JP7508151B2 - 新規な化合物、それを含むコーティング組成物、それを含む有機発光素子およびその製造方法 - Google Patents
新規な化合物、それを含むコーティング組成物、それを含む有機発光素子およびその製造方法 Download PDFInfo
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- JP7508151B2 JP7508151B2 JP2023507455A JP2023507455A JP7508151B2 JP 7508151 B2 JP7508151 B2 JP 7508151B2 JP 2023507455 A JP2023507455 A JP 2023507455A JP 2023507455 A JP2023507455 A JP 2023507455A JP 7508151 B2 JP7508151 B2 JP 7508151B2
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Description
Yz1およびYz2は互いに同一または異なり、それぞれ独立して、直接結合、O、S、CRaRbまたはSiRcRdであり、Yz1およびYz2のいずれか一つが直接結合であると、残りの1つはO、S、CRaRbまたはSiRcRdであり、
Ra、Rb、RcおよびRdは互いに同一または異なり、それぞれ独立して、水素;重水素;置換または非置換のアルキル基;置換または非置換のアリール基;置換または非置換のヘテロアリール基であるか、隣接した基と結合して置換または非置換の環を形成し、
Cy1およびCy2は互いに同一または異なり、それぞれ独立して、置換または非置換のベンゼン環;または置換または非置換のナフタレン環であり、
Lz1~Lz3は互いに同一または異なり、それぞれ独立して、直接結合;または置換または非置換のアリーレン基であり、
Lz11およびLz12は互いに同一または異なり、それぞれ独立して、直接結合;置換または非置換のアルキレン基;または置換または非置換のアリーレン基であり、
Xz1およびXz2は互いに同一または異なり、それぞれ独立して、硬化性基であり、
Rz1およびRz2は互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
Rz3およびRz4は互いに同一または異なり、それぞれ独立して、水素;重水素;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
lz1~lz3はそれぞれ0または1であり、
n1およびn2はそれぞれ0~7の整数であり、n1およびn2がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
n3およびn4はそれぞれ0~4の整数であり、n3およびn4がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m1およびm2はそれぞれ独立に1~5の整数であり、
m1+n3は5以下であり、m2+n4は5以下である。
Yz1およびYz2は互いに同一または異なり、それぞれ独立して、直接結合、O、S、CRaRbまたはSiRcRdであり、Yz1およびYz2のいずれか一つが直接結合であると、残りの1つはO、S、CRaRbまたはSiRcRdであり、
Ra、Rb、RcおよびRdは互いに同一または異なり、それぞれ独立して、水素;重水素;置換または非置換のアルキル基;置換または非置換のアリール基;置換または非置換のヘテロアリール基であるか、隣接した基と結合して置換または非置換の環を形成し、
Cy1およびCy2は互いに同一または異なり、それぞれ独立して、置換または非置換のベンゼン環;または置換または非置換のナフタレン環であり、
Lz1~Lz3は互いに同一または異なり、それぞれ独立して、直接結合;または置換または非置換のアリーレン基であり、
Lz11およびLz12は互いに同一または異なり、それぞれ独立して、直接結合;置換または非置換のアルキレン基;または置換または非置換のアリーレン基であり、
Xz1およびXz2は互いに同一または異なり、それぞれ独立して、硬化性基であり、
Rz1およびRz2は互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
Rz3およびRz4は互いに同一または異なり、それぞれ独立して、水素;重水素;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
lz1~lz3はそれぞれ0または1であり、
n1およびn2はそれぞれ0~7の整数であり、n1およびn2がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
n3およびn4はそれぞれ0~4の整数であり、n3およびn4がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m1およびm2はそれぞれ独立に1~5の整数であり、
m1+n3は5以下であり、m2+n4は5以下である。
Lz1~Lz3、Lz11、Lz12、Xz1、Xz2、Rz1~Rz4、Yz1、Yz2、Cy1、Cy2、lz1~lz3、n1~n4、m1およびm2の定義は化学式1と同じである。
Lz11、Lz12、Xz1、Xz2、Rz1~Rz4、Cy1、Cy2、Yz1、Yz2、n1~n4、m1およびm2の定義は化学式1と同様であり、
Rz21およびRz22は互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
m21は0~4の整数であり、m22は0~6の整数であり、m21およびm22がそれぞれ2以上の整数である場合、2以上の括弧内の置換基は互いに同一または異なる。
Rz11~Rz13は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
m11は0~4の整数であり、m12およびm13はそれぞれ0~6の整数であり、m11~m13がそれぞれ2以上の整数である場合、2以上の括弧内の置換基は互いに同一または異なる。
前記有機物層は、発光層および正孔注入層を含み、
前記正孔注入層は、前記化学式1の化合物、前記コーティング組成物またはその硬化物を含む有機発光素子を提供する。
(1)アノード/正孔輸送層/発光層/カソード
(2)アノード/正孔注入層/正孔輸送層/発光層/カソード
(3)アノード/正孔注入層/正孔バッファ層/正孔輸送層/発光層/カソード
(4)アノード/正孔輸送層/発光層/電子輸送層/カソード
(5)アノード/正孔輸送層/発光層/電子輸送層/電子注入層/カソード
(6)アノード/正孔注入層/正孔輸送層/発光層/電子輸送層/カソード
(7)アノード/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/カソード
(8)アノード/正孔注入層/正孔バッファ層/正孔輸送層/発光層/電子輸送層/カソード
(9)アノード/正孔注入層/正孔バッファ層/正孔輸送層/発光層/電子輸送層/電子注入層/カソード
(10)アノード/正孔輸送層/電子遮断層/発光層/電子輸送層/カソード
(11)アノード/正孔輸送層/電子遮断層/発光層/電子輸送層/電子注入層/カソード
(12)アノード/正孔注入層/正孔輸送層/電子遮断層/発光層/電子輸送層/カソード
(13)アノード/正孔注入層/正孔輸送層/電子遮断層/発光層/電子輸送層/電子注入層/カソード
(14)アノード/正孔輸送層/発光層/正孔遮断層/電子輸送層/カソード
(15)アノード/正孔輸送層/発光層/正孔遮断層/電子輸送層/電子注入層/カソード
(16)アノード/正孔注入層/正孔輸送層/発光層/正孔遮断層/電子輸送層/カソード
(17)アノード/正孔注入層/正孔輸送層/発光層/正孔遮断層/電子輸送層/電子注入層/カソード
(18)アノード/正孔注入層/正孔輸送層/発光層/正孔遮断層/電子輸送層/電子注入層/カソード/カプセル
(19)アノード/正孔注入層/第1の正孔輸送層/第2の正孔輸送層/発光層/正孔遮断層/電子輸送層/電子注入層/カソード/カプセル
<製造例1.化合物1の製造>
1)中間体1-1の合成
化合物1のNMR測定値:1H NMR(500MHz,DMSO-d6)δ8.07(dd,1H)、7.92(d,1H)、7.82(dd,4H)、7.46(dd,4H)、7.39-7.24(m,10H)、7.21(dd,1H)、7.10(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
化合物2のNMR測定値:1H NMR(500MHz,DMSO-d6)δ8.11(s,1H)、8.07(dd,1H)、7.85(d,1H)、7.82(dd,4H)、7.46(dd,4H)、7.39-7.20(m,10H)、7.08(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
化合物3のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.95(dd,1H)、7.90(dd,1H)、7.84(dd,4H)、7.46(dd,4H)、7.39-7.20(m,11H)、7.08(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)、1.68(s,6H)
1)中間体4-1の製造
化合物4のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.07(dd,1H)、7.92(d,1H)、7.63(dd,4H)、7.39-7.24(m,10H)、7.21(dd,1H)、7.10(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、5.75(d,2H)、5.21(d,2H)
化合物5のNMR測定値:1H NMR(500MHz、DMSO-d6)δ7.95(dd,1H)、7.90(dd,1H)、7.84(dd,4H)、7.39-7.20(m,11H)、7.08(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、5.75(d,2H)、5.21(d,2H)、1.68(s,6H)
1)中間体6-1の製造
化合物6のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.07(dd,1H)、7.92(d,1H)、7.63(dd,4H)、7.63-7.50(m,12H)、7.40-7.27(m,17H)、6.97-6.80(m,10H)、6.72(dd,2H)、5.75(d,2H)、5.21(d,2H)
1)中間体7-1の合成
化合物7のNMR測定値:1H NMR(500MHz,DMSO-d6)δ8.04(dd,1H)、7.90(d,1H)、7.78(dd,4H)、7.48-7.41(m,6H)、7.34(t,2H)、7.28-7.18(m,8H)、7.14-7.05(m,5H)、6.97(dd,4H)、6.88-6.81(m,8H)、6.72(dd,2H)、6.60(dd,4H)、5.74(d,2H)、5.21(d,2H)
化合物8のNMR測定値:1H NMR(500MHz,DMSO-d6)δ7.95(dd,1H)、7.90(dd,1H)、7.84(dd,4H)、7.46(dd,4H)、7.39-7.20(m,11H)、7.08(m,2H)、6.97-6.85(m,16H)、6.73(dd,2H)、6.60(dd,4H)、5.75(d,2H)、5.21(d,2H)、1.68(s,6H)
1)中間体9-1の合成
化合物9のNMR測定値:1H NMR(500MHz,DMSO-d6)δ8.04(dd,1H)、7.90(d,1H)、7.78(dd,4H)、7.48-7.41(m,6H)、7.34(t,2H)、7.28-7.18(m,8H)、7.14-7.05(m,5H)、6.97-6.88(m,6H)、6.72(dd,2H)、6.60(dd,4H)、5.74(d,2H)、5.21(d,2H)
化合物10のNMR測定値:1H NMR(500MHz、DMSO-d6)δ7.95(dd,1H)、7.90(dd,1H)、7.82(dd,4H)、7.46(dd,4H)、7.39-7.20(m,11H)、7.08(m,2H)、6.90-6.83(m,10H)、6.72(dd,2H)、6.64(d,4H)、5.75(d,2H)、5.21(d,2H)、1.68(s,6H)
1)中間体11-1の合成
化合物11のNMR測定値:1H NMR(500MHz、DMSO-d6)8.07(dd,1H)、7.92(d,1H)、7.82(dd,4H)、7.46(dd,4H)、7.39-7.24(m,10H)、7.21(dd,1H)、7.10(m,2H)、6.97-6.83(m,16H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)、2.31(s,6H)
(1)中間体12-1の合成
化合物12のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.02(dd,1H)、7.91(d,1H)、7.79(dd,4H)、7.46(dd,4H)、7.42-7.22(m,14H)、7.21(dd,1H)、7.10(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
(1)中間体13-1の合成
化合物13のNMR測定値:1H NMR(500mHz、DMSO-d6)δ8.05(s,1H)、8.00(dd,1H)、7.85(d,1H)、7.80(dd,4H)、7.46(dd,4H)、7.39-7.20(m,14H)、7.08(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
(1)中間体14-1の合成
化合物14のNMR測定値:1H NMR(500mHz、DMSO-d6)δ8.05(dd,1H)、7.92(d,1H)、7.79(dd,4H)、7.46(dd,4H)、7.42-7.22(m,14H)、7.21(dd,1H)、7.10(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
(1)中間体15-1の合成
化合物15のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.05(dd,1H)、7.94(d,1H)、7.75(dd,4H)、7.46(dd,4H)、7.42-7.22(m,16H)、7.15(dd,1H)、7.10(m,2H)、7.01-6.80(m,24H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
化合物16のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.03(dd,1H)、7.92(d,1H)、7.74(dd,4H)、7.45(dd,4H)、7.42-7.22(m,12H)、7.15(dd,1H)、7.10(m,2H)、7.01-6.80(m,24H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
化合物17のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.02(dd,1H)、7.94(dd,1H)、7.85(dd,4H)、7.46(dd,4H)、7.39-7.20(m,11H)、7.08(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)、1.69(s,6H)
(1)中間体18-1の合成
化合物18のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.04(dd,1H)、7.93(d,1H)、7.74(dd,4H)、7.46(dd,4H)、7.42-7.22(m,16H)、7.15(dd,1H)、7.10(m,2H)、7.01-6.80(m,24H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)
(1)中間体19-1の合成
化合物19のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.02(dd,1H)、7.95(dd,1H)、7.80(dd,4H)、7.46(dd,4H)、7.40-7.20(m,15H)、7.08(m,2H)、6.97-6.83(m,18H)、6.72(dd,2H)、6.65(d,4H)、5.75(d,2H)、5.21(d,2H)、1.69(s,6H)
化合物20のNMR測定値:1H NMR(500MHz、DMSO-d6)δ8.00(d,1H)、7.92(d,1H)、7.83(d,4H)、7.50(m,1H)、7.44-7.28(m,10H)、7.28(t,2H)、7.18(dd,1H)、7.13(m,2H)、7.08-6.97(m,15H)、6.92(d,4H)、6.84(t,4H)、6.68(dd,2H)、5.71(d,2H)、5.19(d,2H)
化合物21のNMR測定値:1H NMR(500MHz、DMSO-d6)δ7.77(m,4H)、7.57(m,2H)、7.51-7.46(m,5H)、7.36-7.29(m,5H)、7.24(t,2H)、7.03-6.68(m,29H)、5.74(d,2H)、5.20(d,2H)
<実施例1>
ITO(indium tin oxide)が1,500Åの厚さで薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れ、超音波で洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)の製品を使用し、蒸留水としてはミリポア社(Millipore Co.)の製品のフィルター(Filter)で2次にかけてろ過されたた蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間進行した。蒸留水洗浄が終わった後、イソプロピル、アセトンの溶剤で超音波洗浄をして乾燥させた後、前記基板を5分間洗浄した後、グローブボックスで基板を輸送させた。
正孔注入層の製造時、前記化合物1の代わりに下記の表1に記載の化合物を用いたことを除いては、前記実施例1と同様の方法で有機発光素子を製造した。
<比較実験例1~4>
正孔注入層の製造時に、前記化合物1の代わりに下記の表1に記載のように、下記の化合物CE1~CE4のうちいずれか1つの化合物を用いたことを除いては、前記実施例1と同様の方法で有機発光素子を製造した。
201 ・・・第1の電極
301 ・・・正孔注入層
401 ・・・正孔輸送層
501 ・・・発光層
601 ・・・電子注入および輸送層
701 ・・・第2の電極
Claims (12)
- 下記の化学式1で表される化合物:
前記化学式1において、
Yz1およびYz2は互いに同一または異なり、それぞれ独立して、直接結合、O、S、CRaRbまたはSiRcRdであり、Yz1およびYz2のいずれか一つが直接結合であると、残りの1つはO、S、CRaRbまたはSiRcRdであり、
Ra、Rb、RcおよびRdは互いに同一または異なり、それぞれ独立して、水素;重水素;置換または非置換のアルキル基;置換または非置換のアリール基;置換または非置換のヘテロアリール基であるか、隣接した基と結合して置換または非置換の環を形成し、
Cy1およびCy2は互いに同一または異なり、それぞれ独立して、置換または非置換のベンゼン環;または置換または非置換のナフタレン環であり、
Lz1~Lz3は互いに同一または異なり、それぞれ独立して、直接結合;または置換または非置換のアリーレン基であり、
Lz11およびLz12は互いに同一または異なり、それぞれ独立して、置換または非置換のアリーレン基であり、
Xz1およびXz2は互いに同一または異なり、それぞれ独立して、下記の構造からなる群から選ばれるいずれか一つである、硬化性基であり、
Rz1およびRz2は互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
Rz3およびRz4は互いに同一または異なり、それぞれ独立して、水素;重水素;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
lz1~lz3はそれぞれ0または1であり、
n1およびn2はそれぞれ0~7の整数であり、n1およびn2がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
n3およびn4はそれぞれ0~4の整数であり、n3およびn4がそれぞれ2以上の場合、2以上の括弧内の置換基は互いに同一または異なり、
m1およびm2はそれぞれ独立に1~5の整数であり、
m1+n3は5以下であり、m2+n4は5以下である。 - 前記化学式1は、下記の化学式2で表されるものである、請求項1に記載の化合物:
Lz1~Lz3、Lz11、Lz12、Xz1、Xz2、Rz1~Rz4、Yz1、Yz2、Cy1、Cy2、lz1~lz3、n1~n4、m1およびm2の定義は、前記化学式1と同様である。 - 前記化学式1は、下記の化学式3~式5のいずれかで表されるものである、請求項1に記載の化合物:
Lz11、Lz12、Xz1、Xz2、Rz1~Rz4、Cy1、Cy2、Yz1、Yz2、n1~n4、m1およびm2の定義は化学式1と同様であり、
Rz21およびRz22は互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
m21は0~4の整数であり、m22は0~6の整数であり、m21およびm22がそれぞれ2以上の整数である場合、2以上の括弧内の置換基は互いに同一または異なる。 - 前記Cy1およびCy2は、互いに同一または異なり、それぞれ独立して、下記の構造のいずれか一つで表される、請求項1に記載の化合物:
Rz11~Rz13は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;置換または非置換のアルキル基;置換または非置換のアルコキシ基;置換または非置換のアリール基;または置換または非置換のヘテロアリール基であり、
m11は0~4の整数であり、
m12およびm13はそれぞれ0~6の整数であり、m11~m13がそれぞれ2以上の整数である場合、2以上の括弧内の置換基は互いに同一または異なる。 - Lz11およびLz12が互いに同一または異なり、それぞれが独立して直接結合;置換または非置換の炭素数1~20のアルキレン基;または、置換または非置換の炭素数6~30のアリーレン基である、請求項1に記載の化合物。
- Ra、Rb、RcおよびRdは、互いに同一または異なり、それぞれ独立して、置換または非置換のメチル基;または置換または非置換のフェニル基であるか、隣接した基と結合して置換または非置換のフルオレン環;または、置換または非置換のキサンテン環を形成するものである、請求項1に記載の化合物。
- 前記化学式1の化合物は、以下の化合物からなる群から選択されるいずれかである、請求項1に記載の化合物:
- 請求項1~7のいずれか一項に記載の化合物を含むコーティング組成物。
- 第1の電極;
第2の電極;および
前記第1の電極と前記第2の電極との間に設けられる少なくとも1層の有機物層を含み、
前記1層以上の有機物層の少なくとも1層は、請求項8に記載のコーティング組成物またはその硬化物を含むものである、有機発光素子。 - 前記コーティング組成物またはその硬化物を含む有機物層は、正孔輸送層または正孔注入層である、請求項9に記載の有機発光素子。
- 第1の電極を準備する段階;
前記第1の電極上に1層以上の有機物層を形成する段階;および
前記1層以上の有機物層上に第2の電極を形成する段階を含み、
前記1層以上の有機物層を形成する段階は、請求項8に記載のコーティング組成物を用いて有機物層を形成する段階を含むものである、有機発光素子の製造方法。 - 前記コーティング組成物を用いて有機物層を形成する段階は、
前記第1の電極または1層以上の有機物層上に前記コーティング組成物をコーティングする段階;および
前記コーティングされたコーティング組成物を熱処理または光処理する段階を含むものである、請求項11に記載の有機発光素子の製造方法。
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