WO2007119998A1 - Composé diimidazole et dispositif organique électroluminescent comprenant ce dernier - Google Patents

Composé diimidazole et dispositif organique électroluminescent comprenant ce dernier Download PDF

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Publication number
WO2007119998A1
WO2007119998A1 PCT/KR2007/001851 KR2007001851W WO2007119998A1 WO 2007119998 A1 WO2007119998 A1 WO 2007119998A1 KR 2007001851 W KR2007001851 W KR 2007001851W WO 2007119998 A1 WO2007119998 A1 WO 2007119998A1
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WO
WIPO (PCT)
Prior art keywords
formula
organic electroluminescent
compound
diimidazole
electroluminescent device
Prior art date
Application number
PCT/KR2007/001851
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English (en)
Inventor
Chan-Seok Park
Sang-Ook Kang
Chong-Chan Lee
Jae-Ho Jeong
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
Publication of WO2007119998A1 publication Critical patent/WO2007119998A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Definitions

  • the present invention relates to a diimidazole compound and an organic electroluminescent device using the same and more particularly, to a diimidazole compound having excellent blue luminescent characteristics and hole transmission characteristics and at the same time, capable of not only being used as a blue luminescent material or used as a host to a variety of phosphorescent or fluorescent dopants such as red, green, blue and white but also enabling high efficient luminescence when applied to organic electroluminescent devices and conferring such performances as low voltage, high brightness and long lifetime and an organic electroluminescent device using the same.
  • Background Art
  • organic electroluminescent devices have a structure of an anode which is formed on the top of a substrate, a hole transport layer, emitting layer, electron transport layer, and cathode which are formed on the anode in sequence.
  • the hole transport layer, emitting layer and electron transport layer are organic thin layers consisting of organic compounds.
  • the organic electroluminescent devices having the above structure have the following driving mechanism.
  • the present invention provides a diimidazole compound represented by formula 1 :
  • X is a substituted or unsubstituted alkyl group of 1 to 50 carbon atoms, a substituted or unsubstituted aryl group of 6 to 50 carbon atoms, a substituted or unsubstituted hetero ring group of 6 to 50 carbon atoms or a substituted or unsubstituted heterocyclic ring group of 6 to 50 carbon atoms.
  • the invention provides an organic thin layer of organic electroluminescent device formed from the above diimidazole compound.
  • the invention provides an organic electroluminescent device comprising at least one organic thin layer between anode and cathode characterized in that it comprises at least one or more layers of the above-mentioned organic thin layers.
  • the invention provides a display device comprising the above organic electroluminescent device.
  • the diimidazole compounds in accordance with the present invention have excellent blue luminescent characteristics and hole transmission characteristics and at the same time, they not only can be used as a blue luminescent material or used as a host to a variety of phosphorescent or fluorescent dopants such as red, green, blue and white but also enable high efficient luminescence when applied to organic electroluminescent devices and can confer such performances as low voltage, high brightness and long lifetime.
  • the diimidazole compound represented by above formula 1 of the invention have excellent blue luminescent characteristics and hole transmission characteristics and are suitable to be used as blue luminescent materials and phosphorescent and fluorescent host materials.
  • -X- can be a substituted or unsubstituted alkyl group of 1 to
  • alkyl group of 1 to 50 carbon atoms 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, azindole, alkyl group of 1 to 50 carbon atoms, alken
  • the unsubstituted aryl group in above refers to a carbocycle aromatic system of 6 to
  • 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.
  • diimidazole compounds of the present invention include compounds of the following formulae 1-1 to 1-8:
  • the diimidazole compounds of the invention as described above can be prepared by reacting imidazole and potassium hydroxide and adding a compound having di- bromomethyl to the reaction solution and then reacting them.
  • dibromomethyl there can be used 4,4'-bis(dibromomethyl)bisphenyl, l,4-bis(dibromomethyl)benzene, 1 ,3,5-tris(bromomethyl)benzene, or 2,4,6-tris(dibromomethyl)- 1 ,3,5-triazine.
  • the diimidazole compounds of the present invention can be prepared by methods of the following reaction formulae 1 to 4, but they are merely embodiments for preparing the diimidazole compounds in accordance with the invention and they do not limit the method for preparation of the diimidazole compounds in any way.
  • the invention provides an organic thin layer of organic electroluminescent device formed from the diimidazole compounds represented by the above formula 1 according to the invention and an organic electroluminescent device comprising at least one or more layers of the organic thin layers.
  • the organic electroluminescent devices are prepared by the following procedures.
  • the organic electroluminescent devices can comprise one or more organic thin layers such as hole injection layer (HIL), hole transport layer (HTL), emitting layer (EML), electron transport layer (ETL) and electron injection layer (EIL) between anode and cathode.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emitting layer
  • ETL electron transport layer
  • EIL electron injection layer
  • anode is formed on the top of substrates by depositing materials for anode electrode having high work function.
  • Any substrates used in common organic electroluminescent devices can be employed as the substrates and it is preferable to use organic substrates or clear plastic substrates with excellent mechanical strength, thermal stability, clearness, surface flatness, easy handling and waterproof.
  • materials for anode electrode indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ), zinc oxide (ZnO), etc. can be used.
  • the materials for anode electrode can be deposited by conventional anode forming methods and in particular, they can be deposited by deposition method or sputtering method.
  • hole injection layer (HIL) materials can be formed on the top of the anode electrode by methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, but the formation by vacuum deposition is advantageous because uniform film quality can be easily obtained and pin hole is not likely to occur.
  • deposition conditions can be varied by compounds to be used as materials for hole injection layer, structure and thermal characteristics of intended hole injection layer, etc.
  • Any hole injection layer materials can be used and for example, phthalocyanine compounds such as cupper phthalocyanine disclosed in US Patent No. 4,356,429, starbust type amine derivatives, TCTA, m- MTD ATA, m- MTD APB (Advanced Material, 6, p677 (1994)), etc. can be used as hole injection layer materials.
  • phthalocyanine compounds such as cupper phthalocyanine disclosed in US Patent No. 4,356,429, starbust type amine derivatives, TCTA, m- MTD ATA, m- MTD APB (Advanced Material, 6, p677 (1994)), etc. can be used as hole injection layer materials.
  • hole transport layer (HTL) materials can be formed on the top of the hole injection layer by methods such as vacuum deposition, spin coating, casting and LB method, but the formation by vacuum deposition is advantageous because uniform film quality can be easily obtained and pin hole is not likely to occur.
  • the conditions can be varied by the compounds to be used, but in general, they are preferably chosen within almost the same conditions as used for the formation of the hole injection layer.
  • the hole transport layer materials are not limited to specific ones and for example, the diimidazole compounds represented by formula 1 according to the invention can be used or any conventional materials known to be used in the hole transport layers can be suitably used. Particularly, in addition to the diimidazole compounds represented by formula 1 according to the invention, there can be used carbazol derivatives such as N- phenylcarbazol and polyvinylcarbazol, and conventional amine derivatives having an aromatic condensed ring such as
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[l,l-biphenyl]-4,4'-diamine
  • -NPD N.N'-di(naphthalene-l-yl)-N,N'-diphenyl benzidine
  • emitting layer (EML) materials can be formed on the top of the hole transport layer by methods such as vacuum deposition, spin coating, casting and LB method, but the formation by vacuum deposition is advantageous because uniform film quality can be easily obtained and pin hole is not likely to occur.
  • the conditions can be varied by the compounds to be used, but in general, they are preferably chosen within almost the same conditions as used for the formation of the hole injection layer.
  • the emitting layer materials are not limited to specific ones and for example, the diimidazole compounds represented by formula 1 according to the invention can be used alone or they can be used as a host.
  • phosphorescent or fluorescent dopants can be used together to form the emitting layer.
  • fluorescent dopants IDE102 or IDE105 commercially available from Idemitsu Co., Ltd.
  • the green phosphorescent dopant Ir(ppy)3(fac tris(2-phenylpyridine) iridium), the blue phosphorescent dopant F2Irpic(iridium(ffl)bis[4,6-di-fluorophenyl)-pyridinato-N,C2'] picolinate) and the red phosphorescent dopant RD 61 can be jointly vacuum deposited (doping).
  • the doping concentration of the dopants is not especially limited but it is preferred that the concentration of the dopants is 0.01 to 15 parts by weight of 100 parts by weight of the host. If the content of the dopants is less than 0.01 parts by weight, the doping amount is not sufficiently enough for color development, and if it exceeds 15 parts by weight, efficiency may be rapidly reduced due to concentration quenching.
  • hole blocking layer (HBL) materials are further laminated by vacuum deposition or spin coating method to prevent triplet excited state or hole from diffusing into the electron transport layer (ETL).
  • the hole blocking materials are not limited to specific ones and any known materials that have been used as hole blocking materials can be suitably used.
  • oxadiazole derivatives or triazole derivatives phenanethroline derivatives, or hole blocking materials described in Japan Patent Laid- Open No. 11-329734 (Al)
  • BaIq phenanthroline type compounds
  • the electron transport layer can be formed by methods such as vacuum deposition, spin coating, and casting and preferably, it is formed by the vacuum deposition.
  • the electron transport layer materials function to stably transport electrons injected from electron injection electrode (cathode) and are not limited to specific ones and for example, quinoline derivatives, especially tris(8-quinolinolate)aluminum (Alq3) can be employed. Also, on the top of the electron transport layer can be laminated electron injection layer (EIL) which has materials capable of making the injection of electrons from cathode easy and as the electron injection layer materials, such materials as LiF, NaCl, CsF, Li O, and BaO can be used.
  • EIL electron injection layer
  • the deposition conditions for the electron transport layer can be varied by the compounds to be used, but in general, they are preferably chosen within almost the same conditions as used for the formation of the hole injection layer.
  • EIL electron injection layer
  • the electron injection layer can be formed with ordinary electron injection layer materials by methods such as vacuum deposition, spin coating, and casting, and particularly, it is preferably formed by the vacuum deposition.
  • metals for the formation of cathode are formed on the top of the electron injection layer by methods such as vacuum deposition or sputtering method and this is used as cathode.
  • metals for the formation of cathode there can be used metals, alloys, electrically conductive compounds, and mixture thereof having low work function.
  • transmissive cathode using ITO or IZO can be used.
  • the organic electroluminescent devices of the invention not only can be organic electroluminescent devices having the structure of anode, hole injection layer (HIL), hole transport layer (HTL), emitting layer (EML), electron transport layer (ETL), electron injection layer (EIL) and cathode but also can be embodied in organic electroluminescent devices having various structures, and if necessary, it is possible to form another intermediate layers of one or two layers.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron transport layer
  • EIL electron injection layer
  • the thickness of the organic thin layers formed in accordance with the present invention can be adjusted, depending on the required level and it is preferably 10 to 1,000 D and more preferably, 20 to 150 D.
  • the diimidazole compounds in accordance with the present invention have excellent blue luminescent characteristics and hole transmission characteristics and at the same time, they not only can be used as a blue luminescent material or used as a host to a variety of phosphorescent or fluorescent dopants such as red, green, blue and white but also enable high efficient luminescence when applied to organic electroluminescent devices and can confer such performances as low voltage, high brightness and long lifetime.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne un composé diimidazole et un dispositif organique électroluminescent qui comprend ce dernier. Plus particulièrement, les composés diimidazole selon l'invention présentent d'excellentes caractéristiques de luminescence bleue et des caractéristiques de transmission des trous, de surcroît on peut les utiliser non seulement en tant que matière luminescente bleue ou en tant qu'hôte pour divers dopants phosphorescents ou fluorescents tels que le rouge, le vert, le bleu et le blanc mais ils produisent également une luminescence très efficiente lorsqu'on les utilise dans des dispositifs organiques électroluminescents et peuvent conférer des propriétés telles qu'une faible tension, une haute luminosité et une longue durée de vie.
PCT/KR2007/001851 2006-04-19 2007-04-17 Composé diimidazole et dispositif organique électroluminescent comprenant ce dernier WO2007119998A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020060035186A KR101307497B1 (ko) 2006-04-19 2006-04-19 디이미다졸계 화합물 및 이를 이용한 유기발광소자
KR10-2006-0035186 2006-04-19

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0260744A2 (fr) * 1986-09-15 1988-03-23 Janssen Pharmaceutica N.V. Dérivés de benzimidazoles substitués par un reste 1H-imidazol-1-ylméthyl
EP0371564A2 (fr) * 1988-11-29 1990-06-06 Janssen Pharmaceutica N.V. Dérivés de (1H-azol-1-yl-méthyl)-quinoline, -quinazoline, ou -quinoxaline substitués

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0260744A2 (fr) * 1986-09-15 1988-03-23 Janssen Pharmaceutica N.V. Dérivés de benzimidazoles substitués par un reste 1H-imidazol-1-ylméthyl
EP0371564A2 (fr) * 1988-11-29 1990-06-06 Janssen Pharmaceutica N.V. Dérivés de (1H-azol-1-yl-méthyl)-quinoline, -quinazoline, ou -quinoxaline substitués

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KR20070103529A (ko) 2007-10-24

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