WO2015016498A1 - 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- WO2015016498A1 WO2015016498A1 PCT/KR2014/006184 KR2014006184W WO2015016498A1 WO 2015016498 A1 WO2015016498 A1 WO 2015016498A1 KR 2014006184 W KR2014006184 W KR 2014006184W WO 2015016498 A1 WO2015016498 A1 WO 2015016498A1
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000003118 aryl group Chemical group 0.000 claims description 71
- -1 sulfoxy group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 239000011368 organic material Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 125000002950 monocyclic group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000002560 nitrile group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 125000004434 sulfur atom Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 12
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- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
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- 238000000034 method Methods 0.000 claims description 10
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- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
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- 239000004332 silver Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
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- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
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- 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 2
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- 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
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- 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
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 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
- 239000008096 xylene Substances 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
- 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
Images
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- 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
- C07D403/14—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 three or more 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- 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
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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
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Definitions
- the present specification relates to a heterocyclic compound and an organic light emitting device including the same.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- L 1 is a direct bond; Substituted or unsubstituted phenylene; Or a substituted or unsubstituted divalent monocyclic heterocyclic group containing at least one of N, O and S atoms;
- L 2 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms;
- X 1 is N or CR 11
- X 2 is N or CR 12
- X 3 is N or CR 13
- A is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubsti
- Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstit
- R 1 to R 4 and R 11 to R 13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substitute
- a and c are each an integer of 0 to 4
- b and d are each an integer of 0 to 3
- R 1 is the same or different from each other
- b is 2 or more
- R 2 is the same or different from each other
- R 3 is the same as or different from each other
- R 4 is the same or different from each other.
- an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
- the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
- Compounds according to at least some embodiments may improve efficiency, low driving voltage, and / or lifetime characteristics in organic light emitting diodes.
- the compounds described herein can provide high efficiency and / or long life organic light emitting devices when used as a host of the phosphorescent light emitting layer or as an electron transporting material adjacent to the light emitting layer.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
- FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- 3 to 16 show synthetic confirmation data of the main compounds.
- An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
- substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Thiol group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Silyl groups; Aryl alkenyl group; Aryl group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Carbazole groups; Aryl group; Fluorenyl group; Arylalkyl group; Aryl alkenyl group; And heterocyclic or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of O, N and S, or substituted or unsubstituted with a substituent to which two or more substituents of the above-described substituents are linked.
- a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group and can be interpreted as a substituent to which two phenyl groups are linked.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the amide group may be substituted with one or two of the nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
- Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
- the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
- the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
- the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
- the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted.
- the aryl group in the present specification may mean an aromatic ring.
- the aryl group is a monocyclic aryl group
- carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
- the monocyclic aryl group may be a phenyl group, biphenyl group, terphenyl group, stilbenyl group and the like, but is not limited thereto.
- Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
- the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
- the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
- the present invention is not limited thereto.
- the heterocyclic group is a heterocyclic group including one or more of O, N, and S as a hetero atom, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
- the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group,
- the aryl group in the aryloxy group, the arylthioxy group and the aryl sulfoxy group is the same as the examples of the aryl group described above.
- the aryloxy group phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyl Oxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Oxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy, and the like.
- arylthioxy group examples include a phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenyl.
- Thioxy groups and the like, and aryl sulfoxy groups include, but are not limited to, benzene sulfoxy groups and p-toluene sulfoxy groups.
- alkyl group in the alkyl thioxy group and the alkyl sulfoxy group is the same as the example of the alkyl group mentioned above.
- alkyl thioxy groups include methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group, and the like. But it is not limited thereto.
- an arylene group means one having two bonding positions, that is, a divalent group.
- the description of the aforementioned aryl group can be applied except that they are each divalent.
- the divalent heterocyclic group refers to a group having two binding positions in the heterocyclic group, that is, a divalent group.
- the description of the aforementioned heterocyclic groups can be applied except that they are each divalent.
- a of Formula 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted aromatic or aliphatic monocyclic 6-membered heterocyclic group containing at least one of N, O and S atoms.
- the polycyclic ring is located at the A position, the synthesis is not easy, and the molecular weight is too large, so that the deposition temperature is too high, in which case the processability is not good.
- a of Formula 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted monocyclic 6-membered heterocyclic group containing N.
- Formula 1 may be represented by the following formula (2).
- Z 1 to Z 5 are the same as or different from each other, and each independently is CR 5 or N, where R 5 are the same definitions as R 1 to R 4, Z 1 to Z 5 of the case 2 with at least a CR 5 R 5 Are the same as or different from each other, the remaining substituents are as defined in formula (1).
- a of Formula 1 is a phenyl group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; A biphenyl group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Or a monocyclic 6-membered heterocyclic group which is unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group and contains at least one of N, O and S atoms.
- the monocyclic ring is located at A, the triplet energy is high, making it suitable as a yellow green, green or blue phosphorescent host.
- a in Formula 1 is an phenyl group unsubstituted or substituted with an alkyl group, a phenyl group or an N-containing monocyclic 6-membered heterocyclic group; A biphenyl group unsubstituted or substituted with an alkyl group, a phenyl group or an N-containing monocyclic 6-membered heterocyclic group; Or an N-containing monocyclic 6-membered heterocyclic group unsubstituted or substituted with an alkyl group, a phenyl group or an N-containing monocyclic 6-membered heterocyclic group.
- the N-containing monocyclic 6-membered heterocyclic group may be a monocyclic structure having 1 to 5, preferably 1 to 3 nitrogen atoms, such as a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group.
- the alkyl group may be a C 1 to C 6 alkyl group such as methyl, ethyl, propyl, butyl and the like.
- a of Formula 1 is a phenyl group unsubstituted or substituted with an alkyl group; Or a biphenyl group unsubstituted or substituted with an alkyl group.
- L 1 of Formula 1 is a substituted or unsubstituted phenylene; Or a substituted or unsubstituted divalent monocyclic heterocyclic group containing at least one of N, O and S atoms.
- the polycyclic ring is located at the L 1 position, the synthesis is not easy, and the molecular weight is too large, so that the deposition temperature is too high, in which case the processability is not good.
- the monocyclic ring is located at L 1 , the triplet energy is high, making it suitable as a yellow green, green or blue phosphorescent host.
- L 1 of Formula 1 is a substituted or unsubstituted phenylene; Or a substituted or unsubstituted divalent monocyclic heterocyclic group including N.
- L 1 of Chemical Formula 1 is a phenylene unsubstituted or substituted with a halogen group, a nitrile group, an alkyl group, an aryl group or a heterocyclic group; Or a divalent monocyclic N-containing heterocyclic group unsubstituted or substituted with a halogen, nitrile, alkyl, aryl or heterocyclic group.
- L 1 of Chemical Formula 1 is a phenylene unsubstituted or substituted with a halogen group, a nitrile group, an alkyl group, a phenyl group or an N-containing heterocyclic group; Or a divalent N-containing monocyclic heterocyclic group unsubstituted or substituted with a halogen group, a nitrile group, an alkyl group, a phenyl group or an N-containing heterocyclic group.
- L 1 of Chemical Formula 1 is a phenylene unsubstituted or substituted with a halogen group, a nitrile group, an alkyl group, a phenyl group or an N-containing monocyclic heterocyclic ring; Or a divalent N-containing monocyclic heterocyclic group unsubstituted or substituted with a halogen group, a nitrile group, an alkyl group, a phenyl group or an N-containing monocyclic heterocyclic group.
- the N-containing monocyclic heterocyclic group may be a monocyclic structure having 1 to 5, preferably 1 to 3 nitrogen atoms, such as a pyridine group, pyrimidine group, pyridazine group, pyrazine group or triazine group.
- the alkyl group may be a C 1 to C 6 alkyl group such as methyl, ethyl, propyl, butyl and the like.
- L 1 of the general formula 1 does not include a carbazole structure.
- L 2 of the general formula 1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms.
- L 2 of the general formula 1 is a substituted or unsubstituted monocyclic arylene group; Or a substituted or unsubstituted divalent monocyclic heterocyclic group containing at least one of N, O and S atoms.
- L 2 of the general formula 1 is a substituted or unsubstituted monocyclic arylene group; Or a substituted or unsubstituted divalent monocyclic N-containing heterocyclic group.
- Formula 1 may be represented by the following formula (3).
- Z 1 to Z 5 are the same as or different from each other, and each independently CR 5 or N, wherein R 5 is as defined in R 1 to R 4 , and Z 1 to Z 5 are R 5 when at least two of CR 5 are 5 is the same as or different from each other,
- Y 11 to Y 15 and Y 21 to Y 25 are the same as or different from each other, and are each independently CR 6 or N, wherein R 6 is as defined in R 1 to R 4 , and Y 11 to Y 15 and Y 21 to When at least two of Y 25 are CR 6 , R 6 is the same as or different from each other, provided that one of Y 11 to Y 15 and one of Y 21 to Y 25 are carbon atoms bonded to adjacent carbazole groups,
- L 1 And L 2 In Formula 1 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a halogen group, a nitrile group, an alkyl group or an aryl group; Or a monocyclic N-containing heterocyclic group unsubstituted or substituted with a halogen, nitrile, alkyl, or aryl group.
- L 1 And L 2 In Formula 1 are the same as or different from each other, each independently a phenyl group unsubstituted or substituted with a fluorine group, a nitrile group, an alkyl group or a phenyl group; Or a monocyclic N-containing heterocyclic group unsubstituted or substituted with a fluorine group, a nitrile group, an alkyl group or a phenyl group.
- the N-containing heterocyclic group may be a monocyclic structure having 1 to 5 nitrogen atoms, preferably 1 to 3 nitrogen atoms, such as a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group.
- the alkyl group may be a C 1 to C 6 alkyl group such as methyl, ethyl, propyl, butyl and the like.
- L 1 And L 2 In Formula 1 are the same as or different from each other, each independently represent a phenyl group unsubstituted or substituted with a fluorine group, a nitrile group, or an alkyl group.
- L 1 and L 2 may be represented as follows, respectively.
- R 6 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsub
- f is an integer of 0-4, and when f is 2 or more, R ⁇ 6> is the same or different from each other.
- R 6 Is a halogen group, a nitrile group, an alkyl group or an aryl group.
- Ar 1 and Ar 2 are the same as or different from each other, a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group containing at least one of N, O and S atoms.
- Ar 1 and Ar 2 do not include a carbazole structure. Synthesis is not easy when carbazole is located at the Ar 1 or Ar 2 position.
- Ar 1 and Ar 2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, an aryl group or an N-containing heterocyclic group; Or a substituted or unsubstituted heterocyclic group which is unsubstituted or substituted with an alkyl group, an aryl group or an N-containing heterocyclic group and contains one or more of N, O and S atoms.
- the N-containing heterocyclic group may be a monocyclic structure having 1 to 5 nitrogen atoms, preferably 1 to 3 nitrogen atoms, such as a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group.
- the alkyl group may be a C 1 to C 6 alkyl group such as methyl, ethyl, propyl, butyl and the like.
- Ar 1 and Ar 2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group, a phenyl group or an N-containing heterocyclic group; Fluorenyl unsubstituted or substituted with an alkyl group, a phenyl group or an N-containing heterocyclic group; Or an N-containing heterocyclic group unsubstituted or substituted with an alkyl group, a phenyl group or an N-containing heterocyclic group.
- the N-containing heterocyclic group may be a monocyclic structure having 1 to 5 nitrogen atoms, preferably 1 to 3 nitrogen atoms, such as a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group.
- the alkyl group may be a C 1 to C 6 alkyl group such as methyl, ethyl, propyl, butyl and the like.
- Ar 1 and Ar 2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group or a phenyl group; Fluorenyl unsubstituted or substituted with an alkyl group or a phenyl group; Or an N-containing monocyclic heterocyclic group unsubstituted or substituted with an alkyl group or a phenyl group.
- the N-containing monocyclic heterocyclic group may be a pyridine group, pyrimidine group, pyridazine group, pyrazine group or triazine group.
- the alkyl group may be a C 1 to C 6 alkyl group such as methyl, ethyl, propyl, butyl and the like.
- Formula 1 may be represented by the following formula (4).
- Z 1 to Z 5 are the same as or different from each other, and each independently CR 5 or N, wherein R 5 is as defined in R 1 to R 4 , and Z 1 to Z 5 are R 5 when at least two of CR 5 are 5 is the same as or different from each other,
- Y 11 to Y 15 and Y 21 to Y 25 are the same as or different from each other, and are each independently CR 6 or N, wherein R 6 is as defined in R 1 to R 4 , and Y 11 to Y 15 and Y 21 to When at least two of Y 25 are CR 6 , R 6 is the same as or different from each other, provided that one of Y 11 to Y 15 and one of Y 21 to Y 25 are carbon atoms bonded to adjacent carbazole groups,
- X 11 to X 15 and X 21 to X 25 are the same as or different from each other, and are each independently CR 7 or N, wherein R 7 is as defined in R 1 to R 4 , and X 11 to X 15 and X 21 to when X 25 is at least two are of the CR 7 R 7 are the same as or different from each other, and
- R One To R 4 In Formula 1 is hydrogen.
- the compound of Formula 1 may be represented by the following structural formula.
- the compound represented by Chemical Formula 1 may be prepared based on the preparation examples described below. According to one embodiment, it may be prepared in the same manner as in Scheme 1 or 2.
- organic light emitting device including the compound represented by Formula 1.
- the first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound of Formula 1.
- the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of 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 injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
- the organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer comprises a compound of the formula (1).
- the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1.
- the compound of Formula 1 may be included as a host of the phosphorescent light emitting layer.
- the phosphorescent layer may further include a phosphorescent material.
- the phosphorescent material contains a metal complex, and the metal complex preferably has a metal atom and a ligand selected from Ir, Pt, Os, Au, Cu, Re, and Ru.
- the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of Formula 1.
- the electron transport layer, the electron injection layer or the layer at the same time the electron transport and electron injection comprises a compound of the formula (1).
- the organic material layer includes a light emitting layer and an electron transport layer
- the electron transport layer includes the compound of Formula 1.
- the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group or a benzocarbazole group, in addition to the organic material layer including the compound of Formula 1.
- the organic material layer including the compound of Formula 1 includes the compound of Formula 1 as a host, and includes another organic compound, a metal, or a metal compound as a dopant.
- the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.
- FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
- the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound of Formula 1.
- the organic material layers may be formed of the same material or different materials.
- the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1.
- the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
- an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
- 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 an anode.
- the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
- the positive electrode material that can be used in the present invention 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), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
- the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
- the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
- the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
- the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
- the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
- Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
- 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 containing compound.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
- the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
- At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
- the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
- the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
- the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, 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-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
- the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
- the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
- 2-bromocarbazole (10.0 g, 40.6 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -Yl) phenyl) -1,3,5-triazine (2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl ) -1,3,5-triazine) (18.1 g, 41.5 mmol), and potassium carbonate (17.0 g, 123 mmol) were suspended in a mixture of tetrahydrofuran (100 mL) and water (50 mL).
- 3 to 16 show synthetic confirmation data of the main compounds.
- the glass substrate coated with ITO (indium tin oxide) at a thickness of 1,500 kPa was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
- ITO indium tin oxide
- Fischer Co. was used as a detergent
- distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
- ultrasonic washing was performed twice with distilled water for 10 minutes.
- ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
- the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
- NPB N, N-Bis- (1-naphthalenyl) -N, N-bis-phenyl- (1, 1-biphenyl) -4, 4-diamine
- NPB N, N-Bis- (1-naphthalenyl) -N, N-bis-phenyl- (1, 1-biphenyl) -4, 4-diamine
- the compound of Formula 1-1 prepared in Preparation Example 41 was vacuum-deposited with Ir (ppy) 3 dopant at a concentration of 10% on the hole transport layer to form a light emitting layer.
- the following electron transport material was vacuum deposited to a thickness of 200 ⁇ on the emission layer to form an electron injection and transport layer.
- lithium fluoride (LiF) and aluminum were deposited to a thickness of 2,000 kPa in order to form a cathode.
- the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
- the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
- aluminum is 2 ⁇ / sec
- the vacuum degree during deposition is 2 ⁇ 10 ⁇ 7 to 5 ⁇ 10 ⁇ 8 torr was maintained.
- Experiment 1 was the same except for using the compound of formula 1-2 instead of the compound of formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-4 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-40 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-62 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-74 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-109 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-142 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of Formula 1-152 instead of the compound of Formula 1-1.
- Experiment 1 was the same except for using the compound of formula 1-200 instead of the compound of formula 1-1.
- Experiment 1 was the same except for using the compound of formula 1-211 instead of the compound of formula 1-1.
- Experiment 1 was the same except for using the compound of formula 1-219 instead of the compound of formula 1-1.
- Experimental Example 1 was the same except for using the compound of formula 1-231 instead of the compound of formula 1-1.
- Table 1 shows the device results of using the compounds in Experimental Examples 1 to 16 and Comparative Example 1 as light emitting layers.
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Abstract
Description
No. | Host | 도펀트(Dopant) | 도핑농도(%) | 구동전압(V)@5,000 cd/m2 | 발광효율(Cd/A) |
비교예 1 | H1 | Ir(ppy)3 | 10 | 5.2 | 36 |
실험예 1 | 화학식 1-1 | Ir(ppy)3 | 10 | 4.7 | 40 |
실험예 2 | 화학식 1-2 | Ir(ppy)3 | 10 | 4.9 | 45 |
실험예 3 | 화학식 1-4 | Ir(ppy)3 | 10 | 4.5 | 44 |
실험예 4 | 화학식 1-23 | Ir(ppy)3 | 10 | 4.4 | 43 |
실험예 5 | 화학식 1-29 | Ir(ppy)3 | 10 | 4.7 | 42 |
실험예 6 | 화학식 1-40 | Ir(ppy)3 | 10 | 4.2 | 48 |
실험예 7 | 화학식 1-62 | Ir(ppy)3 | 10 | 4.3 | 44 |
실험예 8 | 화학식 1-74 | Ir(ppy)3 | 10 | 4.6 | 47 |
실험예 9 | 화학식 1-98 | Ir(ppy)3 | 10 | 4.8 | 46 |
실험예 10 | 화학식 1-109 | Ir(ppy)3 | 10 | 4.7 | 47 |
실험예 11 | 화학식 1-142 | Ir(ppy)3 | 10 | 4.7 | 41 |
실험예 12 | 화학식 1-152 | Ir(ppy)3 | 10 | 4.9 | 47 |
실험예 13 | 화학식 1-200 | Ir(ppy)3 | 10 | 4.4 | 40 |
실험예 14 | 화학식 1-211 | Ir(ppy)3 | 10 | 4.7 | 47 |
실험예 15 | 화학식 1-219 | Ir(ppy)3 | 10 | 4.1 | 49 |
실험예 16 | 화학식 1-231 | Ir(ppy)3 | 10 | 4.2 | 48 |
Claims (16)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 화학식 1에 있어서,L1은 직접결합; 치환 또는 비치환된 페닐렌; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 2가의 단환 헤테로고리기이며;L2는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 2가의 헤테로고리기이며;X1은 N 또는 CR11이고, X2는 N 또는 CR12이며, X3는 N 또는 CR13이고,A는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 방향족 또는 지방족의 단환 6원 헤테로고리기이고,Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 플루오레닐기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기이되, 카바졸기를 포함하지 않고,R1 내지 R4 및 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 플루오레닐기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기이고,a 및 c는 각각 0 내지 4의 정수이고, b 및 d는 각각 0 내지 3의 정수이며, a가 2 이상인 경우 R1은 서로 같거나 상이하고, b가 2 이상인 경우 R2는 서로 같거나 상이하며, c가 2 이상인 경우 R3는 서로 같거나 상이하고, d가 2 이상인 경우 R4는 서로 같거나 상이하다.
- 청구항 1에 있어서, A는 알킬기, 페닐기 또는 N 함유 단환 6원 헤테로고리기로 치환 또는 비치환된 페닐기; 알킬기, 페닐기 또는 N 함유 단환 6원 헤테로고리기로 치환 또는 비치환된 바이페닐기; 또는 알킬기, 페닐기로 또는 N 함유 단환 6원 헤테로고리기로 치환 또는 비치환된 N 함유 단환 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, L1은 치환 또는 비치환된 페닐렌; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 2가의 단환 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, L2는 치환 또는 비치환된 아릴렌기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 2가의 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 3으로 표시되는 것인 화합물:[화학식 3]상기 화학식 3에 있어서,Z1 내지 Z5는 서로 같거나 상이하고, 각각 독립적으로 CR5 또는 N이며, 여기서 R5는 R1 내지 R4의 정의와 같고, Z1 내지 Z5는 중 적어도 2개가 CR5인 경우 R5는 서로 같거나 상이하며,Y11 내지 Y15 및 Y21 내지 Y25는 서로 같거나 상이하고, 각각 독립적으로 CR6 또는 N이며, 여기서 R6는 R1 내지 R4의 정의와 같고, Y11 내지 Y15 및 Y21 내지 Y25 중 적어도 2개가 CR6인 경우 R6는 서로 같거나 상이하며, 단, Y11 내지 Y15 중 하나와 Y21 내지 Y25 중 하나는 인접하는 카바졸기에 결합하는 탄소원자이고,나머지 치환기는 화학식 1에서 정의한 바와 같다.
- 청구항 1에 있어서,상기 화학식 1의 L1은 할로겐기, 니트릴기, 알킬기, 페닐기 또는 N 함유 단환 헤테로고리기로 치환 또는 비치환된 페닐렌; 또는 할로겐기, 니트릴기, 알킬기, 페닐기 또는 N 함유 단환 헤테로고리기로 치환 또는 비치환된 2가의 N 함유 단환 헤테로고리기이고,L2는 할로겐기, 니트릴기, 알킬기 또는 아릴기로 치환 또는 비치환된 페닐기; 또는 할로겐기, 니트릴기, 알킬기 또는 아릴기로 치환 또는 비치환된 단환 N 함유 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, 상기 화학식 1의 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 하기 구조식으로부터 선택되는 것인 화합물:R6는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 플루오레닐기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 방향족 또는 지방족의 헤테로고리기이고,f는 0 내지 4의 정수이며, f가 2이상인 경우, R6는 서로 같거나 상이하다.
- 청구항 1에 있어서, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 알킬기, 페닐기 또는 N 함유 헤테로고리기로 치환 또는 비치환된 페닐기; 알킬기, 페닐기로 또는 N 함유 헤테로고리기로 치환 또는 비치환된 플루오레닐; 또는 알킬기, 페닐기 또는 N 함유 헤테로고리기기로 치환 또는 비치환된 N 함유 헤테로고리기인 것인 화합물.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 4로 표시되는 것인 화합물:[화학식 4]상기 화학식 4에 있어서,Z1 내지 Z5는 서로 같거나 상이하고, 각각 독립적으로 CR5 또는 N이며, 여기서 R5는 R1 내지 R4의 정의와 같고, Z1 내지 Z5는 중 적어도 2개가 CR5인 경우 R5는 서로 같거나 상이하며,Y11 내지 Y15 및 Y21 내지 Y25는 서로 같거나 상이하고, 각각 독립적으로 CR6 또는 N이며, 여기서 R6는 R1 내지 R4의 정의와 같고, Y11 내지 Y15 및 Y21 내지 Y25 중 적어도 2개가 CR6인 경우 R6는 서로 같거나 상이하며, 단, Y11 내지 Y15 중 하나와 Y21 내지 Y25 중 하나는 인접하는 카바졸기에 결합하는 탄소원자이고,X11 내지 X15 및 X21 내지 X25는 서로 같거나 상이하고, 각각 독립적으로 CR7 또는 N이며, 여기서 R7은 R1 내지 R4의 정의와 같고, X11 내지 X15 및 X21 내지 X25는 중 적어도 2개가 CR7인 경우 R7은 서로 같거나 상이하며,나머지 치환기는 화학식 1에서 정의한 바와 같다.
- 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 12 중 어느 하나의 항에 따른 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 13에 있어서, 상기 화합물을 포함하는 유기물층은 발광층인 것인 유기 발광 소자.
- 청구항 14에 있어서, 상기 발광층은 인광 발광층인 것인 유기 발광 소자.
- 청구항 14에 있어서, 상기 발광층은 인광 재료를 더 포함하는 것인 유기 발광 소자.
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TWI558699B (zh) | 2016-11-21 |
EP3015465B1 (en) | 2019-09-04 |
JP6231682B2 (ja) | 2017-11-15 |
EP3015465A1 (en) | 2016-05-04 |
US20160204359A1 (en) | 2016-07-14 |
CN105431423A (zh) | 2016-03-23 |
EP3015465A4 (en) | 2016-11-23 |
US11111231B2 (en) | 2021-09-07 |
KR20150014368A (ko) | 2015-02-06 |
TW201518292A (zh) | 2015-05-16 |
CN105431423B (zh) | 2018-07-03 |
US20190127352A1 (en) | 2019-05-02 |
JP2016532686A (ja) | 2016-10-20 |
KR101547065B1 (ko) | 2015-08-25 |
US10253016B2 (en) | 2019-04-09 |
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