JP2004319504A - 有機発光デバイスの形成方法 - Google Patents
有機発光デバイスの形成方法 Download PDFInfo
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- JP2004319504A JP2004319504A JP2004119100A JP2004119100A JP2004319504A JP 2004319504 A JP2004319504 A JP 2004319504A JP 2004119100 A JP2004119100 A JP 2004119100A JP 2004119100 A JP2004119100 A JP 2004119100A JP 2004319504 A JP2004319504 A JP 2004319504A
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- layer
- organic
- light emitting
- anode
- substrate
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- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000010410 layer Substances 0.000 claims abstract description 101
- 239000000463 material Substances 0.000 claims abstract description 71
- 239000000758 substrate Substances 0.000 claims abstract description 52
- 229910052751 metal Inorganic materials 0.000 claims abstract description 32
- 239000002184 metal Substances 0.000 claims abstract description 32
- 239000012044 organic layer Substances 0.000 claims abstract description 25
- 230000005855 radiation Effects 0.000 claims abstract description 19
- 239000002019 doping agent Substances 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 13
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 9
- 230000004888 barrier function Effects 0.000 claims abstract description 5
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 229910001507 metal halide Inorganic materials 0.000 claims description 5
- 150000005309 metal halides Chemical class 0.000 claims description 5
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- -1 gallium nitride Chemical class 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 18
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- 238000005229 chemical vapour deposition Methods 0.000 description 10
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- 238000004544 sputter deposition Methods 0.000 description 5
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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 3
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
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- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910003480 inorganic solid Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
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- 150000004032 porphyrins Chemical class 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 238000001429 visible spectrum Methods 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical compound C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical compound C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
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- VHRHRMPFHJXSNR-UHFFFAOYSA-N 2-phenylpyridin-3-ol Chemical compound OC1=CC=CN=C1C1=CC=CC=C1 VHRHRMPFHJXSNR-UHFFFAOYSA-N 0.000 description 1
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- Electroluminescent Light Sources (AREA)
Abstract
【解決手段】 本発明による有機発光デバイスの形成方法は、a)基板上にアノードを形成させ、b)該アノードから間隔を置いて配置したカソードを用意し、c)発光材料を含むドナー要素を用意し、かつ、該ドナー要素を該基板に対して材料転写関係をなすように配置し、d)該ドナー要素に輻射線を照射することにより、該アノード上に発光材料を転写して付着させることにより発光層を形成させ、そしてe)該発光層と該カソードとの間に、ドナードーパントとして作用し得る低仕事関数金属もしくは金属化合物又はこれらの混合物をドープした有機化合物を含む有機層を形成させることにより、該有機層から該発光層内への電子注入障壁を低下させ、よって該有機発光デバイスの安定性を向上させることを特徴とする。
【選択図】 図1
Description
a)基板上にアノードを形成させ、
b)該アノードから間隔を置いて配置したカソードを用意し、
c)発光材料を含むドナー要素を用意し、かつ、該ドナー要素を該基板に対して材料転写関係をなすように配置し、
d)該ドナー要素に輻射線を照射することにより、該アノード上に発光材料を転写して付着させることにより発光層を形成させ、そして
e)該発光層と該カソードとの間に、ドナードーパントとして作用し得る低仕事関数金属又は金属化合物をドープした有機化合物を含む有機層を形成させることにより、該有機層から該発光層内への電子注入障壁を低下させ、よって該有機発光デバイスの安定性を向上させる
ことを特徴とする方法によって達成される。
Gは、アリーレン、シクロアルキレン又は炭素-炭素結合のアルキレン基のような結合基である。
一つの態様において、Q1及びQ2の少なくとも一方は、多環式縮合環構造体(例、ナフタレン)を含有する。Gがアリール基である場合、それはフェニレン部分、ビフェニレン部分又はナフタレン部分であることが便利である。
構造式(A)を満たし、かつ、2つのトリアリールアミン部分を含有する有用な種類のトリアリールアミンは、下記構造式(B)で表わされる。
R3及びR4は、各々独立に、アリール基であってそれ自体が下記構造式(C)で示されるようなジアリール置換型アミノ基で置換されているものを表わす。
別の種類の芳香族第三アミンはテトラアリールジアミンである。望ましいテトラアリールジアミンは、アリーレン基を介して結合された、構造式(C)で示したようなジアリールアミノ基を2個含む。有用なテトラアリールジアミンには、下記構造式(D)で表わされるものが含まれる。
nは1〜4の整数であり、そして
Ar、R7、R8及びR9は各々独立に選ばれたアリール基である。
典型的な態様では、Ar、R7、R8及びR9の少なくとも一つが多環式縮合環構造体(例、ナフタレン)である。
1,1-ビス(4-ジ-p-トリルアミノフェニル)シクロヘキサン
1,1-ビス(4-ジ-p-トリルアミノフェニル)-4-フェニルシクロヘキサン
4,4’-ビス(ジフェニルアミノ)クアドリフェニル
ビス(4-ジメチルアミノ-2-メチルフェニル)-フェニルメタン
N,N,N-トリ(p-トリル)アミン
4-(ジ-p-トリルアミノ)-4’-[4(ジ-p-トリルアミノ)-スチリル]スチルベン
N,N,N’,N’-テトラ-p-トリル-4,4’-ジアミノビフェニル
N,N,N’,N’-テトラフェニル-4,4’-ジアミノビフェニル
N-フェニルカルバゾール
ポリ(N-ビニルカルバゾール)
N,N’-ジ-1-ナフタレニル-N,N’-ジフェニル-4,4’-ジアミノビフェニル
4,4’-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル
4,4”-ビス[N-(1-ナフチル)-N-フェニルアミノ]-p-ターフェニル
4,4’-ビス[N-(2-ナフチル)-N-フェニルアミノ]ビフェニル
4,4’-ビス[N-(3-アセナフテニル)-N-フェニルアミノ]ビフェニル
1,5-ビス[N-(1-ナフチル)-N-フェニルアミノ]ナフタレン
4,4’-ビス[N-(9-アントリル)-N-フェニルアミノ]ビフェニル
4,4”-ビス[N-(1-アントリル)-N-フェニルアミノ]-p-ターフェニル
4,4’-ビス[N-(2-フェナントリル)-N-フェニルアミノ]ビフェニル
4,4’-ビス[N-(8-フルオルアンテニル)-N-フェニルアミノ]ビフェニル
4,4’-ビス[N-(2-ピレニル)-N-フェニルアミノ]ビフェニル
4,4’-ビス[N-(2-ナフタセニル)-N-フェニルアミノ]ビフェニル
4,4’-ビス[N-(2-ペリレニル)-N-フェニルアミノ]ビフェニル
4,4’-ビス[N-(1-コロネニル)-N-フェニルアミノ]ビフェニル
2,6-ビス(ジ-p-トリルアミノ)ナフタレン
2,6-ビス[ジ-(1-ナフチル)アミノ]ナフタレン
2,6-ビス[N-(1-ナフチル)-N-(2-ナフチル)アミノ]ナフタレン
N,N,N’,N’-テトラ(2-ナフチル)-4,4”-ジアミノ-p-ターフェニル
4,4’-ビス{N-フェニル-N-[4-(1-ナフチル)-フェニル]アミノ}ビフェニル
4,4’-ビス[N-フェニル-N-(2-ピレニル)アミノ]ビフェニル
2,6-ビス[N,N-ジ(2-ナフチル)アミン]フルオレン
1,5-ビス[N-(1-ナフチル)-N-フェニルアミノ]ナフタレン
CO-1:アルミニウムトリスオキシン〔別名、トリス(8-キノリノラト)アルミニウム(III)〕
CO-2:マグネシウムビスオキシン〔別名、ビス(8-キノリノラト)マグネシウム(II)〕
CO-3:ビス[ベンゾ{f}-8-キノリノラト]亜鉛(II)
CO-4:ビス(2-メチル-8-キノリノラト)アルミニウム(III)-μ-オキソ-ビス(2-メチル-8-キノリノラト)アルミニウム(III)
CO-5:インジウムトリスオキシン〔別名、トリス(8-キノリノラト)インジウム〕
CO-6:アルミニウムトリス(5-メチルオキシン)〔別名、トリス(5-メチル-8-キノリノラト)アルミニウム(III)〕
CO-7:リチウムオキシン〔別名、(8-キノリノラト)リチウム(I)〕
第1グループ:水素、又は炭素原子数1〜24のアルキル;
第2グループ:炭素原子数5〜20のアリール又は置換アリール;
第3グループ:アントラセニル、ピレニルまたはペリレニルの縮合芳香族環の完成に必要な4〜24個の炭素原子;
第4グループ:フリル、チエニル、ピリジル、キノリニルその他の複素環式系の縮合芳香族環の完成に必要な炭素原子数5〜24のヘテロアリール又は置換ヘテロアリール;
第5グループ:炭素原子数1〜24のアルコキシルアミノ、アルキルアミノ又はアリールアミノ;及び
第6グループ:フッ素、塩素、臭素又はシアノ
ZはO、NR又はSであり、
R’は、水素、炭素原子数1〜24のアルキル(例えば、プロピル、t-ブチル、ヘプチル、等)、炭素原子数5〜20のアリールもしくはヘテロ原子置換型アリール(例えば、フェニル及びナフチル、フリル、チエニル、ピリジル、キノリニルその他の複素環式系)、ハロ(例、クロロ、フルオロ)、又は縮合芳香族環の完成に必要な原子群、であり、
Lは、アルキル、アリール、置換アルキル又は置換アリールからなる結合ユニットであって、当該複数のベンズアゾール同士を共役的又は非共役的に連結させるものである。
有用なベンズアゾールの一例として2,2’,2”-(1,3,5-フェニレン)トリス[1-フェニル-1H-ベンズイミダゾール]が挙げられる。
例1(発明例)
本発明の構成要件を満たす低仕事関数金属をドープした有機層を具備するOLEDデバイスを以下のように構築した。
1)清浄なガラス基板にインジウム錫酸化物(ITO)を蒸着して厚さ34nmの透明電極を形成した。
2)調製されたITO面にプラズマ酸素エッチング処理を施し、次いで、米国特許第6208075号明細書に記載されているように、厚さ1.0nmのフルオロカーボンポリマー(CFx)層をプラズマ蒸着した。
3)調製された基板に、約10-6トルの真空下で、加熱ボート源から4,4’-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(NPB)の厚さ170nmの正孔輸送層を蒸着する処理をさらに施した。
4)調製された基板を真空状態から取り出し、そして空気に約5分間晒してから、窒素ドライボックス内に配置した。
5)厚さ75μmのポリスルホンシートの上に厚さ40nmのクロムを真空被覆することによりドナー基板を調製した。
6)調製されたドナー基板に、1.25%の2,5,8,11-テトラ-t-ブチルペリレン(TBP)をドープした2-(1,1-ジメチルエチル)-9,10-ビス(2-ナフタレニル)アントラセン(TBADN)からなる厚さ20nmの層をさらに真空被覆し、その後さらに0.8nmのNPBを追加被覆することによりドナー要素を作製した。
7)調製されたドナー要素を真空状態から取り出し、そして空気に約5分間晒してから、窒素ドライボックス内に配置した。
8)調製されたドナー要素を、工程3からの基板に対し、該ドナー要素と該基板の間の間隙を75μmに維持するスペーサを使用し、材料転写関係をなすように配置した。
9)多チャンネル式レーザーを使用してドナー要素に755mJ/cm2のエネルギーで照射を施し、正孔輸送層又は基盤の上に発光層を形成した。
10)上記基板を空気に約10分間晒した後、真空状態に戻した。
11)それぞれAlqとリチウムのための2つの加熱ボート源を含むコーティングステーションにおいて、上記基板上に、1.2体積%のリチウムを含むトリス(8-キノリノラト)アルミニウム(III)(Alq)からなる厚さ35nmの電子輸送層(Alq:Li)を真空蒸着した。
12)1つが銀を含み、1つがマグネシウムを含む独立したタンタルボートを具備したコーティングステーションにおいて受容体要素の上に厚さ220nmのカソード層を付着させた。カソード層は、マグネシウムと銀の体積比が10:1であった。
13)その後、OLEDデバイスをドライボックスへ移送して封入処理した。
工程11(電子輸送層の蒸着)を以下のようにしたことを除き、例1に記載したようにOLEDデバイスを構築した。
11)加熱ボート源を含むコーティングステーションにおいて、上記基板上に、トリス(8-キノリノラト)アルミニウム(III)(Alq)からなる厚さ35nmの電子輸送層を真空蒸着した。
例1及び例2のデバイスを、室温で80mA/cm2の一定電流を電極間に印加して、初期電圧及び輝度が初期輝度の50%に低下するまでの時間(80mA/cm2半減期)を測定することにより試験した。次いで、各例について相対電圧及び相対半減期を、例2の比較対照を基準に計算した。その結果を下記の表に示す。
14…OLEDデバイス
20…アノード
22…正孔注入層
24…正孔輸送層
26…発光層
28…有機層
30…カソード
38…受容面
40…ドナー要素
42…レーザー光
44…レーザー源
46…ドナー支持要素
48…吸光層
50…発光材料
52…非転写面
54…熱
56…間隙
58…隆起表面部分
Claims (10)
- 安定性が向上された有機発光デバイスの形成方法であって、
a)基板上にアノードを形成させ、
b)該アノードから間隔を置いて配置したカソードを用意し、
c)発光材料を含むドナー要素を用意し、かつ、該ドナー要素を該基板に対して材料転写関係をなすように配置し、
d)該ドナー要素に輻射線を照射することにより、該アノード上に発光材料を転写して付着させることにより発光層を形成させ、そして
e)該発光層と該カソードとの間に、ドナードーパントとして作用し得る低仕事関数金属もしくは金属化合物又はこれらの混合物をドープした有機化合物を含む有機層を形成させることにより、該有機層から該発光層内への電子注入障壁を低下させ、よって該有機発光デバイスの安定性を向上させる
ことを特徴とする方法。 - 該低仕事関数金属がLi、Na、K、RbもしくはCs又はこれらの混合物を含む、請求項1に記載の方法。
- 該金属化合物が金属ハロゲン化物を含む、請求項1に記載の方法。
- 該金属ハロゲン化物がLiF、NaF、KF、RbFもしくはCsF又はこれらの混合物を含む、請求項3に記載の方法。
- 安定性が向上された有機発光デバイスの形成方法であって、
a)基板上にアノードを形成させ、
b)該アノードから間隔を置いて配置したカソードを用意し、
c)発光材料を含むドナー要素を用意し、かつ、該ドナー要素を該基板に対して材料転写関係をなすように配置し、
d)該ドナー要素に輻射線を照射することにより、該アノード上に発光材料を転写して付着させることにより発光層を形成させ、そして
e)該発光層と該カソードとの間に、ドナードーパントとして作用し得る低仕事関数金属もしくは金属化合物又はこれらの混合物をドープした有機化合物を含む有機電子輸送層を形成させることにより、該有機電子輸送層から該発光層内への電子注入障壁を低下させ、よって該有機発光デバイスの安定性を向上させる
ことを特徴とする方法。 - 該電子輸送層を該発光層の上に形成させる、請求項5に記載の方法。
- 該電子輸送層の上にさらに電子注入層を形成させ、該電子注入層の上に該カソードを形成させる、請求項5に記載の方法。
- 該低仕事関数金属がLi、Na、K、RbもしくはCs又はこれらの混合物を含む、請求項5に記載の方法。
- 該金属化合物が金属ハロゲン化物を含む、請求項5に記載の方法。
- 該金属ハロゲン化物がLiF、NaF、KF、RbFもしくはCsF又はこれらの混合物を含む、請求項9に記載の方法。
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KR102036635B1 (ko) * | 2011-03-28 | 2019-10-28 | 삼성디스플레이 주식회사 | 금속배선 구조체, 이를 이용한 유기발광표시장치 및 그 제조방법 |
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KR20200026057A (ko) * | 2018-08-30 | 2020-03-10 | 엘지디스플레이 주식회사 | 도포형 유기 전계 발광 소자와, 이를 포함하는 표시장치 및 조명장치 |
KR102209498B1 (ko) * | 2018-08-30 | 2021-01-28 | 엘지디스플레이 주식회사 | 도포형 유기 전계 발광 소자와, 이를 포함하는 표시장치 및 조명장치 |
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Also Published As
Publication number | Publication date |
---|---|
EP1469534A2 (en) | 2004-10-20 |
TW200505276A (en) | 2005-02-01 |
KR20040090925A (ko) | 2004-10-27 |
CN1541036A (zh) | 2004-10-27 |
JP4745619B2 (ja) | 2011-08-10 |
EP1469534A3 (en) | 2006-05-10 |
US6703180B1 (en) | 2004-03-09 |
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