JP5247696B2 - 光電気デバイスの製造方法 - Google Patents
光電気デバイスの製造方法 Download PDFInfo
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- JP5247696B2 JP5247696B2 JP2009522329A JP2009522329A JP5247696B2 JP 5247696 B2 JP5247696 B2 JP 5247696B2 JP 2009522329 A JP2009522329 A JP 2009522329A JP 2009522329 A JP2009522329 A JP 2009522329A JP 5247696 B2 JP5247696 B2 JP 5247696B2
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- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/122—Pixel-defining structures or layers, e.g. banks
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/17—Passive-matrix OLED displays
- H10K59/173—Passive-matrix OLED displays comprising banks or shadow masks
-
- 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
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Electroluminescent Light Sources (AREA)
Description
式中、R1及びR2は、水素又は置換されていてもよいアルキル、アルコキシ、アリール、アリールアルキル、ヘテロアリール及びヘテロアリールアルキルから独立して選択される。より好ましくは、R1及びR2のうちの少なくとも1つは、置換されていてもよいC4−C20アルキル又はアリール基を含む。
− 第1の繰り返し単位のホモポリマー、例えば、9,9−ジアルキルフルオレン−2,7−ジイルのホモポリマーは、電子輸送をもたらすために利用してもよく;
− 第1の繰り返し単位及びトリアリールアミン繰り返し単位を含むコポリマーは、ホール輸送及び/又は発光をもたらすために利用され;又は
− 第1の繰り返し単位及びヘテロアリーレン繰り返し単位を含むコポリマーは、電荷輸送又は発光のために利用してもよい。
式中、X、Y、A、B、C及びDは、H又は置換基から独立して選択される。より好ましくは、X、Y、A、B、C及びDのうちの1つ又はそれ以上は、置換されていてもよい、分枝鎖状又は直鎖状のアルキル、アリール、パーフルオロアルキル、チオアルキル、シアノ、アルコキシ、ヘテロアリール、アルキルアリール及びアリールアルキル基からなる群より独立して選択される。最も好ましくは、X、Y、A及びBは、C1−10アルキルである。ポリマー骨格中の芳香環は、直接的結合又は架橋基又は架橋性原子によって、特に架橋性ヘテロ原子、例えば酸素によって連結されていてもよい。
式中、Hetはヘテロアリール基を表す。
式中、Ar1、Ar2、Ar3、Ar4及びAr5は、互いに独立して、アリール又はヘテロアリール環又はその縮合誘導体を表し;Xは選択的なスペーサー基を表す。
式中、R6及びR7は、同じであるか又は異なり、互いに独立して、水素又は置換基、好ましくは、アルキル、アリール、パーフルオロアルキル、チオアルキル、シアノ、アルコキシ、ヘテロアリール、アルキルアリール又はアリールアルキルである。製造の簡便性のためには、R6及びR7は、好ましくは同じである。より好ましくは、それらが同じであって、それぞれがフェニル基である。
式中、Mは金属であり;L1、L2及びL3のそれぞれは配位基であり;qは整数であり;r及びsは、互いに独立して、0又は整数であり;(a.q)+(b.r)+(c.s)の合計は、Mにおいて利用可能な配位部位の数であって、この場合、aはL1における配位部位の数であり、bはL2における配位部位の数であり、cはL3における配位部位の数である。
− セリウム、サマリウム、ユーロピウム、テルビウム、ジスプロシウム、ツリウム、エルビウム及びネオジム等のランタニド金属;及び
− d−ブロック金属、特に第2列及び第3列のもの、すなわち、元素39〜48及び72〜80、特にルテニウム、ロジウム、パラジウム、レニウム、オスミウム、イリジウム、白金及び金を含む。
式中、Ar4及びAr5は、同じであっても、異なっていてもよく、置換されていてもよいアリール又はヘテロアリールから独立して選択され;X1及びY1は、同じであっても、異なっていてもよく、炭素又は窒素から独立して選択され;Ar4及びAr5は縮合してもよい。X1が炭素であり、Y1が窒素である配位子が特に好ましい。
本発明の方法で用いられる組成物は、塩基性添加物を、導電性又は半導電性有機素材と共に単純にブレンドすることにより、調製することができる。
本手順は以下に示す工程にしたがう:
1)本発明の第1の態様に係るPEDT/PSS組成物を、ガラス基材(Applied Films,Colorado,USAから入手可能)に担持された酸化インジウムスズ上に、スピンコーティングにより堆積する工程。
2)ホール輸送ポリマー層を、2%w/vの濃度を有するキシレン溶液からスピンコーティングにより堆積する工程。
3)ホール輸送素材層を、不活性(窒素)環境中で加熱する工程。
4)選択的に、いくらかでも残存している可溶性のホール輸送素材を除去するために、キシレン中の基材をスピンリンスする工程。
5)キシレン溶液からスピンコーティングにより有機発光素材を堆積する工程。
6)有機発光素材上に金属化合物/導電性素材の2層陰極を堆積する工程、及びSaes Getters SpAから入手可能な気密金属エンクロージャを用いて、デバイスを密閉する工程。
フルカラーディスプレイは、標準的リソグラフ技法を用いて、赤、緑及び青のサブ画素のためのウェルを製造する工程;PEDT/PSSを、各サブ画素のウェル中にインクジェットプリントする工程;ホール輸送素材をインクジェットプリントする工程;及び、赤、緑及び青のサブ画素のためのウェル中に、赤、緑及び青のエレクトロルミネセント素材をそれぞれインクジェットプリントする工程による、EP0880303に記載される方法にしたがって製造することができる。
1.導電性
いくつかの異なるアミンを含むPEDOT:PSS組成物を製剤化し、その影響と抵抗性を試験した。導電性の測定は、交互嵌合された試験構造体上にPEDOT−PSSフィルムを10ミクロンの厚さ(DekTak装置を用いて測定した場合)に延ばし、PEDOTフィルムの底部全体にわたり横方向の抵抗性を記録するために、改良された4点プローブを使用することにより行った。バルクのPEDOTフィルムの抵抗性は同じであると考えられる。
図4は、PEDOT/PSSに添加されたエチレンジアミンの滴定曲線を示す。pHはpH2〜7付近で急激に増加する。本発明者らは、分散物の凝集体に固形物が存在するので、組成物はこのpH範囲で処理性がよくないことを見出した。しかしながら、分散物はこのpH範囲外であるpH8付近かそれ以上では処理性がよい。
エタノールアミンを含む上記組成物を、インクウェルを含む画素化された基体上にインクジェットプリントし、Zygo 白色干渉計を用いて、フィルム厚特性を基体の横列にわたり各画素で測定した。結果は、フィルムは横列にわたり、スウォース接合部においてさえ、同様の特性を有することが示された。
有機ELデバイスは前述した方法にしたがい作製した。デバイスは、PEDOT:PSS組成物中に塩基添加物を含むか又は含まずに作製した。
Claims (17)
- 酸性基を有する導電性又は半導電性有機素材、溶媒、及び第1の添加物を含む組成物を、第1の極性の電荷担体を注入するための第1の電極を含む基材上に、堆積させる工程;及び、第1の極性と反対の第2の極性の電荷担体を注入するための第2の電極を堆積させる工程を含み、前記第1の添加物が塩基性添加物であり、
前記塩基性添加物が、ヒドロキシル基を有する有機アミンであり、かつ、100℃よりも高い沸点を有し、
前記有機素材が、電荷平衡対イオンを有するPEDOTを含むホール注入素材を含む、
光電気デバイスの製造方法。 - 前記組成物が分散体である、請求項1に記載の方法。
- 前記組成物が溶液である、請求項1に記載の方法。
- 前記有機アミンが、トリエタノールアミン、ジエタノールアミン、エタノールアミン、4−アミノ−1−ブタノール、4−アミノ−2−ブタノール、6−アミノ−1−ヘキサノール、及び5−アミノ−1−ペンタノールからなる群より選択される、請求項1に記載の方法。
- 前記塩基性添加物が、容量あたり1〜40%の範囲の量で提供される、請求項1〜4のいずれか1項に記載の方法。
- 前記組成物が水性組成物である、請求項1〜5のいずれか1項に記載の方法。
- 前記有機素材がポリマーである、請求項1〜6のいずれか1項に記載の方法。
- 前記組成物が導電性有機素材を含む、請求項1〜7のいずれか1項に記載の方法。
- 前記組成物が少なくとも8のpHを有する、請求項1〜8のいずれか1項に記載の方法。
- 前記PEDOT:対イオンの比率が1:6〜1:30の範囲である、請求項1〜9のいずれか1項に記載の方法。
- 前記対イオンがPSSである、請求項1〜10のいずれかに記載の方法。
- 前記組成物がインクジェットプリンティングにより堆積される、請求項1〜11のいずれか1項に記載の方法。
- 導電性有機素材を含む組成物が第1の電極の上に堆積され、半導電性有機素材を含む組成物がその上に堆積され、該導電性及び半導電性組成物の少なくとも一つが塩基性添加物を含む、請求項1〜12のいずれか1項に記載の方法。
- 前記基材が、複数のウェルを規定するバンク構造を含み、前記組成物が、ディスプレイを形成させるためにインクジェットプリンティングにより、複数のウェルに堆積される、請求項1〜13のいずれか1項に記載の方法。
- 前記ディスプレイがスウォースに印刷されている、請求項14に記載の方法。
- 第1のスウォースと第2のスウォースが互いに隣接して連続的に印刷され、印刷速度は、第2のスウォースの印刷が完了する前に、第1のスウォースが顕著に乾燥しない程度である、請求項15に記載の方法。
- 光電気デバイスの製造方法における、酸性基を有する導電性又は半導電性有機素材、溶媒、及び塩基性添加物を含む組成物であって、
前記塩基性添加物が、ヒドロキシル基を有する有機アミンであり、かつ、100℃よりも高い沸点を有し、
前記有機素材が、電荷平衡対イオンを有するPEDOTを含むホール注入素材を含む、
組成物の使用。
Applications Claiming Priority (7)
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GB0615278.9 | 2006-08-01 | ||
GBGB0615278.9A GB0615278D0 (en) | 2006-08-01 | 2006-08-01 | Methods of Manufacturing Opto-Electrical Devices |
GBGB0615279.7A GB0615279D0 (en) | 2006-08-01 | 2006-08-01 | Opto-electrical devices and methods of manufacturing the same |
GB0615279.7 | 2006-08-01 | ||
GB0709430.3 | 2007-05-16 | ||
GBGB0709430.3A GB0709430D0 (en) | 2007-05-16 | 2007-05-16 | Methods of manufacturing opto-electrical devices |
PCT/GB2007/002917 WO2008015422A2 (en) | 2006-08-01 | 2007-08-01 | Methods of manufacturing opto-electrical devices |
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JP2009545844A JP2009545844A (ja) | 2009-12-24 |
JP2009545844A5 JP2009545844A5 (ja) | 2012-10-18 |
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2007
- 2007-08-01 EP EP07789093A patent/EP2047542A1/en not_active Withdrawn
- 2007-08-01 WO PCT/GB2007/002922 patent/WO2008015426A1/en active Application Filing
- 2007-08-01 JP JP2009522331A patent/JP2009545870A/ja active Pending
- 2007-08-01 KR KR1020097004255A patent/KR101440164B1/ko active IP Right Grant
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KR101418618B1 (ko) | 2014-07-14 |
US20090263567A1 (en) | 2009-10-22 |
US8084767B2 (en) | 2011-12-27 |
TWI442563B (zh) | 2014-06-21 |
JP2009545844A (ja) | 2009-12-24 |
EP2047541A2 (en) | 2009-04-15 |
JP2009545870A (ja) | 2009-12-24 |
WO2008015422A2 (en) | 2008-02-07 |
KR20090035029A (ko) | 2009-04-08 |
TW200824115A (en) | 2008-06-01 |
EP2047542A1 (en) | 2009-04-15 |
WO2008015426A1 (en) | 2008-02-07 |
US20090315023A1 (en) | 2009-12-24 |
KR101440164B1 (ko) | 2014-09-12 |
KR20090035030A (ko) | 2009-04-08 |
WO2008015422A3 (en) | 2008-03-27 |
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