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21.发明授权公开(公告)号：US11139446B2
公开(公告)日：2021-10-05
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：US20200071276A1
公开(公告)日：2020-03-05
申请号：US16490163
申请日：2018-03-02
申请人： Novaled GmbH
IPC分类号： C07D219/02 , H01L51/00
摘要： The present invention relates to acridine compound of formula structure (I), and to an electron transport layer, which comprises at least one compound of formula (I), an semiconductor layer comprising at least one compound of formula (I) as well as to an electronic device comprising a semiconductor layer thereof.
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公开(公告)号：US20200058880A1
公开(公告)日：2020-02-20
申请号：US16344426
申请日：2017-10-18
发明人： Julien Frey , Domagoj Pavicic , Volodymyr Senkovskyy , Elena Galan , Hyungsun Kim , Byungku Kim
IPC分类号： H01L51/00 , C07D219/02 , C09K11/06 , C07D401/14
摘要： The present invention relates to a compound of an acridine derivate as well as of an organic semiconductor material an organic semiconductor layer, an electronic device comprising the acridine derivative, a device comprising an organic light-emitting diode comprising the acridine derivative, a display device thereof and a method of manufacturing the same. (I) wherein L is selected from phenylene, naphthylene and biphenylene; R1, R2, R3, R4 and R5 are independently selected from unsubstituted or substituted C6 to C18 aryl and unsubstituted or substituted pyridyl; and the substituents are selected from deuterium, C1 to C12 alkyl and C1 to C12 alkoxy; a, b, c, d and e are independently selected from 0 or 1 and 2≤a+b+c+d+e≤5.
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24.发明申请公开(公告)号：US20190322642A1
公开(公告)日：2019-10-24
申请号：US16387645
申请日：2019-04-18
申请人： Novaled GmbH
IPC分类号： C07D401/10 , C07D405/14 , H01L51/00 , H01L51/50 , H01L51/52
摘要： The present invention relates to a compound of the Formula (I) wherein at least one of R1 to R10 and/or Ar4 is a group having the Formula (II) wherein the asterisk symbol “*” in Formula (II) represents the position of binding of the group having the Formula (II); L is selected from substituted or unsubstituted C6 to C18 arylene; Ar1 is selected from substituted or unsubstituted C3 to C24 heteroaryl, wherein the heteroaryl comprises at least two N-atoms; Ar2 and Ar3 are independently selected from substituted or unsubstituted C6 to C24 aryl and/or substituted or unsubstituted C4 to C24 heteroaryl, wherein Ar2 and Ar3 are selected differently from each other; Ar4 is selected from the group consisting of substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl and a group having the general Formula (II); R1 to R10 are independently selected from the group consisting of H, D, F, C1 to C20 alkyl, C6 to C20 aryl, C2 to C20 heteroaryl and a group having the Formula (II); and R1 and R2; or R2 and R3 or R3; and R4; or R5 and R6 may independently from each other form a fused ring or system of fused rings; a semiconducting layer comprising the same, an organic electronic device comprising the same as well as a display or a lighting device comprising the organic electronic device.
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公开(公告)号：US12029117B2
公开(公告)日：2024-07-02
申请号：US17413678
申请日：2019-12-16
申请人： Novaled GmbH
发明人： Benjamin Schulze , Volodymyr Senkovskyy , Francois Cardinali , Pierre Seidenglanz , Ulrich Denker , Stefan Zott
IPC分类号： H10K50/11 , H10K85/60 , H10K101/10 , H10K101/30 , H10K101/40
CPC分类号： H10K85/654 , H10K85/622 , H10K50/11 , H10K2101/10 , H10K2101/30 , H10K2101/40
摘要： Organic electroluminescent device comprising an anode, a cathode, at least one emission layer and an organic semiconducting layer; wherein the organic semiconducting layer is arranged between the at least one emission layer and the cathode; wherein the organic semiconducting layer comprises; a) a first organic compound comprising a first C10 to C42 arene structural moiety and/or a first C2 to C42 heteroarene structural moiety, wherein i) the dipole moment of the first organic compound, computed by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set, is from 0 to 2.5 Debye; and ii) the LUMO energy level of the first organic compound in the absolute scale taking vacuum energy level as zero, computed by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set, is in the range from −1.7 eV to −2.1 eV; and b) a second organic compound comprising a second C10 to C42 arene structural moiety and/or a second C2 to C42 heteroarene structural moiety and in addition at least one polar group selected from phosphine oxide and phosphine sulfide, wherein in) the dipole moment of the second organic compound, computed by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set, is from 1.5 to 10 Debye; and iv) the LUMO energy level of the second organic compound in the absolute scale taking vacuum energy level as zero is less than 0.25 eV higher or lower than the LUMO energy level of the first organic compound; wherein it is provided that the first organic compound and the second organic compound are different from each other.
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公开(公告)号：US11524952B2
公开(公告)日：2022-12-13
申请号：US16387645
申请日：2019-04-18
申请人： Novaled GmbH
IPC分类号： H01L51/50 , C07D401/10 , C07D405/14 , H01L51/00 , H01L51/52
摘要： The present invention relates to a compound of the Formula (I) wherein at least one of R1 to R10 and/or Ar4 is a group having the Formula (II) wherein the asterisk symbol “*” in Formula (II) represents the position of binding of the group having the Formula (II); L is selected from substituted or unsubstituted C6 to C18 arylene; Ar1 is selected from substituted or unsubstituted C3 to C24 heteroaryl, wherein the heteroaryl comprises at least two N-atoms; Ar2 and Ar3 are independently selected from substituted or unsubstituted C6 to C24 aryl and/or substituted or unsubstituted C4 to C24 heteroaryl, wherein Ar2 and Ar3 are selected differently from each other; Ar4 is selected from the group consisting of substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl and a group having the general Formula (II); R1 to R10 are independently selected from the group consisting of H, D, F, C1 to C20 alkyl, C6 to C20 aryl, C2 to C20 heteroaryl and a group having the Formula (II); and R1 and R2; or R2 and R3 or R3; and R4; or R5 and R6 may independently from each other form a fused ring or system of fused rings; a semiconducting layer comprising the same, an organic electronic device comprising the same as well as a display or a lighting device comprising the organic electronic device.
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公开(公告)号：US11407716B2
公开(公告)日：2022-08-09
申请号：US16490163
申请日：2018-03-02
申请人： Novaled GmbH
IPC分类号： H01L51/50 , C07D219/02 , H01L51/00 , H01L51/52
摘要： The present invention relates to acridine compound of formula structure (I), and to an electron transport layer, which comprises at least one compound of formula (I), an semiconductor layer comprising at least one compound of formula (I) as well as to an electronic device comprising a semiconductor layer thereof.
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公开(公告)号：US20220037595A1
公开(公告)日：2022-02-03
申请号：US17413678
申请日：2019-12-16
申请人： Novaled GmbH
发明人： Benjamin Schulze , Volodymyr Senkovskyy , Francois Cardinali , Pierre Seidenglanz , Ulrich Denker , Stefan Zott
IPC分类号： H01L51/00
摘要： Organic electroluminescent device comprising an anode, a cathode, at least one emission layer and an organic semiconducting layer; wherein the organic semiconducting layer is arranged between the at least one emission layer and the cathode; wherein the organic semiconducting layer comprises; a) a first organic compound comprising a first C10 to C42 arene structural moiety and/or a first C2 to C42 heteroarene structural moiety, wherein i) the dipole moment of the first organic compound, computed by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set, is from 0 to 2.5 Debye; and ii) the LUMO energy level of the first organic compound in the absolute scale taking vacuum energy level as zero, computed by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set, is in the range from −1.7 eV to −2.1 eV; and b) a second organic compound comprising a second C10 to C42 arene structural moiety and/or a second C2 to C42 heteroarene structural moiety and in addition at least one polar group selected from phosphine oxide and phosphine sulfide, wherein in) the dipole moment of the second organic compound, computed by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set, is from 1.5 to 10 Debye; and iv) the LUMO energy level of the second organic compound in the absolute scale taking vacuum energy level as zero is less than 0.25 eV higher or lower than the LUMO energy level of the first organic compound; wherein it is provided that the first organic compound and the second organic compound are different from each other.
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公开(公告)号：US20200161559A1
公开(公告)日：2020-05-21
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
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：US20190006589A1
公开(公告)日：2019-01-03
申请号：US16062974
申请日：2016-12-14
申请人： NOVALED GMBH
摘要： The invention relates to Organic light emitting diode comprising at least one emission layer, an electron injection layer and at least one cathode electrode, wherein: the electron injection layer comprises an organic phosphine compound, wherein the electron injection layer is free of a metal, metal salt, metal complex and metal organic compound; the cathode electrode comprises at least a first cathode electrode layer, wherein the first cathode electrode layer comprises a first zero-valent metal selected from the group comprising alkali metal, alkaline earth metal, rare earth metal and/or a group 3 transition metal; and the electron injection layer is arranged in direct contact to the first cathode electrode layer.
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