JP6100806B2 - ドープ正孔輸送層を介して改善されたoled安定性 - Google Patents
ドープ正孔輸送層を介して改善されたoled安定性 Download PDFInfo
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- JP6100806B2 JP6100806B2 JP2015000267A JP2015000267A JP6100806B2 JP 6100806 B2 JP6100806 B2 JP 6100806B2 JP 2015000267 A JP2015000267 A JP 2015000267A JP 2015000267 A JP2015000267 A JP 2015000267A JP 6100806 B2 JP6100806 B2 JP 6100806B2
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- 239000012044 organic layer Substances 0.000 claims description 84
- 150000003384 small molecules Chemical class 0.000 claims description 47
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 23
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- 239000002184 metal Substances 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 238000001429 visible spectrum Methods 0.000 claims description 9
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 claims description 5
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical group [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
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- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 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 1
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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 1
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- 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]
- H10K50/14—Carrier transporting layers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- 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
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- 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
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- Manufacturing & Machinery (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Description
有機発光デバイスの特定の層に有用であるとして本明細書に記述される材料は、デバイス内に存在する広く様々なその他の材料と組み合わせて使用してもよい。例えば、本明細書に開示される発光ドーパントは、広く様々なホスト、輸送層、遮断層、注入層、電極、および存在し得るその他の層と併せて使用してもよい。以下に記述されまたは言及される材料は、本明細書に開示される化合物と組み合わせて役立てることができる材料の非限定的な例であり、当業者なら、組合せで役立てることができるその他の材料を特定するのに、文献を容易に調べることができる。
トリアリールアミンHTL(NPD)を有する緑色および赤色リン光OLEDの寿命は、非ドープ型NPD HTL参照デバイスに比べ、2%の金属キノレート(Alq)をHTL中にドープすることによって、2×を超えて改善されてきた。すべてのドープパーセンテージは、重量%を単位とする。Table 2、3、および4(表2、3、および4)で報告したすべての測定は、室温環境で行った。デバイス寿命の改善は、EMLからNPD HTL内に漏れる電子または励起子に起因する、形成されたNPD励起状態分子の消光によると考えられる。ドープされたHTLは、デバイスELスペクトルを汚染することなく、緑色および赤色リン光OLEDで作用することを示し、ドープされたHTLはR、G、B OLEDの一般的な層構造で使用するのに適していることを示す。
331 正孔注入層
332 非発光層
340 非発光層
350 発光層
380 カソード
Claims (16)
- アノードと、
カソードと、
前記アノードと前記カソードとの間に配置され、第1の有機発光材料を含む発光層である、第1の有機層と、
前記アノードと前記第1の有機層との間に配置され、前記第1の有機層と直接接触し、非発光層である第2の有機層と
を含み、
前記第2の有機層は、
50から99重量%の濃度を有する有機低分子正孔輸送材料と、
0.1から5重量%の濃度を有する有機低分子電子輸送材料と
を含み、
前記第2の有機層と前記アノードとの間に配置され、前記第2の有機層と直接接触し、有機低分子正孔輸送材料を含みかつ有機低分子電子輸送材料を含まない第5の有機層をさらに含み、
前記第5の有機層は、前記第2の有機層と同じ有機低分子正孔輸送材料を含み、
前記有機低分子電子輸送材料が、前記有機低分子正孔輸送材料のHOMO−LUMOの差よりも少なくとも0.2eV少ないHOMO−LUMOの差を有する、
有機発光デバイス。 - 前記有機低分子電子輸送材料が、前記第2の有機層内で0.1から4重量%の濃度を有する、請求項1に記載のデバイス。
- 前記有機低分子電子輸送材料が、前記第2の有機層内で0.1から3重量%の濃度を有する、請求項1に記載のデバイス。
- 前記有機低分子電子輸送材料が、前記第2の有機層内で2から3重量%の濃度を有する、請求項1に記載のデバイス。
- 前記第2の有機層と前記アノードとの間に配置された、正孔注入材料を含む第3の有機層をさらに含み、
前記第3の有機層は前記アノードに直接接触しており、
前記第3の有機層は前記第5の有機層に直接接触している、
請求項1に記載のデバイス。 - 前記第1の有機層と前記カソードとの間に配置された、第2の発光材料を含む発光層である第4の有機層をさらに含む、請求項1に記載のデバイス。
- 前記有機低分子電子輸送材料が、前記有機低分子正孔輸送材料のLUMOエネルギー準位よりも少なくとも0.2eV少ないLUMOエネルギー準位を有する、請求項1に記載のデバイス。
- 前記第1の有機発光材料がリン光性である、請求項1に記載のデバイス。
- 前記発光材料が、600から700nmの可視スペクトル内でピーク発光波長を有する、請求項8に記載のデバイス。
- 前記発光材料が、500から600nmの可視スペクトル内でピーク発光波長を有する、請求項8に記載のデバイス。
- 前記発光材料が、400から500nmの可視スペクトル内でピーク発光波長を有する、請求項8に記載のデバイス。
- 前記有機低分子電子輸送材料が金属キノレートである、請求項1に記載のデバイス。
- 前記有機低分子電子輸送材料がAlq3である、請求項12に記載のデバイス。
- 前記有機低分子正孔輸送材料がアミン含有材料である、請求項1に記載のデバイス。
- 前記有機低分子正孔輸送材料がNPDである、請求項14に記載のデバイス。
- 前記有機低分子電子輸送材料が、前記有機低分子正孔輸送材料よりも高い電子移動度を有する、請求項1に記載のデバイス。
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US12199108P | 2008-12-12 | 2008-12-12 | |
US61/121,991 | 2008-12-12 |
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JP2015000267A Active JP6100806B2 (ja) | 2008-12-12 | 2015-01-05 | ドープ正孔輸送層を介して改善されたoled安定性 |
JP2016215047A Active JP6408532B2 (ja) | 2008-12-12 | 2016-11-02 | ドープ正孔輸送層を介して改善されたoled安定性 |
JP2018102230A Pending JP2018133595A (ja) | 2008-12-12 | 2018-05-29 | ドープ正孔輸送層を介して改善されたoled安定性 |
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JP2018102230A Pending JP2018133595A (ja) | 2008-12-12 | 2018-05-29 | ドープ正孔輸送層を介して改善されたoled安定性 |
Country Status (7)
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US (1) | US8778511B2 (ja) |
EP (1) | EP2377181B1 (ja) |
JP (4) | JP2012511833A (ja) |
KR (2) | KR101932823B1 (ja) |
CN (1) | CN102292839B (ja) |
TW (1) | TWI463914B (ja) |
WO (1) | WO2010068330A1 (ja) |
Cited By (1)
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JP2017028325A (ja) * | 2008-12-12 | 2017-02-02 | ユニバーサル ディスプレイ コーポレイション | ドープ正孔輸送層を介して改善されたoled安定性 |
Families Citing this family (18)
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JP5672077B2 (ja) * | 2011-03-04 | 2015-02-18 | セイコーエプソン株式会社 | 発光素子、発光装置、表示装置および電子機器 |
US8883322B2 (en) * | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
KR101936978B1 (ko) | 2011-07-05 | 2019-01-09 | 닛산 가가쿠 가부시키가이샤 | 수직 상-분리 반도체 유기 물질 층 |
JP6158542B2 (ja) * | 2012-04-13 | 2017-07-05 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、および照明装置 |
CN102694131B (zh) * | 2012-06-04 | 2015-06-03 | 京东方科技集团股份有限公司 | 一种有机电致发光器件及其制备方法以及显示装置 |
KR102035251B1 (ko) | 2013-03-12 | 2019-10-23 | 삼성디스플레이 주식회사 | 유기 발광 표시 장치 |
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JP2017028325A (ja) * | 2008-12-12 | 2017-02-02 | ユニバーサル ディスプレイ コーポレイション | ドープ正孔輸送層を介して改善されたoled安定性 |
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US8778511B2 (en) | 2014-07-15 |
TWI463914B (zh) | 2014-12-01 |
TW201031261A (en) | 2010-08-16 |
CN102292839A (zh) | 2011-12-21 |
US20110240984A1 (en) | 2011-10-06 |
JP2017028325A (ja) | 2017-02-02 |
KR101932823B1 (ko) | 2018-12-27 |
KR20110110172A (ko) | 2011-10-06 |
JP2012511833A (ja) | 2012-05-24 |
EP2377181B1 (en) | 2019-05-01 |
WO2010068330A1 (en) | 2010-06-17 |
JP6408532B2 (ja) | 2018-10-17 |
KR20160055956A (ko) | 2016-05-18 |
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JP2018133595A (ja) | 2018-08-23 |
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