USH2084H1 - Pentacene derivatives as red emitters in organic light emitting devices - Google Patents

Pentacene derivatives as red emitters in organic light emitting devices Download PDF

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USH2084H1
USH2084H1 US09/464,090 US46409099A USH2084H US H2084 H1 USH2084 H1 US H2084H1 US 46409099 A US46409099 A US 46409099A US H2084 H USH2084 H US H2084H
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substituted
red
pat
pentacene
pentacene derivatives
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Lisa Crisafulli Picciolo
Hideyuki Murata
Zakya H. Kafafi
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US Department of Navy
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Priority to US09/464,090 priority Critical patent/USH2084H1/en
Priority to AU19502/01A priority patent/AU1950201A/en
Priority to PCT/US2000/033087 priority patent/WO2001045469A1/fr
Assigned to SECRETARY OF THE NAVY, UNITED STATES OF AMERICA, AS REPRESENTED BY THE reassignment SECRETARY OF THE NAVY, UNITED STATES OF AMERICA, AS REPRESENTED BY THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MURATA, HIDEYUKI, PICCIOLO, LISA A. CRISAFULLI, KAFAFI, ZAKYA
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3

Definitions

  • the present invention relates to red-emitting organic electroluminescent materials and devices in general and in particular to compositions and devices comprising host materials doped with pentacene derivatives.
  • Organic electroluminescent devices have been the subject of considerable research because of their potential applications in a wide variety of flat panel displays, especially ultra thin flat panel displays.
  • Organic electroluminescent devices are very competitive with liquid crystal displays because of their very bright self-emission, low power consumption, low cost of organic materials, ease of color tunability and processability.
  • the present technology will be competing with liquid crystal displays, which are replacing cathode ray tubes as a means of displaying visual information.
  • pentacene derivatives exhibit very narrow emission spectra and produce a very pure red color in a region of the spectrum that is useful for display applications.
  • pentacene derivatives When pentacene derivatives are doped into the active emissive layer of organic light-emitting devices, efficient energy transfer from the host material to the pentacene derivatives and/or carrier recombination on the pentacene derivatives takes place, resulting in red electroluminescence predominantly from the pentacene derivatives.
  • the present invention is directed to an electroluninescent composition
  • an electroluninescent composition comprising a host material and a red dopant, wherein the red dopant is a pentacene derivative substituted with two or more aromatic, substituted aromatic, heteroaromatic or substituted heteroaromatic groups.
  • the present invention is directed to a heterostructured organic light emitting device for producing electroluminescence, the heterostructure having an emissive layer comprised of a host material and a red dopant, wherein the red dopant is a pentacene derivative substituted with two or more aromatic, substituted aromatic, heteroaromatic or substituted heteroaromatic groups.
  • the pentacene derivatives of the present invention have the advantages that they are relatively easy to synthesize and that the synthesis process does not produce a by-product that quenches fluorescence (which is a recurring problem in some fluorescent red dyes such as DCM/DCJ compounds). Moreover, the pentacene derivatives have narrow emission spectra in the red visible spectral region appropriate for display applications.
  • FIG. 1 is a cross-sectional representation of a first embodiment of an organic light emitting device of the present invention.
  • FIG. 2 is a cross-sectional representation of a second embodiment of an organic light emitting device of the present invention.
  • the materials of the present invention are red-emitting electroluminescent composites comprising host materials and red dopants, the red dopants being pentacene derivatives as described below.
  • the host material may be any compound or mixture of compounds typically used or capable of being used in the active emitting layer and/or carrier transporter of an electroluminescent device.
  • the host material is a material that has good electron transport and/or hole transport properties, has good morphological properties so that it forms thin amorphous films by vacuum evaporation and has good electrochemical stability.
  • the photoluminescence spectra of the host material should overlap with the absorption spectra of the guest material so that efficient Mariester/Dexter energy transfer takes place.
  • the host material should not quench the emission from the guest material, should have a bandgap greater than the guest material so that carrier trapping can occur, should have a larger ionization potential than that of the guest material so that hole trapping can occur and should have a smaller electron affinity than that of the guest material so that electron trapping can occur.
  • Typical host materials include hole transport materials such as N,N′-diphenyl-N,N′-bis(3-methylphenyl)1,1′-biphenyl-4,4′diamine (TPD), N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine (NPB), N,N,N,N ′-tetrakis(4-methylphenyl)(1,1′-biphenyl)-4,4′diamine (TTB) and starburst compounds such as 4,4′,4′-tris(1-naphthylphenylamino)triphenylamine(1-TNATA).
  • TPD N,N′-diphenyl-N,N′-bis(3-methylphenyl)1,1′-biphenyl-4,4′diamine
  • NPB N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine
  • TTB N
  • Typical host materials also include electron transport materials such as metal chelate compounds such as tris(8-hydroxyquinolinato)aluminum (ALQ 3 ), tris(8-hydroxyquinolinato) gallium III (Gaq 3 ), tris-(4-methyl-8-hydroxyquinolinato) aluminum (III) (Almq 3 ), bis(10-hydroxybenzo[h]quinolinato) beryllium (BeBq 2 ), tris(4-phenanthridinolato) aluminum III (Alph 3 ), and bis(2-styryl-8-quinolinato) zinc II (Znsq 2 ).
  • metal chelate compounds such as tris(8-hydroxyquinolinato)aluminum (ALQ 3 ), tris(8-hydroxyquinolinato) gallium III (Gaq 3 ), tris-(4-methyl-8-hydroxyquinolinato) aluminum (III) (Almq 3 ), bis(10-hydroxybenzo[h]quinolinato) beryllium (BeBq 2
  • typical electron transport materials include 1,3,4-oxadiazole derivatives such as 1,3,[5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2-yl] benzene (OXD7), 2-(4-biphenylyl)-5-(4-tert-butylphenyl-oxadiazole (butyl-PBD), 1,2,4-triazoles (TAZs) and 5,5′-bis(dimesitylboryl)-2,2′-bithiophene (BMB-2T).
  • 1,3,4-oxadiazole derivatives such as 1,3,[5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2-yl] benzene (OXD7), 2-(4-biphenylyl)-5-(4-tert-butylphenyl-oxadiazole (butyl-PBD), 1,2,4-triazoles (TAZs)
  • the pentacene derivatives of the present invention are compounds comprising a pentacene backbone substituted in two or more positions with aromatic groups, substituted aromatic groups, heteroaromatic groups and substituted heteroaromatic groups.
  • bulky or hindered substituents such as aromatic groups, substituted aromatic groups, heteroaromatic groups and substituted heteroaromatic groups on a pentacene derivative contribute to more efficient electroluminescence due to increase of photoluminescence by the reduction of the aggregation of individual molecules of the pentacene derivative.
  • heteroaromatic substituents or substituents that have longer conjugation may cause a red-shift of the spectra.
  • Suitable heteroaromatic substituents include furyl, thienyl, pyridyl, oxazoly, isoxazoly, thiazoly, isothiazoly, pyridyl, pyridazyl, pyrimidyl and pyrazyl groups.
  • Suitable groups with longer conjugation include styryl groups and styryl groups substituted with alkyl, phenyl, naphthyl, anthracenyl and biphenyl.
  • aromatic and heteroaromatic substituents attached to polycyclic aromatic hydrocarbons such as tetracene reduce intersystem crossing between singlet(S 1 ) to triplet (T n ) states, resulting in higher photoluminescent efficiency.
  • polycyclic aromatic hydrocarbons such as tetracene reduce intersystem crossing between singlet(S 1 ) to triplet (T n ) states, resulting in higher photoluminescent efficiency.
  • Pentacene derivatives of the present invention include, for example, compounds of the formula:
  • R 1 , R 2 , R 3 , and R 4 are independently aromatic, substituted aromatic, heteroaromatic or substituted heteroaromatic groups.
  • R 1 , R 2 , R 3 and R 4 are unsubstituted, alkyl-substituted or aryl-substituted phenyl, naphthyl, anthracenyl, biphenyl, furyl, thienyl, pyridyl, oxazoly, isoxazoly, thiazoly, isothiazoly, pyridyl, pyridazyl, pyrimidyl, or pyrazyl groups.
  • Pentacene derivatives of the present invention may also include, for example, compounds of the formula:
  • R 5 and R 6 are independently aromatic, substituted aromatic, heteroaromatic or substituted heteroaromatic groups.
  • R 5 and R 6 are unsubstituted, alkyl-substituted or aryl-substituted phenyl, naphthyl, anthracenyl, biphenyl, furyl, thienyl, pyridyl, oxazoly, isoxazoly, thiazoly, isothiazoly, pyridyl, pyridazyl, pyrimidyl, or pyrazyl groups.
  • Pentacene derivatives may also include compounds of the following formulae:
  • R 7 -R 56 are independently aromatic, substituted aromatic, heteroaromatic or substituted heteroaromatic groups and wherein preferably, R 7 -R 56 are unsubstituted, alkyl-substituted or aryl-substituted. phenyl, naphthyl, anthracenyl, biphenyl, furyl, thienyl, pyridyl, oxazoly isoxazoly, thiazoly isothiazoly, pyridyl, pyridazyl, pyrimidyl, or pyrazyl groups.
  • the reason for providing a large number of pentacene derivatives in the present invention is to provide a large number of choices in terms of emission wavelengths within the red region. Each derivative is expected to have a slightly different electronic structure and a slightly different emission spectrum. Thus, with a large number of choices, a person skilled in the art may fine-tune an electroluminescent device by selecting a derivative that meets a particular emission requirement.
  • pentacene derivative that exhibits a very narrow emission within the desired range of the red spectrum is 6,13-diphenylpentacene.
  • the pentacene derivatives of the present invention may be synthesized by any method known in the art for attaching other aromatic or heteroaromatic groups to a polycyclic aromatic hydrocarbon.
  • the pentacene derivatives may be synthesized by starting with a pentacene quinone derivative, such as pentacene-5,7,12,14-tetraone or 6,13-pentacenequinone and then treating the pentacene quinone derivative with an excess of an organolithium compound containing the side group (RLi).
  • RLi organolithium compound containing the side group
  • R is the desired substituent.
  • This method of attaching an R group to a polycyclic ring is described generally in the following publication incorporated herein by reference: Maulding et al “Electronic Absorption and Fluorescence of Phenylethynyl-Substituted Acenes” Journal of Organic Chemistry, Vol. 34, No. 6, Jun. 1969, pp 1734-1736.
  • the organic light emitting device of the present invention can have the same configuration as any host-dopant-containing electroluminescent device known in the art.
  • a typical organic light emitting device such as is described, for example, in U.S. Pat. No. 5,409,783 and other patents and publications referenced above, includes an anode separated from a cathode by an electroluminescent medium.
  • the anode is typically a high work function, hole injecting material such as, for example indium tin oxide (ITO).
  • the cathode is typically a low work function, electron-injecting material such as, for example, magnesium-silver alloy (Mg:Ag).
  • the anode and the cathode are connected by conductors to an external power source, which can be a continuous direct current or alternating current voltage source or an intermittent current voltage source. Any convenient conventional power source, including any desired switching circuitry, can be employed which is capable of positively biasing the anode with respect to the cathode. Either the anode or cathode can be at ground potential.
  • the electroluminescent device can be viewed as a diode which is forward biased when the anode is at a higher potential than the cathode. Under these conditions, the anode injects holes (positive charge carriers), into the luminescent medium while the cathode injects electrons into the luminescent medium. The portion of the luminescent medium adjacent to the anode thus forms a hole injecting and transporting zone while the portion of the luminescent medium adjacent to the cathode forms an electron injecting and transporting zone. The injected holes and electrons each migrate toward the oppositely charged electrode, which eventually leads to hole-electron recombination within the organic luminescent medium.
  • the host receives the hole/electron recombination energy and then by Förster or Dexter (i.e. radiationless) energy transfer processes, transfers that excitation energy to the dopant compound, which in turn radiates to produce visible radiation in the desired wavelength.
  • Förster or Dexter i.e. radiationless
  • Reverse biasing of the electrodes interrupts charge injection, reverses the direction of mobile charge migration, and terminates light emission.
  • the most common mode of operating the organic electroluminescent device is to employ a forward biasing DC power source and to rely on external current interruption or modulation to regulate light emission.
  • the term “heterostructure” refers to a device having a layered structure including at least an anode, hole transporting layer, electron transporting layer and a cathode, as described above. In such a device, the host/dopant composition may be part of the hole transporting layer or the electron transporting layer.
  • the term “heterostructure” also includes any variations on the basic device, such as a device having a separate emissive layer between the hole transport layer and the electron transport layer. Examples of devices of the present invention are illustrated in FIGS. 1 and 2.
  • FIG. 1 depicts a device having a substrate 10 having deposited thereon successive layers of an anode 20, a hole transporting layer 30, an electron transporting layer 40 and a cathode 50.
  • FIG. 1 depicts a device having a substrate 10 having deposited thereon successive layers of an anode 20, a hole transporting layer 30, an electron transporting layer 40 and a cathode 50.
  • FIG. 2 depicts a device having a substrate 100 having deposited thereon successive layers of an anode 200, a hole transporting layer 300, and active emitting layer 600 and an electron transporting layer 400 and a cathode 500.
  • Other configurations are possible, such as devices having separate layers for red, blue and green emitting material, as described, for example in International Publication No. WO 98/06242 (Forrest et al).
  • pre-cleaned glass substrates patterned with indium tin oxide (ITO) stripes can be used.
  • the hole transport layer, the emissive layer (if present as a separate layer) and the electron transport layer can be prepared by consecutive vapor deposition of each layer.
  • the layers can be prepared from solution by spin casting or by other means of creating a thin film layer on a substrate.
  • the host/dopant composition, whether it be part of the hole transport layer, a separate emissive layer or the electron transport layer is formed by co-evaporation of the host material and the pentacene derivative.
  • the vapor deposition is carried out in a vacuum chamber under a base pressure of 2 ⁇ 10 ⁇ 7 Torr.
  • a Mg:Ag alloy top layer is deposited through a shadow mask forming metal stripes perpendicular to the indium tin oxide stripes.
  • Photoluminescence and electroluminescence spectra are measured inside a glove box purged with dry nitrogen.
  • the excitation laser beam for photoluminescence is brought into the glove box through an optical fiber.
  • the luminescence is collected and brought out through another optical fiber.
  • Voltage-current-luminance measurements are performed with a high current source and luminance meter.
  • Device performance is evaluated based on the external quantum efficiency defined as the ratio of the number of emitted photons to the number of injected carriers.
  • OLEDs Organic light emitting devices
  • OLEDs were fabricated in high vacuum (10 ⁇ 7 Torr) by sequentially depositing thin films of a hole transport layer, an active emissive layer, an electron transport layer followed by a metal film cathode (reflective) onto an indium tin oxide (transparent anode) patterned glass substrate.
  • the active emissive layer consisted of a derivative of pentacene doped into a hole or an electron transport material that serves as the host.
  • the electroluminescence spectrum of a device where the active layer is 6,13-diphenylpentacene doped into ALQ 3 exhibits a very narrow emission peak in the visible red region centered at 625 nm.
  • a device wherein the active emissive layer consists of a host doped with an optimal concentration of 6,13-diphenylpentacene shows an electroluminescence quantum efficiency of 2.5% at 100 A/m 2 .

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US09/464,090 1999-12-16 1999-12-16 Pentacene derivatives as red emitters in organic light emitting devices Abandoned USH2084H1 (en)

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US09/464,090 USH2084H1 (en) 1999-12-16 1999-12-16 Pentacene derivatives as red emitters in organic light emitting devices
AU19502/01A AU1950201A (en) 1999-12-16 2000-11-30 Pentacene derivatives as red emitters in organic light emitting devices
PCT/US2000/033087 WO2001045469A1 (fr) 1999-12-16 2000-11-30 Derives de pentacene utilises en tant qu'emetteurs rouges dans des dispositifs organiques electroluminescents

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US20020067124A1 (en) * 2000-11-29 2002-06-06 Kafafi Zakya H. Universal host for RG or RGB emission in organic light emitting devices
US20030116755A1 (en) * 2000-02-29 2003-06-26 Tamotsu Takahashi Polyacene derivatives and production thereof
US20040108047A1 (en) * 2002-12-09 2004-06-10 International Business Machines Corporation System and method of transfer printing an organic semiconductor
US20050240061A1 (en) * 2002-03-26 2005-10-27 Japan Science And Technology Agency Functional thin film
US20110130593A1 (en) * 2009-11-30 2011-06-02 Miller Glen P Soluble, persistent nonacene derivatives
US20110130594A1 (en) * 2009-11-30 2011-06-02 Miller Glen P Class of soluble, photooxidatively resistant acene derivatives

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JP2005504811A (ja) 2001-09-27 2005-02-17 スリーエム イノベイティブ プロパティズ カンパニー 置換ペンタセン半導体
US20030097010A1 (en) 2001-09-27 2003-05-22 Vogel Dennis E. Process for preparing pentacene derivatives
US7368659B2 (en) 2002-11-26 2008-05-06 General Electric Company Electrodes mitigating effects of defects in organic electronic devices
US7063900B2 (en) 2002-12-23 2006-06-20 General Electric Company White light-emitting organic electroluminescent devices
KR101184366B1 (ko) 2004-11-05 2012-09-20 크리에이터 테크놀로지 비.브이. 절연체 및 반도체를 동시에 형성하기 위해 유기물을 패턴화하는 방법 및 이러한 방법으로 형성된 디바이스
US7319153B2 (en) 2005-07-29 2008-01-15 3M Innovative Properties Company 6,13-Bis(thienyl)pentacene compounds
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