JP6724211B2 - 安定化されたイミダゾフェナントリジン材料 - Google Patents
安定化されたイミダゾフェナントリジン材料 Download PDFInfo
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- JP6724211B2 JP6724211B2 JP2019090589A JP2019090589A JP6724211B2 JP 6724211 B2 JP6724211 B2 JP 6724211B2 JP 2019090589 A JP2019090589 A JP 2019090589A JP 2019090589 A JP2019090589 A JP 2019090589A JP 6724211 B2 JP6724211 B2 JP 6724211B2
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Description
I.定義
II.配位子
IV.デバイス
(A)アノード/正孔輸送層/発光層/電子輸送層/カソード;
(B)アノード/正孔輸送層/発光層/ブロック層/電子輸送層/カソード;
(C)アノード/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/カソード;
(D)アノード/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/カソード;
(E)アノード/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/カソード;
A.発光層
発光材料:
B.ホスト材料
正孔輸送ホスト材料
C.膜厚
D.層構成
E.正孔注入層及び正孔輸送層
F.電子注入層及び電子輸送層
B.2−ブロモ−4−クロロブタナールの合成:
C.4−ブロモフェナントリジン−6−アミンの合成:
D.5−ブロモ−3−(2−クロロエチル)イミダゾ[1,2−f]フェナントリジンの合成:
E.3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
B.3,5−ジブロモイミダゾ[1,2−f]フェナントリジンの合成:
C.5−ブロモ−3−((クロロメチル)ジメチルシリル)イミダゾ[1,2−f]フェナントリジンの合成:
D.4,4−ジメチル−3,4−ジヒドロ−1,2a1−ジアザ−4−シラベンゾ[fg]アセアントリレン及び3,3−ジメチル−3,4−ジヒドロ−1,2a1−ジアザ−3−シラベンゾ[fg]アセアントリレンの合成:
aR1=Σ||Fo|−|Fc||/Σ|Fo|;wR2=[Σ[w(Fo 2−Fc 2)2]/Σ[w(Fo 2)2]]1/2;GOF=[Σw(|Fo|−|Fc|)2/(n−m)]1/2
B.5−メトキシ−2−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ベンゾニトリルの合成:
C.4−ブロモ−2−イソプロピル−8−メトキシフェナントリジン−6−アミンの合成:
D.6−イソプロピル−10−((9−(4−イソプロピルピリジン−2−イル)−9H−カルバゾール−2−イル)オキシ)−3,4ジヒドロ−ジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
E.6−イソプロピル−10−メトキシ−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
F.6−イソプロピル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−10−オールの合成:
G.4’−ブロモ−2−ニトロ−1,1’−ビフェニルの合成:
H.2−ブロモ−9H−カルバゾールの合成:
I.2−ブロモ−9−(4−イソプロピルピリジン−2−イル)−9H−カルバゾールの合成:
J.6−イソプロピル−10−((9−(4−イソプロピルピリジン−2−イル)−9H−カルバゾール−2−イル)オキシ)−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
K.6−イソプロピル−10−((9−(4−イソプロピルピリジン−2−イル)−9H−カルバゾール−2−イル)オキシ)−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの白金(II)錯体の合成:
B.3−ブロモイミダゾ[1,2−f]フェナントリジンの合成
C.tert−ブチル2−(イミダゾ[1,2−f]フェナントリジン−3−イル)アセテートの合成
D.メチル2−(イミダゾ[1,2−f]フェナントリジン−3−イル)アセテートハイドロクロライドの合成
E.メチル2−(イミダゾ[1,2−f]フェナントリジン−3−イル)−2−プロパン酸メチルの合成
F.2−(イミダゾ[1,2−f]フェナントリジン−3−イル)−2−メチルプロパン酸の合成
G.2−(イミダゾ[1,2−f]フェナントリジン−3−イル)−2−メチルプロパノイルクロライドの合成
H.3,3−ジメチルジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−4(3H)−オンの合成
I.3,3−ジメチル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−4−オールの合成
J.o−(3,3−ジメチル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−4−イル)S−メチルカーバノジチオエート
K.3,3−ジメチル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成
L.(3−クロロプロピル)(メチル)スルファンの合成
N.化合物35の合成
実施例6:スキーム6に従って、化合物48の合成を行った。
B.8−メチルイミダゾ[1,2−f]フェナントリジンの合成:
C.3−ブロモ−8−メチルイミダゾ[1,2−f]フェナントリジンの合成
D.8−メチル−3−(2−メチルプロプ−1−エン−1−イル)イミダゾ[1,2−f]フェナントリジンの合成:
E.4,4,7−トリメチル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
F.2−ブロモ−4,4,7−トリメチル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
G.2,4,4,7−テトラメチル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
H.化合物49の合成:
B.8−クロロイミダゾ[1,2−f]フェナントリジンの合成:
C.8−フェニルイミダゾ[1,2−f]フェナントリジンの合成:
D.3−ブロモ−8−フェニルイミダゾ[1,2−f]フェナントリジンの合成:
E.3−(2−メチルプロプ−1−エン−1−イル)−8−フェニルイミダゾ[1,2−f]フェナントリジンの合成:
F.4,4−ジメチル−7−フェニル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
G.化合物50の合成:
B.4−((トリイソプロピルシリル)オキシ)アニリンの合成:
C.2,6−ジブロモ−4−((トリイソプロピルシリル)オキシ)アニリンの合成:
D.4−ブロモ−8−メトキシ−2−((トリイソプロピルシリル)オキシ)フェナントリジン−6−アミンの合成:
E.5−ブロモ−3−(2−クロロエチル)−11−メトキシ−7−((トリイソプロピルシリル)オキシ)イミダゾ[1,2−f]フェナントリジンの合成:
F.10−メトキシ−6−((トリイソプロピルシリル)オキシ)−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
G.10−メトキシ−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−6−オールの合成:
H.10−メトキシ−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−6−イル トリフルオロメタンスルホネートの合成:
I.10−メトキシ−6−フェニル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
J.6−フェニル−3,4−ジヒドロジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジン−10−オールの合成:
K.10−((9−(4−イソプロピルピリジン−2−イル)−9H−カルバゾール−2−イル)オキシ)−6−フェニル−3,4−ジヒドロ−ジベンゾ[b,ij]イミダゾ[2,1,5−de]キノリジンの合成:
L.化合物108の合成:
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子ブロッキング層
135 発光層
140 正孔ブロッキング層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第一の導電層
164 第二の導電層
200 反転させたOLED、デバイス
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
Claims (24)
- 下記の式(2)で表されることを特徴とする化合物。
式(2)
A1及びA2は、それぞれ、2個〜3個の連結原子を有する第1の連結基であり;前記連結原子は、それぞれ独立して、C、Si、O、S、N、B、又はこれらの組合せからなる群から選択され、R1b〜R1f、R2b〜R2f、Rab、Rac、Rga、及びRgbは独立して、水素、アルキル、アルケニル、アルキニル、アラルキル、CN、CF3、CO2R、C(O)R、C(O)NR2、NR2、NO2、OR、SR、SO2、SOR、SO3R、ハロゲン、アリール、ヘテロアリール、置換されたアリール、置換されたヘテロアリール、又は複素環基から選択され;
Rは、H、ハロゲン、アルキル、アルケニル、アルキニル、ヘテロアルキル、アラルキル、アリール、又はヘテロアリールから選択され;
R ab 及びRac及び/又はRga及びRgbは、結合し、それぞれ独立して、B、N、P、O、S、Se、C、Si、Ge、又はこれらの組合せからなる群から選択される1個〜3個の連結原子を有する第2の連結基を形成する。) - 前記第1の連結基A1及びA2が、それぞれ独立して、−CR’R’’−CR’R’’−、−CR’R’’−CR’R’’−CR’R’’−、−CR’R’’−NR’’−、−CR’=CR’−CR’R’’−、−O−SiR’R’’−、−CR’R’’−S−、−CR’R’’−O−、−C−SiR’R’’−からなる群から選択され、R’及びR’’は、独立して、H、1個〜6個の炭素原子を有するアルキル、フェニル、及び置換されたフェニルである、又はR’及びR’’は、結合し、飽和5員環、又は飽和6員環、及びこれらの組合せを形成する請求項1に記載の化合物。
- 前記化合物が三重項励起状態を有し、前記化合物が三重項励起状態にあるとき、前記連結基が、N2とC1bとの間の結合を開裂から安定化させる請求項1に記載の化合物。
- 前記化合物が、500nm未満のピーク発光波長を有する請求項1に記載の化合物。
- 前記化合物が、480nm未満のピーク発光波長を有する請求項1に記載の化合物。
- 前記化合物が、400nm〜500nmの範囲のピーク発光波長を有する請求項1に記載の化合物。
- 前記第1の連結基A1及びA2が、それぞれ独立して、−CH2−CH2−、−CH2−CH2−CH2−、−CHR’−CHR’’−、−CR’R’’−CH2−、−CR’R’’−CR’R’’−、−CH2−CH2−CH2−、−CH2−S−、−S−CH2−、−O−SiR’R’’−、及び−SiR’R’’−O−から選択され、R’及びR’’が、メチル又はフェニルである請求項1に記載の化合物。
- 前記第2の連結基が、独立して、BR、NR、PR、O、S、Se、C=O、S=O、SO2、CRR’’’、−CRR’’’−CRR’’’−、SiRR’’’、GeRR’’’、−CR’R’’−CR’R’’−、−CR’R’’−CR’R’’−CR’R’’−、−CR’R’’−NR’’−、−CR’=CR’−CR’R’’−、−O−SiR’R’’−、−CR’R’’−S−、−CR’R’’−O−、及び−C−SiR’R’’−から選択され、R、R’、R’’、又はR’’’は、それぞれ独立して、H、ハロ、アルキル、アルケニル、アルキニル、ヘテロアルキル、アラルキル、アリール、及びヘテロアリールから選択される請求項1に記載の化合物。
- 前記化合物が、下記化合物のいずれかである請求項1に記載の化合物。
- 第1の有機発光デバイスを含むデバイスであって、第1の有機発光デバイスが、
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、請求項1から9のいずれかに記載の化合物を含む有機層とを含むことを特徴とするデバイス。 - 前記有機層が、カルバゾール、ジベンゾチフェン、ジベンゾフラン、アザカルバゾール、アザ−ジベンゾチオフェン、及びアザ−ジベンゾフランからなる群から選択される少なくとも1つの基を含むホストを含む請求項10に記載のデバイス。
- 下記の式(3)で表されることを特徴とする化合物。
式(3)
Aは、2個〜3個の連結原子を有する第1の連結基であり、前記連結原子は、それぞれ独立して、C、Si、O、S、N、B、又はこれらの組合せからなる群から選択され;
L2及びL3は、独立して、単結合、BR、NR、PR、O、S、Se、C=O、S=O、SO2、CRR’、SiRR’、及びGeRR’からなる群から選択され;
R1a〜R1f及びR3a〜R3f、R及びR’は、それぞれ独立して、水素、アルキル、アルケニル、アルキニル、アラルキル、CN、CF3、CO2R、C(O)R、C(O)NR2、NR2、NO2、OR、SR、SO2、SOR、SO3R、ハロゲン、アリール、ヘテロアリール、置換されたアリール、置換されたヘテロアリール、又は複素環基から選択され;2つの隣接するR1f、R3a、R3c、R3d、R、及びR’は、結合して、縮合環を形成してもよく;
L 2 及びR1f、又はL2及びR3a、又はL2及びR1fとR3aの両方は、結合して、1つ以上の縮合環を形成してもよく、L3及びR3c、L3及びR3d、又はL3及びR3cとR3dの両方、L3及びR3c、L3及びR3d、又はL3及びR3cとR3dの両方は、結合して、1つ以上の縮合環を形成してもよい。) - 前記第1の連結基が、独立して、−CR’R’’−CR’R’’−、−CR’R’’−CR’R’’−CR’R’’−、−CR’R’’−NR’’−、−CR’=CR’−CR’R’’−、−O−SiR’R’’−、−CR’R’’−S−、−CR’R’’−O−、−C−SiR’R’’−からなる群から選択され、R’及びR’’は、独立して、H、1個〜6個の炭素原子を有するアルキル、フェニル、及び置換されたフェニルである、又はR’及びR’’は、結合し、飽和5員環、又は飽和6員環、及びこれらの組合せを形成する請求項12に記載の化合物。
- 前記化合物が三重項励起状態を有し、前記化合物が三重項励起状態にあるとき、前記連結基が、N2とC1bとの間の結合を開裂から安定化させる請求項12に記載の化合物。
- 前記化合物が、500nm未満のピーク発光波長を有する請求項12に記載の化合物。
- 前記化合物が、480nm未満のピーク発光波長を有する請求項12に記載の化合物。
- 前記化合物が、400nm〜500nmの範囲のピーク発光波長を有する請求項12に記載の化合物。
- 前記第1の連結基が、−CH2−CH2−、−CH2−CH2−CH2−、−CHR’−CHR’’−、−CR’R’’−CH2−、−CR’R’’−CR’R’’−、−CH2−CH2−CH2−、−CH2−S−、−S−CH2−、−O−SiR’R’’−、及び−SiR’R’’−O−から選択され、R’及びR’’が、メチル又はフェニルである請求項12に記載の化合物。
- L2及びL3が、独立して、BR、NR、PR、O、S、Se、C=O、S=O、SO2、CRR’、SiRR’、及びGeRR’からなる群から選択される請求項12に記載の化合物。
- R1f又はR3a及びR又はR’が、結合して、縮合環を形成する請求項12に記載の化合物。
- R3c又はR3d及びR又はR’が、結合して、縮合環を形成する請求項12に記載の化合物。
- 下記からなる群から選択される請求項12に記載の化合物。
- 第1の有機発光デバイスを含むデバイスであって、第1の有機発光デバイスが、
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、請求項12から22のいずれかに記載の化合物を含む有機層とを含むことを特徴とするデバイス。 - 前記有機層が、カルバゾール、ジベンゾチフェン、ジベンゾフラン、アザカルバゾール、アザ−ジベンゾチオフェン、及びアザ−ジベンゾフランからなる群から選択される少なくとも1つの基を含むホストを含む請求項23に記載のデバイス。
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