WO2021029616A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2021029616A1
WO2021029616A1 PCT/KR2020/010441 KR2020010441W WO2021029616A1 WO 2021029616 A1 WO2021029616 A1 WO 2021029616A1 KR 2020010441 W KR2020010441 W KR 2020010441W WO 2021029616 A1 WO2021029616 A1 WO 2021029616A1
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substituted
compound
unsubstituted
deuterium
group
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PCT/KR2020/010441
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한수진
이동훈
장분재
서상덕
정민우
이정하
박슬찬
황성현
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주식회사 엘지화학
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Priority claimed from KR1020200097980A external-priority patent/KR102447008B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202080005495.0A priority Critical patent/CN112789747A/zh
Publication of WO2021029616A1 publication Critical patent/WO2021029616A1/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.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials.
  • 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 made 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.
  • the present invention provides the following organic light emitting device:
  • a cathode provided to face the anode
  • the light-emitting layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2:
  • X is O or S
  • X 1 to X 3 are each independently N or CH, provided that at least one of X 1 to X 3 is N,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms of N, O and S,
  • R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; 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 containing one or more heteroatoms of N, O and S,
  • a+b is an integer from 0 to 6
  • c is an integer from 0 to 8
  • A is a benzene ring fused with two adjacent pentagonal rings
  • Ar 3 and Ar 4 are each independently Substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms of N, O and S,
  • R 4 is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; 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 containing one or more heteroatoms of N, O and S,
  • d is an integer from 0 to 10
  • the above-described organic light-emitting device includes two kinds of host compounds in the light-emitting layer, so that efficiency, driving voltage, and/or lifetime characteristics in the organic light-emitting device can be improved.
  • 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.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport and injection layer.
  • An example of an organic light-emitting device consisting of (8) and a cathode (4) is shown.
  • D means deuterium
  • Ph means a phenyl group
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile 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 a substituted or unsubstituted substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O and S atoms, or linked
  • 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, 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 phenanthryl 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.
  • the heteroaryl group is a heterocyclic group containing one or more heteroatoms of O, N, Si and S as heterogeneous elements, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl groups 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 , Car
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl 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.
  • anode Anode
  • a cathode provided to face the anode
  • an emission layer provided between the anode and the cathode, wherein the emission layer includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.
  • the organic light-emitting device may simultaneously include two types of compounds having a specific structure in the light-emitting layer as host materials, thereby improving efficiency, driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • 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, etc., 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 a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the organic light-emitting device may include a hole injection layer between an anode and a hole transport layer to be described later, if necessary.
  • the hole injection layer is a layer positioned 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 organic light emitting device may include a hole transport layer between the anode and the emission layer.
  • 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 light emitting layer, and includes a hole transport material.
  • a hole transport material a material capable of transporting holes from an anode or a hole injection layer to the light emitting layer and having high mobility for holes is suitable.
  • Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the organic light-emitting device may include an electron blocking layer between the hole transport layer and the emission layer, if necessary.
  • the electron blocking layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer, thereby controlling hole mobility and preventing excessive movement of electrons to increase the probability of hole-electron coupling, thereby increasing the efficiency of the organic light emitting device. It refers to the layer that plays a role in improving the value.
  • the electron blocking layer includes an electron blocking material, and an arylamine-based organic material may be used as an example of the electron blocking material, but is not limited thereto.
  • the organic light-emitting device includes an emission layer between an anode and a cathode, and the emission layer includes the first compound and the second compound as a host material.
  • the first compound functions as an N-type host material having an electron transport ability superior to that of a hole transporting ability
  • the second compound functions as a P-type host material having a hole transport ability greater than an electron transporting ability. It is possible to properly maintain the ratio of the electron to the electron. Accordingly, excitons are evenly emitted from the entire emission layer, so that the luminous efficiency and lifespan characteristics of the organic light-emitting device can be simultaneously improved.
  • the first compound is represented by Chemical Formula 1.
  • the first compound is a compound in which a carbazolyl group and an N-containing 6 membered-heterocyclic group are simultaneously substituted on a dibenzofuran/dibenzothiophene core, and these compounds have an intramolecular charge compared to a compound not having all of these substituents. Since inter charge transfer is well performed, the stability of molecules is high, and holes and electrons can be effectively transported. In addition, this effect can be further maximized when the second compound, which will be described later, is used together as a host of the emission layer.
  • the first compound may contain at least one deuterium.
  • At least one of Ar 1 and Ar 2 is C 6-60 aryl substituted with deuterium; Or C 2-60 heteroaryl containing one or more heteroatoms of N, O and S substituted with deuterium; or
  • At least one of R 1 to R 3 is deuterium; C 6-60 aryl substituted with deuterium; Or C 2-60 heteroaryl including one or more heteroatoms among N, O and S substituted with deuterium, and a+b+c may be 1 or more, or an integer of 1 to 14.
  • C 6-60 aryl in which at least one of Ar 1 and Ar 2 is substituted with deuterium; Or C 2-60 heteroaryl including one or more heteroatoms of N, O and S substituted with deuterium, and at least one of R 1 to R 3 is deuterium; C 6-60 aryl substituted with deuterium; Or C 2-60 heteroaryl including one or more heteroatoms among N, O and S substituted with deuterium, and a+b+c may be 1 or more.
  • the first compound may be represented by the following formula 1':
  • R 21 to R 24 is And the rest are each independently referring to the definition of R 2 , and one of R 11 to R 14 is And, each of the rest independently refers to the definition of R 1 , or
  • R 21 to R 24 each independently refer to the definition of R 2
  • R 14 is And one of R 11 to R 13 is And each of the others independently refers to the definition of R 1 .
  • the first compound when represented by Formula 1', it may be more advantageous in terms of intramolecular charge transfer and molecular stability than a compound in which a carbazolyl group and an N-containing 6-membered heterocyclic group are substituted at other positions. .
  • the first compound may be represented by any one of the following Formulas 1A' to 1E':
  • X, X 1 to X 3 , Ar 1 , Ar 2 , R 1 to R 3 , a+b and c are as defined in Chemical Formula 1.
  • a and b are each an integer of 0 to 3
  • a is an integer of 0 to 2
  • b is an integer of 0 to 4.
  • the compound represented by Formula 1C' is the following Formula 1A (core 6 position), Formula 1B (core 7 position), and Formula 1C according to the substitution position of the N-containing 6-membered heterocyclic group. (Position 8 of the core), or Formula 1D (position 9 of the core) can be represented:
  • a and b are each an integer of 0 to 3
  • X is O.
  • all of X 1 to X 3 are N, or
  • X 1 and X 2 are N, and X 3 is CH, or
  • X 1 and X 3 are N, X 2 is CH, or
  • X 1 is N, X 2 and X 3 are CH, or
  • X 2 is N, and X 1 and X 3 may be CH.
  • Ar 1 and Ar 2 are each independently C 6-20 aryl, or C 2-20 heteroaryl comprising 1 or 2 heteroatoms of N, O and S,
  • Ar 1 and Ar 2 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, naphthyl, phenanthryl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, or benzothiazolyl,
  • Ar 1 and Ar 2 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C 1-10 alkyl and C 6-20 aryl.
  • Ar 1 and Ar 2 may be any one selected from the group consisting of, but is not limited thereto:
  • n is an integer from 0 to 7.
  • At least one of Ar 1 and Ar 2 is , or Can be
  • 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 3 are each independently deuterium; C 6-20 aryl unsubstituted or substituted with deuterium; Or it may be unsubstituted or C 2-20 heteroaryl including one heteroatom of N, O and S substituted with deuterium.
  • R 1 and R 2 may each independently be hydrogen, deuterium, phenyl, phenyl substituted with 1 to 5 deuterium, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.
  • R 3 is hydrogen; heavy hydrogen; Phenyl unsubstituted or substituted with deuterium; Carbazolyl unsubstituted or substituted with deuterium; Dibenzofuranyl unsubstituted or substituted with deuterium; Or it may be unsubstituted or dibenzothiophenyl substituted with deuterium.
  • substituent of Formula 1 May be any one of the substituents represented by the following formulas 3a to 3i:
  • p is an integer from 0 to 7
  • q is an integer from 0 to 8.
  • a+b which means the sum of the number of R 1 and R 2 , may be 0, 1, 2, 3, 4, 5, or 6, and c means the number of R 3 It can be 0, 1, 2, 3, 4, 5, 6, 7, or 8.
  • a+b may be 0, 1, 2, or 6, and c may be 0, 1, 2, or 8.
  • R 1 and R 2 are both deuterium, and when c is 8, R 3 may be deuterium.
  • the compound represented by Formula 1 may be prepared by a manufacturing method such as the following Scheme 1 as an example.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • X a and X' are each independently halogen, preferably X a is fluoro, X'is bromo or chloro, and the definitions for other substituents are as described above.
  • the compound represented by Formula 1 may be prepared through steps 1-1 and 1-2.
  • Step 1-1 is a step of preparing intermediate compound A3 through Suzuki-coupling reaction of starting materials A1 and A2. These Suzuki-coupling reactions are preferably carried out in the presence of a palladium catalyst and a base, respectively, and the reactor for the Suzuki-coupling reaction may be appropriately changed.
  • step 1-2 is a step of preparing a compound represented by Formula 1 in which a carbazole group is introduced into the intermediate compound A3 through an amine substitution reaction between the intermediate compound A3 and the compound A4, and such an amine substitution reaction is performed with a palladium catalyst. It is preferred to carry out in the presence of a base.
  • the reactor for the amine substitution reaction may also be appropriately changed as known in the art.
  • 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 represented by Chemical Formula 2.
  • the second compound is a compound in which Ar 3 and Ar 4 substituents are substituted on each of two N atoms of the indolocarbazole core.
  • the electron transport property may be controlled by substituting Ar 3 and Ar 4 substituents around the indolocarbazole structure. Accordingly, when the second compound is used in the emission layer together with the first compound, the hole and electron transport characteristics can be variously adjusted, which is advantageous in balancing charge in the emission layer.
  • the second compound may be represented by any one of the following Formulas 2-1 to 2-5, depending on the position at which the benzene ring, which is the A ring, is fused with two adjacent pentagonal rings:
  • Each R 4 is independently deuterium; Substituted or unsubstituted C 6-20 aryl; Or a substituted or unsubstituted C 2-20 heteroaryl containing one or more heteroatoms of N, O and S,
  • e is an integer from 0 to 4,
  • f is an integer from 0 to 2
  • g is an integer from 0 to 4,
  • Ar 3 and Ar 4 are as defined in Chemical Formula 2.
  • Ar 3 and Ar 4 may be hole transporting substituents.
  • Ar 3 and Ar 4 are each independently C 6-60 aryl; Carbazolyl; Dibenzofuranyl; Or dibenzothiophenyl,
  • Ar 3 and Ar 4 are unsubstituted or deuterium, C 6-20 aryl, carbazolyl, phenylcarbazolyl, dibenzofuranyl and one or more substituents selected from the group consisting of dibenzothiophenyl Can be substituted.
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, triphenylenyl, carbazolyl, dibenzofuranyl, or dibenzothio Is phenyl,
  • Ar 3 and Ar 4 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, phenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl and dibenzothiophenyl. .
  • Ar 3 and Ar 4 may each independently be any one selected from the group consisting of, but is not limited thereto:
  • R 4 is deuterium; C 6-20 aryl unsubstituted or substituted with deuterium; Or it may be unsubstituted or C 2-20 heteroaryl including one heteroatom of N, O and S substituted with deuterium.
  • R 4 is deuterium; C 6-20 aryl unsubstituted or substituted with deuterium; Carbazolyl unsubstituted or substituted with deuterium; Phenylcarbazolyl unsubstituted or substituted with deuterium; Dibenzofuranyl unsubstituted or substituted with deuterium; Or it may be unsubstituted or dibenzothiophenyl substituted with deuterium.
  • R 4 is deuterium; Phenyl unsubstituted or substituted with deuterium; Carbazolyl unsubstituted or substituted with deuterium; Phenylcarbazolyl unsubstituted or substituted with deuterium; Dibenzofuranyl unsubstituted or substituted with deuterium; Or it may be unsubstituted or dibenzothiophenyl substituted with deuterium.
  • R 4 may be deuterium, or any one selected from the group consisting of, but is not limited thereto:
  • d may be 0, 1, 2, or 10.
  • R 4 may be deuterium.
  • e may be 0, 1, or 4
  • f may be 0, 1, or 2
  • g may be 0, 1, or 4.
  • R 4 may be deuterium.
  • e+f+g is the same as d in Formulas 2-1 to 2-5, e+f+g may be 0, 1, 2, or 10.
  • the compound represented by Formula 2 may be prepared by a manufacturing method as shown in Scheme 2 below, for example.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • X is 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 B1 and B2 through an amine substitution reaction. Each of these amine substitution reactions 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 2 may be more specific in Preparation Examples to be described later.
  • the first compound and the second compound may be included in a weight ratio of 1:9 to 9:1 in the emission layer.
  • the weight ratio of the first compound and the second compound in the emission layer is 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4 or 4:6 to 5:5 Can be
  • the emission layer may further include a dopant material in addition to the two kinds of host materials.
  • dopant substances 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 dopant material may be included in the light emitting layer in an amount of 1 to 25% by weight based on the total weight of the host material (the sum of the weights of the compound represented by Formula 1 and the compound represented by Formula 2) and the dopant material. have.
  • the organic light emitting device may include a hole blocking layer between the light emitting layer and the electron transport layer to be described later, if necessary.
  • 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 the hole-blocking material include: a subazine derivative including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but is not limited thereto.
  • the electron transport layer is formed between the emission layer and the cathode to receive electrons from the electron injection layer and transport electrons to the emission 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.
  • Examples of specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives and the like, but are not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metal complex compounds , Or a nitrogen-containing 5-membered cyclic derivative, but may be used together, but is not limited thereto.
  • the organic light-emitting device may include an electron injection layer between the electron transport layer and the cathode, if necessary.
  • the organic light-emitting device may include an electron transport and injection layer as necessary.
  • the electron transport and injection layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer.
  • an electron injection and transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable.
  • specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives and the like, but are not limited thereto.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds , Or a nitrogen-containing 5-membered cyclic derivative, but may be used, but is not limited thereto.
  • the electron transport and injection layer may be formed as separate layers such as an electron injection layer and an electron transport layer.
  • the electron transport layer is formed on the emission layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer.
  • the electron injection layer is formed on the electron transport layer, and electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzoimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, etc. I can.
  • 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 thereto.
  • 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), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), an electron transport and injection layer.
  • An example of an organic light-emitting device consisting of (8) and a cathode (4) is shown.
  • the first compound and the second compound may be included in the emission layer.
  • the organic light-emitting device according to the present invention may 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) to a thickness of 1,400 ⁇ was placed in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO Indium Tin Oxide
  • Fischer Co. product was used as a detergent
  • distilled water secondarily filtered with a filter made 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 HT-A compound and the following PD compound were thermally vacuum-deposited at a thickness of 100 ⁇ at a weight ratio of 95:5 to form a hole injection layer, and then only the following HT-A compound had a thickness of 1150 ⁇ .
  • the following HT-B compound was thermally vacuum deposited to a thickness of 450 ⁇ to form an electron blocking layer (electron inhibiting layer).
  • a light emitting layer was formed by vacuum depositing the compound 1-1 and compound 2-1 prepared previously as a host compound and the following GD compound as a dopant compound to a thickness of 400 ⁇ at a weight ratio of 85:15. At this time, the weight ratio of the compound 1-1 and the compound 2-1 was 1: 1.
  • the following ET-A compound was vacuum deposited to a thickness of 50 ⁇ to form a hole blocking layer.
  • the following ET-B compound and the following Liq compound were thermally vacuum deposited to a thickness of 250 ⁇ at a weight ratio of 2:1, and then LiF and magnesium were vacuum deposited to a thickness of 30 ⁇ at a weight ratio of 1:1.
  • an electron transport and injection layer was formed.
  • magnesium and silver were deposited to a thickness of 160 ⁇ in a weight ratio of 1:4 to form a cathode, thereby manufacturing an organic light emitting device.
  • the deposition rate of organic materials was maintained at 0.4 to 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the negative electrode was 0.3 ⁇ /sec
  • the deposition rate of silver and magnesium was 2 ⁇ /sec.
  • An organic light-emitting device was manufactured by maintaining ⁇ 10 -7 to 5 ⁇ 10 -6 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in Example 1.
  • Voltage, efficiency, and lifetime were measured by applying a current to the organic light-emitting devices manufactured in the above Examples and Comparative Examples, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . In addition, T95 in Table 1 below means the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
  • Example 1 Compound 1-1, Compound 2-1 3.02 69.8 green 80
  • Example 2 Compound 1-2, Compound 2-3 3.01 70.0 green 86
  • Example 3 Compound 1-3, Compound 2-3 3.05 72.1 green 81
  • Example 4 Compound 1-4, Compound 2-8 3.01 70.0 green 85
  • Example 5 Compound 1-4, Compound 2-4 3.03 72.3 green 82
  • Example 5 Compound 1-5, Compound 2-5 3.08 70.7 green 80
  • Example 6 Compound 1-6, Compound 2-3 3.01 70.2 green 81
  • Example 7 Compound 1-7, Compound 2-6 3.03 71.2 green 86
  • Example 8 Compound 1-8, Compound 2-6 3.09 72.5 green 80
  • Example 9 Compound 1-9, Compound 2-4 3.03 69.5 green 87
  • Example 10 Compound 1-10, Compound 2-4 3.07 71.3 green 82
  • Example 11 Compound 1-10, Compound 2-4 3.07 71.3 green
  • the organic light emitting device of the embodiment using both the first compound and the second compound of the present invention as a host, the organic light emitting device of Comparative Examples 1 to 3 using only the first compound and the first compound And compared with the organic light emitting diodes of Comparative Examples 4 and 5 in which neither of the second compounds was used, it can be seen that it exhibits excellent characteristics in terms of efficiency and lifetime.
  • the organic light-emitting device of the above embodiment used two kinds of hosts, but the higher efficiency and higher efficiency than the organic light-emitting devices of Comparative Examples 6 and 7 employing a combination of other hosts instead of the combination of the first compound and the second compound It can be seen that it shows an excellent service life.
  • the organic light-emitting device employing the compound of the present invention has significantly improved device characteristics compared to the comparative example device. Means to represent.
  • substrate 2 anode

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

Abstract

La présente invention concerne un dispositif électroluminescent organique ayant une tension d'attaque et/ou une durée de vie améliorée en comprenant deux types de composés hôtes dans une couche électroluminescente.
PCT/KR2020/010441 2019-08-09 2020-08-06 Dispositif électroluminescent organique WO2021029616A1 (fr)

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KR10-2019-0097650 2019-08-09
KR1020200097980A KR102447008B1 (ko) 2019-08-09 2020-08-05 유기 발광 소자
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WO2021137565A1 (fr) * 2019-12-30 2021-07-08 엘티소재주식회사 Composé hétérocyclique, diode électroluminescente organique le comprenant, son procédé de fabrication et composition pour couche organique
EP4074706A1 (fr) * 2021-04-16 2022-10-19 LG Display Co., Ltd. Composé hétérocyclique deutéré et dispositif électroluminescent organique le comprenant et composition pour une couche organique de dispositif électroluminescent organique
EP4231804A3 (fr) * 2022-02-16 2023-09-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
TWI820989B (zh) * 2021-12-30 2023-11-01 南韓商樂金顯示科技股份有限公司 有機化合物與包含其的有機發光裝置
GB2625904A (en) * 2022-12-22 2024-07-03 Lg Display Co Ltd Organic compound, organic light emitting diode and organic light emitting device having the compound
EP4276924A4 (fr) * 2021-02-24 2024-07-24 Lg Chemical Ltd Dispositif électroluminescent organique

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WO2021137565A1 (fr) * 2019-12-30 2021-07-08 엘티소재주식회사 Composé hétérocyclique, diode électroluminescente organique le comprenant, son procédé de fabrication et composition pour couche organique
EP4276924A4 (fr) * 2021-02-24 2024-07-24 Lg Chemical Ltd Dispositif électroluminescent organique
EP4074706A1 (fr) * 2021-04-16 2022-10-19 LG Display Co., Ltd. Composé hétérocyclique deutéré et dispositif électroluminescent organique le comprenant et composition pour une couche organique de dispositif électroluminescent organique
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TWI820989B (zh) * 2021-12-30 2023-11-01 南韓商樂金顯示科技股份有限公司 有機化合物與包含其的有機發光裝置
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GB2625904A (en) * 2022-12-22 2024-07-03 Lg Display Co Ltd Organic compound, organic light emitting diode and organic light emitting device having the compound

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