CN111848542B - Novel hole transport material - Google Patents
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- CN111848542B CN111848542B CN202010697420.5A CN202010697420A CN111848542B CN 111848542 B CN111848542 B CN 111848542B CN 202010697420 A CN202010697420 A CN 202010697420A CN 111848542 B CN111848542 B CN 111848542B
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- 239000000463 material Substances 0.000 title claims abstract description 25
- 230000005525 hole transport Effects 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 20
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 6
- 238000001514 detection method Methods 0.000 abstract description 5
- 230000005669 field effect Effects 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 120
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 229910052757 nitrogen Inorganic materials 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000010992 reflux Methods 0.000 description 27
- 238000010438 heat treatment Methods 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 17
- 238000005070 sampling Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 12
- 238000010791 quenching Methods 0.000 description 12
- 230000000171 quenching effect Effects 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000011049 filling Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 description 5
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 5
- UUOZYACCZRHIJK-UHFFFAOYSA-N 5-(4-bromophenyl)-1,2,3-trifluorobenzene Chemical group FC1=C(F)C(F)=CC(C=2C=CC(Br)=CC=2)=C1 UUOZYACCZRHIJK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- -1 organofluorine compounds Chemical class 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002991 phenoxazines Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- XTEBLARUAVEBRF-UHFFFAOYSA-N 4-(1,1,1,3,3,3-hexafluoropropan-2-yl)aniline Chemical compound NC1=CC=C(C(C(F)(F)F)C(F)(F)F)C=C1 XTEBLARUAVEBRF-UHFFFAOYSA-N 0.000 description 1
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- GBQZGEGKNCBKLE-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 Chemical compound FC1=CC=C(C=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 GBQZGEGKNCBKLE-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 238000001941 electron spectroscopy Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004407 fluoroaryl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JHEFOJNPLXSWNZ-UHFFFAOYSA-N n-(4-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1 JHEFOJNPLXSWNZ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- UYCAUPASBSROMS-UHFFFAOYSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)F UYCAUPASBSROMS-UHFFFAOYSA-M 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Abstract
The invention discloses a novel hole transport material, which is a compound with a general formula (I),
Description
Technical Field
The invention relates to the technical field of novel organic compounds, which is mainly applied to the fields of Organic Photoconductors (OPCS), organic Light Emitting Diodes (OLED), organic solar cells (OPVCS), organic Field Effect Transistors (OFETS), photoelectric detection, sensors and the like.
Background
Organic electroluminescent devices (OLEDs) have excellent characteristics such as active light emission, high energy efficiency, wide viewing angle, and fast response speed, and particularly have potential application prospects in full-color display and light sources, and have recently been increasingly attracting research interests in the scientific and commercial industries. Of all the elements, fluorine has the greatest electronegativity, and its value is 4, and the bond energy of the C-F bond is 480 kJ.mol-1 due to polarization. In addition, the negative induction Effect (σi=0.51) and the positive conjugation Effect (Mesomeric Effect, σr= -0.34) of fluorine atoms affect not only the reaction properties of organofluorine compounds but also the intramolecular and intermolecular interactions of fluorine compounds. Fluorination can enhance the stability and electron transport properties of materials by lowering the highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) energy levels of the materials, making them bipolar in nature. In addition, the fluorination can change the photophysical property of the material to realize blue shift of the emission peak of the material, and the organic iridium-phenylpyridine complex in the OLED reduces non-radiative decay through fluoro of the ligand, so that the luminous efficiency is improved. The fluorination can reduce the sublimation temperature of the organic material, which is beneficial to the purification of the material. In 2007 Francesco Naso et al summarised the use of fluoro conjugated organic materials with semiconducting properties in OLEDs and Organic Field Effect Transistors (OFETs). The organic conjugated material modified by fluorine atoms, fluoroalkyl groups or fluoroaryl groups can obviously reduce HOMO and LUMO, the low LUMO is beneficial to electron injection, and the work functions of the matched LUMO and the metal cathode can adopt durable aluminum as an electrode. At the same time, hole-electron injection balancing can increase the efficiency of the device. In addition, the reduced HOMO energy level renders the fluoroconjugated organic material less susceptible to oxidative degradation, thus increasing the lifetime of the device to some extent, for N, N '-diphenyl-N, N' -bis (3-methylphenyl) - (1, 1 '-biphenyl) -4,4' -diamine (TPD) type materials the HOMO energy level is adjusted in two ways, (1) the HOMO energy level is increased with electron-donating substituents such as alkoxy and alkyl groups, and the HOMO energy level is reduced with electron-accepting groups such as chlorine, fluorine, CF3 or SO 2; (2) substitution at different positions on the central core of the biphenyl distorts the plane, further lowering the HOMO level by reducing the delocalization of the electrons. By changing the substitution pattern, not only the HOMO level of the material can be adjusted, but also the hole mobility can be changed. The maximum luminous efficiency of the manufactured OLED device with the single hole transmission layer has a certain relation with the HOMO energy level of the material, the maximum efficiency is located at the middle of the HOMO energy levels of PEDOT, PSS and PVK, and the hole injection barrier is divided into two equal parts.
Cornil J et al studied the molecular front-line orbitals of TPD modified with methoxy and F atoms by gas phase UV electron spectroscopy and quantitative calculation, and could change the HOMO energy level of the material by introducing substituent groups on the backbone induced effect, thus adjusting the energy barrier of the metal/organic, organic/organic layer interface.
Disclosure of Invention
The invention aims to improve the defects of the prior art and provide a novel hole transport material which has good hole transport capacity, can effectively prevent the formation of molecular traps and has better chemical and physical stability.
The object of the invention is achieved in that a novel hole transport material is characterized in that the material is a compound having the general formula (I):
Further, R in the compound 1 、R 2 And R is 3 Identical or identicalDifferent, selected from
Further, R in the compound 1 、R 2 And R is 3 Identical or different, selected from
Further, Z and Z in the compound 1 Identical or different, selected from
Or a carbon-carbon single bond.
Further, Z and Z in the compound 1 Identical or different, selected from
Further, the compound is selected from the group consisting of:
due to CF 3 (trifluoromethyl) has strong electron withdrawing property and hydrophobicity, and CF is introduced into organic molecule 3 Can change the acidity, chemical and metabolic stability, lipophilicity and bonding selectivity of the compound obviously. While the invention adopts the electron-accepting group CF 3 Decreasing the HOMO level, thereby changing hole mobility.
Compared with the prior hole transport material TPD, the novel hole transport material containing the double trifluoromethyl substituted phenoxazine groups has better current transport efficiency in the same type of devices. The material can be applied to various fields such as Organic Photoconductors (OPCS), organic electroluminescent diodes (OLED), organic solar cells (OPVCS), organic Field Effect Transistors (OFETS), photoelectric detection, sensors and the like.
Detailed Description
Example 1 preparation of N4- ([ 1,1' -biphenyl ] -4-yl) -N4' - (4- (3, 7-bistrifluoromethyl) -10H-phenoxazin-10-yl) phenyl) -N4, N4' -biphenyl- [1,1' -biphenyl ] -4,4' -diamine having the structure shown in formula I-1,
15.7g of p-chlorobromobenzene, 15.2g of phenoxazine, 0.56g of Pd (OAc) 2, 11.38g of Buona and 800mL of toluene are sequentially added into a 2L four-port bottle, a heating, stirring, refluxing and nitrogen protection device is installed, after 5 times of nitrogen replacement, 19.8g of 10% toluene solution of P (t-Bu) 3 is rapidly added into the bottle by a 25mL syringe, the temperature is raised to 110 ℃ and reflux is carried out for 6-8 hours, sampling and detecting GC, the phenoxazine content is less than 0.5%, the reaction can be stopped, after the nitrogen protection is cooled to room temperature, the mixture is quenched, washed, dried, subjected to column chromatography, desolventized and recrystallized from isopropanol, 16.82g I-1a-2 is obtained, and the yield is 70%.
15g I-1a-2 and 150mL of toluene are added into a 2L four-mouth bottle, an ice bath, stirring, dropwise adding and nitrogen protection device are installed, after nitrogen replacement is carried out for 5 times, the temperature is reduced to 0 ℃ by an ice salt bath, 18g of 450mL of dichloromethane solution of NBS is dropwise added under the protection of nitrogen, the temperature is controlled to 0-5 ℃, the GC is detected by sampling, the content of I-1a-2 is less than 1%, the monobromination content is less than 0.2%, the reaction can be stopped, after the nitrogen protection is cooled to room temperature, the reaction is finished, and the reaction product is obtained through filtration, quenching, washing, drying, column chromatography, desolventizing and methanol recrystallization, so that 19.93g I-1a-1 is obtained, and the yield is 87%.
19.93g of I-1a-1, 57.3g of CF3COONa,81.6g of CuI and 1.2LNMP are sequentially added into a 2L four-mouth bottle, a heating, stirring, refluxing, temperature control and nitrogen protection device are installed, nitrogen is replaced for 5 times, the temperature is raised to 160 ℃ and reflux is carried out for 16-24 hours, sampling and detection are carried out, GC is carried out, the content of I-1a-1 is less than 2%, the monobrominated content is less than 1%, the reaction can be stopped, after the nitrogen protection is cooled to room temperature, the reaction is carried out, and 11.79g I-1a is obtained through filtration, quenching, water washing, drying, column chromatography, desolventizing and n-heptane recrystallization, and the yield is 61.9%.
Into a 5L three-necked flask were successively placed 202g of N, N' -diphenylbiphenyl diamine, 139.2g of bromobiphenyl, 34.3g of CuI, 3.5L of xylene and 90g t-Buona, and a heating stirrer, a thermometer, a bulb condenser, a water separator and a nitrogen gas protection device were installed. And (5) filling nitrogen, evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And continuously separating out low-boiling tertiary butanol in the reflux process, keeping the temperature of the reaction solution at 140-142 ℃ for 36-43h, sampling and detecting HPLC (high performance liquid chromatography), wherein the content of N, N' -diphenyl diamine is less than 5%, terminating the reaction, and obtaining 198.9g I-1b with the yield of 67.9% through filtration, quenching, water washing, drying, column chromatography, desolventizing and methanol recrystallization.
11.79g I-1a, 12.8g I-1b and 3L toluene are added into a 5L three-necked flask, and an oil bath heating and stirring device, a nitrogen protection device, a reflux device and a temperature control device are arranged. The mixture was purged 10 times with nitrogen, 9.23g g t-Buona was added, the oil bath was heated to 60℃and a 10% toluene solution of 0.15g Pd (dba) 2 and 1g t-Bu3P was added under nitrogen (syringe). After the addition, the nitrogen is filled and emptied for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8 hours, the HPLC is sampled and detected, the reaction can be stopped, and the 17.825g I-1 is obtained after filtration, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 77.15%.
Through element analysis: c:76.17%, H:4.21%, F:12.87%, N:4.89%, O:1.89%, substantially in accordance with the theoretical value.
Example 2 Synthesis of N4- ([ 1,1' -biphenyl ] -4-yl) -N4' - (4- (3, 7-bistrifluoromethyl) -10H-phenoxazin-10-yl) phenyl) -N4, N4' -bis (4-fluorophenyl) - [1,1' -biphenyl ] -4,4' -diamine having the structural formula shown in formula I-2,
to a 2L three-necked flask, 61.2g g N-acetyl-4-fluoroaniline, 31g 4,4' -dibromobiphenyl, 38g CuI, 1.2L xylene and 48.05g t-Buona were successively placed, and a heating stirrer, a thermometer, a bulb condenser, a water separator and a nitrogen gas protecting device were installed. And (5) filling nitrogen, evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And continuously separating out low-boiling tertiary butanol in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for reflux for 24-32h, sampling and detecting GC, wherein the content of 4,4' -dibromobiphenyl is less than 0.5 percent, the monobrominated content is less than 0.2 percent, stopping the reaction, and obtaining 30.94g I-2b-2 through filtering, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 67.83 percent.
Into a 1L three-necked flask, 30.94g g I-2b-2, 42g of potassium hydroxide and 500ml of ethanol were successively placed, and a heating stirrer, a thermometer, a bulb-shaped condenser and a nitrogen protection device were installed. And (3) filling nitrogen, evacuating for about 10 times, slowly heating and refluxing under the protection of nitrogen, keeping the temperature of the reaction liquid at 75-80 ℃ for 24-32h, sampling and detecting GC, wherein the content of I-2b-2 is less than 0.05%, the content of monoacetyl is less than 0.1%, terminating the reaction, and obtaining 24.56g I-2b-2 by distillation, filtration, column chromatography, desolventizing and toluene recrystallization, wherein the yield is 97.3%.
Into a 2L three-necked flask, 24.56g g I-2b-2, 30.6g bromodiphenyl oxide, 2.5g CuI, 3.5L xylene and 16g t-Buona were successively placed, and a heating stirrer, a thermometer, a bulb condenser, a water separator and a nitrogen gas protection device were installed. And (5) filling nitrogen, evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And continuously separating out low-boiling tertiary butanol in the reflux process, keeping the temperature of the reaction solution at 140-142 ℃ for 36-43h, sampling and detecting HPLC, wherein the content of I-2b-1 is less than 0.2%, terminating the reaction, and obtaining 26.5g I-2b with the yield of 76.5% through filtration, quenching, water washing, drying, column chromatography, desolventizing and methanol recrystallization.
26. 26g I-1a, 26.5g I-2b and 3L toluene are added into a 5L three-necked flask, and an oil bath heating and stirring device, a nitrogen protection device, a reflux device and a temperature control device are arranged. The mixture was purged 10 times with nitrogen, 7.3. 7.3g t-Buona was added, the oil bath was heated to 60℃and a 10% toluene solution of 0.15g Pd (dba) 2 and 1g t-Bu3P (taken by syringe) was added under nitrogen. After the addition, the nitrogen is filled and emptied for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8 hours, the HPLC is sampled and detected, the reaction can be stopped, and the yield is 81.6 percent through filtration, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization.
Through element analysis: c:73.15%, H:3.87%, F:16.47%, N:4.72%, O:1.83%, substantially in accordance with the theoretical value.
Example 3 Synthesis of N4- (4- (3, 7-bistrifluoromethyl-10H-phenoxazin-10-yl) phenyl) -N4, N4 '-bis (4-fluorophenyl) -N4' - (3 ',4',5 '-trifluoro- [1,1' -biphenyl ] -4-yl) - [1, 1'-biphenyl ] -4,4' -diamine having the structure shown in formula I-3,
4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl was synthesized with reference Journal of Organometallic Chemistry,2019, vol.883, p.78-85.
Synthesis of 37.7g of 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl in place of 30.6g of bromobiphenyl in example 2 gave 25.5g I-3b in 66.8% yield.
26g I-1a, 25.5g I-3b and 3L toluene are added into a 5L three-necked flask, and an oil bath heating and stirring device, a nitrogen protection device, a reflux device and a temperature control device are arranged. The mixture was purged 10 times with nitrogen, 7.3. 7.3g t-Buona was added, the oil bath was heated to 60℃and a 10% toluene solution of 0.15g Pd (dba) 2 and 1g t-Bu3P (taken by syringe) was added under nitrogen. After the addition, the nitrogen is filled and emptied for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8 hours, the HPLC is sampled and detected, the reaction can be stopped, and 35.8g of I-3 is obtained after filtration, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 83.7%.
Through element analysis: c:69.17%, H:3.29%, F:21.63%, N:4.92%, O:1.72%, substantially in accordance with the theoretical value.
Example 6, N 1 - (4- (3, 7-bistrifluoromethyl) -10H-phenoxazin-10-yl) phenyl) -N 1 - (4- (1, 3-hexafluoro-2- (4- ((3 ',4',5 '-trifluoro- [1,1' -biphenyl))]-4-yl) (4-trifluoromethylphenyl l) amino) phenyl l) propan-2-yl) phenyl) -N 4 ,N 4 The synthesis of the bis (4-trifluoromethyl phenyl) benzene-1, 4-diamine has the structural formula shown in the general formula I-10,
1500g of trifluoromethyl bromobenzene, 166.2g of aniline and 1.5L of xylene are placed in a 5L three-necked flask, and an oil bath is installed for heating and stirring, nitrogen protection, reflux and temperature control. The mixture was purged 10 times with nitrogen, 430g t-Buona was added, the oil bath was heated to 60℃and 5g of Pd (dba) 2 and 50g t-Bu3P in 10% toluene (taken by syringe) under nitrogen. After the addition, the nitrogen is filled and emptied for 8 times, low-boiling tertiary butanol is continuously separated in the reflux process, the temperature of the reaction liquid is kept at 140-142 ℃ for reflux for 26-32 hours, sampling and detecting GC, trifluoromethyl bromobenzene is less than 0.2%, diarylamine is less than 0.5%, the reaction can be stopped, xylene and trifluoromethyl bromobenzene are recovered under reduced pressure, n-heptane is added for filtration, quenching, water washing, drying, column chromatography, desolventizing and isopropanol recrystallization are carried out, and 111.6g I-10b-6 is obtained, and the yield is 73.2%.
111.6g I-10b-6 and 1LmL methylene dichloride are added into a 5L three-port bottle, an ice bath is arranged, stirring, dropwise adding and a nitrogen protection device are arranged, after nitrogen replacement is carried out for 5 times, an ice salt bath is cooled to 0 ℃, 60g of NBS 1L methylene dichloride solution is dropwise added under the protection of nitrogen, the temperature is controlled to 0-5 ℃, sampling and detecting GC is carried out, the content of I-10b-6 is less than 1%, the monobromination content is less than 0.2%, the reaction can be stopped, after the nitrogen protection is cooled to room temperature, the reaction is finished, and then the reaction product is obtained through filtration, quenching, washing, drying, column chromatography, desolventizing and methanol recrystallization, so that 123g I-10b-5 is obtained, and the yield is 91.5%.
Into a 5L three-necked flask, 500g of 2, 2-bis (4-aminophenyl) hexafluoropropane and 2500ml of acetic anhydride were successively placed, and a heating stirrer, a thermometer, a bulb condenser and a nitrogen gas protecting device were installed. And (3) filling nitrogen, evacuating for about 10 times, slowly heating and refluxing for 36-45h under the protection of nitrogen, sampling and detecting that the GC, 2-bis (4-aminophenyl) hexafluoropropane content is less than 0.05 percent and the monoacetyl content is less than 0.1 percent, terminating the reaction, and obtaining 610.4g I-10b-4 by distillation, filtration, column chromatography, desolventizing and isopropanol recrystallization, wherein the yield is 97.6 percent.
Into a 5L three-necked flask were successively placed 209g g I-10b-4, 112g of trifluoromethyl bromobenzene, 9.5g of CuI, 2.5L of xylene and 69g of anhydrous potassium carbonate, and a heating stirrer, a thermometer, a spherical condenser, a water separator and a nitrogen protection device were installed. And (5) filling nitrogen, evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And continuously separating out low-boiling tertiary butanol in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for 20-26h, sampling and detecting GC, and stopping the reaction after the content of trifluoromethyl bromobenzene is less than 2%, and obtaining 189.2g I-10b-3 with the yield of 67.3 percent through filtration, column chromatography, desolventizing and isopropanol recrystallization.
143g I-10b-3, 123g I-10b-5 and 3L toluene were added to a 5L three-necked flask, and an oil bath heating and stirring apparatus, nitrogen protection, reflux and temperature control apparatus were installed. The mixture was purged 10 times with nitrogen, 38.6g t-Buona was added, the oil bath was heated to 60℃and a 10% toluene solution of 0.5g Pd (dba) 2 and 6g t-Bu3P (taken by syringe) was added under nitrogen. After the addition, the nitrogen is filled and emptied for 8 times, the temperature is controlled to be 80-85 ℃ for 20-28 hours, the HPLC is sampled and detected, the reaction can be stopped, and 183.3g I-10b-2 is obtained after filtration, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 76.5%.
Into a 5L three-necked flask, 183.3-g I-10b-2, 80g of potassium hydroxide and 2500ml of ethanol were successively placed, and a heating stirrer, a thermometer, a bulb-shaped condenser and a nitrogen protection device were installed. And (3) filling nitrogen, evacuating for about 10 times, slowly heating and refluxing under the protection of nitrogen, keeping the temperature of the reaction liquid at 75-80 ℃ for 50-60h, sampling and detecting HPLC, wherein the content of I-10b-2 is less than 0.05%, the content of monoacetyl is less than 0.1%, terminating the reaction, and obtaining 156.55g I-10b-1 with the yield of 93.8% through distillation, filtration, column chromatography, desolventizing and toluene recrystallization.
Into a 5L three-necked flask were successively 156.55g I-10b-1, 112g of 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl, 5g of CuI, 2.5L of xylene and 27.8g of anhydrous potassium carbonate, and a heating stirrer, a thermometer, a spherical condenser, a water separator and a nitrogen protection device were mounted. And (5) filling nitrogen, evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. Continuously separating out low-boiling tertiary butanol in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for reflux for 32-38h, sampling and detecting HPLC, wherein the content of 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl is less than 1%, terminating the reaction, and obtaining 136.9g I-10b with the yield of 70.5% through filtration, column chromatography, desolventizing and toluene recrystallization.
26-g I-1a, 58.58g I-10b and 3L toluene are added into a 5L three-necked flask, and an oil bath heating and stirring device, a nitrogen protection device, a reflux device and a temperature control device are arranged. The mixture was purged 10 times with nitrogen, 7.3. 7.3g t-Buona was added, the oil bath was heated to 60℃and a 10% toluene solution of 0.15g Pd (dba) 2 and 1g t-Bu3P (taken by syringe) was added under nitrogen. After the addition, the nitrogen is filled and emptied for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8 hours, the HPLC is sampled and detected, the reaction can be stopped, and the 64.35g I-3 is obtained after filtration, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 80.2%.
Through elemental analysis, C is 61.05%, H is 2.76%, F is 31.16%; 3.96 percent of N; o is 1.18%, which is basically consistent with the theoretical value.
Example 7 ITO/TPD (60 nm)/Alq 3 (60 nm)/Li F (1 nm)/Al (70 nm) devices, HTMs were TPD, alq3 as the electron transporting and light emitting layer, maximum current efficiency was measured to be 2.41 cd.A -1 。
Example 8 ITO/I-1 (60 nm)/Alq 3 (60 nm)/Li F (1 nm)/Al (70 nm) devices with HTMs of I-1 and Alq3 as electron transporting and light emitting layers, maximum current efficiency of 4.3 cd.A was measured -1 。
Example 9 ITO/I-2 (60 nm)/Alq 3 (60 nm)/Li F (1 nm)/Al (70 nm) devices with HTMs of I-2 and Alq3 as electron transporting and light emitting layers, maximum current efficiency of 4.5 cd.A was measured -1 。
Example 10 ITO/I-3 (60 nm)/Alq 3 (60 nm)/Li F (1 nm)/Al (70 nm) devices with HTMs of I-3 and Alq3 as electron transporting and emitting layers, maximum current efficiency of 4.8 cd.A was measured -1 。
Example 11 ITO/I-5 (60 nm)/Alq 3 (60 nm)/Li F (1 nm)/Al (70 nm) devices with HTMs of I-5 and Alq3 as electron transporting and light emitting layers, maximum current efficiency of 4.6 cd.A was measured -1 。
Example 12 ITO/I-10 (60 nm)/Alq 3 (60 nm)/Li F (1 nm)/Al (70 nm) devices with HTMs of I-10 and Alq3 as the electron transporting and emitting layer, maximum current efficiency of 4.8 cd.A was measured -1 。
By comparing examples 8, 9, 10, 11 and 12 with example 7, it can be obtained that the novel hole transport material containing the bistrifluoromethyl-substituted phenoxazine group is designed, and has better current transport efficiency in the same type of device compared with the prior hole transport material TPD.
The material can be applied to various fields such as Organic Photoconductors (OPCS), organic electroluminescent diodes (OLED), organic solar cells (OPVCS), organic Field Effect Transistors (OFETS), photoelectric detection, sensors and the like.
Claims (2)
1. A novel hole transport material characterized in that it is a compound having the general formula (i):
2. The novel hole transport material of claim 1, wherein said compound is selected from the group consisting of:
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06220447A (en) * | 1992-03-27 | 1994-08-09 | Pioneer Electron Corp | Organic electroluminescent device |
| JPH11154594A (en) * | 1997-11-20 | 1999-06-08 | Mitsui Chem Inc | Organic electroluminescent element |
| KR20130113115A (en) * | 2012-04-05 | 2013-10-15 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| CN105367595A (en) * | 2015-11-06 | 2016-03-02 | 莱阳市盛华科技有限公司 | Electroluminescent hole-transporting material and preparation method thereof |
| CN110218185A (en) * | 2018-03-01 | 2019-09-10 | 机光科技股份有限公司 | Heteroaromatics and the organic EL component for using it |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06220447A (en) * | 1992-03-27 | 1994-08-09 | Pioneer Electron Corp | Organic electroluminescent device |
| JPH11154594A (en) * | 1997-11-20 | 1999-06-08 | Mitsui Chem Inc | Organic electroluminescent element |
| KR20130113115A (en) * | 2012-04-05 | 2013-10-15 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| CN105367595A (en) * | 2015-11-06 | 2016-03-02 | 莱阳市盛华科技有限公司 | Electroluminescent hole-transporting material and preparation method thereof |
| CN110218185A (en) * | 2018-03-01 | 2019-09-10 | 机光科技股份有限公司 | Heteroaromatics and the organic EL component for using it |
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