US20070164669A1 - Silicon-contained anthracene compound for organic electroluminescent device - Google Patents
Silicon-contained anthracene compound for organic electroluminescent device Download PDFInfo
- Publication number
- US20070164669A1 US20070164669A1 US11/693,288 US69328807A US2007164669A1 US 20070164669 A1 US20070164669 A1 US 20070164669A1 US 69328807 A US69328807 A US 69328807A US 2007164669 A1 US2007164669 A1 US 2007164669A1
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- US
- United States
- Prior art keywords
- group
- substituted
- electroluminescent device
- organic electroluminescent
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 30
- -1 anthracene compound Chemical class 0.000 title claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 31
- 239000012044 organic layer Substances 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000004020 conductor Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000005033 thiopyranyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 12
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 125000005106 triarylsilyl group Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 0 [1*]C.[2*]C.[3*][Si]([4*])([5*])C1=C2C=CC=CC2=C(C)C2=C1C=CC=C2 Chemical compound [1*]C.[2*]C.[3*][Si]([4*])([5*])C1=C2C=CC=CC2=C(C)C2=C1C=CC=C2 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 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 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- AYQIOGCCWOJSPE-UHFFFAOYSA-N (10-bromoanthracen-9-yl)-triphenylsilane Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AYQIOGCCWOJSPE-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- REYTZSWSCPGKPN-UHFFFAOYSA-N (10-naphthalen-2-ylanthracen-9-yl)-triphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C2=CC=CC=C2C(C=2C=C3C=CC=CC3=CC=2)=C2C=CC=CC2=1)(C=1C=CC=CC=1)C1=CC=CC=C1 REYTZSWSCPGKPN-UHFFFAOYSA-N 0.000 description 2
- BSHSCWRTJSBWLY-UHFFFAOYSA-N 1-cyclohexyl-4-phenylbenzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC=CC=2)C=C1 BSHSCWRTJSBWLY-UHFFFAOYSA-N 0.000 description 2
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 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 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 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 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 1
- CAOLYVDEAADIOK-UHFFFAOYSA-N BrC1=C2C=CC=CC2=C(Br)C2=C1C=CC=C2.BrC1=C2C=CC=CC2=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C21.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C([Si](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=CC=CC=C32)C=C1.Cl[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Li]CCCC.[Li]CCCC Chemical compound BrC1=C2C=CC=CC2=C(Br)C2=C1C=CC=C2.BrC1=C2C=CC=CC2=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C21.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C([Si](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=CC=CC=C32)C=C1.Cl[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Li]CCCC.[Li]CCCC CAOLYVDEAADIOK-UHFFFAOYSA-N 0.000 description 1
- BPQRIFGIXZGFPU-UHFFFAOYSA-N BrC1=C2C=CC=CC2=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=C1C=CC=C2.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4C=CC=CC4=C3)C3=C2C=CC=C3)C=C1.OB(O)C1=CC=C2C=CC=CC2=C1 Chemical compound BrC1=C2C=CC=CC2=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C2=C1C=CC=C2.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4C=CC=CC4=C3)C3=C2C=CC=C3)C=C1.OB(O)C1=CC=C2C=CC=CC2=C1 BPQRIFGIXZGFPU-UHFFFAOYSA-N 0.000 description 1
- METIXWSDODWHAJ-UHFFFAOYSA-N C1=CC=C(C2=C3C=CC=CC3=C([Si](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C2C=CC=C3)C=C1.C1=CC=C(C2=CC(C3=CC=CC=C3)=CC(C3=C4C=CC=CC4=C([Si](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C4=C3C=CC=C4)=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C([Si](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C4=C3C=CC=C4)C=C2)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4C=CC=CC4=C3)C3=C2C=CC=C3)C=C1 Chemical compound C1=CC=C(C2=C3C=CC=CC3=C([Si](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C2C=CC=C3)C=C1.C1=CC=C(C2=CC(C3=CC=CC=C3)=CC(C3=C4C=CC=CC4=C([Si](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C4=C3C=CC=C4)=C2)C=C1.C1=CC=C(C2=CC=C(C3=C4C=CC=CC4=C([Si](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C4=C3C=CC=C4)C=C2)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4C=CC=CC4=C3)C3=C2C=CC=C3)C=C1 METIXWSDODWHAJ-UHFFFAOYSA-N 0.000 description 1
- JWNUQMBJPKKQLU-UHFFFAOYSA-N C1=CC=C(N2C3=CC=C(C4=C5C=CC=CC5=C([Si](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)C5=C4C=CC=C5)C=C3C3=C2C=CC=C3)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4/C=C\C5=CC=CC6=C5C4=C3C=C6)C3=C2C=CC=C3)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4C=CC=CC4=N3)C3=C2C=CC=C3)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=CC=N3)C3=C2C=CC=C3)C=C1.CCC1(CC)C2=CC(C3=C4C=CC=CC4=C([Si](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C4=C3C=CC=C4)=CC=C2C2=C1C=CC=C2.C[Si](C)(C)C1=C2C=CC=CC2=C([Si](C)(C)C)C2=CC=CC=C21 Chemical compound C1=CC=C(N2C3=CC=C(C4=C5C=CC=CC5=C([Si](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)C5=C4C=CC=C5)C=C3C3=C2C=CC=C3)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4/C=C\C5=CC=CC6=C5C4=C3C=C6)C3=C2C=CC=C3)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=C4C=CC=CC4=N3)C3=C2C=CC=C3)C=C1.C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C(C3=CC=CC=N3)C3=C2C=CC=C3)C=C1.CCC1(CC)C2=CC(C3=C4C=CC=CC4=C([Si](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C4=C3C=CC=C4)=CC=C2C2=C1C=CC=C2.C[Si](C)(C)C1=C2C=CC=CC2=C([Si](C)(C)C)C2=CC=CC=C21 JWNUQMBJPKKQLU-UHFFFAOYSA-N 0.000 description 1
- PBRKCNMSBIMTKC-UHFFFAOYSA-N C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C([Si](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=CC=CC=C32)C=C1 Chemical compound C1=CC=C([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=C3C=CC=CC3=C([Si](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=CC=CC=C32)C=C1 PBRKCNMSBIMTKC-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N C1=CC=C2C(=C1)C(C1=CC3=C(C=CC=C3)C=C1)=C1C=CC=CC1=C2C1=CC2=C(C=CC=C2)C=C1 Chemical compound C1=CC=C2C(=C1)C(C1=CC3=C(C=CC=C3)C=C1)=C1C=CC=CC1=C2C1=CC2=C(C=CC=C2)C=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- QDEGDEVWWPKPMD-UHFFFAOYSA-N FB1(F)N2C(=CC3=N1C1=C(C=CC=C1)C=C3)C=CC1=C2C=CC=C1 Chemical compound FB1(F)N2C(=CC3=N1C1=C(C=CC=C1)C=C3)C=CC1=C2C=CC=C1 QDEGDEVWWPKPMD-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 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
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Definitions
- This invention relates to anthracene compound, particular on the position 9 and 10, and at least one having a substituted silyl group, the anthracene compound can be an organic light emitting diode (OLED) material and used for organic electroluminescent device.
- OLED organic light emitting diode
- the organic electroluminescent device having high efficiency and fluorescent dyes can be used for the flat panel displays bring this technology commercialization.
- an OLED being developed later than a liquid crystal display (LCD)
- LCD liquid crystal display
- beneficial characteristics such as a spontaneous light source, a wide viewing angle, high response velocity, high brightness, strong contrast, small thickness, power saving, and a wide operating temperature
- the OLED has been used extensively in small and medium scale portable display fields.
- the emitting layer is between the metal cathode and transparent anode in the organic electroluminescent device.
- a DC voltage is applied to the OLED structure, electrons in the cathode and holes in the transparent conductive layer will be injected into the emitting layer through the electron transport layer and the hole transport layer respectively. Due to the potential difference incurred from the external electrical field, electrons and holes will move in the emitting layer and recombine as excitions. When the excitions come back to the ground state by way of releasing energy, the quantum efficiency is released in a form of photos to emit light downwards through the transparent anode. This is the organic electroluminescent principle.
- anthracene compound on the hole transport layer which on position 9 and 10 having aryl group, the structure as following: wherein substituents R 1 to R 4 are each individually hydrogen, or alkyl of from 1 to 24 carbon atoms; aryl or substituted aryl of from 5 to 20 carbon atoms; or heteroaryl or substituted of from 5 to 24 carbon atoms; or fluorine, chlorine, bromine; or cyano group.
- each of A 1 to A 4 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms
- each of R 1 to R 8 is a hydrogen atom independently, a halogen atom, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group or a substituted or unsubstituted amino group.
- This invention provides an organic light emitting diode (OLED) material, which at least one having a substituted silyl group on the position 9 and 10 of the anthracene compound, said the anthracene compound represented by the following formula:
- X represents a substituted silyl group (more preferably triphenylsilyl group), a trialkylsilyl group having 1 to 20 carbon atoms (more preferably trimethylsilyl group, triethylsilyl group, or tripropylsilyl group, particularly preferably trimethylsilyl group), a substituted or unsubstituted aryl group having 6 to 20 carbon atoms (more preferably benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, triphenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, or pyrenyl group, particularly preferably benzyl group, naphthyl group, biphenyl group, triphenyl group, particularly
- each R 1 and R 2 represents hydrogen, halogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (more preferably hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, fluorine, chlorine, or bromine, particularly preferably hydrogen, methyl group, ethyl group, propyl group, butyl group, fluorine, chlorine, or bromine), wherein R 1 and R 2 can be the same or not the same.
- each R 3 , R 4 and R 5 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms (more preferably benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, triphenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, or pyrenyl group, particularly preferably benzyl group, naphthyl group, biphenyl group, triphenyl group, or pyrenyl group etc.), or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms (more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, particularly preferably methyl group
- anthracene compound (A) there are some compounds but not limited:
- the invention also represents an organic electroluminescent device, which comprising:
- a second electrode layer which is on the organic layer.
- the substrate more preferably glass substrate, the first electrode layer more preferably a transparent conductive material, perfect preferably indium tin oxide film, the organic layer more preferably including a hole injection layer, a hole transport layer, a light emitting layer, a electron transport layer and a electron injection layer, wherein the anthracene compound (A) is in the light emitting layer; the second electrode layer more preferably a metal layer, perfect preferably Aluminum in the organic electroluminescent device.
- Typical organic emitting materials were formed of a conjugated organic host material and a conjugated organic activating agent having condensed benzene rings.
- a conjugated organic host material for the production of full color OLED display panel, it is necessary to have efficient red, green and blue (RGB) EL materials with proper chromaticity and sufficient luminance efficiency.
- RGB red, green and blue
- the guest-host doped system offers a ready avenue fir achieving such an objective, mainly because doping an emissive dopant of high luminescent property into a host can raise the efficiency of radiative recombination. In this application also having dopant in the emissive layer, such as BDM. etc.
- FIG. 1 shows the PL intensity in different waves about compound (1) and compound (2)
- FIG. 2 shows the efficiency of organic light emitting diode material in example 5 and compare example 1;
- FIG. 3 ( a ) and FIG. 3 ( b ) show the different of organic light emitting diode material in the CIE chromaticity coordinates between example 5 and compare example 1, wherein both the horizontal axis represent voltage, the vertical axis represents CIEx in FIG. 3 ( a ), and the vertical axis represents CIEy in FIG. 3 ( b ).
- the host material of emitting layer being the anthracene compound, as Example 4 and 6, the CIE chromaticity coordinates (Y axis) from 0.14 to 0.13. So the organic electroluminescent element approaches to blue light. Furthermore, this invention also can be dopant, as Example 5.
- Example 5 Comparing the Example 5 with the Example 1, it is known the efficiency and the color gamut of the present compound (Example 5) better than the Example 1 from FIG. 2 , FIG. 3 ( a ) and FIG. 3 ( b ).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/693,288 US20070164669A1 (en) | 2005-04-08 | 2007-03-29 | Silicon-contained anthracene compound for organic electroluminescent device |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW094111260 | 2005-04-08 | ||
| TW094111260A TWI287568B (en) | 2005-04-08 | 2005-04-08 | Silicon-contained anthracene compound for organic electroluminescent device |
| US11/179,573 US20060226768A1 (en) | 2005-04-08 | 2005-07-13 | Silicon-contained anthracene compound for organic electroluminescent device |
| US11/693,288 US20070164669A1 (en) | 2005-04-08 | 2007-03-29 | Silicon-contained anthracene compound for organic electroluminescent device |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/179,573 Division US20060226768A1 (en) | 2005-04-08 | 2005-07-13 | Silicon-contained anthracene compound for organic electroluminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20070164669A1 true US20070164669A1 (en) | 2007-07-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/179,573 Abandoned US20060226768A1 (en) | 2005-04-08 | 2005-07-13 | Silicon-contained anthracene compound for organic electroluminescent device |
| US11/693,266 Active US7449593B2 (en) | 2005-04-08 | 2007-03-29 | Silicon-contained anthracene compound for organic electroluminescent device |
| US11/693,288 Abandoned US20070164669A1 (en) | 2005-04-08 | 2007-03-29 | Silicon-contained anthracene compound for organic electroluminescent device |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/179,573 Abandoned US20060226768A1 (en) | 2005-04-08 | 2005-07-13 | Silicon-contained anthracene compound for organic electroluminescent device |
| US11/693,266 Active US7449593B2 (en) | 2005-04-08 | 2007-03-29 | Silicon-contained anthracene compound for organic electroluminescent device |
Country Status (2)
| Country | Link |
|---|---|
| US (3) | US20060226768A1 (US20070164669A1-20070719-C00010.png) |
| TW (1) | TWI287568B (US20070164669A1-20070719-C00010.png) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090108735A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with fluoranthene electron transport materials |
| US20090110957A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with certain fluoranthene host |
| US20090108736A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Phosphorescent oled device with certain fluoranthene host |
| US20100117520A1 (en) * | 2008-11-12 | 2010-05-13 | Begley William J | Oled device with fluoranthene electron injection materials |
| US20100244677A1 (en) * | 2009-03-31 | 2010-09-30 | Begley William J | Oled device containing a silyl-fluoranthene derivative |
| CN102816179A (zh) * | 2007-05-21 | 2012-12-12 | 葛来西雅帝史派有限公司 | 有机电致发光化合物和使用该化合物的有机发光二极管 |
| US8420229B2 (en) | 2007-10-26 | 2013-04-16 | Global OLED Technologies LLC | OLED device with certain fluoranthene light-emitting dopants |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5420249B2 (ja) * | 2005-12-08 | 2014-02-19 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセンス素子のための新規な材料 |
| JP2007230951A (ja) * | 2006-03-02 | 2007-09-13 | Canon Inc | シリル化合物、発光材料およびそれを用いた有機発光素子 |
| WO2007129702A1 (ja) * | 2006-05-09 | 2007-11-15 | Idemitsu Kosan Co., Ltd. | ケイ素含有化合物及びそれを利用した有機エレクトロルミネッセンス素子 |
| JP5580733B2 (ja) * | 2007-05-09 | 2014-08-27 | 東進セミケム株式会社 | 新規なアントラセン系化合物及びこれを利用した有機発光素子 |
| KR101442240B1 (ko) | 2007-10-01 | 2014-10-01 | 동우 화인켐 주식회사 | 유기실란 화합물, 이를 포함하는 유기전기발광소자용 재료,및 유기전기발광소자 |
| KR100991416B1 (ko) * | 2007-12-31 | 2010-11-03 | 다우어드밴스드디스플레이머티리얼 유한회사 | 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
| KR101950474B1 (ko) * | 2012-08-22 | 2019-02-21 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US10381569B2 (en) * | 2014-11-25 | 2019-08-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
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| US5635308A (en) * | 1994-04-26 | 1997-06-03 | Tdk Corporation | Phenylanthracene derivative and organic EL element |
| US5972247A (en) * | 1998-03-20 | 1999-10-26 | Eastman Kodak Company | Organic electroluminescent elements for stable blue electroluminescent devices |
| US6777111B1 (en) * | 1999-08-04 | 2004-08-17 | Kabushiki Kaisha Chuo Kenkyusho | Electro luminescent element |
| US7129386B2 (en) * | 2003-06-27 | 2006-10-31 | Canon Kabushiki Kaisha | Substituted anthryl derivative and electroluminescence device using the same |
-
2005
- 2005-04-08 TW TW094111260A patent/TWI287568B/zh active
- 2005-07-13 US US11/179,573 patent/US20060226768A1/en not_active Abandoned
-
2007
- 2007-03-29 US US11/693,266 patent/US7449593B2/en active Active
- 2007-03-29 US US11/693,288 patent/US20070164669A1/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5635308A (en) * | 1994-04-26 | 1997-06-03 | Tdk Corporation | Phenylanthracene derivative and organic EL element |
| US5972247A (en) * | 1998-03-20 | 1999-10-26 | Eastman Kodak Company | Organic electroluminescent elements for stable blue electroluminescent devices |
| US6777111B1 (en) * | 1999-08-04 | 2004-08-17 | Kabushiki Kaisha Chuo Kenkyusho | Electro luminescent element |
| US7129386B2 (en) * | 2003-06-27 | 2006-10-31 | Canon Kabushiki Kaisha | Substituted anthryl derivative and electroluminescence device using the same |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816179A (zh) * | 2007-05-21 | 2012-12-12 | 葛来西雅帝史派有限公司 | 有机电致发光化合物和使用该化合物的有机发光二极管 |
| US20090108735A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with fluoranthene electron transport materials |
| US20090110957A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with certain fluoranthene host |
| US20090108736A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Phosphorescent oled device with certain fluoranthene host |
| US8076009B2 (en) | 2007-10-26 | 2011-12-13 | Global Oled Technology, Llc. | OLED device with fluoranthene electron transport materials |
| US8129039B2 (en) | 2007-10-26 | 2012-03-06 | Global Oled Technology, Llc | Phosphorescent OLED device with certain fluoranthene host |
| US8420229B2 (en) | 2007-10-26 | 2013-04-16 | Global OLED Technologies LLC | OLED device with certain fluoranthene light-emitting dopants |
| US8431242B2 (en) | 2007-10-26 | 2013-04-30 | Global Oled Technology, Llc. | OLED device with certain fluoranthene host |
| US20100117520A1 (en) * | 2008-11-12 | 2010-05-13 | Begley William J | Oled device with fluoranthene electron injection materials |
| US8088500B2 (en) | 2008-11-12 | 2012-01-03 | Global Oled Technology Llc | OLED device with fluoranthene electron injection materials |
| US20100244677A1 (en) * | 2009-03-31 | 2010-09-30 | Begley William J | Oled device containing a silyl-fluoranthene derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070173658A1 (en) | 2007-07-26 |
| US7449593B2 (en) | 2008-11-11 |
| US20060226768A1 (en) | 2006-10-12 |
| TW200636042A (en) | 2006-10-16 |
| TWI287568B (en) | 2007-10-01 |
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