Composition and its application in optoelectronic field

Abstract

Disclosed is a composition comprising at least one compound having a structural unit of chemical formula (1) or (2) and an organic resin; the organic resin can be easily formed into a thin film by printing or coating, and can be cured by heating or ultraviolet curing; the photoluminescence spectrum of the compound has a narrow half-width at half maximum, and a color conversion layer made with the compound can absorb incident light with a wide half-width at half maximum and then emit outgoing light with a narrow half-width at half maximum; the peak position of the photoluminescence spectrum of the compound can be adjusted by modifying its molecular structure, and different types of color conversion layers can be prepared using compounds with different chemical structures, each capable of emitting a spectrum of different colors. These different-color narrow half-width light-emitting devices can be used to manufacture display devices with a high color gamut.

Description

Technical Field

[0001] The present invention relates to the field of organic optoelectronic materials and technologies, and in particular to an organic composition, an organic film comprising or prepared from the organic composition, and applications thereof in the optoelectronic field. Background Art

[0002] According to the principles of colorimetry, the narrower the half-width at half-maximum of light entering the human eye, the higher the color purity and the brighter the color. Display devices made with red, green, and blue primary colors with narrow half-width at half-maximum display a wide color gamut, realistic images, and high-quality images.

[0003] Currently, there are two mainstream approaches to achieving full-color displays. The first involves display devices actively emitting light in the three primary colors of red, green, and blue, a typical example being RGB-OLED displays. The currently mature technology uses vacuum evaporation with fine metal masks to produce three-color light-emitting devices. This process is complex, costly, and difficult to achieve high-resolution displays exceeding 600ppi. The second approach involves using a color converter to convert the single-color light emitted by the light-emitting device into multiple colors, thereby achieving full-color display. For example, Samsung's blue OLED combined with red and green quantum dot (QD) films acts as a color converter. The light-emitting device in this approach features simple manufacturing processes and high yield rates. Furthermore, the color converter can be implemented through various technologies, such as evaporation, inkjet printing, transfer printing, and photolithography. This allows for applications in display products with varying resolution requirements, ranging from as low as 50ppi for large-screen TVs to over 3000ppi for silicon-based microdisplays.

[0004] Currently, there are two main types of color conversion materials used in mainstream color converters. One is inorganic nanocrystals, commonly known as quantum dots. These are nanoparticles (specifically quantum dots) of inorganic semiconductor materials (such as InP, CdSe, CdS, and ZnSe) with diameters ranging from 2 to 8 nm. Due to the limitations of current quantum dot synthesis and separation technology, the half-width (FWHM) of the emission peak of Cd-containing quantum dots currently ranges from 25 to 40 nm, with color purity that meets NTSC display requirements. The FWHM of Cd-free quantum dots ranges from 35 to 75 nm. However, due to the environmental pollution and serious toxicity of Cd to human health, the use of Cd-containing quantum dots in electronic products is prohibited in most countries. Furthermore, inorganic quantum dot dispersions are essentially suspensions. To ensure stability and uniform distribution after film formation, stabilizers and dispersants must be added, as disclosed in CN110799621A. Therefore, developing a suitable composition for printing or coating quantum dots is crucial and challenging. Furthermore, the extinction coefficient is generally low, requiring thicker films, typically over 10 microns, to fully absorb blue light. This poses a significant challenge for mass production, particularly for Samsung's blue-light OLEDs with red and green quantum dots. The second type of material is organic dyes, including various organic conjugated small molecules with chromophores. While these dyes generally have high extinction coefficients, due to intramolecular thermal relaxation and the high vibrational energy within the organic molecules, the emission peaks of these materials are broad, typically exceeding 60 nm at half maximum. Furthermore, color converters or thin films are typically prepared using solution processing. Currently used organic conjugated systems are relatively rigid and have limited solubility in organic solvents, resulting in poor processability and making them difficult to use in the preparation of blue-light-plus-color converter displays.

[0005] In three patent applications filed concurrently with the present invention, the inventors disclosed small molecule and polymer materials with narrow half-widths, but compositions suitable for printing or coating processes (ie, printing inks) still need to be developed. Summary of the Invention

[0006] Based on this, the object of the present invention is to provide an organic composition and its application in the optoelectronic field.

[0007] The specific technical solutions are as follows:

[0008] The present invention provides a composition comprising:

[0009] 1) at least one organic resin;

[0010] 2) at least one compound comprising a structural unit represented by chemical formula (1) or (2),

[0011]

[0012] The symbols and marks used have the following meanings:

[0013] Ar 1 ~Ar 3 the same or different ones selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms;

[0014] Ar 4 ~Ar 5 the same or different selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms;

[0015] When Ar 4 ~Ar 5 When not empty, X a , X b Selected from N, C(R 9 )、Si(R 9 );Y a , Y b Selected from B, P=O, C(R 9 )、Si(R 9 );

[0016] When Ar 4 ~Ar 5 When it is empty, the corresponding X a or Y b Selected from N(R 9 )、C(R 9 R 10 )、Si(R 9 R 10 )、C=O、O、C=N(R 9 ), C=C(R 9 R 10 )、P(R 9 ), P(=O)R 9 , S, S=O or SO2, X b Selected from N, C(R 9 )、Si(R 9 ), Y a Selected from B, P=O, C(R 9 )、Si(R 9 );

[0017] X 1 、X 2 is empty or a bridging group;

[0018] R 4 ~R 10and -H, D, -F, -Cl, Br, I, -CN, -NO2, -CF3, a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group or a silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)NH2), a cyclopent ... )-X wherein X represents a halogen atom), a formyl group (-C(=O)-H), an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamino or heteroarylamino group having 5 to 40 ring atoms, a disubstituted unit at any position of the above substituents or a combination of these systems, wherein one or more substituents can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bonded.

[0019] Preferably, the composition further comprises at least one solvent.

[0020] The present invention also provides an organic functional material film, which is prepared using the above-mentioned composition.

[0021] The present invention also provides a photoelectric device comprising the organic functional material film as described above.

[0022] Beneficial effects: A composition according to the present invention is very suitable for use in inks for printing or coating processes; and the compounds contained in the composition have a narrow luminescence half-width and a large extinction coefficient, which is convenient for preparing various color converters for realizing displays with a high color gamut. DETAILED DESCRIPTION

[0023] The present invention can be implemented in many different forms and is not limited to the embodiments described herein. Instead, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this invention pertains. The terms used herein in the specification of the present invention are for the purpose of describing specific embodiments only and are not intended to limit the present invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0025] In the present invention, main body material, matrix material, host material and matrix material have the same meaning and can be interchanged.

[0026] In the present invention, metal organic complex, metal organic complex and organometallic complex have the same meaning and can be used interchangeably.

[0027] In the present invention, composition, printing ink, ink, and ink have the same meaning and can be interchanged.

[0028] The present invention provides a composition comprising:

[0029] 1) at least one organic resin;

[0030] 2) at least one compound comprising a structural unit represented by chemical formula (1) or (2),

[0031]

[0032] The symbols and marks used have the following meanings:

[0033] Ar 1 ~Ar 3 the same or different ones selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms;

[0034] Ar 4 ~Ar 5 the same or different selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms;

[0035] When Ar 4 ~Ar 5 When not empty, X a , X b Selected from N, C(R 9 )、Si(R 9 );Y a , Y b Selected from B, P=O, C(R 9 )、Si(R 9 );

[0036] When Ar 4 ~Ar 5 When it is empty, the corresponding X a or Y b Selected from N(R 9 )、C(R 9 R 10 )、Si(R 9 R 10 )、C=O、O、C=N(R 9 ), C=C(R 9R 10 )、P(R 9 ), P(=O)R 9 , S, S=O or SO2, X b Selected from N, C(R 9 )、Si(R 9 ), Y a Selected from B, P=O, C(R 9 )、Si(R 9 );

[0037] X 1 、X 2 is empty or a bridging group;

[0038] R 4 ~R 10 and -H, D, -F, -Cl, Br, I, -CN, -NO2, -CF3, a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group or a silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)NH2), a cyclopent ... )-X wherein X represents a halogen atom), a formyl group (-C(=O)-H), an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamino or heteroarylamino group having 5 to 40 ring atoms, a disubstituted unit at any position of the above substituents or a combination of these systems, wherein one or more substituents can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bonded.

[0039] In a preferred embodiment, the composition comprises two or more organic resins. In another preferred embodiment, the composition comprises three or more organic resins. For the purposes of the present invention, the organic resin refers to a resin prepolymer or a resin formed after crosslinking or curing.

[0040] Organic resins suitable for the present invention include, but are not limited to, polystyrene, polyacrylate, polymethacrylate, polycarbonate, polyurethane, polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl chloride, polybutylene, polyethylene glycol, polysiloxane, polyacrylate, epoxy resin, polyvinyl alcohol, polyacrylonitrile, polyvinylidene chloride (PVDC), polystyrene-acrylonitrile (SAN), polybutylene terephthalate (PBT), polyethylene terephthalate (PET), polyvinyl butyrate (PVB), polyvinyl chloride (PVC), polyamide, polyoxymethylene, polyimide, polyetherimide, or mixtures thereof.

[0041] Furthermore, organic resins suitable for the present invention include but are not limited to those formed by homopolymerization or copolymerization of the following monomers (resin prepolymers): styrene derivatives, acrylate derivatives, acrylonitrile derivatives, acrylamide derivatives, vinyl ester derivatives, vinyl ether derivatives, maleimide derivatives, and conjugated diene derivatives.

[0042] Examples of styrene derivatives include alkylstyrenes such as α-methylstyrene, o-, m- and p-methylstyrene, p-butylstyrene, especially p-tert-butylstyrene, and alkoxystyrenes such as p-methoxystyrene, p-butoxystyrene and p-tert-butoxystyrene.

[0043] Examples of acrylate derivatives include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl meth ...ethyl acrylate, 2-hydroxypropyl acrylate 2-Hydroxybutyl methacrylate, 2-Hydroxybutyl methacrylate, 3-Hydroxybutyl acrylate, 3-Hydroxybutyl methacrylate, 4-Hydroxybutyl acrylate, 4-Hydroxybutyl methacrylate, Allyl acrylate, Allyl methacrylate, Benzyl acrylate, Benzyl methacrylate, Cyclohexyl acrylate, Cyclohexyl methacrylate, Phenyl acrylate, Phenyl methacrylate, 2-Methoxyethyl acrylate, 2-Methoxyethyl methacrylate, 2-Phenoxyethyl acrylate, 2-Phenoxyethyl methacrylate, Methoxydiglycol acrylate, Methoxydiglycol methacrylate, Methoxytriglycol acrylate, Methoxy Oxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate, adamantyl (meth)acrylate, norbornyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glyceryl monoacrylate and glyceryl monomethacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate Methylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, N,N-dimethyl-1,3-propylenediamine benzyl (meth)acrylate, 3-dimethylaminopropyl acrylate and 3-dimethylaminopropyl methacrylate; glycidyl acrylate and glycidyl methacrylate;

[0044] Examples of acrylonitrile derivatives are: acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and vinylidene cyanide;

[0045] Examples of acrylamide derivatives are: acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide and N-2-hydroxyethylmethacrylamide;

[0046] Examples of vinyl ester derivatives are: vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate;

[0047] Examples of vinyl ether derivatives are vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether;

[0048] Examples of maleimide derivatives are maleimide, benzylmaleimide, N-phenylmaleimide and N-cyclohexylmaleimide;

[0049] Examples of conjugated diene derivatives are: 1,3-butadiene, isoprene, and chloroprene;

[0050] The homopolymer or copolymer can be prepared by, for example, free radical polymerization, cationic polymerization, anionic polymerization or organometallic catalytic polymerization (such as Ziegler-Natta catalysis). The polymerization process can be suspension polymerization, emulsion polymerization, solution polymerization or bulk polymerization.

[0051] The organic resin generally has an average molar mass Mn (determined by GPC) of 10,000 to 1,000,000 g / mol, preferably 20,000 to 750,000 g / mol, more preferably 30,000 to 500,000 g / mol.

[0052] In some preferred embodiments, the organic resin is a thermosetting resin or an ultraviolet (UV) curable resin.In some embodiments, the organic resin is cured using a method that will facilitate roll-to-roll processing.

[0053] Thermosetting resins require curing, during which they undergo an irreversible molecular crosslinking process that renders the resin infusible. In some embodiments, the thermosetting resin is an epoxy resin, a phenolic resin, a vinyl resin, a melamine resin, a urea-formaldehyde resin, an unsaturated polyester resin, a polyurethane resin, an allyl resin, an acrylic resin, a polyamide resin, a polyamide-imide resin, a phenolamine polycondensation resin, a urea-melamine polycondensation resin, or a combination thereof.

[0054] In some embodiments, the thermosetting resin is an epoxy resin. Epoxy resins cure easily without volatile emissions or byproducts from a wide range of chemicals. Epoxy resins are also compatible with most substrates and tend to wet surfaces easily. See Boyle, MA et al., "Epoxy Resins," Composites, Vol. 21, ASM Handbook, pages 78-89 (2001).

[0055] In some embodiments, the organic resin is a silicone thermosetting resin. In some embodiments, the silicone thermosetting resin is 0E6630A or 0E6630B (Dow Corning Corporation (Auburn, Michigan)).

[0056] In some embodiments, a thermal initiator is used. In some embodiments, the thermal initiator is AIBN [2,2'-azobis(2-methylpropionitrile)] or benzoyl peroxide.

[0057] UV curable resins are polymers that cure and harden quickly when exposed to light of a specific wavelength. In some embodiments, UV curable resins are resins having free radical polymerization groups, such as (meth)acryloyloxy groups, vinyloxy groups, styryl groups, or vinyl groups, or cationic polymerizable groups as functional groups; and cationic polymerizable groups such as epoxy groups, thioepoxy groups, vinyloxy groups, or oxetane groups. In some embodiments, UV curable resins are polyester resins, polyether resins, (meth)acrylic resins, epoxy resins, polyurethane resins, alkyd resins, spiroacetal resins, polybutadiene resins, or thioolefin resins.

[0058] In some embodiments, the UV curable resin is selected from the group consisting of polyurethane acrylate, allyloxylated cyclohexyl diacrylate, bis(acryloyloxyethyl)hydroxyisocyanurate, bis(acryloyloxyneopentyl glycol) adipate, bisphenol A diacrylate, bisphenol A dimethacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,3-butanediol diacrylate, 1,3-butanediol dimethacrylate, dicyclopentyl diacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol monohydroxypentaacrylate, di(trimethylolpropane) tetraacrylate, triethylene glycol dimethacrylate, glyceryl methacrylate, 1,6-hexanediol diacrylate, neopentyl glycol dimethacrylate, neopentyl glycol hydroxypivalic acid diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate. Acrylates, phosphoric acid dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene glycol diacrylate, tetrabromobisphenol A diacrylate, triethylene glycol divinyl ether, triglycerol diacrylate, trimethylolpropane triacrylate, tripropylene glycol diacrylate, tris(acryloyloxyethyl) isocyanurate, phosphoric acid triacrylate, phosphoric acid diacrylate, monopropyl acrylate, vinyl-terminated polydimethylsiloxane, vinyl-terminated diphenylsiloxane-dimethylsiloxane copolymer, vinyl-terminated polyphenylmethylsiloxane, vinyl-terminated difluoromethylsiloxane-dimethylsiloxane copolymer, vinyl-terminated diethylsiloxane-dimethylsiloxane copolymer, vinylmethylsiloxane, monomethacryloxypropyl-terminated polydimethylsiloxane, monovinyl-terminated polydimethylsiloxane, monoallyl-monotrimethylsiloxy-terminated polyethylene oxide, and combinations thereof.

[0059] In some embodiments, the UV curable resin is a thiol functional compound that can be crosslinked with an isocyanate, epoxy resin, or unsaturated compound under UV curing conditions. In some embodiments, the thiol functional compound is a polythiol. In some embodiments, the polythiol is pentaerythritol tetrakis (3-mercaptopropionate) (PETMP); trimethylolpropane tris (3-mercaptopropionate) (TMPMP); ethylene glycol di (3-mercaptopropionate) (GDMP); tris [25- (3-mercapto-propionyloxy) ethyl] isocyanurate (TEMPIC); dipentaerythritol hexa (3-mercaptopropionate) (Di-PETMP); ethoxylated trimethylolpropane tris (3-mercaptopropionate) (ETTMP 1300 and ETTMP 700); polycaprolactone tetrakis (3-mercaptopropionate) (PCL4MP1350); pentaerythritol tetrakis mercaptoacetate (PETMA); trimethylolpropane tris mercaptoacetate (TMPMA); or ethylene glycol dimercaptoacetate (GDMA). These compounds are commercially available from Bruno Bock (Marschacht, Germany) under the trade name sell.

[0060] In some embodiments, the UV curable resin further comprises a photoinitiator. The photoinitiator will initiate a crosslinking and / or curing reaction of the photosensitive material during exposure to light. In some embodiments, the photoinitiator is an acetophenone-based, benzoin-based, or thioxanthone-based compound that can initiate polymerization of monomers for crosslinking and curing.

[0061] In some embodiments, the UV curable resin comprises a mercapto functional compound and a methacrylate, acrylate, isocyanate, or a combination thereof. In some embodiments, the UV curable resin comprises a polythiol and a methacrylate, acrylate, isocyanate, or a combination thereof.

[0062] In some embodiments, the photoinitiator is MINS-311RM (Minuta Technology Co., Ltd (Korea)).

[0063] In some embodiments, the photoinitiator is 127. 184. 184D, 2022, 2100, 250, 270, 2959, 369, 369EG, 379, 500, 651, 754, 784, 819, 819DW, 907, 907FF, OxeOl, TPO-L, 1173, 1173D, 4265, BP or MBF (BASF Corporation (Wyandotte, Michigan)). In some embodiments, the photoinitiator is TPO (2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide) or MBF (methyl benzoylformate).

[0064] In some embodiments, the organic resin is present in an amount by weight of the composition (weight / weight) of about 50% to about 99%, about 50% to about 95%, about 50% to about 90%, about 50% to about 85%, about 50% to about 80%, about 50% to about 70%, about 50% to about 60%, about 60% to about 99%, about 60% to about 95%, about 60% to about 90%, about 60% to about 85%, about 60% to about 80%, about 60% to about 70%, about 50% to about 60%, about 60% to about 99%, about 60% to about 95%, about 60% to about 90%, about 60% to about 85%, about 60% to about 80%, about 60% to about 70%. About 70%, about 70% to about 99%, about 70% to about 95%, about 70% to about 90%, about 70% to about 85%, about 70% to about 80%, about 80% to about 99%, about 80% to about 95%, about 80% to about 90%, about 80% to about 85%, about 85% to about 99%, about 85% to about 95%, about 85% to about 90%, about 90% to about 99%, about 90% to about 95%, or between about 95% and about 99%.

[0065] In a more preferred embodiment, in the composition, the compound comprising the structural unit represented by chemical formula (1) or (2), wherein R 1 R 4 ~R 10 and D, which may be the same or different and are independently selected from H, D, a linear alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 C atoms, or a silyl group, or a substituted keto group having 1 to 10 C atoms, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 7 to 10 C atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH 2), a haloformyl group (—C(═O)—X wherein X represents a halogen atom), a formyl group (—C(═O)—H), an isocyanate group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted 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 one or more radicals R 2 The rings which may be bonded to one another and / or to the radicals in question form a monocyclic or polycyclic aliphatic or aromatic ring system.

[0066] In certain preferred embodiments, the bridging group X 1 、X 2 At least one is empty; particularly preferably, both are empty, and the compound is selected from the group consisting of the following chemical formula (1b) or (2b) or the structural unit shown:

[0067]

[0068] In some preferred embodiments, X 1 、X 2 At least one is a single bond; particularly preferably, both are single bonds, and the compound is selected from the group consisting of structural units represented by the following chemical formula (1c) or (2c):

[0069]

[0070] In certain embodiments, X 1 、X 2 In each occurrence, the same or different two-bridge groups are present. Preferred two-bridge groups are:

[0071]

[0072]

[0073] The symbols R3, R4, R5, and R6 are defined as above. 4 , and the dotted bonds shown in the above groups represent bonds to adjacent structural units.

[0074] For the purposes of the present invention, aromatic ring systems contain 5 to 10 carbon atoms in the ring system, and heteroaromatic ring systems contain 1 to 10 carbon atoms and at least one heteroatom in the ring system, provided that the total number of carbon atoms and heteroatoms is at least 4. The heteroatoms are preferably selected from Si, N, P, O, S, and / or Ge, particularly preferably from Si, N, P, O, and / or S. For the purposes of the present invention, aromatic or heteroaromatic ring systems include not only systems containing aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N, or O atoms). Thus, systems such as 9,9′-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered aromatic ring systems for the purposes of this invention.

[0075] For the purposes of the present invention, any H atom on the compound may be replaced by R 4 Group substitution, R 4The definition of is as described above, preferably, (1) C1 to C10 alkyl, particularly preferably refers to the following groups: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-methylheptyl, trifluoromethyl, pentafluoromethylethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl and octynyl; (2) C1-C10 alkoxy, particularly preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or 2-methylbutoxy; (3) C2 to C10 aryl or heteroaryl, which may be monovalent or divalent depending on the application and may in each case also be replaced by the above-mentioned radicals R 4 Substituted and can be attached to the aromatic or heteroaromatic ring via any desired position, particularly preferably the following radicals are meant: benzene, naphthalene, anthracene, pyrene, dihydropyrene, chrysene, fluoranthene, butacene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthromimidazole, pyridimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzooxazole oxazole, naphthoxazole, anthraxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, diazaanthracene, 1,5-naphthyridine, nitrogen carbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole. 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole. For the purposes of the present invention, aromatic and heteroaromatic ring systems are taken to mean, in addition to the aryl and heteroaryl radicals mentioned above, in particular biphenylene, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, tetrahydropyrene and cis- or trans-indenofluorene.

[0076] In a preferred embodiment, the compound comprising chemical formula (1)-(1e) or (2)-(2e), wherein Ar 1 ~Ar5 The same or different in each occurrence can be selected from aromatic and heteroaromatic groups having 5 to 20 ring atoms; preferably selected from aromatic and heteroaromatic groups having 5 to 18 ring atoms; more preferably selected from aromatic and heteroaromatic groups having 5 to 15 ring atoms; most preferably selected from aromatic and heteroaromatic groups having 5 to 10 ring atoms; they can be unsubstituted or replaced by one or two R 4 Preferred aryl or heteroaryl groups include benzene, naphthalene, anthracene, phenanthrene, pyridine, pyrene or thiophene.

[0077] In another preferred embodiment, Ar 1 ~Ar 5 Selected from the following structural formula:

[0078]

[0079] X 3 It's CR 6 or N;

[0080] Y7 is selected from CR 7 R 8 , SiR 9 R 10 ,NR 6 or, C(=O), S, or O; R 6 , R 7 , R 8 , R 9 , R 10 The definition of is as above.

[0081] Further, Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Can be independently selected from one or a combination of the following chemical formulae, which can be further substituted arbitrarily:

[0082]

[0083] For the purposes of the present invention, the structural units of formula (1)-(1e) or (2)-(2e) are, in a particularly preferred embodiment, 1 ~Ar 5 It is a phenyl group.

[0084] In a particularly preferred embodiment, the compound comprises a structural unit represented by the following chemical formula (1a) or (2a):

[0085]

[0086] Among them, X 1 and X2 It is preferably selected from O and S, and particularly preferably selected from O.

[0087] In another particularly preferred embodiment, the compound comprises a structural unit represented by the following chemical formula (1d) or (2d) or (1e) or (2e):

[0088]

[0089] Preferably, Y in formula (2d) and (2e) b The same or different are independently selected from C=O, O, P(=O)R 9 , S=O or SO2; particularly preferably selected from C=O.

[0090] Preferably, X in formula (1d) and (1e) a The same or different are independently selected from N(R 9 )、C(R 9 R 10 )、Si(R 9 R 10 ), O, S.

[0091] In certain preferred embodiments, in the structural units according to chemical formula (1), (2), (1a)-(1e), (2a)-(2e), wherein R 4 ~R 8 When present multiple times, the following structural units or combinations thereof may be included identically or differently:

[0092]

[0093] Where n1 is 1 or 2 or 3 or 4.

[0094] In a particularly preferred embodiment, the compound has the structure shown below:

[0095]

[0096] Among them, R 21 -R 25It may be H, D, a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X wherein X is halogen atom), formyl group (—C(═O)—H), isocyano group, isocyanate group, thiocyanate group or isothiocyanate group, hydroxyl group, nitro group, CF3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted 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 one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded; and R 21 -R 25 At least one of the compounds contains an alcohol-soluble or water-soluble group.

[0097] m and n are integers of 0-4; o and q are integers of 0-5; and p is an integer of 0-3.

[0098] Preferably, R 21 -R 25 It can be H, D, a linear alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 C atoms, or a silyl group, or a substituted keto group having 1 to 10 C atoms, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 7 to 10 C atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X wherein X represents a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted 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, where one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded.

[0099] In the embodiments of the present invention, the triplet energy level (T1) and singlet energy level (S1), HOMO, and LUMO play a key role in the energy level structure of organic materials. The following is an introduction to the determination of these energy levels.

[0100] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0101] The triplet energy level T1 of an organic material can be measured by low-temperature time-resolved luminescence spectroscopy, or obtained by quantum simulation calculations (eg, by Time-dependent DFT), such as by the commercial software Gaussian 03W (Gaussian Inc.).

[0102] The singlet energy level S1 of an organic material can be determined by absorption or emission spectroscopy, or obtained by quantum simulation calculation (such as Time-dependent DFT).

[0103] It should be noted that the absolute values ​​of HOMO, LUMO, T1, and S1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. In the description of the embodiments of the present invention, the values ​​of HOMO, LUMO, T1, and S1 are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0104] In certain preferred embodiments, the compounds according to the present invention have (S1-T1) ≤ 0.30 eV, preferably ≤ 0.25 eV, more preferably ≤ 0.20 eV, even more preferably ≤ 0.15 eV, and most preferably ≤ 0.10 eV.

[0105] In some preferred embodiments, the full width at half maximum (FWHM) of the photoluminescence spectrum of the compound is ≤50 nm, preferably ≤45 nm, more preferably ≤40 nm, particularly preferably ≤35 nm, and most preferably ≤30 nm.

[0106] In certain embodiments, the composition, wherein the compound is selected from small molecules or polymers.

[0107] In certain embodiments, the compound has good solubility in the resin or resin prepolymer.

[0108] In a preferred embodiment, the compound contains at least one alcohol-soluble or water-soluble group, as disclosed in the concurrent patent application with application number CN202110370884.X, the entire contents of which are hereby incorporated herein by reference.

[0109] In some preferred embodiments, the compound comprises at least two alcohol-soluble or water-soluble groups.

[0110] In other preferred embodiments, the compound contains at least three alcohol-soluble or water-soluble groups.

[0111] In a preferred embodiment, in the compound, the alcohol-soluble or water-soluble group is selected from alcohols, aldehydes, acids, crown ethers, polyethers, primary amines and the like.

[0112] Preferably, the alcohol-soluble or water-soluble group is selected from the following structure:

[0113]

[0114] R 31 -R 37 It may be a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X wherein X is halogen atom), formyl group (—C(═O)—H), isocyano group, isocyanate group, thiocyanate group or isothiocyanate group, hydroxyl group, nitro group, CF3 group, Cl, Br, F, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system with 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group with 5 to 40 ring atoms, or a combination of these systems, where one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded.

[0115] t is an integer greater than 0.

[0116] In addition, the individual H atoms or CH2 groups of the present invention may be replaced by the above-mentioned groups or groups R, R being selected from alkyl groups having 1 to 40 C atoms, preferably selected from the following groups: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, ethylhexyl, trifluoromethane, 1,2-di ... 1-40 C atoms, such as methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or methylbutoxy.

[0117] Examples of compounds containing alcohol-soluble or water-soluble groups according to the present invention are given below, but are not limited to:

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] In other embodiments, the compound contains at least one cross-linkable group, as disclosed in the concurrent patent application with application number CN202110370910.9, the entire contents of which are hereby incorporated herein by reference; the advantage of this is that when the resin prepolymer undergoes copolymerization or homopolymerization, the compound can at least partially or completely participate in the polymerization.

[0125] In some preferred embodiments, the compound comprises at least two cross-linkable groups.

[0126] In other preferred embodiments, the compound comprises at least three cross-linkable groups.

[0127] In certain embodiments, the compound is a polymer comprising at least one repeating structural unit represented by formula (1)-(1e) or (2)-(2e). Preferably, the polymer is a side chain polymer, as disclosed in the concurrent patent application with application number CN202110370854.9, the entire contents of which are hereby incorporated herein by reference.

[0128] In certain embodiments, the composition according to the present invention further comprises at least one organic functional material, which can be selected from hole (also known as electron) injection or transport materials (HIM / HTM), hole blocking materials (HBM), electron injection or transport materials (EIM / ETM), electron blocking materials (EBM), organic host materials (Host), singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), thermally excited delayed fluorescence materials (TADF materials), and organic dyes. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0129] In a preferred embodiment, the composition further comprises a fluorescent host material (or singlet matrix material).

[0130] In a more preferred embodiment, the composition further comprises a fluorescent emitter (or singlet emitter) and a fluorescent host material. In this embodiment, the compound according to the present invention can serve as a co-luminescent material, preferably with a weight ratio of the compound to the other fluorescent emitter ranging from 1:20 to 20:1.

[0131] The following is a detailed description of the fluorescent host material and the fluorescent light-emitting body.

[0132] 1. Singlet host material (SingletHost):

[0133] Examples of singlet host materials are not particularly limited, and any organic compound may be used as a host as long as its singlet energy is higher than that of a light emitter, particularly a singlet light emitter or a fluorescent light emitter.

[0134] Examples of organic compounds used as singlet host materials may be selected from aromatic hydrocarbon compounds containing rings, such as benzene, biphenyl, triphenylbenzene, triphenylene, naphthalene, anthracene, phenanthrene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole, carbazole, pyridine, indole, pyrrole, dipyridine, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, , indoleazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthalene, phthalide, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuran pyridine, furandipyridine, benzothiophene pyridine, thiophene dipyridine, benzoselenophene pyridine and selenophene dipyridine; containing groups having 2 to 10 ring structures, which can be cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups of the same or different types, and are linked to each other directly or through at least one of the following groups, such as oxygen atoms, nitrogen atoms, sulfur atoms, silicon atoms, phosphorus atoms, boron atoms, chain structural units and aliphatic ring groups.

[0135] In a preferred embodiment, the singlet host material may be selected from compounds comprising at least one of the following groups:

[0136]

[0137] Among them, R 1 Ar may be independently selected from the following groups: hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl; 1 is an aryl or heteroaryl group, which is the same as the above-defined Ar 1 Same meaning; n2 is an integer from 0 to 20; X1-X8 are selected from CH or N; X 9 and X 10 Selected from CR 1 R 2 or NR 1 .

[0138] Some examples of anthracene-based singlet host materials are listed in the table below:

[0139]

[0140] 2. Singlet Emitter

[0141] Singlet emitters often have longer conjugated π-electron systems. To date, there have been many examples, such as styrylamine and its derivatives disclosed in JP2913116B and WO2001021729A1, and indenofluorene and its derivatives disclosed in WO2008 / 006449 and WO2007 / 140847.

[0142] In a preferred embodiment, the singlet emitter can be selected from monostyrylamines, distyrylamines, tertiary styrylamines, tetrastyrylamines, styrylphosphines, styrylethers and aromatic amines.

[0143] A monostyrylamine is a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A distyrylamine is a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tert-styrylamine is a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tetrastyrylamine is a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styrene is diphenylethylene, which may be further substituted. The corresponding phosphines and ethers are defined similarly to the amines. An arylamine or aromatic amine is a compound comprising three unsubstituted or substituted aromatic or heterocyclic rings directly attached to nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably a fused ring system and preferably has at least 14 aromatic ring atoms. Preferred examples include aromatic anthracenamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, and aromatic chrysenediamines. An aromatic anthracenamine is a compound in which a diarylamine group is directly attached to anthracene, preferably at the 9-position. An aromatic anthracenediamine is a compound in which two diarylamine groups are directly attached to anthracene, preferably at the 9- and 10-positions. Aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysamines, and aromatic chrysenediamines are similarly defined, with the diarylamine groups preferably attached to the 1- or 1,6-positions of the pyrene group.

[0144] Examples, also preferred examples, of singlet emitters based on vinylamines and aromatic amines 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 the above-mentioned patent documents are hereby incorporated herein by reference.

[0145] Examples of singlet emitters based on stilbene and its derivatives are disclosed in US Pat. No. 5,121,029.

[0146] Further preferred singlet emitters can be selected from indenofluorene-amines and indenofluorene-diamines, as disclosed in WO 2006 / 122630, benzindenofluorene-amines and benzindenofluorene-diamines, as disclosed in WO 2008 / 006449, and dibenzoindenofluorene-amines and dibenzoindenofluorene-diamines, as disclosed in WO 2007 / 140847.

[0147] Other materials that can be used as singlet emitters are polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-bis(2-naphthoanthracene), naphthalene, tetraphenyl, xanthene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, phenylene such as (4,4'-bis(9-ethyl-3-carbazolylvinyl)-1,1'-biphenyl), diindenopyrene, decacyclopentane, hexabenzophenone, fluorene, spirobifluorene, Arylpyrene (such as US20060222886), arylidene vinyl (such as US5121029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyran such as 4-(dicyanomethylene)-6-(4-(p-dimethylaminophenyl)-2-methyl)-4H-pyran (DCM), thiopyran, bis(azinyl)imine boron compounds (US 2007 / 0092753A1), bis(azinyl)methylene compounds, carbostyryl compounds, oxazinones, benzoxazoles, benzothiazoles, benzimidazoles and dione pyrrolopyrroles. Materials for some singlet emitters can be found in the following patent documents: US20070252517 A1, US 4769292, US 6020078, US 2007 / 0252517 A1, US 2007 / 0252517 A1. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0148] Some examples of suitable singlet emitters are listed in the table below:

[0149]

[0150] The organic functional materials publications mentioned above are incorporated herein by reference for disclosure purposes.

[0151] In certain embodiments, the composition according to the present invention further comprises at least one solvent.

[0152] In a preferred embodiment, the composition according to the invention is a solution.

[0153] In another preferred embodiment, the composition according to the invention is a suspension.

[0154] The composition in the embodiment of the present invention may include 0.01 to 20 wt % of the compound, preferably 0.1 to 20 wt %, more preferably 0.2 to 20 wt %, and most preferably 1 to 15 wt % of the compound.

[0155] The composition of the present invention can be used to form a color conversion layer using methods such as inkjet printing, transfer printing, and photolithography. In this case, the compound, alone or in combination with other materials, is dissolved in a resin (prepolymer) and / or an organic solvent to form an ink. The mass concentration of the compound (i.e., the color conversion material) in the ink is not less than 0.1 wt%. The color conversion capability of the color conversion layer can be improved by adjusting the concentration of the color conversion material in the ink and the thickness of the color conversion layer. Generally speaking, a higher concentration of the color conversion material or a greater thickness of the color conversion layer results in a higher color conversion efficiency of the color conversion layer.

[0156] In some preferred embodiments, the solvent is selected from water, alcohol, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, or borate or phosphate, or a mixture of two or more solvents.

[0157] In other embodiments, suitable and preferred solvents are aliphatic, cycloaliphatic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, diols or polyols.

[0158] In other embodiments, alcohols represent a suitable class of solvents. Preferred alcohols include alkylcyclohexanols, particularly methylated aliphatic alcohols, naphthols, and the like.

[0159] Other examples of suitable alcohol solvents include: dodecanol, phenyl tridecanol, benzyl alcohol, ethylene glycol, ethylene glycol methyl ether, glycerol, propylene glycol, propylene glycol ethyl ether and the like.

[0160] The solvent can be used alone or as a mixture of two or more organic solvents.

[0161] Further, examples of organic solvents include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0162] In some preferred embodiments, according to a composition of the present invention, the solvent is selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate esters or phosphate esters, or a mixture of two or more solvents.

[0163] Examples of aromatic or heteroaromatic solvents according to the present invention include, but are not limited to: 1-tetralone, 3-phenoxytoluene, acetophenone, 1-methoxynaphthalene, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, 1-methylnaphthalene, 1,2,4 -Trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, diphenyl ether, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.

[0164] In other embodiments, suitable and preferred solvents are aliphatic, alicyclic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers.

[0165] The solvent may be a cycloalkane, such as decalin.

[0166] In other preferred embodiments, a composition according to the present invention comprises at least 50 wt% of an alcohol solvent; preferably at least 80 wt% of an alcohol solvent; and particularly preferably at least 90 wt% of an alcohol solvent.

[0167] In some preferred embodiments, the solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter within the following ranges:

[0168] δ d (Dispersion force) 17.0~23.2MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 scope;

[0169] δ p (Polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0170] δ h (Hydrogen bond force) 0.9~14.2MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0171] In the composition of the present invention, the organic solvent should be selected based on its boiling point. In the present invention, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging in inkjet printheads. The organic solvent can be evaporated from the solvent system to form a film containing the functional material.

[0172] In some preferred embodiments, a composition according to the present invention is characterized in that

[0173] 1) Its viscosity @25°C is in the range of 1 cPs to 100 cPs, and / or

[0174] 2) Its surface tension @25℃ is in the range of 19 dyne / cm to 50 dyne / cm.

[0175] In the composition of the present invention, the resin (prepolymer) or organic solvent should be selected based on its surface tension. Suitable ink surface tension parameters are tailored to the specific substrate and printing method. For example, for inkjet printing, in a preferred embodiment, the surface tension of the resin (prepolymer) or organic solvent at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably, in the range of 22 dyne / cm to 35 dyne / cm; and most preferably, in the range of 25 dyne / cm to 33 dyne / cm.

[0176] In a preferred embodiment, the surface tension of the ink according to the present invention at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; and most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0177] According to the composition of the present invention, the viscosity parameters of the ink need to be considered when selecting the resin (prepolymer) or organic solvent. The viscosity can be adjusted by different methods, such as by selecting a suitable resin (prepolymer) or organic solvent and the concentration of the functional material in the ink. In a preferred embodiment, the viscosity of the resin (prepolymer) or organic solvent is less than 100 cps; more preferably less than 50 cps; and most preferably 1.5 to 20 cps. The viscosity here refers to the viscosity at the ambient temperature during printing, generally 15-30°C, preferably 18-28°C, more preferably 20-25°C, and most preferably 23-25°C. The composition thus formulated will be particularly suitable for inkjet printing.

[0178] In a preferred embodiment, the composition according to the present invention has a viscosity at 25°C in the range of about 1 cps to 100 cps; more preferably in the range of 1 cps to 50 cps; and most preferably in the range of 1.5 cps to 20 cps.

[0179] The ink obtained from the organic solvent that meets the above-mentioned boiling point, surface tension parameters and viscosity parameters can form a functional material film with uniform thickness and composition properties.

[0180] Salt compounds are difficult to purify and can easily introduce impurities, which can affect photoelectric performance. For the purposes of the present invention, in certain preferred embodiments, the compositions according to the present invention do not contain any salt compounds, and preferably do not contain any organic acid salts formed from organic acids and metals. For cost considerations, the present invention preferably excludes organic acid salts containing transition metals and lanthanides.

[0181] The present invention further relates to an organic functional material film, which is prepared using the composition as described above.

[0182] The present invention also provides a method for preparing the organic functional material thin film, comprising the following steps:

[0183] 1) preparing a composition according to the present invention;

[0184] 2) coating the composition on a substrate to form a thin film by printing or coating, wherein the printing or coating method is selected from inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, and slot extrusion coating;

[0185] 3) The obtained film is heated at at least 50 degrees Celsius or exposed to ultraviolet light to cause a cross-linking reaction and solidify the film.

[0186] The thickness of the organic functional material film is generally 50nm-200μm, preferably 100nm-150μm, more preferably 500nm-100μm, even more preferably 1μm-50μm, and most preferably 1μm-20μm.

[0187] In another preferred embodiment, the thickness of the organic functional material film is between 20 nm and 20 μm, preferably less than 15 μm, more preferably less than 10 μm, even better less than 8 μm, particularly preferably less than 6 μm, most preferably less than 4 μm, and most preferably less than 2 μm.

[0188] The present invention also provides applications of the organic composition and the organic functional material film in optoelectronic devices.

[0189] In certain embodiments, the optoelectronic device may be selected from an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic light emitting field effect transistor, or an organic laser.

[0190] Furthermore, the present invention provides a photoelectric device comprising the above-mentioned organic functional material film.

[0191] Preferably, the optoelectronic device is an electroluminescent device, such as an organic light-emitting diode (OLED), an organic light-emitting cell (OLEEC), an organic light-emitting field-effect transistor (OLED), a perovskite light-emitting diode (PeLED), and a quantum dot light-emitting diode (QD-LED), wherein a functional layer comprises a thin film of one of the above-mentioned organic functional materials. The functional layer can be selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a light-emitting layer, and a cathode passivation layer (CPL).

[0192] In a preferred embodiment, the optoelectronic device is an electroluminescent device comprising two electrodes, wherein the functional layer is located on the same side of the two electrodes.

[0193] In another preferred embodiment, the optoelectronic device comprises a light-emitting unit and a color conversion layer, wherein the color conversion layer comprises a thin film of the above-mentioned organic functional material.

[0194] In certain preferred embodiments, the light-emitting unit is selected from a solid-state light-emitting device, preferably selected from an LED, an organic light-emitting diode (OLED), an organic light-emitting cell (OLEEC), an organic light-emitting field-effect transistor (OLED), a perovskite light-emitting diode (PeLED), and a quantum dot light-emitting diode (QD-LED).

[0195] In a preferred embodiment, the light emitting unit emits blue light, which is converted into green light or red light by the color conversion layer.

[0196] The present invention further relates to a display comprising at least three types of pixels, red, green and blue, wherein the blue pixel comprises a blue light emitting unit, and the red and green pixels comprise a blue light emitting unit and corresponding red and green color conversion layers.

[0197] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0198] The following structural formula molecules are used in the specific embodiments of the present invention:

[0199]

[0200] Synthesis of compound H1:

[0201]

[0202] Synthesis of intermediate 1:

[0203] In a clean three-necked flask, accurately weigh 3,6-di-tert-butylcarbazole (8.0 g, 25.1 mmol, 1.0 eq), 2-bromo-1,3-difluoro-5-iodobenzene (14.02 g, 50.2 mmol, 2.0 eq), and cesium carbonate (16.35 g, 50.2 mmol, 1.2 eq). Add 250 mL of DMF, protect with nitrogen, and react at 85°C overnight. After the reaction, cool to room temperature, concentrate to remove DMF, add 200 mL of water, extract with DCM (100 mL each) three times, dry over anhydrous magnesium sulfate, add 600 mL of petroleum ether, decolorize on silica gel, and concentrate to obtain 117.85 g of the intermediate (85% yield).

[0204] Synthesis of intermediate 2:

[0205] In a clean three-necked flask, accurately weigh Intermediate 1 (16 g, 19.1 mmol, 1.0 eq), o-fluorophenylboronic acid (2.94 g, 21.0 mmol, 1.0 eq), and 0.5 g of tetrakistriphenylphosphine palladium were added. 100 mL of 2M potassium carbonate solution and 200 mL of 1,4-dioxane were added under nitrogen and reacted at 85°C overnight. After the reaction, the mixture was cooled to room temperature, the aqueous layer was separated, and the organic layer was concentrated. 200 mL of dichloromethane and 600 mL of petroleum ether were added, and the mixture was decolorized by passing through silica gel. Concentration afforded 211.5 g of the intermediate (75% yield).

[0206] Synthesis of compound H1

[0207] In a clean three-necked flask, accurately weighed intermediate 2 (8.06 g, 10 mmol, 1.0 eq) was placed under nitrogen. 100 mL of m-xylene was injected via syringe and the mixture was cooled to -78°C. n-Butyl lithium (2.5 M) (4.8 mL, 12 mmol, 1.2 eq) was slowly added dropwise. The temperature was gradually raised to room temperature and stirred for 1 hour. The temperature was then lowered to -30°C, and boron tribromide (7.5 g, 30 mmol, 3.0 eq) was slowly added dropwise. The temperature was gradually returned to room temperature and stirred overnight. 10 mL of DIPEA was added, and the mixture was stirred at room temperature for 30 minutes before being heated to 80°C for reaction. After the reaction, 200 mL of methanol was added, the mixture was stirred at room temperature, and then filtered. The filter cake was rinsed with methanol. The filter cake was collected to obtain 1.47 g of the final product (20% yield).

[0208] The synthesis of compounds 5, 9, 11, and 12 is described in the patent application filed concurrently with application number CN202110370884.X.

[0209] 1) Dissolve the green and red color-converting materials in n-butyl acetate at a concentration of 100 mg / ml. Add 100 mg / ml of polymethyl acrylate and 5 mg / ml of silica nanospheres (3-5 microns in diameter) to the solution. Spin-coat the solution to form a thin film approximately 2 microns thick on the surface of the light guide plate, serving as the red and green color-converting layers.

[0210] Green color converters, red color converters, and transparent film layers are arranged in an alternating array to form three types of pixels.

[0211] A blue self-luminous device is provided below the above three film layers. The blue self-luminous device emits blue light with a luminescence peak between 400-490nm. The blue light is directed to the green color converter, the red color converter, and the transparent film layer respectively. The blue light passes through the green color converter and emits green light with a luminescence peak between 490-550nm. The blue light passes through the red color converter and emits red light with a luminescence peak between 550-700nm. The blue light passes through the transparent film layer and emits blue light with a luminescence peak between 400-490nm.

[0212] 2) Dissolve the blue, green, and red color-converting materials in n-butyl acetate at concentrations of 50 mg / ml, 50 mg / ml, and 50 mg / ml, respectively. Form a film using a doctor blade or spin coating. Bake on a hot plate at 100°C for 10 minutes to obtain a 200-500 nm color-converting film.

[0213] The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, not all possible combinations of the technical features in the above-mentioned embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0214] The above-described embodiments merely illustrate several implementations of the present invention, and while their descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent. It should be noted that a person skilled in the art would be able to make numerous variations and improvements without departing from the spirit of the present invention, all of which fall within the scope of protection of the present invention. Therefore, the scope of protection of the patent for this invention shall be determined by the appended claims.

Claims

1. A composition, characterized in that: The composition comprises: 1) at least one organic resin; 2) at least one compound comprising a structural unit represented by formula (1a), Chemical formula (1a) The symbols and marks used have the following meanings: Ar 1 ~Ar 3 the same or different ones selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms; Ar 4 ~Ar 5 the same or different selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms; X 1 、X 2 is empty or a bridging group; R 4 ~R 8 The same or different radicals are independently selected from -F, -Cl, -Br, -I, -CN, -NO2, -CF3, a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group or silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms. a group, or an aryloxycarbonyl group having 7 to 20 C atoms, a carbamoyl group (—C(═O)NH 2 ), a haloformyl group (—C(═O)—X wherein X represents a halogen atom), a formyl group (—C(═O)—H), an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a nitro group, a crosslinkable group or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamino or heteroarylamino group having 5 to 40 ring atoms, a disubstituted unit at any position of the above substituents or a combination of these systems, wherein one or more substituent groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bonded; The compound comprises at least one alcohol-soluble or water-soluble group, wherein the alcohol-soluble or water-soluble group is selected from: alcohols, acids, and primary amine groups; The half-maximum width of the photoluminescence spectrum of the compound is less than or equal to 50 nm; and the viscosity of the composition at 25° C. is 1 cps-100 cps.

2. The composition according to claim 1, wherein: The at least one organic resin is a thermosetting resin or a UV curable resin; and / or the composition further comprises a thermal initiator or a photoinitiator.

3. The composition according to claim 1, wherein: The compound comprises a structural unit represented by one of the following chemical formulas (1b) to (1e): Among them, X a Selected from N(R 9 ), R 9 The meaning of the symbol is the same as R in claim 1 4 .

4. The composition according to claim 1, wherein: The compound is selected from the following chemical formula: 。 5. The composition according to claim 1, wherein: The composition also includes at least one solvent.

6. The composition according to claim 5, characterized in that The solvent is selected from at least one of water, alcohol, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, borate ester, and phosphate ester.

7. An organic functional material film, characterized in that: The organic functional material film comprises a film prepared according to the composition according to any one of claims 1 to 6.

8. A photoelectric device, characterized in that: The optoelectronic device comprises the organic functional material thin film according to claim 7.

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