WO2011081423A2 - Composé de triphénylène et dispositif à électroluminescence organique incluant celui-ci - Google Patents

Composé de triphénylène et dispositif à électroluminescence organique incluant celui-ci Download PDF

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WO2011081423A2
WO2011081423A2 PCT/KR2010/009459 KR2010009459W WO2011081423A2 WO 2011081423 A2 WO2011081423 A2 WO 2011081423A2 KR 2010009459 W KR2010009459 W KR 2010009459W WO 2011081423 A2 WO2011081423 A2 WO 2011081423A2
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WO2011081423A3 (fr
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류동완
김태형
김경수
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주식회사 두산
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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

Definitions

  • the present invention includes a novel triphenylene compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or luminous ability, and including the same in at least one organic layer, such as luminous efficiency, luminance, thermal stability, driving voltage, and lifetime. This is an improved organic electroluminescent device.
  • Organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') are self-luminous display devices, and thus have excellent contrast ratio, wide viewing angle, and fast response time, which are suitable for high performance displays.
  • an organic EL device has a thin film multilayer structure in which an anode is formed on a substrate and a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially formed on the anode. It is.
  • organic EL devices currently used include a hole injection layer that receives holes into a substrate, an anode, and an anode, a hole transport layer that transfers holes, a light emitting layer that recombines holes and electrons to emit light, an electron transport layer that transfers electrons, It consists of an electron injection layer and a cathode which receive an electron from a cathode.
  • the reason why the organic EL device is manufactured in multiple layers is that the movement speeds of the holes and the electrons are different. Therefore, the holes and the electrons can be effectively transferred by making the appropriate hole injection layer, the transfer layer, the electron transfer layer, and the electron injection layer. This is because the light emission efficiency can be improved by balancing holes and electrons in the device.
  • Electrons injected from the electron injection layer and holes transferred from the hole injection layer recombine in the light emitting layer to form excitons, and fall from the singlet excited state to the ground state and are called fluorescence, and fall from the triplet excited state to the ground state.
  • Luminescence is called phosphorescence.
  • the exciton is generated when the carrier is recombined in the emission layer, the ratio of singlet and triplet excitons is generated at a ratio of 1: 3, and when phosphorescence is used, the internal quantum efficiency may be 100%.
  • CBP 4,4-dicarbazolybiphenyl
  • a metal containing heavy atoms such as Ir and Pt as a phosphorescent guest material Complex compounds (US 6830828, etc.) have been widely reported.
  • CBP which is currently used phosphorescent host material
  • Tg glass transition temperature
  • an object of the present invention is to provide a triphenylene-based compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or light emitting ability (fluorescence or phosphorescence) and light emission efficiency, brightness, and thermal stability by including the same in at least one organic layer.
  • a triphenylene-based compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or light emitting ability (fluorescence or phosphorescence) and light emission efficiency, brightness, and thermal stability by including the same in at least one organic layer.
  • A is Indole derivatives of
  • R 1 to R 22 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted heterocyclic ring having 3 to 60 nuclear atoms, substituted or unsubstituted C1- C40 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted (C6-C60 aryl) C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl , Substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted (C6-C60 aryl) C1-C40 alkylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40
  • the present invention the anode; cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound described above.
  • the compound of formula 1 according to the present invention has a wide energy bandgap and has excellent thermal stability, and thus, when adopted as a blue, green, or red fluorescent or phosphorescent host material, a lower power than conventional 4,4-dicarbazolybiphenyl (CBP) High efficiency, high brightness and improved durability and lifespan can be achieved.
  • CBP 4,4-dicarbazolybiphenyl
  • the organic EL device including the compound of the present invention can be greatly improved in terms of light emitting performance and lifetime, and thus can be effectively applied to a full color display panel and the like.
  • FIG. 1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.
  • the present invention relates to a compound represented by the formula (1), specifically to a triphenylene moiety that is inadequate in the triplet energy level and thus does not sufficiently exhibit its properties as a phosphorescent host, through a linker (L) or through a direct bond.
  • a linker (L) or through a direct bond By connecting indole derivative moieties to achieve a sufficiently high triplet energy level, the phosphorescent properties are improved while improving the electron and / or hole transport ability, luminous efficiency, driving voltage, and lifetime characteristics. It provides a triphenylene-based compound (triphenylene-based compound).
  • R 1 to R 22 are each independently hydrogen or any substituent, and non-limiting examples of such substituents include deuterium, halogen, cyano, substituted or unsubstituted C1-C40 alkyl (preferably C1-C8 alkyl) , Substituted or unsubstituted heterocyclic ring having 3 to 60 nuclear atoms (preferably heterocyclic ring having 3 to 18 nuclear atoms), substituted or unsubstituted C1-C40 alkoxy (preferably C1-C24 alkoxy), substitution Or unsubstituted C6-C60 aryl (preferably C6-C24 aryl), substituted or unsubstituted C6-C60 aryloxy (preferably C6-C18 aryloxy), substituted or unsubstituted (C6-C60 aryl) C1-C40 alkyl (preferably (C6-C24 aryl) C1-C8 alkyl), substituted or unsubstituted C2-C40
  • R 14 and R 15 may be bonded to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring having 3 to 8 nuclear atoms.
  • R 13 , R 16 to R 19 are as defined above,
  • R 23 to R 26 are each independently the same as defined for R 1 to R 22 .
  • Representative compounds of Formula 1 of the present invention are compounds of Formula 1a:
  • L, A, n, R 1 , R 3 to R 12 are as defined above.
  • the compound of formula 1b in which the triphenylene moiety is bonded to the nitrogen atom of the indole derivative or the compound of formula 1c bonded to the R 17 position of the indole derivative having the highest HOMO orbital level is preferable in terms of orbital balance. This is inferred because it has less influence on the triphenylene orbital level.
  • L, n, R 1 , R 3 to R 19 are as defined above.
  • the linker L may be selected from the group of compounds of formula
  • X is CR 33 or a nitrogen atom
  • Y is CR 34 R 35 , SiR 36 R 37 , oxygen (O), sulfur (S), or PR 38 ;
  • R 27 to R 38 are each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted heterocyclic ring having 3 to 40 nuclear atoms, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C6-C40 arylthio, substituted or unsubstituted (C6-C40 aryl) C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted (C6-C40 aryl) C1-C40 alkylamino, substituted or unsubstituted C3-C20 Alkylsilyl
  • Alkyl, heterocyclic, alkoxy, aryl, aryloxy, arylthio, arylalkyl, alkenyl, alkylamino, arylalkylamino, alkylsilyl, arylsilyl, ketoaryl, haloalkyl, and arylene of R 27 to R 38 are Each independently may be further substituted with C1-C40 alkyl, C6-C40 aryl, heteroaryl having 5 to 40 nuclear atoms, and the like.
  • Unsubstituted heterocycle means a monoheterocyclic or polyheterocyclic aromatic or non-aromatic ring having 3 to 60 nuclear atoms, and at least one carbon, preferably 1 to 3, of the rings Carbon is substituted with a heteroatom such as Si, N, OS or P.
  • a heteroatom such as Si, N, OS or P.
  • Non-limiting examples thereof include morpholine, heterocycloalkyl such as piperazine, heteroaryl such as indole, and the like.
  • heterocycles as used herein are to be understood to include those in which an aromatic or non-aromatic heteroatom-containing ring is condensed (fused) with one or more aromatic or non-aromatic rings.
  • Unsubstituted aryl means an aromatic moiety having 6 to 60 carbon atoms, either singly or in combination of two or more rings, and is referred to herein as "aryloxy”, “arylalkyl”, “arylsilyl”, and the like. Two or more rings may be attached in a simple or fused form with one another. Examples of aryl include, but are not limited to, phenyl, hydroxyphenyl, alkoxyphenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Unsubstituted heteroaryl means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 60 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, P Or a heteroatom such as S. do. It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form 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 It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Unsubstituted arylene means a divalent aromatic hydrocarbon having a single ring or fused ring of 6 to 40 carbon atoms.
  • arylene may include, but are not limited to, phenylene, biphenylene, triphenylene, naphthylene, fluorene, and the like.
  • the compound of Formula 1 of the present invention may be synthesized according to a general synthetic method (eg, Suzuki coupling). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • the invention also includes an anode; Cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises a compound represented by Formula 1 above. To provide.
  • the compound of Formula 1 may be included alone or in plurality.
  • the organic layer including the compound of Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, an electron transport layer and a light emitting layer.
  • the light emitting layer may include a phosphorescent dopant material or a fluorescent dopant material.
  • the compound of formula 1 of the present invention may be included in the organic EL device as a blue, green, and / or red phosphorescent host, a fluorescent host, a hole transport material, a hole injection material and / or an electron transport material.
  • the compound of formula 1 of the present invention may be used as a phosphorescent host.
  • the compound of the present invention has a high glass transition temperature of 150 °C or more, when the compound is used as an organic layer of the organic EL device, since the crystallization is minimized in the organic EL device, the driving voltage of the device can be lowered, luminous efficiency, luminance , Thermal stability, and lifetime characteristics can be improved.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked, wherein the light emitting layer, hole injection layer, At least one of the hole transport layer and the electron transport layer may include a compound represented by Chemical Formula 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.
  • the organic layer including the compound of Formula 1 may be formed by vacuum deposition or solution coating.
  • the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
  • the organic EL device of the present invention forms an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers is formed to include the compound represented by the formula (1) of the present invention. can do.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • 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 oxides with metals 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 and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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),
  • Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer are not particularly limited, and conventional materials known in the art may be used.
  • FIG. 1 A schematic structure of an organic EL device according to an embodiment of the present invention is shown in FIG. Referring to FIG. 1, an anode, a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (emitting, EML), a hole blocking layer (HBL) on a substrate, An electron transport layer (ETL), an electron injection layer (EIL), and a cathode are sequentially stacked.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • Triphenylene 50 g, 219.0 mmol was dissolved in 750 ml of Chloroform and 51 ml (438.0 mmol) of Trimethyl phosphate, and the solution was heated and stirred at 60 ° C. in a nitrogen atmosphere.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After the washing of distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used as a light emitting host material, instead of the compound prepared in Synthesis Example, to form an emission layer.
  • Example 1-10 For each organic EL device manufactured in Example 1-10 and Comparative Example 1, the driving voltage, current efficiency, emission peak, and luminance were measured, and the results are shown in Table 1 below.
  • Example 1 Table 1 device Host Voltage (V) Luminance (cd / m 2 ) EL peak (nm) Efficiency (cd / A) color
  • Example 1 A-1 6.12 524 520 45.4 green
  • Example 2 A-2 6.32 491 521 42.7 green
  • Example 3 A-16 6.82 455 520 39.4 green
  • Example 4 A-27 6.25 479 520 41.6 green
  • Example 5 A-61 6.05 503 521 43.5 green
  • Example 6 A-66 6.08 464 519 40.4 green
  • Example 7 A-70 6.12 430 518 37.5 green
  • Example 8 A-81 6.45 412 518 35.6 green
  • Example 9 B-2 7.01 384 520 33.1 green
  • Example 10 B-41 6.89 427 520 36.8 green Comparative Example 1 CBP 6.93 445 516 38.2 green

Abstract

L'invention concerne un composé de triphénylène et un dispositif à électroluminescence organique incluant celui-ci. Le composé de l'invention présente une bonne aptitude à l'injection de trous et/ou une bonne aptitude au transport, et une bonne aptitude au transport d'électrons et/ou une bonne capacité d'émission lumineuse ; le dispositif à électroluminescence organique comprenant cette composition comme matière hôte fluorescente ou phosphorescente possède ainsi des caractéristiques améliorées telles que d'excellentes caractéristiques d'efficacité lumineuse, de luminosité, de tension d'attaque et de durée de vie.
PCT/KR2010/009459 2009-12-30 2010-12-29 Composé de triphénylène et dispositif à électroluminescence organique incluant celui-ci WO2011081423A2 (fr)

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WO2013061805A1 (fr) 2011-10-24 2013-05-02 保土谷化学工業株式会社 Nouveau dérivé triphénylène et élément électroluminescent organique utilisant ledit dérivé
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US20160126472A1 (en) * 2013-09-06 2016-05-05 Samsung Sdi Co., Ltd. Composition for organic optoelectronic device, organic optoelectronic device, and display device
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