CN109790456A - Fused ring compound and its application, mixture, organic electronic device - Google Patents
Fused ring compound and its application, mixture, organic electronic device Download PDFInfo
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- CN109790456A CN109790456A CN201780059175.1A CN201780059175A CN109790456A CN 109790456 A CN109790456 A CN 109790456A CN 201780059175 A CN201780059175 A CN 201780059175A CN 109790456 A CN109790456 A CN 109790456A
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- STKKCWNZZPGJHR-UHFFFAOYSA-N phosphane;styrene Chemical group P.C=CC1=CC=CC=C1 STKKCWNZZPGJHR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KAVSMINTEBGDTI-UHFFFAOYSA-N pyridine;thiophene Chemical compound C=1C=CSC=1.C1=CC=NC=C1 KAVSMINTEBGDTI-UHFFFAOYSA-N 0.000 description 1
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical class C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Abstract
A kind of fused ring compound and its application, mixture, organic electronic device, shown in the structure of the fused ring compound such as general formula (1), the definition of the substituent group in the general formula (1) is identical as in specification.
Description
This application claims on November 30th, 2016 submit Patent Office of the People's Republic of China, application No. is a kind of 201611086394.2, priority of the Chinese patent application of entitled " fused ring compound and its application in organic electronic device ", entire contents are hereby incorporated by reference in the application.
The present invention relates to organic photoelectrical material technical fields, more particularly to a kind of fused ring compound and its application, mixture, organic electronic device.
The optics and electric property for having diversity, manufacturing cost relatively low and excellent in synthesis due to organic semiconducting materials, Organic Light Emitting Diode (Organic Light-Emitting Diode, OLED) has very big potentiality in the application aspect of photoelectric device (such as flat-panel monitor and illumination).
Organic electroluminescent phenomenon refers to the phenomenon that converting electrical energy into luminous energy using organic substance.Anode, cathode are generally included using the organic electroluminescent device of organic electroluminescent phenomenon and positioned at the organic matter layer between them.In order to improve efficiency and the service life of organic electroluminescent device, organic matter layer has multilayered structure, and each layer includes different organic substance.Specifically, organic matter layer may include hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc..In this organic electroluminescent device, apply voltage between two electrodes, then inject hole from anode to organic matter layer, injects electronics from cathode to organic matter layer, form exciton when injected holes meets with electronics, which issues light when returning ground state.This organic electroluminescent device has the characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast and high responsiveness.
In order to improve the luminous efficiency of organic electroluminescent device, the various luminescent material systems based on fluorescence and phosphorescence are developed, regardless of being fluorescent material or phosphor material, the exploitation of blue light material is all a huge challenge.In general, the organic light emitting diode reliability of blue-light fluorescent material used at present is higher.Nevertheless, the emission spectrum of most of blue-light fluorescent materials is wide at present, excitation purity is poor, it is unfavorable for high-end display, and the synthesis of this kind of fluorescent material is also more complex, is unfavorable for scale of mass production, while the OLED stability of this kind of blue fluorescent material also needs to further increase.Therefore, the blue fluorescent material that exploitation has narrow band emission spectra, stability good, is on the one hand conducive to obtain the blue-light device of more long-life higher efficiency, is on the other hand conducive to the raising of colour gamut, and then improve display effect.
Generally, blue-ray organic electroluminescent element luminescent layer uses host-guest system structure.Common Blue-light emitting host material is the condensed ring analog derivative based on anthracene, as described in patent CN1914293B, CN102448945B, US2015287928A1 etc., however the problem that these compounds have luminous efficiency and brightness is insufficient and device lifetime is poor.Common blue light-emitting guest compound, adoptable is aryl vinyl aminated compounds (WO 04/013073, WO 0,4/0 16575, WO 04/018587).However, the thermal stability of these compounds is poor, easily decomposes, cause the service life of device poor, be most important disadvantage in current industry.In addition, the excitation purity of these compounds is poor, it is difficult to realize navy blue shine.In addition, the patents such as US 7233019, KR 2006-0006760 disclose the organic electroluminescent device of the pyrene based compound using arylamine substituent group, but because the excitation purity of blue light is low, it is difficult to realize dark blue luminous therefore problematic in terms of the full color display for embodying natural colour.
Summary of the invention
According to the various embodiments of the application, a kind of organic compound and its application, organic mixture, organic electronic device are provided, solve the problems, such as one or more involved in background technique.
A kind of fused ring compound for organic electronic device, shown in the structure of the fused ring compound such as general formula (1):
Wherein,
X1Selected from CR1R2, O, S or NR3；
R1-R3、R11-R19And R110-R112Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of, wherein R1-R3、R11-R19And R110-R112At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding1-R3、R11-R19And R110-R112In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other；The Z is H or D.
A kind of polymer, at least one repetitive unit includes above-mentioned fused ring compound in the polymer.
A kind of mixture, the mixture include at least one organic functional material and above-mentioned fused ring compound or above-mentioned polymer；Wherein, the organic functional material is selected from hole-injecting material, hole mobile material, hole barrier materials, electron injection material, electron transport material, electron-blocking materials, organic host materials, luminescent material or organic dyestuff.
A kind of composition, the composition include organic solvent and above-mentioned fused ring compound or above-mentioned polymer or said mixture.
A kind of organic electronic device, including perhaps the functional layer of said mixture or the organic electronic device is prepared by above-mentioned composition for above-mentioned fused ring compound or above-mentioned polymer.
A kind of preparation method of organic electronic device, comprising the following steps:
Above-mentioned fused ring compound or above-mentioned organic mixture are deposited on substrate, forms functional layer.
A kind of preparation method of organic electronic device, comprising the following steps:
By the way of printing or coating, above-mentioned composition is coated on substrate, forms functional layer.
The details of one or more embodiments of the invention proposes in following attached drawing and description.Other features, objects, and advantages of the present invention will become obvious from specification, attached drawing and claims.
In ord to more clearly illustrate embodiments of the present application or technical solution in the prior art, the drawings to be used in the description of the embodiments or prior art will be briefly described below, apparently, the drawings in the following description are only some examples of the present application, for those of ordinary skill in the art, without creative efforts, it is also possible to obtain other drawings based on these drawings.
Fig. 1 is the structural schematic diagram of the organic electronic device of an embodiment.
In order to make the objectives, technical solutions, and advantages of the present invention clearer, the present invention is further described in detail below with reference to the accompanying drawings and embodiments.It should be appreciated that specific embodiment described herein is used only for explaining the present invention, it is not intended to limit the present invention.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.Term as used herein in the specification of the present invention, which is only for the purpose of describing specific embodiments, is not intended to limit the present invention.Term as used herein "and/or" includes any and all combinations of one or more related listed items.
Herein, composition, printing ink and ink have the same meaning, and can be interchanged between them.Material of main part, host material, Host material and Matrix material have the same meaning, and can be interchanged between them.Metallo-organic complex, metal organic complex and organometallic complex have the same meaning, and can be interchanged between them.
The fused ring compound for organic electronic device of one embodiment, shown in the structure of the fused ring compound such as general formula (1):
Wherein,
X1Selected from CR1R2, O, S or NR3；
R1-R3、R11-R19And R110-R112Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of, wherein R1-R3、R11-R19And R110-R112At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding1-R3、R11-R19And R110-R112In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other.Wherein, R1、R2、R3、R11、R12、R13、R14、R15、R16、R17、R18、R19、R110、R111Or R112In one or more H optionally further replaced by D.
It should be noted that R1-R3、R11-R19And R110-R112Independently selected from H, D, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；R1、R2、R3、R11、R12、R13、R14、R15、R16、R17、R18、R19、R110、R111Or R112In one or more H optionally further replaced by D.
The luminescent spectrum of the fused ring compound shows as the half-peak breadth for having narrow, so that such fused ring compound is with navy blue
Fluorescent emission, and there is high luminous efficiency.
X in one of the embodiments,1Selected from CR1R2Or NR3。
X in one of the embodiments,1Selected from O or S.
R in one of the embodiments,1-R3、R11-R19And R110-R112Independently selected from the straight chained alkyl with 1 to 10 C atom, alkoxy with 1 to 10 C atom, thio alkoxy with 1 to 10 C atom, branch or cricoid alkyl with 3 to 10 C atoms, branch or cricoid alkoxy with 3 to 10 C atoms, branch or cricoid thio alkoxy with 3 to 10 C atoms, substituted ketone group with 1 to 10 C atom, alkoxy carbonyl with 2 to 10 C atoms, aryloxycarbonyl with 7 to 10 C atoms, substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 20 annular atoms and one of the aryloxy group with 5 to 20 annular atoms or heteroaryloxy group or a variety of.
R in one of the embodiments,1-R3、R11-R19And R110-R112In at least one be selected from aromatic ring or aromatic heterocycle system.Aromatic ring includes 5~15 carbon atoms in ring system in one of the embodiments,.Aromatic ring includes 5~10 carbon atoms in ring system in one of the embodiments,.Miscellaneous aromatic ring includes 2~15 carbon atoms and at least one hetero atom in ring system in one of the embodiments, and carbon atom and heteroatomic sum are at least 4.Miscellaneous aromatic ring includes 2~10 carbon atoms and at least one hetero atom in ring system in one of the embodiments, and carbon atom and heteroatomic sum are at least 4.Hetero atom is selected from one of Si, N, P, O, S and Ge or a variety of in one of the embodiments,.Hetero atom is selected from one of Si, N, P, O and S or a variety of in one of the embodiments,.Hetero atom is selected from N, O or S in one of the embodiments,.
It should be noted that aromatic group refers to containing at least one the alkyl of aromatic ring.Aromatic ring refers to including monocyclic groups and polycyclic loop system.Above-mentioned heteroaromatic group refers to the alkyl comprising at least one hetero-aromatic ring (containing hetero atom).Miscellaneous aromatic ring refers to including monocyclic groups and polycyclic loop system.These polycyclic rings can have two or more rings, and two of them carbon atom is shared by two adjacent rings, i.e. condensed ring.These polycyclic ring species, at least one is aromatics or heteroaromatic.For the purpose of the present invention, aromatic series or heteroaromatic ring system not only include the system of aromatic radical or heteroaryl perfume base, moreover, plurality of aryl or heteroaryl can also be interrupted (< 10% non-H atom, such as C, N or O atom) by short non-aromatic unit.Multiple aryl or heteroaryl can also be interrupted (less than the non-H atom of 5% atomicity accounting) by short non-aromatic unit in one of the embodiments,., two fluorenes of 9'- spiral shell, 9,9- diaryl fluorenes, triaryl amine, the systems such as diaryl ether, for the goal of the invention it also hold that being aromatic ring system.
Aromatic group is selected from benzene, naphthalene, anthracene, phenanthrene, perylene, aphthacene, pyrene, BaP, triphenylene, acenaphthene, fluorenes, spiro fluorene or their derivative in one of the embodiments,.
In one of the embodiments, heteroaromatic group is selected from furans, benzofuran, dibenzofurans, thiophene, benzothiophene, dibenzothiophenes, pyrroles, pyrazoles, triazole, imidazoles, oxazole, oxadiazoles, thiazole, tetrazolium, indoles, carbazole, pyrrolo- imidazoles, pyrrolopyrrole, Thienopyrroles, thienothiophene, furans and pyrroles, furans and furans, thienofuran, benzo isoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinolin, cinnoline, quinoxaline, phenanthridines, primary pyridine, quinazoline, quinazolinone or their derivative.
In one of the embodiments, shown in the structure of fused ring compound such as general formula (2):
Wherein,
Ar1-Ar3Independently selected from H, the straight chained alkyl with 1 to 20 C atom, the alkoxy with 1 to 20 C atom, the thio alkoxy with 1 to 20 C atom, the branch with 3 to 20 C atoms or cricoid alkyl, the branch with 3 to 20 C atoms or cricoid alkoxy, the branch with 3 to 20 C atoms or cricoid thio alkoxy, substituted or unsubstituted silicyl, the substituted ketone group with 1 to 20 C atom, have 2
To the alkoxy carbonyl of 20 C atoms, the aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Ar1-Ar3At least one of form monocycle or polycyclic aliphatic series or aromatic ring or Ar with the ring of the group bonding1-Ar3In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other；Ar1、Ar2Or Ar3In one or more H optionally replaced by D.
X in one of the embodiments,1Selected from CR1R2.In other embodiments, X1Selected from O or S.
Ar in one of the embodiments,1-Ar3、R1-R3Independently with the straight chained alkyl of 1 to 10 C atom, straight chained alkyl alkoxy with 1 to 10 C atom, straight chained alkyl thio alkoxy with 1 to 10 C atom, branch or cricoid alkyl with 3 to 10 C atoms, branch or cricoid alkoxy with 3 to 10 C atoms, branch or cricoid thio alkoxy with 3 to 10 C atoms, substituted ketone group with 1 to 10 C atom, alkoxy carbonyl with 2 to 10 C atoms, aryloxycarbonyl with 7 to 10 C atoms, substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 20 annular atoms and one of the aryloxy group with 5 to 20 annular atoms or heteroaryloxy group or a variety of.
R in one of the embodiments,11-R19、R110-R112And Ar1-Ar3At least one of selected from following any group:
Wherein,
R41-R42、R410-R411And R413-R433Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, person substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Wherein, R41-R42、R410-R411And R413-R433At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding41-R42、R410-R411And R413-R433In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other；R41、R42、R410、R411、R413、R414、R415、R416、R417、R418、R419、
R420、R421、R422、R423、R424、R425、R426、R427、R428、R429、R430、R431、R432Or R433In one or more H optionally replaced by D；
M is 0,1,2 or 3；N, p and s independently is 0,1,2,3 or 4；T and q independently is 0,1,2,3,4 or 5；
P is selected from the saturation cycloalkane with 3 to 8 C atoms；
L indicates singly-bound or linking group；Wherein, the linking group is selected from one of substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；One or more H in the linking group are optionally replaced by D；
Dotted line indicates the singly-bound that L is connect with other groups.
M is 0,1 or 2 in one of the embodiments,.M is 0 or 1 in one of the embodiments,.
N, p and s independently are 0,1,2 or 3 in one of the embodiments,.N, p and s independently are 0,1 or 2 in one of the embodiments,.N, p and s independently are 0 or 1 in one of the embodiments,.
T and q independently is 0,1,2 or 3 in one of the embodiments,.T and q independently is 0,1 or 2 in one of the embodiments,.T and q independently is 0 or 1 in one of the embodiments,.
The saturation cycloalkane that P is selected from as 4 to 6 C atoms in one of the embodiments,.P is selected from the saturation cycloalkane of 5 to 6 C atoms in one of the embodiments,.
R in one of the embodiments,41-R42、R410-R411And R413-R433Independently selected from the straight chained alkyl with 1 to 10 C atom, alkoxy with 1 to 10 C atom, thio alkoxy with 1 to 10 C atom, branch or cricoid alkyl with 3 to 10 C atoms, branch or cricoid alkoxy with 3 to 10 C atoms, branch or cricoid thio alkoxy with 3 to 10 C atoms, substituted ketone group with 1 to 10 C atom, alkoxy carbonyl with 2 to 10 C atoms, aryloxycarbonyl with 7 to 10 C atoms, substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 30 annular atoms and one of the aryloxy group with 5 to 30 annular atoms or heteroaryloxy group or a variety of.
L is selected from the deuterated or not deuterated substituted or unsubstituted aromatics with 5 to 20 annular atoms or heteroaromatic ring system and one of the deuterated or not deuterated aryloxy group with 5 to 20 annular atoms or heteroaryloxy group or a variety of in one of the embodiments,.
L is selected from the deuterated or not deuterated substituted or unsubstituted aromatics with 10 to 25 annular atoms or heteroaromatic ring system and one of the deuterated or not deuterated aryloxy group with 10 to 25 annular atoms or heteroaryloxy group or a variety of in one of the embodiments,.
The structure of fused ring compound is as shown in any general formula in general formula (3)-(8) in one of the embodiments:
The structure of fused ring compound such as general formula (5) or (6) are shown in one of the embodiments,.
R in one of the embodiments,11-R19、R110-R112And Ar1-Ar3Independently selected from following any group:
Wherein,
R51-R59、R510-R548Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, person substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Wherein, R32-R33、R41-R42、R410-R411And R413-R431At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding32-R33、R41-R42、R410-R411And R413-R431In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other；R32、R33、R41、R42、R410、R411、R413、R414、R415、R416、R417、R418、R419、R420、R421、R422、R423、R424、R425、R426、R427、R428、R429、R430Or R431In one or more H optionally replaced by D；
M is 0,1,2 or 3；N is 0,1,2,3 or 4；S is 0,1,2,3,4 or 5；U is 0,1,2,3,4,5 or 6；V is 0,1,2,3,4,5,6 or 7；
L indicates singly-bound or linking group；Wherein, the linking group is selected from one of substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；One or more H in the linking group are optionally replaced by D；
Dotted line indicates the singly-bound that L is connect with other groups.
M is 0,1 or 2 in one of the embodiments,.M is 0 or 1 in one of the embodiments,.
N is 0,1,2,3 or 4 in one of the embodiments,.N is 0,1,2 or 3 in one of the embodiments,.In one of the embodiments, 0,1 or 2 n.N is 0 or 1 in one of the embodiments,.
S is 0,1,2 or 3 in one of the embodiments,.S is 0,1 or 2 in one of the embodiments,.S is 0 or 1 in one of the embodiments,.
U is 0,1,2 or 3 in one of the embodiments,.U is 0,1 or 2 in one of the embodiments,.U is 0 or 1 in one of the embodiments,.
V is 0,1,2 or 3 in one of the embodiments,.V is 0,1 or 2 in one of the embodiments,.V is 0 or 1 in one of the embodiments,.
R in one of the embodiments,51-R59、R510-R548Independently selected from the straight chained alkyl with 1 to 10 C atom, the alkoxy of 1 to 10 C atom, the thio alkoxy of 1 to 10 C atom, branch or cricoid alkyl with 3 to 10 C atoms, branch or cricoid alkoxy with 3 to 10 C atoms, branch or cricoid thio alkoxy with 3 to 10 C atoms, substituted ketone group with 1 to 10 C atom, alkoxy carbonyl with 2 to 10 C atoms, aryloxycarbonyl with 7 to 10 C atoms, substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 20 annular atoms and one of the aryloxy group with 5 to 20 annular atoms or heteroaryloxy group or a variety of.
L is selected from the deuterated or not deuterated substituted or unsubstituted aromatics with 5 to 30 annular atoms or heteroaromatic ring system and one of the deuterated or not deuterated aryloxy group with 5 to 30 annular atoms or heteroaryloxy group or a variety of in one of the embodiments,.
L is selected from the deuterated or not deuterated substituted or unsubstituted aromatics with 10 to 25 annular atoms or heteroaromatic ring system and one of the deuterated or not deuterated aryloxy group with 10 to 25 annular atoms or heteroaryloxy group or a variety of in one of the embodiments,.
L is selected from singly-bound in one of the embodiments,.
Linking group L is selected from following any group in one of the embodiments:
Wherein:
X1Selected from CR61Or N；
Y is selected from CR62R63、SiR64R65、NR66, C (=O), S or O；
R61-R66Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy group with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy group with 3 to 20 C atoms, silyl-group, substituted keto group with 1 to 20 C atom, alkoxycarbonyl groups with 2 to 20 C atoms, aryloxycarbonyl group with 7 to 20 C atoms, cyano group, carbamoyl group, halogen formyl group, formyl group (- C (=O)-H), isocyano group group, isocyanate groups, thiocyanates group, isothiocyanates group, hydroxyl group, Nitryl group, CF3One of group, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and aryloxy group with 5 to 40 annular atoms or heteroaryloxy group are a variety of；Wherein, R61、R62、R63、R64、R65And R66At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding61、R62、R63、R64、R65And R66At least two form monocycles or polycyclic aliphatic series or aromatic ring between each other.
Linking group L is selected from following any group in one of the embodiments:
Wherein, dotted line indicates the singly-bound that L is connect with other groups.It should be noted that Da indicates the number that the H on ring is replaced by D, a 1,2,3 or 4.
The emission wavelength of fused ring compound is 300 between 800nm in one of the embodiments,.The emission wavelength of fused ring compound is 350 between 600nm in one of the embodiments,.The emission wavelength of fused ring compound is 400 between 500nm in one of the embodiments,.
Fused ring compound photoluminescence quantum efficiencies with higher in one of the embodiments, photoluminescence quantum efficiencies >=15%.Photoluminescence quantum efficiencies >=25% in one of the embodiments,.Photoluminescence quantum efficiencies >=35% in one of the embodiments,.Photoluminescence quantum efficiencies >=50% in one of the embodiments,.
Glass transition temperature >=100 DEG C of fused ring compound in one of the embodiments,.Glass transition temperature >=110 DEG C of fused ring compound in one of the embodiments,.Glass transition temperature >=120 DEG C of fused ring compound in one of the embodiments,.Glass transition temperature >=140 DEG C of fused ring compound in one of the embodiments,.
At least part of H is deuterated in fused ring compound according to the invention in one of the embodiments,.10% H is deuterated in fused ring compound in one of the embodiments,.20% H is deuterated in fused ring compound in one of the embodiments,.30% H is deuterated in fused ring compound in one of the embodiments,.40% H is deuterated in fused ring compound in one of the embodiments,.
Fused ring compound according to the invention is selected from following any structure compound represented in one of the embodiments,.
The fused ring compound is for being deposited type OLED device in one of the embodiments,.At this point, molecular weight≤1000g/mol of the fused ring compound.Molecular weight≤900g/mol of fused ring compound in one of the embodiments,.Molecular weight≤850g/mol of fused ring compound in one of the embodiments,.Molecular weight≤800g/mol of fused ring compound in one of the embodiments,.Molecular weight≤700g/mol of fused ring compound in one of the embodiments,.
The fused ring compound is used for printed form OLED in one of the embodiments,.At this point, molecular weight >=700g/mol of the fused ring compound.Molecular weight >=800g/mol of fused ring compound in one of the embodiments,.Molecular weight >=900g/mol of fused ring compound in one of the embodiments,.Molecular weight >=1000g/mol of fused ring compound in one of the embodiments,.Molecular weight >=1100g/mol of fused ring compound in one of the embodiments,.
Application of the above-mentioned fused ring compound in organic electronic device.The organic electronic device being prepared using such fused ring compound as object, especially organic electroluminescent device have dark blue chromaticity coordinates, high luminous efficiency and higher device lifetime.
The polymer of one embodiment, at least one repetitive unit includes above-mentioned fused ring compound in the polymer.The polymer is non-conjugated highpolymer in one of the embodiments, wherein the structure as shown in general formula (1) or (2) is on side chain.In another embodiment, which is conjugated highpolymer.
In one of the embodiments, at 25 DEG C, the solubility >=2mg/ml of above-mentioned fused ring compound or polymer in toluene.In one of the embodiments, at 25 DEG C, the solubility >=3mg/ml of above-mentioned fused ring compound or polymer in toluene.In one of the embodiments, at 25 DEG C, the solubility >=5mg/ml of above-mentioned fused ring compound or polymer in toluene.
Application of the above-mentioned polymer in organic electronic device.
The synthetic method of the fused ring compound of one embodiment, wherein the raw material containing active group is used to be reacted.These activated feedstocks include at least one leaving group, such as: bromine, iodine, boric acid or borate.Form the appropriate anti-of C-C connection
It should be well known to those skilled in the art and be described in document.Coupling reaction is SUZUKI, STILLE and HECK coupling reaction in one of the embodiments,.
The mixture for organic electronic device of one embodiment includes above-mentioned fused ring compound and at least another organic functional material.Wherein, organic functional material is selected from hole (also referred to as electric hole) injection or transmission material (HIM/HTM), hole barrier materials (HBM), electron injection or transmission material (EIM/ETM), electron-blocking materials (EBM), organic host materials (Host), luminescent material or organic dyestuff.Luminescent material is singlet emitters (fluorescent illuminant), triplet emitters (phosphorescent emitter) or thermal excitation delayed fluorescence material (TADF material) in one of the embodiments,.Such as various organic functional materials are described later in detail in WO2010135519A1, US20090134784A1 and WO 2011110277A1, the full content in this three patent documents is incorporated herein by reference hereby.
The mixture includes a kind of above-mentioned fused ring compound and a kind of fluorescent host material (or singlet state host material) in one of the embodiments,.At this point, the fused ring compound can be used as object, and weight percent≤15wt% of fused ring compound.Weight percent≤12wt% of fused ring compound in one of the embodiments,.Weight percent≤9wt% of fused ring compound in one of the embodiments,.Weight percent≤8wt% of fused ring compound in one of the embodiments,.Weight percent≤7wt% of fused ring compound in one of the embodiments,.
The mixture includes a kind of above-mentioned fused ring compound, a kind of fluorescent illuminant (or singlet emitters) and a kind of fluorescent host material in one of the embodiments,.At this point, the fused ring compound can be used as auxiliary light emission material, the weight ratio with fluorescent illuminant is 1:2 to 2:1.
The mixture includes above-mentioned fused ring compound and a kind of TADF material in one of the embodiments,.
The mixture includes a kind of above-mentioned fused ring compound and a kind of HTM material in one of the embodiments,.
Some more detailed descriptions (but not limited to this) are made to HTM, singlet state host material, singlet emitters and TADF material below.
1、HIM/HTM/EBM
Suitable organic HIM/HTM material is optional include following structural unit compound: phthalocyanine, porphyrin, amine, aromatic amine, biphenyl class triaryl amine, thiophene, bithiophene such as dithienothiophene and bithiophene, pyrroles, aniline, carbazole, indolocarbazole or their derivative.HIM further includes self assembly monomer in one of the embodiments, such as: compound, metal complex or cross-linking compounds containing phosphonic acids and sliane derivative.
Electronic barrier layer (EBL) is used to stop the electronics from successive functional layers, especially luminescent layer.Compared to the luminescent device on not barrier layer, the presence of EBL would generally improve luminous efficiency.The electron-blocking materials (EBM) of electronic barrier layer (EBL) are needed than successive functional layers, such as luminescent layer, have higher LUMO.Wherein, LUMO indicates the minimum non-occupied orbital of compound.EBM has the excited level bigger than adjacent luminescent layer in one of the embodiments, such as singlet state or triplet, which depends on illuminator.Meanwhile EBM has the function of hole transport.The HIM/HTM material with high lumo energy also can be used as EBM in one of the embodiments,.
The structure of the cyclophane perfume (or spice) amine derivative compounds as HIM, HTM or EBM is as shown in flowering structure in one of the embodiments:
Wherein, Ar1-Ar9Independently selected from aromatic hydrocarbon ring compound, heteroaromatic compound or include 2 to 10 ring structures group.Ar1-Ar9It can be the aromatic hydrocarbon ring group or aromatic heterocycle group of identical or different type, and link together directly with one another or by least one group below, such as oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structural unit or aliphatic cyclic group.
Aromatic hydrocarbon ring compound is selected from benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, that non-alkene, phenanthrene, fluorenes, pyrene, in the wrong or Azulene in one of the embodiments,.In one of the embodiments, heteroaromatic compound be selected from dibenzothiophenes,
Dibenzofurans, furans, thiophene, benzofuran, benzothiophene, carbazole, pyrazoles, imidazoles, triazole, isoxazole, thiazole, oxadiazoles, dislike triazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, dislike thiazine, oxadiazines, indoles, benzimidazole, indazole, indolizine, benzoxazoles, benzisoxazole, benzothiazole, quinoline, isoquinolin, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, phenthazine, phenoxazine, dibenzo selenophen, benzo selenophen, benzofuran pyridine, indole carbazole, pyridine indoles, two pyridine of pyrroles, two pyridine of furans, benzothiophene pyridine, thiophene pyridine, two pyridine of benzo selenophen pyridine or selenophen.Wherein, each Ar can be further substituted, and substituent group is chosen as hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl and heteroaryl.
Ar in one of the embodiments,1-Ar9Independently selected from following any group:
Wherein, the integer that n is 1 to 20；X1-X8Independently selected from CH or N；Ar1As defined above.
The other example of cyclophane perfume (or spice) amine derivative compounds can be found in US3567450, US4720432, US5061569, US3615404, and US5061569.
The example of the metal complex as HTM or HIM includes but is not limited to following general structure in one of the embodiments:
M is metal, and the atomic weight of M is greater than 40；
(Y1-Y2) it is one liang of tooth ligand；Y1And Y2Independently selected from C, N, O, P or S；L is assistant ligand；M is integer, maximum coordination number of the value from 1 to M；M+n is the maximum coordination number of M.
(Y in one of the embodiments,1-Y2) it is 2- phenylpyridine derivative.In another embodiment, (Y1-Y2) it is carbenes.
In one of the embodiments.M is selected from Ir, Pt, Os or Zn.
The HOMO of metal complex is greater than -5.5eV in one of the embodiments, (relative to vacuum level).Wherein, HOMO indicates the highest occupied molecular orbital of metal complex.
The example that suitably can be used as HIM/HTM compound is listed in following table.
2, singlet state host material (Singlet Host):
The example of singlet state material of main part is not particularly limited, and any organic compound may all be used as main body, as long as its singlet energy is higher than illuminator, especially singlet emitters or fluorescent illuminant.
The organic compound used in one of the embodiments, as singlet state material of main part be selected from containing aromatic hydrocarbon ring compound, heteroaromatic compound or include 2 to 10 ring structures group.
Benzene, biphenyl, triphenyl, benzo, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene, in the wrong or Azulene are selected from containing aromatic hydrocarbon ring compound in one of the embodiments,.In one of the embodiments, heteroaromatic compound is selected from dibenzothiophenes, dibenzofurans, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo selenophen, carbazole, indole carbazole, pyridine indoles, two pyridine of pyrroles, pyrazoles, imidazoles, triazole, isoxazole, thiazole, oxadiazoles, dislike triazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazines, dislike thiazine, oxadiazines, indoles, benzimidazole, indazole, indolizine, benzoxazoles, benzisoxazole, benzothiazole, quinoline, isoquinolin, cinnolines, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, phenthazine, phenoxazine, benzofuran pyridine, two pyridine of furans, benzothiophene pyridine, two pyridine of thiophene, two pyridine of benzo selenophen pyridine or selenophen.In one of the embodiments, it include that the group of 2 to 10 ring structures can be the aromatic hydrocarbon ring group or aromatic heterocycle group of identical or different type, and link together directly with one another or by least one group below, such as oxygen atom, nitrogen-atoms, sulphur atom, silicon atom, phosphorus atoms, boron atom, chain structural unit or aliphatic cyclic group.
Singlet state material of main part is selected from following any group compound represented in one of the embodiments:
Wherein, R1Selected from hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl or heteroaryl；Ar1Selected from aryl or heteroaryl, with Ar defined in above-mentioned HTM1Meaning is identical；N is the integer in 0 to 20；X1-X8Independently selected from CH or N；X9And X10Independently selected from CR1R2Or NR1；R2Selected from hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl or heteroaryl.
The example of some anthryl singlet state material of main parts is listed in following table.
3, singlet emitters (Singlet Emitter)
Singlet emitters often have longer conjugated pi electron system.So far, there are many examples, such as the styrylamine disclosed in JP2913116B and WO2001021729A1 and its derivative and the indenofluorene disclosed in WO2008/006449 and WO2007/140847 and its derivative.
Singlet emitters are selected from unitary styrylamine, binary styrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether or arylamine in one of the embodiments,.
Unitary styrylamine refers to a compound, it includes a unsubstituted or styryl group replaced and at least one amine.Amine is aromatic amine in one of the embodiments,.Binary styrylamine refers to a compound, it includes two unsubstituted or styryl groups replaced and at least one amine.Amine is aromatic amine in one of the embodiments,.Ternary styrylamine refers to a compound, it includes three unsubstituted or styryl groups replaced and at least one amine.Amine is aromatic amine in one of the embodiments,.Quaternary styrylamine refers to a compound, it includes four unsubstituted or styryl groups replaced and at least one amine.Amine is aromatic amine in one of the embodiments,.Styrene is talan in one of the embodiments, can be further substituted.The definition of corresponding phosphine and ethers is similar to amine.Arylamine or aromatic amine refer to a kind of compound, the aromatic rings or heterocyclic ring system for directly coupling the unsubstituted of nitrogen it includes three or replacing.At least one in the loop system of these aromatic series or heterocycle is selected from fused ring system in one of the embodiments, and has at least 14 aromatic ring atoms.Aromatic rings is selected from fragrant anthranylamine, fragrant anthradiamine, fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong or fragrance diamines in the wrong in one of the embodiments,.Fragrant anthranylamine refers to that a compound, one of binary arylamine group are attached directly on anthracene.Binary arylamine group is connected on 9 position of anthracene in one of the embodiments,.Fragrant anthradiamine refers to that a compound, wherein two binary arylamine group are directly linked on anthracene.Binary arylamine group is connected in the 9 of anthracene in one of the embodiments, on 10 position.The definition that fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong and fragrance bend diamines is similar,.Binary arylamine group is connected to the 1 or 1 of pyrene, on 6 positions in one of the embodiments,
The example of singlet emitters based on vinylamine and arylamine, it is also preferred example, it can be found in following patent documents: WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007/115610,1583691 A of US 7250532 B2, DE 102005058557 A1, CN, 08053397 A of JP, the full content in the above-mentioned patent document listed is simultaneously hereby by US 6251531 B1, US 1957606 A1 of 2006/210830 A, EP and 2008/0113101 A1 of US Enter herein as reference.
The example of singlet emitters based on stibene extremely derivative has US 5121029.
In one of the embodiments, singlet emitters are selected from indenofluorene-amine and indenofluorene-diamines, as disclosed in WO 2006/122630, or benzo indenofluorene-amine and benzo indenofluorene-diamines, as disclosed in WO 2008/006449, or dibenzo indenofluorene-amine and dibenzo indenofluorene-diamines, as disclosed in WO2007/140847.
In other embodiments, material as singlet emitters is selected from polycyclic aromatic hydrocarbon compounds, the derivative of especially following any compound: anthracene such as 9, 10- bis- (2- naphthanthracene), naphthalene, four benzene, xanthene, it is luxuriant and rich with fragrance, pyrene (such as 2, 5, 8, tetra--t- butyl of 11-), indeno pyrene, penylene is (such as: 4, 4 '-bis- (9- ethyl -3- carbazole vinyl) -1, 1 '-biphenyl), two indeno pyrenes, decacyclene, coronene, fluorenes, two fluorenes of spiral shell, aryl pyrene (such as: US20060222886), arylene ethylene is (such as: US5121029, US5130603), cyclopentadiene (such as: tetraphenyl cyclopentadiene), rubrene, cumarin, rhodamine, quinacridone, pyrans is (such as: 4 (4- pairs of -6- of (dicyano methylene) Dimethylaminostyryl -2- methyl) -4H- pyrans), thiapyran, bis- (azine) imines boron compounds (2007/0092753 A1 of US), bis- (azine) methylene compounds, carbostyryl compound, oxazinone, benzoxazoles, benzothiazole, benzimidazole or pyrrolo-pyrrole-dione.The material of some singlet emitters can be found in following patent documents: 2007/0252517 A1 of US 20070252517 A1, US 4769292, US 6020078, US 2007/0252517 A1, US.The full content in the above-mentioned patent document listed is incorporated herein by reference hereby.
The example of some suitable singlet emitters is listed in following table.
4, thermal excitation delayed fluorescence luminescent material (TADF material)
Traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, and the internal quantum efficiency of device is lower (up to 25%).Although phosphor material passes through between being since the strong SO coupling in heavy atom center enhances, it can efficiently use and be electrically excited the singlet exciton to be formed and Triplet exciton, the internal quantum efficiency of device is made to reach 100%.But phosphor material is expensive, and stability of material is poor, and device efficiency the problems such as serious of roll-offing limits its application in OLED.Hot activation delayed fluorescence luminescent material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Such material generally has small singlet-triplet poor (Δ Est), triplet excitons can by it is counter be between pass through be transformed into singlet exciton shine.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation.Device internal quantum efficiency can reach 100%.Meanwhile material structure is controllable, property is stable and cheap woth no need to noble metal, in having a extensive future for the field OLED.
TADF material needs to have lesser singlet-triplet poor, Δ Est < 0.3eV.Δ Est < 0.2eV in one of the embodiments,.Δ Est < 0.1eV in one of the embodiments,.TADF in one of the embodiments,
There is preferable fluorescence quantum efficiency.Some TADF luminous material can be found in following patent documents: CN103483332 (A), TW201309696 (A), TW201309778 (A), TW201343874 (A), TW2013 50558 (A), US20120217869 (A1), WO2013133359 (A1), WO2013154064 (A1), Adachi, et.al.Adv.Mater., 21,2009,4802, Adachi, et.al.Appl.Phys.Lett., 98,2011,083302, Adachi, et.al.Appl.Phys.L Ett., 101,2012,093306, Adachi, et.al.Chem.Commun., 48,2012,11392, Adachi, et.al.Nature Photonics, 6,2012,253, Adachi, et.al.Nature, 492,2012,234, Adachi, et.al.J.Am.Chem.Soc, 134,2012,14706, Adachi, et.al.Angew.Chem.Int.Ed, 51,2012,11311, Adachi, et.al.Chem.Commun., 48,2012 9580, Adachi, et.al.Chem.Commun., 48,2013,10385, Adachi, et.al.Adv.Mater., 25,2013,3319, Adachi, et.al.Adv.Mater., 25,2013,3707, Adachi, et.al.Chem.Mater., 25,2013,3038, Adachi, et.al.Chem.Mater., 25,2013,3766, Adachi, et.al.J.Mater.Chem.C., 1,2013,4599, Adachi, et.al.J.Phys. Chem.A., 117,2013,5607, the full content in the above-mentioned patent listed or article file is incorporated herein by reference hereby.
The example of some suitable TADF luminescent materials is listed in following table.
The organic functional material publication appeared above is that disclosed purpose is incorporated herein in way of reference.
The organic mixture of another embodiment includes above-mentioned polymer and at least one organic functional material.Described in the mixture of an embodiment as above such as selection and property about material, details are not described herein.
The composition of one embodiment includes or mixtures thereof at least one above-mentioned fused ring compound and organic solvent.
In one of the embodiments, in the composition, fused ring compound is as singlet emitters material.
The composition also includes material of main part in one of the embodiments,.
The composition also includes a kind of material of main part and a kind of singlet emitters in one of the embodiments,.
The composition also includes at least two material of main parts in one of the embodiments,.
The composition also includes a kind of material of main part and a kind of hot activation delayed fluorescence luminescent material in one of the embodiments,.
The composition also includes a kind of hole mobile material (HTM) in one of the embodiments,.HTM includes crosslinkable groups in one of the embodiments,.
In one embodiment, the composition can be solution or suspension.This is determined according to the compatibility between organic mixture and organic solvent.
In one embodiment, the weight percent of organic compound is 0.01 to 20wt% in the composition.In one embodiment, the weight percent of organic compound is 0.1 to 15wt% in the composition.In one embodiment, the weight percent of organic compound is 0.2 to 10wt% in the composition.In one embodiment, the weight percent of organic compound is 0.25 to 5wt% in the composition.
Organic solvent includes the first organic solvent, the first organic solvent is selected from one of aromatics or heteroaromatic, ester, aromatic ketone, aromatic oxide, aliphatic ketone, fatty ether, alicyclic or alkenes compounds and inorganic ester type compound or a variety of in one of the embodiments,.Wherein, inorganic ester type compound can be borate or phosphate.
The composition includes at least aromatics of 50wt% or heteroaromatic solvent in one of the embodiments,.The composition includes at least aromatics of 80wt% or heteroaromatic solvent in one of the embodiments,.The composition includes at least aromatics of 90wt% or heteroaromatic solvent in one of the embodiments,.
Example according to the invention based on aromatics or heteroaromatic solvent has, but it is not limited to: 1-tetralone, 3- phenoxytoluene, acetophenone, 1- methoxynaphthalene, to diisopropyl benzene, penta benzene, naphthane, cyclohexyl benzene, chloronaphthalene, 1, 4- dimethylnaphthalene, 3- isopropyl biphenyl, p-Methylisopropylbenzene, diamyl benzene, adjacent diethylbenzene, NSC 62102, p-Diethylbenzene, 1, 2, 3, 4- durene, 1, 2, 3, 5- durene, 1, 2, 4, 5- durene, butylbenzene, detergent alkylate, 1- methyl naphthalene, 1, 2, 4- trichloro-benzenes, 1, 3- dipropoxy benzene, 4, 4- difluoro-diphenylmethane, diphenyl ether, 1, 2- dimethoxy-4 '-(1- acrylic) benzene, diphenyl-methane, 2- phenylpyridine, 3- phenylpyridine, 2- phenoxy group methyl ether, 2- phenoxy group four Hydrogen furans, ethyl -2- naphthyl ether, N- methyldiphenylamine, 4- isopropyl biphenyl, α, α-dichloro diphenyl methane, 4- (3- phenyl propyl) pyridine, Ergol, 1, bis- (3, the 4- 3,5-dimethylphenyl) ethane of 1-, 2- isopropyl naphthalene, benzyl ether etc..
The first organic solvent is selected from aliphatic, alicyclic or aromatic hydrocarbons race, amine, mercaptan, amide, nitrile, ester, ether, polyethers, alcohol, glycol or polyalcohol in one of the embodiments,.
Alcohol represents the solvent of appropriate classification in one of the embodiments,.Alcohol is selected from alkyl cyclohexanol in one of the embodiments,.The first organic solvent is aliphatic alcohol or naphthols of methylation etc. in one of the embodiments,.
The first organic solvent is cycloalkane, such as decahydronaphthalenes in one of the embodiments,.
It should be noted that the first organic solvent can be used alone, the mixture that can also be used as two or more organic solvents is used.
The organic solvent further includes the second organic solvent in one of the embodiments,.Second solvent is selected from methanol, ethyl alcohol, 2-methyl cellosolve, methylene chloride, chloroform, chlorobenzene, o-dichlorohenzene, tetrahydrofuran, methyl phenyl ethers anisole, morpholine, toluene, ortho-xylene, meta-xylene, paraxylene, 1,4 dioxanes, acetone, methyl ethyl ketone, 1,2 dichloroethanes, 3- phenoxytoluene, 1,1,1- trichloroethanes, 1,1, one of 2,2- tetrachloroethanes, ethyl acetate, butyl acetate, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide, naphthane, naphthalane and indenes are a variety of.
Organic solvent is solvent of Hansen (Hansen) solubility parameter in following range in one of the embodiments:
δd(dispersion force) is in 17.0~23.2MPa1/2Range；δp(polar forces) are in 0.2~12.5MPa1/2Range；δh(hydrogen bond force) is in 0.9~14.2MPa1/2Range.
δ in one of the embodiments,dIn 18.5~21.0MPa1/2Range.δ in one of the embodiments,pIn 2.0~6.0MPa1/2Range.δ in one of the embodiments,hIn 2.0~6.0MPa1/2Range.
Composition according to the invention, wherein organic solvent need to consider its boiling point parameter when choosing.Boiling point >=150 DEG C of organic solvent in one of the embodiments,.Boiling point >=180 DEG C of organic solvent in one of the embodiments,.Boiling point >=200 DEG C of organic solvent in one of the embodiments,.Boiling point >=250 DEG C of organic solvent in one of the embodiments,.Boiling point >=275 DEG C of organic solvent in one of the embodiments,.Boiling point >=300 DEG C of organic solvent in one of the embodiments,.Organic solvent of the boiling point within the scope of these is beneficial to the spray nozzle clogging of ink jet printing head is prevented.The organic solvent can be evaporated from dicyandiamide solution, include functional membranes to be formed.
Viscosity of the composition at 25 DEG C is in 1cPs to 100cPs range in one of the embodiments,.Surface tension of the composition at 25 DEG C is in 19dyne/cm to 50dyne/cm range in one of the embodiments,.Viscosity of the composition at 25 DEG C is in 1cPs to 100cPs range in one of the embodiments, and surface tension of the composition at 25 DEG C is in 19dyne/cm to 50dyne/cm range.
Composition according to the invention, wherein organic solvent need to consider its surface tension parameter when choosing.Suitable ink surface tension parameter is suitable for specific substrate and specific printing process.Such as to ink jet printing, surface tension of the organic solvent at 25 DEG C is about in 19dyne/cm to 50dyne/cm range in one of the embodiments,.Surface tension of the organic solvent at 25 DEG C is in 22dyne/cm to 35dyne/cm range in one of the embodiments,.Surface tension of the organic solvent at 25 DEG C is in 25dyne/cm to 33dyne/cm range in one of the embodiments,.
Surface tension of the composition at 25 DEG C is in 22dyne/cm to 35dyne/cm range in one of the embodiments,.Surface tension of the composition at 25 DEG C is in 25dyne/cm to 33dyne/cm range in one of the embodiments,.
Composition according to the invention, wherein organic solvent need to consider the viscosity parameter of its ink when choosing.Viscosity can be adjusted by different methods, such as pass through the concentration of functional material in the selection of suitable organic solvent and ink.The viscosity of organic solvent is lower than 100cps in one of the embodiments,.The viscosity of organic solvent is lower than 50cps in one of the embodiments,.The viscosity of organic solvent is 1.5 to 20cps in one of the embodiments,.Here viscosity refers to that the viscosity under the environment temperature in printing, environment temperature are 15-30 DEG C.Environment temperature when printing in one of the embodiments, is 18-28 DEG C.Environment temperature when printing in one of the embodiments, is 20-25 DEG C.Environment temperature when printing in one of the embodiments, is 23-25 DEG C.The composition so prepared will be particularly suitable for ink jet printing.
Viscosity of the composition at 25 DEG C is in 1cps to 50cps range in one of the embodiments,.Viscosity of the composition at 25 DEG C is in 1.5cps to 20cps range in one of the embodiments,.
The ink for meeting the organic solvent acquisition of above-mentioned boiling point and surface tension parameter and viscosity parameter is capable of forming the functional membranes with uniform thickness and composition and property.
Above-mentioned composition is preparing the application in organic electronic device.The composition is preparing the application in organic electronic device as printing ink in one of the embodiments, when preparing organic electronic device in particular by printing or the mode being coated with.
In one of the embodiments, organic electronic device is selected from Organic Light Emitting Diode (OLED), organic photovoltaic battery (OPV), organic light emission battery (OLEEC), organic field-effect tube (OFET), organic light-emitting field effect pipe, organic laser, organic spin electric device, organic sensor or organic plasmon emitting diode (OrganicPlasmonEmitting
Diode)。
The organic electronic device of one embodiment includes functional layer, which includes that perhaps said mixture or the functional layer are prepared by above-mentioned composition for above-mentioned fused ring compound or above-mentioned polymer.
The organic electronic device contains at least one cathode, an anode and a functional layer between cathode and anode in one of the embodiments, wherein the functional layer includes at least a kind of above-mentioned fused ring compound.
The organic electronic device is electroluminescent device in one of the embodiments,.The electroluminescent device is OLED in one of the embodiments,.As shown in Figure 1, the OLED includes the substrate 101 stacked gradually, anode 102, luminescent layer 104 and cathode 106.
Substrate 101 can be opaque or transparent.Transparent substrate 101 can be used to manufacture a transparent light emitting component, refer to the Nature1996 such as Bulovic, 380, p29 and Gu etc., Appl.Phys.Lett.1996, and 68, p2606.Substrate can be rigid or elasticity.Substrate is also possible to plastics, metal, semiconductor wafer or glass.Substrate has smooth surface in one of the embodiments,.Substrate free of surface defects is especially desirable selection.In an embodiment, substrate is flexible, optional in thin polymer film or plastics, and glass transition temperature Tg is 150 DEG C or more, preferably more than 200 DEG C, more preferably more than 250 DEG C, preferably more than 300 DEG C.Flexible base board can be poly- (ethylene glycol terephthalate) (PET) or polyethylene glycol (2,6- naphthalene) (PEN).
Anode 102 may include conductive metal, metal oxide or conducting polymer.Anode can be easily injected into hole into hole injection layer (HIL) or hole transmission layer (HTL) or luminescent layer.The absolute value of the difference of the HOMO energy level or valence-band level of the illuminator in the work function and luminescent layer of anode or the p-type semiconductor material as HIL or HTL or electronic barrier layer (EBL) is less than 0.5eV in one of the embodiments,.The absolute value of the difference of the HOMO energy level or valence-band level of the illuminator in the work function and luminescent layer of anode or the p-type semiconductor material as HIL or HTL or electronic barrier layer (EBL) is less than 0.3eV in one of the embodiments,.The absolute value of the difference of the HOMO energy level or valence-band level of the illuminator in the work function and luminescent layer of anode or the p-type semiconductor material as HIL or HTL or electronic barrier layer (EBL) is less than 0.2eV in one of the embodiments,.The example of anode material includes but is not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminium-doped zinc oxide (AZO) etc..Other suitable anode materials be it is known, those of ordinary skill in the art are readily able to select use.Any suitable technology deposition, such as a suitable physical vaporous deposition, including rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc. can be used in anode material.Anode is patterning in one of the embodiments,.Patterned ITO electrically-conductive backing plate is commercially available, and can be used to prepare device according to the present invention.
Cathode 106 may include conductive metal or metal oxide.Cathode can be easily injected into electronics to EIL or ETL or directly into luminescent layer.The absolute value of the difference of the lumo energy or conduction level of illuminator or the n-type semiconductor as electron injecting layer (EIL) or electron transfer layer (ETL) or hole blocking layer (HBL) is less than 0.5eV in the work function of cathode and luminescent layer in one of the embodiments,.The absolute value of the difference of the lumo energy or conduction level of illuminator or the n-type semiconductor as electron injecting layer (EIL) or electron transfer layer (ETL) or hole blocking layer (HBL) is less than 0.3eV in the work function of cathode and luminescent layer in one of the embodiments,.The absolute value of the difference of the lumo energy or conduction level of illuminator or the n-type semiconductor as electron injecting layer (EIL) or electron transfer layer (ETL) or hole blocking layer (HBL) is less than 0.2eV in the work function of cathode and luminescent layer in one of the embodiments,.In principle, the material of all cathodes that can be used as OLED all may be as the cathode material of device of the present invention.The example of cathode material includes but is not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO etc..Any suitable technology deposition, such as a suitable physical vaporous deposition, including rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc. can be used in cathode material.
OLED can also include other function layer, such as hole injection layer (HIL), hole transmission layer (HTL), electronic barrier layer (EBL), electron injecting layer (EIL), electron transfer layer (ETL) or hole blocking layer (HBL).It is described later in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1 suitable for the material in these functional layers, is hereby incorporated herein by reference the full content in this three patent documents.As shown in Figure 1, the OLED further includes the hole transmission layer 103 between anode 102 and luminescent layer 104 and the electron-transport between luminescent layer 104 and cathode 106
Layer 105.
Luminescent layer 104 is formed by the way of vacuum evaporation in one of the embodiments, and evaporation source includes above-mentioned fused ring compound.
Luminescent layer 104 is prepared by above-mentioned composition by printing type in one of the embodiments,.
The emission wavelength of electroluminescent device is 300 between 1000nm in one of the embodiments,.The emission wavelength of electroluminescent device is 350 between 900nm in one of the embodiments,.The emission wavelength of electroluminescent device is 400 between 800nm in one of the embodiments,.
The application of above-mentioned organic electronic device in the electronic device.The electronic equipment is display equipment, lighting apparatus, light source or sensor etc..
The electronic equipment of one embodiment includes above-mentioned organic electronic device.The electronic equipment is display equipment, lighting apparatus, light source or sensor etc..
The preparation method of the organic electronic device of one embodiment, comprising the following steps:
Above-mentioned fused ring compound or above-mentioned organic mixture are deposited on substrate, forms functional layer.
In one of the embodiments, the functional layer with a thickness of 5nm-1000nm.
The preparation method of the organic electronic device of another embodiment, comprising the following steps:
By the way of printing or coating, above-mentioned composition is coated on substrate, and the organic solvent evaporation in the composition is fallen, form functional layer.
Mode of printing is inkjet printing, spray printing, typographic printing, silk-screen printing, roller printing, torsion roller printing, lithographic printing, bat printing, flexographic printing or rotary printing in one of the embodiments,.Coating method is dip-coating, rotary coating, blade coating, spraying, brushing or the coating of slit-type squash type.
Wherein, suitable printing or coating technique include but is not limited to inkjet printing, typographic printing, silk-screen printing, dip-coating, roller printing, lithographic printing are reversed in rotary coating, blade coating, roller printing, flexographic printing, rotary printing, spraying, brushing or bat printing, slit-type squash type coating etc..It is preferred that intaglio printing, silk-screen printing and ink jet printing.Intaglio printing, ink jet printing will apply in an embodiment of the present invention.Solution or suspension can also comprise one or more components such as surface active cpd, and lubricant, wetting agent, dispersing agent, hydrophobing agent, bonding agent etc., for adjusting viscosity, filming performance improves adhesion etc..Related printing technique, and its to the related request in relation to solution, such as solvent and concentration, viscosity etc., details refer to Helmut Kipphan chief editor " print media handbook: technology and production method " (Handbook of Print Media:Technologies and Production Methods), ISBN 3-540-67326-1.
In one of the embodiments, the functional layer with a thickness of 5nm-1000nm.
Embodiment 1: the synthesis of compound 1
Under nitrogen flowing in the 250mL three-necked flask with condenser pipe, it is added 3,9- bis- bromo- 7,7- dimethyl-naphtho- [2,1,8,7-defg] aphthacene (6.7g, 14mmol), (9,9- dimethyl fluorene -3- base) boric acid (6.7g, 28mmol), Pd (PPh3)4(920mg, 0.8mmol), potassium carbonate (11g, 80mmol), toluene 120mL and water 40mL, 90 DEG C are stirred overnight.After reaction, column chromatography purifies to obtain faint yellow solid powder (8.1g, 83%).
Embodiment 2: the synthesis of compound 2
Under nitrogen flowing in the 250mL three-necked flask with condenser pipe, 3,9- bis- bromo- 7 is added, 7- dimethyl-naphtho- [2,1,8,7-defg] aphthacene (7.1g, 15mmol), two tolyl amine (5.9g, 30mmol), Pd (dba)2(520mg,0.9mmol)、NaOtBu(8.7g,90mmol)、(tBu)3P (545mg, 2.7mmol) and dry toluene 150mL, 100 DEG C are stirred overnight.After reaction, column chromatography purifies to obtain faint yellow solid powder (7.0g, 66%).
Embodiment 3: the synthesis of compound 3
Under nitrogen flowing in the 250mL three-necked flask with condenser pipe, it is added 3,9- bis- bromo- 7,7- dimethyl-naphtho- [2,1,8,7-defg] aphthacene (7.6g, 16mmol), N- ([1,1'- biphenyl] -2- base) dibenzofurans -4- amine (10.7g, 32mmol), Pd (dba)2(520mg,0.9mmol)、NaOtBu(8.7g,90mmol)、(tBu)3P (545mg, 2.7mmol) and dry toluene 150mL, 100 DEG C are stirred overnight.After reaction, column chromatography purifies to obtain faint yellow solid powder (11.7g, 74%).
Embodiment 4: the synthesis of compound 4
Under nitrogen flowing in the 250mL three-necked flask with condenser pipe, it is added 3,9- bis- bromo- 7,7- dimethyl-naphtho- [2,1,8,7-defg] aphthacene (4.7g, 10mmol), N- (4- isopropyl phenyl) dibenzofurans -4- amine (6.03g, 20mmol), Pd (dba)2(350mg,0.6mmol)、NaOtBu(5.7g,60mmol)、(tBu)3P (360mg, 1.8mmol) and dry toluene 100mL, 100 DEG C are stirred overnight.After reaction, column chromatography purifies to obtain faint yellow solid powder (7.2g, 79%).
Embodiment 5: the synthesis of compound 5
Under nitrogen flowing in the 250mL three-necked flask with condenser pipe, 3,9- bis- bromo- 7 is added, 7- dimethyl-naphtho- [2,1,8,7-defg] aphthacene (5.7g, 12mmol), (4a, 9a- dimethyl -9- phenyl -1,2,3,4,4a, 9a- hexahydro-carbazole) -6- boric acid (7.7g, 24mmol), Pd (PPh3)4(800mg, 0.7mmol), potassium carbonate (9.7g, 70mmol), toluene 120mL and water 30mL, 90 DEG C are stirred overnight.After reaction, column chromatography purifies to obtain faint yellow solid powder (7.3g, 70%).
Embodiment 6: the synthesis of compound 6
Under nitrogen flowing in the 250mL three-necked flask with condenser pipe, it is added 3,9- bis- bromo- 7,7- dimethyl-naphtho- [2,1,8,7-defg] aphthacene (4.7g, 10mmol), N- (2,7- dimethylnaphthalene -1- base) dibenzofurans -4- amine (6.7g, 20mmol), Pd (dba)2(350mg,0.6mmol)、NaOtBu(5.7g,60mmol)、(tBu)3P (360mg, 1.8mmol) and dry toluene 100mL, 100 DEG C are stirred overnight.After reaction, column chromatography purifies to obtain faint yellow solid powder (8.6g, 87%).
Comparative example 1: the synthesis of control compounds 1
Under nitrogen flowing in the 500mL three-necked flask with condenser pipe, 1,6- dibromo pyrene (7.2g, 20mmol), di-o-tolyl amine (7.9g, 40mmol), Pd (dba) is added2(690mg,1.2mmol)、NaOtBu(11.5g,120mmol)、(tBu)3P (730mg, 3.6mmol) and dry toluene 150mL, 100 DEG C are stirred overnight.After reaction, the solid for filtering out precipitation washs to obtain faint yellow solid powder (10.7g, 90%) with toluene and methanol.
The preparation and representation of OLED device
The used material of each layer of OLED device:
HIL: triarylamine derivative；HTL: triarylamine derivative；Host: anthracene derivant；Dopant: compound 1- compound 6 or control compounds 1.
It is as follows with ITO/HIL (50nm)/HTL (35nm)/Host:5%Dopant (25nm)/ETL (28nm)/LiQ (1nm)/Al (150nm)/cathode OLED device preparation step:
A, the cleaning of electro-conductive glass substrate: for the first time in use, can be cleaned with multi-solvents, such as chloroform, ketone, isopropanol are cleaned, and then carry out UV ozone plasma treatment；
B, HIL (50nm), HTL (35nm), EML (25nm), ETL (28nm): in high vacuum (1 × 10-6Millibar, mbar) in hot evaporation form.
C, cathode: LiQ/Al (1nm/150nm) is in high vacuum (1 × 10-6Millibar) in hot evaporation form；
D, encapsulate: device is encapsulated in nitrogen glove box with ultraviolet hardening resin.
Current Voltage (J-V) characteristic of each OLED device is characterized by characterization equipment, while recording important parameter such as efficiency, service life and external quantum efficiency.Through detecting, control compounds 1 are better than as the chromaticity coordinates of blue-light device prepared by EML layers of illuminator using compound 1- compound 6, such as the chromaticity coordinates of device prepared by compound 3 is (0.148,0.076).In addition, using compound 1- compound 6 as blue-light device prepared by EML layers of illuminator luminous efficiency all in 6-8cd/A range, there is more excellent luminous efficiency.In terms of device lifetime, control compounds 1 are more better than as the service life of blue-light device prepared by EML layers of illuminator using compound 1- compound 6, such as T95 of the device prepared by compound 3 at 1000nits is 1.45 times of control compounds 1.
Claims (16)
- A kind of fused ring compound for organic electronic device, which is characterized in that shown in the structure of the fused ring compound such as general formula (1):Wherein,X1Selected from CR1R2, O, S or NR3；R1-R3、R11-R19And R110-R112Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Wherein, R1-R3、R11-R19And R110-R112At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding1-R3、R11-R19And R110-R112In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other.
- Fused ring compound according to claim 1, which is characterized in that shown in the structure of the fused ring compound such as general formula (2):Wherein,Ar1-Ar3Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Ar1-Ar3At least one of form monocycle or polycyclic aliphatic series or aromatic ring or Ar with the ring of the group bonding1-Ar3In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other.
- Fused ring compound according to claim 1 or 2, which is characterized in that the structure of the fused ring compound is as shown in any structure in general formula (3)-(8):
- Fused ring compound according to any one of claim 1-3, which is characterized in that R11-R19、R110-R112And Ar1-Ar3At least one of selected from following any group:Wherein,R41-R42、R410-R411And R413-R433Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy with 3 to 20 C atoms, substituted or unsubstituted silicyl, substituted ketone group with 1 to 20 C atom, alkoxy carbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanates, thiocyanates, isothiocyanates, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and one of aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Wherein, R41-R42、R410-R411And R413-R433At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding41-R42、R410-R411And R413-R433In at least two form monocycles or polycyclic aliphatic series or aromatic ring between each other.M is 0,1,2 or 3；N, p and s independently is 0,1,2,3 or 4；T and q independently is 0,1,2,3,4 or 5；P is selected from the saturation cycloalkane with 3 to 8 C atoms；L indicates singly-bound or linking group；Wherein, the linking group is selected from one of substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and aryloxy group with 5 to 40 annular atoms or heteroaryloxy group or a variety of；Dotted line indicates the singly-bound that L is connect with other groups.
- Fused ring compound according to claim 4, which is characterized in that the linking group is selected from following any group:Wherein:X1Selected from CR61Or N；Y is selected from CR62R63、SiR64R65、NR66, C (=O), S or O；R61-R66Independently selected from H, straight chained alkyl with 1 to 20 C atom, alkoxy with 1 to 20 C atom, thio alkoxy group with 1 to 20 C atom, branch or cricoid alkyl with 3 to 20 C atoms, branch or cricoid alkoxy with 3 to 20 C atoms, branch or cricoid thio alkoxy group with 3 to 20 C atoms, silyl-group, substituted keto group with 1 to 20 C atom, alkoxycarbonyl groups with 2 to 20 C atoms, aryloxycarbonyl group with 7 to 20 C atoms, cyano group, carbamoyl group, halogen formyl group, formyl group, isocyano group group, isocyanate groups, thiocyanates group, isothiocyanates group, hydroxyl group, nitryl group, CF3One of group, Cl, Br, F, crosslinkable group, the substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system and aryloxy group with 5 to 40 annular atoms or heteroaryloxy group are a variety of；Wherein, R61、R62、R63、R64、R65And R66At least one of form monocycle or polycyclic aliphatic series or aromatic ring or R with the ring of the group bonding61、R62、R63、R64、R65And R66At least two form monocycles or polycyclic aliphatic series or aromatic ring between each other.
- Fused ring compound according to claim 5, which is characterized in that the linking group is selected from following any group:
- Fused ring compound according to claim 1 to 6, which is characterized in that at least one H atom in the fused ring compound is replaced by D atom.
- A kind of polymer, which is characterized in that at least one repetitive unit includes such as claim 1-7 in the polymer Any one of described in fused ring compound.
- A kind of mixture, which is characterized in that the organic mixture includes at least one organic functional material and such as fused ring compound of any of claims 1-7 or polymer as claimed in claim 8；Wherein, the organic functional material is selected from hole-injecting material, hole mobile material, hole barrier materials, electron injection material, electron transport material, electron-blocking materials, organic host materials, singlet emitters, triplet emitters, thermal excitation delayed fluorescence material or organic dyestuff.
- A kind of composition, which is characterized in that the composition includes organic solvent and such as fused ring compound of any of claims 1-7 or polymer as claimed in claim 8 or mixture as claimed in claim 9.
- A kind of organic electronic device, it is characterized in that, the organic electronic device includes that perhaps the functional layer of mixture as claimed in claim 9 or the organic electronic device is prepared by composition as claimed in claim 10 for such as fused ring compound of any of claims 1-7 or polymer as claimed in claim 8.
- Organic electronic device according to claim 11, it is characterized in that, the organic electronic device is selected from Organic Light Emitting Diode, organic photovoltaic battery, organic light emission battery, organic field-effect tube, organic light-emitting field effect pipe, organic laser, organic spin electric device, organic sensor or organic plasmon emitting diode.
- Organic electronic device according to claim 12, it is characterized in that, the organic electronic device is Organic Light Emitting Diode, the Organic Light Emitting Diode, which includes at least, a luminescent layer, the luminescent layer includes that the fused ring compound or the polymer or the mixture or the luminescent layer are prepared by the composition.
- A kind of preparation method of organic electronic device, which comprises the following steps:Vapor deposition such as fused ring compound of any of claims 1-7 or organic mixture as claimed in claim 9, forms functional layer on substrate.
- A kind of preparation method of organic electronic device, which comprises the following steps:By the way of printing or coating, composition as claimed in claim 10 is coated on substrate, forms functional layer.
- The preparation method of organic electronic device according to claim 15, it is characterized in that, the mode of printing is inkjet printing, spray printing, typographic printing, silk-screen printing, roller printing, torsion roller printing, lithographic printing, bat printing, flexographic printing or rotary printing；The coating method is dip-coating, rotary coating, blade coating, spraying, brushing or the coating of slit-type squash type.
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| PCT/CN2017/113944 WO2018099433A1 (en) | 2016-11-30 | 2017-11-30 | Fused ring compound and use thereof, mixture and organic electronic device |
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| CN112479987A (en) * | 2020-12-22 | 2021-03-12 | 吉林奥来德光电材料股份有限公司 | Fluorene phosphorescent compound, preparation method thereof and organic electroluminescent device |
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Application publication date: 20190521 |