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WO2017061785A1 - Composé de type spiro et diode électroluminescente organique comprenant celui-ci - Google Patents

Composé de type spiro et diode électroluminescente organique comprenant celui-ci Download PDF

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WO2017061785A1
WO2017061785A1 PCT/KR2016/011181 KR2016011181W WO2017061785A1 WO 2017061785 A1 WO2017061785 A1 WO 2017061785A1 KR 2016011181 W KR2016011181 W KR 2016011181W WO 2017061785 A1 WO2017061785 A1 WO 2017061785A1
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group
substituted
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compound
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Korean (ko)
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하재승
곽지원
서상덕
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020160071269A external-priority patent/KR101991049B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201680031485.8A priority Critical patent/CN107635983B/zh
Priority to EP16853901.3A priority patent/EP3360868B1/fr
Priority to JP2017558480A priority patent/JP6729858B2/ja
Priority to US15/575,148 priority patent/US11075342B2/en
Publication of WO2017061785A1 publication Critical patent/WO2017061785A1/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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

Definitions

  • the present specification relates to a spiro compound and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present specification provides a spiro compound and an organic light emitting device including the same.
  • spiro type compound represented by the following formula (1).
  • X 1 is O or S
  • R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boro
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar1 to Ar6 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, Ar1 and Ar2; Ar3 and Ar4; And one or more of Ar5 and Ar6 combine with each other to form a substituted or unsubstituted ring,
  • r1, r2, r3 and r4 are each an integer of 1 to 4,
  • n and p are each an integer of 0 to 3
  • n and p are each an integer of 2 or more, the structures in two or more parentheses are the same or different from each other.
  • the spiro compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using this, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.
  • FIG. 1 illustrates an organic light emitting device 10 according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting device 11 according to another exemplary embodiment of the present specification.
  • the present specification provides a spiro type compound represented by Chemical Formula 1.
  • 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; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted or unsubstituted
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • 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. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the ester group may be substituted with oxygen of the ester group having a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, 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, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, 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 are not limited thereto. It is not.
  • 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-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, 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 may be, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine 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.
  • the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
  • the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
  • the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above.
  • the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
  • the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30.
  • 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 silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • 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.
  • phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
  • the aryl group is not particularly limited, but preferably has 6 to 50 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 50 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C50.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an 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" groups.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above.
  • the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like.
  • arylthioxy group examples include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned,
  • An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the carbon number is not particularly limited, but is preferably 2 to 50 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.
  • the arylene group refers to a divalent group having two bonding positions in the aryl group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group.
  • the description of the aforementioned heteroaryl group can be applied except that they are each divalent.
  • a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
  • the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
  • the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
  • the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.
  • Formula 1 is represented by the following formula 1-1 or 1-2.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3 to 1-6.
  • R1 to R4, L1 to L3, Ar1 to Ar6, r1 to r4, m, n, and p are the same as in Chemical Formula 1.
  • R1 to R4 is hydrogen.
  • L1 to L3 is a direct bond; Or a substituted or unsubstituted arylene group.
  • L1 to L3 is a direct bond; Or an arylene group.
  • L1 to L3 is a direct bond; Or a phenylene group.
  • Ar1 to Ar6 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar1 to Ar6 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.
  • Ar1 to Ar6 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; Or a heteroaryl group.
  • Ar1 to Ar6 are the same as or different from each other, each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted carbazolyl group; Substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar1 to Ar6 are the same as or different from each other, and each independently an aryl group, or a phenyl group unsubstituted or substituted with a heteroaryl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Spirobifluorenyl group; Carbazolyl group; Dibenzofuranyl group; Or a dibenzothiophene group.
  • Ar1 to Ar6 are the same as or different from each other, and each independently a phenyl group or a phenyl group unsubstituted or substituted with a carbazolyl group; Biphenyl group; Naphthyl group and phenanthrenyl group; Fluorenyl group substituted by the methyl group or the phenyl group; Spirobifluorenyl group; Carbazolyl group; Dibenzofuranyl group; Or a dibenzothiophene group.
  • X2 is CRR ', NR ", O or S,
  • R, R ', R ", R201 and R202 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
  • r201 and r202 are each an integer of 1 to 4,
  • R and R ' are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group.
  • R and R ' are the same as or different from each other, and each independently an alkyl group.
  • R and R ' is a methyl group.
  • R is a substituted or unsubstituted aryl group.
  • R is an aryl group.
  • R is a phenyl group.
  • R201 and R202 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group.
  • R201 and R202 are the same as or different from each other, and each independently hydrogen; Or an aryl group.
  • R201 and R202 are the same as or different from each other, and each independently hydrogen; Or a phenyl group.
  • Formula A is represented by any one of the following structures.
  • Formula 1 is selected from the following compounds.
  • the 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 aforementioned spiro-type compound.
  • 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, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20.
  • 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • FIG. 2 illustrates a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90, and a second electrode on a substrate 20.
  • a structure of an organic light emitting device in which 50) is sequentially stacked is illustrated.
  • 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the organic material layer includes a hole injection layer, and the hole injection layer includes a spiro type compound represented by Chemical Formula 1.
  • the organic material layer includes a hole transport layer
  • the hole transport layer comprises a spiro-type compound represented by the formula (1).
  • the organic material layer includes a hole control layer, and the hole control layer includes a spiro type compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a spiro type compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a spiro-type compound represented by Chemical Formula 1 as a dopant of the light emitting layer.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1-A.
  • n1 is an integer of 1 or more
  • Ar7 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,
  • L4 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,
  • n1 is 2 or more
  • the structures in two or more parentheses are the same or different from each other.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-A as a dopant of the light emitting layer.
  • L4 is a direct bond.
  • n1 is 2.
  • Ar7 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, or tert-butyl groups; Or a divalent chrysene group unsubstituted or substituted with deuterium, methyl, ethyl or tert-butyl group.
  • Ar8 and Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar8 and Ar9 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is an aryl group.
  • Ar8 and Ar9 are the same or different from each other, and each independently an aryl group unsubstituted or substituted with a silyl group substituted with an alkyl group.
  • Ar8 and Ar9 are the same or different from each other, and each independently an aryl group unsubstituted or substituted with a trimethylsilyl group.
  • Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.
  • Ar8 and Ar9 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or trimethylsilyl group.
  • Ar8 and Ar9 are the same or different from each other, and each independently a biphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group.
  • Ar8 and Ar9 are the same as or different from each other, and each independently a terphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or a trimethylsilyl group.
  • Ar8 and Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.
  • Ar8 and Ar9 are the same as or different from each other, and each independently substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group or a phenyl group It is an aryl group.
  • Ar8 and Ar9 are the same as or different from each other, and each independently substituted or unsubstituted with a methyl group, ethyl group, tert-butyl group, nitrile group, trimethylsilyl group or phenyl group to be.
  • Formula 1-A is selected from the following compounds.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 2-A.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
  • G1 to G8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a compound represented by Formula 2-A as a host of the light emitting layer.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted polycyclic aryl group.
  • Ar11 and Ar12 are the same as or different from each other, and each independently represent a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted naphthyl group.
  • Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted 1-naphthyl group.
  • Ar11 and Ar12 are 1-naphthyl group.
  • the G1 to G8 is hydrogen.
  • Formula 2-A is selected from the following compounds.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound represented by Formula 1-A as a dopant of the light emitting layer
  • the compound represented by Formula 2-A as a host of the light emitting layer Include as.
  • the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • 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 a spiro-type compound of the present specification, that is, a spiro-type compound represented by Formula 1 above. Can be.
  • 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
  • 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 a first electrode, 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 second electrode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
  • the spiro compound represented by 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.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the 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); ZnO: Al or SnO 2 : Combination of metals and oxides such as 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, Mg / Ag, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode with a hole injection material, and has a capability of transporting holes with a hole injection material, and thus has a hole injection effect at an anode, and an excellent hole injection effect with respect to a light emitting layer or a light emitting material.
  • generated in the light emitting layer 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 that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer 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 hole control layer effectively receives holes from the hole transport layer and serves to control hole mobility to adjust the amount of holes transferred to the light emitting layer.
  • it may simultaneously serve as an electron barrier to prevent electrons supplied from the light emitting layer from falling into the hole transport layer. This can maximize the balance of holes and electrons in the light emitting layer to increase the luminous efficiency, improve the life of the device through the electron stability of the hole control layer, it is possible to use materials known in the art.
  • the light emitting material of the light emitting layer 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, benzothiazole 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 layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a hetero ring-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transporting material of the electron transporting layer is a layer for receiving electrons from the electron injection layer and transporting 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. This large material is 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 that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a 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 like and 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.
  • the spiro compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Benzofuran-2-boronic acid (20 g, 123.4 mmol) and 1-bromo-3-chloro-6-iodobenzene (39.36 g, 124.6 mmol) were added to dioxane (300 ml), followed by 2M aqueous potassium carbonate solution ( 100 ml) was added, tetrakistriphenyl-phosphinopalladium (2.85 g, 2 mol%) was added thereto, and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed to separate the layers.
  • Compound A-1 (33.97g, yield 90%) was prepared by column with hexane after solvent removal.
  • Compound A- was synthesized in the same manner as in Production Example A-1, except that 1-bromo-4-chloro-2-iodobenzene was used instead of 1-bromo-3-chloro-6-iodobenzene. 2 was prepared.
  • Compound A-3 was prepared by the same method as in Preparation Example A-2, except that benzofuran-3-boronic acid was used instead of benzofuran-2-boronic acid.
  • Compound A- was synthesized in the same manner as in Production Example A-1, except that 1-bromo-3-chloro-2-iodobenzene was used instead of 1-bromo-3-chloro-6-iodobenzene. 4 was prepared.
  • Compound A-5 was prepared by the same method as in Preparation Example A-1, except that benzothiophene-2-boronic acid was used instead of benzofuran-2-boronic acid.
  • Compound B-2 was synthesized in the same manner as in Production Example B-1, except that 4-bromo-9H-fluoren-9-one was used instead of 2-bromo-9H-fluoren-9-one. Prepared.
  • Compound B-3 was prepared in the same manner as in Preparation Example B-1, except that Compound A-2 was used instead of Compound A-1.
  • Compound B-5 was prepared in the same manner as in Preparation Example B-1, except that Compound A-4 was used instead of Compound A-1.
  • Compound B-7 was prepared in the same manner as in Preparation Example B-1, except that Compound A-6 was used instead of Compound A-1.
  • Compound C-2 was prepared in the same manner as in Preparation Example C-1, except that Compound B-2 was used instead of Compound B-1.
  • Compound C-3 was prepared in the same manner as in Preparation Example C-1, except that Compound B-3 was used instead of Compound B-1.
  • Compound C-4 was prepared in the same manner as in Preparation Example C-1, except that Compound B-4 was used instead of Compound B-1.
  • Compound C-5 was prepared in the same manner as in Preparation Example C-1, except that Compound B-5 was used instead of Compound B-1.
  • Compound C-6 was prepared by the same method as the preparation method C-1 except that compound B-6 was used instead of compound B-1.
  • Compound C-7 was prepared in the same manner as in Preparation Example C-1, except that Compound B-7 was used instead of Compound B-1.
  • Compound 2 was prepared in the same manner as in Preparation Example 1, except that D-1 was used instead of Compound C-1 and N-phenylnaphthalen-1-amine was used instead of diphenylamine.
  • Compound D-2 was prepared by the same method as in Preparation Example 2, except that C-3 was used instead of Compound C-2 in the preparation of Compound D-1.
  • D-2 was used instead of the compound C-1 in Preparation Example 1, and N-([1,1'-biphenyl] -4-yl)-[1,1 ''-biphenyl]-was used instead of diphenylamine.
  • Compound 3 was prepared by synthesis in the same manner except 3-amine was used.
  • Compound D-3 was prepared by the same method as Preparation Example 2, except that C-4 was used instead of Compound C-2 in the preparation of Compound D-1.
  • Compound 3 was prepared in the same manner as in Preparation Example 1, except that D-3 was used instead of Compound C-1 and di ([1,1'-biphenyl] -4-yl) amine was used instead of diphenylamine. 4 was prepared.
  • Compound 6 was prepared in the same manner as in Preparation Example 1, except that D-5 was used instead of compound C-1.
  • a compound of Compound 7 was prepared by the same method as in Preparation Example 1, except that D-6 was used instead of Compound C-1.
  • Compound Compound 7 was prepared by the same method as in Preparation Example 1, except that D-7 was used instead of Compound C-1.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Compound 1 (900 kPa), which is a material for transporting holes, was vacuum deposited thereon, followed by vacuum deposition of HT2 at a film thickness of 100 kPa on the hole transport layer to form a hole control layer.
  • the host H1 and the dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 kPa.
  • E1 compound 300 kPa was thermally vacuum deposited sequentially into the electron injection and transport layer.
  • An organic light emitting device was manufactured by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • the organic light emitting diodes of Examples 1-1 to 1-6 manufactured by using a spiro type compound according to an exemplary embodiment of the present specification have a lower voltage and higher efficiency than those of Comparative Example 1-1, which are benzidine-type materials. It can be seen that it exhibits characteristics.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • HT1 900 kPa
  • Compound 2 was vacuum-deposited at a film thickness of 100 kPa on the hole transport layer to form a hole control layer.
  • the host H1 and the dopant D1 compound 25: 1 were vacuum deposited to a thickness of 300 GPa.
  • E1 300 kPa
  • An organic light emitting device was manufactured by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • the organic light emitting diodes of Examples 2-1 to 2-3 manufactured by using a spiro type compound represented by Formula 1 according to an exemplary embodiment of the present specification are compared using HT2, which is a carbazole type material. It can be seen that the characteristics of lower voltage and higher efficiency are shown than the organic light emitting element of Example 2-1.
  • the spiro compound represented by Formula 1 may play a role of hole transport and hole control in an organic electronic device including an organic light emitting device, and the organic light emitting device according to the present specification may include efficiency, driving voltage, Excellent properties in terms of stability.

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Abstract

La présente invention concerne un composé de type double spiro et une diode électroluminescente organique comprenant celui-ci.
PCT/KR2016/011181 2015-10-06 2016-10-06 Composé de type spiro et diode électroluminescente organique comprenant celui-ci Ceased WO2017061785A1 (fr)

Priority Applications (4)

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CN201680031485.8A CN107635983B (zh) 2015-10-06 2016-10-06 螺环型化合物和包含其的有机发光二极管
EP16853901.3A EP3360868B1 (fr) 2015-10-06 2016-10-06 Composé de type spiro et diode électroluminescente organique comprenant celui-ci
JP2017558480A JP6729858B2 (ja) 2015-10-06 2016-10-06 スピロ型化合物およびこれを含む有機発光素子
US15/575,148 US11075342B2 (en) 2015-10-06 2016-10-06 Spiro-type compound and organic light emitting diode comprising same

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KR20150140436 2015-10-06
KR10-2015-0140436 2015-10-06
KR1020160071269A KR101991049B1 (ko) 2015-10-06 2016-06-08 스피로형 화합물 및 이를 포함하는 유기 발광 소자
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CN111052427A (zh) * 2017-11-28 2020-04-21 株式会社Lg化学 有机发光器件
CN111201624A (zh) * 2018-01-11 2020-05-26 株式会社Lg化学 有机发光二极管
EP4041709A1 (fr) * 2019-10-11 2022-08-17 Merck Patent GmbH Composés pour dispositifs électroniques

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WO2013120577A1 (fr) * 2012-02-14 2013-08-22 Merck Patent Gmbh Composés de spirobifluorène pour dispositifs organiques électroluminescents
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KR20150010016A (ko) * 2013-07-17 2015-01-28 롬엔드하스전자재료코리아유한회사 유기 전계 발광 소자
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WO2013120577A1 (fr) * 2012-02-14 2013-08-22 Merck Patent Gmbh Composés de spirobifluorène pour dispositifs organiques électroluminescents
KR20130096666A (ko) * 2012-02-22 2013-08-30 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
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CN111052427A (zh) * 2017-11-28 2020-04-21 株式会社Lg化学 有机发光器件
CN111052427B (zh) * 2017-11-28 2023-09-12 株式会社Lg化学 有机发光器件
CN111201624A (zh) * 2018-01-11 2020-05-26 株式会社Lg化学 有机发光二极管
CN111201624B (zh) * 2018-01-11 2023-09-12 株式会社Lg化学 有机发光二极管
EP4041709A1 (fr) * 2019-10-11 2022-08-17 Merck Patent GmbH Composés pour dispositifs électroniques

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