WO2019059577A1 - Composé organique, composition, élément photoélectronique organique et dispositif d'affichage - Google Patents

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

Info

Publication number
WO2019059577A1
WO2019059577A1 PCT/KR2018/010709 KR2018010709W WO2019059577A1 WO 2019059577 A1 WO2019059577 A1 WO 2019059577A1 KR 2018010709 W KR2018010709 W KR 2018010709W WO 2019059577 A1 WO2019059577 A1 WO 2019059577A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
group
compound
organic
Prior art date
Application number
PCT/KR2018/010709
Other languages
English (en)
Korean (ko)
Other versions
WO2019059577A8 (fr
Inventor
김병구
강기욱
김형선
류동완
신창주
이한일
장기포
정성현
Original Assignee
삼성에스디아이(주)
삼성전자 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 삼성에스디아이(주), 삼성전자 주식회사 filed Critical 삼성에스디아이(주)
Priority to CN201880060688.9A priority Critical patent/CN111108108A/zh
Publication of WO2019059577A1 publication Critical patent/WO2019059577A1/fr
Publication of WO2019059577A8 publication Critical patent/WO2019059577A8/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur

Definitions

  • Organic optoelectronic diodes are devices that can convert between electrical and optical energy.
  • Organic optoelectronic devices can be roughly classified into two types according to the operating principle.
  • One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole and electrons and holes are transferred to different electrodes to generate electric energy.
  • Emitting device that generates light energy from energy.
  • organic optoelectronic devices examples include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.
  • OLEDs organic light emitting diodes
  • OLEDs organic light emitting diodes
  • An organic light emitting device is an element that converts electrical energy into light. The performance of an organic light emitting device is greatly affected by an organic material located between electrodes.
  • One embodiment provides an organic compound capable of realizing a high-efficiency and long-lived organic optoelectronic device.
  • compositions capable of implementing high-efficiency and long-lived organic optoelectronic devices.
  • Another embodiment provides an organic optoelectronic device comprising the organic compound or composition.
  • Another embodiment provides a display device comprising the organic opto-electronic device.
  • an organic compound represented by the following general formula (1) represented by the following general formula (1). [Chemical Formula 1]
  • X 1 and X 2 are each independently 0 or S,
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,
  • L 1 is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group or a combination thereof,
  • R 1 to R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, .
  • composition comprising a first organic compound and a second organic compound comprising a carbazole moiety represented by the following general formula (4).
  • ⁇ ⁇ is a group a single bond, a substituted or unsubstituted C6 to C30 arylene group or a divalent substituted or unsubstituted C2 to C30 heterocyclic group,
  • a 1 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaromatic group
  • R 9 to R 14 each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 To C30 heterocyclic group,
  • R 9 and R 10 are independently present or fused together to form a ring; R 11 to R 14 are each independently present; or adjacent groups of R 11 to R 14 are connected to each other to form a ring.
  • the anode and the cathode facing each other,
  • an organic layer disposed between the anode and the cathode, wherein the organic charge provides the organic compound or the organic optoelectronic device including the composition.
  • a display device including the organic opto-electronic device is provided.
  • 1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.
  • At least one hydrogen in the substituent or compound is replaced with a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, A C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 aryl group, A C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.
  • a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C
  • substituted means that at least one hydrogen in the substituent or compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30
  • substituted means that at least one hydrogen in the substituent or compound is deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 Means a group substituted with a heteroaryl group.
  • substituted means that at least one hydrogen in the substituent or compound is deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, a quinolinyl group, an isoquinolinyl group,
  • substituted means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a dibenzofuranyl group or a dibenzothiophenyl group it means.
  • substituted means that at least one hydrogen in a substituent or a compound is substituted with a substituent selected from the group consisting of deuterium, methyl, ethyl, propanyl, butyl, phenyl, biphenyl, terphenyl, A benzofuranyl group or a dibenzothiophenyl group.
  • aryl group is intended to encompass a group having at least one hydrocarbon aromatic moiety, wherein all elements of the hydrocarbon aromatic moiety have a P-orbital, and these P- Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, Non-aromatic fused rings fused directly or indirectly, such as fluorenyl groups, and the like.
  • the aryl group includes a monocyclic, polycyclic or fused ring cyclic (i. E., A ring having adjacent pairs of carbon atoms) functional groups.
  • heterocyclic group is a superordinate concept including a heteroaryl group, and includes N, O, N, and O substituents in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from the group consisting of S, P and Si.
  • the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.
  • heteroaryl group means containing at least one heteroatom selected from the group consisting of N, O, S, P and Si in the aryl group. 2 or more
  • the heteroaryl group may be directly connected through a sigma bond, or, when the heteroaryl group includes two or more rings, two or more rings may be fused together. remind
  • each ring may contain 1 to 3 of the above heteroatoms.
  • the heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like.
  • Substituted or unsubstituted phenanthryl groups substituted or unsubstituted phenothiazyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted dibenzofuranyl groups, or substituted or unsubstituted dibenzoyl groups, Thiophene group, or a combination thereof, but is not limited thereto.
  • the hole property refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer.
  • the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied.
  • the electron characteristic has a conduction characteristic along the LUMO level so that electrons formed in the cathode are injected into the light emitting layer, electrons generated in the light emitting layer migrate to the cathode, Which means a characteristic that facilitates the movement of the object . do.
  • the organic compound according to one embodiment is represented by the following formula (1).
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,
  • L 1 is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group or a combination thereof,
  • R 1 to R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, .
  • the organic compound represented by the general formula (1) can exhibit fast electron transporting characteristics by including a substituted pyrimidine ring and a fused ring to which benzofuran or benzothiophene is bonded, and can exhibit fast electron transporting properties, and the benzofuran or benzothiophene side of the fused ring Or a dibenzothiophenyl group may be bonded to each other to exhibit faster electron transporting characteristics. Accordingly, when an organic compound is applied to a device, a low driving voltage and a high efficiency Device can be implemented.
  • the organic compound represented by the general formula (1) has a relatively high glass transition temperature, when the organic compound is applied to the device, it can reduce or prevent deterioration of the organic compound during the process or operation, thereby improving the thermal stability and improving the lifetime of the device .
  • the organic compound may have a glass transition temperature of about 50 to 300 ° C.
  • X 1 and X 2 in Formula (1) may be the same or different.
  • X 1 and X 2 may be the same, X 1 and X 2 may be 0, and X 1 and X 2 may be S, respectively.
  • X 1 and X 2 may be different from each other, X 1 may be S, X 2 may be 0, X 1 may be 0, and X 2 may be S.
  • Ar 1 and Ar 2 in the formula (1) each independently represent a substituted or unsubstituted C6 to C30 aryl group, and examples thereof include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted A phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylene group.
  • the substitution may be such that at least one hydrogen is replaced by deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.
  • L < 1 &gt may be a single bond or a substituted or unsubstituted C6 to C30 arylene group.
  • L 1 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthracenylene .
  • L < 1 &gt may be a single bond or a substituted or unsubstituted phenylene group.
  • substitution may be such that at least one hydrogen is replaced by deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.
  • each of R 1 to R 6 may independently be a hydrogen, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C6 to C30 aryl group substituted with a cyano group.
  • R 1 to R 6 each independently may be a hydrogen, a cyano group, a C 1 to C 4 alkyl group, a C 6 to C 12 aryl group, or a C 6 to C 12 aryl group substituted with a cyano group.
  • the organic compound may be represented by, for example, any one of the following formulas (2) to (5), but is not limited thereto.
  • [Chemical Formula 2] < EMI ID
  • X 1 , X 2 , R 1, R 2 and R 1 to R 6 are as described above.
  • the organic compound may be represented by, for example, any one of the following formulas (2a) to (2d), (3a), (3d), (4a) to (4d) and
  • L 1 may be a single bond or a substituted or unsubstituted phenylene group.
  • L 1 may be a single bond.
  • the organic compound may be, for example, selected from the compounds listed in the following Group 1, but is not limited thereto.
  • the above-mentioned organic compounds can be applied to organic optoelectronic devices alone or together with other organic compounds.
  • the above-mentioned organic compounds can be applied in the form of a composition.
  • composition according to one embodiment will be described below.
  • composition according to one embodiment may include the above-mentioned organic compound (hereinafter referred to as a "first organic compound”) and an organic compound having a hole property (hereinafter referred to as "second organic compound").
  • first organic compound organic compound having a hole property
  • second organic compound organic compound having a hole property
  • the organic compound may include, for example, a carbazole moiety and may be, for example, a substituted or unsubstituted carbazole compound, a substituted or unsubstituted biscarbazole compound, or a substituted or unsubstituted indolocarbazole compound, But is not limited thereto.
  • the second organic compound may include a carbazole moiety represented by the following general formula (4). In Formula 4,
  • Y 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group or a divalent substituted or unsubstituted C2 to C30 heterocyclic group,
  • a 1 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
  • R 9 to R 14 each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
  • R 9 and R 10 are each independently present or fused together to form a ring
  • R 11 to R 14 are each independently present or adjacent groups of R 11 to R 14 are connected to each other to form a ring.
  • the substitution may be such that at least one hydrogen is substituted with deuterium, a C1 to C10 alkyl group, a C6 to C12 aryl group or a C2 to C10 heteroaryl group, for example at least one hydrogen is deuterium, an ortho-biphenyl group, a meta-biphenyl group, a para-biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group or
  • the second organic compound may be a compound represented by the following formula (4A).
  • Y 1 and Y 2 each independently may be a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
  • a 1 and A 2 each independently may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
  • R 9 to R 11 and R 15 to R 17 each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic ring Group, or a combination thereof,
  • n may be an integer of 0 to 2.
  • Y 1 and Y 2 in the general formula (4A) each independently represent a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and examples thereof include a single bond, a meta- A meta-biphenylene group, or a para-biphenylene group.
  • a 1 and A 2 in the formula (4A) may be a substituted or unsubstituted C6 to C30 aryl group, for example, an aryl group may be selected from a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group.
  • a 1 and A 2 each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted An anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazole group, A substituted or unsubstituted fluorenyl group, or a combination thereof.
  • V and A 2 in Formula 4A are each independently a substituted or unsubstituted phenyl group, An unsubstituted biphenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.
  • R 9 substituents R 11 and R 15 to R 17 in Formula 4A are hydrogen, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30
  • a heterocyclic group may be, for example, all hydrogen.
  • n in Formula 4A may be 0 or 1, e.g., m may be 0.
  • the bonding position of two carbazole groups may be a 2,3-bond, a 3,3-bond, or a 2,2-bond, for example, a 3,3-bond.
  • the compound represented by the formula (4A) can be represented by the following formula (4A-1).
  • R 11 , R 11 and R 15 to R 17 are as described above.
  • the compound represented by Formula 4A may be a compound in which one of the carbazole cores listed in Group 2 is combined with the substituents-Y'-A 1 and * -Y 2 -A 2 listed in Group 3 below, But is not limited thereto.
  • the compound represented by Formula 4A may be, but is not limited to, one of the compounds listed in Group 4 below .
  • the ternary organic compound may be an indolocarbazole compound represented by a combination of the following formulas (4B-1) and (4B-2).
  • Y 1 and Y 3 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
  • a 1 and A 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,
  • the two adjacent * in the formula 4B-1 are bonded to two of the * in the formula 4B-2, and the remaining two * in the formula 4B-1 are each independently CR 11 , wherein R 11 are the same or different from each other,
  • R 9 to R U , R 18 and R 19 each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocycle Or a combination thereof.
  • Y 1 and Y 3 in formulas (4B-1) and (4B-2) may each independently be a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.
  • a 1 and A 3 in the formulas 4B-1 and 4B-2 may be substituted or unsubstituted C6 to C30 aryl groups.
  • the aryl group may be a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, More preferably a biphenyl group, a naphthyl group, a terphenyl group or a phenyl group.
  • a 1 and A 3 in formulas (4B-1) and (4B-2) each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group , Substituted or unsubstituted
  • An anthracenyl group or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted A dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
  • the indolocarbazole compound represented by the combination of the formulas 4B-1 and 4B-2 can be represented by any of the following formulas 4B-a to 4B-e.
  • the indolocarbazole compound represented by the combination of the formulas 4B-1 and 4B-2 may be represented by the following formula 4B-C or 4B-d.
  • the indolocarbazole compound represented by the combination of the formulas 4B-1 and 4B-2 may be represented by the following formula 4B-c.
  • the compound represented by the combination of the formulas 4B-1 and 4B-2 may be, for example, one of the compounds listed in the following group 5, but is not limited thereto.
  • the first organic compound and the second organic compound may include various compositions by various combinations.
  • the composition may comprise the gauze organic compound and the second compound in a weight ratio of about 1:99 to 99: 1, such as about 10:90 to 90:10, about 20:80 to 80:20, about 30:70 To about 70: 30, from about 40: 60 to about 60: 40, or about 50: 50.
  • the composition may contain one or more organic
  • the ancestor may further include a dramatome.
  • the splittable can be red, green or blue.
  • a material such as a metal complex which emits light by multiple excitation which excites a triplet state abnormality generally can be used as the material which generates a trace amount of light emission.
  • the dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.
  • the dopant may comprise from about 0.1 to 20 parts by weight 0/0 with respect to the total amount of the composition.
  • dopants examples include phosphorescent dopants.
  • examples of phosphorescent dopants include Ir, Pt,
  • the phosphorescent scavenger is, for example,
  • M is a metal
  • L and X are the same or different from each other and are ligands which complex with M.
  • the L may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, Lt; / RTI >
  • an organic optoelectronic device to which the above-described organic compound or composition is applied
  • the organic optoelectronic device may be, for example, an organic light emitting device, an organic photoelectric device, Battery or the like.
  • the organic optoelectronic device can be, for example, an organic light emitting device.
  • the organic optoelectronic device may include an anode and a cathode facing each other, and an organic charge located between the anode and the cathode, and the organic layer may include the above-described organic compound or the above-described composition.
  • the organic layer may include an active layer such as a light emitting layer or a light absorbing layer, and the above-described organic compound or the above-described composition may be included in the active layer.
  • an active layer such as a light emitting layer or a light absorbing layer
  • the organic layer may include an auxiliary layer located between the anode and the active layer and / or between the cathode and the active layer, and the above-described organic compound or the above-described composition may be included in the auxiliary layer.
  • FIG. 1 is a cross-sectional view showing an example of an organic light emitting device as an example of an organic optoelectronic device.
  • an organic light emitting device 100 includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 disposed between the anode 110 and the cathode 120 .
  • the anode 110 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
  • the anode 110 may be made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (?
  • Metal oxides such as indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, But is not limited thereto.
  • the cathode 120 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
  • the cathode 120 may be formed of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca.
  • the organic layer 105 may comprise the above-described organic compounds or the above-described compositions.
  • the organic layer 105 may include a light emitting layer 130.
  • the light emitting layer 130 may include the above-described organic compound as a host or the above-described composition.
  • the light emitting layer 130 may further include another organic compound as a host.
  • the light emitting layer 130 may further include a dopant, and the splitter may be, for example, a phosphorescent dopant.
  • the organic layer 105 may further include an auxiliary layer (not shown) positioned between the anode 110 and the light emitting layer 130 and / or the cathode (1 20) and the light emitting layer (130).
  • the auxiliary layer may be a hole injection layer, a hole transporting layer, an electron blocking layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, or a combination thereof.
  • the auxiliary layer may comprise the above-described organic compounds or the above-described compositions.
  • FIG. 2 is a cross-sectional view of an organic light emitting device according to another embodiment.
  • an organic light emitting device 200 includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 between the anode 110 and the cathode 120 .
  • the organic charge 105 is an electron (electron) positioned between the light emitting layer 230 and the cathode 120,
  • the electron assist layer 140 may be, for example, an electron injection layer, an electron transport layer, and / or a hole blocking layer, and may facilitate injection and movement of electrons between the cathode 120 and the light emitting layer 230.
  • the above-described organic compound or the above-described composition may be included in the light emitting layer 230.
  • the light emitting layer 230 may further include another organic compound as a host.
  • the light emitting layer 230 may further include a splint, and the dopant may be, for example, a phosphorescent splitter.
  • the above-described organic compound may be included in the electron-assisted layer 140.
  • the electron-assisted layer 140 may include the above-described organic compounds alone or may include at least two of the above-described organic compounds commonly or may include other organic compounds than the above-described organic compounds.
  • the organic layer 105 may further include at least one hole-assist layer (not shown) positioned between the anode 110 and the light-emitting layer 230.
  • the organic light emitting device described above can be applied to an organic light emitting display.
  • intermediate 1-1 (216.0 g, 0.7 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- (21.8 g, 0.8 mol), potassium acetate (KOAc, 197.4 g, 2.0 mol) and 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride 0.03 mol) and tricyclohexylphosphine (45.1 g, 0.2 mol) were placed in 3 L of N, N-dimethylformamide and stirred for 12 hours at 130 DEG C. After completion of the reaction, And water was removed from the obtained organic layer using a magnesium sulfate. The filtrate was concentrated and purified by column chromatography to obtain Intermediate 1-2 as a white solid (205.5 g, 83% yield).
  • Tetrakis (triphenylphosphine) palladium (0) (1.2 & 1.04 ⁇ 1) was dissolved in 80 mL of 1,4-dioxane, 40 mL of water (40 mL), potassium carbonate (11.93 g, 86.3 mmol) mL, and then heated at 70 ° C for 12 hours in a stream of nitrogen. The organic layer was separated, and 240 mL of methanol was added thereto. The crystallized solid was filtered, and then dissolved in monochlorobenzene. The filtrate was purified by silica gel /
  • the glass substrate on which the ITO electrode was formed was cut into a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, and then subjected to UV ozone cleaning for 30 minutes.
  • M-MTDATA was vacuum-deposited on the? Voltage electrode at a deposition rate of 1 A / sec to form a hole injection layer having a thickness of 600 A, and the? -NUMB was vapor deposited at a deposition rate of 1 A / sec on the hole injection layer To form a hole transporting layer having a thickness of 300 A.
  • Ir (ppy) 3 (dopant 1) and compound 2 (host) were deposited on the hole transporting layer at a deposition rate
  • a luminescent layer of 400A thickness was formed by co-deposition with Ol A / sec and l A / sec.
  • BAlq was vacuum deposited on the light emitting layer at a deposition rate of 1 A / sec to form a hole blocking layer having a thickness of 50 A
  • Alq 3 was vacuum deposited on the hole blocking layer to form an electron transporting layer having a thickness of 300 A .
  • LiF lOA electron injection layer
  • Examples 2 to 25 An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound described in Table 1 was used in place of Compound 2 as a host during luminescence.
  • Comparative Compound 18, 40, 48, 155, or 189 was used instead of Compound 2 as a light emitting layer host. Comparative compound 18, 40, 48, 155 or 189 was prepared by the method disclosed in JP 5604848 or JP publication No. 2015- 134745.
  • the driving voltage, the efficiency, and the luminance of the organic luminescent devices according to Examples 1 to 25 and Comparative Examples 1 to 5 were supplied with power from a current voltmeter (Kethley SMU 236), and the luminance was measured using a luminance meter PR650 Spectroscan Source Measurement Unit ).
  • the specific measurement method is as follows.
  • the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.
  • luminance was measured using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0 V to 10 V, and the result was obtained.
  • the current efficiency (cd / A) at the same current density (10 mA / cm 2) was calculated using the luminance, current density and voltage measured from the above (1) and (2).
  • the T 95 lifetime is an evaluation of the time (hr) required for the luminance to become 95% of the initial luminance of 100%.
  • the host used in the light emitting layer of the organic light emitting device according to Examples 1 to 25 has excellent charge transporting properties as a phosphorescent host material, and the absorption spectrum and the light emitting wavelength region of the dopant are overlapped, It can be seen that the improvement in performance such as excellent driving voltage reduction and the ability as an OLED material are maximized. Above all, it can be confirmed that the life span remarkably improves.
  • Comparative Example 18 had a poor electron transporting ability and thus it was difficult to achieve a balance between hole transport and electron transport, and thus the current efficiency of the organic light emitting device according to Comparative Example 1, which was used as a host of the light emitting layer, was poor.
  • Comparative Compounds 18, 40, 48, and 156 used as hosts in the organic light emitting device according to Comparative Examples 2 to 5 have a structure in which carbon adjacent to N of pyridine, pyrimidine and quinoxaline in the fused ring is unsubstituted, that is, CH.
  • the thermal stability and electrical stability of the light-emitting layer of the organic light-emitting device to which the organic light-emitting device is applied may be weak, and thus the life characteristics of the organic light-emitting device according to the comparative example using the same as the host of the light- have.
  • An organic light emitting device was fabricated using Compound 3 obtained in Synthesis Example 7 as a host and (piq) 2 Ir (acac) (dopant 2) as a dopant.
  • ITO As the anode, ITO was used in a thickness of 1000 A, and aluminum (A1) was used as a cathode
  • the ITO glass substrate having a sheet resistance value of 15Q / cm 2 is cut into a size of 50 mm x 50 mm x 0.7 mm, and is coated with a mixture of acetone, isopropyl alcohol and pure water in an amount of 15 Min for 30 minutes, and then rinsed with UV ozone for 30 minutes.
  • N4, N4'-di (naphthalene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-dicarboxylate was vapor-deposited on the substrate at a degree of vacuum of 650 ⁇ 10 7 Pa and a deposition rate of 0.1 to 0.3 nm / (N4, N4'-di (naphthylene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'- diamine: NPB) (80 nm) was deposited thereon to form a hole transport layer of 800 A.
  • the phosphorescent dopant (piq) 2 Ir (acac) was deposited at the same time by using the compound 3 obtained in Synthesis Example 7 under the same vacuum deposition conditions to form a light emitting layer having a thickness of 300 A. At this time, To adjust the total amount of the light emitting layer to 100 wt%, the phosphorescent dopant was vapor-deposited in an amount of 3 wt%.
  • the structure of an organic optoelectronic device is ⁇ / ⁇ (80 nm) / EML ( Compound 3 (97 parts by weight 0/0) + (piq) 2 Ir (acac) (3 Increased 0/0), 30nm) / Balq (5nm) / Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).
  • An organic light emitting device was prepared in the same manner as in Example 52 except that Comparative Compound 18, 40, 48, 155, 156, 189, 327 and 328 were used instead of Compound 3 as a light emitting layer host.
  • Comparative compounds 18, 40, 48, 155, or 189 were prepared by the method disclosed in JP Patent No. 5604848 or JP Patent No. 2015-134745.
  • the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.
  • luminance was measured using a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from 0 V to 10 V, and the result was obtained.
  • the current efficiency (cd / A) at the same current density (10 mA / cm 2) was calculated using the luminance, current density and voltage measured from the above (1) and (2).
  • the decrease in efficiency was calculated as% in (3) (Max value - Numerical value at 5000 cd / m 2 / Max value).
  • Example 26 Compound 3 Dopant 2 4.66 14.3 15.5 125
  • Example 27 Compound 9 Said 2 4.50 15.2 14.8 131
  • Example 28 Compound 17 Said 2 4.60 14.4 15.0 133
  • Example 29 Compound 18 Dopent 2 4.32 14.5 14.1 142
  • Example 30 Compound 19 Dopant 2 4.23 14.2 14.4 140
  • Example 31 Compound 23 Dopant 2 4.19 14.8 14.5 139
  • Example 32 Compound 41 Dopant 2 4.42 14.0 15.4 133
  • Example 33 Compound 97 Capsule 2 4.48 14.6 15.6 135
  • Example 34 Compound 131 Capsule 2 4.43 14.7 14.3 119
  • Example 35 Compound 256 Capsule 2 4.31 14.8 14.9 118 Comparative Example 6 Comparative Compound 18 Capsule 2 5.51 13.4 13.0 85 Comparative Example 7 Comparison Compound 40 Dopant 2 4.44 13.9 16.9 64 Comparative Example 8 Comparative Compound 48 Dopant 2 4.50 14.0 15.1 60 Comparative Example
  • the host used in the light emitting layer of the organic light emitting device according to Examples 26 to 35 has excellent charge transporting properties as a phosphorescent host material, and the absorption spectrum and the emission wavelength region of the fragments overlap with each other, It can be seen that the improvement of the performance such as the reduction of the voltage and especially the long life and the capability as the OLED material are maximized.
  • An organic light emitting device was fabricated in the same manner as in Example 1, except that the first host and the second host described in Table 6 were used in place of the compound 2 as the host of the light emitting layer. At this time, the dopant: the first host: the second host has a weight ratio of 10:45:45
  • the driving voltage, efficiency, luminance, and lifetime of the organic light emitting devices of Examples 36 to 60 and Comparative Examples 14 to 21 were measured using a luminance meter PR650 Spectroscan Source Measurement Unit (manufactured by PhotoResearch Co., Ltd.) by supplying power from a current voltmeter (Kethley SMU 236) The results are shown in Table 5. < tb >< TABLE > The T 95 lifetime is an evaluation of the time (hr) required for the luminance to become 95% of the initial luminance of 100%.
  • An organic luminescent device was fabricated in the same manner as in Example 26 except that the first host and the second host described in Table 7 were used in place of the compound 2 as the host of the luminescent layer. At this time, the dopant: first host: second host is in a weight ratio of 3: 48.5: 48.5
  • the driving voltage, efficiency, luminance, and lifetime of the organic light emitting devices according to Examples 61 to 75 and Comparative Examples 22 to 25 were measured using a luminance meter PR650 Spectroscan Source Measurement Unit (PhotoResearch Co., Ltd.) by supplying power from a current voltmeter (Kethley SMU 236) Product).
  • Example 61 Compound 3 E-99 Dibutane 2 4.10 17.9 152
  • Example 62 Compound 3 F-104 Dopant 2 3.91 19.4 181
  • Example 63 Compound 3 F-106 Dopant 2 3.87 19.7 187
  • Example 64 Compound 3 F-107 Dipant 2 3.95 18.9 177
  • Example 65 Compound 3 E-99 Dibutane 2 4.10 17.9 152
  • Example 62 Compound 3 F-104 Dopant 2 3.91 19.4 181
  • Example 63 Compound 3 F-106 Dopant 2 3.87 19.7 187
  • Example 64 Compound 3 F-107 Dipant 2 3.95 18.9 177
  • Example 65 Compound 3 F-107

Abstract

La présente invention concerne un composé organique représenté par la formule chimique 1, une composition le comprenant, un élément photoélectronique organique et un dispositif d'affichage.
PCT/KR2018/010709 2017-09-20 2018-09-12 Composé organique, composition, élément photoélectronique organique et dispositif d'affichage WO2019059577A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880060688.9A CN111108108A (zh) 2017-09-20 2018-09-12 有机化合物、组合物、有机光电装置和显示装置

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2017-0121273 2017-09-20
KR1020170121273A KR102235262B1 (ko) 2017-09-20 2017-09-20 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치

Publications (2)

Publication Number Publication Date
WO2019059577A1 true WO2019059577A1 (fr) 2019-03-28
WO2019059577A8 WO2019059577A8 (fr) 2020-03-26

Family

ID=65810953

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/010709 WO2019059577A1 (fr) 2017-09-20 2018-09-12 Composé organique, composition, élément photoélectronique organique et dispositif d'affichage

Country Status (3)

Country Link
KR (1) KR102235262B1 (fr)
CN (1) CN111108108A (fr)
WO (1) WO2019059577A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022063744A1 (fr) 2020-09-24 2022-03-31 Merck Patent Gmbh Dispositif électroluminescent organique
WO2022090108A1 (fr) 2020-10-27 2022-05-05 Merck Patent Gmbh Dispositif électroluminescent organique
WO2022207678A1 (fr) 2021-03-30 2022-10-06 Merck Patent Gmbh Dispositif électroluminescent organique
WO2023052377A1 (fr) 2021-09-30 2023-04-06 Merck Patent Gmbh Appareil électroluminescent organique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI766884B (zh) 2016-09-30 2022-06-11 德商麥克專利有限公司 具有二氮雜二苯并呋喃或二氮雜二苯并噻吩結構的化合物、其製法及其用途

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150083786A (ko) * 2014-01-10 2015-07-20 삼성에스디아이 주식회사 축합환 화합물, 및 이를 포함한 유기 발광 소자
KR20150088176A (ko) * 2014-01-23 2015-07-31 유니버셜 디스플레이 코포레이션 Ｏｌｅｄ용 유기 재료
WO2015114102A1 (fr) * 2014-02-03 2015-08-06 Basf Se Azadibenzofuranes substitués par silyle et azadibenzothiophènes
KR20150136942A (ko) * 2014-05-28 2015-12-08 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
US20170186971A1 (en) * 2015-12-25 2017-06-29 Semiconductor Energy Laboratory Co., Ltd. Compound, Light-Emitting Element, Display Device, Electronic Device, and Lighting Device
WO2018060307A1 (fr) * 2016-09-30 2018-04-05 Merck Patent Gmbh Composés comprenant des structures diazadibenzofurane ou diazadibenzothiophène

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101447959B1 (ko) * 2012-05-25 2014-10-13 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
US9502656B2 (en) * 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
KR101842584B1 (ko) * 2015-02-13 2018-03-27 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
JP2018127402A (ja) * 2017-02-06 2018-08-16 国立大学法人山形大学 新規なベンゾフロピリミジン化合物、及びそれを用いた有機ｅｌ素子

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150083786A (ko) * 2014-01-10 2015-07-20 삼성에스디아이 주식회사 축합환 화합물, 및 이를 포함한 유기 발광 소자
KR20150088176A (ko) * 2014-01-23 2015-07-31 유니버셜 디스플레이 코포레이션 Ｏｌｅｄ용 유기 재료
WO2015114102A1 (fr) * 2014-02-03 2015-08-06 Basf Se Azadibenzofuranes substitués par silyle et azadibenzothiophènes
KR20150136942A (ko) * 2014-05-28 2015-12-08 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
US20170186971A1 (en) * 2015-12-25 2017-06-29 Semiconductor Energy Laboratory Co., Ltd. Compound, Light-Emitting Element, Display Device, Electronic Device, and Lighting Device
WO2018060307A1 (fr) * 2016-09-30 2018-04-05 Merck Patent Gmbh Composés comprenant des structures diazadibenzofurane ou diazadibenzothiophène

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022063744A1 (fr) 2020-09-24 2022-03-31 Merck Patent Gmbh Dispositif électroluminescent organique
WO2022090108A1 (fr) 2020-10-27 2022-05-05 Merck Patent Gmbh Dispositif électroluminescent organique
WO2022207678A1 (fr) 2021-03-30 2022-10-06 Merck Patent Gmbh Dispositif électroluminescent organique
WO2023052377A1 (fr) 2021-09-30 2023-04-06 Merck Patent Gmbh Appareil électroluminescent organique

Also Published As

Publication number Publication date
KR102235262B1 (ko) 2021-04-02
CN111108108A (zh) 2020-05-05
WO2019059577A8 (fr) 2020-03-26
KR20190032884A (ko) 2019-03-28

Similar Documents

Publication Publication Date Title
CN109970724B (zh) 有机化合物、组合物、有机光电子装置和显示装置
WO2019124550A1 (fr) Élément électroluminescent organique et son procédé de production
KR101912107B1 (ko) 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR101773363B1 (ko) 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
EP2182039A2 (fr) Composés aromatiques électroluminescents et dispositif électroluminescent organique les utilisant
KR102171533B1 (ko) 조성물, 유기 광전자 소자 및 표시 장치
CN111018843B (zh) 化合物、电子元件及电子装置
WO2019059577A1 (fr) Composé organique, composition, élément photoélectronique organique et dispositif d'affichage
TWI721318B (zh) 有機化合物、組成物、有機光電裝置以及顯示裝置
KR101972802B1 (ko) 유기 화합물, 조성물 및 유기 광전자 소자
KR102275343B1 (ko) 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR20170057856A (ko) 스피로형 화합물 및 이를 포함하는 유기 발광 소자
JP7285221B2 (ja) 有機ｅｌ素子、ベンゾアゾール環構造を有するアミン化合物、およびそれを有機ｅｌ素子のキャッピング層に用いる方法
KR102171534B1 (ko) 조성물, 유기 광전자 소자 및 표시 장치
WO2019066340A1 (fr) Composé organique, composition, dispositif opto-électronique organique et dispositif d'affichage
KR20220124697A (ko) 유기 일렉트로루미네센스 소자
KR101734459B1 (ko) 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
CN107880045B (zh) 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
KR20220148837A (ko) 유기 일렉트로 루미네선스 소자
CN107868035B (zh) 用于有机光电装置的化合物、用于有机光电装置的组合物及有机光电装置及显示装置
WO2022264974A1 (fr) Composé amine ayant une structure cyclique d'azabenzoxazole, et élément électroluminescent organique l'utilisant
KR101865051B1 (ko) 신규한 유기발광화합물 및 이를 포함하는 유기 발광 소자
KR102008895B1 (ko) 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
KR102262471B1 (ko) 조성물, 유기 광전자 소자 및 표시 장치
KR101921217B1 (ko) 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18857731

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18857731

Country of ref document: EP

Kind code of ref document: A1