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WO2019114611A1 - Composé amine aromatique, dispositif électronique organique le comprenant et application - Google Patents

Composé amine aromatique, dispositif électronique organique le comprenant et application Download PDF

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Publication number
WO2019114611A1
WO2019114611A1 PCT/CN2018/119622 CN2018119622W WO2019114611A1 WO 2019114611 A1 WO2019114611 A1 WO 2019114611A1 CN 2018119622 W CN2018119622 W CN 2018119622W WO 2019114611 A1 WO2019114611 A1 WO 2019114611A1
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organic
aromatic amine
aromatic
amine compound
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Chinese (zh)
Inventor
谭甲辉
张晨
潘君友
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Guangzhou Chinaray Optoelectronic Materials Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to an aromatic amine compound, including mixtures thereof, compositions, and organic electronic devices thereof, particularly in organic light emitting diodes.
  • OLEDs Organic light-emitting diodes
  • Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic matter.
  • An organic electroluminescence device utilizing an organic electroluminescence phenomenon generally has a structure in which a positive electrode and a negative electrode and an organic layer are contained therebetween.
  • the organic layer has a multilayer structure, and each layer contains a different organic substance. Specifically, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like may be included.
  • Such an organic electroluminescence device when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, electrons are injected from the negative electrode into the organic layer, and excitons are formed when the injected holes meet the electrons. The excitons emit light when they transition back to the ground state.
  • Such an organic electroluminescence device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.
  • the OLED device needs to be further improved in luminous efficiency and service life. Because OLED is used as a current-driven device, it is in a high current density state during operation, and the material is prone to Joule heat, resulting in device degradation, especially between the anode and the hole transport layer. .
  • the commonly used hole transporting materials have a low glass transition temperature, and the accumulation of Joule heat causes a change in the morphology of the film, and at the same time accelerates the decomposition of the material, thereby affecting the life of the device.
  • the hole mobility of the organic semiconductor material is generally higher than the electron mobility, resulting in a hole-electron transport imbalance that affects the device's luminous efficiency.
  • the devices of the above disclosed compounds have to be improved in power efficiency, luminous efficiency and working life, so new OLED materials still need to be proposed to improve the performance of the device.
  • an object of the present invention to provide a novel class of aromatic amine compounds having excellent current efficiency, mixtures and compositions thereof, and their use in organic electronic devices.
  • an aromatic amine group derivative of an anthracene heterocyclic skeleton can be used as an electroluminescent material, particularly as a hole transporting or hole injecting material, to obtain an OLED device having high luminous efficiency and long life.
  • Ea electron affinity
  • L 1 -L 3 is a linking group selected from a single bond, an aromatic group or a heteroaromatic group
  • Each occurrence of Ar 1 -Ar 6 may be independently selected from an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms. Or a combination of these systems, wherein Ar 1 and Ar 2 , Ar 3 and Ar 4 and Ar 5 and Ar 6 may be linked to each other to form a monocyclic or polycyclic aliphatic or aromatic ring system.
  • o, p, q each independently represent an integer of 0 to 1, and o + p + q ⁇ 1;
  • n and n each independently represent an integer of 0 to 3.
  • a high polymer characterized by comprising at least one repeating structural unit represented by the general formula (I).
  • a mixture comprising at least one aromatic amine compound or polymer as described above, and at least one other organic functional material, said another organic functional material being selected from the group consisting of hole injecting materials (HIM), hole transport material (HTM), p-dopant, electron transport material (ETM), electron injecting material (EIM), electron blocking material (EBM), hole blocking material (HBM), luminescent material (Emitter) , host material (Host) and organic dyes.
  • HIM hole injecting materials
  • HTM hole transport material
  • ETM electron transport material
  • EIM electron injecting material
  • EBM electron blocking material
  • Emitter hole blocking material
  • Hos host material
  • organic dyes organic dyes
  • a composition comprising at least one aromatic amine compound, polymer or mixture as described above, and at least one organic solvent.
  • An organic electronic device comprising at least one aromatic amine compound, polymer or mixture as described above.
  • An electroluminescent device characterized in that the luminescent layer comprises at least one aromatic amine compound, polymer, or mixture according to the above.
  • the aromatic amine compound of the present invention contains an anthracene heterocyclic skeleton, and when used as a hole transporting or hole injecting material, an OLED device having high luminous efficiency and long life can be obtained.
  • EA electron affinity
  • EA electron affinity
  • the present invention provides an aromatic amine compound, an organic electronic device comprising the same, and an application thereof.
  • an aromatic amine compound an organic electronic device comprising the same, and an application thereof.
  • the host material, the matrix material, the Host material, and the Matrix material have the same meaning and are interchangeable.
  • the singlet states and the singlet states have the same meaning and are interchangeable.
  • the triplet state and the triplet state have the same meaning and are interchangeable.
  • composition and the printing ink, or ink have the same meaning and are interchangeable.
  • the complex excited state, exciplex, and Exciplex have the same meaning and are interchangeable.
  • 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, preferably ⁇ 1500 g/mol.
  • the present invention relates to an aromatic amine compound of the formula (I):
  • L 1 -L 3 is a linking group selected from a single bond, an aromatic group or a heteroaromatic group
  • Each occurrence of Ar 1 -Ar 6 may be independently selected from an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms. Or a combination of these systems, wherein between Ar 1 and Ar 2 , between Ar 3 and Ar 4 , and between Ar 5 and Ar 6 may be linked to form a monocyclic or polycyclic aliphatic or aromatic ring system.
  • o, p, q each independently represent an integer of 0 to 1, and o + p + q ⁇ 1;
  • n and n each independently represent an integer of 0 to 3.
  • R 0 is selected from H, or D, or a substituted or unsubstituted aromatic or heteroaromatic ring system having from 5 to 20 ring atoms. In a most preferred embodiment, R 0 is selected from H, or D.
  • an aromatic amine compound according to the present invention is characterized in that the aromatic amine compound has a structure represented by the general formula (II-1)-(II-8):
  • Ar 1 -Ar 6 , o, p, q, m, n, R 0 , R 1 , R 2 , L 1 -L 3 have the same meaning as in claim 1.
  • each of Ar 1 -Ar 6 may be independently selected from an aromatic or heteroaromatic ring system having 5 to 30 ring atoms. Or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, or a combination of these systems, wherein one or more groups may form a single ring to each other and/or to the ring to which the group is bonded Or a polycyclic aliphatic or aromatic ring system;
  • each of Ar 1 -Ar 6 may be independently selected from an aromatic or heteroaromatic ring system having 5 to 20 ring atoms. Or an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these systems, wherein between Ar 1 and Ar 2 , between Ar 3 and Ar 4 , and between Ar 5 and Ar 6 It may be linked to form a monocyclic or polycyclic aliphatic or aromatic ring system.
  • Ar 1 -Ar 6 may be independently selected from the following structures:
  • each occurrence of Z may be independently selected from N or CR 5 , and two adjacent Zs may not be N at the same time; when Z is connected to N in the general formula (I), Z is C;
  • R 3 , R 4 and R 5 have the same meanings as R 1 ;
  • P represents a saturated cycloalkane or heterocycloalkane having 3 to 10 ring atoms; preferably represents a saturated cycloalkane or heterocycloalkane having 3 to 8 ring atoms; more preferably represents a saturation having 3 to 5 ring atoms a cycloalkane or a heterocycloalkane;
  • the dotted line indicates a single bond in which the group is bonded to the N atom of the aromatic amine.
  • Ar 1 to Ar 6 are independently selected from the following structures:
  • L 1 -L 3 is a linking group selected from a single bond, an aromatic group or a heteroaromatic group
  • An aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including a monocyclic group and a polycyclic ring system.
  • Heteroaromatic groups refer to hydrocarbyl groups (containing heteroatoms) comprising at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems. These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, a fused ring. At least one of these heterocyclic rings is an aromatic or heteroaromatic group.
  • an aromatic group or a heteroaromatic group includes not only a system of an aromatic group or a heteroaryl group, but also a plurality of aryl or heteroaryl groups may also be interrupted by short non-aromatic units (for example, ⁇ 10). % of non-H atoms, 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 groups for the purposes of the present invention.
  • aromatic group preferred examples include: benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, anthracene, benzopyrene, triphenylene, anthracene, anthracene, and derivatives thereof.
  • heteroaromatic groups are: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, hydrazine, hydrazine 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 L 1 -L 3 of the present invention is selected from an aromatic group having 6 to 40 carbon atoms or a heteroaromatic group having 3 to 40 carbon atoms. Further, L 1 -L 3 is selected from an aromatic group having 6 to 30 carbon atoms or a heteroaromatic group having 3 to 30 carbon atoms. Further, L 1 -L 3 is selected from an aromatic group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms.
  • Suitable aromatic or heteroaromatic groups which may be L 1 -L 3 are, but not limited to, benzene, naphthalene, anthracene, phenanthrene, anthracene, pyridine, pyrimidine, triazine, anthracene, sulfonium, silicon germanium. , carbazole, thiophene, furan, thiazole, triphenylamine, triphenylphosphine oxide, tetraphenyl silicon, snail, spirosilicone and the like.
  • linking group L 1 -L 3 of the present invention may comprise one or more combinations of the following structural formulas:
  • linking group L 1 -L 3 of the present invention may be selected from the following structural units, which may be further substituted:
  • the energy level structure of the organic compound the triplet energy level E T , the highest occupied orbital energy level HOMO, and the lowest occupied orbital energy level LUMO play an important role.
  • the following is an introduction to the determination of these energy levels.
  • the HOMO and LUMO levels can be measured by photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (UV photoelectron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV).
  • photoelectric effect such as XPS (X-ray photoelectron spectroscopy) and UPS (UV photoelectron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV).
  • quantum chemical methods such as density functional theory (hereinafter referred to as DFT) have also become effective methods for calculating molecular orbital energy levels.
  • the triplet energy level E T of organic materials can be measured by low temperature time-resolved luminescence spectroscopy, or by quantum simulation calculations (eg by Time-dependent DFT), as by commercial software Gaussian 03W (Gaussian Inc.), specific simulation methods. See WO2011141110 or as described below in the examples.
  • the absolute values of HOMO, LUMO, E T depend on the measurement method or calculation method used. Even for the same method, different evaluation methods, such as starting point and peak point on the CV curve, can give different HOMO/ LUMO value. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method.
  • the values of HOMO, LUMO, and E T are simulations based on Time-dependent DFT, but do not affect the application of other measurement or calculation methods. The energy level values determined by different methods should be calibrated against each other.
  • (HOMO-1) is defined as the second highest occupied orbital level
  • (HOMO-2) is the third highest occupied orbital level
  • (LUMO+1) is defined as the second lowest unoccupied orbital level
  • (LUMO+2) is the third lowest occupied orbital level, and so on.
  • the compound according to the invention is at least partially deuterated, preferably 10% of H is deuterated, more preferably 20% of H is deuterated, very preferably 30% H It is best to be replaced by 40% of H.
  • the compounds according to the invention can be used in various functional layers of organic electronic devices.
  • the compound according to the invention is used as a hole transporting material, a hole injecting material, and a host material.
  • the compound according to the invention has a HOMO ⁇ -5.5 eV, preferably ⁇ - 5.2 eV, more preferably ⁇ - 5.1 eV, most preferably ⁇ - 5.0 eV.
  • the compound according to the invention ((HOMO-(HOMO-1)) ⁇ 0.15 eV, preferably ⁇ 0.25 eV, more preferably ⁇ 0.3 eV, more preferably ⁇ 0.35 eV, very good is ⁇ 0.4eV, preferably ⁇ 0.5eV.
  • the compound according to the invention has a LUMO ⁇ -3.0 eV, preferably ⁇ -2.3 eV, more preferably ⁇ -2.2 eV, most preferably ⁇ - 2.0 eV.
  • the compound according to the invention has a triplet energy level E T ⁇ 2.4 eV, preferably ⁇ 2.6 eV, more preferably ⁇ 2.7 eV, most preferably ⁇ 2.8 eV.
  • hole mobility is sometimes a very important parameter.
  • the compounds according to the present invention has a high hole mobility, typically ⁇ 10 -5 cm 2 / Vs, Jiaoyou ⁇ 10 -4 cm 2 / Vs, and most ⁇ 10 -3 cm 2 /Vs.
  • the compound according to the invention has a glass transition temperature of ⁇ 100 ° C, preferably ⁇ 110 ° C, more preferably ⁇ 120 ° C, most preferably ⁇ 140 ° C.
  • a compound according to the invention is preferably, but not limited to, the following structure:
  • the aromatic amine compound according to the present invention also has luminescent properties with an emission wavelength of between 300 and 1000 nm, preferably between 350 and 900 nm, more preferably between 400 and 800 nm.
  • the luminescence referred to herein means photoluminescence or electroluminescence.
  • the aromatic amine compound according to the present invention has a photo or electroluminescence efficiency of ⁇ 30%, preferably ⁇ 40%, more preferably ⁇ 50%, most preferably ⁇ 60%.
  • the aromatic amine compound according to the present invention may also be a hole transport material or an electron injecting material.
  • the invention still further relates to a high polymer comprising at least one repeating unit comprising a structural unit represented by the general formula (I).
  • the method for synthesizing the high polymer is selected from the group consisting of SUZUKI-, YAMAMOTO-, STILLE-, NIGESHI-, KUMADA-, HECK-, SONOGASHIRA-, HIYAMA-, FUKUYAMA-, HARTWIG-BUCHWALD- and ULLMAN.
  • the polymer according to the invention has a glass transition temperature (Tg) ⁇ 100 ° C, preferably ⁇ 120 ° C, more preferably ⁇ 140 ° C, more preferably ⁇ 160 ° C, optimal. It is ⁇ 180 °C.
  • the polymer according to the present invention preferably has a molecular weight distribution (PDI) in the range of from 1 to 5; more preferably from 1 to 4; more preferably from 1 to 3, still more preferably 1 ⁇ 2 is most preferably 1 to 1.5.
  • PDI molecular weight distribution
  • the weight average molecular weight (Mw) of the high polymer according to the present invention preferably ranges from 10,000 to 1,000,000; more preferably from 50,000 to 500,000; more preferably from 100,000 to 40. More preferably, it is 150,000 to 300,000, and most preferably 200,000 to 250,000.
  • the present invention also provides a mixture comprising at least one of the above-described aromatic amine compounds or polymers, and at least one other organic functional material, said at least one other organic functional material being selectable In hole injection material (HIM), hole transport material (HTM), p-dopant, electron transport material (ETM), electron injecting material (EIM), electron blocking material (EBM), hole blocking material (HBM), Emitter, host material and organic dye.
  • HIM hole injection material
  • HTM hole transport material
  • ETM electron transport material
  • EIM electron injecting material
  • EBM electron blocking material
  • Emitter Emitter
  • host material and organic dye Emitter
  • organic functional materials are described in detail in, for example, WO2010135519A1, US20090134784A1, and WO 2011110277A1, the entire disclosure of which is hereby incorporated by reference.
  • the mixture of the ones comprises at least one aromatic amine compound or polymer according to the invention and a p-dopant, wherein the p-dopant weight percentage is ⁇ 10 wt%, preferably ⁇ 9 wt%, more preferably ⁇ 7 wt%, particularly preferably ⁇ 6 wt%, most preferably ⁇ 5 wt%.
  • the mixture comprises at least one aromatic amine compound or polymer according to the present invention, and a fluorescent host material.
  • a mixture may be used as a fluorescent host material, and may further comprise a fluorescent illuminant, wherein the fluorescent illuminant has a weight percentage of ⁇ 10% by weight, preferably ⁇ 9wt%, more preferably ⁇ 8wt%, particularly preferably ⁇ 7wt% Preferably, it is ⁇ 5 wt%.
  • the mixture of said one comprises at least one aromatic amine compound or polymer according to the invention and a phosphorescent host material.
  • a mixture may be used as a phosphorescent host material, and may further comprise a phosphorescent emitter, wherein the phosphorescent emitter has a weight percentage of ⁇ 25 wt%, preferably ⁇ 20 wt%, more preferably ⁇ 15 wt%.
  • the fluorescent host material singlet illuminant, phosphorescent host material, triplet illuminant and p-dopant material are described in detail below (but are not limited to):
  • Singlet emitters tend to have longer conjugated pi-electron systems.
  • styrylamine and its derivatives disclosed in JP 2913116 B and WO 2001021729 A1, indenoindoles and derivatives thereof disclosed in WO 2008/006449 and WO 2007/140847, and disclosed in US Pat. No. 7,233,019, KR2006-0006760 A quinone triarylamine derivative.
  • the singlet emitter can be selected from the group consisting of monostyrylamine, dibasic styrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether and aromatic amine.
  • a monostyrylamine refers to a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine.
  • a dibasic styrylamine refers to a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a ternary styrylamine refers to a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a quaternary styrylamine refers to a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a preferred styrene is stilbene, which may be further substituted.
  • the corresponding phosphines and ethers are defined similarly to amines.
  • An arylamine or an aromatic amine refers to a compound comprising three unsubstituted or substituted aromatic ring or heterocyclic systems directly bonded to a nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably selected from the fused ring system and 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.
  • An aromatic amide refers to a compound in which a diaryl arylamine group is attached directly to the oxime, preferably at the position of 9.
  • An aromatic quinone diamine refers to a compound in which two diaryl arylamine groups are attached directly to the oxime, preferably at the 9,10 position.
  • the definitions of aromatic decylamine, aromatic quinone diamine, aromatic thiamine and aromatic quinone diamine are similar, wherein the diaryl aryl group is preferably bonded 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 7250532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US 6251531 B1, US 2006/210830 A, EP 1957606 A1 and US 2008/0113101 A1 are hereby incorporated by reference in their entirety. This article is incorporated herein by reference.
  • Further preferred singlet emitters can be selected from indenoindole-amines and indenofluorene-diamines, as disclosed in WO 2006/122630, benzoindoloindole-amines and benzoindenoindole-diamines , as disclosed in WO 2008/006449, dibenzoindolo-amine and dibenzoindeno-diamine, as disclosed in WO 2007/140847.
  • Further preferred singlet emitters are selected from the group consisting of ruthenium-based fused ring systems as disclosed in US2015333277A1, US2016099411A1, US2016204355A1.
  • More preferred singlet emitters may be selected from the derivatives of hydrazine, such as those disclosed in US2013175509A1; triarylamine derivatives of hydrazine, such as triarylamine derivatives of hydrazine containing dibenzofuran units disclosed in CN102232068B; A triarylamine derivative of hydrazine having a specific structure, as disclosed in CN105085334A, CN105037173A.
  • 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
  • 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 different and is an organic ligand. It is bonded to the metal atom M by one or more positional bonding or coordination, and n is an integer greater than 1, preferably 1, 2, 3, 4, 5 or 6.
  • these metal complexes are coupled to a polymer by one or more positions, preferably by an organic ligand.
  • the metal atom M is selected from a transition metal element or a lanthanide or a lanthanide element, preferably Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy Re, Cu or Ag, with Os, Ir, Ru, Rh, Re, Pd, Au or Pt being particularly preferred.
  • the triplet emitter comprises 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 pairs Tooth or multidentate ligand.
  • Chelating ligands are beneficial for increasing the stability of metal complexes.
  • Examples of the organic ligand may be selected from a phenylpyridine derivative, a 7,8-benzoquinoline derivative, a 2(2-thienyl)pyridine derivative, a 2(1-naphthyl)pyridine derivative, or a 2 benzene.
  • a quinolinol 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 has the following form:
  • M is a metal selected from a transition metal element or a lanthanide or actinide element, particularly preferably Ir, Pt, Au;
  • Ar 1 may be the same or different at each occurrence, and is a cyclic group containing 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 a metal.
  • Ar 2 may be the same or different each time it appears, is a cyclic group containing at least one C atom through which a cyclic group is attached to the metal; Ar 1 and Ar 2 are bonded by a covalent bond Together, each may carry one or more substituent groups, which may also be joined together by a substituent group; L' may be the same or different at each occurrence, and is a bidentate chelate auxiliary ligand, preferably Is a monoanionic bidentate chelate ligand; q1 can be 0, 1, 2 or 3, preferably 2 or 3; q2 can be 0, 1, 2 or 3, preferably 1 or 0.
  • triplet emitters Some examples of suitable triplet emitters are listed in the table below:
  • the fluorescent host material is also referred to as a singlet host material, and the example of the fluorescent host material is not particularly limited, and any organic compound may be used as a host as long as it has a singlet energy ratio illuminant, particularly a singlet illuminant. Or the fluorescent illuminant is higher.
  • Examples of the organic compound used as the fluorescent host material may be selected from the group consisting of a cyclic aromatic hydrocarbon compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, anthracene, phenanthrene, anthracene, anthracene, fluorene, fluorene, fluorene, fluorene, fluorene; Aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, carbazole, pyridinium , pyrrole dipyridine, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, triazole, dioxazole, thiadiazole, pyridine, pyridazin
  • the fluorescent host material can be selected from compounds comprising at least one of the following groups:
  • R 1 may be independently of one another selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl; n is a An integer from 0 to 20; X 1 -X 8 is selected from CH or N; X 9 and X 10 are selected from CR 1 R 2 or NR 1 . R 2 has the same meaning as R 1 .
  • the fluorescent host is selected from the group consisting of hydrazine derivatives, such as those disclosed in the patent documents CN102224614 B, CN 100471827 C, CN 1914293 B, WO2015033559A1, US2014246657A1, WO2016117848A1, WO2016117861A1, WO2016171429A2, CN102369256B, CN102428158B.
  • hydrazine derivatives such as those disclosed in the patent documents CN102224614 B, CN 100471827 C, CN 1914293 B, WO2015033559A1, US2014246657A1, WO2016117848A1, WO2016117861A1, WO2016171429A2, CN102369256B, CN102428158B.
  • fluorenyl-based fluorescent host materials are listed in the table below:
  • the fluorenyl-based fluorescent host material is deuterated, that is, the host material molecule contains at least one ruthenium atom, such as disclosed in the patent documents CN102369256B, CN102428158B, CN102639671B, US2015021586A1, and the like. Specific examples are:
  • the phosphorescent host material is also referred to as a triplet host material, and the example of the triplet host material is not particularly limited, and any metal complex or organic compound may be used as a host as long as its triplet level is higher than that of the illuminant, especially
  • the triplet emitter or phosphorescent emitter is higher, and examples of metal complexes that can be used as a triplet host include, but are not limited to, the following general structure:
  • M is a metal
  • (Y 3 -Y 4 ) is a bidentate ligand, Y 3 and Y 4 are independently selected from C, N, O, P, and S
  • L is an ancillary ligand
  • m is an integer The value is from 1 to the maximum coordination number of the metal; in a preferred embodiment, the metal complex that can be used as the triplet host has the following form:
  • (O-N) is a two-tooth ligand in which a metal is coordinated to an O and N atom.
  • m is an integer whose value ranges from 1 to the maximum coordination number of the metal;
  • M is optional for Ir and Pt.
  • Examples of the organic compound which can be used as the host of the triplet state are selected from compounds containing a cyclic aromatic hydrocarbon group such as benzene, biphenyl, triphenylbenzene, benzindene; compounds containing an aromatic heterocyclic group such as dibenzothiophene, Dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, oxazole, dibenzoxazole, carbazole, pyridinium, pyrrole dipyridine, Pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxazine , oxadiazin
  • each Ar may be further substituted, and the substituent may be hydrogen, hydrazine, cyano, halogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl. base.
  • the triplet host material can be selected from compounds comprising at least one of the following groups:
  • R 2 -R 7 have the same meaning as R 1
  • X 9 is selected from CR 1 R 2 or NR 1
  • Y is selected from CR 1 R 2 or NR 1 or O or S.
  • R 1 , n, X 1 -X 8 , and Ar 1 to Ar 3 have the same meanings as described above.
  • triplet host materials examples include:
  • Such an organic semiconductor material may be composed of a compound having good electron donating properties or good electron withdrawing properties.
  • strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4- Benzoyl dimethane (F4TCNQ) is well known. See article M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, App. Phys. Lett., 73 (22), 3202-3204 (1998) and J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, App. Phys. Lett., 73 (6), 729-731 (1998).
  • P-type dopants Due to defects in TCNQ and F4TCNQ in specific applications (molecular weight is too small, too volatile), a series of hydroquinone derivatives can be used as P-type dopants, the structure of which includes but is not limited to the following structure (patent TW200629362A):
  • R 8 to R 19 are independently F, Cl, CN, NO 2 , CF 3 , perfluoroalkyl, SO 3 R 20 , aryl or heteroaryl, wherein the aryl and heteroaryl are from one to the other F, Cl, CN, NO 2 , CF 3 , perfluoroalkyl, SO 3 R;
  • A, B, C, and D are independently selected from C(CN) 2 , (CF 3 )C(CN), (NO 2 )C(CN), C(halogen) 2 , C(CF 3 ) 2 , NCN , O, S, NR 20 and the following structure:
  • n2 is selected from a natural number from 1 to 4; each of X 1 , X 2 , and X 3 is independently selected from the group consisting of C(CN) 2 , (CF 3 )C(CN), (NO 2 )C(CN), C ( Halogen) 2 , C(CF 3 ) 2 , NCN, O, S, NR1 and the following structures:
  • the compounds according to the invention have a molecular weight of ⁇ 1100 g/mol, preferably ⁇ 1000 g/mol, very preferably ⁇ 950 g/mol, more preferably ⁇ 900 kg/mol, most preferably ⁇ 800 g/mol.
  • Another object of the invention is to provide a material solution for printing OLEDs.
  • the compounds according to the invention have a molecular weight of ⁇ 700 g/mol, preferably ⁇ 800 g/mol, very preferably ⁇ 900 g/mol, more preferably ⁇ 1000 g/mol, most preferably ⁇ 1100 g/mol.
  • the compound according to the invention has a solubility in toluene of > 2 mg/ml, preferably > 3 mg/ml, more preferably > 4 mg/ml, most preferably > 5 mg/ml at 25 °C.
  • Another object of the invention is a solution for providing materials for printing OLEDs.
  • the invention further relates to a composition or ink comprising the aromatic amine compound, polymer or mixture of any of the above, and at least one organic solvent.
  • the at least one organic solvent is selected from the group consisting of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic a compound, or a borate or phosphate compound, or a mixture of two or more solvents.
  • a composition according to the invention is characterized in that said at least one organic solvent is selected from solvents based on aromatic or heteroaromatic.
  • aromatic or heteroaromatic solvents suitable for the present invention are, but are not limited to, p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene.
  • aromatic ketone solvents suitable for the present invention are, but are not limited to, 1-tetralone, 2-tetralone, 2-(phenyl epoxy) tetralone, 6-(methoxy Tetrendanone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.;
  • aromatic ether-based solvents suitable for the present invention are, but are not limited to, 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H -pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxy Toluene, 4-ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans-p-propenyl anisole, 1,2-dimethoxybenzene, 1-methyl Oxynaphthalene, diphenyl ether
  • the at least one organic solvent may be selected from the group consisting of: an aliphatic ketone, for example, 2-fluorenone, 3-fluorenone, 5-fluorenone, 2 - anthrone, 2,5-hexanedione, 2,6,8-trimethyl-4-indanone, anthrone, phorone, isophorone, di-n-pentyl ketone, etc.; or an aliphatic ether
  • the at least one organic solvent may be selected from ester-based solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, benzene. Alkyl formate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkanolide, alkyl oleate, and the like. Particularly preferred are octyl octanoate, diethyl sebacate, diallyl phthalate, isodecyl isononanoate.
  • the solvent may be used singly or as a mixture of two or more organic solvents.
  • a composition according to the present invention comprising the organic compound or composition of any one of the above, and at least one organic solvent, may further comprise another organic solvent,
  • an organic solvent including but 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, tetrahydronaphthalene ,
  • the invention further relates to the use of a composition as a printing ink for the preparation of organic electronic devices, particular preference being given to a preparation process by printing or coating.
  • suitable printing or coating techniques include, but are not limited to, inkjet printing, typography, screen printing, dip coating, spin coating, blade coating, roller printing, twist roll printing, lithography, flexography Printing, rotary printing, spraying, brushing or pad printing, slit-type extrusion coating, etc.
  • Preferred are gravure, screen printing and inkjet printing. Gravure printing, ink jet printing will be applied in embodiments of the invention.
  • the solution or suspension may additionally comprise one or more components such as surface active compounds, lubricants, wetting agents, dispersing agents, hydrophobic agents, binders and the like for adjusting viscosity, film forming properties, adhesion, and the like.
  • the invention further relates to the use of an aromatic amine compound, polymer, mixture or composition according to any of the preceding claims in an organic electronic device.
  • An organic electronic device characterized by comprising an aromatic amine compound, a polymer, or a mixture thereof according to any one of the 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 cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, and an organic Lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diode), etc., particularly preferred are organic electroluminescent devices such as OLED, OLEEC, organic light-emitting field effect transistors.
  • the organic electronic device is an electroluminescent device comprising a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer comprising at least An aromatic amine compound, polymer, or mixture as described above.
  • a substrate an anode, at least one light-emitting layer, and a cathode are included.
  • the substrate can be opaque or transparent.
  • a transparent substrate can be used to make a transparent light-emitting component. 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 plastic, metal, semiconductor wafer or glass.
  • the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice.
  • the substrate is flexible, optionally in the form of a polymer film or plastic, having a glass transition temperature Tg of 150 ° C or higher, preferably more than 200 ° C, more preferably more than 250 ° C, preferably More than 300 ° C. Examples of suitable flexible substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).
  • PET poly(ethylene terephthalate)
  • PEN polyethylene glycol (2,6-na
  • 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) or a hole transport layer (HTL) or a light-emitting layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • the absolute value of the difference between the work function of the anode and the HOMO level or the valence band level of the illuminant in the luminescent layer or the p-type semiconductor material as the HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably 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 a suitable physical vapor deposition process, including radio frequency 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 include a conductive metal or 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 of the illuminant or the n-type semiconductor material as an electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) in the luminescent layer or
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the absolute value of the difference in conduction band 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, BaF 2 /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 further include other functional layers such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer.
  • 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 device has an emission wavelength of between 300 and 1000 nm, preferably between 350 and 900 nm, more preferably between 400 and 800 nm.
  • the invention further relates to the use of an electroluminescent device according to the invention in various electronic devices, including, but not limited to, display devices, illumination devices, light sources, sensors and the like.
  • the energy structure of the organic repeating structural unit 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 09W, and the unit is eV.
  • Compound 1, Compound 4, Compound 5, Ref-1, NPB are used as hole transport materials
  • DNTPD is used as hole injection material
  • B3PYMPM is used as electron transport material
  • the device structure is ITO/HATCN/empty.
  • ITO indium tin oxide
  • a conductive glass substrate cleaning using a variety of solvents (such as one or several of chloroform, acetone or isopropanol) cleaning, and then UV ozone treatment;
  • DNTPD 60 nm
  • hole transport material 20 nm
  • BH: BD 95:5; 20 nm
  • B3PYMPM 30 nm
  • Al 100 nm
  • high vacuum (1 ⁇ 10 -6 m Ba
  • the device is encapsulated in a nitrogen glove box with an ultraviolet curable resin.
  • the current and voltage (IVL) characteristics of each OLED device are characterized by characterization equipment, as described in Table 2.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé amine aromatique et son application dans un dispositif électronique organique, et en particulier, dans une diode électroluminescente organique. La présente invention concerne également un dispositif électronique organique comprenant le composé amine aromatique selon la présente invention, et en particulier, une diode électroluminescente organique, et une application associée dans une technologie d'affichage et d'éclairage. La présente invention concerne également un dispositif électronique organique comprenant le composé amine aromatique selon la présente invention.
PCT/CN2018/119622 2017-12-14 2018-12-06 Composé amine aromatique, dispositif électronique organique le comprenant et application Ceased WO2019114611A1 (fr)

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US20130234118A1 (en) * 2012-03-06 2013-09-12 Samsung Display Co. Ltd. Amine-based compound, organic light-emitting diode including the same, and organic light-emitting apparatus including the amine-based compound
JP2016219490A (ja) * 2015-05-15 2016-12-22 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置

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US20130234118A1 (en) * 2012-03-06 2013-09-12 Samsung Display Co. Ltd. Amine-based compound, organic light-emitting diode including the same, and organic light-emitting apparatus including the amine-based compound
JP2016219490A (ja) * 2015-05-15 2016-12-22 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置

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