CN115703786A - Heterocyclic aromatic compound and application thereof - Google Patents
Heterocyclic aromatic compound and application thereof Download PDFInfo
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- CN115703786A CN115703786A CN202110914965.1A CN202110914965A CN115703786A CN 115703786 A CN115703786 A CN 115703786A CN 202110914965 A CN202110914965 A CN 202110914965A CN 115703786 A CN115703786 A CN 115703786A
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- heterocyclic aromatic
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 title claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 14
- -1 heterocyclic aromatic hydrocarbon compound Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 230000005525 hole transport Effects 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 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
- 125000005560 phenanthrenylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000005551 pyridylene group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005564 oxazolylene group Chemical group 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000005558 triazinylene group Chemical group 0.000 claims description 2
- 125000005556 thienylene group Chemical group 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- 229940125904 compound 1 Drugs 0.000 description 14
- 238000012512 characterization method Methods 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000005401 electroluminescence Methods 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
- 230000009477 glass transition Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LGHFDZYDDIPIQK-UHFFFAOYSA-N 11-phenylbenzo[a]carbazole Chemical compound C1=CC=CC=C1N1C2=C3C=CC=CC3=CC=C2C2=CC=CC=C21 LGHFDZYDDIPIQK-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- QSOAYCUFEQGHDN-UHFFFAOYSA-N 9-naphthalen-1-ylcarbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=CC2=CC=CC=C12 QSOAYCUFEQGHDN-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention provides a heterocyclic aromatic compound and application thereof, wherein the heterocyclic aromatic compound has a structure shown in a formula I. The heterocyclic aromatic compound can be used as an electron transmission material of an organic electroluminescent device, so that the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life, the current efficiency reaches 4.53-4.83Cd/A, the T95 reaches more than 325h, and the driving voltage is reduced to 3.48-3.87V.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to a heterocyclic aromatic compound and application thereof.
Background
The organic electroluminescence phenomenon is a phenomenon that a luminescent material converts electric energy into light energy under the action of an electric field. Compared with the earlier developed inorganic electroluminescence, the organic electroluminescence has the advantages of wide material selectivity, capability of realizing full-color display from a blue light region to a red light region, low driving voltage, high brightness and luminous efficiency, wide viewing angle, high response speed, relatively simple manufacturing process, low cost, capability of realizing flexible display and the like. At present, the organic light-emitting diode is mainly applied to the aspects of organic flat panel display (OLED), organic solar cells, organic electronic circuits and the like, and the material selection range is quite wide; according to statistics, the visual information accounts for about 70% of the total amount of the obtained information, so that the display technology is a main bridge for connecting modern society people and information, and with the rapid development of the information technology, people urgently need lighter and thinner high-performance flat panel display devices. Organic electroluminescent devices (OLEDs), which are a member of flat panel displays, especially white organic electroluminescent devices, have recently been under intense research worldwide due to their great potential advantages in full color displays, liquid crystal backlights, and solid state lighting.
Although the organic electroluminescent display device has been developed in a large scale, there are still many important basic problems in the aspects of the OLED light emitting material, the colorization technology, the film making technology, the active driving technology, the encapsulation technology, etc., which result in short device lifetime, low efficiency, and high cost due to the inexhaustible process.
CN109369669A discloses a triazine bibenzothiophene pyrimidine organic compound, which has the following structure:
wherein R is 1 、R 2 Is one or two of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene, binaphthyl, bianthracene, fluoranthene, benzanthracene, fluorene, benzofluorene, N-phenylcarbazole, N-naphthylcarbazole, N-phenylbenzocarbazole, dibenzofuran and dibenzothiophene; the organic compound has the characteristics of higher glass transition temperature, good thermal stability, easy formation of amorphous film and long luminescent life. However, in the prior art, the glass transition temperature is high, and the amorphous film is not easy to form, so that the stability is poor.
Therefore, in the art, it is desired to develop an organic light emitting compound capable of allowing an organic electroluminescent device to have a lower driving voltage and higher current efficiency.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide a heterocyclic aromatic compound and application thereof. The heterocyclic aromatic compound can be used as an electron transmission material of an organic electroluminescent device, so that the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a heterocyclic aromatic compound having a structure represented by formula I:
wherein, L is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group; r 1 And R 2 The same or different from each other, and each independently is hydrogen, deuterium, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C1-C20 silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C5-C30 heteroarylamine group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C30 heteroaryl group; ar (Ar) 1 And Ar 2 Each independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; x 1 To X 3 The same or different from each other, and each independently is N or CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; y is divalent S or O.
In the present invention, the heterocyclic aromatic compound may be used as an electron transport material for an organic electroluminescent device. Higher glass transition temperature and good thermal stability, easily forms an amorphous film, and realizes lower driving voltage, higher current efficiency and longer service life.
Preferably, the L is a direct bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C6-C60 heteroarylene.
Preferably, L is any one of a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrenylene group, a fluorenylene group, a furanylene group, a thiophenylene group, a pyrrolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a carbazylene group, an acridinylene group, an imidazolyl group, an oxazolylene group, a thiazolyl group, an indolyl group, a benzofuranylene group, a benzothiophene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzimidazolylene group, a quinolylene group, or an isoquinolylene group.
Preferably, L is any one of a direct bond, phenylene, biphenylene, naphthylene, anthracenylene, phenanthrenylene, and pyridinylene.
Preferably, L is a direct bond,
Any one of them.
Preferably, R 1 And R 2 Each independently phenyl, pyridyl or pyrimidinyl.
Preferably, ar 1 And Ar 2 Each independently selected from substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C6 to C60 heteroaryl;
preferably, ar 1 And Ar 2 Each independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, N-phenylcarbazolyl, furyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, carbazolyl, acridinyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, benzimidazolyl, quinolyl or isoquinolyl, with phenyl and biphenyl being more preferred.
Preferably, said X 1 To X 3 Are each CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl or substitutedOr unsubstituted C6-C60 heteroaryl.
Further preferably, R' is any one of hydrogen, deuterium, cyano, methyl, ethyl, propyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, N-phenylcarbazolyl, furyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, carbazolyl, acridinyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, quinolyl or isoquinolyl.
Preferably, said X 1 To X 3 At least one of which is N.
Preferably, said X 1 To X 3 Wherein both are N or X 1 To X 3 Are all N.
In the present invention, when a substituent is present in the group as described above, the substituent is selected from deuterium, halogen, cyano, nitro, hydroxy, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C5-C30 aryloxy, C5-C30 aryl, and C5-C30 heteroaryl.
The term "C6-C60" as used herein refers to the number of carbon atoms in the group, and is analogous to the term "C1-C20".
The C6 to C60 may be C6, C7, C8, C9, C10, C12, C15, C18, C20, C22, C24, C25, C27, C29, C32, C35, C38, C40, C42, C45, C48, C50, C52, C55, C57, C59, or the like.
The C1-C20 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C15, C18, C20, etc.
The C3-C20 can be C3, C4, C5, C6, C7, C8, C9, C10, C12, C15, C18, C20, etc.
The C5-C30 can be C6, C7, C8, C9, C10, C12, C15, C18, C20, C22, C24, C25, C27, C29, and the like.
Preferably, the heterocyclic aromatic compound is any one of the following compounds:
In the present invention, the heterocyclic aromatic compound is synthesized, illustratively, by the following synthetic route:
in another aspect, the present invention provides an electron transport material comprising any of the heterocyclic aromatic compounds described above.
In another aspect, the present invention provides an OLED device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked, wherein the material of the electron transport layer comprises any one of the heterocyclic aromatic hydrocarbon compounds described above.
In another aspect, the present invention provides an electronic device comprising an OLED device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the heterocyclic aromatic compound can be used as an electron transmission material of an organic electroluminescent device, so that the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life, the current efficiency reaches 4.53-4.83Cd/A, the T95 reaches more than 325h, and the driving voltage is reduced to 3.48-3.87V.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation of example 1
Preparation of Compound 1
In a 200mL three-necked flask were added 0.5mmol of Compound A,1g of anhydrous cesium carbonate powder, and 0.2g of Pd in this order 2 dba 3 (tris (dibenzylideneacetone) dipalladium) followed by 100mL of anhydrous 1,4-dioxane was added and stirred well. In the process, nitrogen is supplemented and vacuum pumping is carried out at the same time, so that the reaction is in a nitrogen atmosphere. Heating and keeping at 140 ℃, dropwise adding 0.5mmol of compound B, refluxing and reacting for 18h in the dark, and tracing a dot plate until the reaction is complete. And (4) cooling, recrystallizing and carrying out chromatographic column chromatography to obtain the required target compound.
Characterization data for compound 1:
1 H NMR(400MHz，DMSO)δ7.49(2H)，δ7.41(2H)，δ7.75(2H)，δ7.55(2H)，δ7.37(2H)，δ7.14(2H)，δ7.15(1H)，δ7.67(1H)，δ7.98(1H)，δ8.01(1H)δ7.31(1H)，δ7.39(2H)，δ7.54(2H)。
MS[M+H]：556。
elemental analysis: c,75.66; o,2.88; n,17.65; h,3.81.
Preparation of example 2
Preparation of Compound 2
The preparation method is the same as that of the compound 1.
Characterization data for compound 2:
1 H NMR(400MHz，DMSO)δ7.44(2H)，δ7.52(2H)，δ7.76(2H)，δ7.58(2H)，δ7.37(2H)，δ7.14(2H)，δ7.17(1H)，δ7.66(1H)，δ7.98(1H)，δ7.31(1H)，δ8.07(1H)，δ7.39(2H)，δ7.54(2H)。
MS[M+H]：555。
elemental analysis: c,77.96; o,2.88; n,15.15; h,4.
Preparation of example 3
Preparation of Compound 3
The preparation method is the same as that of the compound 1.
Characterization data for compound 3:
1 H NMR(400MHz，DMSO)δ7.41(2H)，δ7.42(2H)，δ7.74(2H)，δ7.48(2H)，δ7.57(2H)，δ7.04(2H)，δ7.27(1H)，，δ7.49(2H)，δ7.57(2H)δ7.67(1H)，δ7.88(1H)，δ7.31(1H)，δ8.07(1H)，δ7.39(2H)，δ7.54(2H)。MS[M+H]：632。
elemental analysis: c,77.96; o,2.53; n,15.52; h,3.99.
Preparation of example 4
Preparation of Compound 4
The preparation method is the same as that of the compound 1.
Characterization data for compound 4:
1 H NMR(400MHz，DMSO)δ7.21(2H)，δ7.32(2H)，δ7.74(2H)，δ7.48(2H)，δ7.57(2H)，δ7.34(4H)，δ7.27(1H)，，δ7.39(4H)，δ7.57(2H)δ7.67(1H)，δ7.89(1H)，δ7.31(1H)，δ8.07(1H)，δ7.39(2H)，δ7.54(2H)。
MS[M+H]：732。
elemental analysis: c,80.42; o,2.19; n,13.4; h,3.99.
Preparation of example 5
Preparation of Compound 5
The preparation method is the same as that of the compound 1.
Characterization data for compound 5:
1 H NMR(400MHz，DMSO)δ7.39(2H)，δ7.31(2H)，δ7.65(2H)，δ7.45(2H)，δ7.39(2H)，δ7.18(2H)，δ7.19(1H)，δ7.87(1H)，δ7.78(1H)，δ8.01(1H)δ7.35(1H)，δ7.47(2H)，δ7.74(2H)。
MS[M+H]：573。
elemental analysis: c,73.54; s,5.61; n,17.15; h,3.7.
Preparation of example 6
Preparation of Compound 6
The preparation method is the same as that of the compound 1.
Characterization data for compound 6:
1 H NMR(400MHz，DMSO)δ7.35(2H)，δ7.47(2H)，δ7.81(2H)，δ7.49(2H)，δ7.40(2H)，δ7.15(2H)，δ7.17(1H)，δ7.66(1H)，δ7.98(1H)，δ7.31(1H)，δ8.07(1H)，δ7.23(2H)，δ7.64(2H)。
MS[M+H]：571。
elemental analysis: c,75.77; s,5.62; n,14.73; h,3.89.
Preparation of example 7
Preparation of Compound 7
The preparation method is the same as that of the compound 1.
Characterization data for compound 7:
1 H NMR(400MHz，DMSO)δ7.39(2H)，δ7.40(2H)，δ7.72(2H)，δ7.51(2H)，δ7.53(2H)，δ7.25(2H)，δ7.27(1H)，，δ7.49(2H)，δ7.59(2H)δ7.67(1H)，δ7.88(1H)，δ7.31(1H)，δ8.07(1H)，δ7.33(2H)，δ7.54(2H)。
MS[M+H]：648。
elemental analysis: c,76.02; s,4.95; n,15.14; h,3.89.
Preparation of example 8
Preparation of Compound 8
The preparation method is the same as that of the compound 1.
Characterization data for compound 8:
characterization data for compound 8:
1 H NMR(400MHz，DMSO)δ7.33(2H)，δ7.41(2H)，δ7.74(2H)，δ7.48(2H)，δ7.57(2H)，δ7.50(4H)，δ7.27(1H)，，δ7.40(4H)，δ7.57(2H)δ7.67(1H)，δ7.89(1H)，δ7.31(1H)，δ8.06(1H)，δ7.27(2H)，δ7.55(2H)。
MS[M+H]：748。
elemental analysis: c,78.69; o,4.29; n,13.11; h,3.91.
Device example 1
Coating thereon with thickness
The glass substrate of Indium Tin Oxide (ITO) thin film of (a) was put in distilled water in which a detergent was dissolved, and cleaned using ultrasonic waves. In this case, a product manufactured by Fischer co. was used as a detergent, and distilled water filtered twice by a filter manufactured by Millipore c. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes using distilled water. After the washing with distilled water was completed, ultrasonic washing was performed using solvents of isopropyl alcohol, acetone, and methanol, and the resultant product was dried and then transferred to a plasma washing machine. Furthermore, by using oxygen plasmaThe substrate was bulk cleaned for 5 minutes and then transferred to a vacuum depositor.
The following structure of hexanitrile Hexaazatriphenylene (HAT) is used for thermal vacuum deposition on the transparent electrode prepared thereby
A thickness of, a deposition rate of
Thereby forming a hole injection layer;
the compound N4, N4, N4', N4' -tetrakis ([ 1,1' -biphenyl) of the following structure was used]-4-yl) - [1,1' -biphenyl]-4,4' -diamine
As a hole transport layer material is vacuum deposited on the hole injection layer at a deposition rate of
Thereby forming a hole transport layer;
subsequently, the following BH and BD were used to vacuum deposit on the hole transport layer at a weight ratio of 25
Film thickness of, deposition rate of
Thereby forming a light emitting layer.
The compound 1 prepared in preparation example 1 and the compound LiQ (lithium quinolinate) were vacuum-deposited on the light-emitting layer at a weight ratio of 1:1 at a deposition rate of
Thereby forming a thickness of
Electron injection and transport layers. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron injection and transport layers respectively
And
the thickness of (a), the lithium fluoride (LiF) and the aluminum deposition rate are respectively maintained at
And
thus, a negative electrode was formed, thereby obtaining an organic light-emitting device. The vacuum degree during deposition is maintained at 5X 10 -6 And supporting the substrate, thereby fabricating an organic light emitting device.
Device example 2
An organic light-emitting device was fabricated in the same manner as in device example 1, except that compound 2 was used instead of compound 1 in device example 1.
Device example 3
An organic light-emitting device was manufactured in the same manner as in device example 1 except that compound 3 was used instead of compound 1 in device example 1.
Device example 4
An organic light-emitting device was produced in the same manner as in device example 1 except that compound 4 was used instead of compound 1 in device example 1.
Device example 5
An organic light-emitting device was fabricated in the same manner as in device example 1, except that compound 5 was used instead of compound 1 in device example 1.
Device example 6
An organic light-emitting device was fabricated in the same manner as in device example 1, except that compound 6 was used instead of compound 1 in device example 1.
Device example 7
An organic light-emitting device was produced in the same manner as in device example 1 except that compound 7 was used instead of compound 1 in device example 1.
Device example 8
An organic light-emitting device was fabricated in the same manner as in device example 1, except that compound 8 was used instead of compound 1 in device example 1.
Comparative example 1
An organic light-emitting device was fabricated in the same manner as in device example 1, except that ET1 was used instead of compound 1 in device example 1.
Comparative example 2
An organic light-emitting device was fabricated in the same manner as in device example 1, except that ET2 was used instead of compound 1 in device example 1.
Comparative example 3
An organic light-emitting device was fabricated in the same manner as in device example 1, except that ET3 was used instead of compound 1 in device example 1.
Comparative example 4
An organic light-emitting device was fabricated in the same manner as in device example 1, except that ET4 was used instead of compound 1 in device example 1.
When a current (10 mA/cm) was applied to the organic light emitting devices manufactured in device examples 1 to 8 and comparative examples 1 to 4 2 ) Voltage, current density, brightness, color coordinates and service life were measured, and the results are shown in table 1 below. T95 refers to the time it takes for the luminance to decrease to 95% of the original luminance (5000 nits). The test results are shown in table 1.
TABLE 1
As shown in table 1, it can be seen that the compounds of device examples 1 to 8, as electron transport layers of organic light emitting devices, exhibited better performance in terms of current efficiency, driving voltage, luminance and lifespan than the compounds of comparative examples 1 to 4, and the organic light emitting devices of the present invention had lower driving voltage (3.87V or less), higher current efficiency (4.53 to 4.83 Cd/a), and longer lifespan (325 h or more).
The applicant states that the present invention is illustrated by the above examples of the heterocyclic aromatic compounds of the present invention and their applications, but the present invention is not limited to the above examples, i.e. it is not meant to imply that the present invention must be practiced by relying on the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A heterocyclic aromatic compound having a structure according to formula I:
wherein L is a direct bond, a substituted or unsubstituted arylene, a substituted or unsubstituted heteroarylene; r 1 And R 2 The same or different from each other, and each independently is hydrogen, deuterium, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C1-C20 silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C5-C30 heteroarylamine group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C30 heteroaryl group; ar (Ar) 1 And Ar 2 Each independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; x 1 To X 3 The same or different from each other, and each independently is N or CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; y is divalent S or O.
2. The heterocyclic aromatic hydrocarbon compound according to claim 1, wherein L is a direct bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 heteroarylene group;
preferably, L is any one of a direct bond, phenylene, biphenylene, terphenylene, naphthylene, anthracenylene, phenanthrenylene, fluorenylene, furylidine, thienylene, pyrrolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, carbazolyl, acridinylene, imidazolyl, oxazolylene, thiazolyl, indolyl, benzofuranylene, benzothiophene, dibenzofuranylene, dibenzothiophenylene, benzimidazolylene, quinolylene or isoquinolylene;
preferably, L is any one of a direct bond, phenylene, biphenylene, naphthylene, anthracenylene, phenanthrenylene, and pyridinylene.
3. The heterocyclic aromatic compound according to claim 1 or 2, wherein L is a direct bond,
Any one of them.
4. The heterocyclic aromatic compound according to any one of claims 1 to 3, wherein R is 1 And R 2 Each independently is phenyl, pyridyl or pyrimidinyl.
5. The heterocyclic aromatic compound according to any one of claims 1 to 4, wherein Ar is Ar 1 And Ar 2 Each independently selected from substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C6 to C60 heteroaryl;
preferably, ar 1 And Ar 2 Each independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, N-phenylcarbazolyl, furyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, carbazolyl, acridinyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, benzimidazolyl, quinolyl or isoquinolyl, further preferably phenyl, anthryl or naphthyl.
6. The heterocyclic aromatic compound according to any one of claims 1 to 5, wherein X is 1 To X 3 Are each CR ', wherein R' is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C6-C60 heteroAn aryl group;
further preferably, R' is any one of hydrogen, deuterium, cyano, methyl, ethyl, propyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, N-phenylcarbazolyl, furyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, carbazolyl, acridinyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, quinolyl or isoquinolyl;
preferably, said X 1 To X 3 At least one of which is N;
preferably, said X 1 To X 3 Wherein both are N or X 1 To X 3 Are all N;
preferably, when a substituent is present in said group, said substituent is selected from deuterium, halogen, cyano, nitro, hydroxy, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C5-C30 aryloxy, C5-C30 aryl, C5-C30 heteroaryl.
7. The heterocyclic aromatic compound according to any one of claims 1 to 6, wherein the heterocyclic aromatic compound is any one of the following compounds:
8. An electron transport material comprising any one of the heterocyclic aromatic hydrocarbon compounds according to any one of claims 1 to 7.
9. An OLED device comprising at least an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked, wherein a material of the electron transport layer comprises any one of the heterocyclic aromatic hydrocarbon compounds according to any one of claims 1 to 7.
10. An electronic device, characterized in that it comprises an OLED device as claimed in claim 9.
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