WO2020231242A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2020231242A1
WO2020231242A1 PCT/KR2020/095068 KR2020095068W WO2020231242A1 WO 2020231242 A1 WO2020231242 A1 WO 2020231242A1 KR 2020095068 W KR2020095068 W KR 2020095068W WO 2020231242 A1 WO2020231242 A1 WO 2020231242A1
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group
substituted
unsubstituted
light emitting
organic light
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차용범
김진주
홍성길
이우철
이성재
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주식회사 엘지화학
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Priority to CN202080015228.1A priority Critical patent/CN113454803B/zh
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Definitions

  • the present invention relates to an organic light-emitting device having a low driving voltage, high luminous efficiency, and excellent lifespan.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often made 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, and the like.
  • a voltage is applied between the two electrodes
  • holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to an organic light-emitting device having a low driving voltage, high luminous efficiency, and excellent lifespan.
  • the present invention provides the following organic light emitting device.
  • a negative electrode provided opposite to the positive electrode
  • a light emitting layer provided between the anode and the cathode
  • a hole transport region provided between the anode and the emission layer
  • the hole transport region includes a first compound represented by the following formula (1),
  • the emission layer includes a second compound represented by Formula 2 below,
  • L 1 to L 3 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,
  • Ar 1 is substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 1-60 haloalkoxy; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
  • a and b are each an integer of 0 to 9
  • L 4 and L 5 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; Or substituted or unsubstituted C 2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,
  • Ar 2 and Ar 3 are each independently a substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
  • R 3 is substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted carbazolyl; Substituted or unsubstituted dibenzofuranyl; Or substituted or unsubstituted dibenzothiophenyl.
  • the above-described organic light-emitting device may include a compound having a specific structure in each of the emission layer and the hole transport region, and thus exhibit low driving voltage, high luminous efficiency, and long lifespan characteristics.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 10, an anode 20, a hole transport region 30, an emission layer 40, an electron transport region 50, and a cathode 60.
  • the hole transport region 30 is an anode ( A hole injection layer 31, a hole transport layer 33, and an electron blocking layer 35 are sequentially stacked from 20), and the electron transport region 50 is a hole blocking layer 51 sequentially stacked from the light emitting layer 40. ), an example of an organic light-emitting device including an electron transport layer 53 and an electron injection layer 55 is shown.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an oxygen of the ester group 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.
  • 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 it 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 is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms 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, 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-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another 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-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, 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, or a terphenyl group, but the monocyclic aryl group is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a 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.
  • Etc When the fluorenyl group is substituted, Etc.
  • Etc it is not limited thereto.
  • heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole group, be
  • the aryl group among 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 aforementioned alkyl group.
  • heteroaryl among heteroarylamines the above-described description of heteroaryl may be applied.
  • the alkenyl group of 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 except that the arylene is a divalent group.
  • the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.
  • the present invention provides an organic light emitting device having the following structure:
  • a negative electrode provided opposite to the positive electrode
  • a light emitting layer provided between the anode and the cathode and including the second compound
  • a hole transport region provided between the anode and the emission layer and including the first compound
  • An electron transport region provided between the emission layer and the cathode.
  • the cathode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the cathode 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); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the organic light-emitting device includes a hole transport region for receiving holes from an anode provided between the anode and the emission layer and transporting holes to the emission layer, and the hole transport region includes the first compound represented by Formula 1 do.
  • the first compound has a tertiary amine structure substituted with two phenanthrene-9-yl groups, has excellent hole injection characteristics and characteristics of moving holes to the light emitting layer, and thus organic light emission in which the first compound is employed.
  • the device can exhibit a low driving voltage and high efficiency.
  • L 1 to L 3 may each independently be a single bond, or any one selected from the group consisting of:
  • X 1 is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
  • X 1 is O, S, N (phenyl), C (methyl) 2 , or C (phenyl) 2 .
  • L 1 to L 3 are each independently a single bond; Or any one selected from the group consisting of:
  • both L 1 and L 2 may not be single bonds.
  • L 1 is a single bond
  • L 2 is any one selected from the group consisting of
  • L 1 is any one selected from the group consisting of:
  • Ar 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, or spirobifluorenyl,
  • Ar 1 may be unsubstituted or substituted with 1 to 5 substituents each independently selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl.
  • Ar 1 is any one selected from the group consisting of:
  • a and b are each 0, 1 or 2.
  • the structures in parentheses are the same or different, respectively. More preferably, a and b are each 0 or 1.
  • R 1 and R 2 are the same as each other, and in this case, R 1 and R 2 may be both hydrogen or both may be phenyl.
  • the first compound is represented by the following formula 1-1:
  • L 1 to L 3 , Ar 1 , R 1 and R 2 are as defined in Chemical Formula 1.
  • the first compound may be prepared by the same method as in Scheme 1 below, when R 1 is the same as R 2 and a and b are the same as each other.
  • T is each independently halogen, preferably bromo or chloro, and the definition of other substituents is as described above.
  • the compound represented by Formula 1 is prepared by combining starting materials through a Suzuki coupling reaction.
  • a Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked from the anode.
  • the electron blocking layer is located in contact with the light emitting layer, and the first compound is included in the hole transport layer or the electron blocking layer. More preferably, the first compound is included in the electron blocking layer.
  • the hole injection layer is disposed on the anode and injects holes from the anode, and includes a hole injection material.
  • a hole injection material has the ability to transport holes, has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material.
  • a compound having excellent thin film formation ability is preferable.
  • the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene Organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is formed on the hole injection layer to receive holes from the hole injection layer and transport holes to the light emitting layer.
  • the hole transport layer includes a hole transport material, and a material having high mobility for holes capable of transporting holes from the anode or the hole injection layer and transferring them to the light emitting layer is suitable as the hole transport material.
  • the first compound represented by Formula 1 is used as the hole transport material.
  • an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion may be used as the hole transport material, but the present invention is not limited thereto.
  • the electron blocking layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby increasing the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device.
  • the electron blocking layer includes an electron blocking material, and a material having a stable structure in which electrons do not flow out of the emission layer is suitable as the electron blocking material.
  • the first compound represented by Formula 1 is used as the electron blocking material.
  • an arylamine-based organic material may be used as the electron blocking material, but is not limited thereto.
  • the organic light-emitting device includes an anthracene compound in which positions 2, 9, and 10, which are the second compound represented by Chemical Formula 2, are substituted as a host material.
  • the second compound has a structure in which the same or different substituents are introduced at positions 9 and 10 and a substituent is introduced at the second position, so that the material stability is higher than that of the compound in which the substituent is not introduced at the 2nd position. It is excellent and can contribute to the improvement of lifespan characteristics when used in organic light emitting devices.
  • L 4 and L 5 may each independently be a single bond, or any one selected from the group consisting of:
  • Y 1 is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
  • Y 1 is O, S, N (phenyl), C (methyl) 2 , or C (phenyl) 2 .
  • L 4 and L 5 are each independently a single bond or phenylene.
  • Ar 2 and Ar 3 are each independently C 6-20 aryl; Or C 2-60 heteroaryl including O or S.
  • Ar 2 and Ar 3 are each independently phenyl, biphenylyl, naphthyl, or dibenzofuranyl.
  • R 3 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,
  • R 3 is unsubstituted or by 1 to 5 substituents each independently selected from the group consisting of deuterium, C 1-10 alkyl, tri(C 1-4 alkyl) silyl and C 6-20 aryl Can be substituted.
  • R 3 is any one selected from the group consisting of:
  • Q is hydrogen, C 1-10 alkyl, Si(C 1-4 alkyl) 3 , or C 6-20 aryl,
  • Y 2 is O, S, N(C 6-20 aryl), C(C 1-4 alkyl) 2 , or C(C 6-20 aryl) 2 .
  • Q is hydrogen, tert-butyl, Si(methyl) 3 , phenyl, or naphthyl,
  • Y 2 is O, S, N (phenyl), C (methyl) 2 , or C (phenyl) 2 .
  • the second compound is represented by the following formula 2-1 or 2-2:
  • L 5 , Ar 3 and R 3 are as defined in Chemical Formula 2.
  • the second compound may be prepared by a manufacturing method as shown in Scheme 2 below, for example.
  • T is halogen, preferably bromo, or chloro, and the definition of other substituents is as described above.
  • the compound represented by Chemical Formula 2 is prepared by introducing an R 3 substituent into a starting material through a Suzuki coupling reaction.
  • a Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the emission layer may further include a dopant material.
  • the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • At least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the emission layer may include an iridium complex as a dopant material.
  • the organic light-emitting device including the emission layer including the host material and the dopant material described above may exhibit a maximum wavelength ⁇ max in the emission spectrum at about 400 nm to about 500 nm. Accordingly, the organic light-emitting device is a blue light-emitting organic light-emitting device.
  • the organic light-emitting device includes an electron transport region provided between the emission layer and the cathode.
  • the electron transport region is a region for transporting electrons from the cathode to the light emitting layer, and generally includes an electron transport layer.
  • the electron transport region includes a hole blocking layer and an electron transport layer sequentially stacked from the light emitting layer; Hole blocking layer and electron injection and transport layer; Or a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the hole blocking layer is formed on the emission layer, and specifically, the hole blocking layer is provided in contact with the emission layer to prevent excessive movement of holes, thereby increasing the probability of hole-electron bonding, thereby improving the efficiency of the organic light-emitting device. Do it.
  • the hole blocking layer includes a hole blocking material, and as such a hole blocking material, a material having a stable structure in which holes do not flow out of the emission layer is suitable.
  • the hole blocking material examples include azine derivatives including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is not limited thereto.
  • the electron transport layer is formed between the light emitting layer and the cathode, preferably between the hole blocking layer and an electron injection layer to be described later to receive electrons from the electron injection layer to transport electrons to the light emitting layer.
  • the electron transport layer includes an electron transport material, and the electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable.
  • the electron transport material include pyridine derivatives; Pyrimidine derivatives; Triazole derivatives; Triazine derivatives; Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer may include a metal complex compound together with the electron transport material.
  • the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. ,
  • the electron injection layer is located between the electron transport layer and the cathode, and serves to inject electrons from the cathode.
  • the electron injection layer includes an electron injection material, and a material having excellent electron injection effect with respect to the light-emitting layer or the light-emitting material while having the ability to transport electrons and having excellent thin film formation ability is suitable as the electron injection material.
  • the electron injection material include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, Derivatives thereof, such as perylene tetracarboxylic acid, preorenylidene methane, anthrone, and the like, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • FIGS. 1 and 2 The structure of the organic light emitting device according to the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 10, an anode 20, a hole transport region 30, an emission layer 40, an electron transport region 50, and a cathode 60.
  • the first compound may be included in the hole transport region 30 and the second compound may be included in the emission layer 40.
  • the second compound is composed of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50 and a cathode 60
  • the hole transport region 30 is an anode
  • a hole injection layer 31, a hole transport layer 33, and an electron blocking layer 35 are sequentially stacked from 20
  • the electron transport region 50 is a hole blocking layer 51 sequentially stacked from the light emitting layer 40.
  • an organic light-emitting device including an electron transport layer 53 and an electron injection layer 55 is shown.
  • the first compound may be included in the hole transport layer 33 or the electron blocking layer 35
  • the second compound may be included in the emission layer 40, respectively.
  • the organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configurations. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming each of the above-described layers thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, 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.
  • PVD physical vapor deposition
  • the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray 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 from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a compound of the following compound HI-1 and the following compound HI-2 was thermally vacuum deposited to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) to form a hole injection layer.
  • HT-1 (1150 ⁇ ), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.
  • compound 1-1 prepared in Preparation Example 1 with a film thickness of 50 ⁇ was vacuum deposited on the hole transport layer to form an electron blocking layer.
  • a light emitting layer was formed by vacuum depositing the compound 2-1 (host) prepared in Preparation Example 4 and the compound BD-1 (dopant) below at a weight ratio of 40:1 on the electron blocking layer with a film thickness of 200 ⁇ .
  • Compound HB-1 was vacuum-deposited on the emission layer with a thickness of 50 ⁇ to form a hole blocking layer.
  • the following compound ET-1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron transport layer having a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 2,000 ⁇ were sequentially deposited on the electron transport layer to form an electron injection layer and a negative electrode, respectively.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec, the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec, and the deposition rate of aluminum was 2 ⁇ /sec, and the vacuum degree during deposition was 2 x10 -7 by keeping the ⁇ 5 x10- 6 torr, it was produced in the organic light emitting device.
  • Example 1 The compound used in Example 1 is as follows.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of the host compound 2-1 and the electron blocking layer compound 1-1 in Example 1.
  • the compounds used in Examples and Comparative Examples are as follows.
  • T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • the organic light-emitting device of the embodiment in which the compound represented by Formula 1 is used as an electron blocking layer material and the compound represented by Formula 2 is used as the host material of the emission layer at the same time the formulas 1 and 2 Compared to the organic light-emitting device of Comparative Example in which only one of the compounds represented by or neither is used, excellent characteristics are exhibited in terms of driving voltage, luminous efficiency and lifetime.
  • the compound represented by Formula 1 is a compound EB-1 and two phenanthrenyls in which positions 1, 2 and 4 of the triphenylenyl group are substituted with a phenyl group.
  • the hole injection property and the property of moving holes to the light emitting layer are superior, thus contributing to the improvement of the efficiency of the device.
  • Comparative Examples 4 to 7 Comparative Examples 9 and 10
  • the compound represented by Chemical Formula 2 is material stability compared to Comparative Examples Compounds BH-1 and BH-2 which do not have a substituent at the anthracene position 2 It can be seen that this is excellent and contributes to the long life characteristics of the device.
  • the organic light emitting device of the embodiment according to the present invention employing both the compound and the compound represented by Chemical Formula 2 improves efficiency and lifetime characteristics at the same time.
  • the organic light-emitting device employing a combination of the compounds of the present invention has significantly improved device characteristics compared to the comparative example device. It can be seen that it represents.
  • substrate 20 anode

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Abstract

La présente invention concerne un élément électroluminescent organique comprenant une électrode positive ; une électrode négative disposée à l'opposé de l'électrode positive ; une couche électroluminescente disposée entre l'électrode positive et l'électrode négative ; une région de transport d'électrons disposée entre l'électrode positive et la couche électroluminescente ; et une région de transport de trous disposée entre la couche électroluminescente et l'électrode négative, la région de transport de trous comprenant un premier composé contenant un groupe amine tertiaire, et la couche électroluminescente comprenant un second composé contenant un groupe phénanthrényle.
PCT/KR2020/095068 2019-05-10 2020-04-14 Élément électroluminescent organique WO2020231242A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060050915A (ko) * 2004-09-02 2006-05-19 주식회사 엘지화학 안트라센 유도체 및 이를 발광 물질로서 이용한 유기 발광소자
KR20100110725A (ko) * 2009-04-03 2010-10-13 소니 주식회사 유기 전계 발광 소자 및 표시 장치
US20110024736A1 (en) * 2008-04-03 2011-02-03 Sony Corporation Organic electroluminescent element and display
KR20110034977A (ko) * 2009-09-29 2011-04-06 에스에프씨 주식회사 방향족 화합물 및 이를 이용한 유기전계발광소자
KR20150030659A (ko) * 2012-06-12 2015-03-20 소니 주식회사 유기 전계발광 소자 및 표시장치

Family Cites Families (8)

* 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
KR102098221B1 (ko) * 2017-02-24 2020-04-07 주식회사 엘지화학 유기 발광 소자
KR102109075B1 (ko) * 2017-02-24 2020-05-11 주식회사 엘지화학 유기 발광 소자
KR102331322B1 (ko) * 2017-03-08 2021-11-24 주식회사 엘지화학 유기 발광 소자
KR102053325B1 (ko) * 2017-03-09 2019-12-06 주식회사 엘지화학 유기 발광 소자
KR102022689B1 (ko) * 2017-03-30 2019-09-18 주식회사 엘지화학 유기 발광 소자
KR102138410B1 (ko) * 2017-06-30 2020-07-27 주식회사 엘지화학 유기 발광 소자
KR102550505B1 (ko) * 2017-08-01 2023-07-04 삼성디스플레이 주식회사 모노아민 화합물 및 이를 포함하는 유기 전계 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060050915A (ko) * 2004-09-02 2006-05-19 주식회사 엘지화학 안트라센 유도체 및 이를 발광 물질로서 이용한 유기 발광소자
US20110024736A1 (en) * 2008-04-03 2011-02-03 Sony Corporation Organic electroluminescent element and display
KR20100110725A (ko) * 2009-04-03 2010-10-13 소니 주식회사 유기 전계 발광 소자 및 표시 장치
KR20110034977A (ko) * 2009-09-29 2011-04-06 에스에프씨 주식회사 방향족 화합물 및 이를 이용한 유기전계발광소자
KR20150030659A (ko) * 2012-06-12 2015-03-20 소니 주식회사 유기 전계발광 소자 및 표시장치

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