WO2018236066A1 - 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자 - Google Patents
신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자 Download PDFInfo
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- WO2018236066A1 WO2018236066A1 PCT/KR2018/006165 KR2018006165W WO2018236066A1 WO 2018236066 A1 WO2018236066 A1 WO 2018236066A1 KR 2018006165 W KR2018006165 W KR 2018006165W WO 2018236066 A1 WO2018236066 A1 WO 2018236066A1
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 5
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- 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
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer 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
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000010345 tape casting 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
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 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
- 238000007740 vapor deposition Methods 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- 239000011787 zinc oxide Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- H10K50/16—Electron transporting 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
- the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.
- the organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode.
- the organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device.
- the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
- Patent Literature [Patent Document 0001] Korean Patent Publication No. 10-2013-073537 [0003]
- the present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.
- the present invention provides a compound represented by the following formula (1).
- Each of 3 ⁇ 4 and 3 ⁇ 4 is independently a substituted or unsubstituted d- 60 alkyl or a substituted or unsubstituted C 6 -60 aryl,
- Li and L 3 are each independently a direct bond or a substituted or unsubstituted C 6 -60 arylene,
- Xi, 3 ⁇ 4 and 3 ⁇ 4 are each independently N or CR 'with the proviso that at least one of them is N,
- R ' is hydrogen or a substituted or unsubstituted ( 60 alkyl
- An and Ar 2 are each independently substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted C 5 -C 60 heteroaryl containing at least one of O and S, pyridinyl, pyrimidinyl, triazinyl , ≪ / RTI > carbazolyl, isoquinolinyl or quinazolinyl,
- the present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes the compound of the present invention.
- the compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device.
- the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.
- Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
- the present invention provides a compound represented by the following formula (1).
- Each of 3 ⁇ 4 and 3 ⁇ 4 is independently substituted or unsubstituted d-60 alkyl or substituted or unsubstituted C 6 -60 aryl, , And each independently represent a direct bond, or a substituted or unsubstituted
- X 2 and X 3 are each independently N or CR 'with the proviso that at least one of them is N,
- R ' is hydrogen or substituted or unsubstituted alkyl
- An and Ar 2 are each independently substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted C 5 -C 60 heteroaryl containing at least one of O and S, pyridinyl, pyrimidinyl, triazinyl , Wherein at least one of An and Ar 2 is a substituted or unsubstituted C 5 -C 60 heteroarylpyridinyl containing at least one of O and S, Lower alkoxy, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl, lower alkoxycarbonyl,
- I and i mean a bond connected to another substituent.
- substituted or unsubstituted 1 refers to a substituent selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxyl, carbonyl, ester, An aryloxy group, an aryloxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, An arylamine group, an arylphosphine group, or a heterocyclic group containing at least one of N, O and S atoms, or may be substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms, The substituent group to which at least two substituents
- the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group.
- it may be a compound of the following structural form, but is not limited thereto.
- the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group
- the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
- alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, Pentyl, neopentyl, tert-pentyl, n-butyl, n-butyl, 1-methylpentyl, 2-methylpentyl, N-heptyl, 1-methylnucleosilyl, cyclopentylmethyl, cyclohectylmethyl, octyl, n -octyl, tert-octyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like.
- the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms.
- the number of carbon atoms of the cycloalkyl group is 3 to 20.
- the cycloalkyl group has 3 to 6 carbon atoms.
- Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- , 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
- the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. When the aryl group is a monocyclic
- Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
- a fluorenyl group may be substituted, and a fluorenyl group having two substituents
- the heterocyclic group is a hetero ring group containing at least one of O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
- heterocyclic group examples include a thiophene group, a furan group, a pyrrolyl group, a pyrrolyl group, a pyrrolyl group, a triaryl group, a triazole group, a thiophene group, , An acridyl group, a pyridazine group, a pyrazinyl group quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrimidinyl group, a pyrazinopyranyl group isoquinoline group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a phenanthroline group, a thiazolyl group, a thiazoly
- the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.
- the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.
- the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.
- the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
- the description of the aryl group described above can be applied except that arylene is a divalent group.
- the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.
- the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other.
- the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
- the compound represented by the formula (1) may be a compound represented by any one of the following formulas (1-1) to (1-5).
- L 1 and L 3 are each independently composed of -
- L < 3 > are each independently a direct bond or two Lt; / RTI >
- each of 3 ⁇ 4 and 3 ⁇ 4 may independently be methyl or benzyl.
- the compound represented by the formula (1) may be any one selected from the group consisting of
- the first intermediates 1, 2 and 3 can be produced according to the reaction formula 1-1 to 1-3.
- first intermediates 1, 2 and 3 may be reacted with the second intermediates 4, 5 and 6 according to the reaction scheme 2.
- the compound of the formula (1) of the present invention can be prepared according to the reaction scheme 4 using the first intermediates 1, 2 and 3 as reactants.
- the present invention provides an organic light emitting device including the compound represented by Formula 1.
- the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.
- the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
- the structure of the organic light emitting device it is not limited to this but may comprise a smaller number of organic layers.
- the organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And a compound to be displayed.
- the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
- the organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1).
- the electron transporting layer, the electron injecting layer, or the layer which simultaneously injects electrons and transports electrons includes the compound represented by the above formula (1).
- the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or more, high triple energy (ET), and hole stability
- n-type interpolymers used in the art can be commonly used.
- the organic material layer may include a light emitting layer and an electron transporting layer
- the electron transporting layer may include a compound represented by the general formula (1).
- the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
- FIGS. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
- the compound represented by Formula 1 may be included in the light emitting layer.
- the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.
- the organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
- the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
- the organic light emitting device includes a first electrode, An organic material layer and a gate electrode may be successively laminated.
- a PVD (physico-vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity on the substrate or an alloy thereof A hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a substance usable as a cathode is deposited thereon.
- an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
- the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
- the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, coating, and the like, but is not limited thereto.
- an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode and the second electrode is a cathode.
- the anode material a material having a large work function is preferably used so as to smoothly inject holes into the organic material layer.
- the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ⁇ 0: ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; Poly (3-methylthiophene), poly [3, 4- (ethylene-1,2-dioxy) thiophene KPED0T), but are polypyrrole and polyaniline, but are not limited thereto.
- the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
- the negative electrode material include metals such as magnes, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but the present invention is not limited thereto.
- the hole injecting layer is a layer for injecting holes from an electrode.
- the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
- a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable.
- the HOMO concentration of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer.
- the hole injecting material include organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material.
- the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
- the light emitting layer may include a host material and a dopant material.
- the host material is a condensed aromatic ring derivative or a heterocyclic compound.
- condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
- heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, but are not limited thereto.
- splittable material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
- aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
- styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
- the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
- the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
- the electron harvest can be used with any desired cathode material as used according to the prior art.
- An example of a material is a conventional material having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
- the electron injection layer is a layer for injecting electrons from the electrode.
- the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
- a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphthalato) gallium, and the like But is not limited thereto.
- the organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
- the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
- the preparation of the compound represented by Formula 1 and the organic light emitting device including the compound represented by Formula 1 will be described in detail below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
- compound D 10.10 g, 20.86 liters
- 2-chi or o-4,6-di pyridi ⁇ -2-
- tetrakis (triphenylphosphine) palladium 0.63 g , 0.54 ol ol
- ITOC indium tin oxide ITOC indium tin oxide thin film coated with a thickness of 1,000A was placed in distilled water containing detergent and washed with ultrasonic waves.
- Fischer Co. was used as a detergent
- distilled water which was filtered with a filter of a product manufactured by Mi 11 ipore Co.
- ITO was washed for 30 minutes and then repeated twice with distilled water for 10 minutes.
- isopropyl alcohol, acetone, and methane were ultrasonically washed with a solvent, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
- Hexa nitrile tetra phenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 100A on the ⁇ key transparent electrode thus prepared to form a hole injection layer.
- BH and BD were vacuum deposited on the electron blocking layer to a thickness of 200 A at a weight ratio of 25: 1 to form a light emitting layer.
- the compound [HB 1] was vacuum deposited on the hole transporting layer to a thickness of 50 A on the light emitting layer to form a hole blocking layer.
- the compound ET 1 and the compound LiQCLi thium quinolate were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 310A.
- Lithium fluoride (LiF) and aluminum were deposited on the electron injecting and transporting layer sequentially to a thickness of 12A and thickness of ⁇ and ⁇ to form a cathode.
- the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
- the deposition rate of the lyrium fluoride of the cathode was 0.3 A / sec
- the deposition rate of the aluminum was 2 A / sec. - 7 ⁇ 5 ⁇ 1 ( ⁇ 6 torr) to fabricate an organic light emitting device.
- An organic light emitting device was prepared by using the compound described in Table 1 instead of the compound HB 1 used in Experimental Example 1.
- An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compound HB 2 was used instead of the compound EB 1 in Example 1-1.
- An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that the following compound EB 3 was used instead of the compound EB 1 in Example 1 (1).
- T95 means the time required for the luminance to decrease from the initial luminance (1300 n t) to 95%.
- the organic light emitting device manufactured using the compound of the present invention as a hole blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device. High efficiency and long life characteristics than the organic light emitting devices prepared using Comparative Example 1 and 9 of Spirob et al. Core and Comparative Example 2 of 10-dimetyl fluorouene core as the hole blocking layer.
- the core of the present invention has a relatively higher electron content than Spirobium luorene and 9,10-dimetyl fluorouene, and shows a stronger voltage and efficiency without sacrificing lifetime when used as a hole blocking layer .
- Table 1 it was confirmed that the compounds according to the present invention are excellent in hole blocking ability and applicable to organic light emitting devices. ≪ Examples 2-1 to 2-22 >
- An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that ET2 was used in place of ET1 as the electron transport layer in Experimental Example 1.
- the device was fabricated.
- An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of ET 4 was used instead of ET 1 as a layer in Example 1.
- T95 means the time required for the luminance to decrease from the initial luminance (1300 n t) to 95%.
- Example 2-6 Compound 6 4.53 46.55 (0.142, 0.047) 295
- Example 2-6 Compound 7 4.64 46.68 (0.141, 0.045) 280
- Example 2-7 Compound 8 4.65 46.77 (0.142, 0.044) 290
- Example 2-8 Compound 9 4.56 46.89 310
- Example 2-9 Compound 10 4.67 46.63 (0.143, 0.045) 295
- Example 2-10 Compound 11 4.68 46.47 (0.138, 0.044) 285
- Example 2-11 Compound 12 4.69 45.75 (0.142, 0.045) 275
- Examples 2-12 Compound 13 Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No. Compound No
- the core of the present invention has a higher electron content than Spirobif luorene and 9,10-dimetylf luorene core, and the lifetime is increased by 153 ⁇ 4 to 30% when used as an electron transport layer.
- substrate 2 anode
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Abstract
본 발명은 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자를 제공한다.
Description
【발명의 명칭】
신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
【기술분야】
관련 출원 (들)과의 상호 인용
본 출원은 2017년 6월 21일자 한국 특허 출원 제 10-2017-0078694호 에 기초한 우선권의 이익을 주장하며， 해당 한국 특허 출원의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다. 본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.
【배경기술】
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각， 우수한 콘트라스트， 빠른 응답 시간을 가지며, 휘도， 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며， 예컨대 정공주입층， 정공수송층， 발광층， 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이， 음극에서는 전자가 유기물층에 주입되게 되고， 주입된 정공과 전자가 만났을 때 엑시톤 (exci ton)이 형성되며， 이 액시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.
【선행기술문헌】
【특허문헌】
(특허문헌 0001) 한국특허 공개번호 제 10-2013-073537호 【발명의 내용】
【해결하려는 과제】
본 발명은 신규한 헤테로고리 화합물 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.
【과제의 해결 수단】
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.
상기 화학식 1에서，
¾ 및 ¾ 는 각각 독립적으로 치환 또는 비치환된 d-60의 알킬 또는 치환 또는 비치환된 C6-60 아릴이고，
Li , 및 L3는 각각 독립적으로， 직접결합， 또는 치환 또는 비치환된 C6-60 아릴렌이고，
Xi, ¾ 및 ¾는 각각 독립적으로 N 또는 CR' 이고， 단， 이들 중 하나 이상이 N이고，
R' 은 수소 또는 치환 또는 비치환된 ( 60의 알킬이고，
An 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴, 0 및 S 중 1개 이상을 포함하는 치환 또는 비치환된 C5-60 헤테로아릴， 피리디닐， 피리미디닐， 트리아지닐， 카바졸릴， 이소퀴놀리닐 또는 퀴나졸리닐이고, 단，
An 및 Ar2 중 하나 이상이， 0 및 S 중 1개 아상을 포함하는 치환 또는 비치환된 C5-60 헤테로아릴， 피리디닐， 피리미디닐, 트리아지닐， 카바졸릴， 이소퀴놀리닐 또는 퀴나졸리닐이다.
또한， 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 게 2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 전술한 본 발명의 화합물을 포함하는 유기 발광 소자를 제공한다.
【발명의 효과】
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며， 유기 발광 소자에서 효율의 향상， 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 특히， 상술한 화학식 1로 표시되는 화합물은 정공주입， 정공수송， 정공주입 및 수송, 발광， 전자수송， 또는 전자주입 재료로 사용될 수 있다.
【도면의 간단한 설명】
도 1은 기판 (1)， 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1)， 양극 (2)， 정공주입층 (5)， 정공수송층 (6)， 발광층 (7)， 전자수송층 (8) 및 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 【발명을 실시하기 위한 구체적인 내용】
이하， 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다. 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.
상기 화학식 1에서 ,
. ¾ 및 ¾ 는 각각 독립적으로 치환 또는 비치환된 d-60의 알킬 또는 치환 또는 비치환된 C6-60 아릴이고，
, 및 는 각각 독립적으로， 직접결합， 또는 치환 또는 비치환된
Cg-60 아릴렌이고，
， X2 및 X3는 각각 독립적으로 N 또는 CR' 이고， 단, 이들 중 하나 이상이 N이고，
R' 은 수소 또는 치환 또는 비치환된 의 알킬이고，
An 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴， 0 및 S 중 1개 이상을 포함하는 치환 또는 비치환된 C5— 60 헤테로아릴， 피리디닐, 피리미디닐， 트리아지닐, 카바졸릴， 이소퀴놀리닐 또는 퀴나졸리닐이고， 단， An 및 Ar2 중 하나 이상이， 0 및 S 중 1개 이상을 포함하는 치환 또는 비치환된 C5-60 헤테로아릴 피리디닐， 피리미디닐， 트리아지닐， 카바졸릴， 이소퀴놀리닐 또는 퀴나졸리닐이다.
본 명세서에서, I 및 i 는 다른 치환기에 연결되는 결합을 의미한다. 본 명세서에서 "치환 또는 비치환된1' 이라는 용어는 중수소; 할로겐기 ; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N , 0 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대， "2 이상의 치환기가 연결된 치환기 "는 비페닐기일 수 있다. 즉， 비페닐기는 아릴기일 수도 있고， 2개의 페닐기가 연결된 치환기로 해석될 수 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.
^릴기. 페닐기， 바이페닐기， 터페닐기 등이 될 수 있으나， 이에 한정되 것은 아니다. 상기 다환식 아릴기로는 나프틸기， 안트라세닐기， 페난트릴기， 파이레닐기， 페릴레닐기， 크라이세닐기， 플루오레닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 본 명세서에 있어서， 플루오레닐기는 치환될 수 있고， 치환기 2개가 되는
등0
본 명세서에 있어서， 헤테로고리기는 이종 원소로 0， N , Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서， 탄소수는 특별히 한정되지 않으나ᅳ 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기， 퓨란기 , 피를기， 이미다졸기， 티아졸기， 옥사졸기， 옥사디아졸기， 트리아졸기， 피리딜기， 비피리딜기, 피리미딜기， 트리아진기， 트리아졸기， 아크리딜기, 피리다진기， 피라지닐기 퀴놀리닐기， 퀴나졸린기， 퀴녹살리닐기， 프탈라지닐기, 피리도 피리미디닐기， 피리도 피라지닐기， 피라지노 피라지닐기 이소퀴놀린기， 인돌기， 카바졸기， 벤조옥사졸기， 벤조이미다졸기， 벤조티아졸기， 벤조카바졸기， 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기， 페난쓰를린기 (phenanthrol ine) , 티아졸릴기 , 이소옥사졸릴기， 옥사디아졸릴기， 티아디아졸릴기， 벤조티아졸릴기， 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다. 본 명세서에 있어서， 아르알킬기， 아르알케닐기， 알킬아릴기， 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서， 아르알킬기， 알킬아릴기， 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서， 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서， 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 탄화수소 고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 헤테로고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 바람직하게는， 상기 화학식 1로 표시되는 화합물은， 하기 화학식 1-1 내지 1-5 중 어느 하나로 표시되는 화합물일 수 있다.
[화학식 1-4]
상기 화학식 1—1 내지 1-5 에서,
Ri, ， L1; L2, , An 및 Ar2는 앞서 정의한 바와 같다. 바람직하게는， , 및 L3는 각각 독립적으로 하기로 구성되- 군으로
.
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
PLil/ l\H IU\Q / U U D D 0
//: O8SSMI>d 9909ΏAV
마지막으로, 제 2 중간체 4， 5， 6을 반웅물로 반응식 3을 따라서， 본 발명의 화학식 1의 화합물이 제조될 수 있다.
[반웅식 3]
제 2 중간체를 거치는 경우， 이 직접결합이 되는 경우의 화합물이 제조될 수 있다. 본 발명의 다른 일 구현예에 따르면， 제 1 중간체 1 , 2， 3을 반응물로 반응식 4를 따라서, 본 발명의 화학식 1의 화합물이 제조될 수 있다.
<제조예 1>화합물 1의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 A (8.46g,
21.58mmol )， (4ᅳ (4,6_di (pyr idin-2-yl )— 1,3,5— triazin_2_yl ) henyl )boronic acid (10.34g, 29.14瞧 ol)을 테트라하이드로퓨란 280ml에 완전히 녹인 후 2M 탄산칼륨수용액 (140ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0 76g, 0.66匪01)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 220ml로 재결정하여 화합물 1 (8.12g, 56%)를 제조하였다.
MS[M+H]+= 668
MS[M+H]+= 668
<제조예 3>화합물 3의 제조
MS[M+H]+= 743
<제조예 4>화합물 4의 제조
[화합물 4]
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 A (5.96g, 15.20mmol) , (4-(4,6-di (pyr idin-4-yl )-1,3, 5-tr iazin-2-yl ) henyl )boronic acid (7.29g, 20.53瞧 ol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액 (120ml)을 첨가하고, 테트라키스- (트리페닐포스핀)팔라듬 (0.53g, 0.46醒01)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 은도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 250ml로 재결정하여 화합물 4 (7.76g, 76%)를 제조하였다.
MS[M+H]+= 668
<제조예 5>화합물 5의 제조
MS[M+H]+= 756
<제조예 6>화합물 6의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 A (5.96g, 15.20mmo 1 )， ( 3— ( 4-pheny 1— 6— ( 3— ( pyr idin-2-yl ) heny 1)— 1,3,5— triazin_2_ yOphenyDboronic acid (8.83g, 20.53隱 ol)을 테트라하이드로퓨란 180ml에 완전히 녹인 후 2M 탄산칼륨수용액 (90ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.53g, 0.46隱 ol)을 넣은 후 6시간 동안 가열 교반하였다. 상온으로 은도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 190ml로 재결정하여 화합물 6 (4.78g, 42%)를 제조하였다.
MS[M+H]+= 743
：제조예 7>화합물 7의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 D (10.10g, 20.86画 01 )， 2-ch 1 or o-4 , 6-d i (pyr i d i η-2-y I ) - 1 , 3 , 5- 1 r i az i ne (4.88g, 18.14隱 ol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액 (120ml)을 첨가하고, 테트라키스ᅳ (트리페닐포스핀)팔라듐 (0.63g, 0.54睡 ol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고 아세토니트릴 230ml로 재결정하여 화합물 7 (6.16g, 57¾>)를 제조하였다.
MS[M+H] = 592
：제조예 8>화합물 8의 제조
MS[M+H]+= 666
<제조예 9>화합물 9의 제조
19.81mmol )， 4— chloro—2— phenyl— 6— (3— (pyr idin—2— yl ) henyl )pyr imidine (6.47g, 18.86醒 ol)을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M. 탄산칼륨수용액 (100ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.65g, 0.57隱01)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고
아세토니트릴 240ml로 재결정하여 화합물 9 (8.43g, 67%)를 제조하였다.
MS[M+H]+= 666
：제조예 10>화합물 10의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 D (7.71g, 15.93mmol ) , 2—chloro— 6— phenyl— 4— (4— (pyr idin—2— yl ) henyl )pyr idine (5.19g, 15.18隱 ol)을 테트라하이드로퓨란 210ml에 완전히 녹인 후 2M 탄산칼륨수용액 (100ml)을 첨가하고， 테트라키스— (트리페닐포스핀)팔라듐 (0.53g, 0.46隱01)을 넣은 후 4 시간 동안 가열 교반하였다. 상은으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세토니트릴 190ml로 재결정하여 화합물 10 (6.95g, 69%)를 제조하였다.
MS[M+H]+= 665
<제조예 11>화합물 11의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 D (9.35g 19.32mmo 1 ) , 8- ( 4- ( 4-ch 1 or ο-6-pheny 1-1,3,5-triazi η-2-y 1 ) heny 1 ) qu i no 1 ine (7.25g, 18.40隱 ol)을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M 탄산칼륨수용액 (100ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.63g, 0.54睡01)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고
아세토니트릴 200ml로 재결정하여 화합물 11 (7.22g, 55%)를 제조하였다.
MS[M+H]+= 717
：제조예 12>화합물 12의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 A (5.29g, 13.49画 o 1 )， (3-( 4-pheny l-6-(4-(pyr idin-3-yl ) heny l)-l,3,5-triazin-2- yDphenyOboronic acid (6.09g, 14.17瞧 ol)을 테트라하이드로퓨란 160ml에 완전히 녹인 후 2M 탄산칼륨수용액 (80ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.47g, 0.40mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한후 감압농축 시키고 테트라하이드로퓨란 150ml로 재결정하여 화합물 12 (6.27g, 63%)를 제조하였다.
MS[M+H]+= 743
<제조예 13>화합물 13의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 E (9.53g, 19.69匪 01 ) , 2-chl or o_4ᅳ pheny 1-6-(4-( yr i d i nᅳ 2—y 1 ) heny l)-l,3,5-triazine (5.89g, 17.12隱 ol)을 테트라하이드로퓨란 220ml에 완전히 녹인 후 2M
탄산칼륨수용액 (110ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.59g, 0.51mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세트니트릴 280ml로 재결정하여 화합물 13 (10.07g, 69%)를 제조하였다.
MS[M+H]+= 590
<제조예 14>화합물 14의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 E (8.53g,
17.63mmo 1 )， 2一 chloro— 4— (dibenzo[b,d] furan-4-yl )-6-(dibenzo[b,d] thiophen- 2-yl)-l,3,5-triazine (8.53g, 78.63隱 ol)을 테트라하이드로퓨란 210ml에 완전히 녹인 후 2M 탄산칼륨수용액 (105ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.64g, 0.56麵 ol)을 넣은 후 7 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고 아세토니트릴 270ml로 재결정하여 화합물 14 (10.25g, 70%)를 제조하였다.
MS[M+H]+= 786 <제조예 15>화합물 15의 제조
[화합물 15]
MS[M+H]+= 743
：제조예 16>화합물 16의 제조
MS[M+H]+= 592
<제조예 17>화합물 17의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 F (9.69g, 20.02隱 01 ) , 2— ch lor o_4_ ( d i benzo [b,d] fur an_3_y 1 ) 6— pheny 1-1,3,5-triazine (7.52g, 21.06睡 ol)을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M 탄산칼륨수용액 (100ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.73g, 0.63隱01)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 200ml로 재결정하여 화합물 17 (12.23g, 74%)를 제조하였다.
MS[M+H]+= 680
<제조예 18>화합물 18의 제조
[화합물 18]
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 F (10.20g, 21.07mmo 1 ) , 2-chl oro-4-pheny 1 _6— ( 3— ( yr i d i n— 2— y 1 ) heny 1 )— 1 , 3， 5— t r i az i ne (7.63g, 22.18隱 ol)을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M 탄산칼륨수용액 (100ml)을 첨가하고, 테트라키스- (트리페닐포스핀)팔라듐 (0.77g, 0.67mmol)을 넣은 후 6 시간 동안 가열 교반하였다. 상온으로 은도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 220ml로 재결정하여 화합물 18 (9.79g, 66%)를 제조하였다.
MS[M+H]+= 667
<제조예 19>화합물 19의 제조
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 C (6.86g, 17.50隱 01 )， ( 3— ( 4-pheny l-6-(4-(pyr idin-2-yl ) heny l)-l,3,5-triazin-2- yDphenyOboronic acid (7.15g, 16.63隱 ol)을 테트라하이드로퓨란 210ml에 완전히 녹인 후 2M 탄산칼륨수용액 (105ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.61g, 0.53瞧 ol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한후 감압농축 시키고 테트라하이드로퓨란 210ml로 재결정하여 화합물 19
(10.07g, 77%)를 제조하였다.
MS[M+H]+= 743
<제조예 20>화합물 20의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 C (8.03g, 20.48匪 01), ( 4- ( 4-pheny l-6-(4-(quinol in-8-yl ) heny 1 )— 1 , 3， 5— t r i az i n-2- yOphenyDboronic acid (10.32g, 21.51mmol )을 테트라하이드로퓨란 200ml에 완전히 녹인 후 2M 탄산칼륨수용액 (100ml)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.71g, 0.61隱 ol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 210ml로 재결정하여 화합물 20 (10.19g, 63%)를 제조하였다.
MS[M+H]+= 793
<제조예 21>화합물 21의 제조
질소 분위기에서 500ml 등근 바닥 플라스크에 화합물 D (5.93g,
12.25國 01 )， 3ᅳ (4-ch 1 or o— 6— pheny I -1 ,3,5-triazi η-2-yl ) -9— pheny 1ᅳ 9H-
carbazole (5.29g, 12.25隱 ol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액 (120ml)을 첨가하고， 테트라키스-
(트리페닐포스핀)팔라듐 (0.42g, 0.37誦 ol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슴으로 건조한 후 감압농축 시키고 아세토니트릴 250ml로 재결정하여 화합물 21 (6.39g, 69%)를 제조하였다.
MS[M+H]+= 755
MS[M+H]+= 831
<제조예 23>화합물 23의 제조
[화합물 23]
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 E (8.69g, 17.96讓 01 )， 2- (4-chl or o— 6-pheny 1-1,3,5-triazi n— 2-y 1 ) -9-pheny 1 -9H- carbazole (7.76g, 17.96匪 ol)을 테트라하이드로퓨란 230ml에 완전히 녹인 후 2M 탄산칼륨수용액 (115ml)을 첨가하고， 테트라키스-
(트리페닐포스핀)팔라듐 (0.62g, 0.54腿 ol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세트니트릴 260ml로 재결정하여 화합물 23 (9.76g, 72%)를 제조하였다.
MS[M+H]+= 755
<실험예 1>
ITOCindium tin oxide)가 1,000A의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때， 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며， 증류수로는 밀러포어사 (Mi 11 ipore Co.) 제품의 필터 (Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세착을 10분간 진행하였다. 증류수 세척이 끝난 후， 이소프로필알콜, 아세톤， 메탄을의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한， 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다. 이렇게 준비된 ΠΌ 투명 전극 위에 하기 화학식의 핵사니트릴 핵사아자트리페닐렌 (hexaazatr i pheny lene; HAT)를 100A의 두께로 열 진공 증착하여 정공 주입층을 형성하였다.
[HAT]
상기 정공 주입층 위에 정공을 수송하는 물질인 하기 화합물 4，4'-(9- phenyl-9H-carbazo le-3,6-diyl )bis(N,N-di heny laniline) [HT 1 ] ( 1150 A )를 진공 증착하여 정공 수송층을 형성하였다.
이어서, 상기 정공 저지층 위에 화합물 ET 1과 상기 화합물 LiQCLi thium Quinolate)를 1 : 1의 중량비로 진공증착하여 310A의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12A두께로 리튬플로라이드 (LiF)와 Ι ,ΟΟΟΑ 두께로 알루미늄을 증착하며 음극을 형성하였다.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 A/sec를 유지하였고, 음극의 리륨플로라이드는 o .3A/sec , 알루미늄은 2A/sec의 증착 속도를 유지하였으며， 증착시 진공도는 2 x 10— 7 ~ 5 χ 1(Γ6 torr를 유지하여， 유기 발광 소자를 제작하였다.
<실시예 1-1 내지 1-16>
상기 실험예 1과 동일한 방법으로 제조하되， 실험예 1에서 사용한 화합물 HB 1 대신 하기 표 1에 기재된 화합물을 사용하여， 유기 발광 소자를 제조하였다.
<비교예 1>
상기 실시예 1-1에서 화합물 EB 1 대신 하기 HB 2의 화합물을 사용한 것을 제외하고는 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.
<비교예 2>
상기 실시예 1ᅳ1에서 화합물 EB 1 대신 하기 EB 3의 화합물을 사용한 것을 제외하고는 상기 실험예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다.
[EB 3]
【표 11
본원 발명의 코어는 Spi robi f luorene 및 9， 10-dimetyl f luorene 코어보다 전자의 함량이 상대적으로 높으며 정공차단층으로 사용하였을 때 수명을 떨어뜨리지 않으면서 전압 및 효율에서 강점을 보인다는 결과를 얻었다. 상기 표 1의 결과와 같이， 본 발명에 다른 화합물은 정공 차단 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다. <실시예 2-1 내지 2-22>
상기 실험예 1에서 전자수송층으로 ET 1를 사용하는 대신 상기 화합물 1 내지 23을 사용한 것을 제외하고는 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. <비교예 3>
상기 실험예 1에서 전자수송층으로 ET 1를 사용하는 대신 하기 ET 2의 화합물을 사용한 것을 제외하고는 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.
<비교예 4>
상기 실험예 1에서 전자수송층으로 ET 1를 사용하는 대신 하기 ET 3의 화합물을 사용한 것을 제외하고는 상기 실험예 1과 동일한 방법으로
소자를 제작하였다.
<비교예 5>
상기 실시예 1에서 층으로 ET 1를 사용하는 대신 하기 ET 4의 화합물을 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.
【표 2】
o
상기 표 2에서 보는 바와 같이， 본원 발명의 화합물을 전자수송층으로 사용하여 제조된 유기 발광 소자의 경우에 유기 발광 소자의 o
o효율， 구동전압 o
및 /또는 안정성 면에서 우수한 특성을 나타낸다.
Spirobif luorene 코어의 비교예 1 및 9， 10-dimetyl f luorene 코어의 비교예 2의 화합물을 전자수송층으로 사용하여 제조된 유기 발광 소자보다 저전압， 고효율 및 장수명의 특성을 보인다.
본원 발명의 코어는 Spirobif luorene 및 9， 10— dimetylf luorene 코어보다 전자의 함량이 상대적으로 높으며 전자수송층으로 사용하였을 때 수명이 15¾>~30% 상승하면서 전압 및 효율에서도 강점을 보인다는 결과를 얻었다.
벤조이미다졸이 치환된 트리아진을 연결한 비교예 4 및 5의 경우에는 수명이 크게 떨어지는 것을 알 수 있다. 이상을 통해 본 발명의 바람직한 실시예 (정공차단층, 전자수송층)에 대하여 설명하였지만， 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이
가능하고 이 또한 발명의 범주에 속한다. 【부호의 설명】
1: 기판 2: 양극
3： 발광층 4： 음극
5： 정공주입층 6: 정공수송층
7： 발광층 8: 전자수송층
Claims
【청구항 1】
하기 화학식 1로 표시되는 화합물:
상기 화학식 1에서，
¾ 및 ¾ 는 각각 독립적으로 치환 또는 비치환된 d-60의 알킬 또는 치환 또는 비치환된 C6-60 아릴이고，
, 및 L3는 각각 독립적으로, 직접결합， 또는 치환 또는 비치환된 C6-6o 아릴렌이고，
Xi , X2 및 ¾는 각각 독립적으로 N 또는 CR' 이고， 단， 이들 중 하나 이상이 N이고，
' 은 수소 또는 치환 또는 비치환된 C -60의 알킬이고,
An 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴, 0 및 S 중 1개 이상을 포함하는 치환 또는 비치환된 C5-60 헤테로아릴， 피리디닐， 피리미디닐, 트리아지닐， 카바졸릴, 이소퀴놀리닐 또는 퀴나졸리닐이고, 단，
An 및 Ar2 중 하나 이상이， 0 및 S 중 1개 이상을 포함하는 치환 또는 비치환된 C5-60 헤테로아릴， 피리디닐, 피리미디닐， 트리아지닐， 카바졸릴， 이소퀴놀리닐 또는 퀴나졸리닐임 .
【청구항 2]
제 1항에 있어서，
상기 화학식 1로 표시되는 화합물은 하기 화학식 1—1 내지 1-5로 표시되는 화합물 중에서 선택되는 어느 하나인， 화합물:
[화학식 1-4]
【청구항 3】
거1 1항에 있어서，
Ri 및 R2는 각각 독립적으로 메틸 또는 벤질인， 화합물.
[청구항 4】
게 1항에 있어서，
Li , L2 및 L3는 각각 독립적으로 직접결합 또는 하기로 구성되 군으로
【청구항 5】
게 1항에 있어서，
Li, L2 및 L3는 각각 독립적으로 직접결합 또는
화합물
【청구항 6]
제 1항에 있어서,
An 및 Ar2는 각각 독립적으로 하기로 구성되는 군으로부터 선택되는 어느
【청구항 7】
게 1항에 있어서，
상기 화학식 1로 표시되는 화합물은， 하기로 구성되는 군으로부터 선택되는 어느 하나인， 화합물:
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
//: O8SSMI>d 9909ΏAV
【청구항 8】
제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 게 1 전극과 상기 게 2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기
발광 소자로서， 상기 유기물층 중 1층 이상은 제 1항 내지 제 7항 중 어느 하나의 항에 따른 화합물을포함하는 것인， 유기 발광소자.
【청구항 9】
제 8항에 있어서，
상기 화합물을 포함하는 유기물층은 전자주입층; 전자수송층; 또는 전자주입과 전자수송을 동시에 하는 층인 것을 특징으로 하는， 유기 발광 소자.
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| CN113166128A (zh) * | 2018-12-07 | 2021-07-23 | 出光兴产株式会社 | 新型化合物和使用了其的有机电致发光元件 |
| CN113939505A (zh) * | 2019-10-18 | 2022-01-14 | 株式会社Lg化学 | 化合物及包含其的有机发光元件 |
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| KR20190009994A (ko) * | 2017-07-20 | 2019-01-30 | 주식회사 두산 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
| CN109574908B (zh) * | 2017-09-28 | 2022-03-29 | 江苏三月科技股份有限公司 | 一种含螺二甲基蒽芴的化合物及其在有机电致发光器件上的应用 |
| CN109748880A (zh) * | 2017-11-02 | 2019-05-14 | 江苏三月光电科技有限公司 | 一种含螺二甲基蒽芴和含氮六元杂环的化合物及其在有机电致发光器件上的应用 |
| CN110746409B (zh) * | 2018-12-10 | 2023-10-17 | 广州华睿光电材料有限公司 | 有机化合物、混合物、组合物及电子器件和应用 |
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| KR20170038748A (ko) * | 2015-09-30 | 2017-04-07 | 주식회사 엘지화학 | 스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
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| KR101742436B1 (ko) * | 2015-12-15 | 2017-05-31 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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| CN113939505A (zh) * | 2019-10-18 | 2022-01-14 | 株式会社Lg化学 | 化合物及包含其的有机发光元件 |
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| KR20180138457A (ko) | 2018-12-31 |
| CN110494426B (zh) | 2022-12-30 |
| KR102006433B1 (ko) | 2019-10-08 |
| CN110494426A (zh) | 2019-11-22 |
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