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WO2019004612A1 - Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant Download PDF

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Publication number
WO2019004612A1
WO2019004612A1 PCT/KR2018/006166 KR2018006166W WO2019004612A1 WO 2019004612 A1 WO2019004612 A1 WO 2019004612A1 KR 2018006166 W KR2018006166 W KR 2018006166W WO 2019004612 A1 WO2019004612 A1 WO 2019004612A1
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formula
substituted
unsubstituted
group
compound
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PCT/KR2018/006166
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English (en)
Korean (ko)
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허정오
이동훈
장분재
허동욱
한미연
양정훈
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주식회사 엘지화학
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Priority claimed from KR1020180059817A external-priority patent/KR102106121B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US16/625,589 priority Critical patent/US11542258B2/en
Priority to CN201880040226.0A priority patent/CN110753687B/zh
Publication of WO2019004612A1 publication Critical patent/WO2019004612A1/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
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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

  • organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode.
  • the organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-201373537
  • the present invention relates to a novel heterocyclic compound compound and a light emitting device including the same.
  • the present invention provides a compound represented by the following formula (1).
  • X is O or S
  • Y 2 and ⁇ 3 are each independently CR or ⁇ 'and, provided that two or more of them is ⁇ ,
  • R ' is substituted or in combination with hydrogen, or, R 7 and the adjacent 3 ⁇ 4 unsubstituted
  • Each of 3 ⁇ 4 and 3 ⁇ 4 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted d-
  • n is an integer of 1 to 4,
  • n is an integer of 1 to 3, A direct bond; Substituted or unsubstituted C 6 - 60 arylene; Or N, a substituted or unsubstituted heteroarylene 5 -60 C comprising one or more heteroatoms selected from the group consisting of 0 and S,
  • R 7 and 3 ⁇ 4 are each independently a substituted or unsubstituted C 6 - substitution or containing 60 aryl, substituted or unsubstituted one or more heteroatoms selected from the group consisting of unsubstituted silyl, or a N, 0, S and Si Unsubstituted C 5 -C 60 heteroaryl,
  • R < 7 > and R < 7 &gt is a compound represented by the following formula (2)
  • L 2 is a direct bond; Or substituted or unsubstituted C 6 - 60 arylene; 60 is heteroarylene, or N, a substituted or unsubstituted C 5 containing one or more heteroatoms selected from the group consisting of 0 and S
  • Het is silyl substituted or unsubstituted with at least one d- 60 alkyl or C 6 -60 aryl; C 6 -60 aryl substituted with at least one -CN or -CF 3 ; Or N, 0, S and Si, a substituted or unsubstituted ring containing one or more heteroatoms, C is selected from the group consisting of 5-60 heteroaryl.
  • the present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one layer of organic material disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound of the present invention.
  • the compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device.
  • the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.
  • FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron receiver 8 and a cathode 4 Respectively.
  • the present invention provides a compound represented by the following formula (1).
  • X is O or S
  • Yi, Y 2 and ⁇ 3 are each independently ⁇ or CR ', and and, provided that two of them or more is ⁇ , R' is hydrogen or, in combination with an adjacent R 7, and 3 ⁇ 4 substituted or unsubstituted C 6 _ 60 aryl, < / RTI >
  • Ri, R 2 , 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted d- 60 alkyl; Or a substituted or unsubstituted C 6 -. 60 aryl, all of which are combined with an adjacent substituent may form a substituted or unsubstituted benzene ring,
  • Each of 3 ⁇ 4 and 3 ⁇ 4 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted d
  • n is an integer of 1 to 4,
  • n 1 to 3
  • R ? And? Are each independently a substituted or unsubstituted C 6 -C 60 aryl, a substituted or unsubstituted silyl, or a substituted or unsubstituted aryl group containing at least one heteroatom selected from the group consisting of N, O, S and Si 60 is a heteroaryl group, - a C 5
  • R 7 and R 4 is a compound represented by the following formula (2)
  • L 2 is a direct bond; Or substituted or unsubstituted C 6 - 60 arylene; 60 is heteroarylene, or N, a substituted or unsubstituted C 5 comprising one or more heteroatoms selected from the group consisting of 0 and S
  • Het is silyl, substituted or unsubstituted with at least one alkyl or C 6 -60 aryl; Substituted by at least one CN or -CF 3 C 6 - 60 aryl; Or N, 0, S and Si, a substituted or unsubstituted ring containing one or more heteroatoms, C is selected from the group consisting of 5-60 heteroaryl.
  • substituted or unsubstituted 1 refers to a substituent selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxyl, carbonyl, ester, An aryloxy group, an aryloxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, A heterocyclic amine group, an arylamine group, an arylphosphine group, or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted heterocyclic group substituted with at least one substituent selected from the group consisting of N, O and S atoms, Substituted or unsubstituted &lt
  • the "substituent group to which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound of the following structure
  • the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, N-pentyl, n-pentyl, n-pentyl, neopentyl, tert-pentyl, N-heptyl, 1-methylnucleosilyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, - dimethylheptyl, 1-ethyl-propyl, 1,1- But are not limited to, dimethyl-p-chlorophyl, isohexyl, 2-methylpentyl, 4-methylphenyl, 5-methylpyridyl and the like.
  • the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms.
  • the cycloalkyl group has 3 to 6 carbon atoms.
  • Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like, But is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
  • the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, An isoquinoline group, an indole group, an indole group, an indole group, an indole group, an indole group, an indole group, an indolyl group, A benzothiazole group, a benzoxazole group, a benzothiophene group, a benzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, An oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazo
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.
  • the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group is the same as the alkyl group described above.
  • the heteroaryl among the heteroarylamines is the same as that described above The description about the heterocyclic group may be applied.
  • the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
  • the description of the aryl group described above can be applied except that arylene is a divalent group.
  • the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.
  • the description of the above-mentioned aryl group or cycloalkyl group can be applied, except that the hydrocarbon ring is not a monocyclic and the two substituents are bonded to each other.
  • the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
  • the compound represented by the formula (1) may be any one selected from the compounds represented by the following formulas (3) to (9).
  • n and m are as defined above,
  • R 8 is a compound represented by the formula (2).
  • the compound represented by the formula (1) may be any one selected from the compounds represented by the following formulas (10) to (12).
  • the Het may be any one selected from the compounds represented by the following chemical formulas [1-1] to [1-31]:
  • Each Ra independently is hydrogen; Alkyl of substituted or unsubstituted d-so; Or a substituted or unsubstituted C 6 ring - A 60 aryl, 1 is each independently an integer of 1 to 4.
  • R 3 and R 4 are each independently hydrogen, methyl,
  • n is 1 or 2
  • m may be 0 or 1.
  • L < 2 > are each independently a direct bond or any one selected from the group consisting of:
  • the compound represented by the formula (1) is composed of
  • the compound represented by the general formula (1) of the present invention has a core structure in which xanthene (or thioxanthene) and a fluorene are spiro bonded to each other and the substituent of the fluorene triazine (or pyrimidine)
  • xanthene or thioxanthene
  • fluorene triazine or pyrimidine
  • asymmetric compound since it has a lower crystallinity than a symmetric structure, a dense film quality is formed at the time of film formation, and the lifetime is improved.
  • such arrangement between molecules improves the electron injecting and transporting ability, thereby realizing device characteristics of low voltage and high efficiency.
  • the triazine (or pyrimidine), the P- or N-type sex Het is introduced to act as a kind of retarder to control the electron mobility efficiency - to minimize the trade ⁇ f of the phenomenon of life implement a high efficiency and long life at the same time .
  • the organic light emitting device using the organic light emitting device can have a high efficiency, a low driving voltage, a high brightness and a long life.
  • the compound represented by the formula (1) can be prepared by the following reaction scheme A and scheme B. The above production method can be more specific in the production example to be described later.
  • the Hwang A and Hw B may proceed sequentially.
  • Hwan A and Hwan B X, Y 1; Y 2 , Y 3 , Ri, R 2 , R 5 , R 6 and R 7 ( 3 ⁇ 4, Li, m and n are as defined above and may further include additional substituents.
  • the reaction is carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction.
  • the types of catalysts and catalysts used in the reaction schemes can be suitably changed. The above manufacturing. The method can be further specified in the production example to be described later.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention provides a display device comprising: a first electrode; A second electrode facing the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.
  • 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 may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
  • 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 may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, Displayed rui / ⁇ ⁇ ⁇ ⁇ uiu / uu
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
  • the organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1).
  • the electron transporting layer, the electron injecting layer, or the layer which simultaneously injects electrons and transports electrons includes a compound represented by the above formula (1).
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability and has a deep HOMO level of 6.0 eV or more, a high triple energy (ET), and a hole stability.
  • the organic material layer may include a light emitting layer and an electron transporting layer
  • the electron transporting layer may include a compound represented by the general formula (1).
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • FIGS. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
  • the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.
  • the organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
  • the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials. When there are two or more organic layers, each layer may be formed as a component emitting light at different wavelengths. For example, one layer may be an organic light-emitting layer including a fluorescent dopant, And may be an organic light emitting layer containing a phosphorescent dopant.
  • each layer may be sequentially stacked between the anode and the cathode, and a functional layer may be optionally included between the organic layers.
  • the one organic layer may be formed of two different components, in which case a layer of two components may be divided into a single layer.
  • 3 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
  • the light emitting layer 3 is divided into two different portions 3-1 and 3-2, and the compound represented by Formula 1 may be included in one or both of the respective portions of the light emitting layer have.
  • Emitting layer, and the blue fluorescent light-emitting layer may be included in three or more layers.
  • the respective layers may be sequentially stacked between the anode and the cathode, and each blue fluorescent light-emitting layer may optionally include a functional layer therebetween.
  • the organic light emitting device according to the present invention can be manufactured by sequentially laminating a gate electrode, an organic material layer, and a system two electrode on a substrate.
  • a PVD (physi cal vapor deposition) method such as a sputtering method or an e-beam evaporation method is used to deposit a metal or a conductive metal oxide or an alloy thereof A hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a substance usable as a cathode is deposited thereon.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, coating, and the like, but is not limited thereto.
  • an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is a cathode.
  • hole injection can be smoothly performed A material having a large work function is preferable.
  • the positive electrode material 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), and indium zinc oxide (IZO); ⁇ : ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, no.
  • the negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO 2 / Al, but the present invention is not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable.
  • the HOMO highest occupied mole ar orbital of the hole injecting material is between the work function of the anode material and H0M0 of the surrounding organic layer.
  • the hole injecting material include a metal porphyrin, a thiophene, an organic material of an arylamine series, an organic material of a quinacridone series, a quinacridone series organic material, a perylene perylene based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for transporting holes from the hole injection layer to the light emitting layer, and is a layer for transporting holes from the anode or the hole injection layer
  • a material having high mobility to holes is suitable as a material capable of transporting holes to the light emitting layer.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • splittable material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherane having an arylamino group.
  • styrylamine compound include substituted or unsubstituted As the compound in which at least one aryl vinyl group is substituted with an arylamine, one or two unsubstituted substituents are substituted or unsubstituted in the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group.
  • the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds, and hydroxyflavone-metal complexes, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, Bis (2-methyl-8-quinolinato) (0-cresolato) gallium, bis (10-hydroxybenzo [h] quinolinato) (2-methyl-8-quinolinato) (1-naphthalato) aluminum, bis (2-methyl-8-quinolinato) (2-naphthalato) gallium and the like. .
  • the organic light emitting device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • the preparation of the compound represented by the formula (1) of the present invention and the organic light emitting device including the compound represented by formula (1) will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • 1-C-9 (1-B-1) was prepared in the same manner as in Example 1, except that trimethylsilylquinazoline was used instead of triazinecarbazole 10 g, yield 60%).
  • ITO indium tin oxide
  • Hexanitrile hexaazatrhenylane was thermally vacuum deposited to a thickness of 500 A on the ⁇ key transparent electrode thus prepared to form a hole injection layer.
  • HTK400 A was vacuum deposited on the hole transport material, and host HI and dopant D1 compound were vacuum deposited to a thickness of 300 A as a light emitting layer.
  • (1-B-1 and LiQ Lithium Quinolate) prepared in Preparation Example 1 were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 A.
  • Lithium fluoride (LiF) and aluminum having a thickness of 2,000 A were sequentially deposited on the electron injection and transport layer to a thickness of 12 A to form a cathode. Thereby preparing an organic light emitting device.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
  • the lithium fluoride at the cathode was maintained at 0.3 A / sec
  • the deposition rate of aluminum was maintained at 2 A / sec. "7 - holding a 5 xlO- 6 torr, was produced in the organic light emitting device.
  • An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of the compound represented by Formula 1-B-1 as the electron transporting layer in Example 1.
  • the compounds according to the invention have a core structure and only one side of triazine (or Pyrimidine) as compared with the comparative examples using a compound having a symmetric structure, it was confirmed that since the crystallinity was low, a dense film quality was formed at the time of film formation and the lifetime improvement effect was remarkably improved.
  • substrate 2 anode

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

Abstract

La présente invention porte sur un nouveau composé hétérocyclique et sur un dispositif électroluminescent organique l'utilisant.
PCT/KR2018/006166 2017-06-29 2018-05-30 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant WO2019004612A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US16/625,589 US11542258B2 (en) 2017-06-29 2018-05-30 Heterocyclic compound and organic light emitting device comprising the same
CN201880040226.0A CN110753687B (zh) 2017-06-29 2018-05-30 新的杂环化合物和包含其的有机发光器件

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KR20170082779 2017-06-29
KR10-2017-0082779 2017-06-29
KR1020180059817A KR102106121B1 (ko) 2017-06-29 2018-05-25 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR10-2018-0059817 2018-05-25

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020116615A1 (fr) * 2018-12-07 2020-06-11 出光興産株式会社 Nouveau composé et élément électroluminescent organique l'utilisant
WO2021033730A1 (fr) * 2019-08-19 2021-02-25 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2024144212A1 (fr) * 2022-12-27 2024-07-04 솔루스첨단소재 주식회사 Composé organique et dispositif électroluminescent organique l'utilisant

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CN101440082A (zh) * 2008-12-12 2009-05-27 南京邮电大学 螺芴氧杂蒽材料及其制备和应用方法
JP2009191232A (ja) * 2008-02-18 2009-08-27 Toppan Printing Co Ltd 蛍光性化合物、発光性インク組成物および有機ｅｌ素子
US20150115241A1 (en) * 2012-04-02 2015-04-30 Novaled Gmbh Use of a Semiconducting Compound in an Organic Light Emitting Device
KR101593368B1 (ko) * 2015-04-22 2016-02-11 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20170032414A (ko) * 2014-07-21 2017-03-22 메르크 파텐트 게엠베하 전자 소자용 재료
KR101742436B1 (ko) * 2015-12-15 2017-05-31 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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JP2009191232A (ja) * 2008-02-18 2009-08-27 Toppan Printing Co Ltd 蛍光性化合物、発光性インク組成物および有機ｅｌ素子
CN101440082A (zh) * 2008-12-12 2009-05-27 南京邮电大学 螺芴氧杂蒽材料及其制备和应用方法
US20150115241A1 (en) * 2012-04-02 2015-04-30 Novaled Gmbh Use of a Semiconducting Compound in an Organic Light Emitting Device
KR20170032414A (ko) * 2014-07-21 2017-03-22 메르크 파텐트 게엠베하 전자 소자용 재료
KR101593368B1 (ko) * 2015-04-22 2016-02-11 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR101742436B1 (ko) * 2015-12-15 2017-05-31 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020116615A1 (fr) * 2018-12-07 2020-06-11 出光興産株式会社 Nouveau composé et élément électroluminescent organique l'utilisant
WO2021033730A1 (fr) * 2019-08-19 2021-02-25 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2024144212A1 (fr) * 2022-12-27 2024-07-04 솔루스첨단소재 주식회사 Composé organique et dispositif électroluminescent organique l'utilisant

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