WO2014101178A1 - Composé à base de tétraphénylène éthylène et dispositif oled le contenant - Google Patents

Composé à base de tétraphénylène éthylène et dispositif oled le contenant Download PDF

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WO2014101178A1
WO2014101178A1 PCT/CN2012/088034 CN2012088034W WO2014101178A1 WO 2014101178 A1 WO2014101178 A1 WO 2014101178A1 CN 2012088034 W CN2012088034 W CN 2012088034W WO 2014101178 A1 WO2014101178 A1 WO 2014101178A1
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composition
layer
hydrocarbon
combinations
electronic device
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PCT/CN2012/088034
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English (en)
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Jean Jing YAN
Xiaofan Ren
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Dow Global Technologies LLC (Formerly known as Dow Global Technologies Inc.)
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Priority to PCT/CN2012/088034 priority Critical patent/WO2014101178A1/fr
Priority to TW102146936A priority patent/TW201434802A/zh
Priority to KR1020130163804A priority patent/KR20140088017A/ko
Priority to JP2013270610A priority patent/JP2014129347A/ja
Priority to CN201310743948.1A priority patent/CN104064689A/zh
Publication of WO2014101178A1 publication Critical patent/WO2014101178A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • 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]
    • 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

  • An OLED is a light-emitting diode (LED), in which the emissive electroluminescent layer is a film of an organic compound, which emits light in response to an electric current.
  • a typical OLED has a multi-layer structure, and typically includes an indium tin oxide (ITO) anode, and a metal cathode. Sandwiched between the ITO anode and the metal cathode are several organic layers, such as a hole injection layer (HIL), a hole transfer layer (HTL), an emitting material layer (EML), an electron transfer layer (ETL), and an electron injection layer (EIL).
  • HIL hole injection layer
  • HTL hole transfer layer
  • EML emitting material layer
  • ETL electron transfer layer
  • EIL electron injection layer
  • HIL hole injection layer
  • the most commonly used HIL material is poly(3,4- ethylenedioxythiophene)/poly(styrene sulfonic acid) complex (PEDOT/PSS).
  • PEDOT/PSS poly(3,4- ethylenedioxythiophene)/poly(styrene sulfonic acid) complex
  • OLED fabricated from PEDOT PSS shows a short lifetime due to corrosion, induced by the high acidity of the PEDOT/PSS.
  • the PEDOT/PSS solution is often aqueous-based. When it is used in an OLED, trace moisture residue in the film may cause corrosion to the electrical circuit and lead to device decay. Thus, there is a continuous need for HIL materials, especially non-aqueous HIL compositions, for OLED application.
  • the present disclosure provides a composition comprising a tetraphenylene ethylene of Structure (I), a tetraphenylene ethylene of Structure (IA), or a combination thereof as shown below.
  • Ri, R 2 , R 3 , and R 4 are the same or different.
  • Each of Ri, R 2 , R 3 , and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; or
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and R 3 and R 4 form a ring structure; or
  • each of R3 and R4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and Ri and R 2 form a ring structure; or
  • Ri and R 2 form a ring structure
  • R 3 and R 4 form a ring structure
  • the present disclosure also provides a film formed from the present composition comprising the tetraphenylene ethylene of Structure (I), the tetraphenylene ethylene of Structure (IA), or a combination thereof.
  • the present disclosure also provides an electronic device comprising at least one component formed the present composition comprising the tetraphenylene ethylene of Structure (I), the tetraphenylene ethylene of Structure (IA), or a combination thereof.
  • An advantage of the present composition is that it can be used in both thermal evaporation and solution processes.
  • Figure 1 is a current-voltage curve for OLED devices in accordance with embodiments of the present disclosure.
  • Figure 2 is a graph showing the luminance efficiency of OLED devices in accordance with embodiments of the present disclosure.
  • Figure 3 is a graph showing the decay of luminance intensity with time for OLED devices in accordance with embodiments of the present disclosure.
  • the present disclosure provides a composition comprising the following: a tetraphenylene ethylene of Structure (I), a tetraphenylene ethylene of Structure (IA), or a combination thereof as shown below.
  • Ri, R 2 , R 3 , and R 4 are the same or different.
  • Each of Ri, R 2 , R 3 , and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, or a combination thereof; or
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, or a combination thereof; and R 3 and R 4 form a ring structure; or
  • each of R 3 and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, or a combination thereof; and Ri and R 2 form a ring structure; or [0020] Ri and R 2 form a ring structure, and R 3 and R 4 form a ring structure.
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, or a combination thereof; and R 3 and R 4 form a ring structure.
  • each of R3 and R4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, or a combination thereof; and Ri and R 2 form a ring structure.
  • Ri and R 2 form a ring structure
  • R 3 and R 4 form a ring structure
  • the non-identified substituents of Structure (I) and Structure (IA) may be selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, or a combination thereof. In an embodiment, the non-identified substituents of Structure (I) and Structure (IA) are hydrogen.
  • a "hydrocarbon,” as used herein, is a compound that contains only hydrogen and carbon.
  • the hydrocarbon contains 1 to 50 carbon atoms.
  • the hydrocarbon can be (i) branched or unbranched, (ii) saturated or unsaturated or aromatic, (iii) cyclic or acyclic, and (iv) any combination if (i)-(iii).
  • the term “hydrocarbon” includes "a hydrocarbylgroup,” (or “hydrocarbonyl group”)which is a hydrocarbon substituent having a valence (typically univalent).
  • the hydrocarbon contains 1 to 30 carbon atoms, or 1 to 24 carbon atoms, or 1 to 20 carbon atoms, or 1 to 12 carbon atoms, or 1 to 6 carbon atoms.
  • a “substituted hydrocarbon,” as used herein, is a hydrocarbon that includes one or more heteroatoms.
  • a “heteroatom” refers to an atom other than carbon or hydrogen.
  • Nonlimiting examples of heteroatoms include: F, CI, Br, N, O, P, B, S, Si, Sb, Al, Sn, As, Se and Ge.
  • An "unsubstituted hydrocarbon” is a hydrocarbon that contains no heteroatoms.
  • a "ring structure,” as used herein, is a ring composed of a hydrocarbon or a substituted hydrocarbon, and the ring structure can be saturated or unsaturated and the ring structure can contain one, or two, or more than two rings.
  • the composition includes a tetraphenylene ethylene (TPE) with the Structure (I) and isomers thereof.
  • TPE tetraphenylene ethylene
  • Structure (I) is provided below.
  • Ri, R 2 , R3, and R 4 are the same or different.
  • Each of R 1 -R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof.
  • each of R 1 -R 4 is independently selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and combinations thereof.
  • alkyl group is a straight-chain, branched or unbranched, saturated hydrocarbon radical. Suitable alkyl radicals include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, i-butyl (or 2-methylpropyl), hexyl, octyl, etc. In an embodiment, the alkyl group has between 1 and 30, or between 1 and 24, or between 1 and 20, or between 1 and 12, or between 1 and 6 carbon atoms.
  • substituted alkyl group refers to an alkyl group as just described in which the hydrocarbon radical includes one or more heteroatoms.
  • aryl group is an aromatic substituent which may be a single aromatic ring or multiple aromatic rings which are fused together, linked covalently, or linked to a common group such as a methylene moiety or an ethylene moiety.
  • the aromatic ring(s) may include phenyl, naphthyl, anthracenyl, and biphenyl, among others.
  • the aryl group has between 6 and 50, or between 6 and 30, or between 6 and 24, or between 6 and 20, or between 6 and 12 carbon atoms.
  • substituted aryl group refers to an aryl group as just described, in which the aromatic substituent includes one or more heteroatoms.
  • the present composition includes isomers of Structure (I).
  • the TPE of Structure (I) includes a Z-isomer, an E-isomer, and combinations thereof.
  • the Z-isomer has the Structure (I) shown below.
  • the composition comprises Structure (I), wherein Ri, R 2 , R3, and R4are as defined above.
  • the E-isomer has the Structure (IA) shown below.
  • the composition comprises Structure (IA), wherein Ri, R 2 , R 3 , and R 4 are as defined above.
  • the present composition may comprise from greater than zero, or 1 wt % to 99wt % Z-isomer (Structure I) and from less the 100 wt %, or 99 wt % to 1 wt % E-isomer (Structure IA).
  • the composition comprises from greater than zero,orl wt %, or 10 wt %, or 25 wt %, or 50 wt %, or 75 wt%, or 90 wt%, or 99 wt% Z-isomer; and from less than 100 wt %, or 99 wt %, or 90 wt %, or 75 wt %, or 50 wt %, or 25 wt%, or 10 wt%, or 1 wt% E-isomer. Weight percent is based on total weight of the composition.
  • one, some, or all of Ri through R 4 include one or more aryl groups.
  • each of R1-R4 includes at least one or more aryl groups.
  • Ri and R 2 form a ring structure.
  • each of Ri and R 2 includes an aryl group, and Riand R 2 form a ring structure.
  • R3 and R4 form a ring structure.
  • each of R 3 and R 4 include an aryl group, and R 3 and R 4 form a ring structure.
  • Ri and R 2 form a ring structure, and R 3 and R 4 form another ring structure.
  • each of Riand R 2 includes an aryl group, and Riand R 2 form a ring structure, and each of R 3 and R 4 includes an aryl group, and R 3 and R 4 form a ring structure.
  • each of Rithrough R 4 is a phenyl group.
  • the TPE has the Structure (II) below.
  • each of Ri through R 4 of the TPE is a phenyl group.
  • the TPE is a mixture of Z-isomer (II) and E-isomer ( ⁇ ) as shown below.
  • the TPE of Structure (I), Structure (IA), and combination thereof has an calculated Highest Occupied Molecular Orbital (HOMO) level from -4.30 electron volts, eV) to -5.20 eV, or from -4.3 eV to -4.9 eV.
  • HOMO Highest Occupied Molecular Orbital
  • the TPE of Structure (I), Structure (IA), or combinations thereof has a calculated HOMO level from -4.3 eV to -4.6 eV.
  • the TPE of Structure (I) has a molecular weight (MW) from 700 to 1300 g/mole. In a further embodiment, the TPE of Structure (I) has a molecular weight from 800 to 1200 g/mole.
  • the TPE containing Structure (I), Structure (IA), or combinations thereof has a weight average molecular weight (Mw) from 500 to 1500 g/mole.
  • the composition is a solution.
  • the solution includes an aromatic solvent and the present TPE composition.
  • the TPE has Structure (I), Structure (IA), or a combination thereof.
  • the TPE is dissolved in the solvent.
  • the aromatic solvent is selected from xylene, toluene, benzene, anisole and combinations thereof.
  • the present composition may comprise two or more embodiments disclosed herein. 2.
  • the present disclosure provides a film formed from a composition comprising the following: the TEP of Structure (I), the TEP of Structure (IA), or a combination thereof.
  • the TEP of Structure (I) and the TEP of Structure (IA) can be any respective TEP as described above.
  • the film includes a TEP of Structure (I), a TEP of Structure (IA), or a combination thereof with the structures below.
  • Ri, R 2 , R 3 , and R 4 are the same or different.
  • Each of Ri, R 2 , R 3 , and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; or
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and R 3 and R 4 form a ring structure; or
  • each of R3 and R4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and Ri and R 2 form a ring structure; or
  • Ri and R 2 form a ring structure
  • R 3 and R 4 form a ring structure
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and R 3 and R 4 form a ring structure.
  • each of R 3 and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and Ri and R 2 form a ring structure.
  • Ri and R 2 form a ring structure
  • R 3 and R 4 form a ring structure
  • the film includes at least two layers, Layer A and Layer B.
  • Layer A includes the present TPE composition or is otherwise formed from a composition containing the TPE of Structure (I), the TPE of Structure (IA), or combinations thereof.
  • each of Ri through R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof.
  • Layer A is a hole injection layer.
  • the Layer A is a hole injection layer formed from the composition comprising the TEP of Structure (I), the TEP of Structure (IA), or combinations thereof and the composition has a HOMO level from -4.3 eV to -4.6 eV.
  • Layer B is a hole transport layer.
  • the thickness of Layer A is from 5nm to 500nm, or from 5nm to 100 nm, or from 5nm to 50nm
  • the thickness of Layer B is from 5nm to 500nm, or from 5nm to lOOnm, or from 5nm to 50nm.
  • Layer A further comprises a p-type dopant.
  • the p-type dopant is an organometal compound or an organometal salt.
  • the p-type dopant is an organometal salt comprising at least one phenyl group.
  • the anion component of the salt comprises a boron atom.
  • the organometal salt has a structure selected from one of the following:
  • the amount of dopant in Layer A is from 1 weight percent (wt%) to 99 wt%, or from 1 wt% to 50 wt%, or from 1 wt% to 30wt%, based upon the weight of the composition.
  • the present film may comprise a combination of two or more embodiments disclosed herein. 3. Electronic Device
  • the present disclosure provides an electronic device comprising at least one component formed from a composition comprising the tetraphenylene ethylene of Structure (I), the tetraphenylene ethylene of Structure (IA), or combinations thereof.
  • the TEP of Structure (I) and the TEP of Structure (IA) can be any respective TEP as described above.
  • the electronic device includes a TEP of Structure (I), a TEP of Structure (IA), or combination thereof with the structures below.
  • Ri, R 2 , R 3 , and R 4 are the same or different.
  • Each of Ri, R 2 , R 3 , and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; or
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and R 3 and R 4 form a ring structure; or
  • each of R 3 and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and Ri and R 2 form a ring structure; or
  • Ri and R 2 form a ring structure
  • R 3 and R 4 form a ring structure
  • each of Ri and R 2 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and R 3 and R 4 form a ring structure.
  • each of R 3 and R 4 is independently selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, and combinations thereof; and Ri and R 2 form a ring structure. [0077] In an embodiment, Ri and R 2 form a ring structure, and R 3 and R4 form a ring structure.
  • the electronic device includes at least one layer containing the present composition with the TPE of Structure (I), the TPE of Structure (IA), or combinations thereof.
  • the electronic device includes a first electrode.
  • the electronic device includes a second electrode disposed over the first electrode.
  • the electronic device includes an organic layerdisposed between the first electrode and the second electrode.
  • the organic layer includes the present composition comprising the TPE of Structure (I), the TPE of Structure (IA), or combinations thereof.
  • the organic layer is Layer A and Layer A is a hole injection layer.
  • the electronic device includes a second Layer B.
  • Layer B is a hole transport layer.
  • Layer A is in contact with Layer B.
  • the electronic device includes an emitting layer.
  • the thickness of Layer A is from lnm to lOOOnm, or from 2 nm to 500 nm, or from 5 nm to 200 nm.
  • the thickness of Layer B is from 1 nm to 1000 nm, or from 2 nm to 500 nm, or from 5 nm to 200 nm.
  • the electronic device is an OLED (Organic Light Emitting
  • the electronic device includes a first electrode that is an ITO layer.
  • the electronic device also includes an HIL Layer, Layer A, containing the present TPE composition with the TPE of Structure (I), the TPE of structure (II), or combinations thereof.
  • the electronic device also includes a HTL Layer, Layer B.
  • the TPE composition of Layer A has a HOMO level that is between the HOMO level for the ITO layer and the HOMO level of the HTL material.
  • the TPE composition of Layer A has a calculated HOMO value from -4.3 eV to -4.6 eV.
  • the present electronic device may comprise a combination of two or more embodiments disclosed herein.
  • compositions claimed through use of the term “comprising” may include any additional additive, adjuvant or compound, whether polymeric or otherwise, unless stated to the contrary.
  • Dopant refers to an electron acceptor or a donator that increases the conductivity of an organic layer of an organic electronic device, when added to the organic layer as an additive.
  • Organic semiconductors may likewise be influenced, with regard to their electrical conductivity, by doping.
  • Such organic semiconducting matrix materials may be made up either of compounds with electron-donor properties or of compounds with electron-acceptor properties.
  • Emitting layer and like terms, mean a layer which consists of host and dopant.
  • the host material could be bipolar or unipolar, and may be used alone or by combination of two or more host materials.
  • the opto-electrical properties of the host material may differ to which type of dopant(Phosphorescent or Fluorescent) is used.
  • the assisting host materials should have good spectral overlap between adsorption of the dopant and emission of the host to induce good Foester transfer to dopants.
  • the assisting host materials should have high triplet energy to confine triplets of the dopant.
  • HTL Hole transport layer
  • High hole mobility is recommended for OLED devices.
  • the HTL is used to help block passage of electrons transported by the emitting layer. Small electron affinity is typically required to block electrons.
  • the HTL should desirably have larger triplets to block exciton migrations from an adjacent EML layer.
  • HTL compounds include, but are not limited to, di(p-tolyl)aminophenyl]cyclohexane (TP AC), N,N-diphenyl- N,N-bis(3-methylphenyl)-l ,l -biphenyl-4,4-diamine (TPD), and N,N '-diphenyl- ⁇ , ⁇ '-bis(l- naphthyl)-(l ,1 '-biphenyl)-4,4'-diamine (NPB).
  • TP AC di(p-tolyl)aminophenyl]cyclohexane
  • TPD N,N '-diphenyl- ⁇ , ⁇ '-bis(l- naphthyl)-(l ,1 '-biphenyl)-4,4'-diamine
  • Solvent A: THF; B: 0.1%FA in water/THF 95/5
  • UV detector Diode Array 254 nm
  • HPLC High Pressure Liquid Chromatography
  • Cyclicvoltammetry (CV):CV for the compounds was carried out on a CHI voltammetric analyzerin a three-electrode cell with a Pt counter electrode, an Hg Hg 2 Cl2reference electrode, and a Platinum plate electrode at a scan rate of lOmV/s with 0.1 M tetrabutylammonium hexafluorophosphateas the supporting electrolyte. Ferrocene was added as the internal standard. The potential values were calculated according to the peak difference of the oxidation peak of the hole injection material and ferrocene standard.
  • Atomic Force Microscope AFM was applied to visualize the surface morphology and determine the surface roughness as well as the film thickness of the spin coated FflL film.
  • the AFM measurement was performed by a tapping mode on a Dimension V instrument produced by Veeco.
  • the amplitude (A) of the vertical deviations was used to calculate the roughness of the surface.
  • the amplitude parameters R a and R q are used to describe the surface roughness.
  • Ra is the arithmetic average of absolute amplitude values
  • Rq is the root mean square of the amplitude values, which are described as:
  • A is the amplitude (height or depth) of a pixel i (means a point on the surface) in the AFM image
  • n is the total number of pixels in the image.
  • part of the film was removed from the ITO substrate by a sharp blade, and then scanned by the cantilever. The thickness of the film was revealed by the gap between the two sections.
  • the mixture was centrifuged and the supematant was concentrated and purified on a silica gel column using a mixture of petroleum ether and dichloromethane (2:1) as eluent.
  • the product (3) was a bright yellow powder (60%).
  • the yellow powder was purified by sublimation at 360°C to obtain a pure product, which has a HPLC purity of 99.4%(Z isomer: 55.7%, E isomer:46.7%).
  • Nonlimiting examples of the present TPE with Structure (I), Structure (IA) are provided in Table 2 below. Table 2
  • the HOMO level is calculated by the method described below
  • ITO glass (Sodalime glass: 2 cm*2 cm) was pre-treated by ultrasonicating in soap water, acetone, ethanol and w -propanol in sequence and drying thoroughly in air.
  • the composition (3) was prepared in the synthesis example (above) and was dissolved in anisole with a concentration of 5 mg/mL. Then the solution was spin-coated on clean ITO.
  • the surface roughness of the spin-coated film of compound 3on ITO was characterized by Atomic Force Microscopy (AFM) (shown in Table 4). Compared to the original ITO, which has a surface roughness of 5.3 nm, the surface roughness (R q ) after spin-coating compound 3 on it decreased to 0.5 nm after spin-coating compound 3 on ITO.
  • AFM Atomic Force Microscopy
  • OLEDs were fabricated onto an ITO coated glass substrate that served as the anode, and topped with an aluminum cathode. All organic layers were thermally deposited by chemical vapor deposition in a vacuum chamber with a base pressure of less than 1 x 10 "7 Torr.The deposition rates of organic layers were maintained at 0.1-0.05 nm/s.
  • the aluminum cathode was deposited at 0.5 nra/s.
  • the active area of the OLED device was "3 mm x 3mm," as defined by the shadow mask for cathode deposition.
  • the glass substrate (20mm by 20mm) was available from Samsung Corning with ITO layer thickness of 1500 Angstrom.
  • ITO glass (2 cm x 2 cm) was cleaned as described in the film example above, and treated with oxygen plasma.
  • Compound 3 was prepared in the synthesis example (above), and was dissolved in anisole with a concentration of approximately 20 mg/mL.
  • the solution of compound 3 was spin-coated onto the ITO glass substrates as HIL in glove box.
  • the film was annealed at 80°C for 20 min. Then the film substrates were transferred into a thermal evaporator, under a vacuum of approximately 1 x 10 "7 Torr.
  • HTL1, HTL2, Fl Blue EML Aluminum 8 -Hydroxy quinolinate (Alq 3 ) and Lithium quinolate (Liq) were deposited, in sequence, with a thickness of 5nm, 25nm, 20nm,30nm and 2nm,respectively.
  • the deposition rates of organic layers were maintained at 0.1-0.05 nm/s.
  • the deposition rates of organic layers were maintained at 0.1-0.05 nm/s.
  • the aluminum cathode was deposited at 0.5nm/s.
  • the active area of the OLED was "3 mm by 3 mm," as defined by the shadow mask for cathode deposition.
  • composition (3) is vacuum deposited onto ITO instead of being spin-coated.
  • the device structure is as follows:
  • J-V-L current-voltage-brightness
  • KEITHLY 2308 Luminescence meter
  • EL spectra of the OLED devices were collected by a calibrated CCD spectrograph.
  • FIGS 1 -3 and Table 5 show that inventive devicesl and 2 using inventive composition (3) as HIL (either deposited by thermo-evaporation or solution process), exhibit comparable driving voltage and efficiency as comparative examples3 and 4. However, device examples 1 and 2 exhibit better lifetime compared to the comparative examples. After 600 min with a starting luminance of 4000 Cd/m 2 , the luminance of device remains the same (100%) as the beginning for the devices comprising compound 3 applied by evaporation process(Device example 1) and it becomes slightly higher (102.3%) than the beginning for the devices comprising compound 3 applied by solution process (Device example 2). However, for the devices comprising polythiophene (Comparative example 3) and 2-TNATA (Comparative example 4) as HIL, respectively, decreased to 01.3% and 07.3% after the same duration.
  • the Applicant has developed hole-injection material formed from the composition comprising TPE of Structure (I), TPE of structure (IA), or a combination thereof.
  • the present TPE composition is suitable for both thermo-evaporation and solution processes.
  • Devices comprising such material as HIL show comparable driving voltage and efficiency as those using polythiophenes and 2-TNATAas HIL but longer lifetime than those using polythiophenes and 2-TNATAas HIL.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne une composition, un film contenant la composition, et un dispositif électronique contenant la composition. La composition comprend un tétraphénylène éthylène de structure (I), un tétraphénylène éthylène de structure (IA), ou une combinaison de ceux-ci, où pour chaque structure (I) et (IA), R1, R2, R3, et R4 sont identiques ou différents, et où R1, R2, R3 et R4 sont chacun indépendamment sélectionnés parmi le groupe constitué de l'hydrogène, d'un hydrocarbure, d'un hydrocarbure substitué, et des combinaisons de ceux-ci.
PCT/CN2012/088034 2012-12-31 2012-12-31 Composé à base de tétraphénylène éthylène et dispositif oled le contenant WO2014101178A1 (fr)

Priority Applications (5)

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PCT/CN2012/088034 WO2014101178A1 (fr) 2012-12-31 2012-12-31 Composé à base de tétraphénylène éthylène et dispositif oled le contenant
TW102146936A TW201434802A (zh) 2012-12-31 2013-12-18 以四伸苯乙烯爲主之化合物及包含該化合物之ｏｌｅｄ裝置
KR1020130163804A KR20140088017A (ko) 2012-12-31 2013-12-26 테트라페닐렌 에틸렌 기재 화합물 및 그를 함유하는 ｏｌｅｄ 장치
JP2013270610A JP2014129347A (ja) 2012-12-31 2013-12-27 テトラフェニレンエチレン系化合物及びそれを含むｏｌｅｄデバイス
CN201310743948.1A CN104064689A (zh) 2012-12-31 2013-12-30 基于四苯基乙烯的化合物和含有该化合物的oled器件

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CN112920057A (zh) * 2019-12-06 2021-06-08 三星显示有限公司 有机电致发光装置及用于有机电致发光装置的胺化合物

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CN104119861B (zh) * 2013-04-27 2016-03-09 广东阿格蕾雅光电材料有限公司 有机电子材料
EP3160007B1 (fr) 2014-06-06 2018-12-26 IHI Corporation Dispositif émetteur de puissance, dispositif récepteur de puissance, et système d'alimentation électrique sans fil
KR102622078B1 (ko) * 2018-12-13 2024-01-05 엘지디스플레이 주식회사 유기발광다이오드 및 이를 포함하는 유기발광장치

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CN101928559A (zh) * 2010-07-07 2010-12-29 中山大学 同时含三苯乙烯和四苯乙烯结构的聚集诱导发光材料及其合成方法和应用
CN102190627A (zh) * 2010-12-10 2011-09-21 吉林大学 9,10-菲并咪唑衍生物及其作为电致发光材料的应用

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CN101928559A (zh) * 2010-07-07 2010-12-29 中山大学 同时含三苯乙烯和四苯乙烯结构的聚集诱导发光材料及其合成方法和应用
CN102190627A (zh) * 2010-12-10 2011-09-21 吉林大学 9,10-菲并咪唑衍生物及其作为电致发光材料的应用

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CN112920057A (zh) * 2019-12-06 2021-06-08 三星显示有限公司 有机电致发光装置及用于有机电致发光装置的胺化合物
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EP3831807A3 (fr) * 2019-12-06 2021-07-07 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé d'amine pour dispositif électroluminescent organique
CN112920057B (zh) * 2019-12-06 2024-02-09 三星显示有限公司 有机电致发光装置及用于有机电致发光装置的胺化合物

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