CN106410026B - 有机半导体器件的空穴导电层及其应用和有机电子器件 - Google Patents
有机半导体器件的空穴导电层及其应用和有机电子器件 Download PDFInfo
- Publication number
- CN106410026B CN106410026B CN201610206776.8A CN201610206776A CN106410026B CN 106410026 B CN106410026 B CN 106410026B CN 201610206776 A CN201610206776 A CN 201610206776A CN 106410026 B CN106410026 B CN 106410026B
- Authority
- CN
- China
- Prior art keywords
- hole transporting
- bis
- electronic device
- transporting layers
- transition metal
- 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.)
- Active
Links
- 239000004065 semiconductor Substances 0.000 title description 5
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000002019 doping agent Substances 0.000 claims abstract description 20
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 19
- 150000003624 transition metals Chemical class 0.000 claims abstract description 19
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 239000011159 matrix material Substances 0.000 claims abstract description 11
- XCBBNTFYSLADTO-UHFFFAOYSA-N Methyl-pentyl-glyoxal Natural products CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 claims abstract description 4
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims abstract 6
- 230000005693 optoelectronics Effects 0.000 claims abstract 3
- 229910052802 copper Inorganic materials 0.000 claims description 16
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 230000002269 spontaneous effect Effects 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 85
- 239000010410 layer Substances 0.000 description 47
- 239000010949 copper Substances 0.000 description 46
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- -1 metal complex compound Chemical class 0.000 description 14
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 150000002220 fluorenes Chemical class 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 238000000103 photoluminescence spectrum Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 240000002853 Nelumbo nucifera Species 0.000 description 4
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 4
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- QKYZQKJXAKNEPA-UHFFFAOYSA-N 3-hydroxy-5-methyl-1-phenylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(O)C(=O)C=2C(C)=CSC=2N1C1=CC=CC=C1 QKYZQKJXAKNEPA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 101000606537 Homo sapiens Receptor-type tyrosine-protein phosphatase delta Proteins 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 102100039666 Receptor-type tyrosine-protein phosphatase delta Human genes 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- JBAKCAZIROEXGK-LNKPDPKZSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O JBAKCAZIROEXGK-LNKPDPKZSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000006617 triphenylamine group Chemical class 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-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
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical class C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 1
- YVXIQVXKXBYVRO-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid 1,1,1-trifluoropentane-2,4-dione Chemical compound OC(=O)C(F)(F)F.CC(=O)CC(=O)C(F)(F)F YVXIQVXKXBYVRO-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical class CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- RJEGEQUPVPJVCG-UHFFFAOYSA-N C.C(#N)C1=NC2=CC=CC=C2C=C1 Chemical compound C.C(#N)C1=NC2=CC=CC=C2C=C1 RJEGEQUPVPJVCG-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000003283 Pachira macrocarpa Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 240000001085 Trapa natans Species 0.000 description 1
- 235000014364 Trapa natans Nutrition 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004411 aluminium Substances 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000010866 blackwater Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YIJNDODLHQLWIC-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-2-naphthalen-1-ylaniline Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC=C1C1=CC=CC2=CC=CC=C12 YIJNDODLHQLWIC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000009165 saligot Nutrition 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Photovoltaic Devices (AREA)
Abstract
本发明涉及有机电子器件的空穴导电层及其应用和有机光电子器件。用于有机电子器件的空穴导电层包含单核二次平面过渡金属络合物掺杂材料被引入到空穴导电基体中,其中所述二次平面过渡金属络合物包含中心原子和配位体,并且所述配位体选自乙酰丙酮、三氟乙酰丙酮、六氟乙酰丙酮、6,6,7,7,8,8,8‑七氟‑2,2‑二甲基‑3,5‑辛二酮酸和2,2,6,6,‑四甲基‑3,5‑庚二酮酸。
Description
本发明申请是于申请日为2011年3月31日提交的、申请号为201180018027.8(国际申请号为PCT/EP2011/001645)以及发明名称为“用于有机半导体器件的空穴导电层的掺杂材料及其应用”的发明专利申请的分案申请。
技术领域
本发明涉及用于在有机电子器件中的空穴注入层的新型的金属有机物材料,其中所述有机电子器件尤其为如有机发光二极管(OLED)或者有机发光电化学池(OLEEC)或者有机场效应晶体管或者有机太阳能电池或者有机光检测器的发光器件。
背景技术
在参考文献中多次说明用于掺杂具有电子受主的有机金属以提高空穴导电层的导电性(例如见G.He,O.Schneider,D.Qin,X.Zhou,M.Pfeiffer和K.Leo,Journal ofApplied Physics 95,5773-5777(2004))。
通过掺杂能够将材料的导电性提高一定数量级。
原则上存在用于空穴运输层的、尤其低成本的掺杂材料的其他需要。
发明内容
本发明的目的是,提供一种使用在空穴导电材料中的其他掺杂材料。
因此,该目的的实现和本发明的主题是实现一种掺杂的空穴导电层以使用在有机电子器件中,所述空穴导电层至少包括空穴导电的基体和二次平面单核过渡金属络合物作为掺杂材料。此外,本发明的目的是提供这种空穴导电层的应用,以及最后提供一种有机电子器件。
根据本发明的实施形式,掺杂材料是具有铜、钯、铂、钴、或者镍原子作为中心原子的二次平面单核过渡金属络合物。
在此,每个下述络合物形式称作为二次平面的,所述络合物形式与根据晶体结构分析的四面体的络合物配置偏差大于通常的测量不精确性。在任何情况下都不限制围绕中心原子的配位体平面的布置。
优选相对于空穴导电的基体具有相对低的LUMO(分子最低未占轨道),因为所述化合物在基体中的特征在于更高的路易斯(Lewis)酸度。因此,在那里掺杂效果尤其显著。
由于二次平面的特性,络合物在总式相同的情况下能够存在于其顺式或者反式。在一般情况下,尤其在小的取代基R的情况下同样良好地掺杂两种同分异构体。下面,仅仅讨论反式同分异构体来代表两种同分异构体。
对于二次平面过渡金属络合物的总体种类的例举是具有铜2+作为中心原子的单核络合物的种类。
为了建立化合物的二次平面特性,优选桥联的或者“二齿”的配位体,例如乙酰丙酮。当然,在铜作为中心原子的情况下比例如在钯作为中心原子的情况更重,因为所述作为中心原子的铜无论如何示出构成二次平面金属络合物的趋势。
通用结构式I
结构式I示出根据本发明的二次平面铜(II)络合物的实例。在总式相同的情况下,络合物能够存在于顺式或者反式。
在结构式I中,桥Y1或者Y2彼此独立地由N或者C-R组成,其中R能够是任意的脂肪族或者芳香族取代基,如所述取代基在下面针对R1a、R1b、R2a和R2b来讨论。
尤其优选的是桥C-H。所述桥应用在全部实施例中。
X1和X2能够是彼此无关的O或者N-R,其中R能够代表任意的脂肪族或者芳香族的取代基,如所述取代基稍后例如针对R1a、R1b、R2a和R2b来讨论。尤其优选的是,X1、X2=O。在此,乙酰丙酮络合物借助Yi=C-R(i=1和/或2)形成。特别地,所述种类的缺乏电子的代表形成在用于空穴导电材料的在此公开的掺杂材料之内的优选的种类。借助Xi=N-R(i=1和/或2)形成希夫碱络合物(Schiff-Base-Komplexe)。
取代基R1a、R1b、R2a和R2b能够是彼此独立的氢或者氘、甲基、乙基、广义未支化的、支化的、缩合的(十氢萘基)、环形的(环己基)或者完全或部分取代的烷基残基(C1-C20)。所述烷基残基能够包含醚基团(乙氧基、甲氧基等)、酯、酰胺、碳酸基基团等还或者尤其是F的卤素。在本发明的范围内,也是取代的或者未取代的脂肪环或者例如环己基的环体系。
R1a、R1b、R2a和R2b不限制于饱和的体系,而是也包括取代的或未取代的芳香基,例如为苯基、联苯、萘基、菲基等或苯甲基等。在表格1中示出适合用作取代基的杂环的总结。为了简单性仅仅示出芳香基的基体。原则上,所述基体能够由类似地从此处限定的残基R1a、R1b、R2a和R2b中衍生出的其他残基R取代。
表1
表1示出取代的或者未取代的杂环的选择,所述杂环彼此独立地用作残基R1a、R1b、R2a和R2b。为了简单性仅仅示出基本单元。与配位体的结合能够在基体的任意有结合能力的部位进行。如果取代基R1a、R1b、R2a和R2b带有具有直接地在键合碳原子处的氟的吸电子的取代基(见化学式3.3a至3.3c),那么更尤其优选的是缺电子的变体。
化学式III示出不同类型的用于残基R1a、R1b、R2a和R2b的尤其优选的取代基。
在此,在化学式3.3a中能够是n=1至20,尤其优选n=2且R=F。否则R能够如残基R1a、R1b、R2a和R2b那样选择。尤其优选的是,在此为脂肪链和/或芳香部分。
在化学式3.3b中,n、m、o能够独立地为0至20,然而尤其优选n=m=2并且O在1至5的范围内且R=F和B=O。否则,R能够如残基R1a、R1b、R2a和R2b那样选择。尤其优选的是,在此为脂肪链和/或芳香部分。
在化学式3.3c中,R1至R7能够彼此独立地如残基R1a、R1b、R2a和R2b那样选择。然而尤其优选的是,具有彼此独立的H或F的R1至R7的完全或者部分氟化的体系。
不详细深入络合物的合成,因为已经极其彻底地研究了所述合成。(引用:书目“The Chemistry of Metal CVD”,T.Kodas、M.Hampden Smith、VCH 1994、ISBN 3-527-29071-0,第178–192页)。特别地,所述络合物作为前体用于在半导体工业中的铜CVD(化学气相沉积)。因此,商业上可获得多种易挥发的衍生物。
将根据本发明的材料以0.1%-50%的浓度、优选以5%-30%的浓度掺杂到空穴运输材料中,以制造空穴运输层。层的沉积不仅能够从气相中也能够从液相中进行。
在此,作为从气相中沉积的空穴运输体能够使用但不限制于:
N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-二甲基芴
N,N'-双(3-甲基苯基)-N,N'-双(苯基)-9,9-二苯基芴
N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-二苯基芴
N,N'-双(萘-1-基)-N,N'-双(苯基)-2,2-二甲基联苯胺
N,N'-双(3-甲基苯基)-N,N'-双(苯基)-9,9-螺二芴
2,2',7,7'-四(N,N-二苯氨)-9,9'-螺二芴
N,N'-双(萘-1-基)-N,N'-双(苯基)-联苯胺
N,N'-双(萘-2-基)-N,N'-双(苯基)-联苯胺
N,N'-双(3-甲基苯基)-N,N'-双(苯基)-联苯胺
N,N'-双(3-甲基苯基)-N,N'-双(苯基)-9,9-二甲基芴
N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-螺二芴
二-[4-(N,N-联甲苯-氨基)-苯基]环己烷
2,2',7,7'-四(N,N-二-甲苯基)氨基-螺-二芴
9,9-双[4-(N,N-双-联苯基-4-基-氨基)苯基]-9H-芴
2,2',7,7'-四[N-萘基(苯基)-氨基]-9,9-螺二芴
2,7-双[N,N-双(9,9-螺-二芴-2-基)-氨基]-9,9-螺二芴
2,2'-双[N,N-双(联苯基-4-基)氨基]-9,9-螺二芴
N,N'-双(菲-9-基)-N,N'-双(苯基)-联苯胺
N,N,N',N'-四-萘基-2-基-联苯胺
2,2'-双(N,N-二-苯基-氨基)-9,9-螺二芴
9,9-双[4-(N,N-双-萘-2-基-氨基)苯基]-9H-芴
9,9-双[4-(N,N'-双-萘基-2-基-N,N'-双-苯基-氨基)-苯基]-9H-芴氧钛酞菁
铜酞菁
2,3,5,6-四氟-7,7,8,8,-四氰基-喹啉甲烷
4,4',4"–三(N-3-甲基苯基-N-苯基-氨基)三苯胺
4,4',4"-三(N-(2-萘基)-N-苯基-氨基)三苯胺
4,4',4"-三(N-(1-萘基)-N-苯基-氨基)三苯胺
4,4',4"-三(N,N-二苯基-氨基)三苯胺
吡嗪[2,3-f][1,10]菲咯啉-2,3-二腈
N,N,N',N'–四(4-甲氧基-苯基)联苯胺
2,7-双[N,N-双(4-甲氧基-苯基)氨基]-9,9-螺二芴
2,2'-双[N,N-双(4-甲氧基-苯基)氨基]-9,9-螺二芴
N,N'-二(萘-2-基)-N,N'-联三苯-1,4-二元胺
N,N'-二-苯基-N,N'-二-[4-(N,N-二-甲苯基-氨基)苯基]联苯胺
N,N'-二-苯基-N,N'-二-[4-(N,N-二-苯基-氨基)苯基]联苯胺。
所述单分子空穴运输材料也能够从液相中沉积或者混合成下面提出的聚合物材料。如果将低分子量的和聚合的材料混合,那么改进薄膜形成特性。混合比例位于0-100%之间。
首先从液相中沉积的聚合的空穴运输体见下例如为:PEDOT、PVK、PTPD、P3HT和PANI(PVK=聚(9-乙烯基咔唑),PTPD=聚(N,N’-双(4-丁基苯基)-N,N’-双(苯基)-联苯胺),P3HT=聚(3-己基噻吩)和PANI=聚苯胺),但是不限制于此,
表2
表2示出优选从液相中沉积的典型的空穴运输的聚合物。
所述材料也能够存在为任意的混合物。
能够使用常用的有机溶剂来作为溶剂,然而主要为氯苯、氯仿、苯、苯甲醚、甲苯、二甲苯、THF、丙二醇甲醚醋酸酯、苯乙醚、甲基乙基酮、N-甲基砒喀酮、γ-丁内酯等。
化学式能够通过将1-2个空穴导电分子(在此为NPB)配位到二次平面的过渡金属络合物的轴线位置中来进行掺杂。
以铜2+络合物为实例来说明,所述铜2+络合物如下:
通过二次平面过渡金属络合物形式的在此第一次示出的掺杂材料能够将便宜的并且容易得到的化合物首次引入到所述掺杂材料添加物技术中。
例如,多种铜2+化合物是容易得到的,因为其使用在半导体工业中的铜CVD方法中。此外,良好地制定制造方法,掺杂材料通常是适宜的,借助于此制成的构件在关断的状态下具有中性的外观并且最后所述材料适合于从气相或者液相中沉积掺杂的空穴导体。
附图说明
图1示意地示出OLEEC的结构;
图2示出NPB(参考曲线)和借助Cu(acac)2掺杂的NPB的电流电压特征曲线;
图3示出NPB和借助Cu(acac)2掺杂的NPB的吸收光谱;
图4示出NPB和借助Cu(acac)2掺杂的NPB的PL光谱;
图5示出NPB和借助Cu(tcac)2掺杂的NPB的电流电压特征曲线;
图6示出NPB和以两种浓度中借助Cu(tfac)2掺杂的NPB的吸收光谱;
图7最后示出NPB和借助Cu(tfac)2掺杂的NPB的PL光谱。
具体实施方式
下面还根据五个实施例和附图1至7详细阐明本发明:
图1示意地示出OLEEC的结构。
OLED 7在大多数情况下通过在两个有机辅助层、电子运输层5和空穴运输层6之间引入有机层3来构成。因此,OLED的包括层3、5和6的所述有机有源部分置于两个电极2和4之间。光在施加电压的情况下出射。OLED的优选有源发射层3由基体组成,发射的物质嵌入到所述基体中。层3也包括例如用于红色、绿色、蓝色的发射体的层堆叠。
在透明衬底1上存在下部的透明电极层2,例如阳极。之后为空穴运输层6,所述空穴运输层的掺杂是本发明的主题。在有机有源层的与空穴导电层相对置的一侧上存在电子注入层5,在所述电子注入层上存在例如金属电极的上部电极4。
OLED7通常被封装,这在此没有示出。
实例1
为了净化和研究升华点,将用于掺杂空穴导电层的五种已经提及的铜乙酰丙酮在升华设备中以小于1.0E-5mbar的基本压强升华。所述升华得到关于材料的颜色变化和升华温度的在下表中列出的结果:
材料 | 初始颜色 | 升华范围 | 升华后的颜色 |
Cu(acac)<sub>2</sub> | 蓝紫色 | 110-120℃ | 蓝紫色 |
Cu(tfac)<sub>2</sub> | 紫色 | 95-100℃ | 紫色 |
Cu(hfac)<sub>2</sub> | 深绿色 | 70℃@1E-2mbar | 黑绿色 |
Cu(fod)<sub>2</sub> | 绿色 | 60-70℃ | 绿色 |
Cu(dpm)<sub>2</sub> | 紫色 | 70-80℃ | 紫色 |
表格4:5种铜乙酰丙酮的颜色特性和升华点
这些试验示出:两种材料Cu(acac)2和Cu(tfac)2良好适合于真空处理。
此外,在该上下文中研究五种铜乙酰丙酮在THF、甲苯和氯苯中的可溶性,以便解释可能的溶液处理。在此示出,全部材料在所述的溶剂中能够短时间内完全地溶解并且因此也适合于承担溶液处理。
例如,从氯苯中使用Cu(hfac)2溶液作为掺杂材料是成功的、即具有显著的掺杂效果。同样地,能够在氯苯中测试来自溶液中的Cu(fod)2,其中能够观察到显著的掺杂效果。溶剂浓度在这两种情况下大约为1.5%并且层厚度为90nm至100nm。
实例2
通过热蒸发在ITO(氧化铟锡=氧化锡掺杂的氧化铟)电极(下部的透明电极2)上沉积200nm厚的空穴导电NPB(=双-N,N,N’,N’-(萘基-苯基)联苯胺)层。150nm厚的铝层(上部电极4)用作反向电极。4mm2大的器件通过黑色菱形标记的电流电压特征曲线(IV特征曲线)得到参考曲线,所述参考曲线在图2中示出。
在两个其他的试验中,将掺杂材料Cu(acac)2以相对于蒸发率5%和10%的浓度掺杂到NPB中。器件的衬底、层厚度和大小如已经在第一试验中提及。
在此,具有5%浓度的器件得到借助正方形表示的特征曲线,并且具有10%浓度的器件通过三角形标记的特征曲线来表示。
图2示出试验的图形化的总结,即NPB(参考曲线)和借助Cu(acac)2掺杂的NPB的电流电压特征曲线。
针对两种浓度能够示出,掺杂作用于IV特征曲线。
具有5%特征曲线(正方形)的负电压的少量上升的不对称关系示出,掺杂在器件中引起所选择的浓度不足的效果。10%特征曲线(三角形)的对称关系是成功掺杂的典型标志,但是不能够特别地对于正电压识别电流密度的显著的上升。
实例3
在实例2的试验期间,未掺杂的NPB层和借助Cu(acac)2掺杂的NPB层附加地分别沉积在石英玻璃盘上。所述样品不具有电接触部并且仅用于测量各个层的吸收光谱和发射光谱。
在此,纯NPB层(参考曲线)得到吸收光谱或者光致发光光谱的在图3中借助黑色菱形标记的示出的特征曲线。具有5%掺杂的Cu(acac)2的样品得出以正方形示出的光谱,并且具有10%掺杂的Cu(acac)2的样品得出以三角形标记的光谱。
与吸收光谱(图3)相比较而示出:纯NPB在吸收最大值(334nm)处具有提高至3倍的吸收。为此,借助Cu(acac)2掺杂的层在410nm-440nm的范围内具有升高至纯NPB的吸收。这表明荷移络合物的形成,进而表明掺杂效果。在吸收光谱中,5%的样品与10%的样品相比具有更高一些的吸收,但是整体上两者相当接近并且具有在实例2中根据电特征曲线示出的掺杂效果。
图3示出NPB和借助Cu(acac)2掺杂的NPB的吸收光谱。
与PL光谱(图4)相比较而示出:借助Cu(acac)2掺杂的样品与纯NPB样品相比具有更高的发射。同时,能够观察到发射朝向更低波长的微小的移动。纯NPB在444nm处发射,而5%或10%掺杂的层在440nm或438nm处发射。由于掺杂引起的发射的移动又能够根据荷移络合物来解释。当然,在此新颖的是,铜乙酰丙酮的强化发射的效果。在掺杂物本身作为发射抑制剂(猝灭剂)已知的范围内,强化是不寻常的。
实例4
类似于实例2,在两个其他试验中,以相对于蒸发率5%和10%的浓度将Cu(tfac)2掺杂材料掺杂到NPB中。器件的衬底、层厚度和大小如在实例1中提及。
在此,具有5%浓度的器件得到借助正方形表示的特征曲线,并且具有10%浓度的器件通过三角形标记的特征曲线来表示。借助黑色菱形标记的特征曲线又示出来自纯NPB中的参考构件。
对于两种浓度能够看出电流密度的上升以及类似对称的关系,这两者示出存在掺杂效果。在此,5%线的水平区域在构件的方面不是电流边界,而是测量设备的遵从(测量边界)。5%样品相对于10%样品更高的电流密度示出:掺杂材料浓度的最佳值位于10%之下。但是最佳浓度不必须强制地位于5%和10%之间,而是也能够还更低并且由此能够引起还更大的掺杂效果。
来自具有Cu(acac)2的实例2和具有Cu(tfac)2的所述实例的试验中的比较示出:配位体的氟化在络合物中改进掺杂效果。因此能够认为,借助Cu(hfac)2来进一步改进是可能的。如在实例1中已经提及,Cu(hfac)2当然对于真空处理是不可能的,而是仅对于溶液处理是可能的(见下面的实例)。
图5示出NPB和借助Cu(tcac)2掺杂的NPB的电流电压特征曲线。
实例5
在来自实例4的试验期间,未掺杂的NPB层和借助Cu(tfac)2掺杂的NPB层附加地分别沉积在石英玻璃盘上。所述样品不具有电接触部并且仅用于测量各个层的吸收光谱和发射光谱。
在此,纯NPB参考层得到吸收光谱或者光致发光光谱的借助黑色菱形标记的特征曲线。具有5%掺杂的Cu(tfac)2的样品得出以正方形示出的光谱,并且具有10%掺杂的Cu(tfac)2的样品得出以三角形标记的光谱。
与吸收光谱(图6)相比较而示出:纯NPB在吸收最大值(334nm)处具有高至3-4倍的吸收。为此,借助Cu(tfac)2掺杂的层在410nm-440nm的范围内具有升高至纯NPB的吸收,所述吸收然后在450nm-550nm之间再次低于纯NPB。这表明荷移络合物的形成,进而表明掺杂效果。在吸收光谱中,10%的样品与5%的样品相比具有大致更高的吸收,但是整体上两者显著低于纯NPB,并且具有在实例4中根据电特征曲线示出的掺杂效果。在实例4中的掺杂效果对于10%的样品更低,并且在此,这与5%样品相比通过在吸收中的更小的下降而变得明显。
与PL光谱(图7)相比较而示出:同样如在实例3中,借助Cu(tfac)2掺杂的样品与纯NPB样品相比具有更高的发射。同时,也能够观察到发射朝向更低波长的移动。纯NPB在444nm处发射,而5%或10%掺杂的层在436nm或434nm处发射。由于掺杂引起的发射的移动又能够根据荷移络合物来解释。当然,在此还新颖的是,铜乙酰丙酮的强化发射的效果。在掺杂物本身作为发射抑制剂(猝灭剂)已知的范围内,强化如已经提及的那样原本是不寻常的。
图6示出NPB和以两种浓度中借助Cu(tfac)2掺杂的NPB的吸收光谱。
图7最后示出NPB和借助Cu(tfac)2掺杂的NPB的PL光谱。
如尤其为有机发光二极管(图1)的有机电子器件的辉度(cd/m2)、效率(cd/A)和使用寿命(h)强烈地与在发光层中的激子密度和载流子注入质量相关,并且此外也通过所述激子密度和载流子注入质量来限制。本发明描述一种由二次平面单核过渡金属络合物制成的空穴注入层,例如铜2+-络合物,所述过渡金属络合物嵌入到空穴导电的基体中。
根据上述描述可知,本发明的实施例涵盖但不限于以下技术方案:
方案1.用于有机电子器件的空穴导电层,其中,包含单核二次平面过渡金属络合物掺杂材料被引入到空穴导电基体中,所述过渡金属络合物包含中心原子和配位体。
方案2.根据方案1所述的空穴导电层,其中所述中心原子选自下述过渡金属:Cu、Co、Ni、Pd、Pt。
方案3.根据上述方案之一所述的空穴导电层,其中所述配位体优选是二齿的配位体。
方案4.根据上述方案之一所述的空穴导电层,其中所述配位体选自乙酰丙酮(acac)、三氟乙酰丙酮(tfac)、六氟乙酰丙酮(hfac)、双(6,6,7,7,8,8,8-七氟-2,2-二甲基-3,5-辛二酮酸(fod)、双(2,2,6,6,-四甲基-3,5-庚二酮酸(dpm)。
方案5.根据上述方案1至4之一所述的空穴导电层在有机电子器件中的应用。
方案6.具有掺杂的空穴导电层的有机电子器件,其中掺杂材料包括为单核的且二次平面的过渡金属络合物。
方案7.根据方案6所述的器件,所述器件是自发射的器件。
Claims (6)
1.一种用于有机电子器件的空穴导电层,其中,包含单核的二次平面过渡金属络合物的掺杂材料被引入到空穴导电基体中,其中所述二次平面过渡金属络合物包含中心原子和配位体,并且所述配位体选自三氟乙酰丙酮、六氟乙酰丙酮、6,6,7,7,8,8,8-七氟-2,2-二甲基-3,5-辛二酮酸和2,2,6,6,-四甲基-3,5-庚二酮酸。
2.根据权利要求1所述的空穴导电层,其中所述中心原子选自下述过渡金属:Cu、Co、Ni、Pd、Pt。
3.根据上述权利要求1至2之一所述的空穴导电层在有机电子器件中的应用。
4.一种具有掺杂的空穴导电层的有机电子器件,其中掺杂材料包括单核的二次平面过渡金属络合物,其中所述二次平面过渡金属络合物包含中心原子和配位体,并且所述配位体选自三氟乙酰丙酮、六氟乙酰丙酮、6,6,7,7,8,8,8-七氟-2,2-二甲基-3,5-辛二酮酸和2,2,6,6,-四甲基-3,5-庚二酮酸。
5.根据权利要求4所述的有机电子器件,所述有机电子器件是自发射的器件。
6.一种有机光电子器件,其具有掺杂的空穴导电层,其中掺杂材料包含过渡金属络合物,所述过渡金属络合物是单核的且二次平面的,并且其中所述有机光电子器件是有机发光电化学电池(OLEEC)。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE201010013495 DE102010013495A1 (de) | 2010-03-31 | 2010-03-31 | Dotierstoff für eine Lochleiterschicht für organische Halbleiterbauelemente und Verwendung dazu |
DE102010013495.3 | 2010-03-31 | ||
CN201180018027.8A CN102947414B (zh) | 2010-03-31 | 2011-03-31 | 用于有机半导体器件的空穴导电层的掺杂材料及其应用 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180018027.8A Division CN102947414B (zh) | 2010-03-31 | 2011-03-31 | 用于有机半导体器件的空穴导电层的掺杂材料及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106410026A CN106410026A (zh) | 2017-02-15 |
CN106410026B true CN106410026B (zh) | 2019-05-14 |
Family
ID=44209907
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180018027.8A Active CN102947414B (zh) | 2010-03-31 | 2011-03-31 | 用于有机半导体器件的空穴导电层的掺杂材料及其应用 |
CN201610206776.8A Active CN106410026B (zh) | 2010-03-31 | 2011-03-31 | 有机半导体器件的空穴导电层及其应用和有机电子器件 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180018027.8A Active CN102947414B (zh) | 2010-03-31 | 2011-03-31 | 用于有机半导体器件的空穴导电层的掺杂材料及其应用 |
Country Status (7)
Country | Link |
---|---|
US (2) | US9006716B2 (zh) |
EP (1) | EP2553047B1 (zh) |
JP (1) | JP5847157B2 (zh) |
KR (2) | KR101757888B1 (zh) |
CN (2) | CN102947414B (zh) |
DE (1) | DE102010013495A1 (zh) |
WO (1) | WO2011120709A1 (zh) |
Families Citing this family (85)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102010013495A1 (de) * | 2010-03-31 | 2011-10-06 | Siemens Aktiengesellschaft | Dotierstoff für eine Lochleiterschicht für organische Halbleiterbauelemente und Verwendung dazu |
DE102010062877A1 (de) * | 2010-12-13 | 2012-06-21 | Osram Opto Semiconductors Gmbh | Organisches Lichtemittierendes Bauelement und Verwendung eines Kupferkomplexes in einer Ladungstransportschicht |
CN106025099B (zh) | 2011-04-12 | 2018-09-07 | 精工爱普生株式会社 | 发光元件、发光装置、认证装置以及电子设备 |
JP5765034B2 (ja) | 2011-04-18 | 2015-08-19 | セイコーエプソン株式会社 | チアジアゾール系化合物、発光素子用化合物、発光素子、発光装置、認証装置および電子機器 |
KR20130018547A (ko) | 2011-08-09 | 2013-02-25 | 세이코 엡슨 가부시키가이샤 | 티아디아졸계 화합물, 발광 소자, 발광 장치, 인증 장치, 전자 기기 |
JP5790279B2 (ja) | 2011-08-09 | 2015-10-07 | セイコーエプソン株式会社 | 発光素子、発光装置および電子機器 |
KR102310368B1 (ko) | 2011-11-17 | 2021-10-07 | 메르크 파텐트 게엠베하 | 스피로디히드로아크리딘 유도체 및 이의 유기 전계발광 소자용 재료로서의 용도 |
JP5970811B2 (ja) * | 2011-12-28 | 2016-08-17 | セイコーエプソン株式会社 | 発光素子、発光装置および電子機器 |
EP2814906B1 (en) | 2012-02-14 | 2016-10-19 | Merck Patent GmbH | Spirobifluorene compounds for organic electroluminescent devices |
US9324952B2 (en) | 2012-02-28 | 2016-04-26 | Seiko Epson Corporation | Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device |
KR102268695B1 (ko) | 2012-03-15 | 2021-06-23 | 메르크 파텐트 게엠베하 | 전자 소자 |
DE102012209523A1 (de) | 2012-06-06 | 2013-12-12 | Osram Opto Semiconductors Gmbh | Hauptgruppenmetallkomplexe als p-Dotanden für organische elektronische Matrixmaterialien |
DE102012011335A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Verbindungen für Organische Elekronische Vorrichtungen |
DE102012211869A1 (de) | 2012-07-06 | 2014-01-09 | Osram Opto Semiconductors Gmbh | Organisches Licht emittierendes Bauelement |
JP2014053383A (ja) * | 2012-09-05 | 2014-03-20 | Konica Minolta Inc | タンデム型の有機光電変換素子およびこれを用いた太陽電池 |
US10454040B2 (en) | 2012-09-18 | 2019-10-22 | Merck Patent Gmbh | Materials for electronic devices |
CN103772416B (zh) | 2012-10-18 | 2018-01-19 | 精工爱普生株式会社 | 噻二唑系化合物、发光元件用化合物、发光元件、发光装置、认证装置以及电子设备 |
EP2915199B1 (de) | 2012-10-31 | 2021-03-31 | Merck Patent GmbH | Elektronische vorrichtung |
CN104781247B (zh) | 2012-11-12 | 2017-08-15 | 默克专利有限公司 | 用于电子器件的材料 |
US20150329772A1 (en) | 2013-01-03 | 2015-11-19 | Merck Patent Gmbh | Materials for Electronic Devices |
DE102013106949A1 (de) * | 2013-07-02 | 2015-01-08 | Osram Opto Semiconductors Gmbh | Optoelektronisches Bauelement, organische funktionelle Schicht und Verfahren zur Herstellung eines optoelektronischen Bauelements |
US20160226001A1 (en) | 2013-09-11 | 2016-08-04 | Merck Patent Gmbh | Organic Electroluminescent Device |
US20170092875A1 (en) | 2014-03-18 | 2017-03-30 | Merck Patent Gmbh | Organic electroluminescent device |
EP2960315A1 (de) | 2014-06-27 | 2015-12-30 | cynora GmbH | Organische Elektrolumineszenzvorrichtung |
EP2985799A1 (en) | 2014-08-11 | 2016-02-17 | Dyenamo AB | Solid state hole transport material |
WO2016042070A1 (de) | 2014-09-17 | 2016-03-24 | Cynora Gmbh | Organische moleküle zur verwendung als emitter |
DE102014114224A1 (de) * | 2014-09-30 | 2016-03-31 | Osram Oled Gmbh | Organisches elektronisches Bauteil, Verwendung eines Zinkkomplexes als p-Dotierungsmittel für organische elektronische Matrixmaterialien |
CN115838341A (zh) | 2014-12-12 | 2023-03-24 | 默克专利有限公司 | 具有可溶性基团的有机化合物 |
CN114805091A (zh) | 2015-07-22 | 2022-07-29 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
EP3328825B1 (en) | 2015-07-29 | 2023-06-28 | Merck Patent GmbH | Materials for organic electroluminescent devices |
KR102599157B1 (ko) | 2015-08-14 | 2023-11-06 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 페녹사진 유도체 |
CN108603107B (zh) | 2016-02-05 | 2022-08-26 | 默克专利有限公司 | 用于电子器件的材料 |
CN116283863A (zh) | 2016-06-03 | 2023-06-23 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
DE102017008794A1 (de) | 2016-10-17 | 2018-04-19 | Merck Patent Gmbh | Materialien zur Verwendung in elektronischen Vorrichtungen |
WO2018083053A1 (de) | 2016-11-02 | 2018-05-11 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20230121632A (ko) | 2016-11-08 | 2023-08-18 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
WO2018095888A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
TWI781123B (zh) | 2016-11-25 | 2022-10-21 | 德商麥克專利有限公司 | 用於有機電激發光裝置之材料 |
JP2018110179A (ja) * | 2016-12-31 | 2018-07-12 | 株式会社Flosfia | 正孔輸送層形成用組成物 |
KR102683465B1 (ko) | 2017-02-02 | 2024-07-09 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
EP3583636B1 (en) | 2017-02-20 | 2023-05-24 | Novaled GmbH | Electronic semiconducting device, method for preparing the electronic semiconducting device and compound |
WO2018157981A1 (de) | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materialien für organische elektronische vorrichtungen |
EP3382770B1 (en) * | 2017-03-30 | 2023-09-20 | Novaled GmbH | Ink composition for forming an organic layer of a semiconductor |
JP2018181658A (ja) * | 2017-04-17 | 2018-11-15 | 独立行政法人国立高等専門学校機構 | 有機発光素子の製造方法 |
WO2018234346A1 (en) | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
KR20240059634A (ko) | 2017-06-28 | 2024-05-07 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
US20200212301A1 (en) | 2017-07-28 | 2020-07-02 | Merck Patent Gmbh | Spirobifluorene derivatives for use in electronic devices |
CN118405981A (zh) | 2017-09-08 | 2024-07-30 | 默克专利有限公司 | 用于电子器件的材料 |
CN108675975A (zh) | 2017-10-17 | 2018-10-19 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
JP2021504356A (ja) | 2017-11-23 | 2021-02-15 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
TWI838352B (zh) | 2017-11-24 | 2024-04-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI820057B (zh) | 2017-11-24 | 2023-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
KR102638811B1 (ko) | 2017-12-15 | 2024-02-21 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 치환된 방향족 아민 |
US20210036245A1 (en) | 2017-12-20 | 2021-02-04 | Merck Patent Gmbh | Heteroaromatic compounds |
TW201938761A (zh) | 2018-03-06 | 2019-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI802656B (zh) | 2018-03-06 | 2023-05-21 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
CN111819167A (zh) | 2018-03-16 | 2020-10-23 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TWI823993B (zh) | 2018-08-28 | 2023-12-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TWI837167B (zh) | 2018-08-28 | 2024-04-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
EP3844243B1 (en) | 2018-08-28 | 2022-06-22 | Merck Patent GmbH | Materials for organic electroluminescent devices |
WO2020053150A1 (en) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2020089138A1 (en) | 2018-10-31 | 2020-05-07 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TW202136181A (zh) | 2019-12-04 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
KR20230043106A (ko) | 2020-07-22 | 2023-03-30 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
EP3945090A1 (en) | 2020-07-27 | 2022-02-02 | Novaled GmbH | Metal complexes of 3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pentane-2,4-dione and similar ligands as semiconductor materials for use in electronic devices |
WO2022023260A1 (en) | 2020-07-27 | 2022-02-03 | Novaled Gmbh | Metal complexes of 3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridin-4-yl)pentane-2,4-dione and similar ligands as semiconductor materials for use in electronic devices |
EP3945125A1 (en) | 2020-07-28 | 2022-02-02 | Novaled GmbH | Compound of formula (i), a semiconductor material comprising at least one compound of formula (i), an semiconductor layer comprising at least one compound of formula (i) and an electronic device comprising at least one compound of formula (i) |
CN116249755A (zh) | 2020-07-28 | 2023-06-09 | 诺瓦尔德股份有限公司 | 作为用于电子器件中的半导体材料的4-(2,4-二氧代戊-3-基)-2,3,5,6-四氟苯甲腈和类似配体的金属络合物 |
WO2022097129A1 (es) | 2020-11-05 | 2022-05-12 | Torres Sebastian Agustin | Película plástica laminada para formado de empaques de plástico a alta velocidad |
EP4151642A1 (en) | 2021-09-20 | 2023-03-22 | Novaled GmbH | Compound, semiconductor layer comprising compound and organic electronic device |
EP4405362A2 (en) | 2021-09-20 | 2024-07-31 | Novaled GmbH | Compound, semiconductor layer comprising compound and organic electronic device |
CN118056486A (zh) | 2021-09-28 | 2024-05-17 | 默克专利有限公司 | 用于电子器件的材料 |
WO2023052313A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052275A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20240075872A (ko) | 2021-09-28 | 2024-05-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
WO2023094412A1 (de) | 2021-11-25 | 2023-06-01 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
CN118354991A (zh) | 2021-12-21 | 2024-07-16 | 默克专利有限公司 | 用于制备氘化的有机化合物的方法 |
WO2023117835A1 (en) | 2021-12-21 | 2023-06-29 | Merck Patent Gmbh | Electronic devices |
KR20240127395A (ko) | 2021-12-21 | 2024-08-22 | 메르크 파텐트 게엠베하 | 전자 디바이스 |
CN118647604A (zh) | 2022-02-14 | 2024-09-13 | 默克专利有限公司 | 用于电子器件的材料 |
WO2023222559A1 (de) | 2022-05-18 | 2023-11-23 | Merck Patent Gmbh | Verfahren zur herstellung von deuterierten organischen verbindungen |
WO2024013004A1 (de) | 2022-07-11 | 2024-01-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP4321506A1 (en) | 2022-08-09 | 2024-02-14 | Novaled GmbH | Metal complex, semiconductor layer comprising a metal complex and organic electronic device |
WO2024170605A1 (en) | 2023-02-17 | 2024-08-22 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008051737A1 (de) * | 2007-10-24 | 2009-05-07 | Novaled Ag | Quadratisch planare Übergangsmetallkomplexe und diese verwendende organische halbleitende Materialien sowie elektronische oder optoelektronische Bauelemente |
CN102598342A (zh) * | 2009-10-27 | 2012-07-18 | 大日本印刷株式会社 | 具有空穴注入传输层的器件及其制造方法以及空穴注入传输层形成用油墨 |
CN102947414B (zh) * | 2010-03-31 | 2016-04-27 | 欧司朗光电半导体有限公司 | 用于有机半导体器件的空穴导电层的掺杂材料及其应用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100937900B1 (ko) | 2001-08-29 | 2010-01-21 | 유니버시티 오브 서던 캘리포니아 | 금속착물을 포함하는 캐리어수송층을 구비한 유기발광장치 |
US9157023B2 (en) | 2003-11-18 | 2015-10-13 | Koninklijke Philips N.V. | Light-emitting device with an iridium complex |
US7867676B2 (en) * | 2007-07-31 | 2011-01-11 | Xerox Corporation | Copper containing hole blocking layer photoconductors |
JP2011060998A (ja) * | 2009-09-10 | 2011-03-24 | Konica Minolta Holdings Inc | 有機光電変換素子、その製造方法、有機光電変換素子を用いた太陽電池及び光センサアレイ |
WO2011033023A1 (en) | 2009-09-18 | 2011-03-24 | Osram Opto Semiconductors Gmbh | Organic electronic device and dopant for doping an organic semiconducting matrix material |
-
2010
- 2010-03-31 DE DE201010013495 patent/DE102010013495A1/de active Pending
-
2011
- 2011-03-31 KR KR1020177002902A patent/KR101757888B1/ko active IP Right Grant
- 2011-03-31 CN CN201180018027.8A patent/CN102947414B/zh active Active
- 2011-03-31 KR KR1020127028505A patent/KR101705136B1/ko active IP Right Grant
- 2011-03-31 CN CN201610206776.8A patent/CN106410026B/zh active Active
- 2011-03-31 US US13/638,596 patent/US9006716B2/en active Active
- 2011-03-31 WO PCT/EP2011/001645 patent/WO2011120709A1/de active Application Filing
- 2011-03-31 JP JP2013501693A patent/JP5847157B2/ja not_active Expired - Fee Related
- 2011-03-31 EP EP11714935.1A patent/EP2553047B1/de active Active
-
2015
- 2015-02-27 US US14/633,609 patent/US9276223B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008051737A1 (de) * | 2007-10-24 | 2009-05-07 | Novaled Ag | Quadratisch planare Übergangsmetallkomplexe und diese verwendende organische halbleitende Materialien sowie elektronische oder optoelektronische Bauelemente |
CN102598342A (zh) * | 2009-10-27 | 2012-07-18 | 大日本印刷株式会社 | 具有空穴注入传输层的器件及其制造方法以及空穴注入传输层形成用油墨 |
CN102947414B (zh) * | 2010-03-31 | 2016-04-27 | 欧司朗光电半导体有限公司 | 用于有机半导体器件的空穴导电层的掺杂材料及其应用 |
Also Published As
Publication number | Publication date |
---|---|
CN106410026A (zh) | 2017-02-15 |
KR101757888B1 (ko) | 2017-07-14 |
US9276223B2 (en) | 2016-03-01 |
JP5847157B2 (ja) | 2016-01-20 |
CN102947414A (zh) | 2013-02-27 |
KR101705136B1 (ko) | 2017-02-09 |
US9006716B2 (en) | 2015-04-14 |
US20150200374A1 (en) | 2015-07-16 |
KR20130025897A (ko) | 2013-03-12 |
EP2553047A1 (de) | 2013-02-06 |
CN102947414B (zh) | 2016-04-27 |
DE102010013495A1 (de) | 2011-10-06 |
JP2013527599A (ja) | 2013-06-27 |
EP2553047B1 (de) | 2016-12-21 |
WO2011120709A1 (de) | 2011-10-06 |
US20130099209A1 (en) | 2013-04-25 |
KR20170015573A (ko) | 2017-02-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106410026B (zh) | 有机半导体器件的空穴导电层及其应用和有机电子器件 | |
Yang et al. | Wide‐range color tuning of narrowband emission in multi‐resonance organoboron delayed fluorescence materials through Rational Imine/Amine Functionalization | |
Lee et al. | Deep blue phosphorescent organic light-emitting diodes with very high brightness and efficiency | |
Cao et al. | Near-infrared polymer light-emitting diodes with high efficiency and low efficiency roll-off by using solution-processed iridium (III) phosphors | |
Tao et al. | Multifunctional triphenylamine/oxadiazole hybrid as host and exciton‐blocking material: high efficiency green phosphorescent OLEDs using easily available and common materials | |
Costa et al. | Luminescent ionic transition‐metal complexes for light‐emitting electrochemical cells | |
Uoyama et al. | Highly efficient organic light-emitting diodes from delayed fluorescence | |
US8932730B2 (en) | Doped organic carrier transport materials | |
Yuen et al. | Synthesis, Photophysical and Electrophosphorescent Properties of Fluorene‐Based Platinum (II) Complexes | |
Ma et al. | Carbazole‐Containing Polymer‐Assisted Trap Passivation and Hole‐Injection Promotion for Efficient and Stable CsCu2I3‐Based Yellow LEDs | |
US20100193774A1 (en) | Quinoid Compounds and Their Use in Semiconducting Matrix Materials, Electronic and Optoelectronic Structural Elements | |
Tang et al. | Saturated Red‐Light‐Emitting Gold (III) Triphenylamine Dendrimers for Solution‐Processable Organic Light‐Emitting Devices | |
Giridhar et al. | An Easy Route to Red Emitting Homoleptic IrIII Complex for Highly Efficient Solution‐Processed Phosphorescent Organic Light‐Emitting Diodes | |
Chen et al. | Tailoring the molecular properties with isomerism effect of AIEgens | |
KR102009057B1 (ko) | 도펀트를 사용한 유기 전자 부품, 도펀트의 용도 및 상기 도펀트의 제조 방법 | |
Qiao et al. | Synthesis, crystal structure, and luminescent properties of a binuclear gallium complex with mixed ligands | |
Asatkar et al. | Metallo‐organic Conjugated Systems for Organic Electronics | |
Lipinski et al. | Dual‐Phosphorescent Heteroleptic Silver (I) Complex in Long‐Lasting Red Light‐Emitting Electrochemical Cells | |
Wu et al. | Low Efficiency Roll‐Off Blue Phosphorescent OLEDs at High Brightness Based on [3+ 2+ 1] Coordinated Iridium (III) Complexes | |
Xia et al. | Ruthenium (II) Complexes with the Mixed Ligands 2, 2 ‘-Bipyridine and 4, 4 ‘-Dialkyl Ester-2, 2 ‘-bipyridine as Pure Red Dopants for a Single-Layer Electrophosphorescent Device | |
Zhu et al. | A Highly Efficient Red‐Emitting Ruthenium Complex with 3, 5‐Difluorophenyl Substituents | |
Mulani et al. | Structure properties of a highly luminescent yellow emitting material for OLED and its application | |
Fan et al. | Linkage engineering in hosts for dramatic efficiency enhancement of blue phosphorescent organic light-emitting diodes | |
Shahroosvand et al. | Red–yellow electroluminescence, yellow–green photoluminescence of novel N, O donor ligands–chelated zirconium (IV) complexes | |
CN201084751Y (zh) | 有机电致发光器件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |