WO2016121597A1 - フェナントロリン誘導体、それを含有する電子デバイス、発光素子および光電変換素子 - Google Patents
フェナントロリン誘導体、それを含有する電子デバイス、発光素子および光電変換素子 Download PDFInfo
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- WO2016121597A1 WO2016121597A1 PCT/JP2016/051578 JP2016051578W WO2016121597A1 WO 2016121597 A1 WO2016121597 A1 WO 2016121597A1 JP 2016051578 W JP2016051578 W JP 2016051578W WO 2016121597 A1 WO2016121597 A1 WO 2016121597A1
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- light emitting
- phenanthroline derivative
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 239000010410 layer Substances 0.000 claims description 287
- -1 benzoquinolinyl group Chemical group 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 238000002347 injection Methods 0.000 claims description 49
- 239000007924 injection Substances 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 239000012044 organic layer Substances 0.000 claims description 30
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000005013 aryl ether group Chemical group 0.000 claims description 11
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 11
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- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
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- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
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- 238000003786 synthesis reaction Methods 0.000 description 10
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000001342 alkaline earth metals Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
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- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
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Abstract
Description
一般式(1)で表されるフェナントロリン誘導体について詳細に説明する。
光電変換素子は、アノードとカソード、およびそれらアノードとカソードとの間に介在する有機層を有し、有機層において光エネルギーが電気的信号に変換される。前記有機層は少なくとも光電変換層を有していることが好ましく、さらに前記光電変換層はp型材料とn型材料を含むことがより好ましい。p型材料は、電子供与性(ドナー性)の材料であり、HOMOのエネルギー準位が浅く、正孔を輸送しやすい。n型材料は、電子吸引性(アクセプター性)の材料であり、LUMOのエネルギー準位が深く、電子を輸送しやすい。p型材料とn型材料は積層されていてもよいし、混合されていてもよい。
次に、本発明の発光素子の実施の形態について詳細に説明する。本発明の発光素子は、陽極と陰極、およびそれら陽極と陰極との間に介在する有機層を有し、該有機層が電気エネルギーにより発光する。
本発明の発光素子において、陽極と陰極は素子の発光のために十分な電流を供給するための役割を有するものであり、光を取り出すために少なくとも一方は透明または半透明であることが好ましい。通常、基板上に形成される陽極を透明電極とする。
正孔輸送層は、正孔輸送材料の一種または二種以上を積層または混合する方法、もしくは、正孔輸送材料と高分子結着剤の混合物を用いる方法により形成される。また、正孔輸送材料は、電界を与えられた電極間において正極からの正孔を効率良く輸送することが必要で、正孔注入効率が高く、注入された正孔を効率良く輸送することが好ましい。そのためには適切なイオン化ポテンシャルを持ち、しかも正孔移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。
陽極と正孔輸送層の間に正孔注入層を設けてもよい。正孔注入層を設けることで発光素子が低駆動電圧化し、耐久寿命も向上する。
発光層は単一層、複数層のどちらでもよく、それぞれ発光材料(ホスト材料、ドーパント材料)により形成され、これはホスト材料とドーパント材料との混合物であっても、ホスト材料単独であっても、いずれでもよい。すなわち、本発明の発光素子では、各発光層において、ホスト材料もしくはドーパント材料のみが発光してもよいし、ホスト材料とドーパント材料がともに発光してもよい。電気エネルギーを効率よく利用し、高色純度の発光を得るという観点からは、発光層はホスト材料とドーパント材料の混合からなることが好ましい。
本発明において、電子輸送層とは、陰極と発光層との間にある層である。電子輸送層は単層でも複数層であってもよく、陰極もしくは発光層に接していてもいいし、接していなくてもよい。
本発明において、陰極と電子輸送層の間に電子注入層を設けてもよい。一般的に電子注入層は陰極から電子輸送層への電子の注入を助ける目的で挿入されるが、挿入する場合は、電子受容性窒素を含むヘテロアリール環構造を有する化合物を用いてもよいし、上記のドナー性材料を含有する層を用いてもよい。本発明のフェナントロリン誘導体が電子注入層に含まれていてもよい。
本発明において、電荷発生層とは、上記のタンデム構造型素子における、陽極と陰極の間にある中間層であり、電荷分離により正孔および電子を発生させる層である。電荷発生層は、一般に、陰極側のP型層と陽極側のN型層から形成される。これらの層には、効率的な電荷分離と、生じたキャリアの効率的な輸送が望まれる。
化合物[A-1]の合成
2-アセチルピリジン12.1g、8-アミノキノリン-7-カルボアルデヒド17.2g、水酸化カリウム14.0g、エタノール1000mLを混合し、窒素置換した後に加熱還流した。4.5時間後、室温に冷却した後、トルエン500mL、水1000mLを加え分液した。水層をトルエン500mLで2回抽出した後、先の有機層と合わせ、エタノールを減圧留去した。溶液を硫酸マグネシウムで乾燥し、溶媒を減圧留去した後、真空乾燥することにより、中間体[a]を23.9g得た。
化合物[A-2]の合成
3-アセチルピリジン12.1g、8-アミノキノリン-7-カルボアルデヒド17.2g、水酸化カリウム14.0g、エタノール1000mLを混合し、窒素置換した後に加熱還流した。4.5時間後、室温に冷却した後、トルエン500mL、水1000mLを加え分液した。水層をトルエン500mLで2回抽出した後、先の有機層と合わせ、エタノールを減圧留去した。溶液を無水硫酸ナトリウムで乾燥し、溶媒を減圧留去した後、真空乾燥することにより、中間体[c]を14.4g得た。
化合物[A-3]の合成
4’-クロロアセトフェノン15.5g、8-アミノキノリン-7-カルボアルデヒド17.2g、水酸化カリウム14.0g、エタノール1000mLを混合し、窒素置換した後に加熱還流した。4.5時間後、室温に冷却した後、トルエン500mL、水1000mLを加え分液した。水層をトルエン500mLで2回抽出した後、先の有機層と合わせ、エタノールを減圧留去した。溶液を無水硫酸ナトリウムで乾燥し、溶媒を減圧留去した後、真空乾燥することにより、中間体[e]を25.9g得た。
化合物[A-4]の合成
中間体[e]8.20g、3-フルオランテンボロン酸6.80g、1,4-ジオキサン282.0mL、1.27Mリン酸カリウム水溶液48.9mLを混合し、窒素置換した。この混合溶液にビス(ジベンジリデンアセトン)パラジウム(0)578mg、トリシクロヘキシルホスフィン・テトラフルオロボラン555mgを加え、2時間加熱還流した。室温に冷却した後、水300mlを加え、析出物をろ過した。真空乾燥後、テトラヒドロフラン800mLを加えて溶解し、活性炭1.29mgを加え、1時間加熱還流した。冷却後、シリカパットでろ過した。ろ液の溶媒を留去した後、得られた固体をピリジン/メタノールで再結晶した。得られた固体をろ過し、真空乾燥することにより、中間体[h]を10.9g得た。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として、HAT-CN6を5nm、正孔輸送層として、HT-1を50nm蒸着した。次に、発光層として、ホスト材料H-1、ドーパント材料D-1をドープ濃度が5重量%になるようにして20nmの厚さに蒸着した。次に、電子輸送層として化合物B-1を35nmの厚さに蒸着して積層した。次に、フッ化リチウムを0.5nm蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。この発光素子の1000cd/m2時の特性は、駆動電圧4.3V、外部量子効率4.8%であった。また初期輝度を1000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1500時間であった。なお化合物HAT-CN6、HT-1、H-1、D-1は以下に示す化合物である。
電子輸送層に表1に記載した化合物を用いた以外は実施例1と同様にして発光素子を作製し、評価した。結果を表1に示す。
電子輸送層に表1に記載した化合物を用いた以外は実施例1と同様にして発光素子を作製し、評価した。結果を表1に示す。なお、E-1~E-5は以下に示す化合物である。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として、HAT-CN6を5nm、正孔輸送層として、HT-1を50nm蒸着した。次に、発光層として、ホスト材料H-1、ドーパント材料D-1をドープ濃度が5重量%になるようにして20nmの厚さに蒸着した。次に、第1電子輸送層として化合物B-1を25nmの厚さに蒸着して積層した。さらに第2電子輸送層として電子輸送材料に化合物B-1を、ドナー性材料としてリチウムを用い、化合物B-1とリチウムの蒸着速度比が20:1になるようにして10nmの厚さに積層した。次に、フッ化リチウムを0.5nm蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。この発光素子の1000cd/m2時の特性は、駆動電圧3.9V、外部量子効率5.8%であった。また初期輝度を1000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1650時間であった。
電子輸送層に表2に記載した化合物を用いた以外は実施例13と同様にして発光素子を作製し、評価した。結果を表2に示す。
電子輸送層に表2に記載した化合物を用いた以外は実施例13と同様にして発光素子を作製し、評価した。結果を表2に示す。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として、HAT-CN6を5nm、正孔輸送層として、HT-1を50nm蒸着した。次に、発光層として、ホスト材料H-1、ドーパント材料D-1をドープ濃度が5重量%になるようにして20nmの厚さに蒸着した。さらに電子輸送層として電子輸送材料に化合物B-1を、ドナー性材料として2E-1を用い、化合物B-1と2E-1の蒸着速度比が1:1になるようにして35nmの厚さに積層した。この電子輸送層は表4では第2電子輸送層として示す。次に、フッ化リチウムを0.5nm蒸着した後、マグネシウムと銀を1000nm共蒸着して陰極とし、5×5mm角の素子を作製した。この発光素子の1000cd/m2時の特性は、駆動電圧3.9V、外部量子効率6.0%であった。また初期輝度を1000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1800時間であった。なお、2E-1は下記に示す化合物である。
電子輸送層、ドナー性材料として表3に記載した化合物を用いた以外は実施例25と同様にして発光素子を作製し、評価した。結果を表3に示す。
電子輸送層、ドナー性材料として表3に記載した化合物を用いた以外は実施例25と同様にして発光素子を作製し、評価した。結果を表3に示す。
第1電子輸送層として化合物B-1を25nmの厚さに蒸着して積層し、さらに第2電子輸送層として電子輸送材料に化合物B-1を、ドナー性材料として2E-1を用い、化合物B-1と2E-1の蒸着速度比が1:1になるようにして10nmの厚さに積層した。それ以外は実施例25と同様にして発光素子を作製した。この発光素子の1000cd/m2時の特性は、駆動電圧4.0V、外部量子効率5.9%であった。また初期輝度を1000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1950時間であった。
電子輸送層、ドナー性材料として表4に記載した化合物を用いた以外は実施例37と同様にして発光素子を作製し、評価した。結果を表4に示す。
電子輸送層、ドナー性材料として表4に記載した化合物を用いた以外は実施例37と同様にして発光素子を作製し、評価した。結果を表4に示す。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として、HAT-CN6を5nm、正孔輸送層として、HT-1を50nm蒸着した。この正孔輸送層は表6では第1正孔輸送層として示す。次に、発光層として、ホスト材料H-2、ドーパント材料D-2をドープ濃度が10重量%になるようにして20nmの厚さに蒸着した。次に、電子輸送層として化合物B-2を35nmの厚さに蒸着して積層した。次に、フッ化リチウムを0.5nm蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。この発光素子の4000cd/m2時の特性は、駆動電圧3.9V、外部量子効率10.4%であった。また初期輝度を4000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1400時間であった。なおH-2、D-2は以下に示す化合物である。
電子輸送層として表5記載の化合物を用いた以外は実施例49と同様に発光素子を作製し、評価した。結果を表5に示す。
電子輸送層として表5記載の化合物を用いた以外は実施例49と同様に発光素子を作製し、評価した。結果を表5に示す。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として、HAT-CN6を5nm、第1正孔輸送層として、HT-1を40nm蒸着した。さらに第2正孔輸送層としてHT-2を10nm蒸着した。次に、発光層として、ホスト材料H-2、ドーパント材料D-2をドープ濃度が10重量%になるようにして20nmの厚さに蒸着した。次に、電子輸送層として化合物B-2を35nmの厚さに蒸着して積層した。次に、フッ化リチウムを0.5nm蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。この発光素子の4000cd/m2時の特性は、駆動電圧3.9V、外部量子効率13.3%であった。また初期輝度を4000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1600時間であった。なお、HT-2は以下に示す化合物である。
第2正孔輸送層および電子輸送層として表5記載の化合物を用いた以外は、実施例55と同様にして素子を作製し、評価した。結果を表5に示す。なおHT-3、HT-4、HT-5は以下に示す化合物である。
第2正孔輸送層および電子輸送層として表5記載の化合物を用いた以外は、実施例55と同様にして素子を作製し、評価した。結果を表5に示す。
ITO透明導電膜を165nm堆積させたガラス基板(ジオマテック(株)製、11Ω/□、スパッタ品)を38×46mmに切断し、エッチングを行った。得られた基板を “セミコクリーン56”(商品名、フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に1時間UV-オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10-4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として、HAT-CN6を10nm、正孔輸送層として、HT-6を90nm蒸着した。次に、発光層として、ホスト材料H-1、ドーパント材料D-3をドープ濃度が5重量%になるようにして30nmの厚さに蒸着し、その上に、電子輸送層として化合物ET-1を30nmの厚さに蒸着して積層した。次にN型の電荷発生層として電子輸送材料に化合物B-1を、ドナー性材料としてリチウムを用い、化合物B-1とリチウムの蒸着速度比が20:1になるようにして10nmの厚さに積層し、その上に、P型の電荷発生層として、HT-6を10nm蒸着した。さらに、正孔注入層、正孔輸送層、発光層、電子輸送層を上記と同様の条件で積層した後、フッ化リチウムを0.5nm蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。この発光素子の1000cd/m2時の特性は、駆動電圧8.7V、外部量子効率6.9%であった。また初期輝度を1000cd/m2に設定し、定電流駆動させたところ輝度20%低下する時間は1000時間であった。なおHT-6、ET-1、D-3は以下に示す化合物である。
N型の電荷発生層の電子輸送材料として表6記載の化合物を用いた以外は、実施例70と同様にして素子を作製し、評価した。結果を表6に示す。
N型の電荷発生層の電子輸送材料として表6記載の化合物を用いた以外は、実施例70と同様にして素子を作製し、評価した。結果を表6に示す。
Claims (15)
- 下記一般式(1)で表されるフェナントロリン誘導体。
L1およびL2はそれぞれ同じでも異なっていてもよく、単結合またはフェニレン基のいずれかから選ばれる。
Bは電子受容性窒素を有する置換もしくは無置換のヘテロアリール基、Cは置換もしくは無置換の環形成炭素数が20未満であるアリール基を表す。ただし、Bはフェナントロリン骨格を有さない。
BおよびCが置換される場合、置換基としては、重水素、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、ハロゲン、シアノ基、カルボニル基、カルボキシル基、オキシカルボニル基、カルバモイル基、アミノ基、ボリル基、シリル基、フェニル基、ナフチル基、ピリジル基、キノリニル基および-P(=O)R9R10からなる群より選ばれる。これらの基は、さらに重水素、アルキル基、ハロゲン、フェニル基、ナフチル基、ピリジル基またはキノリニル基で置換されていても良い。) - R1がL1-Bで表される基であり、かつ、R8がL2-Cで表される基である請求項1に記載のフェナントロリン誘導体。
- L2がフェニレン基である請求項1または2に記載のフェナントロリン誘導体。
- Cがフルオレニル基、フェナントレニル基、ピレニル基、トリフェニレニル基またはフルオランテニル基である請求項1~3のいずれかに記載のフェナントロリン誘導体。
- Cがピレニル基またはフルオランテニル基である請求項1~4のいずれかに記載のフェナントロリン誘導体。
- Bがピリジル基、キノリニル基、イソキノリニル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基、キノキサリニル基、キナゾリニル基、ベンゾキノリニル基、アクリジニル基、ベンゾイミダゾリル基またはイミダゾピリジル基である請求項1~5のいずれかに記載のフェナントロリン誘導体。
- Bがピリジル基、キノリニル基またはイソキノリニル基である請求項1~6のいずれかに記載のフェナントロリン誘導体。
- 陽極と陰極の間に発光層を含む複数の有機層を有し、電気エネルギーにより発光する発光素子であって、前記有機層の少なくとも1層に請求項1~7のいずれかに記載のフェナントロリン誘導体を含む発光素子。
- 前記有機層に少なくとも電子輸送層が存在し、電子輸送層が請求項1~7いずれかに記載のフェナントロリン誘導体を含む請求項8記載の発光素子。
- 前記有機層に少なくとも電子注入層が存在し、電子注入層が請求項1~7いずれかに記載のフェナントロリン誘導体を含む請求項8または9に記載の発光素子。
- 前記有機層に少なくとも電荷発生層が存在し、電荷発生層が請求項1~7いずれかに記載のフェナントロリン誘導体を含むことを特徴とする請求項8~10のいずれかに記載の発光素子。
- 第一電極及び第二電極の間に少なくとも一層の有機層があり、光エネルギーを電気エネルギーに変換する光電変換素子であって、前記有機層に請求項1~7のいずれかに記載のフェナントロリン誘導体を含む光電変換素子。
- 前記有機層が光電変換層を含み、該光電変換層に前記有機層に請求項1~7のいずれかに記載のフェナントロリン誘導体を含む請求項12に記載の光電変換素子。
- 前記有機層が、第一電極及び第二電極の間に少なくとも一層の光電変換層と一層の電子取り出し層を含み、該電子取り出し層が前記有機層に請求項1~7のいずれかに記載のフェナントロリン誘導体を含む請求項12または13に記載の光電変換素子。
- 請求項12~14のいずれかに記載の光電変換素子を含むイメージセンサ。
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WO2024043018A1 (ja) * | 2022-08-22 | 2024-02-29 | 東レ株式会社 | 有機el素子、表示装置および照明装置 |
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JP6769303B2 (ja) | 2020-10-14 |
EP3252052A4 (en) | 2018-06-27 |
TW201634461A (zh) | 2016-10-01 |
US20180019407A1 (en) | 2018-01-18 |
KR102214158B1 (ko) | 2021-02-09 |
CN107207503A (zh) | 2017-09-26 |
EP3252052A1 (en) | 2017-12-06 |
EP3252052B1 (en) | 2021-05-19 |
JPWO2016121597A1 (ja) | 2017-11-02 |
TWI680130B (zh) | 2019-12-21 |
KR20170105040A (ko) | 2017-09-18 |
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