CN114478607B - Organic luminescent material, application and device thereof - Google Patents
Organic luminescent material, application and device thereof Download PDFInfo
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- CN114478607B CN114478607B CN202111646135.1A CN202111646135A CN114478607B CN 114478607 B CN114478607 B CN 114478607B CN 202111646135 A CN202111646135 A CN 202111646135A CN 114478607 B CN114478607 B CN 114478607B
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- organic
- phenyl
- methyl
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- cyano
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- 239000000463 material Substances 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000010410 layer Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- -1 nitro, cyano, methyl Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011800 void material Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000001514 detection method Methods 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 230000000171 quenching effect Effects 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 125000005620 boronic acid group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 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 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- COGOHOXNRCFNET-UHFFFAOYSA-N 2,7-dibromo-5,10-diphenylphenazine Chemical group BrC1=CC=2N(C3=CC=C(C=C3N(C=2C=C1)C1=CC=CC=C1)Br)C1=CC=CC=C1 COGOHOXNRCFNET-UHFFFAOYSA-N 0.000 description 1
- QOGDMHZMYYSFPP-UHFFFAOYSA-N 2,7-dibromothianthrene Chemical group BrC1=CC=C2SC3=CC(Br)=CC=C3SC2=C1 QOGDMHZMYYSFPP-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to an organic luminescent material, application thereof and a device thereof. The organic luminescent material provided by the invention takes a functional group formed by singly connecting aryl silicon group and dibenzo six-membered heterocyclic ring with excellent photoelectric property and stability as a core, and is formed by selecting a plurality of aza-benzo multi-membered ring ends. The organic electroluminescent device prepared by using the method has the advantages of remarkably improving the electroluminescent performance, heat stability and service life of the device and meeting the requirement of the industrialization level on the overall performance of the device.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to an organic luminescent material, application thereof and a device thereof.
Background
Organic electroluminescence (OLEDs) has wide application prospects in the field of flat panel display and illumination due to the characteristics of low driving voltage, active light emission, high brightness, wide viewing angle, quick response, impact resistance and the like. Phosphorescent organic electroluminescent diodes (PhOLEDs) have been receiving great attention in the field of novel organic displays because of their ability to simultaneously utilize triplet and singlet excitons, with internal quantum efficiencies theoretically reaching 100%.
To achieve triplet phosphorescence, heavy metal atoms are usually doped with a host material, and the phosphorescence lifetime of heavy metal complexes is relatively long, which is easy to cause concentration quenching and triplet-triplet annihilation, so that it is required to find a suitable host material doped with a phosphorescent emitter of heavy metal to reduce the influence of the above factors, thereby obtaining a high-performance electrophosphorescent device.
The dibenzo six-membered heterocyclic ring has higher fluorescence quantum efficiency and higher rigidity, can well ensure the luminous efficiency and the service life of the device through bonding with the aryl silicon group with good electricity supply property and stability, and how to adjust the property of the whole molecule through carrying out fine structural design on the main structure of the dibenzo six-membered ring bonded aryl silicon group, thereby further improving the comprehensive performance of the device in the aspects of efficiency, thermal stability, service life and the like, solving the problems of concentration quenching of the phosphorescence device and efficiency roll-off in working, and being the key problem discussed by the invention.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides an organic luminescent material, application and a device thereof. The organic luminescent material provided by the invention takes a functional group formed by singly connecting a dibenzo six-membered heterocycle and an aryl silicon group as a main body, and is formed by further modifying a plurality of aza-benzo heterocycles at specific sites through aromatic bridges or single bonds. The technical scheme provided by the invention is as follows:
The invention provides an organic luminescent material which is characterized by having a structural general formula shown in the following formula (I):
wherein X, Y are each independently selected from: o, S, C (R 1)(R2)、N(R3);
r 0 is
* In order to replace the site of the substitution,
L is selected from the group consisting of arylene groups of C 6～30,
N is selected from 0, 1 and 2,
Ar is selected from the group consisting of aryl of C 6～30 and heteroaryl of C 3～30,
R 1-R3 is independently selected from alkyl of C 1～20 or aryl of C 6～30.
Further, each R 1-R3 is independently selected from methyl, phenyl which is unsubstituted or substituted by nitro, cyano, methyl, tert-butyl.
Further, the L is selected from: phenylene which is unsubstituted or substituted by nitro, cyano, methyl, biphenylene which is unsubstituted or substituted by nitro, cyano, methyl, naphthylene which is unsubstituted or substituted by nitro, cyano, methyl.
Further, the saidCan be represented by chemical formula 1, chemical formula 2, or chemical formula 3:
Wherein, Represents a single bond or a void;
q is C, CH or N, the number of Q is N is 0, 1 and 2, and Q of N is not adjacent to each other;
Z is O, S or NR 13,R13 is phenyl which is unsubstituted or substituted by cyano, nitro, methyl, tert-butyl, phenyl;
R 6、R9、R12 is independently selected from hydrogen, nitro, cyano and methyl;
R 4、R5、R7、R8、R10、R11 is independently selected from hydrogen, cyano, nitro, methyl, ethyl, tert-butyl, phenyl which is unsubstituted or substituted by cyano, nitro, methyl, tert-butyl, phenyl, and when Q is selected from N in chemical formula 1 and chemical formula 3, the number of Q is 2, Q is not on a six-membered ring, and when Q is selected from C, R 4、R5、R8、R10、R11 is not hydrogen;
n 1、n2、n3 is selected from 0, 1, 2;
* Is a substitution site.
Further, the saidCan be represented by the following groups:
further, the formula (1) may be represented by the following compounds:
the second aspect of the invention provides application of the organic luminescent material, wherein the organic luminescent material is used for preparing an organic electroluminescent device, an organic field effect transistor and an organic solar cell.
A third aspect of the present invention provides an organic light-emitting device comprising at least a pair of electrodes and an organic layer between the electrodes, the organic light-emitting material being applied to the organic layer between the electrodes.
Further, the organic layer between the electrodes comprises an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer and a hole injection layer, and the organic light emitting material is applied to the light emitting layer.
Further, the organic layer between the electrodes further comprises an exciton blocking layer or a hole blocking layer positioned at both sides of the light emitting layer, and the organic light emitting material is applied to the exciton blocking layer or the hole blocking layer.
The invention has the following advantages and effects:
1. The strong-electricity-supplying aryl silicon group and the dibenzo six-membered heterocyclic ring are bonded to form a main structure, so that the compound has higher fluorescence quantum efficiency, silicon atoms can effectively break the conjugated system of the compound molecules, and the silicon atoms are used as structural units for constructing materials of the weak conjugated system, so that the stacking quenching of the molecules can be effectively reduced, and the thermal stability of the molecules is improved;
2. The main structural unit is connected with the aromatic bridge, and the side groups such as arylamine, carbazole, imidazole, dibenzo six-membered ring and the like are connected with the aromatic bridge, so that the conjugation degree of the molecules can be further reduced through the rigid structure of the compound molecule, the stacking quenching of the molecules can be effectively reduced, and the thermal stability of the molecules can be improved;
3. the aza-benzo multi-ring units such as carbazole, phenazine, benzimidazole and the like designed at the tail end of the molecular chain of the compound are beneficial to reducing the energy level difference of the singlet state and the triplet state of the molecule and improving the luminous efficiency, and the push/pull electronic property of the compound enables the molecule to show trend accumulation, so that the material is endowed with more stable film forming property.
Detailed Description
The principles and features of the present invention are described below with examples only to illustrate the present invention and not to limit the scope of the present invention.
Example 1: synthesis of Compound (1)
S1, adding 2, 7-dibromodibenzo-dioxyhexane (17.10 g,50 mmol) into a reactor, adding tetrahydrofuran with 10 times of volume according to the weight of the 2, 7-dibromodibenzo-dioxyhexane for dissolution, introducing nitrogen for protection, cooling to-80 ℃, dropwise adding 24mL of 2.5M/L n-butyl solution, reacting at constant temperature for 0.5h, adding triphenylchlorosilane (11.79 g,40 mmol), heating to room temperature for reacting for 0.5h, adding dilute hydrochloric acid for quenching reaction, separating liquid, extracting water phase with ethyl acetate, combining with organic phase, concentrating, purifying to obtain 8.34g of intermediate (1 a), and obtaining 40% yield;
S2: adding the intermediate (1 a) (5.21 g,10 mmol), diphenylamine (1.69 g,10 mmol), potassium carbonate (2.76 g,20 mmol) and 60mL of xylene into a reactor, adding cuprous iodide (0.19 g,1 mmol) and phenanthroline (0.36 g,2 mmol) under a nitrogen atmosphere, heating to 145 ℃ for reflux reaction for 8 hours, cooling to room temperature, washing with water, filtering, concentrating the filtrate, and separating by column chromatography to obtain 4.76g of compound (1), wherein the yield is 78%;
the obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 609.8042.
Example 2: synthesis of Compound (17)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 of synthetic example 1 was replaced with 2, 7-dibromothianthrene (18.71 g,50 mmol), and 9.96g of intermediate (17 a) was obtained in the same manner as in S1 of synthetic example 1 in other synthetic procedures, and the yield was 45%;
S2: in a reactor, the above intermediate (17 a) (5.54 g,10 mmol), (4- (5 hydrogen-pyrido [4,3-b ] indol-5-yl) phenyl) boric acid (2.88 g,10 mmol), potassium carbonate (2.76 g,20 mmol) and 60mL of a toluene/ethanol mixed solvent with a volume ratio of 2:1 were added, and under a nitrogen atmosphere, dichlorodi-tert-butyl- (4-dimethylaminophenyl) palladium (0.04 g,0.05 mmol) was added, heated to 85℃and stirred for reaction for about 10 hours, then cooled to room temperature, filtered, and the filtrate was concentrated, then 5.16g of compound (17) was obtained by column chromatography separation, yield 72%.
The obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 716.9895.
Example 3: synthesis of Compound (36)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 in synthetic example 1 is replaced by 2, 6-dibromo-9, 10-tetramethyl-9, 10-dihydro anthracene (19.71 g,50 mmol), 9.64g of intermediate (36 a) is obtained by other synthetic processes with S1 in synthetic example 1, and the yield is 42%;
S2: the intermediate (17 a) in S2 in synthetic example 2 was replaced with intermediate (36 a) (5.74 g,10 mmol), (4- (5-hydro-pyrido [4,3-b ] indol-5-yl) phenyl) boronic acid was replaced with (4- (10-phenylphenazine-5 (10-hydro) -yl) phenyl) boronic acid (3.78 g,10 mmol), and other synthetic procedures were the same as S2 in synthetic example 2, so as to obtain 5.54g of compound (36) in 67% yield;
The obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 827.1545.
Example 4: synthesis of Compound (38)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 in synthetic example 1 was replaced with 2, 7-dibromo-5, 10-diphenyl-5, 10-dihydro-phenazine (24.61 g,50 mmol), and the other synthetic procedures were the same as in S1 in synthetic example 1, so that 9.67g of intermediate (38 a) was obtained in 36% yield;
s2: the intermediate (1 a) in S2 in the synthesis example 1 is replaced by an intermediate (38 a) (6.72 g,10 mmol), diphenylamine is replaced by carbazole (1.67 g,10 mmol), and other synthesis processes are the same as S2 in the synthesis example 1, so that 5.76g of a compound (38) can be obtained, and the yield is 76%;
The obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 758.0161.
Example 5: synthesis of Compound (48)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 in synthetic example 1 was replaced with 7-bromo-2-chlorophenoxazine (15.68 g,50 mmol), and 9.27g of intermediate (48 a) was obtained in the same manner as in S1 in synthetic example 1 in other synthetic procedures, and the yield was 47%;
s2: the intermediate (17 a) in S2 of Synthesis example 2 was replaced with intermediate (48 a) (4.93 g,10 mmol), (4- (5-hydro-pyrido [4,3-b ] indol-5-yl) phenyl) boric acid was replaced with (4- (9-hydro-carbazol-9-yl) phenyl) boric acid (2.87 g,10 mmol), and the other synthesis procedures were the same as S2 of Synthesis example 2, so as to obtain 5.11g of compound (48), yield 73%;
The obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 699.9402.
Example 6: synthesis of Compound (66)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 in synthetic example 1 is replaced by 7-bromo-2-chloro-10-phenyl-10 hydrogen-phenoxazine (18.50 g,50 mmol), 9.46g of intermediate (66 a) is obtained by other synthetic processes with S1 in synthetic example 1, and the yield is 43%;
S2: the intermediate (17 a) in S2 in synthetic example 2 was replaced with intermediate (66 a) (5.52 g,10 mmol), (4- (5-hydro-pyrido [4,3-b ] indol-5-yl) phenyl) boronic acid was replaced with (4- (2-phenyl-1-hydro-benzimidazol-1-yl) phenyl) boronic acid (3.14 g,10 mmol), and other synthetic procedures were the same as S2 in synthetic example 2, so as to obtain 5.50g of compound (66) in 70% yield;
The obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 786.0255.
Example 7: synthesis of Compound (77)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 in synthetic example 1 was replaced with 2-bromo-7-chloro-10-phenyl-10-hydro-phenothiazine (19.5 g,50 mmol), and 9.12g of intermediate (77 a) was obtained in the same manner as in S1 in synthetic example 1 in 40% yield;
S2: the intermediate (1 a) in S2 in synthetic example 1 was replaced with intermediate (77 a) (5.68 g,10 mmol), diphenylamine was replaced with 5 hydrogen-pyrrolo [3,2-b:4,5-c' ] bipyridinyl (1.69 g,10 mmol), and other synthetic procedures were the same as in S2 of synthetic example 1, to obtain 5.26g of compound (77) in 75% yield;
the obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 700.9308.
Example 8: synthesis of Compound (88)
S1: 2, 7-dibromodibenzo-dioxyhexane in S1 in synthetic example 1 is replaced by 2-bromo-7-chloro-10-phenyl-10 hydrogen-phenoxazine (18.5 g,50 mmol), 9.90g of intermediate (88 a) is obtained by other synthetic processes similar to S1 in synthetic example 1, and the yield is 45%;
s2: the intermediate (1 a) in S2 in synthetic example 1 is replaced by an intermediate (88 a) (5.52 g,10 mmol), diphenylamine is replaced by 10 hydrogen-phenoxazine (1.83 g,10 mmol), and other synthetic processes are the same as S2 in synthetic example 1, so that 5.10g of compound (88) is obtained, and the yield is 73%;
The obtained compound was subjected to detection analysis, and the results were as follows: the mass spectrometer MALDI-TOF-MS (m/z) was 698.8997.
Manufacturing example: preparation of electronic components
An Indium Tin Oxide (ITO) glass substrate is sequentially cleaned with ultrasonic waves in a cleaning agent and deionized water for 1h, then sequentially cleaned with acetone and isopropanol for 15min, dried in vacuum for 2h (105 ℃), then treated with UV ozone for 15min, and the ITO glass substrate is conveyed to a vacuum evaporator. Vacuum depositing molybdenum trioxide (MoO 3) on an ITO glass substrate to a thickness of 8nm to form a hole injection layer; vacuum depositing 4,4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC) on the hole injection layer to a thickness of 60nm to form a hole transport layer; vacuum depositing 4,4' -tris (carbazol-9-yl) triphenylamine (TCTA) on the hole transport layer to a thickness of 5nm to form an electron blocking layer; co-vacuum depositing 4,4' -bis (9-Carbazole) Biphenyl (CBP) and tris (2-phenylpyridine) iridium (Ir (ppy) 3) (as a light-emitting layer guest material) on the hole-transporting layer in a weight ratio of 92:8 to a thickness of 20nm to form a light-emitting layer; vacuum depositing 3,3'- [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 '-terphenyl ] -3, 3' -diyl ] bipyridine (TmPyPB) on the light emitting layer to a thickness of 40nm to form an electron transporting layer material; vacuum depositing lithium fluoride (LiF) on the electron transport layer to a thickness of 1nm to form an electron injection layer; aluminum (Al) was vacuum deposited on the electron injection layer to a thickness of 100nm to form a cathode.
The device has the specific structure that: ITO/MoO 3(8nm)/TAPC(60nm)/TCTA(5nm)/CBP:8％Ir(ppy)3 (20 nm)/TmPyPB (40 nm)/LiF (1 nm)/Al
The compounds prepared in examples 1 to 8 and comparative examples A1 and A2 were used instead of CBP described above, respectively, to thereby complete the preparation of electronic components,
The light emitting characteristics, thermal stability and lifetime of the electronic component prepared above were measured by applying a forward bias direct current thereto, and the test results are shown in table 1 below:
Table 1 electronic component performance characterization
The detection result shows that the organic luminescent material obtained through the microstructure design can be used as a single luminescent main material for preparing a green light device, and the preparation is simple and efficient, compared with the comparison compounds CBP, A1 and A2, the obtained luminescent element can remarkably reduce the high starting voltage caused by the wide band gap and the high triplet state energy level of the green light main material in the prior art, improves the concentration quenching and triplet state-triplet state annihilation problems, and further remarkably improves the performances of the device in the aspects of luminescent brightness, current efficiency, stability and the like. In addition, compared with the bipolar main body material CBP in the prior art, the organic luminescent material provided by the invention has higher glass transition temperature and stacking tendency due to the design of the terminal nitrogen-containing multi-ring unit, avoids material crystallization caused by temperature in the evaporation process and in the working state of the device, and solves the problem of device efficiency roll-down from two angles of material stacking form and thermal stability.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (6)
1. An organic luminescent material is characterized in that the structural general formula is shown as the following formula (1):
Wherein X, Y are each independently selected from: o, S, N (R 3);
Each R 3 is independently selected from methyl, phenyl which is unsubstituted or substituted by nitro, cyano, methyl, tert-butyl;
r 0 is * Is a substitution site;
The said Represented by chemical formula 1, chemical formula 2, or chemical formula 3:
Wherein, Represents a single bond or a void;
in chemical formula 1, Q is selected from C, CH or N, Q is N and the number of Q is 0, 1,2, and Q is N are not adjacent to each other;
In chemical formula 2 or chemical formula 3, Q is selected from C or CH;
Z is O, S or NR 13,R13 is phenyl which is unsubstituted or substituted by cyano, nitro, methyl, tert-butyl, phenyl;
R 6、R9、R12 is independently selected from hydrogen, nitro, cyano and methyl;
R 4、R5、R7、R8、R10、R11 is independently selected from hydrogen, cyano, nitro, methyl, ethyl, t-butyl, phenyl unsubstituted or substituted with cyano, nitro, methyl, t-butyl, phenyl, and when Q is selected from C, R 4、R5、R8、R10、R11 is not hydrogen;
n 1、n2、n3 is independently selected from 0 or 1.
2. The organic light-emitting material according to claim 1, wherein the organic light-emitting material comprisesRepresented by the following groups:
3. an organic light-emitting material characterized in that the formula (1) is represented by the following compound:
4. use of an organic light-emitting material according to any of claims 1 to 3 for the preparation of an organic electroluminescent device.
5. An organic electroluminescent device comprising at least a pair of electrodes and an organic layer between the electrodes, wherein the organic luminescent material according to any one of claims 1 to 3 is applied to the luminescent layer.
6. An organic electroluminescent device as claimed in claim 5, wherein the organic layer between the electrodes comprises an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer.
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| CN104904032A (en) * | 2012-11-06 | 2015-09-09 | 巴斯夫欧洲公司 | Phenoxasiline based compounds for electronic application |
| CN105189475A (en) * | 2013-04-09 | 2015-12-23 | 动力欧勒德斯有限公司 | Heterocyclic compounds and their use in electro-optical or opto-electronic devices |
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| CN104904032A (en) * | 2012-11-06 | 2015-09-09 | 巴斯夫欧洲公司 | Phenoxasiline based compounds for electronic application |
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