TWI575054B - 有機發光組合物,裝置及方法 - Google Patents
有機發光組合物,裝置及方法 Download PDFInfo
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- TWI575054B TWI575054B TW101124081A TW101124081A TWI575054B TW I575054 B TWI575054 B TW I575054B TW 101124081 A TW101124081 A TW 101124081A TW 101124081 A TW101124081 A TW 101124081A TW I575054 B TWI575054 B TW I575054B
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- 239000000203 mixture Substances 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 12
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- 229920000642 polymer Polymers 0.000 claims description 71
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- 239000002019 doping agent Substances 0.000 claims description 43
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- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004122 cyclic group Chemical group 0.000 claims description 11
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- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 description 38
- 125000003118 aryl group Chemical group 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 22
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- -1 for example Chemical group 0.000 description 8
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- 125000005264 aryl amine group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
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- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 3
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
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- 238000010348 incorporation Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
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- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
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- GGUFVZFOCZNPEG-UHFFFAOYSA-N 4,5,6-triphenyltriazine Chemical class C1=CC=CC=C1C1=NN=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GGUFVZFOCZNPEG-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- ZIPRMPRBQSJVJY-UHFFFAOYSA-N C(C(=O)C)(=O)O.C(C)(=N)N Chemical compound C(C(=O)C)(=O)O.C(C)(=N)N ZIPRMPRBQSJVJY-UHFFFAOYSA-N 0.000 description 1
- NVKHKMBMLSFNNU-UHFFFAOYSA-N C=CC1=CC=CC=C1.[S] Chemical compound C=CC1=CC=CC=C1.[S] NVKHKMBMLSFNNU-UHFFFAOYSA-N 0.000 description 1
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- 238000005698 Diels-Alder reaction Methods 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910015711 MoOx Inorganic materials 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019897 RuOx Inorganic materials 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- BCZWPKDRLPGFFZ-UHFFFAOYSA-N azanylidynecerium Chemical compound [Ce]#N BCZWPKDRLPGFFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000012966 insertion method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 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
- 238000007650 screen-printing Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920000576 tactic polymer Polymers 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
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Description
本發明係關於有機發光組合物、有機發光裝置及其製造方法。
包含活性有機材料之電子裝置由於在諸如以下等裝置中之用途正吸引愈來愈多的關注:有機發光二極體(OLED)、有機光響應裝置(具體而言有機光伏打裝置及有機光感測器)、有機電晶體及記憶體陣列裝置。包含有機材料之裝置提供多種益處,例如低重量、低電力消耗及撓性。另外,使用可溶性有機材料容許在裝置製造中使用溶液處理,例如噴墨印刷或旋塗。
OLED可包含基板,其攜載陽極、陰極及一或多個陽極與陰極之間之有機發光層。亦可在陽極與陰極之間提供一或多個有機電荷傳輸層及/或一或多個電荷阻擋層。
在裝置之操作期間,電洞經由陽極注入裝置且電子經由陰極注入。發光材料之最高佔據分子軌域(HOMO)中之電洞與最低未佔據分子軌域(LUMO)中之電子組合以形成以光形式釋放能量之激子。
適宜發光材料包括小分子、聚合及樹枝狀材料。適宜發光聚合物包括聚(伸芳基伸乙烯基)(例如聚(對-伸苯基伸乙烯基))及聚伸芳基(例如聚茀)。
發光層可包含半導體主體材料及發光摻雜劑,其中能量自主體材料轉移至發光摻雜劑。舉例而言,J.Appl.Phys.
65,3610,1989揭示摻雜有螢光發光摻雜劑之主體材料(亦即,經由單重態激子之衰變發射光之發光材料)且Appl.Phys.Lett.,2000,77,904揭示摻雜有磷光發光摻雜劑之主體材料(亦即,經由三重態激子之衰變發射光之發光材料)。
OLED之一或多個有機層之形成可藉由自存於溶劑中之溶液沈積用於形成彼等層之材料,之後蒸發溶劑達成。適宜溶液處理方法之實例包括諸如旋塗或浸塗等塗佈方法及諸如噴墨印刷或輥對輥印刷等印刷方法。
在包含多個有機層之裝置中,可藉由以下方法使第一沈積有機層不可溶:在藉由溶液處理方法沈積又一有機層之前交聯以防止第一沈積層被藉由溶液處理又一有機層形成中所用之溶劑溶解。WO 2005/049689揭示包含經可交聯基團(包括雙鍵、三鍵、能夠原位形成雙鍵或雜環狀可加成聚合基團的前體)取代之茀重複單元的聚合物。苯并環丁烷(BCB)揭示為例示性可交聯基團。
WO 2010/013723揭示包含雙鍵基團及BCB基團之聚合物。
來自一個以上OLED層之發射、具體而言以達成白髮光之發射揭示於(例如)WO 2008/131750、DE 102007020644及EP1390962及SPIE(2004),5519,42-47中。
在第一態樣中,本發明提供可交聯發光組合物,其包含至少一種主體材料、至少一種磷光發光摻雜劑、包含不飽
和碳-碳鍵基團之第一交聯劑及包含能夠經歷開環交聯之環系統的第二交聯劑。
視情況,至少一種發光摻雜劑與主體材料摻和。
視情況,將至少一種發光摻雜劑結合至主體材料。
視情況,第一交聯劑包含碳-碳雙鍵,較佳末端雙鍵。
視情況,環系統包含環丁烷。
視情況,環系統包含視情況經取代之多環環系統。
視情況,多環環系統包含視情況經取代之苯并環丁烷基團。
視情況,第一及第二交聯劑中之至少一者係混合於組合物中之交聯化合物。
視情況,至少一種主體材料係聚合物。
視情況,磷光發光摻雜劑係聚合物主鏈、聚合物側基或聚合物端基中之重複單元。
視情況,第一及第二交聯劑中之至少一者係至少一種主體材料之取代基。
視情況,第一及第二交聯劑中之至少一者提供於聚合物之側基或端基中。
視情況,第二交聯劑能夠形成二烯,該二烯能夠與第一交聯劑之不飽和碳-碳鍵基團反應。
在第二態樣中,本發明提供包含第一態樣之可交聯發光組合物及至少一種溶劑的調配物。
在第三態樣中,本發明提供形成有機發光裝置之方法,其包含以下步驟:
藉由將任一前述技術方案之可交聯發光組合物沈積於用於注入第一類型之電荷載子的第一電極上並使可交聯基團交聯來形成第一有機發光層;及在第一有機發光層上形成用於注入第二類型之電荷載子的第二電極。
視情況根據第三態樣,可交聯發光組合物係根據第二態樣之調配物。
視情況根據第三態樣,將有機層自存於溶劑中之溶液沈積至第一有機發光層上。
視情況根據第三態樣,有機層選自第二發光層、電荷傳輸層、電荷阻擋層及激子阻擋層。
在第四態樣中,本發明提供有機發光裝置,其包含自第一態樣之可交聯發光組合物形成的交聯發光層。
視情況根據第四態樣,裝置係白色有機發光裝置。
視情況根據第四態樣,除交聯發光層外,裝置包含至少又一發光層。
現將參照附圖更詳細地闡述本發明。
未按任何比例繪示之圖1示意性闡釋本發明實施例之OLED。OLED攜載於基板1上且包含陽極2、陰極4及介於陽極與陰極之間之發光層3。
OLED可在陽極與陰極之間提供有一或多個額外層(未顯示),包括一或多個其他發光層及/或一或多個電荷傳輸層、電荷阻擋層及/或激子阻擋層。可提供複數個發光
層、具體而言兩個或三個發光層以形成發射白色光之OLED。
至少一個發光層含有交聯主體材料及磷光發光摻雜劑,其各自更詳細闡述於下文中。每一主體材料具有比磷光發光摻雜劑高之三重態能階T1,以使三重態激子可自主體材料轉移至摻雜劑。
在可交聯發光層3已交聯後,可在交聯層上沈積一或多個其他層(未顯示),且可自存於溶劑中之溶液沈積交聯層上形成之層,而不引起交聯層任何顯著溶解。
在OLED之形成期間,較佳在下伏層交聯之前將層溶液沈積至下伏層上,並使用上述交聯劑使至少一個發光層交聯。因此,除使用上述交聯劑使發光層3交聯外,亦可使用與上述交聯劑配置相同或不同之交聯配置使OLED中可存在之一或多個其他有機層交聯。
形成發光層3之組合物含有可交聯基團,其中之一者含有不飽和碳-碳鍵基團且其中之另一者含有能夠經歷開環交聯之環系統。
可交聯基團可與一或多種主體材料結合或混合。在主體材料係聚合物之情形下,可交聯基團可以自聚合物主鏈懸垂之取代基形式提供或附接至聚合物之一或多個端基。
能夠經歷開環交聯之基團之實例包括以下:
其中Ar係視情況經取代之芳基或雜芳基且*代表連接可交聯基團與主體材料或另一載體材料之連接位置。可交聯材料可結合至主體材料及/或另一載體材料,例如具有可交聯基團之非導電聚合物。特定實例包括苯并環丁烷:
含有不飽和碳-碳鍵之可交聯基團之實例具有下式:*-CR7=CH2其中R7係H或取代基且z係0或1。例示性取代基R7包括C1-20烷基及視情況經取代之芳基或雜芳基,例如,經一或多個C1-20烷基取代之苯基。
苯并環丁烷之環丁烷環可開環以形成能夠在Diels-Alder反應中與親二烯物反應之二烯,且可使用任何能夠開環以形成適於與親二烯物反應之二烯的材料。
交聯基團中之每一者可獨立地經一或多個取代基(例如一或多個C1-20烷基)取代。
交聯基團可直接結合至主體材料或另一載體,或由間隔基團與主體材料或另一載體隔開。
例示性間隔基團可形成包括式-(Ar7)p-及-(CH2)m-基團中之一或多者的鏈,其中每一Ar7獨立地代表視情況經取代之芳基或雜芳基,例如視情況經一或多個C1-20烷基取代之苯基,p至少為1,例如1、2或3;m至少為1,例如介於1與10之間之整數;-(CH2)m-中之每一H可獨立地由取代基(例如F或烷基)替代,且-(CH2)m-之一或多個碳原子可由雜原
子(例如O或S)替代。
交聯基團可藉由(例如)熱處理及/或暴露於具有用於交聯之波長及強度之光(例如UV光)來交聯。藉由熱處理之交聯可在100℃至250℃、視情況120℃至200℃之範圍內之溫度下。處理時間可為至少1分鐘,且可高達約3小時,視情況在10分鐘至2小時範圍內。
主體可為具有比與其一起使用之一或多種摻雜劑高之激發態能階、具體而言較高三重激發態能階的任何材料。較佳地,主體與摻雜劑激發態能階之間之能隙係至少kT,以避免激子自摻雜劑反向轉移至主體材料。主體材料視情況可經溶液處理。
主體材料可選自具有適宜能階之小分子、樹枝狀及聚合物材料。主體材料亦可根據其最高佔據分子軌域(HOMO)及/或最低未佔據分子軌域(LUMO)能階選擇以分別對電洞及電子自毗鄰層傳輸至含有主體材料之發光層中提供極小障壁或無障壁。
主體材料可攜載上述不飽和交聯劑及開環交聯劑中之一或多者。
主體材料之實例包括:
(i)三嗪,例如二芳基三嗪或三芳基三嗪。含三嗪之主體材料更詳細闡述於WO 2008/025997中且包括(例如)視情況經取代之三苯基三嗪。苯基之可選取代基包括一或多個烷基,例如C1-20烷基。主體可為包含三嗪重複單元、具體而
言經由一個芳基作為側基附接之視情況經取代之二-或三-芳基三嗪重複單元或經由兩個芳基附接於聚合物主鏈中之重複單元的小分子或聚合物。包含三嗪重複單元之主體聚合物可包含選自以下之其他重複單元:伸(雜)芳基共重複單元,例如苯基、茀或茚并茀重複單元,其中該等伸(雜)芳基重複單元中之每一者皆可視情況經一或多個取代基(例如烷基或烷氧基)取代,例如如下文更詳細闡述之茀重複單元。
(ii)含有(雜)芳基胺重複單元之聚合物,其作為均聚物或具有一或多個共重複單元,例如下文所述伸(雜)芳基重複單元。例示性(雜)芳基胺重複單元包括式(V)之重複單元:
其中Ar1及Ar2在每次出現時獨立地選自視情況經取代之芳基或雜芳基,n大於或等於1,較佳地1或2,R係H或取代基,較佳地取代基,且x及y各自獨立地係1、2或3。
R較佳地係烷基(例如C1-20烷基)、Ar3或Ar3基團之分支鏈或直鏈(例如-(Ar3)r),其中Ar3在每次出現時獨立地選自芳基或雜芳基,且r至少為1,視情況為1、2或3。
Ar1、Ar2及Ar3中之任一者可獨立地經一或多個取代基取代。較佳取代基選自由以下組成之基團R3:烷基(例如C1-20烷基),其中一或多個非毗鄰C原子可由O、S、經取代之N、C=O及-COO-替代,且烷基之一
或多個H原子可由F或視情況經一或多個基團R4取代之芳基或雜芳基替代,視情況經一或多個基團R4取代之芳基或雜芳基,NR5 2、OR5、SR5,氟、硝基及氰基;其中每一R4皆獨立地係烷基(例如C1-20烷基),其中一或多個非毗鄰C原子可由O、S、經取代之N、C=O及-COO-替代,且烷基之一或多個H原子可由F替代,且每一R5皆獨立地選自由烷基及視情況經一或多個烷基取代之芳基或雜芳基組成之群。
R可包含可交聯基團,例如如上文所述可直接結合至式(V)重複單元之N原子或由上述間隔基團與N原子隔開的不飽和或開環交聯基團。
式(V)之重複單元中之芳基或雜芳基中之任一者可由直接鍵或二價連接原子或基團連接。較佳二價連接原子及基團包括O、S;經取代之N;及經取代之C。
若存在,則R3、R4或二價連接基團之經取代之N或經取代之C在每次出現時可分別獨立地係NR6或CR6 2,其中R6係烷基或視情況經取代之芳基或雜芳基。芳基或雜芳基R6之可選取代基可選自R4或R5。
在一個較佳配置中,R係Ar3,且Ar1、Ar2及Ar3中之每一者皆獨立地且視情況經一或多個C1-20烷基取代。
符合式1之尤佳單元包括式1-3之單元:
其中Ar1及Ar2係如上文所定義;且Ar3係視情況經取代之芳基或雜芳基。若存在,則Ar3之較佳取代基包括如針對Ar1及Ar2所述之取代基,具體而言烷基及烷氧基。
Ar1、Ar2及Ar3較佳係苯基,其每一者皆可獨立地經一或多個如上文所述之取代基取代。
在另一較佳配置中,式(V)之芳基或雜芳基係苯基,每一苯基皆視情況經一或多個烷基取代。
在另一較佳配置中,Ar1、Ar2及Ar3係苯基,其每一者皆可經一或多個C1-20烷基取代,且r=1。
在另一較佳配置中,Ar1及Ar2係苯基,其每一者皆可經一或多個C1-20烷基取代,且R係3,5-二苯基苯,其中每一苯基皆可經一或多個烷基取代。
(iii)包含伸(雜)芳基重複單元之聚合物,其作為均聚物或具有一或多個共重複單元,例如下文所述伸(雜)芳基胺重複單元。例示性伸芳基重複單元包括苯基、茀及茚并茀重複單元,其各自可視情況經一或多個取代基(例如烷基或烷氧基)取代。
例示性茀重複單元包括式(IV)之重複單元:
其中R1及R2獨立地係H或取代基,且其中R1及R2可經連接以形成環。
R1及R2視情況選自由以下組成之群:氫;視情況經取代之Ar3或Ar3基團之直鏈或分支鏈,其中Ar3係如上文所述;視情況經取代之烷基,例如C1-20烷基,其中烷基之一或多個非毗鄰C原子可由O、S、經取代之N、C=O及-COO-替代;及如上述交聯基團,其可直接結合至茀單元或由如上述間隔基團與茀單元隔開。
在R1或R2包含烷基之情形下,烷基之可選取代基包括F、CN、硝基以及視情況經一或多個基團R4取代之芳基或雜芳基,其中R4係如上文所述。
在R1或R2包含芳基或雜芳基之情形下,每一芳基或雜芳基皆可獨立地經取代。芳基或雜芳基之較佳可選取代基包括一或多個取代基R3。
除取代基R1及R2以外,茀單元之可選取代基較佳選自由以下組成之群:烷基,其中一或多個非毗鄰C原子可由O、S、經取代之N、C=O及-COO-替代;視情況經取代之芳基;視情況經取代之雜芳基;氟;氰基及硝基。
若存在,則式(IV)重複單元中之經取代之N可在每次出現時獨立地為NR5或NR6。
在一個較佳配置中,R1及R2中之至少一者包含視情況經
取代之C1-C20烷基;或視情況經取代之芳基,具體而言經一或多個C1-20烷基取代之苯基。
包含式(IV)重複單元的主體聚合物可攜載上述不飽和基團及開環可交聯基團中之一者或二者。攜載可交聯基團之例示性式(IV)重複單元包括以下,如WO 2005/049689中所述:
例示性苯基重複單元包括式(V)重複單元:
其中R1係如上文所述;v係0、1、2、3或4;在v係2、3或4之情形下,每一R1相同或不同;且毗鄰基團R1可連接形成環。視情況,v係1或2。視情況,R1在每次出現時係視情況經取代之C1-C20烷基。視情況,式(I)之單元經1,4-連接。
在一個較佳配置中,式(I)重複單元經1,4-連接且取代基R1存於2位中且視情況亦存於5位中。
主體聚合物可包含上述三嗪重複單元、(雜)芳基胺重複單元及伸芳基重複單元中之一者、二者或更多者。
包含芳香族重複單元之主體聚合物可形成芳香族單元之共軛鏈。此共軛可藉由在聚合物主鏈中納入適宜重複單元(例如在聚合物主鏈中形成扭轉之重複單元及破壞共軛之重複單元)來中斷或降低。
可在聚合物主鏈中引起扭轉(例如,藉由位阻)之重複單元之實例係經一或多個基團(例如一或多個烷基或烷氧基,例如C1-20烷基或烷氧基)取代之1,4-伸苯基,具體而言2,5-二取代之-1,4-伸苯基重複單元。
一類可破壞共軛之重複單元包括經由非共軛位置連接至毗鄰重複單元之伸芳基或伸雜芳基重複單元。此類例示性單元包括1,2-伸苯基重複單元及1,3-伸苯基重複單元(其各自可視情況經一或多個取代基(例如一或多個如上文所述取代基R1,具體而言一或多個烷基或烷氧基,例如C1-20烷基或烷氧基)取代)、以及經由2位及/或6位連接之茀重複單元,其可再次視情況經一或多個取代基(例如一或多個如上文所述取代基R1)取代。
另一類可破壞共軛之重複單元包括具有式-Ar6-Sp-Ar6-之重複單元,其中每一Ar6係視情況經取代之芳基或雜芳基且Sp係間隔原子或在兩個Ar基團之間包含至少一個非共軛原子之鏈。例示性Ar6基團包括視情況經取代之苯基。可選取代基可為一或多個如上文所述取代基R1,具體而言一或多個烷基或烷氧基,例如C1-20烷基或烷氧基。例示性基團Sp包括式-(CH2)m-之基團,其中m至少為1,例如介於1至10之間之整數,且其中每一H可獨立地由取代基(例如
烷基)替代,且其中一或多個碳原子可由雜原子(例如O或S)替代。
(iv)包含懸垂電荷傳輸基團之非共軛聚合物。該聚合物之實例係聚乙烯基咔唑(PVK)。
用於交聯層中之發光摻雜劑可為磷光。若存在,則用於裝置之任一其他發光層中的發光摻雜劑可選自螢光及磷光摻雜劑。
磷光發光摻雜劑包括金屬錯合物,其包含視情況經取代之式(II)錯合物:ML1 qL2 rL3 s (II)其中M係金屬;L1、L2及L3之每一者皆係配位基團;q係整數;r及s各自獨立地係0或整數;且(a.q)+(b.r)+(c.s)之和等於M上可用的配位位點數,其中a係L1上之配位位點數,b係L2上之配位位點數且c係L3上之配位位點數。
重元素M誘導強自旋軌道偶合,以允許快速系統間跨越及自三重態或更高態之發射(磷光)。適宜重金屬M包括d區金屬,具體而言彼等在第2列及第3列中者,即元素39至48及72至80,具體而言係釕、銠、鈀、錸、鋨、銥、鉑及金。銥尤佳。
f區金屬之適宜配位基團包括氧或氮供體系統,例如羧酸、1,3-二酮酸鹽、羥基羧酸、希夫鹼(Schiff base,包括醯基苯酚及亞胺基醯基)。如所知,發光鑭金屬錯合物需要敏化基團,其具有比金屬離子之第一激發態高之三重激
發態能階。發射係來自金屬之f-f過渡且因此由金屬之選擇確定發射顏色。尖銳發射通常較窄,從而產生用於顯示器應用之純顏色發射。
d區金屬尤其適於自三重激發態之發射。該等金屬與碳或氮供體(例如卟啉或式(III)二齒配體)形成有機金屬錯合物:
其中Ar4及Ar5可相同或不同且獨立地選自視情況經取代之芳基或雜芳基;X1及Y1可相同或不同且獨立地選自碳或氮;且Ar4及Ar5可稠和在一起。X1係碳(例如,Ar4係視情況經取代且視情況稠合之苯基)且Y1係氮(例如,Ar5係視情況經取代且視情況稠合之吡啶)之配體尤佳。
二齒配體之實例如下所示:
Ar4及Ar5中之每一者皆可攜載一或多個取代基。該等取代基之兩者或更多者可連接以形成環,例如芳香族環。尤佳取代基包括氟或三氟甲基,其可用於使錯合物之發射藍移,如(例如)WO 02/45466、WO 02/44189、US 2002-117662及US 2002-182441中所揭示;烷基或烷氧基,如(例如)JP 2002-324679中所揭示;咔唑,其在使用錯合物作為
發射材料時可用於有助於電洞傳輸至該至錯合物,如(例如)WO 02/81448中所揭示;溴、氯或碘,其可用於官能化配體以便附接其他基團,如(例如)WO 02/68435及EP 1245659中所揭示;及樹枝狀基團(dendron),其可用於獲得或增強金屬錯合物之溶液可處理性,如(例如)WO 02/6655中所揭示。
發光樹枝狀聚合物通常包含結合至一或多個樹枝狀基團之發光核心,其中每一樹枝狀基團皆包含分支點及兩個或更多個樹枝狀分支。較佳地,樹枝狀基團至少部分地共軛,且核心及樹枝狀分枝中之至少一者包含芳基或雜芳基。
適用於d區元素之其他配體包括二酮酸鹽,具體而言乙醯丙酮酸鹽(acac);三芳基膦及吡啶,其每一者皆可經取代。
用於OLED中之一或多種摻雜劑可發生可見譜內之任何顏色的光。
發射藍光摻雜劑可視情況具有在400 nm至480 nm範圍內具有峰之光致發光譜。藍摻雜劑之實例係揭示於WO 2004/101707中之磷光摻雜劑面式-叁(1-甲基-5-苯基-3-丙基-[1,2,4]三唑基)銥(III)。
綠發射摻雜劑可視情況具有在490 nm至560 nm範圍內具有峰之光致發光譜。綠摻雜劑之實例係磷光摻雜劑面式-叁(2-苯基吡啶)銥(III)。
紅發射摻雜劑可視情況在其光致發光發射譜中於約570
nm至630 nm處具有峰。
例示性紅發射體係面式-叁(1-苯基異喹啉)銥(III)。
摻雜劑可以相對於一或多種主體材料高達10 mol%、高達5 mol%、高達2.5 mol%、高達2 mol%、高達1 mol%、高達0.5 mol%或高達0.25 mol%之量提供。
可物理混合主體及發光摻雜劑。或者,發光摻雜劑可化學結合至主體。在聚合物主體之情形下,發光摻雜劑可以附接至聚合物主鏈之取代基形式化學結合,作為聚合物主鏈中之重複單元納入或作為聚合物之端基提供,如(例如)EP 1245659、WO 02/31896、WO 03/18653及WO 03/22908中所揭示。
此結合可使激子自主體聚合物更有效轉移至發光摻雜劑,此乃因其可提供相應混合系統不可用之分子內激子轉移路徑。
此外,出於處理原因,結合可為有利的。舉例而言,若發光摻雜劑具有低溶解性,則將其結合至可溶性主體(具體而言可溶性聚合物)可允許藉由主體在溶液中攜載發光摻雜劑,從而使得使用溶液處理技術進行裝置製造。此外,將發光摻雜劑結合至主體可防止溶液處理之裝置中可對裝置性能有害之相分離效應。
可在陽極與一或多個發光層之間提供電洞傳輸層。同樣,可在陰極與一或多個發光層之間提供電子傳輸層。
類似地,可在陽極與發光層之間提供電子阻擋層且可在
陰極與發光層之間提供電洞阻擋層。傳輸層及阻擋層可組合使用。端視單一層之HOMO及LUMO能階,其可既傳輸電洞及電子中之一者,又阻擋電洞及電子中之另一者。
若存在,則位於陽極與發光層之間之電洞傳輸層較佳具有小於或等於5.5 eV、更佳約4.8 eV至5.5 eV之HOMO能階。可選擇電洞傳輸層之HOMO能階以便在毗鄰層(例如發光層)之0.2 eV內,視情況0.1 eV內,以提供該等層之間之電洞傳輸之較小障壁。
若存在,則位於發光層與陰極之間之電子傳輸層較佳具有約3 eV至3.5 eV之LUMO能階。舉例而言,可在最接近陰極之發光層與陰極之間提供厚度在0.2 nm至2 nm範圍內之一氧化矽或二氧化矽之層或其他薄介電層。可使用循環伏安法量測HOMO及LUMO能階。
電洞傳輸層可含有電洞傳輸(雜)芳基胺,例如包含式(V)之電洞傳輸重複單元的均聚物或共聚物。例示性共聚物包含式(V)之重複單元及視情況經取代之伸(雜)芳基共重複單元,例如如上文所述苯基、茀或茚并茀重複單元,其中該等伸(雜)芳基重複單元中之每一者可視情況經一或多個取代基(例如烷基或烷氧基)取代。特定共重複單元包括如上文所述式(IV)之茀重複單元及視情況經取代之式(I)之伸苯基重複單元。
電子傳輸層可含有包含視情況經取代之伸芳基重複單元之鏈(例如茀重複單元之鏈)的聚合物。
具體而言若電洞傳輸層係藉由自存於溶劑中之溶液沈積
電洞傳輸材料而形成,則電洞傳輸層可交聯。舉例而言,包含式(V)之重複單元、視情況與一或多個伸芳基共重複單元之聚合物可在伸芳基重複單元及式(V)之重複單元中之一或多者上提供有可交聯取代基。
可毗鄰發光層提供激子阻擋層,以防止激子遷移出發光層,此可猝滅激子或吸收及重新發射較長波長下之激子。激子阻擋層可具有比發光層中產生之激子高的單重及/或三重激發態能階。
可在陽極與一或多個發光層之間提供可自導電有機或無機材料形成之導電電洞注入層,以有助於電洞自陽極注入一或多個半導體聚合物層。電洞傳輸層可與電洞注入層組合使用。
摻雜有機電洞注入材料之實例包括視情況經取代之摻雜聚(乙烯二氧噻吩)(PEDT),具體而言摻雜有電荷平衡聚酸(例如如EP 0901176及EP 0947123中揭示之聚磺苯乙烯(PSS)、聚丙烯酸或氟化磺酸,例如Nafion ®)之PEDT;聚苯胺,如US 5723873及US 5798170中揭示;及視情況經取代之聚噻吩或聚(噻吩并噻吩)。導電無機材料之實例包括過渡金屬氧化物,例如VOx、MoOx及RuOx,如Journal of Physics D:Applied Physics(1996),29(11),2750-2753中所揭示。
陰極選自具有允許電子注入一或多個發光層之功函數的材料。其他因素影響陰極之選擇,例如陰極與發光材料之間之不利相互作用的可能性。陰極可由諸如鋁層等單一材料組成。或者,其可包含複數種金屬,例如低功函數材料及高功函數材料(例如鈣及鋁)之雙層,如WO 98/10621中揭示。陰極可含有具有元素鋇之層,如(例如)WO 98/57381,Appl.Phys.Lett.2002,81(4),634及WO 02/84759中所揭示。陰極可在OLED之發光層與陰極之一或多個導電層(例如一或多個金屬層)之間含有金屬化合物之薄層。例示性金屬化合物包括有助於電子注入之鹼金屬或鹼土金屬之氧化物或氟化物,例如氟化鋰,如WO 00/48258中所揭示;氟化鋇,如Appl.Phys.Lett.2001,79(5),2001中所揭示;及氧化鋇。為將電子有效注入裝置中,陰極之功函數較佳地低於3.5 eV,更佳地低於3.2 eV,最佳地低於3 eV。金屬之功函數可參見(例如)Michaelson,J.Appl.Phys.48(11),4729,1977。
陰極可不透明或透明。透明陰極對於主動式矩陣裝置尤其有利,此乃因該等裝置中穿過透明陽極之發射至少部分地受到位於發射像素下方之驅動電路的阻擋。透明陰極包含足夠薄以透明之電子注入材料層。通常,此層之橫向導電率將因其較薄而較低。在此情形下,電子注入材料層與較厚透明導電材料層(例如氧化銦錫)組合使用。
應瞭解,透明陰極裝置無需具有透明陽極(當然,除非期望完全透明之裝置),且因此可用諸如鋁層等反射材料
層替代或補充用於底部發射裝置之透明陽極。透明陰極裝置之實例揭示於(例如)GB 2348316中。
有機光電子裝置往往對水分及氧敏感。因此,基板1較佳具有防止水分及氧侵入裝置之良好障壁性質。基板通常係玻璃,然而,可使用替代基板,具體而言裝置之撓性係合意的。舉例而言,基板可包含如US 6268695(其揭示交替塑膠及障壁層或薄玻璃之壓層的基板)中之塑膠及如EP 0949850中揭示之塑膠。
裝置可經囊封物(未顯示)囊封以防止水分及氧侵入。適宜囊封物包括玻璃片;具有適宜障壁性質之膜,例如二氧化矽、一氧化矽、氮化矽或如(例如)WO 01/81649中所揭示之聚合物及電介質之交替堆疊;或如(例如)WO 01/19142中所揭示之氣密容器。在透明陰極裝置之情形下,透明囊封層(例如一氧化矽或二氧化矽)可沈積至微米厚度等級,但在一個較佳實施例中,該層之厚度在20 nm至300 nm範圍內。用於吸收可滲透穿過基板或囊封物之任何大氣水分及/或氧之吸收劑材料可佈置於基板與囊封物之間。
用於形成組合物之可溶液處理之調配物的適宜溶劑可選自常見有機溶劑,例如單烷基苯或多烷基苯,例如甲苯及二甲苯。
例示性溶液沈積技術包括印刷及塗佈技術,例如旋塗、浸塗、輥對輥塗佈或輥對輥印刷、刮刀塗佈、狹縫模具式
塗佈、凹版印刷、絲網印刷及噴墨印刷。
塗佈方法(例如彼等上文所述者)尤其適於非必要對一或多個發光層實施圖案化之裝置,例如適於照明應用或簡單單色分段顯示器。
印刷尤其適於高資訊容量顯示器,具體而言全彩顯示器。可藉由在第一電極上提供圖案化層並界定用於印刷一種顏色(在單色裝置之情形下)或多種顏色(在多色、具體而言全彩裝置之情形下)之孔來對裝置實施噴墨印刷。圖案化層通常係經圖案化以界定孔之光阻劑層,如在(例如)EP 0880303中所述。
作為孔之替代物,可將油墨印刷至圖案化層內所界定之通道中。具體而言,可將光阻劑圖案化以形成通道,與孔不同的,此通道在複數個像素上延伸,且通道末端可封閉或開放。
製備共軛聚合物(例如包含上述式(IV)及/或(V)之重複單元的聚合物)之較佳方法包含「金屬插入」,其中金屬錯合物觸媒之金屬原子插在芳基或雜芳基與單體之離去基團之間。例示性金屬插入方法係如(例如)WO 00/53656中所述之Suzuki聚合及如(例如)T.Yamamoto,「Electrically Conducting And Thermally Stableπ-Conjugated Poly(arylene)s Prepared by Organometallic Processes」,Progress in Polymer Science 1993,17,1153-1205中所述之Yamamoto聚合。在Yamamoto聚合之情形下,使用鎳錯合物觸媒;在
Suzuki聚合之情形下,使用鈀錯合物觸媒。
舉例而言,在藉由Yamamoto聚合之直鏈聚合物的合成中,使用具有兩個反應性鹵素基團之單體。類似地,根據Suzuki聚合之方法,至少一個反應基團係硼衍生基團,例如酉朋酸或酉朋酸酯,且另一反應基團係鹵素。較佳鹵素係氯、溴及碘,最佳為溴。
因此,應瞭解,貫穿本申請案闡釋之重複單元可衍生自攜載適宜離去基團之單體。同樣,端基或側基可藉由適宜離去基團之反應結合至聚合物。
Suzuki聚合可用於製備立體規則、嵌段及隨機共聚物。具體而言,在一個反應基團係鹵素且另一反應基團係硼衍生基團時,可製備均聚物或隨機共聚物。或者,在第一單體之兩個反應基團均係硼且第二單體之兩個反應基團均係鹵素時,可製備嵌段或立體規則共聚物。
作為鹵化物之替代物,能夠參與金屬插入之其他離去基團包括磺酸及磺酸酯,例如甲苯磺酸酯、甲磺酸酯及三氟甲磺酸酯。
OLED可含有複數個發光層、較佳2個或3個發光層,其經配置以使自該等層之發射觀察為白光。
發光層之例示性配置包括以下:黃發光層/發藍光層
綠發光層/紅發光層/發藍光層
綠發光層+紅發光層/發藍光層
綠發光層/發藍光層+紅發光層
可在該等發光層中之任一者之間提供間隔層以(例如)防止一個層被毗鄰層猝滅。
白光可具有於2500 K至9000 K範圍中之溫度下等效於由黑體發射之CIE x坐標的CIE x坐標及由黑體發射之該光之CIE y坐標之0.05或0.025內的CIE y坐標,視情況於2700 K至4500 K範圍中之溫度下等效於由黑體發射之CIE x坐標的CIE x坐標。
該等裝置之黃、紅、綠及發藍光材料可選自熟習此項技術者已知之如上文所述螢光或磷光發光材料。使用上述不飽和交聯劑及開環交聯劑使該等發光層中之一者交聯。可使用或可不使用上述一或多種交聯劑使其他一或多個發光層交聯。
白OLED可僅包括磷光發光材料或螢光及磷光發光材料之組合。
發藍光層之例示性藍螢光材料係包含上述芳基胺重複單元(V)之聚合物。此聚合物可為均聚物或共聚物,例如具有一或多個伸芳基重複單元(例如茀重複單元(IV)或伸苯基重複單元(I))之共聚物。
如本文所述OLED可用於多種應用中,包括(但不限於)用作顯示器背光燈,例如用作顯示器或用作白光源用於諸如LCD背光燈或區域照明等應用。作為光源之白髮光OLED可包含均勻(未圖案化)發射層。用於顯示器中之
OLED可包含一或多個圖案化發射層及/或圖案化電極以提供個別顯示器像素。
聚合物實例1係藉由包含下文闡釋之莫耳百分比之單體的聚合混合物之Suzuki聚合來形成。聚合係如WO 00/53656中所述實施。
出於比較目的,聚合物係如聚合物實例1中所述製得,只是使用10 mol%苯并環丁烷交聯劑,且不使用雙鍵交聯劑。
在玻璃基板上形成具有以下結構之有機發光裝置:ITO/HIL/HTL/EL/陰極其中ITO係係氧化銦錫陽極;HIL係自Plextronics公司購得之電洞注入材料層;HTL係電洞傳輸層,其包含藉由下述單體之Suzuki聚合形成的共聚物;EL係自聚合物實例1形成之綠磷光發光層;且陰極係包含金屬氟化物及鋁之雙層之陰極。
HIL、HTL及EL各自係藉由旋塗包含該層之組份及溶劑之溶液並蒸發溶劑形成。
形成HTL之共聚物係藉由以下單體之Suzuki聚合形成:
使電洞傳輸聚合物交聯,之後沈積以防止HTL在用於形成EL層之材料沈積時溶解。
在沈積用於形成EL層之組合物後,藉由烘烤使組合物交聯。
出於比較之目的,裝置係如實例1中所述形成,只是在主體-摻雜劑組合物沈積後未使EL層交聯。
出於比較之目的,裝置係如實例1中所述形成,只是使用比較聚合物1替代聚合物實例1。
出於比較之目的,裝置係如比較裝置2中所述形成,只是在主體-摻雜劑組合物沈積後未使EL層交聯。
參照圖2,藉由對比較裝置1(EL層未交聯)及實例1(交聯EL層)進行比較可看出,在EL層交聯時外部量子效率無量測到之變化。
再次參照圖2,藉由對比較裝置2及3進行比較可看出,僅包含苯并環丁烷可交聯基團之EL層的交聯產生外部量子效率之顯著下降。
聚合物實例2係藉由包含下文闡釋之莫耳百分比之單體的聚合混合物之Suzuki聚合來形成。聚合係如WO 00/53656中所述實施。
聚合物之黏度平均重量Mz為1,840,000,重量平均分子量Mw為799,000,峰平均分子量Mp為432,000且數量平均分子量Mn為157,000。聚合物之多分散性為5.09。
比較聚合物2係藉由包含下文闡釋之莫耳百分比之單體之聚合混合物的Suzuki聚合形成,其中用10 mol%具有可交聯苯并環丁烷基團之單體替代5 mol%具有可交聯雙鍵基團之單體及5 mol%具有可交聯苯并環丁烷基團之單體。聚
合係如WO 00/53656中所述實施。
聚合物之黏度平均重量Mz為913,000,重量平均分子量Mw為466,000,峰平均分子量Mp為365,000且數量平均分子量Mn為131,000。聚合物之多分散性為3.58。
裝置係如針對裝置實例1所述製得,只是沈積聚合物實例2替代聚合物實例1且藉由於180℃下加熱60分鐘交聯以形成75 nm厚之發光層,且電洞傳輸層係藉由旋塗下述電洞傳輸聚合物2形成。
形成厚度為50 nm之電洞注入層並於170℃下加熱15分鐘。形成厚度為22 nm之電洞傳輸層並於180℃下加熱60分鐘。
電洞傳輸聚合物2係如WO 00/53656中所述藉由以下單體之Suzuki聚合來形成:
裝置係如針對裝置實例2所述製得,只是於基本上不產生交聯之130℃下對聚合物實例2進行退火。
裝置係如針對裝置實例2所述製得,只是藉由加熱至
180℃替代聚合物實例2使比較聚合物2沈積並交聯,以形成發光層。
裝置係如針對比較裝置5所述製得,只是於基本上不產生交聯之130℃下對比較聚合物2進行退火。參照表1,可看出,比較裝置4-6及裝置實例2之CIE x及y坐標類似,但在交聯時比較裝置5之外部量子效率之下降遠大於裝置實例2。
不希望受限於任何理論,據信兩個環系統(例如苯并環丁烷)之間之交聯可形成具有低激發態能階之物質,該低激發態能階造成具有比該物質高之能量(在此情形下,綠磷光摻雜劑之三重態能階)之任何摻雜劑的發光猝滅。
同時不希望受限於任何理論,據信使用包含不飽和碳-碳鍵基團之交聯劑與包含能夠經歷開環交聯之環系統之交聯劑的組合可在不飽和碳-碳鍵基團與環系統之間產生交聯優,先於在兩個環系統之間產生交聯,藉此防止形成具有低激發態能階之上述物質。
儘管已根據具體例示性實施例闡述了本發明,但應瞭
解,彼等熟習此項技術者將可明瞭本文中所揭示特徵之各種修改、改變及/或組合,而不背離如以下申請專利範圍中所述之本發明範圍。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧發光層
4‧‧‧陰極
圖1示意性闡釋本發明實施例之OLED;且圖2闡釋本發明之裝置及比較裝置之量子效率。
1‧‧‧基板
2‧‧‧陽極
3‧‧‧發光層
4‧‧‧陰極
Claims (19)
- 一種可交聯發光組合物,其包含至少一種主體材料、至少一種磷光發光摻雜劑、包含不飽和碳-碳鍵基團之第一交聯劑及包含能夠經歷開環交聯之環系統的第二交聯劑,其中該第一交聯劑及第二交聯劑為可交聯聚合物之重複單元,且其中該可交聯聚合物為該組合物中唯一的可交聯聚合物。
- 如請求項1之可交聯發光組合物,其中該至少一種發光摻雜劑與該主體材料摻和。
- 如請求項1之可交聯發光組合物,其中該至少一種發光摻雜劑係結合至該主體材料。
- 如請求項1至3中任一項之可交聯發光組合物,其中該第一交聯劑包含碳-碳雙鍵。
- 如請求項1至3中任一項之可交聯發光組合物,其中該環系統包含環丁烷。
- 如請求項1至3中任一項之可交聯發光組合物,其中該環系統包含視情況經取代之多環環系統。
- 如請求項6之可交聯發光組合物,其中該多環環系統包含視情況經取代之苯并環丁烷基團。
- 如請求項4之可交聯發光組合物,其中該第一交聯劑包含末端碳-碳雙鍵。
- 如請求項1至3中任一項之可交聯發光組合物,其中該至少一種主體材料係聚合物。
- 如請求項9之可交聯發光組合物,其中該磷光發光摻雜 劑係該主體材料聚合物主鏈、該主體材料聚合物側基或該主體材料聚合物端基中之重複單元。
- 如請求項1至3中任一項之可交聯發光組合物,其中該第二交聯劑能夠形成二烯,該二烯能夠與該第一交聯劑之該不飽和碳-碳鍵基團反應。
- 一種調配物,其包含如請求項1至11中任一項之可交聯發光組合物及至少一種溶劑。
- 一種形成有機發光裝置之方法,其包含以下步驟:藉由將如請求項1至11中任一項之可交聯發光組合物沈積於用於注入第一類型之電荷載子的第一電極上並使該等可交聯基團交聯來形成第一有機發光層;及在該第一有機發光層上形成用於注入第二類型之電荷載子的第二電極。
- 如請求項13之方法,其中該可交聯發光組合物係如請求項12之調配物。
- 如請求項13或14之方法,其中將有機層自存於溶劑中之溶液沈積至該第一有機發光層上。
- 如請求項15之方法,其中該有機層係選自第二發光層、電荷傳輸層、電荷阻擋層及激子阻擋層。
- 一種有機發光裝置,其包含自如請求項1至11中任一項之可交聯發光組合物形成的交聯發光層。
- 如請求項17之有機發光裝置,其係白色有機發光裝置。
- 如請求項18之有機發光裝置,其除該交聯發光層外亦包含至少又一發光層。
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GB2505834A (en) | 2014-03-12 |
US10270037B2 (en) | 2019-04-23 |
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TW201305315A (zh) | 2013-02-01 |
TW201307426A (zh) | 2013-02-16 |
GB201322587D0 (en) | 2014-02-05 |
TW201312820A (zh) | 2013-03-16 |
WO2013005026A2 (en) | 2013-01-10 |
JP2014518311A (ja) | 2014-07-28 |
US9562136B2 (en) | 2017-02-07 |
KR101986859B1 (ko) | 2019-06-07 |
CN103748132A (zh) | 2014-04-23 |
US20140235800A1 (en) | 2014-08-21 |
US20140217379A1 (en) | 2014-08-07 |
WO2013005026A3 (en) | 2013-04-18 |
TWI625344B (zh) | 2018-06-01 |
KR20140061361A (ko) | 2014-05-21 |
WO2013005029A1 (en) | 2013-01-10 |
US20170098770A1 (en) | 2017-04-06 |
US9493613B2 (en) | 2016-11-15 |
WO2013005031A1 (en) | 2013-01-10 |
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