WO2010062107A1 - Dispositif électroluminescent organique utilisant des composés électroluminescents - Google Patents

Dispositif électroluminescent organique utilisant des composés électroluminescents Download PDF

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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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alkyl
compound
substituent
ring
heteroaryl
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PCT/KR2009/006980
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English (en)
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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Priority claimed from KR1020090042825A external-priority patent/KR20100059653A/ko
Application filed by Gracel Display Inc. filed Critical Gracel Display Inc.
Priority to JP2011537375A priority Critical patent/JP2012510154A/ja
Priority to CN2009801475043A priority patent/CN102227486A/zh
Publication of WO2010062107A1 publication Critical patent/WO2010062107A1/fr

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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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    • C07C13/54—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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    • 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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    • C07D279/18—[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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    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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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    • C07C2603/10—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
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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.

Abstract

L'invention porte sur un dispositif électroluminescent comprenant une couche organique interposée entre une anode et une cathode sur un substrat, dans lequel la couche organique comprend une couche électroluminescente contenant un ou plusieurs composés dopants et un ou plusieurs composés hôtes : comprenant un composé électroluminescent avec un groupe arylamine substitué par au moins un 1-ou 2-naphtyle, le dispositif électroluminescent décrit présente un rendement lumineux supérieur, une excellente pureté de couleur et une très bonne durée de vie de fonctionnement.
PCT/KR2009/006980 2008-11-26 2009-11-25 Dispositif électroluminescent organique utilisant des composés électroluminescents WO2010062107A1 (fr)

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WO2020091506A1 (fr) * 2018-11-02 2020-05-07 주식회사 엘지화학 Composé et élément électroluminescent organique le comprenant
WO2020159135A1 (fr) * 2019-01-30 2020-08-06 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé
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US20120161615A1 (en) * 2009-06-19 2012-06-28 Doosan Corporation Aminoanthracene derivative and an organic electroluminescent element employing the same
US9115112B2 (en) * 2009-06-19 2015-08-25 Doosan Corporation Aminoanthracene derivative and an organic electroluminescent element employing the same
CN102002003A (zh) * 2010-10-14 2011-04-06 华东师范大学 一类二氮杂芴酮和芴及螺二芴衍生物和制备方法及其应用
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US20120319087A1 (en) * 2011-06-16 2012-12-20 Lee Sun-Young Heterocyclic compound and organic light-emitting device containing same
US9312500B2 (en) 2012-08-31 2016-04-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US20160254450A1 (en) * 2013-10-25 2016-09-01 E. I. Du Pont De Nemours And Company Blue luminescent compounds
US9711731B2 (en) * 2013-10-25 2017-07-18 E I Du Pont De Nemours And Company Blue luminescent compounds
US10283716B2 (en) * 2015-02-09 2019-05-07 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using the same, and electronic device comprising same
US10312449B2 (en) 2015-05-27 2019-06-04 Samsung Display Co., Ltd. Organic light-emitting device
US10367147B2 (en) 2015-05-27 2019-07-30 Samsung Display Co., Ltd. Organic light-emitting device
US11427562B2 (en) * 2016-07-06 2022-08-30 Lt Materials Co., Ltd. Heterocyclic compound, and organic light-emitting device using same
WO2019194616A1 (fr) * 2018-04-05 2019-10-10 주식회사 엘지화학 Composé amine et diode électroluminescente organique le comprenant
CN111491913A (zh) * 2018-04-05 2020-08-04 株式会社Lg化学 胺化合物及包含其的有机发光器件
CN111491913B (zh) * 2018-04-05 2023-11-07 株式会社Lg化学 胺化合物及包含其的有机发光器件
WO2020091506A1 (fr) * 2018-11-02 2020-05-07 주식회사 엘지화학 Composé et élément électroluminescent organique le comprenant
KR20200050887A (ko) * 2018-11-02 2020-05-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR102290022B1 (ko) 2018-11-02 2021-08-17 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
WO2020159135A1 (fr) * 2019-01-30 2020-08-06 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique associé

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