WO2023071073A1 - 芳胺类有机化合物及其应用 - Google Patents

芳胺类有机化合物及其应用 Download PDF

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WO2023071073A1
WO2023071073A1 PCT/CN2022/087065 CN2022087065W WO2023071073A1 WO 2023071073 A1 WO2023071073 A1 WO 2023071073A1 CN 2022087065 W CN2022087065 W CN 2022087065W WO 2023071073 A1 WO2023071073 A1 WO 2023071073A1
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atoms
substituted
independently selected
formula
organic compound
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French (fr)
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李涛
龙志飞
宋晶尧
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Priority to EP22884989.9A priority Critical patent/EP4428123A4/en
Priority to US18/681,062 priority patent/US20240199559A1/en
Priority to DE112022005238.4T priority patent/DE112022005238T5/de
Priority to KR1020247012585A priority patent/KR20240063967A/ko
Publication of WO2023071073A1 publication Critical patent/WO2023071073A1/zh
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Definitions

  • the present application relates to the technical field of luminescent materials, in particular to an aromatic amine organic compound, a mixture comprising the aromatic amine organic compound, and an organic electronic device.
  • Organic electroluminescent display equipment is a type of self-luminous display device, which generates excitons through the transfer and recombination of carriers between various functional layers, and relies on organic compounds or metal complexes with high quantum efficiency to emit light. It has self-luminescence, Features such as high brightness, high efficiency, high contrast, and high responsiveness.
  • OLEDs organic light-emitting diodes
  • internal quantum efficiency has approached the theoretical limit.
  • OLEDs organic light-emitting diodes
  • a light-emitting device in which a "covering layer" (light extraction layer) with a high refractive index is provided outside a translucent electrode with a low refractive index.
  • a "covering layer” light extraction layer
  • a translucent electrode with a low refractive index.
  • Hung et al. covered a layer of about 50nm organic compound or inorganic compound on the surface of the metal cathode to improve the performance of the device by controlling the thickness and refractive index.
  • Riel et al. Riel et al.
  • the present application provides an aromatic amine organic compound, a mixture comprising the aromatic amine organic compound, and an organic electronic device.
  • a kind of arylamine organic compound has the structure shown in general formula (1):
  • L 1 -L 4 are independently selected from single bonds, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms;
  • Ar is selected from any structure shown in formula (A-1) or formula (A-2);
  • Ar 2 is selected from any structure shown in formula (A-2)-(A-6);
  • Ar 3 and Ar 4 are independently selected from any structure shown in the above formulas (A-3)-(A-6);
  • n is selected from 0, 1, 2, 3 or 4;
  • Y is selected from O, S or NR 2 ;
  • Each occurrence of X and X 1 -X 8 is independently selected from CR 3 or N, and at least one of X 1 -X 8 is selected from N;
  • R 1 , R 2 , and R 3 is independently selected from -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, Branched alkyl having 3 to 20 C atoms, branched alkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, ring having 3 to 20 C atoms alkoxy, substituted or unsubstituted silyl, cyano, isocyano, hydroxyl, nitro, amino, -CF 3 , -Cl, -Br, -F, -I, with 2 to 20 An alkenyl group with a C atom, or a substituted or unsubstituted aromatic group with 6 to 20 ring atoms, or a combination of these groups.
  • the present application also provides a mixture, the mixture comprising the above aromatic amine organic compound and at least one organic functional material, the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials , an electron blocking material, a hole blocking material, a light emitting material, a host material, a host material or an organic dye.
  • the present application also provides an organic electronic device, comprising two electrodes, one or more organic functional layers disposed between the two electrodes, and a light emitting diode disposed on the surface of one of the electrodes away from the organic functional layer.
  • the light extraction layer includes at least one aromatic amine organic compound mentioned above.
  • the arylamine organic compound of the present application contains phenanthrene, bisarylamine and condensed heterocyclic rings in structure, and has higher glass temperature and higher thermal stability.
  • the arylamine organic compound has a high extinction coefficient for ultraviolet light, and when the arylamine organic compound is used as the light extraction layer of an organic electronic device, it can effectively prevent harmful light from affecting the electrodes and the electrodes of the organic electronic device. Detrimental effects of internal functional layers.
  • the arylamine organic compound has a small extinction coefficient for visible light and a high transmittance for visible light, thereby reducing the influence on the light extraction efficiency of the device.
  • the use of the aromatic amine organic compound as a light extraction layer material in an organic electronic device can effectively improve the light extraction efficiency of visible light from the device.
  • FIG. 1 is a schematic structural view of an organic electronic device provided in an embodiment of the present application.
  • Fig. 2 is the ultraviolet-visible absorption spectrogram of the organic compound C1 of embodiment 1 in dichloromethane;
  • Fig. 3 is an ultraviolet-visible absorption spectrum diagram of the organic compound C21 of Example 2 in dichloromethane.
  • a description of a range from 1 to 6 should be considered to have specifically disclosed subranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and Single numbers within the stated ranges, eg 1, 2, 3, 4, 5 and 6, apply regardless of the range. Additionally, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the indicated range.
  • aromatic groups, aromatics, and aromatic ring systems have the same meaning and can be interchanged.
  • heteroaromatic group heteroaromatic and heteroaromatic ring system have the same meaning and can be interchanged.
  • substituted means that the hydrogen atom in the substituent is replaced by the substituent.
  • R 1 when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R 1 s , R 1 can be independently selected from different groups.
  • substituted or unsubstituted means that the defined group may be substituted or unsubstituted.
  • R substituents
  • the R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro Or halogen, alkyl containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaryl group containing 5-20 ring atoms , -NR'R", silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group , trifluoromethyl, and the above groups can also be further substituted by substituents acceptable in the art;
  • R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro or halogen, alkyl containing 1-10 C atoms, containing 3-10 rings atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, silyl groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, Haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art.
  • the "number of ring atoms” means the number of atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded into a ring.
  • the number of atoms within an atom When the ring is substituted by a substituent, the atoms included in the substituent are not included in the ring-forming atoms.
  • the number of ring atoms of a benzene ring is 6
  • the number of ring atoms of a naphthalene ring is 10
  • the number of ring atoms of a thienyl group is 5.
  • aryl or aromatic group refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a single-ring aromatic group, a fused-ring aromatic group or a polycyclic aromatic group, for Of the polycyclic rings, at least one is an aromatic ring system.
  • a "substituted or unsubstituted aryl group having 6 to 40 ring atoms” refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more A substituted or unsubstituted aryl group having 6 to 18 ring atoms is preferred, a substituted or unsubstituted aryl group having 6 to 14 ring atoms is particularly preferred, and the aryl group is optionally further substituted; suitable examples include but Not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthacene, fluorenyl, perylene , acenaphthyl and its derivatives.
  • aryl groups may also be interrupted by short non-aromatic units (e.g. ⁇ 10% non-H atoms such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9-diaryl Fluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.
  • short non-aromatic units e.g. ⁇ 10% non-H atoms such as C, N or O atoms
  • acenaphthene, fluorene, or 9,9-diaryl Fluorene triarylamine
  • diaryl ether systems should also be included in the definition of aryl.
  • heteroaryl or heteroaromatic group means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be N atom, O atom, S atom, etc.
  • substituted or unsubstituted heteroaryl having 5 to 40 ring atoms refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms group, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, Suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridyl Azinyl, pyrazinyl, quinolinyl, isoquinolinyl, quin
  • alkyl may represent straight chain, branched chain and/or cyclic alkyl.
  • the carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6.
  • Phrases containing this term, for example, "C 1-9 alkyl” refers to an alkyl group containing 1 to 9 carbon atoms, each occurrence of which may be, independently of each other, C 1 alkyl, C 2 alkyl, C 3 alkyl, C 4 alkyl, C 5 alkyl, C 6 alkyl, C 7 alkyl, C 8 alkyl or C 9 alkyl.
  • Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-di Methylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl -2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methyl Heptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-but
  • substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-inter, p-pair, Me methyl, Et ethyl, Pr propyl , Butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.
  • amino group refers to derivatives of amines, having the structural characteristics of formula -N(X) 2 , wherein each "X" is independently selected from H, substituted or unsubstituted alkyl, substituted or Unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group and the like.
  • Non-limiting types of amine groups include -NH 2 , -N(alkyl) 2 , -NH(alkyl), -N(cycloalkyl) 2 , -NH(cycloalkyl), -N(heterocyclyl ) 2 , -NH(heterocyclyl), -N(aryl) 2 , -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(aryl) N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), and the like.
  • hydroxyl refers to -OH
  • carboxyl refers to -COOH
  • amino refers to -NH 2
  • isocyanate refers to -NCO
  • isothiocyanate refers to -NCS.
  • alkoxy refers to a group with the structure "-O-alkyl", ie an alkyl group as defined above is attached to another group via an oxygen atom.
  • Suitable examples of phrases containing this term include, but are not limited to: methoxy ( -O- CH3 or -OMe), ethoxy (-O- CH2CH3 or -OEt) and tert-butoxy (- OC(CH 3 ) 3 or —OtBu).
  • linking site when the linking site is not specified in the group, it means that an optional linkable site in the group is used as the linking site.
  • no fused site when no fused site is specified in the group, it means that the optional fused site in the group is used as the fused site, preferably two or more positions in the ortho position in the group are fused Synthesis point.
  • the fusion site is used as the fusion site, preferably two or more positions in the ortho position in the group are fusion sites;
  • each substituent may be the same or different from each other, for example
  • the 6 R 1s on the benzene ring may be the same or different from each other.
  • the single bond connecting the substituent runs through the corresponding ring, indicating that the substituent can be connected to an optional position of the ring, for example In R, any substitutable position of the benzene ring is connected, such as express can be with The optional substitutable positions on the rings are formed.
  • a kind of arylamine organic compound has the structure shown in general formula (1):
  • L 1 -L 4 are independently selected from single bonds, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, or substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms;
  • Ar is selected from any structure shown in formula (A-1) or formula (A-2);
  • Ar 2 is selected from any structure shown in formula (A-2)-(A-6);
  • Ar 3 and Ar 4 are independently selected from any structure shown in the above formulas (A-3)-(A-6);
  • n is selected from 0, 1, 2, 3 or 4;
  • Y is selected from O, S or NR 2 ;
  • Each occurrence of X and X 1 -X 8 is independently selected from CR 3 or N, and at least one of X 1 -X 8 is selected from N;
  • R 1 , R 2 , and R 3 is independently selected from -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, Branched alkyl having 3 to 20 C atoms, branched alkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, ring having 3 to 20 C atoms alkoxy, substituted or unsubstituted silyl, cyano, isocyano, hydroxyl, nitro, amino, -CF 3 , -Cl, -Br, -F, -I, with 2 to 20 An alkenyl group with a C atom, or a substituted or unsubstituted aromatic group with 6 to 20 ring atoms, or a combination of these groups.
  • each occurrence of R 1 , R 2 , and R 3 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, and an alkyl group having 1 to 10 C atoms.
  • the general formula (1) is selected from any structure shown in formulas (2-1)-(2-6):
  • R 1 , R 3 , Y, X, X 5 -X 8 , L 1 -L 4 , Ar 3 , and Ar 4 have the same meanings as described above.
  • each occurrence of X5-X8 is independently selected from CR 3 or N, and at least one of X 5 -X 8 is selected from N; preferably Ground, X 5 is selected from N.
  • each occurrence of R 3 is independently selected from -H, -D, a straight chain alkyl group with 1 to 10 C atoms, a branched chain alkyl group with 3 to 10 C atoms, a branched chain alkyl group with 3 to 10 C-atom cyclic alkyl, substituted or unsubstituted silyl, cyano, isocyano, hydroxyl, nitro, -CF 3 , -Cl, -Br, -F, -I, or substituted or An unsubstituted aromatic group having 6 to 10 ring atoms, or a combination of these groups.
  • each occurrence of R 1 is independently selected from -H, -D, straight-chain alkyl having 1 to 10 C atoms, A branched chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a combination of these groups combination.
  • L 1 -L 4 are each independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted hetero group having 6 to 20 ring atoms Aromatic group.
  • L 1 -L 4 may be selected from single bonds, substituted or unsubstituted aromatic groups having 6 to 13 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 13 ring atoms.
  • L 1 -L 4 are independently selected from single bond, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene substituted or unsubstituted naphthacene, substituted or unsubstituted fluorenyl, substituted or unsubstituted perylene, substituted or unsubstituted acenaphthyl, substituted or unsubstituted thienyl, substituted or unsubstituted Substituted Substi
  • the "substituted" in the "substituted or unsubstituted” means that the substituent is selected from deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-8 C atoms, A heterocyclic group containing 3-8 ring atoms, an aromatic group containing 6-10 ring atoms, or a heteroaromatic group containing 6-10 ring atoms.
  • L 1 -L 4 are independently selected from single bonds or the following groups:
  • * indicates the linking site.
  • Y is selected from O or S.
  • L 1 -L 4 are independently selected from single bonds or phenyl groups, and further, the general formula (1) is selected from any structure shown in formulas (3-1)-(3-6) :
  • R 1 , Y, X, X 5 -X 8 , L 3 -L 4 , Ar 3 and Ar 4 are the same as above.
  • Y in formulas (3-1)-(3-4) is selected from O or S. In some embodiments, Y is selected from oxygen.
  • X in formula (3-5) and formula ( 3-6 ) is selected from N.
  • general formula (1) is selected from any general formula of formulas (4-1)-(4-6):
  • the organic compound described in the present application is selected from a symmetrical structure.
  • Ar 3 and Ar 4 are independently selected from any group represented by formulas (B-1)-(B-7):
  • * indicates the connection site
  • Each occurrence of R3 is independently selected from -H, -D, straight chain alkyl having 1 to 10 C atoms, branched chain alkyl having 3 to 10 C atoms, having 3 to 10 C atoms Cyclic alkyl, silyl, cyano, isocyano, hydroxyl, nitro, -CF 3 , -Cl, -Br, -F, -I, phenyl, biphenyl, terphenyl, or naphthyl.
  • *-L 3 -Ar 3 and/or *-L 4 -Ar 4 are selected from the following groups:
  • *-L 3 -Ar 3 and *-L 4 -Ar 4 are selected from the same group.
  • the aromatic amine organic compound according to the present application has a refractive index at a wavelength of 630 nm greater than 1.7; preferably greater than 1.78; more preferably greater than 1.83.
  • the aromatic amine organic compound described in the present application has a small extinction coefficient in the wavelength range greater than 430 nm, and has a high transmittance to visible light, thereby reducing the impact on the light extraction efficiency of the device.
  • the extinction coefficient of the aromatic amine organic compound at a wavelength of 430 nm is less than 0.1; preferably, less than 0.003; more preferably, less than 0.001.
  • the aromatic amine organic compound described in the present application has a relatively large extinction coefficient in the wavelength range of less than or equal to 400 nm.
  • the extinction coefficient of the aromatic amine organic compound at a wavelength of 350 nm is ⁇ 0.3; preferably ⁇ 0.5, more preferably ⁇ 0.7, most preferably ⁇ 1.0.
  • the aromatic amine organic compound according to the present application has a higher glass transition temperature to improve the thermal stability of the material.
  • the glass transition temperature of the aromatic amine organic compound is Tg ⁇ 100°C; preferably Tg ⁇ 120°C, more preferably Tg ⁇ 140°C, more preferably Tg ⁇ 160°C.
  • arylamine organic compound of the present application can be selected from but not limited to any one of the following structures:
  • the present application further relates to a mixture comprising at least one of the above-mentioned organic compounds and at least another organic functional material
  • the other organic functional material may be but not limited to a hole injection material (HIM), Hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), light emitting materials (Emitter), host materials (Host) and organic dye.
  • HIM hole injection material
  • HTM Hole transport materials
  • ETM electron transport materials
  • EIM electron injection materials
  • EBM electron blocking materials
  • HBM hole blocking materials
  • Emitter light emitting materials
  • host materials Hos
  • organic dye organic dye
  • the present application also relates to a composition
  • a composition comprising at least one aromatic amine organic compound or mixture as described above, and at least one organic solvent.
  • the organic solvent is selected from aromatic or heteroaromatic based solvents, ester based solvents, aromatic ketone based solvents, aromatic ether based solvents, aliphatic ketones, aliphatic ethers, cycloaliphatic compounds, olefins At least one of compounds, borate compounds and phosphate compounds.
  • the organic solvent is selected from aromatic or heteroaromatic based solvents.
  • the aromatic or heteroaromatic based solvent may be selected from but not limited to p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-iso Propylbiphenyl, p-methylcumene, pentapentylbenzene, tripentylbenzene, amyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzen
  • the ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, maleic acid Alkyl esters, alkyl lactones, alkyl oleates, etc. Particularly preferred is at least one of octyl caprylate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.
  • the aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone Naphthone, acetophenone, propiophenone, benzophenone, and their derivatives.
  • the derivatives can be selected from but not limited to 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylacetophenone, 3-methylacetophenone At least one of propiophenone and 2-methylpropiophenone.
  • the aromatic ether-based solvent may be selected from, but not limited to, 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4- Ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethyl Oxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans-p-propenyl anisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, At least one of diphenyl
  • the aliphatic ketone-based solvent may be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl Base-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, such as pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, Diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether At least one of ether and tetraethylene glycol dimethyl ether.
  • organic solvent can be used alone or as a mixed solvent of two or more organic solvents.
  • the composition of the present application includes at least one aromatic amine organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.
  • the other organic solvent can be selected from but not limited to methanol, ethanol, 2-methoxyethanol, methylene chloride, 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 (DMSO), tetra At least one of hydronaphthalene, decalin and indene.
  • DMSO dimethylformamide
  • DMSO dimethyl sulfoxide
  • the organic solvent suitable for the present application is a solvent with a Hansen solubility parameter in the following ranges:
  • ⁇ d (dispersion force) is in the range of 17.0-23.2MPa1/2, especially in the range of 18.5-21.0MPa1/2;
  • ⁇ p (polar force) is in the range of 0.2-12.5MPa1/2, especially in the range of 2.0-6.0MPa1/2;
  • ⁇ h hydrogen bonding force is in the range of 0.9-14.2 MPa1/2, especially in the range of 2.0-6.0 MPa1/2.
  • the boiling point of the organic solvent should be considered when selecting the organic solvent.
  • the boiling point of the organic solvent is ⁇ 150°C; preferably ⁇ 180°C; more preferably ⁇ 200°C; more preferably ⁇ 250°C; most preferably ⁇ 300°C. A boiling point within these ranges is beneficial for preventing clogging of the nozzles of the inkjet print head.
  • the organic solvent can be evaporated from the solvent system to form a thin film comprising the organic compound.
  • the composition is a solution. In yet other embodiments, the composition is a suspension.
  • the solution or suspension may additionally include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, and the like.
  • the additive can be selected from but not limited to at least one of surface active compounds, lubricants, wetting agents, dispersants, hydrophobic agents and adhesives.
  • the content of the aromatic amine organic compound is 0.01-10wt%, preferably 0.1-8wt%, more preferably 0.2-5wt%, most preferably 0.25-3wt%.
  • the present application also relates to the use of said composition as coating or printing ink in the preparation of organic electronic devices.
  • the composition is used to prepare an organic electronic device by printing or coating.
  • the printing or coating preparation method can be but not limited to inkjet printing, gravure printing, jet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, reverse roller printing, Lithographic printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc.
  • the present application further relates to a light extraction layer material selected from the above organic compounds or mixtures or compositions.
  • the present application further relates to an application of the above-mentioned organic compound, mixture or composition in an organic electronic device.
  • the organic electronic device can be an organic light emitting diode (OLED), an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon Emitter diodes and the like are particularly preferably OLEDs.
  • OLED organic light emitting diode
  • the specific plan is as follows:
  • An organic electroluminescent device comprising two electrodes, one or more organic functional layers arranged between the two electrodes, and a light extraction layer arranged on the surface of one of the electrodes and away from the organic functional layer , the light extraction layer contains an aromatic amine organic compound as described in formula (1).
  • an organic electronic device comprises a bottom electrode, at least one functional layer, a top electrode and a light extraction layer which are sequentially stacked.
  • the light extraction layer contains the aromatic amine organic compound described in this application.
  • the bottom electrode is an anode
  • the top electrode is a cathode
  • the light extraction layer is located on the surface of the cathode.
  • the thickness of the general light extraction layer is 10nm to 200nm, preferably 20nm to 150nm, more preferably 30nm to 100nm, most preferably 40nm to 90nm.
  • the organic electronic device described in the present application includes one or more organic functional layers, and the organic functional layers are selected from electron injection layers, electron transport layers, hole injection layers, hole One or more layers of a transport layer and a light-emitting layer, including at least one light-emitting layer.
  • the light-emitting material in the light-emitting layer is selected from singlet light emitters, triplet light emitters or TADF materials.
  • the organic functional layer is selected from a hole transport layer, a light emitting layer and an electron transport layer.
  • the organic functional layer is selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the organic functional layer includes a light-emitting layer; further, the material of the light-emitting layer is selected from triplet light-emitting materials.
  • the triplet luminescent material has a structure shown in the following general formula:
  • n is selected from 1 or 2 or 3;
  • Ring A is selected from substituted or unsubstituted N-containing heteroaromatic groups with 5-30 ring atoms;
  • Ring B is selected from substituted or unsubstituted aromatic groups or heteroaromatic groups with 6-30 ring atoms;
  • L is a monovalent anionic organic ligand.
  • ring A is selected from any one of the following groups:
  • N is the connection site.
  • ring B is selected from any one of the following groups:
  • each occurrence of X 3 is independently selected from CR 11 or N;
  • Each occurrence of R 11 , R 12 , R 13 , and R 14 is independently selected from hydrogen, deuterium, straight-chain alkyl with 1-20 carbon atoms, branched chain or cyclic with 3-20 carbon atoms Alkyl, cyano, nitro, -CF 3 , -OCF 3 , -Cl, -Br, -F, substituted or unsubstituted aromatic groups with 6-30 ring atoms, substituted or unsubstituted aromatic groups with A heteroaromatic group of 5-30 ring atoms, or a combination of these groups.
  • triplet luminescent material is selected from the following general formula:
  • each occurrence of R 11 is independently selected from hydrogen, deuterium, straight-chain alkyl having 1-10 carbon atoms, branched or cyclic alkyl having 3-10 carbon atoms, cyano, nitro, CF3 , OCF3 , Cl, Br, F, aromatic groups with 6-20 ring atoms, heteroaromatic groups with 5-20 ring atoms, or combinations of these groups;
  • n is independently selected from 0, 1, 2, 3, 4 or 5; m is as above.
  • the triplet light-emitting material according to the present application is selected from the following structures:
  • organic electronic devices described in this application can be, but are not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells, organic light emitting cells, organic field effect transistors, organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic Sensors, organic plasmon emission diodes, and the like are particularly preferably OLEDs.
  • OLEDs organic light emitting diodes
  • organic field effect transistors organic light emitting field effect transistors
  • organic lasers organic spintronic devices
  • organic Sensors organic plasmon emission diodes, and the like are particularly preferably OLEDs.
  • the cathode and anode in the OLED device structure are described below.
  • the anode may comprise a conductive metal or metal oxide, or a conductive polymer.
  • the anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light emitting layer.
  • the absolute value of the difference between the work function of the anode and the emitter in the light-emitting layer or the HOMO energy level or the valence band energy level of the p-type semiconductor material as HIL or HTL or electron blocking layer (EBL) is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2eV.
  • anode materials 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 may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the anode is pattern structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to the present application.
  • the cathode can comprise a conductive metal or metal oxide.
  • the cathode can easily inject electrons into the EIL or ETL or directly into the emissive layer.
  • the work function of the cathode and the LUMO energy level or conductance of the emitter in the light-emitting layer or as an electron injection layer (EIL) or an electron transport layer (ETL) or a hole blocking layer (HBL) n-type semiconductor material
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the absolute value of the difference in band energy levels is less than 0.5 eV, preferably less than 0.3 eV, 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 present application.
  • cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloys, BaF2 /Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like.
  • the cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the light extraction layer is located on the surface of the cathode.
  • the thickness of the general light extraction layer is 10nm to 200nm, preferably 20nm to 150nm, more preferably 30nm to 100nm, most preferably 40nm to 100nm. 90nm.
  • the present application also relates to the application of the electroluminescent device according to the present application in various electronic devices, and the electronic devices may be but not limited to display devices, lighting devices, light sources, sensors and the like.
  • the synthetic route of the organic compound C1 of the present embodiment is as follows:
  • reaction solution Cool the reaction solution to room temperature, add water to separate layers, extract the aqueous layer with ethyl acetate, combine the organic layers, dry and concentrate over anhydrous sodium sulfate, and separate on a silica gel column to obtain 3.15 g of compound Z2 with a yield of 76%.
  • the synthetic route of the organic compound C3 of the present embodiment is as follows:
  • the synthetic route of the organic compound C6 of the present embodiment is as follows:
  • the synthetic route of the organic compound C21 of the present embodiment is as follows:
  • the synthetic route of the organic compound C26 of the present embodiment is as follows:
  • the synthetic route of the organic compound C69 of the present embodiment is as follows:
  • the organic compound of the present embodiment is as follows from the synthetic route of C57:
  • the synthetic route of the organic compound C39 of the present embodiment is as follows:
  • the synthetic route of the organic compound C17 of the present embodiment is as follows:
  • the synthetic route of the organic compound C11 of the present embodiment is as follows:
  • the synthetic route of the organic compound C158 of the present embodiment is as follows:
  • the synthetic route of the organic compound C80 of the present embodiment is as follows:
  • the synthetic route of the organic compound C89 of the present embodiment is as follows:
  • the synthetic route of the organic compound C196 of the present embodiment is as follows:
  • the organic compound in this comparative example is CBP (4,4'-bis(9-carbazole)biphenyl).
  • the ultraviolet-visible absorption spectra of the organic compound C1 of Example 1 and the organic compound C21 of Example 4 in dichloromethane were tested.
  • FIG. 2 for the ultraviolet-visible absorption spectrum of the organic compound C1 of Example 1 in solution
  • FIG. 3 for the ultraviolet-visible absorption spectrum of the organic compound C21 of Example 4 in solution.
  • the organic compounds of Examples 1-14 and Comparative Examples were vapor-deposited on single crystal silicon to form a 50nm thin film by vacuum evaporation.
  • the single crystal silicon was placed on the sample stage of an ellipsometer (ES-01), and the incident angle was 70 degrees.
  • the test environment is the atmospheric environment, the extinction coefficient k (extinction coefficient@430nm) of organic compounds to light with a wavelength of 430nm and the refractive index n (refractive index@630nm) to light with a wavelength of 630nm
  • the test results are fitted by ellipsometer The test results are shown in Table 1 below.
  • Example 1 the organic compound Extinction coefficient@430nm Refractive index@630nm
  • Example 2 C3 0.02 1.91
  • Example 3 C6 0.01 1.92
  • Example 4 C21 0.01 1.87
  • Example 5 C26 0.01 1.89
  • Example 6 C69 0.03 1.91
  • Example 7 C57 0.03 1.87
  • Example 8 C39 0.04 1.88
  • Example 9 C17 0.05 1.91
  • Example 10 C11 0.05 1.92
  • Example 11 C158 0.03 1.90
  • Example 12 C80 0.04 1.92
  • Example 13 C89 0.02 1.89
  • Example 14 C196 0.01 1.88 comparative example CBP 0 1.74
  • the aromatic amine organic compounds of Examples 1-14 have weaker absorption of light in the visible light band, and higher absorption of light in the ultraviolet band.
  • the aromatic amine organic compounds of Examples 1-14 have a higher refractive index.
  • the preparation process of the above-mentioned OLED device is described in detail below through specific examples.
  • the structure of the OLED device is: ITO/Ag/ITO (anode)/HATCN/SFNFB/m-CP:Ir(p-ppy) 3 /NaTzF 2 /LiF/Mg:Ag/light extraction layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • ETL electron transport layer
  • 107 is an electron injection layer
  • 108 is a cathode
  • 109 is a light extraction layer.
  • the hole injection layer material HATCN is evaporated by vacuum evaporation, the thickness is 5nm, and the evaporation rate is On the hole injection layer, the hole transport material SFNFB is evaporated by vacuum evaporation with a thickness of 80nm.
  • m-CP is used as the host material
  • Ir(p-ppy) 3 is used as the dopant material
  • the mass ratio of Ir(p-ppy) 3 and m-CP is 1:9
  • the thickness is 30nm.
  • electron transport material NaTzF 2 is evaporated by vacuum evaporation with a thickness of 30nm.
  • an electron injection layer LiF is vacuum evaporated with a thickness of 1 nm, and this layer is an electron injection layer.
  • a cathode Mg:Ag layer is vacuum evaporated, the Mg:Ag doping ratio is 9:1, and the thickness is 15nm.
  • the light extraction layer organic compound is evaporated by vacuum evaporation with a thickness of 60nm.
  • Example 1 The organic compound of the light extraction layer of an OLED device is C1.
  • the organic compound of the light extraction layer of the OLED device is C3.
  • the organic compound of the light extraction layer of the OLED device is C6.
  • the organic compound of the light extraction layer of an OLED device is C21.
  • the organic compound of the light extraction layer of an OLED device is C26.
  • the organic compound of the light extraction layer of an OLED device is C69.
  • Example 7 The organic compound of the light extraction layer of an OLED device is C57.
  • Example 8 The organic compound of the light extraction layer of an OLED device is C39.
  • the organic compound of the light extraction layer of an OLED device is C17.
  • the organic compound of the light extraction layer of an OLED device is C11.
  • the organic compound of the light extraction layer of an OLED device is C158.
  • Example 12 The organic compound of the light extraction layer of an OLED device is C80.
  • Example 13 The organic compound of the light extraction layer of an OLED device is C89.
  • the organic compound of the light extraction layer of an OLED device is C196.
  • the organic compound of the light extraction layer of the OLED device is CBP.
  • the structures of the compounds involved in OLED devices are as follows:
  • EQE optical testing equipment was used to test the luminous efficiencies of the OLED devices of the examples and comparative examples when the current density was 10 mA/cm 2 , and the results are shown in Table 2 below.
  • OLED device light extraction layer compound Luminous efficiency Device Example 1 C1 1.23 Device Example 2 C3 1.22 Device Example 3 C6 1.24 Device Embodiment 4 C21 1.15 Device Embodiment 5 C26 1.19 Device Embodiment 6 C69 1.22 Device Embodiment 7 C57 1.16 Device Embodiment 8 C39 1.18
  • the arylamine organic compound of the present application contains phenanthrene, bisarylamine and condensed heterocyclic rings in structure, has a high glass temperature and high thermal stability.
  • the arylamine organic compound has a high extinction coefficient for light in the ultraviolet band (i.e., ultraviolet light), and when the arylamine organic compound is used as the light extraction layer of an organic electronic device, harmful light can be effectively avoided. Adverse effects on electrodes and internal functional layers of organic electronic devices.
  • the arylamine organic compound has a small extinction coefficient for visible light and a high transmittance for visible light, thereby reducing the influence of the light extraction layer on the light extraction efficiency of the organic electronic device.
  • the aromatic amine organic compound has a relatively high refractive index, which can effectively reflect as much visible light as possible. Therefore, the use of the aromatic amine organic compound as a light extraction layer material in an organic electronic device can effectively improve the light extraction efficiency of visible light of the organic electronic device.

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Abstract

本申请公开了一种芳胺类有机化合物及其应用，所述芳胺类有机化合物具有如通式(1)所示的结构。所述芳胺类有机化合物具有较高的玻璃温度而具有较高的热稳定性，对可见光的消光系数较小，且具备较高的折射率，将所述芳胺类有机化合物作为光取出层材料用于有机电子器件，可以有效地提高有机电子器件可见光的发光效率。

Description

芳胺类有机化合物及其应用 技术领域
本申请涉及发光材料技术领域，尤其涉及一种芳胺类有机化合物、包括所述芳胺类有机化合物的混合物和有机电子器件。
背景技术
有机电致发光显示设备是一类自发光型的显示装置，通过载流子在各个功能层间的转移、复合产生激子，依靠高量子效率的有机化合物或金属配合物发光，具有自发光、高亮度、高效率、高对比度、高响应性等特点。
近些年，有机电致发光二极管(OLED)的发光效率有了很大的提升，但是其内部量子效率已经接近理论极限。而对于有机电致发光二极管而言，在发光层所发出的光射入其它膜时，若以某个角度以上入射，则会在发光层与其它膜的界面处发生全反射，导致发光层所发出的光无法射出器件，使得仅能够利用发光层所发出的光的一部分。因此，提高光取出效率成为了可进一步提高器件稳定性和电流效率的有效手段。
近年来，为了提高光的取出效率，业界提出了在折射率低的半透明电极的外侧设置折射率高的“覆盖层”(光取出层)的发光器件。如在2001年，Hung等人在金属阴极的表面覆盖了一层约50nm的有机化合物或无机化合物，通过控制厚度及折射率以提高器件的表现性能。在2003年，Riel等人已尝试将具有高折射率(n＝2.6)的无机化合物ZnSe蒸镀于阴极上，利用功能层之间折射率的差异提高光取出效率，但是受限于无机材料蒸发温度高、蒸发速率慢等原因，这类化合物并未在有机电子器件中得到更多应用。
因此，新一类的可提高有机电子器件光取出效率的材料需要被进一步开发。
技术问题
现有技术中的有机电子器件的发光效率有待进一步提高。
技术解决方案
本申请提供一种芳胺类有机化合物、包括所述芳胺类有机化合物的混合物和有机电子器件。
本申请的技术方案如下：
一种芳胺类有机化合物，具有如通式(1)所示的结构：
Figure PCTCN2022087065-appb-000001
其中，L 1-L 4分别独立选自单键、取代或未取代的具有6至30个环原子的芳香基团、或取代或未取代的具有5至30个环原子的杂芳香基团；
Ar 1选自式(A-1)或式(A-2)所示的任一结构；
Ar 2选自式(A-2)-(A-6)所示的任一结构；
Ar 3、Ar 4分别独立选自上述式(A-3)-(A-6)所示的任一结构；
式(A-1)-(A-6)所示的结构式如下：
Figure PCTCN2022087065-appb-000002
其中，n选自0、1、2、3或4；
Y选自O、S或NR 2；
X和X 1-X 8每次出现，分别独立选自CR 3或N，且X 1-X 8中至少有一个选自N；
R 1、R 2、R 3每次出现，分别独立地选自-H、-D、具有1至20个C原子的直链烷基、具有1至20个C原子的直链烷氧基、具有3至20个C原子的支链烷基、具有3至20个C原子的支链烷氧基、具有3至20个C原子的环状的烷基、具有3至20个C原子的环状烷氧基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、胺基、-CF 3、-Cl、-Br、-F、-I、具有2至20个C原子的烯基、或取代或未取代的环原子数为6至20的芳香基团，或这些基团的组合。
本申请还提供一种混合物，所述混合物包括上述芳胺类有机化合物及至少一种有机功能材料，所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光材料、主体材料、主体材料或有机染料。
本申请还提供一种有机电子器件，包含两个电极、设置在所述两个电极之间的一个或多个有机功能层、及设置于其中一电极的表面且远离有机功能层一侧的光取出层，所述光取出层中包括至少一种上述芳胺类有机化合物。
有益效果
本申请的芳胺类有机化合物结构上含有菲、双芳胺以及稠杂环，而具有较高的玻璃温度及较高的热稳定性。此外，所述芳胺类有机化合物对紫外波段光的消光系数高，在使用所述芳胺类有机化合物作为有机电子器件的光取出层时，可以有效地避免有害光对有机电子器件的电极及内部功能层的不利影响。进一步的，所述芳胺类有机化合物对可见光的消光系数较小，对可见光有较高的透射率，从而降低对器件出光效率的影响。将所述芳胺类有机化合物作为光取出层材料用于有机电子器件中，可以有效地提高器件可见光的出光效率。
附图说明
为了更清楚地说明本申请实施例中的技术方案，下面将对实施例描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本申请的一些实施例，对于本领域技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其它的附图。
图1是本申请实施例提供的一种有机电子器件的结构示意图；
图2是实施例1的有机化合物C1在二氯甲烷中的紫外可见吸收光谱图；
图3是实施例2的有机化合物C21在二氯甲烷中的紫外可见吸收光谱图。
本申请的实施方式
下面将结合本申请实施例中的附图，对本申请实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本申请一部分实施例，而不是全部的实施例。基于本申请中的实施例，本领域技术人员在没有做出创造性劳动的前提下所获得的所有其它实施例，都属于本申请保护的范围。此外，应当理解的是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。在本申请中，在未作相反说明的情况下，使用的方位词如“上”和“下”通常是指器件实际使用或工作状态下的上和下。另外，在本申请的描述中，术语“包括”是指“包括但不限于”，术语“多个”是指“两个或两个以上”。本申请的各种实施例可以以一个范围的形式存在；应当理解，以一范围形式的描述仅仅是因为方便及简洁，不应理解为对本申请范围的硬性限制；因此，应当认为所述的范围描述已经具体公开所有可能的子范围以及该范围内的单一数值。例如，应当认为从1到6的范围描述已经具体公开子范围，例如从1到3，从1到4，从1到5，从2到4，从2到6，从3到6等，以及所述范围内的单一数字，例如1、2、3、4、5及6，此不管范围为何皆适用。另外，每当在本文中指出数值范围，是指包括所指范围内的任何引用的数字(分数或整数)。
在本申请中，芳香基团、芳香族、芳香环系具有相同的含义，可以互换。
在本申请中，杂芳香基团、杂芳香族、杂芳香环系具有相同的含义，可以互换。
在本申请中，“取代”表示被取代基中的氢原子被取代基所取代。
在本申请中，同一取代基多次出现时，可独立选自不同基团。如通式含有多个R 1，则R 1可独立选自不同基团。
在本申请中，“取代或未取代”表示所定义的基团可以被取代，也可以不被取代。当所定义的基团为被取代时，应理解为所定义的基团可以被一个或多个取代基R取代，所述R选自但不限于：氘原子、氰基、异氰基、硝基或卤素，含有1-20个C原子的烷基、含有3-20个环原子的杂环基、含有6-20个环原子的芳香基团、含有5-20个环原子的杂芳香基团、-NR’R”、硅烷基、羰基、烷氧基羰基、芳氧基羰基、氨基甲酰基、卤甲酰基、甲酰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、三氟甲基，且上述基团也可以进一步被本领域可接受取代基取代；可以理解，-NR’R”中R’和R”分别独立选自但不限于：H、氘原子、氰基、异氰基、硝基或卤素、含有1-10个C原子的烷基、含有3-20个环原子的杂环基、含有6-20个环原子的芳香基团、含有5-20个环原子的杂芳香基团。优选地，R选自但不限于：氘原子、氰基、异氰基、硝基或卤素、含有1-10个C原子烷基、含有3-10个环原子的杂环基、含有6-20个环原子的芳香基团、含有5-20个环原子的杂芳香基团、硅烷基、羰基、烷氧基羰基、芳氧基羰基、氨基甲酰基、卤甲酰基、甲酰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、三氟甲基，且上述基团也可以进一步被本领域可接受的取代基取代。
在本申请中，“环原子数”表示原子键合成环状而得到的结构化合物(例如，单环化合物、稠环化合物、交联化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的原子数。该环被取代基所取代时，取代基所包含的原子不包括在成环原子内。关于以下所述的“环原子数”，在没有特别说明的条件下也是同样的。例如，苯环的环原子数为6，萘环的环原子数为10，噻吩基的环原子数为5。
在本申请中，“芳基或芳香基团”是指在芳香环化合物的基础上除去一个氢原子衍生的芳族烃基，可以为单环芳基、稠环芳基或多环芳基，对于多环的环中，至少一个是芳族环系。例如，“取代或未取代的具有6至40个环原子的芳基”是指包含6至40个环原子的芳基，优选取代或未取代的具有6至30个环原子的芳基，更优选取代或未取代的具有6至 18个环原子的芳基，特别优选取代或未取代的具有6至14个环原子的芳基，且芳基上任选进一步被取代；合适的实例包括但不限于：苯基、联苯基、三联苯基、萘基、蒽基、菲基、荧蒽基、三亚苯基、芘基、苝基、并四苯基、芴基、二萘嵌苯基、苊基及其衍生物。可以理解，多个芳基也可以被短的非芳族单元间断(例如<10％的非H原子，比如C、N或O原子)，具体如苊、芴，或者9,9-二芳基芴、三芳胺、二芳基醚体系也应该包含在芳基的定义中。
在本申请中，“杂芳基或杂芳香基团”是指在芳基的基础上至少一个碳原子被非碳原子所替代，非碳原子可以为N原子、O原子、S原子等。例如，“取代或未取代的具有5至40个环原子的杂芳基”是指具有5至40个环原子的杂芳基，优选取代或未取代的具有6至30个环原子的杂芳基，更优选取代或未取代的具有6至18个环原子的杂芳基，特别优选取代或未取代的具有6至14个环原子的杂芳基，且杂芳基任选进一步被取代，合适的实例包括但不限于：噻吩基、呋喃基、吡咯基、咪唑基、二唑基、三唑基、咪唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、苯并噻吩基、苯并呋喃基、吲哚基、吡咯并咪唑基、吡咯并吡咯基、噻吩并吡咯基、噻吩并噻吩基、呋喃并吡咯基、呋喃并呋喃基、噻吩并呋喃基、苯并异噁唑基、苯并异噻唑基、苯并咪唑基、邻二氮萘基、菲啶基、伯啶基、喹唑啉酮基、二苯并噻吩基、二苯并呋喃基、咔唑基及其衍生物。
在本申请中，“烷基”可以表示直链、支链和/或环状烷基。烷基的碳数可以为1至50、1至30、1至20、1至10或1至6。包含该术语的短语，例如，“C 1-9烷基”是指包含1-9个碳原子的烷基，每次出现时，可以互相独立地为C 1烷基、C 2烷基、C 3烷基、C 4烷基、C 5烷基、C 6烷基、C 7烷基、C 8烷基或C 9烷基。烷基的非限制性实例包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-乙基丁基、3,3-二甲基丁基、正戊基、异戊基、新戊基、叔戊基、环戊基、1-甲基戊基、3-甲基戊基、2-乙基戊基、4-甲基-2-戊基、正己基、1-甲基己基、2-乙基己基、2-丁基己基、环己基、4-甲基环己基、4-叔丁基环己基、正庚基、1-甲基庚基、2,2-二甲基庚基、2-乙基庚基、2-丁基庚基、正辛基、叔辛基、2-乙基辛基、2-丁基辛基、2-己基辛基、3,7-二甲基辛基、环辛基、正壬基、正癸基、金刚烷基、2-乙基癸基、2-丁基癸基、2-己基癸基、2-辛基癸基、正十一烷基、正十二烷基、2-乙基十二烷基、2-丁基十二烷基、2-己基十二烷基、2-辛基十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、2-乙基十六烷基、2-丁基十六烷基、2-己基十六烷基、2-辛基十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基、2-乙基二十烷基、2-丁基二十烷基、2-己基二十烷基、2-辛基二十烷基、正二十一烷基、正二十二烷基、正二十三烷基、正二十四烷基、正二十五烷基、正二十六烷基、正二十七烷基、正二十八烷基、正二十九烷基、正三十烷基、金刚烷等。
在本申请中，取代基缩写对应为：n-正、sec-仲、i-异、t-叔、o-邻、m-间、p-对、Me甲基、Et乙基、Pr丙基、Bu丁基、Am正戊基、Hx己基、Cy环己基。
在本申请中，“胺基”是指胺的衍生物，具有式-N(X) 2的结构特征，其中每个“X”独立地选自H、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环基等。胺基的非限制性类型包括-NH 2、-N(烷基) 2、-NH(烷基)、-N(环烷基) 2、-NH(环烷基)、-N(杂环基) 2、-NH(杂环基)、-N(芳基) 2、-NH(芳基)、-N(烷基)(芳基)、-N(烷基)(杂环基)、-N(环烷基)(杂环基)、-N(芳基)(杂芳基)、-N(烷基)(杂芳基)等。
在本申请中，如无特别定义，羟基指-OH，羧基指-COOH，羰基指-C(＝O)-，氨基指-NH 2，甲酰基指-C(＝O)H，卤甲酰基指-C(＝O)Z(其中，Z表示卤素)，氨基甲酰基指-C(＝O)NH 2，异氰酸酯基指-NCO，异硫氰酸酯基指-NCS。
在本申请中，术语“烷氧基”是指结构为“-O-烷基”的基团，即如上所定义的烷基经由氧 原子连接至其它基团。包含该术语的短语，合适的实例包括但不限于：甲氧基(-O-CH 3或-OMe)、乙氧基(-O-CH 2CH 3或-OEt)和叔丁氧基(-O-C(CH 3) 3或-OtBu)。
在本申请中，与单键相连的“*”表示连接或稠合位点。
在本申请中，基团中未指明连接位点时，表示基团中任选可连接位点作为连接位点。
在本申请中，基团中未指明稠合位点时，表示基团中任选可稠合位点作为稠合位点，优选基团中处于邻位的两个或多个位点为稠合位点。
在本申请中，稠合位点作为稠合位点，优选基团中处于邻位的两个或多个位点为稠合位点；
在本申请中，当同一基团上含有多个相同符号的取代基时，各取代基可以彼此相同或不同，例如
Figure PCTCN2022087065-appb-000003
苯环上6个R 1可以彼此相同或不同。
在本申请中，取代基相连的单键贯穿相应的环，表述该取代基可与环的任选位置连接，例如
Figure PCTCN2022087065-appb-000004
中R与苯环的任一可取代位点相连，如
Figure PCTCN2022087065-appb-000005
表示
Figure PCTCN2022087065-appb-000006
可与
Figure PCTCN2022087065-appb-000007
上任选可取代位置形成并环。
本申请的技术方案如下：
一种芳胺类有机化合物，具有如通式(1)所示的结构：
Figure PCTCN2022087065-appb-000008
其中：
L 1-L 4分别独立选自单键、取代或未取代的具有6至30个环原子的芳香基团、或取代或未取代的具有5至30个环原子的杂芳香基团；
Ar 1选自式(A-1)或式(A-2)所示的任一结构；
Ar 2选自式(A-2)-(A-6)所示的任一结构；
Ar 3、Ar 4分别独立选自上述式(A-3)-(A-6)所示的任一结构；
式(A-1)-(A-6)所示的结构式如下：
Figure PCTCN2022087065-appb-000009
n选自0、1、2、3或4；
Y选自O、S或NR 2；
X和X 1-X 8每次出现，分别独立选自CR 3或N，且X 1-X 8中至少有一个选自N；
R 1、R 2、R 3每次出现，分别独立地选自-H、-D、具有1至20个C原子的直链烷基、具有1至20个C原子的直链烷氧基、具有3至20个C原子的支链烷基、具有3至20个C原子的支链烷氧基、具有3至20个C原子的环状的烷基、具有3至20个C原子的环状烷氧基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、胺基、-CF 3、-Cl、-Br、-F、-I、具有2至20个C原子的烯基、或取代或未取代的环原子数为6至20的芳香基团，或 这些基团的组合。
在一实施例中，R 1、R 2、R 3每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有1至10个C原子的直链烷氧基、具有3至10个C原子的支链烷基、具有3至10个C原子的支链烷氧基、具有3至10个C原子的环状的烷基、具有3至10个C原子的环状烷氧基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、胺基、-CF 3、-Cl、-Br、-F、-I、具有2至10个C原子的烯基、或取代或未取代的环原子数为6至10的芳香基团，或这些基团的组合。
在一实施例中，所述通式(1)选自式(2-1)-(2-6)所示的任一结构：
Figure PCTCN2022087065-appb-000010
其中，R 1、R 3、Y、X、X 5-X 8、L 1-L 4、Ar 3、Ar 4的含义同上文所述。
在一实施例中，式(2-5)及(2-6)中，X5-X8每次出现，独立选自CR 3或N，且X 5-X 8中至少有一个选自N；优选地，X 5选自N。
在一实施例中，式(2-1)、(2-3)及(2-5)中，Y多次出现时，选自相同的基团。
在一实施例中，式(2-2)、(2-4)及(2-6)中，X多次出现时，独立选自CR 3。进一步地，R 3每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基、具有3至10个C原子的环状的烷基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、-CF 3、-Cl、-Br、-F、-I、或取代或未取代的环原子数为6至10的芳香基团，或这些基团的组合。
在一实施例中，式(2-1)-(2-4)中，R 1每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基、具有3至10个C原子的环状的烷基、或取代或未取代的环原子数为6至10的芳香基团，或这些基团的组合。
在一实施例中，L 1-L 4分别独立选自单键、取代或未取代的具有6至20个环原子的芳香基团、或取代或未取代的具有6至20个环原子的杂芳香基团。
进一步地，L 1-L 4可选自单键、取代或未取代的具有6至13个环原子的芳香基团、或 取代或未取代的具有6至13个环原子的杂芳香基团。
在一实施例中，L 1-L 4分别独立选自单键、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的荧蒽基、取代或未取代的三亚苯基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的并四苯基、取代或未取代的芴基、取代或未取代的二萘嵌苯基、取代或未取代的苊基、取代或未取代的噻吩基、取代或未取代的呋喃基、取代或未取代的吡咯基、取代或未取代的咪唑基、取代或未取代的三唑基、取代或未取代的二唑基、取代或未取代的吡啶基、取代或未取代的联吡啶基、取代或未取代的嘧啶基、取代或未取代的三嗪基、取代或未取代的吖啶基、取代或未取代的哒嗪基、取代或未取代的吡嗪基、取代或未取代的喹啉基、取代或未取代的喹唑啉基、取代或未取代的喹喔啉基、取代或未取代的酞嗪基、取代或未取代的异喹啉基、取代或未取代的吲哚基、取代或未取代的苯并噻吩基、取代或未取代的苯并呋喃基、或者取代或未取代的
Figure PCTCN2022087065-appb-000011
其中，Y的含义同上文所述。
所述“取代或未取代”含义同前文所述。
在一实施例中，所述“取代或未取代”中的“取代”是指取代基选自氘原子、氰基、异氰基、硝基或卤素、含有1-8个C原子烷基、含有3-8个环原子的杂环基、含有6-10个环原子的芳香基团、或含有6-10个环原子的杂芳香基团。
进一步的，L 1-L 4分别独立选自单键或以下基团：
Figure PCTCN2022087065-appb-000012
其中，*表示连接位点。
在一实施例中，Y选自O或S。
在一实施例中，L 1-L 4分别独立选自单键或苯基，进一步，所述通式(1)选自式(3-1)-(3-6)所示的任一结构：
Figure PCTCN2022087065-appb-000013
Figure PCTCN2022087065-appb-000014
其中，R 1、Y、X、X 5-X 8、L 3-L 4、Ar 3、Ar 4的含义同上文所述。
在一实施例中，式(3-1)-(3-4)中Y选自O或S。在一些实施例中，Y选自氧。
在一实施例中，式(3-5)和式(3-6)中X 5选自N。
在一实施例中，通式(1)选自式(4-1)-(4-6)任一通式：
Figure PCTCN2022087065-appb-000015
在一实施例中，当Ar 1和Ar 2选自相同基团时，本申请所述的有机化合物选自对称结构。
在一实施例中，Ar 3和Ar 4分别独立选自式(B-1)-(B-7)所示的任一基团：
Figure PCTCN2022087065-appb-000016
其中，*表示连接位点；
R 3每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基、具有3至10个C原子的环状的烷基、甲硅烷基、氰基、异氰基、羟基、硝基、-CF 3、-Cl、-Br、-F、-I、苯基、联苯基、三联苯基、或萘基。
在一实施例中，*-L 3-Ar 3和/或*-L 4-Ar 4选自如下基团：
Figure PCTCN2022087065-appb-000017
在一实施例中，*-L 3-Ar 3与*-L 4-Ar 4选自相同的基团。
在一实施例中，按照本申请所述的芳胺类有机化合物，其在波长630nm处的折射率大于1.7；优选地，大于1.78；更优选地，大于1.83。
在一实施例中，按照本申请所述的芳胺类有机化合物，其在波长大于430nm的范围有较小的消光系数，对可见光有较高的透射率，从而降低对设备出光效率的影响。所述的芳胺类有机化合物在波长为430nm时的消光系数小于0.1；优选地，小于0.003；更优选地，小于0.001。
在一些实施方案中，按照本申请所述的芳胺类有机化合物，其在小于等于400nm的波长范围有较大的消光系数。作为示例，所述芳胺类有机化合物在波长为350nm时的消光系数≥0.3；较好是≥0.5，更好是≥0.7，最好是≥1.0。
在一些实施例中，按照本申请所述的芳胺类有机化合物，具有较高的玻璃化温度，以提升材料的热稳定性。在一些实施例中，所述芳胺类有机化合物玻璃化温度Tg≥100℃；优选为Tg≥120℃，较为优选为Tg≥140℃，更为优选为Tg≥160℃。
作为示例，本申请的芳胺类有机化合物可以选自但不限于下述结构中的任意一种：
Figure PCTCN2022087065-appb-000018
Figure PCTCN2022087065-appb-000019
Figure PCTCN2022087065-appb-000020
Figure PCTCN2022087065-appb-000021
Figure PCTCN2022087065-appb-000022
Figure PCTCN2022087065-appb-000023
Figure PCTCN2022087065-appb-000024
Figure PCTCN2022087065-appb-000025
可以理解，上述芳胺类有机化合物的结构式中的H可以进一步被取代。
本申请进一步涉及一种混合物，包含有至少一种以上所述的有机化合物及至少另一种有机功能材料，所述另一种的有机功能材料可以为但不限于空穴注入材料(HIM)、空穴传输材料(HTM)、电子传输材料(ETM)、电子注入材料(EIM)、电子阻挡材料(EBM)、空穴阻挡材料(HBM)、发光材料(Emitter)、主体材料(Host)和有机染料。例如在WO2010135519A1、US20090134784A1和WO 2011110277A1中对各种有机功能材料有详细的描述，特此将此3专利文件中的全部内容并入本文作为参考。
本申请还涉及一种组合物，包括至少一种如上所述的有芳胺类机化合物或混合物、及至少一种有机溶剂。
所述有机溶剂选自基于芳族或杂芳族的溶剂、基于酯的溶剂、基于芳族酮的溶剂、基于芳族醚的溶剂、脂肪族酮、脂肪族醚、脂环族化合物、烯烃类化合物、硼酸酯类化合物及磷酸酯类化合物中的至少一种。
在至少一实施例中，所述组合物中，所述有机溶剂选自基于芳族或杂芳族的溶剂。
所述基于芳族或杂芳族的溶剂可以选自但不限于对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、 邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、环己基苯、苄基丁基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、α,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、喹啉、异喹啉、2-呋喃甲酸甲酯及2-呋喃甲酸乙酯中的至少一种。
所述基于酯的溶剂可以选自但不限于辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。特别优选辛酸辛酯、癸二酸二乙酯、邻苯二甲酸二烯丙酯及异壬酸异壬酯中的至少一种。
所述基于芳族酮的溶剂可以选自但不限于1-四氢萘酮、2-四氢萘酮、2-(苯基环氧)四氢萘酮、6-(甲氧基)四氢萘酮、苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物。其中，作为示例，所述衍生物可以选自但不限于4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮及2-甲基苯丙酮中的至少一种。
所述基于芳族醚的溶剂可以选自但不限于3-苯氧基甲苯、丁氧基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,3-二丙氧基苯、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃及乙基-2-萘基醚中的至少一种。
所述基于脂肪族酮的溶剂可以选自但不限于2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、葑酮、佛尔酮、异佛尔酮、二正戊基酮等；或脂肪族醚，例如，戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚及四乙二醇二甲醚中的至少一种。
可以理解，所述有机溶剂可以单独使用，也可以作为两种或多种有机溶剂的混合溶剂使用。
在一实施例中，本申请的组合物包括至少一种如上所述的芳胺类有机化合物或混合物、及至少一种有机溶剂，还可进一步包括另一种有机溶剂。
所述另一种有机溶剂可以选自但不限于甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜(DMSO)、四氢萘、萘烷及茚中的至少一种。
在一些较佳的实施例中，适合本申请的有机溶剂是汉森(Hansen)溶解度参数在以下范围内的溶剂：
δd(色散力)在17.0-23.2MPa1/2范围内，尤其是在18.5-21.0MPa1/2范围内；
δp(极性力)在0.2-12.5MPa1/2范围内，尤其是在2.0-6.0MPa1/2范围内；
δh(氢键力)在0.9-14.2MPa1/2范围内，尤其是在2.0-6.0MPa1/2范围内。
在一实施例中，按照本申请的组合物，所述有机溶剂在选取时需考虑沸点。在至少一些实施例中，所述有机溶剂的沸点≥150℃；优选为≥180℃；较优为≥200℃；更优为≥250℃；最优为≥300℃。这些范围内的沸点对防止喷墨印刷头的喷嘴堵塞是有益的。
可以理解，所述有机溶剂可从溶剂体系中蒸发，以形成包括所述有机化合物的薄膜。
在一实施例中，所述组合物为溶液。在又一些实施例中，所述组合物为悬浮液。所述溶液或悬浮液可以另外包括添加剂，用于调节粘度、调节成膜性能、提高附着性等。所述 添加剂可以选自但不限于表面活性化合物、润滑剂、润湿剂、分散剂、疏水剂及粘接剂中的至少一种。
所述组合物中，所述芳胺类有机化合物的含量为0.01-10wt％，较佳为0.1-8wt％，更佳为0.2-5wt％，最佳为0.25-3wt％。
本申请还涉及所述组合物作为涂料或印刷油墨在制备有机电子器件时的用途。在一实施例中，所述组合物通过打印或涂布的制备方法用于制备有机电子器件。所述打印或涂布的制备方法可以为但不限于喷墨打印、凹版印刷、喷印、活版印刷、丝网印刷、浸涂、旋转涂布、刮刀涂布、辊筒印花、扭转辊印刷、平版印刷、柔版印刷、轮转印刷、喷涂、刷涂、移印、狭缝型挤压式涂布等。首选的是凹版印刷、喷印及喷墨印刷。
本申请进一步涉及一种光取出层材料，选自如上所述的有机化合物或混合物或组合物。
本申请还进一步涉及一种如上所述的有机化合物、混合物或组合物在有机电子器件中的应用。所述有机电子器件可以为有机发光二极管(OLED)、有机光伏电池、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器及有机等离激元发射二极管等、特别优选为OLED。具体方案如下：
一种有机电致发光器件，包含两个电极、设置在所述两个电极之间的一个或多个有机功能层、及设置于其中一电极的表面且远离有机功能层一侧的光取出层，所述光取出层中包含如式(1)所述的芳胺类有机化合物。
进一步，一种有机电子器件，包括依次层叠设置的底电极、至少一功能层、顶电极及光取出层。所述光取出层中包含本申请所述的芳胺类有机化合物。
在一实施例中，所述底电极为阳极，所述顶电极为阴极，所述光取出层位于阴极表面上。
在一些实施例中，按照本申请的有机电子器件，一般光取出层的厚度为10nm至200nm，较好为20nm至150nm，更好为30nm至100nm，最好为40nm至90nm。
在一实施例中，按照本申请所述的有机电子器件，其中包括一个或者更多个有机功能层，所述的有机功能层选自电子注入层、电子传输层、空穴注入层、空穴传输层和发光层的一个或多个层，其中至少包含一个发光层。
在一些实施例中，按照本申请所述的有机电子器件，其中所述发光层中的发光材料选自单重态发光体、三重态发光体或者TADF材料。
在一些实施例中，按照本申请所述的有机电子器件，其中所述有机功能层选自空穴传输层、发光层和电子传输层。
在一些实施例中，按照本申请所述的有机电子器件，其中所述有机功能层选自空穴注入层、空穴传输层、发光层、电子传输层和电子注入层。
关于单重态发光体、三重态发光体及TADF材料的一些描述详见WO2017092619A。
进一步，按照本申请所述的有机电子器件，所述有机功能层包含一发光层；进一步，所述发光层材料选自三重态发光材料。
所述三重态发光材料具有如下通式所示的结构：
Figure PCTCN2022087065-appb-000026
其中，m选自1或2或3；
环A选自取代或未取代的具有5-30个环原子的含N杂芳香基团；
环B选自取代或未取代的具有6-30个环原子的芳香基团或杂芳香基团；
L为一价阴离子有机配体。
在一实施例中，环A选自如下基团中的任意一种：
Figure PCTCN2022087065-appb-000027
其中，N为连接位点。
在一实施例中，环B选自如下基团中的任意一种：
Figure PCTCN2022087065-appb-000028
其中，X 3每次出现，分别独立地选自CR 11或N；
Y 3每次出现，分别独立地选自CR 12R 13、NR 14、O、S、S＝O、SO 2、PR 14、BR 14、SiR 12R 13；
R 11、R 12、R 13、R 14每次出现，分别独立地选自氢、氘、具有1-20个碳原子的直链烷基、具有3-20个碳原子的支链或环状的烷基、氰基、硝基、-CF 3、-OCF 3、-Cl、-Br、-F、取代或未取代的具有6-30个环原子的芳香基团、取代或未取代的具有5-30个环原子的杂芳香基团，或这些基团的组合。
进一步地，所述三重态发光材料选自如下通式：
Figure PCTCN2022087065-appb-000029
进一步地，所述R 11每次出现，分别独立地选自氢、氘、具有1-10个碳原子的直链烷基、具有3-10个碳原子的支链或环状的烷基、氰基、硝基、CF 3、OCF 3、Cl、Br、F、具有6-20个环原子的芳香基团、具有5-20个环原子的杂芳香基团，或这些基团的组合；
n每次出现时，独立的选自0、1、2、3、4或5；m同上文所述。
在一实施例中，按照本申请所述的三重态发光材料选自以下结构：
Figure PCTCN2022087065-appb-000030
Figure PCTCN2022087065-appb-000031
按照本申请所述的有机电子器件可以为但不限于有机发光二极管(OLED)、有机光伏电池、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器及有机等离激元发射二极管等，特别优选为OLED。
下面对OLED的器件结构中阴极、阳极做一描述。
阳极可包含一导电金属或金属氧化物，或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个的实施例中，阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV，较好是小于0.3eV，最好是小于0.2eV。阳极材料的例子包含但不限于：Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的，本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积，如一合适的物理气相沉积法，包含射频磁控溅射，真空热蒸发，电子束(e-beam)等。在某些实施例中，阳极是图案结构化的。图案化的ITO导电基板可在市场上买到，并且可以用来制备根据本申请的器件。
阴极可包含一导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个实施例中，阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV，较好是小于0.3eV，最好是小于0.2eV。原则上，所有可用作OLED的阴极的材料都可能作为本申请器件的阴极材料。阴极材料的例子包含但不限于：Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF 2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积，如一合适的物理气相沉积法，包含射频磁控溅射，真空热蒸发，电子束(e-beam)等。
在一实施例中，按照本申请所述的有机电致发光器件，特别是有机发光二极管中，所述光取出层位于阴极表面上。
在一些更为优选的实施例中，按照本申请的有机电致发光器件，一般光取出层的厚度为10nm至200nm，较好为20nm至150nm，更好为30nm至100nm，最好为40nm至90nm。
本申请还涉及按照本申请的电致发光器件在各种电子设备中的应用，所述电子设备可以为但不限于显示设备、照明设备、光源、传感器等。
下面通过具体实施例来对本申请进行具体说明，以下实施例仅是本申请的部分实施例，不是对本申请的限定。
具体实施例
实施例1
本实施例的有机化合物C1的合成路线如下：
Figure PCTCN2022087065-appb-000032
将化合物Z1(6.5g,30mmol)、联硼酸频哪醇酯(4.06g,16mmol)、乙酸钯(1mmol)、DPEPhos(双(2-二苯基膦)苯醚，2mmol)、t-BuOK(叔丁醇钾，130mmol)加入甲苯中，置换氮气，110℃反应，得到反应液。将反应液冷却至室温，加水分层，乙酸乙酯萃取水层，合并有机层，无水硫酸钠干燥浓缩，硅胶柱分离，得化合物Z2共3.15g，产率为76％。
将化合物Z2(2.5g，9mmol)加入乙酸，升温至100℃反应，加入1g水合肼和乙酸。TLC跟踪反应，待反应完全，冷却到室温加水，并用二氯甲烷进行萃取，合并有机相用去离子水洗，收集有机层，然后进行柱层析提纯，得到白色固体Z3共1.28g，产率为58％。
将化合物Z3(1.23g，5mmol)、化合物Z4(3.14g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.06g有机化合物C1，产率为82％，MS:746[M+]。
实施例2
本实施例的有机化合物C3的合成路线如下：
Figure PCTCN2022087065-appb-000033
将化合物Z3(1.23g，5mmol)、化合物Z5(3.7g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.21g有机化合物C3，产率为76％，MS:846[M+]。
实施例3
本实施例的有机化合物C6的合成路线如下：
Figure PCTCN2022087065-appb-000034
将化合物Z3(1.23g，5mmol)、化合物Z6(4.13g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.28g有机化合物C6，产率为71％，MS:926[M+]。
实施例4
本实施例的有机化合物C21的合成路线如下：
Figure PCTCN2022087065-appb-000035
将化合物Z3(1.23g，5mmol)、化合物Z7(2.86g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.84g有机化合物C21，产率为82％，MS(ASAP)＝694[M+]。
实施例5
本实施例的有机化合物C26的合成路线如下：
Figure PCTCN2022087065-appb-000036
将化合物Z3(1.23g，5mmol)、化合物Z8(3.86g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.54g有机化合物C26，产率为58％，MS:876[M+]。
实施例6
本实施例的有机化合物C69的合成路线如下：
Figure PCTCN2022087065-appb-000037
将化合物Z3(1.23g，5mmol)、化合物Z9(3.14g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.87g有机化合物C69，产率为77％，MS:746[M+]。
实施例7
本实施例的有机化合物从C57的合成路线如下：
Figure PCTCN2022087065-appb-000038
将化合物Z3(2.46g，10mmol)、化合物Z10(3.67g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(1.15g，12mmol)及三二亚苄基丙酮二钯(0.27g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.91g化合物Z11，产率为72％。
将化合物Z11(2.72g，5mmol)、化合物Z12(1.81g，6mmol)溶解在无水甲苯中， 加入叔丁醇钠(0.57g，6mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.36g有机化合物C57，产率为83％，MS:810[M+]。
实施例8
本实施例的有机化合物C39的合成路线如下：
Figure PCTCN2022087065-appb-000039
将化合物Z3(2.46g，10mmol)、化合物Z13(3.4g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(1.15g，12mmol)及三二亚苄基丙酮二钯(0.27g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.58g化合物Z14，产率为69％。
将化合物Z14(2.6g，5mmol)、化合物Z15(2.11g，6mmol)溶解在无水甲苯中，加入叔丁醇钠(0.57g，6mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.13g有机化合物C39，产率为75％，MS:835[M+]。
实施例9
本实施例的有机化合物C17的合成路线如下：
Figure PCTCN2022087065-appb-000040
将化合物Z3(1.23g，5mmol)、化合物Z16(3.97g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.18g有机化合物C17，产率为71％，MS:896[M+]。
实施例10
本实施例的有机化合物C11的合成路线如下：
Figure PCTCN2022087065-appb-000041
将化合物Z3(1.23g，5mmol)、化合物Z17(3.87g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.81g有机化合物C11，产率为64％，MS:878[M+]。
实施例11
本实施例的有机化合物C158的合成路线如下：
Figure PCTCN2022087065-appb-000042
将化合物Z3(2.46g，10mmol)、化合物Z18(3.87g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(1.15g，12mmol)及三二亚苄基丙酮二钯(0.27g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.66g化合物Z19，产率为53％。
将化合物Z19(2.51g，5mmol)、化合物Z20(1.82g，6mmol)溶解在无水甲苯中，加入叔丁醇钠(0.57g，6mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.58g有机化合物C158，产率为67％，MS:771[M+]。
实施例12
本实施例的有机化合物C80的合成路线如下：
Figure PCTCN2022087065-appb-000043
将化合物Z3(1.23g，5mmol)、化合物Z21(3.33g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(0.96g，10mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到1.75g有机化合物C80，产率为45％，MS:780[M+]。
实施例13
本实施例的有机化合物C89的合成路线如下：
Figure PCTCN2022087065-appb-000044
将化合物Z3(2.46g，10mmol)、Z22(2.85g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(1.15g，12mmol)及三二亚苄基丙酮二钯(0.27g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.65g化合物Z23，产率为61％。
将化合物Z23(2.17g，5mmol)、化合物Z24(1.72g，6mmol)溶解在无水甲苯中，加入叔丁醇钠(0.57g，6mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.59g有机化合物C89，产率为72％，MS:719[M+]。
实施例14
本实施例的有机化合物C196的合成路线如下：
Figure PCTCN2022087065-appb-000045
将化合物Z3(2.46g，10mmol)、化合物Z25(3.86g，11mmol)溶解在无水甲苯中，加入叔丁醇钠(1.15g，12mmol)及三二亚苄基丙酮二钯(0.27g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到3.65g化合物Z26，产率为65％。
将化合物Z26(2.8g，5mmol)、化合物Z27(2.11g，6mmol)溶解在无水甲苯中，加入叔丁醇钠(0.57g，6mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应12小时，移开热源。待体系冷却后，加入去离子水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱，得到2.5g有机化合物C196，产率为57％，MS:877[M+]。
对比例
本对比例的有机化合物为CBP(4,4'-二(9-咔唑)联苯)。
测试实施例1的有机化合物C1及实施例4的有机化合物C21在二氯甲烷中的紫外可见吸收光谱。其中，实施例1的有机化合物C1在溶液中的紫外可见吸收光谱图请参图2，实施例4的有机化合物C21在溶液中的紫外可见吸收光谱图请参图3。
消光系数及折射率测试
通过真空蒸镀方式将实施例1-14及对比例的有机化合物蒸镀于单晶硅上形成50nm的薄膜，单晶硅置于椭偏仪(ES-01)样品台，入射角为70度，测试环境为大气环境，有机化合物对波长为430nm的光的消光系数k(消光系数@430nm)与对波长为630nm的光的 折射率n(折射率@630nm)测试结果由椭偏仪拟合得出，测试结果参下表一。
表一：
  有机化合物 消光系数@430nm 折射率@630nm
实施例1 C1 0.01 1.90
实施例2 C3 0.02 1.91
实施例3 C6 0.01 1.92
实施例4 C21 0.01 1.87
实施例5 C26 0.01 1.89
实施例6 C69 0.03 1.91
实施例7 C57 0.03 1.87
实施例8 C39 0.04 1.88
实施例9 C17 0.05 1.91
实施例10 C11 0.05 1.92
实施例11 C158 0.03 1.90
实施例12 C80 0.04 1.92
实施例13 C89 0.02 1.89
实施例14 C196 0.01 1.88
对比例 CBP 0 1.74
由图2-3及表一可知：
相较于对比例的有机化合物，实施例1-14的芳胺类有机化合物对可见光波段的光吸收较弱，对紫外波段的光有较高的吸收。
相较于对比例的有机化合物，实施例1-14的芳胺类有机化合物具有较高的折射率。
OLED器件制备及性能测试
下面通过具体实施例来详细说明采用上述的OLED器件的制备过程，OLED器件的结构为：ITO/Ag/ITO(阳极)/HATCN/SFNFB/m-CP:Ir(p-ppy) 3/NaTzF 2/LiF/Mg:Ag/光取出层。
OLED器件示意图如图1所示，其中101是基板，102是阳极，103是空穴注入层(HIL)，104是空穴传输层(HTL)，105是发光层，106是电子传输层(ETL)，107电子注入层，108是阴极，109是光取出层。
制备步骤如下：
清洗ITO/Ag/ITO导电玻璃阳极层，后用去离子水、丙酮、异丙醇超声清洗15分钟，然后在等离子体清洗器中处理5分钟以提高电极功函。在ITO阳极层上，通过真空蒸镀方式蒸镀空穴注入层材料HATCN，厚度为5nm，蒸镀速率
Figure PCTCN2022087065-appb-000046
在空穴注入层上，通过真空蒸镀方式蒸镀空穴传输材料SFNFB，厚度为80nm。在空穴传输层之上蒸镀发光层，m-CP作为主体材料，Ir(p-ppy) 3作为掺杂材料，Ir(p-ppy) 3和m-CP的质量比为1:9，厚度为30nm。 在发光层之上，通过真空蒸镀方式蒸镀电子传输材料NaTzF 2，厚度为30nm。在电子传输层之上，真空蒸镀电子注入层LiF，厚度为1nm，该层为电子注入层。在电子注入层之上，真空蒸镀阴极Mg:Ag层，Mg:Ag掺杂比例为9:1，厚度15nm。在阴极层之上，通过真空蒸镀方式蒸镀光取出层有机化合物，厚度为60nm。
器件实施例1：OLED器件的光取出层有机化合物为C1。
器件实施例2：OLED器件的光取出层有机化合物为C3。
器件实施例3：OLED器件的光取出层有机化合物为C6。
器件实施例4：OLED器件的光取出层有机化合物为C21。
器件实施例5：OLED器件的光取出层有机化合物为C26。
器件实施例6：OLED器件的光取出层有机化合物为C69。
器件实施例7：OLED器件的光取出层有机化合物为C57。
器件实施例8：OLED器件的光取出层有机化合物为C39。
器件实施例9：OLED器件的光取出层有机化合物为C17。
器件实施例10：OLED器件的光取出层有机化合物为C11。
器件实施例11：OLED器件的光取出层有机化合物为C158。
器件实施例12：OLED器件的光取出层有机化合物为C80。
器件实施例13：OLED器件的光取出层有机化合物为C89。
器件实施例14：OLED器件的光取出层有机化合物为C196。
器件对比例：OLED器件的光取出层有机化合物为CBP。
其中，OLED器件所涉及的化合物的结构如下：
Figure PCTCN2022087065-appb-000047
采用EQE光学测试仪器测试电流密度为10mA/cm 2时各实施例及对比例的OLED器件的发光效率，结果参下表二。
表二：
OLED器件 光取出层化合物 发光效率
器件实施例1 C1 1.23
器件实施例2 C3 1.22
器件实施例3 C6 1.24
器件实施例4 C21 1.15
器件实施例5 C26 1.19
器件实施例6 C69 1.22
器件实施例7 C57 1.16
器件实施例8 C39 1.18
器件实施例9 C17 1.21
器件实施例10 C11 1.25
器件实施例11 C158 1.19
器件实施例12 C80 1.23
器件实施例13 C89 1.20
器件实施例14 C196 1.17
器件对比例 CBP 1
由表二可知：相较于对比例的OLED器件，实施例1-14的OLED器件的发光效率更高。可见，本申请的有机化合物可以有效地提升有机电子器件的发光效率。
本申请的芳胺类有机化合物结构上含有菲、双芳胺以及稠杂环，具有较高的玻璃温度，而具有较高的热稳定性。此外，所述芳胺类有机化合物对紫外波段的光(即，紫外光)的消光系数高，在使用所述芳胺类有机化合物作为有机电子器件的光取出层时，可以有效地避免有害光对有机电子器件的电极及内部功能层的不利影响。此外，所述芳胺类有机化合物对可见光的消光系数较小，而对可见光有较高的透射率，从而降低光取出层对有机电子器件出光效率的影响。进一步的，所述芳胺类有机化合物具备较高的折射率，可以有效地将可见光尽量多的反射出去。因此，所述芳胺类有机化合物作为光取出层材料用于有机电子器件中，可以有效地提高有机电子器件可见光的出光效率。
以上对本申请实施例所提供的芳胺类有机化合物、混合物及有机电子器件进行了详细介绍，本文中应用了具体个例对本申请的原理及实施方式进行了阐述，以上实施例的说明只是用于帮助理解本申请的方法及其核心思想；同时，对于本领域的技术人员，依据本申请的思想，在具体实施方式及应用范围上均会有改变之处，综上所述，本说明书内容不应理解为对本申请的限制。

Claims (20)

  1. 一种芳胺类有机化合物，其中，具有如通式(1)所示的结构：
    Figure PCTCN2022087065-appb-100001
    其中：
    L 1-L 4分别独立选自单键、取代或未取代的具有6至30个环原子的芳香基团、或取代或未取代的具有5至30个环原子的杂芳香基团；
    Ar 1选自式(A-1)或式(A-2)所示的任一结构；
    Ar 2选自式(A-2)-(A-6)所示的任一结构；
    Ar 3、Ar 4分别独立选自上述式(A-3)-(A-6)所示的任一结构；
    式(A-1)-(A-6)所示的结构式如下：
    Figure PCTCN2022087065-appb-100002
    n选自0、1、2、3或4；
    Y选自O、S或NR 2；
    X和X 1-X 8每次出现，分别独立选自CR 3或N，且X 1-X 8中至少有一个选自N；
    R 1、R 2、R 3每次出现，分别独立地选自-H、-D、具有1至20个C原子的直链烷基、具有1至20个C原子的直链烷氧基、具有3至20个C原子的支链烷基、具有3至20个C原子的支链烷氧基、具有3至20个C原子的环状的烷基、具有3至20个C原子的环状烷氧基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、胺基、-CF 3、-Cl、-Br、-F、-I、具有2至20个C原子的烯基、或取代或未取代的环原子数为6至20的芳香基团，或这些基团的组合。
  2. 如权利要求1所述的芳胺类有机化合物，其中，所述通式(1)选自式(2-1)-(2-6)所示的任一结构：
    Figure PCTCN2022087065-appb-100003
    Figure PCTCN2022087065-appb-100004
  3. 如权利要求1所述的芳胺类有机化合物，其中，所述L 1-L 4分别独立选自单键或以下基团：
    Figure PCTCN2022087065-appb-100005
    其中：*表示连接位点。
  4. 如权利要求1所述的芳胺类有机化合物，其中，所述通式(1)选自式(3-1)-(3-6)所示的任一结构：
    Figure PCTCN2022087065-appb-100006
  5. 如权利要求1所述的芳胺类有机化合物，其中，所述Ar 3和Ar 4分别独立选自式(B-1)-(B-7)所示的任一基团：
    Figure PCTCN2022087065-appb-100007
    其中：
    *表示连接位点；
    R 3每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基、具有3至10个C原子的环状的烷基、甲硅烷基、氰基、异氰基、羟基、硝基、-CF 3、-Cl、-Br、-F、-I、苯基、联苯基、三联苯基、或萘基。
  6. 如权利要求1所述的芳胺类有机化合物，其中，所述通式(1)中*-L 3-Ar 3和/或*-L 4-Ar 4选自如下基团：
    Figure PCTCN2022087065-appb-100008
    其中：*表示连接位点。
  7. 如权利要求1所述的芳胺类有机化合物，其中，选自以下任一化合物：
    Figure PCTCN2022087065-appb-100009
    Figure PCTCN2022087065-appb-100010
    Figure PCTCN2022087065-appb-100011
    Figure PCTCN2022087065-appb-100012
    Figure PCTCN2022087065-appb-100013
    Figure PCTCN2022087065-appb-100014
    Figure PCTCN2022087065-appb-100015
    Figure PCTCN2022087065-appb-100016
  8. 一种混合物，包括芳胺类有机化合物及至少一种有机功能材料，所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光材料、主体材料、主体材料或有机染料，其中，所述芳胺类有机化合物，具有如通式(1)所示的结构：
    Figure PCTCN2022087065-appb-100017
    其中：
    L 1-L 4分别独立选自单键、取代或未取代的具有6至30个环原子的芳香基团、或取代或未取代的具有5至30个环原子的杂芳香基团；
    Ar 1选自式(A-1)或式(A-2)所示的任一结构；
    Ar 2选自式(A-2)-(A-6)所示的任一结构；
    Ar 3、Ar 4分别独立选自上述式(A-3)-(A-6)所示的任一结构；
    式(A-1)-(A-6)所示的结构式如下：
    Figure PCTCN2022087065-appb-100018
    n选自0、1、2、3或4；
    Y选自O、S或NR 2；
    X和X 1-X 8每次出现，分别独立选自CR 3或N，且X 1-X 8中至少有一个选自N；
    R 1、R 2、R 3每次出现，分别独立地选自-H、-D、具有1至20个C原子的直链烷基、具有1至20个C原子的直链烷氧基、具有3至20个C原子的支链烷基、具有3至20个C原子的支链烷氧基、具有3至20个C原子的环状的烷基、具有3至20个C原子的环状烷氧基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、胺基、-CF 3、-Cl、-Br、-F、-I、具有2至20个C原子的烯基、或取代或未取代的环原子数为6至20的芳香基团，或这些基团的组合。
  9. 如权利要求8所述的混合物，其中，所述通式(1)选自式(2-1)-(2-6)所示的任一结构：
    Figure PCTCN2022087065-appb-100019
  10. 如权利要求8所述的混合物，其中，所述L 1-L 4分别独立选自单键或以下基团：
    Figure PCTCN2022087065-appb-100020
    其中：*表示连接位点。
  11. 如权利要求8所述的混合物，其中，所述通式(1)选自式(3-1)-(3-6)所示的任一结构：
    Figure PCTCN2022087065-appb-100021
    Figure PCTCN2022087065-appb-100022
  12. 如权利要求8所述的混合物，其中，所述Ar 3和Ar 4分别独立选自式(B-1)-(B-7)所示的任一基团：
    Figure PCTCN2022087065-appb-100023
    其中：
    *表示连接位点；
    R 3每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基、具有3至10个C原子的环状的烷基、甲硅烷基、氰基、异氰基、羟基、硝基、-CF 3、-Cl、-Br、-F、-I、苯基、联苯基、三联苯基、或萘基。
  13. 如权利要求8所述的混合物，其中，所述通式(1)中*-L 3-Ar 3和/或*-L 4-Ar 4选自如下基团：
    Figure PCTCN2022087065-appb-100024
    其中：*表示连接位点。
  14. 如权利要求8所述的混合物，其中，选自以下任一化合物：
    Figure PCTCN2022087065-appb-100025
    Figure PCTCN2022087065-appb-100026
    Figure PCTCN2022087065-appb-100027
    Figure PCTCN2022087065-appb-100028
    Figure PCTCN2022087065-appb-100029
    Figure PCTCN2022087065-appb-100030
    Figure PCTCN2022087065-appb-100031
    Figure PCTCN2022087065-appb-100032
  15. 一种有机电子器件，包括两个电极、设置在所述两个电极之间的一个或多个有机功能层、及设置于其中一电极的表面且远离所述有机功能层一侧的光取出层，所述光取出层中包括芳胺类有机化合物，其中，所述芳胺类有机化合物，具有如通式(1)所示的结构：
    Figure PCTCN2022087065-appb-100033
    其中：
    L 1-L 4分别独立选自单键、取代或未取代的具有6至30个环原子的芳香基团、或取代或未取代的具有5至30个环原子的杂芳香基团；
    Ar 1选自式(A-1)或式(A-2)所示的任一结构；
    Ar 2选自式(A-2)-(A-6)所示的任一结构；
    Ar 3、Ar 4分别独立选自上述式(A-3)-(A-6)所示的任一结构；
    式(A-1)-(A-6)所示的结构式如下：
    Figure PCTCN2022087065-appb-100034
    n选自0、1、2、3或4；
    Y选自O、S或NR 2；
    X和X 1-X 8每次出现，分别独立选自CR 3或N，且X 1-X 8中至少有一个选自N；
    R 1、R 2、R 3每次出现，分别独立地选自-H、-D、具有1至20个C原子的直链烷基、具有1至20个C原子的直链烷氧基、具有3至20个C原子的支链烷基、具有3至20个C原子的支链烷氧基、具有3至20个C原子的环状的烷基、具有3至20个C原子的环状烷氧基、取代或未取代的甲硅烷基、氰基、异氰基、羟基、硝基、胺基、-CF 3、-Cl、-Br、-F、-I、具有2至20个C原子的烯基、或取代或未取代的环原子数为6至20的芳香基团，或这些基团的组合。
  16. 如权利要求15所述的有机电子器件，其中，所述通式(1)选自式(2-1)-(2-6)所示的任一结构：
    Figure PCTCN2022087065-appb-100035
  17. 如权利要求15所述的有机电子器件，其中，所述L 1-L 4分别独立选自单键或以下基团：
    Figure PCTCN2022087065-appb-100036
    其中：*表示连接位点。
  18. 如权利要求15所述的有机电子器件，其中，所述通式(1)选自式(3-1)-(3-6)所示的任一结构：
    Figure PCTCN2022087065-appb-100037
  19. 如权利要求15所述的有机电子器件，其中，所述Ar 3和Ar 4分别独立选自式(B-1)-(B-7)所示的任一基团：
    Figure PCTCN2022087065-appb-100038
    其中：
    *表示连接位点；
    R 3每次出现，分别独立地选自-H、-D、具有1至10个C原子的直链烷基、具有3至10个C原子的支链烷基、具有3至10个C原子的环状的烷基、甲硅烷基、氰基、异氰基、羟基、硝基、-CF 3、-Cl、-Br、-F、-I、苯基、联苯基、三联苯基、或萘基。
  20. 如权利要求15所述的有机电子器件，其中，所述通式(1)中*-L 3-Ar 3和/或*-L 4-Ar 4选自如下基团：
    Figure PCTCN2022087065-appb-100039
    其中：*表示连接位点。
PCT/CN2022/087065 2021-11-01 2022-04-15 芳胺类有机化合物及其应用 Ceased WO2023071073A1 (zh)

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