WO2011136484A1 - Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent associé - Google Patents

Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent associé Download PDF

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WO2011136484A1
WO2011136484A1 PCT/KR2011/002526 KR2011002526W WO2011136484A1 WO 2011136484 A1 WO2011136484 A1 WO 2011136484A1 KR 2011002526 W KR2011002526 W KR 2011002526W WO 2011136484 A1 WO2011136484 A1 WO 2011136484A1
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alkyl
aryl
organic electroluminescent
heteroaryl
cycloalkyl
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PCT/KR2011/002526
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English (en)
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Young Gil Kim
Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Sung Min Kim
Bong Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to JP2013507866A priority Critical patent/JP5782503B2/ja
Priority to CN201180031554.2A priority patent/CN102958906B/zh
Publication of WO2011136484A1 publication Critical patent/WO2011136484A1/fr

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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as a blue electroluminescent material and an organic electroluminescent device employing the same as a dopant.
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials.
  • the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure.
  • Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained and it is expected that a color display device will be realized.
  • the distryl compound system of Idemitsu-Kosan which is known to have highest efficiency up to now, has 6 lm/W power efficiency and beneficial device lifetime of more than 30,000 hr.
  • the lifetime is merely several thousand hours, owing to decrease of color purity over operation time.
  • blue electroluminescence it becomes advantageous from the aspect of the luminous efficiency, if the electroluminescent wavelength is shifted a little toward longer wavelength.
  • it is not easy to apply the material to a display of high quality because of unsatisfactory color purity in blue.
  • the research and development of such materials are urgent because of the problems in color purity, efficiency and thermal stability.
  • the object of the present invention is to provide organic electroluminescent compounds having the backbone with appropriate color coordinates to provide better luminous efficiency and device life compared with conventional dopant material, while overcoming the problems described above, and a highly efficient and long life organic electroluminescent device using the organic electroluminescent compounds.
  • novel organic electroluminescent compounds and an organic electroluminescent device using the same.
  • the organic electroluminescent compound is a compound represented by Chemical Formula 1. With superior luminescence efficiency in blue color and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
  • Ar 1 through Ar 4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or , or Ar 1 and Ar 2 or Ar 3 and Ar 4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR 21 , O, S or SiR 22 R 23 ;
  • R 1 through R 6 and R 11 through R 13 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C1-C30)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl;
  • R 21 through R 23 independently represent (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, halogen, cyano, (C6-C30)aryl, (C2-C30)heteroaryl, tri(C1-C30) alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl, or R 22 and R 23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring; and
  • the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 1 through R 6 ; the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar 1 through Ar 4 ; the fused ring formed by the linkage of each of Ar 1 and Ar 2 or Ar 3 and Ar 4 ; and the alkyl, haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 21 through R 23 may be further substituted by one or more substituent(s) selected
  • alkyl alkoxy and other substituents containing “alkyl” moiety include both linear and branched species.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • Specific examples include monocyclic heteroaryl such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl
  • the alkyl moiety of "(C1-C30)alkyl, (C1-C30)alkoxy, mono or di(C1-C30)alkylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, halo(C1-C30)alkyl, (C1-C30)alkylthio, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, mono or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl" or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the heteroaryl of "(C3-C30)heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the cycloalkyl of "(C3-C30)cycloalkyl” may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the alkylene or alkenylene of "(C3-C30)alkylene or alkenylene” may have 3 to 20 carbon atoms, more specifically 3 to 10 carbon atoms.
  • organic electroluminescent compound according to the present invention may include compounds represented by Chemical Formula 2 below.
  • R 5 and R 6 independently represent hydrogen, (C6-C30)aryl or (C2-C30)heteroaryl;
  • Ar 1 through Ar 4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or , or Ar 1 and Ar 2 or Ar 3 and Ar 4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR 21 , O, S or SiR 22 R 23 ;
  • R 21 through R 23 independently represent (C1-C30)alkyl or (C6-C30)aryl, or R 22 and R 23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring;
  • alkyl or aryl of R 21 through R 23 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30)aryl
  • Ar 1 and Ar 2 and Ar 3 and Ar 4 are independently linked via alkylene or alkenylene are independently selected from following structures, but are not limited thereto:
  • R 21 through R 25 independently represent (C1-C30)alkyl or (C6-C30)aryl.
  • Ar 1 through Ar 4 are independently selected from following structures, but are not limited thereto:
  • organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but the present invention is not limited thereto:
  • organic electroluminescent compound according to the present invention may be prepared as shown in Scheme 1 below but is not limited thereto.
  • Ar 1 through Ar 4 and R 1 through R 6 are the same as defined in Chemical Formula 1.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) of Chemical Formula 1.
  • the organic layer comprises an electroluminescent layer including one or more host(s) when one or more organic electroluminescent compounds of Chemical Formula 1 are used as the electroluminescent dopant.
  • the host used in the organic electroluminescent device of the present invention is not particularly limited but may be selected from the compounds represented by Chemical Formula 3 or 4 below.
  • a specific structure of the host compound of Chemical Formula 3 or 4 below is exemplified in Paragraphs ⁇ 162> to ⁇ 210> of KR Patent Application No. 10-2008-0060393 but is not limited thereto.
  • L 1 represents (C6-C30)arylene or (C4-C30)heteroarylene
  • L 2 represents anthracenylene
  • Ar 11 through Ar 14 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar 11 through Ar 14 may be further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)aryl
  • a, b, c and d independently represent an integer from 0 to 4.
  • the electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer that two or more layers are laminated.
  • the doping concentration may be 0.5 to 10 wt%.
  • the electroluminescent host according to the present invention provides excellent conductivity for holes and electrons, as well as very superior stability and remarkably improved luminescence efficiency and operation life. Accordingly, when the compound represented by Chemical Formula 3 or 4 is selected as an electroluminescent host, it may considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
  • the organic electroluminescent device may comprise the organic electroluminescent compound of Chemical Formula 1 and may comprise one or more compound(s) selected from the group consisting of arylamine or styrylamine compounds.
  • arylamine or styrylamine compounds are provided in Paragraph Nos. ⁇ 212> to ⁇ 224> of KR Patent Application No. 10-2008-0060393 but are not limited thereto.
  • the organic layer may further comprise one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements in addition to the organic electroluminescent compound of Chemical Formula 1.
  • the organic layer may comprise an electroluminescent layer and a charge generating layer.
  • An organic electroluminescent device having a pixel structure of independent light-emitting mode may be embodied, wherein the organic electroluminescent device including the organic electroluminescent compound represented by Chemical Formula 1 of the present invention is taken as a subpixel and one or more subpixel(s) including one or more metal compound(s) selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag are patterned in parallel at the same time.
  • the organic layer may include, in addition to the organic electroluminescent compound, one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. An operation stability may be attained therefrom.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • an organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
  • Organic electroluminescent Compounds 1 to 67 were prepared according to Preparation Example 1.
  • Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was vapor-deposited on the formed layers.
  • DNA (Examples 1 to 3) of a following structure was placed in one cell of the vacuum vapor deposition apparatus and the compound according to the present invention was placed in another cell. Then, an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at a deposition rate of 100:3.
  • Each compound used in the OLED device as an electroluminescent material was purified by vacuum sublimation at 10 -6 torr.
  • the luminous efficiencies of the OLED comprising the organic electroluminescent compounds according to the present invention in the Examples 1-3 were measured at 1,000 cd/m 2 , respectively, and the results are shown in Table 2.
  • the organic electroluminescent compounds of the present invention provide deep blue color. That, when a blue color is required for realizing the color close to the NTSC standard in the organic electroluminescent display, the organic electroluminescent compounds of the present invention may be useful. Since phenanthrene derivatives have high glass transition temperature, superior thermal stability is acquired. As described above, the organic electroluminescent compound of the present invention is used as a blue light-emitting material having high purity.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

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Abstract

La présente invention concerne de nouveaux composés organiques électroluminescents et un dispositif organique électroluminescent associé. Puisque le composé organique électroluminescent présente une efficacité lumineuse élevée dans la couleur bleue et une excellente propriété de vie, il peut être utilisé pour fabriquer des OLED présentant une durée de vie utile très supérieure.
PCT/KR2011/002526 2010-04-30 2011-04-11 Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent associé WO2011136484A1 (fr)

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CN102958906A (zh) 2013-03-06
KR20110121147A (ko) 2011-11-07
CN102958906B (zh) 2015-11-25
TW201213308A (en) 2012-04-01
JP5782503B2 (ja) 2015-09-24

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