公开(公告)号：US09012639B2

公开(公告)日：2015-04-21

申请号：US13380361

申请日：2010-06-24

Applicant: Hartmut Yersin ,  Uwe Monkowius ,  Tobias Fisher ,  Thomas Hofbeck ,  Thomas Baumann ,  Tobias Grab

Inventor： Hartmut Yersin ,  Uwe Monkowius ,  Tobias Fisher ,  Thomas Hofbeck ,  Thomas Baumann ,  Tobias Grab

IPC: C07F15/00 ,  C07F9/00 ,  C07F9/62 ,  C07F1/00 ,  C07F9/58 ,  H01L51/00 ,  C07F9/6512 ,  H01L51/50

CPC classification number: H01L51/0091 ,  C07F1/005 ,  C07F9/58 ,  C07F9/62 ,  C07F9/6512 ,  H01L51/009 ,  H01L51/4253 ,  H01L51/5012 ,  H01L51/5072 ,  Y02E10/52 ,  Y02E10/549 ,  Y02P70/521

Abstract: The invention relates to copper(I) complexes of the formula A wherein X=Cl, Br or I (independently of one another); N*∩E=a bidentate ligand, wherein E=a phosphinyl group including a phosphorus atom or an arsenyl group including an arsenic atom, wherein the phosphinyl group or the arsenyl group is combined with R in the form of R2E (where R=alkyl, aryl, alkoxy, or phenoxy; N*=imine function which is part of an aromatic group selected from pyridyl, pyrimidyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl and imidazolyl, the aromatic group optionally having at least one substituent to increase the solubility of the copper(I) complex in an organic solvent; and ∩=at least one carbon atom which is likewise part of the aromatic group. The carbon atom is located directly adjacent both to the imine nitrogen atom, coordinating to Cu in the case of a bridging ligand and to the phosphorus or arsenic atom. The invention also relates to the use of the copper(I) complexes in optoelectronic assemblies, especially in Organic Light Emitting Diodes (OLEDs).

Abstract translation: 本发明涉及式A的铜（I）络合物，其中X = Cl，Br或I（彼此独立）; N *∩E=双齿配体，其中E =包括磷原子或包含砷原子的砷基的氧膦基，其中所述氧膦基或所述亚砷基与R 2的形式R（其中R =烷基 ，芳基，烷氧基或苯氧基; N * =亚胺官能团，其是选自吡啶基，嘧啶基，哒嗪基，三嗪基，恶唑基，噻唑基和咪唑基的芳族基团的一部分，芳族基团任选具有至少一个取代基以增加溶解度 在有机溶剂中的铜（I）络合物;∩=至少一个同样是芳族基团一部分的碳原子，碳原子位于与亚胺氮原子直接相邻的位置，在与 桥联配体和磷或砷原子。本发明还涉及铜（I）配合物在光电组件中的应用，特别是在有机发光二极管（OLED）中。

公开(公告)号：US20130264518A1

公开(公告)日：2013-10-10

申请号：US13806948

申请日：2011-06-28

Applicant: Hartmut Yersin

Inventor： Hartmut Yersin

IPC: H01L51/00

CPC classification number: H01L51/0072 ,  H01L51/005 ,  H01L51/0062 ,  H01L51/0071 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/5016 ,  H01L51/5028 ,  H05B33/14

Abstract: The invention relates to a composition comprising an organic emitter molecule, this molecule having a ΔE(S1−T1) value between the lowermost excited singlet state (S1) and the triplet state beneath it (T1) of less than 2500 cm−1, and an optically inert atom or molecule for reducing the inter-system crossing time constant of the organic molecule to less than 10−6 s.

Abstract translation: 本发明涉及包含有机发射体分子的组合物，该分子具有低于2500cm -1的最低激发单态（S1）和其下三重态（T1）之间的DeltaE（S1-T1）值，以及 用于将有机分子的系统间交叉时间常数降低至10-6秒的光学惰性原子或分子。

公开(公告)号：US20130025649A1

公开(公告)日：2013-01-31

申请号：US13574329

申请日：2011-01-19

Applicant: Hartmut Yersin ,  Rafal Czerwieniec ,  Tobias Fischer

Inventor： Hartmut Yersin ,  Rafal Czerwieniec ,  Tobias Fischer

IPC: C07F15/00 ,  C09K11/06 ,  H01L31/042

CPC classification number: H01L51/0087 ,  C09K11/06 ,  C09K2211/185 ,  H01L51/5012 ,  H01L51/5016 ,  H05B33/14 ,  Y02E10/549

Abstract: The invention relates to the use of a platinum-dicyano-bisisocyanide complex cluster, having a small ΔE distance, in particular between 500 cm−1 and 3000 cm−1, between the lowest triplet state and the overlying singlet state that is populated by means of thermal repopulation from the triplet, in an organic-electronic device for emission of blue light and for absorption in the ultraviolet and blue spectral range. The invention also relates to the use of the singlet harvesting method. Furthermore, the invention relates to the use of the high degrees of absorption of such platinum-dicyano-bisisocyanide complex clusters.

Abstract translation: 本发明涉及使用铂 - 二氰基 - 二异氰酸酯复合物簇，其具有小的Dgr.E距离，特别是在500cm -1和3000cm -1之间，在最低三重态和上覆的单重态之间，其被填充 通过来自三联体的热再生，在用于发射蓝光的有机电子装置中并在紫外和蓝光谱范围内进行吸收。 本发明还涉及单线收割方法的应用。 此外，本发明涉及使用这种铂 - 二氰基 - 二异氰酸酯复合物簇的高吸收度。

公开(公告)号：US20120184738A1

公开(公告)日：2012-07-19

申请号：US13380361

申请日：2010-06-24

Applicant: Hartmut Yersin ,  Uwe Monkowius ,  Tobias Fischer ,  Thomas Hofbeck ,  Thomas Baumann ,  Tobias Grab

Inventor： Hartmut Yersin ,  Uwe Monkowius ,  Tobias Fischer ,  Thomas Hofbeck ,  Thomas Baumann ,  Tobias Grab

IPC: C07F9/28

CPC classification number: H01L51/0091 ,  C07F1/005 ,  C07F9/58 ,  C07F9/62 ,  C07F9/6512 ,  H01L51/009 ,  H01L51/4253 ,  H01L51/5012 ,  H01L51/5072 ,  Y02E10/52 ,  Y02E10/549 ,  Y02P70/521

Abstract: The invention relates to copper(I) complexes of the formula (A) with X═Cl, Br or I (independently of one another) N*∩E=bidentate ligand, with E=phosphinyl/arsenyl radical of the form R2E (where R=alkyl, aryl, alkoxy, phenoxy, amide); N*=imine function. Which is part of an aromatic group selected from pyridyl, pyrimidyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl and imidazolyl, the aromatic group optionally having at least one substituent for increasing the solubility of the copper(I) complex in an organic solvent, and “∩”=at least one carbon atom, which is likewise part of the aromatic group, the carbon atom being located both directly adjacent to the imine nitrogen atom and to the phosphorus or arsenic atom, and also to the use thereof in optoelectronic assemblies, especially in OLEDs.

Abstract translation: 本发明涉及式（A）与X = Cl，Br或I（彼此独立）N（∩E）=二齿配体的式（A）的铜（I）络合物，其中E = R2E形式的氧化基/ R =烷基，芳基，烷氧基，苯氧基，酰胺）; N * =亚胺功能。 哪个是选自吡啶基，嘧啶基，哒嗪基，三嗪基，恶唑基，噻唑基和咪唑基的芳族基团的一部分，芳族基团任选具有至少一个用于增加铜（I）络合物在有机溶剂中的溶解度的取代基， ∩“=至少一个碳原子，其同样是芳族基团的一部分，碳原子位于与亚胺氮原子直接相邻的位置以及磷或砷原子，以及其在光电子组件中的用途，特别是 在OLED中。

公开(公告)号：US20110062858A1

公开(公告)日：2011-03-17

申请号：US12375220

申请日：2007-07-27

Applicant: Hartmut Yersin ,  Oliver Reiser ,  Luo Qun Li ,  Stefan Eibauer

Inventor： Hartmut Yersin ,  Oliver Reiser ,  Luo Qun Li ,  Stefan Eibauer

IPC: H01J1/63 ,  C07F15/00 ,  C07D413/10

CPC classification number: C09K11/06 ,  C07D263/32 ,  C07D263/34 ,  C07D263/42 ,  C07D263/57 ,  C07F15/002 ,  C07F15/0033 ,  C07F15/0046 ,  C07F15/006 ,  C07F15/0086 ,  C09K2211/1033 ,  C09K2211/185 ,  H01L51/0084 ,  H01L51/0087 ,  H01L51/5016

Abstract: The present invention relates to compounds which can be used in particular as ligands, to complexes and also to light-emitting devices and in particular to organic light-emitting devices (OLEDs). In particular, the invention relates to the use of luminescent oxazole-chelate metal complexes as emitters in such devices.

Abstract translation: 本发明涉及可特别用作配体，配合物以及发光器件，特别是有机发光器件（OLED）的化合物。 特别地，本发明涉及在这种装置中使用发光的恶唑 - 螯合金属络合物作为发射体。

公开(公告)号：US09252372B2

公开(公告)日：2016-02-02

申请号：US13001703

申请日：2009-06-23

Applicant: Hartmut Yersin ,  Uwe Monkowius

Inventor： Hartmut Yersin ,  Uwe Monkowius

IPC: H01L51/54 ,  C09K11/06 ,  H01L51/00 ,  H01L51/50 ,  H05B33/14

CPC classification number: H01L51/009 ,  C09K11/06 ,  C09K2211/185 ,  H01L51/0072 ,  H01L51/0084 ,  H01L51/0087 ,  H01L51/0091 ,  H01L51/5012 ,  H01L51/5016 ,  H05B33/14 ,  Y02E10/549 ,  Y02P70/521

Abstract: The invention relates to the use of a multinuclear metal or transition metal complex in an organic electronic device, said complex having a small ΔE spacing, particularly between 50 cm−1 and 2000 cm−1, between the lowest triplet state and the singlet state that is higher and is achieved by thermal backfilling from the triplet. The invention further relates to the use of the strong absorptions of such multinuclear metal complexes, particularly in OSCs.

Abstract translation: 本发明涉及多有机金属或过渡金属络合物在有机电子器件中的应用，所述复合物在最低三重态和单重态之间具有小的Dgr.E间距，特别是50cm -1和2000cm -1之间 状态较高，并且通过三联体的热回填实现。 本发明还涉及这种多核金属络合物的强吸收的用途，特别是在OSC中。

公开(公告)号：US09024026B2

公开(公告)日：2015-05-05

申请号：US13810848

申请日：2011-07-20

Applicant: Hartmut Yersin ,  Rafal Czerwieniec ,  Uwe Monkowius

Inventor： Hartmut Yersin ,  Rafal Czerwieniec ,  Uwe Monkowius

IPC: C09K11/06 ,  C07D471/04 ,  C07F5/02 ,  C07F9/50 ,  C07F9/6561 ,  H01L51/00 ,  H01L51/50

CPC classification number: C09K11/06 ,  C07D471/04 ,  C07F5/027 ,  C07F9/5027 ,  C07F9/5045 ,  C07F9/6561 ,  C09B57/00 ,  C09B57/008 ,  C09B57/10 ,  C09B69/109 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/188 ,  H01L51/0072 ,  H01L51/008 ,  H01L51/009 ,  H01L51/0091 ,  H01L51/5012 ,  Y02E10/549 ,  Y02P70/521

Abstract: The invention relates to neutral mononuclear copper (I) complexes for emitting light and with a structure according to formula (A) in which: M represents: Cu(I); L∩L represents: a single, negatively charged, bidentate ligand; N∩N represents: a diimine ligand (substituted with R and FG), in particular a substituted 2,2′-bipyridine derivative (bpy) or a substituted 1,10-phenanthroline derivative (phen); R represents: at least one sterically demanding substituent for preventing the planarization of the complex in the excited state; FG=functional group, and represents: at least one second substituent for increasing solubility in organic solvents. The substituent can also be used for electron transport or alternatively for hole transport, said functional group being bound to the diimine ligands either directly or by means of suitable bridges; and the copper (I) complex: having a ΔE(S1−T1) value of less than 2500 cm−1 between the lowest excited singlet state (S1) and the triplet state (T1) which lies below; having an emission lifespan of at most 20 μs; having an emission quantum yield of greater than 40%, and a solubility of at least 1 g/L in organic solvents, in particular polar organic hydrocarbons such as acetone, methyl ethyl ketone, benzene, toluene, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, dichloroethane, tetrachloroethylene, alcohols, acetonitrile or water.

Abstract translation: 本发明涉及用于发光并具有式（A）结构的中性单核铜（I）配合物，其中：M表示：Cu（I）; L∩L表示：单个带负电荷的二齿配体; N∩N表示：二亚胺配体（被R和FG取代），特别是取代的2,2'-联吡啶衍生物（bpy）或取代的1,10-菲咯啉衍生物（phen）; R表示：至少一个空间要求的取代基，用于防止复合物在激发态下的平面化; FG =官能团，并且表示：用于增加在有机溶剂中的溶解度的至少一个第二取代基。 该取代基也可以用于电子传输或者可以用于空穴传输，所述官能团直接或通过合适的桥结合到二亚氨配体; 和铜（I）配合物：在最低激发单态（S1）和位于下面的三重态（T1）之间具有小于2500cm -1的＆Dgr; E（S1-T1）值; 排放寿命至多为20μs; 具有大于40％的发光量子产率和至少1g / L的溶解度在有机溶剂中，特别是极性有机烃如丙酮，甲基乙基酮，苯，甲苯，氯苯，二氯苯，二氯甲烷，氯仿， 二氯乙烷，四氯乙烯，醇，乙腈或水。

公开(公告)号：US20140213806A1

公开(公告)日：2014-07-31

申请号：US14234781

申请日：2012-07-19

Applicant: Lars Wesemann ,  Fritz-Robert Küchle ,  Hermann August Mayer ,  Sophie Wernitz ,  Hartmut Yersin ,  Markus Leitl

Inventor： Lars Wesemann ,  Fritz-Robert Küchle ,  Hermann August Mayer ,  Sophie Wernitz ,  Hartmut Yersin ,  Markus Leitl

IPC: H01L51/00

CPC classification number: H01L51/009 ,  C07F1/08 ,  C09K11/06 ,  C09K2211/1096 ,  H01L51/0004 ,  H01L51/0091 ,  H01L51/5012 ,  H05B33/14 ,  Y02E10/549

Abstract: The invention describes electronic devices comprising a metal complex compound having at least one ligand contain-ing an N donor and a P donor having the formula (I), in which the carbons C1 and C2 are part of an aromatic or non-aromatic ring system F1, P and N are phosphorus and nitrogen, where the nitrogen is in sp2-hybridised form, the radicals R3 and R4 are, indepen-dently of one another, hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cyclo-alkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, hetero-aryl, aralkyl or heteroaralkyl radical having up to 40 C atoms, and R1 and R2 are, independently of one another, an atom or radical from the group comprising hydrogen, halogen, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, hetero-cycloalkyl, hetero-alkyl-cycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms and X=1, 2 or 3. The invention furthermore describes a process for the production of an electronic device of this type and processes for the generation of light or blue emission using a metal complex compound of this type.

Abstract translation: 本发明描述了包含具有至少一个含有N供体的配位体和具有式（I）的P给体的金属络合物的电子器件，其中碳C1和C2是芳族或非芳族环系的一部分 F1，P和N是磷和氮，其中氮是sp2杂交形式，基团R3和R4彼此独立地是氢或烷基，环烷基，烯基，环烯基，炔基，环炔基 具有至多40个C原子的烷基环烷基，杂烷基，杂环烷基，杂烷基环烷基，芳基，杂芳基，芳烷基或杂芳烷基，R 1和R 2彼此独立地为包含氢，卤素，R ，RO-，RS-，RCO-，RCOO-，RNH-，R2N-，RCONR-和-Si（R）X（OR）3-X，其中R =烷基，环烷基，烯基，环烯基，炔基， 烷基环烷基，杂烷基，杂环烷基，杂 - 烷基 - 环烷基，芳基，杂芳基，芳烷基或它 具有至多40个C原子且X = 1,2或3的三芳基烷基。本发明还描述了一种用于生产这种类型的电子器件的方法，并且使用这种金属络合物来产生光或蓝色发射的方法 类型。

公开(公告)号：US20140203225A1

公开(公告)日：2014-07-24

申请号：US14234857

申请日：2012-07-18

Applicant: Lars Wesemann ,  Hartmut Schubert ,  Hermann August Mayer ,  Hartmut Yersin ,  Andreas Rausch

Inventor： Lars Wesemann ,  Hartmut Schubert ,  Hermann August Mayer ,  Hartmut Yersin ,  Andreas Rausch

IPC: H01L51/00

CPC classification number: H01L51/0004 ,  C09K11/06 ,  C09K2211/1096 ,  C09K2211/183 ,  C09K2211/185 ,  C09K2211/188 ,  H01L51/009 ,  H01L51/0091 ,  H01L51/5016 ,  H05B33/14 ,  Y02E10/549

Abstract: The invention describes electronic devices comprising a metal complex compound having at least one anionic ligand containing two P donors, having the formula (I), in which R1 to R4 are, independently of one another, an atom or radical from the group comprising hydrogen, a halogen, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=a C1-C40-hydrocarbon and X=1, 2 or 3, and E is a bridge atom from the group with carbon or boron, where an atom or radical from the group with hydrogen, halogen, —CN, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=the C1-C40-hydrocarbon and X=1, 2 or 3, is optionally bonded to the carbon, and two radicals from the group with halogen, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=the C1-C40-hydrocarbon and X=1, 2 or 3, are optionally bonded to the boron. The invention furthermore describes a process for the production of an electronic device of this type and processes for the generation of light or blue emission using a metal complex compound of this type.

Abstract translation: 本发明描述了包含具有至少一种含有两个具有式（I）的P供体的阴离子配位体的金属络合物的电子器件，其中R 1至R 4彼此独立地为包含氢的原子或基团， 卤素，R，RO-，RS-，RCO-，RCOO-，RNH-，R2N-，RCONR-和-Si（R）X（OR）3-X，其中R = C1-C40-烃和X = 1,2或3，E是来自具有碳或硼的基团的桥原子，其中与氢，卤素，-CN，R，RO-，RS-，RCO-，RCOO- ，RNH-，R2N-，RCONR-和-Si（R）X（OR）3-X，其中R = C1-C40烃，X = 1,2或3任选地键合到碳上，两个 具有卤素，R，RO-，RS-，RCO-，RCOO-，RNH-，R2N-，RCONR-和-Si（R）X（OR）3-X的基团的基团，其中R = C1-C40 - 烃和X = 1,2或3任选地键合到硼上。 本发明还描述了用于生产这种类型的电子器件的方法，并且使用这种类型的金属络合物来产生光或蓝色发射的方法。

公开(公告)号：US08716510B2

公开(公告)日：2014-05-06

申请号：US13574329

申请日：2011-01-19

Applicant: Hartmut Yersin ,  Rafal Czerwieniec ,  Tobias Fischer

Inventor： Hartmut Yersin ,  Rafal Czerwieniec ,  Tobias Fischer

IPC: C07F15/00 ,  C09K11/06 ,  H01L31/042

CPC classification number: H01L51/0087 ,  C09K11/06 ,  C09K2211/185 ,  H01L51/5012 ,  H01L51/5016 ,  H05B33/14 ,  Y02E10/549

Abstract: The invention relates to the use of a platinum-dicyano-bisisocyanide complex cluster, having a small ΔE distance, in particular between 500 cm−1 and 3000 cm−1, between the lowest triplet state and the overlying singlet state that is populated by means of thermal repopulation from the triplet, in an organic-electronic device for emission of blue light and for absorption in the ultraviolet and blue spectral range. The invention also relates to the use of the singlet harvesting method. Furthermore, the invention relates to the use of the high degrees of absorption of such platinum-dicyano-bisisocyanide complex clusters.

Abstract translation: 本发明涉及使用铂 - 二氰基 - 二异氰酸酯复合物簇，其具有小的Dgr.E距离，特别是在500cm -1和3000cm -1之间，在最低三重态和上覆的单重态之间，其被填充 通过来自三联体的热再生，在用于发射蓝光的有机电子装置中并在紫外和蓝光谱范围内进行吸收。 本发明还涉及单线收割方法的应用。 此外，本发明涉及使用这种铂 - 二氰基 - 二异氰酸酯复合物簇的高吸收度。