JP2020508572A - 電子デバイス、当該電子デバイスを製造するための方法、ならびに当該電子デバイスを含むディスプレイデバイス - Google Patents
電子デバイス、当該電子デバイスを製造するための方法、ならびに当該電子デバイスを含むディスプレイデバイス Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 71
- 238000002347 injection Methods 0.000 claims description 44
- 239000007924 injection Substances 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000758 substrate Substances 0.000 claims description 32
- 238000000151 deposition Methods 0.000 claims description 23
- -1 boron halide Chemical class 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- 229910052796 boron Inorganic materials 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 229910052693 Europium Inorganic materials 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052712 strontium Inorganic materials 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 229910052772 Samarium Inorganic materials 0.000 claims description 3
- 229910052771 Terbium Inorganic materials 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims description 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 2
- 229910052779 Neodymium Inorganic materials 0.000 claims description 2
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 2
- 229910052776 Thorium Inorganic materials 0.000 claims description 2
- 229910052775 Thulium Inorganic materials 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
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- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052745 lead Inorganic materials 0.000 claims description 2
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- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
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- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 229910052689 Holmium Inorganic materials 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004327 boric acid Substances 0.000 abstract description 2
- 230000032258 transport Effects 0.000 description 43
- 230000000903 blocking effect Effects 0.000 description 34
- 230000005525 hole transport Effects 0.000 description 29
- 239000002019 doping agent Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000306 component Substances 0.000 description 18
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- 239000011159 matrix material Substances 0.000 description 17
- 230000008021 deposition Effects 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000011777 magnesium Substances 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 238000001771 vacuum deposition Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000013086 organic photovoltaic Methods 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 7
- 239000011575 calcium Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
- 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 4
- 239000012448 Lithium borohydride Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007764 slot die coating Methods 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 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 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 2
- NNMZRNJTHCMELD-UHFFFAOYSA-N 4,5,6,7-tetrafluoro-3-(trifluoromethyl)-2h-indazole Chemical compound FC1=C(F)C(F)=C2C(C(F)(F)F)=NNC2=C1F NNMZRNJTHCMELD-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
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- 125000000732 arylene group Chemical group 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
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- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 125000000962 organic group Chemical group 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
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- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
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- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)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 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
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- UUZLADCDKJUECN-UHFFFAOYSA-N 4-(cyanomethyl)-2,3,5,6-tetrafluorobenzonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1CC#N UUZLADCDKJUECN-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
(i)H、
(ii)F、
(iii)CN、
(iv)C6〜C60アリール、
(v)C7〜C60アリールアルキル、
(vi)C1〜C60アルキル、
(vii)C2〜C60アルケニル、
(viii)C2〜C60アルキニル、
(ix)C3〜C60シクロアルキル、および
(x)C2〜C60ヘテロアリールから選択され;
式(I)中、(iv)、(v)、(vi)、(vii)、(viii)、(ix)および(x)の基は、式(I)中に存在する場合、F、Cl、Br、I、CN、非置換またはハロゲン化アルキル、非置換またはハロゲン化(ヘテロ)アリール、非置換またはハロゲン化(ヘテロ)アリールアルキル、非置換またはハロゲン化アルキルスルホニル、非置換またはハロゲン化(ヘテロ)アリールスルホニル、非置換またはハロゲン化(ヘテロ)アリールアルキルスルホニル、非置換またはハロゲン化ホウ素含有ヒドロカルビル、非置換またはハロゲン化ケイ素含有ヒドロカルビルからなる群の少なくとも1つの置換基で置換され、(iv)、(v)、(vi)、(vii)、(viii)、(ix)および(x)の前記基の各々における炭素原子の全体数は、それぞれ60を超えない。これにより、特に動作電圧および/またはその効率に関して、電子デバイスの特性をさらに改善することが可能である。
(i)ホウ酸塩を高温、かつ任意選択で、減圧下で、蒸発させる工程、および
(ii)蒸発したホウ酸塩を基板上に堆積させる工程
を含む。
本発明によれば、電子デバイスは、既に上述した層の他に、さらなる層を含んでもよい。それぞれの層の例示的な実施形態を以下に説明する。
基板は、有機発光ダイオードなどの電子デバイスの製造に一般的に使用される任意の基板であってよい。光が基板を通して放出される場合、基板は、透明または半透明材料、例えばガラス基板または透明プラスチック基板でなければならない。光が上面を通して放出される場合、基板は透明材料、不透明材料のどちらでもよく、例えば、ガラス基板、プラスチック基板、金属基板またはシリコン基板であってよい。
第1の電極または第2の電極のいずれかは、陽電極であってもよい。陽電極は、陽電極を形成するために使用される材料を堆積またはスパッタリングすることによって形成されてもよい。陽電極を形成するために使用される材料は、正孔注入を促進するために、高仕事関数を有する材料であってもよい。陽極の材料はまた、低仕事関数を有する材料から選択されてもよい(すなわち、アルミニウム)。陽電極は、透明電極または反射電極であってもよい。陽電極を形成するために、酸化インジウムスズ(ITO)、酸化インジウム亜鉛(IZO)、二酸化スズ(SnO2)、酸化アルミニウム亜鉛(AlZO)および酸化亜鉛(ZnO)などの透明導電性酸化物を使用してもよい。陽電極はまた、金属、典型的には銀(Ag)、金(Au)、または金属合金を使用して形成されてもよい。
本発明によれば、上述で詳細に説明したように、正孔注入層は、ホウ酸塩を主な成分として含んでもよく、またはホウ酸塩から構成されてもよい。正孔注入層(HIL)は、真空蒸着、スピンコーティング、プリンティング、キャスティング、スロットダイコーティング、ラングミュア・ブロジェット(LB)蒸着などによって陽電極上に形成することができる。真空蒸着を使用してHILを形成する場合、蒸着条件は、HILを形成するために使用される化合物、ならびにHILの所望の構造および熱特性に応じて変化し得る。しかし、一般的に、蒸着条件には、蒸着温度100℃〜500℃、圧力10−8〜10−3トル(1トル=133.322Pa)、蒸着速度0.1〜10nm/秒が含まれてもよい。
本発明によれば、上述で詳細に説明したように、正孔輸送層は、主な成分としてホウ酸塩を含んでいてもよく、またはホウ酸塩からなっていてもよい。
電子阻止層(EBL)の機能は、電子が発光層から正孔輸送層に移動することを防ぎ、それによって電子を発光層に閉じ込めることである。これにより、効率、動作電圧および/または寿命が改善される。典型的には、電子阻止層は、トリアリールアミン化合物を含む。トリアリールアミン化合物は、正孔輸送層のLUMO準位よりも真空準位に近いLUMO準位を有し得る。電子阻止層は、正孔輸送層のHOMO準位と比較して、真空準位からさらに離れたHOMO準位を有し得る。電子阻止層の厚さは、2〜20nmの間で選択され得る。
Ar1〜Ar3は、互いに同じかまたは異なり、それぞれ独立して、水素、6〜30個の炭素原子を有する置換もしくは非置換のアリール基、および5〜30個の炭素原子を有する置換もしくは非置換のヘテロアリール基から選択され、
Ar4は、置換もしくは非置換のフェニル基、置換もしくは非置換のビフェニル基、置換もしくは非置換のテルフェニル基、置換もしくは非置換のトリフェニレン基、および5〜30個の炭素原子を有する置換もしくは非置換のヘテロアリール基からなる群から選択され、
Lは、6〜30個の炭素原子を有する置換もしくは非置換のアリール基である。
EMLは、真空蒸着、スピンコーティング、スロットダイコーティング、プリンティング、キャスティング、LB蒸着などによってHTL上に形成することができる。EMLが真空蒸着またはスピンコーティングを用いて形成される場合、蒸着およびコーティングのための条件は、HILの形成のための条件と同様であり得る。しかし、蒸着およびコーティングの状態は、EMLを形成するために使用される化合物に応じて変化し得る。
正孔阻止層(HBL)は、ETLへの正孔の拡散を防止するために、真空蒸着、スピンコーティング、スロットダイコーティング、プリンティング、キャスティング、LB蒸着などを用いることによって、EML上に形成することができる。EMLが燐光性ドーパントを含む場合、HBLは三重項励起子阻止機能も有することができる。
本発明に係るOLEDは、電子輸送層(ETL)を含んでいてもよい。
陰極からの電子の注入を促進できる任意のEILは、ETL上に、好ましくは電子輸送層上に直接形成することができる。EILを形成するための材料の例には、当該技術分野で知られているリチウム8−ヒドロキシキノリノレート(LiQ)、LiF、NaCl、CsF、Li2O、BaO、Ca、Ba、Yb、Mgが含まれる。EILを形成するための蒸着およびコーティング条件は、HILの形成のための条件と同様である。しかし、EILを形成するために使用される材料に応じて、蒸着およびコーティング状態は変化し得る。
陰電極は、EILが存在する場合、EIL上に形成される。陰電極は、金属、合金、導電性化合物、またはそれらの混合物から形成されてもよい。陰電極は、低い仕事関数を有し得る。例えば、陰電極は、リチウム(Li)、マグネシウム(Mg)、アルミニウム(Al)、アルミニウム(Al)−リチウム(Li)、カルシウム(Ca)、バリウム(Ba)、イッテルビウム(Yb)、マグネシウム(Mg)−インジウム(In)、マグネシウム(Mg)−銀(Ag)などから形成されてもよい。あるいは、陰電極は、ITOまたはIZOなどの透明導電性酸化物から形成されてもよい。
電荷発生層(CGL)は、二重層で構成されてもよい。電荷発生層、特にp型電荷発生層(正孔発生層)は、主な成分としてホウ酸塩を含んでいてもよく、またはホウ酸塩からなっていてもよい。
本発明の一態様によれば、基板;基板上に形成された陽電極;正孔注入層、正孔輸送層、発光層、および陰電極を含む有機発光ダイオード(OLED)が提供される。
[工程1:4,5,6,7−テトラフルオロ−3−(トリフルオロメチル)−1H−インダゾール]
GCMS:予想されるM/z(質量/電荷)比258を確認した。
[工程1:4,5,6,7−テトラフルオロ−3−(パーフルオロフェニル)−1H−インダゾール]
GC−MS:予想されるM/z(質量/電荷)比356を確認した。
実施例1(タンデムOLED、ボトムエミッション型白色OLEDピクセルのモデル)
厚さ90nmのITO陽極を備えたガラス基板上に、8重量%のPD−2でドープされたF1から作製される10nmの正孔注入層と、純粋なF1からなる厚さ140nmの非ドープ正孔輸送層と、3重量%のBD200でドープされたABH113(両方とも韓国、SFC社によって提供される)から形成される厚さ20nmの第1の発光層と、純粋なF2から作製される厚さ25nmの第1の電子輸送層と、5重量%のYbでドープされたF3から作製される厚さ10nmの電荷発生層の電子発生部(n−CGL)と、F4から作製される厚さ2nmの中間層と、PB−1から作製される厚さ30nmの電荷発生層の正孔発生部(p−CGL)と、純粋なF1から作製される厚さ10nmの第2の正孔輸送層と、第1の発光層と同じ厚さおよび組成の20nmの第2の発光層と、純粋なF2から作製される厚さ25nmの第1の電子輸送層と、5重量%のYbでドープされたF3から作製される厚さ10nmの電子注入層(EIL)と、100nmのAl陰極と、を順に堆積させた。
次に、装置例1と同じITO陽極を備えたガラス基板上に、以下の層をVTEによって順に堆積させた:化合物PB−1から作製される10nmの正孔注入層;純粋なF1から作製される厚さ120nmのHTL;3重量%のNUBD370でドープされたABH113(両方とも韓国、SFC社によって供給される)から作製される20nmのEML;50重量%のLiQでドープされたF2から作製される36nmのEIL/ETL;100nmのAl陰極。
CV サイクリックボルタンメトリー
DSC 示差走査熱量測定
EBL 電子阻止層
EIL 電子注入層
EML 発光層
eq. 当量
ETL 電子輸送層
ETM 電子輸送マトリックス
Fc フェロセン
Fc+ フェリセニウム
HBL 正孔阻止層
HIL 正孔注入層
HOMO 最高被占軌道
HPLC 高速液体クロマトグラフィー
HTL 正孔輸送層
p−HTL p−ドープされた正孔輸送層
HTM 正孔輸送マトリックス
ITO インジウムスズ酸化物
LUMO 最低空軌道
mol% モルパーセント
NMR 核磁気共鳴
OLED 有機発光ダイオード
OPV 有機光起電力
QE 量子効率
Rf TLC遅延因子
RGB 赤−緑−青
TCO 透明導電性酸化物
TFT 薄膜トランジスタ
Tg ガラス遷移温度
TLC 薄層クロマトグラフィー
wt% 重量パーセント
Claims (15)
- ホウ酸塩を含む少なくとも1つの層を含む電子デバイスであって、前記ホウ酸塩が、前記ホウ酸塩を含む前記層において、前記層中に追加で含まれ得る他の成分の総量を超える重量および/または体積量で含まれる電子デバイス。
- 前記ホウ酸塩が、前記ホウ酸塩を含む前記層中において、前記層中に追加で含まれ得る他の成分の総量を超える重量および体積量で含まれる、請求項1に記載の電子デバイス。
- 前記電子デバイスが、第1の電極および第2の電極をさらに含み、前記ホウ酸塩を含む前記層が、前記第1の電極と前記第2の電極との間に配置される、請求項1または2に記載の電子デバイス。
- 前記ホウ酸塩を含む前記層が、電荷注入層、電荷発生層、または電荷輸送層である、請求項3に記載の電子デバイス。
- 前記電荷注入層が、正孔注入層であり、および/または、前記電荷発生層が正孔発生層である、請求項4に記載の電子デバイス。
- 前記ホウ酸塩がホウ酸金属塩である、請求項1〜5のいずれか1項に記載の電子デバイス。
- 前記ホウ酸金属塩が、少なくとも1つの金属カチオンおよび少なくとも1つのアニオン性リガンドからなり、前記アニオン性リガンドが、少なくとも6個の共有結合原子からなり、前記共有結合原子のうちの少なくとも1つが、ホウ素原子である、請求項6に記載の電子デバイス。
- 前記アニオン性リガンドが、少なくとも7個、あるいは少なくとも8個、あるいは少なくとも9個、あるいは少なくとも10個、あるいは少なくとも11個、あるいは少なくとも12個の共有結合原子からなる、請求項7に記載の電子デバイス。
- 前記金属が、Li、Na、K、Rb、Cs、Be、Mg、Ca、Sr、Ba、Al、Ga、In、Tl、Sn、Pb、Bi、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Y、Zr、Nb、Mo、Ru、Rh、Pd、Ag、Cd、La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Ho、Er、Tm、Yb、Lu、Hf、Ta、W、Re、Os、Ir、Pt、Au、Hg、Th、Uおよびこれらの混合物からなる群から選択される、請求項6〜8のいずれか1項に記載の電子機器。
- 前記ホウ酸塩が、以下の式(I)を有するアニオンを含む、請求項1〜9のいずれか1項に記載の電子デバイス:
(i)H、
(ii)F、
(iii)CN、
(iv)C6〜C60アリール、
(v)C7〜C60アリールアルキル、
(vi)C1〜C60アルキル、
(vii)C2〜C60アルケニル、
(viii)C2〜C60アルキニル、
(ix)C3〜C60シクロアルキル、および
(x)C2〜C60ヘテロアリールから選択され;
式(I)中、(iv)、(v)、(vi)、(vii)、(viii)、(ix)および(x)の基は、式(I)中に存在する場合、F、Cl、Br、I、CN、非置換またはハロゲン化アルキル、非置換またはハロゲン化(ヘテロ)アリール、非置換またはハロゲン化(ヘテロ)アリールアルキル、非置換またはハロゲン化アルキルスルホニル、非置換またはハロゲン化(ヘテロ)アリールスルホニル、非置換またはハロゲン化(ヘテロ)アリールアルキルスルホニル、非置換またはハロゲン化ホウ素含有ヒドロカルビル、非置換またはハロゲン化ケイ素含有ヒドロカルビルからなる群の少なくとも1つの置換基で置換され、(iv)、(v)、(vi)、(vii)、(viii)、(ix)および(x)の前記基の各々における炭素原子の全体数は、それぞれ60を超えない。 - A1〜A4のうちの少なくとも1つが、F、CN、ヒドロカルビル、ホウ素含有ヒドロカルビル、ケイ素含有ヒドロカルビルおよびヘテロアリールからなる群から選択され、前記ヒドロカルビル、前記ホウ素含有ヒドロカルビル、前記ケイ素含有ヒドロカルビルおよび前記ヘテロアリールのそれぞれにおいて、含まれる水素原子の50%以上が、F、Cl、Br、IおよびCNからなる群の1つによって置き換えられている、請求項10に記載の電子デバイス。
- 前記ホウ酸塩を含む前記層が、前記ホウ酸塩を含む前記層の総重量に対して、少なくとも60重量%、あるいは少なくとも75重量%、あるいは少なくとも90重量%、あるいは少なくとも95重量%、あるいは少なくとも98重量%、あるいは少なくとも99重量%、あるいは少なくとも99.5重量%、あるいは少なくとも99.9重量%の量で前記ホウ酸塩を含む、請求項1〜11のいずれか1項に記載の電子デバイス。
- 前記電子デバイスが、エレクトロルミネセンスデバイスであり、好ましくは有機発光ダイオードである、請求項1〜12のいずれか1項に記載の電子デバイス。
- 請求項13に記載の前記電子デバイスを含むディスプレイデバイス。
- 請求項1〜13のいずれか1項に記載の電子デバイスを製造するための方法であって、前記方法は、
(i)ホウ酸塩を高温、かつ任意選択で、減圧下で、蒸発させる工程、および
(ii)蒸発したホウ酸塩を基板上に堆積させる工程
を含む、方法。
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