JP7004804B2 - コーティング組成物、これを用いた有機発光素子およびその製造方法 - Google Patents
コーティング組成物、これを用いた有機発光素子およびその製造方法 Download PDFInfo
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- JP7004804B2 JP7004804B2 JP2020514741A JP2020514741A JP7004804B2 JP 7004804 B2 JP7004804 B2 JP 7004804B2 JP 2020514741 A JP2020514741 A JP 2020514741A JP 2020514741 A JP2020514741 A JP 2020514741A JP 7004804 B2 JP7004804 B2 JP 7004804B2
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 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
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Description
Lは、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
T1~T6は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
X1~X4は、互いに同一または異なり、それぞれ独立に、光硬化性基または熱硬化性基であり、
R1~R20のうちの少なくとも1つは、F、シアノ基、または置換もしくは非置換のフルオロアルキル基であり、少なくとも他の1つは、光硬化性基または熱硬化性基であり、
残りのR1~R20は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトロ基;-C(O)R100;-OR101;-SR102;-SO3R103;-COOR104;-OC(O)R105;-C(O)NR106R107;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R100~R107は、互いに同一または異なり、それぞれ独立に、水素;重水素;または置換もしくは非置換のアルキル基であり、
n1およびn2は、それぞれ独立に、0~4の整数であり、
n3およびn4は、それぞれ独立に、0~3の整数であり、
n1~n4がそれぞれ2以上の場合、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、0~12の整数である。
Lは、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
T1~T6は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
X1~X4は、互いに同一または異なり、それぞれ独立に、光硬化性基または熱硬化性基であり、
R1~R20のうちの少なくとも1つは、F、シアノ基、または置換もしくは非置換のフルオロアルキル基であり、少なくとも他の1つは、光硬化性基または熱硬化性基であり、
残りのR1~R20は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトロ基;-C(O)R100;-OR101;-SR102;-SO3R103;-COOR104;-OC(O)R105;-C(O)NR106R107;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R100~R107は、互いに同一または異なり、それぞれ独立に、水素;重水素;または置換もしくは非置換のアルキル基であり、
n1およびn2は、それぞれ独立に、0~4の整数であり、
n3およびn4は、それぞれ独立に、0~3の整数であり、
n1~n4がそれぞれ2以上の場合、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、0~12の整数である。
A1~A3は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数1~6のアルキル基である。
T1~T6、X1~X4、L、Ar1、Ar2、n1~n4、m1およびm2の定義は、化学式1と同じである。
Zは、重水素;ハロゲン基;ニトロ基;シアノ基;アミノ基;-C(O)R100;-OR101;-SR102;-SO3R103;-COOR104;-OC(O)R105;-C(O)NR106R107;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
lは、1~4の整数であり、lが2以上の場合、Zは、互いに同一または異なり、
R100~R107は、互いに同一または異なり、それぞれ独立に、水素;重水素;または置換もしくは非置換のアルキル基である。
R201は、水素;重水素;または置換もしくは非置換のアルキル基であり、
R30~R32は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であるか、隣接した基は、互いに結合して環を形成し、
pは、0~10の整数であり、
aは、1または2であり、bは、0または1であり、a+b=2である。
X100~X143は、互いに同一または異なり、それぞれ独立に、水素;シアノ基;ニトロ基;ヒドロキシ基;ハロゲン基;-COOR201;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアミン基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のフルオロアルキル基;または置換もしくは非置換のアリール基であるか、光硬化性基または熱硬化性基であり、
R201は、置換もしくは非置換のアルキル基であり、
R30~R32は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であるか、隣接した基は、互いに結合して環を形成する。
R33~R41は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシクロアルキル基;または置換もしくは非置換のアリール基であり、
L1は、置換もしくは非置換のアリーレン基であり、
L2は、直接結合;O;S;またはC=Oであり、
R42は、置換もしくは非置換のカルボニル基であり、sは、0または1である。
製造例.コーティング組成物の製造
コーティング組成物1は、下記のH1 16mgと下記のD1 4mgをトルエン980mgに溶かして製造し、コーティング組成物2~9および比較コーティング組成物1~5は、下記表1に記載の化合物を用いて製造した。
実施例1.有機発光素子1の製造
ITO透明電極上にコーティング組成物1をITO表面上にスピンコーティングし、220℃で30分間熱処理(硬化)して30nmの厚さに正孔注入層を形成した。前記形成された正孔注入層上にα-NPD(N,N-ジ(1-ナフチル)-N,N-ジフェニル-(1,1’-ビフェニル)-4,4’-ジアミン)が2wt%含まれたトルエン(toluene)インクをスピンコーティングして正孔輸送層を40nmの厚さに形成した。この後、真空蒸着機に搬送した後、前記正孔輸送層上にANDとDPAVBiの重量比(AND:DPAVBi)を20:1として20nmの厚さに真空蒸着して発光層を形成した。前記発光層上にBCPを35nmの厚さに真空蒸着して電子注入および輸送層を形成した。前記電子注入および輸送層上に順次、1nmの厚さにLiFと100nmの厚さにアルミニウムを蒸着してカソードを形成した。
コーティング組成物1の代わりにコーティング組成物2を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物3を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物4を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物5を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物6を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物7を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物8を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりにコーティング組成物9を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりに比較コーティング組成物1を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりに比較コーティング組成物2を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりに比較コーティング組成物3を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりに比較コーティング組成物4を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
コーティング組成物1の代わりに比較コーティング組成物5を用いたことを除いて、実施例1と同様の方法で有機発光素子を製造した。
201:アノード
301:正孔注入層
401:正孔輸送層
501:発光層
601:電子注入および電子輸送を同時に行う層
701:カソード
Claims (8)
- 下記化学式1-1で表される化合物および下記化学式2で表される化合物を含むコーティング組成物:
Lは、置換もしくは非置換のアリーレン基であり、
T1およびT2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基であり、
T3~T6は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;または置換もしくは非置換のアリール基であり、
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基であり、
X1~X4は、互いに同一または異なり、それぞれ独立に、光硬化性基または熱硬化性基であり、
R1~R20のうちの少なくとも1つは、F、シアノ基、または置換もしくは非置換のフルオロアルキル基であり、少なくとも他の1つは、光硬化性基または熱硬化性基であり、
残りのR1~R20は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ニトロ基;-C(O)R100;-OR101;-SR102;-SO3R103;-COOR104;-OC(O)R105;-C(O)NR106R107;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R100~R107は、互いに同一または異なり、それぞれ独立に、水素;重水素;または置換もしくは非置換のアルキル基であり、
n1およびn2は、それぞれ独立に、0~4の整数であり、
n3およびn4は、それぞれ独立に、0~3の整数であり、
n1~n4がそれぞれ2以上の場合、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、0~12の整数である)
であって、
光硬化性基または熱硬化性基は、下記の硬化基グループ:
[硬化基グループ]
A 1 ~A 3 は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数1~6のアルキル基である)
から選択されるいずれか1つであり、
前記コーティング組成物は、陽イオン基をさらに含み、
前記陽イオン基は、下記構造式:
X 100 ~X 109 は、互いに同一または異なり、それぞれ独立に、水素;シアノ基;ニトロ基;ヒドロキシ基;ハロゲン基;-COOR 201 ;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアミン基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のフルオロアルキル基;または置換もしくは非置換のアリール基であるか、光硬化性基または熱硬化性基であり、
R 201 は、水素;重水素;または置換もしくは非置換のアルキル基であり、
R30~R32は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であるか、隣接した基は、互いに結合して環を形成し、
pは、0~10の整数であり、
aは、1または2であり、bは、0または1であり、a+b=2である)
の中から選択される1価の陽イオン基またはオニウム基であり、
前記化学式2で表される化合物は、下記の化合物:
Zは、重水素;ハロゲン基;ニトロ基;シアノ基;アミノ基;-C(O)R 100 ;-OR 101 ;-SR 102 ;-SO 3 R 103 ;-COOR 104 ;-OC(O)R 105 ;-C(O)NR 106 R 107 ;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
lは、1~4の整数であり、lが2以上の場合、Zは、互いに同一または異なり、
R 100 ~R 107 は、互いに同一または異なり、それぞれ独立に、水素;重水素;または置換もしくは非置換のアルキル基である)
のうちのいずれか1つである、コーティング組成物。 - 前記T1およびT2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数6~60のアリール基である、請求項1に記載のコーティング組成物。
- 第1電極と、第2電極と、前記第1電極と前記第2電極との間に備えられる1層以上の有機物層とを含み、
前記有機物層のうちの1層以上は、請求項1~3のいずれか1項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の硬化物は、前記コーティング組成物を熱処理または光処理によって硬化した状態である、請求項4に記載の有機発光素子。
- 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、正孔注入層、または正孔輸送および正孔注入を同時に行う層である、請求項4又は5に記載の有機発光素子。
- 基板を用意するステップと、
前記基板上に第1電極を形成するステップと、
前記第1電極上に1層以上の有機物層を形成するステップと、
前記有機物層上に第2電極を形成するステップとを含み、
前記有機物層を形成するステップは、請求項1~3のいずれか1項に記載のコーティング組成物を用いて1層以上の有機物層を形成する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形成された有機物層を形成するステップは、
前記第1電極上に前記コーティング組成物をコーティングするステップと、
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ステップとを含むものである、請求項7に記載の有機発光素子の製造方法。
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