EP2616462A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant celui-ci - Google Patents

Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant celui-ci

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Publication number
EP2616462A1
EP2616462A1 EP11825442.4A EP11825442A EP2616462A1 EP 2616462 A1 EP2616462 A1 EP 2616462A1 EP 11825442 A EP11825442 A EP 11825442A EP 2616462 A1 EP2616462 A1 EP 2616462A1
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Prior art keywords
substituted
unsubstituted
alkyl
aryl
organic electroluminescent
Prior art date
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EP11825442.4A
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German (de)
English (en)
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EP2616462A4 (fr
Inventor
Hyo Nim Shin
Soo-Jin Hwang
Hee Sook Kim
Seok Keun Yoon
Mi Ja Lee
Nam Kyun Kim
Young Jun Cho
Hyuck Joo Kwon
Kyung Joo Lee
Bong Ok Kim
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Rohm and Haas Electronic Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Publication of EP2616462A1 publication Critical patent/EP2616462A1/fr
Publication of EP2616462A4 publication Critical patent/EP2616462A4/fr
Withdrawn legal-status Critical Current

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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same.
  • electroluminescent (EL) devices which are self-emissive display devices, are advantageous in that they provide wide viewing angle, superior contrast and a fast response rate.
  • EL electroluminescent
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
  • electroluminescent material The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material.
  • fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism.
  • iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
  • a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
  • CBP is most widely known as a host material for a phosphorescent material.
  • High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported.
  • High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
  • an object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional material.
  • Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the organic electroluminescent compound as an electroluminescent material.
  • organic electroluminescent compound represented by Chemical Formula 1 below, and an organic electroluminescent device using the same.
  • the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
  • ring A represents a monocyclic or polycyclic aromatic ring
  • X 1 and X 2 independently represent N or CR';
  • L 1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar 1 represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
  • Z is independently selected from following structures
  • Z is selected from following structures only when the ring A is a monocyclic aromatic ring;
  • Y represents -O-, -S-, -C(R 11 R 12 )-, -Si(R 13 R 14 )- or -N(R 15 )-;
  • R 1 through R 9 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR 16 R 17
  • R' and R 11 through R 22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of
  • a, c, e and i independently represent an integer of 1 to 4, and when a, c, e and I are an integer of 2 or greater, each of R 1 , R 3 , R 5 and R 9 may be identical or different from each other;
  • b, d, and g independently represent an integer of 1 to 3, and when b, d, and g are an integer of 2 or greater, each R 2 , R 4 and R 7 may be identical or different from each other;
  • f represents an integer of 1 to 6, and when f is an integer of 2 or greater, each R 6 may be identical or different from each other;
  • h represents an integer of 1 to 5, and when h is an integer of 2 or greater, each R 8 may be identical or different from each other;
  • alkyl As described herein, “alkyl”, “alkoxy” and other substituents containing the “alkyl” moiety include both linear and branched species, and the “cycloalkyl” includes polycyclic hydrocarbon ring such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as a monocyclic hydrocarbon ring.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, and even further includes a structure where a plurality of aryls are linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl
  • the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl.
  • the pyrenyl includes 1-pyrenyl, 2-pyrenyl and 4-pyrenyl
  • the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl
  • the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • heteroaryl includes a structure where one or more heteroaryls are linked by single bonds.
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt.
  • Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl
  • the pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl and 7-isoindolyl; the furyl includes 2-furyl and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; the isobenzofur
  • (C1-C30)alkyl includes (C1-C20)alkyl or (C1-C10)alkyl
  • (C6-C30)aryl includes (C6-C20)aryl
  • (C2-C30)heteroaryl includes (C2-C20)heteroaryl
  • (C3-C30)cycloalkyl includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
  • (C2-C30)alkenyl or alkynyl includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
  • each substituent of the L 1 , Ar 1 , R 1 through R 9 , R and R 11 through R 22 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl-substituted or unsubstituted (C2-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic rings, R a R b R c Si-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NR d R e , -BR
  • the organic electroluminescent compound may be represented by Chemical Formulas 2 to 9 below.
  • X 2 is N or CH; Y is -O-, -S-, -C(R 11 R 12 )- or -N(R 15 )-; L 1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (C2-C30)heteroarylene; Ar 1 represents hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl; R 1 through R 9 independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, NR 16 R 17 or SiR 18 R 19 R 20 ; R 11 , R 12 , R 15 and R 16 through R 20 independently represent hydrogen, deuterium, substituted substituted
  • X 2 represents N or CH;
  • Y represents -O-, -S-, -C(R 11 R 12 )- or -N(R 15 )-;
  • L 1 represents a single bond or arylene selected from the following structures:
  • R 31 and R 32 independently represent methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, pyridyl or quinolyl;
  • Ar 1 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, terphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or N-phenylcarbazoly
  • R 1 through R 9 independently represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, amino or carbazolyl;
  • R 11 , R 12 and R 15 independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, 9,9-diphenylfluorenyl, 9,
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
  • organic electroluminescent compound according to the present invention may be prepared as shown in, for example, Scheme 1 below, but is not limited thereto.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds represented by Chemical Formula 1.
  • the organic layer includes an electroluminescent layer, and the organic electroluminescent compound of Chemical Formula 1 may be used as a host in the electroluminescent layer.
  • the organic electroluminescent compound of Chemical Formula 1 when used as a host, one or more phosphorescent dopant(s) is included.
  • the phosphorescent dopant applied to the organic electroluminescent device according to the present invention is not specifically limited, but may be selected from among compounds represented by Chemical Formula 10 below.
  • M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • R 201 through R 203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
  • R 204 through R 219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF 5 , substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl,
  • R 220 through R 223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
  • R 224 and R 225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or halogen, or R 224 and R 225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
  • R 226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
  • R 227 through R 229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen;
  • Q represents , or ;
  • R 231 through R 242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • the dopant compound of Chemical Formula 10 may be exemplified by the following compounds, but is not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • 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) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
  • 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, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
  • Compound 2-2 (9.5g, 19.1mmol, 74%) was prepared by the same method as in the preparation of Compound 1-2 .
  • Compound 2-3 (9.0g, 15.6mmol, 82%) was prepared by the same method as in the preparation of Compound 1-3 .
  • Compound 2-4 (4.0g, 7.4mmol, 47%) was prepared by the same method as in the preparation of Compound 1-4 .
  • Compound 2 (2.8g, 4.6mmol, 51%) was prepared from Compound 2-4 (4.0g, 7.4mmol) and 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 7 (2.8g, 4.6mmol, 51%) was prepared from Compound 2-4 (4.0g, 7.4mmol) and 2-bromodibenzo[b,d]thiophene (5.5g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 12 (6.8g, 9.5mmol, 53%) was prepared from Compound 1-4 (6.9g, 18.05mmol) and 10-bromo-7-phenyl-7H-benzo[c]carbazole (7.8g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 16 (7.6g, 11.0mmol, 61%) was prepared from Compound 2-4 (9.8g, 18.05mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 6-4 (4.3g, 7.5mmol, 76%) was prepared by the same method as in the preparation of Compound 1-3 .
  • Compound 6-5 (1.7g, 3.1mmol, 43%) was prepared by the same method as in the preparation of Compound 1-4 .
  • Compound 25 (7.6g, 10.3mmol, 57%) was prepared from Compound 6-5 (9.8g, 18.05mmol) and 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • An OLED device was manufactured using the compound for organic electronic materials according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and N 1 ,N 1' ([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate it, thereby depositing a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was placed in another cell of the vacuum deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby depositing a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows. Compound 1 as a host was placed in a cell, and Compound D-11 as a dopant was placed in another cell, within a vacuum vapor deposition apparatus.
  • the two materials were evaporated at different rates such that 4 wt% doping taken place, and thereby the electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer. Subsequently, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was placed in a cell and lithium quinolate was placed in another cell, after which the two materials were evaporated at the same rate such that 50 wt% doping taken place, and thereby an electron transport layer was vapor-deposited to a thickness of 30 nm on the electroluminescent layer.
  • Liq lithium quinolate
  • Al cathode was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
  • Each compound used in the OLED device was purified by vacuum sublimation at 10 -6 torr before use.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 2 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 25 was used as the host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 37 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 128 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 139 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that an electroluminescent layer was vapor-deposited using 4,4'-N,N'-dicarbazole-biphenyl used as a host and Compound D-11 as a dopant, and a hole blocking layer was vapor-deposited to a thickness of 10 nm using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate between the electroluminescent layer and the electron transport layer.
  • the organic electroluminescent compounds developed in the present invention showed superior electroluminescent properties compared to the conventional material.
  • the devices using the organic electroluminescent compounds of the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, thereby improving power consumption.
  • an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.

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  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
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Abstract

L'invention concerne de nouveaux composés électroluminescents organiques et un dispositif électroluminescent organique utilisant celui-ci. Du fait que le composé électroluminescent organique selon l'invention présente un bon rendement lumineux et une excellente durée de vie, il peut être utilisé pour fabriquer des dispositifs OLED très supérieurs en termes de durée de vie et qui consomment moins d'énergie grâce au rendement énergétique amélioré.
EP11825442.4A 2010-09-17 2011-09-16 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant celui-ci Withdrawn EP2616462A4 (fr)

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KR20100091545 2010-09-17
KR1020110092422A KR101477614B1 (ko) 2010-09-17 2011-09-14 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
PCT/KR2011/006810 WO2012036482A1 (fr) 2010-09-17 2011-09-16 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant celui-ci

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CN103221406A (zh) 2013-07-24
JP6672416B2 (ja) 2020-03-25
TW201224110A (en) 2012-06-16
WO2012036482A1 (fr) 2012-03-22
TWI560258B (en) 2016-12-01
JP2017031167A (ja) 2017-02-09
KR20120030009A (ko) 2012-03-27
JP2019050382A (ja) 2019-03-28
KR101477614B1 (ko) 2014-12-31

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