WO2019221484A1 - Composé organométallique et diode électroluminescente organique le comprenant - Google Patents

Composé organométallique et diode électroluminescente organique le comprenant Download PDF

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WO2019221484A1
WO2019221484A1 PCT/KR2019/005786 KR2019005786W WO2019221484A1 WO 2019221484 A1 WO2019221484 A1 WO 2019221484A1 KR 2019005786 W KR2019005786 W KR 2019005786W WO 2019221484 A1 WO2019221484 A1 WO 2019221484A1
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compound
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Korean (ko)
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김서연
박종호
서상덕
이동훈
박태윤
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주식회사 엘지화학
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Priority to CN201980010336.7A priority Critical patent/CN111655705B/zh
Publication of WO2019221484A1 publication Critical patent/WO2019221484A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • 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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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

Definitions

  • the present specification relates to an organic metal compound represented by Chemical Formula 1 and an organic light emitting device formed using the same.
  • the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into.
  • the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
  • the electron injection material or the electron transport material an organic material having an n-type property, that is, an organic material which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used.
  • the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and excitons formed by recombination of holes and electrons in the light emitting layer are formed. It is preferable that a material having high luminous efficiency converting the light into light when it is used.
  • the present specification provides an organic metal compound represented by Formula 1 and an organic light emitting device including the same.
  • an organic light emitting device including the organometallic compound is provided.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • X is O, S, Se, NR, CR'R '' or SiR'R '',
  • R, R 'and R' ' are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Carboxyl groups; Imide group; Amide group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted phosphine group; Substituted or unsubstituted sulfonyl group; Substit
  • R5 is a halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Carboxyl groups; Imide group; Amide group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted phosphine group; Substituted or unsubstituted sulfonyl group; Substituted or unsubstituted amine group; Sub
  • n is an integer from 0 to 2
  • n is 2
  • the structures in parentheses [] are the same or different
  • r1 to r4 are integers of 0 to 4, and when r1 to r4 are each 2 or more, the structures in parentheses () are the same or different from each other.
  • An exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the organometallic compound.
  • the organometallic compound described herein can be used as the material of the light emitting layer of the organic light emitting element.
  • the compound according to the exemplary embodiment of the present specification may improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Carboxyl groups; Imide group; Amino group; An alkoxy group; An alkyl group; Cycloalkyl group; Alkenyl groups; Cycloalkenyl group; Silyl groups; Boron group; Amine group; Phosphine oxide groups; Phosphine groups; Sulfonyl group; Aryl group; And one or two or more substituents selected from the group consisting of a heteroaryl group including one or more of N, O, S, Se, and Si atoms, or two or more substituents among the above-described substituents are substituted with a substituent connected thereto, or It means that it does not have a substituent.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • carbon number of an ester group is not specifically limited, It is preferable that it is C1-C30.
  • the carbon number of the carboxy group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30.
  • the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 3 to 40. In addition, it may be 3 to 30, may be 3 to 20, may be 3 to 10. Specific examples include propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, Neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1 -Methylhexyl, cyclopentylmethyl, cyclohexyl, cycl
  • the cycloalkyl group is not particularly limited, but may be 3 to 40 carbon atoms. In addition, it may be 3 to 30, may be 3 to 20, may be 3 to 10. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. It is not limited.
  • the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkenyl group represents a cyclic unsaturated hydrocarbon group containing a carbon-carbon double bond, and the carbon number is not particularly limited, but is preferably 2 to 36. According to an exemplary embodiment, the cycloalkenyl group has 2 to 24 carbon atoms. According to an exemplary embodiment, the cycloalkenyl group has 2 to 12 carbon atoms. Specific examples include, but are not limited to, cyclobutenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, norbornenyl, bicyclo [2.2.2.] Octenyl, and the like.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR 104 R 105 R 106 , R 104 to R 106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.
  • the boron group may be -BR 100 R 101 , wherein R 100 , and R 101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated.
  • carbon number is not specifically limited, It is preferable that it is C6-C60, It may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 40 carbon atoms.
  • the aryl group has 6 to 30 carbon atoms.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a terphenyl group, but are not limited thereto.
  • As said polycyclic aryl group a naphthyl group, anthracenyl group, a phenanthrenyl group, a perrylenyl group, a fluoranthenyl group, a triphenylenyl group, a penalenyl group, a pyrenyl group, a tetrasenyl group, a chrysenyl group, a pentaxenyl group , Fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirofluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 50 carbon atoms.
  • heteroaryl groups include thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, triazole groups, pyridyl groups, bipyridyl groups, pyrimidyl groups, triazine groups, triazole groups, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazo
  • an amine group refers to a monovalent amine in which at least one hydrogen atom of the amino group (-NH 2 ) is substituted with another substituent, represented by -NR 107 R 108 , and R 107 and R 108 are the same as or different from each other.
  • substituents represented by -NR 107 R 108 , and R 107 and R 108 are the same as or different from each other.
  • -NH 2 Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of N-alkylheteroarylamine group, monoheteroarylamine group and diheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • Diphenylamine group ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenyl amine group and the like, but is not limited thereto.
  • phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
  • the phosphine group means an alkyl phosphine group or an aryl phosphine group
  • the alkyl phosphine group means a phosphine group substituted with an alkyl group.
  • carbon number of the said alkyl phosphine group is not specifically limited, It is preferable that it is 1-20.
  • the alkylphosphine group include dimethylphosphine group, diethylphosphine group, di-n-propylphosphine group, diisopropylphosphine group, di-n-butylphosphine group, di-sec-butylphosphine group and di-tert.
  • arylphosphine group refers to a phosphine group substituted with an aryl group. Although carbon number of the said aryl phosphine group is not specifically limited, It is preferable that it is 6-30.
  • arylphosphine group examples include, but are not limited to, a diphenylphosphine group, a dibenzylphosphine group, a methylphenylphosphine group, a benzylhexylphosphine group, a bistrimethylsilylphosphine group, and the like.
  • the sulfonyl group is not particularly limited, but may be 1 to 30 carbon atoms, and examples of the sulfonyl group include alkyl sulfonyl having 1 to 4 carbon atoms such as methanesulfonyl, ethanesulfonyl, and hexanesulfonyl. It is not limited to this.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the corresponding substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on the atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • the ring may be an aromatic or aliphatic ring, preferably an aliphatic ring.
  • the carbon number of the ring is not particularly limited, but may be 3 to 30, specifically 3 to 20, and more specifically 3 to 10.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • X is O, S, Se, NR, CR'R '' or SiR'R '', and R, R 'and R' 'are the same as or different from each other, and each independently , Hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • X is O, S, Se, NR, CR'R '' or SiR'R '', and R, R 'and R' 'are the same as or different from each other, and each independently , Hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • X is O, S, Se, NR, CR'R '' or SiR'R '', and R, R 'and R' 'are the same as or different from each other, and each independently , Hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • X is O, S, Se, NR, CR'R '' or SiR'R '', and R, R 'and R' 'are the same as or different from each other, and each independently , Hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
  • X is O, S or Se.
  • X is O.
  • X is S.
  • X is Se
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Carboxyl groups; Imide group; Amide group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted phosphine group; Substituted or unsubstituted sulfon
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted silyl group.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted silyl group having 1 to 30 carbon atoms.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted silyl group having 1 to 20 carbon atoms.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; Or a substituted or unsubstituted silyl group having 1 to 10 carbon atoms.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted methyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted pentyl group; A substituted or unsubstituted cyclohexyl group; Or trimethylsilyl group.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; Methyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Pentyl group unsubstituted or substituted with deuterium; A cyclohexyl group unsubstituted or substituted with deuterium; Or trimethylsilyl group.
  • R1 to R4 and R6 are the same as or different from each other, and each independently hydrogen; Methyl group; Methyl group substituted with deuterium; Isopropyl group; Isopropyl group substituted with deuterium; Neopentyl group substituted with deuterium; Cyclohexyl group; Cyclohexyl group substituted with deuterium; Or trimethylsilyl group.
  • R1 is hydrogen; Methyl group substituted with deuterium; Or trimethylsilyl group.
  • R2 is hydrogen; Or a methyl group substituted with deuterium.
  • R3 is hydrogen; Methyl group substituted with deuterium; Isopropyl group; Isopropyl group substituted with deuterium; Neopentyl group substituted with deuterium; Or a cyclohexyl group.
  • R4 is hydrogen; Methyl group substituted with deuterium; Methyl group; Isopropyl group; Cyclohexyl group; Or a cyclohexyl group substituted with deuterium.
  • R6 is hydrogen
  • the methyl group substituted with deuterium may be -CD 3 .
  • D means deuterium.
  • the isopropyl group substituted with deuterium may be represented by the following structural formula.
  • the neopentyl group substituted with deuterium may be represented by the following structural formula.
  • the cyclopentyl group substituted with deuterium may be represented by the following structural formula.
  • the cyclohexyl group substituted with deuterium may be represented by the following structural formula.
  • the trimethylsilyl group may be represented by TMS.
  • R5 is a halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Carboxyl groups; Imide group; Amide group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted phosphine group; Substituted or unsubstituted sulfonyl group; Substituted or unsubstit
  • R5 is a substituted or unsubstituted C3-C30 alkyl group; Or a substituted or unsubstituted cycloalkyl group.
  • R5 is a substituted or unsubstituted C3-C30 alkyl group; Or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.
  • R5 is a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.
  • R5 is a substituted or unsubstituted alkyl group having 3 to 10 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms.
  • R5 is a substituted or unsubstituted propyl group; Substituted or unsubstituted butyl group; Substituted or unsubstituted pentyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group.
  • R5 is an isopropyl group unsubstituted or substituted with deuterium; Substituted or unsubstituted isobutyl group; A substituted or unsubstituted tert-butyl group; Substituted or unsubstituted sec-butyl group; A cyclopentyl group unsubstituted or substituted with deuterium; Or a cyclohexyl group unsubstituted or substituted with deuterium.
  • R5 is an isopropyl group; Isopropyl group substituted with deuterium; Isobutyl group; tert-butyl group; sec-butyl group; Cyclopentyl group; A cyclopentyl group substituted with deuterium; Or a cyclohexyl group substituted with deuterium.
  • R5 is an isopropyl group; Isopropyl group substituted with deuterium; Isobutyl group; Cyclopentyl group; A cyclopentyl group substituted with deuterium; Cyclohexyl group; Or a cyclohexyl group substituted with deuterium.
  • n is an integer of 0 to 2
  • n is 2
  • the structures in parentheses [] are the same or different.
  • n is 0 or 1.
  • n 1 or 2.
  • n 0.
  • n 1
  • n is 2.
  • r1 to r4 are integers of 0 to 4, and when r1 to r4 are each 2 or more, the structures in parentheses () are the same as or different from each other.
  • r1 is 0 to 4.
  • r1 is 0 to 2.
  • r2 is 0 to 4.
  • r2 is 0 or 1.
  • r3 is 0 to 4.
  • r3 is 0 to 2.
  • r4 is 0 to 4.
  • r4 is 0 or 1.
  • Chemical Formula 1 may be represented by the following Chemical Formula 2.
  • X, R1 to R6, n and r1 to r4 are as defined in the formula (1).
  • Chemical Formula 1 may be represented by the following Chemical Formula 3.
  • X, R1 to R6, n and r1 to r4 are as defined in the formula (1).
  • Chemical Formula 1 may be represented by the following Chemical Formula 4.
  • X, R1 to R6, n and r1 to r4 are as defined in the formula (1).
  • Chemical Formula 1 may be any one selected from the following compounds.
  • the present specification provides an organic light emitting device including the organometallic compound represented by the formula (1).
  • an organic light emitting device including a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic layer is It provides an organic light emitting device comprising an organometallic compound represented by the formula (1).
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes an organometallic compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the organometallic compound represented by Chemical Formula 1 as a dopant.
  • the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the organometallic compound of Formula 1 may be included in the emission layer (3).
  • the organometallic compound of Formula 1 may be included in the emission layer 7.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the organometallic compound of Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition PVD, physical vapor deposition
  • sputtering e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof on the substrate
  • It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organometallic compound of Chemical Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode.
  • the hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material.
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer.
  • the hole transport material is a material that can transport holes from an anode or a hole injection layer and transfer them to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • the light emitting material may be used in the light emitting layer, and may be used in combination with a host and a dopant.
  • the emission layer may include a host and a dopant, and the dopant includes an organometallic compound represented by Chemical Formula 1.
  • the host includes a condensed aromatic ring derivative or a heterocyclic compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, or triazine derivatives; and the like, but may be a mixture of two or more thereof, but is not limited thereto.
  • the host may be a heterocyclic containing compound, specifically, a carbazole derivative or a triazine derivative, and may be a mixture of carbazole derivatives and triazine derivatives, but is not limited thereto. .
  • the host may be a compound represented by Formula A below.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a 1 to A 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted hetero aryl group,
  • a 1 and a 4 are integers from 0 to 4, and a 2 and a 3 are integers from 0 to 3.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a phenyl group substituted with a phenyl group; Or a biphenyl group.
  • a 1 to A 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms.
  • a 1 to A 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • a 1 to A 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
  • a 1 to A 4 are hydrogen.
  • Formula A may be represented by the following Formula A-1.
  • Ar 1 and Ar 2 , A 1 to A 4 and a 1 to a 4 are the same as defined in Formula A.
  • Formula A may be represented by the following formula.
  • the host may be a compound represented by the following formula (B).
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • B 1 and B 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent substituent to form a substituted or unsubstituted ring,
  • b 1 and b 2 are integers of 0 to 4.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently a phenyl group; A phenyl group substituted with a phenyl group; Or a biphenyl group.
  • L is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.
  • L is a substituted or unsubstituted phenylene group.
  • L is a phenylene group.
  • B 1 and B 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or combine with an adjacent substituent to form a substituted or unsubstituted aromatic ring.
  • B 1 and B 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or combine with an adjacent substituent to form a substituted or unsubstituted aromatic ring.
  • B 1 and B 2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or combine with an adjacent substituent to form a substituted or unsubstituted aromatic ring.
  • B 1 and B 2 are the same as or different from each other, and are each independently hydrogen or combine with an adjacent substituent to form a substituted or unsubstituted fluorenyl group.
  • B 1 and B 2 are the same as or different from each other, and are each independently hydrogen or combine with an adjacent substituent to form a fluorenyl group substituted with a methyl group.
  • Chemical Formula B may be represented by the following Chemical Formula B-1.
  • B 3 and B 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • b 3 is an integer of 0 to 2
  • b 4 is an integer of 0 to 4;
  • B 3 and B 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; Substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms.
  • B 3 and B 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • B 3 and B 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
  • B 3 and B 4 are each hydrogen.
  • Formula B may be represented by the following formula.
  • the content of the dopant may be selected in the range of 5 to 20 parts by weight based on 100 parts by weight of the host content, preferably 6 to 10 days. But it is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons to the electron injection material, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and is generated in the light emitting layer
  • the compound which prevents the movement of the excited excitons to the hole injection layer, and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • iridium chloride (10 g, 33 mmol) and Compound A1 (11.4 g, 0.073 mol) were added to 2-ethoxyethanol (1000 ml) and distilled water (330 ml) in a round bottom flask. Into and stirred for 24 hours. Lowering the temperature to room temperature (25 °C), filtered and washed with 2L of ethanol to prepare a solid compound 1-1a (10.2 g, 59% yield).
  • Intermediate 1-1b was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate A2 was used instead of Intermediate A1 (20 g, 54% yield).
  • Intermediate B2 was prepared by the same method as the method of preparing intermediate B1, except that Intermediate 1-1b was used instead of Intermediate 1-1a (yield 94%).
  • Intermediate 1-1e was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate A3 was used instead of Intermediate A1 (10.2 g, yield 62%).
  • Intermediate 1-1g was prepared in the same manner as the method for preparing intermediate 1-1a, except that intermediate A4 was used instead of intermediate A1 (10.4 g, yield 65%).
  • Intermediate B4 was prepared by the same method as the method of preparing intermediate B1, except that Intermediate 1-1g was used instead of Intermediate 1-1a (yield 87%).
  • Intermediate A5 was prepared by the same method as the method of preparing Intermediate A4, except that Intermediate 1-1h was used instead of Intermediate 1-1f (19 g, Yield 58%).
  • Intermediate 1-1i was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate A5 was used instead of Intermediate A1 (20 g, 55% yield).
  • Intermediate B5 was prepared by the same method as the method of preparing intermediate B1, except that Intermediate 1-1i was used instead of Intermediate 1-1a (yield 90%).
  • Intermediate 2-1a was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate C1 was used instead of Intermediate A1 (33 g, Yield 48%).
  • the intermediate D1 was prepared by the same method as the method of preparing intermediate B1, except that Intermediate 2-1a was used instead of Intermediate 1-1a (yield 87%).
  • Intermediate 2-1d was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate C2 was used instead of Intermediate A1 (26 g, 54% yield).
  • Intermediate D2 was prepared by the same method as the method of preparing Intermediate B1, except that Intermediate 2-1d was used instead of Intermediate 1-1a (23 g, 90% yield).
  • the intermediate was prepared by the same method as the method for preparing intermediate 2-1b, except that 2-iodopropane-2-d was used instead of 2-iodopropane.
  • 2-1e was prepared (54 g, 72% yield).
  • Intermediate 2-1f was prepared in the same manner as the intermediate 2-1c except for using the intermediate 2-1e instead of the intermediate 2-1b (47 g, 79% yield).
  • Intermediate C3 was prepared by the same method as the method of preparing intermediate C2, except that Intermediate 2-1f was used instead of Intermediate 2-1c (45 g, yield 75%).
  • Intermediate 2-1 g was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate C3 was used instead of Intermediate A1 (25 g, yield 57%).
  • Intermediate D3 was prepared by the same method as the method of preparing Intermediate B1, except that Intermediate 2-1g was used instead of Intermediate 1-1a (23 g, 85% yield).
  • Intermediate 2-1h was prepared by the same method as the method of preparing intermediate 2-1b, except for using iodocyclohexane instead of 2-iodopropane (38 g, yield) 71%).
  • Intermediate 2-1i was prepared by the same method as the method of preparing intermediate 2-1c, except that Intermediate 2-1h was used instead of Intermediate 2-1b (33 g, yield 64%).
  • Intermediate C4 was prepared by the same method as the method of preparing intermediate C2, except that Intermediate 2-1i was used instead of Intermediate 2-1c (30 g, 81% yield).
  • Intermediate C5 was prepared by the same method as the method of preparing intermediate A4, except that Intermediate 2-1k was used instead of Intermediate 1-1f (24 g, yield 46%).
  • Intermediate 2-1m was prepared by the same method as the method of preparing intermediate 2-1c, except that Intermediate 2-1l was used instead of Intermediate 2-1b (34g, 83% yield).
  • Intermediate C6 was prepared by the same method as the method of preparing intermediate C2, except that Intermediate 2-1m was used instead of Intermediate 2-1c (32 g, 71% yield).
  • Intermediate 2-1o was prepared by the same method as the method of preparing intermediate 2-1c, except that Intermediate 2-1n was used instead of Intermediate 2-1b (39 g, 81% yield).
  • Intermediate C7 was prepared by the same method as the method of preparing intermediate C2, except that intermediate 2-1o was used instead of intermediate 2-1c (36 g, yield 70%).
  • 2-iodopropane-2-d is used instead of 2-iodopropane and 4-bromo-1-iododibenzofuran (4- Intermediate 2, except that 4-bromo-1-iododibenzo [b, d] thiophene was used instead of bromo-1-iododibenzo [b, d] furan)
  • the intermediate 2-1e was prepared in the same manner as the method for preparing -1b (54 g, 72% yield).
  • Intermediate 2-1f was prepared in the same manner as the intermediate 2-1c except for using the intermediate 2-1e instead of the intermediate 2-1b (47 g, 79% yield).
  • Intermediate C3 was prepared by the same method as the method of preparing intermediate C2, except that Intermediate 2-1f was used instead of Intermediate 2-1c (45 g, yield 75%).
  • Intermediate 2-1 g was prepared by the same method as the method of preparing intermediate 1-1a, except that Intermediate C3 was used instead of Intermediate A1 (25 g, yield 57%).
  • Intermediate D3 was prepared by the same method as the method of preparing Intermediate B1, except that Intermediate 2-1g was used instead of Intermediate 1-1a (23 g, 85% yield).
  • Compound 2 was prepared by the same method as the method of preparing compound 1, except that Intermediate C3 was used instead of Intermediate C2 (yield 49%).
  • Compound 5 was prepared by the same method as the method of preparing compound 1, except that intermediate B4 was used instead of intermediate B3 (yield 44%).
  • Compound 8 was prepared by the same method as the method of preparing compound 1, except that Intermediate B4 instead of Intermediate B3, and Intermediate C5 instead of Intermediate C2 (yield 51%).
  • Compound 9 was prepared by the same method as the method of preparing compound 1, except that Intermediate B5 was used instead of Intermediate B3 (yield 45%).
  • Compound 10 was prepared by the same method as the method of preparing compound 1, except that Intermediate B5 instead of Intermediate B3, and Intermediate C3 instead of Intermediate C2 (yield 42%).
  • Compound 11 was prepared by the same method as the compound 1, except that Intermediate B5 instead of Intermediate B3, and Intermediate C4 instead of Intermediate C2 (yield 51%).
  • Compound 12 was prepared by the same method as the method of preparing compound 1, except that Intermediate B5 instead of Intermediate B3, and Intermediate C5 instead of Intermediate C2 (yield 36%).
  • Compound 15 was prepared by the same method as the method of preparing compound 1, except that Intermediate D2 instead of Intermediate B3, and Intermediate A3 instead of Intermediate C2 (yield 42%).
  • Compound 16 was prepared by the same method as the method of preparing compound 1, except that Intermediate D2 instead of Intermediate B3, and Intermediate A4 instead of Intermediate C2 (yield 41%).
  • Compound 20 was prepared by the same method as the method of preparing compound 1, except that Intermediate D3 instead of Intermediate B3, and Intermediate A3 instead of Intermediate C2 (yield 40%).
  • Compound 21 was prepared by the same method as the method of preparing compound 1, except that Intermediate D3 instead of Intermediate B3, and Intermediate A4 instead of Intermediate C2 (yield 48%).
  • Compound 24 was prepared by the same method as the compound 23, except that Intermediate C3 was used instead of Intermediate C2 (yield 39%).
  • Compound 25 was prepared by the same method as the method of preparing compound 1, except that Intermediate C6 was used instead of Intermediate C2 (yield 49%).
  • Compound 26 was prepared by the same method as the method of preparing compound 1, except that Intermediate C7 was used instead of Intermediate C2 (yield 53%).
  • Compound 27 was prepared by the same method as the method of preparing compound 1, except that Intermediate C8 was used instead of Intermediate C2 (yield 53%).
  • the glass substrate coated with ITO indium tin oxide having a thickness of 1,300 mm 3 was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the HI-1 compound as described below was thermally vacuum deposited to a thickness of 500 kPa to form a hole injection layer.
  • the HT-1 compound was thermally vacuum deposited to a thickness of 800 kPa on the hole injection layer, and the HT-3 compound was vacuum deposited to a thickness of 500 kPa in order to form a hole transport layer.
  • Compound 1 synthesized in Preparation Example as a host H1, H2 mixture and a phosphorescent dopant was vacuum-deposited on the hole transport layer at a weight of 6 or 10 parts by weight based on 100 parts by weight of the host H1, H2 mixture to form a light emitting layer having a thickness of 400 kPa. .
  • ET-3 material was vacuum deposited on the light emitting layer to form a hole blocking layer by vacuum deposition, and an ET-4 material and LiQ were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron transport layer of 250 ⁇ .
  • Lithium fluoride (LiF) having a thickness of 10 ⁇ was sequentially deposited on the electron transport layer, and aluminum was deposited to have a thickness of 1000 ⁇ on the cathode to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 ⁇ / sec
  • aluminum 2 ⁇ / sec the vacuum degree during deposition was 1 ⁇ 10 ⁇ 7 to 5 ⁇ 10 ⁇ 8 torr was maintained.
  • the organic light emitting diodes of Examples 2 to 16 were prepared in the same manner as in Example 1, except that the compounds shown in Table 1 below were used as phosphorescent dopants, respectively, when forming the emission layer.
  • An organic light-emitting device of Comparative Examples 1 to 12 was prepared in the same manner as in Example 1, except that Compound 1, instead of Compound 1, was used as a phosphorescent dopant to form an emission layer.
  • T95 means the time taken for the luminance to decrease to 95% from the initial luminance.
  • the compound of the present invention was used as a phosphorescent dopant material, it was confirmed that the device characteristics were excellent in terms of voltage, efficiency, and color coordinates compared to the comparative example.
  • the present invention by replacing the alkyl group or cycloalkyl group of 3 or more carbon atoms in the position 1 of the dibenzofuran structure of the auxiliary ligand to prevent intermolecular stacking and lower the aggregation phenomenon. Through this, the self-quenching is prevented to increase the efficiency and the wavelength characteristic of the molecule itself is maintained to secure shorter wavelength band.
  • the emission wavelength of the shorter wavelength region was shown than that of Comparative Example 1, and a peak value of a maximum wavelength of 8 nm was obtained.
  • Comparative Examples 5 and 6 in which a methyl group having 1 carbon atom is substituted, the stacking effect described above can be clearly seen.
  • Examples 1 to 16 having a substituent of an alkyl group or a cycloalkyl group of 3 or more carbon atoms at position 1 of dibenzofuran showed low voltage and high efficiency as compared with Comparative Examples 1 to 4.
  • Comparative Examples 7 to 10 show that the structure in which the alkyl group or the cycloalkyl group of 3 or more carbon atoms is substituted at the 1 position of the dibenzofuran structure shows superior performance in voltage, efficiency, and lifetime compared to the structure containing the N atom in the ligand. Can be. [Description of the code]

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Abstract

La présente invention concerne un composé organométallique et une diode électroluminescente organique le comprenant.
PCT/KR2019/005786 2018-05-14 2019-05-14 Composé organométallique et diode électroluminescente organique le comprenant WO2019221484A1 (fr)

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Cited By (5)

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WO2023282138A1 (fr) 2021-07-06 2023-01-12 キヤノン株式会社 Complexe métallique organique, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile contenant chacun celui-ci
WO2023190219A1 (fr) * 2022-03-30 2023-10-05 キヤノン株式会社 Complexe métallique organique, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile contenant chacun un complexe métallique organique

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EP4328285A1 (fr) 2022-08-25 2024-02-28 Beijing Summer Sprout Technology Co., Ltd. Matériau électroluminescent organique et dispositif associé

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CN113278033B (zh) * 2020-02-20 2023-04-28 北京夏禾科技有限公司 有机电致发光材料及器件
WO2023282138A1 (fr) 2021-07-06 2023-01-12 キヤノン株式会社 Complexe métallique organique, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile contenant chacun celui-ci
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WO2023190219A1 (fr) * 2022-03-30 2023-10-05 キヤノン株式会社 Complexe métallique organique, et élément électroluminescent organique, dispositif d'affichage, dispositif d'imagerie, équipement électronique, dispositif d'éclairage et objet mobile contenant chacun un complexe métallique organique

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CN111655705B (zh) 2023-11-07
KR20190130513A (ko) 2019-11-22
CN111655705A (zh) 2020-09-11
KR102230981B1 (ko) 2021-03-23

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