CN113861118A - 一种稠环化合物及其有机电致发光器件 - Google Patents
一种稠环化合物及其有机电致发光器件 Download PDFInfo
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- CN113861118A CN113861118A CN202111082045.4A CN202111082045A CN113861118A CN 113861118 A CN113861118 A CN 113861118A CN 202111082045 A CN202111082045 A CN 202111082045A CN 113861118 A CN113861118 A CN 113861118A
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- Prior art keywords
- substituted
- nitro
- fluoro
- unsubstituted
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- -1 methyl,Methoxy Chemical group 0.000 claims description 44
- 125000001153 fluoro group Chemical group F* 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 239000010410 layer Substances 0.000 claims description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000002825 nitriles Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 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 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000004947 monocyclic arenes Chemical class 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 23
- 238000002347 injection Methods 0.000 abstract description 6
- 239000007924 injection Substances 0.000 abstract description 6
- 230000001276 controlling effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 47
- 230000015572 biosynthetic process Effects 0.000 description 44
- 238000000921 elemental analysis Methods 0.000 description 15
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BSKLSKWOKGVQHF-UHFFFAOYSA-N (4-phenylnaphthalen-1-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=CC=C1C1=CC=CC=C1 BSKLSKWOKGVQHF-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- YOFJBRZKRZUDGB-UHFFFAOYSA-N 1,3-oxazole-5-carbaldehyde Chemical compound O=CC1=CN=CO1 YOFJBRZKRZUDGB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- CFPFMAGBHTVLCZ-UHFFFAOYSA-N (4-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(Cl)C=C1 CFPFMAGBHTVLCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HGROHYJKYOVLRM-UHFFFAOYSA-N (3-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(Cl)=C1 HGROHYJKYOVLRM-UHFFFAOYSA-N 0.000 description 1
- RWFHQVIXOZBUCA-UHFFFAOYSA-N (4-diphenylphosphanylphenyl)boronic acid Chemical compound C1(=CC=CC=C1)P(C1=CC=C(C=C1)B(O)O)C1=CC=CC=C1 RWFHQVIXOZBUCA-UHFFFAOYSA-N 0.000 description 1
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- QKRIYDBRCKMXHD-UHFFFAOYSA-N (8-phenyldibenzofuran-2-yl)boronic acid Chemical compound C1=C2C3=CC(B(O)O)=CC=C3OC2=CC=C1C1=CC=CC=C1 QKRIYDBRCKMXHD-UHFFFAOYSA-N 0.000 description 1
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 description 1
- UQKYXSFVOIMJCD-UHFFFAOYSA-N 2-fluoro-1-nitro-3-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC(C=2C=CC=CC=2)=C1F UQKYXSFVOIMJCD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QCKVUTCVXGLZQC-UHFFFAOYSA-N 3-hydroxy-1,2-dimethyl-1,2,3,9-tetrahydrocarbazol-4-one Chemical compound N1C2=CC=CC=C2C2=C1C(C)C(C)C(O)C2=O QCKVUTCVXGLZQC-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
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 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
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- RGJWSGXVPCZTRR-UHFFFAOYSA-N OB(O)OC1=CC=C(C2=CC=CC=C2)C2=CC=CC=C12 Chemical compound OB(O)OC1=CC=C(C2=CC=CC=C2)C2=CC=CC=C12 RGJWSGXVPCZTRR-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 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
- QHZHWFKZIRMHRT-UHFFFAOYSA-N [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical group C1=CC(B(O)O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 QHZHWFKZIRMHRT-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- KEQRPCPOINRCDB-UHFFFAOYSA-N iridium(3+);pentane-2,4-dione;1-phenylisoquinoline Chemical compound [Ir+3].CC(=O)CC(C)=O.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 KEQRPCPOINRCDB-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及光电材料应用科技领域,公开了一种稠环化合物及其有机电致发光器件。该稠环化合物通过引入具有较高三线态能级的菲并五元杂环核心结构,以及使用不同种类电子供受体基团对核心结构进行精细调控,提供了一种综合性能优良的发光主体材料,有效解决了目前发光主体材料由于电荷注入困难而导致的驱动电压高、荧光量子效率低等问题,达到了兼顾发光效率与驱动电压的技术效果,作为发光主体材料在有机电致发光器件中具有显著的应用价值。
Description
技术领域
本发明属于光电材料应用科技领域,具体涉及一种稠环化合物及其有机电致发光器件。
背景技术
有机电致发光装置(OLED)是一种自发光显示装置,其优点在于它可以提供更宽的视角、更高的对比率和更快的响应时间。有机电致发光装置结构类似“三明治”,通常包含阳极、阴极和在这两个电极之间形成的有机层。
在有机电致发光装置中,通过施加电压可以将来自阳极的空穴和来自阴极的电子注入到发光层中,并且通过空穴和电子的再结合产生具有高能量的激子,从而,发光层化合物分子能量被活化转变为激发态,当发光层化合物分子从不稳定的激发态返回到基态时的,能量被释放,发出光。
决定有机电致发光装置发光效率的最重要因素是发光材料。根据发光颜色的不同,发光材料可以分为蓝色、绿色和红色发光材料,并且可进一步包括黄色和橙色发光材料,根据功能的不同,发光材料可以分为主体材料和客体材料。无论何种分类,优良的发光材料都要求具有以下特征:高量子效率、高的电子和空穴结合率、所形成的发光层均匀性和稳定性良好。为满足目前制备高效率和长寿命有机电致发光装置的迫切需要,开发出具有上述优良性质的发光材料势在必行。
发明内容
本发明的目的在于提供一种高效稳定的可用于有机电致发光器件的主体材料,该主体材料应用于有机电致发光器件中能够有效解决目前器件驱动电压高,器件发光效率低等问题。
本发明第一个方面提供了一种稠环化合物,其化合物为为式(I)所示结构:
其中,X和Y分别独立地选自N、N(R2)、O或S,且X和Y中的一个为N,X和Y中的另一个选自N(R2)、O或S;
L0选自单键,或者未取代的或由C1~20的烷烃基、C1~20的烷氧基、腈基、硝基、氟基取代的亚苯基,或者未取代的或由C1~20的烷烃基、C1~20的烷氧基、腈基、硝基、氟基取代的亚联苯基,或者未取代的或由C1~20的烷烃基、烷氧基、腈基、硝基、氟基取代的亚萘基;
R1选自C1~20的烷基、C6~50的芳基、C3~50的杂芳基;
R0选自下列A1、A2、A3、A4或A5所示基团中的一种:
其中,
Z为C、CH或N,Z为N的个数为1、2或3,且相邻2个Z不同时为N,Z为C时,为R0桥接L0的取代位点或R3-R8的取代位点;
Q1选自O、S、N(R11)、C(R12)(R13);
Q2选自N、P、P(=O);
Ar表示为不存在或为单环芳烃,所述Ar与连接的萘环之间直接稠合;
R2-R13分别独立的选自氢、氟基、硝基、氰基、C1-20的烷基、C1-20的硅烷基、C6-50的芳基、C3-50的杂芳基、C6-50的芳氧基或C6-50的芳硫基中的一种。
进一步的,R1选自:未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的苯基,未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的联苯基,未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的萘基。
进一步的,R1为苯基。
进一步的,R2选自:未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基取代的苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基取代的联苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基取代的萘基。
进一步的,L0选自单键、苯基、联苯基、萘基。
其中,
Z1为C、CH或N,Z1为N的个数为1、2或3,且相邻2个Z1不同时为N,Z1为C时,为R0桥接L0的取代位点或R21、R24、R25的取代位点;
Q3、Q4分别独立选自O、S、N(R32)、C(R33)(R34);
R14-R34分别独立的选自氢,氟基,硝基,氰基,C1-C6的烷烃基,未取代的或由氟基、硝基、氰基、C1-C6的烷烃基、萘基取代的苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷烃基、苯基取代的联苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷烃基、苯基取代的萘基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的二苯并呋喃基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的二苯并噻吩基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的芴基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的咔唑基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的二苯胺基。
其中,Z1为CH或N,Z1为N的个数为1、2或3;
其中,Q4分别独立的选自O、S、C(CH3)2、N(R32),R32选自苯基、甲苯基、叔丁基苯基、氰基苯基、硝基苯基、氟代苯基、联苯基、三联苯基、萘基;
进一步的,式(I)所示稠环化合物选自下述化合物:
本发明第二个方面提供了一种有机电致发光器件,主要包括阴极、阳极和两电极之间的有机层,两电极之间的有机层包含上述任一所述的稠环化合物。
进一步的,两电极之间的有机层包括发光层,发光层由发光主体和发光客体组成,发光主体包上述任一所述的稠环化合物。
本发明提供的稠环化合物分子核心结构包含菲并五元杂环大共轭平面结构,因此具有较高的三线态能级,将其作为主体材料,可以有效防止发光过程中的能量回传,从而化合物材料可以获得更高的荧光量子效率;核心结构中苯基的引入可以有效抑制分子间的相互作用,减少化合物分子间的π-π堆集,此外,引入不同种类的空穴传输型基团或电子传输型基团对核心结构进行修饰,可以有效提高发光层空穴与电子的平衡性,当其作为主体材料时,这可以有效避免因其较宽的带隙而造成的发光层电荷注入困难,从而器件驱动电压降低,使用本发明化合物作为发光层主体材料所制得的器件在驱动电压、电流效率、寿命等综合性能上取得显著进步。
具体实施方式
应当理解的是,此处所描述的具体实施方式仅用于说明和解释本发明,并不用于限制本发明。
中间体1:合成3-氯-9-苯基菲并[2,3-d]噁唑
S1.在500mL反应瓶中,加入6-溴-2-苯基苯并[d]噁唑-5-甲醛(26.59g,88mmol)、(4-氯苯基)硼酸(12.51g,80mmol)、碳酸钾(22.08g,160mmol)、250mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.46g,0.4mmol),加热至85℃,搅拌反应8h左右,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用乙醇和/或四氢呋喃进行纯化,即可得到17.35g中间体a1,收率65%;
S2.在500mL反应瓶中,加入甲氧基甲基三苯基氯化膦(20.57g,60mmol)、叔丁醇钾(6.73g,60mmol),200mL四氢呋喃,降温至0℃下搅拌反应0.5小时,然后加入中间体a1(13.35g,40mmol),室温下搅拌反应2小时,加水猝灭反应,用乙酸乙酯萃取,水洗,无水硫酸钠干燥,过滤,浓缩后通过柱色谱即可得到12.59g中间体b1,产率87%;
S3.在100mL反应瓶中,加入中间体b1(7.24g,20mmol)、氯化镍(0.13g,1mmol)、60mL1,2-二氯乙烷,室温下搅拌反应2小时,过滤,滤液浓缩,然后通过柱色谱分离即可得到5.47g中间体1,收率83%。
质谱仪MALDI-TOF-MS(m/z)=329.7864,理论分子量:329.7830,元素分析:理论值:C21H12N(%):C76.48;H3.67;N4.25;实测值:C76.50;H3.66;N4.23。
中间体2:合成2-氯-9-苯基菲并[3,2-d]噻唑
S1.将中间体1中步骤S1的6-溴-2-苯基苯并[d]噁唑-5-甲醛替换为5-溴-2-苯基苯并[d]噻唑-6-甲醛(28.00g,88mmol)、(4-氯苯基)硼酸替换为(3-氯苯基)硼酸(12.51g,80mmol),其他合成过程按照中间体1的步骤S1,即可得到18.75g中间体a2,收率67%;
S2.将中间体1中步骤S2的中间体a1替换为中间体a2(14.00g,40mmol)、其他合成过程按照中间体1的步骤S2,即可得到12.55g中间体b2,收率83%;
S3.将中间体1中步骤S3的中间体b1替换为中间体b2(7.56g,20mmol)、其他合成过程按照中间体1的步骤S3,即可得到5.53g中间体2,收率80%。
质谱仪MALDI-TOF-MS(m/z)=345.8405,理论分子量:345.8440,元素分析:理论值:C21H12N(%):C72.93;H3.50;N4.05;实测值:C72.91;H3.52;N4.07。
中间体3:合成3-氯-9,10-二苯基-10氢-菲并[2,3-d]咪唑
S1.将中间体1中步骤S1的6-溴-2-苯基苯并[d]噁唑-5-甲醛替换为6-溴-1,2-二苯基-1氢-苯并[d]咪唑-5-甲醛(33.20g,88mmol),其他合成过程按照中间体1的步骤S1,即可得到20.28g中间体a3,收率62%;
S2.将中间体1中步骤S2的中间体a1替换为中间体a3(16.36g,40mmol)、其他合成过程按照中间体1的步骤S2,即可得到13.98g中间体b3,收率80%;
S3.将中间体1中步骤S3的中间体b1替换为中间体b3(8.74g,20mmol)、其他合成过程按照中间体1的步骤S3,即可得到6.88g中间体3,收率85%。
质谱仪MALDI-TOF-MS(m/z)=404.8941,理论分子量:404.8970,元素分析:理论值:C27H17N2(%):C80.09;H4.23;N6.92;实测值:C80.10;H4.21;N6.93。
按照中间体1、中间体2及中间体3的合成方法,以基本相同的合成方法(相同的反应摩尔比与反应条件),即可制备得到:
合成实施例1:合成化合物(1-1)
S1.在50mL反应瓶中,加入3-氯-9-苯基菲并[2,3-d]噁唑(3.30g,10mmol)、(4-苯基萘-1-基)硼酸(2.48g,10mmol)、碳酸钾(2.76g,20mmol)、25mL体积比为2:1:1的甲苯/乙醇/水混合溶剂,通入氮气排空气,然后,加入四(三苯基膦)钯(0.06g,0.05mmol),加热至85℃,搅拌反应8h左右,然后冷却至室温,过滤,滤液分液,有机相浓缩,与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗,浓缩,即可得到3.88g化合物(1-1),收率78%。
质谱仪MALDI-TOF-MS(m/z)=497.6008,理论分子量:497.5970,元素分析:理论值:C37H23N(%):C89.31;H4.66;N2.81;实测值:C89.30;H4.64;N2.82。
合成实施例2:合成化合物(1-11)
S1.将合成实施例1步骤S1的3-氯-9-苯基菲并[2,3-d]噁唑替换为2-氯-9-苯基菲并[3,2-d]噻唑(3.46g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(萘-1-基)苯基硼酸(2.48g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到3.75g化合物(1-11),收率73%。
质谱仪MALDI-TOF-MS(m/z)=513.6529,理论分子量:513.6580,元素分析:理论值:C37H23N(%):C86.52;H4.51;N2.73;实测值:C86.52;H4.53;N2.72。
合成实施例3:合成化合物(1-18)
S1.将合成实施例1步骤S1的3-氯-9-苯基菲并[2,3-d]噁唑替换为2-氯-8,9-二苯基-8氢-菲并[2,3-d]咪唑(4.05g,10mmol)、(4-苯基萘-1-基)硼酸替换成(10-苯基蒽-9-基)硼酸(2.98g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到4.36g化合物(1-18),收率70%。
质谱仪MALDI-TOF-MS(m/z)=622.7754,理论分子量:622.7710,元素分析:理论值:C47H30N2(%):C90.65;H4.86;N4.50;实测值:C90.67;H4.85;N4.49。
合成实施例4:合成化合物(1-22)
S1.将合成实施例1步骤S1的3-氯-9-苯基菲并[2,3-d]噁唑替换为2-氯-9-苯基菲并[3,2-d]噁唑(3.3g,10mmol)、(4-苯基萘-1-基)硼酸替换成(8-苯基二苯并[b,d]呋喃-2-基)硼酸(2.88g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到3.98g化合物(1-22),收率74%。
质谱仪MALDI-TOF-MS(m/z)=537.6180,理论分子量:537.6221,元素分析:理论值:C39H23N(%):C87.13;H4.31;N2.61;实测值:C87.12;H4.32;N2.62。
合成实施例5:合成化合物(1-26)
S1.将合成实施例1步骤S1的3-氯-9-苯基菲并[2,3-d]噁唑替换为2-氯-9-苯基菲并[3,2-d]噁唑(3.5g,10mmol)、(4-苯基萘-1-基)硼酸替换成(9-苯基-氢-咔唑-3-基)硼酸(2.87g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到4.20g化合物(1-26),收率76%。
质谱仪MALDI-TOF-MS(m/z)=552.6995,理论分子量:552.6950,元素分析:理论值:C39H24N2(%):C84.75;H4.38;N5.07;实测值:C84.77;H4.38;N5.05。
合成实施例6:合成化合物(1-33)
S1.在50mL反应瓶中,加入3-氯-9,10-苯基-10氢-菲并[2,3-d]咪唑(4.05g,10mmol)、9氢-咔唑(2.00g,12mmol)、碳酸钾(2.76g,20mmol)和30mL N,N-二甲基乙酰胺。通入氮气,加入碘化亚铜0.19g(1mmol)和邻菲啰啉0.36g(2mmol),加热回流搅拌8h,将温度冷却至室温,加水,分液,有机相减压蒸馏,乙醇纯化,即可得到4.40g化合物(1-33),收率82%。
质谱仪MALDI-TOF-MS(m/z)=535.6538,理论分子量:535.6500,元素分析:理论值:C39H25N3(%):C87.45;H4.70;N7.84;实测值:C87.44;H4.68;N7.85。
合成实施例7:合成化合物(1-48)
S1.将合成实施例6步骤S1的3-氯-9,10-苯基-10氢-菲并[2,3-d]咪唑替换为2-氯-8,9-二苯基-8氢-菲并[2,3-d]咪唑(4.05g,10mmol)、9氢-咔唑替换成二苯基胺(2.03g,12mmol),其他合成过程按照合成实施例6步骤S1,即可得到4.63g化合物(1-48),收率86%。
质谱仪MALDI-TOF-MS(m/z)=537.6609,理论分子量:537.6660,元素分析:理论值:C39H27N3(%):C87.12;H5.06;N7.82;实测值:C87.14;H5.07;N7.81。
合成实施例8:合成化合物(2-1)
S1.将合成实施例1步骤S1的(4-苯基萘-1-基)硼酸替换成(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸(3.53g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到4.28g化合物(2-1),收率71%。
质谱仪MALDI-TOF-MS(m/z)=602.6951,理论分子量:602.6970,元素分析:理论值:C42H26N4(%):C83.70;H4.35;N9.30;实测值:C83.69;H4.36;N9.32。
合成实施例9:合成化合物(2-15)
S1.将合成实施例1步骤S1的3-氯-9-苯基菲并[2,3-d]噁唑替换为2-氯-9,10-二苯基-10氢-菲并[2,3-d]咪唑(4.05g,10mmol)、(4-苯基萘-1-基)硼酸替换成呋喃并[2,3-b:5,4-b']二吡啶-3-基硼酸(2.14g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到3.93g化合物(2-15),收率73%。
质谱仪MALDI-TOF-MS(m/z)=538.6128,理论分子量:538.6100,元素分析:理论值:C37H22N4(%):C82.51;H4.12;N10.40;实测值:C82.53;H4.10;N10.40。
合成实施例10:合成化合物(2-23)
S1.将合成实施例6步骤S1的3-氯-9,10-苯基-10氢-菲并[2,3-d]咪唑替换为3-氯-9-苯基菲并[2,3-d]噻唑(3.46g,10mmol)、9氢-咔唑替换成9氢-吡啶并[3,4-b]吲哚(2.02g,12mmol),其他合成过程按照合成实施例6步骤S1,即可得到4.02g化合物(2-23),收率84%。
质谱仪MALDI-TOF-MS(m/z)=477.5817,理论分子量:477.5850,元素分析:理论值:C32H19N3(%):C80.48;H4.01;N8.80;实测值:C80.47;H4.03;N8.78。
合成实施例11:合成化合物(2-31)
S1.将合成实施例1步骤S1的3-氯-9-苯基菲并[2,3-d]噁唑替换为2-氯-9-苯基菲并[3,2-d]噁唑(3.3g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(二苯基磷)苯基)硼酸(3.06g,10mmol),其他合成过程按照合成实施例1步骤S1,即可得到4.17g化合物(2-31),收率75%。
质谱仪MALDI-TOF-MS(m/z)=555.6124,理论分子量:555.6168,元素分析:理论值:C39H26N(%):C84.31;H4.72;N2.52;实测值:C84.33;H4.71;N2.50。
合成实施例12:合成化合物(2-35)
S1.将合成实施例6步骤S1的3-氯-9,10-苯基-10氢-菲并[2,3-d]咪唑替换为3-氯-9-苯基菲并[3,2-d]噻唑(3.46g,10mmol)、9氢-咔唑替换成二苯基氧膦(2.43g,12mmol),其他合成过程按照合成实施例6步骤S1,即可得到4.10g化合物(2-35),收率80%。
质谱仪MALDI-TOF-MS(m/z)=511.5806,理论分子量:511.5788,元素分析:理论值:C33H22N(%):C77.48;H4.33;N2.74;实测值:C77.49;H4.31;N2.76。
器件实施例1
将带有120nm ITO透明薄膜的玻璃基板依次用丙酮、异丙醇和去离子水各超声清洗10min,105℃下真空干燥2h,然后进行UV臭氧洗涤15min,即将ITO玻璃基板传送至真空蒸镀机。
在形成有ITO薄膜一侧的面上,真空蒸镀三氧化钼(MoO3),以形成10nm厚的空穴注入层;
下一步,在上述空穴注入层上,真空蒸镀4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC),以形成70nm厚的空穴传输层;
下一步,在上述空穴传输层上,共同真空蒸镀上述合成实施例1中所制备的化合物1-1(作为发光主体材料,95wt%)与二(1-苯基-异喹啉)(乙酰丙酮)合铱(III)(Ir(piq)2(acac))(作为发光客体材料,5wt%),以形成30nm厚度的发光层;
下一步,在上述发光层上,真空蒸镀3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1”-三联苯]-3,3”-二基]二吡啶(TmPyPB),以形成40nm厚度的电子传输层;
下一步,在上述电子传输层上,真空蒸镀氟化锂(LiF),以形成1nm厚度的电子注入层;
最后,在上述电子注入层上,真空蒸镀铝(Al),以形成100nm的阴极。
器件实施例2至器件实施例13
按照与器件实施例1相同的方法制备有机电致发光器件,不同的是分别使用上述合成实施例2至合成实施例12中所合成的化合物及4,4'-二(9-咔唑)联苯(CBP)分别替换上述合成实施例1中所制备的化合物1-1。
对上述器件实施例所制备的有机电致发光器件进行性能测试,结果如表1所示:
表1
从上表1的数据可看出,与传统的4,4'-二(9-咔唑)联苯(CBP)相比,本发明提供的以菲并五元杂环接苯基为核心结构,键接空穴传输型或电子传输型侧基的稠环化合物由于三线态能级较高的菲并五元杂环的引入以及不同种类电子供受体基团对化合物电子及空穴平衡性的精细调控,使得使用本发明化合物作为发光主体材料所制得的有机电致发光器件实现了纯正的红色光发射,并且器件在驱动电压、电流效率、使用寿命等综合性能上具有显著进步,有效解决了目前有机电致发光器件因主体材料电荷注入困难而导致的驱动电压高、荧光量子效率低的问题。
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (10)
1.一种稠环化合物,其特征在于,所述稠环化合物为式(I)所示结构:
其中,X和Y分别独立地选自N、N(R2)、O或S,且X和Y中的一个为N,X和Y中的另一个选自N(R2)、O或S;
L0选自单键,或者未取代的或由C1~20的烷烃基、C1~20的烷氧基、腈基、硝基、氟基取代的亚苯基,或者未取代的或由C1~20的烷烃基、C1~20的烷氧基、腈基、硝基、氟基取代的亚联苯基,或者未取代的或由C1~20的烷烃基、烷氧基、腈基、硝基、氟基取代的亚萘基;
R1选自C1~20的烷基、C6~50的芳基、C3~50的杂芳基;
R0选自下列A1、A2、A3、A4或A5所示基团中的一种:
其中,
Z为C、CH或N,Z为N的个数为1、2或3,且相邻2个Z不同时为N,Z为C时,为R0桥接L0的取代位点或R3-R8的取代位点;
Q1选自O、S、N(R11)、C(R12)(R13);
Q2选自N、P、P(=O);
Ar表示为不存在或为单环芳烃,所述Ar与连接的萘环之间直接稠合;
R2-R13分别独立的选自氢、氟基、硝基、氰基、C1-20的烷基、C1-20的硅烷基、C6-50的芳基、C3-50的杂芳基、C6-50的芳氧基或C6-50的芳硫基中的一种。
2.根据权利要求1所述的一种稠环化合物,其特征在于:所述R1为选自:未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的苯基,未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的联苯基,未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的萘基。
3.根据权利要求2所述的一种稠环化合物,其特征在于:所述R1为苯基。
4.根据权利要求1所述的一种稠环化合物,其特征在于:所述R2选自:未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基取代的苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基取代的联苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基取代的萘基。
5.根据权利要求1所述的一种稠环化合物,其特征在于:所述L0选自单键、亚苯基、亚联苯基、亚萘基。
其中,
Z1为C、CH或N,Z1为N的个数为1、2或3,且相邻2个Z1不同时为N,Z1为C时,为R0桥接L0的取代位点或R21、R24、R25的取代位点;
Q3、Q4分别独立选自O、S、N(R32)、C(R33)(R34);
R14-R34分别独立的选自氢,氟基,硝基,氰基,C1-C6的烷烃基,未取代的或由氟基、硝基、氰基、C1-C6的烷烃基、萘基取代的苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷烃基、苯基取代的联苯基,未取代的或由氟基、硝基、氰基、C1-C6的烷烃基、苯基取代的萘基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的二苯并呋喃基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的二苯并噻吩基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的芴基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的咔唑基,未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的二苯胺基。
9.一种有机电致发光器件,主要包括阴极、阳极和两电极之间的有机层,其特征在于:所述两电极之间的有机层包含权利要求1-8任一所述的稠环化合物。
10.根据权利要求9所述的有机电致发光器件,其特征在于,所述两电极之间的有机层包括发光层,所述发光层由发光主体和发光客体组成,所述发光主体包含权利要求1-8任一所述的稠环化合物。
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