TWI408128B - 間-三聯苯衍生物及其在有機發光二極體之應用 - Google Patents
間-三聯苯衍生物及其在有機發光二極體之應用 Download PDFInfo
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- TWI408128B TWI408128B TW099142097A TW99142097A TWI408128B TW I408128 B TWI408128 B TW I408128B TW 099142097 A TW099142097 A TW 099142097A TW 99142097 A TW99142097 A TW 99142097A TW I408128 B TWI408128 B TW I408128B
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- Prior art keywords
- organic light
- emitting diode
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- terphenyl
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- -1 M-terphenyl compound Chemical class 0.000 title description 9
- 239000000463 material Substances 0.000 claims abstract description 45
- 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 abstract description 17
- 230000000903 blocking effect Effects 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 238000002347 injection Methods 0.000 claims abstract description 9
- 239000007924 injection Substances 0.000 claims abstract description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 239000011368 organic material Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 abstract description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 abstract description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 43
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 15
- 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 12
- LLQQCDJVSYEQQQ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1 LLQQCDJVSYEQQQ-UHFFFAOYSA-N 0.000 description 10
- 101150003085 Pdcl gene Proteins 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 230000004888 barrier function Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 6
- 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 5
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- LCAYWZTYDNYFSJ-UHFFFAOYSA-N 2-(3-bromophenyl)-5-propan-2-yl-1,3,4-oxadiazole Chemical compound O1C(C(C)C)=NN=C1C1=CC=CC(Br)=C1 LCAYWZTYDNYFSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000005712 elicitor Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- NCXADAULCYRZML-UHFFFAOYSA-N (carbamothioylamino)urea Chemical compound NC(=O)NNC(N)=S NCXADAULCYRZML-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- WKAUICDGONASOP-UHFFFAOYSA-N 2-(3-bromophenyl)-1,3,4-oxadiazole Chemical compound BrC1=CC=CC(C=2OC=NN=2)=C1 WKAUICDGONASOP-UHFFFAOYSA-N 0.000 description 1
- YWBMLIUPPQEWMA-UHFFFAOYSA-N 2-(3-bromophenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(Br)C=CC=2)O1 YWBMLIUPPQEWMA-UHFFFAOYSA-N 0.000 description 1
- PJHHEWRHJXZUJR-UHFFFAOYSA-N 2-(3-bromophenyl)-5-tert-butyl-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=CC=CC(Br)=C1 PJHHEWRHJXZUJR-UHFFFAOYSA-N 0.000 description 1
- UGBVZNXXRZISHN-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3,4-oxadiazole Chemical compound C1=CC(Br)=CC=C1C1=NN=CO1 UGBVZNXXRZISHN-UHFFFAOYSA-N 0.000 description 1
- QTTKXUVFAFOLAC-UHFFFAOYSA-N 2-(4-bromophenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(Br)=CC=2)O1 QTTKXUVFAFOLAC-UHFFFAOYSA-N 0.000 description 1
- XTCMBMSIEIDQOZ-UHFFFAOYSA-N 2-(4-bromophenyl)-5-tert-butyl-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=CC=C(Br)C=C1 XTCMBMSIEIDQOZ-UHFFFAOYSA-N 0.000 description 1
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(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 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- LDUMDMTWZXLCIA-UHFFFAOYSA-N 4-(3-bromophenyl)-3,5-diphenyl-1,2,4-triazole Chemical compound BrC1=CC=CC(N2C(=NN=C2C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LDUMDMTWZXLCIA-UHFFFAOYSA-N 0.000 description 1
- UYROTQZLUVRLJT-UHFFFAOYSA-N 4-(4-bromophenyl)-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC(Br)=CC=C1N1C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 UYROTQZLUVRLJT-UHFFFAOYSA-N 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005277 alkyl imino group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 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 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004467 aryl imino group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002468 redox effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Description
本發明是關於一種化合物及其有機發光二極體,尤其是一種間-三聯苯衍生物及其有機發光二極體。
有機發光二極體(Organic light-emitting diode,OLED)為應用有機材料或有機半導體材料製作之有機發光二極體,其工作原理為電洞及電子分別在電洞傳輸材料及電子傳輸材料中傳遞至發光層中,進行電子電洞再結合以形成激子(exciton),激子再進行能量的轉移以發光,其顏色受發光材料所控制。有機發光二極體具有自發光、廣視角(>170°)、反應時間短(~μs)、高對比、高效率、省電、高亮度、低操作電壓(3-10V)、更輕薄(<2mm)、可撓曲性等優點,因此近年來備受矚目。
電洞和電子之再結合而產生的激子可具有三重態(triplet state)或單重態(singlet state)之自旋態(spin state)。由單重態激子(singlet exciton)所產生的發光為螢光(fluorescence),而由三重態激子(triplet exciton)所產生的發光為磷光(phosphorescence)。磷光的發光效率是螢光的三倍,藉由引入重金屬在發光體結構中,造成強烈的自旋軌道耦合(spin-orbital coupling),進而使得單重態及三重態激發狀態之間的混合,以致於元件的內部量子效率(internal quantum efficiency,IQE)可大幅提升至100%,因此近年來有機發光二極體多採用發磷光的金屬錯合物做為發光層中的磷光摻雜劑。因此,在發光層中通常會以掺雜技術的製程,將發光材料掺雜在主體發光材料中,以抑制發光材料自我淬息(self-quenching)的發生。
然而,因為磷光分子其三重態能階較高,容易造成能量回傳至元件其它材料中,三重態較低之材料造成放光,好的電子傳輸材料必須具備1.具有可逆的電化學氧化還原性質,2.合適的HOMO、LUMO值這是為了使電子有良好的注入降低操作電壓,且最好具有阻擋電洞之能力,目前已知若電子傳輸材料需要具有電洞阻擋性質者,其材料HOMO之性質需為6.0 eV以上3.具有較高之電子移動率,這樣才能把在結合區遠離陰極且增加激子產生速率4.具有高熱穩定性,如此可以避免元件驅動時所產生的熱能造成元件壽命縮短,5.具有良好之成膜性。
為了使元件有更好的效能,達成電子與電洞在元件中的平衡是相當重要的課題,所以載子傳輸材料的開發是相當迫切且亟需的。
本發明之目的為提供一種新穎化合物及其在有機發光二極體之應用。
依據本發明之一實施例,一種間-三聯苯衍生物,具有化學式(I)或(II):
其中,A及B為含氮之五元雜環,以及取代基R、R1
及R2
可獨立選自由氫、鹵素、氰基、三氟甲烷基、胺基、C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、芳基及雜芳基所組成的群組。依據本發明之另一實施例,一種有機發光二極體,包括一陰極、一陽極、設置於陰極及陽極之間的一發光層,以及設置於發光層及陰極之間的有機材料層,其中有機材料層包含上述的間-三聯苯衍生物。
本發明上述及其他態樣、特性及優勢可由附圖及實施例之說明而可更加了解。
本發明之具有雜環取代基之間-三聯苯化合物,其具有化學式(I)或(II):
其中,A及B可為相同或相異之含氮之五元雜環,例如為吡咯(pyrrole)、吡唑(pyrazole)、咪唑(imidazole)、1,2,3三氮唑(1,2,3-triazole)、1,2,4-三氮唑(1,2,4-triazole)、1,2,3,4-四氮唑(1,2,3,4-tetrazole)、1,2-噁唑(1,2-oxazole)、1,3-噁唑(1,3-oxazole)、1,3,4-噁二唑(1,3,4-oxadiazole)、1,2,4-噁二唑(1,2,4-oxadiazole)、1,2-噻唑(1,2-thiazole)及1,3-噻唑(1,3-thiazole)。此外,A及B可以碳原子或氮原子鍵結至間-三聯苯。
間-三聯苯之R取代基、A之取代基R1
及B之取代基R2
可為一或多個,其可獨立選自由氫、鹵素、氰基(cyano,CN)、氟甲烷基(trifluoromethyl,CF3
)、胺基(amino)、C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、芳基及雜芳基所組成的群組。
在此「芳基」指的是具有一或多個芳香環之碳氫基團。芳基基團範例包括苯基(phenyl,Ph)、亞苯基(phenylene)、萘基(naphthyl)、亞萘基(naphthylene)、芘基(pyrenyl)、蒽基(anthryl)、及菲基(phenanthryl)。「雜芳基」指的是具有一或多個芳香環之碳氫基團,且該芳香環包含至少一雜原子(例如,氮、氧或硫)。雜芳基基團範例可包括呋喃基(furyl)、亞呋喃基(furylene)、茀基(fluorenyl)、吡咯基(pyrrolyl)、噻吩基(thienyl)、噁唑基(oxazolyl)、咪唑基(imidazolyl)、噻唑基(thiazolyl)、吡啶基(pyridyl)、嘧啶基(pyrimidinyl)、喹唑啉基(quinazolinyl)、喹啉基(quinolyl)、異喹啉基(isoquinolyl)及吲哚基(indolyl)。
在此應註明的是烷基、烯基、炔基、環烷基、環烯基、雜環烷基、雜環烯基、芳基、以及雜芳基可包括經取代及未經取代之基團。
可能取代於環烷基、環烯基、雜環烷基、雜環烯基、芳基、以及雜芳基之取代基包含但不受限於C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、C1
-C10
烷氧基、芳基、芳氧基、雜芳基、雜芳氧基、胺基、C1
-C10
烷胺基、C1
-C20
二烷胺基、芳胺基、二芳胺基、C1
-C10
烷基磺胺(C1
-C10
alkylsulfonamino)、芳基磺胺(arylsulfonamino)、C1
-C10
烷基亞胺(C1
-C10
alkylimino)、芳基亞胺(arylimino)、C1
-C10
烷基磺亞胺(C1
-C10
alkylsulfonimino)、芳基磺亞胺(arylsulfonimino)、氫氧基、鹵素、硫代基(thio)、C1
-C10
烷硫基、芳硫基、C1
-C10
烷磺醯基(alkylsulfonyl)、芳磺醯基(arylsulfonyl)、醯基胺(acylamino)、胺基醯(aminoacyl)、胺基硫醯(aminothioacyl)、醯胺基(amido)、脒基(amidino)、胍基(guanidine)、脲基(ureido)、硫脲基(thioureido)、腈基、硝基、亞硝基、疊氮基(azido)、醯基、硫醯基、醯氧基(acyloxy)、羧基、及羧酸酯等。另一方面,可能取代於烷基、烯基、或炔基之取代基包含除C1
-C10
烷基外之上述所有取代基。環烷基、環烯基、雜環烷基、雜環烯基、芳基、及雜芳基亦可互相稠合(fused)。
在一較佳實施例中,A與B為相同,以及A之取代基R1
及B之取代基R2
為相同。A可為1,3,4-噁二唑或1,2,4-三氮唑。1,3,4-噁二唑及1,2,4-三氮唑已知具有良好的電子吸引力,並且其最高佔據軌道能階(highest occupied molecular orbital,HOMO)非常低,因此容易阻絕電洞傳遞。因此1,3,4-噁二唑、1,2,4-三氮唑與三聯苯搭配可作為電子傳輸層。
在一實施例中,具有雜環取代基之間-三聯苯化合物,其具下列化學式(a)至式(e)。
在另一實施例中,具有雜環取代基之間-三聯苯化合物,其具下列化學式式(f)至式(j)。
此外,請參照圖1,為示意圖顯示具有雜環取代基之間-三聯苯化合物的有機發光二極體結構之一實施例。有機發光二極體結構具有設置於陽極1及陰極2之間包含化合物的發光層3。發光層3係將發光材料摻雜至主體發光材料中所構成。有機發光二極體結構還包括從陽極1上方依序形成之電洞注入層7、電洞傳輸層4、電子阻擋層9、發光層3、激發子阻擋層10、電洞阻擋層6、電子傳輸層5及電子注入層8。其中,各層之實際厚度與圖中所顯示之尺寸並無關係。其中,本有機發光二極體之激發子阻擋層10、電子阻擋層9、電洞阻擋層6及電子注入層8為選擇性包含。其中具有雜環取代基之間-三聯苯化合物可為一電子傳輸材料、一電子注入材料、電洞阻擋材料或一激發子阻擋材料。
請參照下列反應途徑,以下簡述本發明之間-三聯苯化合物之合成方式。
以化合物m
-2a Bis(1,3,4-oxadiazole-5-diyl) 3,3’-m-terphenyl為例,其可由反應物m
-1a 2-(3-bromophenyl)-1,3,4-oxadiazole與1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene在K2
CO3
及PdCl2
(PPh3
)2
存在之下進行反應而得。
同理p
-2a Bis(1,3,4-oxadiazole-5-diyl) 4,4’-m-terphenyl為例,其可由反應物p
-1a 2-(4-bromophenyl)-1,3,4-oxadiazole與1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene在K2
CO3
及PdCl2
(PPh3
)2
存在之下進行反應而得。
請參照下列反應式,同理可選擇不同的起始物質m
-1b、p
-1b、m
-1c或p
-1c進行反應,以得到產物m
-2b、p
-2b、m
-2c或p
-2c。
以下更加詳細舉出本發明化合物範例。然而,本發明之範圍並不以這些範例為限,而應參照之後的申請專利範圍。
將2-(3-bromophenyl)-5-isopropyl-1,3,4-oxadiazole(5 g,18.79 mmol)、K2
CO3
(12.96 g,93.98 mmol)、PdCl2
(PPh3
)2
(10 mol%)及1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(3.10 g,9.39 mmol)以及40 mL DMSO加到100 mL雙頸瓶。於80-120 ℃攪拌進行反應直到以TLC(薄層色層分析)監測起始物質消失。接著過濾以將催化劑移除,並以氯仿清洗。以水對粗產物進行五至六次的萃取以移除DMSO。將有機層以硫酸鎂過濾並以低壓濃縮,接由以矽膠管柱層析純化(己烷/乙酸乙酯=2:1)以得到產物,產率:75%。
1
H-NMR(400 MHz,CDCl3
,δ): 8.31(s,2H),8.04-8.02(d,J
=8 Hz,2H),7.86(s,1H),7.80-7.78(d,J
=8 Hz,2H),7.66-7.65(d,J
=4 Hz,2H),7.65-7.55(m,3H),3.29-3.26(m,2H),1.46-1.44(d,J
=8 Hz,12H).
13
C-NMR(100 MHz,CDCl3
,δ): 170.79,164.28,141.59,140.48,130.09,129.53,126.57,125.84,125.58,125.22,124.52,26.26,19.89.
HRMS(EI) Calcd for C28
H26
N4
O2
(M+
): 450.2056. Found: 450.2060.
將2-(3-bromophenyl)-5-isopropyl-1,3,4-oxadiazole(5 g,18.79 mmol)、K2
CO3
(12.96 g,93.98 mmol)、PdCl2
(PPh3
)2
(10 mol%)及1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(3.10 g,9.39 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:82%。
1
H-NMR(400 MHz,CDCl3
,δ): 8.13-8.11(d,J
=8 Hz,4H),7.85(s,1H),7.77-7.75(d,J
=8 Hz,4H),7.66-7.64(d,J
=8 Hz,2H),7.58-7.55(m,1H),3.29-3.26(m,2H),1.47-1.45(d,J
=8 Hz,12H).
13
C-NMR(100 MHz,CDCl3
,δ): 170.88,164.34,143.78,140.63,129.56,127.66,127.25,126.84,125.39,123.17,26.42,20.03.
HRMS(EI) Calcd for C28
H26
N4
O2
(M+
): 450.2056. Found: 450.2058.
將2-(3-bromophenyl)-5-tert-butyl-1,3,4-oxadiazole(5 g,17.85 mmol)、K2
CO3
(12.31 g,89.27 mmol)、PdCl2
(PPh3
)2
(10 mol%) and 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(2.94 g,8.92 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:78%。
1
H-NMR(400 MHz,CDCl3
,δ): 8.29(s,2H),8.04-8.02(d,J
=8 Hz,2H),7.86(s,1H),7.80-7.78(d,J
=8 Hz,2H),7.67-7.65(d,J
=8 Hz,2H),7.61-7.57(m,3H),1.48(s,18H).
13
C-NMR(100 MHz,CDCl3
,δ): 173.31,164.53,141.89,140.85,130.34,129.54,126.86,126.20,125.85,125.52,124.87,32.54,28.28.
HRMS(FAB) Calcd for C30
H30
N4
O2
(M+
+1): 479.2447. Found: 479.2457.
將2-(4-bromophenyl)-5-tert-butyl-1,3,4-oxadiazole(5 g,17.85 mmol)、K2
CO3
(12.31 g,89.27 mmol)、PdCl2
(PPh3
)2
(10 mol%) and 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(2.94 g,8.92 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:86%。
1
H-NMR(400 MHz,CDCl3
,δ): 8.15-8.13(d,J
=8 Hz,4H),7.87(s,1H),7.79-7.77(d,J
=8 Hz,4H),7.68-7.66(d,J
=8 Hz,2H),7.60-7.57(m,1H),1.51(s,18H).13
C-NMR(100 MHz,CDCl3
,δ): 173.19,164.36,143.78,140.68,129.57,127.67,127.28,126.85,125.96,123.26,32.48,28.22.
HRMS(FAB) Calcd for C30
H30
N4
O2
(M+
+1): 479.2447. Found: 479.2449.Anal. calcd. For C30
H30
N4
O2
: C 75.29,H 6.32,N 11.71;Found: C 75.18,H6.34,N 11.50.
將2-(3-bromophenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole(5 g,14.04 mmol)、K2
CO3
(9.61 g,70.20 mmol)、PdCl2
(PPh3
)2
(10 mol%) and 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(2.31 g,7.02 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:76%。
1
H-NMR(400 MHz,CDCl3
,δ): 8.41(s,2H),8.14-8.12(d,J
=8 Hz,2H),8.09-8.07(d,J
=8 Hz,4H),7.92(s,1H),7.84-7.82(d,J
=8 Hz,2H),7.68-7.66(d,J
=8 Hz,2H),7.64-7.53(m,7H),1.34(s,18H).
13
C-NMR(100 MHz,CDCl3
,δ): 164.73,164.21,155.33,141.81,140.63,130.36,129.70,129.58,129.54,126.76,126.05,125.99,125.82,125.52,124.57,120.94,35.02,31.04.
HRMS(EI) Calcd for C42
H38
N4
O2
(M+
): 630.2995. Found: 630.2995.
將2-(4-bromophenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole(5 g,14.04 mmol)、K2
CO3
(9.61 g,70.20 mmol)、PdCl2
(PPh3
)2
(10 mol%) and 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(2.31 g,7.02 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:85%。
1
H-NMR(400 MHz,CDCl3
,δ): 8.22-8.20(d,J
=8 Hz,4H),8.07-8.05(d,J
=8 Hz,4H),7.88(s,1H),7.81-7.79(d,J
=8 Hz,4H),7.67-7.65(d,J
=8 Hz,2H),7.59-7.53(m,5H),1.35(s,18H).13
C-NMR(100 MHz,CDCl3
,δ): 164.66,164.10,155.33,143.87,140.58,129.59,127.72,127.36,126.86,126.73,126.00,125.92,123.03,120.98,35.03,31.06. HRMS(EI) Calcd for C42
H38
N4
O2
(M+
): 630.2995. Found: 630.2999.
將4-(3-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole(5 g,13.33 mmol)、K2
CO3
(9.2 g,66.66 mmol)、PdCl2
(PPh3
)2
(10 mol%)、1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(2.2 g,6.6 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:80%。
1
H-NMR(400 MHz,CDCl3
,δ): 7.65-7.63(m,4H),7.51-7.28(m,24H),7.14-7.12(m,4H).13
C-NMR(100 MHz,CDCl3
,δ): 154.62,142.35,139.76,135.66,130.28,129.64,128.83,128.42,128.04,126.87,126.68,126.59,126.17,125.69. HRMS(EI) Calcd for C46
H32
N6
(M+
): 668.2688. Found: 668.2688.
將4-(4-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole(5 g,13.33 mmol)、K2
CO3
(9.2 g,66.66 mmol)、PdCl2
(PPh3
)2
(10 mol%)、1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene(2.2 g,6.6 mmol)以及40 mL DMSO加到100 mL雙頸瓶,並進行範例1之步驟以得到產物,以得到產物,產率:83%。
1
H-NMR(400 MHz,CDCl3
,δ): 7.84(s,1H),7.73-7.71(d,J
=8 Hz,4H),7.67-7.26(m,27H).
13
C-NMR(100 MHz,CDCl3
,δ): 154.76,141.82,140.00,134.46,129.66,128.83,128.44,128.18,126.58,125.91.
HRMS(EI) Calcd for C46
H32
N6
(M+
): 668.2688. Found: 668.2699.
上述化合物之LUMO、HOMO及能階如表1所列。
註:對照組化合物OXD-7(1,3-Bis[(p-tert-butyl)phenyl-1,3,4-oxadiazoyl]benzene)為電子傳輸材料。
在有機發光二極體元件中,當電子傳輸材料三重態能階越高,則在元件中可以避免激發子之擴散至電子傳輸層放光,並避免元件不必要之漏光。藉此增加元件之光色純度及發光效率。本發明之範例化合物1~6之三重態能階為2.77~2.9 eV,大於對照組OXD-7(2.70 eV),因此具有較佳之效能,其材料適合作為激發子阻擋材料。
所形成的裝置結構之中,ITO做為基板及電極,測試的電極材料包括LiF/Al;測試的發光材料包括Bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium(Firpic)、Iridium、fac-tris(2-phenylpyridine) iridium(III)(Ir(ppy)3
)、Bis(1-phenylisoquinoline)(acetylacetonate) iridium(III)(Ir(piq)2
acac);測試的電子傳輸層包括Bhen(4,7-diphenyl-1,10-phenanthrolin)及Alq3
(tris(8-hydroxyquinoline)aluminum(III)),其可做為電洞阻擋層或者同時做為電洞阻擋層及電子傳輸層。測試的電洞傳輸層包括(4,4’-bis[N
-(1-naphthyl)-N
-phenyl-amino]bipheny) NPB及(1,1-bis(di-4-tolylaminophenyl) cyclohexane) TAPC,其可做為電子阻擋層或者同時做為電子阻擋層及電洞傳輸層。本發明之化合物m
-2a、m
-2b則用以作為電子傳輸材料及/或電子注入層。
測試裝置的個別詳細架構及其厚度(單位為nm)如下列,其中裝置A、B、E為藍光OLED,裝置C、D為綠光OLED,裝置F為紅光OLED,裝置G為摻雜在發光層中OLED;對照組所使用電子傳輸材料為OXD-7:
裝置A: NPB(50)/TAPC(15)/11% Firpic:發光主體材料(host)
(40)/m
-2b(12.5)/BPhen(12.5)/LiF(1)/Al(100).
裝置B: NPB(50)/TAPC(15)/11% Firpic:發光主體材料(host)
(40)/m
-2a(12.5)/BPhen(12.5)/LiF(1)/Al(100).
裝置AB之對照組(Ref-A,B): NPB(50)/TAPC(15)/11% Firpic:發光主體材料(host)
(40)/OXD-7(12.5)/Bphen(12.5)/LiF(1)/Al(100).
裝置C: NPB(50)/TAPC(15)/5% Ir(PPy)3
:發光主體材料(host)
(40)/m
-2b(12.5)/TAZ(12.5)/LiF(1)/Al(100).
裝置D: NPB(20)/TAPC(15)/16% Ir(ppy)3
:發光主體材料(host)
(40)/m
-2b(12.5)/TAZ(12.5)/LiF(1)/Al(100).
裝置CD之對照組(Ref-C,D): NPB(20)/TAPC(15)/16% Ir(ppy)3
:發光主體材料(host)
(40)/OXD-7(12.5)/TAZ(12.5)/LiF(1)/Al(100).
裝置E: TAPC(30)/發光主體材料(host)
11% Firpic: mcp(50)/m-2b(30)/LiF(1)/Al(100).
裝置E之對照組(Ref-E):: TAPC(30)/發光主體材料(host)
mcp: 11% Firpic(50)/OXD-7(30)/LiF(1)/Al(100).
裝置F: TAPC(50)/發光主體材料(host)
: 10% Ir(piq)2
acac(50)/m
-2a(30)/LiF(1)/Al(100).
裝置F之對照組(Ref-F): TAPC(50)/發光主體材料(host)
: 10% Ir(piq)2
acac(50)/OXD-7(30)/LiF(1)/Al(100).
裝置G: TAPC(30)/發光主體材料(host)
Firpic: m-2a(50)/m-2a(30)/LiF(1)/Al(100)
上述測試裝置之發光效能如表3所列。
a.V d
:驅動電壓(Drive voltage);
b.L max
:最大亮度(maximum luminescence);
c. η ext
:最大外部量子效率(maximum external quantum efficiency);
d. η c
:最大電流效率(maximum current efficiency);
e. η p
:最大電能效率(maximum power efficiency);
f. λmax
:最大發射波長(maximum emission wavelength)
請參照表3,相較於對照組,使用本發明之間-三聯苯衍生物m
-2a、m
-2b之有機發光二極體在各項指標方面都有較佳表現,因此具有較佳之效能。
綜合上述,本發明之間-三聯苯衍生物具有良好的電子吸引力,並且其最高佔據軌道能級較低,因此容易阻絕電洞,為一個良好的電子傳輸材料。
以上所述之實施例僅是為說明本發明之技術思想及特點,其目的在使熟習此項技藝之人士能夠瞭解本發明之內容並據以實施,當不能以之限定本發明之專利範圍,即大凡依本發明所揭示之精神所作之均等變化或修飾,仍應涵蓋在本發明之專利範圍內。
1...陽極
2...陰極
3...發光層
4...電洞傳輸層
5...電子傳輸層
6...電洞阻擋層
7...電洞注入層
8...電子注入層
9...電子阻擋層
10...激發子阻擋層
圖1為示意圖顯示具有間-三聯苯衍生物的有機發光二極體結構。
1...陽極
2...陰極
3...發光層
4...電洞傳輸層
5...電子傳輸層
6...電洞阻擋層
7...電洞注入層
8...電子注入層
9...電子阻擋層
10...激發子阻擋層
Claims (10)
- 一種間-三聯苯衍生物,具有化學式m-2a,p-2a,m-2b或p-2b:
- 如請求項1之間-三聯苯衍生物,其具下列化學式(a)~(j):
- 一種有機發光二極體,包括:一陰極; 一陽極;一發光層,設置於該陰極及該陽極之間;以及一有機材料層,設置於該發光層及該陰極之間,其中該有機材料層包含一間-三聯苯衍生物,其具有化學式m-2a,p-2a,m-2b或p-2b:
- 如請求項3之有機發光二極體,其中該間-三聯苯衍生物具有具下列化學式(a)~(j):
- 如請求項3之有機發光二極體,其中該有機發光二極體為一藍光有機發光二極體、一綠光有機發光二極體、藍色磷光有機發光二極體或一綠色磷光有機發光二極體。
- 如請求項3所述之有機發光二極體,其中該有機材料層為一電子傳輸層,以及該間-三聯苯衍生物為一電子傳輸材料。
- 如請求項3所述之有機發光二極體,其中該有機材料層為一電子注入層,以及該間-三聯苯衍生物為一電子注入材料。
- 如請求項3所述之有機發光二極體,其中該有機材料層為一電洞阻擋層,以及該間-三聯苯衍生物為一電洞阻擋材料。
- 如請求項3所述之有機發光二極體,其中該有機材料層為一激發子阻擋層,以及該間-三聯苯衍生物為一激發子阻擋材料。
- 如請求項3之有機發光二極體,其中該有機發光二極體為一紅光有機發光二極體或一紅色磷光有機發光二極體。
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