WO2017104946A1 - Composé organique, composition, élément optoélectronique organique et dispositif d'affichage - Google Patents

Composé organique, composition, élément optoélectronique organique et dispositif d'affichage Download PDF

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WO2017104946A1
WO2017104946A1 PCT/KR2016/010521 KR2016010521W WO2017104946A1 WO 2017104946 A1 WO2017104946 A1 WO 2017104946A1 KR 2016010521 W KR2016010521 W KR 2016010521W WO 2017104946 A1 WO2017104946 A1 WO 2017104946A1
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substituted
unsubstituted
group
formula
organic
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이한일
유은선
정성현
한수진
강동민
신창주
이병관
정수영
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삼성에스디아이 주식회사
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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
    • 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
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • An organic compound a composition, an organic optoelectronic device, and a display device.
  • Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
  • Organic optoelectronic devices can be divided into two types according to the principle of operation.
  • One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electric energy.
  • Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
  • organic light emitting diodes have attracted much attention recently as demand for flat panel displays increases.
  • An organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has an organic layer interposed between an anode and a cathode.
  • the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic material included in the organic layer.
  • One embodiment provides an organic compound capable of implementing high efficiency and long life organic optoelectronic devices.
  • One embodiment provides an organic optoelectronic device composition comprising the organic compound. Another embodiment provides an organic optoelectronic device including the organic compound. Another embodiment provides a display device including the organic optoelectronic device.
  • an organic compound represented by Chemical Formula 1 is provided.
  • Z 1 to Z 13 are each independently N or CR a
  • At least one of Z 1 to Z 13 is N,
  • L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group
  • R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 12 aryl group, or a combination thereof,
  • R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 12 aryl group, a substituted or unsubstituted C 3 to C 12 hate Logo or a combination thereof,
  • R 1 to R 14 and R a are each independently present or two adjacent groups combine to form a ring
  • nl and n2 are each independently an integer of 0 to 2.
  • the organic compound includes a first organic compound, and at least one crab 2 organic compound having a carbazole moiety.
  • an organic optoelectronic device It provides a composition for an organic optoelectronic device.
  • a display device including the organic optoelectronic device is provided.
  • FIG. 1 is a cross-sectional view illustrating an organic light emitting diode according to an embodiment.
  • substituted means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C10 trifluoro such as C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group, C2 to C30 heterocyclic group, C1 to C20 alkoxy group, trifluoromethyl group, etc.
  • substituted herein refers to a deuterium, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C 1 to C40 silyl group, C1 to It may be substituted with a C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 aryl group or C2 to C30 heterocyclic group.
  • substituted means a deuterium, a substituted or unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group or C6 to C30 aryl group Can be substituted have.
  • substituted halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to Two adjacent substituents of C 1 to C 10 trifluoroalkyl group or cyano group such as C 30 aryl group, C 3 to C 30 heterocyclic group, C 1 to C 20 alkoxy group, trifluoromethyl group, etc. may be fused to form a ring.
  • the substituted C6 to C30 aryl group may be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
  • hetero 'includes at least one heteroatom in one functional group and the remainder is carbon, said heteroatom selected from N, 0, S, P and Si. Can be.
  • aryl group refers to a group having one or more carbocyclic aromatic moieties, and broadly the form in which the carbocyclic aromatic moieties are connected in a single bond and the carbocyclic aromatic moieties are directly or
  • Aryl groups include monocyclic, polycyclic or fused polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
  • heterocyclic group refers to at least one hetero atom selected from N, 0, S, P and Si in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof or a combination thereof. Containing, and the rest is carbon.
  • the heterocyclic group may include one or more heteroatoms for all or each ring.
  • a substituted or unsubstituted aryl group and / or a substituted or unsubstituted heterocyclic group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted group Substituted phenanthryl groups, substitutions or
  • Naphthyridinyl groups substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted
  • Phenazineyl group substituted or unsubstituted phenothiazineyl group, substituted or unsubstituted
  • a dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a combination thereof, or a combination thereof may be in a fused form, but is not limited thereto.
  • the substituted or unsubstituted aryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted It may be a quarterphenyl group or a substituted or unsubstituted fluorenyl group.
  • a substituted or unsubstituted indenyl group a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group , Substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted Done
  • Dibenzofuran group may be a substituted or unsubstituted di banjo a thiophenyl group, a substituted or unsubstituted carbazole, a combination thereof or a combination thereof fused form, but is not The "May eu
  • the hole characteristic refers to electrons when an electric field is applied. It refers to a property that can form holes by donating, and has conductivity characteristics along the HOMO level to facilitate injection of holes formed in the anode into the light emitting layer, movement of holes formed in the light emitting layer into the anode, and movement in the light emitting layer. Means to come.
  • the electron characteristic refers to a characteristic that can receive electrons when an electric field is applied, and has a conductivity characteristic along the LUMO level, and injects electrons formed in the cathode into the light emitting layer, moves electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.
  • An organic compound according to one embodiment may be represented by Formula 1 below.
  • Z 1 to Z 13 are each independently N or CR a ,
  • At least one of Z 1 to Z 13 is N,
  • L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group
  • R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
  • R 1 1 to R 14 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 'heterocyclic group Or a combination thereof,
  • R 1 to R 14 and R a are each independently present or two adjacent groups combine to form a ring
  • nl and n2 are each independently an integer of 0 to 2.
  • the organic compound may include a dibenzoquinoxaline moiety and a ring having at least one nitrogen, and thus may have a structure in which electrons are easily received when an electric field is applied, and thus driving voltage of the organic optoelectronic device to which the organic compound is applied. This can lower the efficiency and increase efficiency.
  • the LUMO energy of the organic compound calculated by the B3LYP / 6-31G ** method using Gaussian 09 can be, for example, -1.5 eV to -2.0 eV. Within this range, for example, about 1.7 eV to -1.8 eV.
  • the organic compound may implement an asymmetric structure by including a nitrogen-containing ring substituent that extends to one side about the dibenzoquinoxaline, thereby lowering the crystallinity by inhibiting the interaction of molecules.
  • the organic compound has an asymmetric structure so that
  • Effectively preventing stacking can increase process stability while lowering the deposition temperature.
  • At least two of Z 1 to Z 13 may be N.
  • at least three of Z 1 to Z 13 may be N.
  • at least one of Z 1 to Z 3 may be N.
  • at least one of ⁇ to Z 3 may be N, and each of Z 4 to Z 13 may independently be CR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group. , A substituted or unsubstituted C6 internal C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
  • at least two of Z 1 to Z 3 may be N.
  • At least two of Z 1 to Z 3 may be N, and each of ⁇ 4 to ⁇ 13 may independently be N or CR a , wherein R a is hydrogen, hydrogen, substituted or unsubstituted. Or a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
  • Z 1 to Z 3 may be all N, ⁇ 4 to ⁇ 13 may be each independently ⁇ or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted Or an unsubstituted C3 to C12 heterocyclic group or a combination thereof.
  • R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
  • L 1 may be, for example, a single bond or have at least one kink structure.
  • the fold structure refers to a structure in which two connecting portions do not form a straight structure.
  • o-phenylene and meta-phenylene in which the connecting portions do not form a straight structure, are represented.
  • P-phenylene having a folding structure and the connecting portions forming a straight structure does not have a bending structure.
  • L 1 is, for example, a single bond, a substituted or unsubstituted phenylene group having a folding structure, a substituted or unsubstituted biphenylene group having a folding structure, a substituted or unsubstituted terphenylene group having a folding structure, a folding structure It may be a substituted or unsubstituted quarterphenylene group, a substituted or unsubstituted pentaphenylene group having a folding structure.
  • L 1 may include, for example, at least one of a single bond or a substituted or unsubstituted 0-phenylene group and a substituted or unsubstituted m-phenylene group.
  • L 1 may be, for example, a single bond or one selected from substituted or unsubstituted groups listed in Group 1 below.
  • R 30 to R 57 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 heteroarylamine group, substituted or unsubstituted C1 to C30 alkoxy Group, halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, ferrocenyl group, or a combination thereof.
  • the molecular weight of the organic compound may be, for example, about 750 or less. Within this range may be greater than or equal to about 538 and less than 750. By having a molecular weight in the above range it is possible to reduce the thermal decomposition of the organic compound by the high temperature during the deposition process and to improve the heat resistance. It may be about 538 to 749 within the range, may be about 550 to 730 within the range, may be about 600 to 700 within the range.
  • the organic compound may be represented by, for example, the following Chemical Formula 2.
  • ⁇ 1 to Z ⁇ R 1 to R 14 , nl and n 2 are as described above,
  • R 15 to R 17 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof Can,
  • n3 and n4 may be each independently an integer of 0 to 2.
  • At least two of Z 1 to Z 13 may be N.
  • at least three of Z 1 to Z 13 may be N.
  • at least one of Z 1 to Z 3 may be N.
  • at least one of Z 1 to Z 3 may be N, and Z 4 to Z 13 may each independently be CR a , wherein R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group , A substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
  • at least two of Z 1 to Z 3 may be N.
  • At least two of Z 1 to Z 3 may be N, and each of ⁇ 4 to ⁇ 13 may independently be ⁇ or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted C1.
  • R a is hydrogen, deuterium, substituted or unsubstituted C1.
  • C10 alkyl group a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
  • Z 1 to Z 3 may be all N
  • Z 4 to Z 13 may be each independently N or CR a
  • R a is hydrogen, deuterium, substituted or unsubstituted C1 to It may be a C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
  • R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
  • the organic compound may be represented by, for example, the following Chemical Formula 3 or 4.
  • X 1 to Z ⁇ R 1 to R 17 , nl to n4 are as described above.
  • at least two of Z 1 to Z 13 may be N.
  • At least three of, for example Z 1 to Z 13 may be a N.
  • At least one of Z 1 to Z 3 may be N.
  • Z 1 to Z 3, at least one of which may be N and, ⁇ 4 to ⁇ 13 each independently represent CR a may be, in which R a is an unsubstituted C1 hydrogen, heavy hydrogen, substituted or unsubstituted To C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
  • At least two of Z 1 to Z 3 may be N.
  • at least two of Z 1 to Z 3 may be N, and each of ⁇ 4 to ⁇ 13 may independently be N or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted. It may be a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof.
  • Z 1 to Z 3 may be all N, ⁇ 4 to ⁇ 13 may be each independently ⁇ or CR a , wherein R a is hydrogen, deuterium, substituted or unsubstituted Or a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
  • R 1 to R 4 may be each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, and R 1 to R 4 may be each independently hydrogen.
  • the organic compound may be one of the compounds listed in the following Group 2, but is not limited thereto. . .
  • the aforementioned organic compound can be applied to organic optoelectronic devices.
  • the aforementioned organic compounds may be applied to the organic optoelectronic device alone or in combination with other organic compounds.
  • the above-mentioned organic compound is used together with other organic compounds, it can be applied in the form of a composition.
  • the composition may include at least one organic compound having the above-described organic compound and a carbazole moiety.
  • the above-described organic compound is referred to as a 'first organic compound' and at least one organic compound having a carbazole moiety is referred to as a 'second organic compound'.
  • the second organic compound may be, for example, a compound represented by Formula 5 below.
  • ⁇ ⁇ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 divalent Heterocyclic group or a combination thereof,
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,
  • R 60 to R 63 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ,
  • At least one of R 60 to R 63 and Ar 1 includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazolyl group.
  • the second organic compound represented by Chemical Formula 5 may be, for example represented by at least one of 5-III in Chemical Formula 5-1.
  • X ', X 4 and X 5 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, substituted Or an unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
  • Ar 1 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted : C2 to C30 heterocyclic group or a combination thereof,
  • R 60 to R 63 and R 6S to R 79 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocycle Groups or a combination thereof.
  • the second organic compound represented by Chemical Formula 5 may be, for example, a compound listed in Group 3, but is not limited thereto.
  • the second organic compound may be, for example, a compound made of a combination of a moiety represented by Formula 6 and a moiety represented by Formula 7. [Formula 6] [Formula 7]
  • Y 2 and Y 3 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 divalent heterocyclic group or a combination thereof,
  • Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,
  • R 64 to R 67 are each independently hydrogen, hydrogen, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C50 aryl group, substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,
  • Adjacent two * of Formula 6 combines with two * of Formula 7 to form a fused ring, and * which does not form a fused ring in Formula 6 is each independently CR b , wherein R b is hydrogen, deuterium Or a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof.
  • the second organic compound consisting of a combination of the moiety represented by Formula 6 and the moiety represented by Formula 7 may be selected from, for example, a compound listed in Group 4 below, but is not limited thereto.
  • the second organic compound may include at least one compound compound consisting of a compound represented by Chemical Formula 5 and a combination of a moiety represented by Chemical Formula 6 and a moiety represented by Chemical Formula 7.
  • the composition may include the first organic compound and the second organic compound in an increase ratio of about 1: 10 to 10: 1.
  • the composition may be applied to an organic layer of an organic optoelectronic device, and the first organic compound and the second organic compound may serve as a host.
  • the first organic compound may be a compound having a bipolar characteristic having a relatively strong electronic property
  • the second organic compound is a compound having a bipolar characteristic having a relatively strong hole characteristic, and used together with the first organic compound to transfer charges. And it is possible to further improve the luminous efficiency and lifetime characteristics by increasing the stability.
  • composition may further include one or more organic compounds in addition to the first organic compound and the second organic compound described above.
  • the composition may further comprise a dopant.
  • the dopant may be a red, green or blue dopant, for example, a phosphorescent dopant.
  • the dopant is a substance that is mixed with the first host compound and the second host compound in a small amount to emit light, and is generally a metal complex that emits light by multiple excitation which excites above a triplet state. Materials such as may be used.
  • the dopant may be, for example, an inorganic, organic, or inorganic compound, and may be included in one kind or two or more kinds.
  • Examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh,
  • the phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.
  • ⁇ is a metal
  • L and X are the same or different from each other and a ligand forming a complex with ⁇ .
  • the ⁇ can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, wherein L and X are, for example, bidentate It may be a ligand.
  • the composition may be formed into a thin film by a dry film forming method or a solution process.
  • the dry film forming method may be, for example, chemical vapor deposition, sputtering, plasma plating, and ion plating, and two or more compounds may be simultaneously formed or a compound having the same deposition temperature may be mixed and formed together.
  • the solution process may be, for example, inkjet printing, spin coating, slit coating, bar coating. And / or dip coating.
  • the organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and light energy, and examples thereof include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photosensitive drums.
  • the organic optoelectronic device may include an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the organic compound or the composition described above.
  • the organic layer may include a light emitting layer including the organic compound or the composition.
  • the organic layer may include an auxiliary layer positioned between the emission layer, the anode and the emission layer, and / or between the cathode and the emission layer, and the auxiliary layer may include the organic compound or the composition.
  • an organic light emitting diode 100 includes an anode 1 10 and a cathode 120 facing each other, and an organic layer 105 positioned between the anode 1 10 and the cathode 120. ).
  • the anode 1 10 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the anode 1 10 is, for example, a metal such as nickel, platinum, vanadium, crumb, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide ( ⁇ ),
  • Metal oxides such as rhodium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene Xpolyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. .
  • IZO rhodium zinc oxide
  • Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene Xpolyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. .
  • the cathode 120 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the cathode 120 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Multilayer structure materials such as LiF / Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
  • the organic layer 105 includes an emission layer 130 comprising the above-mentioned organic compound or the above-described composition.
  • the light emitting layer 130 may include the organic compound or the composition as a host, may include the above-described organic compound alone, or may include at least two kinds of the above-described organic compounds in combination or as described above.
  • the composition may be contained, or may contain a mixture of the above-mentioned organic compound or another organic compound with the above-described composition.
  • the light emitting layer 130 may further include a dopant.
  • the dopant may be a red, green or blue dopant, for example a phosphorescent dopant.
  • the dopant is as described above.
  • the organic layer 105 may further include an auxiliary layer (not shown) positioned between the anode 1 10 and the light emitting layer 130 and / or between the cathode 120 and the light emitting layer 130.
  • the auxiliary layer is a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole Barrier layers or combinations thereof.
  • the auxiliary layer may comprise the aforementioned organic compound or composition.
  • the organic light emitting diode described above may be applied to an organic light emitting diode display. [Form for implementation of invention]
  • intermediate 1-10 (45 g, 9 mmol 5 mmol) was dissolved in 0.4 L of dimethylforamide (DMF), followed by bis (pinacolato) diboron (29.7 g, 117 mmol) and ( ⁇ , ⁇ '- bis (diphenylphosphine). ) ferrocene) dichloropalladium (II) (0.80 g, 0.98 mmol) and potassium acetate (28.7 g, 293 mmol) were added and refluxed at 150 ° C for 18 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate I-11 (32.2 g, 65%).
  • intermediate 1-9 (10 g, 19.7 mmol) was dissolved in 0.1 L of tetrahydrofuran (THF), followed by 2-chloro- purchased from Tokyo Chemical Industry (http://www.tcichemicals.com/). 4,6-diphenyl-l, 3,5-triazine (5.27 g, 19.7 mmol)
  • An organic light emitting device was manufactured using Compound 1 obtained in Synthesis Example 16 as a host and Ir (PPy) 3 as a dopant.
  • ⁇ was used as a positive electrode with a thickness of 1000 A.
  • Aluminum (Al) was used at a thickness of 1000 A.
  • the method of manufacturing the organic light emitting device the anode is cut into a glass substrate having a sheet resistance value of 15 ⁇ / ⁇ 2 to a size of 50mm x 50 mm x 0.7 mm in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was used for 30 minutes.
  • the amount of the phosphorescent dopyeon agent was deposited such that the weight 7 0 /.
  • the total amount of the light-emitting layer 100 parts by weight 0/0.
  • Bis (2-methyl-8- qumolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the emission layer to form a hole blocking layer having a thickness of 50 A. Subsequently, the same vacuum deposition was performed. Alq3 was deposited under the conditions to form an electron transport layer having a thickness of 200 A. As a cathode on the electron transport layer
  • LiF and A1 were sequentially deposited to manufacture an organic photoelectric device.
  • the structure of the organic photoelectric device is nO / NPB (80 nm) / EML (Compound 1 (93 weight 0 /.) + Ir (PPy) 3 (7 weight 0 /.), 30 nm) / Balq (5 nm) / It was produced in the structure of Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).
  • the organic light emitting diodes of Comparative Examples 1 to 3 were prepared in the same manner as in Example 1, except that CBP, Compound Host 1 obtained in Synthesis Example 23, and Compound Host 2 obtained in Synthesis Example 24 were used instead of Compound 1 obtained in Synthesis Example 16.
  • the structure of NPB, BAlq, CBP and Ir (PPy) 3 used in the organic light emitting device is as follows.
  • the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
  • the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
  • a luminance meter Minolta Cs-IOOOA
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
  • Comparative Example 3 HOST2 4.3 Green 18.5
  • Table 1 it can be seen that the organic light emitting diode according to Example 1 to 7 exhibits low driving voltage and high luminous efficiency compared to the organic light emitting diode according to Comparative Examples 1 to 3.
  • the temperature was measured when the HOST of the light emitting layer was deposited during the manufacturing process of the organic light emitting device according to Example 1, which means a temperature at which a thickness of 1 A may be stacked per second (A / sec).
  • the energy input difference was measured as a function of temperature while changing the temperature of the sample and reference using a DSC1 instrument from Metier Teledo.
  • Samples of the compounds were collected lg and filled with nitrogen in a glass container and sealed. After the glass container was stored in an oven at 200 ° C. for 200 hours, the purity was measured in the same manner as the method for measuring the room temperature purity.
  • HOST 2 obtained in Synthesis Example 24 is lower than the compound 3 and Synthesis 12 obtained in Synthesis Example 18 and the compound 12 obtained in Synthesis Example 19 it can be seen that the lower the glass transition temperature, the higher the deposition process temperature and lower the high temperature purity .
  • Compound A was vacuum deposited on the ITO substrate using the prepared ⁇ transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then compound C was deposited to a thickness of 50 A on the injection layer. Depositing a thickness of 1020 A to form a hole transport layer.
  • the oil-emitting light emitting device has a structure having five organic thin film layers, specifically as follows.
  • the organic light emitting diodes of Examples 9 to 13 were obtained by the same method as Example 8, except for using the known compounds B-10, B-31, B-34, B-43, and E-1 instead of the compound C-10. Produced.
  • Comparative Examples 4 to 9 Compound C-10 is used as the sole host, Compound B-10 is used as the sole host, Compound B-10 is used as the sole host, Compound B-31 is used as the sole host, Compound B-34 is the sole host.
  • the organic light emitting diodes of Comparative Examples 4 to 9 were prepared in the same manner as in Example 8, except that Compound B-43 was used as the sole host and Compound E-1 was the sole host. Evaluation II
  • the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
  • the luminance was measured by using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0V to 10V to obtain a result.
  • a luminance meter Minolta Cs-IOOOA
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the brightness, current density and voltage measured from (1) and (2) above.
  • Example 1 Compound 12 B-34 48.5 150 Example 12 Compound 12 B-43 51.0 140
  • Comparative Example 9 E-1 1.4 30 Referring to Table 3, the organic light emitting diode according to Examples 8 to 13 is significantly improved in the luminous efficiency and reception characteristics compared to the organic light emitting diode according to Comparative Example 4 Nag ' 9 You can see that. In addition, it can be seen that the organic light emitting device according to Examples 8 to 13 further improved luminous efficiency and lifespan than the organic light emitting device according to the reference example.
  • the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

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  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé organique représenté par la formule chimique 1, une composition comprenant ledit composé organique, un élément optoélectronique organique comprenant ledit composé organique et/ou ladite composition, et un dispositif d'affichage.
PCT/KR2016/010521 2015-12-18 2016-09-21 Composé organique, composition, élément optoélectronique organique et dispositif d'affichage WO2017104946A1 (fr)

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KR20190001116A (ko) * 2017-06-26 2019-01-04 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
WO2022124367A1 (fr) * 2020-12-11 2022-06-16 日鉄ケミカル＆マテリアル株式会社 Matériau pour élément électroluminescent organique et élément électroluminescent organique
US11588116B2 (en) 2020-03-11 2023-02-21 Lg Chem, Ltd. Organic light emitting device

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KR102162404B1 (ko) * 2017-12-27 2020-10-06 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR20200125080A (ko) * 2019-04-26 2020-11-04 롬엔드하스전자재료코리아유한회사 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
JP2024504058A (ja) * 2021-04-30 2024-01-30 エルジー・ケム・リミテッド 有機発光素子

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WO2022124367A1 (fr) * 2020-12-11 2022-06-16 日鉄ケミカル＆マテリアル株式会社 Matériau pour élément électroluminescent organique et élément électroluminescent organique

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