WO2014011483A1 - Matériaux hôtes ambipolaires à base de n-phénylcarbazole lié en position méta par oxadiazole et triazole - Google Patents

Matériaux hôtes ambipolaires à base de n-phénylcarbazole lié en position méta par oxadiazole et triazole Download PDF

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WO2014011483A1
WO2014011483A1 PCT/US2013/049329 US2013049329W WO2014011483A1 WO 2014011483 A1 WO2014011483 A1 WO 2014011483A1 US 2013049329 W US2013049329 W US 2013049329W WO 2014011483 A1 WO2014011483 A1 WO 2014011483A1
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compound
optionally substituted
group
alkyl
linear
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PCT/US2013/049329
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Carlos Zuniga
Seth R. Marder
Wojciech HASKE
Bernard Kippelen
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Georgia Tech Research Corporation
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • OLEDs organic light-emitting diodes
  • Such OLEDs often contain a light emissive layer comprising a luminescent material as a guest, dispersed and/or dissolved in a mixture of host/carrier materials capable of transporting holes, electrons, and/or excitons into contact with the luminescent guest.
  • the light emissive layer is typically disposed between an anode and a cathode.
  • Compounds comprising the carbazole group have been utilized as hole transporter and/or electron blocking materials in OLED applications, and in some cases as hole- transporting hosts for luminescent guests.
  • small-molecule 2,5-diaryl oxadiazoles are known as suitable electron transport materials for use in making electron transport layers for OLED devices, and have also been used as electron transport hosts for luminescent guests.
  • Identifying host materials that can efficiently perform important functions can be difficult, especially for use with guest materials that emit at relatively high photon energy at the blue part of the visible spectrum.
  • the energies of both the singlet and triplet states of the hole and/or electron transport materials in the host should be at least somewhat higher than the energies of the corresponding singlet and triplet states of the guest emitters.
  • the conjugation of the organic host materials must be limited, in order to provide for singlet and triplet energy levels higher than those of the guest emitters. This can be challenging for OLEDs employing high photon energy guest emitters.
  • mixtures of hole transport and electron transport materials have been used to form a host material for phosphorescent guests in the emissions layers of multi-layer OLEDs.
  • devices based on such mixtures of hole transport and electron transport materials in their emission layers can undergo undesirable phase separations, partial crystallizations, and/or otherwise degrade upon extended OLED device operation, decreasing OLED device efficiency and/or lifetimes over time.
  • Progress on efficient hosts for higher photon energy phosphorescent emitters has been significantly slower, and the efficiencies and lifetimes of such PhOLEDs remain in need of significant improvement. Accordingly, there remains an unmet need in the art for improved host materials that can efficiently and stably transport holes and electrons into contact with phosphorescent emitters in OLED emission layers.
  • Embodiments described herein include compounds and compositions, and methods of making and using the same. Also described are articles and devices.
  • one embodiment provides a compound represented by formula (I):
  • R 2 , R 3 , P and R 5 are represented by and the remaining of R 2 , R 3 , R4 and R 5 are independently selected from hydrogen, halogen and a Ci_ 2 o organic group;
  • R 7 , Rs, R and Rio are optionally substituted carbazole groups; and the remaining of R5, R 7 , Rs, R and Rio are independently selected from hydrogen, halogen and a Ci_ 2 o organic group;
  • RI is an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group;
  • R 2 , R3, R4 and R 5 are independently selected from hydrogen, fluoro, cyano, alkyl, fluoroalkyl, alkoxide and fluoroalkoxide group;
  • the carbazole group is unsubstituted or is substituted with one or more groups selected from fluoro, cyano, alkyl, fluoroalkyl, alkoxide, fluoroalkoxide and an optionally substituted carbazole;
  • R 6 , R7, R 8 , R and Rio are independently selected from hydrogen, fluoro, cyano, alkyl, fluoroalkyl, alkoxide and fluoroalkoxide group.
  • Ri, Rn and R 12 are unsubstituted or substituted with one or more groups selected from hydroxyl, fluoro, cyano, alkyl, fluoroalkyl, alkoxide, and fluoroalkoxide.
  • Another embodiment provides that is present at R3 and/or R4 but not at R 2 or R 5 , and wherein the optionally substituted carbazole group is present at R 7 and/or R 9 but not at R 6 , R 8 or R 10 .
  • each R13, R14, Ri 5 , Ri 6 and Rn is independently hydrogen, fluoro, cyano, a Ci_ 2 o linear or branched alkyl, a Ci_ 2 o linear or branched fluoroalkyl, a Ci_ 2 o linear or branched alkoxide, or a Ci_ 2 o linear or branched fluoroalkoxide group.
  • Another embodiment provides that is selected from formulae (VII) and
  • each Rig and R 1 is independently hydrogen, fluoro, cyano, a Ci_ 2 o linear or branched alkyl, a Ci_ 2 o linear or branched fluoroalkyl, a Ci_ 20 linear or branched alkoxide, a Ci_ 20 linear or branched fluoroalkoxide group, or an optionally substituted carbazole.
  • Another embodiment provides that the compound is selected from formulae (IX) and
  • Another embodiment provides that I Y >- IS R ⁇ .11
  • Another embodiment provides that Another embodiment provides that the compound comprises at least one triscarbazole group represented by
  • Another embodiment provides a method for making the compounds described herein, comprising reacting a first compound with a second compound, wherein: (a) the first compound is represented by wherein
  • R 2 , R 3 , R 4 and R 5 are Br, and the remaining of R 2 , R 3 , R 4 and R 5 in the formula representing the first compound have the same definition as their R 2 , R3, R 4 and R 5 homologues as described herein;
  • Ri in the formula representing the first compound has the same definition as its Ri homologues contained in the formula of the compound described herein;
  • R 12 in the formula representing the first compound have the same definition as their Rn and R 12 homologues contained in the formula of the compound described herein;
  • the second compound is represented by R 6 , R 7 , R 8 , R and Rio in the formula representing the second compound have the same definition as their R 6 , R 7 , R 8 , R 9 and Rio homologues contained in the formula of the compound described herein.
  • compositions comprising the compounds described herein or made by the methods described herein.
  • Another embodiment is an electroluminescence device, comprising an anode, a cathode, and an emissive layer, wherein the emissive layer comprises the compound as described herein or made by the methods as described herein, or the composition as described herein.
  • the emissive layer comprises at least one phosphorescent emitter, and wherein the external quantum efficiency of the
  • FIG. 1 shows performance of OLED devices with spin-coated Compound H hole transport layer and evaporation-deposited Compound A: Ir(ppy)3 emitting layer.
  • FIG. 2 shows performance of OLED devices with spin-coated Compound H hole transport layer and evaporation-deposited Compound A: FIrpic emitting layer.
  • Optionally substituted groups can refer to, for example, functional groups that may be substituted or unsubstituted by additional functional groups.
  • groups for example, when a group is unsubstituted, it can be referred to as the group name, for example alkyl or aryl.
  • groups when a group is substituted with additional functional groups, it may more generically be referred to as substituted alkyl or substituted aryl.
  • Alkyl can refer to, for example, linear, branched, or cyclic alkyl groups. This term is exemplified by groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, ethylhexyl, dodecyl, isopentyl, etc.
  • Aryl can refer to, for example, aromatic carbocyclic groups having one or more single rings (e.g., phenyl or biphenyl) or multiple condensed rings (e.g., naphthyl or anthryl).
  • Heteroalkyl can refer to, for example, an alkyl group wherein one or more carbon atoms are substituted with heteroatoms.
  • Heteroaryl can refer to, for example, an aryl group wherein one or more carbon atoms are substituted with heteroatoms.
  • Alkoxide can refer to, for example, the group “alkyl-O-”. This term is exemplified by groups such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, t-butyloxy, etc.
  • Fluoroalkyl can refer to, for example, an alkyl group wherein one or more hydrogen atoms are substituted with fluorine. Fluoroalkyl described herein include partially fluorinated alkyl groups as well as perfluoroalkyl groups.
  • Fluoroalkoxide can refer to, for example, an alkoxide group wherein one or more hydrogen atoms are substituted with fluorine. Fluoroalkoxide described herein include partially fluorinated alkoxide groups as well as perfluoroalkoxide groups.
  • Triscarbazole can refer to, for example, three or more carbazole groups connected to each other through aryl carbon-nitrogen bond and/or aryl carbon-carbon bond.
  • Ambipolar host compounds are described in, for example, WO 2010149618,
  • Ri is an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group;
  • R 2 , R 3 , R 4 and R 5 are represented by and the remaining of R 2 , R 3 , R 4 and R 5 are independently selected from hydrogen, halogen and a Ci_ 2 o organic group;
  • R5, R7, Rs, R and Rio are optionally substituted carbazole groups; and the remaining of R 6 , R7, Rs, R and Rio are independently selected from hydrogen, halogen and a Ci_ 2 o organic group; and (d) Y is selected from from from
  • R u i an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group, and wherein R12 is hydrogen, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group.
  • Ri can be, for example, an optionally substituted C 5 _3o aryl or heteroaryl group, or an optionally substituted C 5 _2o aryl or heteroaryl group, or an optionally substituted C 5 _i4 aryl or heteroaryl group, including the optional substituent.
  • Ri can be, for example, an optionally substituted Ci_ 3 o linear or branched alkyl or heteroalkyl group, or an optionally substituted Ci_ 20 linear or branched alkyl or heteroalkyl group, or an optionally substituted C 1-12 linear or branched alkyl or heteroalkyl group, or an optionally substituted Ci_ 6 linear or branched alkyl or heteroalkyl group, including the optional substituent.
  • Ri can be, for example, an optionally substituted Ci_ 3 o monocyclic, bicyclic or tricyclic alkyl or heteroalkyl group, or an optionally substituted Ci_ 2 o monocyclic, bicyclic or tricyclic alkyl or heteroalkyl group, or an optionally substituted C 1-12 monocyclic, bicyclic or tricyclic alkyl or heteroalkyl group, or an optionally substituted Ci_ 6 monocyclic, bicyclic or tricyclic alkyl or heteroalkyl group, including the optional substituent.
  • Ri can be, for example, unsubstituted. Ri can be, for example, substituted with one or more substituents selected from fluoro, cyano, hydroxyl, alkyl, fluoroalkyl, alkoxide, and fluoroalkoxide.
  • Ri comprises at least one crosslinkable or polymerizable group. In one embodiment, Ri comprises at least two crosslinkable or polymerizable groups.
  • Ri is an optionally substituted phenyl group. In one embodiment, Ri is a phenyl group substituted with at least one or at least two crosslinkable or
  • Y is— O—
  • the ambipolar host material comprises an
  • Y is
  • ambipolar host material comprises a triazole moiety represented by R n .
  • Y is— --N— C— -
  • the ambipolar host material comprises a triazine moiety
  • ambipolar host material comprises a tetrazine moiety represented by N— N Rii and R12 can be, for example, an optionally substituted Ci_ 3 o alkyl or heteroalkyl group, or an optionally substituted Ci_ 2 o alkyl or heteroalkyl group, or an optionally substituted Ci_ 6 alkyl or heteroalkyl group, including the optional substituent.
  • Rn and R12 can also be, for example, an optionally substituted C5-30 aryl or heteroaryl group, or an optionally substituted C 5 _ 2 o aryl or heteroaryl group, or an optionally substituted C 5 _i4 aryl or heteroaryl group, including the optional substituent.
  • Rn and R12 can be, for example, unsubstituted. Rn and R12 can also be, for example, substituted with one or more substituents selected from fluoro, cyano, hydroxyl, alkyl, fluoroalkyl, alkoxide, and fluoro alkoxide.
  • the moiety is present at R 3 or R 4 . In another embodiment, the moiety is present at R 3 or R 4 .
  • R 2 , R 3 , R 4 and R5 can be, for example, independently selected from hydrogen, fluoro, cyano, alkyl, fluoroalkyl, alkoxide and fluoro alkoxide.
  • the ambipolar host compound is represented by formula (IX):
  • the ambipolar host compound is represented by formul
  • R 7 or R is an optionally substituted carbazole group.
  • R 8 is an optionally substituted carbazole group.
  • R 6 or Rio is an optionally substituted carbazole group.
  • both R 7 and R are optionally substituted carbazole groups.
  • R 6 , R 7 , R 8 , R9 and Rio can be, for example, hydrogen, fluoro, cyano, alkyl, fluoroalkyl, alkoxide and fluoroalkoxide.
  • the remaining of R 6 , R 7 , R 8 , R9 and Rio are each hydrogen.
  • the moiety is present at R 3 and/or R 4 but not at
  • the optionally substituted carbazole groups can comprise, for example, a
  • the monocarbazole group or triscarbazole group can be unsubstituted.
  • the monocarbazole group or triscarbazole group can also be substituted with one or more groups selected from fluoro, cyano, alkyl, fluoroalkyl, alkoxide, fluoroalkoxide, and carbazole.
  • the optionally substituted carbazole groups described herein can be represented by, for example, formulae (II), (III), (IV), (V) and (VI).
  • each of R13, R14, R15, Ri6 and Rn is independently hydrogen, fluoro, cyano, a Ci_2o or Ci_6 linear or branched alkyl, a Ci_ 2 o or Ci_ 6 linear or branched fluoroalkyl, a Ci_ 2 o or Ci_6 linear or branched alkoxide, or a Ci_ 2 o or Ci_ 6 linear or branched fluoroalkoxide group.
  • each of R13, R14, R15, Ri 6 and Rn is hydrogen.
  • R is an optionally substituted carbazole group
  • R 6 , R7, Re and Rio are each hydrogen, the R e R / moiety is represented by formula (VII): (VII), wherein Rig is independently hydrogen, fluoro, cyano, a Ci_ 2 o or Ci_ 6 linear or branched alkyl, a Ci_ 2 o or Ci_6 linear or branched perfluoroalkyl, a Ci_ 2 o or Ci_6 linear or branched alkoxide, a Ci_ 2 o or Ci_ 6 linear or branched fluoroalkoxide group, or an optionally substituted carbazole.
  • Rig is independently hydrogen, fluoro, cyano, a Ci_ 2 o or Ci_ 6 linear or branched alkyl, a Ci_ 2 o or Ci_6 linear or branched perfluoroalkyl, a Ci_ 2 o or Ci_6 linear or branched alkoxide, a Ci_ 2 o or Ci_ 6 linear or branched fluoroalk
  • the carbazole gro position is an unsubstituted
  • the carbazole group at the R 9 position is an unsubstituted
  • R 7 and R 9 are each an optionally substituted carbazole
  • R e R / moiety is represented by
  • R13 is independently hydrogen, carbazole, fluoro, cyano, a Ci_ 20 or Ci_ 6 linear or branched alkyl, a Ci_ 20 or Ci_ 6 linear or branched perfluoroalkyl, a Ci_ 20 or Ci_ 6 linear or branched alkoxide, a Ci_ 20 or Ci_ 6 linear or branched fluoroalkoxide group, or an optionally substituted carbazole.
  • the carbazole group at the R 7 and R position are each an
  • the carbazole group at the R 7 and R position are each an
  • the ambipolar host material described herein comprises at least one optionally substituted triscarbazole group. In a further embodiment, the ambipolar host material described herein comprises at least one unsubstituted triscarbazole group represented
  • ambipolar host compounds described herein include the folio wings:
  • ambipolar host compounds described herein are either sublimable under high vacuum or readily soluble in common organic solvent, and therefore can be readily processed to form compositions useful in organic electronic devices, especially when mixed and/or co-deposited with phosphorescent guest emitters to form the emissive layers of OLED devices.
  • the ambipolar host compounds described herein have high glass transition temperature which is advantageous for OLED applications.
  • the glass transition temperature can be at least 120°C, or at least 130°C, or at least 140°C, or at least 150°C, or at least 160°C, or at least 170°C, or at least 180°C, or at least 190°C, or at least
  • a first compound can be reacted with a second compound, wherein the first compound is represented by one or two of R 2 , R 3 ,
  • R 4 and R 5 are halogen such as Br or I, and second compound is represented by
  • the ambipolar host compound described herein are synthesized according to the following general schemes.
  • the solution-processed ambipolar transport layer described herein can be used in various electronic devices, including electroluminescence devices such as OLED devices.
  • the OLED devices comprise at least an anode layer, a hole transport layer, an emission layer, an electron transport layer, and a cathode layer. Such devices are illustrated in the diagram below.
  • the thickness of the anode layer, the cathode layer, the emissive layer, the hole transport layer, and the electron transport layer can be, for example, about 0.001-100 ⁇ , about 0.005-10 ⁇ , or about 0.01-1 ⁇ , or about 0.02-0.1 ⁇ .
  • ITO indium gallium
  • suitable materials for anode in electroluminescence devices include, for example, ITO, which can be applied, for example, as a vacuum-deposited layer over an inert and transparent substrate such as glass.
  • Other examples include metal oxide with high work function, such as zinc oxide and indium zinc oxide.
  • cathode in electroluminescence devices include, for example, a combination of LiF as electron injecting material coated with a vacuum deposited layer of Al, and optionally an additional layer of Ag.
  • Suitable hole transporting materials include, for example, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)
  • the hole transport layer is fabricated by solution processing (e.g., spin coating) from a solution comprising the hole transporting material.
  • the electron transport layer is fabricated by solution processing (e.g., spin coating) from a solution comprising the electron transporting material (see
  • the emissive layer can comprise at least one blue emitter, at least one green emitter, at least one red emitter, or a
  • the OLED devices described herein comprise a solution- processed hole transport layer and a solution-processed emissive layer. In another embodiment, the OLED devices described herein comprise a solution-processed hole transport layer and a vacuum-deposited emissive layer. In a further embodiment, the OLED devices described herein comprise a solution-processed hole transport layer, a solution- processed emissive layer, and a solution-processed electron transport layer.
  • the OLED device described herein comprises an emitter having wavelengths between, for example, 400-700 nm including red, green, and blue phosphorescent emitters.
  • the external quantum efficiency of said OLED device at 1,000 cd/m can be, for example, at least 5%, or at least 8%, or at least 10%, or at least 12%, or at least 15%, or at least 18%, or at least 20%.
  • the OLED device described herein comprises a green phosphorescent emitter.
  • the external quantum efficiency of said OLED device at 1 ,000 cd/m can be, for example, at least 5%, or at least 8%, or at least 10%, or at least 12%, or at least 15%, or at least 18%, or at least 20%.
  • the OLED device described herein comprises a blue phosphorescent emitter.
  • the external quantum efficiency of said OLED device at 1 ,000 cd/m can be, for example, at least 5%, or at least 8%, or at least 10%, or at least 12%, or at least 15%, or at least 18%, or at least 20%.
  • ITO substrates Indium tin oxide (ITO)-coated glass slides (Colorado Concept Coatings LLC) with a sheet resistivity of -15 ⁇ /sq were used as substrates for the OLEDs fabrication.
  • the ITO substrates were masked partially with kapton tape and the exposed ITO was etched in acid vapor (1 :3 by volume, HNO 3 : HCl) for 5 min at 60 °C.
  • the substrates were cleaned in an ultrasonic bath in the following solutions: detergent water, distilled water, acetone, and isopropanol for 20 min in each step. At the end the substrates were blown dry with nitrogen. Subsequently, ITO substrates were 0 2 plasma treated for 2 min.
  • Polymer H was synthesized according to US provisional serial no. 61/579394 filed December 22, 2011, incorporated by reference in its entirety. Polymer H was processed in the glove box under nitrogen. 10 mg of Compound H was dissolved in 1ml of anhydrous chlorobenzene (Aldrich). 35 nm thick films of the hole-transport material were spin-coated at 1500 rpm, acceleration 1,000 rpm/sec for 60 sec. The films were then heated on a hot plate at 120 °C for 20 minutes.
  • the emissive layer consisting of a host, Compound A, and an emitter, Ir(ppy) 3 (Lumtec), was deposited by co-evaporation of the two components at 0.94 A/s and 0.06 A/s respectively.
  • the pressure in the vacuum chamber was 1 x 10 "7 Torr.
  • the active area of the tested devices was about 0.1 cm 2 .
  • the devices were tested in a glove box under nitrogen. The performance of the device is shown in Figure 1.
  • ITO substrates Indium tin oxide (ITO)-coated glass slides (Colorado Concept Coatings LLC) with a sheet resistivity of -15 ⁇ /sq were used as substrates for the OLEDs fabrication.
  • the ITO substrates were masked partially with kapton tape and the exposed ITO was etched in acid vapor (1 :3 by volume, ⁇ 0 3 : HC1) for 5 min at 60 °C.
  • the substrates were cleaned in an ultrasonic bath in the following solutions: detergent water, distilled water, acetone, and isopropanol for 20 min in each step. At the end the substrates were blown dry with nitrogen. Subsequently, ITO substrates were 0 2 plasma treated for 2 min.
  • Compound H was processed in the glove box under nitrogen. 10 mg of Compound H was dissolved in 1ml of anhydrous chlorobenzene (Aldrich). 35 nm thick films of the hole- transport material were spin-coated at 1500 rpm, acceleration 1,000 rpm/sec for 60 sec. The films were then heated on a hot plate at 120 °C for 20 minutes.
  • anhydrous chlorobenzene Aldrich
  • the emissive layer consisting of a host, Compound A, and an emitter, FIrpic (Lumtec), was deposited by co-evaporation of the two components at 0.88 A/s and 0.12 A/s respectively.
  • the electron transport layer, BCP (Aldrich), the electron-injection layer, LiF (Aldrich) and aluminum were thermally evaporated at 1 A/s, 0.2 A/s and 2 A/s respectively.
  • the pressure in the vacuum chamber was 1 x 10 "7 Torr.
  • the active area of the tested devices was about 0.1 cm 2 .
  • the devices were tested in a glove box under nitrogen.
  • the performance of the device is shown in Figure 2.
  • the performance of the device is shown in Figure 2.
  • the plot on the left shows current density voltage characteristic of the diode.
  • the plot on the right shows luminance values (solid symbols) and external quantum efficiency (EQE) (empty symbols) as a function of applied voltage.
  • EQE external quantum efficiency

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Abstract

L'invention concerne des composés ambipolaires, comprenant par exemple des fragments carbazole et des fragments oxadiazole, pouvant être utilisés pour des dispositifs électroniques organiques, y compris des DELO comportant des couches de transfert d'électrons et des hôtes émetteurs. Les composés peuvent présenter un noyau déficient en électrons présentant un substituant comprenant un premier groupe phényle qui est substitué par un second groupe phényle qui est substitué par un fragment relativement riche en électrons.
PCT/US2013/049329 2012-07-09 2013-07-03 Matériaux hôtes ambipolaires à base de n-phénylcarbazole lié en position méta par oxadiazole et triazole WO2014011483A1 (fr)

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EP2933849A1 (fr) 2014-04-15 2015-10-21 cynora GmbH Matériaux hôtes pour des diodes électroluminescentes organiques
TWI609864B (zh) * 2016-11-30 2018-01-01 Yuan Ze University 咔唑衍生物材料以及有機發光二極體元件
CN109400596A (zh) * 2018-10-30 2019-03-01 内蒙古科技大学 一种噁二唑衍生物及其应用

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