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  • Y02E10/549—Organic PV cells

Definitions

• Organometallic compounds and organic light emitting devices containing them Organometallic compounds and organic light emitting devices containing them
• the present invention relates to an organometallic compound and an organic light emitting device comprising the same.
• organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
• An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, a high contrast, a fast response time, and is excellent in luminance, driving voltage, and speed characteristics.
• the organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device.
• the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
• Patent Literature Korean Patent Publication No. 10-2000-0051826
• the present invention relates to a novel organometallic 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, S, Y, or Se
• R a , and R c are hydrogen, deuterium, or substituted or unsubstituted d 10 alkyl
• R < 3 > and R < 4 &gt are each independently hydrogen; heavy hydrogen; halogen; Cyanoamino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d- 60 haloalkyl substituted or unsubstituted d-60 alkoxy; A substituted or unsubstituted d-60 haloalkoxy, substituted or unsubstituted C 3 - 60 cycloalkyl; Substituted or unsubstituted C 2 - 60 alkenyl, substituted or unsubstituted C 6 - 60 aryl; Substituted or unsubstituted C 6 -C 60 aryloxy; Or a substituted or unsubstituted N, C 2 containing one or more heteroatoms selected from the group consisting of 0 and S -, and 60 heterocyclic group,
• a and b are each 0 and 1, or 1 and 0,
• n 1 or 2;
• the present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers is a light emitting layer, and the light emitting layer comprises a compound represented by Formula 1, An organic light emitting device is provided.
• the compound represented by the formula (1) can be used as a material of the organic material layer of the organic light emitting device, and can improve the efficiency, the driving voltage and / or the lifetime special effect in the organic light emitting device.
• the compound represented by the above-mentioned formula (1) can be used as a material for the light emitting 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.
• FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
• a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
• the carbon number 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 a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group.
• it may be a compound of the following structural formula,
• the number of carbon atoms of the imide group is not particularly limited, but 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 specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, although this limited-7 does. In this specification.
• boron group examples include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
• halogen group examples include fluorine, chlorine,
• 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 one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl. Propyl, 11-propyl, isopropyl. Butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl.
• the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to one embodiment, the number of carbon atoms of the alkenyl group is a "2-6.
• the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms.
• the cycloalkyl group has 3 to 6 carbon atoms.
• Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, .2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, , 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
• the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
• the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like, But is not limited thereto.
• polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
• a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
• the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
• heterocyclic group examples include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group benzothiazole group, a benzocarbazole group, a benzo
• the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group is preferably an alkyl group As an example.
• the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.
• the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
• the description of the aryl group described above can be applied except that arylene is a divalent group.
• the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.
• Formula 1 may be represented by Formula 1-1, 1-2, 1-3, 1-4, or 1-5.
• Ri is -Si (C < 3 >) 3 .
• 3 ⁇ 4 it is hydrogen, methyl, CD 3, ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or bicyclo haeksil microporous.
• 3 ⁇ 4 is hydrogen, methyl, CD 3, ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, or bicyclo haeksil.
• 3 ⁇ 4 is hydrogen.
• the triplet energy level of the compound represented by Formula 1 is 2.6 eV or less, more preferably 2.45 eV to 2.6 eV.
• the compound represented by the above formula (1) has a maximum photoluminescence wavelength of 500 nm to 550 nm, more preferably 520 nm to 535 nm. Representative examples of the compound represented by the above formula (1) are as follows:
• the compound represented by the formula (1) can be prepared by the same method as in the following reaction formula (1).
• the present invention provides an organic light emitting device including the compound represented by Formula 1.
• the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is a light emitting layer, and the light emitting layer comprises a compound represented by Formula 1 , And an organic light emitting element.
• the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
• the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
• the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
• 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 layers, and a cathode are sequentially stacked on a substrate.
• the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
• a cathode a cathode
• an organic material layer a cathode
• an anode a cathode
• FIGS. Fig. 1 shows an example of an organic light emitting element made up of a substrate 1, an anode 2, a light emitting bulb 3, and a cathode 4.
• the compound represented by Formula 1 may be included in the light emitting layer.
• the organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
• the compound represented by Formula 1 may be included in the light emitting layer.
• the organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
• the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
• the organic light emitting device can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
• a metal oxide or a metal oxide having conductivity or an alloy thereof may be formed on the substrate by using a PVD (Physico-Volatile Deposition) method such as a sputtering method or an electron beam evaporation method
• PVD Physical-Volatile Deposition
• a hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a substance usable as a cathode is deposited thereon.
• An organic light emitting device can be made by sequentially depositing a material, an organic layer, and a cathode material.
• the compound represented by Formula 1 may be formed into an organic layer by vacuum deposition as well as solution coating in the production of an organic light emitting device.
• the solution coating method includes spin coating, dip coating, doctor blading , Inkjet printing, screen printing, spraying, coating, and the like, but is not limited thereto.
• an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode 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 and the second electrode is a cathode.
• the anode material a material having a large work function is preferably used so as to smoothly inject holes into the organic material charge.
• the positive electrode 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); ⁇ : ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; And conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] no.
• the negative electrode material is preferably 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, fowl, sodium, potassium, titanium, indium yttrium, lyrium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or Li / Al, and the like, no.
• the hole injecting layer is a layer for injecting holes from an electrode.
• the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
• a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable.
• the HOMO highest occupied molecular orbital of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer.
• the hole injecting material include organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, organic nitrile nitrile-tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
• the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material.
• a hole transport material Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
• the light emitting layer may include a host material and a dopant material.
• the host material is a condensed aromatic ring derivative or a heterocyclic compound.
• 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, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
• dopant material include an aromatic amine derivative, a styrylamine compound, a boron-containing L Fluoranthene compounds, and metal complexes.
• the compound represented by Formula 1 is used as a dopant.
• the electron-transporting layer receives electrons from the electron-injecting layer and reaches the light-emitting layer
• the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer, and is preferably a material having high mobility to electrons. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
• the electron transporting layer can be used with any desired cathode material, such as 10 used according to the prior art.
• an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver bull. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
• the electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to the hole injection layer and is excellent in the thin film forming ability is preferable.
• Specific examples thereof include fluorenone, anthraquinodimethane,
• Oxadiazole triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, etc. But is not limited thereto.
• 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
• the organic light emitting device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
• the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device. The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
• the compound 1-lb was prepared (10 g, yield 57%) in the same manner as the compound A-la except that the compound A2 was used instead of the compound A1.
• the compound 1-le was prepared (4 g, yield 60%) in the same manner as the compound 1-la except that the compound A3 was used instead of the compound A1.
• the compound A4 was prepared (14 g, yield 78%) in the same manner as the compound A3 except for using iodocyclopropane instead of iodomethane-d3.
• the compound 1-lf was prepared (8 g, yield 63%) in the same manner as the compound 1-la except that the compound A4 was used instead of the compound A1.
• Compound A6 was prepared in the same manner as Compound A3 except that iodocyclohexane was used instead of iodomethane-d3 (18 g, yield 6).
• the compound 2-la was prepared in the same manner as the compound 1-la except that the compound C1 was used instead of the compound A1 (21 g, yield 48%).
• the compound 2-le was prepared (26 g, yield 55%) in the same manner as the compound 1-la except that the compound C3 was used instead of the compound A1.
• the compound D3 was prepared in the same manner as the compound B1 except that the compound 2-le was used instead of the compound 1-la (yield 93%).
• the compound ' C4 was prepared (49 g, 92% yield) in the same manner as the compound C2 was prepared except that the compound 2-lf was used instead of the compound 2-lb.
• the compound 2-li was prepared (22 g, yield 48%) in the same manner as the compound 1-la except that the compound C5 was used instead of the compound A1.
• Compound D5 was prepared (yield 90%) in the same manner as compound B1, except that compound 2-li was used in place of compound 1-la.
• Compound 2 was prepared in the same manner as Compound 1 except that Compound C3 was used instead of Compound C2 (yield: 49%).
• Compound 3 was prepared in the same manner as Compound 1 except that Compound C4 was used instead of Compound C2 (yield: 41%).
• Compound 4 was prepared in the same manner as Compound 1 except that Compound C5 was used instead of Compound C2 (yield: 38%).
• Compound 7 was prepared (yield: 43%) in the same manner as Compound 1 except that Compound B2 and Compound C4 were used instead of Compound B1 and Compound C2, respectively.
• Compound 8 was prepared in the same manner as Compound 1 except that Compound B2 and Compound C5 were used instead of Compound B1 and Compound C2, respectively (yield: 51%).
• Compound 9 was prepared in the same manner as Compound 1 except that Compound B3 was used instead of Compound B1 (yield: 45%).
• Compound 10 was prepared in the same manner as Compound 1 except that Compound B3 and Compound C3 were used instead of Compound B1 and Compound C2, respectively (yield 39%).
• Compound 11 was prepared (yield 45%) in the same manner as Compound 1 except that Compound B3 and Compound C4 were used instead of Compound B1 and Compound C2, respectively.
• Compound 12 was prepared (yield 45%) in the same manner as Compound 1 except that Compound B3 and Compound C5 were used instead of Compound B1 and Compound C2, respectively.
• Compound 13 was prepared (yield 41%) in the same manner as Compound 1 was prepared, except that Compound B4 was used in place of Compound B1.
• Compound 14 was prepared (yield 41%) in the same manner as Compound 1 except that Compound B4 and Compound C3 were used instead of Compound B1 and Compound C2, respectively.
• Compound 16 was prepared (yield 45%) in the same manner as Compound 1 except that Compound B4 and Compound C5 were used instead of Compound B1 and Compound C2, respectively.
• Compound 17 was prepared in the same manner as Compound 1 except that Compound B5 was used in place of Compound B1 (yield: 43%).
• Compound 18 was prepared (yield 40%) in the same manner as Compound 1 except that Compound B5 and Compound C3 were used instead of Compound B1 and Compound C2, respectively.
• Compound 19 was prepared in the same manner as Compound 1 except that Compound B5 and Compound C4 were used instead of Compound B1 and Compound C2 (yield: 41%).
• Compound 20 was prepared (yield 44%) in the same manner as Compound 1 except that Compound B5 and Compound C5 were used instead of Compound B1 and Compound C2.
• Compound 21 was prepared in the same manner as Compound 1 except that Compound B6 was used instead of Compound B1 (yield 39%).
• Compound 22 was prepared (yield 48%) in the same manner as Compound 1 except that Compound B6 and Compound C3 were used instead of Compound B1 and Compound C2, respectively.
• Compound 24 was prepared in the same manner as Compound 1 except that Compound B6 and Compound C5 were used instead of Compound B1 and Compound C2, respectively (yield 46%).
• the compound was prepared in the same manner as the compound 1 except that the compound D2 and the compound A1 were used instead of the compound B1 and the compound C2, respectively (yield 39%).
• Compound 27 was prepared (yield 39%) in the same manner as Compound 1 except that Compound D4 and Compound A1 were used instead of Compound B1 and Compound C2, respectively.
• Compound 28 was prepared (yield 35%) in the same manner as Compound 1 except for using Compound D5 and Compound A1 instead of Compound B1 and Compound C2, respectively.
• the glass substrate coated with ITO indium tin oxide
• ITO indium tin oxide
• a Fischer Co. product was used as a detergent
• distilled water which was filtered with a filter of Millipore Co.
• ITO was washed for 30 minutes and then washed twice with distilled water and sonicated. 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
• the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
• the following HI-1 compound was thermally vacuum-deposited to a thickness of 50 A on the thus prepared ⁇ 'key transparent electrode to form a hole injection layer.
• the following HT-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer, and the HT-2 compound was vacuum-deposited to a thickness of 50 A on the HT-1 vapor deposition layer to form an electron blocking layer .
• the following HI compound, the following H2 compound, and the above-prepared Compound 1 were co-deposited on the HT-2 deposited film as a host at a weight ratio of 44: 44: 12 to form a 400 A thick light emitting layer.
• the following ET-1 compound was vacuum deposited on the light-emitting layer to a thickness of 250 A, and further, the following ET-2 compound was co-deposited with Li in a weight ratio of Li to a thickness of 100 A to form an electron transport layer and an electron injection layer.
• Aluminum was deposited on the electron injection layer to a thickness of 1000 A to form a cathode.
• Emitting layer were formed in the same manner as in Experimental Example 1, except that the compound described in Table 2 was used instead of Compound 1 in the formation of the light- Respectively. Comparative Experimental Examples 1 to 4
• T95 means the time required for the luminance to be reduced to 95% from the initial luminance.

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