WO2026022085A1 - Composé, matériau semi-conducteur organique, dispositif électronique organique et dispositif d'affichage - Google Patents

Composé, matériau semi-conducteur organique, dispositif électronique organique et dispositif d'affichage

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Publication number
WO2026022085A1
WO2026022085A1 PCT/EP2025/070850 EP2025070850W WO2026022085A1 WO 2026022085 A1 WO2026022085 A1 WO 2026022085A1 EP 2025070850 W EP2025070850 W EP 2025070850W WO 2026022085 A1 WO2026022085 A1 WO 2026022085A1
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Prior art keywords
aryl
independently
compound
group
layer
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PCT/EP2025/070850
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English (en)
Inventor
Johannes Scholz
Jerome Ganier
Thomas STENNET
Susanne MAI
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NovaLED GmbH
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NovaLED GmbH
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Classifications

    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • a typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate.
  • the HTL, the EML, and the ETL are thin films formed from organic compounds.
  • DE 10 2021 100 597 A1 discloses a plurality of host materials and an organic electroluminescent device comprising the same.
  • DE 102022102199 A1 an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same.
  • US 2021/0098716 A1 discloses an organic electroluminescence device, comprising: a first electrode; a second electrode on the first electrode; and an emission layer between the first electrode and the second electrode, wherein the emission layer comprises host compounds and dopant compounds.
  • the object of the present invention to provide compounds and semiconducting materials for preparing organic electronic devices, such as organic light emitting diodes and display devices overcoming drawbacks of the prior art, in particular with respect to current efficiency and/or operating voltage and/or lifetime and/or operating voltage stability.
  • an organic semiconducting material comprising a compound represented by one of the following formulas (Ia), (Ib) or E4 E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and R 6 are independently C6 to C18 aryl; and/or - R 6 is C6 to C18 aryl; - R 1 is
  • This object is further achieved by an organic electronic device comprising the organic semiconducting material according to the present invention.
  • a display device comprising at least one organic electronic device according to the present invention.
  • Organic semiconducting material is related to an organic semiconducting material.
  • the organic semiconducting material comprises the compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the invention as described herein. This includes the possibility that the organic semiconducting material comprises a mixture of two or more of the compound of formula (Ia), the compound of formula (Ib) and the compound E4. Whenever herein, reference is made to “the compound of formula (Ia), the compound of formula (Ib) or the compound E4” mixture of two or more of the compound of formula (Ia), the compound of formula (Ib) and the compound E4 are included.
  • the organic semiconducting material may be an electron transporting material.
  • the organic semiconducting material may comprise the compound of formula (Ia), the compound of formula (Ib) or the compound E4 in an amount of at least 50 wt.-% with respect to the total weight of the organic semiconducting material, or in higher amounts, such as e.g. at least 60 wt.-%, at least 70 wt.-%, at least 80 wt.-%, at least 90 wt.-%, at least 95 wt.-% or at least 98 wt.-% with respect to the total weight of the organic semiconducting material.
  • the organic semiconducting material may consist of the compound of formula (Ia), the compound of formula (Ib) or the compound E4.
  • the organic semiconducting material may comprise besides the compound of formula (Ia), the compound of formula (Ib) or the compound E4 an electrical dopant, especially an electrical n- dopant.
  • electrical dopant especially n-type dopant, it is understood a compound which, if embedded into an electron transport matrix, improves, in comparison with the neat matrix under the same physical conditions, the electron properties of the formed organic material, particularly in terms of electron injection and/or electron conductivity.
  • “embedded into an electron transport matrix” means homogenously mixed with the electron transport matrix.
  • the electrical dopant as referred to herein is especially selected from elemental metals, metal salts, metal complexes and organic radicals.
  • the electrical dopant is selected from alkali metal salts and alkali metal complexes; preferably from lithium salts and lithium organic complexes; more preferably from lithium halides and lithium organic chelates; even more preferably from lithium fluoride, a lithium quinolinolate, lithium borate, lithium phenolate, lithium pyridinolate or from a lithium complex with a Schiff base ligand; most preferably, - the lithium complex has the formula II, III or IV: wherein A 1 to A 6 are same or independently selected from CH, CR, N, O; R is same or independently selected from hydrogen, halogen, alkyl or aryl or heteroaryl with 1 to 20 carbon atoms; and more preferred A 1 to A 6 are CH, - the borate based organic ligand is a tetra(1H-pyrazol-1-yl)borate, - the phenolate is a 2-(pyridin-2-yl)phenolate, a 2-(diphenylphosphoryl)
  • Electrically neutral metal complexes suitable as n-type dopants may be e.g. strongly reductive complexes of some transition metals in low oxidation state.
  • Particularly strong n-type dopants may be selected for example from Cr(II), Mo(II) and/or W(II) guanidinate complexes such as W2(hpp)4, as described in more detail in WO2005/086251.
  • Electrically neutral organic radicals suitable as n-type dopants may be e.g.
  • any metal-doped covalent material prepared by vacuum thermal evaporation contains the metal at least partially in its elemental form.
  • Compound of formula (Ia), compound of formula (Ib) and compound E4 in the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4.
  • the compound of formulas (Ia), (Ib) and E4 may be unsubstituted or substituted. If the compound of formulas (Ia), (Ib) and E4 are substituted, one or more substituents independently selected from the group consisting of D and C1 to C6 alkyl may be attached to the structure by formally replacing a terminal hydrogen atom.
  • the compound of formulas (Ia), (Ib) and E4 may be substituted with one or more D (deuterium).
  • the compound of formulas (Ia), (Ib) and E4 is unsubstituted.
  • the compound of formula (Ib) is unsubstituted.
  • the compound of formula (Ib) is unsubstituted, and the compound of formulas (Ia) and E4 may be unsubstituted or substituted.
  • the one or more substituents are independently selected from the group consisting of D and C1 to C6 alkyl, wherein “substituted” means that the respective substituent is attached to the structure by formally replacing a terminal hydrogen atom.
  • the compound of formulas (Ia) and E4 is substituted, the compound may be substituted with one or more D (deuterium). Most preferred, the compound of formulas (Ia) and E4 is unsubstituted.
  • the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C 6 to C 18 aryl, wherein - R 2 is C 6 to C 18 aryl; and/or - R 2 and R 3 are independently C 6 to C 18 aryl; and/or - R 3 and R 4 are independently C 6 to C 18 aryl; and/or - R 4 and R 5 are independently C 6 to C 18 aryl; and/or - R 5 and R 6 are independently C 6 to C 18 aryl; and/or - R 6 is C 6 to C 18 aryl; - R 1 is selected from the group consisting of C 6
  • the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and R 6 are independently C6 to C18 aryl; and/or - R 6 is C6 to C18 aryl; - R 1 is selected from the group consisting of C6
  • the arbitrary group A in a formula showing the following binding situation, may be bound to any suitable binding position. In the following situation, where it is shown that the bond of A crosses more than one ring the arbitrary group A may be bound to any suitable binding position of each ring crossed with the bond.
  • m is an integer selected from the group consisting of 0, 1, 2, 3, and 4.
  • m may be an integer selected from the group consisting of 0, 1, 2, and 3.
  • m may be an integer selected from the group consisting of 0, 1, and 2.
  • m may be an integer selected from the group consisting of 1 and 2.
  • m may be an integer selected from the group consisting of 0 and 1.
  • m may be 1. If m is 0, a single bond is formed at the respective position, that is, the compound of formula (Ia) has the following structure .
  • n, p, and q are independently integers selected from the group consisting of 1, 2, 3 and 4.
  • n, p, and q may be independently integers selected from the group consisting of 1, 2, and 3.
  • n, p, and q may be independently integers selected from the group consisting of 1 and 2.
  • the respective one phenylene is independently ortho-phenylene, meta- phenylene or para-phenylene, preferably independently meta-phenylene or para-phenylene.
  • the compound of formula (Ia) has the following structure
  • the respective biphenyl-diyl may be selected from wherein *1 and *2 are the binding positions to the remaining parts of the respective structure.
  • the respective biphenyl-diyl is the respective biphenyl-diyl is to form the following structure (in which, as an example, p is 2)
  • Ar 1 to Ar 9 are independently selected from C6 to C30 aryl.
  • Ar 1 to Ar 9 may be independently selected from C6 to C24 aryl.
  • Ar 1 to Ar 9 may be independently selected from C6 to C18 aryl.
  • Ar 1 to Ar 9 may be independently selected from C6 to C12 aryl.
  • Ar 1 to Ar 9 may be independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl.
  • Ar 1 to Ar 9 may be each phenyl.
  • R 2 to R 6 are independently selected from the group consisting of H, D and C 6 to C 18 aryl.
  • R 2 to R 6 may be independently selected from the group consisting of H, D and C 6 to C 12 aryl.
  • R 2 to R 6 may be independently selected from the group consisting of H, D, phenyl, biphenyl-yl, and naphthyl.
  • R 2 to R 6 may be independently selected from the group consisting of H, D, and phenyl.
  • R 2 is C 6 to C 18 aryl; and/or R 2 and R 3 are independently C 6 to C 18 aryl; and/or R 3 and R 4 are independently C 6 to C 18 aryl; and/or R 4 and R 5 are independently C 6 to C 18 aryl; and/or R 5 and R 6 are independently C 6 to C 18 aryl; and R 6 is C 6 to C 18 aryl. It may be provided that R 2 is phenyl; and/or R 2 and R 3 are both phenyl; and/or R 3 and R 4 are both phenyl; and/or R 4 and R 5 are both phenyl; and/or R 5 and R 6 are both phenyl; and R 6 is phenyl.
  • R 2 to R 6 are C 6 to C 18 aryl, preferably phenyl, and adjacent to each other and/or one or both of R 2 to R 6 which are adjacent to the binding position is/are C 6 to C 18 aryl, preferably phenyl.
  • the moiety in which * represents the binding position to may be selected from the following structures
  • R 1 is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C54 aryl and C3 to C53 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C48 aryl and C3 to C47 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C42 aryl and C3 to C41 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C36 aryl and C3 to C35 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C30 aryl and C3 to C29 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C24 aryl and C3 to C23 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C18 aryl and C3 to C17 heteroaryl.
  • R 1 may be selected from the group consisting of C6 to C12 aryl and C3 to C11 heteroaryl.
  • R 1 is selected from the group consisting of C6 to C60 aryl.
  • R 1 may be selected from C6 to C54 aryl.
  • R 1 may be selected from C6 to C48 aryl.
  • R 1 may be selected from C6 to C42 aryl.
  • R 1 may be selected from C6 to C36 aryl.
  • R 1 may be selected from C6 to C30 aryl.
  • R 1 may be selected from C6 to C24 aryl.
  • R 1 may be selected from C6 to C18 aryl.
  • R 1 may be selected from C6 to C12 aryl.
  • R 1 may be selected from the group consisting of phenyl, biphenyl-yl and naphthyl.
  • R 1 may be phenyl.
  • R 1 may be selected from the group C6 to C60 aryl and C3 to C59 heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six- membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2.
  • R 1 may be aryl or heteroaryl consisting of only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2.
  • R 1 may be selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 54 aryl and C 3 to C 53 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 48 aryl and C 3 to C 47 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 42 aryl and C 3 to C 41 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 36 aryl and C 3 to C 35 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 30 aryl and C 3 to C 29 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 24 aryl and C 3 to C 23 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 18 aryl and C 3 to C 17 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C 6 to C 12 aryl and C 3 to C 11 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2, respectively matching with the number of carbon atoms in the different embodiments.
  • R 1 may be selected from the group consisting of phenyl, biphenyl-yl and naphthyl.
  • R 1 may be phenyl.
  • the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and R 6 are independently C6 to C18 aryl; and/or - R 6 is C6 to C18 aryl; - R 1 is selected from the group consisting
  • the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C 6 to C 18 aryl, wherein - R 2 is C 6 to C 18 aryl; and/or - R 2 and R 3 are independently C 6 to C 18 aryl; and/or - R 3 and R 4 are independently C 6 to C 18 aryl; and/or - R 4 and R 5 are independently C 6 to C 18 aryl; and/or - R 5 and R 6 are independently C 6 to C 18 aryl; and/or - R 6 is C 6 to C 18 aryl; - R 1 is selected from the group consisting of C
  • the organic semiconducting material comprises a compound represented by one of the following formulas (Ia), (Ib) or E4 E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and R 6 are independently C6 to C18 aryl; and/or - R 6 is C6 to C18 aryl; - R 1 is selected from the group consisting
  • R 7 is selected from the group consisting of C 10 to C 30 condensed aryl and C 5 to C 29 condensed heteroaryl, wherein the C 10 to C 30 condensed aryl, respectively the C 5 to C 29 condensed heteroaryl comprise only six-membered aromatic rings.
  • Examples of a respective C 10 to C 30 condensed aryl are naphthyl or phenathryl.
  • Examples of respective C 5 to C 29 condensed heteroaryl are quinolinyl or acridinyl.
  • R 7 An example of a condensed heteroaryl not encompassed by the definition of R 7 is dibenzofuranyl which is, on the one hand, a condensed heteroaryl but does not only comprise six-memberd rings because it comprises also a five membered ring bearing the oxygen atom.
  • R 7 may be selected from the group consisting of C 10 to C 24 condensed aryl and C 5 to C 23 condensed heteroaryl, wherein the C 10 to C 24 condensed aryl, respectively the C 5 to C 23 condensed heteroaryl comprise only six-membered aromatic rings.
  • R 7 may be selected from the group consisting of C 10 to C 18 condensed aryl and C 5 to C 17 condensed heteroaryl, wherein the C 10 to C 18 condensed aryl, respectively the C 5 to C 17 condensed heteroaryl comprise only six- membered aromatic rings.
  • R 7 may be C 10 to C 24 condensed aryl, wherein the C 10 to C 24 condensed aryl comprises only six- membered aromatic rings.
  • R 7 may be C 10 to C 18 condensed aryl, wherein the C 10 to C 18 condensed aryl comprises only six-membered aromatic rings.
  • R 7 may be selected from the group consisting of naphthyl and phenanthryl.
  • R 7 may be selected from the group consisting of 1-naphthyl and 2-naphthyl. R 7 may be 2-naphthyl.
  • the compound of formula (Ia) may by E2 or E3
  • the compound of formula (Ib) may be E1
  • an organic semiconducting material comprising a compound represented by one of the following formulas (Ia), (Ib) or E4 wherein - m is 0 or 1; - n, p, and q are independently integers selected as 1 or 2; - Ar 1 to Ar 9 are independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl; - R 2 to R 6 are independently selected from the group consisting of H, D, and phenyl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C
  • the organic semiconducting material does not comprise the5 following compounds
  • the following compounds are excluded as a compound represented by formulas (Ia), Ib) or E4 in the organic semiconducting material according to the present invention
  • An organic semiconducting material comprising a compound represented by one of the5 following formulas (Ia), (Ib) or E4 wherein - m is an integer selected from 0, 1, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and R 6 are independently C6 to C18 aryl; and/or - R 6 is C6 to C18 aryl; - R 1 is selected from the group consisting of C6 to
  • the organic electronic device comprises a first electrode, a second electrode and an organic semiconducting layer.
  • the organic semiconducting layer is arranged between the first electrode and the second electrode.
  • the organic semiconducting layer consists of the organic semiconducting material according to the present invention, that is, comprises or consists of the compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the present invention.
  • the organic electronic device may be an organic light emitting diode (OLED).
  • the organic light emitting diode may comprise an anode, a cathode, a first light emitting layer and a semiconducting layer wherein - the first light emitting layer is arranged between the anode and the cathode; - the semiconducting layer is arranged between the first light emitting layer and the cathode; and - the semiconducting layer comprises the organic semiconducting material according to the present invention.
  • the semiconducting layer may consist of the organic semiconducting material according to the present invention.
  • the organic light emitting diode may comprise two or more semiconducting layers comprising a semiconducting material in accordance with the invention, respectively.
  • the semiconducting layer may be an electron injection layer, an electron transport layer, a hole blocking layer, or a n-type charge generation layer.
  • the semiconducting layer may be an electron transport layer.
  • the semiconducting layer may be an electron transport layer and OLED may further comprise an electron injection layer and the electron transport layer may be arranged between the first light emitting layer and the electron injection layer.
  • the semiconducting layer may be an electron transport layer and OLED may further comprise a hole blocking layer and the electron transport layer may be arranged between the hole blocking layer and the cathode.
  • the semiconducting layer may be an electron transport layer and OLED may further comprise an electron injection layer and a hole blocking layer; and the electron transport layer may be contacting sandwiched between the electron injection layer and the hole blocking layer.
  • the organic electronic device especially the organic light emitting diode in accordance with the invention may comprise especially, besides the semiconducting layer comprising or consisting of the semiconducting material according to the invention, further layers. Exemplary embodiments of respective layers are described in the following:
  • Substrate may be any substrate that is commonly used in manufacturing of, electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate shall be a transparent or semitransparent material, for example a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate may be both a transparent as well as a non-transparent material, for example a glass substrate, a plastic substrate, a metal substrate or a silicon substrate.
  • Anode electrode Either a first electrode or a second electrode comprised in the inventive organic electronic device may be an anode electrode.
  • the anode electrode may be formed by depositing or sputtering a material that is used to form the anode electrode.
  • the material used to form the anode electrode may be a high work-function material, so as to facilitate hole injection.
  • the anode material may also be selected from a low work function material (i.e. aluminum).
  • the anode electrode may be a transparent or reflective electrode.
  • Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin-dioxide (SnO 2 ), aluminum zinc oxide (AlZO) and zinc oxide (ZnO), may be used to form the anode electrode.
  • the anode electrode may also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.
  • Hole injection layer A hole injection layer (HIL) may be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like.
  • the deposition conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. In general, however, conditions for vacuum deposition may include a deposition temperature of 100° C to 500° C, a pressure of 10 -8 to 10 -3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm/sec.
  • coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 80° C to about 200° C.
  • the HIL may be formed of any compound that is commonly used to form a HIL.
  • examples of compounds that may be used to form the HIL include a phthalocyanine compound, such as copper phthalocyanine (CuPc), 4,4',4"-tris (3-methylphenylphenylamino) triphenylamine (m- MTDATA), TDATA, 2T-NATA, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), and polyaniline)/poly(4-styrenesulfonate (PANI/PSS).
  • CuPc copper phthalocyanine
  • m- MTDATA 4,4',4"-tris (3-methylphenylphenylamino) triphenylamine
  • the HIL may comprise or consist of p-type dopant and the p-type dopant may be selected from tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), 2,2'-(perfluoronaphthalen-2,6- diylidene) dimalononitrile or 2,2',2''-(cyclopropane-1,2,3-triylidene)tris(2-(p- cyanotetrafluorophenyl)acetonitrile) but not limited hereto.
  • the HIL may be selected from a hole-transporting matrix compound doped with a p-type dopant.
  • CuPc copper phthalocyanine
  • F4TCNQ tetrafluoro-tetracyanoquinonedimethane
  • ZnPc zinc phthalocyanine
  • ⁇ -NPD N,N'-Bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine
  • ⁇ -NPD doped with 2,2'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile The p- type dopant concentrations can be selected from 1 to 20 wt.-%, more preferably from 3 wt.-% to 10 wt.-%.
  • the thickness of the HIL may be in the range from about 1 nm to about 100 nm, and for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injecting characteristics, without a substantial penalty in driving voltage.
  • Hole transport layer A hole transport layer may be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL.
  • the conditions for the vacuum or solution deposition may vary, according to the compound that is used to form the HTL.
  • the HTL may be formed of any compound that is commonly used to form a HTL. Compounds that can be suitably used are disclosed for example in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953 ⁇ 1010 and incorporated by reference.
  • Examples of the compound that may be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl- [1,1-biphenyl]-4,4'-diamine (TPD), or N,N'-di(naphthalen-1-yl)-N,N'-diphenyl benzidine (alpha-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N- carbazolyl)triphenylamine (TCTA).
  • carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole
  • benzidine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl- [1,1-biphenyl]-4,4'-diamine (TPD
  • TCTA can transport holes and inhibit excitons from being diffused into the EML.
  • the thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably, about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm.
  • a preferred thickness of the HTL may be 170 nm to 200 nm.
  • Electron blocking layer The function of an electron blocking layer (EBL) is to prevent electrons from being transferred from an emission layer to the hole transport layer and thereby confine electrons to the emission layer. Thereby, efficiency, operating voltage and/or lifetime are improved.
  • the electron blocking layer comprises a triarylamine compound.
  • the triarylamine compound may have a LUMO level closer to vacuum level than the LUMO level of the hole transport layer.
  • the electron blocking layer may have a HOMO level that is further away from vacuum level compared to the HOMO level of the hole transport layer.
  • the thickness of the electron blocking layer may be selected between 2 and 20 nm.
  • the electron blocking layer has a high triplet level, it may also be described as triplet control layer.
  • the function of the triplet control layer is to reduce quenching of triplets if a phosphorescent green or blue emission layer is used. Thereby, higher efficiency of light emission from a phosphorescent emission layer can be achieved.
  • the triplet control layer is selected from triarylamine compounds with a triplet level above the triplet level of the phosphorescent emitter in the adjacent emission layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2722908 A1.
  • Photoactive layer (PAL) The photoactive layer converts an electrical current into photons or photons into an electrical current.
  • the PAL may be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the PAL. It may be provided that the photoactive layer does not comprise the compound of formula (Ia), the compound of formula (Ib) or the compound E4.
  • the photoactive layer may be a light-emitting layer or a light-absorbing layer.
  • EML Emission layer
  • the EML may be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL.
  • the respective emission layer (EML) may be formed of a combination of a host and an emitter dopant.
  • the emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters which emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency.
  • the emitter may be a small molecule or a polymer.
  • the amount of the emitter dopant may be in the range from about 0.01 to about 50 parts by weight, based on 100 parts by weight of the host.
  • the emission layer may consist of a light-emitting polymer.
  • the EML may have a thickness of about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission, without a substantial penalty in driving voltage.
  • Hole blocking layer (HBL) A hole blocking layer (HBL) may be formed on the EML, by using vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like, in order to prevent the diffusion of holes into the ETL.
  • the HBL may have also a triplet exciton blocking function.
  • the HBL may also be named auxiliary ETL or a-ETL.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the HBL. Any compound that is commonly used to form a HBL may be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.
  • the HBL may have a thickness in the range from about 5 nm to about 100 nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties, without a substantial penalty in driving voltage.
  • the hole blocking layer may be made of the organic semiconducting material according to the invention, that is, may be the organic semiconducting layer in the organic light emitting diode according to the invention.
  • Electron transport layer (ETL) The organic electronic device according to the present invention may comprise an electron transport layer (ETL).
  • the OLED may comprise an electron transport layer or an electron transport layer stack comprising at least a first electron transport layer and at least a second electron transport layer.
  • the electron transport layer may comprise ETM materials comprising one or more electron transport compound(s) known in the art.
  • the electron transport layer comprises an electron transport compound, wherein the electron transport compound comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings may be substituted with C 1 to C 4 alkyl.
  • an aromatic, respectively heteroaromatic ring is a single aromatic ring, for example a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, a 5-membered heteroaromatic ring such as pyrrolyl etc.
  • each ring is considered as a single ring in this regard.
  • naphthalene comprises two aromatic rings.
  • the electron transport compound may comprise at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, and optionally 1 or 2 heteroaromatic rings.
  • the aromatic or heteroaromatic rings of the electron transport compound may be 6-membered rings.
  • the heteroaromatic rings of the electron transport compound may be a N-containing heteroaromatic ring, optionally all of the heteroaromatic rings are N-containing heteroaromatic rings, optionally all of the heteroaromatic rings heteroaromatic rings contain N as the only type of heteroatom.
  • the electron transport compound may comprise at least one six-member heteroaromatic ring containing one to three N-atoms in each heteroaromatic ring, optionally one to three 6- membered heteroaromatic rings containing one to three N-atoms in each heteroaromatic ring, respectively.
  • the at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be an azine.
  • the at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be triazine, diazine, pyrazine, pyrimidine, pyridine, quinazoline or bonzoquinazoline, preferably triazine. If the electron transport compound comprises two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least one aromatic ring which is free of a heteroatom. In an embodiment, the heteroatoms in the heteroaromatic rings of the electron transport compound are bound into the molecular structure of the electron transport compound by at least one double bond. Further, the electron transport layer may comprise one or more additives. The additive may be an n-type dopant.
  • the additive can be alkali metal, alkali metal compound, alkaline earth metal, alkaline earth metal compound, transition metal, transition metal compound or a rare earth metal.
  • the metal can be one selected from a group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb.
  • the n-type dopant can be one selected from a group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu and Yb.
  • the alkali metal compound may be 8-Hydroxyquinolinolato-lithium (LiQ), Lithium tetra(1H-pyrazol-1-yl)borate or Lithium 2-(diphenylphosphoryl)phenolate.
  • Suitable compounds for the ETM (which may be used in addition to the inventive compound as defined above) are not particularly limited.
  • the electron transport matrix compounds consist of covalently bound atoms.
  • the electron transport matrix compound comprises a conjugated system of at least 6, more preferably of at least 10 delocalized electrons.
  • the conjugated system of delocalized electrons may be comprised in aromatic or heteroaromatic structural moieties, as disclosed e.g.
  • the electron transport layer may have a thickness from about 1 to about 100 nm, such as from about 10 to about 50 nm.
  • the electron transport layer may comprise or consist of the organic semiconducting material according to the invention, that is, may be the organic semiconducting layer in the organic electronic device according to the invention.
  • Electron injection layer (EIL) The optional EIL, which may facilitate injection of electrons from the cathode, may be formed on the ETL, preferably directly on the electron transport layer.
  • Examples of materials for forming the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, Li 2 O, BaO, Ca, Ba, Yb, Mg, especially Yb which are known in the art.
  • Deposition and coating conditions for forming the EIL are similar to those for formation of the HIL, although the deposition and coating conditions may vary, according to the material that is used to form the EIL.
  • the thickness of the EIL may be in the range from about 0.1 nm to about 10 nm, for example, in the range from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron-injecting properties, without a substantial penalty in driving voltage.
  • the electron injection layer may comprise the organic semiconducting material according to the invention, that is, may be the organic semiconducting layer in the organic electronic device according to the invention.
  • Cathode electrode The cathode electrode is formed on the EIL if present.
  • the cathode electrode may be formed of a metal, an alloy, an electrically conductive compound, or a mixture thereof.
  • the cathode electrode may have a low work function.
  • the cathode electrode may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like.
  • the cathode electrode may be formed of a transparent conductive oxide, such as ITO or IZO.
  • the cathode may comprise more that 50 volume % of metal selected from Ag and Au.
  • the thickness of the cathode electrode may be in the range from about 5 nm to about 1000 nm, for example, in the range from about 10 nm to about 100 nm.
  • the cathode electrode When the thickness of the cathode electrode is in the range from about 5 nm to about 50 nm, the cathode electrode may be transparent or semitransparent even if formed from a metal or metal alloy.
  • the cathode may be a semi-transparent metal cathode having a thickness less than 20 nm, preferably less than 15 nm. It is to be understood that the cathode electrode is not part of an electron injection layer or the electron transport layer.
  • Charge generation layer/hole generation layer The organic electronic device according to the present invention may comprise a charge generation layer.
  • the charge generation layer (CGL) is composed of a double layer.
  • the charge generation layer is a pn junction joining an n-type charge generation layer (electron generation layer) and a p-type charge generation layer (hole generation layer).
  • the n-side of the pn junction generates electrons and injects them into the layer which is adjacent in the direction to the anode.
  • the p-side of the p-n junction generates holes and injects them into the layer which is adjacent in the direction to the cathode.
  • Charge generation layers are used in tandem devices, for example, in tandem OLEDs comprising, between two electrodes, two or more emission layers.
  • the n-type charge generation layer provides electrons for the first light emission layer arranged near the anode, while the p-type charge generation layer provides holes to the second light emission layer arranged between the first emission layer and the cathode.
  • the hole generation layer (p-type charge generation layer) can be composed of an organic matrix material doped with p-type dopant. Suitable matrix materials for the hole generation layer may be materials conventionally used as hole injection and/or hole transport matrix materials. Also, p-type dopant used for the hole generation layer can employ conventional materials.
  • the p-type dopant can be one selected from a group consisting of tetrafluore-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, radialene derivatives, iodine, FeCl3, FeF3, and SbCl5.
  • F4-TCNQ tetrafluore-7,7,8,8-tetracyanoquinodimethane
  • radialene derivatives iodine
  • FeCl3, FeF3, and SbCl5 tetrafluore-7,7,8,8-tetracyanoquinodimethane
  • the host can be one selected from a group consisting of N,N'-di(naphthalen-1-yl)-N,N-diphenyl- benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD) and N,N',N'-tetranaphthyl-benzidine (TNB).
  • the n-type charge generation layer can be layer of a neat n-dopant, for example of an electropositive metal, or can consist of an organic matrix material doped with the n-dopant.
  • the n-type dopant can be alkali metal, alkali metal compound, alkaline earth metal, or alkaline earth metal compound.
  • the metal can be one selected from a group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb.
  • the n-type dopant can be one selected from a group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu and Yb.
  • Suitable matrix materials for the electron generating layer may be the materials conventionally used as matrix materials for electron injection or electron transport layers.
  • the matrix material can be for example one selected from a group consisting of triazine compounds, hydroxyquinoline derivatives like tris(8-hydroxyquinoline)aluminum, benzazole derivatives, and silole derivatives.
  • the n-type charge generation layer may comprise the semiconducting material according to the invention, that is, may be the semiconducting layer in the organic light emitting diode according to the invention.
  • the OLED according to the present invention can comprise a layer structure of a substrate that is adjacent arranged to an anode electrode, the anode electrode is adjacent arranged to a first hole injection layer, the first hole injection layer is adjacent arranged to a first hole transport layer, the first hole transport layer is adjacent arranged to a first electron blocking layer, the first electron blocking layer is adjacent arranged to a first emission layer, the first emission layer is adjacent arranged to an electron blocking layer, the electron blocking layer is adjacent arranged to an electron transport layer, the electron transport layer is adjacent arranged to an electron injection layer, the electron injection layer is adjacent arranged to a cathode, wherein the electron transport layer consists of the organic semiconducting material according to the present invention.
  • the OLED according to the present invention can comprise a layer structure of a substrate that is adjacent arranged to an anode electrode, the anode electrode is adjacent arranged to a first hole injection layer, the first hole injection layer is adjacent arranged to a first hole transport layer, the first hole transport layer is adjacent arranged to a first electron blocking layer, the first electron blocking layer is adjacent arranged to a first emission layer, the first emission layer is adjacent arranged to a first electron transport layer, the first electron transport layer is adjacent arranged to an n-type charge generation layer (n- type sub-layer), the n-type charge generation layer is adjacent arranged to a hole generating layer (p-type sub-layer), an interlayer may be provided between the n-type sub-layer, and the p-type sub-layer, the hole generating layer is adjacent arranged to a second hole transport layer, the second hole transport layer is adjacent arranged to a second electron blocking layer, the second electron blocking layer is adjacent arranged to a second emission layer, between the second emission layer and the ca
  • the invention is related to a display device comprising the organic light emitting diode according to the invention.
  • the display device may be a television, a tablet, or a mobile phone.
  • Process for preparing the organic light emitting diode is related to a process for preparing the organic electronic device according to the present invention, wherein the process comprises a step of depositing compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the present invention on a solid support.
  • the method for depositing may comprise: - deposition via vacuum thermal evaporation; - deposition via solution processing, preferably the processing is selected from spin- coating, printing, casting; and/or - slot-die coating.
  • the invention relates a compound represented by one of the following formulas (IIa), (IIb) or E4.
  • the compound of formulas (IIa), (IIb) and E4 may be unsubstituted or substituted. If the compound of formulas (IIa), (IIb) and E4 are substituted, one or more substituents independently selected from the group consisting of D and C 1 to C 6 alkyl may be attached to the structure by formally replacing a terminal hydrogen atom.
  • the compound of formulas (IIa), (IIb) and E4 is substituted, the compound may be substituted with one or more D (deuterium).
  • the compound of formulas (IIa), (IIb) and E4 is unsubstituted.
  • the compound of formula (IIb) is unsubstituted.
  • the compound of formula (IIb) is unsubstituted, and the compound of formulas (IIa) and E4 may be unsubstituted or substituted. If the compound of formulas (IIa) and E4 are substituted, one or more substituents independently selected from the group consisting of D and C 1 to C 6 alkyl may be attached to the structure by formally replacing a terminal hydrogen atom.
  • the compound of formulas (IIa) and E4 may be substituted with one or more D (deuterium).
  • D deuterium
  • the compound of formulas ((IIa) and E4 is unsubstituted.
  • the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C 6 to C 30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C 6 to C 18 aryl, wherein - R 2 is C 6 to C 18 aryl; and/or - R 2 and R 3 are independently C 6 to C 18 aryl; and/or - R 3 and R 4 are independently C 6 to C 18 aryl; and/or - R 4 and R 5 are independently C 6 to C 18 aryl; and/or - R 5 and R 6 are independently C 6 to C 18 aryl; and/or - R 6 is C 6 to C 18 aryl; - R 1 is a C 6 to C 60 aryl or a C
  • the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C6 to C30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C6 to C18 aryl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and R 6 are independently C6 to C18 aryl; and/or - R 6 is C6 to C18 aryl; - R 1 is a C6 to C60 aryl or a C
  • the arbitrary group A in a formula showing the following binding situation, may be bound to any suitable binding position. In the following situation, where it is shown that the bond of A crosses more than one ring the arbitrary group A may be bound to any suitable binding position of each ring crossed with the bond.
  • m is an integer selected from the group consisting of 0, 1, 2, 3, and 4.
  • m may be an integer selected from the group consisting of 0, 1, 2, and 3.
  • m may be an integer selected from the group consisting of 0, 1, and 2.
  • m may be an integer selected from the group consisting of 1 and 2.
  • m may be an integer selected from the group consisting of 0 and 1. In formula (IIa), m may be 1. If m is 0, a single bond is formed at the respective position, that is, the compound of formula (IIa) has the following structure .
  • n, p, and q are independently integers selected from the group consisting of 1, 2, 3 and 4.
  • n, p, and q may be independently integers selected from the group consisting of 1, 2, and 3.
  • n, p, and q may be independently integers selected from the group consisting of 1 and 2.
  • the respective one phenylene is independently ortho-phenylene, meta- phenylene or para-phenylene, preferably independently meta-phenylene or para-phenylene.
  • the compound of formula (IIa) has the following structure
  • the respective biphenyl-diyl may be selected from wherein *1 and *2 are the binding positions to the remaining parts of the respective structure.
  • Ar 1 to Ar 9 are independently selected from C 6 to C 30 aryl.
  • Ar 1 to Ar 9 may be independently selected from C 6 to C 24 aryl.
  • Ar 1 to Ar 9 may be independently selected from C 6 to C 18 aryl.
  • Ar 1 to Ar 9 may be independently selected from C 6 to C 12 aryl.
  • Ar 1 to Ar 9 may be independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl.
  • Ar 1 to Ar 9 may be each phenyl.
  • R 2 to R 6 are independently selected from the group consisting of H, D and C 6 to C 18 aryl.
  • R 2 to R 6 may be independently selected from the group consisting of H, D and C 6 to C 12 aryl.
  • R 2 to R 6 may be independently selected from the group consisting of H, D, phenyl, biphenyl-yl, and naphthyl.
  • R 2 to R 6 may be independently selected from the group consisting of H, D, and phenyl.
  • R 2 is C 6 to C 18 aryl; and/or R 2 and R 3 are independently C 6 to C 18 aryl; and/or R 3 and R 4 are independently C 6 to C 18 aryl; and/or R 4 and R 5 are independently C 6 to C 18 aryl; and/or R 5 and R 6 are independently C 6 to C 18 aryl; and R 6 is C 6 to C 18 aryl. It may be provided that R 2 is phenyl; and/or R 2 and R 3 are both phenyl; and/or R 3 and R 4 are both phenyl; and/or R 4 and R 5 are both phenyl; and/or R 5 and R 6 are both phenyl; and R 6 is phenyl.
  • R 2 to R 6 are C 6 to C 18 aryl, preferably phenyl, and adjacent to each other and/or one or both of R 2 to R 6 which are adjacent to the binding position is/are C 6 to C 18 aryl, preferably phenyl.
  • the moiety in which * represents the binding position to may be selected from the following structures In formula (IIa), R 1 is aryl or heteroaryl comprising only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2.
  • R 1 may be aryl or heteroaryl consisting of only six-membered aromatic rings, and the number of the comprised six-membered aromatic rings is 1, 2, 3, 4, 5, 6 or 7; alternatively 1, 2, 3, 4, 5, or 6; alternatively 1, 2, 3, 4, or 5; alternatively 1, 2, 3, or 4; alternatively 1, 2, or 3; alternatively 1 or 2.
  • R 1 is selected from the group consisting of C6 to C60 aryl and C3 to C59 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C54 aryl and C3 to C53 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C48 aryl and C3 to C47 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C42 aryl and C3 to C41 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C36 aryl and C3 to C35 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C30 aryl and C3 to C29 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C24 aryl and C3 to C23 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C18 aryl and C3 to C17 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of C6 to C12 aryl and C3 to C11 heteroaryl, respectively comprising or consisting of only six-membered aromatic rings.
  • R 1 may be selected from the group consisting of phenyl, biphenyl-yl and naphthyl. R 1 may be phenyl.
  • R 7 is selected from the group consisting of C 10 to C 30 condensed aryl and C 5 to C 29 condensed heteroaryl, wherein the C 10 to C 30 condensed aryl, respectively the C 5 to C 29 condensed heteroaryl comprise only six-membered aromatic rings.
  • Examples of a respective C 10 to C 30 condensed aryl are naphthyl or phenythryl.
  • Examples of respective C 5 to C 29 condensed heteroaryl are quinolinyl or acridinyl.
  • R 7 An example of a condensed heteroaryl not encompassed by the definition of R 7 is dibenzofuranyl which is, on the one hand, a condensed heteroaryl but does not only comprise six-memeberd rings but also a five membered ring bearing the oxygen atom.
  • R 7 may be selected from the group consisting of C 10 to C 24 condensed aryl and C 5 to C 23 condensed heteroaryl, wherein the C 10 to C 24 condensed aryl, respectively the C 5 to C 23 condensed heteroaryl comprise only six-membered aromatic rings.
  • R 7 may be selected from the group consisting of C 10 to C 18 condensed aryl and C 5 to C 17 condensed heteroaryl, wherein the C 10 to C 18 condensed aryl, respectively the C 5 to C 17 condensed heteroaryl comprise only six- membered aromatic rings.
  • R 7 may be C 10 to C 24 condensed aryl, wherein the C 10 to C 24 condensed aryl comprises only six- membered aromatic rings.
  • R 7 may be C 10 to C 18 condensed aryl, wherein the C 10 to C 18 condensed aryl comprises only six-membered aromatic rings.
  • R 7 may be selected from the group consisting of naphthyl and phenanthryl.
  • R 7 may be selected from the group consisting of 1-naphthyl and 2-naphthyl.
  • R 7 may be 2-naphthyl.
  • a compound represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is 0 or 1; - n, p, and q are independently integers selected as 1 or 2; - Ar 1 to Ar 9 are independently selected from the group consisting of phenyl, biphenyl-yl and naphtyl; - R 2 to R 6 are independently selected from the group consisting of H, D, and phenyl, wherein - R 2 is C6 to C18 aryl; and/or - R 2 and R 3 are independently C6 to C18 aryl; and/or - R 3 and R 4 are independently C6 to C18 aryl; and/or - R 4 and R 5 are independently C6 to C18 aryl; and/or - R 5 and
  • the compound of formula (IIa) may by E2 or E3
  • the compound of formula (IIb) may be E1 According to an embodiment, the following compounds are excluded from the compound According to an embodiment, the following compounds are excluded from the compound comprising a compound represented by formulas (IIa), (IIb) or E4
  • the compound is represented by one of the following formulas (IIa), (IIb) or E4 wherein - m is an integer selected from 01, 2, 3 and 4; - n, p, and q are independently integers selected from 1, 2, 3 and 4; - Ar 1 to Ar 9 are independently selected from C 6 to C 30 aryl; - R 2 to R 6 are independently selected from the group consisting of H, D and C 6 to C 18 aryl, wherein - R 2 is C 6 to C 18 aryl; and/or - R 2 and R 3 are independently C 6 to C 18 aryl; and/or - R 3 and R 4 are independently C 6 to C 18 aryl; and/or - R 4 and R 5 are independently C 6 to C 18 aryl; and/or - R 5 and R 6 are independently C 6 to C 18 aryl; and/or - R 6 is C 6 to C 18 aryl; - R 1 is a C 6 to C 60 aryl or a C
  • organic compound used herein also encompasses compounds such as organometallic compounds, for example metallocenes etc. If not mentioned else explicitly, all compounds, groups, moieties, substituents etc. shown herein, especially by structural formulas, by systematic names etc. encompass the respective partially and fully deuteriated derivatives thereof.
  • zero-valent refers to a metal in the oxidation state 0, i.e. particular to metals from which no electron has been removed. The zero-valent metal may be present in the form of zero-valent atoms, neat metal, alloys etc.
  • trimvalent refers to a nitrogen atom with a single bond and a double bond and containing a lone pair of electrons.
  • hydrocarbyl group as used herein shall be understood to encompass any organic group comprising carbon atoms, in particular organic groups, such as alkyl, aryl, heteroaryl, heteroalkyl, in particular such groups which are substituents usual in organic electronics.
  • conjuggated system refer to a system of alternating ⁇ - and ⁇ -bonds or a molecule having alternating single and multiple bonds i.e. double bond or a system having one or more two-atom structural units having the ⁇ -bond between its atoms can be replaced by an atom bearing at least one lone electron pair, typically by a divalent O or S atom.
  • alkyl as used herein shall encompass linear as well as branched and cyclic alkyl.
  • C 3 -alkyl may be selected from n-propyl and iso-propyl.
  • C 4 -alkyl encompasses n-butyl, sec-butyl and t-butyl.
  • C 6 -alkyl encompasses n-hexyl and cyclo- hexyl.
  • the subscribed number n in C n relates to the total number of carbon atoms in the respective alkyl, arylene, heteroarylene or aryl group.
  • aryl or “arylene” as used herein shall encompass phenyl (C 6 -aryl), fused aromatics, such as naphthalene, anthracene, phenanthrene, tetracene etc.. Further encompassed are biphenyl and oligo- or polyphenyls, such as terphenyl, phenyl-substituted biphenyl, phenyl- substituted terphenyl (such as tetraphenyl benzene groups) etc.
  • aryl group or “arylene group” may refer to a group comprising at least one hydrocarbon aromatic moiety, and all the elements of the hydrocarbon aromatic moiety may have p-orbitals which form conjugation, for example a phenyl group, a napthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluorenyl group and the like.
  • spiro compounds in which two aromatic moieties are connected with each other via a spiro-atom, such as 9,9’-spirobi[9H-fluorene]yl.
  • the aryl or arylene group may include a monocyclic or fused ring polycyclic (i.e., links sharing adjacent pairs of carbon atoms) functional group.
  • heteroaryl refers to aryl groups in which at least one carbon atom is substituted with a heteroatom.
  • heteroaryl may refer to aromatic heterocycles with at least one heteroatom, and all the elements of the hydrocarbon heteroaromatic moiety may have p-orbitals which form conjugation.
  • the heteroatom may be selected from N, O, S, B, Si, P, Se, preferably from N, O and S.
  • a heteroarylene ring may comprise at least 1 to 3 heteroatoms.
  • a heteroarylene ring may comprise at least 1 to 3 heteroatoms individually selected from N, S and/or O.
  • heteroaryl comprises, for example, spiro compounds in which two aromatic moieties are connected with each other, such as spiro[fluorene-9,9’-xanthene].
  • heteroaryl groups are diazine, triazine, dibenzofurane, dibenzothiofurane, acridine, benzoacridine, dibenzoacridine etc.
  • a group is “substituted with” another group if one of the hydrogen atoms comprised in this group is replaced by another group, wherein the other group is the substituent.
  • the arbitrary group A in a formula showing the following binding situation, may be bound to any suitable binding position. In the following situation, where it is shown that the bond of A crosses more than one ring the arbitrary group A may be bound to any suitable binding position of each ring crossed with the bond.
  • the expression “between” with respect to one layer being between two other layers does not exclude the presence of further layers, which may be arranged between the one layer and one of the two other layers.
  • the expression “in direct contact” with respect to two layers being in direct contact with each other means that no further layer is arranged between those two layers. One layer deposited on the top of another layer is deemed to be in direct contact with this layer.
  • the term “essentially non-emissive” or “non- emissive” means that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10 %, preferably less than 5 % relative to the visible emission spectrum.
  • the visible emission spectrum is an emission spectrum with a wavelength of about ⁇ 380 nm to about ⁇ 780 nm.
  • the compounds mentioned in the experimental part may be most preferred.
  • the organic electroluminescent device may be a bottom- or top-emission device.
  • Another aspect is directed to a device comprising at least one organic electroluminescent device (OLED).
  • a device comprising organic light-emitting diodes is for example a display or a lighting panel.
  • the term “different” or “differs” in connection with the matrix material means that the matrix material differs in their structural formula.
  • the energy levels of the highest occupied molecular orbital, also named HOMO, and of the lowest unoccupied molecular orbital, also named LUMO, are measured in electron volt (eV).
  • organic electroluminescent device may comprise both organic light emitting diodes as well as organic light emitting transistors (OLETs).
  • OLETs organic light emitting transistors
  • jobsweight percent As used herein, usuallywt.-%”, wt%, whopercent by weight”, apparently% by weight”, and variations thereof refer to a composition, component, substance or agent as the weight of that component, substance or agent of the respective electron transport layer divided by the total weight of the respective electron transport layer thereof and multiplied by 100. It is understood that the total weight percent amount of all components, substances and agents of the respective electron transport layer and electron injection layer are selected such that it does not exceed 100 wt.-%.
  • the term “free of”, “does not contain”, “does not comprise” does not exclude impurities. Impurities have no technical effect with respect to the object achieved by the present invention.
  • the term “free of” a compound means that such compound/material is not deliberately added to the layer during processing.
  • the semiconducting layer according to the invention and layers in an OLED formed thereof are essentially non-emissive or non-emitting.
  • the operating voltage, also named U is measured in Volt (V) at 10 milliAmpere per square centimeter (mA/cm 2 ).
  • the candela per Ampere efficiency also named cd/A efficiency is measured in candela per ampere at 10 milliAmpere per square centimeter (mA/cm 2 ).
  • the external quantum efficiency also named EQE, is measured in percent (%).
  • the color space is described by coordinates CIE-x and CIE-y (International Commission on Illumination 1931). For blue emission the CIE-y is of particular importance. A smaller CIE-y denotes a deeper blue color. Efficiency values are compared at the same CIE-y.
  • the highest occupied molecular orbital, also named HOMO, and lowest unoccupied molecular orbital, also named LUMO, are measured in electron volt (eV).
  • OLED organic light emitting diode
  • organic light emitting device organic optoelectronic device
  • organic light-emitting diode are simultaneously used and have the same meaning.
  • life-span and “lifetime” are simultaneously used and have the same meaning.
  • the anode and cathode may be described as anode electrode / cathode electrode or anode electrode / cathode electrode or anode electrode layer / cathode electrode layer.
  • Room temperature also named ambient temperature, is 23 o C.
  • FIG.1 is a schematic sectional view of an organic light emitting diode (OLED), according to an exemplary embodiment of the present invention
  • FIG.2 is a schematic sectional view of an OLED, according to an exemplary embodiment of the present invention
  • FIG.3 is a schematic sectional view of an OLED, according to an exemplary embodiment of the present invention
  • FIG.4 is a schematic sectional view of an OLED comprising a charge generation layer and two emission layers, according to an exemplary embodiment of the present invention.
  • FIG.1 is a schematic sectional view of an organic semiconducting device 100, according to an exemplary embodiment of the present invention.
  • the organic semiconducting device 100 includes a substrate 110, an anode 120, a light emission layer (EML) 125, a semiconducting layer comprising or consisting of the organic semiconducting material according to the invention 160.
  • EML light emission layer
  • FIG.2 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention.
  • the OLED 100 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an emission layer (EML) 150, an electron transport layer (ETL) 160.
  • the electron transport layer (ETL) 160 is formed on the EML 150.
  • the electron transport layer is the organic semiconducting layer according to the invention.
  • FIG. 3 is a schematic sectional view of an OLED 100, according to another exemplary embodiment of the present invention. Fig.3 differs from Fig.2 in that the OLED 100 of Fig.3 comprises an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155. Referring to Fig.
  • the OLED 100 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode electrode 190.
  • the ETL 160 is the organic semiconducting layer comprising the compound according to the present invention.
  • Fig. 4 is a schematic sectional view of an OLED 100, according to another exemplary embodiment of the present invention.
  • the OLED 100 includes a substrate 110, an anode 120, a first hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first emission layer (EML) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generation layer (n-type CGL) 185, a hole generating layer (p-type charge generation layer; p-type GCL) 135, a second hole transport layer (HTL) 141, a second electron blocking layer (EBL) 146, a second emission layer (EML) 151, a second hole blocking layer (EBL) 156, a second electron transport layer (ETL) 161, a second electron injection layer (EIL) 181 and
  • the first electron transport layer (ETL) 160 is the organic semiconducting layer comprising the compound of formula (Ia), the compound of formula (Ib) or the compound E4 according to the present invention.
  • a sealing layer may further be formed on the cathode electrodes 190, in order to seal the OLEDs 100.
  • various other modifications may be applied thereto.
  • the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples.
  • Tested compounds Compounds according to the invention: OLED Tests To assess the performance of the inventive examples compared to the prior art, the current efficiency is measured at 20°C.
  • the current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between 0V and 10V.
  • the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd/m2 using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Ak elastic istsstelle (DAkkS)) for each of the voltage values.
  • the cd/A efficiency at 15 mA/cm2 is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.
  • the emission In bottom emission devices, the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE). To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA/cm2. In top emission devices, the emission is forward directed, non-Lambertian and also highly dependent on the mirco-cavity. Therefore, the efficiency EQE will be higher compared to bottom emission devices. To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA/cm 2 .
  • Lifetime LT of the device is measured at ambient conditions (20°C) and 30 mA/cm2, using a Keithley 2400 sourcemeter, and recorded in hours.
  • the brightness of the device is measured using a calibrated photo diode.
  • the lifetime LT is defined as the time till the brightness of the device is reduced to 97 % of its initial value.
  • the increase in operating voltage ⁇ U is used as a measure of the operational voltage stability of the device. This increase is determined during the LT measurement and by subtracting the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 100 hours.
  • ⁇ U [U100 h)- U(1h)]. The smaller the value of ⁇ U the better is the operating voltage stability.
  • Example 1 Blue fluorescent top emission OLED Blue fluorescent top emission OLEDs with a layer stack in accordance with Table 1 have been prepared.
  • Table 1 The observed device performance is shown in Table 2.
  • Table 2 In comparison with state-of-art compound C2, the inventive compounds E1 enabled lower operational voltage, higher current efficiency, longer lifetime and higher voltage stability.
  • Example 2 Blue fluorescent top emission OLED Blue fluorescent top emission OLEDs with a layer stack in accordance with Table 3 have been prepared.
  • Table 3 The observed device performance is shown in Tables 4 and 5.
  • Table 4 In comparison with state-of-art compound C2, the inventive compounds E1 and E4 enable lower operational voltage, longer lifetime and higher voltage stability.
  • Table 5 In comparison with state-of-art compounds C1 and C3, the inventive compounds E2 and E3 enable longer lifetime and higher voltage stability.

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  • Chemical & Material Sciences (AREA)
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  • Materials Engineering (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé. La présente invention concerne en outre un matériau semi-conducteur organique comprenant le composé, un dispositif électronique organique comprenant le matériau semi-conducteur, un dispositif d'affichage comprenant le dispositif électronique, et un procédé de préparation du dispositif électronique organique.
PCT/EP2025/070850 2024-07-26 2025-07-21 Composé, matériau semi-conducteur organique, dispositif électronique organique et dispositif d'affichage Pending WO2026022085A1 (fr)

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