JP6507161B2 - ポリマーおよび有機電子デバイス - Google Patents
ポリマーおよび有機電子デバイス Download PDFInfo
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- JP6507161B2 JP6507161B2 JP2016530603A JP2016530603A JP6507161B2 JP 6507161 B2 JP6507161 B2 JP 6507161B2 JP 2016530603 A JP2016530603 A JP 2016530603A JP 2016530603 A JP2016530603 A JP 2016530603A JP 6507161 B2 JP6507161 B2 JP 6507161B2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
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- 238000009472 formulation Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
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- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000012966 insertion method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000008096 xylene Substances 0.000 description 1
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Description
R1は、各存在において、独立にHまたは置換基であり;
R2は、各存在において、独立に置換基であり;
Ar1は、各存在において、独立に、非置換であってもよくもしくは1つ以上の置換基で置換されてもよいアリールまたはヘテロアリール基であり;
R3は、各存在において、独立に置換基であり;
各nは、独立に0、1、2または3であるが、ただし少なくとも1つのnは1であり;および
各mは独立に0または1である。
(i)アノードおよびカソードのうちの一方の上に、第4の態様に従う配合物を堆積させる工程;
(ii)少なくとも1つの溶媒を蒸発させて、第1の態様に従うポリマーを含む有機半導体層を形成する工程;および
(iii)有機半導体層の上に、アノードおよびカソードのうちの他方を形成する工程
を含む。
アノード/正孔注入層/発光層/カソード
アノード/正孔輸送層/発光層/カソード
アノード/正孔注入層/正孔輸送層/発光層/カソード
アノード/正孔注入層/正孔輸送層/発光層/電子輸送層/カソード。
C1−30アルキル(ここで1つ以上の非隣接C原子が、O、S、NR4(ここでR4は置換基である)、C=Oおよび−COO−で置き換えられてもよく、ここでC1−20アルキルの1つ以上のH原子は、Fで置き換えられてもよい);および
1つ以上の置換基で置換されてもよくまたは非置換であってもよいアリールまたはヘテロアリール
からなる群から選択されてもよい。R4は、C1−20ヒドロカルビル基、例えばC1−20アルキル、フェニル、または1つ以上のアルキル基で置換されるフェニルであってもよい。
C1−20アルキル(ここで1つ以上の非隣接C原子はO、S、NR4、C=Oおよび−COO−で置き換えられてもよく、式中、R4は上記で記載される通りであり、ここでC1−20アルキルの1つ以上のH原子はFで置き換えられてもよい);および
1つ以上の置換基で置換されてもよくもしくは非置換であってもよいアリールまたはヘテロアリール
からなる群から選択されてもよい。
−アルキル(任意にはC1−20アルキル)(ここで1つ以上の非隣接C原子は、置換されてもよいアリールまたはヘテロアリール、O、S、置換N、C=Oまたは−COO−で置き換えられてもよく、1つ以上のH原子がFで置き換えられてもよい);
−アリールおよびヘテロアリール基(非置換または1つ以上の置換基で置換されてもよい)、好ましくは1つ以上のC1−20アルキル基で置換されたフェニル;
−線状または分岐状鎖のアリールまたはヘテロアリール基(これらの基のそれぞれは、独立に置換されてもよい)、例えば式−(Ar3)rの基(式中、各Ar3は、独立にアリールまたはヘテロアリール基であり、rは少なくとも2である)、好ましくは分岐状または線状鎖のフェニル基(それぞれ非置換であってもよくまたは1つ以上のC1−20アルキル基で置換されてもよい);および
−架橋性基、例えば二重結合を含む基、例えばビニルまたはアクリレート基、またはベンゾシクロブタン基からなる群から選択されてもよい。
アルキル、例えばC1−20アルキル(ここで1つ以上の非隣接C原子は、O、S、置換N、C=Oおよび−COO−で置き換えられてもよく、アルキル基の1つ以上のH原子は、Fで置き換えられてもよい);
NR9 2、OR9、SR9、SiR9 3およびフッ素、ニトロおよびシアノ(ここで各R9は、独立に、アルキル、好ましくはC1−20アルキルから選択される);および
アリールまたはヘテロアリール、好ましくはフェニル(1つ以上のC1−20アルキル基で置換されてもよい)。
−置換または非置換アルキル(任意にはC1−20アルキル)、ここで1つ以上の非隣接C原子は、置換されてもよいアリールまたはヘテロアリール、O、S、置換N、C=Oまたは−COO−で置き換えられてもよく、1つ以上のH原子はFで置き換えられてもよい;および
−フルオレン単位に直接結合したまたはスペーサー基によって間隔をあけた架橋性基、例えば二重結合を含む基、例えばビニルまたはアクリレート基またはベンゾシクロブタン基
からなる群から選択されてもよい。
本明細書に記載されるようなポリマーの調製のための好ましい方法は、「金属挿入」を含み、ここで金属錯体触媒の金属原子は、アリールまたはヘテロアリール基とモノマー(Im)の脱離基との間に挿入される。例示的な金属挿入方法は、例えば国際公開第00/53656号に記載されるようなSuzuki重合および例えばT.Yamamoto,「Electrically Conducting And Thermally Stable π−Conjugated Poly(arylene)s Prepared by Organometallic Processes」,Progress in Polymer Science 1993,17,1153−1205に記載されるYamamoto重合である。Yamamoto重合の場合、ニッケル錯体触媒が使用される;Suzuki重合の場合に、パラジウム錯体触媒が使用される。
OLEDの発光層は、パターニングされていなくてもよく、またはパターニングされて区別可能なピクセルを形成してもよい。各ピクセルはさらに、サブピクセルに分割されてもよい。発光層は、単一発光材料、例えばモノクロディスプレイまたは他のモノクロデバイスのための単一発光材料を含有してもよく、またはフルカラーディスプレイのための異なる色を発光する材料、特に赤、緑および青色発光材料を含有してもよい。
式中、Mは金属であり;L1、L2およびL3のそれぞれは配位基であり;qは整数であり;rおよびsはそれぞれ独立に、0または整数であり;(a.q)+(b.r)+(c.s)の合計は、Mにて利用可能な配位部位の数に等しく、ここでaは、L1の配位部位の数であり、bはL2の配位部位の数であり、cはL3の配位部位の数である。
正孔輸送層は、OLEDのアノードと(1または複数の)発光層との間に提供されてもよい。同様に、電子輸送層は、カソードと(1または複数の)発光層との間に提供されてもよい。
−式(I)(ここで各mは0である)の1つ以上の繰り返し単位および式(IX)の1つ以上のアミン共繰り返し単位を含むコポリマー;および
−式(I)(ここで各mは1である)の1つ以上の繰り返し単位を含むホモポリマーまたはコポリマーが挙げられる。
伝導性有機または無機材料から形成され得る伝導性正孔注入層は、図1に示されるようなOLEDのアノード101と発光層103との間に提供されて、アノードから半導体ポリマーの(1または複数の)層への正孔注入を補助してもよい。ドープされた有機正孔注入材料の例としては、置換されてもよいドープされたポリ(エチレンジオキシチオフェン)(PEDT)、特に欧州特許第0901176号明細書および欧州特許第0947123号明細書に開示されるような、電荷平衡ポリ酸、例えばポリスチレンスルホネート(PSS)でドープされたPEDT、ポリアクリル酸またはフッ素化スルホン酸、例えばNafion(登録商標);米国特許第5723873号明細書および米国特許第5798170明細書に開示されるようなポリアニリン;および置換されてもよいポリチオフェンまたはポリ(チエノチオフェン)が挙げられる。伝導性無機材料の例としては、遷移金属酸化物、例えばJournal of Physics D:Applied Physics(1996),29(11),2750−2753に開示されるような、VOx、MoOxおよびRuOxが挙げられる。
カソード105は、OLEDの発光層に電子注入を可能にする仕事関数を有する材料から選択される。カソードと発光材料との間の不利な相互作用の可能性といった他の要因がカソードの選択に影響を及ぼす。カソードは、アルミニウムの層のような単一材料からなってもよい。あるいは、それは、複数の伝導性材料を含んでいてもよく、例えば国際公開第98/10621号に開示されるように、カルシウムおよびアルミニウムのような低仕事関数材料および高仕事関数材料の二層を含んでいてもよい。カソードは、例えば国際公開第98/57381号、Appl.Phys.Lett.2002,81(4),634および国際公開第02/84759号に開示されるように、元素状バリウムを含んでいてもよい。カソードは、金属化合物、特にアルカリ金属またはアルカリ土類金属の酸化物またはフッ化物の薄い(例えば1〜5nm)層を、デバイスの有機層と、1つ以上の伝導性カソード層との間に含んで電子注入を補助してもよく、例えば国際公開第00/48258号に開示されるようにフッ化リチウム;Appl.Phys.Lett.2001,79(5),2001に開示されるようなフッ化バリウム;および酸化バリウムである。電子の効率の良いデバイスへの注入を提供するために、カソードは、好ましくは3.5eV未満、より好ましくは3.2eV未満、最も好ましくは3eV未満の仕事関数を有する。金属の仕事関数は、例えばMichaelson,J.Appl.Phys.48(11),4729,1977に見出され得る。
有機オプトエレクトロニクスデバイスは、湿分および酸素に対して感受性である傾向がある。従って、基材は、好ましくはデバイスへの湿分および酸素の進入を防止するための良好なバリア特性を有する。基材は、一般にガラスであるが、代替基材が、特にデバイスの可撓性が所望される場合に、使用されてもよい。例えば、基材は、1つ以上のプラスチック層、例えば交互のプラスチックおよび誘電体バリア層または薄いガラスおよびプラスチックのラミネートを含んでいてもよい。
電荷輸送または発光層を形成するのに好適な配合物は、溶媒または溶媒混合物中に溶解した式(I)の繰り返し単位を含む組成物またはポリマーから形成されてもよい。組成物は、式(I)の繰り返し単位を含むポリマーおよび(1または複数の)溶媒からなってもよく、またはそれは、さらなる構成成分、例えば発光ドーパントを含有してもよい。
国際公開第00/53656号に記載される方法に従って、表1に示す量で以下のモノマーのSuzuki重合によってポリマーを調製した。ポリマーの分子量を、ボロン酸エステル:ハロゲンモノマーの不均衡(非50:50比)を用いることによって制御した。
ポリマー実施例1、比較ポリマー1Aおよび比較ポリマー1Bの1重量%溶液を、ポリマーを、体積で80%のシクロヘキシルベンゼンおよび20%の4−メチルアニソールの溶媒混合物中に溶解させることによって調製した。得られた溶液の粘度を表2に示す。
以下の構造を有する青色有機発光デバイスを調製した:
ITO/HIL/HTL/LE/カソード
ここでITOはインジウムスズオキシドアノードであり;HILは正孔注入層であり;HTLは正孔輸送層であり;LEは発光層であり;カソードは、発光層と接触したフッ化ナトリウムの層および銀層およびアルミニウム層を含む。
デバイスは、ポリマー実施例2を比較ポリマー1Bと置き換えた以外は、デバイス実施例1に関して記載される通りに調製した。図3〜5に示されるように、デバイス実施例1および比較デバイス1のデバイス性能は同様である。
Claims (17)
- 式(III):
(式中:
R1は、各存在において、独立に、C 1−30 アルキル(ここで、1つ以上の非隣接C原子が、O、S、NR 4 (ここで、R 4 はC 1−20 ヒドロカルビル基である)、C=Oおよび−COO−で置き換えられてもよく、ここで、C 1−30 アルキルの1つ以上のH原子は、Fで置き換えられてもよい);および1つ以上の置換基で置換されてもよくまたは非置換であってもよいアリールまたはヘテロアリールからなる群から選択され;
R2は、各存在において、独立に、C 1−20 アルキル(ここで、1つ以上の非隣接C原子が、O、S、NR 4 (ここで、R 4 は置換基である)、C=Oおよび−COO−で置き換えられてもよく、ここで、C 1−20 アルキルの1つ以上のH原子は、Fで置き換えられてもよい)からなる群から選択され;
Ar1は、各存在において、独立に、非置換であってもよくまたは1つ以上の置換基で置換されてもよいアリールまたはヘテロアリール基であり;
R3は、各存在において、独立に置換基であり;
nは、0、1、2または3であり;
各mは、独立に0または1である)
の繰り返し単位を含むポリマー。 - 各R2が独立にC1−10アルキル基である、請求項1に記載のポリマー。
- nが0である、請求項1または2に記載のポリマー。
- 各mが0である、請求項1から3のいずれか一項に記載のポリマー。
- 少なくとも1つのmが1である、請求項1から3のいずれか一項に記載のポリマー。
- Ar1が、各存在において、独立に、非置換であってもよくまたは1つ以上の置換基で置換されてもよいフェニル基である、請求項5に記載のポリマー。
- R3が、各存在において、独立にC1−40ヒドロカルビル基である、請求項5または6に記載のポリマー。
- 前記ポリマーが、1〜50mol%の前記式(III)の繰り返し単位を含む、請求項1から7のいずれか一項に記載のポリマー。
- 各LGが、独立に、ボロン酸、ボロン酸エステル、ハロゲンおよびスルホン酸エステルから選択される、請求項9に記載のモノマー。
- 請求項9または10に記載のモノマーを重合する工程を含む、請求項1から8のいずれか一項に記載のポリマーを形成する方法。
- 前記重合が、金属触媒の存在下で行われる、請求項11に記載の方法。
- 請求項1から8のいずれか一項に記載のポリマーおよび1つ以上の溶媒を含む配合物。
- 請求項1から8のいずれか一項に記載のポリマーを含む層を含む有機電子デバイス。
- 前記デバイスが、アノード、カソードおよび前記アノードとカソードとの間に有機発光層を含む少なくとも1つの有機半導体層を含む有機発光デバイスであり、ここで前記少なくとも1つの有機半導体層は、請求項1から8のいずれか一項に記載のポリマーを含む、請求項14に記載の有機電子デバイス。
- 請求項15に記載の有機発光デバイスを形成する方法であって、前記方法は、
(iv)アノードおよびカソードのうちの一方の上に、請求項13に記載の配合物を堆積させる工程;
(v)前記少なくとも1つの溶媒を蒸発させて、請求項1から8のいずれか一項に記載のポリマーを含む前記有機半導体層を形成する工程;および
(vi)前記有機半導体層の上に、前記アノードおよびカソードのうちの他方を形成する工程を含む、方法。 - 前記配合物がインクジェット印刷によって堆積される、請求項16に記載の方法。
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