US20100013377A1 - Compounds for use in Opto-Electrical Devices - Google Patents
Compounds for use in Opto-Electrical Devices Download PDFInfo
- Publication number
- US20100013377A1 US20100013377A1 US12/439,163 US43916307A US2010013377A1 US 20100013377 A1 US20100013377 A1 US 20100013377A1 US 43916307 A US43916307 A US 43916307A US 2010013377 A1 US2010013377 A1 US 2010013377A1
- Authority
- US
- United States
- Prior art keywords
- triazine
- composition according
- host material
- opto
- polarity
- 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
Links
- 150000001875 compounds Chemical class 0.000 title description 13
- 239000000463 material Substances 0.000 claims abstract description 88
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 229920000642 polymer Polymers 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 27
- -1 small molecule triazine compound Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 18
- 230000003381 solubilizing effect Effects 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 239000002800 charge carrier Substances 0.000 claims description 10
- 238000000151 deposition Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000005829 chemical entities Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 150000003918 triazines Chemical class 0.000 description 22
- 239000010408 film Substances 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 16
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 0 *C.Cc1ccc(-c2nc(-c3ccccc3)nc(-c3ccc(C)cc3)n2)cc1 Chemical compound *C.Cc1ccc(-c2nc(-c3ccccc3)nc(-c3ccc(C)cc3)n2)cc1 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000005259 triarylamine group Chemical group 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
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- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003384 small molecules Chemical class 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 239000011970 polystyrene sulfonate Substances 0.000 description 4
- 229960002796 polystyrene sulfonate Drugs 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- YGXMMMPUTDCEAF-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis-phenyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1=CC=CC=C1N(C=1N=C(N=C(N=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 YGXMMMPUTDCEAF-UHFFFAOYSA-N 0.000 description 2
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HOJGZLCCYUQBTK-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C2=CC=C(C3=NC(C4=CC=C(C5=CC=C(C(C)(C)C)C=C5)C=C4)=NC(C4=CC=C(C5=CC=C(C(C)(C)C)C=C5)C=C4)=N3)C=C2)C=C1.CC(C)(C)C1=CC=C(C2=CC=C(C3=NC(C4=CC=CC=C4)=NC(C4=CC=C(C5=CC=C(C(C)(C)C)C=C5)C=C4)=N3)C=C2)C=C1.CC1=C(C2=CC=C(C(C)(C)C)C=C2)C=CC(C2=NC(C3=CC(C)=C(C4=CC=C(C(C)(C)C)C=C4)C=C3)=NC(C3=CC(C)=C(C4=CC=C(C(C)(C)C)C=C4)C=C3)=N2)=C1 Chemical compound CC(C)(C)C1=CC=C(C2=CC=C(C3=NC(C4=CC=C(C5=CC=C(C(C)(C)C)C=C5)C=C4)=NC(C4=CC=C(C5=CC=C(C(C)(C)C)C=C5)C=C4)=N3)C=C2)C=C1.CC(C)(C)C1=CC=C(C2=CC=C(C3=NC(C4=CC=CC=C4)=NC(C4=CC=C(C5=CC=C(C(C)(C)C)C=C5)C=C4)=N3)C=C2)C=C1.CC1=C(C2=CC=C(C(C)(C)C)C=C2)C=CC(C2=NC(C3=CC(C)=C(C4=CC=C(C(C)(C)C)C=C4)C=C3)=NC(C3=CC(C)=C(C4=CC=C(C(C)(C)C)C=C4)C=C3)=N2)=C1 HOJGZLCCYUQBTK-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical compound O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 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
- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- CDBMGJUEACTJIC-UHFFFAOYSA-N 2-n,4-n,6-n-trinaphthalen-2-yl-2-n,4-n,6-n-triphenyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1=CC=CC=C1N(C=1N=C(N=C(N=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=CC=C2)C2=C1 CDBMGJUEACTJIC-UHFFFAOYSA-N 0.000 description 1
- GGUFVZFOCZNPEG-UHFFFAOYSA-N 4,5,6-triphenyltriazine Chemical group C1=CC=CC=C1C1=NN=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GGUFVZFOCZNPEG-UHFFFAOYSA-N 0.000 description 1
- SKXUZFJOLNNWIG-UHFFFAOYSA-N 4-bromo-3-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC=C1Br SKXUZFJOLNNWIG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Definitions
- This invention relates to compositions comprising triazine host compounds for use in fabricating phosphorescent opto-electrical devices, and methods of fabricating opto-electrical devices using these compositions.
- One class of opto-electrical devices is that using an organic material for light emission or detection.
- the basic structure of these devices is a light emissive organic layer, for instance a film of a poly(p-phenylenevinylene) (“PPV”) or polyfluorene, sandwiched between a cathode for injecting negative charge carriers (electrons) and an anode for injecting positive charge carriers (holes) into the organic layer.
- PV poly(p-phenylenevinylene)
- holes positive charge carriers
- the organic light-emissive material is a polymer.
- the organic light-emissive material is of the class known as small molecule materials, such as (8-hydroxyquinoline)aluminium (“Alq3”).
- small molecule materials such as (8-hydroxyquinoline)aluminium (“Alq3”).
- Alq3 (8-hydroxyquinoline)aluminium
- one of the electrodes is transparent, to allow the photons to escape the device.
- a typical organic light-emissive device is fabricated on a glass or plastic substrate coated with a transparent first electrode such as indium-tin-oxide (“ITO”).
- ITO indium-tin-oxide
- a layer of a thin film of at least one electroluminescent organic material covers the first electrode.
- a cathode covers the layer of electroluminescent organic material.
- the cathode is typically a metal or alloy and may comprise a single layer, such as aluminium, or a plurality of layers such as calcium and aluminium. Other layers can be added to the device, for example to improve charge injection from the electrodes to the electroluminescent material.
- a hole injection layer such as poly(ethylene dioxythiophene)/polystyrene sulfonate (PEDOT-PSS) or polyaniline may be provided between the anode and the electroluminescent material.
- PEDOT-PSS polystyrene sulfonate
- polyaniline may be provided between the anode and the electroluminescent material.
- holes are injected into the device through the anode and electrons are injected into the device through the cathode.
- the holes and electrons combine in the organic electroluminescent layer to form an exciton which then undergoes radiative decay to give light.
- binding energies measured with respect to the vacuum level of the electronic energy levels, particularly the “highest occupied molecular orbital” (HOMO) and the “lowest unoccupied molecular orbital” (LUMO) level. These can be estimated from measurements of photoemission and particularly measurements of the electrochemical potentials for oxidation and reduction. It is well understood in this field that such energies are affected by a number of factors, such as the local environment near an interface, and the point on the curve (peak) from which the value is determined. Accordingly, the use of such values is indicative rather than quantitative.
- optical and electronic properties of an organic semiconductor are highly dependent on the energy of the aforementioned HOMO and LUMO levels. Furthermore, these energy levels are highly dependent on the chemical structure of the organic semiconductor. By selecting suitable materials, or combinations of materials, device performance can be improved.
- WO 99/48610 discloses blending of hole transporting polymers, electron transporting polymers and electroluminescent polymers.
- a 1:1 copolymer of dioctylfluorene and triphenylamine is disclosed as a hole transporting polymer in this document.
- the type of charge transporting material which is most effective will be dependent on the HOMO and LUMO of the other components in the device.
- WO 02/083760 discloses copolymers for use as charge transporting materials and fluorescent emissive materials in organic opto-electrical devices.
- the co-polymers comprise a first repeat unit which may be a triazine unit as shown in formula (a):
- R′′ is selected from hydrogen, branched or linear C1-C20 alkyl or alkoxy.
- the copolymers comprise a second repeat unit which may be selected from the group consisting of optionally substituted phenylenes, fluorenes, heteroaryls and triarylamines.
- Triazines as components of blue electroluminescent devices are disclosed in WO 2004/077885.
- U.S. Pat. No. 6,821,643 discloses arylated triazines that are deposited by evaporation to form a blue fluorescent light-emitting layer or an electron transport layer of an OLED.
- U.S. Pat. No. 6,352,791 discloses arylated triazines that are deposited by evaporation to form an electron transport layer of an OLED.
- WO 2005/105950 discloses certain tri-substituted triazines used as a blue fluorescent light-emitting layer of an OLED.
- EP 1385221 discloses a light-emitting device comprising a luminescent region comprising an anthracene derivative compound and a triazine derivative compound.
- Phosphorescent materials are also useful and in some applications may be preferable to fluorescent materials.
- One type of phosphorescent material comprises a host and a phosphorescent emitter in the host.
- the emitter may be bonded to the host or provided as a separate component in a blend.
- hosts for phosphorescent emitters are described in the prior art including “small molecule” hosts such as 4,4′-bis(carbazol-9-yl)biphenyl), known as CBP, and (4,4′,4′′-tris(carbazol-9-yl)triphenylamine), known as TCTA, disclosed in Ikai et al. ( Appl. Phys. Lett., 79 no. 2, 2001, 156); and triarylamines such as tris-4-(N-3-methylphenyl-N-phenyl)phenylamine, known as MTDATA.
- Homopolymers are also known as hosts, in particular poly(vinyl carbazole) disclosed in, for example, Appl. Phys. Lett.
- a problem with known host-phosphor systems is that the host may quench emission from the phosphor.
- Polymerisation can exacerbate this problem by reducing the triplet energy level to below that of a monomer when forming a host polymer. Accordingly, there is a need to produce materials with a high triplet energy level for use as hosts in phosphorescent systems.
- JP 2005071983 discloses tris-carbazolyl substituted triazines as a host for Irppy, for example:
- WO 2005029923 discloses tris-benzimidazolyl substituted triazine as a host for the red phosphor, Ir(piq):
- US2005/0287393 discloses a light emissive composition
- a light emissive composition comprising a phosphorescent dopant and a host including a carbazole compound and a small molecule triazine compound.
- Exemplary triazine compounds are given as 2,4,6-tris(diarylamino)-1,3,5-triazine, 2,4,6-tris(diphenylamino)-1,3,5-triazine, 2,4,6-tricarbazolo-1,3,5-triazine, 2,4,6-tris(N-phenyl-2-naphthylamino)-1,3,5-triazine, 2,4,6-tris(N-pheyl-1 -naphthyl amino)-1,3,5-triazine, or 2,4,6-trisbiphenyl-1,3,5-triazine.
- All of the above-identified small molecule triazines for use as hosts in phosphorescent compositions are amino derivative except for the last example, 2,4,6-trisbiphenyl-1,3,5-triazine, given in the list of examples in US2005/0287393.
- the amino derivatives all have a nitrogen atom directly bonding the aryl substituents to the central triazine ring.
- this nitrogen linkage is not completely stable which can reduce the lifetime of these compositions.
- none of the above-identified small molecule compounds are soluble enough to be readily solution processed and instead these compounds are more suited to vacuum thermal deposition.
- Host-emitter systems are not limited to phosphorescent devices.
- a wide range of fluorescent low molecular weight metal complexes are known and have been demonstrated in organic light emitting devices [see, e. g., Macromol. Sym. 125 (1997) 1-48, U.S. Pat. No. 5,150,006, U.S. Pat. No. 6,083,634 and U.S. Pat. No. 5,432,014].
- a problem with known host-fluorescent emitter systems is that the host may quench emission from the fluorescent emitter. It is advantageous to provide a host having a higher LUMO than that of the emitter to inject electrons into the emitter. It is advantageous to provide a host having a lower HOMO than that of the emitter to inject holes into the emitter. Accordingly, there is a need to produce materials with a large band gap between the HOMO and LUMO for use as hosts in fluorescent systems.
- Another factor affecting the performance of opto-electonic devices is morphology of the films which make up the device.
- semiconductive organic materials it is advantageous to have an amorphous rather than a crystalline film.
- composition for use in fabricating opto-electrical devices comprising a solution processable triazine host material and a phosphorescent moiety.
- the solution processable triazine host material is a small molecule triazine compound.
- the solution processable triazine host material is a polymer comprising a triazine repeat unit.
- small molecule we mean non-polymeric.
- small molecule is often used in this art to have this meaning as there are two main families of organic opto-electrical materials: polymers and small molecules. Oligomers consist of 1 to 10 repeat units, more preferably, 1 to 5 repeat units.
- the triazine host material comprises a solubilising substituent.
- solvents suitable for opto-electrical device fabrication include xylene, toluene, chlorobenzene, chloroform or tetrahydrofuran but preferably toluene or xylene.
- the prior art compound 2,4,6-tris(biphenyl)-1,3,5-triazine has a solubility ⁇ 5 mg ml ⁇ 1 in all of these solvents and thus is not a suitable material for fabricating an OLED device by solution processing.
- compositions comprising small molecule triazine compounds of the present invention can be deposited to form a film by, for example, ink-jet printing or spin-coating rather than thermal vapour deposition.
- solubilising substituents reduce the crystallinity of a film formed by depositing triazine compounds when compared with prior art small molecule triazine compounds resulting in a better film morphology.
- solubilizing substituent can be used to tune the physical properties of a film.
- the present invention provides triazine compounds which can be solution processed and which produce films having a good morphology and tunable physical properties for use in opto-electrical devices.
- the triazine compounds of the present invention have both a deep LUMO and a deep HOMO.
- the triazine compounds readily accept electrons but do not readily accept holes in an opto-electrical device.
- these compounds serve as electron transporting host materials for emissive materials without quenching emission from the emissive materials.
- the LUMO level is intermediate in energy between the fermi level of the electron injecting material in the cathode and the LUMO level (or triplet level in phosphorescent emissive materials) of the emissive material or at least not significantly higher than the fermi level of the electron injecting material or significantly lower than the LUMO (or triplet level) of the emissive material as to require a high drive voltage.
- the HOMO level of the triazine compounds is lower than the HOMO level of the emissive material. Due to the poor hole accepting/hole transporting properties of the triazines, it is preferable to use them in conjunction with a hole transporting material or with an emissive material which is a good hole transporting material.
- the LUMO levels of the triazine compounds are preferably intermediate in energy between the injecting cathode and the emitter. If a barrier to electron injection is present it is preferably not more than 0.4 eV above the work function of the cathode.
- the HOMO level of the triazine should be such as to maintain an optical band-gap large enough to maintain a triplet level energy gap that will not quench the phosphorescence from the emitter species.
- the electrical characteristics of the triazine compounds of the present invention are such that in additional to acting as good host materials, they can also be used as blue emissive materials, electron transporting materials (either in a separate electron transporting layer located between the cathode and the emissive layer of a device or incorporated into the emissive layer of the device as a blend with an emissive material or bonded to the emissive material) and/or hole blocking materials (located in a layer between the emissive layer and the cathode in a device). Furthermore, the low LUMO of the triazine compounds also allows cathode materials with higher work-functions to be used.
- Triazine compounds with LUMO level of, for example, 2.8 eV will allow the use of higher work function cathodes where the energy gap is not greater than 0.4 eV.
- cathode materials with work functions in the range 2.6 to 3.2 eV are preferred.
- the at least one solubilizing substituent comprises a C 4 -C 20 alkyl chain. It has been found that alkyl chains within this range render the triazine compound sufficiently soluble to be readily solution processed and form films having a good morphology. The length and composition of the alkyl chain can be tailored to tune the physical properties of the film according to its specific use.
- the central triazine ring is substituted with at least one aryl group.
- the aryl group is directly bonded to the central triazine ring.
- the aryl group may be a phenyl ring.
- the triazine compound is a tris-aryl triazine with at least one of the aryl groups having a solubilizing substituent bonded thereto. More preferably, two or three of the aryl groups have solubilizing substituents bonded thereto.
- the solubilizing groups may be the same or different.
- tris-aryl triazine compounds having solubilizing groups thereon form films with a good physical morphology and good physical properties.
- the aryl groups and the solubilising groups provide a film which is amorphous but does not have too much disorder. These films have better opto-electrical properties and produce a device with better performance.
- the at least one solubilizing substituent is directly bonded to the central triazine ring via a carbon atom.
- the prior art triazine compounds which have substituents bonded to the central triazine ring via a nitrogen atom may be unstable in an opto-electrical device thus reducing the lifetime of the device.
- the nitrogen linking atom may act as a reactive site for substitution of the substituent during device operation.
- carbon bonded substituents according to embodiments of the present invention are more stable in an opto-electrical device.
- the triazine structures are simple triaryl substituted compounds without heteroatom linkages but with alkyl substituents or preferably aryl substituents having alkyl groups thereon, selected to allow tuning of the physical properties of the films formed using these structures, e.g. Tg>150° C., good film morphology, appropriate HOMO and LUMO levels etc.
- Tg>150° C. good film morphology
- appropriate HOMO and LUMO levels etc An example of such a structure is shown in the formula below:
- R groups are solubilizing substituents.
- Asymmetric structures where R on one ring can differ from R on the other two rings are also possible. Further examples are given in the formulas below:
- triphenyl triazine moiety that is common to the above structures is more chemically and electrochemically inert and is therefore more stable in the device when compared with standard hosts, for example CBP, optionally substituted with solubilising groups such as alkyl or alkoxy groups.
- the triazines are also advantageous as they have good electron transport properties, which make them much more suitable for use in common device structures, as they can be used in conjunction with an electron-blocking/hole transporting layer disposed between the light-emissive layer and a hole injecting layer. There is also no need for a hole-blocking/electron transporting layer disposed between the light-emissive layer and the cathode, which is commonly required in phosphorescent devices.
- solution processable triazine materials are excellent hosts for phosphorescent emissive materials as their deep LUMO provide enhanced electron-injection/transport and their wide triplet band-gap reduces quenching.
- the advantageous features described in relation to the first aspect of the invention are also applicable to the second aspect of the invention.
- the triazine units may be provided in a copolymer with, for example, hole transporting units such as a triaryl amine or a twisted co-monomer which will maintain the triplet level of the polymer so as not to quench the emission from the phosphorescent emitter.
- hole transporting units such as a triaryl amine or a twisted co-monomer which will maintain the triplet level of the polymer so as not to quench the emission from the phosphorescent emitter.
- the co-polymer may comprise the phosphorescent moiety.
- the phosphorescent moiety may be provided in the polymer backbone or in a pendent side chain.
- the phosphorescent moiety is a green emitter.
- Known hosts for green emitters such as solution processable polyfluorene host materials generally have triplet levels that are too low to be efficient hosts for green phosphorescent moieties.
- embodiments of the present invention are efficient host materials for green phosphorescent moieties.
- the solution processable triazines may also be used as hosts for red phosphorescent moieties.
- these monomers can be used to prepare wide band-gap polymers with similarly good electron injection/transport, but that avoid the need for polyfluorenes that generally have triplet levels that are too low to use as a green phosphorescent host.
- these monomers can be used to prepare wide band-gap polymers with similarly good electron injection/transport, but that avoid the need for polyfluorenes that generally have triplet levels that are too low to use as a green phosphorescent host.
- This polymer has the processing properties of a conjugated polymer with the triplet band-gap and electron injection properties of the triazine.
- Other monomers could also be introduced to fine-tune the charge injection/conduction properties, or to add luminescent centres.
- a method of fabricating an opto-electrical device comprising the steps: depositing from solution, on a substrate comprising a first electrode for injecting charge carriers of a first polarity, a composition according to the first aspect of the present invention; and depositing thereover a second electrode for injecting charge carriers of a second polarity opposite to the first polarity.
- an opto-electrical device comprising: a substrate; a first electrode disposed over the substrate for injecting charge carriers of a first polarity; a layer disposed over the first electrode comprising a composition according to the first aspect of the present invention; and a second electrode disposed thereover for injecting charge carriers of a second polarity opposite to the first polarity.
- FIG. 1 shows an organic light emitting device according to an embodiment of the present invention.
- the device shown in FIG. 1 comprises a transparent glass or plastic substrate 1 , an anode 2 of indium tin oxide and a cathode 4 .
- An electroluminescent layer 3 is provided between anode 2 and cathode 4 .
- Further layers may be located between anode 2 and cathode 3 , such as charge transporting, charge injecting or charge blocking layers.
- a conductive hole injection layer formed of a doped organic material located between the anode 2 and the electroluminescent layer 3 to assist hole injection from the anode into the layer or layers of semiconducting polymer.
- doped organic hole injection materials include: poly(ethylene dioxythiophene) (PEDT), in particular PEDT doped with a charge-balancing polyacid such as polystyrene sulfonate (PSS) as disclosed in EP 0901176 and EP 0947123, polyacrylic acid or a fluorinated sulfonic acid, for example Nafion®; polyaniline as disclosed in U.S. Pat. No. 5,723,873 and U.S. Pat. No.
- PES polystyrene sulfonate
- Conductive inorganic materials may also be employed as hole injection layers. Suitable inorganic materials include transition metal oxides such as VOx MoOx and RuOx as disclosed in Journal of Physics D: Applied Physics (1996), 29(11), 2750-2753.
- a hole transporting layer located between anode 2 and electroluminescent layer 3 preferably has a HOMO level of less than or equal to 5.5 eV, more preferably around 4.8-5.5 eV.
- an electron transporting layer located between electroluminescent layer 3 and cathode 4 preferably has a LUMO level of around 3-3.5 eV.
- Electroluminescent layer 3 may consist of the electroluminescent material alone or may comprise the electroluminescent material in combination with one or more further materials.
- the electroluminescent material may be blended with hole and/or electron transporting materials as disclosed in, for example, WO 99/48160.
- the electroluminescent material may be covalently bound to a charge transporting material.
- Cathode 4 is selected from materials that have a workfunction allowing injection of electrons into the electroluminescent layer. Other factors influence the selection of the cathode such as the possibility of adverse interactions between the cathode and the electroluminescent material.
- the cathode may consist of a single material such as a layer of aluminium. Alternatively, it may comprise a plurality of metals, for example a bilayer of a low workfunction material and a high workfunction material such as calcium and aluminium as disclosed in WO 98/10621, elemental barium disclosed in WO 98/57381, Appl. Phys. Left.
- the cathode preferably has a workfunction of less than 3.5 eV, more preferably less than 3.2 eV, yet more preferably less than 3 eV, most preferably less than 2.8 eV.
- the substrate preferably has good barrier properties for prevention of ingress of moisture and oxygen into the device.
- the substrate is commonly glass, however alternative substrates may be used, in particular where flexibility of the device is desirable.
- the substrate may comprise a plastic as in U.S. Pat. No. 6,268,695 which discloses a substrate of alternating plastic and barrier layers or a laminate of thin glass and plastic as disclosed in EP 0949850.
- the device is preferably encapsulated with an encapsulant (not shown) to prevent ingress of moisture and oxygen.
- encapsulants include a sheet of glass, films having suitable barrier properties such as alternating stacks of polymer and dielectric as disclosed in, for example, WO 01/81649 or an airtight container as disclosed in, for example, WO 01/19142.
- a getter material for absorption of any atmospheric moisture and/or oxygen that may permeate through the substrate or encapsulant may be disposed between the substrate and the encapsulant.
- At least one of the electrodes is semi-transparent in order that light may be absorbed (in the case of a photoresponsive device) or emitted (in the case of an OLED).
- the anode is transparent, it typically comprises indium tin oxide. Examples of transparent cathodes are disclosed in, for example, GB 2348316.
- FIG. 1 illustrates a device wherein the device is formed by firstly forming an anode on a substrate followed by deposition of an electroluminescent layer and a cathode.
- the device of the invention could also be formed by firstly forming a cathode on a substrate followed by deposition of an electroluminescent layer and an anode.
- Semiconductive polymers may be provided for the purpose of charge transport, emission or as host polymers. A range of repeat units for such polymers are described in more detail below. These polymers may be used separately from the triazines of the present invention (for example as a separate emissive centre in a multicolour device).
- these repeat units may be used in combination with the triazines.
- the solution processable triazine host material according to the second aspect of the invention may comprise a triazine repeat unit and one or more further repeat units selected from those described below.
- the polymer formed from such repeat units used in combination with the triazine repeat units must have a triplet energy higher than that of the phosphorescent dopant.
- Polymers may comprise a first repeat unit selected from arylene repeat units, in particular: 1,4-phenylene repeat units as disclosed in J. Appl. Phys. 1996, 79, 934; fluorene repeat units as disclosed in EP 0842208; indenofluorene repeat units as disclosed in, for example, Macromolecules 2000, 33(6), 2016-2020; and spirofluorene repeat units as disclosed in, for example EP 0707020.
- substituents include solubilising groups such as C 1-20 alkyl or alkoxy; electron withdrawing groups such as fluorine, nitro or cyano; and substituents for increasing glass transition temperature (Tg) of the polymer.
- Polymers may comprise optionally substituted, 2,7-linked fluorenes, for example repeat units of formula:
- R 1 and R 2 are independently selected from hydrogen or optionally substituted alkyl, alkoxy, aryl, arylalkyl, heteroaryl and heteroarylalkyl. More preferably, at least one of R 1 and R 2 comprises an optionally substituted C 4 -C 20 alkyl or optionally substituted aryl group.
- Polymers may provide one or more of the functions of hole transport, electron transport and emission depending on which layer of the device it is used in and the nature of co-repeat units.
- a homopolymer of fluorene repeat units such as a homopolymer of 9,9-dialkylfluoren-2,7-diyl, may be utilised to provide electron transport.
- a polymer preferably a copolymer, comprising a triarylamine repeat unit, in particular a repeat unit selected from formulae 1-6, may be utilised to provide hole transport and/or emission of a different colour to that of the composition of the invention:
- X, Y, A, B, C and D are independently selected from H or a substituent group. More preferably, one or more of X, Y, A, B, C and D is independently selected from the group consisting of optionally substituted, branched or linear alkyl, aryl, perfluoroalkyl, thioalkyl, cyano, alkoxy, heteroaryl, alkylaryl and arylalkyl groups. Most preferably, X, Y, A and B are C 1-10 alkyl.
- the aromatic rings in the backbone of the polymer may be linked by a direct bond or a bridging group or bridging atom, in particular a bridging heteroatom such as oxygen or sulfur.
- Particularly preferred hole transporting polymers of this type are copolymers of arylene repeat units, in particular fluorene repeat units,and a triarylamine repeat unit.
- a copolymer comprising a first repeat unit and heteroarylene repeat unit may be utilised for charge transport or emission.
- Heteroarylene repeat units may be selected from formulae 7-21:
- R 6 and R7 are the same or different and are each independently hydrogen or a substituent group, preferably alkyl, aryl, perfluoroalkyl, thioalkyl, cyano, alkoxy, heteroaryl, alkylaryl or arylalkyl.
- R 6 and R 7 are preferably the same. More preferably, they are the same and are each a phenyl group.
- Electroluminescent copolymers may comprise an electroluminescent region and at least one of a hole transporting region and an electron transporting region as disclosed in, for example, WO 00/55927 and U.S. Pat. No. 6,353,083. If only one of a hole transporting region and electron transporting region is provided then the electroluminescent region may also provide the other of hole transport and electron transport functionality.
- the different regions within such a polymer may be provided along the polymer backbone, as per U.S. Pat. No. 6,353,083, or as groups pendent from the polymer backbone as per WO 01/62869.
- Suzuki polymerisation as described in, for example, WO 00/53656
- Yamamoto polymerisation as described in, for example, T. Yamamoto, “Electrically Conducting And Thermally Stable ⁇ -Conjugated Poly(arylene)s Prepared by Organometallic Processes”, Progress in Polymer Science 1993, 17, 1153-1205.
- These polymerisation techniques both operate via a “metal insertion” wherein the metal atom of a metal complex catalyst is inserted between an aryl group and a leaving group of a monomer.
- a nickel complex catalyst is used
- Suzuki polymerisation a palladium complex catalyst is used.
- a monomer having two reactive halogen groups is used.
- at least one reactive group is a boron derivative group such as a boronic acid or boronic ester and the other reactive group is a halogen.
- Preferred halogens are chlorine, bromine and iodine, most preferably bromine.
- repeat units and end groups comprising aryl groups as illustrated throughout this application may be derived from a monomer carrying a suitable leaving group.
- Suzuki polymerisation may be used to prepare regioregular, block and random copolymers.
- homopolymers or random copolymers may be prepared when one reactive group is a halogen and the other reactive group is a boron derivative group.
- block or regioregular, in particular AB, copolymers may be prepared when both reactive groups of a first monomer are boron and both reactive groups of a second monomer are halogen.
- a single polymer or a plurality of polymers may be deposited from solution to form layer 5 .
- Suitable solvents for polyarylenes include mono- or poly-alkylbenzenes such as toluene and xylene.
- Particularly preferred solution deposition techniques are spin-coating and inkjet printing.
- Spin-coating is particularly suitable for devices wherein patterning of the electroluminescent material is unnecessary—for example for lighting applications or simple monochrome segmented displays.
- Inkjet printing is particularly suitable for high information content displays, in particular full colour displays.
- Inkjet printing of OLEDs is described in, for example, EP 0880303.
- Preferred phosphorescent metal complexes comprise optionally substituted complexes of formula (34):
- M is a metal; each of L 1 , L 2 and L 3 is a coordinating group; q is an integer; r and s are each independently 0 or an integer; and the sum of (a. q)+(b. r)+(c.s) is equal to the number of coordination sites available on M, wherein a is the number of coordination sites on L 1 , b is the number of coordination sites on L 2 and c is the number of coordination sites on L 3 .
- Heavy elements M induce strong spin-orbit coupling to allow rapid intersystem crossing and emission from triplet states (phosphorescence).
- Suitable heavy metals M include:
- lanthanide metals such as cerium, samarium, europium, terbium, dysprosium, thulium, erbium and neodymium;
- d-block metals in particular those in rows 2 and 3 i.e. elements 39 to 48 and 72 to 80, in particular ruthenium, rhodium, palladium, rhenium, osmium, iridium, platinum and gold.
- Suitable coordinating groups for the f-block metals include oxygen or nitrogen donor systems such as carboxylic acids, 1,3-diketonates, hydroxy carboxylic acids, Schiff bases including acyl phenols and iminoacyl groups.
- oxygen or nitrogen donor systems such as carboxylic acids, 1,3-diketonates, hydroxy carboxylic acids, Schiff bases including acyl phenols and iminoacyl groups.
- luminescent lanthanide metal complexes require sensitizing group(s) which have the triplet excited energy level higher than the first excited state of the metal ion. Emission is from an f-f transition of the metal and so the emission colour is determined by the choice of the metal. The sharp emission is generally narrow, resulting in a pure colour emission useful for display applications.
- the d-block metals form organometallic complexes with carbon or nitrogen donors such as porphyrin or bidentate ligands of formula (35):
- Ar 4 and Ar 5 may be the same or different and are independently selected from optionally substituted aryl or heteroaryl; X 1 and Y 1 may be the same or different and are independently selected from carbon or nitrogen; and Ar 4 and Ar 5 may be fused together.
- Ligands wherein X 1 is carbon and Y 1 is nitrogen are particularly preferred.
- Each of Ar 4 and Ar 5 may carry one or more substituents.
- substituents include fluorine or trifluoromethyl which may be used to blue-shift the emission of the complex as disclosed in WO 02/45466, WO 02/44189, US 2002-117662 and US 2002-182441; alkyl or alkoxy groups as disclosed in JP 2002-324679; carbazole which may be used to assist hole transport to the complex when used as an emissive material as disclosed in WO 02/81448; bromine, chlorine or iodine which can serve to functionalise the ligand for attachment of further groups as disclosed in WO 02/68435 and EP 1245659; and dendrons which may be used to obtain or enhance solution processability of the metal complex as disclosed in WO 02/66552.
- ligands suitable for use with d-block elements include diketonates, in particular acetylacetonate (acac); triarylphosphines and pyridine, each of which may be substituted.
- Main group metal complexes show ligand based, or charge transfer emission.
- the emission colour is determined by the choice of ligand as well as the metal.
- the host material and metal complex may be combined in the form of a physical blend.
- the metal complex may be chemically bound to the host material.
- the metal complex may be chemically bound as a substituent attached to the polymer backbone, incorporated as a repeat unit in the polymer backbone or provided as an end-group of the polymer as disclosed in, for example, EP 1245659, WO 02/31896, WO 03/18653 and WO 03/22908.
- Embodiments of the present invention can also be used as hosts for fluorescent emitters.
- a wide range of fluorescent low molecular weight metal complexes may be used with the present invention.
- Suitable ligands for di or trivalent metals include: oxinoids, e. g.
- oxygen-nitrogen or oxygen-oxygen donating atoms generally a ring nitrogen atom with a substituent oxygen atom, or a substituent nitrogen atom or oxygen atom with a substituent oxygen atom such as 8-hydroxyquinolate and hydroxyquinoxalinol-10-hydroxybenzo (h) quinolinato (II), benzazoles (III), schiff bases, azoindoles, chromone derivatives, 3-hydroxyflavone, and carboxylic acids such as salicylato amino carboxylates and ester carboxylates.
- Optional substituents include halogen, alkyl, alkoxy, haloalkyl, cyano, amino, amido, sulfonyl, carbonyl, aryl or heteroaryl on the (hetero) aromatic rings which may modify the emission colour.
- a 1 L three-necked round bottomed flask was fitted with a magnetic stirrer, a reflux condenser with N 2 inlet bubbler, and a 500 ml pressure-equalising dropping funnel.
- the flask was charged with trifluoromethane sulfonic acid (60 g, 35 ml) that was stirred at room temperature.
- trifluoromethane sulfonic acid 60 g, 35 ml
- 4-bromobenzonitrile (36.4 g, 0.20 mol) was dissolved in anhydrous CHCl 3 (500 ml) and the solution transferred into the dropping funnel under N 2 via cannula.
- the benzonitrile solution was added dropwise and then the reaction mixture was heated to reflux at 90-95° C. for 20-24 hours.
- a glass substrate comprising an ITO electrode was deposited, in sequence, a layer of PEDOT/PSS (available from H C Starck of Leverkusen, Germany as Baytron P®); a hole transport layer comprising a copolymer of fluorene and triarylamine repeat units; an emissive layer comprising compound (6) as a host material and the green-emitting iridium-cored dendrimer illustrated below, and as disclosed in WO 02/066552; and a cathode comprising a layer of barium oxide (5 nm) and thick capping layer of aluminium. All layers were deposited by spin-coating from solution.
- PEDOT/PSS available from H C Starck of Leverkusen, Germany as Baytron P®
- a hole transport layer comprising a copolymer of fluorene and triarylamine repeat units
- an emissive layer comprising compound (6) as a host material and the green-emitting iridium-cored dendrimer
- a device was prepared as per the Device Example above except that a solution processable version of the commonly used host material 4,4′-di(N-carbazole)biphenyl (CBP) was used in place of the solution processable triazine host material (6).
- CBP was rendered solution processable by substitution with alkyl groups.
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US9048442B2 (en) | 2008-06-23 | 2015-06-02 | Sumitomo Chemical Company, Limited | Composition containing a metal complex and organic compound, and light-emitting element using said compound |
US9666806B2 (en) | 2009-09-16 | 2017-05-30 | Merck Patent Gmbh | Formulations for the production of electronic devices |
US10714691B2 (en) | 2009-09-16 | 2020-07-14 | Merck Patent Gmbh | Formulations for the production of electronic devices |
WO2011141714A1 (en) | 2010-05-14 | 2011-11-17 | Cambridge Display Technology Limited | Organic light-emitting polymer and device |
DE112011101651T5 (de) | 2010-05-14 | 2013-03-21 | Cambridge Display Technology, Ltd. | Organisches lichtemittierendes Polymer und Einrichtung |
US8981354B2 (en) | 2010-05-14 | 2015-03-17 | Cambridge Display Technology Limited | Organic light-emitting polymer and device |
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US20150001509A1 (en) * | 2012-12-21 | 2015-01-01 | Cambridge Display Technology Limted | Composition |
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JP2015167230A (ja) | 2015-09-24 |
CN101522857B (zh) | 2013-07-10 |
JP6167126B2 (ja) | 2017-07-19 |
EP3211056B1 (en) | 2020-07-22 |
KR20090047547A (ko) | 2009-05-12 |
US20150207081A1 (en) | 2015-07-23 |
US9680110B2 (en) | 2017-06-13 |
CN103325962B (zh) | 2016-12-07 |
WO2008025997A1 (en) | 2008-03-06 |
EP2057249B1 (en) | 2017-11-08 |
CN101522857A (zh) | 2009-09-02 |
JP2010503193A (ja) | 2010-01-28 |
CN103325962A (zh) | 2013-09-25 |
US20140335638A1 (en) | 2014-11-13 |
KR20150071010A (ko) | 2015-06-25 |
TWI482760B (zh) | 2015-05-01 |
JP5721948B2 (ja) | 2015-05-20 |
EP3211056A1 (en) | 2017-08-30 |
TW200823179A (en) | 2008-06-01 |
EP2057249A1 (en) | 2009-05-13 |
GB0617167D0 (en) | 2006-10-11 |
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