CN111848542A - Novel hole transport material - Google Patents
Novel hole transport material Download PDFInfo
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- CN111848542A CN111848542A CN202010697420.5A CN202010697420A CN111848542A CN 111848542 A CN111848542 A CN 111848542A CN 202010697420 A CN202010697420 A CN 202010697420A CN 111848542 A CN111848542 A CN 111848542A
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- 239000000463 material Substances 0.000 title claims abstract description 28
- 230000005525 hole transport Effects 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 23
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 230000005669 field effect Effects 0.000 abstract description 5
- 238000001514 detection method Methods 0.000 abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 4
- 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
- 230000005540 biological transmission Effects 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
- 238000010992 reflux Methods 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000010438 heat treatment Methods 0.000 description 25
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- 238000005070 sampling Methods 0.000 description 18
- 238000001914 filtration Methods 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- 238000003756 stirring 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
- 238000010791 quenching Methods 0.000 description 12
- 230000000171 quenching effect Effects 0.000 description 12
- 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 12
- 238000005406 washing Methods 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000011049 filling Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer 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
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- 239000000243 solution Substances 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
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 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
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 238000003682 fluorination reaction 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
- 230000001012 protector Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation 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
- 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
- -1 4- (3, 7-bis-trifluoromethyl-10H-phenoxazin-10-yl) phenyl Chemical group 0.000 description 2
- 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 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
- 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
- 230000008859 change Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 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
- 238000002360 preparation method Methods 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
- FJATXOTUCMTUJI-UHFFFAOYSA-N 1-n,2-n,3-triphenylbenzene-1,2-diamine Chemical compound C=1C=CC(C=2C=CC=CC=2)=C(NC=2C=CC=CC=2)C=1NC1=CC=CC=C1 FJATXOTUCMTUJI-UHFFFAOYSA-N 0.000 description 1
- UMZHRNWFDBZQLC-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2C=CC(=CC=2)C(F)(F)F)=C1 UMZHRNWFDBZQLC-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241001274216 Naso Species 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
- 239000004305 biphenyl Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000005266 diarylamine group Chemical group 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
- 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
- 150000002991 phenoxazines Chemical group 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
Classifications
-
- 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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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- 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
- 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
- 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
- H10K85/60—Organic compounds having low molecular weight
- 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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- Engineering & Computer Science (AREA)
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- Optics & Photonics (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 are mainly applied to the fields of Organic Photoconductors (OPCS), organic electroluminescent diodes (OLED), organic solar cells (OPVCS), Organic Field Effect Transistors (OFETS), photoelectric detection, sensors and the like.
Background
Organic electroluminescent devices (OLEDs) have many excellent characteristics such as active light emission, high energy efficiency, wide viewing angle, and fast response speed, and especially have potential application prospects in full-color display and light sources, and have been increasingly attracting research interests in the scientific and commercial fields in recent years. Among all elements, fluorine has the greatest electronegativity with a value of 4, and the bond energy of the C-F bond is 480 kJ. mol-1 due to polarization. In addition, the negative induction Effect (In-reactive Effect, σ I ═ 0.51) and the positive conjugation Effect (Mesomeric Effect, σ R ═ 0.34) of fluorine atoms affect not only the reaction properties of the organofluorine compound, but also the intramolecular and intermolecular interactions of the fluorine compound. Fluorination can enhance the stability and electron transport properties of materials by lowering their Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energy levels, giving them bipolar transport properties. In addition, the fluorination can change the photophysical characteristics of the material to realize the blue shift of the emission peak of the material, and the organic iridium-phenylpyridine complex in the OLED reduces the non-radiative decay by the fluorination of the ligand, thereby improving the luminous efficiency. Fluorination can lower the sublimation temperature of the organic material and is beneficial to the purification of the material. In 2007, France co Naso et al concluded the use of fluorinated conjugated organic materials with semiconducting properties in OLEDs and Organic Field Effect Transistors (OFETs). The fluorine atom, fluoroalkyl or fluoroaryl modified organic conjugated material can significantly reduce HOMO and LUMO, the low LUMO is beneficial to electron injection, and the work function of the matched LUMO and a metal cathode can adopt durable aluminum as an electrode. At the same time, the hole-electron injection balance can increase the efficiency of the device. In addition, the reduced HOMO energy level enables the fluorinated conjugated organic material not to be easily oxidized and degraded, SO that the service life of the device is prolonged to a certain extent, and for N, N '-diphenyl-N, N' -bis (3-methylphenenyl) - (1, 1'-biphenyl) -4, 4' -diamine (TPD) materials, the HOMO energy level is adjusted in two ways, namely firstly, the HOMO energy level is increased by adopting electron-donating substituents (such as alkoxy and alkyl), and the HOMO energy level is reduced by electron-accepting groups (such as chlorine, fluorine, CF3 or SO 2); ② the plane is distorted by the substitution of different positions on the central nucleus of biphenyl, and the HOMO energy level is further reduced because the delocalization of electrons is reduced. 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 OLED device with the single hole transport layer has a certain relation with the HOMO energy level of the material, the maximum efficiency is just positioned in the middle of the HOMO energy levels of PEDOT, PSS and PVK, and the hole injection barrier is divided into two parts with the same quantity.
Cornil J et al studied the molecular front orbitals of TPD modified with methoxy and F atoms by means of gas-phase ultraviolet photoelectron spectroscopy and quantitative calculation, and the HOMO energy level of the material can be changed by introducing the induction effect of substituent groups on the skeleton, so that the energy barrier of the metal/organic, organic/organic layer interface can be adjusted.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a novel hole transport material which has good hole transport capability, can effectively prevent the formation of molecular traps and has better chemical and physical stability.
The object of the present invention is achieved by a novel hole transport material, characterized in that the material is a compound having the general formula (I):
Further, R in the compound1、R2And R3Same or different, are selected from
Further, R in the compound1、R2And R3Same or different, are selected from
Further, Z and Z in the compound1Same or different, are selected from
Or a carbon-carbon single bond.
Further, Z and Z in the compound1Same or different, are selected from
Further, the compound is selected from the group consisting of:
Due to CF3(trifluoromethyl) has strong electron withdrawing property and hydrophobicity, and CF is introduced into organic molecules3Can obviously change the acidity, chemical and metabolic stability, lipophilicity and bonding selectivity of the compound. The invention adopts electron-accepting group CF3The HOMO energy level is lowered, thereby changing the hole mobility.
Compared with the conventional hole transport material TPD, the novel hole transport material containing the bis-trifluoromethyl substituted phenoxazine group has better current transport efficiency in devices of the same type. The material can be applied to various fields such as Organic Photoconductors (OPCS), organic light-emitting 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, the structure of which is shown in general formula I-1,
adding 15.7g of p-chlorobromobenzene, 15.2g of phenoxazine, 0.56g of Pd (OAc)2, 11.38gt-BuONa and 800mL of toluene in a 2L four-mouth bottle in sequence, installing a heating, stirring, refluxing, temperature control and nitrogen protection device, after nitrogen replacement is carried out for 5 times, quickly adding 19.8g of P (t-Bu)3 10% toluene solution by using a 25mL injector, heating to 110 ℃ and refluxing for 6-8 h, sampling and detecting GC, stopping the reaction when the phenoxazine content is less than 0.5%, cooling to room temperature under the protection of nitrogen, quenching, washing with water, drying, column chromatography, desolventizing, and recrystallizing with isopropanol to obtain 16.82g I-1a-2 with the yield of 70%.
Adding 15g I-1a-2 and 150mL of toluene into a 2L four-mouth bottle, installing an ice bath, stirring, dropwise adding, controlling the temperature and a nitrogen protection device, after 5 times of nitrogen replacement, cooling the ice salt bath to 0 ℃, dropwise adding 450mL of dichloromethane solution of 18g of NBS under the protection of nitrogen, controlling the temperature to 0-5 ℃, sampling and detecting GC, stopping the reaction until the content of I-1a-2 is less than 1% and the monobromo content is less than 0.2%, cooling to room temperature under the protection of nitrogen, filtering, quenching, washing with water, drying, carrying out column chromatography, desolventizing, and recrystallizing with methanol to obtain 19.93g I-1a-1 with the yield of 87%.
19.93g of I-1a-1, 57.3g of CF3COONa, 81.6g of CuI and 1.2 g of LNMP are sequentially added into a 2L four-mouth bottle, a heating, stirring, refluxing, temperature control and nitrogen protection device is installed, after nitrogen replacement is carried out for 5 times, the temperature is raised to 160 ℃ and refluxed for 16-24 hours, the reaction can be stopped after sampling and detecting GC, the content of I-1a-1 is less than 2 percent and the monobromo content is less than 1 percent, after the nitrogen protection is cooled to room temperature, the reaction is filtered, quenched, washed with water, dried, subjected to column chromatography, desolventization and n-heptane recrystallization to obtain 11.79g I-1a, and the yield is 61.9 percent.
202g N g of N' -diphenyl-biphenyldiamine, 139.2g of bromobiphenyl, 34.3g of CuI, 3.5L of xylene and 90g t-BuONa were placed in a 5L three-necked flask in this order, and a heating stirrer, a thermometer, a spherical condenser tube, a water separator and a nitrogen gas protector were installed. Filling nitrogen and evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And (3) continuously separating tert-butyl alcohol with low boiling point in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for reflux for 36-43h, sampling and detecting HPLC, stopping the reaction when the content of the N, N' -diphenyl-biphenyldiamine is less than 5%, filtering, quenching, washing with water, drying, performing column chromatography, desolventizing and recrystallizing with methanol to obtain 198.9g I-1b, wherein the yield is 67.9%.
11.79g I-1a, 12.8g I-1b and 3L of toluene are added into a 5L three-neck flask, and an oil bath heating stirring device, a nitrogen protection device, a reflux device and a temperature control device are installed. After 10 nitrogen purges, 9.23g t-BuONa was added, the oil bath was heated to 60 ℃ and 0.15g of Pd (dba)2 and 1g t-Bu3P in 10% toluene (taken up by syringe) were added under nitrogen. After the addition, nitrogen is filled for emptying for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8h, the reaction can be stopped when the I-1b is less than 0.2 percent by sampling and detecting HPLC, and 17.825g I-1 is obtained by filtering, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 77.15 percent.
By element analysis: c: 76.17%, H: 4.21%, F: 12.87%, N: 4.89%, O: 1.89%, which is substantially in accordance with the theoretical value.
Example 2, a 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 a structural formula shown in formula I-2,
61.2g N-acetyl-4-fluoroaniline, 31g of 4,4' -dibromobiphenyl, 38g of CuI, 1.2L of xylene and 48.05g t-BuONa were placed in a 2L three-necked flask in this order, and a heating stirrer, a thermometer, a spherical condenser tube, a water separator and a nitrogen gas protector were installed. Filling nitrogen and evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And (3) continuously separating out the tert-butyl alcohol with low boiling point in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for refluxing for 24-32h, sampling and detecting that the content of the 4,4' -dibromobiphenyl is less than 0.5 percent and the content of the monobromo is less than 0.2 percent, then terminating the reaction, and obtaining 30.94g I-2b-2 with the yield of 67.83 percent through filtering, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization.
30.94g I-2b-2, 42g potassium hydroxide and 500ml ethanol were put into a 1L three-necked flask in this order, and a heating and stirring device, a thermometer, a bulb condenser tube and a nitrogen gas protector were installed. Filling nitrogen and evacuating for about 10 times, slowly heating and refluxing under the protection of nitrogen, maintaining the temperature of the reaction solution at 75-80 ℃ and refluxing for 24-32h, sampling and detecting GC, stopping the reaction when the content of I-2b-2 is less than 0.05 percent and the content of monoacetyl is less than 0.1 percent, and obtaining 24.56g I-2b-2 by distillation, filtration, column chromatography, desolventization and toluene recrystallization, wherein the yield is 97.3 percent.
A2L three-necked flask is sequentially filled with 24.56g I-2b-2 g, 30.6g of brominated biphenyl, 2.5g of CuI, 3.5L of dimethylbenzene and 16gt-BuONa, and a heating stirrer, a thermometer, a spherical condenser, a water separator and a nitrogen protection device are arranged. Filling nitrogen and evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And (3) continuously separating the low-boiling-point tert-butyl alcohol in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for reflux for 36-43h, sampling and detecting HPLC, stopping the reaction when the content of I-2b-1 is less than 0.2%, and obtaining 26.5g I-2b through filtration, quenching, water washing, drying, column chromatography, desolventizing and methanol recrystallization, wherein the yield is 76.5%.
26g I-1a, 26.5g I-2b and 3L toluene are added into a 5L three-neck flask, and an oil bath heating stirring device, a nitrogen protection device, a reflux device and a temperature control device are installed. After 10 nitrogen purges, 7.3g t-BuONa was added, the oil bath was heated to 60 ℃ and 0.15g of Pd (dba)2 and 1g t-Bu3P in 10% toluene (taken in by syringe) were added under nitrogen. After the addition, nitrogen is filled for emptying for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8h, the reaction can be stopped when the I-2b is less than 0.2 percent by sampling and detecting HPLC, and 37.8g I-2 is obtained by filtering, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 81.6 percent.
By element analysis: c: 73.15%, H: 3.87%, F: 16.47%, N: 4.72%, O: 1.83%, which is substantially in accordance with the theoretical value.
Example 3 Synthesis of N4- (4- (3, 7-bis-trifluoromethyl-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, the structure of which is shown in formula I-3,
4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl was synthesized with reference to Journal of Organometallic Chemistry, 2019, vol.883, p.78-85.
The synthesis using 37.7g of 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl instead 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-neck flask, and an oil bath heating stirring device, a nitrogen protection device, a reflux device and a temperature control device are installed. After 10 nitrogen purges, 7.3g t-BuONa was added, the oil bath was heated to 60 ℃ and 0.15g of Pd (dba)2 and 1g t-Bu3P in 10% toluene (taken in by syringe) were added under nitrogen. After the addition, nitrogen is filled for emptying for 8 times, the temperature is controlled to be 80-85 ℃ for reaction for 5-8h, the reaction can be stopped when the I-2b is less than 0.2 percent by sampling and detecting HPLC, and 35.8g of I-3 is obtained by filtering, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 83.7 percent.
By element analysis: c: 69.17%, H: 3.29%, F: 21.63%, N: 4.92%, O: 1.72%, which is substantially in accordance with the theoretical value.
Example 6A preparation of N1- (4- (3, 7-bistrifluoromethyl) -10H-phenoxazin-10-yl) phenyl) -N1- (4- (1,1,1,3,3, 3-hexafluoro-2- (4- ((3',4',5 '-trifluoro- [1,1' -biphenyl)]-4-yl) (4-trifluoromethylphenyl l) amino) phenyl l) propan-2-yl) phenyl) -N4,N4The synthesis of the (4-trifluoromethyl phenyl) benzene-1, 4-diamine with the structural formula as shown in the general formula I-10,
1500g of trifluoromethyl bromobenzene, 166.2g of aniline and 1.5L of xylene are added into a three-neck flask with 5L, and an oil bath heating stirring device, a nitrogen protection device, a reflux device and a temperature control device are installed. After 10 nitrogen purges, 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 in by syringe) were added under nitrogen. After the addition, nitrogen is filled for emptying for 8 times, tert-butyl alcohol with low boiling point is continuously separated out in the reflux process, the temperature of the reaction liquid is kept at 140 ℃ and 142 ℃ for reflux for 26-32h, sampling and detecting GC, the trifluoromethyl bromobenzene is less than 0.2 percent, the diarylamine is less than 0.5 percent, the reaction can be stopped, the dimethylbenzene and the trifluoromethyl bromobenzene are recovered under reduced pressure, n-heptane is supplemented for filtering, quenching, water washing, drying, column chromatography, desolventization and isopropanol recrystallization are carried out, 111.6g I-10b-6 is obtained, and the yield is 73.2 percent.
Adding 111.6g I-10b-6 and 1LmL dichloromethane into a 5L three-necked bottle, installing an ice bath, stirring, dropwise adding, controlling the temperature and a nitrogen protection device, after 5 times of nitrogen replacement, cooling the ice salt bath to 0 ℃, dropwise adding 60g of 1L dichloromethane solution of NBS under the protection of nitrogen, controlling the temperature to be 0-5 ℃, sampling and detecting GC, stopping the reaction until the content of I-10b-6 is less than 1% and the monobromo content is less than 0.2%, cooling to room temperature under the protection of nitrogen, filtering, quenching, washing with water, drying, performing column chromatography, desolventizing, and recrystallizing with methanol to obtain 123g I-10b-5, wherein the yield is 91.5%.
Into a 5L three-necked flask were placed 500g of 2, 2-bis (4-aminophenyl) hexafluoropropane and 2500ml of acetic anhydride in this order, followed by heating and stirring, a thermometer, a spherical condenser tube and a nitrogen blanket. Filling nitrogen and evacuating for about 10 times, slowly heating and refluxing for 36-45h under the protection of nitrogen, sampling and detecting GC, wherein the content of 2, 2-bis (4-aminophenyl) hexafluoropropane is less than 0.05 percent, the content of monoacetyl is less than 0.1 percent, then terminating the reaction, and obtaining 610.4g I-10b-4 by distillation, filtration, column chromatography, desolventization and isopropanol recrystallization, and the yield is 97.6 percent.
A5L three-necked flask is sequentially filled with 209g I-10b-4, 112g of trifluoromethyl bromobenzene, 9.5g of CuI, 2.5L of dimethylbenzene and 69g of anhydrous potassium carbonate, and is provided with a heating stirrer, a thermometer, a spherical condenser tube, a water separator and a nitrogen protection device. Filling nitrogen and evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And (3) continuously separating out the tert-butyl alcohol with low boiling point in the reflux process, keeping the temperature of the reaction solution at 140-142 ℃ for refluxing for 20-26h, sampling and detecting GC, stopping the reaction when the content of the trifluoromethyl bromobenzene is less than 2%, and obtaining 189.2g I-10b-3 through filtration, column chromatography, desolventization and isopropanol recrystallization, wherein the yield is 67.3%.
143g I-10b-3, 123g I-10b-5 and 3L toluene are added into a 5L three-neck flask, and an oil bath heating stirring device, a nitrogen protection device, a reflux device and a temperature control device are installed. After 10 nitrogen purges, 38.6g t-BuONa was added, the oil bath was heated to 60 ℃ and 0.5g of Pd (dba)2 and 6g t-Bu3P in 10% toluene (taken in by syringe) were added under nitrogen. After the addition, nitrogen is filled for emptying for 8 times, the temperature is controlled to be between 80 and 85 ℃, the reaction lasts for 20 to 28 hours, the reaction is stopped when the I-10b-3 is less than 0.05 percent by sampling and detecting HPLC, and 183.3g I-10b-2 is obtained by filtering, quenching, washing with water, drying, column chromatography, desolventizing and toluene recrystallization, and the yield is 76.5 percent.
183.3g I-10b-2, 80g of potassium hydroxide and 2500ml of ethanol were placed in a 5L three-necked flask in this order, and a heating and stirring device, a thermometer, a bulb condenser and a nitrogen gas protector were installed. Filling nitrogen and evacuating for about 10 times, slowly heating and refluxing under the protection of nitrogen, keeping the temperature of the reaction solution at 75-80 ℃ and refluxing for 50-60h, sampling and detecting HPLC, stopping the reaction until the content of I-10b-2 is less than 0.05 percent and the content of monoacetyl is less than 0.1 percent, and obtaining 156.55g I-10b-1 by distillation, filtration, column chromatography, desolventization and toluene recrystallization, wherein the yield is 93.8 percent.
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 are sequentially placed in a 5L three-necked flask, and a heating stirrer, a thermometer, a spherical condenser tube, a water separator and a nitrogen protection device are installed. Filling nitrogen and evacuating for about 10 times, and slowly heating and refluxing under the protection of nitrogen. And (2) continuously separating the low-boiling-point tert-butyl alcohol in the reflux process, keeping the temperature of the reaction liquid at 140-142 ℃ for refluxing for 32-38h, sampling and detecting HPLC, wherein the content of 4 '-bromo-3, 4, 5-trifluoro-1, 1' -biphenyl is less than 1%, then terminating the reaction, and obtaining 136.9g I-10b through filtration, column chromatography, desolventization and toluene recrystallization, wherein the yield is 70.5%.
26g I-1a, 58.58g I-10b and 3L of toluene are added into a 5L three-neck flask, and an oil bath heating stirring device, a nitrogen protection device, a reflux device and a temperature control device are installed. After 10 nitrogen purges, 7.3g t-BuONa was added, the oil bath was heated to 60 ℃ and 0.15g of Pd (dba)2 and 1g t-Bu3P in 10% toluene (taken in by syringe) were added under nitrogen. After the addition, nitrogen is filled for emptying for 8 times, the temperature is controlled to be between 80 and 85 ℃, the reaction is carried out for 5 to 8 hours, the reaction is stopped when the I-10b is less than 0.2 percent by sampling and detecting HPLC, and the reaction is finished after filtration, quenching, water washing, drying, column chromatography, desolventizing and toluene recrystallization, 64.35g I-3 is obtained, and the yield is 80.2 percent.
By element analysis, C is 61.05 percent, H is 2.76 percent, and F is 31.16 percent; 3.96 percent of N; 1.18% of O, which is substantially in accordance with the theoretical value.
Example 7 an ITO/TPD (60nm)/Alq3(60nm)/Li F (1nm)/Al (70nm) device, HTMs being TPD, Alq3 as electron transporting and light emitting layer, was found to have a maximum current efficiency of 2.41 cd.A-1。
Example 8 an ITO/I-1(60nm)/Alq3(60nm)/Li F (1nm)/Al (70nm) device having HTMs of I-1 and Alq3 as the electron transporting and light emitting layer and having a maximum current efficiency of 4.3 cd. A-1。
Example 9 ITO/I-2(60nm)/Alq3(60nm)/Li F (1nm)/Al (70nm) devices having HTMs of I-2 and Alq3 as the electron transporting and light emitting layer, the maximum current efficiency was measured to be 4.5 cd. A -1。
Example 10 ITO/I-3(60nm)/Alq3(60nm)/Li F (1nm)/Al (70nm) devices having HTMs of I-3 and Alq3 as the electron transporting and light-emitting layer, the maximum current efficiency was measured to be 4.8 cd. A-1。
Example 11 ITO/I-5(60nm)/Alq3(60nm)/Li F (1nm)/Al (70nm) devices having HTMs of I-5 and Alq3 as the electron transporting and light-emitting layer, the maximum current efficiency measured was 4.6 cd. A-1。
Example 12 ITO/I-10(60nm)/Alq3(60nm)/Li F (1nm)/Al (70nm) devices having HTMs of I-10 and Alq3 as the electron transporting and light-emitting layer, the maximum current efficiency measured was 4.8 cd. A-1。
By comparing examples 8, 9, 10, 11 and 12 with example 7, it can be seen that the novel hole transport material containing bis-trifluoromethyl-substituted phenoxazinyl group designed by the invention has better current transport efficiency in the same type of device compared with the existing hole transport material TPD.
The material can be applied to various fields such as Organic Photoconductors (OPCS), organic light-emitting diodes (OLED), organic solar cells (OPVCS), Organic Field Effect Transistors (OFETS), photoelectric detection, sensors and the like.
Claims (6)
1. A novel hole transport material, characterized in that it is a compound having the general formula (i):
Z and Z1Same or different, are selected from
2. A novel hole transporting material according to claim 1, wherein R in said compound is1、R2And R3Same or different, are selected from
3. A novel hole transporting material according to claim 2, wherein R in said compound is1、R2And R3Same or different, are selected from
4. A novel hole transporting material according to claim 1, wherein Z and Z in said compound are1Same or different, are selected from
Or a carbon-carbon single bond.
5. A novel hole transporting material according to claim 4, wherein Z and Z in said compound are1The same or different, and the same or different,is selected from
6. The novel hole transport material according to claim 1, wherein the compound is selected from the group consisting of:
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06220447A (en) * | 1992-03-27 | 1994-08-09 | Pioneer Electron Corp | Organic electroluminescent element |
| 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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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06220447A (en) * | 1992-03-27 | 1994-08-09 | Pioneer Electron Corp | Organic electroluminescent element |
| 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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