JP6825194B2 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JP6825194B2 JP6825194B2 JP2019073261A JP2019073261A JP6825194B2 JP 6825194 B2 JP6825194 B2 JP 6825194B2 JP 2019073261 A JP2019073261 A JP 2019073261A JP 2019073261 A JP2019073261 A JP 2019073261A JP 6825194 B2 JP6825194 B2 JP 6825194B2
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- 238000004528 spin coating Methods 0.000 description 1
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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
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Description
(a)イオン化ポテンシャル[Ip(LEL)]が5.5eV以上であり、
(b)EHOMO−ELUMO>2.9eV、
(c)三重項エネルギーが2.3eV以上であり、
(d)ΔEst<0.5eV(ΔEstは、前記化合物の一重項エネルギーと三重項エネルギーとの差を示す)。
Y1〜Y4は、互いに同一又は異なって、それぞれ独立に、N又はC(R1)であり、この時、複数のR1は、同様な表示であっても、それぞれ同一又は異なっており、これらは隣り合う基と縮合環を形成することができ、
X2及びX3は、互いに同一又は異なって、それぞれ独立に、N又はC(R2)であり、この時、複数のR2は、同様な表示であっても、それぞれ同一又は異なっており、これらは隣り合う基と縮合環を形成することができ、
前記R1〜R2及びAr1〜Ar5は、互いに同一又は異なって、それぞれ独立に、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
前記R1〜R2及びAr1〜Ar5における、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキサイド基、及びアリールアミン基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C40のアリール基、核原子数5〜40のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上で置換されるか又は置換されていない。
X4は、X1と同じであり、この時、複数のAr1〜Ar5は、それぞれ同一又は異なっている。
前記R3における、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキサイド基、及びアリールアミン基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C40のアリール基、核原子数5〜40のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上で置換されるか又は置換されていない。
R1〜R3は、それぞれ独立に、水素、置換或いは非置換のC1〜C40のアルキル基、置換或いは非置換のC6〜C40のアリール基、又は、置換或いは非置換の核原子数5〜40のヘテロアリール基であることが好ましい。
Y5〜Y14は、互いに同一又は異なって、それぞれ独立にN又はC(R3)であり、いずれもC(R3)であることが好ましい。なお、複数のR3は、同一又は異なっている。
Ar6〜Ar8は、互いに同一又は異なって、それぞれ独立に、水素、重水素、C6〜C40のアリール基、及び核原子数5〜40のヘテロアリール基からなる群から選択され(但し、Ar6〜Ar8がいずれも同一である場合を除く)、
R4〜R6は、互いに同一又は異なって、それぞれ独立に、水素、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C60のアリール基、核原子数5〜60のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択され、
a乃至cは、それぞれ独立に0〜3の整数であり、
前記L1〜L3、R4〜R6及びAr6〜Ar8における、アリーレン基、ヘテロアリーレン基、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アルキルオキシ基、アリールオキシ基、アルキルシリル基、アリールシリル基、アルキルボロン基、アリールボロン基、ホスフィン基、ホスフィンオキサイド基、及びアリールアミン基は、それぞれ独立に、重水素、ハロゲン基、シアノ基、ニトロ基、アミノ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C2〜C40のアルキニル基、C3〜C40のシクロアルキル基、核原子数3〜40のヘテロシクロアルキル基、C6〜C40のアリール基、核原子数5〜40のヘテロアリール基、C1〜C40のアルキルオキシ基、C6〜C60のアリールオキシ基、C1〜C40のアルキルシリル基、C6〜C60のアリールシリル基、C1〜C40のアルキルボロン基、C6〜C60のアリールボロン基、C1〜C40のホスフィン基、C1〜C40のホスフィンオキサイド基、及びC6〜C60のアリールアミン基からなる群から選択される1種以上で置換されるか又は置換されていない。
ITO(Indium Tin Oxide)が1500Åの厚さで薄膜コーティングされたガラス基板を蒸留水で超音波洗浄を行った。蒸留水洗浄が終わると、イソプロピルアルコール、アセトン、メタノールなどの溶剤で超音波洗浄を行い、乾燥させた後、UV OZONE洗浄機(Power Sonic 405、Hwashin Tech社製)へ移送させた後、UVを用いて前記基板を5分間洗浄し、真空蒸着機へ基板を移送した。
寿命改善層を使用せずに電子輸送層を30nmで蒸着したこと以外は、前述の実施例1と同様にして素子を製造した。
LE−01に代えて、下記の構造を有するBCPを使用する以外は、前述の実施例1と同様にして素子を製造した。
前述の実施例1〜36及び比較例1、2で製造されたそれぞれの素子について、電流密度10mA/cm2での駆動電圧、電流効率、発光波長及び寿命(T97)を測定し、その結果を下記の表3に示した。
ITO(Indium Tin Oxide)が1500Åの厚さで薄膜コーティングされたガラス基板を蒸留水で超音波洗浄を行った。蒸留水洗浄が終わると、イソプロピルアルコール、アセトン、メタノールなどの溶剤で超音波洗浄を行い、乾燥させた後、UV OZONE洗浄機(Power Sonic 405、Hwashin Tech社製)へ移送させた後、UVを用いて前記基板を5分間洗浄し、真空蒸着機へ基板を移送した。
寿命改善層を使用せずに電子輸送層を30nmで蒸着したこと以外は、前述の実施例37と同様にして素子を製造した。
LE−02に代えて、前述の比較例2で使用されたBCPを使用する以外は、前述の実施例37と同様にして素子を製造した。
前述の実施例37〜51及び比較例3、4で製造されたそれぞれの素子について、電流密度10mA/cm2での駆動電圧、電流効率、発光波長及び寿命(T97)を測定し、その結果を下記の表5に示した。
200:負極
301:正孔注入層
302:正孔輸送層
303:発光層
304:寿命改善層
305:電子輸送層
306:電子注入層
Claims (1)
- 正極;
負極;及び
前記正極と負極との間に、正孔注入層、正孔輸送層、発光層、電子輸送層及び電子注入層からなる群から選択される有機物層が1層以上設けられており、
前記発光層と電子輸送層との間に、寿命改善層(Lifetime Enhancement Layer、LEL)をさらに含む有機電界発光素子であって、
前記寿命改善層は、下記の化合物LE−33及びLE−35からなる群から選択された双極性(bipolar)化合物を含み、
前記双極性化合物は、下記の(a)〜(d)の条件を満たすことを特徴とする有機電界発光素子:
(a)イオン化ポテンシャル[Ip(LEL)]が5.5eV以上であり、
(b)EHOMO−ELUMO>2.9eV、
(c)三重項エネルギーが2.3eV以上であり、
(d)ΔEst<0.5eV(ΔEstは、前記化合物の一重項エネルギーと三重項エネルギーとの差を示す)。
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