WO2007119954A1 - Preparing method for organic thin layer of organic light emitting devices using electrochemical deposition - Google Patents

Preparing method for organic thin layer of organic light emitting devices using electrochemical deposition Download PDF

Info

Publication number
WO2007119954A1
WO2007119954A1 PCT/KR2007/001721 KR2007001721W WO2007119954A1 WO 2007119954 A1 WO2007119954 A1 WO 2007119954A1 KR 2007001721 W KR2007001721 W KR 2007001721W WO 2007119954 A1 WO2007119954 A1 WO 2007119954A1
Authority
WO
WIPO (PCT)
Prior art keywords
organic thin
light emitting
thin layer
emitting device
organic
Prior art date
Application number
PCT/KR2007/001721
Other languages
English (en)
French (fr)
Inventor
Chan-Seok Park
Chong-Chan Lee
Sang-Ook Kang
Won-Sik Han
Ho-Jin Son
Jong-Hyub Baek
Original Assignee
Dongjin Semichem Co., Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dongjin Semichem Co., Ltd filed Critical Dongjin Semichem Co., Ltd
Priority to JP2009505292A priority Critical patent/JP5113153B2/ja
Priority to DE112007000924T priority patent/DE112007000924T5/de
Publication of WO2007119954A1 publication Critical patent/WO2007119954A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour

Definitions

  • the invention relates to a method for preparing an organic thin layer of organic light emitting device using electrochemical deposition and more particularly, to a method for preparing an organic thin layer of organic light emitting device that has simple process by virtue of the use of monomolecular compounds that are easily purchased and prepared, has high productivity, makes it easy to control the thickness of thin layers to be prepared and has excellent adhesion to substrates and further, fundamentally improves erosion that may occur in a firstly-formed organic thin layer during the process of formation of a second organic thin layer especially when two or more organic thin layers are to be prepared in OLED devices and has excellent morphology stability, and an organic light emitting device prepared by the same method.
  • Background Art
  • OLED organic light emitting devices
  • General organic EL devices have a structure of an anode which is formed on the top of a substrate, a light emitting layer in the form of an organic thin film which is formed on the anode, and a cathode formed thereon in sequence. Further, they may have a hole injection layer or hole transport layer between the anode and the light emitting layer, or they may have a electron transport layer or electron injection layer between the light emitting layer and the cathode.
  • the hole injection layer, hole transport layer, electron transport layer and electron injection layer are organic thin layers consisting of organic compounds.
  • Such organic thin layers are formed through vacuum heat deposition, sputtering or spin coating.
  • the vacuum heat deposition or sputtering requires expensive equipments and has low productivity
  • the spin coating involves the problem that when two or more organic thin layers are formed, the previously-formed lower layer is melted by solvents in the process of spin coating of upper layer.
  • the present invention provides a method for preparing an organic thin layer of organic light emitting device comprising one or more organic thin layers between an anode and cathode, characterized in that the organic thin layer is formed by electrochemical deposition of a compound having bis(phenylcarbazol) group in molecule.
  • the compound having bis(phenylcarbazol) group in molecule is represented by formula 1 :
  • the invention provides the organic thin layer of organic light emitting device prepared by the above method. [13] Also, the invention provides an organic light emitting device comprising the organic thin layer prepared by the above method. [14] Also, the invention comprises a display device comprising the above organic light emitting device.
  • the method for preparation of the organic thin layer of organic light emitting device through electrochemical deposition according to the invention has simple process by virtue of the use of monomolecular compounds that are purchased or easily prepared without requiring special equipments, has high productivity, can make it easy to control the thickness of thin layers to be prepared and can fundamentally improve erosion of the pre-formed organic thin layers that occurred in the preparation of two or more organic thin layers by spin coating.
  • the organic thin layers in accordance with the invention have excellent adhesion to substrates, have uniform surface because their thickness can be adjusted at molecular level, and have excellent morphology stability and especially, in case of the organic thin layers formed through consecutive electrochemical deposition of two or more layers, interfaces between layers are even, erosion due to solvents does not occur, adhesion between interfaces is strong and they have fine patterns. Moreover, as they are not melted in most organic solvents, erosion due to solvents can be fundamentally reduced even in case of forming organic thin layers by known spin coating on the organic thin layers in accordance with the invention. Brief Description of the Drawings
  • Fig. 1 is a cyclic voltammonogram showing electrochemical deposition by a compound having bis(phenylcarbazol) group in a molecule according to an embodiment of the present invention.
  • Fig. 2 is a cyclic voltammonogram showing electrochemical deposition by a compound having bis(phenylcarbazol) group in a molecule according to another embodiment of the invention.
  • Fig. 3 is a cyclic voltammonogram showing electrochemical deposition by a compound having bis(phenylcarbazol) group in a molecule according to still another embodiment of the invention.
  • Fig. 4 is a cyclic voltammonogram showing electrochemical deposition by a compound having one phenylcarbazol group in a molecule according to comparative example of the invention.
  • Fig. 5 is a cyclic voltammonogram showing electrochemical deposition by a compound having bis (phenylcarbazol) group in a molecule according to another embodiment of the invention.
  • Fig. 6 is a cyclic voltammonogram showing electrochemical deposition by a compound having bis (phenylcarbazol) group in a molecule according to still another embodiment of the invention.
  • organic thin layers could be formed using electrochemical deposition by compounds having bis(phenylcarbazol) group in molecules as monomolecular compounds having small molecular weight and have thus completed the invention.
  • the present invention is directed to a method for preparing an organic thin layer of organic light emitting device comprising one or more organic thin films between anode and cathode characterized in that the organic thin layer is formed by electrochemical deposition of a compound having bis(phenylcarbazol) group in molecule.
  • the compound is a compound represented by the above formula 1 or one with two phenyl carbazol groups linked directly.
  • the divalent linking group, -X- is not limited to specific ones as long as phenyl carbazol groups can be bound to its both ends, and -SiR R -, -PR -, -NR
  • R to R are each independently a substituted or unsubstituted alkyl group of C -C , substituted or unsubstituted aryl group of C -C , substituted or unsubstituted hetero ring group of C -C , or substituted or unsubstituted heterocyclic ring group of C -C .
  • alkyl group of C -C include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and so on, and one or more hydrogen atoms of the alkyl group may be substituted by a halogen atom, hydroxyl group, nitro group, cyano group, amino group, amidino group, hydrazine, hydrozone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, indole, azaindole, alkyl group of C -C , alkenyl group of C -C , alkynyl group of C -C , aryl group of C -C , arylalkyl group of C -C , heteroaryl group of C -C , or het- eroarylalkyl group of C -C and of them
  • the unsubstituted aryl group in above refers to a carbocycle aromatic system of C -
  • the aryl includes aromatic radicals such as phenyl, naphthyl and tetrahydronaphthyl and one or more hydrogen atoms of the aryl group may be substituted by the same substituents as enumerated for the alkyl group.
  • the unsubstituted hetero ring group refers to a monovalent monocyclic or bicyclic aromatic organic compound of 6 to 50 ring atoms containing 1, 2 or 3 hetero atoms selected from N, O, P or S and having C as remaining ring atoms.
  • One or more hydrogen atoms of the hetero aryl group may be substituted by the same substituents as enumerated for the alkyl group.
  • the unsubstituted heterocyclic ring group refers to a ring type moiety formed by the fusion of two or more rings constituting the aryl group or hetero ring as defined above and one or more hydrogen atoms of the heterocyclic ring group may be substituted by the same substituents as enumerated for the alkyl group.
  • n is an integer of 1 to 3
  • R is each independently a hydrogen atom or methyl
  • electrochemical deposition refers to a method of forming organic thin layers by putting substrates to be deposited into a reaction vessel where the above compounds forming the organic thin layers which are intended to deposit and electrolytes are dissolved and depositing the compounds intended to deposit onto the substrates to be deposited by application of power.
  • the compounds forming the organic thin layers which are intended to deposit can be chosen among the above described compounds, depending on the organic thin layers to be formed on the substrates to be deposited, and the organic thin layer is one of the organic layers formed between anode and cathode and can be a hole injection layer (HIL), hole transport layer (HTL), emitting layer (EML), hole blocking layer (HBL), electron transport layer (ETL) or electron injection layer (EIL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EML hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • Any solvents capable of dissolving the electrolytes and the compounds intended to deposit can be used in the above reaction vessel and as specific examples, there are dichloromethane (CH Cl ), tetrahydrofuran (THF), acetonitrile (CH CN), benzonitrile (C H CN), propylene carbonate (1,2-propanediol cycliccarbonate), and toluene (C H
  • the amount of the solvents to be used is preferably 0.01 to 10 mM on the basis of the concentration of the compounds. If the concentration is too thin, there is a possibility that the electrochemical deposition is not performed properly and if it is too thick, problems may happen in connection with the control of the electrochemical deposition film thickness and voltage drop.
  • the electrolytes that can be used in the reaction vessel are dissolved in the above solvents and they are not limited to specific ones as long as they are able to ionize the compounds intended to deposit when power is applied, and as specific examples, there are Me NBF , Et NBF , Pr NBF , Bu NBF , Me NClO , Et NClO , Pr NClO , Bu NClO 4 , Me 4 NPF 6 , Et 4 NPF 6 , Pr 4 NPF 6 , Bu 4 NPF 6 , LiClO 4 , LiBF 4 , LiPF 6 , and LiBOB.
  • the concentration of the supporting electrolytes is preferably 50 mM to 500 mM. If the concentration of the electrolytes is too thin, such problems as voltage drop may happen.
  • any conventional substrates used to form organic thin layers in OLED devices can be used.
  • they can be a substrate with anode formed thereon; or a substrate on which anode and at least one layer from hole injection layer (HIL), hole transport layer (HTL), emitting layer (EML), hole blocking layer (HBL) and electron transport layer (ETL) are deposited in sequence.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emitting layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • any substrates used in common organic EL devices can be employed as the substrates and it is preferable to use organic substrates or clear plastic substrates with excellent clearness, surface flatness, easy handling and waterproof.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • SnO tin oxide
  • ZnO zinc oxide
  • the one or more organic layers among the hole injection layer (HIL), hole transport layer (HTL), emitting layer (EML), hole blocking layer (HBL) and electron transport layer (ETL) to be formed on the substrates to be deposited can be formed by known methods or by the electrochemical deposition of the invention.
  • the above organic layers are formed using the electrochemical deposition of the invention.
  • the electrochemical deposition is preferably used to form the organic thin layers in this step.
  • the cathode can be formed by any known methods and for example, the cathode can be formed by vacuum heat deposition of or sputtering metals for the formation of cathode.
  • metals for the formation of cathode there can be used lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- silver (Mg-Ag) and the like.
  • clear substances such as ITO or IZO can be used as cathode.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emitting layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the thickness of the organic thin layers formed through the electrochemical deposition in accordance with the present invention can be adjusted by power cycle control, depending on the required level and it is preferably 10 to 1,000 D and more preferably, 20 to 150 D.
  • power is applied preferably using CV (cyclic voltammetry). Voltage is applied in the range of voltage within potential window showing no oxidation-reduction of solvents or electrolytes or electrodes, and when CV is used, although there are slight variations in each compound, voltage is scanned starting from 0.30 V vs S.C.E. up to 1.65(+0.1) V vs S.C.E. at a voltage scan rate of 0.1 V/s and returned to 0.30 V vs S.C.E.
  • CV cyclic voltammetry
  • electrochemical deposition proceeds.
  • the thickness of thin layers of compounds can be adjusted by varying the number of cycles, the concentration of the compounds, voltage scan rate, voltage scan range and so on.
  • washing step or dry step can be further carried out, if required.
  • electrolyte substances that might be present on the organic thin layers, and those used as the solvent component of the reaction vessel are preferably used as the washing solution.
  • the dry step is not limited to specific ones, and any known dry methods that can be carried out after the formation of known organic thin layers of organic light emitting devices can be applied.
  • the concentration of the compound of the above formula can be 0.5 mM and the concentration of the electrolyte can be 0.1 M.
  • the substrate to be deposited can be a glass substrate with ITO as anode deposited thereon, a substrate of the glass substrate-ITO-hole injection layer being laminated in order, or a substrate of the glass substrate-ITO-hole injection layer- hole transport layer being laminated in order.
  • the compound dissolved in the reaction vessel is deposited onto the substrate to be deposited and the thickness to be deposited can be adjusted by the number of cycles of CV (cyclic voltammetry).
  • the substrate deposited with the above compound may be further deposited with one or more organic thin layers such as electron transport layer and electron injection layer, if necessary, after washing and dry and then, cathode is formed on the organic layers through vacuum heat deposition or sputtering, thereby completing an organic light emitting device.
  • the method for preparation of the organic thin layer of organic light emitting device through electrochemical deposition according to the invention has simple process by virtue of the use of monomolecular compounds that are purchased or easily prepared without requiring special equipments, has high productivity, can make it easy to control the thickness of thin layers to be prepared and can fundamentally improve erosion of the pre-formed organic thin layers that occurred in the preparation of two or more organic thin layers by spin coating.
  • the invention provides the organic thin layers of organic light emitting device prepared by the electrochemical deposition and organic light emitting devices comprising the organic thin layers as well.
  • the organic thin layers have excellent adhesion to substrates, have uniform surface because their thickness can be adjusted at molecular level, and have excellent morphology stability and especially, in case of the organic thin layers formed through consecutive electrochemical deposition of two or more layers, interfaces between layers are even, erosion due to solvents does not occur, adhesion between interfaces is strong and they have fine patterns.
  • the organic thin layers in accordance with the invention are not melted in most organic solvents, erosion due to solvents can be fundamentally reduced even in case of forming organic thin layers by known spin coating.
  • BAS 100 electrochemical analyzer was used for the CV experiment.
  • Three-electrode system - glassy carbon as a working electrode, platinum electric wire as a counter electrode and silver electric wire as a reference electrode - was used.
  • Methylene chloride that is neat, distilled and degassed was used as a solvent and 0.1 M tetra-normal-butylammonium hexafluorophosphate was used as an electrolyte.
  • Normal-butyllithium diluted in 1,4-dibromobenzene 2.5 M hexane was purchased from Aldrich Co., Ltd. and used without further purification.
  • Teflon magnetic stir bar 1,4-dibromobenzene (25.184 g, 200 mmol), carbazol (8.36 g, 50 mmol), K CO (13.82 g, 100 mmol), and CuSO (7.98 g, 50 mmol) were put in a 100-mL one-neck flask and stirred at 210 0 C for 16 hours without solvents. After the completion of the reaction, the mixture was diluted with methylenechloride and filtered and then, the filtered solution was washed with distilled water and brine. The thus obtained organic layer was dehydrated using MgSO .
  • Bromophenylcarbazol was converted into an organic lithium compound in tetrahydrofuran (THF) solvent using normal-butyllithium at -78 0 C and then reacted with trichlorosilane, dimethyldichloridesilane, and trichloromethylsilane to synthesize mono-, bis-, tirs-(9-(phenylcarbozol)) (Compound 4-6), respectively with yields of 40-75%.
  • Compound 5 and Compound 6 were separated through silica gel column and Compound 4 could be obtained by re- crystallization using ether without separation with column.
  • the method for preparation of the organic thin layer of organic light emitting device through electrochemical deposition according to the invention has simple process by virtue of the use of monomolecular compounds that are purchased or easily prepared without requiring special equipments, has high productivity, can make it easy to control the thickness of thin layers to be prepared and can fundamentally improve erosion of the pre-formed organic thin layers that occurred in the preparation of two or more organic thin layers by spin coating.
  • the organic thin layers in accordance with the invention have excellent adhesion to substrates, have uniform surface because their thickness can be adjusted at molecular level, and have excellent morphology stability and especially, in case of the organic thin layers formed through consecutive electrochemical deposition of two or more layers, interfaces between layers are even, erosion due to solvents does not occur, adhesion between interfaces is strong and they have fine patterns. Moreover, as they are not melted in most organic solvents, erosion due to solvents can be fundamentally reduced even in case of forming organic thin layers by known spin coating on the organic thin layers in accordance with the invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/KR2007/001721 2006-04-14 2007-04-10 Preparing method for organic thin layer of organic light emitting devices using electrochemical deposition WO2007119954A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2009505292A JP5113153B2 (ja) 2006-04-14 2007-04-10 電気化学的蒸着による有機発光素子の有機薄膜層形成方法
DE112007000924T DE112007000924T5 (de) 2006-04-14 2007-04-10 Verfahren zur Herstellung einer organischen Dünnschicht von organischen lichtemittierenden Vorrichtungen mittels elektrochemischer Abscheidung

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2006-0034296 2006-04-14
KR1020060034296A KR101299098B1 (ko) 2006-04-14 2006-04-14 전기화학적 증착을 통한 유기발광소자의 유기박막층형성방법

Publications (1)

Publication Number Publication Date
WO2007119954A1 true WO2007119954A1 (en) 2007-10-25

Family

ID=38609689

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2007/001721 WO2007119954A1 (en) 2006-04-14 2007-04-10 Preparing method for organic thin layer of organic light emitting devices using electrochemical deposition

Country Status (4)

Country Link
JP (1) JP5113153B2 (ko)
KR (1) KR101299098B1 (ko)
DE (1) DE112007000924T5 (ko)
WO (1) WO2007119954A1 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103881067A (zh) * 2012-12-24 2014-06-25 海洋王照明科技股份有限公司 一种聚合物蓝光主体材料及其制备方法与应用

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101352021B1 (ko) * 2006-05-17 2014-01-15 주식회사 동진쎄미켐 분자 내 비스(페닐카바졸)기를 가지는 실리콘계 화합물 및이를 이용한 유기발광소자의 유기박막층 형성방법
DE102012217574A1 (de) 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Phosphoroxo-Salze als n-Dotierstoffe für die organische Elektronik
KR102167045B1 (ko) * 2013-12-17 2020-10-19 삼성디스플레이 주식회사 실란계 화합물 및 이를 포함한 유기 발광 소자
KR101612319B1 (ko) 2014-08-28 2016-04-15 주식회사 네패스 시안계 호스트 화합물 및 이를 채용한 유기발광 소자
KR101775891B1 (ko) 2014-12-23 2017-09-12 주식회사 네패스 질소 헤테로 고리계 호스트 화합물 및 이를 채용한 유기발광 소자
CN107275521A (zh) * 2017-05-24 2017-10-20 华南理工大学 一种高分辨阵列有机薄膜的制备方法及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10168443A (ja) * 1996-12-17 1998-06-23 Sanyo Shinku Kogyo Kk 有機発光素子の正孔または電子輸送層等に用いられるフェニルカルバゾール誘導体
JP2002008860A (ja) * 2000-04-18 2002-01-11 Mitsubishi Chemicals Corp 有機電界発光素子
US6653654B1 (en) * 2002-05-01 2003-11-25 The University Of Hong Kong Electroluminescent materials
EP1480281A2 (en) * 2003-05-22 2004-11-24 Samsung SDI Co., Ltd. Electroluminescent display device

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0845668A (ja) * 1994-07-27 1996-02-16 Casio Comput Co Ltd 電界発光素子の製造方法
JPH0997679A (ja) * 1995-09-28 1997-04-08 Casio Comput Co Ltd 電界発光素子の製造方法
KR100522697B1 (ko) * 2003-09-22 2005-10-20 삼성에스디아이 주식회사 4,4'-비스(카바졸-9-일)-비페닐계 실리콘 화합물 및 이를이용한 유기 전계 발광 소자

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10168443A (ja) * 1996-12-17 1998-06-23 Sanyo Shinku Kogyo Kk 有機発光素子の正孔または電子輸送層等に用いられるフェニルカルバゾール誘導体
JP2002008860A (ja) * 2000-04-18 2002-01-11 Mitsubishi Chemicals Corp 有機電界発光素子
US6653654B1 (en) * 2002-05-01 2003-11-25 The University Of Hong Kong Electroluminescent materials
EP1480281A2 (en) * 2003-05-22 2004-11-24 Samsung SDI Co., Ltd. Electroluminescent display device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103881067A (zh) * 2012-12-24 2014-06-25 海洋王照明科技股份有限公司 一种聚合物蓝光主体材料及其制备方法与应用

Also Published As

Publication number Publication date
KR20070102305A (ko) 2007-10-18
KR101299098B1 (ko) 2013-08-28
DE112007000924T5 (de) 2009-09-03
JP5113153B2 (ja) 2013-01-09
JP2009533816A (ja) 2009-09-17

Similar Documents

Publication Publication Date Title
KR100611885B1 (ko) 호스트용 화합물과 도판트용 화합물이 연결된 유기 금속화합물, 이를 이용한 유기 전계 발광 소자 및 그의제조방법
JP5281270B2 (ja) イリジウム錯体化合物、それを用いた有機エレクトロルミネッセンス素子およびその用途
CN107011183B (zh) 新颖化合物及包含其的有机电子装置
KR101434632B1 (ko) 아릴아민 화합물 및 전자 장치
WO2007119954A1 (en) Preparing method for organic thin layer of organic light emitting devices using electrochemical deposition
WO2019143153A1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
JP2013509390A (ja) 電子材料のための新規化合物およびこれを使用する有機電子素子
CN107382926B (zh) 化合物及其有机电子装置
JPWO2006070817A1 (ja) 有機ホウ素π電子系化合物及びその合成中間体
KR20110086043A (ko) 발광다이오드용 호스트 물질
CN107556310A (zh) 咪唑衍生物、包含该咪唑衍生物的材料和有机电致发光器件
WO2018216913A1 (ko) 신규한 헤테로고리 화합물 및 이를 이용한 유기발광 소자
WO2019103423A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
CN108864195A (zh) 一种金属铱配合物及其有机发光器件
WO2007132986A1 (en) Silicon type compound having bisphenylcarbazol in molecule and method for preparing organic thin layer of organic light emitting devices using the same
CN103468245A (zh) 一种具有载流子传输能力的oled材料及其制备方法和应用
WO2019078443A1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2019093623A1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20190082236A (ko) 고분자 전하 수송층 및 이를 포함하는 유기 전자 디바이스
EP4230630A1 (en) Novel compound and organic light emitting device comprising same
JP2023547680A (ja) 新規な化合物およびこれを利用した有機発光素子
CN109912575B (zh) 一种以含氮五元杂环为核心的化合物及其在有机电致发光器件上的应用
CN105348325A (zh) 一种含有螺芴结构的双膦杂环有机电致发光化合物、合成方法及其应用
KR20070111189A (ko) 전기화학적 증착을 통한 유기발광소자의 유기박막층형성방법
JP7334886B2 (ja) 新規な化合物およびこれを利用した有機発光素子

Legal Events

Date Code Title Description
DPE2 Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07745884

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2009505292

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 1120070009241

Country of ref document: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07745884

Country of ref document: EP

Kind code of ref document: A1

RET De translation (de og part 6b)

Ref document number: 112007000924

Country of ref document: DE

Date of ref document: 20090903

Kind code of ref document: P