CN101891673A - Organic material and application thereof in organic electroluminescence devices - Google Patents
Organic material and application thereof in organic electroluminescence devices Download PDFInfo
- Publication number
- CN101891673A CN101891673A CN2009102347608A CN200910234760A CN101891673A CN 101891673 A CN101891673 A CN 101891673A CN 2009102347608 A CN2009102347608 A CN 2009102347608A CN 200910234760 A CN200910234760 A CN 200910234760A CN 101891673 A CN101891673 A CN 101891673A
- Authority
- CN
- China
- Prior art keywords
- compound
- organic
- reaction
- product
- purity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 23
- 239000011368 organic material Substances 0.000 title claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 38
- 230000005540 biological transmission Effects 0.000 claims abstract description 11
- -1 heterocycle aromatic hydrocarbons Chemical class 0.000 claims description 13
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 10
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 61
- 150000001875 compounds Chemical group 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000000047 product Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 28
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 19
- 239000004327 boric acid Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 238000010992 reflux Methods 0.000 description 7
- 150000004056 anthraquinones Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- TVOAXRDXTGCPBB-UHFFFAOYSA-N 2-bromo-5-phenylpyridine Chemical compound C1=NC(Br)=CC=C1C1=CC=CC=C1 TVOAXRDXTGCPBB-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- HCQHVQSQHXZRGA-UHFFFAOYSA-N 4-bromo-2-phenylpyridine Chemical compound BrC1=CC=NC(C=2C=CC=CC=2)=C1 HCQHVQSQHXZRGA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AMLIKSUQSLZDGW-UHFFFAOYSA-N 1-pyridin-3-ylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C1=CC=CN=C1 AMLIKSUQSLZDGW-UHFFFAOYSA-N 0.000 description 2
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 2
- HSNBRDZXJMPDGH-UHFFFAOYSA-N 5-bromo-2-iodopyridine Chemical compound BrC1=CC=C(I)N=C1 HSNBRDZXJMPDGH-UHFFFAOYSA-N 0.000 description 2
- PRNGIODVYLTUKH-UHFFFAOYSA-N 5-bromo-2-phenylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=CC=C1 PRNGIODVYLTUKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- LEMABCWCFKCYQC-UHFFFAOYSA-N OBO.C1=CC=CC2=CC=CC=C21 Chemical class OBO.C1=CC=CC2=CC=CC=C21 LEMABCWCFKCYQC-UHFFFAOYSA-N 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XMWJLKOCNKJERQ-UHFFFAOYSA-N 1-bromoanthracene Chemical compound C1=CC=C2C=C3C(Br)=CC=CC3=CC2=C1 XMWJLKOCNKJERQ-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical class C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
- KRIILKQTJUOQCJ-UHFFFAOYSA-N 2-bromo-4-phenylpyridine Chemical compound C1=NC(Br)=CC(C=2C=CC=CC=2)=C1 KRIILKQTJUOQCJ-UHFFFAOYSA-N 0.000 description 1
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical class C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 1
- AWCQJXPOCRXHNK-UHFFFAOYSA-N 3-bromo-5-phenylpyridine Chemical compound BrC1=CN=CC(C=2C=CC=CC=2)=C1 AWCQJXPOCRXHNK-UHFFFAOYSA-N 0.000 description 1
- NRQUDOHCJMLGNP-UHFFFAOYSA-N B(O)(O)O.C1(=CC=CC=C1)C1=NC=CC=C1 Chemical compound B(O)(O)O.C1(=CC=CC=C1)C1=NC=CC=C1 NRQUDOHCJMLGNP-UHFFFAOYSA-N 0.000 description 1
- CKTZQETVIDMASY-UHFFFAOYSA-N BrC(C=C1)=CN=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 Chemical compound BrC(C=C1)=CN=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 CKTZQETVIDMASY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent 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
- 150000002979 perylenes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organic material and organic electroluminescence devices made of the same. The structural formula of the material is shown in the specification, wherein Ar is C6-C30 sub-polycyclic aromatic hydrocarbon, or C6-C30 polyheterocyclic aromatic hydrocarbon; and n is an integer from 1 to 3. The organic material of the invention can be used as an electronic transmission layer in the organic electroluminescence devices.
Description
Technical field
The present invention relates to a kind of novel organic materials, and the application in organic electroluminescence device, the ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field belonged to.
Background technology
The electron transport material that tradition is used in electroluminescence device is Alq
3, but Alq
3Electronic mobility lower (greatly about 10
-6Cm
2/ Vs).In order to improve the electronic transmission performance of electroluminescence device, the researchist has done a large amount of exploratory study work.The LG chemistry has been reported the derivative of a series of pyrenes in the patent specification of China, be used as electric transmission and injecting material in electroluminescence device, has improved the luminous efficiency (publication number CN 101003508A) of device.People such as Cao Yong synthesize FFF-Blm4 (J.Am.Chem.Soc.; (Communication); 2008; 130 (11); 3282-3283) as electric transmission and input horizon material (with Ba/Al and compare as negative electrode with Al separately), improved the electronics injection of device widely and transmitted, improved electroluminescence efficient.Kodak is in United States Patent (USP) (publication number US 2006/0204784 and US 2007/0048545), mention the mixed electronic transport layer, adopt a kind of material of low lumo energy and another kind of electron transport material and doping such as other materials such as metallic substance of having hanged down bright voltage to form.Based on the device of this mixed electronic transport layer, efficient and life-span etc. all is improved, but has increased the complicacy of device fabrication, is unfavorable for reducing the OLED cost.The electron transport material and/or the electronics injecting material of exploitation stability and high efficiency, thus bright voltage reduced, improve device efficiency, prolong device lifetime, have very important application value.
The ideal electron transport material should have the characteristic of following several respects: have the reversible electrochemical reducting reaction; HOMO and lumo energy are suitable; The electronic mobility height; Good film-forming property; The Tg height; Preferably can blocking hole.From the compound structure aspect, require molecule to contain the electron deficiency structural unit, have the good electronic capability of accepting; Molecular weight is enough big, guarantees to have higher Tg, thereby has good thermostability, and molecular weight can not be too big simultaneously, is beneficial to the vacuum evaporation film forming.
The compound that contains phenylpyridyl is typical electron deficiency system, has the good electronic capability of accepting.Therefore the present invention introduces phenyl ring and links to each other with the phenylpyridyl of electron deficiency on condensed ring system basis, forms to a certain degree song and turn round on space multistory, increases its film-forming properties.Consider the difficulty or ease and the Practical Performance of vacuum evaporation, its molecular weight of electron transport material of the present invention generally is no more than 800.
Based on above consideration, this patent is developed a kind of novel organic materials, and this material has good thermostability, and high electron mobility can be used as electron transfer layer in organic electroluminescence device.
Summary of the invention
The objective of the invention is to propose a kind of novel organic materials, its general structure is as follows:
In the following formula, it is 6 to 30 inferior condensed-nuclei aromatics that Ar is selected from carbonatoms, or to be selected from carbonatoms be 6 to 30 inferior fused heterocycle aromatic hydrocarbons, for example, Ar can be naphthylidene, connection naphthylidene, anthrylene, benzo anthrylene, Ya perylene base, inferior pyrenyl, phenylene pyridyl, diphenylene pyridyl,
Dibenzo
Deng; N is selected from 1 to 3 integer.
In the above-mentioned general formula, the structure of Ar is as follows when n=1:
The structure of Ar is as follows during n=2:
The structure of Ar is as follows during n=3:
The structure of the phenylpyridine group in the material general formula of the present invention is as follows:
In order more to clearly demonstrate content of the present invention, the preferred structure in the type of compounds that following mask body narration the present invention relates to:
1, when n=1, some main electron transport material structures following (only be that example illustrates it here with the anthracene, the compound that other Ar residue forms is therewith in like manner):
2, when n=2, some main electron transport material structures are as follows:
6, the described organic materials of claim 1 is used as the electric transmission layer material in organic electroluminescence device.
7, a kind of organic electroluminescence device wherein comprises pair of electrodes and is arranged on organic light emitting medium between this counter electrode, comprises a kind of described material of claim 1 that is selected from this organic light emitting medium at least.
8, organic electroluminescence device according to claim 7 is characterized in that, the described material that is selected from claim 1 is arranged in the electron transfer layer of this organic light emitting medium.
3, when n=3, typical electronic transport material structure is as follows:
Organic materials of the present invention is used as electron transfer layer in organic electroluminescence device.
The present invention also proposes a kind of organic electroluminescence device, comprises above-mentioned general formula compound in its organic function layer, and this compounds is as the electron transport material in the organic function layer.
Organic materials of the present invention has higher electronic mobility, can be used as electron transfer layer in display of organic electroluminescence.
Embodiment
Used various phenylpyridine boric acid among the present invention, various bromo anthracene, bromine for basic chemical industry raw materials such as perylene, bromo pyrene, anthraquinone, benzo anthraquinone all at home Chemicals market conveniently bought, all available common organic method of various phenylpyridine ylboronic acids is synthetic.
Embodiment
The synthetic method of compound in the present invention divides work three classes: the synthetic of asymmetric compound (during n=1) all can carry out with reference to embodiment 1; Symmetrical compound and a part of asymmetric compound (during n=2) can carry out with reference to embodiment 5, embodiment 7 and embodiment 18 methods; Part symmetrical compound and a part of asymmetric compound (during n=3) can carry out with reference to embodiment 18 methods.Set forth the synthetic method of part main compound in this patent below.
Embodiment 1 compound 1-1's is synthetic
(1) the first step reaction
The experimental equation formula
Reflux condensing tube and nitrogen protection device are installed on a there-necked flask.Add 9-bromine anthracene 4g (purity 91.40%, 0.0142), 1-naphthalene boronic acids 3.18g (purity 99.0%, 0.0183mol), Palladous chloride 0.19g (purity AR, 0.0011mol), triphenylphosphine 0.58g (purity AR, 0.0022mol), salt of wormwood 6.99g (purity AR, 0.0066mol), toluene 50ml, ethanol 38ml, water 25ml wherein naphthalene boronic acids graded add.With water pump bleed the ventilation three times after, back flow reaction under nitrogen protection.
React 2.5hr again after adding the 1g naphthalene boronic acids behind the reaction 1hr, the some plate, raw material point disappears.Stopped reaction.Separatory filters with the high silicagel column of 15cm, and organic impurity does not separate.Cross post with the high silicagel column of 35cm, pure sherwood oil flushing, colour band digs out product silica gel after separating, and ethyl acetate drip washing obtains the 3.95g intermediate, and HPLC analyzes: 83.78/3.212min, pure yield 76.66%.
The reaction of (2) second steps
Reaction equation
In the 1000ml there-necked flask, and adding the first step product 4g (purity 83.78%, 0.01102mol), cupric bromide 10g (purity AR, 0.04433mol), chlorobenzene 300ml, magnetic agitation, reflux, reaction 1.5hr, do not have obvious HBr and emit, off-response is after the room temperature, the silicagel column high with about 10cm filters out CuBr, and toluene is washed silica gel, and decompression is spin-dried for and obtains the brown dope, add petroleum ether and stirring, obtain yellow-green colour solid 4.9g, HPLC 89.39/4.891min.Pure productive rate: 100%.Further do not handle and directly drop into the next step.
(3) three-step reactions
Reaction equation
Reflux condensing tube and nitrogen protection device are installed on a there-necked flask, and second step of adding reaction product 7.5g (purity 89.39%, 0.01755mol); 2-phenylpyridine-4-boric acid 5.1g (purity 90.0%, 0.0228mol), Palladous chloride 0.5g (purity AR; 0.00282mol); triphenylphosphine 1.49g (purity AR, 0.005687mol), salt of wormwood 23.5g (purity AR; 0.1703mol); toluene 124ml, ethanol 80ml, water 113ml.With water pump bleed the ventilation three times after, back flow reaction under nitrogen protection.
Put plate behind the reaction 5hr, react completely stopped reaction.Put cold filtration, solid extracts with apparatus,Soxhlet's, and toluene is extracting solution, obtains the faint yellow solid product.Product is used chlorobenzene/toluene=1/10, and heat is boiled, and puts cold filtration, and this process reaches more than 99% until purity repeatedly, obtains the 5.67g product, molecular weight 457, purity 99.1%, yield 70.4%.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.85%, H:5.08%, N:3.07%.
Embodiment 2 compound 1-3's is synthetic
Select 9-bromine anthracene for use, the 1-naphthalene boronic acids, 5-phenylpyridine-3-boric acid is raw material, the three-step reaction through identical with embodiment 1 obtains compound 1-3.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.77%, H:5.15%, N:3.08%.
Embodiment 3 compound 1-5's is synthetic
Select 9-bromine anthracene for use, the 2-naphthalene boronic acids, 5-phenylpyridine-2-boric acid is raw material, the three-step reaction through identical with embodiment 1 obtains compound 1-5.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.87%, H:5.08%, N:3.05%.
Embodiment 4 compound 1-7's is synthetic
Select 9-bromine anthracene for use, the 2-naphthalene boronic acids, 5-phenylpyridine-3-boric acid is raw material, the three-step reaction through identical with embodiment 1 obtains compound 1-5.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.71%, H:5.18%, N:3.11%.
Embodiment 5 compound 2-1's is synthetic
(1) the first step reaction
500 milliliters of there-necked flasks are joined magnetic agitation, after the argon replaces successively by above-mentioned amount add 2-iodo-5-bromopyridine 13.4g (purity 99%, 0.0473mol), THF200ml.-83 ℃ drip down BuLi19ml (concentration 2.5M, 0.0475mol), add immediately anthraquinone 4.8g (purity 99%, 0.023mol).After adding, be warming up to room temperature naturally, solution is glassy yellow.Add the hydrolysis of 200ml water, use ethyl acetate extraction, solvent evaporated adds acetate 300ml, the KI of 18g and the inferior sodium phosphate of 18g, reflux, reacted 1 hour, cooling, evaporate to dryness acetate, wash it with water, obtain the 5.05g yellow product, purity 87.42%, productive rate 39.19%.
The reaction of (2) second steps
Under the N gas shiled, in a 500mL there-necked flask, add 9,10-two (5-bromopyridine-2-yl) anthracene 6.0g (molecular weight 490; purity 87.42%, 0.0106mol), phenylo boric acid 3.73g (purity 98%; 0.03mol), Palladous chloride 0.21g (purity AR, 0.00124mol); triphenylphosphine 0.63g (purity AR, 0.0024mol), salt of wormwood 5.3g (purity AR; 0.0486mol); toluene 86ml, ethanol 60ml, water 72ml.Above-mentioned material, reflux is added secondary phenylo boric acid (each 1g).Stopped reaction after 4 hours is put coldly, filters, and filter cake boils filtration with toluene heat, removes catalyzer, and toluene is fallen in steaming, and solid boils with water/THF of 1/10, puts cold leaching, and repeats two times.Obtain 4.1g lime look product, purity 99.14%, productive rate 77.97%.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.10%, H:5.08%, N:5.82%.
Embodiment 6 compound 2-3's is synthetic
Select anthraquinone for use, 2-iodo-5-bromopyridine, phenylo boric acid, the two steps reaction through identical with embodiment 5 obtains faint yellow compound 2-3.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.21%, H:5.05%, N:5.74%.
Embodiment 7 compound 2-5's is synthetic
500 milliliters of there-necked flasks are joined magnetic agitation, behind the nitrogen replacement successively by above-mentioned amount add 2-phenyl-5-bromopyridine 6.75g (purity 95.45%, 0.0274mol), THF110mol.Dropping butyllithium 13ml under-70 ℃ (concentration 2.5M 0.0325mol), stirs after 10 minutes, and adding anthraquinone 2.6g (purity 99%, 0.0124mol).After adding, be warming up to room temperature naturally, solution is glassy yellow.Add the hydrolysis of 200ml water, use ethyl acetate extraction, solvent evaporated.Add acetate 220ml, each 22g of KI and inferior sodium phosphate refluxes.Reacted 1 hour, cooling, cooling leaches, and gets the faint yellow product of 2.8g.Water/THF with 15/100 boiled 1 hour, put cold leaching, and repeated multiple times obtains 2.1g pale solid product, purity 99.0%, productive rate 20.48%.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.30%, H:5.01%, N:5.69%.
Embodiment 8 compound 2-7's is synthetic
Select anthraquinone for use, 2-phenyl-4-bromopyridine, the reaction through identical with embodiment 7 obtains faint yellow compound 2-7.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.22%, H:5.03%, N:5.75%.
Embodiment 9 compound 2-9's is synthetic
Select anthraquinone for use, 2-phenyl-4-bromopyridine, the reaction through identical with embodiment 7 obtains faint yellow compound 2-9.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.18%, H:5.03%, N:5.79%.
Embodiment 10 compound 2-11's is synthetic
Select 2 for use, 6-two (3-pyridyl) anthraquinone, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-11.
Product MS (m/e): 484; Ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.40%, H:4.79%, N:8.81%.
Embodiment 11 compound 2-13's is synthetic
Select 2 for use, 6-two (3-pyridyl) anthraquinone, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-13.
Product MS (m/e): 638; Ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.40%, H:4.79%, N:8.81%.
Embodiment 12 compound 2-15's is synthetic
Select the benzo anthraquinone for use, 4-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-15.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.80%, H:4.91%, N:5.29%.
Embodiment 13 compound 2-17's is synthetic
Select the benzo anthraquinone for use, 2-phenyl-4-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-17.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.85%, H:4.82%, N:5.33%.
Embodiment 14 compound 2-19's is synthetic
Select the benzo anthraquinone for use, 2-phenyl-5-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-19.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.70%, H:5.02%, N:5.28%.
Embodiment 15 compound 2-21's is synthetic
Select the benzo anthraquinone for use, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-21.
Product MS (m/e): 584; Ultimate analysis (C
44H
28N
2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.46%, H:4.70%, N:4.84%.
Embodiment 16 compound 2-23's is synthetic
Select phenanthrenequione for use, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-23.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.40%, H:4.85%, N:5.75%.
Embodiment 17 compound 2-25's is synthetic
Select phenanthrenequione for use, 5-phenyl-3-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-25.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.25%, H:4.88%, N:5.87%.
Embodiment 18 compound 2-27's is synthetic
Under the N gas shiled, in a 500mL there-necked flask, add 3,9-2-Xiu perylene 4.32g (purity 95%; 0.01mol), 6-phenylpyridine-3-boric acid 5.1g (purity 98%, 0.025mol); Palladous chloride 0.21g (purity AR, 0.0012mol), triphenylphosphine 0.63g (purity AR; 0.0024mol); salt of wormwood 5.3g (purity AR, 0.0486mol), toluene 86ml; ethanol 60ml, water 72ml.Above-mentioned material, reflux.Stopped reaction after 4 hours is put coldly, filters, and filter cake boils filtration with toluene heat, removes catalyzer, and toluene is fallen in steaming, and solid boils with water/THF of 1/10, puts cold leaching, and repeats two times.Obtain 4.2g beige product, purity 99.10%, productive rate 75.26%.
Product MS (m/e): 558; Ultimate analysis (C
42H
26N
2): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.11%, H:4.88%, N:5.01%.
Embodiment 18 compound 2-29's is synthetic
Select 3 for use, 9-2-Xiu perylenes, 5-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-29.
Product MS (m/e): 558; Ultimate analysis (C
42H
26N
2): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.11%, H:4.88%, N:5.01%.
Embodiment 19 compound 2-31's is synthetic
Select 6 for use, 12-two-bromine is bent, 4-phenylpyridine-2-boric acid, and the reaction through identical with embodiment 18 obtains yellow compound 2-31.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:90.01%, H:4.86%, N:5.13%.
Embodiment 20 compound 2-33's is synthetic
Select 6 for use, 12-two-bromine is bent, 5-phenylpyridine-3-boric acid, and the reaction through identical with embodiment 18 obtains yellow compound 2-33.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.80%, H:4.93%, N:5.27%.
Embodiment 21 compound 2-35's is synthetic
Select 1 for use, 6-two-bromine pyrene, 4-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-35.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.51%; Measured value C:89.81%, H:4.70%, N:5.49%.
Embodiment 22 compound 2-37's is synthetic
Select 1 for use, 6-two-bromine pyrene, 2-phenylpyridine-4-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-37.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.51%; Measured value C:89.70%, H:4.81%, N:5.49%.
Embodiment 23 compound 2-39's is synthetic
Select 1 for use, 6-two-bromine pyrene, 5-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-39.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.51%; Measured value C:89.68%, H:4.71%, N:5.61%.
Embodiment 24 compound 2-41's is synthetic
Select 4 for use, 9-two-bromonaphthalene and thiadiazoles, 6-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains red compound 2-41.
Product MS (m/e): 492; Ultimate analysis (C
32H
20N
4S): theoretical value C:78.02%, H:4.09%, N:11.37%, S:6.51%; Measured value C:78.10%, H:4.06%, N:11.42%, S:6.42%.
Embodiment 25 compound 2-42's is synthetic
Select 4 for use, 9-two-bromonaphthalene and thiadiazoles, 5-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains red compound 2-42.
Product MS (m/e): 492; Ultimate analysis (C
32H
20N
4S): theoretical value C:78.02%, H:4.09%, N:11.37%, S:6.51%; Measured value C:78.05%, H:4.10%, N:11.40%, S:6.45%.
Embodiment 26 compound 3-1's is synthetic
Select 1,3 for use, 5-three bromonaphthalenes, 5-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains faint yellow compound 3-1.
Product MS (m/e): 587; Ultimate analysis (C
43H
29N
3): theoretical value C:87.88%, H:4.97%, N:7.15%; Measured value C:87.81%, H:4.95%, N:5.24%.
Embodiment 27 compound 3-3's is synthetic
Select 4,6 for use, 8-three bromoquinolines, 5-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 3-3.
Product MS (m/e): 588; Ultimate analysis (C
42H
28N
4): theoretical value C:85.69%, H:4.79%, N:9.52%; Measured value C:85.72%, H:4.85%, N:9.43%.
Be the Application Example of The compounds of this invention below:
Embodiment 28: the preparation of electroluminescence device and result
The preferred implementation of fabricate devices:
(1) designs
The transmission performance that compares these electron transport materials for convenience, the present invention has designed a simple electroluminescence device (substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode), only use compound 2-1 and 2-5 as the electron transport material illustration, efficent electronic transport material Bphen is material as a comparison, (EM1 is a material of main part to EM1 as the luminescent material illustration, it is not luminescent material, purpose is not to pursue high-level efficiency, but verifies the possibility of these material practicalities).The structure of Bphen and EM1 is:
Substrate can use the substrate in traditional organic luminescent device, for example: glass or plastics.Select glass substrate for use in element manufacturing of the present invention, ITO makes anode material.
Hole transmission layer can adopt various tri-arylamine group materials.Selected hole mobile material is NPB in element manufacturing of the present invention.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., also can be electron injecting layer/metal-layer structure, as LiF/Al, Li
2Common cathode construction such as O.Electronics injecting material selected in element manufacturing of the present invention is LiF, and cathode material is Al.
(2) element manufacturing
Sheet glass supersound process in commercial clean-out system of ITO transparency conducting layer will be coated with, wash in deionized water, at acetone: ultrasonic oil removing in the alcohol mixed solvent is baked under clean environment and removes moisture content fully, with UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned anodic glass substrate that has is placed in the vacuum chamber, be evacuated to 1 * 10
-5～9 * 10
-3Pa, vacuum evaporation NPB is as hole transmission layer on above-mentioned anode tunic, and evaporation speed is 0.1nm/s, and the evaporation thickness is 50nm;
Vacuum evaporation EM1 or EM2 are as the luminescent layer of device on hole transmission layer, and evaporation speed is 0.1nm/s, and the evaporation total film thickness is 30nm;
Vacuum evaporation one deck compound 1-7 or 2-7 be as the electron transfer layer of device on luminescent layer, and other adopts Bphen of the prior art as the electron transfer layer of device as a comparison case, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 50nm;
Go up the negative electrode of vacuum evaporation Al layer as device at electron transfer layer (ETL), thickness is 150nm.
Device performance see the following form (device architecture: ITO/NPB (40nm)/EM1 (30nm)/ETL material (20nm)/LiF (0.5nm)/Al (150nm))
Above result shows that novel organic materials of the present invention can be preferably used as electron transfer layer in organic electroluminescence device.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to the foregoing description, should be appreciated that those skilled in the art can carry out various modifications and improvement under the guiding of the present invention's design, and claims have been summarized scope of the present invention.
Claims (8)
1. organic materials, its general structure is as follows:
In the following formula, it is 6 to 30 inferior condensed-nuclei aromatics that Ar is selected from carbonatoms, or to be selected from carbonatoms be 6 to 30 inferior fused heterocycle aromatic hydrocarbons; N is selected from 1 to 3 integer.
2. according to the organic materials of claim 1, it is characterized in that, Ar be selected from naphthylidene, connection naphthylidene, anthrylene, benzo anthrylene, Ya perylene base, inferior pyrenyl, phenylene pyridyl, diphenylene pyridyl,
Dibenzo
3. according to the organic materials of claim 1, it is characterized in that:
The structure of Ar is as follows during n=1:
The structure of Ar is as follows during n=2:
The structure of Ar is as follows during n=3:
4. according to the organic materials of claim 1, it is characterized in that the structure of the phenylpyridine group in the material general formula is as follows:
5. the described organic materials of claim 1, structural formula is as follows:
6. the described organic materials of claim 1 is used as the electric transmission layer material in organic electroluminescence device.
7. organic electroluminescence device wherein comprises pair of electrodes and is arranged on organic light emitting medium between this counter electrode, comprises a kind of described material of claim 1 that is selected from this organic light emitting medium at least.
8. organic electroluminescence device according to claim 7 is characterized in that the described material that is selected from claim 1 is arranged in the electron transfer layer of this organic light emitting medium.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910234760 CN101891673B (en) | 2009-11-13 | 2009-11-13 | Organic material and application thereof in organic electroluminescence devices |
| PCT/CN2009/076276 WO2011057461A1 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| KR1020127004954A KR101411122B1 (en) | 2009-11-13 | 2009-12-30 | Organic material and organic EL device using the same material |
| US13/497,131 US9412951B2 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| JP2012527175A JP5498580B2 (en) | 2009-11-13 | 2009-12-30 | ORGANIC MATERIAL AND ORGANIC EL DEVICE USING THE MATERIAL |
| PL09851216T PL2500343T3 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| EP09851216.3A EP2500343B1 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910234760 CN101891673B (en) | 2009-11-13 | 2009-11-13 | Organic material and application thereof in organic electroluminescence devices |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101891673A true CN101891673A (en) | 2010-11-24 |
| CN101891673B CN101891673B (en) | 2013-03-20 |
Family
ID=43101048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200910234760 Active CN101891673B (en) | 2009-11-13 | 2009-11-13 | Organic material and application thereof in organic electroluminescence devices |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101891673B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102916134A (en) * | 2012-10-31 | 2013-02-06 | 昆山维信诺显示技术有限公司 | Electron transfer layer, organic electroluminescent device with electron transfer layer and manufacturing method thereof |
| CN103579528A (en) * | 2012-07-31 | 2014-02-12 | 昆山维信诺显示技术有限公司 | Electronic transfer layer, organic light-emitting device comprising electronic transfer layer and manufacturing method of organic light-emitting device |
| CN103794731A (en) * | 2013-12-31 | 2014-05-14 | 北京维信诺科技有限公司 | Organic light-emitting display device and organic light-emitting display thereof |
| JPWO2012070535A1 (en) * | 2010-11-25 | 2014-05-19 | Jnc株式会社 | Electron transport material and organic electroluminescent device using the same |
| CN103762318B (en) * | 2013-12-31 | 2017-01-18 | 昆山工研院新型平板显示技术中心有限公司 | Top emission OLED device |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103700775B (en) | 2013-12-31 | 2017-08-25 | 北京维信诺科技有限公司 | A kind of organic electroluminescence device and preparation method thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1239447C (en) * | 2002-01-15 | 2006-02-01 | 清华大学 | Organic electroluminescent material |
| CN101077971B (en) * | 2006-05-25 | 2010-08-11 | 清华大学 | Organic electroluminescent phosphorescence luminescent material and application thereof |
-
2009
- 2009-11-13 CN CN 200910234760 patent/CN101891673B/en active Active
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2012070535A1 (en) * | 2010-11-25 | 2014-05-19 | Jnc株式会社 | Electron transport material and organic electroluminescent device using the same |
| JP5907069B2 (en) * | 2010-11-25 | 2016-04-20 | Jnc株式会社 | Electron transport material and organic electroluminescent device using the same |
| CN103579528A (en) * | 2012-07-31 | 2014-02-12 | 昆山维信诺显示技术有限公司 | Electronic transfer layer, organic light-emitting device comprising electronic transfer layer and manufacturing method of organic light-emitting device |
| CN103579528B (en) * | 2012-07-31 | 2016-03-30 | 昆山维信诺显示技术有限公司 | Electron transfer layer, containing the organic electroluminescence device of this electron transfer layer and preparation |
| CN102916134A (en) * | 2012-10-31 | 2013-02-06 | 昆山维信诺显示技术有限公司 | Electron transfer layer, organic electroluminescent device with electron transfer layer and manufacturing method thereof |
| CN102916134B (en) * | 2012-10-31 | 2016-06-29 | 昆山维信诺科技有限公司 | Electron transfer layer, organic electroluminescence device containing this layer and manufacture method thereof |
| CN103794731A (en) * | 2013-12-31 | 2014-05-14 | 北京维信诺科技有限公司 | Organic light-emitting display device and organic light-emitting display thereof |
| CN103762318B (en) * | 2013-12-31 | 2017-01-18 | 昆山工研院新型平板显示技术中心有限公司 | Top emission OLED device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101891673B (en) | 2013-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101875637B (en) | Organic material and application thereof in organic electroluminescence devices | |
| CN101407493B (en) | Organic material and use thereof in organic EL device | |
| CN100425599C (en) | Organic electroluminescent material and its application | |
| CN101987822B (en) | Organic electroluminescent material and application thereof | |
| CN101597259B (en) | Organic material and application thereof in organic electroluminescence device (OELD) | |
| CN103833507A (en) | Organic electroluminescent materials, and preparation method and application thereof | |
| CN101891673B (en) | Organic material and application thereof in organic electroluminescence devices | |
| CN104513247B (en) | A kind of benzo ［ c ］ benzo ［ 3,4 ］ carbazole and carbazole derivates and application | |
| CN104628581A (en) | 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compound and organic electroluminescence device containing same | |
| CN101898996A (en) | Organic material and application thereof to organic electroluminescent devices | |
| CN109824672A (en) | A kind of quinazo triazole derivatives and its application in field of organic electroluminescence | |
| CN106554319A (en) | A kind of * analog derivatives containing quinazoline group and its application | |
| CN110437081A (en) | Organic compound containing tricycloheptane and preparation method thereof and organic electroluminescence device comprising the compound | |
| CN106554352A (en) | A kind of condensed-nuclei aromatics derivant containing naphthyridines group and its application | |
| CN102532002B (en) | Tetrahydroanthracene compound containing terpyridyl group and application thereof | |
| CN109020979A (en) | A kind of electroluminescent organic material and preparation method and application with heterocycle structure | |
| CN109054810A (en) | Using diphenylsulfide as the thermal excitation delayed fluorescence material of main part of parent and its preparation and application | |
| CN108440554A (en) | A kind of electroluminescent organic material, application and its device | |
| CN110526905A (en) | A kind of compound containing ketone and its application on organic electroluminescence device | |
| CN110903282B (en) | Compound and organic electroluminescent device | |
| CN1931803B (en) | Organic electroluminescent material and its application | |
| CN110015994A (en) | Thermal activation delayed fluorescence material and preparation method thereof, display device | |
| CN109608384A (en) | A kind of organic material and preparation method thereof and its application in electroluminescent device | |
| CN101597255A (en) | A kind of organic materials and the application in organic electroluminescence device thereof | |
| CN117143030A (en) | Naphthyl substituted electricity-absorbing fragment compound, electron transport material and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20101124 Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO., LTD. Assignor: Kunshan visionox Technology Co., Ltd. |Beijing weixinnuo Technology Co. Ltd Contract record no.: 2014990000306 Denomination of invention: Organic material and application thereof in organic electroluminescence devices Granted publication date: 20130320 License type: Exclusive License Record date: 20140516 |
|
| LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model |