CN109790087A - Deuterated fused ring compound, high polymer, mixture, composition and organic electronic device - Google Patents
Deuterated fused ring compound, high polymer, mixture, composition and organic electronic device Download PDFInfo
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- CN109790087A CN109790087A CN201780059202.5A CN201780059202A CN109790087A CN 109790087 A CN109790087 A CN 109790087A CN 201780059202 A CN201780059202 A CN 201780059202A CN 109790087 A CN109790087 A CN 109790087A
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- organic
- deuterated
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- atoms
- alkoxy
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 125000004429 atom Chemical group 0.000 claims description 52
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- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
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- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
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- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003220 pyrenes Chemical class 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 241000894007 species Species 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
- 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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
Abstract
The invention discloses a kind of deuterated fused ring compound, high polymer, composition, mixture and its applications in the application of organic electronic device, especially in organic electroluminescent LED.The invention also discloses the organic electronic devices including the deuterated fused ring compound, especially organic electroluminescent LED, and its application in display and lighting engineering.The present invention is optimized by device architecture, can reach preferable device performance, high performance OLED device especially can be achieved, and provides preferable material and technology of preparing option to full-color display and illumination application.
Description
Related application
The present patent application required filed on November 23rd, 2016, and application No. is 201611059687.1, the priority of the Chinese patent application of entitled " deuterated fused ring compound and its application in electronic device " is incorporated herein by reference in its entirety.
The present invention relates to technical field of organic electroluminescence, more particularly to a kind of deuterated fused ring compound, high polymer, mixture, composition and organic electronic device.
Due to optics and electric property that organic semiconducting materials have diversity, manufacturing cost relatively low and excellent in synthesis, 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.Usually there are positive electrode and negative electrode using the organic electroluminescent device of organic electroluminescent phenomenon and among them comprising the structure of organic matter layer.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, 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, 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 outstanding 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.
Conventional blu-ray organic electroluminescent device luminescent layer uses host-guest system structure.What it is as conventional blu-ray material of main part 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.As traditional blue light-emitting object
Compound, adoptable is aryl vinyl aminated compounds (WO 04/013073, WO 04/016575, WO 04/018587).However, the thermal stability of these compounds is poor, easily decomposes, cause the service life of device poor, be the most important disadvantage of OLED material 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.
Therefore, it still needs to be further improved material.For Nan dian Yao, material of main part is the critical material for determining its service life.High performance Blue-light emitting host material is always the developing focus of people.
Summary of the invention
Based on this, the object of the present invention is to provide a kind of deuterated fused ring compound, high polymer, mixture, composition and organic electronic devices.
Specific technical solution is as follows:
The present invention provides a kind of deuterated fused ring compound as shown in logical formula (I):
Wherein,
R11-R19And R110It is separately H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms;
Also, R11-R19And R110In at least one contain one in structure shown in logical formula (II)-(IV):
Wherein,
R21-R25In, R31-R37In or R41-R47In; at least one is the singly-bound being connected with other groups; remaining is separately H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms.
In some preferential embodiments, R13And/or R18Contain one in the structure as shown in the logical formula (II)-(IV).
In some more preferential embodiments, a kind of deuterated fused ring compound has structure shown in general formula (V-1)-(V-3):
Wherein,
R510-R545It is separately H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms.
L indicates linking group, it can be singly-bound or the deuterated or not deuterated substituted or unsubstituted aromatics with 5 to 40 annular atoms or heteroaromatic ring system, or the combination of the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms.
Ar3And Ar4It is separately the combination of the deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms with 5 to 40 annular atoms.
M and n is separately the integer of 0-6.
The present invention also provides a kind of high polymer, the repetitive unit of the high polymer includes that at least one of structure as shown in logical formula (I) and general formula (V-1)-(V-3) loses the group formed after at least one hydrogen atom.
The present invention furthermore provides a kind of mixture, including the deuterated fused ring compound or high polymer and the second organic functional material.Second organic functional material is optional in 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), singlet emitters (fluorescent illuminant), triplet emitters (phosphorescent emitter), thermal excitation delayed fluorescence material (TADF material) and
At least one of organic dyestuff.
The present invention also provides a kind of compositions, including deuterated fused ring compound as described above or high polymer and organic solvent.
The present invention also provides a kind of organic electronic devices, including the deuterated fused ring compound or high polymer.
The organic electronic device is optional in 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 and organic phasmon emitting diode (Organic Plasmon Emitting Diode).
In a more preferential embodiment, the organic electronic device is an organic electroluminescence device, wherein at least includes a luminescent layer, and the luminescent layer includes the deuterated fused ring compound or high polymer.
The utility model has the advantages that deuterated fused ring compound according to the invention, can be used as material of main part and is used to prepare the organic electroluminescent device with blue-light-emitting, and it is opposite without deuterated fused ring compound, longer device lifetime can be obtained.
Fig. 1 is a kind of structural schematic diagram of organic electronic device provided by the invention,
In figure, 101 be substrate, and 102 be anode, and 103 be hole injection layer (HIL) or hole transmission layer (HTL), and 104 be luminescent layer, and 105 be electron injecting layer (EIL) or electron transfer layer (ETL), and 106 be cathode.
To facilitate the understanding of the present invention, a more comprehensive description of the invention is given in the following sections with reference to the relevant attached drawings.Presently preferred embodiments of the present invention is given in attached drawing.But the invention can be realized in many different forms, however it is not limited to embodiment described herein.It is made the disclosure of the present invention more thorough and comprehensive on the contrary, purpose of providing these embodiments is.
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.
In the present invention, material of main part, host material, Host material and Matrix material have the same meaning, and can be interchanged.
In the present invention, metallo-organic complex, metal organic complex, organometallic complex have the same meaning, and can be interchanged.
In the present invention, composition, printing ink, ink and ink have the same meaning, and can be interchanged.
The present invention provides a kind of deuterated fused ring compound as shown in logical formula (I):
Wherein,
R11-R19And R110It is separately H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl, or Br, or F, or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or aryloxy group or heteroaryloxy group with 5 to 40 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
Also, R11-R19And R110In at least one contain one in structure shown in logical formula (II)-(IV):
Wherein,
R21-R25In, R31-R37Neutralize R41-R47In; at least one is the singly-bound being connected with other groups respectively; remaining is H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, or have 5 to
The substituted or unsubstituted aromatics of 40 annular atoms or heteroaromatic ring system, or aryloxy group or heteroaryloxy group with 5 to 40 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In some preferential embodiments, R21-R25In, R31-R37Neutralize R41-R47In; at least one is the singly-bound being connected with logical formula (I) respectively; remaining is H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl, or Br, or F, or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or aryloxy group or heteroaryloxy group with 5 to 40 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In certain preferential embodiments, R11-R19And R110It is separately H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 10 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 10 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 10 C atom; or the alkoxy carbonyl with 2 to 10 C atoms; or the aryloxycarbonyl with 7 to 10 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl, or Br, or F, or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 20 annular atoms, or aryloxy group or heteroaryloxy group with 5 to 20 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In certain more preferential embodiments, R11-R19And R110In other than structure shown at least one contains logical formula (II)-(IV), mutually independent it can be selected from H, D, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, the preferably substituted or unsubstituted aromatics with 5 to 30 annular atoms or heteroaromatic ring system, the more preferably substituted or unsubstituted aromatics with 5 to 20 annular atoms or heteroaromatic ring system.In a more preferential embodiment, aromatic ring includes 5~15 carbon atoms in ring system, and more excellent is 5~10 carbon atoms;Miscellaneous aromatic ring includes 2~15 carbon atoms in ring system, and more excellent is 2~10 carbon atoms and at least one hetero atom, and condition is that carbon atom and heteroatomic sum are at least 4.Hetero atom is preferably selected from Si, N, P, O, S and/or Ge, is particularly preferably selected from Si, N, P, O and/or S, more special
N, O or S are not preferably selected from it.
Above-described aromatic ring or aromatic group refer to the alkyl for containing at least one aromatic ring, including monocyclic groups and polycyclic loop system.Above-described miscellaneous aromatic ring or heteroaromatic group refer to the alkyl (containing hetero atom) comprising at least one hetero-aromatic ring, 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 by short non-aromatic unit, preferably smaller than 5% non-H atom, such as C, N or O atom)., 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.
Specifically, the example of aromatic group has: benzene, naphthalene, anthracene, phenanthrene, perylene, aphthacene, pyrene, BaP, triphenylene, acenaphthene, fluorenes, spiro fluorene and its derivative.
Specifically, the example of heteroaromatic group has: 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, and its derivative.
The R in certain preferred embodiments11-R19And R110It can also further select in H, D or comprising one of following building stone or multiple combinations:
Wherein,
A1、A2、A3、A4、A5、A6、A7、A8Independently indicate CR3Or N;
Y1Selected from CR4R5、SiR4R5、NR3, C (=O), S or O;
R3、R4、R5It is separately H; D; or straight chained alkyl, alkoxy or thio alkoxy group with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy group with 3 to 20 C atoms; either silyl-group; or the substituted keto group with 1 to 20 C atom; or the alkoxycarbonyl groups with 2 to 20 C atoms; or the aryloxycarbonyl group with 7 to 20 C atoms; or cyano group (- CN) or carbamoyl group (- C (=O) NH2); or halogen formyl group (- C (=O)-X; wherein, X represents halogen atom) or formyl group (- C (=O)-H); or isocyano group group; or isocyanate groups or thiocyanates group or isothiocyanates group or hydroxyl group; or nitryl group or CF3Group or Cl or Br or F or crosslinkable group, or there are 5 to 40
The substituted or unsubstituted aromatics of annular atom or heteroaromatic ring system, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms, wherein one or more groups R3, R4, R5Monocycle or polycyclic aliphatic series or aromatic ring can be formed each other and/or with the ring of the group bonding.
The R in certain more preferential embodiments11-R19And R110It is also optional in H, D or comprising one of following building stone or multiple combinations, the H in middle ring can arbitrarily be replaced:
In the preferential embodiment of a comparison, R in the deuterated fused ring compound13And/or R18Contain one in the structure as shown in the logical formula (II)-(IV).
In other preferential embodiments, R11、R12、R14、R15-R17、R19And R110It is separately H or D or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or aryloxy group or heteroaryloxy group with 5 to 40 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In other more preferential embodiments, R11、R12、R14、R15-R17、R19And R110It is separately H, or D, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 10 annular atoms, or aryloxy group or heteroaryloxy group with 5 to 10 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In an embodiment the most preferential, R11、R12、R14、R15-R17、R19And R110It is separately H or D.
In some preferential embodiments, Ar1And Ar2One be separately selected from structure shown in (II)-(IV).
In some very preferential embodiments, a kind of deuterated fused ring compound has structure shown in general formula (V-1)-(V-3):
Wherein,
R510-R545It is separately H or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl, or Br, or F, or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or aryloxy group or heteroaryloxy group with 5 to 40 annular atoms, or the combination of these systems, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In some preferential embodiments, R510-R545It is separately H; or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 10 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 10 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 10 C atom; or the alkoxy carbonyl with 2 to 10 C atoms; or the aryloxycarbonyl with 7 to 10 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates or isothiocyanates; or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, or the substituted or unsubstituted aromatics with 5 to 20 annular atoms or
Heteroaromatic ring system, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 20 annular atoms, wherein one or more groups can form monocycle or polycyclic aliphatic series or aromatics ring system each other and/or with the ring of the group bonding;One or more H in above-described various groups can also be further replaced D.
In some more preferential embodiments, a kind of deuterated fused ring compound has structure shown in general formula (V ' -1)-(V ' -3):
Wherein,
R512-R517、R518-R522、R531-R535And R543-R547It is separately the combination of the deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 20 annular atoms with 5 to 20 annular atoms.And adjacent substituent group can form aromatics or heteroaromatic ring system with 5-20 annular atom between each other.
L indicates linking group, it can be singly-bound, or the combination of the deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms with 5 to 40 annular atoms.
In some preferential embodiments, L indicates singly-bound.
In other preferential embodiments, L is the deuterated or not deuterated substituted or unsubstituted aromatics with 5 to 20 annular atoms or heteroaromatic ring system, or the combination of the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 20 annular atoms.
Ar3And Ar4It is separately the combination of the deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms with 5 to 40 annular atoms.The combination of the preferably deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 20 annular atoms with 5 to 20 annular atoms.Ar3With
Ar4Preferential embodiment with it is above-mentioned be applicable in and R11-R19And R110Aromatics or heteroaromatic group.
M and n is separately the integer of 0-6, preferably the integer of 0-3, the more excellent integer for 0-2, and optimal is 0 or 1.
A kind of deuterated fused ring compound according to the invention, specific example is as follows, but is not limited only to this:
The invention further relates to the synthetic methods of deuterated fused ring compound described in more than one, including using the raw material containing active group to be reacted.Structural unit of these activated feedstocks comprising above-mentioned general formula and at least one leaving group in each case, for example, bromine, iodine, boric acid or borate.The reaction appropriate for forming C-C connection is well known to those skilled in the art and is described in document that especially appropriate and preferred coupling reaction is SUZUKI, STILLE and HECK coupling reaction.
The present invention is further directed to a kind of high polymer, and repetitive unit includes to lose the group formed after at least one H just like structure shown in general formula (I).In certain embodiments, the high polymer is non-conjugated highpolymer, wherein the structural unit as shown in logical formula (I) is on side chain.In another preferred embodiment, the high polymer is conjugated highpolymer.
The present invention also provides a kind of mixtures, including above-described deuterated fused ring compound or high polymer and the second organic functional material.Second organic functional material is optional in 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), singlet emitters (fluorescent illuminant), triplet emitters (phosphorescent emitter), thermal excitation delayed fluorescence material (TADF material) and have
At least one of engine dyeing material.Such as various organic functional materials are described later in detail in WO2010135519A1, US20090134784A1 and WO 2011110277A1, the full content in this 3 patent document is incorporated herein by reference hereby.
In a preferred embodiment, second organic functional material is fluorescent illuminant (or singlet emitters) material.The deuterated fused ring compound or high polymer are as host-guest, and fluorescent illuminant is as object, weight percent≤15wt% of object, preferably≤12wt%, more preferably≤9wt%, more more preferably≤8wt%, preferably≤7wt%.
In a more preferential preferred embodiment, second organic functional material is fluorescent illuminant material and=fluorescent host material (or singlet emitters).In such an embodiment, the deuterated fused ring compound or high polymer can be used as total material of main part, and the weight ratio with the fluorescent host material is from 3:7 to 7:3.
In some embodiments, second organic functional material is fluorescent host material and TADF material.
In other preferred embodiments, the second organic functional material fluorescent host material and HTM material.
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 and their derivative.In addition, suitable HIM also includes self assembly monomer, such as compound containing phosphonic acids and sliane derivative;Metal complex and cross-linking compounds etc..
Electronic barrier layer (EBL) is used to stop the electronics from successive functional layers, especially luminescent layer.The luminescent device on one not no barrier layer of comparison, the presence of EBL normally result in the raising of luminous efficiency.The electron-blocking materials (EBM) of electronic barrier layer (EBL) are needed than successive functional layers, such as the higher LUMO of luminescent layer.In a preferential embodiment, HBM has the excited level bigger than adjacent emissive layers, such as singlet state or triplet, depends on illuminator, meanwhile, EBM has hole transfer function.Usually the HIM/HTM material with high lumo energy can be used as EBM.
The example that can be used as the cyclophane perfume (or spice) amine derivative compounds of HIM, HTM or EBM includes but is not limited to following general structure:
Each Ar1To Ar9Aromatic hydrocarbon ring compound can be independently selected from, such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, that non-alkene, phenanthrene, fluorenes, pyrene, bend, Azulene;Heteroaromatic compound, as 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, two pyridine of thiophene pyridine, benzo selenophen pyridine and selenophen;It include the group of 2 to 10 ring structures, they 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 and aliphatic cyclic group.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.
In one aspect, Ar1To Ar9It can be independently selected from comprising the group such as the following group:
N is 1 to 20 integer;X1To X8It is 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 that can be used as the metal complex of HTM or HIM includes but is not limited to following general structure:
M is a metal, there is the atomic weight greater than 40;
(Y1-Y2) it is one liang of tooth ligand, Y1And Y2Independently selected from C, N, O, P and S;L is an assistant ligand;M is an integer, value from 1 to this metal maximum coordination number;M+n is the maximum coordination number of this metal.
In one embodiment, (Y1-Y2) it is 2- phenylpyridine derivative
In another embodiment, (Y1-Y2) it is a carbenes
In another embodiment, M choosing is in Ir, Pt, Os and Zn.
On the other hand, the HOMO of metal complex is greater than -5.5eV (relative to vacuum level)
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 example of the organic compound used as singlet state material of main part can be selected from containing aromatic hydrocarbon ring compound, such as benzene, biphenyl, triphenyl, benzo, naphthalene, En, Fu, phenanthrene, fluorenes, pyrene, bend, Azulene;Heteroaromatic compound, as 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 two pyridine of thiophene, benzo selenophen pyridine and selenophen;It include the group of 2 to 10 ring structures, they 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 and aliphatic cyclic group.
In a preferential embodiment, singlet state material of main part is optional in the compound comprising at least one following group:
Wherein, R1It can select independently of each other in following group: hydrogen, alkyl, alkoxy, amino, alkene, alkynes, aralkyl, miscellaneous alkyl, aryl and heteroaryl;Ar1It is aryl or heteroaryl, Ar defined in it and above-mentioned HTM1Meaning is identical;N is an integer from 0 to 20;X1-X8It selects in CH or N;X9And X10It selects in CR1R2Or NR1。
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.
In a preferential embodiment, singlet emitters can be selected from unitary styrylamine, binary styrylamine, ternary benzene
Vinylamine, quaternary styrylamine, styrene phosphine, styrene ether and arylamine.
One unitary styrylamine refers to a compound, it includes a styryl group and at least one amine, preferably aromatic amine unsubstituted or replace.One binary styrylamine refers to a compound, it includes two styryl groups and at least one amine, preferably aromatic amine unsubstituted or replace.One ternary styrylamine refers to a compound, it includes three styryl groups and at least one amine, preferably aromatic amine unsubstituted or replace.One quaternary styrylamine refers to a compound, it includes four styryl groups and at least one amine, preferably aromatic amine unsubstituted or replace.One preferred styrene is talan, may 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 comprising three or replacing.At least one in the loop system of these aromatic series or heterocycle is preferentially selected in fused ring system, and is preferably formed at least 14 aromatic ring atoms.Wherein preferred example has fragrant anthranylamine, fragrant anthradiamine, fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong and fragrance diamines in the wrong.One fragrant anthranylamine refers to a compound, and one of binary arylamine group is directly linked on anthracene, preferably on 9 position.One fragrant anthradiamine refers to a compound, and wherein two binary arylamine group is directly linked on anthracene, preferably on 9,10 position.Fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong is similar with the fragrance definition of diamines in the wrong, and wherein binary arylamine group is preferably linked to the 1 or 1 of pyrene, on 6 positions
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 of US 6251531 B1, US 1957606 A1 of 2006/210830 A, EP and 2008/0113101 A1 of US hereby in the above-mentioned patent document listed is incorporated to Herein as reference.
The example of singlet emitters based on stibene extremely derivative has US 5121029.
Further preferred singlet emitters are optional in indenofluorene-amine and indenofluorene-diamines, as disclosed in WO 2006/122630, benzo indenofluorene-amine and benzo indenofluorene-diamines, as disclosed in WO 2008/006449, dibenzo indenofluorene-amine and dibenzo indenofluorene-diamines, as disclosed in WO2007/140847.
Other materials that can be used as singlet emitters have polycyclic aromatic hydrocarbon compounds, the derivative of especially following 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 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 (such as US5121029, US5130603), cyclopentadiene such as tetraphenyl cyclopentadiene, rubrene, cumarin, rhodamine, quinacridone, pyrans such as 4 (dicyano methylene) -6- (4- is to dimethylaminostyryl -2- methyl) -4 H- pyrans (DCM), thiapyran, bis- (azine) imines boron compounds (2007/0092753 A1 of US), bis- (azine) methylene compounds, carbostyryl compound, oxazinone, benzoxazoles, benzothiazole, benzimidazole and 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%.Material structure is controllable simultaneously, and property is stablized, 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, preferably Δ Est < 0.3eV, and secondary is Δ Est < 0.2eV well, preferably Δ Est < 0.1eV.In a preferential embodiment, TADF material has smaller Δ Est, and in another preferential embodiment, TADF has preferable fluorescence quantum efficiency.Some TADF luminous material can be found in following patent documents: CN103483332 (A), TW201309696 (A), TW201309778 (A), TW201343874 (A), TW201350558 (A), US20120217869 (A1), WO2013133359 (A1), WO2013154064 (A1), Adachi, et.al.Adv.Mater., 21,2009,4802, Adachi, et.al.Appl.Phys.Lett., 98,2011,083302, Adachi, et.al.Appl.Phys.Le Tt., 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., 48,2012,9 580, 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 publication for the above organic functional material occur is that disclosed purpose is incorporated herein in way of reference.
In a preferred embodiment, the deuterated fused ring compound or high polymer are used for vapor deposition property OLED device.For this purpose, molecular weight≤1000mol/kg of the deuterated fused ring compound or high polymer, preferably≤900mol/kg, very preferably≤850mol/kg, more preferably≤800mol/kg, most preferably≤700mol/kg.
Another object of the present invention is to provide material solution for printing OLED.
For this purpose, molecular weight >=700mol/kg of the deuterated fused ring compound or high polymer, preferably >=900mol/kg, very preferably >=900mol/kg, more preferably >=1000mol/kg, most preferably >=1100mol/kg.
In other preferred embodiments, at 25 DEG C, the deuterated fused ring compound or high polymer solubility >=10mg/ml in toluene, preferably >=15mg/ml, most preferably >=20mg/ml.
The present invention also provides a kind of compositions, including the deuterated fused ring compound or high polymer and the first organic solvent.
In some embodiments, in the composition, the deuterated fused ring compound can be used as material of main part.
In other embodiments, the composition further comprises singlet emitters material.
In a preferential embodiment, the composition further comprises material of main part and singlet emitters.
In another preferential embodiment, the composition includes at least two material of main parts and a kind of singlet emitters.
In another preferential embodiment, the composition further comprises material of main part and hot activation delayed fluorescence luminescent material.
In other preferential embodiments, the composition further comprises hole mobile material (HTM), and more preferential, the HTM includes a crosslinkable groups.
In a preferred embodiment, composition according to the invention is solution.
In another preferred embodiment, composition according to the invention is suspension.
It may include 0.01 to 20wt% deuterated fused ring compound or high polymer in composition in the embodiment of the present invention, preferably 0.1 to 15wt%, preferably 0.2 to 10wt%, most preferably 0.25 to 5wt% deuterated fused ring compound or high polymer.
In some preferential embodiments, a kind of composition according to the invention, wherein first organic solvent is selected from aromatics or heteroaromatic, ester, aromatic ketone or aromatic oxide, aliphatic ketone or fatty ether, alicyclic or alkenes compounds, or the mixture of the inorganic ester type compound such as borate or phosphate or two kinds and two or more solvents.
In other preferential embodiments, a kind of composition according to the invention, wherein including at least aromatics of 50wt% or heteroaromatic solvent;The preferably at least aromatics of 80wt% or heteroaromatic solvent;The particularly preferred at least aromatics of 90wt% or heteroaromatic solvent.
It is according to the invention based on aromatics or the example of the first heteroaromatic organic 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 tetrahydrofuran, ethyl -2- naphthyl ether, N- methyldiphenylamine, 4- isopropyl biphenyl, α, α-dichloro diphenyl methane, 4- (3- phenyl propyl) pyridine, Ergol, 1, bis- (3,4- 3,5-dimethylphenyl) ethane of 1-, 2- isopropyl naphthalene, benzyl ether etc..
In further embodiments, the first organic solvent appropriate and preferred be aliphatic, alicyclic or aromatic hydrocarbons race, amine, mercaptan, amide, nitrile, ester, ether, polyethers, alcohol, glycol or polyalcohol.
In further embodiments, alcohol represents the first organic solvent of appropriate classification.Preferred alcohol includes alkyl cyclohexanol, the aliphatic alcohol especially to methylate, naphthols etc..
First organic solvent can be cycloalkane, such as decahydronaphthalenes.
First organic solvent can be single use, and be also possible to use as the mixture of two or more organic solvents.
In certain embodiments, composition according to the invention, it further include the second organic solvent, the example of second organic solvent, including but not limited to: 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, 2, 2- tetrachloroethanes, ethyl acetate, butyl acetate, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide, naphthane, naphthalane, indenes and/or their mixture.
In some preferred embodiments, being particularly suitable for organic solvent of the invention is solvent of Hansen (Hansen) solubility parameter in following range:
δd(dispersion force) is in 17.0~23.2MPa1/2Range, especially in 18.5~21.0MPa1/2Range;
δp(polar forces) are in 0.2~12.5MPa1/2Range, especially in 2.0~6.0MPa1/2Range;
δh(hydrogen bond force) is in 0.9~14.2MPa1/2Range, especially in 2.0~6.0MPa1/2Range.
Composition according to the invention, wherein organic solvent need to consider its boiling point parameter when choosing.In the present invention, boiling point >=150 DEG C of the organic solvent;Preferably >=180 DEG C;It is more preferably >=200 DEG C;More excellent is >=250 DEG C;Optimal is >=275 DEG C or >=300 DEG C.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.
In some preferential embodiments, the composition:
1) its viscosity arrives 100cPs range in 1cPs (mpas) at 25 DEG C, and/or
2) its surface tension arrives 50dyne/cm range in 19dyne/cm (dynes per centimeter) at 25 DEG C.
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, in a preferred embodiment, surface tension of the organic solvent at 25 DEG C is about in 19dyne/cm to 50dyne/cm range;More excellent is in 22dyne/cm to 35dyne/cm range;Optimal is in 25dyne/cm to 33dyne/cm range.
In a preferred embodiment, surface tension of the ink according to the invention at 25 DEG C is about in 19dyne/cm to 50dyne/cm range;More preferably in 22dyne/cm to 35dyne/cm range;Preferably in 25dyne/cm to 33dyne/cm range.
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.In a preferred embodiment, the viscosity of the organic solvent is lower than 100cps;More excellent is lower than 50cps;Optimal is 1.5 to 20cps.Here viscosity refers to the viscosity under the environment temperature in printing, generally at 15-30 DEG C, preferably 18-28 DEG C, more preferably 20-25 DEG C, preferably 23-25 DEG C.The composition so prepared will be particularly suitable for ink jet printing.
In a preferred embodiment, composition according to the invention, the viscosity at 25 DEG C is about in 1cps to 100cps range;More preferably in 1cps to 50cps range;Preferably in 1.5cps to 20cps range.
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.
It is a further object of the present invention to provide the application of above-mentioned deuterated fused ring compound and high polymer in organic electronic device.
The organic electronic device is optional in 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 and organic phasmon emitting diode (Organic Plasmon Emitting Diode).
It is a further object of the present invention to provide the preparation method of above-mentioned organic electronic device,
It include: in the method that is deposited by above-mentioned deuterated fused ring compound, high polymer or mixture in forming a functional layer on a substrate;Or the deuterated fused ring compound or high polymer and the second organic functional material one are arised from and form a functional layer on a substrate in the method for total vapor deposition;Or the method that combinations of the above object is printed or is coated with is coated on a substrate and forms a functional layer.The method wherein printed or be coated with is optional in (but being not limited to) inkjet printing, spray printing (Nozzle Printing), typographic printing, silk-screen printing, dip-coating, rotary coating, roller printing is reversed in blade coating, roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brushing or bat printing, slit-type squash type coating etc..
Purposes the invention further relates to the composition as printing ink when preparing organic electronic device, particularly preferably passes through the preparation method of printing or coating.
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.
Preparation method as described above, the thickness of the functional layer is in 5nm-1000nm.
The invention further relates to a kind of organic electronic devices, including the deuterated fused ring compound or high polymer.The organic electronic device may include a functional layer, is prepared using the composition.In general, the organic electronic device contains at least one cathode, an anode and a functional layer between cathode and anode, wherein the functional layer includes deuterated fused ring compound or high polymer as described above.
In a particularly preferred embodiment, above-described organic electronic device is electroluminescent device, especially OLED, as shown in Figure 1, the organic electronic device includes a substrate 101, an anode 102, at least a luminescent layer 104, a cathode 106.
Substrate 101 can be opaque or transparent.One transparent substrate can be used to manufacture a transparent light emitting component.It see, for example, the Nature such as Bulovic 1996,380, p29 and Gu etc., Appl.Phys.Lett.1996,68,
p2606.Substrate can be rigid or elasticity.Substrate can be plastics, metal, semiconductor wafer or glass.Preferably substrate has a smooth surface.Substrate free of surface defects is especially desirable selection.In a preferred 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.The example of suitable flexible base board has poly- (ethylene glycol terephthalate) (PET) and polyethylene glycol (2,6- naphthalene) (PEN).
Anode 102 may include a conductive metal or 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.In one embodiment, the absolute value of the difference of the HOMO energy level or valence-band level of 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, preferably it is less than 0.3eV, preferably less than 0.2eV.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.In certain embodiments, anode is patterning.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 a conductive metal or metal oxide.Cathode can be easily injected into electronics to EIL or ETL or directly into luminescent layer.In one embodiment, 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 and luminescent layer of cathode, preferably it is less than 0.3eV, preferably less than 0.2eV.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) or hole transmission layer (HTL) 103, electronic barrier layer (EBL), electron injecting layer (EIL) or electron transfer layer (ETL) 105, 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 3 patent documents.
In a preferred embodiment, luminescent layer 104 is by vacuum evaporation, and evaporation source includes the deuterated fused ring compound or high polymer.
In another preferred embodiment, luminescent layer 104 is prepared by printing the composition.
Electroluminescent device according to the invention, emission wavelength 300 between 1000nm, preferably 350 between 900nm, preferably 400 between 800nm.
The invention further relates to the application of the organic electronic device in electronic equipment of various, include, but are not limited to show equipment,
Lighting apparatus, light source, sensor etc..
The invention further relates to the electronic equipment for including organic electronic device according to the invention, include, but are not limited to show equipment, lighting apparatus, light source, sensor etc..
Below in conjunction with preferred embodiment, the present invention is described, but the present invention is not limited to the following examples, it should be understood that, appended claims summarise the scope of the present invention under the guidance of present inventive concept it should be appreciated by one skilled in the art that, to certain change that various embodiments of the present invention are carried out, will all be covered by the spirit and scope of claims of the present invention.
Embodiment 1: the synthesis of compound 1
Under nitrogen flowing in the 250mL three-necked flask equipped with condenser pipe, 2- (3- bromophenyl -5-d) naphthalene (5.7g is added, 20mmol), (10- (naphthalene -1- base) anthracene -9- base) boric acid (7.0g, 20mmol), potassium carbonate (8.3g, 60mmol), Pd (PPh3)4(690mg, 0.6mmol), 100mL toluene and 30mL water, 90 DEG C are stirred overnight.After reaction, organic phase is washed, collection organic phase is spin-dried for column chromatography and purifies to obtain white solid product (8.1g, 80%).
Embodiment 2: the synthesis of compound 2
Under nitrogen flowing in the 250mL three-necked flask equipped with condenser pipe, 2- (3- bromophenyl -5-d) naphthalene (5.1g, 18mmol), (10- (d is added5Phenyl) anthracene -9- base) boric acid (5.5g, 18mmol), potassium carbonate (7.5g, 54mmol), Pd (PPh3)4(624mg, 0.54mmol), 80mL toluene and 20mL water, 90 DEG C are stirred overnight.After reaction, organic phase is washed, collection organic phase is spin-dried for column chromatography and purifies to obtain white solid product (7.1g, 85%).
Embodiment 3: the synthesis of compound 3
Under nitrogen flowing in the 250mL three-necked flask equipped with condenser pipe, 2- (3- bromophenyl -5-d) -7-d- naphthalene (7.1g is added, 25mmol), (10- (naphthalene -1- base -4-d) anthracene -9- base) boric acid (8.7g, 25mmol), potassium carbonate (10.4g, 75mmol), Pd (PPh3)4(870mg, 0.75mmol), 120mL toluene and 30mL water, 90 DEG C are stirred overnight.After reaction, organic phase is washed, collection organic phase is spin-dried for column chromatography and purifies to obtain white solid product (9.3g, 73%).
Embodiment 4: the synthesis of compound 4
Under nitrogen flowing in the 250mL three-necked flask equipped with condenser pipe, 2- (4- bromophenyl) -6-d- naphthalene (5.7g is added, 20mmol), (10- (4-d- naphthalene -1- base) anthracene -9- base) boric acid (7.0g, 20mmol), potassium carbonate (8.3g, 60mmol), Pd (PPh3)4(690mg, 0.6mmol), 120mL toluene and 30mL water, 90 DEG C are stirred overnight.After reaction, organic phase is washed, collection organic phase is spin-dried for column chromatography and purifies to obtain white solid product (8.4g, 83%).
Embodiment 5: the synthesis of compound 5
Under nitrogen flowing in the 250mL three-necked flask equipped with condenser pipe, 2- (the bromo- d of 4- is added4Phenyl) -6-d- naphthalene (4.6g, 16mmol), (10- (4-d- naphthalene -1- base) anthracene -9- base) boric acid (5.6g, 16mmol), potassium carbonate (6.6g, 48mmol), Pd (PPh3)4(570mg, 0.5mmol), 80mL toluene and 20mL water, 90 DEG C are stirred overnight.After reaction, organic phase is washed, collection organic phase is spin-dried for column chromatography and purifies to obtain white solid product (6.3g, 77%).
Comparative example 1: the synthesis of control compounds 1
Under nitrogen flowing in the 250mL three-necked flask equipped with condenser pipe, 2- (4- bromophenyl) naphthalene (8.5g is added, 30mmol), (10- (naphthalene -1- base) anthracene -9- base) boric acid (10.4g, 30mmol), potassium carbonate (12.4g, 90mmol), Pd (PPh3)4(1.0g, 0.9mmol), 150mL toluene and 40mL water, 90 DEG C are stirred overnight.After reaction, organic phase is washed, collection organic phase is spin-dried for column chromatography and purifies to obtain white solid product (12.8g, 84%).
The preparation and representation of embodiment 6:OLED device:
The used material of each layer of OLED device:
A kind of HIL: triarylamine derivative;
A kind of HTL: triarylamine derivative;
Host: compound 1- compound 5, control compounds.
Dopant: pyrene derivatives.
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 layer main body using compound 1- compound 5, such as the chromaticity coordinates of device prepared by compound 5 is (0.149,0.086);In addition, using compound 1- compound 5 as blue-light device prepared by EML layer main body 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 layer main body using compound 1- compound 5, such as T95 of the device prepared by compound 5 at 1000nits is greater than 1000 hours.
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, combination not all possible to each technical characteristic in above-described embodiment is all described, however, as long as there is no contradiction in the combination of these technical features, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, and but it cannot be understood as the limitations to patent of invention range.It should be pointed out that for those of ordinary skill in the art, without departing from the inventive concept of the premise, various modifications and improvements can be made, and these are all within the scope of protection of the present invention.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
- A kind of deuterated fused ring compound as shown in logical formula (I):Wherein,R11-R19And R110It is separately H; or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates; or isothiocyanates or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms;Also, R11-R19And R110In at least one contain one in the structure as shown in general formula (II)-(IV):Wherein,R21-R25In, R31-R37Neutralize R41-R47In, at least one is the singly-bound being connected with the condensed ring of the logical formula (I) respectively, remaining is H, or D, or the straight chained alkyl with 1 to 20 C atom, alkoxy or thio alkoxy, or branch or cricoid alkyl with 3 to 20 C atoms, alkoxy or thio alkoxy, either substituted or unsubstituted silicyl, or the substituted ketone group with 1 to 20 C atom, or the alkoxy carbonyl with 2 to 20 C atoms, or the aryloxycarbonyl with 7 to 20 C atoms, or cyano (- CN), or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates; or isothiocyanates or hydroxyl or nitro or CF3Or Cl or Br or F or crosslinkable group, Or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms.
- Deuterated fused ring compound according to claim 1, which is characterized in that R13And/or R18Contain one in the structure as shown in the logical formula (II)-(IV).
- - 2 described in any item deuterated fused ring compounds according to claim 1, which is characterized in that there is the structure as shown in general formula (V-1)-(V-3):Wherein,R510-R545It is separately H; or D; or straight chained alkyl, alkoxy or thio alkoxy with 1 to 20 C atom; or branch or cricoid alkyl, alkoxy or thio alkoxy with 3 to 20 C atoms; either substituted or unsubstituted silicyl; or the substituted ketone group with 1 to 20 C atom; or the alkoxy carbonyl with 2 to 20 C atoms; or the aryloxycarbonyl with 7 to 20 C atoms; or cyano (- CN) or carbamoyl (- C (=O) NH2) or halogen formoxyl (- C (=O)-X, wherein X represents halogen atom); or formoxyl (- C (=O)-H) or isocyano group or isocyanates or thiocyanates; or isothiocyanates or hydroxyl or nitro or CF3Or Cl or Br or F, or can The group of crosslinking, or substituted or unsubstituted aromatics or heteroaromatic ring system with 5 to 40 annular atoms, or the combination of aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms;L indicates the combination of singly-bound or the deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms with 5 to 40 annular atoms;Ar3And Ar4It is separately the combination of the deuterated or not deuterated substituted or unsubstituted aromatics or heteroaromatic ring system or the deuterated or not deuterated aryloxy group or heteroaryloxy group or these systems with 5 to 40 annular atoms with 5 to 40 annular atoms;M and n is separately the integer of 0-6.
- Deuterated fused ring compound according to claim 1-3, which is characterized in that the H on the deuterated fused ring compound is at least partly deuterated.
- A kind of high polymer, which is characterized in that its repetitive unit includes that deuterated fused ring compound according to any one of claims 1-4 loses the group formed after at least one hydrogen atom.
- A kind of mixture, it is characterized in that, including deuterated fused ring compound according to any one of claims 1-4 and the second organic functional material, or including high polymer as claimed in claim 5 and the second organic functional material, second organic functional material is 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), singlet emitters (fluorescent illuminant), triplet emitters (phosphorescent emitter), at least one of thermal excitation delayed fluorescence material (TADF material) and organic dyestuff.
- A kind of composition, which is characterized in that including deuterated fused ring compound according to any one of claims 1-4 and organic solvent, or including high polymer as claimed in claim 5 and organic solvent, or including mixture as claimed in claim 6 and organic solvent.
- A kind of organic electronic device, including deuterated fused ring compound according to any one of claims 1-4 or high polymer as claimed in claim 5 or mixture as claimed in claim 6.
- Organic electronic device according to claim 8, it is characterized in that, the organic electronic device is 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 phasmon emitting diode.
- Organic electronic device according to claim 8, which is characterized in that be organic electroluminescence device, including luminescent layer, the luminescent layer includes the deuterated fused ring compound or high polymer or mixture.
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CN113087725B (en) * | 2021-04-06 | 2022-07-22 | 广州追光科技有限公司 | Benzothiadiazole deuterated derivative and application thereof in organic electronic device |
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