WO2019231212A1 - Composé hétérocyclique et dispositif électroluminescent organique le comprenant - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique le comprenant Download PDF

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WO2019231212A1
WO2019231212A1 PCT/KR2019/006383 KR2019006383W WO2019231212A1 WO 2019231212 A1 WO2019231212 A1 WO 2019231212A1 KR 2019006383 W KR2019006383 W KR 2019006383W WO 2019231212 A1 WO2019231212 A1 WO 2019231212A1
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group
substituted
unsubstituted
carbon atoms
light emitting
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PCT/KR2019/006383
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Korean (ko)
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정민우
이동훈
장분재
이정하
한수진
박슬찬
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주식회사 엘지화학
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Priority to CN201980011994.8A priority Critical patent/CN111683947B/zh
Publication of WO2019231212A1 publication Critical patent/WO2019231212A1/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
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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 heterocyclic 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 heterocyclic compound and an organic light emitting device including the same.
  • X1 to X3 are the same as or different from each other, and each independently N or CH
  • At least one of X1 to X3 is N,
  • Z is O or S
  • R1 and R2 are the same as or different from each other, and each independently, hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted Or an unsubstituted heteroaryl group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • L is a straight bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Y is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
  • a is an integer from 0 to 5
  • b is an integer from 0 to 4,
  • R1 is the same as or different from each other
  • the R2s are the same as or different from each other.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound. .
  • the heterocyclic 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 the same, 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 according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
  • the present specification provides a heterocyclic 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; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • the alkoxy group may be linear, branched or cyclic.
  • carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferable that it is C1-C20. More specifically, it is preferable that it is C1-C10.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20.
  • Specific examples include vinyl groups; 1-propenyl group; Isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; Allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl group; 2, 2-bis (diphenyl- 1-yl) vinyl- 1-yl group; Stilbenyl group; Styrenyl group and the like, but is not limited thereto.
  • the alkynyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20.
  • the phosphine oxide group is specifically a diphenylphosphine oxide group; And dinaphthylphosphine oxide groups, but are 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 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 aryl group is not particularly limited, but preferably has 6 to 30 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 30 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 C10-30.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • the aryl group in the aryloxy group is the same as the example 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. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, 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 Sleepyl 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
  • the arylene group is the same as the definition of the aryl group, except that the arylene group.
  • heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.
  • Formula 1 is represented by any one of the following formula (2) and formula (3).
  • X1 to X3, L, Y, Ar1, Ar2, R1, R2, a and b are the same as defined in Formula 1.
  • X1 is N
  • X2 and X3 are CH.
  • X2 is N
  • X1 and X3 are CH.
  • X3 is N, and X1 and X2 are CH.
  • X1 and X2 are N, and X3 is CH.
  • X1 and X3 are N, and X2 is CH.
  • X2 and X3 are N, and X2 is CH.
  • X1 to X3 is N.
  • R1 and R2 are hydrogen.
  • Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group containing any one or more of N, O, and S having 3 to 30 carbon atoms.
  • Y is an aryl group; Or a heteroaryl group,
  • the aryl group; Or a heteroaryl group is unsubstituted or substituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted phosphine oxide group do.
  • Y is an aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms,
  • the aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms is deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted phosphine oxide. Substituted or unsubstituted with a group.
  • Y is a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Triphenylene group; Phenanthrene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; Benzofury pyrimidine group; Benzothienopyrimidine group; Phosphine oxide groups; Pyridine group; Pyrimidine groups; Triazine group,
  • Y is a monocyclic aryl group having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl group having 3 to 30 carbon atoms or polycyclic heteroaryl group having 3 to 30 carbon atoms,
  • the monocyclic aryl group having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl group having 3 to 30 carbon atoms or polycyclic heteroaryl group having 3 to 30 carbon atoms is deuterium, nitrile group, halogen group, alkyl group having 1 to 10 carbon atoms unsubstituted or substituted, substituted or unsubstituted C 6 Substituted or unsubstituted aryl group of 30 to 30, substituted or unsubstituted heteroaryl group containing any one or more of N, O or S having 3 to 30 carbon atoms, or a phosphine oxide group unsubstituted or substituted with an alkyl group or an aryl group do.
  • Y is a phenyl group unsubstituted or substituted with a nitrile group, triphenylmethyl group, naphthyl group, phenylnaphthyl group, triphenylsilyl group, or trimethylsilyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Terphenyl group; Triphenylene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; A benzopuropyrimidine group unsubstituted or substituted with a phenyl group; A benzothienopyrimidine group unsubstituted or substituted with a phenyl group; Phosphine oxide groups substituted with phenyl groups; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubsti
  • Y may be any one selected from the following substituents.
  • Ar1 and Ar2 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 3 to 30 carbon atoms to be.
  • Ar1 and Ar2 are the same as each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic polycyclic group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
  • Ar1 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
  • Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.
  • L is a direct bond, or a substituted or unsubstituted arylene group.
  • L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a direct bond or a monocyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a direct bond, or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms.
  • L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted bivalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, substituted Or an unsubstituted divalent quarterphenyl group, a substituted or unsubstituted divalent fluorene group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent triphenylene group Or a substituted or unsubstituted divalent phenanthrene group.
  • L is a phenylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a naphthylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A substituted or unsubstituted bivalent biphenyl group, a divalent terphenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent quarterphenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A divalent fluorene group unsubstituted or substituted with a divalent anthracene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent pyrene group unsubstituted or
  • L is a phenylene group, naphthylene group, divalent biphenyl group, divalent terphenyl group, divalent quarterphenyl group, divalent fluorene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms Group, a bivalent anthracene group, a bivalent pyrene group, a bivalent triphenylene group, or a bivalent phenanthrene group.
  • L may be represented by the following substituents.
  • L is a direct bond
  • L is a phenylene group.
  • L is a divalent naphthyl group.
  • heterocyclic compound of Formula 1 may be represented by the following structural formula.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers may include the aforementioned heterocyclic compound.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
  • the first electrode 2 the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the electron transport layer 9, and the electron injection layer
  • the structure of the organic light emitting device in which 10) and the second electrode 4 are sequentially stacked is illustrated.
  • the compound of the present invention may be included in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and preferably may be included in a light emitting layer.
  • 1 and 2 illustrate an organic light emitting device and are not limited thereto.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
  • the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 50:50.
  • the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 60:40.
  • the organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 80:20.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include an additional host.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include an organic compound as an additional host.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include a carbazole derivative as an additional host.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a bicarbazole compound as an additional host.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound of Formula X as an additional host.
  • Ax and Ay are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
  • Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or Unsubstituted heteroaryl group,
  • x and y are each an integer of 0 to 7,
  • Ax and Ay are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms.
  • Ax and Ay are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a fluorene group, or a pyrene group.
  • Ax and Ay are the same as or different from each other, and are each independently a phenyl group or a biphenyl group.
  • Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group.
  • Rx and Ry are hydrogen.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include an additional dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a fluorescent dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a phosphorescent dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a metal complex as a dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include an iridium-based dopant.
  • the organic material layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the heterocyclic compound. have.
  • the organic material layer may include an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer may include the heterocyclic compound. have.
  • the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.
  • 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.
  • 2-chloro-4,6-diphenyl-1,3,5-triazine (50.0 g, 187 mmol) and (2-chloro-3-fluorophenyl) boronic acid (48.9 g, 280 mmol) in a nitrogen atmosphere was added to 400 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561 mmol) was dissolved in 210 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 3 mol%) was added thereto.
  • Compound 2 (10.6 g, 71%) was synthesized in the same manner as in the preparation of Compound 1, except that 1-bromonaphthalene was used instead of 2-bromobenzene.
  • Compound 3 (8.6 g, 55%) was synthesized in the same manner as in the preparation of Compound 1, except that 4-bromobiphenyl was used instead of 2-bromobenzene.
  • Compound 5 (10.2 g, 63%) was synthesized in the same manner as in the preparation of Compound 1, except that 9-bromophenanthrene was used instead of 2-bromobenzene.
  • Compound 8 (6.3 g, 44%) was synthesized in the same manner as in the preparation of Compound 1, except that 3-bromobenzonatrile was used instead of 2-bromobenzene.
  • the glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put 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 hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 kPa on the prepared ITO transparent electrode.
  • a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 GPa on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound to 50 GPa on the HT-1 deposition film.
  • ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer
  • the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW.
  • Aluminum was deposited to a thickness of 1000 ⁇ on the electron injection layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the aluminum was maintained at the deposition rate of 2 ⁇ / sec
  • the vacuum during deposition was maintained at 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr It was.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1.
  • the compounds of CE1 to CE3 in Table 1 are as follows.
  • the organic light emitting diode was measured voltage and efficiency at a current density of 10mA / cm 2 , the lifetime was measured at a current density of 50mA / cm 2 and the results are shown in Table 1 below.
  • LT95 means a time of 95% of the initial luminance.
  • the compounds of the present invention showed lower voltage, higher efficiency and longer life compared to CE1 without the dibenzofuran core,
  • N-containing monocyclic ring such as CE2
  • binds to position 2 of dibenzofuran it showed lower efficiency and significantly shorter lifespan than Experimental Examples 1 to 9 using the compound of the present invention. Even when there is no short life compared to Experimental Examples 1 to 9.
  • the compound of the present invention When the compound of the present invention is used as a light emitting layer material, it was confirmed that exhibits excellent efficiency and lifespan as compared to the comparative experiment. It is believed that the electron stability is increased by substituting benzothiazole at the 8 position while replacing hydrogen using the aryl and hetero aryl groups at the 6 position of the dibenzofuran substituent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne : un composé hétérocyclique de formule chimique 1; et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/006383 2018-05-29 2019-05-28 Composé hétérocyclique et dispositif électroluminescent organique le comprenant WO2019231212A1 (fr)

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KR101385216B1 (ko) * 2012-11-07 2014-04-14 주식회사 엘엠에스 신규한 화합물, 이를 포함하는 발광 소자 및 전자 장치
WO2016198144A1 (fr) * 2015-06-10 2016-12-15 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20170003502A (ko) * 2016-12-27 2017-01-09 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
WO2017178311A1 (fr) * 2016-04-11 2017-10-19 Merck Patent Gmbh Composés hétérocycliques à structures dibenzofuranes et/ou dibenzothiophènes

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DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten
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KR102210699B1 (ko) * 2018-02-08 2021-02-01 주식회사 엘지화학 유기 발광 소자

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KR20100118690A (ko) * 2009-04-29 2010-11-08 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR101385216B1 (ko) * 2012-11-07 2014-04-14 주식회사 엘엠에스 신규한 화합물, 이를 포함하는 발광 소자 및 전자 장치
WO2016198144A1 (fr) * 2015-06-10 2016-12-15 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2017178311A1 (fr) * 2016-04-11 2017-10-19 Merck Patent Gmbh Composés hétérocycliques à structures dibenzofuranes et/ou dibenzothiophènes
KR20170003502A (ko) * 2016-12-27 2017-01-09 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자

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