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WO2010062107A1 - Organic electroluminscent device using electroluminescent compounds - Google Patents

Organic electroluminscent device using electroluminescent compounds Download PDF

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Publication number
WO2010062107A1
WO2010062107A1 PCT/KR2009/006980 KR2009006980W WO2010062107A1 WO 2010062107 A1 WO2010062107 A1 WO 2010062107A1 KR 2009006980 W KR2009006980 W KR 2009006980W WO 2010062107 A1 WO2010062107 A1 WO 2010062107A1
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Prior art keywords
alkyl
compound
substituent
ring
heteroaryl
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PCT/KR2009/006980
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French (fr)
Inventor
Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Gracel Display Inc
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Gracel Display Inc
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Priority claimed from KR1020090042825A external-priority patent/KR20100059653A/en
Application filed by Gracel Display Inc filed Critical Gracel Display Inc
Priority to CN2009801475043A priority Critical patent/CN102227486A/en
Priority to JP2011537375A priority patent/JP2012510154A/en
Publication of WO2010062107A1 publication Critical patent/WO2010062107A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
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    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
    • C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
    • C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
    • C07D223/26—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a double bond between positions 10 and 11
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    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
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    • C07D333/76—Dibenzothiophenes
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • 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
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    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Definitions

  • the present invention relates to an electroluminescent device in which an organic layer is interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1 and one or more host compound (s) represented by Chemical Formula 2:
  • electroluminescence (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • EL electroluminescence
  • Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as electroluminescent materials [Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) , an electron and a hole are paired and emit light as the electron-hole pair is extinguished.
  • the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color. Since an organic EL device can exhibit green, blue and red colors, it is drawing a lot of attention as a full-color display device of the next generation.
  • Aprocess of manufacturing an organic EL device is as follows: (1) First, an anode material is coated on a transparent substrate. Indium tin oxide (ITO) is frequently used as the anode material.
  • ITO Indium tin oxide
  • a hole injection layer (HIL) is formed thereupon.
  • the hole injection layer is typically formed by coating copper phthalocyanine (CuPc) to a thickness of 10 to 30 nm.
  • a hole transport layer (HTL) is formed.
  • the hole transport layer is formed by depositing 4, 4 '-bis [N- (1-naphthyl) -N-phenylamino]biphenyl (NPB) to a thickness of about 30 to 60 nm.
  • An organic electroluminescent layer (organic emitting layer) is formed thereupon. If required, a dopant is added thereto. In case of green electroluminescence, an organic emitting layer is formed frequently by depositing tris (8-hydroxyquinolato) aluminum (AIq 3 ) to a thickness of about 30 to 60 nm. For the dopant, N-methylquinacridone (MQD) is commonly used.
  • An electron transport layer (ETL) and an electron injection layer (EIL) are formed sequentially, or an electron injection/transport layer is formed thereupon. In case of green electroluminescence, the ETL and/or EIL may be unnecessary because Alq3 has good electron transport ability.
  • a cathode is formed, and, finally, a protective layer is formed thereupon.
  • the electroluminescent material In an organic EL device, the most important factor affecting such quality as luminous efficiency, life property, etc. is the electroluminescent material.
  • Several requirements of the electroluminescent material include high fluorescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform and thin film, and good stability.
  • Organic electroluminescent materials may be roughly classified into high-molecular-weight materials and low-molecular-weight materials .
  • the low-molecular-weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure.
  • Chelate complexes such as tris (8-quinolato) aluminum, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from the blue to the red region can be obtained using these materials, and the realization of full-color display devices is being expected.
  • the present inventors have invented an electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, the organic layer comprising a combination of specific compounds, in order to realize an electroluminescent device having
  • An object of the present invention is to provide an electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more
  • Another object of the present invention is to provide an electroluminescent device having excellent luminous efficiency, superior color purity, low driving voltage and good operation life.
  • the electroluminescent device according to the 135 present invention comprises an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1 and one or more host compound (s) represented by Chemical Formula 2:
  • Ar 1 through Ar 4 independently represent (C6-C30)aryl with or without substituent or (C3-C30) heteroaryl with or without substituent or each of them may be linked to an adjacent substituent via
  • L represents (C3-C30) heteroarylene with or without substituent
  • Ar 11 , Ar 12 and R 1 I through R 1 S independently represent hydrogen, (C6-C30)aryl with or without substituent or (C3-C30) heteroaryl with or without substituent, with the proviso that at least one of Rn through
  • Ri 8 is linked to an adjacent substituent via or to form a fused ring; the substituent substituted at the aryl or heteroaryl of Ari through Ar 4 , Arn, Ar i2 and Rn through Ri 8 and the heteroarylene or stilbenylene of L is one or more substituent (s) selected from a group 160 consisting of deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30) bicycloalky
  • 175 represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, 5- to
  • hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring; the aromatic ring or heteroaromatic ring of the ring A, ring B, ring C and ring D and the alkyl, aryl, heteroaryl, heterocycloalkyl,
  • 190 cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl, alkylcarbonyl or arylcarbonyl of R 1 through R4, R21 through R24 and R31 through R 38 may be further substituted by one or more substituent (s)
  • 195 selected from deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C4-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl,
  • An represents anthracenylene with or without one or more 210 substituent (s) or -Zi-LiOo-Z 2 -;
  • L 10O represents (C6-C30) arylene or (C5-C30) heteroarylene with or without one or more substituent (s) ;
  • Ario and Ar 2O independently represent (C6-C30) aryl with or without 215 substituent or (C5-C30) heteroaryl with or without substituent; the substituent substituted at An, Ario, Ar2o or L100 is one or more selected from deuterium, halogen, (C1-C30) alkyl, halo(Cl-C30)alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or
  • 220 more heteroatom(s) selected from N, O and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl,
  • substituents including "alkyl” moiety may be either linear or branched.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single
  • 235 bond (S) Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • ring backbone atoms being carbon. It maybe 5- or 6-memberedmonocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with abenzene ring, andmaybe partially saturated. Further, theheteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s)
  • 250 in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt.
  • Specific examples include monocyclic heteroaryl suchasfuryl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl,
  • N-oxide thereof e.g., pyridy
  • arylene includes those formed as identical or different arylenes are fused
  • heteroarylene 265 includes those formed as identical or different heteroarylenes are fused.
  • (Cl-C30)alkyloxycarbonyloxy, (C1-C30) alkylcarbonyloxy, etc.” may have 1 to 20 carbon atoms, specifically 1 to 10 carbon atoms.
  • the heteroaryl of “ (C3-C30) heteroaryl” may have 4 to 20 carbon atoms, specifically 4 to 12 carbon atoms.
  • the cycloalkyl of “ (C3-C30) cycloalkyl” may have 280 3 to 20 carbon atoms, specifically 3 to 7 carbon atoms .
  • the alkenyl or alkynyl of " (C2-C30) alkenyl or alkynyl” may have 2 to 20 carbon atoms, specifically 2 to 10 carbon atoms.
  • a dopant may provide good, high-efficiency EL characteristics through improved electron density distribution. Further, it can overcome the problems associated with the existing materials, i.e., decrease of initial efficiency, short operation life, etc., and can provide high-performance EL characteristics with high 290 efficiency and long operation life for individual colors.
  • R 41 through R 6 g independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from
  • R 42 and R 43 may be linked via (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
  • L is selected from the following structures, but not limited thereto: wherein
  • Ar u , Ar i2 , Ri ? and R i8 are the same as defined in Chemical Formula 1 ;
  • R 7 i through R 79 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,
  • the dopant compound represented by Chemical Formula 1 may be exemplified by the following compounds, but not limited thereto :
  • the host compound represented by Chemical Formula 2 may be exemplified by the compounds represented by Chemical Formulas 3 to 5:
  • R ⁇ i and R 82 independently represent (C6-C60) aryl
  • (C4-C60) heteroaryl 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S or (C3-C60) cycloalkyl,
  • R ⁇ 3 through R 8 6 independently represent hydrogen, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60)aryl, and the heteroaryl, cycloalkyl or aryl of R 83 through
  • R 86 may be further substituted by one or more substituent (s) selected 375 from a group consisting of (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (Cl-C ⁇ O)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl;
  • G 1 and G 2 independently represent a chemical bond or 380 (C6-C6Q) arylene with or without one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl,
  • Ar 30 and Ar 4 O independently represent (C4-C60) heteroaryl or aryl selected from the following structures:
  • the aryl or heteroaryl of Ar3 0 and Ar ⁇ 0 may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;
  • Lioi represents (C6-C60) arylene, (C4-C60) heteroarylene or a 390 compound of the following formula:
  • the arylene or heteroarylene of Lioi may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;
  • R 91 through R 94 independently represent hydrogen, (C1-C60) alkyl or (C6-C60) aryl, or each of themmay be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic ring;
  • R 95 through R 9 e independently represent hydrogen, (C1-C60) alkyl
  • Lio2 represents anthracenylene
  • Lio3 and L104 independently represent a chemical bond, (Cl-C ⁇ O)alkyleneoxy, (C1-C60) alkylenethio, (C6-C60) aryleneoxy, (C6-C60)arylenethio, (C6-C60) arylene or (C3-C60) heteroarylene 410 containing one or more heteroatom(s) selected from N, O and S;
  • Ar 50 represents (C6-C60)aryl or (C5-C60) heteroaryl with or without one or more substituent (s) selected from deuterium, halogen,
  • (C1-C60) alkyl halo (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl 415 containing one or more heteroatom (s) selected from N, 0 and S,
  • (C3-C60)cycloalkyl tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,
  • Rioi through Ri O6 independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl,
  • the host compound represented by any of Chemical Formulas 3 to 5 may be exemplified by the following compounds, but not limited thereto:
  • the electroluminescent layer means a layer where electroluminescence occurs. It may be either a single layer or may
  • the electroluminescent device according to the present invention comprises the electroluminescent compounds represented by Chemical
  • Formula 1 and Chemical Formula 2 may further comprise one or more compound (s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time.
  • arylamine compound or the styrylarylamine compound are disclosed in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or
  • the organic layer may further comprise, in addition to the electroluminescent compounds represented by Chemical Formulas 1 and 2, one or more metal (s) selected from a group consisting of organic
  • the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
  • the organic layer may further comprise, in addition to the electroluminescent compounds represented by Chemical Formulas
  • one or more organic compound layer (s) emitting blue, green and red light at the same time to form a white-emitting electroluminescent device examples include:
  • a 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)
  • a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent layer.
  • a driving stability may be attained
  • the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1-5), SiON, SiAlON, etc.
  • the metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • 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 may be placed on the inner surface of one or both electrode (s) among the pair of electrodes.
  • the oxidative dopant include various Lewis acids and acceptor compounds .
  • Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
  • a white-emitting electroluminescent device having two or more electroluminescent layer (s) maybe fabricated
  • Compound 2-2 (9.4 g, 29.0 mmol) was obtained from Compound 2-1 in the same manner as the preparation of Compound 1-2 in Preparation Example 1. 560 Preparation of Compound 2-3 Compound 2-2 (50 g, 0.17 mol) was added to a flask and stirred for 10 minutes after adding AcOH (1 L). After adding H 3 PO 2 (380 g, 5.76 mol) and HI (781 g, 6.11 mol), the mixture was stirred at 150 0C for one day. Upon completion of reaction, after neutralization 565 with NaOH solution and HCl, the produced solid was filtered, added to ethyl acetate and recrystallized at 100 0 C under reflux. Compound 2-3 (40 g, 90%) was obtained.
  • Compound 3-3 (40 g, 90%) was obtained from Compound 3-2 in the same manner as the preparation of Compound 2-3 in Preparation Example 600 2.
  • Compound 4-4 was obtained from Compound 4-3 in the same manner as the preparation of Compound 1-3 in Preparation Example 1, except for using 2-bromonaphthalene. Compound 4-4 was used in the next 640 reaction without purification. Compound 4-5 (2.1 g, 3.56 mmol) was obtained from Compound 4-4 in the same manner as the preparation of Compound 1-4 in Preparation Example 1.
  • Compound 5-6 was obtained from Compound 5-5 in the same manner as the preparation of Compound 4-4 in Preparation Example 4. Compound 5-6 was used in the next reaction without purification. Compound 5-7 (6.4 g, 10.86 mmol) was obtained from Compound 5-6 in the same manner as the preparation of Compound 4-5 in Preparation Example 4.
  • Electroluminescent compounds (Compounds 1 to 66) were prepared according to the method of Preparation Examples 1 to 6. Table 1 shows 1H NMR and MS/FAB data of the prepared electroluminescent compounds. Table 1
  • a transparent electrode ITO film (15 ⁇ /D) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
  • the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. After filling
  • (2-TNATA) in a cell of the vacuum deposition apparatus the pressure inside the chamber was reduced to ICT 6 torr. Then, 2-TNATA was evaporatedbyapplying electrical current to the cell . Ahole injection layer having a thickness of 60 nm was formed on the ITO substrate. Subsequently, after filling
  • NPB N, W -bis ( ⁇ -naphthyl) -N, W -diphenyl-4, 4' -diamine (NPB) in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current.
  • An electroluminescent layer was formed on the hole transport layer as follows.
  • Compound H-I was filled in a cell of a vacuum deposition apparatus as a host, and Compound 2 was filled in another cell as a dopant .
  • the two materials were evaporated at different speed, so that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
  • Each OLED electroluminescent material was purified by vacuum sublimation at 10 "6 torr.
  • OLED was manufactured in the same manner as Example 1, except for using dinaphthylanthracene (DNA) as a host and Compound A as a dopant in the electroluminescent layer.
  • DNA dinaphthylanthracene
  • the electroluminescent device according to the present invention which comprises an electroluminescent compound with at least one arylamine group (s) substituted by 1- or 2-naphthyl, exhibits superior luminous efficiency, excellent color purity and very good operation life.

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Abstract

Provided is an electroluminescent device including an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer includes an electroluminescent layer containing one or more dopant compound(s) of formula (I) and one or more host compound(s) of formula (II), wherein at least one of Ar1to Ar4 in the arylamines of formula (I) is 1- or 2-naphthyl and the compounds of formula (II) are aromatic-substituted anthracene compounds. The disclosed electroluminescent device exhibits superior luminous efficiency, excellent color purity and very good operation life.

Description

[DESCRIPTION] [invention Title]
ORGANIC ELECTROLUMINSCENT DEVICE USING ELECTROLUMINESCENT COMPOUNDS
[Technical Field]
The present invention relates to an electroluminescent device in which an organic layer is interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1 and one or more host compound (s) represented by Chemical Formula 2:
Figure imgf000002_0001
wherein at least one of Ari through Ar4 is 1- or 2-naphthyl with or without substituent; Ar10-(An)3-Ar20 (2)
[Background Art!
Among display devices, electroluminescence (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as electroluminescent materials [Appl. Phys. Lett. 51, 913, 1987].
In an organic EL device, when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) , an electron and a hole are paired and emit light as the electron-hole pair is extinguished. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color. Since an organic EL device can exhibit green, blue and red colors, it is drawing a lot of attention as a full-color display device of the next generation. Aprocess of manufacturing an organic EL device is as follows: (1) First, an anode material is coated on a transparent substrate. Indium tin oxide (ITO) is frequently used as the anode material.
(2) Then, a hole injection layer (HIL) is formed thereupon. The hole injection layer is typically formed by coating copper phthalocyanine (CuPc) to a thickness of 10 to 30 nm. (3) Then, a hole transport layer (HTL) is formed. The hole transport layer is formed by depositing 4, 4 '-bis [N- (1-naphthyl) -N-phenylamino]biphenyl (NPB) to a thickness of about 30 to 60 nm.
(4) An organic electroluminescent layer (organic emitting layer) is formed thereupon. If required, a dopant is added thereto. In case of green electroluminescence, an organic emitting layer is formed frequently by depositing tris (8-hydroxyquinolato) aluminum (AIq3) to a thickness of about 30 to 60 nm. For the dopant, N-methylquinacridone (MQD) is commonly used. (5) An electron transport layer (ETL) and an electron injection layer (EIL) are formed sequentially, or an electron injection/transport layer is formed thereupon. In case of green electroluminescence, the ETL and/or EIL may be unnecessary because Alq3 has good electron transport ability. (6) Then, a cathode is formed, and, finally, a protective layer is formed thereupon.
With such a structure, blue, green and red EL devices are obtained respectively depending on how the electroluminescent layer is formed. The existing green electroluminescent compounds used to create green EL devices do not have good life property or luminous efficiency.
In an organic EL device, the most important factor affecting such quality as luminous efficiency, life property, etc. is the electroluminescent material. Several requirements of the electroluminescent material include high fluorescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform and thin film, and good stability.
Organic electroluminescent materials may be roughly classified into high-molecular-weight materials and low-molecular-weight materials . The low-molecular-weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure. Chelate complexes such as tris (8-quinolato) aluminum, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from the blue to the red region can be obtained using these materials, and the realization of full-color display devices is being expected.
[Disclosure] 80 [Technical Problem]
The present inventors have invented an electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, the organic layer comprising a combination of specific compounds, in order to realize an electroluminescent device having
85 high color purity, high luminous efficiency and long operation life.
An object of the present invention is to provide an electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more
90 host compound (s) and one or more dopant compound (s) . Another object of the present invention is to provide an electroluminescent device having excellent luminous efficiency, superior color purity, low driving voltage and good operation life. [Technical Solution]
95 Exemplary embodiments now will be described more fully hereinafter with reference to the accompanying drawings, in which exemplary embodiments are shown. This disclosure may, however, be embodied in many different forms and should not be construed as limited to the exemplary embodiments set forth therein. Rather, these 100 exemplary embodiments are provided so that this disclosure will be thorough and complete, andwill fully convey the scope of this disclosure to those skilled in the art . In the description, details of well-known features and techniques maybe omitted to avoid unnecessarily obscuring the presented embodiments. 105 The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of this disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Furthermore, the use of the terms
110 a, an, etc. does not denote a limitation of quantity, but rather denotes the presence of at least one of the referenced item. The use of the terms "first", "second", and the like does not imply any particular order, but they are included to identify individual elements . Moreover, the use of the terms first, second, etc. does not denote any order
115 or importance, but rather the terms first, second, etc. are used to distinguish one element from another. It will be further understood that the terms "comprises" and/or "comprising", or "includes" and/or "including" when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements,
120 and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly
125 understood by one of ordinary skill in the art. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized
130 or overly formal sense unless expressly so defined herein.
The shape, size and regions, and the like, of the drawing may be exaggerated for clarity. The present invention relates to an electroluminescent device. More particularly, the electroluminescent device according to the 135 present invention comprises an organic layer interposed between an anode and a cathode on a substrate, wherein the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1 and one or more host compound (s) represented by Chemical Formula 2:
Figure imgf000007_0001
wherein
Ar1 through Ar4 independently represent (C6-C30)aryl with or without substituent or (C3-C30) heteroaryl with or without substituent or each of them may be linked to an adjacent substituent via
) 145 (C3-C30)alkylene with or without substituent or (C3-C30) alkenylene with or without substituent to form a fused ring, with the proviso that at least one of Ar1 through Ar4 is 1- or 2-naphthyl with or without substituent;
L represents (C3-C30) heteroarylene with or without substituent,
150 stilbenylene with or without substituent,
Figure imgf000007_0002
Figure imgf000007_0003
Ar11, Ar12 and R1I through R1S independently represent hydrogen, (C6-C30)aryl with or without substituent or (C3-C30) heteroaryl with or without substituent, with the proviso that at least one of Rn through
155 Ri8 is linked to an adjacent substituent via
Figure imgf000008_0001
or to form a fused ring; the substituent substituted at the aryl or heteroaryl of Ari through Ar4, Arn, Ari2 and Rn through Ri8 and the heteroarylene or stilbenylene of L is one or more substituent (s) selected from a group 160 consisting of deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30) bicycloalkyl, 165 (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino, (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy and (C6-C30)arylthio; ring A, ring B, ring C and ring D are independently an aromatic 170 ring or a heteroaromatic ring, with the proviso that the ring C and the ring D are not benzene rings at the same time; X represents -Si(R31) (R32)- or -N(R33)-;
Y represents - (CR34R35)m-, -(R36)C=C(R37)-, -N (R3B) -# -S- or -O-;
Ri through R4, R21 through R24 and R3x through R38 independently
175 represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, 5- to
7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl,
180 (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (Cl-C30)alkylamino, mono- or di (C6-C30) arylamino, (C6-C30)ar (C1-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or
185 hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring; the aromatic ring or heteroaromatic ring of the ring A, ring B, ring C and ring D and the alkyl, aryl, heteroaryl, heterocycloalkyl,
190 cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl, alkylcarbonyl or arylcarbonyl of R1 through R4, R21 through R24 and R31 through R38 may be further substituted by one or more substituent (s)
195 selected from deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C4-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl,
200 (Cl-C30)alkoxy, cyano, (C1-C30) alkylamino, (C6-C30) arylamino, (C6-C30)ar(Cl-C30)alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, carboxyl, nitro and hydroxyl; the heterocycloalkyl and heteroaryl includes one or more hetero
205 atom(s) selected from B, N, Or S, P(=0), Si and P; and m represents an integer 1 or 2.
Ario- (An)3-Ar2O (2) wherein
An represents anthracenylene with or without one or more 210 substituent (s) or -Zi-LiOo-Z2-;
Zi and Z2 independently represent anthracenylene; L10O represents (C6-C30) arylene or (C5-C30) heteroarylene with or without one or more substituent (s) ;
Ario and Ar2O independently represent (C6-C30) aryl with or without 215 substituent or (C5-C30) heteroaryl with or without substituent; the substituent substituted at An, Ario, Ar2o or L100 is one or more selected from deuterium, halogen, (C1-C30) alkyl, halo(Cl-C30)alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or
220 more heteroatom(s) selected from N, O and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl,
(C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,
225 (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy,
(C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl,
(C6-C30) arylcarbonyl, carboxyl, nitro and hydroxyl; and a represents an integer from 1 to 4.
In the present invention, "alkyl", "alkoxy" and other
230 substituents including "alkyl" moietymay be either linear or branched.
In the present invention, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single
235 bond (S) . Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the
240 fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
In the present invention, "heteroaryl" means aryl group containing 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), other remaining aromatic
245 ring backbone atoms being carbon. It maybe 5- or 6-memberedmonocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with abenzene ring, andmaybe partially saturated. Further, theheteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s)
250 in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt. Specific examples include monocyclic heteroaryl suchasfuryl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl,
255 pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, 260 phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but not limited thereto.
In the present invention, "arylene" includes those formed as identical or different arylenes are fused, and "heteroarylene" 265 includes those formed as identical or different heteroarylenes are fused.
In the present invention, the alkyl of " (C1-C30) alkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, 270 (Cl-C30)alkyloxycarbonylr (C1-C30) alkylcarbonyl,
(Cl-C30)alkyloxycarbonyloxy, (C1-C30) alkylcarbonyloxy, etc." may have 1 to 20 carbon atoms, specifically 1 to 10 carbon atoms. The aryl of " (C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) aryloxy, 275 (C6-C30)arylthio, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, etc. " may have 6 to 20 carbon atoms, specifically 6 to 12 carbon atoms . The heteroaryl of " (C3-C30) heteroaryl" may have 4 to 20 carbon atoms, specifically 4 to 12 carbon atoms. The cycloalkyl of " (C3-C30) cycloalkyl" may have 280 3 to 20 carbon atoms, specifically 3 to 7 carbon atoms . And, the alkenyl or alkynyl of " (C2-C30) alkenyl or alkynyl" may have 2 to 20 carbon atoms, specifically 2 to 10 carbon atoms.
The electroluminescent device according to the present invention exhibits an effective energy transfer mechanism between a host and
285 a dopant and, therefore, may provide good, high-efficiency EL characteristics through improved electron density distribution. Further, it can overcome the problems associated with the existing materials, i.e., decrease of initial efficiency, short operation life, etc., and can provide high-performance EL characteristics with high 290 efficiency and long operation life for individual colors.
In the dopant compound represented by Chemical Formula 1, Ari through Ar4 are independently selected from the following structures, but not limited thereto:
Figure imgf000013_0001
295 wherein
R41 through R6g independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from
300 N, O and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl,
(C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,
(Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy or
305 (C6-C30)arylthio, and R42 and R43 may be linked via (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
In the dopant compound represented by Chemical Formula 1, at
least one of
Figure imgf000014_0001
is selected from the following
310 structures :
Figure imgf000015_0001
And, in the dopant compound represented by Chemical Formula 1, L is selected from the following structures, but not limited thereto:
Figure imgf000016_0001
wherein
Aru, Ari2, Ri? and Ri8 are the same as defined in Chemical Formula 1 ; and
R7i through R79 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,
(C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano,
325 mono- or di (C1-C30) alkylaminor mono- or di (C6-C30) arylamino, (C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (Cl-C30)alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or hydroxyl or each of them may be linked to an adjacent substituent
330 to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring.
Specifically, the dopant compound represented by Chemical Formula 1 may be exemplified by the following compounds, but not limited thereto :
Figure imgf000017_0001
Figure imgf000018_0001
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
355
The host compound represented by Chemical Formula 2 may be exemplified by the compounds represented by Chemical Formulas 3 to 5:
Figure imgf000021_0002
wherein
Rβi and R82 independently represent (C6-C60) aryl,
(C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S or (C3-C60) cycloalkyl,
365 and the aryl or heteroaryl of Rsi and R82 may be further substituted by one or more substituent (s) selected from a group consisting of
(C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy,
(C3-C60) cycloalkyl, (C6-C60) aryl, (C4-C60) heteroaryl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and
370 tri (C6-C60) arylsilyl;
Rβ3 through R86 independently represent hydrogen, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60)aryl, and the heteroaryl, cycloalkyl or aryl of R83 through
R86 may be further substituted by one or more substituent (s) selected 375 from a group consisting of (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (Cl-CβO)alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl;
G1 and G2 independently represent a chemical bond or 380 (C6-C6Q) arylene with or without one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl,
(C4-C60) heteroaryl and halogen;
Ar30 and Ar4O independently represent (C4-C60) heteroaryl or aryl selected from the following structures:
Figure imgf000022_0001
the aryl or heteroaryl of Ar30 and Ar^0 may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;
Lioi represents (C6-C60) arylene, (C4-C60) heteroarylene or a 390 compound of the following formula:
Figure imgf000022_0002
the arylene or heteroarylene of Lioi may be substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;
395 R91 through R94 independently represent hydrogen, (C1-C60) alkyl or (C6-C60) aryl, or each of themmay be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic ring;
R95 through R9e independently represent hydrogen, (C1-C60) alkyl,
400 (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or each of themmay be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic ring;
Figure imgf000023_0001
405 wherein
Lio2 represents anthracenylene;
Lio3 and L104 independently represent a chemical bond, (Cl-CβO)alkyleneoxy, (C1-C60) alkylenethio, (C6-C60) aryleneoxy, (C6-C60)arylenethio, (C6-C60) arylene or (C3-C60) heteroarylene 410 containing one or more heteroatom(s) selected from N, O and S;
Ar50 represents (C6-C60)aryl or (C5-C60) heteroaryl with or without one or more substituent (s) selected from deuterium, halogen,
(C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl 415 containing one or more heteroatom (s) selected from N, 0 and S,
(C3-C60)cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,
(C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino,
420 (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl;
Rioi through RiO6 independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl,
425 (C3-C60) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from
N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl,
(C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano,
430 mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxyl; and b represents an integer from 1 to 4.
435 Specifically, the host compound represented by any of Chemical Formulas 3 to 5 may be exemplified by the following compounds, but not limited thereto:
Figure imgf000025_0001
H-I H-2 H-3 H-4 H-5
Figure imgf000025_0002
H-6 H-7 H-8 H-9 H-IO
Figure imgf000025_0003
H-Il H-12 H-13 H-14 H-15
Figure imgf000025_0004
H-16 H-17 H-18 H-19 H-20
Figure imgf000026_0001
H-21 H-22 H-23 H-24 H-25 H-26 H-27
Figure imgf000026_0002
H-28 H-29 H-30 H-31 H-32 H-33
Figure imgf000026_0003
H-34 H-35 H-36 H-37 H-38
Figure imgf000026_0004
H-39 H-40 H-41 H-42
Figure imgf000027_0001
H-43 H-44 H-45 H-46
Figure imgf000027_0002
H-47 H-48 H-49 H-50
Figure imgf000027_0003
H-51 H-52 H-53 H-54 H-55
Figure imgf000027_0004
H-56 H-57 H-58 H-59
Figure imgf000028_0001
H-60 H-61 H- 62 H-63
Figure imgf000028_0002
H-64 H-65 H-66 H-67
Figure imgf000028_0003
H- 68 H-69 H-70 H-71
Figure imgf000028_0004
H-72 H-73 H-74 H-75
Figure imgf000029_0001
H-76 H-77 H-78 H-79
Figure imgf000029_0002
H-80 H-81 H-82 H-83
Figure imgf000029_0003
H-84 H-85 H-86 H-87
Figure imgf000029_0004
H-88 H-89 H-90
Figure imgf000029_0005
H-91 H-92
Figure imgf000030_0001
H-93 H-94
Figure imgf000030_0002
H-95 H-96
Figure imgf000030_0003
H-97 H-98 H-99
Figure imgf000030_0004
H-IOO H-IOl
Figure imgf000030_0005
H-102 H-103
Figure imgf000030_0006
H-104 H-105
Figure imgf000030_0007
H-106 H-107
The electroluminescent layer means a layer where electroluminescence occurs. It may be either a single layer or may
440 comprise two or more layers. In case a dopant and a host are used together in accordance with the present invention, remarkable improvement in luminous efficiency may be attained.
The electroluminescent device according to the present invention comprises the electroluminescent compounds represented by Chemical
445 Formula 1 and Chemical Formula 2 and may further comprise one or more compound (s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time. Examples of the arylamine compound or the styrylarylamine compound are disclosed in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or
450 10-2008-0118428, but are not limited thereto. Further, in the electroluminescent device according to the present invention, the organic layer may further comprise, in addition to the electroluminescent compounds represented by Chemical Formulas 1 and 2, one or more metal (s) selected from a group consisting of organic
455 metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements. Also, the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time. The organic layer may further comprise, in addition to the electroluminescent compounds represented by Chemical Formulas
460 1 and 2, one or more organic compound layer (s) emitting blue, green and red light at the same time to form a white-emitting electroluminescent device. Examples of the compound emitting blue, green or red light are disclosed in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not
465 limited thereto. In the electroluminescent device according to the present invention, 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)
470 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 layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent layer. A driving stability may be attained
475 therefrom.
The chalcogenide may be, for example, SiOx (1 ≤ x ≤ 2), AlOx (1 ≤ x ≤ 1-5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
480 Further, in the electroluminescent device according to the present invention, 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 may be placed on the inner surface of one or both electrode (s) among the pair of electrodes. In that case,
485 transport of electrons from the mixed region to the electroluminescent layer becomes easier, because the electron transport compound is reduced to an anion. Further, transport of holes from the mixed region to the electroluminescent layer becomes easier, because the hole transport compound is oxidized to a cation, preferred examples of
490 the oxidative dopant include various Lewis acids and acceptor compounds . Preferred examples of the reductive dopant 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 layer (s) maybe fabricated
495 by using a reductive dopant layer as a charge generating layer. [Best Mode]
Hereinafter, electroluminescence characteristics of the devices according to the present invention will be described for the understanding of the present invention. However, the following
500 examples are for illustrative purposes only and not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 8
Figure imgf000033_0001
505 Preparation of Compound 1-1
2-Bromo-9, 9-dimethylfluorene (20.Og, 102.9mmol) andAlCl3 (27.5 g, 205.9mmol) were dissolved indichloromethane (50OmL) . Afteradding 5-bromoisobenzofuran-l, 3-dione (35.Og, 154.4 mmol), the mixture was stirred while heating at 40 0C. 12 hours later, after terminating
510 the reaction by adding distilled water, followed by addition of 1 M HCl aqueous solution, the product was extracted with MC. Compound 1-1 (40.6 g, 96.4 mmol) was obtained by distillation under reduced pressure followed by column separation.
Preparation of Compound 1-2
515 Compound 1-1 (40.6 g, 96.4 mmol) was added to a mixture solvent of sulfuric acid (300 mL) and acetic acid (300 iuL) and stirred at 120 0C. 10 hours later, when distilled water was added after cooling to room temperature, a solid was produced. The solid was filtered under reduced pressure and recrystallized with methanol and ethyl 520 acetate. Compound 1-2 (11.6 g, 29.0 mmol) was obtained.
Preparation of Compound 1-3
1-Bromonaphthalene (15.O g, 72.5 mmol) was dissolved in THF (100 mL) and n-BuLi (35 mL, 87.0 mmol, 2.5 M in hexane) was slowly added dropwise at -78 0C. One hour later, after adding Compound 1-2 (10.6 525 g, 26.5 mmol), the mixture was stirred at room temperature for 12 hours. Upon completion of reaction, the product was extracted with ethyl acetate, dried with magnesium sulfate and filtered under reduced pressure. Compound 1-3 was obtained, which was used in the next reaction without purification. 530 Preparation of Compound 1-4
Unpurified Compound 1-3, KI (19.5 g, 117.6 mmol) and NaH2PO3H2O (23.8 g, 174.0 mmol) were dissolved in acetic acid (100 mL) and stirred at 1200C under reflux . 6 hours later, after cooling to roomtemperature, distilled water was added. The produced solid was filtered under 535 reduced pressure. Compound 1-4 (4.2 g, 6.1 mmol, 45%) was obtained by column separation.
Preparation of Compound 8
Compound 1-4 (4.Og, 6.79mmol), N-phenylnaphthalen-2-amine (3.3 g, 16.99 mmol) , Pd(OAc)2 (0.07 q, 0.33 mmol) , P(t-Bu) 3 (50% in toluene, 540 0.3 mLf 0.67 iranol) and Cs2CO3 (6.6 g, 20.38 iranol) were added to toluene
(50 inL) and stirred at 110 0C for 5 hours. After adding methanol (50 inL) , the produced solid was filtered under reduced pressure and washed with distilled water, methanol and hexane. The solid was added to
EA (100 mL) and stirred for 2 hours under reflux. After filtration
545 under reduced pressure, followed by column separation, the obtained solid was dissolved in THF. After adding methanol, the produced solid was filtered under reduced pressure. Compound 8 (1.6 g, 1.95 mmol) was obtained.
[Preparation Example 2] Preparation of Compound 11
Figure imgf000035_0001
Preparation of Compound 2-1
Compound 2-1 (33.O g, 96.4 mmol) was obtained in the same manner as the preparation of Compound 1-1 in Preparation Example 1, except for using 9, 9-dimethylfluorene (20.0 g, 102.9 mmol) and 555 isobenzofuran-1, 3-dione as starting materials. Preparation of Compound 2-2
Compound 2-2 (9.4 g, 29.0 mmol) was obtained from Compound 2-1 in the same manner as the preparation of Compound 1-2 in Preparation Example 1. 560 Preparation of Compound 2-3 Compound 2-2 (50 g, 0.17 mol) was added to a flask and stirred for 10 minutes after adding AcOH (1 L). After adding H3PO2 (380 g, 5.76 mol) and HI (781 g, 6.11 mol), the mixture was stirred at 150 0C for one day. Upon completion of reaction, after neutralization 565 with NaOH solution and HCl, the produced solid was filtered, added to ethyl acetate and recrystallized at 1000C under reflux. Compound 2-3 (40 g, 90%) was obtained.
Preparation of Compound 2-4
Compound 2-3 (4.4 g, 10.7 mmol) was dissolved in MC (100 mL)
570 and NBS (4.38 g, 24.64 mmol) was added. After stirring at room temperature for 12 hours, followed by distillation under reduced pressure and recrystallization with EA and methanol, Compound 2-4
(5.2 g, 9.14 mmol, 85.42%) was obtained.
Preparation of Compound 11
575 Compound 11 (1.6 g, 1.95 mmol) was obtained in the same manner as the preparation of Compound 8 in Preparation Example 1, except for using Compound 2-4 and dinaphthalen-2-ylamine.
[Preparation Example 3] Preparation of Compound 22
Figure imgf000036_0001
580 Preparation of Compound 3-1
2-Bromopyridine (12.4 mL, 127 mmol) was dissolved in ethyl ether (630 mL) and n-BuLi (51 mL, 127 mmol, 2.5 M in hexane) was slowly added at -78 0C. One hour later, the mixture was added to a solution in which dimethyl phthalate (12.4 g, 127 mmol) was dissolved in ethyl 585 ether (1,270 mL) . After stirring for 5 hours, distilled water was added and the product was extracted with EA. After drying with magnesium sulfate followed by column separation, Compound 3-1 (16 g, 66.32 mmol, 52.22%) was obtained.
Preparation of Compound 3-2
590 Compound 3-1 (16g) was dissolved in THF (43OmL) andLTMP [prepared by dissolving TMP (36mL) in THF (290 mL) and slowly adding n-BuLi (78.3 mL, 2.5 M in hexane) at 0 0C] was added at 0 0C. After stirring for 8 hours, distilled water was added and the product was extracted with EA. After drying with magnesium sulfate followed by distillation 595 under reduced pressure and column separation, Compound 3-2 (10 g, 47.80 mmol, 72.09%) was obtained.
Preparation of Compound 3-3
Compound 3-3 (40 g, 90%) was obtained from Compound 3-2 in the same manner as the preparation of Compound 2-3 in Preparation Example 600 2.
Preparation of Compound 3-4
Compound 3-4 (5.2 g, 9.14 mmol, 85.42%) was obtained from Compound 3-3 in the same manner as the preparation of Compound 2-4 in Preparation Example 2. 605 Preparation of Compound 22
Compound 22 (1.6 g, 1.95 mmol) was obtained in the same manner as the preparation of Compound 11 in Preparation Example 2, except for using Compound 3-4 and N-phenylnaphthalen-2-amine.
[Preparation Example 4] Preparation of Compound 26
Figure imgf000038_0001
Preparation of Compound 4-1
Compound 3-2 (10 g, 47.80 mmol) was added to acetic acid (100 πiL) and sulfuric acid (12.7 mL, 239.0 mmol) and nitric acid (16.8 iiiL, 239.0 mmol) were added. After stirring at room temperature for 615 10 hours, distilled water was added. After neutralizing with NaOH aqueous solution, the product was extracted with EA and dried with magnesium sulfate. After distillation under reduced pressure followed by column separation, Compound 4-1 (4 g, 13.36mmol, 27.96%) was obtained. 620 Preparation of Compound 4-2
Compound 4-1 (4 g, 13.36 mmol) was added to TEA (28 mL) . After adding Pd/C (0.4 g) , formic acid (5.04 mL, 133.68 mmol) was slowly added. After stirring at 80 0C for 4 hours, followed by cooling to room temperature, distilledwater was added. Theproduct was extracted 625 with EA and dried with magnesium sulfate. After distillation under reduced pressure followed by column separation, Compound 4-2 (2.6 g, 7.08 mmol, 53.02%) was obtained. Preparation of Compound 4-3
CuBr2 (2.37 g, 10.62 mmol) and t-BuNO2 (1.26 mL, 10.62 mmol) were 630 added to acetonitrile (100 mL) . After heating to 40 0C, Compound 4-2 was added. After stirring at 80 °C for 12 hours, the mixture was cooled to room temperature. After adding distilled water, the product was extracted with EA. After drying with magnesium sulfate, followed by distillation under reduced pressure and column separation, Compound 635 4-3 (1.8 g, 4.90 mmol, 70.06%) was obtained.
Preparation of Compound 4-5
Compound 4-4 was obtained from Compound 4-3 in the same manner as the preparation of Compound 1-3 in Preparation Example 1, except for using 2-bromonaphthalene. Compound 4-4 was used in the next 640 reaction without purification. Compound 4-5 (2.1 g, 3.56 mmol) was obtained from Compound 4-4 in the same manner as the preparation of Compound 1-4 in Preparation Example 1.
Preparation of Compound 26
Compound 26 (1.2 g, 1.56 mmol, 44.08%) was obtained in the same 645 manner as the preparation of Compound 8 in Preparation Example 1, except for using Compound 4-5 and N-phenylnaphthalen-2-amine.
[Preparation Example 5] Preparation of Compound 43
Figure imgf000039_0001
Preparation of Compound 5-1
650 Compound 5-1 (16 g, 66.32 mmol, 52.22%) was obtained in the same manner as the preparation of Compound 3-1 in Preparation Example 3, except for using 3-bromopyridine as a starting material.
Preparation of Compound 5-2
Compound 5-2 (1Og, 47.80 mmol, 72.09%) was obtained from Compound 655 5-1 in the same manner as the preparation of Compound 3-2 in Preparation Example 3.
Preparation of Compound 5-3
Compound 5-3 (7.5 g, 25.06 mmol) was obtained from Compound 5-2 in the same manner as the preparation of Compound 4-1 in Preparation 660 Example 4.
Preparation of Compound 5-4
Compound 5-4 (6-9 g, 23.53 mmol) was obtained from Compound 5-3 in the same manner as the preparation of Compound 4-2 in Preparation Example 4. 665 Preparation of Compound 5-5
Compound 5-5 (7.2 g, 19.62 mmol) was obtained from Compound 5-4 in the same manner as the preparation of Compound 4-3 in Preparation Example 4.
Preparation of Compound 5-7
670 Compound 5-6 was obtained from Compound 5-5 in the same manner as the preparation of Compound 4-4 in Preparation Example 4. Compound 5-6 was used in the next reaction without purification. Compound 5-7 (6.4 g, 10.86 mmol) was obtained from Compound 5-6 in the same manner as the preparation of Compound 4-5 in Preparation Example 4.
675 Preparation of Compound 43 Compound 43 (5.3 g, 5.93 mmol) was obtained in the same manner as the preparation of Compound 26 in Preparation Example 4, except for using Compound 5-7 and N-p-tolylnaphthalen-2-amine.
[Preparation Example 6] Preparation of Compound 47
Figure imgf000041_0001
Preparation of Compound 6-1
Compound 6-1 (9.8 g, 37.37 mmol) was obtained in the same manner as the preparation of Compound 5-1 in Preparation Example 5, except for using 3-bromopyridine and dimethylpyridine-3, 4-dicarboxylate.
685 Preparation of Compound 6-2
Compound 6-2 (6.3 g, 29.97 mmol) was obtained from Compound 6-1 in the same manner as the preparation of Compound 5-2 in Preparation Example 5.
Preparation of Compound 6-3
690 Compound 6-3 (6.4 g, 21.32 mmol) was obtained from Compound 6-2 in the same manner as the preparation of Compound 5-3 in Preparation Example 5. Preparation of Compound 6-4
Compound 6-4 (3.5 g, 14.47 mmol) was obtained from Compound 6-3 695 in the same manner as the preparation of Compound 5-4 in Preparation Example 5.
Preparation of Compound 6-5
Compound 6-5 (4.1 g, 11.14 mmol) was obtained from Compound 6-4 in the same manner as the preparation of Compound 5-5 in Preparation 700 Example 5.
Preparation of Compound 6-7
Compound 6-6 was obtained from Compound 6-5 in the same manner as the preparation of Compound 5-6 in Preparation Example 5. Compound 6-6 was used in the next reaction without purification. Compound 6-7 705 (4.2 g, 7.11 mmol) was obtained from Compound 6-6 in the same manner as the preparation of Compound 5-7 in Preparation Example 5. Preparation of Compound 47
Compound 47 (3.5 g, 3.99 mmol) was obtained in the same manner as the preparation of Compound 43 in Preparation Example 5, except 710 for Compound 6-7 and N-D5-phenylnaphthalen-2-amine.
Electroluminescent compounds (Compounds 1 to 66) were prepared according to the method of Preparation Examples 1 to 6. Table 1 shows 1H NMR and MS/FAB data of the prepared electroluminescent compounds. Table 1
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
δ = 3.52 (8H , m) , 6.11 (2H m) , 6.54 (2H, m) , 6.63 (2H, hi) , 6.71 (2H, m) , (IH, , 6.95 (2H , m) , 7 .2-7.23
66 6. 81 m)
862.09 861.32
(4H, m) , 7.3 (2H , m) , 7 .36-7.38 (4H, m) , 7.45-7 .5 (bH, m) , 7.74-7.' 77 (4H, m) , 7 84-7 .88 (4H, m)
[Example 1] Manufacture of electroluminescent device
First, a transparent electrode ITO film (15 Ω/D) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
Next, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. After filling
4, 4 ' , 4"-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine
(2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to ICT6 torr. Then, 2-TNATA was evaporatedbyapplying electrical current to the cell . Ahole injection layer having a thickness of 60 nm was formed on the ITO substrate. Subsequently, after filling
N, W -bis (α-naphthyl) -N, W -diphenyl-4, 4' -diamine (NPB) in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current. A hole transport layer having a thickness of 20 nm was formed on the hole injection layer.
An electroluminescent layer was formed on the hole transport layer as follows. Compound H-I was filled in a cell of a vacuum deposition apparatus as a host, and Compound 2 was filled in another cell as a dopant . The two materials were evaporated at different speed, so that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on the host.
Figure imgf000046_0001
740 H-I Compound 2
Thereafter, tris (8-hydroxyquinoline) -aluminum (III) (AIq) was deposited with a thickness of 20 nm as an electron transport layer. Then, lithium quinolate (Liq) was deposited with a thickness of 1 to 2 nm as an electron injection layer. Then, an Al cathode having 745 a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Each OLED electroluminescent material was purified by vacuum sublimation at 10"6 torr.
750 [Comparative Example 1] Manufacture ofOLEX) device usingexisting electroluminescent material
OLED was manufactured in the same manner as Example 1, except for using dinaphthylanthracene (DNA) as a host and Compound A as a dopant in the electroluminescent layer.
Figure imgf000046_0002
DKfA Compound A Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 1,000 cd/m2. The result is given in Table. Table 2
Figure imgf000047_0001
[industrial Applicability]
The electroluminescent device according to the present invention, which comprises an electroluminescent compound with at least one arylamine group (s) substituted by 1- or 2-naphthyl, exhibits superior luminous efficiency, excellent color purity and very good operation life.
While the exemplary embodiments have been shown and described, it will be understood by those skilled in the art that various changes in form and details may be made thereto without departing from the spirit and scope of this disclosure as defined by the appended claims.
In addition, many modifications can be made to adapt a particular situation or material to the teachings of this disclosure without 775 departing from the essential scope thereof. Therefore, it is intended that this disclosure not be limited to the particular exemplary embodiments disclosed as the best mode contemplated for carrying out this disclosure, but that this disclosure will include all embodiments falling within the scope of the appended claims. 780

Claims

[CLAIMS]
[Claim l]
An electroluminescent device comprising an organic layer interposed between an anode and a cathode on a substrate, wherein
785 the organic layer comprises an electroluminescent layer comprising one or more dopant compound (s) represented by Chemical Formula 1 and one or more host compound (s) represented by Chemical Formula 2:
Figure imgf000049_0001
wherein
790 Ari through Ar4 independently represent (C6-C30)aryl with or without substituent or (C5-C30) heteroaryl with or without substituent or each of them may be linked to an adjacent substituent via
(C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form a fused ring, with the proviso that at least one of Ari through
795 Ar4 is 1- or 2-naphthyl with or without substituent;
L represents (C3-C30) heteroarylene with or without substituent,
stilbenylene with or without substituent,
Figure imgf000049_0002
Figure imgf000049_0003
Ar11, Ari2 and R11 through R18 independently represent hydrogen,
800 (C6-C30)aryl with or without substituent or (C6-C30) heteroaryl with or without substituent, with the proviso that at least one of R11 through Ri8 is linked to an adjacent substituent via
Figure imgf000050_0001
or to form a fused ring; the substituent substituted at the aryl or heteroaryl of Ar1
805 through Ar4, Aru, Ari2 and Rn through Ri8 and the heteroarylene or stilbenylene of L is one or more substituent (s) selected from a group consisting of deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl,
810 tri(Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C60) alkylamino, mono- or di (C6-C60) arylamino, (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy and
815 (C6-C30)arylthio; ring A, ring B, ring C and ring D are independently an aromatic ring or a heteroaromatic ring, with the proviso that the ring C and the ring D are not benzene rings at the same time; X represents -Si(R31) (R32)- or -N(R33)-;
820 Y represents -(CR34R3S)1n-, -(R36)C=C(R37)-, -N(R38)-, -S- or -O- ;
R1 through R4, R21 through R24 and R3i through R38 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, 5- to
7-membered heterocycloalkyl, (C3-C30) cycloalkyl,
825 tri(Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, (C6-C30)ar(Cl-C30)alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio,
830 (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring;
835 the aromatic ring or heteroaromatic ring of the ring A, ring B, ring C and ring D and the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, alkylamino, arylamino, aralkyl, alkyloxy, alkylthio, aryloxy, arylthio, alkoxycarbonyl,
840 alkylcarbonyl or arylcarbonyl of Ri through R4, R21 through R24 and R31 through R38 may be further substituted by one or more substituent (s) selected from deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C4-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl,
845 di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (Cl-C30)alkoxy, cyano, (C1-C30) alkylamino, (C6-C30) arylamino, (C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl,
850 (C1-C30) alkylcarbonyl, carboxyl, nitro and hydroxyl; the heterocycloalkyl and heteroaryl includes one or more hetero atom(s) selected from B, N, O, S, P(=0), Si and P; and m represents an integer 1 or 2;
Figure imgf000052_0001
)
855 wherein
An represents anthracenylene with or without one or more substituent (s) or -Z1-L100-Z2-;
Z1 and Z2 independently represent anthracenylene; Lioo represents (C6-C30) arylene or (C5-C30) heteroarylene with 860 or without one or more substituent (s) ;
Ario and Ar20 independently represent (C6-C30) aryl with or without substituent or (C5-C30) heteroaryl with or without substituent; the substituent substituted at An, Ario, Ar2o or Lioo is one or more selected from deuterium, halogen, (C1-C30) alkyl, 865 halo (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C30) cycloalkyl, tri(Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri(C6-C30)arylsilyl, adamantyl, (C7-C30)bicycloalkyl, 870 (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, (Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro and hydroxyl; and 875 a represents an integer from 1 to 4.
[Claim 2]
The electroluminescent device according to claim 1, wherein Ari through Ar4 are independently selected from the following structures:
Figure imgf000053_0001
wherein
R41 through Reg independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,
(C3-C30) heteroaryl, morpholino, thiomorpholino, 5- or 6-meitibered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di(Cl-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl,
(C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,
(Cl-C30)alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy or (C6-C30)arylthio, andR52 and R53 may be linked via (C3-C30) alkylene or (C3-C30) alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
[Claim 3]
The electroluminescent device according to claim 2, wherein at
least one of
Figure imgf000054_0001
is selected from the following structures :
Figure imgf000054_0002
[Claim 4]
The electroluminescent device according to claim 1, wherein Ls selected from the following structures:
Figure imgf000055_0001
wherein
Arn, Ar12, Ri7 and Ris are the same as defined in Chemical Formula 905 1 ; and
R7i through R79 independently represent hydrogen, deuterium, halogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C6-C30) aryl,
(C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl,
(C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl,
910 di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl,
(C7-C30)bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino,
(C6-C30)ar(Cl-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio,
(C6-C30)aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl,
915 (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, carboxyl, nitro or hydroxyl or each of them may be linked to an adjacent substituent to form a saturated or unsaturated mono- or polycyclic aromatic ring or heteroaromatic ring. [Claim 5]
920 The electroluminescent device according to claim 1, wherein the dopant is selected from the following compounds:
Figure imgf000056_0001
Figure imgf000057_0001

Figure imgf000058_0001
Figure imgf000058_0003
Figure imgf000058_0002
Figure imgf000059_0001

Figure imgf000060_0001
[Claim 6]
The electroluminescent device according to claim 1, wherein the ost is selected from the following compounds:
Figure imgf000060_0002
Figure imgf000061_0001
60
Figure imgf000062_0001
61
Figure imgf000063_0001
Figure imgf000063_0002
Figure imgf000063_0003
Figure imgf000063_0004
62
Figure imgf000064_0001
63
Figure imgf000065_0001
[Claim 7]
The electroluminescent device according to claim 1, wherein the 935 organic layer comprises one or more compound (s) selected fromarylamine compounds and styrylarylamine compounds. [Claim 8]
The electroluminescent device according to claim 1, wherein the organic layer further comprises one or more metal (s) selected from 940 a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements. [Claim 9]
The electroluminescent device according to claim 1, wherein the 945 organic layer further comprises a compound having an electroluminescence peak with red, green or blue wavelength. [Claim 10]
The electroluminescent device according to claim 1, wherein the organic layer comprises an electroluminescent layer and a charge 950 generating layer. [Claim 11]
The electroluminescent device according to claim 1, wherein one or more layer (s) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer is placed on the inner surface of one 955 or both electrode (s) among the pair of electrodes. [Claim 12]
The electroluminescent device according to claim 1, wherein a mixed region of a reductive dopant and an organic material or an oxidative dopant and an organic material is placed on the inner surface 960 of one or both electrode (s) among the pair of electrodes.
PCT/KR2009/006980 2008-11-26 2009-11-25 Organic electroluminscent device using electroluminescent compounds Ceased WO2010062107A1 (en)

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