WO2015053524A1 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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WO2015053524A1
WO2015053524A1 PCT/KR2014/009403 KR2014009403W WO2015053524A1 WO 2015053524 A1 WO2015053524 A1 WO 2015053524A1 KR 2014009403 W KR2014009403 W KR 2014009403W WO 2015053524 A1 WO2015053524 A1 WO 2015053524A1
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group
aryl
formula
alkyl
boron
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김태형
이용환
이인혁
김은진
백영미
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주식회사 두산
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Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
  • a host / dopant system may be used as a light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
  • a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
  • the existing materials have advantages in terms of light emission characteristics, but the thermal stability is low due to the low glass transition temperature, and thus the materials are not satisfactory in terms of lifespan of the organic EL device.
  • an object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.
  • Another object of the present invention is to provide an organic electroluminescent device having an improved driving voltage, luminous efficiency, and the like, including the organic compound.
  • the present invention provides a compound represented by the following formula (1).
  • L 1 and L 2 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 18 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 18 nuclear atoms,
  • X 1 to X 3 are each independently N or C (R 11 ), wherein at least one is N,
  • R 1 to R 4 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ C 40 cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ aryl boronic of C 40, a C 6 ⁇ C 40 An arylphosphine group, a C 6 -C 40 arylphosphine oxide group and a C 6 -C 40 arylsilyl group
  • R 11 and Ar 1 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ C 40 cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ aryl boronic of C 40, a C 6 ⁇ C 40 An aryl phosphine group, a C 6 ⁇ C 40 aryl phosphine oxide group and a C 6 ⁇ C 40 arylsily
  • Arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, arylsilyl group are each independently deuterium, halogen, cyano group, C 1 a ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the Aryloxy group, C 1 to C 40 alkyloxy group, C 6
  • n are each independently an integer of 0-4.
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
  • the organic material layer including the compound of Formula 1 may be a phosphorescent layer.
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like. There is no limitation.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. ), Isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2- Propanyl (2-propynyl) and the like, but are not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined.
  • a form in which two or more rings are pendant or condensed with each other may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 40 carbon atoms.
  • R means aryl having 6 to 40 carbon atoms.
  • Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and includes a linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Aryl amine in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Substituted with a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the novel compound according to the present invention forms a basic skeleton by combining dibenzofuran (dibenzo [b, d] furan), a 6-membered heterocycle, an indole moiety, and a structure in which various substituents are bonded to the basic skeleton. It is characterized in that represented by the formula (1).
  • Dibenzofuran (dibenzo [b, d] furan) has a large triplet energy and is electrochemically stable.
  • a six-membered nitrogen-containing heterocyclic ring eg, pyridine, pyrimidine, triazine
  • EWG electron withdrawing group
  • EWG electron withdrawing group
  • EWG electron withdrawing group
  • EWG electron withdrawing group
  • the entire molecule has an electron donating group (EDG) and exhibits bipolar characteristics, the bonding force between the holes and the electrons is high, so that the molecules can be used not only as a host in the phosphorescent layer but also in the hole transport layer and the hole injection layer.
  • the compound represented by the general formula (1) of the present invention is significantly increased in molecular weight of the compound due to the aromatic ring (aromatic ring) or heteroaromatic ring (heteroaromatic ring) substituents, the glass transition temperature is improved as the conventional CBP (4, 4-dicarbazolybiphenyl) shows higher thermal stability.
  • the compound represented by the formula (1) of the present invention is also effective in suppressing crystallization of the organic material layer.
  • the efficiency of the organic electroluminescent device and the conventional organic material layer for example, CBP
  • the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • L 1 and L 2 are a divalent group linker, a single bond, a substituted or unsubstituted C 6 ⁇ C 40 arylene group, or substituted or It is an unsubstituted heteroarylene group having 5 to 40 nuclear atoms.
  • the C 6 to C 40 arylene group and the heteroarylene group having 5 to 40 nuclear atoms are not particularly limited, a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, and a pyrantrenylene group , Carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group, pyrimididi And a nylene group.
  • L 1 and L 2 are each independently a single bond, a phenylene group, or a biphenylene group.
  • X 1 to X 3 are each independently N or C (R 11 ), at least one includes N, it is preferable that all of X 1 to X 3 are N Do.
  • X 1 to X 3 are C (R 11 )
  • a plurality of R 11 are the same or different from each other, and R 11 is preferably hydrogen.
  • R 1 and R 2 may be bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, and a condensed heteroaromatic ring.
  • R 1 and R 2 are preferably bonded to each other to form benzene, naphthalene, indole, fluorene, carbazole.
  • R 3 and R 4 are each independently hydrogen, a C 6 ⁇ C 40 aryl group, or a heteroaryl group having 5 to 40 nuclear atoms.
  • R 3 is more preferably selected from the group consisting of hydrogen, phenyl group, naphthyl group, fluorene group, carbazole group, dibenzothiophene group, dibenzofuran group, dibenzoselenophene group and dibenzosilol group.
  • Ar 1 is preferably a hydrogen, a C 6 ⁇ C 40 aryl group, or a heteroaryl group having 5 to 40 nuclear atoms.
  • the compound represented by the formula (1) of the present invention is preferably selected from the group consisting of the compound represented by the following formula (2 to 10).
  • Y 1 is selected from the group consisting of N (R 12 ), O, S, Se, C (R 13 ) (R 14 ) and Si (R 15 ) (R 16 ),
  • R 5 , R 6 and R 12 to R 16 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 ⁇ 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 It is selected from the group consisting of arylsilyl group,
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R 5, R 6 , R 12 to R 16 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycl
  • Examples of the compound represented by Formula 1 of the present invention include the following compounds (C-1 to C-129), but the compound represented by Formula 1 of the present invention is not limited to the following compounds.
  • the present invention includes an anode, a cathode and at least one organic layer interposed between the anode and the cathode, and at least one of the at least one organic layer includes the compound represented by Formula 1 It provides an organic electroluminescent device.
  • the compound may be used alone, or two or more may be used in combination.
  • the at least one organic material layer may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the organic material layer including the compound represented by Chemical Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and in this case, the host material may include a compound represented by Formula 1 above.
  • the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material.
  • the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention is another organic material layer using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Formula 1 above. And it can be manufactured by forming an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • a silicon wafer quartz, glass plate, metal plate, plastic film, or the like may be used.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black and the like can be used.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), poly
  • the negative electrode material may be magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or a metal such as lead or an alloy thereof, and a multilayer such as LiF / Al or LiO 2 / Al. Structural materials and the like can be used.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.
  • IC-3 (18.85 g, 46.17 mmol), 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol), K 2 CO 3 ( 6.38 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C. for 12 hours.
  • IC-7 (18.44 g, 46.17 mmol) is used instead of IC-3, and 1-bromo-4-iodobenzene (19.59 g, 69.26 mmol) is used instead of 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol). Except for the same procedure as in Preparation Example 4 to obtain an IC-8.
  • IC-4 (336.96 g, 598 mmol) was used instead of bromobenzene, and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] was used instead of IC-1. Except for using furan-2-yl) -1,3,5-triazine (259.46 g, 598 mmol), the same procedure as in ⁇ Step 1> of Synthesis Example 1 was performed, thereby obtaining C-2 (369.21) as a target compound. g, yield 70%) was obtained.
  • IC-4 (336.96 g, 598 mmol) is used instead of bromobenzene, and 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine is used instead of IC-1. Except for using (267.82 g, 598 mmol) was carried out in the same manner as in ⁇ Step 1> of Synthesis Example 1 to obtain the target compound C-3 (289.33 g, yield 54%).
  • IC-6 (405.81 g, 598 mmol) was used instead of bromobenzene, and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (pyridin-2-yl)-was used instead of IC-1. Except for using 1,3,5-triazine (214.55 g, 598 mmol) to carry out the same process as in ⁇ Step 1> of Synthesis Example 1 to give the target compound C-5 (181.95 g, 33% yield) Got it.
  • IC-8 (331.59 g, 598 mmol) was used instead of bromobenzene, and 9- (4- (4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3, Except for using 5-triazin-2-yl) phenyl) -9H-carbazole (312.74 g, 598 mmol), and was subjected to the same process as in ⁇ Step 1> of Synthesis Example 1 C-7 (253.15 g, yield 44%).
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.
  • ITO Indium tin oxide
  • a device was manufactured in the same manner as in Example 1, except that CBP and Ref-1 were used instead of the compound of Synthesis Example 1 as a light emitting host material when forming the emission layer.
  • Examples 1 to 9 in which the compound of the present invention was applied to the light emitting layer of the green organic electroluminescent device were compared to Comparative Examples 1 and 2 in which the conventional CBP and Ref-1 were applied to the light emitting layer of the green organic electroluminescent device. It was confirmed that the efficiency and the driving voltage is excellent.
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then washed the substrate for 5 minutes using UV and vacuum The substrate was transferred to the evaporator.
  • ITO Indium tin oxide
  • M-MTDATA 60 nm) / TCTA (80 nm) / each compound synthesized in Synthesis Examples 6 to 8 + 10% (piq) 2 Ir (acac) (30nm) / BCP on the thus prepared ITO transparent substrate (electrode)
  • the device was manufactured by stacking in the order of (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • a device was manufactured in the same manner as in Example 10, except that CBP was used instead of the compound of Synthesis Example 6 as a light emitting host material when forming the emission layer.
  • Examples 10 to 12 in which the compound of the present invention is applied to the light emitting layer of the red organic electroluminescent device have a higher efficiency and driving voltage compared to Comparative Example 3 in which the conventional CBP is applied to the light emitting layer of the red organic electroluminescent device. It was confirmed that it was excellent.
  • the compound represented by Formula 1 according to the present invention can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence properties.
  • an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le contenant. Le composé selon la présente invention est utilisé dans une couche organique d'un dispositif électroluminescent organique et de préférence dans une couche luminescente pour conférer à un un dispositif électroluminescent organique un meilleur rendement lumineux, une meilleure tension d'attaque, et une plus longue durée de vie de fonctionnement.
PCT/KR2014/009403 2013-10-10 2014-10-07 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2015053524A1 (fr)

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WO2019191454A1 (fr) * 2018-03-28 2019-10-03 Kyulux, Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
CN110444693A (zh) * 2018-05-04 2019-11-12 材料科学有限公司 有机电致发光器件
CN113666919A (zh) * 2021-09-23 2021-11-19 南京高光半导体材料有限公司 一种含有咔唑、二苯并呋喃及三嗪结构的化合物及有机电致发光器件
CN114373872A (zh) * 2020-10-15 2022-04-19 江苏三月科技股份有限公司 一种有机电致发光器件
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices

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KR102054277B1 (ko) 2016-07-29 2019-12-10 삼성에스디아이 주식회사 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
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WO2018128255A1 (fr) * 2017-01-05 2018-07-12 삼성에스디아이 주식회사 Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage
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KR102008897B1 (ko) 2017-06-22 2019-10-23 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
US20190198772A1 (en) 2017-06-22 2019-06-27 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display deivce
KR102162402B1 (ko) 2017-07-21 2020-10-06 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
KR102537898B1 (ko) * 2018-05-28 2023-05-31 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN111989326B (zh) 2018-10-22 2024-03-05 株式会社Lg化学 新的杂环化合物和包含其的有机发光器件
WO2020085740A1 (fr) * 2018-10-22 2020-04-30 주식회사 엘지화학 Nouveau composé hétérocyclique et diode électroluminescente organique l'utilisant
KR102368409B1 (ko) 2019-05-30 2022-02-25 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR102429537B1 (ko) 2019-06-28 2022-08-03 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치

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WO2015190789A1 (fr) * 2014-06-09 2015-12-17 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
WO2019191454A1 (fr) * 2018-03-28 2019-10-03 Kyulux, Inc. Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
CN110444693A (zh) * 2018-05-04 2019-11-12 材料科学有限公司 有机电致发光器件
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US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
CN114373872A (zh) * 2020-10-15 2022-04-19 江苏三月科技股份有限公司 一种有机电致发光器件
CN113666919A (zh) * 2021-09-23 2021-11-19 南京高光半导体材料有限公司 一种含有咔唑、二苯并呋喃及三嗪结构的化合物及有机电致发光器件
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