WO2012150826A1 - Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant - Google Patents

Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant Download PDF

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WO2012150826A1
WO2012150826A1 PCT/KR2012/003472 KR2012003472W WO2012150826A1 WO 2012150826 A1 WO2012150826 A1 WO 2012150826A1 KR 2012003472 W KR2012003472 W KR 2012003472W WO 2012150826 A1 WO2012150826 A1 WO 2012150826A1
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group
substituted
unsubstituted
compound
organic electroluminescent
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PCT/KR2012/003472
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Chi-Sik Kim
Soo-Jin Yang
Hee-Sook Kim
Kyoung-Jin Park
Seung-Ae Kim
Kyung-Joo Lee
Hyuck-Joo Kwon
Bong-Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020120046340A external-priority patent/KR101396171B1/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to JP2014509244A priority Critical patent/JP6046701B2/ja
Priority to EP12779767.8A priority patent/EP2694619A4/fr
Priority to CN201280031410.1A priority patent/CN103764786B/zh
Publication of WO2012150826A1 publication Critical patent/WO2012150826A1/fr

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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

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.
  • light-emitting materials can be used as a system prepared by mixing a dopant with a host material.
  • the host material has a great influence on the efficiency and performance of an EL device, and thus its selection is important.
  • 4,4’-bis(carbazol-9-yl)-biphenyl (CBP) is the most widely known host material for phosphorescent materials.
  • Pioneer (Japan) developed a high performance organic EL device employing, as a host material, bathocuproine (BCP) or aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq), which had been a material used for a hole blocking layer.
  • Korean Patent No. 948700 discloses compounds for organic electroluminescent materials whose arylcarbazole backbone has a nitrogen-containing aryl. However, it does not disclose compounds whose carbazole backbone has both dibenzothiophene and a nitrogen-containing aryl. Further, an organic EL device comprising said compounds fails to provide satisfactory luminous efficiency, driving voltage and operation lifetime.
  • An objective of the present invention is to provide organic electroluminescent compounds, which impart excellent luminous efficiency, a long operation lifetime and a low driving voltage to a device; and an organic electroluminescent device, which has high efficiency and a long operation lifetime, using said compounds.
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
  • X 1 and X 2 each independently represent CR’ or N;
  • Y represents S, O or -CR 21 R 22 ;
  • Ar 1 , Ar 2 , R’, R 21 and R 22 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;
  • R 1 to R 4 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, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano group, a nitro group or a hydroxyl group;
  • 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 or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced by at least one atom selected from nitrogen, oxygen and sulfur;
  • a and d each independently represent an integer of 1 to 4; where a or d is an integer of 2 or more, each of R 1 or each of R 4 is the same or different;
  • Substituents of the substituted groups in L 1 , L 2 , Ar 1 , Ar 2 , R’, R 1 to R 4 , R 11 to R 17 , R 21 and R 22 each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl group, a (C1-C30)alkyl group substituted with a halogen, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, a 3- to 30-membered heteroaryl group substituted with a (C6-C30)aryl group, a (C6-C30)aryl group substituted with a 3- to 30-membered heteroaryl group, a (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group, a tri(C1-C30)alkylsilyl group, a tri(C6-C30)aryl
  • alkyl alkoxy and any “alkyl” moiety which is comprised in substituents include both a linear structure and a branched structure; and the term “cycloalkyl” includes a mono- or polycyclic hydrocarbon such as a substituted or unsubstituted adamantyl group or a substituted or unsubstituted (C7-C30)bicycloalkyl group.
  • aryl refers to an organic radical derived from an aromatic hydrocarbon by removing one hydrogen atom; includes a monocyclic ring or fused ring each of whose rings has 4 to 7, preferably 5 or 6, ring backbone atoms; may be one formed by linking two or more aryl groups to one another via a single bond(s); and includes phenyl, biphenyl, terphenyl, naphthyl, anthryl, indenyl, fluorenyl, phenanthrenyl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., wherein said naphthyl includes 1-naphthyl and 2-naphthyl, said anthryl includes 1-anthryl, 2-anthryl and 9-anthryl and said fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-
  • the “(C1-C30)alkyl(ene)” group is preferably a (C1-C20)alkyl(ene) group and more preferably a (C1-C10)alkyl(ene) group;
  • the “(C6-C30)aryl(ene)” group is preferably a (C6-C20)aryl(ene) group and more preferably a (C6-C12)aryl(ene) group;
  • the “3- to 30-membered heteroaryl(ene)” group is preferably a 3- to 20-membered heteroaryl(ene) group and more preferably a 5- to 13-membered heteroaryl(ene) group;
  • the “(C3-C30)cycloalkyl” group is preferably a (C3-C20)cycloalkyl group and more preferably a (C3-C7)cycloalkyl group; and the “(C2-C30)alkenyl(ene) or al
  • L 1 and L 2 each independently represent a single bond; or a substituted or unsubstituted phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, perylenylene, chrysenylene, naphthacenylene, fluoranthenylene, thiophenylene, pyrrolylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylene, benzofuranylene, benzothiophenylene, indolene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, benzothiadiazolylene, dibenzofuranylene or dibenz
  • Ar 1 , Ar 2 , R’, R 21 and R 22 each independently represent hydrogen; or a substituted or unsubstituted 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, fluorenyl, fluoranthenyl, terphenyl, pyrenyl, chrysenyl, naphthacenyl, perylene, pyri
  • R 1 to R 4 each independently represent hydrogen, deuterium, chloro, fluoro, 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, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pyridyl, pyrroly
  • a to d each independently represent an integer of 1 to 2, more preferably 1;
  • L 1 , L 2 , Ar 1 , Ar 2 , R’, R 1 to R 4 , R 21 and R 22 each independently may be further substituted with at least one selected from the group consisting of deuterium, chloro, fluoro, 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, fluorenyl, fluoranthenyl, triphenylenyl,
  • Organic electroluminescent compounds according to the present invention include the following, but are not limited thereto:
  • Organic electroluminescent compounds according to the present invention can be prepared according to the following reaction scheme 1.
  • Ar 1 , Ar 2 , L 1 , L 2 , Y, X 1 , X 2 , R 1 to R 4 , a, b, c and d are as defined in formula 1 above, and X represents a halogen.
  • the present invention provides an organic electroluminescent device comprising the compound of formula 1.
  • the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer between the first and second electrodes.
  • the organic layer comprises at least one compound of formula 1 according to the present invention.
  • One of the first electrode and the second electrode is an anode and the other is a cathode.
  • the organic layer comprises a light-emitting layerand may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.
  • the compound of formula 1 is comprised in at least one of the light-emitting layer and the hole transport layer.
  • the hole transport layer comprises the compound of formula 1
  • the compound may be used as a hole transport material.
  • the light-emitting layer comprises the compound of formula 1
  • the compound may be used as a host material; preferably, the light-emitting layer may further comprise at least one dopant; and if necessary, the light-emitting layer may further comprise another host material in addition to the compound of formula 1.
  • the dopant at least one phosphorescent dopant is preferable.
  • the phosphorescent dopant is not particularly limited; however, preferably, a complex compound comprising a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metalated complex compound comprising a metal atom selected from Ir, Os, Cu and Pt, and even more preferably, an ortho-metalated complex compound comprising Ir is comprised.
  • the phosphorescent dopant from the group consisting of compounds represented by the following formulae 2 to 4:
  • L is selected from the following structure:
  • R 100 represents hydrogen or a substituted or unsubstituted (C1-C30)alkyl group
  • R 101 to R 109 and R 111 to R 127 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group substituted or unsubstituted with a halogen, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, or a (C1-C30)alkyl group substituted or unsubstituted with a halogen
  • f and g each independently represent an integer of 1 to 3
  • h represents an integer of 1 to 2
  • f, g, or h are integers of 2 or more, each of R 100 is the same or different
  • n represents an integer of 1 to 3.
  • the phosphorescent dopant includes the following
  • the organic electroluminescent device of the present invention comprises a first electrode, a second electrode and at least one organic layer between the first electrode and the second electrode; the organic layer comprises a light-emitting layer; the light-emitting layer comprises a composition for the organic electroluminescent device of the present invention and a phosphorous dopant; and the composition for the organic electroluminescent device is used as a host material.
  • the organic electroluminescent device of the present invention may further comprise, in addition to the compound of formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.
  • the organic layer may further comprise, in addition to the compound of formula 1, 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 of the present invention may emit a 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, in addition to the compound of the present invention. If necessary, the organic electroluminescent device may further comprise a yellow light-emitting layer or an orange light-emitting layer.
  • 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).
  • the chalcogenide (includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer
  • the 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 SiO X (1 ⁇ X ⁇ 2), AlO X (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 a 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 the 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 a white light.
  • the organic electroluminescent compound of the present invention provides an organic electroluminescent device which has high luminous efficiency and a long operation lifetime and requires a low driving voltage, to thereby have improved power efficiency and power consumption.
  • EA ethyl acetate
  • THF tetrahydrofuran
  • MC methylene chloride
  • n-Bu normal-butyl
  • 2,4-dichloropyrimidine 7 g (0.047 mol), compound 2-3 10 g (0.036 mol), 2M Na 2 CO 3 45 mL, toluene 182 mL and ethanol 45 mL were mixed.
  • the mixture was stirred under reflux for 12 hours, and then was cooled to room temperature. After adding distilled water thereto, the mixture was extracted with EA, was dried with MgSO 4 , and was distilled under reduced pressure.
  • Compound 2-4 9 g (0.026 mol, 72.9%) was obtained by purifying via column chromatography.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an OLED device 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. 2-TNATA [4,4’,4”-tris(N,N-(2-naphthyl)phenylamino)triphenylamine] 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.
  • the two materials were evaporated at different rates and was deposited in a doping amount of 4 to 20 wt% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 9,10-di(1-naphthyl)-2-(4-phenyl-1-phenyl-1H-benzo[d]imidazole)anthracene was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at different rates and were deposited in a doping amount of 30 to 70 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • All the materials used for producing the OLED device were those purified by vacuum sublimation at 10 -6 torr.
  • the produced OLED device showed green-light emission having a luminance of 1,000 cd/m 2 and a current density of 2.41 mA/cm 2 at a driving voltage of 3.2 V.
  • An OLED device was produced in the same manner as one of Example 1, except for using compound C-31 and compound D-28 as a host material and a dopant, respectively.
  • the produced OLED device showed orange-light emission having a luminance of 1,000 cd/m 2 and a current density of 2.55 mA/cm 2 at a driving voltage of 3.7 V.
  • An OLED device was produced in the same manner as one of Example 1, except for using compound C-31 and compound D-44 as a host material and a dopant, respectively.
  • the produced OLED device showed dark orange-light emission having a luminance of 1,000 cd/m 2 and a current density of 6.67 mA/cm 2 at a driving voltage of 4.0 V.
  • An OLED device was produced in the same manner as one of Example 1, except for using compound C-41 and compound D-1 as a host material and a dopant, respectively.
  • the produced OLED device showed green-light emission having a luminance of 1,000 cd/m 2 and a current density of 2.46 mA/cm 2 at a driving voltage of 3.1 V.
  • An OLED device was produced in the same manner as one of Example 1, except for using compound C-66 and compound D-1 as a host material and a dopant, respectively.
  • the produced OLED device showed green-light emission having a luminance of 1,000 cd/m 2 and a current density of 2.65 mA/cm 2 at a driving voltage of 3.0 V.
  • An OLED device was produced in the same manner as one of Example 1, except for using compound C-53 and compound D-1 as a host material and a dopant, respectively.
  • the produced OLED device showed green-light emission having a luminance of 1,000 cd/m 2 and a current density of 2.56 mA/cm 2 at a driving voltage of 3.0 V.
  • An OLED device was produced in the same manner as one of Example 1, except for depositing a light-emitting layer having a thickness of 30 nm on the hole transport layer by using CBP as a host material and compound D-1 as a dopant and depositing a hole blocking layer having a thickness of 10 nm by using BAlq.
  • the produced OLED device showed green-light emission having a luminance of 1,000 cd/m 2 and a current density of 2.86 mA/cm 2 at a driving voltage of 4.9 V.
  • An OLED device was produced in the same manner as one of Example 1, except for depositing a light-emitting layer having a thickness of 30 nm on the hole transport layer by using CBP as a host material and compound D-28 as a dopant and depositing a hole blocking layer having a thickness of 10 nm by using BAlq.
  • the produced OLED device showed orange-light emission having a luminance of 1,000 cd/m 2 and a current density of 3.05 mA/cm 2 at a driving voltage of 4.6 V.
  • An OLED device was produced in the same manner as one of Comparative Example 1, except for using compound D-44 as a dopant.
  • the produced OLED device showed dark orange-light emission having a luminance of 1,000 cd/m 2 and a current density of 8.2 mA/cm 2 at a driving voltage of 5.2 V.
  • the compounds of the present invention have superior luminescent properties than conventional compounds, and thus provide an organic electroluminescent device which has high luminous efficiency and requires a low driving voltage, to thereby have improved power efficiency and power consumption.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention porte sur un composé organique électroluminescent de la formule (1) et sur un dispositif électroluminescent organique le comportant. Le composé organique luminescent permet d'obtenir un dispositif électroluminescent organique dont l'efficacité lumineuse est élevée et dont la durée de vie de fonctionnement est longue, et qui requiert une faible tension d'excitation, afin d'avoir un rendement énergétique et une consommation d'énergie améliorés.
PCT/KR2012/003472 2011-05-03 2012-05-03 Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant WO2012150826A1 (fr)

Priority Applications (3)

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JP2014509244A JP6046701B2 (ja) 2011-05-03 2012-05-03 新規な有機電界発光化合物および同化合物を使用した有機電界発光素子
EP12779767.8A EP2694619A4 (fr) 2011-05-03 2012-05-03 Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant
CN201280031410.1A CN103764786B (zh) 2011-05-03 2012-05-03 新型有机电致发光化合物以及使用该化合物的有机电致发光器件

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KR10-2011-0041819 2011-05-03
KR20110041819 2011-05-03
KR1020120046340A KR101396171B1 (ko) 2011-05-03 2012-05-02 신규한 유기 발광 화합물 및 이를 채용하는 유기 전계 발광 소자
KR10-2012-0046340 2012-05-02

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US10199580B2 (en) 2011-11-22 2019-02-05 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
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WO2014054912A1 (fr) * 2012-10-04 2014-04-10 Rohm And Haas Electronic Materials Korea Ltd. Composés organiques électroluminescents et dispositif organique électroluminescent comprenant lesdits composés
JPWO2014091958A1 (ja) * 2012-12-10 2017-01-05 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2014091958A1 (fr) * 2012-12-10 2014-06-19 コニカミノルタ株式会社 Matériau pour élément électroluminescent organique, élément électroluminescent organique, dispositif d'éclairage, et dispositif d'affichage
KR101995191B1 (ko) * 2012-12-10 2019-07-02 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자 재료, 유기 일렉트로루미네센스 소자, 조명 장치 및 표시 장치
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JP2016515098A (ja) * 2013-02-27 2016-05-26 ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ ブロモドメイン阻害剤として有用なカルバゾール化合物
WO2014188947A1 (fr) * 2013-05-20 2014-11-27 保土谷化学工業株式会社 Nouveau dérivé pyrimidine et élément électroluminescent organique
JPWO2014188947A1 (ja) * 2013-05-20 2017-02-23 保土谷化学工業株式会社 新規なピリミジン誘導体および有機エレクトロルミネッセンス素子
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JPWO2015033894A1 (ja) * 2013-09-04 2017-03-02 出光興産株式会社 カルバゾール誘導体、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器
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US10510963B2 (en) 2014-04-04 2019-12-17 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting element comprising same
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US10381572B2 (en) 2014-04-04 2019-08-13 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting element comprising same
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US10916710B2 (en) 2014-04-04 2021-02-09 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting element comprising same
US10964892B2 (en) 2014-04-04 2021-03-30 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting device comprising same
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US11362280B2 (en) 2014-04-04 2022-06-14 Lg Chem, Ltd. Organic light-emitting device
US11271167B2 (en) 2014-04-04 2022-03-08 Lg Chem, Ltd. Organic light-emitting device
JP7270099B2 (ja) 2014-04-08 2023-05-09 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 多成分ホスト材料及びそれを含む有機電界発光デバイス
JP2022123051A (ja) * 2014-04-08 2022-08-23 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 多成分ホスト材料及びそれを含む有機電界発光デバイス
US20220216430A1 (en) * 2014-04-18 2022-07-07 Rohm And Haas Electronic Materials Korea Ltd. Multi-component host material and an organic electroluminescence device comprising the same
US20230020540A1 (en) * 2014-04-29 2023-01-19 Rohm And Haas Electronic Materials Korea Ltd. Multi-component host material and organic electroluminescent device comprising the same
KR20150124902A (ko) * 2014-04-29 2015-11-06 롬엔드하스전자재료코리아유한회사 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
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US20210210697A1 (en) * 2014-05-14 2021-07-08 Rohm And Haas Electronic Materials Korea Ltd. Multi-component host material and organic electroluminescent device comprising the same
US20220102644A1 (en) * 2014-07-22 2022-03-31 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent device
US11917907B2 (en) * 2014-07-22 2024-02-27 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent device
US20220102633A1 (en) * 2014-07-22 2022-03-31 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent device
US11098019B2 (en) 2015-07-30 2021-08-24 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2018016724A1 (fr) * 2016-07-22 2018-01-25 삼성에스디아이 주식회사 Composé pour dispositif optoélectronique organique, composition pour dispositif optoélectronique organique, dispositif optoélectronique organique et dispositif d'affichage
US10833276B2 (en) 2016-11-21 2020-11-10 Universal Display Corporation Organic electroluminescent materials and devices
US11339143B2 (en) 2018-06-26 2022-05-24 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
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