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WO2018095384A1 - Composé cyclique fusionné deutéré, polymère, mélange et composition, et dispositif électronique organique - Google Patents

Composé cyclique fusionné deutéré, polymère, mélange et composition, et dispositif électronique organique Download PDF

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Publication number
WO2018095384A1
WO2018095384A1 PCT/CN2017/112705 CN2017112705W WO2018095384A1 WO 2018095384 A1 WO2018095384 A1 WO 2018095384A1 CN 2017112705 W CN2017112705 W CN 2017112705W WO 2018095384 A1 WO2018095384 A1 WO 2018095384A1
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group
atoms
organic
deuterated
substituted
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潘君友
杨曦
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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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to the field of organic electroluminescence technology, and in particular to a deuterated fused ring compound, a polymer, a mixture, a composition, and an organic electronic device.
  • 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 development of a blue fluorescent material having a narrow-band emission spectrum and good stability is advantageous for obtaining a longer-life and higher-efficiency blue light device, and on the other hand, it is advantageous for the improvement of the color gamut, thereby improving the display effect.
  • the light-emitting layer of the conventional blue organic electroluminescent device adopts a host-guest doping structure.
  • ruthenium-based fused ring derivatives are described, for example, in the patents CN1914293B, CN102448945B, US2015287928A1, etc.
  • these compounds have problems of insufficient luminous efficiency and brightness, and poor lifetime of the device.
  • an arylvinylamine compound (WO 04/013073, WO 04/016575, WO 04/018587) can be used as the compound.
  • the host material is the key material that determines its lifetime. High-performance blue body materials have always been the focus of people's development.
  • the present invention provides a deuterated fused ring compound of the formula (I):
  • R 11 -R 19 and R 110 are each independently H or D, or a linear alkyl group having 1 to 20 C atoms, an alkoxy group or a thioalkoxy group, or a branch having 3 to 20 C atoms. a chain or cyclic alkyl, alkoxy or thioalkoxy group, or a substituted or unsubstituted silyl group, or a substituted ketone group having 1 to 20 C atoms, or having 2 to 20 C
  • R 11 - R 19 and R 110 contains one of the structures represented by the general formulae (II) - (IV):
  • R 13 and/or R 18 contain one of the structures shown in the general formulae (II)-(IV).
  • the one deuterated fused ring compound has the structure of the formula (V-1)-(V-3):
  • R 510 -R 545 are each independently H or D, or a linear alkyl group having 1 to 20 C atoms, an alkoxy group or a thioalkoxy group, or a branch or ring having 3 to 20 C atoms.
  • L represents a linking group which may be a single bond, or a substituted or unsubstituted, substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or deuterated or unsubstituted An aryloxy or heteroaryloxy group of 5 to 40 ring atoms, or a combination of these systems.
  • Ar 3 and Ar 4 are independently deuterated or undeuterated substituted or unsubstituted aromatic or heteroaromatic ring systems having 5 to 40 ring atoms, or deuterated or unsubstituted having 5 to 40 An aryloxy or heteroaryloxy group of a ring atom, or a combination of these systems.
  • n are each independently an integer of 0-6.
  • the present invention also provides a high polymer, the repeating unit of the high polymer comprising at least one of the structures represented by the general formula (I) and the general formula (V-1) - (V-3) losing at least one hydrogen A group formed after an atom.
  • the invention still further provides a mixture comprising the deuterated fused ring compound or polymer, and a second organic functional material.
  • the second organic functional material may be selected from 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), singlet illuminant (fluorescent illuminant), triplet illuminant (phosphorescent illuminant), thermally excited delayed fluorescent material (TADF material) and At least one of organic dyes.
  • HIM/HTM hole injection or transport material
  • HBM hole blocking material
  • EIM/ETM electron injecting or transporting material
  • EBM organic matrix material
  • TADF material thermally excited delayed fluorescent material
  • the present invention also provides a composition comprising a deuterated fused ring compound or polymer as described above, and an organic solvent.
  • the invention also provides an organic electronic device comprising the deuterated fused ring compound or polymer.
  • the organic electronic device can be selected from 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, and an organic spin.
  • OLED organic light emitting diode
  • OCV organic photovoltaic cell
  • OEEC organic light emitting cell
  • OFET organic field effect transistor
  • organic light emitting field effect transistor an organic laser
  • organic spin organic spin.
  • Electronic devices, organic sensors and organic plasmon emitting diodes Organic Plasmon Emitting Diode.
  • the organic electronic device is an organic electroluminescent device comprising at least one luminescent layer comprising the deuterated fused ring compound or polymer.
  • the deuterated fused ring compound according to the present invention can be used as a host material for preparing an organic electroluminescence element having blue luminescence, and a relatively long device life can be obtained with respect to a fused ring compound having no deuteration.
  • 101 is a substrate
  • 102 is an anode
  • 103 is a hole injection layer (HIL) or a hole transport layer (HTL)
  • 104 is a light-emitting layer
  • 105 is an electron injection layer (EIL) or an electron transport layer (ETL).
  • 106 is a cathode.
  • the host material In the present invention, the host material, the matrix material, the Host material, and the Matrix material have the same meaning and are interchangeable.
  • metal organic complexes metal organic complexes, metal organic complexes, and organometallic complexes have the same meaning and are interchangeable.
  • composition printing ink, ink, and ink have the same meaning and are interchangeable.
  • the present invention provides a deuterated fused ring compound of the formula (I):
  • R 11 -R 19 and R 110 are each independently H or D, or a linear alkyl group having 1 to 20 C atoms, an alkoxy group or a thioalkoxy group, or a branch having 3 to 20 C atoms. a chain or cyclic alkyl, alkoxy or thioalkoxy group, or a substituted or unsubstituted silyl group, or a substituted ketone group having 1 to 20 C atoms, or having 2 to 20 C
  • R 11 - R 19 and R 110 contains one of the structures represented by the general formulae (II) - (IV):
  • R 21 -R 25 , R 31 -R 37 and R 41 -R 47 at least one of them is a single bond to the formula (I), and the rest is H.
  • At least one of R 11 -R 19 and R 110 may be independently selected from H, D, or A substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, preferably a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 30 ring atoms, more preferably A substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms.
  • the aromatic ring system contains from 5 to 15 carbon atoms, more preferably from 5 to 10 carbon atoms in the ring system;
  • the heteroaromatic ring system contains from 2 to 15 carbon atoms in the ring system. More preferably, it is 2 to 10 carbon atoms, and at least one hetero atom, provided that the total number of carbon atoms and hetero atoms is at least 4.
  • the hetero atom is 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, and more particularly preferably selected from N, O or S.
  • the above aromatic ring system or aromatic group means a hydrocarbon group containing at least one aromatic ring, and includes a monocyclic group and a polycyclic ring system.
  • the heteroaromatic ring or heteroaromatic group described above refers to a hydrocarbon group (containing a hetero atom) containing at least one heteroaromatic ring, and includes a monocyclic group and a polycyclic ring system.
  • 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 rings of the polycyclic ring is aromatic or heteroaromatic.
  • aromatic or heteroaromatic ring systems include not only aromatic or heteroaromatic systems, but also multiple aryl or heteroaryl groups may also be interrupted by short non-aromatic units ( ⁇ 10%).
  • 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, etc., are also considered to be aromatic ring systems for the purposes of the present invention.
  • examples of the aromatic group are: benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, anthracene, benzopyrene, triphenylene, anthracene, anthracene, snail, and derivatives thereof.
  • heteroaromatic groups are: furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole , thiazole, tetrazole, anthracene, oxazole, pyrroloimidazole, pyrrolopyrrol, thienopyrrole, thienothiophene, furopyrrol, furanfuran, thienofuran, benzisoxazole, benzisothiazole , benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthyridine, quinoxaline, phenanthridine, pyridine, quinazoline, quinazolinone,
  • R 11 -R 19 and R 110 may be further selected from H, D or a combination of one or more of the following structural groups:
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 respectively represent CR 3 or N;
  • R 11 -R 19 and R 110 may also be selected from H, D or a combination of one or more of the following structural groups, wherein H on the ring may be optionally substituted:
  • R 13 and/or R 18 in the deuterated fused ring compound contains one of the structures shown in the general formulae (II) to (IV).
  • R 11 , R 12 , R 14 , R 15 -R 17 , R 19 and R 110 are each independently H or D, or substituted or unsubstituted having 5 to 40 ring atoms.
  • the group-bonded ring forms a monocyclic or polycyclic aliphatic or aromatic ring system; one or more of the various groups described above may be further substituted with D.
  • R 11 , R 12 , R 14 , R 15 -R 17 , R 19 and R 110 are each independently H, or D, or have a substitution of 5 to 10 ring atoms or An unsubstituted aromatic or heteroaromatic ring system, or an aryloxy or heteroaryloxy group having 5 to 10 ring atoms, or a combination of these systems, wherein one or more of the groups may be and/or The ring bonded to the group forms a monocyclic or polycyclic aliphatic or aromatic ring system; one or more of the various groups described above may be further substituted with D.
  • R 11 , R 12 , R 14 , R 15 -R 17 , R 19 and R 110 are each independently H or D.
  • Ar 1 and Ar 2 are each independently selected from one of the structures shown in (II)-(IV).
  • the one deuterated fused ring compound has the structure shown by the general formulae (V-1)-(V-3):
  • R 510 -R 545 are each independently H or D, or a straight-chain alkyl group having 1 to 20 C atoms, alkoxy or thioalkoxy groups, or branched chain having 3-20 C atoms or cycloalkyl An alkyl, alkoxy or thioalkoxy group, or a substituted or unsubstituted silyl group, or a substituted ketone group having 1 to 20 C atoms, or an alkane having 2 to 20 C atoms.
  • the one deuterated fused ring compound has the structure of the formula (V'-1)-(V'-3):
  • R 512 -R 517 , R 518 -R 522 , R 531 -R 535 and R 543 -R 547 are each independently substituted or unsubstituted substituted or unsubstituted aromatic having 5 to 20 ring atoms or A heteroaromatic ring system, or an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, deuterated or undeuterated, or a combination of these systems. And adjacent substituent groups may form an aromatic or heteroaromatic ring system having 5 to 20 ring atoms with each other.
  • L represents a linking group which may be a single bond, or a substituted or unsubstituted, substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or deuterated or unsubstituted An aryloxy or heteroaryloxy group of 5 to 40 ring atoms, or a combination of these systems.
  • L represents a single bond
  • L is a substituted or unsubstituted, substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms, or deuterated or undeuterated having 5 An aryloxy or heteroaryloxy group of up to 20 ring atoms, or a combination of these systems.
  • Ar 3 and Ar 4 are each independently deuterated or deuterated substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or deuterated or deuterated having 5-40 An aryloxy or heteroaryloxy group of a ring atom, or a combination of these systems.
  • Preferred are deuterated or undeuterated substituted or unsubstituted aromatic or heteroaromatic ring systems having 5 to 20 ring atoms, or deuterated or undeuterated aryloxy groups having 5 to 20 ring atoms. Or a heteroaryloxy group, or a combination of these systems.
  • Preferred embodiments of Ar 3 and Ar 4 are the same as those described above for the aromatic or heteroaromatic groups of R 11 -R 19 and R 110 .
  • n and n are each independently an integer of 0-6, preferably an integer of 0-3, more preferably an integer of 0-2, most preferably 0 or 1.
  • a specific example of a deuterated fused ring compound according to the present invention is as follows, but is not limited thereto:
  • the present invention also relates to a method for synthesizing the above-described deuterated fused ring compound, which comprises carrying out a reaction using a raw material containing a reactive group.
  • active starting materials comprise structural units of the above formula and, in each case, at least one leaving group, for example bromine, iodine, boric acid or boric acid ester.
  • Suitable reactions to form C-C linkages are well known to those skilled in the art and are described in the literature.
  • Particularly suitable and preferred coupling reactions are SUZUKI, STILLE and HECK coupling reactions.
  • the present invention still further relates to a high polymer having a repeating unit comprising a group formed by losing a structure of at least one H as shown in the formula (I).
  • the high polymer is a non-conjugated high polymer wherein the structural unit of formula (I) is on the side chain.
  • the high polymer is a conjugated high polymer.
  • the present invention also provides a mixture comprising the above-described deuterated fused ring compound or polymer, and a second organic functional material.
  • the second organic functional material may be selected from 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), singlet emitter (fluorescent emitter), triplet emitter (phosphorescent emitter), thermally excited delayed fluorescent material (TADF material) and At least one of machine dyes.
  • Various 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 second organic functional material is a fluorescent illuminant (or singlet illuminant) material.
  • the deuterated fused ring compound or polymer is used as a host guest, and the fluorescent illuminant is used as a guest.
  • the weight percentage of the guest is ⁇ 15 wt%, preferably ⁇ 12 wt%, more preferably ⁇ 9 wt%, more preferably ⁇ 8 wt%. Preferably, it is ⁇ 7 wt%.
  • the deuterated fused ring compound or polymer can be used as a co-host material having a weight ratio to the fluorescent host material of from 3:7 to 7:3.
  • the second organic functional material is a fluorescent host material and a TADF material.
  • the second organic functional material is a fluorescent host material and an HTM material.
  • HTM singlet matrix materials
  • singlet emitters singlet emitters
  • Suitable organic HIM/HTM materials may optionally comprise compounds having the following structural units: phthalocyanine, porphyrin, amine, aromatic amine, biphenyl triarylamine, thiophene, thiophene such as dithienothiophene and thiophene, pyrrole, aniline , carbazole, azide and azepine and their derivatives.
  • suitable HIMs also include self-assembling monomers such as compounds containing phosphonic acid and sliane derivatives; metal complexes and crosslinking compounds and the like.
  • An electron blocking layer is used to block electrons from adjacent functional layers, particularly the luminescent layer.
  • the electron blocking material (EBM) of the electron blocking layer (EBL) requires a higher LUMO than an adjacent functional layer such as a light emitting layer.
  • the HBM has a larger excited state level than the adjacent luminescent layer, such as a singlet or triplet, depending on the illuminant, while the EBM has a hole transport function.
  • HIM/HTM materials that typically have high LUMO levels can be used as EBMs.
  • cyclic aromatic amine-derived compounds useful as HIM, HTM or EBM include, but are not limited to, the following general structures:
  • Each of Ar 1 to Ar 9 may be independently selected from the group consisting of a cyclic aromatic hydrocarbon compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalrene, phenanthrene, anthracene, anthracene, fluorene, anthracene, anthracene; Heterocyclic compounds such as dibenzothiophene, dibenzofuran, furan, thiophene, benzofuran, benzothiophene, oxazole, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, evil Triazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, acesulfazine, oxadiazine, hydrazine
  • Ar 1 to Ar 9 may be independently selected from the group consisting of:
  • n is an integer from 1 to 20; X 1 to X 8 are CH or N; and Ar 1 is as defined above.
  • metal complexes that can be used as HTM or HIM include, but are not limited to, the following general structures:
  • M is a metal having an atomic weight greater than 40
  • (Y 1 -Y 2 ) is a two-dentate ligand, Y 1 and Y 2 are independently selected from C, N, O, P and S; L is an ancillary ligand; m is an integer from 1 to The maximum coordination number of this metal; m+n is the maximum coordination number of this metal.
  • (Y 1 -Y 2 ) is a 2-phenylpyridine derivative.
  • (Y 1 -Y 2 ) is a carbene ligand.
  • M is selected from Ir, Pt, Os, and Zn.
  • the HOMO of the metal complex is greater than -5.5 eV (relative to the vacuum level).
  • the example of the singlet host material is not particularly limited, and any organic compound may be used as the host as long as its singlet energy is higher than that of the illuminant, particularly the singlet illuminant or the luminescent illuminant.
  • Examples of the organic compound used as the singlet host material may be selected from the group consisting of a cyclic aromatic compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, anthracene, phenanthrene, anthracene, anthracene, fluorene, fluorene, fluorene, An aromatic heterocyclic compound such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, oxazole, carbazole, pyridine Anthraquinone, pyrrole dipyridine, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, triazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrim
  • the singlet host material can be selected from compounds comprising at least one of the following groups:
  • R 1 may be independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl;
  • Ar 1 is an aryl group Or a heteroaryl group, which has the same meaning as Ar 1 defined in the above HTM;
  • n is 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 .
  • Singlet emitters tend to have longer conjugated pi-electron systems.
  • styrylamine and its derivatives disclosed in JP 2913116 B and WO 2001021729 A1
  • indenoindenes and derivatives thereof disclosed in WO 2008/006449 and WO 2007/140847.
  • the singlet emitter can be selected from the group consisting of monostyrylamine, dibasic styrylamine, and ternary benzene. Vinylamine, 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, the entire contents of which are hereby incorporated by reference. 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.
  • 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
  • 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 ( ⁇ Est), and triplet excitons can be converted into singlet exciton luminescence by anti-intersystem 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 material structure is controllable, the property is stable, the price is cheap, no precious metal is needed, and the application prospect in the OLED field is broad.
  • the TADF material needs to have a small singlet-triplet energy level difference, preferably ⁇ Est ⁇ 0.3 eV, and secondly ⁇ Est ⁇ 0.2 eV, preferably ⁇ Est ⁇ 0.1 eV.
  • the TADF material has a relatively small ⁇ Est, and in another preferred embodiment, the TADF has a better fluorescence quantum efficiency.
  • 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:
  • the deuterated fused ring compound or polymer is used in an evaporated OLED device.
  • the molecular weight of the deuterated fused ring compound or polymer is ⁇ 1000 mol/kg, preferably ⁇ 900 mol/kg, very preferably ⁇ 850 mol/kg, more preferably ⁇ 800 mol/kg, most preferably ⁇ 700 mol/kg.
  • Another object of the invention is to provide a material solution for printing OLEDs.
  • the deuterated fused ring compound or polymer has a molecular weight of ⁇ 700 mol/kg, preferably ⁇ 900 mol/kg, very preferably ⁇ 900 mol/kg, more preferably ⁇ 1000 mol/kg, most preferably ⁇ 1100 mol/kg.
  • the halo fused ring compound or polymer has a solubility in toluene of > 10 mg/ml, preferably > 15 mg/ml, most preferably > 20 mg/ml at 25 °C.
  • the present invention also provides a composition comprising the deuterated fused ring compound or polymer, and a first organic solvent.
  • the deuterated fused ring compound can be used as a host material in the composition.
  • the composition further comprises a singlet emitter material.
  • the composition further comprises a host material and a singlet emitter.
  • the composition comprises at least two host materials and a singlet emitter.
  • the composition further comprises a host material and a thermally activated delayed fluorescent luminescent material.
  • the composition further comprises a hole transporting material (HTM), and more preferably, the HTM comprises a crosslinkable group.
  • HTM hole transporting material
  • the composition according to the invention is a solution.
  • composition according to the invention is a suspension.
  • composition in the examples of the present invention may comprise from 0.01 to 20% by weight of a deuterated fused ring compound or polymer, preferably from 0.1 to 15% by weight, more preferably from 0.2 to 10% by weight, most preferably from 0.25 to 5 wt% deuterated fused ring compound or polymer.
  • a composition according to the invention wherein the first organic solvent is selected from the group consisting of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether An alicyclic or olefinic compound, or an inorganic ester compound such as a boronic acid ester or a phosphate ester, or a mixture of two or more solvents.
  • a composition according to the invention comprises at least 50% by weight of an aromatic or heteroaromatic solvent; preferably at least 80% by weight of an aromatic or heteroaromatic solvent; particularly preferably at least 90% by weight Aromatic or heteroaromatic solvents.
  • aromatic or heteroaromatic-based first organic solvent examples include, but not limited to, 1-tetralone, 3-phenoxytoluene, acetophenone, 1-methoxynaphthalene, p- Diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, o-di Ethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, ten Dialkylbenzene, 1-methylnaphthalene, 1,2,4-t
  • suitable and preferred first organic solvents are aliphatic, cycloaliphatic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, glycols or polyols. .
  • the alcohol represents a suitable class of first organic solvent.
  • Preferred alcohols include alkylcyclohexanols, especially methylated aliphatic alcohols, naphthols and the like.
  • the first organic solvent may be a cycloalkane such as decalin.
  • the first organic solvent may be used singly or as a mixture of two or more organic solvents.
  • the composition according to the present invention further comprises a second organic solvent, examples of which include, but are not limited to, methanol, ethanol, 2-methoxyethanol, dichloro Methane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, A Ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate Esters, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, hydrazine and/or mixtures thereof.
  • a second organic solvent examples of which include,
  • the organic solvent particularly suitable for the present invention is a solvent having Hansen solubility parameters in the following ranges:
  • ⁇ d (dispersion force) is in the range of 17.0 to 23.2 MPa 1/2 , especially in the range of 18.5 to 21.0 MPa 1/2 ;
  • ⁇ p polar forces in the range of 0.2 ⁇ 12.5MPa 1/2, especially in the 2.0 ⁇ 6.0MPa 1/2;
  • the organic solvent is selected in consideration of its boiling point parameter.
  • the organic solvent has a boiling point of ⁇ 150 ° C; preferably ⁇ 180 ° C; more preferably ⁇ 200 ° C; more preferably ⁇ 250 ° C; optimally ⁇ 275 ° C or ⁇ 300 ° C.
  • the boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.
  • the organic solvent can be evaporated from the solvent system to form a film comprising the functional material.
  • composition :
  • the surface tension is at 25 ° C, in the range of 19 dyne / cm (dyne / cm) to 50 dyne / cm.
  • the organic solvent is selected in consideration of its surface tension parameter. Suitable ink surface tension parameters are suitable for a particular substrate and a particular printing method.
  • the organic solvent has a surface tension at 25 ° C of from about 19 dyne / cm to 50 dyne / cm; more preferably from 22 dyne / cm to 35 dyne / cm; Most preferably in the range of 25 dyne/cm to 33 dyne/cm.
  • the ink according to the invention has a surface tension at 25 ° C in the range of from about 19 dyne/cm to 50 dyne/cm; more preferably in the range of from 22 dyne/cm to 35 dyne/cm; preferably in 25 dyne/ Cm to the 33dyne/cm range.
  • compositions according to the invention wherein the organic solvent is selected taking into account the viscosity parameters of the ink.
  • the viscosity can be adjusted by different methods, such as by the selection of a suitable organic solvent and the concentration of the functional material in the ink.
  • the organic solvent has a viscosity of less than 100 cps; more preferably less than 50 cps; most preferably from 1.5 to 20 cps.
  • the viscosity herein refers to the viscosity at ambient temperature at the time of printing, and is usually 15 to 30 ° C, preferably 18 to 28 ° C, more preferably 20 to 25 ° C, and most preferably 23 to 25 ° C.
  • Compositions so formulated will be particularly suitable for ink jet printing.
  • the composition according to the invention has a viscosity at 25 ° C in the range of from about 1 cps to about 100 cps; 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.
  • the ink obtained by the organic solvent satisfying the above boiling point and surface tension parameters and viscosity parameters can form a functional material film having uniform thickness and composition properties.
  • Another object of the present invention is to provide the use of the above-described deuterated fused ring compounds and polymers in organic electronic devices.
  • the organic electronic device can be selected from 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, and an organic spintronic device.
  • OLED organic light emitting diode
  • OCV organic photovoltaic cell
  • OEEC organic light emitting cell
  • OFET organic field effect transistor
  • OLED organic light emitting field effect transistor
  • Another object of the present invention is to provide a method of preparing the above organic electronic device
  • the method comprises: forming a functional layer on a substrate by evaporation of the above-mentioned deuterated fused ring compound, high polymer or mixture; or co-evaporating the deuterated fused ring compound or polymer with a co-evaporation method
  • the two organic functional materials together form a functional layer on a substrate; or the above composition is applied to a substrate by printing or coating to form a functional layer.
  • the method of printing or coating may be selected from, but 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, slit-type extrusion coating, etc.
  • the invention further relates to the use of the composition as a printing ink in the preparation of an organic electronic device, 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 functional layer has a thickness of from 5 nm to 1000 nm.
  • the invention further relates to an organic electronic device comprising the deuterated fused ring compound or polymer.
  • the organic electronic device can include a functional layer that is prepared using the composition.
  • 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 a deuterated fused ring compound or polymer as described above.
  • the organic electronic device described above is an electroluminescent device, particularly an OLED.
  • the organic electronic device includes a substrate 101, an anode 102, and at least one Light-emitting layer 104, a cathode 106.
  • the substrate 101 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 102 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.
  • Cathode 106 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, 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 further include other functional layers such as a hole injection layer (HIL) or a hole transport layer (HTL) 103, an electron blocking layer (EBL), an electron injection layer (EIL) or an electron transport layer (ETL) 105, and a hole. Barrier layer (HBL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL Barrier layer
  • the luminescent layer 104 is by vacuum evaporation, the source of which includes the deuterated fused ring compound or polymer.
  • the luminescent layer 104 is prepared by printing the composition.
  • the electroluminescent 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.
  • the present invention also relates to the use of the organic electronic device in various electronic devices, including, but not limited to, display devices, Lighting equipment, light sources, sensors, etc.
  • the invention further relates to an electronic device comprising an organic electronic device according to the invention, including, but not limited to, a display device, a lighting device, a light source, a sensor and the like.
  • HIL a triarylamine derivative
  • HTL a triarylamine derivative
  • Dopant anthraquinone derivative.
  • a, cleaning of the conductive glass substrate when used for the first time, can be washed with a variety of solvents, such as chloroform, ketone, isopropyl alcohol, and then UV ozone plasma treatment;
  • HIL 50 nm
  • HTL 35 nm
  • EML 25 nm
  • ETL 28 nm
  • cathode LiQ / Al (1nm / 150nm) in a high vacuum (1 ⁇ 10 -6 mbar) in the thermal evaporation;
  • the device is encapsulated in a nitrogen glove box with an ultraviolet curable resin.
  • 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. It has been found that the color coordinates of the blue light device prepared by using Compound 1 - Compound 5 as the main body of the EML layer are better than that of Comparative Compound 1, for example, the color coordinates of the device prepared by Compound 5 are (0.149, 0.086); 5
  • the luminous efficiency of the blue light device prepared as the main body of the EML layer is in the range of 6-8 cd/A, which has more excellent luminous efficiency. In terms of device lifetime, the lifetime of the blue light device prepared by using Compound 1 - Compound 5 as the main body of the EML layer is further improved.
  • a device superior to Comparative Compound 1, such as Compound 5, has a T95 of greater than 1000 hours at 1000 nits.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé cyclique fusionné deutéré, un polymère, un mélange et une composition, et son application dans un dispositif électronique organique, en particulier son application dans une diode électroluminescente organique. L'invention concerne également un dispositif électronique organique, en particulier une diode électroluminescente organique, comprenant le composé cyclique fusionné deutéré, et son application dans le domaine de la technologie d'affichage et d'éclairage. Au moyen d'une optimisation de structure de dispositif, une meilleure performance de ce dernier peut être obtenue, en particulier un dispositif OLED ayant une performance élevée peut être réalisé, ce qui permet d'obtenir de meilleures options de matériaux et de techniques de préparation pour l'affichage en couleur et l'application d'éclairage.
PCT/CN2017/112705 2016-11-23 2017-11-23 Composé cyclique fusionné deutéré, polymère, mélange et composition, et dispositif électronique organique Ceased WO2018095384A1 (fr)

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