WO2020190116A1 - Diode électroluminescente organique - Google Patents

Diode électroluminescente organique Download PDF

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WO2020190116A1
WO2020190116A1 PCT/KR2020/095039 KR2020095039W WO2020190116A1 WO 2020190116 A1 WO2020190116 A1 WO 2020190116A1 KR 2020095039 W KR2020095039 W KR 2020095039W WO 2020190116 A1 WO2020190116 A1 WO 2020190116A1
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김민준
이동훈
서상덕
김동희
김서연
이다정
최승원
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주식회사 엘지화학
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Priority claimed from KR1020200030989A external-priority patent/KR102311643B1/ko
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Priority to CN202080005872.0A priority Critical patent/CN113056831A/zh
Publication of WO2020190116A1 publication Critical patent/WO2020190116A1/fr

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    • 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

  • 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 second electrode provided to face the first electrode
  • the emission layer includes a first compound represented by Formula 1 below and a second compound represented by Formula 2 below,
  • X 1 to X 3 are each independently N or CH, but at least two of X 1 to X 3 are N,
  • Ar 1 and Ar 2 are each independently deuterium; 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,
  • Z is each independently hydrogen, or deuterium, or two adjacent ones of Z are bonded to each other to include a C 6-60 aromatic ring or any one or more heteroatoms selected from the group consisting of N, O and S Can form 2-60 heteroaromatic rings,
  • the C 6-60 aromatic ring and the C 2-60 heteroaromatic ring are unsubstituted or substituted with deuterium,
  • n is an integer from 0 to 6
  • A is a substituent represented by the following formula 1-1,
  • R 1 to R 4 are each independently hydrogen or deuterium, or two adjacent ones of R 1 to R 4 are bonded to each other to form a C 6-60 aromatic ring or any one selected from the group consisting of N, O and S Can form a C 2-60 heteroaromatic ring containing more than one heteroatom
  • the C 6-60 aromatic ring and the C 2-60 heteroaromatic ring are unsubstituted or substituted with deuterium,
  • n is an integer from 0 to 6
  • T 1 to T 4 are each independently a substituted or unsubstituted C 6-60 aromatic ring fused with a neighboring pentagonal ring; Or a substituted or unsubstituted C 2-60 heteroaromatic ring containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • L 1 and L 2 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 3 and Ar 4 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.
  • the organic light-emitting device described above may simultaneously include the first compound and the second compound as a host material in the emission layer, thereby exhibiting low driving voltage, high luminous efficiency, and long lifespan characteristics.
  • 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 cathode 4 shows an example of an organic light emitting device.
  • 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 trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron 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, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhex
  • 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 heterogeneous elements, and the number of carbons is not particularly limited, but it 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, benzo
  • aromatic ring refers to condensation having a plurality of aromatics such as a fluorene ring as well as a condensed monocyclic or condensed polycyclic ring having only carbon as a ring-forming atom and having aromaticity in the entire molecule. It is understood that the monocyclic ring also includes a condensed polycyclic ring formed by linking adjacent substituents. At this time, the number of carbon atoms of the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto.
  • the aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a fluorene ring, and the like, but is not limited thereto.
  • heterocyclic ring refers to a hetero-condensed monocyclic or hetero-condensed ring containing at least one heteroatom among O, N, and S other than carbon as a ring-forming atom and having aromaticity in the entire molecule. It means a polycyclic ring.
  • the number of carbon atoms of the hetero ring is 2 to 60, or 2 to 30, or 2 to 20, but is not limited thereto.
  • the hetero ring may be a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, and the like, but is not limited thereto.
  • 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 the heteroarylamines may be described above for heteroaryl.
  • 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.
  • An organic light-emitting device includes a first electrode on a substrate and a second electrode provided opposite to the first electrode, and in this case, when the first electrode is an anode, the second electrode is a cathode and When the first electrode is a cathode, the second electrode is an anode.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, an emission layer, and a cathode are sequentially stacked on a substrate.
  • the organic light-emitting device may be an organic light-emitting device of an inverted type in which a cathode, an emission layer, and an anode are sequentially stacked on a substrate.
  • 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); A combination of a metal and an oxide 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 light emitting layer provided between the first electrode and the second electrode, which is a layer that emits light in a visible light region by combining holes and electrons transported from the hole transport layer and the electron transport layer,
  • the emission layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2.
  • both the first compound and the second compound are used as host materials.
  • the first compound is an N-type host material
  • the second compound is a P-type host material
  • the emission layer of the organic light emitting device includes the N-type host material and the P-type host material at the same time, a single material host Compared to the case of use, it can exhibit improved effects in terms of efficiency and life.
  • the first compound has a structure in which both an N-containing 6-membered heterocyclic group and an A substituent (benzocarbazolyl-based substituent) are bonded to one benzene ring of a dibenzothiophene-based core.
  • the first compound having such a structure includes a compound having a structure in which an N-containing 6-membered heterocyclic group and an A substituent (benzocarbazolyl-based substituent) are each bonded to another benzene ring of a dibenzothiophene-based core, and the A substituent (Compared to a compound in which a substituted/unsubstituted carbazolyl substituent instead of a benzocarbazolyl substituent) is bonded, stability against electrons and holes is high, and the balance between electrons and holes can be stably maintained.
  • an N-containing 6 membered-heterocyclic group and an A substituent are each bonded to another benzene ring of the dibenzothiophene-based core.
  • an organic light-emitting device employing a compound having a structure and a compound in which a substituted/unsubstituted carbazolyl substituent is combined instead of the A substituent (benzocarbazolyl-based substituent) the characteristics of low driving voltage, high efficiency and long life Show.
  • the first compound is represented by any one of the following Formulas 1A to 1D, depending on the bonding position of the N-containing 6-membered heterocyclic group in the dibenzothiophene-based core:
  • all of X 1 to X 3 are N.
  • each of Z is independently hydrogen or deuterium, or two adjacent to Z may be bonded to each other to form an unsubstituted or deuterated C 6-20 aromatic ring, for example a benzene ring. .
  • n which means the number of Z, is 0, 1, 2, 3, 4, 5, or 6.
  • the first compound may be represented by any one of the following Formulas 1A-1 to 1D-1:
  • Z 1 to Z 3 is a substituent A represented by Formula 1-1, and the others are each independently hydrogen or deuterium, or two of Z 1 to Z 3 that are adjacent to each other are unsubstituted or deuterium Can form a benzene ring substituted with,
  • Z 4 to Z 7 are each independently hydrogen or deuterium, or two adjacent two of Z 4 to Z 7 may be bonded to each other to form a benzene ring unsubstituted or substituted with deuterium,
  • Ar 1 and Ar 2 are as defined in Chemical Formula 1.
  • Z 1 is A
  • Z 2 and Z 3 are each independently hydrogen or deuterium, or Z 2 and Z 3 are combined with each other to form a benzene ring unsubstituted or substituted with deuterium;
  • Z 2 is A, and Z 1 and Z 3 are each independently hydrogen or deuterium; or
  • Z 3 is A, and Z 1 and Z 2 are each independently hydrogen or deuterium, or Z 1 and Z 2 may be bonded to each other to form a benzene ring unsubstituted or substituted with deuterium.
  • Z 1 is A
  • Z 2 and Z 3 are each independently hydrogen or deuterium, or Z 2 and Z 3 are combined with each other to form a benzene ring unsubstituted or substituted with deuterium;
  • Z 2 is A, and Z 1 and Z 3 are each independently hydrogen or deuterium; or
  • Z 3 is A, and Z 1 and Z 2 may each independently be hydrogen or deuterium.
  • Z 1 is A, and Z 2 and Z 3 are each independently hydrogen or deuterium;
  • Z 2 is A, and Z 1 and Z 3 are each independently hydrogen or deuterium; or
  • Z 3 is A, and Z 1 and Z 2 are each independently hydrogen or deuterium, or Z 1 and Z 2 may be bonded to each other to form a benzene ring unsubstituted or substituted with deuterium.
  • Z 1 is A
  • Z 2 and Z 3 are each independently hydrogen or deuterium, or Z 2 and Z 3 are combined with each other to form a benzene ring unsubstituted or substituted with deuterium;
  • Z 2 is A, and Z 1 and Z 3 are each independently hydrogen or deuterium; or
  • Z 3 is A, and Z 1 and Z 2 are each independently hydrogen or deuterium, or Z 1 and Z 2 may be bonded to each other to form a benzene ring unsubstituted or substituted with deuterium.
  • the first compound may be represented by any one of the following Formulas 3-1 to 3-7:
  • Each R is independently hydrogen or deuterium
  • Ar 1 and Ar 2 are as defined in Chemical Formula 1.
  • Ar 1 and Ar 2 are each independently unsubstituted or substituted with heavy hydrogen, or C 6-20 aryl C 6-20 aryl.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzothiophenyl, dibenzofuranyl, or carbazolyl,
  • Ar 1 and Ar 2 may be unsubstituted or substituted with 1 to 5 substituents each independently selected from the group consisting of deuterium and C 6-20 aryl.
  • Ar 1 and Ar 2 are each independently any one selected from the group consisting of:
  • Ar 1 and Ar 2 may be the same as each other, or Ar 1 and Ar 2 may be different.
  • R 1 to R 4 are each independently hydrogen or deuterium, or two adjacent to R 1 to R 4 are bonded to each other to be unsubstituted or deuterium It can form a substituted benzene ring.
  • m which means the number of deuterium (D)
  • D deuterium
  • A is any one of the substituents represented by the following formulas a1 to a4:
  • the compound represented by Formula 1 may be prepared by a manufacturing method such as the following Scheme 1 as an example.
  • each of X is independently halogen, preferably bromo or chloro, and definitions for other substituents are as described above.
  • the compound represented by Formula 1 is prepared by combining starting materials SM1 and SM2 through an amine substitution reaction.
  • This amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base.
  • the reactor for the amine substitution reaction may be appropriately changed, and the method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.
  • the second compound is a biscarbazole-based compound, and preferably, T 1 to T 4 have a structure in which each independently a C 6-20 aromatic ring. More preferably, T 1 to T 4 are unsubstituted or deuterium-substituted benzene rings, or unsubstituted or deuterium-substituted naphthalene rings.
  • T 1 to T 4 are benzene rings, wherein the second compound is represented by the following formula 2-1:
  • r and s are each independently an integer of 0 to 7,
  • L 1 and L 2 are each independently a single bond or an unsubstituted C 6-20 arylene.
  • L 1 and L 2 are each independently a single bond, phenylene, or naphthylene.
  • Ar 3 and Ar 4 are each independently C 6-20 aryl unsubstituted or substituted with C 1-10 alkyl or C 6-20 aryl; Or C 2-20 heteroaryl including O or S.
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, spirobifluorenyl, fluoranthenyl, Dibenzothiophenyl, dibenzofuranyl,
  • Ar 3 and Ar 4 may be unsubstituted or substituted with 1 to 4 substituents each independently selected from the group consisting of C 1-10 alkyl and C 6-20 aryl.
  • Ar 3 and Ar 4 are each independently any one selected from the group consisting of:
  • Ar 3 and Ar 4 may be the same as each other, or Ar 3 and Ar 4 may be different.
  • the second compound is represented by the following formula 2-2:
  • L 1 and L 2 are each independently a single bond, phenylene, or naphthylene,
  • Ar 3 and Ar 4 are as defined in Chemical Formula 2.
  • the compound represented by Formula 2 may be prepared by a manufacturing method as shown in Scheme 2 below, for example.
  • each of X is independently halogen, preferably bromo or chloro, and the definition of other substituents is as described above.
  • the compound represented by Formula 2 is prepared by combining the starting materials SM3 and SM4 through a Suzuki-coupling reaction.
  • This Suzuki-coupling reaction is preferably carried out in the presence of a palladium catalyst and a base.
  • the reactor for the Suzuki-coupling reaction may be appropriately changed, and the method of preparing the compound represented by Formula 2 may be more specific in Preparation Examples to be described later.
  • the first compound and the second compound are preferably included in the light-emitting layer in a weight ratio of 99:1 to 1:99, more preferably 50:50, to implement a device having high efficiency and long life.
  • the emission layer further includes a dopant material in addition to the host material.
  • dopant materials 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 light emitting layer may include the following iridium complex compound as a dopant material, but is not limited thereto.
  • the organic light emitting device may further include a hole injection layer on the anode.
  • the hole injection layer is made of a hole injection material, and the hole injection material has the ability to transport holes, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material.
  • a compound that prevents migration to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene )-Based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
  • the organic light-emitting device may further include a hole transport layer on the anode or on the hole injection layer formed on the anode.
  • the hole transport layer is a layer that receives holes from an anode or a hole injection layer formed on the anode and transports holes to the emission layer, and the hole transport material included in the hole transport layer receives holes from the anode or the hole injection layer to the emission layer.
  • a transferable material a material with high mobility for holes is suitable.
  • the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.
  • the organic light-emitting device may further include an electron suppression layer on the hole transport layer.
  • the electron suppression 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. It means a layer that plays a role in improving
  • the electron-suppressing layer includes an electron-blocking material, and examples of such an electron-blocking material include a compound represented by Formula 1 or an arylamine-based organic material, but are not limited thereto.
  • the organic balsop device may further include a hole blocking layer on the emission layer.
  • the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by increasing the probability of hole-electron coupling by controlling electron mobility and preventing excessive movement of holes. It means the layer that plays a role.
  • the hole-blocking layer includes a hole-blocking material, and examples of such hole-blocking materials include: a subazine derivative 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 organic light-emitting device may include an electron transport layer on the emission layer or on the hole blocking layer.
  • the electron transport layer is a layer that receives electrons from a cathode or an electron injection layer to be described later and transports electrons to the emission layer.
  • an electron transport material included in the electron transport layer electrons capable of receiving electrons from the cathode and transferring them to the emission layer Materials with high mobility are suitable.
  • the electron transport material include pyridine derivatives; Pyrimidine derivatives; Triazole 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 can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.
  • the organic light-emitting device may further include an electron injection layer between the electron transport layer and the cathode.
  • the electron injection layer is a layer that injects electrons from the cathode, and the electron injection material included in the electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and excellent electron injection to the light emitting layer or the light emitting material A compound having an effect, preventing the movement of excitons generated in the light emitting layer to the hole injection layer, and having excellent thin film formation ability is preferable.
  • materials that can be used as the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, tria Sol, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and the like, derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples 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. It is not limited to this.
  • the electron transport layer and the electron injection layer may be provided in the form of an electron injection and transport layer that simultaneously serves as an electron transport layer and an electron injection layer for transporting received electrons to the emission layer.
  • 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 first compound and the second compound may be included in the emission layer.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron suppressing layer 7, a hole blocking layer 8, an electron injection and transport layer ( 8) and the cathode 4 shows an example of an organic light emitting device.
  • the first compound and the second compound may be included in the emission layer.
  • 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.
  • intermediate 2-1-1 (10g, 25.2mmol) and intermediate 2-1-2 (8g, 27.7mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.9g, 100.7mmol) was dissolved in water and added. After sufficient stirring, reflux was performed, and then bis (tri-tert-butylphosphine) palladium (0) (0.1 g, 0.3 mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-2-1 (10g, 25.2mmol) and intermediate 2-2-2 (8g, 27.7mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.9g, 100.7mmol) was dissolved in water and added. After sufficient stirring, reflux was performed, and then bis (tri-tert-butylphosphine) palladium (0) (0.1 g, 0.3 mmol) was added. After the reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-4-1 (10g, 25.2mmol) and intermediate 2-4-2 (9.3g, 27.7mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.9g, 100.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis (tri-tert-butylphosphine) palladium(0) (0.1g, 0.3mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-5-1 (10g, 25.2mmol) and intermediate 2-5-2 (10.1g, 27.7mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.9g, 100.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis (tri-tert-butylphosphine) palladium(0) (0.1g, 0.3mmol) was added. After the reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-6-1 (10g, 25.2mmol) and intermediate 2-6-2 (11.4g, 27.7mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.9g, 100.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis (tri-tert-butylphosphine) palladium(0) (0.1g, 0.3mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-7-1 (10g, 22.4mmol) and intermediate 2-7-2 (10.2g, 24.6mmol) were added to 200 ml of THF, stirred, and potassium carbonate (12.4g, 89.5mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-8-1 (10g, 17.9mmol) and intermediate 2-8-2 (5.6g, 19.7mmol) were added to 200 ml of THF, stirred, and potassium carbonate (9.9g, 71.5mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-9-1 (10g, 21.1mmol) and intermediate 2-9-2 (6.7g, 23.3mmol) were added to 200 ml of THF, stirred, and potassium carbonate (11.7g, 84.6mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-10-1 (10g, 27mmol) and intermediate 2-10-2 (10g, 29.6mmol) were added to 200 ml of THF, stirred, and potassium carbonate (14.9g, 107.8mmol) was dissolved in water and added. After sufficiently stirring and refluxing, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.3mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-11-1 (10g, 27mmol) and intermediate 2-11-2 (11.5g, 29.6mmol) were added to 200 ml of THF, stirred, and potassium carbonate (14.9g, 107.8mmol) was dissolved in water and added. After sufficient stirring, reflux was performed, and then bis (tri-tert-butylphosphine) palladium (0) (0.1 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-12-1 (10g, 23.8mmol) and intermediate 2-12-2 (8.8g, 26.1mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.1g, 95mmol) was dissolved in water and added. Then, after sufficiently stirring, refluxed, and then bis (tri-tert-butylphosphine) palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-13-1 (10g, 24.3mmol) and intermediate 2-13-2 (11.1g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-14-1 (10g, 24.3mmol) and intermediate 2-14-2 (7.7g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-15-1 (10g, 24.3mmol) and intermediate 2-15-2 (9g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water and added. Then, after sufficiently stirring, refluxed, and then bis (tri-tert-butylphosphine) palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-16-1 (10g, 24.3mmol) and intermediate 2-16-2 (11.1g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-17-1 (10g, 24.3mmol) and intermediate 2-17-2 (10.1g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-18-1 (10g, 24.3mmol) and intermediate 2-18-2 (10.5g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-19-1 (10g, 24.3mmol) and intermediate 2-19-2 (10.5g, 26.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (13.5g, 97.3mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-20-1 (10g, 23.4mmol) and intermediate 2-20-2 (9.4g, 25.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (12.9g, 93.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-21-1 (10g, 23.4mmol) and intermediate 2-21-2 (10.6g, 25.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (12.9g, 93.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-22-1 (10g, 23.4mmol) and intermediate 2-22-2 (11.3g, 25.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (12.9g, 93.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • intermediate 2-23-1 (10g, 23.4mmol) and intermediate 2-23-2 (10.1g, 25.8mmol) were added to 200 ml of THF, stirred, and potassium carbonate (12.9g, 93.7mmol) was dissolved in water. The mixture was added, stirred sufficiently, and refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.2mmol) was added. After the reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Comparative example 1 Fabrication of an organic light emitting device
  • a glass substrate coated with a thin film of ITO (indium tin oxide) to 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.
  • the following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 ⁇ , but the following compound A-1 was p-doping at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ⁇ .
  • an electron suppressing layer was formed by vacuum depositing the following EB-1 compound with a film thickness of 150 ⁇ on the hole transport layer.
  • the compound 1-1 prepared in Preparation Example 1-1 and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition film to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed by vacuum depositing the following HB-1 compound with a film thickness of 30 ⁇ on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ . Lithium fluoride (LiF) at a thickness of 12 ⁇ and aluminum at a thickness of 1,000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • LiF lithium fluoride
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 2 x 10 ⁇ Maintaining 7 to 5 x 10 -6 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 below was used instead of compound 1-1 in the organic light-emitting device of Comparative Example 1.
  • the organic light-emitting device of the embodiment in which the first compound represented by Formula 1 and the second compound represented by Formula 2 were simultaneously used as the host material of the emission layer is a compound represented by Formulas 1 and 2 Compared to the organic light-emitting device of Comparative Example in which only one of or neither is employed, the same or superior luminous efficiency, low driving voltage, and remarkably improved lifetime characteristics are exhibited.
  • the device according to the example exhibited higher efficiency and longer life than the device of the comparative example employing the compound represented by Formula 1 as a single host.
  • the device according to the embodiment has improved efficiency and lifespan characteristics compared to the device of Comparative Example employing Comparative Examples Compounds C-1 to C-12 as a first host and a compound represented by Formula 2 as a second host. Became.
  • Comparative Example employing Comparative Examples Compounds C-1 to C-12 as a first host and a compound represented by Formula 2 as a second host. Became.
  • the combination of the first compound represented by Formula 1 and the second compound represented by Formula 2 was used as a cohost, it was confirmed that energy was effectively transferred to the red dopant in the red light emitting layer. This can be determined because the first compound has high stability against electrons and holes, and also because the amount of holes increased as the second compound was used simultaneously, and a more stable balance of electrons and holes was maintained in the red light emitting layer. It is judged as.
  • the organic light-emitting device when considering that the luminous efficiency and lifetime characteristics of the organic light-emitting device have a trade-off relationship with each other, 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 as representing.
  • substrate 2 anode

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  • Physics & Mathematics (AREA)
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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une diode électroluminescente organique.
PCT/KR2020/095039 2019-03-15 2020-03-13 Diode électroluminescente organique WO2020190116A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150126756A (ko) * 2014-05-02 2015-11-13 삼성디스플레이 주식회사 유기 발광 소자
KR20170111387A (ko) * 2016-03-28 2017-10-12 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20190007789A (ko) * 2017-07-13 2019-01-23 에스에프씨 주식회사 고효율 및 장수명 특성을 가지는 유기 발광 소자
KR20190013139A (ko) * 2017-07-31 2019-02-11 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20190024772A (ko) * 2017-08-28 2019-03-08 주식회사 엘지화학 헤테로고리 화합물 및 이를 이용한 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150126756A (ko) * 2014-05-02 2015-11-13 삼성디스플레이 주식회사 유기 발광 소자
KR20170111387A (ko) * 2016-03-28 2017-10-12 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20190007789A (ko) * 2017-07-13 2019-01-23 에스에프씨 주식회사 고효율 및 장수명 특성을 가지는 유기 발광 소자
KR20190013139A (ko) * 2017-07-31 2019-02-11 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20190024772A (ko) * 2017-08-28 2019-03-08 주식회사 엘지화학 헤테로고리 화합물 및 이를 이용한 유기 발광 소자

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