CN105384759A - Aromatic heterocycle derivative and organic light emitting diode (OLED) device using same - Google Patents
Aromatic heterocycle derivative and organic light emitting diode (OLED) device using same Download PDFInfo
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- CN105384759A CN105384759A CN201510691075.3A CN201510691075A CN105384759A CN 105384759 A CN105384759 A CN 105384759A CN 201510691075 A CN201510691075 A CN 201510691075A CN 105384759 A CN105384759 A CN 105384759A
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- 239000000463 material Substances 0.000 claims abstract description 36
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- LGKDIHUXRXRYJV-UHFFFAOYSA-N 9h-carbazole;quinoline Chemical class N1=CC=CC2=CC=CC=C21.C1=CC=C2C3=CC=CC=C3NC2=C1 LGKDIHUXRXRYJV-UHFFFAOYSA-N 0.000 claims description 31
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000002390 heteroarenes Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- -1 Spirofluorene-based Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical class C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 abstract description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 6
- 230000001476 alcoholic effect Effects 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical group N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 abstract 2
- 238000007641 inkjet printing Methods 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- 230000005311 nuclear magnetism Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004770 highest occupied molecular orbital Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical compound BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 6
- 230000005281 excited state Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000013461 design Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229960000935 dehydrated alcohol Drugs 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000003252 repetitive effect Effects 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 238000005201 scrubbing Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000003245 working effect Effects 0.000 description 3
- XZWYAMYRMMMHKM-UHFFFAOYSA-N 1-(2-phenylphenyl)ethanone Chemical group CC(=O)C1=CC=CC=C1C1=CC=CC=C1 XZWYAMYRMMMHKM-UHFFFAOYSA-N 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012858 packaging process Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an aromatic heterocycle derivative and an organic light emitting diode (OLED) device using the same. An organic compound represented by a formula (I) shown in the description is an organic phosphorescent luminescent material. According to the organic compound disclosed by the invention, carbazoline is bonded to an aromatic ring, so that the organic compound has very good solubility property in an alcoholic solvent; in addition, a pyrimidine skeleton in the molecule is also an alcohol-soluble group. According to the organic compound, the designed structure has a carbazoline structure, so that the organic compound has high triplet and electron migration rate and serves as a blue phosphorescent main body and electron transmission material; and meanwhile, the organic compound is soluble to alcoholic solvents, so that purification and the like are facilitated, and the organic compound can also serve as an inkjet printing OLED material.
Description
Technical field
The present invention relates to a kind of aromatic heterocycle derivative and a kind of Organic Light Emitting Diode (OLED) device, more specifically, relate to and a kind ofly because of high triplet energy and electronic transmission performance, there is the aromatic heterocycle derivative of higher luminous efficiency and a kind of OLED using this aromatic heterocycle derivative.
Background technology
In recent years, extensive research and development had been carried out to organic electroluminescence device.In the basic structure of this luminous element, the layer containing luminophore is inserted between pair of electrodes, by applying voltage on this element, can obtain the light emission of self-luminescent material.
Because this luminous element is self-emission device, therefore they have advantage with saving in backlight demand in high pixel visibility relative to liquid-crystal display, are such as regarded as thus being suitable for flat panel displaying element.Luminous element has advantage equally, because they are thin and lightweight.Response very is at a high speed one of feature of this element.
In addition, due to this luminous element can be formed in the form of a film, therefore planar light emission can be provided.Therefore, easily can be formed there is large-area element.This is adopt with incandescent light and the LED pointolite that is representative or take luminescent lamp as the feature that the linear light sorurce of representative is difficult to obtain.Therefore, luminous element also has large potentiality as the planar light source etc. that can be applicable to throw light on.
The excited state formed by organic compound can be singlet or triplet state.From singlet excited state (S
*) transmitting be fluorescence, and from triplet excited states (T
*) transmitting be called as phosphorescence.In addition, think that in luminous element, it adds up generation than being S
*: T
*=1:3.Being in photoemissive compound by the energy conversion of singlet excited state, at room temperature not observing the transmitting from triplet excited states, and only observing the transmitting from singlet excited state.Therefore, think and the theoretical limit using the internal quantum of the luminous element of fluorescent chemicals to have 25% be based upon the S of 1:3
*with T
*ratio.Therefore organic electromechanical phosphorescent material is the class material recently attracted attention, there is high luminous efficiency and the electroluminescent organic material of luminosity, it is by introducing the method for heavy metal atom, originally the triplet transition prohibited under make use of room temperature, thus enable internal quantum theory reach 100%, be single fluorescent material 4 times (1, CaoY., ParkerI.D., HeegerJ., Nature, 1999,397:414-417.2, WohlgenannM., etal.Nature, 2001,409:494-497.).The heavy metal atom that organic electromechanical phosphorescent material is conventional mostly is transition metal, wherein with iridium most widely used, research is the most detailed, this is because the phosphorescent emissions stronger under having high efficiency, room temperature of metal iridium complex and emission wavelength can be regulated by the adjustment of ligand structure to make the color of electroluminescent device cover whole visible region.Therefore the efficient metal iridium complex of design studies synthesizing new, splits phosphorescing materia and is significant.
But the efficiency of doping agent acutely reduces because of Quenching, and the luminescent layer thus for the doping agent without main body exists restriction.Therefore, it is desirable that, form luminous material layer by doping agent and the main body with more high thermal stability and triplet energy state.
In the OLED comprising phosphorescent compound, the hole from anode and the electronics from negative electrode combine at the main body place of luminous material layer.The singlet of singlet exciton to doping agent of main body or the energy level transition of triplet occur, and the triplet excitons of concurrent autonomous agent is from birth to the energy level transition of the triplet of doping agent.The exciton transitting to the singlet energy level of doping agent transits to the triplet of doping agent again.The exciton transition of the triplet of doping agent, to ground state, makes light emitting layer luminesces.
For realizing the high-effect order transition transitting to doping agent, the triplet energy state of main body should be greater than the triplet energy state of doping agent.When the triplet of main body is less than the triplet energy state of doping agent, to occur by doping agent, to the anti-transition of main body energy, luminous efficiency to be reduced.
The CBP being widely used in main body has the triplet of 2.6eV, about has the most high level of-6.3eV, the lowest energy level of peace treaty-2.8eV.Therefore utilizing triplet 2.8eV, can there is the anti-transition of energy level of doping agent to main body, luminous efficiency is reduced in the blue light doping agent FCNIr of most high level-5.8eV and lowest energy level-3.0eV.Particularly, the generation of luminous efficiency reduction is more remarkable under cryogenic.
Pyrimidine structure, as electrophilic group, can design bipolar host material and electronic material, has high triplet state and electron transport ability.Bright dipping Xing Chan company is engaged in the material of main part of pyrimidine serial and the exploitation of electronic material always, develops some materials.A (referenced patent US20040086745) B (referenced patent US20140151647)
A energy level (HOMO-5.71, LUMO-2.16, singlet 3.55eV, triplet state 2.90eV) B energy level (HOMO-6.13, LUMO-2.62, singlet 3.51eV, triplet state 2.65eV) two structures have difference a little, and triplet state and HOMO have very large difference.Electric transmission can to 10
-6, the existence of pyrimidine group is described, enhances electron transport ability.Although A triplet is high, HOMO, can not effective blocking hole less than-6.0eV.Although B can effective blocking hole, triplet is somewhat low, can only as the material of main part of ruddiness and green glow.
Summary of the invention
The present invention relates to a kind of aromatic heterocycle derivative and a kind of OLED using phosphorescent compound, both solve one or more problems that restriction and defect because of prior art cause substantially.
An object of the present invention is to provide a kind of phosphorescent compound, described phosphorescent compound has high triplet energy state and electronic transmission performance, can use as the main body of phosphorescent devices and electron transport material.
Another object of the present invention is to provide a kind of OLED with higher luminous efficiency.Seemingly, because have pyridine structure in structure, triplet state is higher than carbazole for carbazole quinoline structure and carbazoles, same structure material triplet state is also high, and electronic mobility also strengthens (ChilWonLeeandJunYeobLee, Adv.Mater.2013 greatly, 25,5450 – 5454).In order to meet the requirement of blue phosphor materials in triplet state, electronic mobility etc., structure introducing carbazole quinoline group is a good selection.
Heteroaromatic compound shown in formula (I),
Wherein R1 to R5 independently represents that hydrogen, carbonatoms are alkyl, the substituted or unsubstituted phenyl of C1-C4 or the biphenyl of 1 to 4,
Ar3, Ar4 are independently the substituted or unsubstituted carbazole quinoline of C1-C4, carbazole or hydrogen; And have one at least for carbazole quinoline, carbazole or carbazole quinoline are linked by 9 nitrogen-atoms,
One of 1,2,3,4 four positions of click oxazoline ring are nitrogen-atoms, constitute 4 isomerss of carbazole quinoline respectively:
Ar5 represents that hydrogen, carbonatoms are alkyl, the substituted or unsubstituted aromatic base of C6-C40, the substituted or unsubstituted heterocyclic aromatic base of 1 to 4,
A3, a4 independently represent that C1-C4 replaces or non-substituted phenylene, and j, k independently represent 0 or 1, and the heteroatoms of described heteroaryl is N, O, S.
Preferred: wherein R1 is hydrogen or benzene, biphenyl, and R2 to R5 represents hydrogen, j, k represent that 0, Ar5 is expressed as the phenyl or xenyl replacing or do not get.
Organic compound is represented by general formula (II) below:
Wherein R6 to R8 independently represents that hydrogen, carbonatoms are alkyl, the substituted or unsubstituted aryl of C6-C40, substituted or unsubstituted heteroaryl, substituted or unsubstituted fused ring aryl, the substituted or unsubstituted fused ring heteroaryl of 1 to 4.
Ar6, Ar7 represent hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted aryl, substituted or unsubstituted diphenylene-oxide, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted aphthothiophenes, carbazole quinoline, pyridine, the substituted or unsubstituted heterocyclic aryl of phenanthroline; Carbazole quinoline is linked by 9 nitrogen-atoms,
One of 1,2,3,4 four positions of click oxazoline ring are nitrogen-atoms, constitute 4 isomerss of carbazole quinoline respectively:
A6, a7 independently represent replacement or non-substituted phenylene, and m, n independently represent 0 or 1.
Preferred: R1 is hydrogen or benzene, and R2 to R5, R6, R8 represent hydrogen, and j, km, n represent 0, Ar6, and Ar7 represents hydrogen, R7 does not replace or phenyl, xenyl that 1-4 carbon atom replaces, naphthyl, fluorenyl, Spirofluorene-based, aromatic base, heterocyclic aryl.
Preferred: Ar3, Ar4 are independently carbazole quinoline, hydrogen atom, carbazole, wherein have one at least for carbazole quinoline.
This organic compound is represented by general formula below:
Wherein R9, R10 independently represent that hydrogen, carbonatoms are alkyl, the substituted or unsubstituted phenyl of C1-C4 or the biphenyl of 1 to 4.
Preferred: R1 is hydrogen or benzene, and R2 to R5, R6, R8 to R10 represent hydrogen, j, n represent that 0, Ar3 is carbazole quinoline, and Ar7 represents hydrogen, and R7 does not replace or phenyl, xenyl that 1-4 carbon atom replaces, the heterocyclic aryl of naphthyl, fluorenyl, Spirofluorene-based, C6-C20.
As the structure that this patent general formula describes, following structure of illustrating, but the present invention does not limit to structure below.
The example that this patent is enumerated just is enumerated in the scope of patent requirements, but patent is not limited to current example, as long as the structure meeting claim is all at the protection domain of this patent.
A kind of organic light emitting diode device, comprising: the first electrode; Second electrode relative with the first described electrode; Between the first electrode and the second electrode, described luminescent layer comprises above-mentioned arbitrary organic compound to luminescent layer.
The material of described luminescent layer comprises main body and adulterate body, and described above-mentioned organic compound is as material of main part.
Described material of main part is blue phosphorescent material of main part.
Described device is display device and illuminating device.
The structure of the compound mainly pyrimidine scaffold of our design, be two compd As for pointing out in background technology, B structure is improved, and is ensureing that HOMO is less than-6.0eV, needs to improve triplet.Carbazole quinoline is and carbazole similar structures, has the performance of carbazole, but triplet state and electronic transmission performance are better than carbazole.We replace the carbazole in structure above carbazole quinoline structure, obtain some row Hete rocyclic derivatives.The carbazole quinoline derivant obtained remains with pyrimidine scaffold, and carbazole quinoline structure, and carbazole quinoline is connected by 9 nitrogen-atoms keys, and molecular weight does not have that great changes will take place.Carbazole quinoline has good solubility property in alcoholic solvent, and key is linked above aromatic ring, still maintains this performance; Adding in molecule and have pyrimidine scaffold, is also the group being dissolved in alcohol.Carbazole group is the group of rigidity, and A, B structure solvability obtained is very low, is unfavorable for purifying.
The structure of this patent design, because with carbazole quinoline structure, is dissolved in alcoholic solvent, is convenient to purifying etc.Be soluble in alcoholic solvent, can use as spray ink Printing OLED material.
Accompanying drawing explanation
The nuclear-magnetism of Fig. 1 compound 3,
The nuclear-magnetism of Fig. 2 compound 4,
The nuclear-magnetism of Fig. 3 first main body,
The nuclear-magnetism of Fig. 4 second main body,
The nuclear-magnetism of Fig. 5 the 4th main body.
Embodiment
The preparation of embodiment 1, first main body
The synthesis of compound 1: 3,5-dibromo benzaldehyde obtains white solid (CN100366703) by 1,3,5-tribromo-benzene lithiumation.
The synthesis of compound 3:
Add 50.8 gram of 3,5-dibromo benzaldehyde, 37.8 grams of acetyl biphenyl in 1000ML ethanol, stirring at room temperature, drip the 70ML aqueous solution of dissolving 14.2 grams, stirring at room temperature 2 hours, TLC detects does not have raw material, stopped reaction.
The product water obtained, ethanol repetitive scrubbing, obtain 81G light yellow solid, yield 98%.Nuclear-magnetism is shown in Fig. 1.
The synthesis of compound 4:
In 1000L dehydrated alcohol, add 81G product obtained in the previous step, 30G NSC 2020,15G sodium hydroxide adds, and stir, backflow is spent the night.Obtain a large amount of solids, filter, washing, washing with alcohol, obtain white solid.Obtain 50G, 60% yield.Nuclear-magnetism is shown in Fig. 2.
The synthesis of the first material of main part:
1L four-hole bottle adds 800MLDMF, and add 46G compound 4,50G1-carbazole quinoline, copper powder, salt of wormwood, inflated with nitrogen stirs 30 minutes, temperature rising reflux.24 hours TLC detect does not have intermediate, stopped reaction, filters.Be poured into water by the solution obtained, separate out solid, filter, toluene purifying, obtains 40G product.Nuclear-magnetism is shown in Fig. 3.
The preparation of embodiment 2: the second main body
The synthesis of compound 1: 3,5-dibromo benzaldehyde obtains white solid by 1,3,5-tribromo-benzene lithiumation.
The synthesis of compound 3:
Add 50.8 gram of 3,5-dibromo benzaldehyde, 37.8 grams of acetyl biphenyl in 1000ML ethanol, stirring at room temperature, drip the 70ML aqueous solution of dissolving 14.2 grams, stirring at room temperature 2 hours, TLC detects does not have raw material, stopped reaction.
The product water obtained, ethanol repetitive scrubbing, obtain 81G light yellow solid, yield 98%.Nuclear-magnetism is shown in Fig. 1.
The synthesis of compound 4:
In 1000L dehydrated alcohol, add 81G product obtained in the previous step, 30G NSC 2020,15G sodium hydroxide adds, and stir, backflow is spent the night.Obtain a large amount of solids, filter, washing, washing with alcohol, obtain white solid.Obtain 50G, 60% yield.Nuclear-magnetism is shown in Fig. 2.
The synthesis of the second material of main part:
1L four-hole bottle adds 800MLDMF, and add 46G compound 4,50G3-carbazole quinoline, copper powder, salt of wormwood, inflated with nitrogen stirs 30 minutes, temperature rising reflux.24 hours TLC detect does not have intermediate, stopped reaction, filters.Be poured into water by the solution obtained, separate out solid, filter, toluene purifying, obtains 50G product.Nuclear-magnetism is shown in Fig. 4.
Embodiment 3, the 3rd main body synthesis
Using δ-carbazole quinoline as reactant, obtain compound and obtain the 3rd material of main part.
Embodiment 4,
By 9,9-dimethyl acridinium as reactant, obtain compound and obtain the 4th material of main part.Nuclear-magnetism Fig. 5.
The synthesis of embodiment five, the 5th main body
The synthesis of compound 1: 3,5-dibromo benzaldehyde obtains white solid by 1,3,5-tribromo-benzene lithiumation.
The synthesis of compound 6:
Add 50.8 gram of 3,5-dibromo benzaldehyde, 27.8 grams of 2-acetopyridine in 1000ML ethanol, stirring at room temperature, drip the 70ML aqueous solution of dissolving 14.2 grams, stirring at room temperature 2 hours, TLC detects does not have raw material, stopped reaction.
The product water obtained, ethanol repetitive scrubbing, obtain 61G light yellow solid, yield 98%.
The synthesis of compound 7:
In 1000L dehydrated alcohol, add 61G product obtained in the previous step, 30G NSC 2020,15G sodium hydroxide adds, and stir, backflow is spent the night.Obtain a large amount of solids, filter, washing, washing with alcohol, obtain white solid.Obtain 50G, 65% yield.By the analysis 467.15 of FD-MS, be defined as compound 7.
The synthesis of the 5th material of main part:
1L four-hole bottle adds 800MLDMF, and add 46G compound 7,50G1-carbazole quinoline, copper powder, salt of wormwood, inflated with nitrogen stirs 30 minutes, temperature rising reflux.24 hours TLC detect does not have intermediate, stopped reaction, filters.Be poured into water by the solution obtained, separate out solid, filter, toluene purifying, obtains 40G product.By the analysis 641.71 of FD-MS, be defined as the 5th host compound.
The synthesis of embodiment six, the 6th main body
The synthesis of compound 8:
Compound 8 synthesizes the synthesis technique according to the second main body, and just the amount of substance of carbazole quinoline is half, and obtaining compound 8 is light yellow solid, yield 65%.
6th main body synthesis:
According to the synthesis technique of the second main body, the amount of carbazole is 1.3 times of compound 8, reacts 24 hours, and cross pillar purifying and obtain white solid, FD-MS is detected as 715.8, is defined as target product.
First to six material of main part by above-mentioned synthesis example prepared of mensuration according to the invention process method and the material by the comparative example of following chemical formulation are at low temperature (such as, ultra-violet absorption spectrum 77K) and photoluminescence spectra, during its display result is shown below.
Comparative example
Table 1:
| UV(nm) | PL(nm) | Energy level (eV) | LUMO(eV) | HOMO(eV) | Triplet (eV) | |
| Comparative example | 365 | 425 | 3.51 | -2.62 | -6.13 | 2.65 |
| Embodiment 1 | 358 | 443 | 3.47 | -2.78 | -6.25 | 2.95 |
| Embodiment 2 | 363 | 424 | 3.43 | -2.85 | -6.28 | 2.94 |
| Embodiment 3 | 360 | 434 | 3.50 | -2.75 | -6.25 | 2.95 |
| Embodiment 4 | 355 | 424 | 3.46 | -2.20 | -5.66 | 2.93 |
| Embodiment 5 | 355 | 429 | 3.53 | -2.87 | -6.30 | 2.92 |
| Embodiment 6 | 355 | 432 | 3.43 | -2.77 | -6.20 | 2.93 |
As can be seen from Table 1, main body one all higher than 2.92eV, can meet the requirement of blue phosphor materials main body to main body six triplet state.Compare with comparative example, the introducing of carbazole quinoline, adds triplet state, and HOMO, LUMO reduce than comparative example, illustrates that the electron attraction of carbazole quinoline is obvious.Main body five introduces electron-withdrawing substituent pyridine, and HOMO, LUMO also reduce greatly, and triplet state is smaller.Embodiment four, introducing group is acridine structure, and be electron-donating group, LUMO, HOMO obviously increase, and transmission electronic performance reduces.
Below description uses the Production Example of material as the Organic Light Emitting Diode of blue main body of blue phosphorescent compound and the comparative example formed by the above-mentioned first to the 6th material of main part.
Patterning is carried out to ito substrate, makes its light-emitting area 3mmX3mm, then clean.After ito substrate is put into vacuum chamber, base pressure is made to be 1X10
-6holder.Then, for the formation of on the ITO of anode, forming thickness is that the HATCN of about 50 dusts is for hole injection layer, forming thickness is that the NPD of about 550 dusts is for hole transmission layer, formed thickness be the TAPC of about 100 dusts for hole injection layer, to form thickness be the second material of main part of about 300 dusts and doping content is that the FCNIr of about 15% is for luminescent layer.Then, formed thickness be the TmPyPb of 400 dusts for electron supplying layer, formed thickness be the LiF of about 5 dusts for electron injecting layer, and form the Al layer negative electrode of 1100 dusts.Then, use UV solidified nature encapsulants and moisture adsorbent to carry out packaging process, form photodiode.
TmPyPb：
Comparative example
Adopt the technique identical with Production Example 1, manufacture Organic Light Emitting Diode, uniquely unlike adopting comparative example main body as light emitting host.
As shown in table 2, can confirm, compared with comparative example, according to Production Example 1,2,3,5,6 Organic Light Emitting Diodes manufactured, when showing the chromaticity coordinates of par, demonstrate luminous efficiency, quantum yield and the improvement in work-ing life.Particularly, the work-ing life of Organic Light Emitting Diode is greatly improved.The introducing of embodiment 4 acridine, add the transmission in hole, therefore trigger voltage is lower, and system transporting holes ability is stronger, and positive and negative charge transmission is unbalanced, and life-span and efficiency are affected, less better relative to the subjectivity property introducing carbazole quinoline.System introduces carbazole quinoline, and the electron deficiency performance of carbazole quinoline is embodied, and electric transmission and injection are improved, and efficiency and life-span also significantly improve.
As mentioned above, implementation method of the present invention has manufactured the blue phosphorescent compound with high triplet energy, and the blue phosphorescent compound described in using is as the main body of the luminescent layer of Organic Light Emitting Diode, thereby promote the energy trasfer in luminescent layer, and improve blue emission efficiency and the work-ing life of organic luminous layer.
Although embodiments of the present invention are described by reference to its numerous description embodiment, but should be appreciated that those skilled in the art can design by fall into disclosure principle scope within many other improvement and embodiment.More specifically, various changes and modifications within the scope of the disclosure, accompanying drawing and claims subject combination arrangement component part and/or arrangement in be possible.Except the changes and improvements of component part and/or arrangement aspect, replaceability application also will be apparent for a person skilled in the art.
Claims (10)
1. the heteroaromatic compound shown in formula (I),
Wherein R1 to R5 independently represents that hydrogen, carbonatoms are alkyl, the substituted or unsubstituted phenyl of C1-C4 or the biphenyl of 1 to 4,
Ar3, Ar4 are independently the substituted or unsubstituted carbazole quinoline of C1-C4, carbazole or hydrogen; And have one at least for carbazole quinoline, carbazole or carbazole quinoline are linked by 9 nitrogen-atoms,
Ar5 represents that hydrogen, carbonatoms are the alkyl of 1 to 4, the substituted or unsubstituted aromatic base of C6-C40 or heteroaryl,
A3, a4 independently represent that C1-C4 replaces or non-substituted phenylene, and j, k independently represent 0 or 1, and in described heteroaryl, heteroatoms is N, O, S.
2. heteroaromatic compound according to claim 1, wherein R1 is hydrogen or benzene, biphenyl, and R2 to R5 represents hydrogen, and j, k represent that 0, Ar5 is expressed as the phenyl or xenyl replacing or do not get.
3. heteroaromatic compound according to claim 1, is represented by general formula (II) below:
Wherein R6 to R8 independently represents that hydrogen, carbonatoms are the alkyl of 1 to 4, the substituted or unsubstituted aryl of C6-C40 or heteroaryl or fused ring aryl or fused ring heteroaryl,
Ar6, Ar7 represent hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted aryl, substituted or unsubstituted diphenylene-oxide, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted aphthothiophenes, carbazole quinoline, pyridine, the substituted or unsubstituted heterocyclic aryl of phenanthroline; Carbazole quinoline is linked by 9 nitrogen-atoms,
A6, a7 independently represent replacement or non-substituted phenylene, and m, n independently represent 0 or 1.
4. heteroaromatic compound according to claim 3, wherein R1 is hydrogen or benzene, and R2 to R5, R6, R8 represent hydrogen, j, km, n represent 0, Ar6, and Ar7 represents hydrogen, R7 does not replace or phenyl, xenyl that 1-4 carbon atom replaces, naphthyl, fluorenyl, Spirofluorene-based, aromatic base, heteroaryl.
5. heteroaromatic compound according to claim 4, Ar3 is carbazole quinoline, one in Ar4 carbazole quinoline, hydrogen atom, carbazole.
6. heteroaromatic compound according to claim 3, this organic compound is represented by general formula (III) below:
Wherein R9, R10 independently represent that hydrogen, carbonatoms are alkyl, the substituted or unsubstituted phenyl of C1-C4 or the biphenyl of 1 to 4.
7. heteroaromatic compound according to claim 6, R1 is hydrogen or benzene, R2 to R5, R6, R8 to R10 represent hydrogen, j, n represents that 0, Ar3 is carbazole quinoline, and Ar7 represents hydrogen, R7 does not replace or phenyl, xenyl that 1-4 carbon atom replaces, the heterocyclic aryl of naphthyl, fluorenyl, Spirofluorene-based, C6-C20.
8. heteroaromatic compound according to claim 1, has structure below:
9. an organic light emitting diode device, comprising: the first electrode; Second electrode relative with the first described electrode; Between the first electrode and the second electrode, described luminescent layer comprises the arbitrary organic compound of claim 1-8 to luminescent layer.
10. organic light emitting diode device according to claim 9, the material of described luminescent layer comprises main body and adulterate body, the described arbitrary organic compound of claim 1-8 that comprises is as blue phosphorescent material of main part and electron transport material, and described device is display device and illuminating device.
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| WO2017067422A1 (en) * | 2015-10-22 | 2017-04-27 | 北京拓彩光电科技有限公司 | Pyrimidine phenyl carbazoline derivative, and organic light-emitting diode device therefor |
| JP2017175099A (en) * | 2016-03-25 | 2017-09-28 | ▲いく▼▲雷▼光電科技股▲分▼有限公司 | Compound for organic electroluminescent device, and organic electroluminescent device using the compound |
| WO2018164545A1 (en) * | 2017-03-10 | 2018-09-13 | 주식회사 엘지화학 | Novel heterocyclic compound and organic light emitting element using same |
| CN108929338A (en) * | 2018-03-19 | 2018-12-04 | 北京拓彩光电科技有限公司 | Aromatic heterocycle delayed fluorescence compound and and its organic light emitting diode device |
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