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WO2013032284A1 - Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés - Google Patents

Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés Download PDF

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Publication number
WO2013032284A1
WO2013032284A1 PCT/KR2012/007008 KR2012007008W WO2013032284A1 WO 2013032284 A1 WO2013032284 A1 WO 2013032284A1 KR 2012007008 W KR2012007008 W KR 2012007008W WO 2013032284 A1 WO2013032284 A1 WO 2013032284A1
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substituted
unsubstituted
alkyl
aryl
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Inventor
Hee-Choon Ahn
Young-Jun Cho
Nam-Kyun Kim
Hyo-Nim Shin
Hyuck-Joo Kwon
Kyung-Joo Lee
Bong-Ok Kim
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DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Priority to CN201280049555.4A priority Critical patent/CN103857680A/zh
Priority to JP2014528289A priority patent/JP2014531747A/ja
Publication of WO2013032284A1 publication Critical patent/WO2013032284A1/fr
Anticipated expiration legal-status Critical
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
  • phosphorescent materials including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)pic
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • Pioneer (Japan) et al. developed a high performance organic EL device employing a derivative of BAlq as a host material.
  • WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a compound having a nitrogen-containing condensed bicyclic group together with a carbazole group which is fused with an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
  • the objective of the present invention is to provide an organic electroluminescent compound which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device having high efficiency and a long lifetime, using said compounds.
  • L 1 and L2 each independently represent a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C3-C30)cycloalkylene group;
  • X 1 represents CH or N
  • Y 1 and Y 2 each independently represent -O-, -S-, -CR 6 R 7 - or -NR 8 -;
  • R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano group, a nitro group, or a hydroxyl group; or R 4 and R 5 each independently are linked to an adjacent substituent(s) via a substituted or unsubstituted (
  • R 6 to R 8 and R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; or are linked to an adjacent substituent(s) via a substituted or unsubstituted (C3-C30)alkylene or a substituted or unsubstituted (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur;
  • a, b, c and e each independently represent an integer of 1 to 4; where a, b, c or e is an integer of 2 or more, each of R1, each of R 2 , each of R 3 or each of R 5 is the same or different;
  • d represents an integer of 1 to 3; where d is an integer of 2 or more, each of R 4 is the same or different; and
  • he organic electroluminescent compounds according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
  • the organic electroluminescent compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing a device. Further, the compounds have good layer formability and improve the current characteristics of the device. Therefore, they can produce an organic electroluminescent device having lowered driving voltages and enhanced power efficiency.
  • the present invention relates to a compound represented by the above formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc., but are not limited thereto.
  • (C2-C30) alkenyl(ene) is meant to be a linear or branched alkenyl(ene) having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc., but are not limited thereto.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc., but are not limited thereto.
  • (C1-C30)alkoxy is a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc., but are not limited thereto.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., but are not limited thereto.
  • (C3-C30)cycloalkylene is one formed by removing a hydrogen from cycloalkyl having 3 to 30, preferably 3 to 20, more preferably 3 to 7 carbon atoms.
  • halogen includes F, Cl, Br and I.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 12, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl, 2-naphthyl, etc.; the anthracenyl includes 1-anthracenyl, 2- anthracenyl, 9-anthracenyl, etc.; the phenanthrenyl includes 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, etc.; the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, etc.; the pyrenyl includes 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, etc.; the biphenyl includes 2-biphenyl, 3-biphenyl, 4- biphenyl, etc.; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-
  • the heteroaryl(ene) includes a divalent aryl group, which forms an N-oxide, a quaternary salt, etc., by oxidation or quaternarization of a heteroatom existing in a ring.
  • the heteroaryl(ene) includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenz
  • the pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, etc.; the pyridyl includes 2-pyridyl, 3-pyridyl, 4-pyridyl, etc.; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, etc.; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, etc.; the furyl includes 2-furyl, 3-furyl, etc.; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
  • L 1 and L 2 each independently represent a single bond, a 3- to 30-membered heteroarylene group, a (C6-C30)arylene group, or a (C6-C30)cycloalkylene group;
  • X 1 is CH or N;
  • Y 1 and Y 2 each independently represent -O-, -S-, -CR 6 R 7 - or -NR 8 -;
  • R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, a N-carbazolyl group, -NR 11 R 12 , or -SiR 13 R 14 R 15 ; or
  • R 4 and R 5 each independently are linked to an adjacent substituent(s) via a (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or poly
  • L 1 and L 2 each independently are preferably selected from the group consisting of a single bond, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, phenylene, methylphenylene, naphthylene, biphenylene, terphenylene, anthracenylene, indenylene, fluorenylene, phenanthrenylene, triphenylenylene, pyrenylene, phenylenylene, crycenylene, naphthacenylene, fluoranthenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, tri
  • Y 1 and Y 2 each independently selected from the following structures:
  • R 1 to R 5 each independently are preferably a (C6-C20)aryl group, an 5- to 21-membered heteroaryl group, -NR 11 R 12 or -SiR 13 R 14 R 15 ; or are linked to an adjacent substituent(s) via a substituted or unsubstituted (C3-C30)alkylene or a substituted or unsubstituted (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably phenyl, carbazolyl, diphenylamino or methyldiphenylsilyl; or are linked to an adjacent substituent(s) via a substituted or unsubstituted (C3-C30)alkylene or a substituted or unsubstituted (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring.
  • the R 11 to R 15 each independently are preferably are
  • R 6 to R 8 each independently are preferably hydrogen, a (C1-C6)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 5- to 21-membered heteroaryl group, more preferably hydrogen; methyl; phenyl; biphenyl; naphthyl; phenyl substituted with deuterium; phenyl substituted with fluorine; fluorenyl substituted with methyl; or naphthylphenyl.
  • the representative organic electroluminescent compounds of the present invention include the following compounds, but are not limited thereto:
  • organic electroluminescent compounds according to the present invention can be prepared according to the following reaction scheme.
  • L 1 , L 2 , X 1 , Y 1 , Y 2 , R 1 to R 5 , a, b, c, d and e are as defined in formula 1 above, and Hal represents a halogen.
  • the present invention provides an organic electroluminescent material comprising the compound of formula 1 and an organic electroluminescent device comprising the material.
  • the above material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
  • Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes.
  • Said organic layer comprises at least one organic electroluminescent compound of formula 1 according to the present invention.
  • said organic layer comprises a light-emitting layer in which the organic electroluminescent compound of formula 1 is comprised as a host material.
  • a phosphorescent dopant which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from compounds represented by the following formula 2:
  • M 1 is selected from the group consisting of Ir, Pt, Pd and Os;
  • L 101 , L 102 and L 103 are each independently selected from the following structures:
  • R 201 to R 203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
  • R 204 to R 219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF 5 , a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)aryl
  • R 220 to R 223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
  • R 224 and R 225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R 224 and R 225 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring;
  • R 226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- or 30-membered heteroaryl group or a halogen;
  • R 227 to R 229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
  • R 231 to R 242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R 231 to R 242 may be linked to an adjacent substituent via (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R 207 or R 208 via a (C2-C30)alkylene group or (C2-C30)alkenylene group to form a saturated or unsaturated fused ring.
  • the dopants of formula 2 include the following, but are not limited thereto:
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides the organic electroluminescent compound according to the present invention.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • said chalcogenide includes SiOX(1 ⁇ X ⁇ 2), AlOX(1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • reaction mixture was extracted with ethyl acetate (EA) 1 L and an aqueous layer was further extracted with dichloromethane (1 L).
  • EA ethyl acetate
  • dichloromethane 1 L
  • the obtained organic layer was dried with anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure.
  • the obtained solid was filtered through silica gel, and the solvent was removed under reduced pressure.
  • the obtained solid was washed with EA (100 mL) to obtain compound 1-1 (50 g, 74%).
  • An OLED device was produced using the compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an OLED device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • ITO indium tin oxide
  • 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 introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming 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 introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • compound C-18 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material
  • compound D-7 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 4 wt% of dopant with respect to the total amount of the host material and the dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole was introduced into one cell and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rates and were deposited in a doping amount of 50 wt% for each material to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 1 to 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced.
  • the produced OLED device showed red emission having a luminance of 3,400 cd/m 2 and a current density of 44.7 mA/cm 2 at a driving voltage of 5.6 V.
  • Comparative Example 1 Production of an OLED device using conventional
  • An OLED device was produced in the same manner as that of Device Example 1, except that a light-emitting layer was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl (CBP) as a host material and compound D-11 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited between the light-emitting layer and a electron transport layer by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • the produced OLED device showed red emission having a luminance of 1,000 cd/m 2 and a current density of 20.0 mA/cm 2 at a driving voltage of 8.2 V.

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Abstract

La présente invention concerne un nouveau composé électroluminescent organique, et un dispositif électroluminescent organique contenant ce composé. Les composés électroluminescents organiques selon la présente invention permettent un transport très efficace des électrons, ce qui permet d'empêcher la cristallisation pendant la fabrication d'un dispositif. En outre, ces composés présentent une bonne aptitude à la formation en couche et améliorent les caractéristiques du dispositif concernant le courant. Ces composés permettent ainsi de produire un dispositif électroluminescent organique se distinguant par des tensions d'excitation moindres et un rendement énergétique meilleur.
PCT/KR2012/007008 2011-09-01 2012-08-31 Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés Ceased WO2013032284A1 (fr)

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CN201280049555.4A CN103857680A (zh) 2011-09-01 2012-08-31 新有机电致发光化合物和使用该化合物的有机电致发光器件
JP2014528289A JP2014531747A (ja) 2011-09-01 2012-08-31 新規有機エレクトロルミネッセンス化合物およびこれを使用した有機エレクトロルミネッセンス素子

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US20210013411A1 (en) * 2018-04-17 2021-01-14 Lt Materials Co., Ltd. Heterocyclic compound and organic light-emitting device comprising same
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US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US20160293854A1 (en) 2015-04-06 2016-10-06 Universal Display Corporation Organic Electroluminescent Materials and Devices
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
KR102717189B1 (ko) * 2016-12-20 2024-10-15 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
JP6954275B2 (ja) * 2017-03-28 2021-10-27 東レ株式会社 化合物、それを含有する電子デバイス、有機薄膜発光素子、表示装置および照明装置
CN114933591B (zh) * 2018-04-27 2024-06-04 北京鼎材科技有限公司 吡啶衍生物及其应用
KR20200011873A (ko) * 2018-07-25 2020-02-04 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
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