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WO2016064102A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2016064102A1
WO2016064102A1 PCT/KR2015/010233 KR2015010233W WO2016064102A1 WO 2016064102 A1 WO2016064102 A1 WO 2016064102A1 KR 2015010233 W KR2015010233 W KR 2015010233W WO 2016064102 A1 WO2016064102 A1 WO 2016064102A1
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group
aryl
formula
layer
alkyl
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Korean (ko)
Inventor
신진용
박호철
김영배
김회문
이창준
백영미
김태형
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Doosan Corp
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Doosan Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the organic EL device when current or voltage is applied to two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, an exciton is formed, and the exciton falls to the ground and shines.
  • the organic EL device may be classified into a fluorescent EL device in which singlet excitons contribute to light emission and a phosphorescent EL device in which triplet excitons contribute to light emission according to the electron spin type of the formed exciton.
  • FIG. 1 is a cross-sectional view illustrating an organic EL device according to an exemplary embodiment of the present invention.
  • the bipolar compound may be used as an electron transport layer, an electron injection layer, or both materials in addition to the life improvement layer.
  • the hole injection layer 301 and the hole transport layer 302 included in the organic material layer 300 of the present invention serve to move the holes injected from the anode 100 to the light emitting layer 303.
  • the material forming the hole injection layer 301 and the hole transport layer 302 is not particularly limited as long as the hole injection barrier is low and the hole mobility is high, and the hole injection layer / transport layer material used in the art can be used without limitation. have. Non-limiting examples thereof include arylamine derivatives.
  • the host when the light emitting layer 303 is blue fluorescence, green fluorescence or red fluorescence, the host may include 80 to 99.9 wt% and the dopant may include 0.1 to 20 wt%. In addition, when the light emitting layer 303 is blue fluorescence, green fluorescence, or red phosphorescence, the host may include 70 to 99 wt% and the dopant 1 to 30 wt%.
  • the dopant included in the emission layer 303 is not particularly limited as long as it is known in the art, and non-limiting examples thereof include anthracene derivative, pyrene derivative, arylamine derivative, iridium (Ir) or platinum (Pt).
  • the metal complex compound to contain is mentioned.
  • the bipolar compound has an ionization potential of 5.5 eV or more, when it is used in the life improvement layer 304, holes can be prevented from diffusing or moving to the electron transport layer 305, thereby improving the life of the organic EL device.
  • the two or more kinds of bipolar compounds included in the life improvement layer 304 of the present invention exhibit hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / V ⁇ s or more at room temperature by an electron donor (EDG),
  • the electron mobility is 1 ⁇ 10 ⁇ 6 cm 2 / V ⁇ s or more at room temperature by dragging (EWG), and when used in the life improvement layer 304, electrons may be effectively injected into the light emitting layer 303.
  • EWG electron donor
  • EWG electron donor
  • a 1 to A 11 are the same as or different from each other, each independently N or C (R), and at least one is N, wherein a plurality of R's are the same or different from each other even if they are the same, or they are adjacent It may form condensed rings with groups.
  • a plurality of A 1 to A 6 which is C (R) other than N, such as A 1 and A 2 , A 2 and A 3 , A 3 and A 4 , A 4 and A 5 , A 5 and A 6 ,
  • a 6 and A 1 may be bonded to each other to form a condensed ring.
  • the electron attracting (EWG) moiety is a nitrogen-containing heteroaromatic hydrocarbon having 5 or 6 nuclear atoms in which 1-3 carbons are substituted with nitrogen.
  • the moiety may include a form in which two or more rings are simply attached to or condensed with each other, and may also include a form in which an aryl group is condensed.
  • EWG electron attracting property
  • the bipolar compound which is included as the material for improving the lifespan layer 304 of the present invention and differs from each other in electron mobility, is characterized by including an electron donor (EDG) moiety represented by the following Chemical Formula 1.
  • EDG electron donor
  • non-limiting examples of the moiety having the electron donor (EDG) characteristics of the electron donor include condensed nitrogen heteroaromatic rings such as indole, carbazole, and azepine; Or a condensed polycyclic aromatic ring such as biphenyl, triphenylene, fluoranthene and the like may be used, more specifically it may be represented by the following formula (1).
  • Y 1 to Y 4 are the same as or different from each other, and each independently N or C (R 1 ), wherein a plurality of R 1 are each the same or different even if represented the same, and they may form a condensed ring with an adjacent group There is;
  • X 2 and X 3 are the same as or different from each other, and each independently N or C (R 2 ), wherein a plurality of R 2 are the same or different, even though they are the same, and they may form condensed rings with adjacent groups There is;
  • R 1 to R 2 and Ar 1 to Ar 5 are the same as or different from each other, and each independently, hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, is selected from the group consisting of C 6 ⁇ C group 60 arylboronic of, C 1 ⁇ C 40 of the phosphine group, C 1 ⁇ C 40 phosphine
  • Chemical Formula 1 may be more embodied as any one of the following A-1 to A-24. However, it is not limited thereto.
  • R 2 , Y 1 to Y 4, and Ar 1 to Ar 5 are the same as those of Formula 1 described above. In this case, considering the physical and chemical properties of the compound, it is preferable that the A-1 to A-6.
  • Formula 1 which is an electron donor (EDG) moiety
  • EDG electron donor
  • a plurality of R 3 non-forming a condensed ring may be the same or different from each other even if they are the same, and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C 1 to C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, a nuclear Heteroaryl group of 5 to 60 atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ alkyl boron C 40 group, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40
  • the phosphine group, the phosphine oxide group and the arylamine group are each independently deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 1 to C 40 Alkyloxy group, C 6 ⁇ C
  • X 1 to X 4 and Y 1 to Y 8 are as defined in the formula (1) and (2).
  • Y 1 to Y 4 which form a condensed ring are N or C (R 1 ), all of which are preferred when C (R 1 ), and Y 5 to Y 8 are N Or C (R 3 ), all of which are C (R 3 ).
  • R 1 and R 3 are the same or different, respectively.
  • Ar 1 and R 1 to R 3 are the same as defined in the formula (1) and (2).
  • the compounds of Formulas B-1 to B-30 having a condensed structure of Formula 1 and Formula 2 include one or more condensed indole or condensed carbazole moieties.
  • Y 1 to Y 4 are the same or different and are each independently N or C (R 1), and double-Y 1 to Y is and preferably 4 are both C (R 1), wherein a plurality of R 1 are the same Or different.
  • X 3 are each independently N or C (R 2 ),
  • Y 5 to Y 14 are the same as or different from each other, and each independently N or C (R 3 ), preferably Y 5 to Y 14 are all C (R 3 ), wherein a plurality of R 3 are the same Or different.
  • Ar 1 and R 1 to R 3 are the same as defined in the formula (1) and (3).
  • Ar 1 is preferably a substituted or unsubstituted C 6 ⁇ C 60 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms
  • Ar 2 to Ar 5 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 40 alkyl group (specifically, a methyl group) or a substituted or unsubstituted C 6 to C 60 aryl group (specifically Phenyl group) is preferable.
  • bipolar compounds which are included in the life improvement layer material and differ in electron mobility from each other, may include a moiety having an electron donor (EDG) characteristic of an electron donor represented by the following general formula (4). Can be.
  • EDG electron donor
  • Ar 6 to Ar 8 are the same as or different from each other, and each independently selected from hydrogen, deuterium, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 5 to 40 nuclear atoms, provided that Ar 6 Except that when Ar 8 is the same,
  • R 4 to R 6 are the same or different and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl, C alkenyl group of 2 ⁇ C 40, C Alkynyl group of 2 to C 40 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ aryloxy C 60, C 1 ⁇ C 40 alkyl silyl group, C 6 ⁇ aryl silyl group of C 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 aryl boron group, C 1 ⁇ C 40 of the phosphine is selected from the pingi, C 1 ⁇ C 40 phosphine oxide group, and the group consisting of
  • a to c are each independently an integer of 0 to 3
  • the time period, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, phosphine group, phosphine oxide group and arylamine group are each independently deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, C 3 ⁇ 40 Heterocycloalkyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 1
  • L One To L 3 are the same as or different from each other, each independently selected from a single bond, an arylene group of C 6 ⁇ C 60 , a hetero arylene group of 5 to 60 nuclear atoms
  • it may be a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms.
  • it may be selected from a single bond, phenylene, biphenylene, carbazolylene.
  • Ar 6 to Ar 8 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, an aryl group having 6 to 40 carbon atoms, and a heteroaryl group having 5 to 40 nuclear atoms, wherein Ar 6 At least one of Ar to 8 is preferably selected from a heteroaryl group having 5 to 40 nuclear atoms including at least one element selected from the group consisting of N, O, and S. However, the case where Ar 6 to Ar 8 are all the same is excluded.
  • At least one of R 1 to R 6 and Ar 1 to Ar 8 is the moiety having an electron-withdrawing (EWG) property of high electron absorption Form a bond with.
  • EWG electron-withdrawing
  • 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.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • aryls include 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 pendant or condensed with each other may also be included, and may also include a form condensed with an aryl group.
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 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 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 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 5 to 40 carbon atoms.
  • the mixing ratio between two or more kinds of bipolar compounds having different electron mobility is not particularly limited.
  • the two bipolar compounds may be mixed in a weight ratio of 1:99 to 99: 1, preferably in the range of 10:90 to 90:10 weight ratio.
  • the method for manufacturing the life improvement layer 304 is not particularly limited as long as it is known in the art, and may be manufactured by, for example, the following two methods.
  • the first method is a co-deposition method of placing two different bipolar compounds in the first heat source and the second heat source, respectively, and simultaneously applying heat to form the life improvement layer 304.
  • the second method is to reduce the number of heat sources used, and to mix the bipolar compounds used to form the life improvement layer 304 in an appropriate ratio to place a single heat source to heat the life improvement layer to simplify the formation process Co-deposition is performed to form 304.
  • the light emitting layer can be formed.
  • the usage-amount of each bipolar compound used at this time is not specifically limited.
  • the electron transport layer 305 and the electron injection layer 306 included in the organic material layer 300 of the present invention serve to move the electrons injected from the cathode 200 to the emission layer 303.
  • the material constituting the electron transport layer 305 and the electron injection layer 306 is not particularly limited as long as it is easy to inject electrons and has high electron mobility, but is not limited thereto.
  • the bipolar compound, anthracene derivative, and heteroaromatic compound may be used. And alkali metal complex compounds.
  • the electron transport layer 305 and / or the electron injection layer 306 of the present invention may use the same bipolar material as the life improvement layer 304.
  • the electron transport layer 305 and / or the electron injection layer 306 may be a co-deposited alkali metal complex compound to facilitate the injection of electrons from the cathode.
  • the alkali metal complex compound may be an alkali metal, an alkaline earth metal or a rare earth metal.
  • the organic material layer 300 of the present invention configured as described above may further include an organic film layer (not shown) for blocking electrons and excitons between the hole transport layer 302 and the light emitting layer 303.
  • the organic layer has a high LUMO value to prevent electrons from moving to the hole transport layer 302 and a high triplet energy to prevent the excitons of the light emitting layer 303 from diffusing into the hole transport layer 302.
  • the material constituting such an organic film layer is not particularly limited, and examples thereof include carbazole derivatives or arylamine derivatives.
  • the method of manufacturing the organic material layer 300 of the present invention is not particularly limited, and non-limiting examples thereof include a vacuum deposition method and a solution coating method.
  • the solution coating method may be spin coating, dip coating, doctor blading, inkjet printing, thermal transfer method and the like.
  • the organic electroluminescent device of the present invention has a structure in which the anode 100, the organic material layer 300 and the cathode 200 are sequentially stacked, between the anode 100 and the organic material layer 300 or between the cathode 200 and the organic material layer An insulating layer or an adhesive layer may be further included between the 300.
  • Such an organic electroluminescent device of the present invention may have excellent life characteristics because the half-life of the initial brightness is increased while maintaining the maximum luminous efficiency when voltage and current are applied.
  • Embodiment compounds LE-01 to LE-16 of the present invention are shown below.
  • the relative electron mobility of LE-01, LE-06, LE-08 and LE-10 in the bipolar compound of the present invention was measured as follows.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • the device was fabricated by depositing the structure of Table 2 on the prepared ITO transparent electrode (substrate) as described above, and the current density and driving voltage were measured and shown in FIG. 2.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • Hole injection layer DS-205 (Doosan Corporation) 80 nm Hole transport layer NPB 15 nm Light emitting layer ADN + 5% DS-405 (Doosan Corporation) 30 nm Life Improvement Layer LE-01 to LE-36 5 nm Electron transport layer Alq 3 25 nm Electron injection layer LiF 1nm cathode Al 200 nm
  • a device was manufactured in the same manner as in Example 1, except that the electron transport layer was deposited at 30 nm without using the life improving layer.
  • a device was manufactured in the same manner as in Example 1, except that BCP, LE-08, and LE-10 were respectively used as the life improvement layer.
  • the organic electroluminescent device of Examples 1 to 20 of the present invention including two or more kinds of bipolar compounds having different electron mobility as the life improvement layer is more current than the organic electroluminescent device of Comparative Examples 1 to 4 It was confirmed that the efficiency and life is excellent. In particular, the organic electroluminescent device of the present invention was confirmed to have improved life compared with Comparative Examples 3 to 4 using one kind of bipolar compound as the life improvement layer.

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

Abstract

La présente invention concerne un dispositif électroluminescent organique qui comprend : une anode, une cathode, et une ou plusieurs couches organiques qui sont disposées entre l'anode et la cathode, ces couches étant sélectionnées dans le groupe comprenant une couche d'injection de trous, une couche de transport de trous, une couche électroluminescente, une couche de transport d'électrons et une couche d'injection d'électrons; et qui comprend en outre une couche d'augmentation de la durée de vie située entre la couche électroluminescente et la couche de transport d'électrons.
PCT/KR2015/010233 2014-10-22 2015-09-25 Dispositif électroluminescent organique Ceased WO2016064102A1 (fr)

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KR1020140143556A KR101708097B1 (ko) 2014-10-22 2014-10-22 유기 전계 발광 소자

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US20160322583A1 (en) * 2013-12-27 2016-11-03 Doosan Corporation Organic electroluminescent device
US10230053B2 (en) * 2015-01-30 2019-03-12 Samsung Display Co., Ltd. Organic light-emitting device
US10280171B2 (en) 2016-05-31 2019-05-07 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
CN110698485A (zh) * 2019-11-21 2020-01-17 北京鼎材科技有限公司 一种化合物及其应用
US10954243B2 (en) 2018-05-02 2021-03-23 Navire Pharma, Inc. Substituted heterocyclic inhibitors of PTPN11
US11104675B2 (en) 2018-08-10 2021-08-31 Navire Pharma, Inc. PTPN11 inhibitors
US11168093B2 (en) 2018-12-21 2021-11-09 Celgene Corporation Thienopyridine inhibitors of RIPK2
CN114736220A (zh) * 2022-04-27 2022-07-12 中国科学院福建物质结构研究所 一种线性三核铜(i)配合物及其制备方法和有机电致发光二极管
US11466017B2 (en) 2011-03-10 2022-10-11 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11

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KR102611320B1 (ko) * 2016-09-21 2023-12-07 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102673509B1 (ko) * 2016-09-28 2024-06-10 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102344831B1 (ko) * 2016-12-21 2021-12-30 솔루스첨단소재 주식회사 전자수송층 재료
KR102282799B1 (ko) * 2016-12-21 2021-07-29 솔루스첨단소재 주식회사 전자수송층 재료
KR102216993B1 (ko) * 2016-12-21 2021-02-18 솔루스첨단소재 주식회사 유기 전계 발광 소자
KR101884130B1 (ko) * 2017-08-29 2018-07-31 주식회사 두산 유기 전계 발광 소자

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