JP7051877B2 - 有機エレクトロルミネッセンス(el)素子を形成する方法 - Google Patents
有機エレクトロルミネッセンス(el)素子を形成する方法 Download PDFInfo
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- JP7051877B2 JP7051877B2 JP2019541145A JP2019541145A JP7051877B2 JP 7051877 B2 JP7051877 B2 JP 7051877B2 JP 2019541145 A JP2019541145 A JP 2019541145A JP 2019541145 A JP2019541145 A JP 2019541145A JP 7051877 B2 JP7051877 B2 JP 7051877B2
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- DZEFNRWGWQDGTR-UHFFFAOYSA-N tetradec-1-yne Chemical compound CCCCCCCCCCCCC#C DZEFNRWGWQDGTR-UHFFFAOYSA-N 0.000 description 1
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Description
背景技術
ディスプレイ製造業者は、ディスプレイ用途向けの有機発光ダイオード(OLED)に高い関心を持っている。特に、インクジェット印刷されたOLEDのTVには、その高い性能と潜在的な低製造コストに関する高い可能性から、関心がある。インクジェット印刷技法を使用することの利点は、高度に正確な位置およびインク体積の制御と、大量生産の場合の潜在的に高いスループットである。従来のパネルは、少なくとも赤色、緑色、および青色(R、G、およびB)を含んでいる。通常、各色は、多層デバイス構造を有する。有望なディスプレイ製造に関する技術水準は、いわゆる青色共通層(BCL)構造である。BCL構造用に設定されるインクセットは、赤色用正孔注入層(R-HIL)、緑色用正孔注入層(G-HIL)、青色用正孔注入層(B-HIL)、赤色用正孔輸送層(R-HTL)、緑色用正孔輸送層(G-HTL)、青色用正孔輸送層(B-HTL)、緑色発光層(G-EML)、および赤色発光層(R-EML)を形成するためのインクを含む。
技術的課題および本発明の目的
インクジェット印刷用の有機エレクトロルミネッセンス(EL)において、多くのインクが提案されている。しかし、堆積および乾燥のプロセス中に役割を果たす重要なパラメータの数が、堆積するインクの選択を非常に困難なものにしている。さらなる課題は、先行技術のインクおよび堆積法が、低効率で短寿命のデバイスをもたらし得るという点である。
発明の概要
本発明は、正孔注入層(HIL)、正孔輸送層(HTL)および発光層(EML)を含む少なくとも3つの異なる層を含む少なくとも1つの画素タイプを有する有機EL素子を形成する方法であって、少なくとも1つの画素タイプのHIL、HTLおよびEMLが、インクを堆積させることによって得られ、ここで、層は、前記堆積工程後に第1、第2および第3のアニーリング工程においてアニーリングされ、第1および第2のアニーリング工程のアニーリング温度の差は、35℃未満、好ましくは30℃未満、より好ましくは25℃未満であり、第3のアニーリング工程のアニーリング温度は、第1および/または第2のアニーリング工程のアニーリング温度を5℃以上超えず、好ましくは、第3のアニーリング工程のアニーリング温度は、第1および第2のアニーリング工程のアニーリング温度以下であり、第1のアニーリング工程は、第2のアニーリング工程の前に遂行され、第2のアニーリング工程は、第3のアニーリング工程の前に遂行されることを特徴とする方法に関する。
発明の効果
本発明者らは、驚くべきことに、正孔注入層(HIL)、正孔輸送層(HTL)および発光層(EML)を含む少なくとも3つの異なる層を含む少なくとも1つの画素タイプを有する有機EL素子を形成する方法であって、少なくとも1つの画素タイプのHIL、HTLおよびEMLが、インクを堆積させることによって得られ、ここで、層は、前記堆積工程後に第1、第2および第3のアニーリング工程においてアニーリングされ、第1および第2のアニーリング工程のアニーリング温度の差は、35℃未満、好ましくは30℃未満、より好ましくは25℃未満であり、第3のアニーリング工程のアニーリング温度は、第1および/または第2のアニーリング工程のアニーリング温度を5℃以上超えず、好ましくは、第3のアニーリング工程のアニーリング温度は、第1および第2のアニーリング工程のアニーリング温度以下であり、第1のアニーリング工程は、第2のアニーリング工程の前に遂行され、第2のアニーリング工程は、第3のアニーリング工程の前に遂行されることを特徴とする方法が、良好な層特性および非常に良好な性能を有する均一かつ明確に画定された機能材料の有機層を形成するための効果的なインクの堆積を可能にすることを発見した。
発明の詳細な説明
正孔注入層(HIL)、正孔輸送層(HTL)および発光層(EML)を含む少なくとも3つの異なる層を含む少なくとも1つの画素タイプを有する有機EL素子を形成する方法。これらの層は、先行技術において周知である。
T1-T2≦35℃、好ましくは≦30℃、より好ましくは≦25℃;
T2-T1≦35℃、好ましくは≦30℃、より好ましくは≦25℃;
T3-T1≦5℃、好ましくは≦0℃、より好ましくは≦-5℃;
T3-T2≦5℃、好ましくは≦0℃、より好ましくは≦-5℃.
好ましい態様において、第1の堆積工程のアニーリング温度は好ましくは少なくとも180℃、より好ましくは少なくとも190℃、さらにより好ましくは少なくとも200℃である。
HOMO(eV)=((HEh*27.212)-0.9899)/1.1206
LUMO(eV)=((LEh*27.212)-2.0041)/1.385
この出願の目的のため、これらの値をそれぞれ材料のHOMOおよびLUMOエネルギー準位とみなすこととする。
DCyは、出現する毎に同一であるかまたは異なり、少なくとも1個の供与体原子、好ましくは窒素、カルベンの形態の炭素、またはリンを含有する環状基であり、この環状基はこの供与体原子を介して金属に結合し、また、1つ以上の置換基Raを有していてもよく;基DCyとCCyは、共有結合を介して互いに結合しており;
CCyは、出現する毎に同一であるかまたは異なり、炭素原子を含有する環状基であり、この環状基はこの炭素原子を介して金属に結合しており、また、1つ以上の置換基Raを有していてもよく;
Aは、出現する毎に同一であるかまたは異なり、モノアニオン性二座キレート配位子、好ましくはジケトナート配位子であり;
Raは、それぞれの場合において同一であるかまたは異なり、F、Cl、Br、I、NO2、CN、1~20個の炭素原子を有する直鎖、分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1つ以上の隣接していないCH2基は、-O-、-S-、-NRb-、-CONRb-、-CO-O-、-C=O-、-CH=CH-または-C≡C-によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)、または4~14個の炭素原子を有し、1つ以上のRcラジカルによって置換されていてもよいアリールもしくはヘテロアリール基であり、複数の置換基Raはまた、同じ環上または2つの異なる環上のいずれかで、一緒になって単環もしくは多環式の脂肪族もしくは芳香族環系を形成してもよく;
Rbは、それぞれの場合において同一であるかまたは異なり、1~20個の炭素原子を有する直鎖、分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1つ以上の隣接していないCH2基は、-O-、-S-、-CO-O-、-C=O-、-CH=CH-または-C≡C-によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)、または4~14個の炭素原子を有し、1つ以上のRcラジカルによって置換されていてもよいアリールもしくはヘテロアリール基であり;
Rcは、それぞれの場合において同一であるかまたは異なり、1~20個の炭素原子を有する直鎖、分枝もしくは環状アルキルもしくはアルコキシ基(ここで、1つ以上の隣接していないCH2基は、-O-、-S-、-CO-O-、-C=O-、-CH=CH-または-C≡C-、によって置きかえられていてもよく、1個以上の水素原子は、Fによって置きかえられていてもよい)である)
の化合物である。
群1:正孔注入および/または正孔輸送特性を生成することができる構造要素;
群2:電子注入および/または電子輸送特性を生成することができる構造要素;
群3:群1および群2に関連して記載される特性を併せ持つ構造要素;
群4:発光特性、特にリン光基を有する構造要素;
群5:いわゆる一重項状態から三重項状態への移行を改善する構造要素;
群6:結果として得られるポリマーの形態または発光色に影響を与える構造要素;
群7:典型的には骨格として使用される構造要素。
Ar1は、各場合において、異なる反復単位に対して同一であるかまたは異なり、単結合、または任意に置換されていてもよい単環式もしくは多環式アリール基であり;
Ar2は、各場合において、異なる反復単位に対して同一であるかまたは異なり、任意に置換されていてもよい単環式または多環式アリール基であり;
Ar3は、各場合において、異なる反復単位に対して同一であるかまたは異なり、任意に置換されていてもよい単環式または多環式アリール基であり;
mは、1、2または3である)。
Raは、出現する毎に同一であるかまたは異なり、H、置換もしくは無置換芳香族もしくはヘテロ芳香族基、アルキル、シクロアルキル、アルコキシ、アラルキル、アリールオキシ、アリールチオ、アルコキシカルボニル、シリルもしくはカルボキシル基、ハロゲン原子、シアノ基、ニトロ基、またはヒドロキシ基であり;
rは、0、1、2、3または4であり、
sは、0、1、2、3、4または5である)。
T1およびT2は、チオフェン、セレノフェン、チエノ[2,3-b]チオフェン、チエノ[3,2-b]チオフェン、ジチエノチオフェン、ピロールおよびアニリンから独立して選択され、ここで、これらの基は1つ以上のラジカルRbによって置換されていてもよく;
Rbは、出現する毎にハロゲン、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X、-C(=O)R0、-NH2、-NR0R00、-SH、-SR0、-SO3H、-SO2R0、-OH、-NO2、-CF3、-SF5、任意に置換されていてもよく任意に1個以上のヘテロ原子を含有していてもよい、1~40個の炭素原子を有する任意に置換されていてもよいシリル、カルビルまたはヒドロカルビル基から独立して選択され;
R0およびR00は、それぞれ独立してH、または任意に置換されていてもよく任意に1個以上のヘテロ原子を含有していてもよい、1~40個の炭素原子を有する任意に置換されていてもよいカルビルもしくはヒドロカルビル基であり;
Ar7およびAr8は、互いに独立して、任意に置換されていてもよく任意に隣接するチオフェンまたはセレノフェン基の一方または両方の2,3位に結合していてもよい、単環式または多環式アリールまたはヘテロアリール基を表し;
cおよびeは、互いに独立して0、1、2、3または4であり、ここで、1<c+e≦6であり;
dおよびfは、互いに独立して0、1、2、3または4である)。
A、BおよびB’はそれぞれ、また、異なる反復単位に対して同一であるかまたは異なっており、好ましくは-CRcRd-、-NRc-、-PRc-、-O-、-S-、-SO-、-SO2-、-CO-、-CS-、-CSe-、-P(=O)Rc-、-P(=S)Rc-および-SiRcRd-から選択される二価基であり;
RcおよびRdは、出現する毎にH、ハロゲン、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X、-C(=O)R0、-NH2、-NR0R00、-SH、-SR0、-SO3H、-SO2R0、-OH、-NO2、-CF3、-SF5、任意に置換されていてもよく任意に1個以上のヘテロ原子を含有していてもよい1~40個の炭素原子を有する任意に置換されていてもよいシリル、カルビルまたはヒドロカルビル基から独立して選択され、ここで、RcおよびRdは、任意にそれらが結合しているフルオレンラジカルと共にスピロ基を形成してもよく;
Xは、ハロゲンであり;
R0およびR00はそれぞれ独立して、H、または任意に置換されていてもよく任意に1個以上のヘテロ原子を含有していてもよい、1~40個の炭素原子を有する任意に置換されていてもよいカルビルもしくはヒドロカルビル基であり;
gは、各場合において、独立して0または1であり、hは、各場合において、独立して0または1であり、ここで、副単位中のgとhの合計は好ましくは1であり;
mは、1以上の整数であり;
Ar1およびAr2は、互いに独立して任意に置換されていてもよく任意にインデノフルオレンの7,8位または8,9位に結合されていてもよい単環式または多環式アリールまたはヘテロアリール基を表し;
aおよびbは、互いに独立して0または1である)。
Lは、H、ハロゲン、または1~12個のC原子を有する任意にフッ素化されていてもよい直鎖状もしくは分枝アルキルもしくはアルコキシ基であり、好ましくはメチル、i-プロピル、t-ブチル、n-ペントキシまたはトリフルオロメチルを表し;
L’は、1~12個のC原子を有する任意にフッ素化されていてもよい直鎖状または分枝アルキルまたはアルコキシ基であり、好ましくはn-オクチルまたはn-オクチルオキシを表す)。
1.本発明による方法を用いて得ることができる電子デバイスは、従来の方法を用いて得られる電子デバイスと比較して、非常に高い安定性と非常に長い寿命を呈する。
2.本発明による方法を用いることにより得ることができる電子デバイスは、高効率、とりわけ高い輝度効率と高い外部量子効率を呈する。
3.本発明に有用なインクは、従来の方法を用いて加工することができ、その結果、費用優位性を実現することができる。
4.本発明による方法に利用される有機機能材料は、特定の制約を何ら受けることなく、本発明の方法を包括的に利用することを可能とする。
5.本発明の方法を用いて得ることができる層は、特に層の均一性に関して優れた品質を呈する。
6.本発明に有用なインクは、従来の方法を用いて非常に迅速かつ簡便な方法で製造することができ、そのため、コスト上の利点も達成することができる。
本発明において開示されるそれぞれの特徴は、明確に排除されない限り、同一、同等または類似の目的を果たす代替的特徴によって置きかえることができる。したがって、本発明において開示されるそれぞれの特徴は、特に断らない限り、包括的シリーズの一例、または同等もしくは類似の特徴とみなすべきである。
真空蒸着法によって得られる青色発光層を有する青色画素のみを有するデバイスを製造する。カソードの厚さは100nm、ETLの厚さは20nm、青色共通層の厚さは25nm、青色HTL(B-HTL)の厚さは40nm、HILの厚さは30nm、ITOアノードの厚さは50nmである。
Keithley230電圧源によって供給される定電圧によりデバイスを駆動する。デバイスにかかる電圧およびデバイスを通る電流をKeithley199DMMマルチメーターで測定する。デバイスの明度をフォトダイオードとフォトニックフィルターの組合せであるSPL-025Y明度センサで検出する。光電流をKeithley617電位計で測定する。スペクトルの場合、明度センサを分光計入力に接続したガラス繊維に置きかえる。デバイスの寿命は、初期輝度を有する所定電流の下で測定される。次いで、輝度が較正されたフォトダイオードにより経時的に測定される。
下記の画素特性を有する図1に示すようなデバイスを調製する:
予め構造化されたITOとバンク材料で被覆したガラス基板をイソプロパノール中とその後の脱イオン水中での超音波処理を用いて洗浄し、次いでエアガンを用いて乾燥させ、続いてホットプレート上にて230℃で2時間アニーリングした。
原則的に例2を繰り返すが、下記のインクセットを使用する:
Claims (17)
- 正孔注入層(HIL)、正孔輸送層(HTL)および発光層(EML)を含む少なくとも3つの異なる層を含む少なくとも1つの画素タイプを有する有機EL素子を形成する方法であって、少なくとも1つの画素タイプの前記HIL、前記HTLおよび前記EMLが、インクを堆積させることによって得られ、ここで、前記層は、前記堆積工程後に第1、第2および第3のアニーリング工程においてアニーリングされ、前記第1および第2のアニーリング工程のアニーリング温度の差は、35℃未満であり、前記第3のアニーリング工程のアニーリング温度は、前記第1および/または前記第2のアニーリング工程のアニーリング温度以下であり、前記第1のアニーリング工程は、前記第2のアニーリング工程の前に遂行され、前記第2のアニーリング工程は、前記第3のアニーリング工程の前に遂行され、
第1の画素タイプと第2の画素タイプを含む少なくとも2つの異なる画素タイプを有する有機EL素子が製造され、両画素タイプの前記HILおよび前記HTLと少なくとも1つの画素タイプの前記EMLがインクを堆積させることによって得られ、両画素タイプの少なくとも1つの層は、インクを同時に塗布することによって堆積され、
第3の堆積工程のアニーリング温度が、少なくとも140℃であることを特徴とする、有機EL素子を形成する方法。 - 少なくとも3つの異なる画素タイプを有する有機EL素子が製造され、全ての画素タイプの前記HILおよび前記HTLと少なくとも1つの画素タイプの前記EMLがインクを堆積させることによって得られ、全ての画素タイプの少なくとも1つの層は、インクを同時に塗布することによって堆積させることを特徴とする、請求項1に記載の有機EL素子を形成する方法。
- 全ての画素タイプが、HILを含み、HILを得るためのインクが有機溶媒を含むことを特徴とする、請求項2に記載の有機EL素子を形成する方法。
- 全ての画素タイプが、HILを含み、全ての画素タイプの前記HILが、同時にインクを堆積させ、乾燥し、アニーリングすることによって製造され、ここで、前記アニーリング工程が、アニーリング温度T1で遂行されることを特徴とする、請求項1~3の何れか1項に記載の有機EL素子を形成する方法。
- 前記有機EL素子が、第1の画素タイプ、第2の画素タイプおよび第3の画素タイプを含む3つの異なる画素タイプを有し、前記第2の画素タイプと前記第3の画素タイプの前記HTLが、同時にインクを堆積させ、乾燥し、アニーリングすることによって製造され、ここで、前記アニーリング工程が、アニーリング温度T2で遂行されることを特徴とする、請求項2~4の何れか1項に記載の有機EL素子を形成する方法。
- 前記第1の画素タイプの前記HTLと前記第2の画素タイプのEMLが、同時にインクを堆積させ、乾燥し、アニーリングすることによって製造され、ここで前記アニーリング工程が、アニーリング温度T3で遂行されることを特徴とする、請求項1~5の何れか1項に記載の有機EL素子を形成する方法。
- 第1の堆積工程のアニーリング温度が、少なくとも180℃であることを特徴とする、請求項1~6の何れか1項に記載の有機EL素子を形成する方法。
- 第2の堆積工程のアニーリング温度が、少なくとも180℃であることを特徴とする、請求項1~7の何れか1項に記載の有機EL素子を形成する方法。
- 第3の堆積工程のアニーリング温度が、少なくとも150℃であることを特徴とする、請求項1~8の何れか1項に記載の有機EL素子を形成する方法。
- 第1の堆積工程のアニーリング温度が、250℃以下であることを特徴とする、請求項1~9の何れか1項に記載の有機EL素子を形成する方法。
- 第2の堆積工程のアニーリング温度が、250℃以下であることを特徴とする、請求項1~10の何れか1項に記載の有機EL素子を形成する方法。
- 第3の堆積工程のアニーリング温度が、200℃以下であることを特徴とする、請求項1~11の何れか1項に記載の有機EL素子を形成する方法。
- 少なくとも1つの層が、堆積工程におけるアニーリング中に架橋されることを特徴とする、請求項1~12の何れか1項に記載の有機EL素子を形成する方法。
- 第1の工程においてHILが形成され、第2の工程においてHTLが形成され、第3の工程においてEMLが形成され、ここで、前記HILが前記HTLの前に形成され、前記HTLが前記EMLの前に形成されることを特徴とする、請求項1~13の何れか1項に記載の有機EL素子を形成する方法。
- 前記アニーリング工程を遂行する前に、前記インクを乾燥させ、乾燥工程が、減圧下で遂行されることを特徴とする、請求項1~14の何れか1項に記載の有機EL素子を形成する方法。
- インクを堆積させることによって得られる少なくとも1つの層が、インクジェット印刷されることを特徴とする、請求項1~15の何れか1項に記載の有機EL素子を形成する方法。
- 共通層を、真空蒸着技法により堆積させることを特徴とする、請求項1~16の何れか1項に記載の有機EL素子を形成する方法。
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TW201841408A (zh) | 2018-11-16 |
US11081679B2 (en) | 2021-08-03 |
CN110168765A (zh) | 2019-08-23 |
US20200259125A1 (en) | 2020-08-13 |
WO2018138319A1 (en) | 2018-08-02 |
TWI791481B (zh) | 2023-02-11 |
CN110168765B (zh) | 2023-04-04 |
KR20190110597A (ko) | 2019-09-30 |
JP2020505742A (ja) | 2020-02-20 |
EP3574534A1 (en) | 2019-12-04 |
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