer material.
- the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
- at least one of the light emitting auxiliary layer, the light emitting layer, the electron transport layer, and the electron injection layer may include the compound represented by Formula 1 above.
- an electron injection layer may be additionally stacked on the electron transport layer.
- the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
- the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. have.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
- the substrate usable in the present invention is not particularly limited, and non-limiting examples include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.
- examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.
- metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof
- metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
- combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb
- conductive polymers such as polythiophene, poly(3
- examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- the hole injection layer, the light emitting layer, the electron transport layer and the electron injection layer are not particularly limited, and common materials known in the art may be used.
- a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was ultrasonically cleaned with distilled water. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE washer (Power sonic 405, Hwashin Tech), washed for 5 minutes using UV, and coated with a vacuum evaporator. The substrate was transferred.
- ITO indium tin oxide
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were respectively used as the electron transport layer material instead of the compound 2 used as the light emitting layer material in Example 1.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compounds Alq 3 , T-1, and T-2 were respectively used instead of Compound 2 as the electron transport layer material.
- Example 10 compound 211 3.9 456 10.3
- Example 16 compound 321 3.6 456 8.2 Comparative Example 1 Alq 3 5.4 458 5.5 Comparative Example 2 T-1 4.5 459 5.9 Comparative Example 3 T-2 4.4 458 6.0
- the blue organic electroluminescent device (Examples 1 to 16) using the compound according to the present invention for the electron transport layer is a blue organic electroluminescent device using the conventional Alq 3 for the electron transport layer (Comparative Example 1) Compared to that, it was found to exhibit superior performance in terms of driving voltage, luminescence peak and current efficiency.
- a blue organic electroluminescent device was prepared in the same manner as in Example 18, except that the compounds shown in Table 2 below were used as the electron transport auxiliary layer material instead of the compound 2 used as the electron transport auxiliary layer material in Example 18. produced.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that compounds Alq 3 , T-1, and T-2 were respectively used instead of compound 2 as the electron transport auxiliary layer material.
- Example 17 compound 2 3.8 454 8.5
- Example 18 compound 7 3.7 456 8.9
- Example 19 compound 30 3.9 457 8.7
- Example 20 compound 50 3.5 452 9.3
- Example 21 compound 61 3.4 455 9.5
- Example 22 compound 98 3.6 452 9.2
- Example 23 compound 125 3.7 453 9.5
- Example 24 compound 138 3.2 454 8.8
- Example 25 compound 161 3.8 455 8.7
- Example 26 compound 211 3.2 454 10.0
- Example 27 compound 231 3.2 454 10.0
- Example 28 compound 286 3.3 456 10.1
- Example 30 compound 311 3.5 452 8.7
- Example 31 compound 312 3.1 455 10.3
- Example 32 compound 321 3.6 452 10.1 Comparative Example 4 - 4.8 458 6.0 Comparative Example 5 T-1 4.7 457 6.1 Comparative Example 6 T-2 4.6 456 6.2
- the blue organic electroluminescent devices (Examples 17 to 32) using the compound according to the present invention as the electron transport auxiliary layer were blue organic electroluminescent devices that did not include the electron transport auxiliary layer (Comparative Example 4). ), it was found that it showed superior performance in terms of driving voltage, luminescence peak and current efficiency.
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Abstract
Description
샘플 | 전자 수송층 재료 | 구동전압 (V) |
발광피크 (nm) |
전류효율 (cd/A) |
실시예 1 | 화합물 2 | 3.2 | 454 | 10.0 |
실시예 2 | 화합물 7 | 3.3 | 456 | 10.1 |
실시예 3 | 화합물 30 | 3.2 | 457 | 9.9 |
실시예 4 | 화합물 50 | 3.5 | 452 | 8.7 |
실시예 5 | 화합물 61 | 3.1 | 455 | 10.3 |
실시예 6 | 화합물 98 | 3.6 | 452 | 10.1 |
실시예 7 | 화합물 125 | 3.7 | 453 | 9.9 |
실시예 8 | 화합물 138 | 3.2 | 454 | 8.8 |
실시예 9 | 화합물 161 | 3.8 | 455 | 8.7 |
실시예 10 | 화합물 211 | 3.9 | 456 | 10.3 |
실시예 11 | 화합물 231 | 4.0 | 456 | 10.1 |
실시예 12 | 화합물 286 | 3.6 | 456 | 9.9 |
실시예 13 | 화합물 295 | 3.7 | 456 | 9.9 |
실시예 14 | 화합물 311 | 3.8 | 456 | 8.8 |
실시예 15 | 화합물 312 | 3.5 | 456 | 8.7 |
실시예 16 | 화합물 321 | 3.6 | 456 | 8.2 |
비교예 1 | Alq3 | 5.4 | 458 | 5.5 |
비교예 2 | T-1 | 4.5 | 459 | 5.9 |
비교예 3 | T-2 | 4.4 | 458 | 6.0 |
샘플 | 전자수송 보조층 재료 | 구동전압 (V) |
발광피크 (nm) |
전류효율 (cd/A) |
실시예 17 | 화합물 2 | 3.8 | 454 | 8.5 |
실시예 18 | 화합물 7 | 3.7 | 456 | 8.9 |
실시예 19 | 화합물 30 | 3.9 | 457 | 8.7 |
실시예 20 | 화합물 50 | 3.5 | 452 | 9.3 |
실시예 21 | 화합물 61 | 3.4 | 455 | 9.5 |
실시예 22 | 화합물 98 | 3.6 | 452 | 9.2 |
실시예 23 | 화합물 125 | 3.7 | 453 | 9.5 |
실시예 24 | 화합물 138 | 3.2 | 454 | 8.8 |
실시예 25 | 화합물 161 | 3.8 | 455 | 8.7 |
실시예 26 | 화합물 211 | 3.2 | 454 | 10.0 |
실시예 27 | 화합물 231 | 3.2 | 454 | 10.0 |
실시예 28 | 화합물 286 | 3.3 | 456 | 10.1 |
실시예 29 | 화합물 295 | 3.2 | 457 | 9.9 |
실시예 30 | 화합물 311 | 3.5 | 452 | 8.7 |
실시예 31 | 화합물 312 | 3.1 | 455 | 10.3 |
실시예 32 | 화합물 321 | 3.6 | 452 | 10.1 |
비교예 4 | - | 4.8 | 458 | 6.0 |
비교예 5 | T-1 | 4.7 | 457 | 6.1 |
비교예 6 | T-2 | 4.6 | 456 | 6.2 |
Claims (15)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 화학식 1에서,Q1 내지 Q3은 서로 동일하거나 상이하며, 각각 독립적으로 C6 내지 C10의 방향족고리이고,L은 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노아릴포스피닐기, C6~C60의 디아릴포스피닐기, C6~C60의 아릴아민기, C5~C60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택되며,A는 하기 화학식 a로 표시되는 치환기이며,[화학식 a]상기 화학식 a에서,*는 화학식 1에 결합되는 부분을 의미하고,Y는 S 또는 O이고,X1 내지 X4는 서로 동일하거나 상이하며, 각각 독립적으로 CH 또는 N이고, 다만 X1 내지 X4 중 적어도 2개는 N이고,Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노아릴포스피닐기, C6~C60의 디아릴포스피닐기, C6~C60의 아릴아민기, C5~C60의 아릴헤테로아릴아민기 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택되고,a 내지 d와 n은 각각 0 내지 3의 정수이고,상기 L의 아릴렌기, 헤테로아릴렌기와 R1 내지 R4, 및Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노아릴포스피닐기, 디아릴포스피닐기, 아릴아민기, 아릴헤테로아릴아민기 및 헤테로아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기, C6~C60의 아릴아민기, C5~C60의 아릴헤테로아릴아민기, 및 핵원자수 5 내지 60개의 헤테로아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제1항에 있어서,상기 X1 내지 X4는 중 2개는 N인 화합물.
- 제1항에 있어서,상기 Ar1은 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 구성된 군에서 선택되고,상기 A1의 아릴기 및 헤테로아릴기는, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이한 것인 화합물.
- 제1항에 있어서,상기 화학식 1로 표시되는 화합물은 전자수송층 또는 전자수송 보조층 재료인 화합물.
- 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제12항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.
- 제13항에 있어서,상기 화합물을 포함하는 유기물층은 발광층, 발광보조층, 정공주입층, 정공수송층, 전자주입층, 전자수송층, 및 전자수송 보조층으로 구성된 군에서 선택되는 유기 전계 발광 소자.
- 제13항에 있어서,상기 화합물을 포함하는 유기물층은 발광층, 전자수송층 또는 전자수송 보조층인 유기 전계 발광 소자.
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