JP7084698B2 - 多環化合物及びこれを含む有機電界発光素子 - Google Patents
多環化合物及びこれを含む有機電界発光素子 Download PDFInfo
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- JP7084698B2 JP7084698B2 JP2017091996A JP2017091996A JP7084698B2 JP 7084698 B2 JP7084698 B2 JP 7084698B2 JP 2017091996 A JP2017091996 A JP 2017091996A JP 2017091996 A JP2017091996 A JP 2017091996A JP 7084698 B2 JP7084698 B2 JP 7084698B2
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 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
化合物10は、化合物9の合成でビス(4-ビフェニリル)アミンの代わりにN-[4-(1-ナフタレニル)フェニル]-1-ナフタレンアミンを使用したことを除き、同一の方法で合成した。FAB-MSによって測定された化合物10の分子量は、738であった。また、1H-NMR(CDCl3)で測定された化合物10のケミカルシフト値(δ)は、8.09(d、2H、J=7.10Hz)、7.96(d、1H、J=8.10Hz)7.89-7.85(m、9H)、7.80-7.74(m、5H)、7.73(s、1H)、7.71-7.66(m、3H)、7.48-7.21(m、18H)であった。
化合物30は、化合物28の合成で9-(2-ナフタレニル)-アントラセンの代わりに6-フェニル-クリセンを使用したことを除き、同一の方法で合成した。FAB-MSにより測定された化合物30の分子量は、621であった。また、1H-NMR(CDCl3)で測定された化合物30のケミカルシフト値(δ)は、8.20-8.10(m、9H)、8.02(d、2H、J=7.20Hz)、7.90(d、1H、J=8.10Hz)、7.87(s、1H)、7.82-7.77(m、10H)、7.70-7.54(m、9H)であった。
化合物36は、化合物28の合成で9-(2-ナフタレニル)-アントラセンの代わりにN、N-ジフェニル-9-アントラセンアミンを使用したことを除き、同一の方法で合成した。FAB-MSによって測定された化合物30の分子量は、662であった。また、1H-NMR(CDCl3)で測定された化合物30のケミカルシフト値(δ)は、8.32(s、1H)、8.22-8.10(m、9H)、8.02(d、2H、J=7.20Hz)、7.95(d、1H、J=8.10Hz)、7.93(d、2H、J=8.10Hz)、7.92(s、1H)7.89-7.82(m、9H)、7.80-7.74(m、10H)であった。
EL1 第1電極
HTR 正孔輸送領域
EML 発光層
ETR 電子輸送領域
EL2 第2電極
Claims (11)
- 下記の化学式(12)で示される多環化合物。
(12)
前記化学式(12)において、
Xは、O、S、NR13、CR14R15又はSiR16R17であり、
R13~R17は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
Ar 1 及びAr 2 の一方は、置換もしくは無置換のアントラセニル基、置換もしくは無置換のピレニル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のカルバゾリル基、又は置換もしくは無置換のピリジル基から選択され、
Ar 1 及びAr 2 の他方は、置換もしくは無置換のフェニル基であり、
R 1 ~R 3 及びR 6 ~R 12 は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基から選択され、隣接する基と互いに結合して環を形成することができる。 - 下記の化学式(13)で示される多環化合物。
(13)
前記化学式(13)において、
Xは、O、S、NR13、CR14R15又はSiR16R17であり、
R3及びR6は、各々独立に置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
R13~R17は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
Ar 1 及びAr 2 の一方は、置換もしくは無置換のアントラセニル基、置換もしくは無置換のピレニル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のカルバゾリル基、又は置換もしくは無置換のピリジル基から選択され、
Ar 1 及びAr 2 の他方は、置換もしくは無置換のフェニル基である。 - 下記の化学式(15)で示される多環化合物。
(15)
前記化学式(15)において、
Xは、O、S、NR13、CR14R15又はSiR16R17であり、
Yは、O、S、NR20、又は置換若しくは無置換のホスフィンオキシド基であり、
R13~R17は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
R20は、水素、重水素、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
Ar 1 及びAr 2 の一方は、置換もしくは無置換のアントラセニル基、置換もしくは無置換のピレニル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のカルバゾリル基、又は置換もしくは無置換のピリジル基から選択され、
Ar 1 及びAr 2 の他方は、置換もしくは無置換のフェニル基であり、
R1~R3、R6、R7及びR10~R12は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基から選択され、隣接する基と互いに結合して環を形成することができる。 - 下記の化学式(16)で示される多環化合物。
(16)
前記化学式(16)において、
Xは、O、S、NR13、CR14R15又はSiR16R17であり、
R13~R17は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
R1~R3及びR6~R12は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基から選択され、隣接する基と互いに結合して環を形成することができる。 - 第1電極と、
前記第1電極上に配置された正孔輸送領域と、
前記正孔輸送領域上に配置された発光層と、
前記発光層上に配置された電子輸送領域と、
前記電子輸送領域上に配置された第2電極と、を含み、
前記正孔輸送領域及び前記発光層の中の少なくとも1つは、下記の化学式(1)または化学式(3)で示される多環化合物を含む有機電界発光素子。
(1)
(3)
前記化学式(1)において、
Ar 1 及びAr 2 の一方は、置換若しくはもしくは無置換のアントラセニル基、置換もしくは無置換のピレニル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のカルバゾリル基、置換もしくは無置換のピリジル基から選択され、或いは互いに結合して環を形成し、
Ar 1 及びAr 2 の他方は、置換もしくは無置換のフェニル基であり、
Aは、下記の化学式(2-1)で示され、
(2-1)
前記化学式(2-1)において、
R1~R12は、各々独立に水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換のアリールアミノ基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、又は置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であるか、或いは隣接する基と互いに結合して環を形成し、
前記化学式(3)で、
Wは、水素、重水素、ハロゲン基、シリル基、置換若しくは無置換の炭素数1以上20以下のアルキル基、置換若しくは無置換の環形成炭素数6以上60以下のアリール基、又は置換若しくは無置換の環形成炭素数5以上60以下のヘテロアリール基であり、
pは、0以上8以下の整数であり、
pが2以上である場合、複数のWは、互いに同一であるか、或いは異なり、
EはO、S、またはNR’であり、
mは0または1であり、
ZおよびR’は、それぞれ独立して、以下の化学式(4)で表され、
前記化学式(4)において、
U1およびU2は、それぞれ独立して、環を形成するための6個以上30個以下の炭素原子を有する置換もしくは無置換のアリール基、または環を形成するための2個以上30個以下の炭素原子を有する置換もしくは無置換のヘテロアリール基であり、
L’は、環を形成するための6個以上30個以下の炭素原子を有する置換または非置換のアリーレン基であり
nは0または1であり、
EがNR’の場合、mは0であり、EがOまたはSの場合、mは1である。
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