EP3201962A1 - Composant électronique organique, utilisation d'un complexe de zinc comme dopant p pour matériau de matrice électronique organique - Google Patents

Composant électronique organique, utilisation d'un complexe de zinc comme dopant p pour matériau de matrice électronique organique

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Publication number
EP3201962A1
EP3201962A1 EP15771577.2A EP15771577A EP3201962A1 EP 3201962 A1 EP3201962 A1 EP 3201962A1 EP 15771577 A EP15771577 A EP 15771577A EP 3201962 A1 EP3201962 A1 EP 3201962A1
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EP
European Patent Office
Prior art keywords
zinc
group
alkyl
component according
complex
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP15771577.2A
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German (de)
English (en)
Inventor
Günter Schmid
Anna Maltenberger
Sébastien PECQUEUR
Florian Kessler
Stefan Regensburger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Osram Oled GmbH
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Osram Oled GmbH
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Publication date
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Publication of EP3201962A1 publication Critical patent/EP3201962A1/fr
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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
    • H10K85/30—Coordination compounds
    • H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • Zinc complex as a p-dopant for organic
  • the invention relates to the use of zinc complexes as p-dopants for organic electronic matrix materials.
  • organic electronics can be in
  • the first field of technology deals with applications of organic matrix materials for the conversion of light into electricity and vice versa, and the other field focuses on the construction of electrical components by means of organic semiconductor material.
  • Examples of the former category include photodetectors and organic solar cells, shown schematically in Figure 1, which convert light into an electrical signal or into electrical current, and organic light-emitting diodes (OLEDs), which
  • WO 2005 086251 A2 describes dopants for the production of n-type layers, which, inter alia, may also have the following structure:
  • Matrix material can be used as n-dopants.
  • DE 10 2012 209 520 A1 claims metal complexes of groups 5-7 as p-type dopants for organic electronic components and in this connection describes chromium and molybdenum-based complex compounds which are described as binuclear
  • Metal complexes form a paddle wheel structure.
  • Oxidation stages III and V are presented. The shown
  • WO 2011/033023 A1 describes copper complexes, in particular Cu (I) complexes as p-type dopants, which may be polynuclear.
  • Polynuclear copper complexes are always characterized by an even number of copper atoms, e.g. 2, 4 or 6 copper atoms.
  • an organic electronic component with a matrix contains as p-dopant a zinc complex, which in turn contains at least one ligand L of the following structure:
  • R 1 and R 2 may independently be oxygen, sulfur, selenium, NH or NR 4 , wherein R 4 is selected from the group consisting of alkyl or aryl and may be linked to R 3 ;
  • R 3 is selected from the group containing alkyl
  • alkyl long-chain alkyl, cycloalkyl, haloalkyl, aryl, arylenes, haloaryl, heteroaryl, heteroarylenes, heterocycloalkylenes, heterocycloalkyl, haloheteroaryl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, ketoaryl, haloketoaryl,
  • Ketoheteroaryl, ketoalkyl, Halogenketoalkyl, Ketoalkenyl, Halogenketoalkenyl, haloalkylaryl Halogenalkylheteroaryl wherein at suitable radicals one or more non-adjacent CH 2 groups ⁇ independently replaced by -0-, -S-, -NH-, -NR 000 -, -SiR ° R °°, -CO-, -COO-, -COR ° OR °°, -OCO-, -OCO-O-, -SO 2 -, -S-CO-, -CO-S-, -O -CS-, -CS-O-, -CY1 CY2 or -C ⁇ c- can be replaced in such a way that 0 and / or S atoms are not directly connected to each other, also optionally with aryl or heteroaryl preferably containing 1 until 30 C atoms have been replaced (terminal CH
  • each of R °, R °°, Y1 and Y2 may independently be selected from the group consisting of hydrogen, alkyl or aryl.
  • R °°° may for example be selected from the group consisting of alkyl and aryl.
  • Matrix materials can be used in organic electronic components.
  • Figs. 5-8 Some examples of zinc complexes are shown in Figs. 5-8.
  • both mononuclear and polynuclear complexes are mouldable with zinc.
  • polynuclear complexes of zinc with the ligands described above are not limited to paddle wheel structures nor to an even number of metal centers. Such a diversity of
  • Zinc complexes allow the doping strength in the matrix of organic electronic components largely independent of the sublimation temperature of the zinc complex
  • Doping strength and sublimation temperature of the metal complex is characteristic of the zinc complexes according to the invention.
  • the doping strength can also be adjusted more easily than with many conventional dopants of the respective matrix.
  • the materials described are easy to prepare and do not require expensive
  • the zinc complexes are also simply from different sources with the matrix material through
  • Dopant can be adapted to the particular requirements.
  • Haldrogen not limited to hydrogen ( i- H) alone, but includes in particular all other isotopes of hydrogen, in particular deuterium ( 2 H or D).
  • organic electronic component means and / or comprises
  • organic transistors in particular organic transistors, organic
  • p-dopant in particular includes or means materials which have a Lewis acidity and / or are able to form complexes with the matrix material in which these
  • Such a zinc complex matrix material may, for example, have the following structure:
  • Charges can be "hopped" from one hole transport molecule to another, but conduction paths are helpful for charge transport but not required.
  • Alkyl linear and branched C 1 -C 8 -alkyls long-chain alkyls: linear and branched C 5 -C 20 -alkyls
  • Alkenyl C2-C6-alkenyl
  • Cycloalkyl C3-C8-cycloalkyl, also adamantyl and
  • Alkylenes selected from the group comprising:
  • Aryl selected from aromatics with a molecular weight below 300Da.
  • Arylenes selected from the group comprising: 1, 2-phenylenes; 1,3-phenylenes; 1, 4-phenylene; 1, 2-naphthylenes; 1,3-naphthalenylenes; 1,4-naphthylenes; 2, 3-naphthylenes; 1-hydroxy-2, 3-phenylene; 1-hydroxy-2, 4-phenylene; 1-hydroxy-2, 5-phenylene; and 1-hydroxy-2, 6-phenylene, heteroaryl: selected from the group consisting of: pyridinyl; pyrimidinyl; pyrazinyl; triazolyl; pyridazinyl; 1,3,5-triazinyl; chinoninyl; isoquinoninyl; quinoxalinyl;
  • heteroaryl may be linked to the compound via any atom in the ring of the selected heteroaryl.
  • Heteroarylenes selected from the group comprising:
  • heteroarylene serves as a bridge in the compound via any atom in the ring of the selected heteroaryl
  • pyridine-2 4-diyl; pyridine-2, 5-diyl; pyridine-2, 6-diyl;
  • heteroaryl may be linked to the C 1 -C 6 alkyl via any atom in the ring of the selected heteroaryl.
  • Heterocycloalkylenes selected from the group comprising: piperidin-1, 2-ylene; piperidin-2, 6-ylene; piperidin-4, 4-ylidenes; 1, 4-piperazine-1,4-ylene; 1, 4-piperazine-2, 3-ylene; 1, 4-piperazine-2, 5-ylene; 1, 4-piperazine-2, 6-ylene; 1,4-piperazine-1,2-ylene; 1, 4-piperazine-1,3-ylene; 1, 4-piperazine-1, 4-ylene; tetrahydrothiophene-2, 5-ylene; tetrahydrothiophene-3, 4-ylene; tetrahydrothiophen-2, 3-ylene; tetrahydrofuran-2, 5-ylene; tetrahydrofuran-3, 4-ylene; tetrahydrofuran-2, 3-ylene; pyrrolidin-2, 5-ylene; pyrrolidin-3, 4-ylene; pyrrolidine-2, 3-ylene; pyrrolidin-1, 2-
  • Heterocycloalkyl selected from the group comprising:
  • heterocycloalkyl may be linked to the compound via any atom in the ring of the selected heterocycloalkyl.
  • Amines the group - (R) 2 wherein each R is independently selected from: hydrogen; Cl-C6-alkyl; Cl-C6-alkyl-C6H5; and phenyl, wherein when both R 'are C1-C6 alkyl, both R' can form a -NC3 to NC5 heterocyclic ring wherein the remaining alkyl chain is an alkyl substituent on the
  • Halogen selected from the group comprising: F; Cl; Br and I are haloalkyl: selected from the group comprising mono-, di-, tri-, poly- and perhalogenated linear and branched C 1 -C 8 -alkyl, more preferably -CF 3
  • Pseudohalogen selected from the group comprising -CN, -SCN, -OCN, N3, -CNO, -SeCN
  • Carboxylate the group -C (O) OR, wherein R is selected from: hydrogen; Cl-C6-alkyl; phenyl; Cl-C6-alkyl-C6H5; Carbonyl: the group -C (O) R, where R is selected from:
  • Alkyl linear and branched C 1 -C 6 -alkyl
  • long-chain alkyls linear and branched C5-C10 alkyl, preferably C6-C8 alkyl
  • Alkenyl C3-C6 alkenyl
  • Cycloalkyl C6-C8-cycloalkyl
  • Alkylenes selected from the group comprising: methylenes; 1,2-ethylene; 1, 3-propylene; butan-2-ol-1,4-diyl; 1,4-butylenes; cyclohexane-1, 1-diyl; cyclohexane-1,2-diyl;
  • Aryl selected from the group comprising: phenyl; biphenyl; naphthalenyl; anthracenyl; and phenanthrenyl, arylenes: selected from the group comprising: 1, 2-phenylenes;
  • Heteroaryl selected from the group comprising:
  • Heteroaryl may be linked to the compound via each atom in the ring of the selected heteroaryl,
  • Heteroarylenes selected from the group comprising: pyridine
  • Heterocycloalkyl selected from the group comprising:
  • pyrrolidinyl morpholinyl; piperidinyl; piperidinyl; 1,4-piperazinyl; tetrahydrofuranyl; 1, 4, 7-triazacyclononanyl; 1,4,8,11-tetraazacyclotetradecanyl; 1,4,7,10, 13-pentaazacyclopentadecanyl; 1,4,7,10-tetraazacyclododecanyl; and piperazinyl, wherein the heteroaryl is linked to the compound every atom in the ring of the selected heteroaryl can be connected
  • Heterocycloalkylenes selected from the group comprising: piperidin-2, 6-ylene; piperidin-4, 4-ylidenes; 1,4-piperazine-1,4-ylene; 1, 4-piperazine-2, 3-ylene; 1, 4-piperazine-2, 6-ylene; tetrahydrothiophene-2, 5-ylene; tetrahydrothiophene-3, 4-ylene; tetrahydrofuran-2, 5-ylene; tetrahydrofuran-3, 4-ylene;
  • Heterocycloalkyls may be connected
  • Amine the group -N (R) 2, where each R is independent
  • Halogen selected from the group comprising: F and Cl,
  • Carboxylate the group -C (O) OR, wherein R is selected from hydrogen; Cl-C6-alkyl; and benzyl,
  • Carbonyl the group: -C (O) R, wherein R is selected from: hydrogen; Cl-C6-alkyl; Benzyl and amines selected from the group: -NR'2, wherein each R 'is independently selected from: hydrogen; Cl-C6-alkyl; and benzyl,
  • R 3 is haloalkyl, more preferably perfluoroalkyl of 1 to 8 carbons, even more preferably 1 to 4, haloaryl, more preferably perfluoroaryl, haloalkylaryl, most preferably (per) fluoroalkylaryl and halo heteroaryl, especially
  • ligands L fluorinated benzoic acids, e.g. 2
  • 2,3,4,5-tetrafluorobenzoic acid fluorinated or non-fluorinated phenylacetic acid, e.g. 2-fluoro-phenylacetic acid; 3-fluoro-phenylacetic acid; 4-fluoro-phenylacetic acid; 2, 3-difluoro-phenylacetic acid; 2,4-difluoro-phenylacetic acid; 2, 6-difluoro-phenylacetic acid; 3,4-difluoro-phenylacetic acid; 3,5-difluoro-phenylacetic acid; Pentafluoro-phenylacetic acid; 2-Chloro-6-fluoro-phenylacetic acid; 2-chloro-3,6-difluoro-phenylacetic acid; 3-chloro-2, 6-difluoro-phenylacetic acid; 3-chloro-4-fluoro-phenylacetic acid; 5-chloro-2-fluoro-phenylacetic acid; 2, 3, 4-trifluoro-phenylacetic acid
  • Trifluoro-phenylacetic acid 2,4,5-trifluoro-phenylacetic acid; 2,4,6-trifluoro-phenylacetic acid; 3, 4, 5-trifluoro-phenylacetic acid; 3-chloro-2-fluoro-phenylacetic acid; Fluoro-phenylacetic acid; 4-Chloro-2-fluoro-phenylacetic acid; 2-chloro-4-fluoro-phenylacetic acid; , -Difluoro-
  • Phenylacetic acid Ethyl 2, 2-difluoro-2-phenylacetates; and fluorinated or non-fluorinated acetic acid such as methyl trifluoroacetate; Allyl trifluoroacetate; Ethyl trifluoroacetate; Isopropyl trifluoroacetate; 2,2,2-trifluoroethyl trifluoroacetate; difluoroacetate;
  • Trifluoroacetic acid Methyl chlorodifluoroacetate; Ethyl bromodifluoroacetate; Chlorodifluoroacetic acid; Ethyl chlorofluoroacetate; Ethyl difluoroacetate; (3-chlorophenyl) difluoroacetic acid; (3, 5-difluorophenyl) -difluoroacetic acid; (4-butylphenyl) difluoroacetic acid; (4-tert-butylphenyl) difluoroacetic acid; (3, 4-dimethylphenyl) difluoroacetic acid; (3-chloro-4-fluorophenyl) difluoroacetic acid; (4-chlorophenyl) -difluoroacetic acid; 2-biphenyl-3 ', 5'-difluoroacetic acid; 3-biphenyl-3 ', 5'-difluoroacetic acid; 4-biphen
  • Halogens such as fluorine possess high levels of
  • Electronegativity a strong electron-withdrawing effect. This is important for the adaptation of the electronic properties of the complex.
  • the electron-withdrawing groups allow an enhancement of the Lewis acidity of the zinc complex and thus its action as a p-donor.
  • electron-withdrawing groups such as halogens and haloalkyls have a stabilizing effect on the zinc complex according to the invention.
  • An alternative preferred embodiment relates to an inventive organic electrical component with a Zinc complex, wherein the radical R 3 of the ligand L is selected from the group comprising:
  • Such zinc complexes are particularly stable and are therefore particularly well suited for use as a p-dopant.
  • R 3 is selected from the group comprising:
  • R 3 is selected from the group comprising:
  • R 3 is selected from the group consisting of halogenated, preferably perhalogenated and / or pseudohalogenated pteridines,
  • the metal complex (without the presence of matrix material) is Lewis acidic, ie it acts as an electron pair acceptor. This has become one Interaction with the matrix materials has been found to be particularly preferred.
  • the metal complex (without the presence of
  • Matrix material at least one open or partial
  • Ligands L of the zinc complex are each oxygen atoms.
  • the ligand L is a carboxylate ligand.
  • the inventors of the present invention have recognized that the zinc complexes of the carboxylates are stable and at the same time
  • carboxylate ligands represent particularly effective p-dopants.
  • the carboxylate ligands are also readily available and inexpensive because the respective associated carboxylic acids are widely available and inexpensive.
  • the metal complex may contain at least one ligand L selected from the group of unsubstituted, partially fluorinated or perfluorinated organic carboxylic acids.
  • Organic carboxylic acids can generally be selected from the groups of aliphatic, saturated monocarboxylic acids; aliphatic, unsaturated monocarboxylic acids; aliphatic, saturated dicarboxylic acids; aliphatic, saturated
  • tricarboxylic aliphatic, unsaturated dicarboxylic acids
  • aromatic carboxylic acids aromatic carboxylic acids
  • heterocyclic carboxylic acids aliphatic, unsaturated, cyclic monocarboxylic acids.
  • Particularly preferred partial or perfluorinated ligands L are selected from substituted or unsubstituted compounds of acetic acid, phenylacetic acid and / or
  • Benzoic acid and are exemplified above. Particularly preferred is non-fluorinated, partially fluorinated or perfluorinated acetic acid.
  • the zinc complex is a heteroleptic complex.
  • the Lewis acidities of the zinc atom (s) of the complex can be better controlled, whereby particularly effective p-dopants can be achieved.
  • An embodiment of the invention relates to a component according to the invention, wherein the zinc complex in addition to the ligand L comprises at least one different ligand, which is bonded via an adhesive atom to a zinc central atom of the zinc complex.
  • the adhesive atom may be, for example, oxygen.
  • the ligand is then an alcoholate.
  • the zinc complex in addition to the ligand L comprises at least one further ligand L c , which via a carbon atom to a zinc central atom is bound.
  • the zinc complex thus comprises at least one zinc-carbon bond.
  • the at least one further ligand L c may independently of one another be, for example, a substituted or unsubstituted, branched or linear, as well as a cyclic alkyl. It may also be a substituted or unsubstituted aryl or heteroaryl. For example, without being limited thereto, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, pentyl, hexyl, phenyl, benzyl, naphthyl , Cyclohexyl, adamantyl, or other typical ones
  • Ligands known organometallic complexes of zinc act as ligand L c .
  • L c may be a haloalkyl.
  • Such complexes have a higher Lewis acidity. This is especially the case when the halogen is fluorine.
  • Ligand L c comprise at least one fluorine atom.
  • the at least one ligand L c can be independent of one another
  • L c may be a fluorinated aryl or heteroaryl.
  • Fluorination were modified, i. one or more
  • Hydrogen atoms were replaced by fluorine atoms.
  • the inventors of the present invention have found that by using fluorinated ligands L c, the Lewis acidity of the zinc complex is not fluorinated
  • Ligands L c can be further increased, resulting in a further improvement of the dopant effect.
  • zinc is the coordination number 4, 5 and 6 may have.
  • zinc is often tetrahedral and octahedral coordinated.
  • the inventors have recognized that also the different coordination possibilities of the zinc are useful for the
  • zinc has the oxidation state II.
  • Oxidation stage II has a particularly high Lewis acidity and is therefore particularly suitable as a p-dopant.
  • Zinc complex not a mononuclear complex, but a
  • polynuclear metal complex for example, the
  • Metal complex 2, 3, 4, 5, 6 or more metal atoms include.
  • the zinc complex is a trinuclear or pentanuclear
  • Zinc is unlike others
  • Metal complexes with the ligand L are not limited to mononuclear, di-, tetra and hexanuclear complexes, but
  • polynuclear zinc complexes with an odd number of central atoms. For example, three or even five zinc atoms may be present in the complex. In the presence of three zinc atoms, they can be bridged in a nearly linear arrangement, for example by the ligand L.
  • a structure with a trinuclear zinc complex is shown for example in FIG. Figure 7 shows an example of a pentanuclear complex.
  • Zinc complex chemistry allows new flexibility in doping.
  • At least one ligand L is terminally attached to a zinc atom.
  • At least one ligand L it is possible for at least one ligand L to coordinate to zinc only with an adhesive atom, that is, with only one of the two groupings R 1 or R 2 .
  • the zinc complex comprises at least one ligand L which coordinates with both of the bonding atoms to the same zinc atom. This can be represented schematically as follows:
  • L is a carboxylate ligand, ie a ligand L in which both R 1 and R 2 are an oxygen atom, this means that both oxygen atoms are bonded to the zinc atom.
  • Organic electrical component according to the invention wherein the zinc complex is a polynuclear metal complex and at the same time at least one of the ligands L coordinately connects two metal atoms.
  • Zinc complex a polynuclear metal complex comprising
  • At least two ligands L wherein at least one of the ligands L coordinately connects two metal atoms, while at least one further ligand L is terminally attached to a metal center of the zinc complex.
  • the zinc complex comprises at least two zinc atoms.
  • the complex may have exactly two zinc atoms, but it may also have three, four, five or six zinc atoms or even more zinc atoms.
  • Organic electrical component according to the invention wherein the zinc complex in addition to zinc has at least one other metal other than zinc.
  • the ligand L can act bridging, which
  • M is a metal atom other than zinc, which forms another central atom of the zinc complex.
  • Another embodiment of the invention relates to a device according to the invention, as just described, wherein the metal other than zinc is selected from the group consisting of Mn, Mg, Ca, Sr, Ba, Cu.
  • the inventors of the present invention have recognized that complexes comprising both zinc and metals of said group form stable p-dopants which have sufficiently high Lewis acidity to act as effective dopants and good ones
  • Liquid phase to be processed In the vapor deposition both dopant and matrix material are common, preferably from different sources in a high vacuum
  • Matrix material dissolved in a solvent and by means of printing techniques, spin coating, knife coating, slot coating etc.
  • the finished layer is obtained by evaporation of the solvent. It can be through the set different ratios of metal complex to the matrix material any doping ratios.
  • P3HT Poly (3-hexylthiophene)
  • matrix materials which are referred to as "small molecules" can be processed by means of a solvent process and are known to those skilled in the art and include, for example, spiro-TAD (2, 2 ', 7, 7' tetrakis (N, -diphenylamino) -9,9'-spirobifluorene) and spiro-TTB (2, 2 ', 7, 7' tetrakis (N, '- di-p-methylphenylamino) -9,9'-spirobifluorene and others
  • the matrix material of the organic according to the invention comprises
  • NPB N, '-Bis (naphthalen-1-yl) -N,' -bis (phenyl) -benzidine
  • ⁇ -NPB N N '-bis (naphthalen-2-yl) -N,' -bis ( phenyl) benzidine
  • TPD N, '- bis (3-methylphenyl) -N,' - bis (phenyl) benzidine
  • spiro-TPD N, '- bis (3-methylphenyl) -N,' - bis (phenyl) benzidine
  • DMFL-NPB ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9,9-dimethyl-fluorene
  • DPFL-NPB ⁇ , ⁇ '-bis (naphthalen-1-yl) - ⁇ , ⁇ '-bis (phenyl) -9, 9-diphenyl-fluorene
  • PAPB N '-bis (phenanthrene-9-yl) -N,' -bis (phenyl) -benzidine, 2, 7-bis [N, N-bis (9,9-spiro-bifluoren-2-yl) - amino] -9,9-spirobifluorene,
  • PPDN pyrazino [2, 3-f] [1, 10] phenanthroline-2, 3-dicarbonitrile, MeO-TPD N, N, N ', N'-tetrakis (4-methoxyphenyl) benzidine.
  • the possible matrix materials are not limited to the materials mentioned.
  • Other materials such as the commercially available matrix materials from Merck, Novaled and Hodogaya with the product ⁇ designations HTM014, HTM081, HTM163, HTM222, NHT5, NHT49, NHT51, EL-301, EL-22T are particularly well suited. But also comparable commercially available materials can be used.
  • the degree of doping in moles of metal complex is based on mol
  • Matrix material from> 0.1% to> 50%. This has turned out to be
  • Electron blocking layers are used when co-evaporated together with an at least partially electron-conducting material.
  • Typical electron-conducting materials are:
  • OLEDs Light emitting diodes
  • Organic electronic components according to the present invention may, according to further embodiments, comprise a number of further layers, as commonly used in organic electronic components. The following are some ways to specify this, without the same being to be regarded as limiting.
  • the component according to the invention may have, for example, a hole blocking layer (HBL).
  • HBL hole blocking layer
  • the material for the hole-blocking layer may be selected from a group consisting of
  • organic electronic components according to the invention may have an electron injection layer ⁇ .
  • Electron injection layer may be selected from a group comprising NET-18, NET-218 (each product name of Novaled), ET093 (product name of Idemitsu Kosan), ETM020, ETM033, ETM034, ETM036 (each product name of Merck) and comparable commercial 2, 2 ', 2 "- (1,3,5-triethylenetriyl) tris (1-phenyl-1H-benzimidazole),
  • the electron injection layer may also comprise an n-type dopant.
  • n-type dopant may be one or more
  • NDN-1 Materials that are selected from a group, the NDN-1, NDN-26 (each product name of the company
  • organic electronic components according to the invention may have an emitter layer.
  • the emitter layer may comprise organic materials which are fluorescent and / or phosphorescent materials.
  • organic or organometallic compounds such as derivatives of polyfluorene, polythiophene and polyphenylene, for example 2- or 2, 5-substituted poly-p-phenylenvinylen) and / or metal complexes, for example iridium complexes, such as blue phosphorescent FIrPic
  • the organic electronic component has a substrate.
  • one of the electrodes is arranged on the substrate.
  • the substrate may for example be one or more materials in the form of a layer, a plate, a foil or a laminate
  • the substrate comprises or consists of glass.
  • the invention also relates to the use of a
  • Zinc complex as p-dopant for matrix materials of electronic components.
  • the zinc complex comprises at least one ligand L of the following structure: wherein R 1 and R 2 may independently be oxygen, sulfur, selenium, NH or NR 4 , wherein R 4 is selected from the group consisting of alkyl or aryl and may be linked to R 3 ; and
  • R 3 is selected from the group containing alkyl
  • alkenyl alkenyl
  • Haloketoaryl ketoheteroaryl, ketoalkyl, halo-ketoalkyl, ketoalkenyl, halo-ketoalkenyl, haloalkylaryl,
  • Haloalkylheteroaryl wherein, with suitable radicals, one or more non-adjacent CH 2 groups independently of one another by -O-, -S-, -NH-, -NR 000 -, -SiR ° R °° -, -CO-, -COO- .
  • -COR ° OR °°, -OCO-, -OCO-O-, -SO 2 -, -S-CO-, -CO-S-, -O-CS-, -CS-O-, -CY1 CY2 or -C ⁇ c- can be replaced in such a way that 0 and / or S atoms are not directly connected to each other, also optionally with aryl or heteroaryl preferably containing 1 to 30 C atoms are replaced
  • terminal CH 3 groups are understood as CH 2 ⁇ groups in the sense of CH 2 -H).
  • Embodiments described to be used according to the invention are subject in their size,
  • Fig. 1 shows schematically the structure of an organic compound
  • the light-emitting diode comprises or consists of the following layers: glass layer (1); Transparent
  • Conductive oxide i.e. a transparent conductive oxide
  • PEDOT PPS or PANI layer (2)
  • Hole injector layer (3) Hole transport layer (HTL) (4)
  • Emitter layer Emitter layer
  • HBL Hole Blocker Layer
  • ETL Electron Transport Layer
  • FIG. 2 shows schematically the structure of an organic solar cell with PIN structure (20), which converts light (21) into electricity.
  • the solar cell comprises or consists of a layer of indium tin oxide (22); a p-doped layer (23); an absorption layer (24); an n-doped layer (25) and a metal layer (26);
  • Fig. 3 shows schematically a possible cross section of an organic field effect transistor (30).
  • a gate electrode (32), a gate dielectric (33), a source and drain contact (34 + 35) and an organic semiconductor (36) are applied.
  • the hatched areas show the places where a contact doping is helpful.
  • Fig. 4 shows a mononuclear zinc complex described by Zelenak et al. in "Preparation, characterization and crystal structure of two zinc (11) benzoate complexes with pyridine-based ligands nicotinamide and methyl-3-pyridylcarbamate” Inorganica Chimica Acta 357 (2004) 2049-2059.
  • Fig. 5 shows a dinuclear zinc complex
  • Fig. 7 shows a pentanuclear zinc complex comprising ethyl units described by Katherine L. Orchard et al. in "Pentanuclear Complexes for a Series of Alkylzinc
  • HTM014, Merck KGaA the current density versus the voltage for the undoped matrix material (HTM014, Merck KGaA) as well as for the Zn3-doped matrix material.
  • the co-evaporation of the zinc complex and the matrix material takes place in a temperature range of 169-182 ° C.
  • the content of HTM014 on the obtained layer is 85
  • Example II Sublimation observed than in Example I. It is therefore not the same compound. 10 for example III, Zn (3,5), the current density versus the voltage for the undoped matrix material (HTM014) as well as for the Zn (3, 5-tfmb) doped matrix material.
  • HTM014 the current density versus the voltage for the undoped matrix material (HTM014) as well as for the matrix material doped with Zn (tfa).
  • the proportion of HTM014 on the doped layer is 85% by volume. A very good doping effect is observed.
  • Fig. 12A for Example IV Zn (tfa), the current density against the voltage.
  • the commercially available matrix material ⁇ NHT49 Novaled with Zn (TFA) was doped.
  • the current-voltage curve demonstrates an excellent p-type dopant effect of the zinc complexes according to the invention.
  • the current-voltage curve also shows an excellent p-dopant effect here.
  • FIGS. 12A and 12B illustrate the broad substitutability and good p-doping effect of zinc complexes according to the invention for various matrix materials.
  • different p-dopant concentrations were tested in both cases. Measurements between 3 and 15 vol.% Of the p-dopant on the entire p-doped layer are in the two counts shown.
  • the zinc complexes of the invention can be used in a wide range of different concentrations in the doped layer. Particularly good values are achieved between 1 and 25% by volume of the zinc complex, more preferably in the range from 3 to 15% by volume. The latter area is shown in the figures, respectively. The best values are in each case between 5 and 10% by volume of the zinc complex, based on the p-doped organic region, or the p-doped one
  • Fig. 13A shows the schematic structure of an embodiment of an organic according to the invention
  • the OLED of Fig. 13A has an anode
  • ITO Indium tin oxide
  • the anode is followed by the hole injection layer, which has the zinc complex to be tested as p-dopant.
  • the hole injection layer has a layer thickness of 70 nm.
  • Fig. 13B shows the experimental data obtained by means of
  • Dopant NDP9 used by Novaled All further measurements were carried out with zinc trifluoroacetate complexes, Zn (tfa), as p-dopants with volume concentrations between 3 and 15% by volume, based on the doped layer.
  • the matrix material used in each case was the commercially available hole-conducting matrix material NHT49 from Novaled.
  • the measurements were carried out in each case at the same luminance, resulting in a comparable current density and operating voltage for the components doped with the Zn dopant as for the components doped with NDP9.
  • the efficiency measures luminous efficacy (Peff), current efficiency (Ieff) and external
  • Zinc complexes allow improved light yields, current yields and external quantum yields. This is due, at least in part, to the very low absorption of layers doped with the zinc complexes. Thus, losses due to absorption by the dopant in the component are reduced, which is especially true for organic
  • Fig. 14 shows the absorption spectrum of one with a
  • FIG. 14A compares the absorption spectrum of quartz showing excellent light transmittance with FIG. 14A
  • the doped layer shows surprisingly low values for the absorbance, which represents a measure of the absorption.
  • FIG. 14B shows the detail enlarged between 450 and 800 nm. Here it can be seen that in the visible range the absorbance of the doped
  • organic light-emitting diodes or organic solar cells are suitable.
  • the zinc complexes of the organic electrical component according to the invention are, for example, by reaction of di-alkyl or di-aryl zinc with the corresponding
  • L c in this case corresponds to the ligands L described above and c is an alkyl or aryl.
  • L c * is also an alkyl or aryl independently of L c where L c and L c * may be the same or different.
  • R 3 corresponds to the rest of the R 3 of the ligand L of the given exemplary manufacturing method
  • Example I relates to a zinc pentafluorobenzoate complex, Zn (pfb), hereinafter abbreviated to Zn3, obtained in the synthetic route described below:
  • a matrix layer with p-dopant, as measured in FIG. 8 for Example I, is obtained by coevaporation of the matrix material and of the zinc complex.
  • the hole transport layer is thus obtained directly from the gas phase by reaction of the components on the substrate.
  • the layers to be measured are generated as follows
  • ITO prestructured glass substrates were heated for 10 min.
  • Evaporator was transferred to an argon glove box in which the oxygen and water concentration is less than 2ppm. All evaporations were carried out at a vacuum of less than 2 x 10 "6 mbar base pressure is performed (during the evaporation the pressure then rises).
  • the total evaporation rate was about 1 A / s, with the evaporation rate of the dopant over the
  • Evaporation rate of the matrix material was adjusted. After the shutters were closed, it was at 40 ° C
  • the electrode consisted of a 150 nm thick layer
  • Example II to IV application Example II to IV application.
  • FIGS. 9 to 11 relate to doped and undoped HTM-014 (matrix material, Merck KGaA). In each case, 200 nm thick layers of HTM-014 (Merck
  • Example II also relates to the preparation of a second zinc pentafluorobenzoate complex Zn (pfb) different from Example I, abbreviated to Zn8. 30, 59 mmol
  • Pentafluorobenzoic acid are cooled in 60 ml of diethyl ether and at 0 ° C. 15.29 mmol Diethylzinkates (1.0 M in hexane) is diluted with 20 ml of diethyl ether, also cooled and carefully added dropwise under inert gas to the pentafluorobenzoic acid solution. While stirring, the solution is brought up
  • Example II The substance obtained by the synthesis procedure presented in Example II surprisingly has a significantly higher sublimation temperature than the compound as obtained by the process presented in Example I, so that it can be assumed that this is a substance obtained from Example I.
  • Example III relates to the preparation of a zinc complex with 3, 5-bis (trifluoromethyl) benzoate ligands,
  • Example IV relates to the preparation of a zinc complex with trifluoroacetate ligands, abbreviated to Zn (tfa).
  • Zn (tfa) 48.16 mmol of trifluoroacetic acid are mixed with 60 mmol of benzene and cooled to 10 ° C.
  • diethylzinc solution 15% in toluene
  • One third of the solvent is stripped off, the white product is filtered off with suction through a P4 frit and three times with cyclohexane

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Abstract

La présente invention concerne un composant électronique organique comprenant une matrice. La matrice contient comme dopant P un complexe de zinc qui contient à son tour au moins un ligand L ayant la formule suivante : formule (I) où R1 et R2 peuvent être, indépendamment l'un de l'autre, de l'oxygène, du soufre, du sélénium, du NH ou du NR4, où R4 est choisi dans le groupe contenant un alkyle ou un aryle et peut être lié à R3 ; et R3 est choisi dans le groupe constitué par : alkyle, alkyle à longue chaîne, cycloalkyle, haloalkyle, aryle, arylène, haloaryle, hétéroaryle, hétéroarylène, hétérocycloalcylène, hétérocycloalkyle, hétéroaryle halogéné, alcényle, alcényle halogéné, alcinyle, alcinyle halogéné, cétoaryle, cétoaryle halogéné, cétohétéroaryle, cétoalkyle, cétoalkyle halogéné, cétoalcényle, cétoalcényle halogéné, alkylaryle halogéné, alkylhétéroaryle halogéné. En présence de résidus appropriés, un ou plusieurs groupes CH2 non voisins peuvent être remplacés indépendamment les uns des autres par -O-, -S-, -NH-, -NR°°°-, -SiR°R°°-, -CO-, -COO-, -COR°OR°°-, -OCO-, -OCO-O-, -SO2-, -S-CO-, -CO-S-, -O-CS-, -CS-O-, -CY1=CY2 ou -C≡C-, et ce telle sorte que les atomes d'O et/ou de S ne sont pas liés directement ensemble, et sont aussi remplacés facultativement par un aryle ou un hétéroaryle contenant de préférence 1 à 30 atomes de C (les groupes CH3 terminaux sont interprétés comme des groupes CH2 dans le sens de CH2 -H).
EP15771577.2A 2014-09-30 2015-09-28 Composant électronique organique, utilisation d'un complexe de zinc comme dopant p pour matériau de matrice électronique organique Withdrawn EP3201962A1 (fr)

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DE102014114224.1A DE102014114224A1 (de) 2014-09-30 2014-09-30 Organisches elektronisches Bauteil, Verwendung eines Zinkkomplexes als p-Dotierungsmittel für organische elektronische Matrixmaterialien
PCT/EP2015/072283 WO2016050705A1 (fr) 2014-09-30 2015-09-28 Composant électronique organique, utilisation d'un complexe de zinc comme dopant p pour matériau de matrice électronique organique

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DE102015121844A1 (de) 2015-12-15 2017-06-22 Osram Oled Gmbh Organisches elektronisches Bauelement und Verwendung eines fluorierten Sulfonimid-Metallsalzes
DE102016101710A1 (de) 2016-02-01 2017-08-03 Osram Oled Gmbh OLED und Verfahren zur Herstellung einer OLED
KR102078435B1 (ko) * 2016-07-14 2020-02-17 주식회사 엘지화학 유기 전계 발광 소자 및 이의 제조 방법
DE102017111425A1 (de) 2017-05-24 2018-11-29 Osram Oled Gmbh Organisches elektronisches Bauelement und Verfahren zur Herstellung eines organischen elektronischen Bauelements

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JP2017538283A (ja) 2017-12-21
JP6552612B2 (ja) 2019-07-31
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US20170301872A1 (en) 2017-10-19

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