WO2018117369A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2018117369A1
WO2018117369A1 PCT/KR2017/009096 KR2017009096W WO2018117369A1 WO 2018117369 A1 WO2018117369 A1 WO 2018117369A1 KR 2017009096 W KR2017009096 W KR 2017009096W WO 2018117369 A1 WO2018117369 A1 WO 2018117369A1
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unsubstituted
substituted
light emitting
group
organic light
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PCT/KR2017/009096
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Korean (ko)
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천민승
이우철
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주식회사 엘지화학
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Priority to CN201780002448.9A priority Critical patent/CN108463535B/zh
Publication of WO2018117369A1 publication Critical patent/WO2018117369A1/fr

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    • HELECTRICITY
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    • H10K50/00Organic light-emitting devices
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    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C09K11/025Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018Heterocyclic compounds
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018Heterocyclic compounds
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
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    • H10K2101/00Properties of the organic materials covered by group H10K85/00
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have 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 layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the light emitting layer of the organic light emitting device is composed of a light emitting dopant material which actually emits light with one or more host materials.
  • the emission spectrum exhibits a unique emission spectrum for each of the materials of the light emitting dopant, a spectrum shift occurs due to the kind or combination of host materials to be used, and thus a desired color is often not obtained. Accordingly, in the organic light emitting device using the color filter, the light filter does not meet the light transmission range of the color filter, resulting in a problem in that the efficiency is reduced. In addition, even in the organic light emitting device that does not use a color filter, a color different from the color of the actually intended light emitting dopant is generated, causing problems in color or luminance. Accordingly, the present inventors confirmed the present invention by identifying an organic light emitting device that can solve the above problems as described below.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826 ' ⁇ Contents of the Invention ⁇
  • the present invention is to provide an organic light emitting device without distortion of the emission spectrum.
  • the present invention is an anode; cathode; And a light emitting layer between the anode and the cathode, wherein the light emitting layer includes a compound having a dipole moment value of 4.5 or less as a first host.
  • the organic light emitting device can provide an organic light emitting device without distortion of the emission spectrum by using a material of a host and a dopant satisfying a specific dipole moment value.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4.
  • FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4.
  • An example of the organic light emitting element made is shown.
  • the term "substituted or unsubstituted" is deuterium; halogen; nitrile; nitro, hydroxy, carbonyl; ester, imide; amino; phosphine oxide; alkoxy; aryloxy; Alkylthioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkyl An amine group; heteroarylamine group; arylamine group; arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, 0 and S atoms, Substituted or two unsubstituted or two unsubstituted.
  • the compound may have a structure as follows.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms may be a compound of the following structural formula,
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is 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 boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, micropropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl 1-methyl-butyl, 1-ethyl-butyl, pentyl, n- Pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2 ⁇ prop
  • the alkenyl number may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Another one According to an exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • 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-hexyl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In a according to an embodiment of 'the number of carbon atoms of the cycloalkyl group has from 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • 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.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the 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 including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic groups include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group and triazole group.
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that the two substituents are bonded to each other.
  • the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the present invention the anode; cathode; And a light emitting insect between the anode and the cathode, wherein the light emitting layer includes, as a host, a compound having a dipole moment value of 4.5 or less as a host.
  • the shift of the emission spectrum of the dopant may occur depending on the type or combination of hosts included in the light emitting layer of the organic light emitting element. This is due to the solid state solvation effect (sol id state solvat ion ef fect) generated by the dipole moment of the host, and fails to obtain the intended emission spectrum, causing problems such as defects and reduced efficiency.
  • the present invention is characterized in that a compound having a dipole moment value of 4.5 or less is used as a host of the light emitting layer so that the shift of the emission spectrum of the light emitting layer of the organic light emitting device is minimized.
  • dipole moment means a physical quantity indicating the degree of polarity, and may be calculated as in Equation 3 below.
  • the molecular density (molecular densi ty) can be obtained by calculation, and the value of the dipole moment can be obtained.
  • the molecular density can be obtained by calculating charges and dipoles for each atom using the Hirshfeld Charge Analysis method, and calculating them according to the following equation, and the dipole moment ( Dipole Moment).
  • the light emitting layer comprises a light emitting dopant
  • the host and the light emitting dopant satisfy the following Equation 1:
  • DM host and DM (light emitting dopant) are the dipole moment values of the host and the light emitting dopant, respectively,
  • fh means the weight of the host divided by the total weight of the host and the light emitting dopant
  • the light emitting layer includes n different materials, wherein n is an integer of 2 or more, at least one of the n materials is a light emitting dopant, and the n materials satisfy the following Equation 2. do:
  • Ai denotes the weight of each substance divided by the total weight of the n substances.
  • n is 2, 3, or 4. That is, the light emitting layer of the organic light emitting device according to the present invention, the dipole moment value is
  • the compounds having 4.5 or less may include compounds having a dipole moment value of more than 4.5, but the total dipole moment value should be 4.5 or less depending on their concentration.
  • a compound having a dipole moment value of 4.5 or less may be used, and for example, a compound represented by the following Chemical Formula 1, or a compound represented by the following Chemical Formula 2 may be used:
  • Ar n and 12 are, each independently, a substituted or unsubstituted C 6 - C 2 containing 60 aryl, or a substituted or unsubstituted one or more heteroatoms selected from the group consisting of unsubstituted N eu 0 and S - 60 Heteroaryl,
  • Ln and L 12 are each independently a single bond or a substituted or unsubstituted
  • 3 ⁇ 4 is each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; C HO haloalkyl; Substituted or unsubstituted
  • h and i are each independently 1 or 2
  • X is an integer from 0 to 8
  • Ar 2 i, Ar 22 and Ar 23 each independently include one or more heteroatoms selected from the group consisting of substituted or unsubstituted C 6 60 aryl, or substituted or unsubstituted N, 0 and 3 60 is a heteroaryl, - C 2
  • L 21 , L 22 and L 23 are each independently a single bond or a substituted or unsubstituted C 6 -60 arylene,
  • 3 ⁇ 4 is each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted alkyl; Substituted or unsubstituted haloalkyl; Substituted or unsubstituted d— 60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; A substituted or unsubstituted C 2 -60 alkenyl group; Substituted or unsubstituted C 6 -60 aryloxy; Substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted amines; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C 2 -60 heterocyclic group containing at least one of 0, N, Si and S,
  • n, n and 0 are each independently 1 or 2
  • the light-emitting insect includes both the compound represented by Formula 1 and the compound represented by Formula 2 as a host.
  • the compound represented by Chemical Formula 1 has an anthracene structure, and is characterized by having a small dipole moment value by replacing an aromatic ring or a heteroaromatic ring at positions 9 and 10 of anthracene.
  • Ar u and 12 are each independently phenyl , naphthyl Biphenylyl, or a group consisting of: wherein Ar u and ⁇ 12 are unsubstituted:
  • L u and L 12 are each independently a single bond, phenylene, naphthylene, anthracenylene, or thiophenylene.
  • the compound represented by Formula 1 is any one compound selected from the group consisting of:
  • the production method is a reaction for introducing a substituent into No. 9 or No. 10 of anthracene as a Suzuki coupling reaction, which may be more specific in the production examples described later.
  • the compound represented by Chemical Formula 2 has an anthracene structure, an aromatic ring or a heteroaromatic ring is substituted at positions 1 and 8 of the anthracene, and an aromatic ring or heteroaromatic ring is substituted at the position 10, thereby reducing a small dipole moment value.
  • Ar 21 , Ar 22 and Ar 23 are each independently selected from phenyl, dimethylphenyl, naphthyl, biphenylrin, terphenyl, or a group consisting of:
  • 3 ⁇ 4 is S, 0, N (R 3 ), or C (R4) (R 5 )
  • 3 ⁇ 4 are, each independently, a substituted or non-substituted d-60 alkyl, substituted or unsubstituted C 6 unsubstituted - 60 aryl, or R4 and together are a substituted or unsubstituted Forms C 6 -60 aryl.
  • Ar 21 and ⁇ 22 are the same as each other.
  • L 21 , L 22 and L 23 are each independently a single bond, phenylene, or naphthylenyl.
  • the compound represented by Formula 2 is any one compound selected from the group consisting of:
  • the compound represented by Chemical Formula 2 may be prepared by the same method as in Banung Formula 2.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ⁇ : ⁇ 1 or SN0 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 KPED0T), polypyri and polyaniline, and the like, but are not limited thereto.
  • As the negative electrode material an electron is easily injected 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 Li0 2 / Al, and the like, but are not limited thereto.
  • Hole injection layer includes 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 Li0 2 / Al, and the like, but are not limited thereto.
  • the organic light emitting device may include a hole injection layer for injecting holes from the electrode.
  • the hole injection material it has the ability to transport holes, has an effect of hole injection at the anode, excellent hole injection effect on the light emitting layer or light emitting material, and prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material.
  • the compound excellent in the thin film formation ability is preferable. It is preferable that the HOMCKhighest occupied molecular orbital of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • hole injecting materials include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • Hole transport layer includes metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the organic light emitting device may include a hole transport layer that receives holes from an anode or a hole injection layer and transports holes to the light emitting layer.
  • a material for transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material a material having high mobility to holes is suitable.
  • 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 layer of the organic light emitting device according to the present invention may include a dopant in addition to the host described above.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • aromatic amine derivative a condensed aromatic ring having a substituted or unsubstituted arylamino group
  • the derivative examples include pyrene, anthracene, chrysene and periplanthene having an arylamino group
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine.
  • Substituents which are selected from 1 or 2 ′ or more from the group consisting of silyl groups, alkyl groups, cycloalkyl groups and arylamino groups are substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the compound represented by the following Formula 3 may be used as the dopant:
  • Ri to 3 ⁇ 4 are each independently hydrogen, halogen, substituted or unsubstituted
  • An to Ar 4 are each independently a substituted or unsubstituted C 6 - C 2 containing 30 aryl or a substituted or unsubstituted 0, N, Si and S 1 out of more than 60 heterocyclic contribution, provided that, A to At least one of Ar 4 is represented by the following general formula (4):
  • X is 0 or S
  • R 9 and R 10 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d- 60 haloalkyl; Substituted or unsubstituted alkoxy; Substituted or unsubstituted d- 60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted C 2 -60 alkenyl; Substituted or unsubstituted C 6 — eo aryloxy; Substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted amines; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C 2 -60 heterocyclic group containing at least one of
  • the organic light emitting device may include an electron transport layer that receives electrons from a cathode or an electron injection layer and transports electrons to the light emitting layer.
  • an electron transport layer that receives electrons from a cathode or an electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples 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.
  • 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 an aluminum or silver layer in each case.
  • Electron injection layer is conventional materials having a low work function followed by an aluminum or silver layer— specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum or silver layer in each case.
  • the organic light emitting device may include an electron injection layer for injecting electrons from an electrode.
  • the electron injection material has the ability to transport electrons, has the effect of electron injection from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, prevents the excitation of the excitons generated in the light emitting layer to the hole injection layer, and
  • the compound which is excellent in thin film formation ability is preferable.
  • polonorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, Perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal complex compounds and 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) ( Ecrezolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl ⁇ 8-quinolinato) (2-naprlato) gallium Or not limited thereto.
  • Organic light emitting device examples include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tri
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, and a cathode 4.
  • FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4.
  • An example of an organic light emitting device is shown.
  • the organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configuration. At this time, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporat ion.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the light emitting layer may be formed of a host and a dopant not only by vacuum deposition but also by solution coating.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the organic light emitting device according to the invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited thereto.
  • reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distillation under reduced pressure, and recrystallized with Tol (luluene) / EA (ethyl acetate) to prepare a compound (12.8 g). , 93%) was prepared.
  • Example 1-18 A compound was prepared.
  • step 2 of Preparation Example 2-1 naphthalene—1 yl ylbonmic acid was used instead of di benzo [b, d] fur an-4-ylboronic acid. ”In step 4, di benzo [instead of naphthalene-1- ylboronic acid. b, d] f ur an-4-y 1 bor on ic acid, to prepare a compound of Preparation Example 2-2.
  • Step 4 of Preparation Example 2-1 compound of Preparation Example 2-3 was prepared by using d i benzo [b, d] f ur an-4-y 1 bor on i c acid instead of naphthalene—1-ylboronic acid.
  • step 4 of Preparation Example 2-1 a compound of Preparation Example 2-10 was prepared using naphthalene—1-ylboronic acid phenylboronic acid.
  • step 2 of Preparation Example 2-1 napht ha 1 ene- 1-y 1 bor on ic acid was used instead of dibenzo [b, d] fur n-4-ylboronic acid, and naphtha 1 ene- (1,1'-biphenyl) 2-ylboronic acid was used instead of 1-ylboronic acid to prepare Preparation Example 2-46.
  • step 2 of Preparation Example 2-1 instead of dibenzo [b, d] f ur an-4-ylboroni c acid, (3, 5-dimethy 1 pheny 1) bor on ic acid was used, and in step 4 napht pheny lboronic acid was used instead of ha 1 ene-1 ylboronic acid to prepare Preparation Example 2—47.
  • Step 2 of Preparation Example 2-1 naphthalene-l-ylboronic acid was used instead of dibenzo [b, d] fur an-4-y lboronic acid to prepare Preparation Example 2-50.
  • MS [M + ] found 556.63, calc. 556.22
  • Step 2 of Preparation Example 2-1 instead of dibenzo [b, d] furan-4-ylboronic acid (9, 9-di pheny 1 -9H-f 1 uor en-4-y 1) bor on ic acid
  • step 4 pheny 1 bor on ic acid was used instead of naphthalene-l-ylboronic acid, to prepare Preparation Example 2-51.
  • Step 2 of Preparation Example 2-1 instead of dibenzo [b, d] f uran-4-ylboroni c acid (9, 9-di pheny 1 -9H- f 1 uor en-4-y 1) bor on ic acid
  • dibenzo [b, d] furan I 4 ⁇ ylboronic acid was used to prepare a compound of Preparation Example 2-52.
  • a glass substrate coated with a thin film having an indium tin oxide (ITO) of 150 nm was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, and drying Transported.
  • the substrate was cleaned for 5 minutes using nitrogen plasma, and then the substrate was transferred to a vacuum evaporator.
  • HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm on the prepared IT0 transparent electrode to form a hole injection layer.
  • HTL1 was thermally vacuum deposited to a thickness of 100 nm
  • HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer.
  • BH1 as a host and BD (weight ratio 95: 5) as a dopant were simultaneously vacuum deposited to form a light emitting layer having a thickness of 20 nm.
  • ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer.
  • LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer.
  • aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting device.
  • the organic light emitting device was manufactured by the same method as Example 1, but using the material and the content of the following Table 1 and 2 as the host and the dopant. 1-13, 2-1, etc., corresponding to the materials of Tables 1 and 2 below, mean that the compounds prepared in each preparation example are used, and the total EML of DM is obtained by multiplying the content of the dipole moment of each host and dopant by the content. Calculated in total.
  • Example 57 1-38 0,07 0.200 2-47 1,12 0.150 BH3 4,92 m 0.68 DM 3.i? Examples 5S 1-3 $ 0.33 2-48 1.40 0.050 BH4 5.15 0,300 0.68 0.05 1.85 Example 59 1-43 0.12 0.800 2-49 1.18 0,050 BH5 5.57 O.D.
  • the total light emitting layer DM of Example 1 and Example 2 was 0.09 and 4.47, respectively, and the total light emitting layer DM of Comparative Example 1 was 4.93.
  • the peak max positions of the spectra are 458 nm, 464 nm, and 476 nm in the order of Example 1, Example 2, and Comparative Example 1, respectively. Moving toward longer wavelengths, the FWHM increases rapidly when the dipole moment of the host exceeds 4.5.
  • Examples 1, 2 and Comparative Example 1 are (0.137, 0.092), (0.131, 0.152) and (0.156, 0.22), respectively. )
  • the dipole moment value of the host exceeds 4.5, the spectrum shifts to longer wavelengths and the color purity rapidly deteriorates due to the increase in FWHM.
  • Substrate 2 Anode

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Abstract

La présente invention concerne un élément électroluminescent organique n'ayant pas de distorsion d'un spectre d'émission.
PCT/KR2017/009096 2016-12-20 2017-08-21 Élément électroluminescent organique WO2018117369A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020075759A1 (fr) * 2018-10-09 2020-04-16 出光興産株式会社 Élément électroluminescent organique et dispositif électronique l'utilisant
WO2020209293A1 (fr) * 2019-04-08 2020-10-15 出光興産株式会社 Élément électroluminescent organique et dispositif électronique le comprenant
WO2020209292A1 (fr) * 2019-04-08 2020-10-15 出光興産株式会社 Élément électroluminescent organique et appareil électronique équipé de celui-ci
CN112996779A (zh) * 2019-02-20 2021-06-18 株式会社Lg化学 蒽衍生物和使用其的有机电子器件
US20220013737A1 (en) * 2018-11-05 2022-01-13 Samsung Display Co., Ltd. Organic light-emitting device
WO2022163626A1 (fr) * 2021-01-26 2022-08-04 出光興産株式会社 Composition, poudre, élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique et dispositif électronique

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200373496A1 (en) * 2017-09-19 2020-11-26 Lg Chem, Ltd. Organic light emitting element
CN108997345B (zh) * 2018-08-20 2024-08-02 上海弗屈尔光电科技有限公司 一种氮杂螺环化合物及含有该化合物的有机光电器件
KR102299734B1 (ko) 2018-10-16 2021-09-09 주식회사 엘지화학 유기 화합물 및 이를 포함하는 유기 발광 소자
WO2020209299A1 (fr) * 2019-04-08 2020-10-15 出光興産株式会社 Élément électroluminescent organique, et dispositif électronique le comprenant
CN113631543A (zh) 2019-04-08 2021-11-09 出光兴产株式会社 有机电致发光元件和使用其的电子设备
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EP3998322B1 (fr) * 2019-12-26 2024-04-17 Idemitsu Kosan Co., Ltd. Élément électroluminescent organique, composition, poudre, équipement électronique et nouveau composé
CN113666929B (zh) * 2021-09-08 2023-04-07 南京高光半导体材料有限公司 一种含有咔唑芴类螺环化合物及有机电致发光器件
CN115611873A (zh) * 2022-12-20 2023-01-17 吉林省元合电子材料有限公司 一种含有苯并咪唑和蒽结合结构的有机光电功能材料及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020059256A (ko) * 2001-01-02 2002-07-12 로버트 디. 크루그 개선된 휘도 효율을 갖는 유기 발광 다이오드 장치
KR20060121288A (ko) * 2004-01-08 2006-11-28 이스트맨 코닥 캄파니 아미노안트라센을 사용한 안정한 유기 발광 디바이스
KR20140121123A (ko) * 2013-04-05 2014-10-15 에스에프씨 주식회사 헤테로아릴기를 포함하는 아민기가 치환된 비대칭 피렌 유도체 및 이를 포함하는 유기 발광 소자
KR20160049500A (ko) * 2014-10-27 2016-05-09 주식회사 엘지화학 유기 전계 발광 소자
KR20160052526A (ko) * 2013-09-06 2016-05-12 이데미쓰 고산 가부시키가이샤 안트라센 유도체 및 그것을 사용한 유기 전계 발광 소자
US9437833B2 (en) * 2011-08-30 2016-09-06 Konica Minolta, Inc. Organic electroluminescence element

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법
JP4984891B2 (ja) * 2004-07-02 2012-07-25 Jnc株式会社 発光材料およびこれを用いた有機電界発光素子
KR101115255B1 (ko) * 2008-07-11 2012-02-15 주식회사 엘지화학 신규한 안트라센 유도체 및 이를 이용한 유기전자소자
US8431250B2 (en) * 2009-04-24 2013-04-30 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
KR20120135501A (ko) * 2012-10-29 2012-12-14 에스에프씨 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
US9947879B2 (en) * 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
KR102316683B1 (ko) * 2015-01-21 2021-10-26 삼성디스플레이 주식회사 유기 발광 소자
KR102100008B1 (ko) * 2016-04-12 2020-04-10 주식회사 엘지화학 안트라센계 화합물 및 이를 포함하는 유기 발광 소자
KR101869657B1 (ko) * 2016-08-09 2018-06-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기전계 발광 소자
KR101899728B1 (ko) * 2016-09-07 2018-09-17 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020059256A (ko) * 2001-01-02 2002-07-12 로버트 디. 크루그 개선된 휘도 효율을 갖는 유기 발광 다이오드 장치
KR20060121288A (ko) * 2004-01-08 2006-11-28 이스트맨 코닥 캄파니 아미노안트라센을 사용한 안정한 유기 발광 디바이스
US9437833B2 (en) * 2011-08-30 2016-09-06 Konica Minolta, Inc. Organic electroluminescence element
KR20140121123A (ko) * 2013-04-05 2014-10-15 에스에프씨 주식회사 헤테로아릴기를 포함하는 아민기가 치환된 비대칭 피렌 유도체 및 이를 포함하는 유기 발광 소자
KR20160052526A (ko) * 2013-09-06 2016-05-12 이데미쓰 고산 가부시키가이샤 안트라센 유도체 및 그것을 사용한 유기 전계 발광 소자
KR20160049500A (ko) * 2014-10-27 2016-05-09 주식회사 엘지화학 유기 전계 발광 소자

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020075759A1 (fr) * 2018-10-09 2020-04-16 出光興産株式会社 Élément électroluminescent organique et dispositif électronique l'utilisant
US20220013737A1 (en) * 2018-11-05 2022-01-13 Samsung Display Co., Ltd. Organic light-emitting device
CN112996779A (zh) * 2019-02-20 2021-06-18 株式会社Lg化学 蒽衍生物和使用其的有机电子器件
CN112996779B (zh) * 2019-02-20 2024-08-02 株式会社Lg化学 蒽衍生物和使用其的有机电子器件
WO2020209293A1 (fr) * 2019-04-08 2020-10-15 出光興産株式会社 Élément électroluminescent organique et dispositif électronique le comprenant
WO2020209292A1 (fr) * 2019-04-08 2020-10-15 出光興産株式会社 Élément électroluminescent organique et appareil électronique équipé de celui-ci
WO2022163626A1 (fr) * 2021-01-26 2022-08-04 出光興産株式会社 Composition, poudre, élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique et dispositif électronique

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