WO2021045470A1 - 신규한 화합물 및 이를 이용한 유기 발광 소자 - Google Patents

신규한 화합물 및 이를 이용한 유기 발광 소자 Download PDF

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WO2021045470A1
WO2021045470A1 PCT/KR2020/011677 KR2020011677W WO2021045470A1 WO 2021045470 A1 WO2021045470 A1 WO 2021045470A1 KR 2020011677 W KR2020011677 W KR 2020011677W WO 2021045470 A1 WO2021045470 A1 WO 2021045470A1
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서상덕
이동훈
김민준
김영석
김동희
오중석
김서연
이다정
최승원
심재훈
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주식회사 엘지화학
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Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by 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.
  • An 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 multilayer 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.
  • 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. When it falls back to the ground, it glows.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1):
  • X is O, or S
  • Ar is substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
  • R 1 , R 2 , R 3 , and R 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 2-60 alkynyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S; Substituted or unsubstituted tri(C 1-60 alkyl)silyl; Or a substituted or unsubstituted tri(C 6-60 aryl)silyl, or two adjacent substituents are bonded to form a C 6-60
  • n1 is an integer from 0 to 2
  • n2 to n4 are each independently an integer of 0 to 3
  • L is any one of the following,
  • Y is O, or S
  • Each R 5 is independently hydrogen; heavy hydrogen; halogen; Cyano; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 2-60 alkynyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 6-60 aryl; C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S; Substituted or unsubstituted tri(C 1-60 alkyl)silyl; Or a substituted or unsubstituted tri(C 6-60 aryl)silyl, or two adjacent substituents are bonded to form a C 6-60 aromatic ring,
  • n5 is an integer from 0 to 4.
  • the present invention the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 to provide.
  • the compound represented by Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • 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 is an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4 Is shown.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituent
  • 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 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 a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group.
  • 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, a phenyl boron group, and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to 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 preferably has 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 monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but 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.
  • the fluorenyl group is substituted, Can be, etc. However, it is not limited thereto.
  • heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms.
  • heteroaryl include xanthene, thioxanthen, 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, iso
  • the aryl group among 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.
  • the 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 cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.
  • the present invention provides a compound represented by Chemical Formula 1.
  • Ar is phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothio Phenyl, carbazol-9-yl, or 9-phenyl-carbazolyl, wherein Ar is unsubstituted or substituted with one or more deuterium.
  • R 1 , R 2 , R 3 and R 4 are hydrogen. At this time, preferably, n1 to n4 are 0.
  • one of R 1 , R 2 , R 3 and R 4 is phenyl and the other is hydrogen.
  • one of n1 to n4 is 1, and the other is 0.
  • two adjacent R 1 , two adjacent R 2 , two adjacent R 3 , or two adjacent R 4 are bonded to each other to form a benzene ring, and the remaining R 1 to R 4 are hydrogen.
  • one of n1 to n4 is 2, and the others are 0.
  • R 5 is all hydrogen, or R 5 is all deuterium.
  • n5 is 0 or 4.
  • n5 is 2.
  • the present invention provides a method for preparing a compound represented by Formula 1, such as the following Scheme 1 as an example:
  • reaction Scheme 1 the definitions other than X'are as previously defined, and X'is halogen, more preferably chloro or bromo.
  • the reaction is an amine substitution reaction, and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction may be changed as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the present invention provides an organic light-emitting device including the compound represented by Formula 1 above.
  • the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to the present invention.
  • the organic light-emitting device according to the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light-emitting device according to the present invention may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the emission layer.
  • the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the emission layer.
  • the organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except for using the compound according to the present invention.
  • the organic light emitting device may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate.
  • the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate.
  • a PVD physical vapor deposition
  • the organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
  • 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 first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • 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; Conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), 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 hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer.
  • a compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film 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 materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes.
  • the material is suitable. Specific examples include an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • 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, periflanthene and the like having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like 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
  • styrylamine styryldiamine
  • styryltriamine examples of the metal complex
  • styryltetraamine examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.
  • an electron transport material a material capable of injecting electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include 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 electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • a compound that prevents migration to the layer and is excellent in thin film forming ability is preferable.
  • Complex compounds and nitrogen-containing 5-membered ring derivatives but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( 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 organic light-emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Compound 2 was prepared in the same manner as in the preparation method of compound 1, except that intermediate b was used instead of intermediate a.
  • Compound 3 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate c was used instead of the intermediate a.
  • Compound 4 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate d was used instead of the intermediate a.
  • Compound 5 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate e was used instead of the intermediate a.
  • Compound 6 was prepared in the same manner as in the preparation method of compound 1, except that the intermediate B was used instead of the intermediate A and the intermediate f was used instead of the intermediate a.
  • Compound 7 was prepared in the same manner as in the preparation method of compound 1, except that intermediate B was used instead of intermediate A and intermediate g was used instead of intermediate a.
  • Compound 8 was prepared in the same manner as in the preparation method of compound 1, except that intermediate B was used instead of intermediate A and intermediate h was used instead of intermediate a.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 ⁇ was put 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 washing 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-A compound and the following HAT-CN compound were sequentially thermally vacuum deposited to a thickness of 800 ⁇ and 50 ⁇ , respectively, to form a hole injection layer.
  • the following HT-A compound was vacuum-deposited to a thickness of 800 ⁇ to form a hole transport layer, followed by thermal vacuum evaporation of the following EB-A compound to a thickness of 600 ⁇ to form an electron blocking layer.
  • the compound 1 prepared above and the following RD compound were vacuum-deposited to a thickness of 400 ⁇ at a weight ratio of 98:2 to form a light emitting layer.
  • the following ET-A compound and the following Liq compound were thermally vacuum deposited to a thickness of 360 ⁇ at a weight ratio of 1:1 to form an electron transport layer, and then the following Liq compound was vacuum deposited to a thickness of 5 ⁇ to form an electron injection layer. Formed.
  • An organic light-emitting device was manufactured by sequentially depositing magnesium and silver on the electron injection layer to a thickness of 220 ⁇ at a weight ratio of 10:1 and aluminum to a thickness of 1000 ⁇ to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec, and the vacuum degree during deposition was maintained at 2X10 -7 ⁇ 5X10 -6 torr, thereby fabricating an organic light-emitting device.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1.
  • RH-A, RH-B and RH-C each mean the following compounds.
  • the compound represented by Formula 1 according to the present invention is configured in a form in which a substituent structure serving as an electron acceptor and a parent nucleus structure serving as an electron donor are connected.
  • a substituent structure serving as an electron acceptor and a parent nucleus structure serving as an electron donor are connected.
  • the two units of completely different properties are directly bonded, they have a small band gap by exchanging charges inside the molecule, which is advantageous for energy transfer to the red dopant and is suitable for use as a host of the red light emitting layer.
  • the parental structure serving as an electron donor exhibits high stability by condensing both benzocarbazole and benzofuran or benzothiophene to form a ring.
  • the unit serving as an electron acceptor has excellent properties in electron transfer compared to the quinazoline structure applied in the comparative example, and thus exhibits high efficiency characteristics.
  • the compounds according to the present invention when applied as a host of the red emission layer of an organic electroluminescent device, they exhibit characteristics of low voltage, high efficiency, and long life, thereby obtaining an optimal device.
  • substrate 2 anode

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