CN106588935A - Derivative of tetra-substituted pyrrolo [3,2-b] pyrrole and organic electroluminescence device based on same - Google Patents
Derivative of tetra-substituted pyrrolo [3,2-b] pyrrole and organic electroluminescence device based on same Download PDFInfo
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- CN106588935A CN106588935A CN201611089243.2A CN201611089243A CN106588935A CN 106588935 A CN106588935 A CN 106588935A CN 201611089243 A CN201611089243 A CN 201611089243A CN 106588935 A CN106588935 A CN 106588935A
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- phenyl
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- butyl
- pyrrolo
- phenyls
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 15
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 title claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 13
- 241001597008 Nomeidae Species 0.000 claims description 12
- 150000003233 pyrroles Chemical class 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- -1 substituted-phenyl group Chemical group 0.000 claims description 6
- 241000790917 Dioxys <bee> Species 0.000 claims description 4
- 229910000085 borane Inorganic materials 0.000 claims description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical class C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- HMDVVKCPUGASAD-UHFFFAOYSA-N 1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole Chemical class C(C)(C)(C)C1=CC=C(C=C1)N1C2=C(C=C1)N(C=C2)C1=CC=C(C=C1)C(C)(C)C HMDVVKCPUGASAD-UHFFFAOYSA-N 0.000 abstract 2
- 230000002950 deficient Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000012043 crude product Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- OFZOVFCBBFJMNV-UHFFFAOYSA-N 4-(benzenesulfonyl)benzaldehyde Chemical class C1=CC(C=O)=CC=C1S(=O)(=O)C1=CC=CC=C1 OFZOVFCBBFJMNV-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000035126 Facies Diseases 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical class OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AJRXJTDIDFRAOI-UHFFFAOYSA-N CC1OC1C(C)=N Chemical compound CC1OC1C(C)=N AJRXJTDIDFRAOI-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- WRLRISOTNFYPMU-UHFFFAOYSA-N [S].CC1=CC=CC=C1 Chemical compound [S].CC1=CC=CC=C1 WRLRISOTNFYPMU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical class Br* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- ONEFTMYLUCWUOY-UHFFFAOYSA-N difluoro-(2,3,4-trimethylphenyl)borane Chemical compound CC1=C(C(=C(C=C1)B(F)F)C)C ONEFTMYLUCWUOY-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 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
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- SRJQTHAZUNRMPR-UYQKXTDMSA-N spinosyn A Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRJQTHAZUNRMPR-UYQKXTDMSA-N 0.000 description 1
- 238000010025 steaming Methods 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
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical class CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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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- 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
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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
- H10K85/649—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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention provides a derivative of 2,5-substituted 1,4-di(4-tert-butyl-phenyl) pyrrolo [3,2-b] pyrrole, and application of the derivative. The derivative has the following structural formula as shown in the specification; in the formula, R represents an electron deficient substituted phenyl group. An organic film layer prepared from the derivative of the 2,5-substituted 1,4-di(4-tert-butyl-phenyl) pyrrolo [3,2-b] pyrrole has the advantages of low voltage driving, high efficiency, long service life and the like when being used as an organic electroluminescence device of a light emitting layer.
Description
One technical field
The present invention relates to 2,5 replacement 1,4- bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles derivant and
Based on its organic electroluminescence device, belong to organic electroluminescence device field.
Two background technologies
Organic electroluminescent LED (OLEDs) as follow-on flat panel display, with self-luminous, it is all solid state,
Wide viewing angle, fast response time, driving voltage are low, low energy consumption, efficiency high, it is flexible many advantages, such as, application prospect is huge.Device
Structure is that the luminescent layer containing luminous organic material is sandwiched between electron transfer layer and hole transmission layer, by applying external electrical
Electronics and hole are injected in pressing to device and exciton is compounded to form in luminescent layer outwards launch photon in the form of fluorescence or phosphorescence.
Luminescent layer is typically made up of material of main part and dopant.In recent years, hot activation delayed fluorescence material is due to can be same
The singlet excitons of Shi Liyong 25% and 75% triplet exciton obtain high luminous efficiency and are widely used in OLED
Among.
Simultaneously [3,2, b] pyrroles is electron rich group that electron donation is better than carbazole and diphenylamines to Isosorbide-5-Nitrae-pyrrolin, its
Similar compound thieno [3,2-b] thiophene is commonly used for p-type organic field effect tube.But not yet have 1,4- bis- at present
Hydrogen pyrrolo- [3,2, b] pyrroles is applied to the report in OLED as electron donor fragment.
1,4- bis- (4- tert-butyl-phenyls) pyrrolo- of with hot activation delayed fluorescence property 2,5 replacements of the present invention
The derivant of [3,2-b] pyrroles is new, and the Isosorbide-5-Nitrae position connection of Isosorbide-5-Nitrae-pyrrolin simultaneously [3,2, b] pyrroles is with the tert-butyl group
To increase its dissolubility, 2,5 connection electron withdraw groups can be formed organic film by solwution method, be made using them phenyl
Luminescent layer for organic electroluminescence device can realize low driving voltage and high external quantum efficiency.
Three content of the invention
The invention solves the problems that first technical problem be to provide a kind of 2,5 replacement 1,4- bis- (4- tert-butyl-phenyls)
The derivant of pyrrolo- [3,2-b] pyrroles.
The invention solves the problems that second technical problem there is provided 2,5 replacement 1,4- bis- (4- tert-butyl-phenyls) pyrroles
Cough up application of the derivant of simultaneously [3,2-b] pyrroles in organic electroluminescence device.
A kind of organic electroluminescence device, which includes negative electrode, anode and organic thin film layer, and the organic thin film layer is to arrange
The luminescent layer containing luminescent material between a cathode and an anode；Wherein, the luminescent layer is comprising single or as mixing group
Bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles' of 1,4- of as claimed in claim 1 or 22,5 replacements for dividing spreads out
It is biological.
To solve above-mentioned first technical problem, the present invention provides a kind of-two (4- tert-butyl benzenes of Isosorbide-5-Nitrae of 2,5 replacements
Base) pyrrolo- [3,2-b] pyrroles derivant, it have following structural formula:
In formula, R represents the substituted-phenyl group of electron deficiency.
Preferably, R is respectively 4- cyano-phenyls, 4- (benzenesulfonyl) phenyl, 5,5- dioxy -2- dibenzothiophenes bases, 4-
Two (2,4,6- trimethylphenyls) borine phenyl, 4- (2,1,3- diazosulfide bases) phenyl, 4- (diphenyl phosphine oxide) phenyl,
4- (4,6- diphenyl -1,3,5- triazines) phenyl, 4- (2,1,3- diazosulfide bases) thienyls and 4- (7- phenyl benzos [1,
2,5] thiadiazolyl group) one kind in phenyl.
To solve above-mentioned second technical problem, the present invention provides a kind of organic electroluminescence device, and which includes negative electrode, sun
Pole and organic thin film layer, the organic thin film layer are provided in the luminescent layer containing luminescent material between negative electrode and anode；Its
In, the luminescent layer includes single or as blending ingredients as claimed in claim 1 or 22,5 Isosorbide-5-Nitraes-two for replacing
The derivant of (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles.
The representative instance of organic electroluminescence device structure of the present invention includes：
(1) anode/luminescent layer/negative electrode；
(2) anode/hole transmission layer/luminescent layer/negative electrode；
(3) anode/electronic barrier layer/luminescent layer/negative electrode；
(4) anode/luminescent layer/electron transfer layer/negative electrode；
(5) anode/hole transmission layer/electronic barrier layer/luminescent layer/negative electrode；
(6) anode/hole transmission layer/electronic barrier layer/luminescent layer/electron transfer layer/negative electrode；
(7) anode/hole transmission layer/electronic barrier layer/luminescent layer/hole blocking layer/electron transfer layer/negative electrode；
In said structure, preferred structure (6).But the structure of organic electroluminescence device be not limited to it is recited above this
A little examples.
Derivant institute to 1,4- bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles of 2,5 replacements of the present invention
The luminescent layer of the organic electroluminescence device of formation is prepared using spin-coating method.If other layers are without specified otherwise using steaming
It is prepared by plating method.
The material of the present invention has advantages below：
The derivant of 1,4- bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles of 2,5 replacements of the present invention has
High fluorescence quantum yield, belongs to hot activation delayed fluorescence material, can be used for the luminescent layer of organic electroluminescence device.With 2,5
The organic thin film layer that the derivant of 1,4- bis- (4- tert-butyl-phenyls) pyrroles [3,2-b] pyrroles that position replaces is formed is used as luminescent layer
Organic electroluminescence device there is low voltage drive, high efficiency and long-life.
Four description of the drawings
Fig. 1 is the structure of the derivant of 1,4- bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles of 2,5 replacements
Formula.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of compounds I 1 prepared by embodiment 1.
Fig. 3 is the hydrogen nuclear magnetic resonance spectrogram of compounds I 2 prepared by embodiment 2.
Fig. 4 is the hydrogen nuclear magnetic resonance spectrogram of compounds I 3 prepared by embodiment 3.
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram of compounds I 4 prepared by embodiment 4.
Fig. 6 is the hydrogen nuclear magnetic resonance spectrogram of compounds I 5 prepared by embodiment 5.
Five specific embodiments
Embodiment 1：The synthesis of compounds I 1
Synthetic route is as follows：
Reaction is comprised the following steps that：
Under nitrogen protection, 2.62g (20mmol) is added to cyanogen in two mouthfuls of round-bottomed flasks of the 50ml equipped with condensing tube
Benzaldehyde, 3.18ml (20mmol) p-tert-butyl-aniline, 0.398g (2mmol) p-methyl benzenesulfonic acid, 20ml glacial acetic acid, are heated to
90 DEG C of reaction 30min, are then slowly added into 0.88ml 2, and 3- diacetyl continues to react 3h afterwards at 90 DEG C.Reaction terminates
After be cooled to room temperature, filter and simultaneously washed two to three times with glacial acetic acid, the crude product for obtaining dichloromethane/petroleum ether (2:1) make
For eluant, silica gel column chromatography purification obtains I 1 (greenish yellow solid) 1.5g, and yield is 26%.
Embodiment 2：The synthesis of compounds I 2
Synthetic route is as follows：
The first step, adds 60ml DMSO, in the round-bottomed flask equipped with 100ml of the condensing tube with stirring then to bottle
Middle addition 8.2g (0.05mol) benzene sulfinic acid sodium salt, 6.2g (0.05mol) 4-Fluorobenzaldehyde, then react and stir 4 at 120 DEG C
My god.Reaction is cooled to room temperature after terminating, and reacted mixture is poured in a large amount of water, and the precipitation of precipitation is filtered and washed with water many
It is secondary, then by the mixed solvent recrystallization three times of this precipitation ethyl acetate/dichloromethane, obtain 4- benzenesulfonyl benzaldehydes
9.8g, yield 80%；
Second step, under nitrogen protection, adds in two mouthfuls of round-bottomed flasks equipped with 50ml of the condensing tube with stirring
2.46g (10mmol) 4- benzenesulfonyl benzaldehydes, 1.59ml (10mmol) p-tert-butyl-aniline, 0.2g (1mmol) are to toluene sulphur
Acid, 20ml glacial acetic acid, are heated to 90 DEG C of reaction 30min, are then slowly added into 0.44ml 2,3- diacetyl, afterwards at 90 DEG C
It is lower to continue reaction 3h.Reaction is cooled to room temperature after terminating, filter and washed two to three times with glacial acetic acid, the crude product second for obtaining
Acetoacetic ester recrystallization 3 times, obtains I 2 (yellow solid) 1.18g, and yield is 29%.
Embodiment 3：The synthesis of compounds I 3
Synthetic route is as follows：
The first step, takes the round-bottomed flask of 1L, weighs 9.2g (50mmol) dibenzothiophenes and is dissolved in 600ml CH2Cl2In, by
Drop Deca 2.3ml (45mmol) Br2, and be stirred vigorously, after completion of dropwise addition, continue 10h is stirred at room temperature.After reaction terminates,
Sodium sulfite aqueous solution is added in reaction system, by organic phase separation and anhydrous sodium sulfate drying is used, vacuum distillation removes molten
Crude product white solid is obtained after agent, crude product re-crystallizing in ethyl acetate is obtained into the pure 2- bromine dibenzo thiophenes of 8.2g for three times
Fen, yield 72%.Drying is follow-up to continue ensuing reaction, under nitrogen atmosphere, takes 2- bromine dibenzothiophenes 7.04g
(27.15mmol) it is dissolved in 30ml anhydrous tetrahydro furans, with liquid nitrogen maintenance system temperature at -78 DEG C, N2Syringe is used under atmosphere
Be slowly injected into n-BuLi (1.6M normal hexane) 16.92ml (27.1mmol), then stir 1h at -78 DEG C, backward system
Then reaction system is heated to reflux 3h by the anhydrous DMF (DMF) of middle addition 2.07ml (27mmol).Reaction knot
Shu Hou, add water quenching, and reactant mixture is extracted 4 times with ether, and collected organic layer uses anhydrous Na2SO4It is dried, vacuum distillation is removed
Crude product is obtained after removing solvent, then pure dibenzothiophenes -2- formaldehyde (4.0g), yield is obtained for three times with ethyl alcohol recrystallization
71%.Take dibenzothiophenes -2- formaldehyde 3.18g (15mmol) and be dissolved in 100ml CH2Cl2In, stirring is lower to add 25.9g
(0.15mmol) metachloroperbenzoic acid (m-CPBA), reacts 24h under room temperature.After reaction terminates, add in reaction system
200ml saturations NaHCO3Solution is quenched, organic faciess saturation NaHCO3Solution is cleaned two to three times, uses anhydrous MgSO afterwards4It is dry
Dry, vacuum distillation obtains 3.48g white solids 5,5- dioxy -2- dibenzothiophenes formaldehyde, yield 95% after removing solvent.
Second step, under nitrogen protection, adds in equipped with condensing tube, two mouthfuls of round-bottomed flasks of the 50ml with stirring
2.44g (10mmol) 5,5- dioxy -2- dibenzothiophenes formaldehyde, 1.59ml (10mmol) p-tert-butyl-aniline, 0.2g (1mmol)
P-methyl benzenesulfonic acid, 20ml glacial acetic acid, are heated to 90 DEG C of reaction 30min, are then slowly added into 0.44ml 2,3- diacetyl, it
Continue to react 3h afterwards at 90 DEG C.Reaction is cooled to room temperature after terminating, filter and washed two to three times with glacial acetic acid, and what is obtained is thick
Product re-crystallizing in ethyl acetate 3 times, obtains I 3 (yellow solid) 1.04g, and yield is 26%.
Embodiment 4：The synthesis of compounds I 4
Synthetic route is as follows：
The first step, under nitrogen protection, in the reaction tube of 100ml, will be 3.15g (13.43mmol) Isosorbide-5-Nitrae-dibromobenzene molten
In 30ml anhydrous tetrahydro furans, with liquid nitrogen maintenance system temperature at -78 DEG C, N2It is slowly added dropwise with Dropping funnel under atmosphere
8.2ml (13.41mmol) n-BuLi (in 1.6M normal hexane), Deca are reacted one hour completely afterwards.Then by bis- -2,4,6- of 3g
Trimethylphenyl boron fluoride is dissolved in the solution of 20ml anhydrous tetrahydro furans and is added rapidly in reaction system.Terminate after stirring 10h
Reaction, adds deionized water, product to be extracted with ethyl acetate repeatedly toward system.The organic faciess isolated are dry with anhydrous magnesium sulfate
It is dry, after vacuum distillation removes solvent, the crude product for obtaining normal hexane/dichloromethane (30:1) as eluant, silica gel column chromatography
Post purification obtains 3.6g 4- bromophenyls two -2,4,6- trimethylphenyl borines, yield 79%.Under nitrogen atmosphere, by 3g
(7.4mmol) 4- bromophenyls two -2,4,6- trimethylphenyl borines are dissolved in 30ml anhydrous tetrahydro furans, use liquid nitrogen maintenance system
Temperature is slowly added dropwise n-BuLi (1.6M normal hexane) 4.63ml (7.4mmol) with syringe, then at -78 DEG C at -78 DEG C
Stirring 1h, backward system in add 1.14ml (14.8mmol) anhydrous DMF (DMF), recovery system temperature
Stir to room temperature and persistently.The dilute hydrochloric acid of 10ml 2mol/L after 6h, is added, continues stirring 4h.Backward system in add water,
Reactant mixture is extracted with ethyl acetate, and collected organic layer simultaneously uses anhydrous Na2SO4It is dried.After vacuum distillation removes solvent, obtain
Crude product petrol ether/ethyl acetate (99:1) as eluant, silica gel column chromatography purification obtains 2.0g 4- bis- (2,4,6-
Trimethylphenyl) borine benzaldehyde, yield 76%.
Second step, under nitrogen protection, adds in two mouthfuls of round-bottomed flasks equipped with 50ml of the condensing tube with stirring
2.0g (5.6mmol) 4- bis- (2,4,6- trimethylphenyls) borine benzaldehyde, 0.89ml (5.6mmol) p-tert-butyl-aniline,
0.11g (0.56mmol) p-methyl benzenesulfonic acid, 20ml glacial acetic acid, are heated to 90 DEG C of reaction 30min, are then slowly added into 0.25ml
2,3- diacetyl, continue to react 3h afterwards at 90 DEG C.Reaction is cooled to room temperature after terminating, filter and wash two with glacial acetic acid and arrive
Three times, the crude product for obtaining petroleum ether/dichloromethane (2:1) as eluant, silica gel column chromatography purification obtains I 4 (yellow greens
Solid) 0.856g, yield is 30%.
Embodiment 5：The synthesis of compounds I 5
The first step, adds 10g (73.52mmol) 2,1,3- diazosulfide (1) to be suspended in the round-bottomed flask of 100ml
In 50ml HBr solution (48%), dropwise Deca 2.8ml (54.26mmol) bromine is stirred vigorously simultaneously, all drips post-heating
Flow back 2 hours to 150 DEG C.Reaction is cooled to room temperature after terminating, and reactant mixture is poured in 500ml water, the solid that will be separated out
Filter, obtain 10.4g crude products；The product replaced containing a small amount of double bromines in crude product and raw material.Will be this crude product direct
Input next step reaction.Under nitrogen protection, in two mouthfuls of round-bottomed flasks of the 500ml equipped with condensing tube 8.556g is added slightly to produce
Thing (it is assumed that be entirely the bromo- 2,1,3- diazosulfides (2) of 4-, 40mmol), 10.208g (44mmol) 4- formylphenylboronic acids frequency which
Alcohol ester, 2.32g (2.0mmol) tetrakis triphenylphosphine palladiums and 200ml THF, afterwards add 200ml potassium carbonate (11.06g,
Aqueous solution 80mmol), is heated to backflow, stirs 12h.Room temperature is cooled to after terminating reaction, mixture is extracted with dichloromethane
Three times, detached organic layer anhydrous sodium sulfate drying.The crude product dichloromethane that vacuum distillation is obtained after removing solvent/
Petroleum ether (2:1) as eluant, silica gel column chromatography purification obtains flaxen 4- Fonnylphenyl -2 of 8.2g, 1,3- benzo thiophene
Diazole (3).
Second step, under nitrogen protection, adds in two mouthfuls of round-bottomed flasks equipped with 50ml of the condensing tube with stirring
4.8g (20mmol) 4- Fonnylphenyl -2,1,3- diazosulfides, 3.18ml (20mmol) p-tert-butyl-aniline, 0.398g
(2mmol) p-methyl benzenesulfonic acid, 30ml glacial acetic acid, are heated to 90 DEG C of reaction 30min, are then slowly added into 0.88ml 2,3- fourths
Diketone, continues to react 3h afterwards at 90 DEG C.Reaction is cooled to room temperature after terminating, filter and washed two to three times with glacial acetic acid,
The crude product for obtaining dichloromethane/petroleum ether (2:1) as eluant, silica gel column chromatography purification obtains 1.58g red solids I
5, yield (20%).
Claims (4)
1. the derivant of Isosorbide-5-Nitrae-two (4- tert-butyl-phenyls) pyrrolo- [3, the 2-b] pyrroles of a kind of 2,5 replacements, its feature exists
In it has following structural formula：
In formula, R represents the substituted-phenyl group of electron deficiency.
2. 1,4- bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles of according to claim 12,5 replacements spread out
It is biological, it is characterised in that R is respectively 4- cyano-phenyls, 4- (benzenesulfonyl) phenyl, 5,5- dioxy -2- dibenzothiophenes bases, 4-
Two (2,4,6- trimethylphenyls) borine phenyl, 4- (2,1,3- diazosulfide bases) phenyl, 4- (diphenyl phosphine oxide) phenyl,
4- (4,6- diphenyl -1,3,5- triazines) phenyl, 4- (2,1,3- diazosulfide bases) thienyls and 4- (7- phenyl benzos [1,
2,5] thiadiazolyl group) one kind in phenyl.
3. according to the compound described in claim 1 and 2, it is characterised in that during the compound is following (formulas 1)-(formula 5)
Any one：
。
4. a kind of organic electroluminescence device, which includes negative electrode, anode and organic thin film layer, and the organic thin film layer is provided in
The luminescent layer containing luminescent material between negative electrode and anode；Wherein, the luminescent layer is comprising single or as blending ingredients
As claimed in claim 1 or 22,5 replacements 1,4- bis- (4- tert-butyl-phenyls) pyrrolo- [3,2-b] pyrroles it is derivative
Thing.
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