WO2015111848A1 - Composé organique, composition, dispositif opto-électronique organique et dispositif d'affichage - Google Patents

Composé organique, composition, dispositif opto-électronique organique et dispositif d'affichage Download PDF

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WO2015111848A1
WO2015111848A1 PCT/KR2014/012749 KR2014012749W WO2015111848A1 WO 2015111848 A1 WO2015111848 A1 WO 2015111848A1 KR 2014012749 W KR2014012749 W KR 2014012749W WO 2015111848 A1 WO2015111848 A1 WO 2015111848A1
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formula
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한수진
이한일
민수현
유은선
정호국
조평석
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삼성에스디아이 주식회사
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Priority claimed from KR1020140184653A external-priority patent/KR101829745B1/ko
Application filed by 삼성에스디아이 주식회사 filed Critical 삼성에스디아이 주식회사
Priority to US15/037,419 priority Critical patent/US11177441B2/en
Priority to CN201480073378.2A priority patent/CN105916847B/zh
Publication of WO2015111848A1 publication Critical patent/WO2015111848A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • 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
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • An organic compound a composition, an organic optoelectronic device, and a display device.
  • An organic optoelectric diode is a device capable of converting 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.
  • It is a light emitting device that generates light energy from 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.
  • the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material.
  • the organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode.
  • the organic layer may include a light emitting layer and an auxiliary layer, and the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron transport auxiliary layer to increase efficiency and stability of the organic light emitting device. And at least one layer selected from an electron injection layer and a hole blocking layer.
  • the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the increase is also affected by the organic materials included in the organic layer.
  • One embodiment provides an organic compound capable of implementing high efficiency and long life organic optoelectronic devices.
  • Another embodiment provides a composition for an organic optoelectronic device including the organic compound.
  • Yet 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 the following Chemical Formula 1 and having a molecular weight of 538 or more and less than 750 is provided:
  • Z are each independently N, C or CR a ,
  • At least one of Z is N,
  • R 'to R 1 1 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 C 12 heterotero An aryl group or a combination thereof,
  • R 1 and R 2 are independently present or linked together to form a ring
  • R 5 and R 6 are independently present or linked together to form a ring
  • R 7 and R 8 are independently present or connected to each other to form a ring
  • R 9 and R ′ 0 are independently present or linked together to form a ring, nl is an integer from 1 to 5,
  • n2 is an integer of 0 to 2
  • n3 and n4 are 0 or 1 each independently.
  • a composition for an organic optoelectronic device including at least one second organic compound having a first organic compound and a carbazole moiety, which is the aforementioned organic compound, is provided.
  • a display device including the organic optoelectronic device is provided.
  • FIG. 1 and 2 are cross-sectional views illustrating organic light emitting diodes according to example embodiments. [Best form for implementation of the invention]
  • 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 C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C6 to C30 heteroaryl group, C1 to C20 alkoxy group It means substituted with a C1 to C10 trifluoroalkyl group or a cyano group, such as a, fluoro group, trifluoromethyl group.
  • Two adjacent substituents of C1 to CI 0 trifluoroalkyl or cyano groups such as heterocycloalkyl group, C6 to C30 aryl group, C6 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group, and trifuluromethyl group May be fused to form a ring.
  • the substituted C6 to C30 aryl group can be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
  • hetero means one to three heteroatoms selected from the group consisting of ⁇ , ⁇ , S, ⁇ and Si in one functional group, and the remainder is carbon unless otherwise defined. do.
  • an "alkyl group” is aliphatic
  • the alkyl group may be a "saturated alkyl group" that does not contain any double bonds or triple bonds.
  • the alkyl group may be an alkyl group of C 1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group.
  • a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and ' t-butyl It is selected from the group consisting of.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
  • an "aryl group” refers to a substituent in which all elements of a cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic and polycyclic. Or fused ring polycyclic (ie, rings that divide adjacent carbon atoms with adjacent pairs) functional groups.
  • heteroaryl group means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S, P, and Si in the aryl group, and the rest are carbon.
  • heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
  • a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted A substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, Substituted or unsubstitute
  • the hole characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and injecting holes formed at the anode into the light emitting layer having conductive properties along the HOMO level, and emitting layer. It refers to a property that facilitates the movement of the hole formed in the anode and movement in the light emitting layer.
  • the electron characteristic refers to a characteristic in which electrons can be received when an electric field is applied.
  • the electron characteristic has conductivity characteristics along the LUMO level, and the electrons formed in the cathode are injected into the light emitting layer, the electrons formed in the light emitting layer move to the cathode, and in the light emitting layer It means a property that facilitates movement.
  • Z is independently N, C or CR a ,
  • At least one of Z increase is N
  • R 1 to R 1 1 and R a are each independently hydrogen, hydrogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C3 to C 12 heteroaryl Groups or a combination thereof,
  • R 5 and R 6 are independently present or linked together to form a ring
  • R 7 and R 8 are independently present or linked together to form a ring
  • R 9 and R 10 are independently present or linked together to form a ring, nl is an integer from 1 to 5,
  • n2 is an integer of 0 to 2
  • n3 and n4 are 0 or 1 each independently.
  • the organic compound represented by Chemical Formula 1 includes two or more substituted or unsubstituted aryl groups and at least one heteroaryl group having at least one nitrogen centered on two phenylene groups bonded to a me ta position.
  • the organic compound may include a ring containing at least one nitrogen, and thus may have a structure in which electrons are easily received when an electric field is applied, thereby lowering a driving voltage of the organic optoelectronic device to which the organic compound is applied.
  • the organic compound may include a plurality of substituted or unsubstituted aryl group moieties that are susceptible to holes and a nitrogen-containing ring moiety that is susceptible to electrons to form a bipolar structure to properly balance the flow of holes and electrons. Therefore, the efficiency of the organic optoelectronic device to which the organic compound is applied can be improved. have.
  • the meta position by including two phenylene groups bonded to the meta position, it is appropriate to localize a plurality of substituted or unsubstituted aryl group moieties that are susceptible to holes and nitrogen-containing ring moieties that are susceptible to electrons in the aforementioned bipolar structured compound.
  • By controlling the flow of the conjugated system can exhibit excellent bipolar characteristics.
  • one or two of the two phenylene groups may be an unsubstituted phenylene group. Accordingly, the lifespan of the organic optoelectronic device to which the organic compound is applied can be improved.
  • the organic compound since the organic compound has a substantially linear structure, the organic compound may be self-arranged during deposition to increase process stability and to increase thin film uniformity.
  • the organic compound may have a molecular weight of about 538 or more and less than 750.
  • a molecular weight in the above range it is possible to reduce the thermal decomposition of the compound by a high degree of silver 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 1-A.
  • Formula 1 -A may be an unsubstituted phenylene group of both phenylene groups bonded to the meta position.
  • the organic compound may be represented by any one of the following Chemical Formulas 2 to 4, for example. [Formula 2] [Formula 3
  • ⁇ ⁇ may be an integer of 1 to 3, and the sum of nl and n2 may satisfy ⁇ + !.
  • nl may be, for example, an integer of 1 to 4, and the sum of nl and n2 may satisfy 1 ⁇ 11 + 0 2 ⁇ 4.
  • the organic compound may be represented by, for example, the following Chemical Formula 5 or 6.
  • R 'to R 11 , ⁇ and n 4 are the same as described above, R 3a and 1 315 are the same as R 3 , and R a and R 4b are the same as R 4 .
  • the compound represented by Chemical Formula 5 may be represented by any one of the following Chemical Formulas 5a to 5g. [Formula 5a]
  • At least one of R ⁇ R ⁇ R ⁇ R ⁇ R ⁇ R ⁇ R 413 and R 11 in Chemical Formulas 5a to 5g may be a substituted or unsubstituted C6 to C12 aryl group.
  • at least one of R ⁇ R ⁇ R ⁇ R 48 , R 3b , R 4b, and R ′′ of Formulas 5a to 5 g may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
  • the compound represented by Chemical Formula 6 may be, for example represented by Chemical Formula 6a. 6a]
  • At least one of R 1 to R 6 and R 1 1 of Formula 6a is substituted or unsubstituted
  • R ′ to R 6 and R 1 1 in Formula 6a may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
  • R 7 to R 10 may be each independently hydrogen or a substituted or unsubstituted C6 to C12 aryl group, for example, R 7 to R 10 are each independently hydrogen, substituted or unsubstituted It may be a substituted phenyl group, a substituted or unsubstituted naphthyl group or a substituted or unsubstituted biphenyl group.
  • R 7 to R 10 of Chemical Formulas 1 to 6 when at least one of R 7 to R 10 of Chemical Formulas 1 to 6 is a substituted or unsubstituted C6 to C12 aryl group, the substituted or unsubstituted C6 to C12 aryl group may not be bonded at an ortho position. Can be.
  • R 7 to R 10 in Chemical Formulas 1 to 6 when at least one of R 7 to R 10 in Chemical Formulas 1 to 6 is a substituted or unsubstituted phenyl group, the phenyl group may not be bonded to an olso and para position.
  • the organic compound may be represented by, for example, the following Chemical Formula 7.
  • R 'to R 6 , R a and nl to n 4 may be as described above,
  • R 7 to R 10 may be each independently hydrogen or a substituted or unsubstituted C6 to C12 aryl group.
  • the organic compound may be, for example, a compound listed in Group 1, 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.
  • composition for organic optoelectronic devices including the organic compound described above will be described.
  • the composition may include at least one organic compound having the above-described organic compound and a carbazole moiety.
  • 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 the following Formula 8.
  • Y ' is a single bond.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C30 heteroaryl group in C2, or a combination thereof,
  • R 15 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 heteroaryl group, or a combination thereof ,
  • At least one of 1 2 to R 15 and Ar 1 includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazole group.
  • the second organic compound represented by Chemical Formula 8 may be, for example represented by at least one of Chemical Formulas 8-1 to 8-III:
  • 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 heteroarylene group or a combination thereof,
  • Ar 'and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, substituted Or an unsubstituted C2 to C30 heteroaryl group or a combination thereof,
  • R 12 to R IS and R 20 to R 31 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 2 to C 50 Heteroaryl group or a combination thereof.
  • the second organic compound represented by Chemical Formula 8 may be, for example, a compound listed in Group 2, but is not limited thereto.
  • the second organic compound may be, for example, a compound consisting of a combination of a moiety represented by Formula 9 and a moiety represented by Formula 10 below.
  • 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 heteroarylene 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 heteroaryl group or a combination thereof,
  • R 16 to R 19 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 heteroaryl group, or a combination thereof ,
  • Adjacent two * of Formula 9 combines with two * of Formula 10 to form a fused ring, and * which does not form a fused ring in Formula 9 is each independently CR b ,
  • R b is hydrogen, hydrogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C3 to C12 heteroaryl group, or a combination thereof.
  • the organic compound consisting of a combination of the moiety represented by Formula 9 and the moiety represented by Formula 10 may be a compound listed in Group 3 below, but is not limited thereto.
  • the second organic compound may include at least one of a compound represented by Formula 8 and a combination of a moiety represented by Formula 9 and a moiety represented by Formula 10 below.
  • the composition may include the first organic compound and the second organic compound in a weight ratio of about 1:10 to 10: 1.
  • the composition may be applied to an organic layer of an organic optoelectronic device.
  • the first organic compound and the second organic compound may serve as a host of a light emitting insect.
  • 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 may be used together with the first organic compound. It is possible to further improve the luminous efficiency and lifetime characteristics by increasing the mobility and stability of the charge.
  • 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 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 an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof.
  • the phosphorescent dopant may be a compound represented by the following Chemical Formula Z, but is not limited thereto.
  • M is a metal
  • L and X are the same or different from each other and a ligand to form a complex with M.
  • M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, wherein L and X are, for example, bidentate It may be a ligand.
  • the composition may be applied to an organic layer of an organic optoelectronic device.
  • the first organic compound and the second organic compound may be applied to an electron transport auxiliary layer positioned between the light emitting layer and the electron transport layer.
  • the first compound and the second compound are combined in various ratios
  • the electron transport auxiliary layer converts the excitons generated from the holes and / or the light emitting layer from the anode to the light emitting layer into excitons of lower energy than the energy of the axtone of the light emitting layer so that the holes and / or excitons pass through the light emitting layer to the electron transport layer. You can effectively block the movement. Accordingly, the efficiency and lifespan of the organic optoelectronic device can be improved.
  • the first compound and the second compound may be included, for example, in a weight ratio of about 1:99 to 99: 1.
  • the composition may be formed by a dry film formation method or a solution process such as chemical vapor deposition.
  • 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, at least one layer of organic worms positioned between the anode and the cathode, and the organic worm may include the aforementioned organic compound or the above-described composition. .
  • an organic optoelectronic device 100 includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110. Include.
  • the anode 120 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 120 may be, for example, a metal such as nickel, platinum, barn, crucible, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide ( ⁇ ),
  • Metal oxides such as indium 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) (polyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, and the like. It is not.
  • the cathode 1 10 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 negative electrode 1 10 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 / AI, and BaF 2 / Ca, but are not limited thereto.
  • Organic layer 105 comprises an organic compound as described above or a composition as described above
  • the light emitting layer 130 may include, for example, the above-described organic compound alone, may include at least two kinds of the above-described organic compound, or may include the above-described composition.
  • the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130.
  • the hole auxiliary layer 140 is a hole injection between the anode 120 and the light emitting layer 130 And / or further increase hole mobility and block electrons.
  • the hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
  • an organic light emitting device further comprising an electron transport layer, an electron transport auxiliary layer, an electron injection layer, etc. as the organic thin film layer 105 in FIG.
  • the organic light emitting diodes 100 and 200 may form an anode or a cathode on a substrate, and then form an organic layer by dry deposition such as evaporation, sputtering, plasma plating, or ion plating.
  • the above compounds can be formed simultaneously, or a compound having the same deposition temperature can be mixed and formed together. Then it can be prepared by forming a cathode or an anode thereon.
  • the organic light emitting diode described above may be applied to an organic light emitting diode display.
  • the representative synthesis method is as shown in the following representative Banungsik.
  • the compound 1-6 (20 g, 71 mmol) was dissolved in 1 L of THF, followed by 1 -bromo-2-iodobenzene (22 g, 78 mmol) and tetrakis (triphenylphosphine) palladium (0.8 g, 0.71 mmol) was added and stirred.
  • 1 « ⁇ 53 0 ⁇ : ⁇ 13011 6 (25 177 010101) saturated in water was added thereto, and the mixture was heated and refluxed at 80 I: for 12 hours.
  • water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1-7 (19 g, 87%).
  • the compound 1-8 (20 g, 71 mmol) was dissolved in 1 L of THF, followed by l-bromo-3-iodobenzene (22 g, 78 mn l) and tetrakis (triphenylphosphine) palladium (0.8 g, 0.71 mmol) and stirred.
  • (5013551) 10 ⁇ & 011 6 (25 177 1 ⁇ 01) saturated in water was added thereto, and the mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), and then water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound I-9 (20 g, 91%).
  • the compound 1-12 (50 g, 129 mmol) was dissolved in 1 L of Dioxane in a nitrogen environment, and then (3-chlotOphenyl) boronic acid (24 g, 155 mmol) was added thereto.
  • the compound 1-14 (50 g, 98 mmol) was dissolved in 1 L of THF, followed by 1 -bromo-3-iodobenzene (33 g, 1 17 mmol) and tetrakis (triphenylphosphine) palladium (1 g, 0.98 mmol) was added and stirred. Potassuim carbonate (34 g, 245 mmol) ol saturated in water was added thereto, and the mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound II 5 (50 g, 95%).
  • DCM dichloromethane
  • the compound 1-17 (50 g, 129 mmol) was dissolved in 1 L of THF, followed by (3-chlorophenyl) boronic acid (24 g, 155 mmol) and tetrakis (triphenylphosphine) palladium (1.5 g, 1.3 mmol) was added and stirred. Potassium carbonate saturated in water (45 g, 322 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1-18 (50 g, 92%).
  • DCM dichloromethane
  • the compound 1-19 (50 g, 98 mmol) was dissolved in 1 L of THF, followed by 1 -bromo-3-iodobenzene (33 g, 117 mmol) and tetrakis (triphenylphosphine) pal ladium (1 g, 0.98 mmol) was added and stirred. Potassium carbonate saturated in water (34 g, 245 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1-20 (50 g, 95%).
  • DCM dichloromethane
  • the compound 1-24 (50 g, 98 mmol) was dissolved in 1 L of THF, followed by -bromo-3-iodobenzene (33 g, 1 17 mmol) and tetrakis (triphenylphosphine) palladium (1 g, 0.98). mmol) was added and stirred. Potassium carbonate saturated in water (34 g, 245 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1-25 (50 g, 96%).
  • DCM dichloromethane
  • the compound 1-29 (50 g, 140 mmol) was dissolved in 1 L of THF, followed by 1 -bromo-4-iodobenzene (47 g, 168 mmol) and tetrakis (triphenylphosphine) palladium (1.6 g, 1.4 mmol) was added and stirred. Potassium carbonate saturated in water (48 g, 350 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 12 hours. After completion of reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1-30 (44 g, 89%).
  • DCM dichloromethane
  • Dissolve compound 1-35 (30 g, 95 tnmol) THF 1 1 ⁇ 1 in a nitrogen environment, and add phenylboronic acid (14 g, 1 14 mmol) and tetrakis (triphenylphosphine) palladium (1 g, 0.95 mmol). Put and stirred. Potassium carbonate saturated in water (33 g, 237 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 1-36 (32 g, 75%).
  • DCM dichloromethane
  • the compound 1-38 (20 g, 71 mmol) was dissolved in 1 L of THF, followed by -bromo-3-iodobenzene (24 g, 85 mnrol) and tetrakis (triphenylphosphine) palladium (0.8 mg, 0.7 tnmol) was added and stirred.
  • -bromo-3-iodobenzene 24 g, 85 mnrol
  • tetrakis (triphenylphosphine) palladium 0.8 mg, 0.7 tnmol
  • the compound 1-45 (22.43, 83.83 mmol) was dissolved in 500 mL of THF, followed by 3-biphenyl boronic acid (23.3 g, 1 17.36 mmol) and tetrakis (triphenylphosphine) palladium (2.9 g, 2.5 mmol). Put and stirred. Potassuim carbonate saturated in water (46 g,
  • Tetrakis (triphenylphosphine) palladium (0.45 g, 0.39mmol) was added thereto and stirred.
  • Potassium carbonate saturated in water (9.7 g, 99 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C for 20 hours.
  • water was added to the reaction solution and extracted with dichloromethane (DCM), followed by removing water with anhydrous MgS04, followed by concentration under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound 19 (20 g, 83%).
  • the molecular weight of compound 19 is 613.2518.
  • Tetmkis (triphenylphosphine) palladium (0.45 g, 0.39 mmol) was added and stirred. Potassium carbonate saturated in water (13.5 g, 97 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 20 hours. After completion of reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), and water was removed using anhydrous MgS04. , Filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining HOST 1 (16 g, 78%). The molecular weight of HOST 1 is 537.2205.
  • the compound 1-1 (20 g, 51 mmol) was dissolved in 0.2 L of tetrahydroftiran (THF), followed by 1-31 (26.5 g, 61.2 mmol) and tetrakis (tripheny lphosph ine) pal lad ium (0.6 g, 0.51 mmol) and stirred. Potassium carbonate saturated in water (l 7.5 g, 127 mmol) was added thereto, and the resulting mixture was heated and refluxed at 80 ° C. for 20 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining HOST 4 (23 g, 75%). The molecular weight of HOST 4 is 613.2518.
  • DCM dichloromethane
  • An organic light emitting device was manufactured using Compound 1 obtained in Synthesis Example 54 as a host and Ir (PPy) 3 as a dopant.
  • ITO was used as the anode at a thickness of 1000 A
  • aluminum (A1) was used as the cathode at a thickness of 1000 A.
  • the manufacturing method of the organic light emitting device the anode is cut into ⁇ glass substrate having a sheet resistance value of 15 ⁇ / ⁇ to the size of 50mm ⁇ 50 mm ⁇ 0.7 mm in each of acetone, isopropyl alcohol and pure water For 15 minutes. After ultrasonic cleaning, UV ozone cleaning was used for 30 minutes.
  • N4, N4 , -di (naphthalen-l -yl) -N4, N4'-diphenylbiphenyl-4,4'-diamine (with a vacuum degree of 650x KT 7 Pa, deposition rate of 1 to 0.3 nm / s on the substrate) NPB) (80 nm) was deposited to form a 800 A hole transport layer.
  • NPB N4'-diphenylbiphenyl-4,4'-diamine
  • Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) alurninium (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 A.
  • Alq 3 was deposited under deposition conditions to form an electron transport layer having a thickness of 200 A.
  • An organic photoelectric device was manufactured by sequentially depositing LiF and A1 as a cathode on the electron transport layer.
  • the structure of the organic photoelectric device is ITO / NPB (80 nm) / EML ( Compound 1 (93 parts by weight 0/0) + Ir (PPy ) 3 (7 parts by weight 0 /.), 30 nm) / Balq (5 nm) / It was produced in the structure of Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 2 of Synthesis Example 55 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 3 of Synthesis Example 56 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 56 of Synthesis Example 62 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 57 of Synthesis Example 63 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 74 of Synthesis Example 64 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 68 of Synthesis Example 65 was used instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting device was manufactured in the same manner as in Example I, except that Compound 105 of Synthesis Example 66 was used instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 135 of Synthesis Example 67 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using CBP of the following structure instead of compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound HOST1 of Comparative Synthesis Example 69 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound HOST2 of Comparative Synthesis 70 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound HOST4 of Comparative Synthesis Example 72 instead of Compound 1 of Synthesis Example 54.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound HOST5 of Comparative Synthesis Example 73 instead of Compound 1 of Synthesis Example 54.
  • 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 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-1000 A) while increasing the voltage from 0V to 10V to obtain a result.
  • Example 1 Compound 1 4.6 Green 81.7 2,460 Example 2 Compound 2 4.8 Green 95.1 1,300 Example 3 Compound 3 4.7 Green 88.9 1,930 Example 4 Compound 10 4.3 Green 78.0 2,770 Example 5 Compound 13 4.2 Green 73.3 900 Example 6 Compound 19 4.5 Green 72.6 930 Example 7 Compound 28 4.5 Green 80.9 2,320 Example 8 Compound 37 4.3 Green 88.2 2,120 Example 9 Compound 56 4.4 Green 91.1 2,000 Example 10 Compound 57 4.2 Green 94.4 1,990 Example U Compound 74 4.3 Green 75.7 950 Example 12 Compound 68 4.5 Green 77.3 1,000
  • the temperature was measured when the host of the light emitting layer was deposited during fabrication of the organic light emitting diode of Example 1, which means a silver having a thickness of 1 A per second (A / sec) (2) Glass Transitional Silver (Tg)
  • 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 Metter Teledo.
  • Samples of the compound were taken lg, layered with nitrogen in a glass vessel and sealed. After the glass container was stored in an oven for 200 hours for 200 hours, the purity was measured in the same manner as the method for measuring the room temperature purity.
  • the organic light emitting device according to Examples 1 to 14 is the same or better than the organic light emitting device in Comparative Example 1 and Reference Examples 1 to 5 It can be seen that the life characteristics are significantly improved while having the driving voltage and efficiency. Specifically, the device results of Examples 1, 4, and 7 using compounds containing linear meta bonds continuously have the best lifetime. This is because the terminal phenyl group, which plays a role of hole characteristics, and the triazine structure, which plays an electronic characteristic role, are satisfactory.
  • the terminal phenyl group acts as a weak hole property and shows an interference effect with a moiety having electronic properties. For this reason, it is estimated that element life is reduced.
  • the compound used in the organic light emitting device according to Reference Example 1 has a low glass transition temperature (Tg) as shown in Table 2, not only the film formation is poor in the device deposition process, but also a subsequent process such as an encapsulation process. It can be expected that the service life is greatly reduced due to the influence of temperature.
  • the terminal phenyl group is substituted with the naphthyl group compared with HOST1.
  • the naphthyl group is a strong electron withdrawing group, so the weak hole properties can be concentrated well with the naphthyl group, which effectively leads to localization, which can significantly improve lifespan than HOST1.
  • the glass transition temperature (Tg) of the naphthyl group due to the improvement effect of the glass transition temperature (Tg) is higher than 40 volts compared to HOST1, it can be seen that it is stable in the encapsulation process, which is a subsequent process.
  • phenylcarbazolyl bromide (9.97 g, 30.95 mmol) was dissolved in 0.2 L of toluene, followed by phenylcarbazolylboronic acid (9.78 g, 34.05 mmol) and tetrakis (triphenylp osphine) palladium (1.07 g, 0.93 mmmol) -i: Put and stirred. Potassium carbonate saturated in water (12.83 g, 92.86 mmol) was added thereto, and the resulting mixture was heated and refluxed at 120 ° C. for 12 hours.
  • Tris (dibenzylideneacetone) dipalladium (0) (0.439g, 0.48mmol) and Tr-tert-buty Ip ho sphine (0.388g : 1.92mmol) were added and refluxed at 120 ° C for 12 hours. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), water was removed with anhydrous MgS04, filtered and concentrated under reduced pressure. The residue thus obtained is flash column
  • Step 5 Synthesis of Compound B-1 16 18 g (84) of Compound B-116 was obtained in the same manner as in Synthesis Example 3 of the second host compound using 13 g (33.1 mmol) of Compound B and 16.2 g (36.4 mmol) of Compound D. %) was obtained.
  • Step 1 Synthesis of Compound E 33 g (77%) of Compound E was prepared in the same manner as in Synthesis Example 3 of Compound 2 using 43.2 g (108.4 mmol) of Compound C and 14.5 g (l 19 mmol) of Phenylboronic acid. Got it.
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol and the like
  • Compound A was vacuum deposited on the ⁇ ⁇ substrate using the prepared ⁇ transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then Compound B was deposited to a thickness of 50 A on the injection layer, and then Compound C was 1020 A.
  • the organic light emitting device has a structure having five organic thin film layers, specifically as follows.
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using Compound 1 and Compound B-10 as 1: 1.
  • An organic light emitting device was manufactured in the same manner as in Example 15, except that Compound 1 and Compound B-10 were used as 1: 4.
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound B-31 obtained in Synthesis Example 3 of the second host compound instead of the compound B-10.
  • Example 19
  • An organic light emitting diode was manufactured according to the same method as Example 18 except for using Compound 1 and Compound B-31 as 1: 1.
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound B-1 obtained in Synthesis Example 1 of the second host compound instead of the compound B-10.
  • Example 21
  • An organic light emitting diode was manufactured according to the same method as Example 20 except for using Compound 1 and Compound B-1 as 1: 1.
  • Example 22 An organic light emitting diode was manufactured according to the same method as Example 20 except for using Compound 1 and Compound B-1 in 1: 4.
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound B-34 obtained in Synthesis Example 4 of the second host compound instead of the compound B-10.
  • Example 24
  • An organic light emitting diode was manufactured according to the same method as Example 23 except for using Compound 1 and Compound B-34 at 1: 1.
  • Example 26 An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound B-43 obtained in Synthesis Example 5 of the compound 1 and the second host compound in a 1: 1 manner.
  • Example 26 An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound B-43 obtained in Synthesis Example 5 of the compound 1 and the second host compound in a 1: 1 manner.
  • the compound was obtained in the same manner as in Example 15, except that Compound 135, which was obtained in Synthesis Example 63 instead of Compound 1, and Compound B-114 obtained in Synthesis Example 6 of the second host compound instead of Compound B-10 were used as 7: 3. A light emitting device was manufactured.
  • An organic light emitting diode was manufactured according to the same method as Example 26 except for using Compound 135 and Compound B-114 at 1: 1.
  • An organic light emitting diode was manufactured according to the same method as Example 26 except for using Compound 135 and Compound B-114 at 3: 7.
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using Compound 1 as a single host instead of two hosts of Compound 1 and Compound B-10. Comparative Example 2
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using a CBP-only host instead of two hosts of Compound 1 and Compound B-10.
  • An organic light emitting diode was manufactured according to the same method as Example 15 except for using Compound B-10 as a host instead of two hosts of Compound 1 and Compound B-10. Comparative Example 4
  • An organic light emitting diode was manufactured according to the same method as Example 20 except for using the compound B-1 single host instead of the two hosts of the compound 1 and the compound B-1.
  • An organic light emitting diode was manufactured according to the same method as Example 23 except for using Compound B-34 alone as a host instead of two hosts of Compound 1 and Compound B-34. Comparative Example 7
  • An organic light emitting diode was manufactured according to the same method as Example 25 except for using Compound B-43 alone as a host instead of two hosts of Compound 1 and Compound B-43. Rating 1
  • 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-I OOOA) while increasing the voltage from 0V to 10V to obtain a result.
  • a luminance meter Minolta Cs-I OOOA
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2) was calculated using the luminance, current density and voltage measured from (0 and (2) above.
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, and the like
  • Compound P was vacuum-deposited on the ⁇ substrate using the prepared ⁇ transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then deposited Compound Q on the injection layer to a thickness of 50 A, and then Compound R 1020A.
  • a hole transport layer was formed by evaporation at a thickness of ⁇ .
  • a blue fluorescent light emitting host and a dopant were doped with BH113 and BD370 (purchased by SFC Co., Ltd.) at a concentration of 5wt 0 /. It was. Thereafter, Compound 28 and Compound B-116 were vacuum-deposited at 50:50 (wt / wt) on the emission layer to form an electron transport auxiliary layer having a thickness of 50A.
  • Compound S and Liq were vacuum-deposited at 50:50 (wt / wt) on the emission layer to form an electron transport auxiliary layer having a thickness of 50A.
  • a light emitting device was manufactured.
  • the organic light emitting device has a structure having five organic thin film layers, specifically, ⁇ /
  • An organic light emitting diode was manufactured according to the same method as Example 29 except for using Compound 28 and Compound B-118 at 30:70.
  • Example 31
  • An organic light emitting diode was manufactured according to the same method as Example 29 except for using Compound 1 12 and Compound B-1 18 at 50:50.
  • An organic light emitting diode was manufactured according to the same method as Example 29 except for using Compound 135 and Compound B-U4 at 50:50.
  • Comparative Example 8 An organic light emitting diode was manufactured according to the same method as Example 29 except for not using an electron transport aid.
  • the organic light emitting diodes according to Examples 29 to 32 have significantly improved luminous efficiency and lifespan characteristics compared to the organic light emitting diode according to Comparative Example 8.
  • 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 it can be implemented as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

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Abstract

La présente invention concerne un composé organique représenté par la formule chimique 1 et ayant un poids moléculaire au moins égal à 538 mais inférieur à 750, une composition pour un dispositif opto-électronique organique contenant le composé organique, un dispositif opto-électronique organique ayant recours au composé organique ou à la composition, et un dispositif d'affichage comportant le dispositif opto-électronique organique.
PCT/KR2014/012749 2014-01-24 2014-12-23 Composé organique, composition, dispositif opto-électronique organique et dispositif d'affichage WO2015111848A1 (fr)

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US15/037,419 US11177441B2 (en) 2014-01-24 2014-12-23 Organic compound, composition, organic optoelectronic device, and display device
CN201480073378.2A CN105916847B (zh) 2014-01-24 2014-12-23 有机化合物、组成物、有机光电元件以及显示元件

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Cited By (21)

* Cited by examiner, † Cited by third party
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WO2016024745A3 (fr) * 2014-08-12 2016-09-01 삼성에스디아이 주식회사 Composé, diode optoélectronique organique comprenant ledit composé et dispositif d'affichage
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CN107580594A (zh) * 2015-06-17 2018-01-12 三星Sdi株式会社 用于有机光电装置的化合物、有机光电装置及显示装置
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