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公开(公告)号:US11950496B2
公开(公告)日:2024-04-02
申请号:US15777274
申请日:2016-11-23
申请人: Novaled GmbH
发明人: Volodymyr Senkovskyy
IPC分类号: H10K85/60 , C07F9/53 , C07F9/576 , C07F9/6506 , C07F9/6521 , C07F9/655 , C07F9/6558 , C07F9/6561 , H10K50/16 , H10K50/165 , H10K50/17 , H10K50/19
CPC分类号: H10K85/615 , C07F9/5325 , C07F9/5765 , C07F9/65068 , C07F9/6521 , C07F9/65517 , C07F9/65522 , C07F9/65586 , C07F9/6561 , H10K50/16 , H10K50/165 , H10K85/624 , H10K85/626 , H10K85/654 , H10K85/6572 , H10K85/6574 , H10K50/171 , H10K50/19
摘要: The present invention relates to an. organic semiconductive layer which is an electron transport layer and/or an electron injection layer and/or an n-type charge generation layer, the organic semiconductive layer comprising at least one compound of formula (1) wherein R1 and R2 are each independently selected from C1 to C16 alkyl; Ar1 is selected from C6 to C14 arylene or C3 to C12 heteroarylene; Ar2 is independently selected from C14 to C40 arylene or C8 to C40 heteroarylene; R3 is independently selected from H, C1 to C12 alkyl or C10 to C20 aryl; wherein each of Ar1, Ar2 and R3 may each independently be unsubstituted or substituted with at least one C1 to C12 alky group; n is 0 or 1; and m is 1 in case of n=0; and m is 1 or 2 in case of n=1, phosphine oxide compounds comprised therein and to organic electroluminescent devices comprising such layers and compounds.
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公开(公告)号:US11539001B2
公开(公告)日:2022-12-27
申请号:US16683508
申请日:2019-11-14
申请人: Novaled GmbH
发明人: Steffen Runge , Benjamin Schulze , Omrane Fadhel , Gregor Schwartz , Volodymyr Senkovskyy , Chao Wu
IPC分类号: H01L51/00 , C07D221/18 , C07D401/10 , C07D401/14 , C09K11/06 , H01L51/50
摘要: The present invention relates to compounds that include a nitrogen heteroatom, including a compound of the formula (I).
Also provided herein is an organic electronic device comprising the compound and a display device or lighting device comprising the organic electronic device.-
13.
公开(公告)号:US20210210708A1
公开(公告)日:2021-07-08
申请号:US15999648
申请日:2017-02-16
申请人: NOVALED GMBH
摘要: The present invention is directed to an organic light emitting diode (100) comprising: at least one anode electrode (120); at least one emission layer (150), wherein the emission layer comprises at least one emitter dopant that emits visible light at operation of the OLED (100); an electron transport layer stack (160) of at least two electron transport layers (161/162), and wherein a) the first electron transport layer (161) comprises i) a first organic aromatic matrix compound having a MW of about ≥400 to about ≤1000 and a dipole moment of about ≥0 Debye and about ≤2.5 Debye, wherein the first electron transport layer (161) is free of a polar organic aromatic phosphine compound; and b) the second electron transport layer (162) comprises two organic aromatic matrix compounds, which are a mixture of: i) the first organic aromatic matrix compound; and ii) a polar organic aromatic phosphine compound having a MW of about ≥400 to about ≤1000, and a dipole moment of about >2.5 Debye and about ≤10 Debye; and at least one cathode electrode layer (190); wherein the electron transport layer stack (160) is arranged between the emission layer (150) and the cathode electrode layer (190), the first electron transport layer (161) is in direct contact with the second electron transport layer (162), and wherein the first electron transport layer (161) is arranged nearer to the emission layer (150) and the second electron transport layer (162) is arranged nearer to the cathode electrode layer (190).
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公开(公告)号:US10749115B2
公开(公告)日:2020-08-18
申请号:US15739143
申请日:2016-06-22
申请人: Novaled GmbH
摘要: The invention relates to a semiconducting material comprising (i) in substantially elemental form, an electropositive element selected from alkaline metals, alkaline earth metals, rare earth metals, and transition metals, and (ii) at least one first compound which is a compound comprising at least one polar group selected from phosphine oxide group or diazole group; a process for manufacturing the semiconducting material; an electronic device comprising a cathode, an anode and the semiconducting material.
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15.
公开(公告)号:US20200161565A1
公开(公告)日:2020-05-21
申请号:US16683508
申请日:2019-11-14
申请人: Novaled GmbH
发明人: Steffen Runge , Benjamin Schulze , Omrane Fadhel , Gregor Schwartz , Volodymyr Senkovskyy , Chao Wu
IPC分类号: H01L51/00 , C07D401/10 , C09K11/06 , C07D401/14 , C07D221/18
摘要: The present invention relates to a compound of the formula (I) wherein all of R1 to R11, except one, are independently selected from the group consisting of H, D, F, substituted or unsubstituted C1 to C18 alkyl, substituted or unsubstituted C6 to C42 aryl, substituted or unsubstituted C3 to C42 heteroaryl; and adjacent groups R1 to R11 may be linked to each other to form a fused ring, wherein the one of R1 to R11 not selected from the above groups is a group G, wherein the group G comprises one atom A having an electron pair in a p-orbital thereof; the group G comprises two 6-membered aryl rings which are attached to the atom A, wherein each of the two 6-membered aryl rings is attached to the atom A via a single bond respectively; and wherein the two 6-membered aryl rings attached to the atom A may be connected with each other via a single bond; the group G comprises 12 to 66 carbon atoms in total; the group G is attached to the benzoacridine part of the compound of formula (I) via a single bond or via a C6 to C18 arylene group, wherein the C6 to C18 arylene group is part of the group G; and the group G is unsubstituted or substituted with one or more substituents independently selected from the group consisting of D, F, C1 to C18 alkyl, C6 to C42 aryl, C6 to C42 heteroaryl, (R12)2P═O, CN or G′, wherein the group G′ is defined likewise the group G with the exception that the group G′ is not attached to the benzoacridine part of the compound of formula (I) but to the group G via a single bond or via a C6 to C18 arylene group, wherein the C6 to C18 arylene group is part of the group G′ provided that in case that the group G is attached to the benzacridine part of the compound of formula (I) via the C6 to C18 arylene group, substituents which may be attached to the C6 to C18 arylene group are only selected from the group consisting of C1 to C18 alkyl, C6 to C42 aryl, (R12)2P═O and CN; wherein in case that at least one of R1 to R11, which is not the group G, is substituted, the respective substituent or substituents are independently selected from the group consisting of D, F, C1 to C18 alkyl, C6 to C36 aryl, C6 to C42 heteroaryl, (R12)2P═O, CN; and wherein R12 are independently selected from the group consisting of C1 to C18 alkyl and C6 to C24 aryl, an organic electronic device comprising the compound and a display device or lighting device comprising the organic electronic device.
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16.
公开(公告)号:US20180145263A1
公开(公告)日:2018-05-24
申请号:US15572336
申请日:2016-05-11
申请人: Novaled GmbH
发明人: Ulrich Denker , Mike Zöllner , Katja Gräf , Volodymyr Senkovskyy , Bodo Wallikewitz , Johannes Scholz , Julien Frey
IPC分类号: H01L51/00 , C07D401/04 , C07D401/14 , C07D405/14
CPC分类号: H01L51/0072 , C07D401/04 , C07D401/14 , C07D405/14 , C09K2211/1007 , C09K2211/1029 , C09K2211/185 , H01L51/0003 , H01L51/001 , H01L51/0052 , H01L51/0054 , H01L51/0058 , H01L51/0067 , H01L51/0073 , H01L51/0077 , H01L51/5076 , H01L51/508 , H01L51/56 , H01L2251/301
摘要: The present invention is directed to matrix compounds and an organic light-emitting diode (OLED) comprising an emission layer and an electron transport layer stack of at least two electron transport layers, wherein a first electron transport layer and a second electron transport layer comprises at least one matrix compound, wherein the matrix compound or compounds of the first electron transport layer is/are different to the matrix compound or compounds of the second electron transport layer; and in addition, the first electron transport layer comprises a dopant of a lithium halide and/or lithium organic complex; and the second electron transport layer is free of a dopant; wherein at least one matrix compound of the second electron transport layer having the chemical formula Ia, Ib and/or Ic: (Ia) (Ib) (Ic) wherein Ar=substituted or unsubstituted arylene with 6 to 20 ring-forming carbon atoms; or carbazolylene; ET=substituted or unsubstituted aryl group with 13 to 40 ring-forming carbon atoms; or a substituted or unsubstituted heteroaryl group with 14 to 40 ring-forming atoms.
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公开(公告)号:US20240147841A1
公开(公告)日:2024-05-02
申请号:US18532375
申请日:2023-12-07
申请人: Novaled GmbH
发明人: Volodymyr Senkovskyy
IPC分类号: H10K85/60 , C07F9/53 , C07F9/576 , C07F9/6506 , C07F9/6521 , C07F9/655 , C07F9/6558 , C07F9/6561 , H10K50/16 , H10K50/165
CPC分类号: H10K85/615 , C07F9/5325 , C07F9/5765 , C07F9/65068 , C07F9/6521 , C07F9/65517 , C07F9/65522 , C07F9/65586 , C07F9/6561 , H10K50/16 , H10K50/165 , H10K85/624 , H10K85/626 , H10K85/654 , H10K85/6572 , H10K85/6574 , H10K50/19
摘要: The present invention relates to an organic semiconductive layer which is an electron transport layer and/or an electron injection layer and/or an n-type charge generation layer, the organic semiconductive layer comprising at least one compound of formula (1)
wherein R1 and R2 are each independently selected from C1 to C16 alkyl; Ar1 is selected from C6 to C14 arylene or C3 to C12 heteroarylene; Ar2 is independently selected from C14 to C40 arylene or C8 to C40 heteroarylene; R3 is independently selected from H, C1 to C12 alkyl or C10 to C20 aryl; wherein each of Ar1, Ar2 and R3 may each independently be unsubstituted or substituted with at least one C1 to C12 alky group; n is 0 or 1; and m is 1 in case of n=0; and m is 1 or 2 in case of n=1, phosphine oxide compounds comprised therein and to organic electroluminescent devices comprising such layers and compounds.-
公开(公告)号:US11502258B2
公开(公告)日:2022-11-15
申请号:US16615211
申请日:2018-05-18
申请人: Novaled GmbH
IPC分类号: H01L51/00 , C07F9/6521 , C07F9/6558 , H01L51/50
摘要: The present invention relates to a compound of formula 1 and an organic electronic device comprising an organic semiconductor layer, wherein at least one organic semiconductor layer comprises a compound of formula (1), wherein L1 has the formula (2) and L2 has the formula (3), wherein L1 and L2 are bonded at “*” via a single bond independently to the same or different arylene groups or heteroarylenes group of Ar1; and wherein X1, X2 are independently selected from O, S and Se; Ar1 is selected from substituted or unsubstituted C20 to C52 arylene or C14 to C64 heteroarylene, wherein the substituent of the substituted C20 to C52 arylene or C14 to C64 heteroarylene are independently selected from C1 to C12 alkyl, C1 to C12 alkoxy, CN, halogen, OH, C6 to C25 aryl and C2 to C21 heteroaryl; R1, R2 are independently selected from substituted or unsubstituted C1 to C16 alkyl, wherein the substituent of substituted C1 to C16 alkyl is selected from C6 to C18 arylene or C2 to C12 heteroarylene; R3, R4 are independently selected from substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C18 arylene, C2 to C20 heteroarylene, wherein the substituent of substituted C1 to C16 alkyl, the substituent of the substituted C6 to C18 arylene, C2 to C20 heteroarylene are independently selected from C6 to C18 arylene or C2 to C12 heteroarylene; n is selected from 1 to 5, wherein n is an integer number.
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公开(公告)号:US11322687B2
公开(公告)日:2022-05-03
申请号:US14426698
申请日:2013-09-06
申请人: Novaled GmbH
摘要: The present invention relates to a charge transporting semi-conducting material comprising: a) optionally at least one electrical dopant, and b) at least one cross-linked charge-transporting polymer comprising 1,2,3-triazole cross-linking units, a method for its preparation and a semiconducting device comprising the charge transporting semi-conducting material.
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20.
公开(公告)号:US20210376259A1
公开(公告)日:2021-12-02
申请号:US17398835
申请日:2021-08-10
申请人: NOVALED GMBH
摘要: The present invention is directed to an organic light emitting diode (100) comprising: at least one anode electrode (120); at least one emission layer (150), wherein the emission layer comprises at least one emitter dopant that emits visible light at operation of the OLED (100); an electron transport layer stack (160) of at least two electron transport layers (161/162), and wherein a) the first electron transport layer (161) comprises i) a first organic aromatic matrix compound having a MW of about ≥400 to about ≤1000 and a dipole moment of about ≥0 Debye and about ≤2.5 Debye, wherein the first electron transport layer (161) is free of a polar organic aromatic phosphine compound; and b) the second electron transport layer (162) comprises two organic aromatic matrix compounds, which are a mixture of: i) the first organic aromatic matrix compound; and ii) a polar organic aromatic phosphine compound having a MW of about ≥400 to about ≤1000, and a dipole moment of about >2.5 Debye and about ≤10 Debye; and at least one cathode electrode layer (190); wherein the electron transport layer stack (160) is arranged between the emission layer (150) and the cathode electrode layer (190), the first electron transport layer (161) is in direct contact with the second electron transport layer (162), and wherein the first electron transport layer (161) is arranged nearer to the emission layer (150) and the second electron transport layer (162) is arranged nearer to the cathode electrode layer (190).
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