WO2017092473A1 - Composé avec hétérocycles d'indole reliés et utilisation de celui-ci dans un dispositif électronique organique - Google Patents

Composé avec hétérocycles d'indole reliés et utilisation de celui-ci dans un dispositif électronique organique Download PDF

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WO2017092473A1
WO2017092473A1 PCT/CN2016/098518 CN2016098518W WO2017092473A1 WO 2017092473 A1 WO2017092473 A1 WO 2017092473A1 CN 2016098518 W CN2016098518 W CN 2016098518W WO 2017092473 A1 WO2017092473 A1 WO 2017092473A1
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organic
ring
aromatic
carbon atoms
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潘君友
何锐锋
杨伟
闫晓林
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广州华睿光电材料有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container

Definitions

  • This invention relates to the field of organic optoelectronic materials, and more particularly to the use of hydrazine heterocyclic compounds, mixtures and compositions thereof, and their use in organic electronic devices, particularly in organic electroluminescent devices.
  • the invention also relates to an electronic device comprising the organic compound and to the use thereof.
  • Organic semiconductor materials have the characteristics of structural diversity, relatively low manufacturing cost, and superior photoelectric performance, and have great application potential in optoelectronic devices such as light-emitting diodes (OLEDs) (for example, flat panel displays and illumination).
  • OLEDs light-emitting diodes
  • various fluorescent and phosphorescent material systems have been widely developed.
  • the organic light-emitting diode based on fluorescent material has high reliability, but its maximum internal quantum efficiency is only 25% under electric field excitation, which is mainly the spin ratio of excited state (single-excited state and triplet excited state). The ratio is 1:3).
  • organic light-emitting diodes based on phosphorescent materials have achieved near-100% internal quantum efficiency.
  • the stability of phosphorescent OLEDs needs to be improved.
  • the factor affecting the stability of the phosphorescent OLED is the key to the host material in addition to the illuminator itself.
  • Helium heterocyclic materials have become the focus of academic and industrial circles due to their high carrier transport capability, photoelectric response properties and thermal stability, and are widely used in organic light-emitting diodes.
  • most of the rhodium-terminated materials currently developed still have the disadvantage of poor chemical/environmental stability, mainly due to the conjugate of lone pairs of electrons on the nitrogen atom in the structure of the material to the benzene ring.
  • the CH bond with high electron cloud density and high reactivity is formed, resulting in poor chemical/environmental stability and relatively short device life of such compounds.
  • One method is to replace the electron-deficient unit on the nitrogen of the heterocyclic ring, so that the electron cloud shifts to the electron-deficient unit, and reduces the degree of conjugation of the lone pair electrons on the nitrogen on the hetero ring.
  • the electron cloud density and reactivity of the CH bond on the aromatic ring are lowered [see Adv. Funct. Mater., 2014, 24, 3551-3561].
  • this method still does not minimize the reactivity of the C-H bond on the aromatic heterocycle.
  • a novel organic compound particularly a hydrazine heterocyclic compound, comprising a mixture and composition of the compound, and its use in an organic electronic device, aiming to solve the existing The problem of stability and low device lifetime of indole carbazole materials and related organic electronic devices.
  • X is an aromatic ring having 6 to 40 ring carbon atoms or an aromatic heterocyclic ring having 3 to 40 ring carbon atoms;
  • Y is a five- or six-membered ring and can be represented as one of the groups having the following structure:
  • M is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 3 to 60 ring carbon atoms;
  • R 1 and R 2 are one or more substituents on the benzene ring, and R 1 and R 2 each independently represent H, D, alkyl, aralkyl, alkenyl, alkynyl, nitrile, amine, One of a nitro group, an acyl group, an alkoxy group, a carbonyl group, a sulfone group, a cycloalkyl group or a hydroxyl group;
  • Ar represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 ring carbon atoms or an aromatic heterocyclic group having 3 to 60 ring carbon atoms;
  • n is an integer of 1 to 10.
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 each independently represent CR 1 or N;
  • X of the formula (1) may be selected from one of the following groups, and it may be further substituted:
  • M may preferably be one of the following groups, and it may be further substituted:
  • the compound may be represented by one of the following chemical formulae (2)-(10):
  • R 1 , R 2 , Ar, M, Z 1 , Z 2 , Z 3 and n have the same meanings as defined above.
  • the above-mentioned compounds have a glass transition temperature Tg ⁇ 100 ° C, preferably ⁇ 120 ° C, more preferably ⁇ 140 ° C, particularly preferably ⁇ 160 ° C, most preferably ⁇ 180 ° C.
  • a polymer comprising at least one repeating unit represented by the formula (1).
  • a mixture comprising a compound or polymer as described above, and at least one organic functional material.
  • the organic functional material may be selected from the group consisting of a hole injecting material (HIM), a hole transporting material (HTM), an electron injecting material (EIM), an electron transporting material (ETM), a hole blocking material (HBM), and an electron blocking material ( Any one or combination of EBM), Emitter, Host, and organic dye.
  • a composition comprising a compound or polymer as described above, and at least one organic solvent.
  • Polymer An electronic device characterized by comprising at least one compound or polymer as described above, or a mixture thereof.
  • the above organic electronic device may be selected from the group consisting of an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic sensor, and an organic plasmon. Any one or combination of emitting diodes (Organic Plasmon Emitting Diodes).
  • the above organic light emitting diode is an electroluminescent device comprising an anode, a cathode, and a light emitting layer between the anode and the cathode, wherein the light emitting layer comprises at least one of the above compounds or polymers And a luminescent material, which may be selected from the group consisting of a fluorescent illuminant, a phosphorescent illuminant, a TADF material or a luminescent quantum dot.
  • a luminescent material which may be selected from the group consisting of a fluorescent illuminant, a phosphorescent illuminant, a TADF material or a luminescent quantum dot.
  • the compound according to the present invention is used in an OLED, particularly as a host material, to extend the life of the OLED.
  • the possible reasons are as follows, but are not limited thereto: replacing the hydrogen atom in the CH bond with an aromatic group is advantageous for lowering the reaction activation energy at the position, thereby improving the stability of the aromatic group at the position, which is to improve the flail.
  • the chemical/environmental stability of rhodium heterocycles and optoelectronic devices offers the potential.
  • the present invention provides a novel organic compound, particularly a hydrazine heterocyclic compound, a mixture and composition of the compound, and its use in an organic electronic device, in order to make the object, technical solution and effect of the present invention clearer It is clear that the present invention will be further described in detail below. It is understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
  • composition and the printing ink, or ink have the same meaning and are interchangeable.
  • the host material In the present invention, the host material, the host material Host or the Matrix material have the same meaning, and they are interchangeable.
  • the metal organic complex, the metal organic complex, and the organometallic complex have the same meaning and are interchangeable.
  • the present invention provides a compound having the formula (1):
  • X is an aromatic ring having 6 to 40 ring carbon atoms or an aromatic heterocyclic ring having 3 to 40 ring carbon atoms;
  • Y is a five- or six-membered ring and can be represented as one of the groups having the following structure:
  • M is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 3 to 60 ring carbon atoms;
  • R 1 and R 2 are one or more substituents on the benzene ring, and R 1 and R 2 each independently represent H, D, alkyl, aralkyl, alkenyl, alkynyl, nitrile or amine groups.
  • R 1 and R 2 each independently represent H, D, alkyl, aralkyl, alkenyl, alkynyl, nitrile or amine groups.
  • Ar represents an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 ring carbon atoms or an aromatic heterocyclic group having 3 to 60 ring carbon atoms;
  • n is an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 4, particularly preferably an integer of 1 to 3, and most preferably 2 or 3.
  • An aromatic ring system or aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including a monocyclic group and a polycyclic ring system.
  • a heteroaromatic or heteroaromatic group refers to a hydrocarbyl group (containing heteroatoms) comprising at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems.
  • the heteroatoms are preferably selected from the group consisting of Si, N, P, O, S and/or Ge, particularly preferably selected from the group consisting of Si, N, P, O and/or S.
  • At least one of the rings of the ring system is aromatic or heteroaromatic.
  • aromatic or heteroaromatic ring systems include not only aromatic or heteroaromatic systems, but also multiple aryl or heteroaryl groups which may also be interrupted by shorter non-aromatic units ( ⁇ 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms).
  • systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether and the like are also considered to be aromatic ring systems.
  • examples of the aromatic group are: benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, anthracene, benzofluorene, triphenylene, anthracene, anthracene, and derivatives thereof.
  • heteroaromatic groups are: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, anthracene, anthracene Oxazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrol, furanfuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, Pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-diazine, quinoxaline, phenanthridine, carbaidine, quinazoline, quinazolinone, and derivatives thereof.
  • the compound of the formula (1), wherein X is an aromatic ring having 6 to 30 carbon atoms or an aromatic heterocyclic ring having 3 to 30 carbon atoms, preferably having 6 to 30 carbon atoms.
  • the aromatic ring of 20 or the aromatic heterocyclic ring having 3 to 20 carbon atoms is most preferably an aromatic ring having 6 to 15 carbon atoms or an aromatic heterocyclic ring having 3 to 15 carbon atoms.
  • the X may be selected from one of the following groups:
  • X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 each independently represent CR 1 or N;
  • X can be selected from one of the following groups, and it can be further substituted:
  • M represented by the formula (1) is an aromatic group having 6 to 30 carbon atoms or an aromatic hetero group having 3 to 30 carbon atoms; more preferably In the examples, M is an aromatic group having 6 to 25 carbon atoms or an aromatic hetero group having 3 to 25 carbon atoms; in a most preferred embodiment, M is 6 to 20 carbon atoms.
  • the number of carbon atoms referred to herein means the number of ring carbon atoms on the aromatic ring or the heteroaryl ring.
  • M can be selected from one of the following groups, and it can be further substituted:
  • the compound according to the invention may be represented by any one of the following formulas (2) to (10):
  • R 1 , R 2 , Ar, M, Z 1 , Z 2 , Z 3 and n are the same as above.
  • Ar in the formula (1) is represented by an aromatic group having 6 to 18 ring carbon atoms or an aromatic heterocyclic group having 3 to 18 ring carbon atoms; In a preferred embodiment, Ar is represented by an aromatic group having 6 to 15 ring carbon atoms or an aromatic heterocyclic group having 3 to 15 ring carbon atoms.
  • the compound according to the invention may be selected from one of the following structural formulae:
  • R 1 , R 2 , Ar, M, X, Y and n are the same as above.
  • the compound according to the present invention can be used as a functional material in an electronic device.
  • Organic functional materials can be classified into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injecting materials (EIM), electron blocking materials (EBM), and hole blocking materials (HBM). , Emitter, Host and Organic Dyes.
  • the compound according to the invention may be used as a host material, or an electron transport material, or a hole transport material.
  • the compounds according to the invention are useful as phosphorescent host materials.
  • the compounds according to the invention have a T 1 ⁇ 2.2 eV, preferably ⁇ 2.4 eV, more preferably ⁇ 2.6 eV, particularly preferably ⁇ 2.65 eV, most preferably ⁇ 2.7 eV.
  • the triplet level T 1 of an organic compound depends on the substructure of the compound having the largest conjugated system. Generally, T 1 decreases as the conjugated system increases. In certain preferred embodiments, in the chemical formula (1), the substructure shown by the formula (1a) has the largest conjugated system.
  • the formula (1a), in the case of excluding a substituent, has no more than 36 ring atoms, preferably no more than 30, more preferably no more than 26, and most preferably no more than 20.
  • the formula (1a) has T 1 ⁇ 2.3 eV, preferably ⁇ 2.5 eV, more preferably ⁇ 2.7 eV, particularly preferably ⁇ 2.75 eV, and most preferably ⁇ 2.8 eV.
  • the compounds according to the invention have a glass transition temperature Tg ⁇ 100 ° C, in a preferred embodiment, Tg ⁇ 120 ° C, in a more preferred embodiment, Tg ⁇ 140 ° C, in a more preferred In the examples, Tg ⁇ 160 ° C, and in a most preferred embodiment, Tg ⁇ 180 ° C.
  • Non-limiting examples of compounds according to the invention are:
  • the organic compound according to the invention is a small molecule material.
  • small molecule refers to a molecule that is not a polymer, oligomer, dendrimer, or blend. In particular, there are no repeating structures in small molecules.
  • the molecular weight of the small molecule is ⁇ 3000 g/mol, preferably ⁇ 2000 g/mol, most preferably ⁇ 1500 g/mol.
  • the polymer ie, the polymer, includes a homopolymer, a copolymer, and a block copolymer. Also in the present invention, the polymer also includes a dendrimer.
  • a dendrimer For the synthesis and application of the tree, see [Dendrimers and Dendrons, Wiley-VCH Verlag GmbH & Co. KGaA, 2002, Ed. George R. Newkome, Charles. N. Moorefield, Fritz Vogtle.].
  • a conjugated polymer is a polymer whose main chain is mainly composed of sp2 hybrid orbitals of C atoms, and typical examples include, but are not limited to, polyacetylene and poly(phenylene vinylene). ], the C atom in its main chain can also be substituted by other non-C atoms, and when the sp2 hybridization in the main chain is interrupted by some natural defects, it is still considered to be a conjugated polymer. Further, in the present invention, the conjugated polymer also includes an arylamine, an arylphosphine, and other heterocyclic aromatic hydrocarbons, an organic metal complex, and the like in the main chain.
  • the present invention also relates to a polymer comprising a repeating unit comprising a structural unit represented by the formula (1).
  • the polymer is a non-conjugated polymer wherein the structural unit of formula (1) is on the side chain.
  • the polymer is a conjugated polymer.
  • the invention further relates to a mixture comprising at least one organic compound or polymer according to the invention, and at least one organic functional material.
  • the organic functional material comprises a hole (also called a hole) injection or transport material (HIM/HTM), a hole blocking material (HBM), an electron injecting or transporting material (EIM/ETM), an electron blocking material (EBM), Organic matrix material (Host), single weight Light emitters (fluorescent emitters), thermally activated delayed fluorescent materials (TADF), triplet emitters (phosphorescent emitters), especially luminescent metal organic complexes, and organic dyes.
  • HIM/HTM hole injection or transport material
  • HBM hole blocking material
  • EIM/ETM electron injecting or transporting material
  • EBM electron blocking material
  • Organic matrix material Hex
  • single weight Light emitters fluorescent emitters
  • TADF thermally activated delayed fluorescent materials
  • phosphorescent emitters especially luminescent metal organic complexes, and organic dyes.
  • Various organic functional materials are described in detail in, for example, WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of each of which
  • the organic functional material can be a small molecule or a polymeric material.
  • the compound is present in the mixture according to the invention in an amount of from 50 to 99.9% by weight, preferably from 60 to 97% by weight, more preferably from 60 to 95% by weight, most preferably from 70 to 90% by weight.
  • the mixture according to the invention comprises a compound or polymer according to the invention and a phosphorescent luminescent material.
  • the mixture according to the invention comprises a compound or polymer according to the invention and a thermally activated delayed fluorescent luminescent material (TADF).
  • TADF thermally activated delayed fluorescent luminescent material
  • the mixture according to the invention comprises a compound or polymer according to the invention, a phosphorescent luminescent material and a TADF material.
  • the mixture according to the invention comprises a compound or polymer according to the invention and a fluorescent luminescent material.
  • fluorescent luminescent materials or singlet illuminants (fluorescent luminescent materials), phosphorescent luminescent materials or triplet illuminants and TADF materials are given below.
  • Singlet emitters tend to have longer conjugated pi-electron systems.
  • singlet illuminants for example, styrylamine and its derivatives (as described in JP2913116B and WO2001021729A1), and indenoindene and its derivatives (WO2008/006449 and WO2007/140847) description).
  • the singlet emitter can be selected from the group consisting of monostyrylamine, dibasic styrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether, and arylamine.
  • Monostyrylamine refers to a compound comprising an unsubstituted or substituted styryl group and at least one amine, most preferably an aromatic amine.
  • Dibasic styrylamine refers to a compound comprising two unsubstituted or substituted styryl groups and at least one amine, most preferably an aromatic amine.
  • Ternary styrylamine refers to a compound comprising three unsubstituted or substituted styryl groups and at least one amine, most preferably an aromatic amine.
  • Tetrastyrylamine refers to a compound comprising four unsubstituted or substituted styryl groups and at least one amine, most preferably an aromatic amine.
  • the preferred styrene is stilbene, which may be further substituted.
  • the definitions of the corresponding phosphines and ethers are similar to the definition of amines.
  • An arylamine or an aromatic amine refers to a compound comprising three unsubstituted or substituted aromatic ring or heterocyclic systems directly bonded to nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably selected from the group consisting of fused ring systems, and most preferably has at least 14 aromatic ring atoms.
  • Preferred examples thereof are aromatic decylamine, aromatic quinone diamine, aromatic decylamine, aromatic quinone diamine, aromatic thiamine and aromatic quinone diamine.
  • Aromatic decylamine refers to a compound in which a diaryl arylamine group is attached directly to the oxime, preferably at the position of 9.
  • Aromatic quinone diamine refers to a compound in which two diaryl arylamine groups are attached directly to the oxime, most preferably at the 9,10 position.
  • Aromatic amine, aromatic The definition of quinone diamine, aromatic thiamine, is similar to the definition of aromatic quinone diamine, wherein the diaryl aryl group is preferably attached to the 1 or 1,6 position of hydrazine.
  • Examples of singlet emitters based on vinylamines and arylamines are also preferred examples and can be found in the following patent documents: WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007 /115610, US Pat. No. 7,250,532, B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US Pat. No. 6,215, 531, B1, US 2006/210830 A, EP 1 957 606 A1 and US 2008/0113101 A1, the entire contents of each of which are hereby incorporated by reference. This article serves as a reference.
  • a non-limiting example of a singlet emitter based on stilbene and its derivatives is US 5,121,029.
  • Further preferred singlet emitters may be selected from the group consisting of indeno-amine and indeno-diamine, benzindole-amine and benzoindole-diamine, dibenzoindenoquinone-amine And dibenzoindenoindole-diamine.
  • polycyclic aromatic hydrocarbon compounds in particular derivatives of the following compounds: for example, 9,10-bis(2-naphthoquinone), naphthalene, tetraphenyl, xanthene, phenanthrene , ⁇ (such as 2,5,8,11-tetra-t-butyl fluorene), anthracene, phenylene such as (4,4'-bis(9-ethyl-3-carbazolevinyl)-1 , 1 '-biphenyl), indenyl hydrazine, decacycloolefin, hexacene benzene, anthracene, spirobifluorene, aryl hydrazine (such as US20060222886), arylene vinyl (such as US5121029, US5130603), cyclopentane Alkene such as tetraphenylcyclopentadiene, rub
  • Non-limiting examples of materials for some singlet emitters can be found in the following patent documents: US 20070252517 A1, US 4769292, US 6020078, US 2007/0252517 A1, US 2007/0252517 A1. The entire contents of the above-identified patent documents are hereby incorporated by reference.
  • Non-limiting examples of some suitable singlet emitters are listed in the table below:
  • TDF Thermally activated delayed fluorescent luminescent material
  • the thermally activated delayed fluorescent luminescent material is a third generation organic luminescent material developed after organic fluorescent materials and organic phosphorescent materials.
  • Such materials generally have a small singlet-triplet energy level difference ( ⁇ E st ), and triplet excitons can be converted into singlet exciton luminescence by inter-system crossing. This can make full use of the singlet excitons and triplet excitons formed under electrical excitation.
  • the quantum efficiency in the device can reach 100%.
  • the TADF material needs to have a small singlet-triplet energy level difference, typically ⁇ E st ⁇ 0.3 eV, preferably ⁇ E st ⁇ 0.2 eV, more preferably ⁇ E st ⁇ 0.1 eV, most preferably ⁇ E st ⁇ 0.05 eV.
  • TADF has better fluorescence quantum efficiency.
  • Non-limiting examples of TADF luminescent materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1) , WO2013154064 (A1), Adachi, et.al. Adv. Mater., 21, 2009, 4802, Adachi, et. al. Appl. Phys. Lett., 98, 2011, 083302, Adachi, et.al. Appl. Phys. Lett., 101, 2012, 093306, Adachi, et. al. Chem.
  • TADF luminescent materials are listed in the table below:
  • Triplet emitters are also known as phosphorescent emitters.
  • the triplet emitter is a metal complex of the formula M(L) n wherein M is a metal atom and each occurrence of L may be the same or a different organic ligand. Attached to the metal atom M by one or more positional bonding or coordination, n is an integer greater than 1, more preferably 1, 2, 3, 4, 5 or 6.
  • these metal complexes are coupled to the polymer by one or more positions, most preferably to the polymer via an organic ligand.
  • the metal atom M may be selected from transition metal elements or lanthanides or actinides, preferably Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy Re, Cu or Ag, particularly preferably Os, Ir, Ru, Rh, Re, Pd or Pt.
  • the triplet emitter may comprise a chelating ligand, ie a ligand, coordinated to the metal by at least two bonding sites, with particular preference being given to the triplet emitter comprising two or three identical or different Double or multidentate ligand.
  • Chelating ligands are beneficial for increasing the stability of metal complexes.
  • Non-limiting examples of organic ligands may be selected from the group consisting of phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2(2-thienyl)pyridine derivatives, 2(1-naphthyl)pyridine derivatives, Or a 2 phenylquinoline derivative. All of these organic ligands may be substituted, for example by fluorine or trifluoromethyl.
  • the ancillary ligand may preferably be selected from the group consisting of acetone acetate or picric acid.
  • the metal complex that can be used as the triplet emitter can have the following form:
  • M is a metal selected from the group consisting of transition metal elements or lanthanides or actinides;
  • Each occurrence of Ar 1 may be the same or different cyclic group, which contains at least one donor atom, that is, an atom having a lone pair of electrons, such as nitrogen or phosphorus, through which a cyclic group is coordinated to the metal;
  • Each occurrence of Ar 2 may be the same or different cyclic group, which contains at least one C atom through which a cyclic group is bonded to the metal;
  • Ar 1 and Ar 2 are linked by a covalent bond, respectively Carrying one or more substituent groups, which may also be linked together by a substituent group;
  • each occurrence of L may be the same or different ancillary ligands, preferably a bidentate chelate ligand, most preferably a monoanion bidentate a chelating ligand;
  • m is 1, 2 or 3, preferably 2 or 3, particularly preferably 3;
  • n is 0, 1, or 2, preferably 0 or 1, particularly preferably 0;
  • Non-limiting examples of materials for some triplet emitters and their applications can be found in the following patent documents and literature: WO 200070655, WO 200141512, WO 200202714, WO 200215645, EP 1191613, EP 1191612, EP1191614, WO 2005033244, WO 2005019373, US 2005/0258742, WO 2009146770, WO2010015307, WO 2010031485, WO 2010054731, WO 2010054728, WO 2010086089, WO2010099852, WO 2010102709, US 20070087219 A1, US 20090061681 A1, US 20010053462 A1, Baldo, Thompson et al.
  • triplet emitters Some non-limiting examples of suitable triplet emitters are listed in the table below:
  • Another aspect of the invention is to provide a material solution for printing OLEDs.
  • the compounds according to the invention have a molecular weight of ⁇ 700 mol/kg, preferably ⁇ 900 mol/kg, more preferably ⁇ 900 mol/kg, particularly preferably ⁇ 1000 mol/kg, most preferably ⁇ 1100 mol/kg.
  • the compound according to the invention has a solubility in toluene of > 10 mg/ml, preferably > 15 mg/ml, most preferably > 20 mg/ml at 25 °C.
  • a further aspect of the invention further relates to a composition or ink comprising a compound or polymer or mixture according to the invention, and at least one organic solvent.
  • Another aspect of the invention further provides a preparation comprising from a solution A method of filming a compound or polymer according to the invention.
  • the viscosity and surface tension of the ink are important parameters when used in the printing process. Suitable surface tension parameters for the ink are suitable for the particular substrate and the particular printing method.
  • the surface tension of the ink according to the invention is in the range of from about 19 dyne/cm to 50 dyne/cm at the working temperature or at 25 ° C; preferably in the range of 22 dyne/cm to 35 dyne/cm; most preferably 25dyne/cm to 33dyne/cm range.
  • the viscosity of the ink according to the invention is in the range of from about 1 cps to 100 cps at the working temperature or at 25 ° C; more preferably in the range of from 1 cps to 50 cps; more preferably in the range of from 1.5 cps to 20 cps; Most preferably it is in the range of 4.0 cps to 20 cps.
  • the composition so formulated will be suitable for ink jet printing.
  • the viscosity can be adjusted by different methods, such as selecting the concentration of the functional material in the ink by a suitable solvent.
  • the ink containing the compound or polymer according to the present invention can facilitate the adjustment of the concentration of the printing ink to an appropriate range in accordance with the printing method used.
  • the composition according to the invention comprises a functional material in a weight ratio ranging from 0.3% to 30% by weight, preferably from 0.5% to 20% by weight, more preferably from 0.5% to 15% by weight, particularly preferably from 0.5% to 10% by weight, Most preferably, it is in the range of 1% to 5% by weight.
  • the at least one organic solvent is selected from the group consisting of aromatic or heteroaromatic based solvents, particularly aliphatic chain/ring substituted aromatic solvents, aromatic ketone solvents, or Aromatic ether solvent.
  • solvents suitable for the present invention are, but are not limited to, aromatic or heteroaromatic based solvents: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethyl Naphthalene, 3-isopropylbiphenyl, p-methyl cumene, dipentylbenzene, triphenylbenzene, pentyltoluene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethyl Benzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, two Hexylbenzene, di
  • the at least one solvent may be selected from the group consisting of aliphatic ketones, for example, 2-fluorenone, 3-fluorenone, 5-fluorenone, 2-nonanone, 2,5-hexyl Diketone, 2,6,8-trimethyl-4-indanone, phorone, di-n-pentyl ketone, etc.; or an aliphatic ether, for example, pentyl ether, hexyl ether, dioctyl ether, ethylene glycol Dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, three Propylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
  • aliphatic ketones for example, 2-fluorenone, 3-fluoren
  • the printing ink further comprises another organic solvent.
  • another organic solvent include, but are not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine , toluene, o-xylene, m-xylene, p-xylene, 1,4 dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1, 1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydrogen Naphthalene, decalin, hydrazine and/or mixtures thereof.
  • the composition according to the invention is a solution.
  • composition according to the invention is a suspension.
  • Another aspect of the invention also relates to the use of the composition as a printing ink in the preparation of an organic electronic device, particularly preferably the use of the composition for the preparation of an organic electronic device by means of printing or coating.
  • suitable printing or coating techniques include, but are not limited to, inkjet printing, Nozzle Printing, typography, screen printing, dip coating, spin coating, blade coating, roller printing, torsion roller Printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, spray printing, slit-type extrusion coating, and the like.
  • Inkjet printing, slit-type extrusion coating, jet printing and gravure printing are preferred.
  • the solution or suspension may additionally contain one or more components, for example, a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobic agent, a binder, etc., for adjusting viscosity, film forming properties, and adhesion. Sex and so on.
  • a surface active compound for example, a lubricant, a wetting agent, a dispersing agent, a hydrophobic agent, a binder, etc.
  • the present invention also provides the use of a compound or polymer as described above in an organic electronic device.
  • the organic electronic device may be selected from, but not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser. , organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diode), especially OLED.
  • the organic compound is preferably used in the luminescent layer of an OLED device.
  • a further aspect of the invention further relates to an organic electronic device comprising at least one compound or polymer as described above.
  • the organic electronic device comprises at least one cathode, an anode and a functional layer between the cathode and the anode, wherein the functional layer comprises at least one compound or polymer as described above.
  • the organic electronic device may be selected from, but not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting battery (OLEEC), and an organic Field effect transistors (OFETs), organic light-emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (Organic Plasmon Emitting Diode).
  • the organic electronic device is an electroluminescent device, in particular an OLED, comprising a substrate, an anode, a cathode, and at least one luminescent layer between the anode and the cathode, optionally further A hole transport layer or an electron transport layer may be included. In certain embodiments, a compound or polymer according to the invention is included in the hole transport layer.
  • the compound or polymer according to the invention is contained in the luminescent layer, more preferably the luminescent layer comprises a compound or polymer according to the invention, and at least one luminescent material
  • the luminescent material may preferably be selected from the group consisting of a fluorescent illuminant, a phosphorescent illuminant, and a TADF material.
  • the device structure of the electroluminescent device is described below without limitation.
  • the substrate can be opaque or transparent. Transparent substrates can be used to make transparent light-emitting components. See, for example, Bulovic et al. Nature 1996, 380, p29, and Gu et al, Appl. Phys. Lett. 1996, 68, p2606.
  • the substrate can be rigid or elastic.
  • the substrate can be made of plastic, metal, semiconductor wafer or glass. Most preferably, the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice.
  • the substrate is flexible and may be selected from polymeric films or plastics having a glass transition temperature Tg of 150 ° C or higher, preferably more than 200 ° C, more preferably more than 250 ° C, and most preferably more than 300 ° C.
  • suitable flexible substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).
  • the anode can comprise a conductive metal or metal oxide, or a conductive polymer.
  • the anode can easily inject holes into a hole injection layer (HIL), a hole transport layer (HTL) or a light-emitting layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • the work function of the anode and the absolute value of the difference between the HOMO level or the valence band level of the luminescent material in the luminescent layer as the p-type semiconductor material of the HIL, HTL or electron blocking layer (EBL) is less than 0.5 eV. Preferably, it is less than 0.3 eV, and most preferably less than 0.2 eV.
  • anode material examples include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like.
  • suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art.
  • the anode material can be deposited using any suitable technique, such as suitable physical vapor deposition, including RF magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices in accordance with the present invention.
  • the cathode can comprise a conductive metal or a metal oxide.
  • the cathode can easily inject electrons into the EIL or ETL or directly into the luminescent layer.
  • the work function of the cathode and the LUMO level or conduction band of the n-type semiconductor material of the illuminant in the luminescent layer as an electron injection layer (EIL), an electron transport layer (ETL) or a hole blocking layer (HBL)
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the absolute value of the difference in energy levels is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV.
  • all materials which can be used as cathodes for OLEDs are possible as cathode materials for the devices of the invention.
  • cathode material examples include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like.
  • the cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the OLED may also include other functional layers such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), Electron injection layer (EIL), electron transport layer (ETL), hole blocking layer (HBL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the light-emitting layer of the light-emitting device according to the present invention comprises the organic compound or polymer of the present invention, which is preferably prepared by a solution processing method.
  • the light-emitting device according to the invention has an emission wavelength of between 300 and 1000 nm, preferably between 350 and 900 nm, more preferably between 400 and 800 nm.
  • Another aspect of the invention also relates to the use of an organic electronic device in accordance with the present invention in various electronic devices, including, but not limited to, applications in display devices, illumination devices, light sources, sensors, and the like.
  • a method for synthesizing a compound according to the present invention is shown in the following examples, but the present invention is not limited to the following examples.
  • reaction solution was transferred to a rotary flask, and most of the solvent was evaporated to dryness, extracted with dichloromethane, washed with water three times, then dried over anhydrous magnesium sulfate, filtered and dried, and the crude product was subjected to column chromatography in a yield of 85%. .
  • N-phenylcarbazole-2-borate (73.8 g, 200 mmol), 2-nitrobromobenzene (44.5 g, 220 mmol), tetratriphenylphosphine palladium (7.0 g, 6 mmol) under argon atmosphere
  • Sodium carbonate (51.0 g, 480 mmol) and water 80 mL and 1,4-dioxane 300 mL were placed in a 1000 mL three-necked flask, heated to 120 ° C, and reacted for 12 hours.
  • the product of the previous step was transferred to a one-neck round bottom flask under an argon atmosphere, 300 mL of triethyl phosphite was added, and the mixture was heated to 160 ° C for 12 hours.
  • the reaction was stopped, and the liquid in the reaction liquid was distilled off by a vacuum distillation apparatus, and the temperature was raised to 120 ° C until the reaction flask had no solvent and was distilled off.
  • the remaining solid of the reaction flask was purified by column chromatography to give a yield of about 60%.
  • reaction was stopped, the reaction solution was transferred to a 1000 mL beaker, water was slowly added while stirring, and dilute hydrochloric acid was added to neutralize. The upper liquid was poured out, and the solid product was washed twice with ethanol, and recrystallized from a tetrahydrofuran/petroleum ether solvent in a yield of about 75%.
  • N-phenylcarbazole-1-borate (73.8 g, 200 mmol), 2-nitrobromobenzene (44.5 g, 220 mmol), tetratriphenylphosphine palladium (7.0 g, 6 mmol) under argon atmosphere
  • Sodium carbonate (51.0 g, 480 mmol) and water 80 mL and 1,4-dioxane 300 mL were placed in a 1000 mL three-necked flask, heated to 120 ° C, and reacted for 12 hours.
  • reaction raw materials The reaction was stopped, the reaction solution was transferred to a rotary flask, and most of the solvent was evaporated to dryness, extracted with dichloromethane, washed three times with water, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. Reaction raw materials.
  • the product of the previous step was transferred to a one-neck round bottom flask under an argon atmosphere, 300 mL of triethyl phosphite was added, and the mixture was heated at 160 ° C for 12 hours.
  • the reaction was stopped, and the liquid in the reaction liquid was distilled off by a vacuum distillation apparatus, and the temperature was raised to 120 ° C until the reaction flask had no solvent and was distilled off.
  • the remaining solid of the reaction flask was purified by column chromatography to give a yield of about 70%.
  • reaction was stopped, the reaction solution was transferred to a 1000 mL beaker, water was slowly added while stirring, and dilute hydrochloric acid was added to neutralize. The upper liquid was poured out, and the solid product was washed twice with ethanol, and recrystallized from a tetrahydrofuran/petroleum ether mixed solvent to give a yield of about 85%. 5)
  • the energy level of the organic material can be obtained by quantum calculation, for example, by TD-DFT (time-dependent density functional theory) by Gaussian 03W (Gaussian Inc.), and the specific simulation method can be found in WO2011141110.
  • TD-DFT time-dependent density functional theory
  • Gaussian 03W Gaussian Inc.
  • the specific simulation method can be found in WO2011141110.
  • the semi-empirical method “Ground State/Semi-empirical/Default Spin/AM1" (Charge 0/Spin Singlet) is used to optimize the molecular geometry, and then the energy structure of the organic molecule is determined by TD-DFT (time-dependent density functional theory) method.
  • TD-SCF/DFT/Default Spin/B3PW91 and the base group "6-31G(d)” (Charge 0/Spin Singlet).
  • the HOMO and LUMO levels are calculated according to the following calibration formula, and S1 and T1 are used directly.
  • HOMO(eV) ((HOMO(G) ⁇ 27.212)-0.9899)/1.1206
  • HOMO(G) and LUMO(G) are direct calculation results of Gaussian 03W, and the unit is Hartree.
  • the results are shown in Table 1:
  • compound (3-2) and Ref1 are used as host materials
  • Ir(ppy) 3 is used as a light-emitting material
  • HATCN is used as a hole injecting material
  • NPB and TCTA are used as a hole transporting material
  • B3PYMPM is used as an electron transporting material.
  • HATCN, NPB, TCTA, B3PYMPM, Ir(ppy) 3 , Ref1 are commercially available, such as from Jilin Elound (Jilin OLED Material Tech Co., Ltd, www.jl-oled.com).
  • Jilin Elound Jilin OLED Material Tech Co., Ltd, www.jl-oled.com.
  • the synthesis methods are all known in the prior art, and the references in the prior art are not described herein.
  • the process of preparing an OLED device using the above materials will be described in detail below by way of specific embodiments.
  • the structure of the OLED device (such as Table 2) is: ITO/HATCN/NPB/TCTA/body material: Ir(ppy) 3 /B3PYMPM/LiF/Al
  • the preparation steps are as follows:
  • ITO indium tin oxide
  • a conductive glass substrate cleaning using a variety of solvents (such as one or several of chloroform, acetone or isopropanol) for cleaning, and then UV ozone treatment;
  • HATCN 5nm
  • NPB 40nm
  • TCTA 10nm
  • host material 15% Ir(ppy) 3 (45nm)
  • B3PYMPM 35nm
  • LiF 1nm
  • Al 100nm
  • high vacuum (1 ⁇ 10 -6 mbar) formed by thermal evaporation
  • the device is encapsulated in a nitrogen glove box with an ultraviolet curable resin.
  • the structure of the solution processed OLED device is as follows: ITO/PEDOT (80 nm) / TFB (20 nm) / host material (2-6): Emitter (15 wt%) (45 nm) / B3PYMPM (35) / LiF (1 nm) / Al ( 100nn). The Emitter is shown below.
  • the hole transport material TFB (H.W. Sands Corp.) is
  • PEDOT, TFB and luminescent layer are all spin-coated.
  • the TFB layer was a solution of TFB in toluene with a solubility of 6 mg/ml.
  • As the light-emitting layer a mixture of the host material (2-6): Emitter (15 wt%) in toluene having a solubility of 20 mg/ml was used.
  • the preparation of EML and cathode was as described in Example 3. Since the solubility of the host material Ref1 is poor, it cannot be prepared by solution processing.
  • the current-voltage (J-V) characteristics of each OLED device are characterized by characterization equipment while recording important parameters such as efficiency, lifetime and external quantum efficiency.
  • the external quantum efficiencies of OLED 1, OLED 2 and RefOELD 1 were determined to be 12.1%, 13.4% and 7.8%, respectively.
  • the lifetime of OLED2 is 15 times that of RefOELD. It can be seen that the OLED device prepared by using the organic compound of the present invention has improved solution processability and greatly improved its life.

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Abstract

La présente invention concerne un composé avec des hétérocycles d'indole reliés, et un mélange, une composition, un dispositif électronique organique contenant le composé, et une utilisation. Dans certains modes de réalisation préférés, l'atome d'hydrogène dans une liaison C-H sur un squelette de conjugué d'indolocarbazole d'un matériau photoélectrique organique est remplacé par un groupe aromatique, et un ou plusieurs motifs hétérocycliques d'indole sont reliés, par conséquent, l'activité de réaction de cet emplacement peut être significativement réduite, et une meilleure stabilité chimique et environnementale est conférée au groupe. Le composé avec des hétérocycles d'indole reliés est appliqué à un dispositif électronique organique, et l'invention concerne en outre une solution pour améliorer la stabilité et la durée de vie d'un dispositif.
PCT/CN2016/098518 2015-12-04 2016-09-09 Composé avec hétérocycles d'indole reliés et utilisation de celui-ci dans un dispositif électronique organique WO2017092473A1 (fr)

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