WO2020076109A1 - 유기발광소자 - Google Patents
유기발광소자 Download PDFInfo
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- WO2020076109A1 WO2020076109A1 PCT/KR2019/013328 KR2019013328W WO2020076109A1 WO 2020076109 A1 WO2020076109 A1 WO 2020076109A1 KR 2019013328 W KR2019013328 W KR 2019013328W WO 2020076109 A1 WO2020076109 A1 WO 2020076109A1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 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
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- 239000011135 tin Substances 0.000 description 1
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- 239000010936 titanium Substances 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
- 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
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- 238000001771 vacuum deposition Methods 0.000 description 1
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- 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
- 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
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Definitions
- the present specification relates to an organic light emitting device.
- the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes.
- a voltage is applied to the organic light emitting device having such a structure, electrons and electrons injected from two electrodes are combined and paired in an organic thin film, and then extinguishes and emits light.
- the organic thin film may be composed of a single layer or multiple layers if necessary.
- a pure organic material or a complex compound in which an organic material and a metal are complex occupies most, and depending on the purpose, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. It can be divided into.
- a hole injection material or a hole transport material an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used.
- an electron injection material or an electron transport material an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used.
- the light emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states, and excitons formed by recombination of holes and electrons in the light emitting layer are formed.
- a material with high luminous efficiency that converts it to light when desired is preferred.
- An exemplary embodiment of the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a compound represented by Formula 1, a compound represented by Formula 2, and a compound represented by Formula 3 below. It provides an organic light emitting device that includes.
- Ar1 and Ar2 are the same as or different from each other, and each independently an substituted or unsubstituted aryl group,
- L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
- R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- n1 and n2 are each an integer of 0 to 4, and when n1 and n2 are each 2 or more, the substituents in 2 or more parentheses are the same or different from each other,
- Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group,
- Ar5 is a substituted or unsubstituted aryl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group,
- L3 to L5 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
- R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- n3 is an integer from 0 to 4, and when n3 is 2 or more, 2 or more R3s are the same as or different from each other,
- n4 is an integer from 0 to 3, and when n4 is 2 or more, 2 or more R4s are the same as or different from each other,
- Y1 is O, S or NRa
- Y2 is O, S or NRb
- Cy1 to Cy3 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle, and Cy1 and Cy2 may combine with each other to form a substituted or unsubstituted ring,
- Ra is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring,
- Rb is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with Cy2 or Cy3 to form a substituted or unsubstituted ring.
- the organic light emitting device of the present invention simultaneously includes a compound represented by Formula 1, a compound represented by Formula 2 and a compound represented by Formula 3 in the light emitting layer, thereby obtaining an organic light emitting device having a low driving voltage, high luminous efficiency, and long life. You can.
- FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer 1 (6), hole transport layer 2 (7), light emitting layer (8), electron transport layer (9), electron injection layer (10) ) And an example of an organic light emitting device made of the cathode 4.
- the organic light emitting device of the present invention comprises a first electrode; A second electrode provided to face the first electrode; And an organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a compound represented by Formula 1, a compound represented by Formula 2, and a compound represented by Formula 3 below.
- the organic light emitting device including the light emitting layer as described above is low driving voltage and high light emission It has the efficiency and has the effect of improving the life of the device.
- Ar1 and Ar2 are the same as or different from each other, and each independently an substituted or unsubstituted aryl group,
- L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
- R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- n1 and n2 are each an integer of 0 to 4, and when n1 and n2 are each 2 or more, the substituents in 2 or more parentheses are the same or different from each other,
- Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group,
- Ar5 is a substituted or unsubstituted aryl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group,
- L3 to L5 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
- R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- n3 is an integer from 0 to 4, and when n3 is 2 or more, 2 or more R3s are the same as or different from each other,
- n4 is an integer from 0 to 3, and when n4 is 2 or more, 2 or more R4s are the same as or different from each other,
- Y1 is O, S or NRa
- Y2 is O, S or NRb
- Cy1 to Cy3 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle, and Cy1 and Cy2 may combine with each other to form a substituted or unsubstituted ring,
- Ra is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring,
- Rb is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with Cy2 or Cy3 to form a substituted or unsubstituted ring.
- substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
- substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Silyl group; Boron group; Alkoxy groups; Aryloxy group; Alkyl groups; Alkenyl group; Alkynyl group; Cycloalkyl group; Aryl group; Amine group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-described substituents, or having no substituents.
- a substituent having two or more substituents may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
- examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
- the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
- the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.
- the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
- the boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, tert-butyl dimethyl boron group, triphenyl boron group, phenyl boron group, and the like.
- the alkyl group may be a straight chain or a branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
- alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but is not limited to these.
- the alkoxy group may be a straight chain, branched chain or cyclic chain.
- the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
- Substituents comprising alkyl, alkoxy, and other alkyl group moieties described herein include both straight-chain or ground forms.
- the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, and the like. Does not work.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.
- the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
- the aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, but is not limited thereto.
- the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
- the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.
- Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
- aryl group in the aryloxy group can be applied to the description of the aryl group described above.
- the heterocyclic group is a heteroatom as a ring group containing at least one of N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
- heterocyclic group examples include pyridine group, pyrrole group, pyrimidinyl group, quinolinyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, Carbazole groups, benzocarbazole groups, naphthobenzofuranyl groups, benzonaphthothiophenyl groups, indenocarbazole groups, and the like, but are not limited thereto.
- heterocyclic group may be applied, except that the heteroaryl group is aromatic.
- the description of the aryl group can be applied, except that the arylene group is divalent.
- ring is a hydrocarbon ring; Or a hetero ring.
- the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group, except for the divalent group.
- heterocyclic group may be applied to the heterocyclic ring except that it is divalent.
- R1 and R2 are the same as or different from each other, and hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
- R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms; Or an aryl group having 6 to 60 carbon atoms.
- R1 and R2 are each hydrogen.
- n1 is an integer of 0 to 4, and when n1 is 2 or more, two or more R1s are the same or different.
- n1 is 0 or 1.
- n2 is an integer of 0 to 4, and when n2 is 2 or more, two or more R2s are the same or different.
- n2 is 0 or 1.
- L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
- L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
- L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.
- L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
- L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
- Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms.
- Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted biphenyl group.
- Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Naphthyl group; Or a biphenyl group.
- the compound represented by Chemical Formula 1 may be any one of the following compounds, but is not limited thereto.
- R3 and R4 are the same as or different from each other, and hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
- R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms; Or an aryl group having 6 to 60 carbon atoms.
- R3 and R4 are each hydrogen.
- n3 is 0 or 1.
- n4 is 0 or 1.
- L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
- L3 and L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
- L3 and L4 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.
- L3 and L4 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
- L3 and L4 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
- Ar3 and Ar4 are the same as or different from each other, and each independently substituted or unsubstituted with a deuterium or aryl group; Or a biphenyl group unsubstituted or substituted with deuterium or aryl groups.
- Ar3 and Ar4 are the same as or different from each other, and each independently substituted or unsubstituted with deuterium or an aryl group having 6 to 60 carbon atoms; Or a biphenyl group unsubstituted or substituted with deuterium or an aryl group having 6 to 60 carbon atoms.
- Ar3 and Ar4 are the same as or different from each other, and each independently substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms; Or a biphenyl group unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.
- Ar3 and Ar4 are the same as or different from each other, and each independently deuterium, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or an anthracenyl group-substituted or unsubstituted phenyl group; Or a biphenyl group unsubstituted or substituted with deuterium, phenyl, biphenyl, terphenyl, naphthyl or anthracenyl.
- Ar3 and Ar4 are the same as or different from each other, and each independently a deuterium, phenyl group, biphenyl group, terphenyl group, or a phenyl group unsubstituted or substituted; Or a biphenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group.
- L5 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
- L5 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
- L5 is a direct bond; Or an arylene group having 6 to 30 carbon atoms.
- L5 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
- L5 is a direct bond; Phenylene group; Or a naphthylene group.
- Ar5 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
- Ar5 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
- Ar5 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium or aryl groups; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
- Ar5 is a deuterium, phenyl group, naphthyl group, phenanthrenyl group or triphenylenyl group substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Dibenzofuranyl group; Or dibenzothiophenyl group.
- the compound represented by Chemical Formula 2 may be any one of the following compounds, but is not limited thereto.
- Chemical Formula 3 may be represented by the following Chemical Formula 3-1.
- Cy1 to Cy3, X1, Ra and Rb are defined as in Chemical Formula 3.
- the Cy1 To Cy3 Is the same as or different from each other, each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms, and Cy1 and Cy2 may combine with each other to form a substituted or unsubstituted ring.
- Cy1 to Cy3 are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms, and Cy1 and Cy2 may combine with each other to form a substituted or unsubstituted ring.
- Ra is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring.
- Ra is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring.
- Ra is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring.
- Rb is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring.
- Rb is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring.
- the Rb is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combine with Cy1 or Cy3 to form a substituted or unsubstituted ring.
- the compound represented by Chemical Formula 3 may be any one of the following compounds, but is not limited thereto.
- the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present invention may have a core structure as shown in Reaction Formula 1, and the compound represented by Chemical Formula 2 according to an exemplary embodiment of the present invention may be used as the following Reaction Formulas 2 and 3
- a core structure may be prepared, and the compound represented by Chemical Formula 3 according to an exemplary embodiment of the present invention may have a core structure as shown in Reaction Scheme 4 below.
- Substituents of Formulas 1 to 3 prepared in Reaction Schemes 1 to 4 may be combined by methods known in the art, and the type, location, or number of substituents may be changed according to techniques known in the art. have.
- Ar1, Ar2, L1, L2, R1, R2, n1 and n2 are defined as defined in Formula 1 above.
- compounds having various energy band gaps may be synthesized by introducing various substituents to the core structures prepared in Reaction Schemes 1 to 4.
- the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.
- the organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming a light emitting layer using the compounds represented by Chemical Formulas 1, 2 and 3 described above.
- the compounds represented by Chemical Formulas 1 to 3 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
- the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
- the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present specification includes at least one of a hole transport layer, a hole injection layer, an electron transport layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer.
- the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
- the organic light emitting device of the present specification includes an organic material layer including a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2, and a compound represented by Chemical Formula 3.
- the compound represented by Chemical Formula 3 may include 1 part by weight to 20 parts by weight compared to 100 parts by weight of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, and according to an example, the compound represented by Chemical Formula 1 And it may include 1 part by weight to 10 parts by weight relative to 100 parts by weight of the compound represented by the formula (2).
- the driving voltage of the manufactured organic light emitting device is low, the light emitting efficiency is high, and there is an advantage of having a long life.
- the light emitting layer of the organic light emitting device includes the compound represented by the formula (1) and the compound represented by the formula (2) as a host of the light emitting layer, the compound represented by the formula (3) the light emitting layer It is included as a dopant.
- the organic material layer may include an electron blocking layer, and the electron blocking layer may be a material known in the art.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode
- the second electrode is an anode
- the organic light emitting device may have a stacked structure as described below, but is not limited thereto.
- the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
- FIG. 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
- an anode 2 on the substrate 1 a hole injection layer 5, a hole transport layer 1 (6), a hole transport layer 2 (7), a light emitting layer 8, an electron transport layer 9, an electron injection layer 10 )
- the structure of the organic light emitting device in which the cathode 4 is sequentially stacked is illustrated.
- the organic light emitting device uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof
- PVD metal vapor deposition
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer, and then depositing a material that can be used as a cathode thereon Can be.
- an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
- the organic material layer may further include at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
- the organic material layer may be a multi-layer structure including a hole injection layer, a hole transport layer, a hole transport and injection layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, but is not limited thereto.
- the organic material layer may be made by using a variety of polymer materials, such as a solvent process (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer), not a deposition method.
- a solvent process e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer
- the positive electrode is an electrode for injecting holes
- a positive electrode material is preferably a material having a large work function to facilitate hole injection into an organic material layer.
- Specific examples of 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), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
- the cathode is an electrode that injects electrons
- the cathode material is preferably a material having a small work function to facilitate electron injection into an 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;
- There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
- the hole injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer.
- a hole injection material can be well injected with holes from the anode, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
- the thickness of the hole injection layer may be 1 nm to 150 nm.
- the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. There is an advantage that can be prevented.
- the hole transport layer may serve to facilitate the transport of holes.
- a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer is suitable for a material having high mobility for holes.
- Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
- an electron blocking layer may be provided between the hole transport layer and the light emitting layer.
- the electron blocking layer may be the compound described above or a material known in the art.
- the organic light-emitting device includes an additional light-emitting layer in addition to the light-emitting layer containing the compounds represented by Formulas 1, 2, and 3, the additional light-emitting layer may emit red, green, or blue, and a phosphor or fluorescent material It can be made of.
- the light emitting material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
- Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
- Alq 3 8-hydroxy-quinoline aluminum complex
- Carbazole-based compounds Dimerized styryl compounds
- BAlq 10-hydroxybenzo quinoline-metal compound
- Benzoxazole, benzthiazole and benzimidazole compounds Benzoxazole, benzthiazole and benzimidazole compounds
- Poly (p-phenylenevinylene) (PPV) polymers Spiro compounds
- Polyfluorene, rubrene, and the like but are not limited to these.
- the host material of the additional light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound.
- condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
- heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- PIQIr (acac) bis (1-phenylisoquinoline) acetylacetonateiridium
- PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium
- PQIr (tris (1-) Phosphorescent materials such as phenylquinoline) iridium
- PtOEP octaethylporphyrin platinum
- fluorescent materials such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used, but are not limited thereto.
- a phosphorescent material such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a fluorescent material such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used as the light emitting dopant. It can, but is not limited to this.
- a phosphorescent material such as (4,6-F2ppy) 2 Irpic is used as a light emitting dopant, but spiro-DPVBi, spiro-6P, distylbenzene (DSB), distriarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.
- the electron transport layer may serve to facilitate the transport of electrons.
- the electron transport material a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these.
- the thickness of the electron transport layer may be 1 nm to 50 nm.
- the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and when it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There are advantages.
- the electron injection layer may serve to facilitate injection of electrons.
- the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
- the hole blocking layer is a layer that prevents the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.
- the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
- the compound according to one embodiment of the present specification may be prepared by a manufacturing method described later.
- the core structure of the compound of Formula 1 structure may be prepared through Reaction Schemes 1 to 4.
- Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be changed according to techniques known in the art.
- n-butyllithium pentane solution (8 ml, 2.5M in hexane) was added at 0 ° C under an argon atmosphere. After completion of the dropwise addition, the temperature was raised to 50 ° C and stirred for 2 hours. After cooling to -40 ° C, boron tribromide (2.88 ml) was added, the temperature was raised to room temperature and stirred for 4 hours. Then, it was cooled to 0 ° C again, N, N-diisopropylethylamine (8 ml) was added, and the reaction solution was further stirred at room temperature for 30 minutes. Sat.aq.
- a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
- Fischer Co. was used as a detergent
- distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
- ultrasonic cleaning was repeated twice for 10 minutes with distilled water.
- ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner.
- the substrate was washed for 5 minutes using nitrogen plasma, and then transferred to a vacuum evaporator.
- HAT-CN compound was thermally vacuum-deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer.
- HTL1 was thermally vacuum-deposited to a thickness of 100 nm, and then HTL2 was thermally vacuum-deposited to a thickness of 10 nm to form a hole transport layer.
- Compound 1, Compound A as a host, and BD-A (weight ratio 47.5: 47.5: 5) as a dopant were simultaneously vacuum-deposited to form a 20 nm thick light emitting layer.
- ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer.
- LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer.
- an organic light emitting device was manufactured by depositing aluminum to a thickness of 100 nm to form a cathode.
- An organic light emitting device was manufactured in the same manner as in Example 1, but as a host and a dopant, using the materials and contents of Table 1 below (parts by weight based on the sum of the host and the dopant 1), and the Example 1 25 and the driving voltage and luminous efficiency were measured at a current density of 10 mA / cm 2 of the organic light-emitting devices prepared in Comparative Examples 1 to 10, and the time at which the luminance was 97% compared to the initial luminance at a current density of 20 mA / cm 2 (LT) was measured, and the results are shown in Table 2 below.
- the organic light emitting device of Examples 1 to 25 including both the compound represented by Formula 1, the compound represented by Formula 2, and the compound represented by Formula 3 includes the compound represented by Formula 2 herein Comparative Examples 1 to 6 and Comparative Examples 7 and 8, which do not contain the compounds represented by Formula 3, can be confirmed to have superior device characteristics.
Abstract
Description
Claims (9)
- 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하는 유기물층을 포함하고,상기 발광층은 하기 화학식 1로 표시되는 화합물, 하기 화학식 2로 표시되는 화합물 및 하기 화학식 3으로 표시되는 화합물을 포함하는 것인 유기발광소자:[화학식 1]상기 화학식 1에 있어서,Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이며,L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 할로겐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,n1 및 n2는 각각 0 내지 4의 정수이고, 상기 n1 및 n2가 각각 2 이상인 경우 2 이상의 괄호 내의 치환기는 서로 같거나 상이하며,[화학식 2]상기 화학식 2에 있어서,Ar3 및 Ar4는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 비페닐기이며,Ar5는 치환 또는 비치환된 아릴기; 치환 또는 비치환된 디벤조퓨라닐기; 또는 치환 또는 비치환된 디벤조티오페닐기이고,L3 내지 L5는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 할로겐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,n3은 0 내지 4의 정수이고, 상기 n3이 2 이상인 경우 2 이상의 R3는 서로 같거나 상이하며,n4는 0 내지 3의 정수이고, 상기 n4가 2 이상인 경우 2 이상의 R4는 서로 같거나 상이하며,[화학식 3]상기 화학식 3에 있어서,X1은 B 또는 P(=O)이며,Y1은 O, S 또는 NRa이고, Y2는 O, S 또는 NRb이며,Cy1 내지 Cy3는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 방향족 헤테로고리이고, 상기 Cy1 및 Cy2는 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며,Ra는 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 Cy1 또는 Cy3와 결합하여 치환 또는 비치환된 고리를 형성하고,Rb는 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 상기 Cy2 또는 Cy3와 결합하여 치환 또는 비치환된 고리를 형성한다.
- 청구항 1에 있어서,상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기인 유기발광소자.
- 청구항 1에 있어서,상기 Ar3 및 Ar4는 서로 같거나 상이하고, 각각 독립적으로 중수소 또는 탄소수 6 내지 60의 아릴기로 치환 또는 비치환된 페닐기; 또는 중수소 또는 탄소수 6 내지 60의 아릴기로 치환 또는 비치환된 비페닐기인 유기발광소자.
- 청구항 1에 있어서,상기 화학식 1로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물은 상기 발광층의 호스트이고,상기 화학식 3으로 표시되는 화합물은 상기 발광층의 도펀트인 유기발광소자.
- 청구항 1에 있어서,상기 화학식 3으로 표시되는 화합물은 상기 화학식 1로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물 100 중량부 대비 1 중량부 내지 20 중량부로 포함되는 유기발광소자.
- 청구항 1에 있어서,상기 유기물층은 정공수송층, 정공주입층, 전자차단층, 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 정공수송 및 주입층 중 1 층 이상을 더 포함하는 유기발광소자.
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150006199A (ko) * | 2013-07-08 | 2015-01-16 | 덕산하이메탈(주) | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
KR20160090444A (ko) * | 2015-01-21 | 2016-08-01 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
WO2017188111A1 (ja) * | 2016-04-26 | 2017-11-02 | 学校法人関西学院 | 有機電界発光素子 |
KR20170130434A (ko) * | 2015-03-24 | 2017-11-28 | 가꼬우 호징 관세이 가쿠잉 | 유기 전계 발광 소자 |
KR20170130435A (ko) * | 2015-03-25 | 2017-11-28 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 및 발광층 형성용 조성물 |
KR20180121843A (ko) | 2018-10-24 | 2018-11-09 | 임선욱 | 기능성 휴대 물건 분실 방지 장치 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100696505B1 (ko) * | 2005-03-31 | 2007-03-19 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 및 그 제조방법 |
US10374166B2 (en) * | 2014-02-18 | 2019-08-06 | Kwansei Gakuin Educational Foundation | Polycyclic aromatic compound |
WO2015194839A1 (en) * | 2014-06-17 | 2015-12-23 | Rohm And Haas Electronic Materials Korea Ltd. | Electron buffering material and organic electroluminescent device |
US9947878B2 (en) * | 2014-08-20 | 2018-04-17 | Lg Chem, Ltd. | Organic light-emitting device |
KR101781739B1 (ko) * | 2015-10-07 | 2017-09-25 | 주식회사 엘지화학 | 신규 화합물 및 이를 포함하는 유기 발광 소자 |
KR101806464B1 (ko) | 2015-11-19 | 2017-12-07 | (주)랩토 | 피리딜기가 결합된 피리미딘 유도체 및 이를 이용한 유기 전계 발광 소자 |
CN110495007B (zh) * | 2017-04-03 | 2022-06-28 | 出光兴产株式会社 | 有机电致发光元件和电子设备 |
JPWO2018186404A1 (ja) * | 2017-04-03 | 2020-02-20 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
US20210005825A1 (en) * | 2017-04-03 | 2021-01-07 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element and electronic device |
CN107507921B (zh) * | 2017-09-29 | 2019-05-14 | 江苏三月光电科技有限公司 | 一种含硼有机电致发光器件及其制备方法 |
-
2019
- 2019-10-11 US US17/055,857 patent/US20210257552A1/en active Pending
- 2019-10-11 KR KR1020190125962A patent/KR102245933B1/ko active IP Right Grant
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20150006199A (ko) * | 2013-07-08 | 2015-01-16 | 덕산하이메탈(주) | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
KR20160090444A (ko) * | 2015-01-21 | 2016-08-01 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR20170130434A (ko) * | 2015-03-24 | 2017-11-28 | 가꼬우 호징 관세이 가쿠잉 | 유기 전계 발광 소자 |
KR20170130435A (ko) * | 2015-03-25 | 2017-11-28 | 가꼬우 호징 관세이 가쿠잉 | 다환 방향족 화합물 및 발광층 형성용 조성물 |
WO2017188111A1 (ja) * | 2016-04-26 | 2017-11-02 | 学校法人関西学院 | 有機電界発光素子 |
KR20180121843A (ko) | 2018-10-24 | 2018-11-09 | 임선욱 | 기능성 휴대 물건 분실 방지 장치 |
Non-Patent Citations (1)
Title |
---|
See also references of EP3767695A4 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020200884A1 (en) * | 2019-03-29 | 2020-10-08 | Cynora Gmbh | Organic molecules for optoelectronic devices |
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KR102245933B1 (ko) | 2021-04-29 |
EP3767695A4 (en) | 2021-09-15 |
JP6989034B2 (ja) | 2022-01-05 |
EP3767695A1 (en) | 2021-01-20 |
US20210257552A1 (en) | 2021-08-19 |
EP3767695B1 (en) | 2022-07-06 |
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