JP6898084B2 - アミン化合物及びこれを含む有機電界発光素子 - Google Patents
アミン化合物及びこれを含む有機電界発光素子 Download PDFInfo
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- JP6898084B2 JP6898084B2 JP2016235499A JP2016235499A JP6898084B2 JP 6898084 B2 JP6898084 B2 JP 6898084B2 JP 2016235499 A JP2016235499 A JP 2016235499A JP 2016235499 A JP2016235499 A JP 2016235499A JP 6898084 B2 JP6898084 B2 JP 6898084B2
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- 0 CN(C)c(cc1*2)ccc1C1=C2CCC=C1 Chemical compound CN(C)c(cc1*2)ccc1C1=C2CCC=C1 0.000 description 6
- SJSQPTWSNOZOOH-UHFFFAOYSA-N CC(c1ccc2)(c3cccc4c3c1c2[o]4)c1ccccc1 Chemical compound CC(c1ccc2)(c3cccc4c3c1c2[o]4)c1ccccc1 SJSQPTWSNOZOOH-UHFFFAOYSA-N 0.000 description 2
- GHMGCRVYVVXFJM-UHFFFAOYSA-N c1ccc(C(c2ccc3)(c4c5c2c3[o]c5ccc4)c(cc2)ccc2N(c2ccc(c3ccccc3[o]3)c3c2)c2cccc3c2cccc3)cc1 Chemical compound c1ccc(C(c2ccc3)(c4c5c2c3[o]c5ccc4)c(cc2)ccc2N(c2ccc(c3ccccc3[o]3)c3c2)c2cccc3c2cccc3)cc1 GHMGCRVYVVXFJM-UHFFFAOYSA-N 0.000 description 2
- PDZQAFZWDFKKFL-UHFFFAOYSA-N C(C1C(c2ccc3)(c4ccccc4)c(cc4)ccc4N(c(cc4)ccc4-c4c(cccc5)c5ccc4)c4ccc(c(cccc5)c5[o]5)c5c4)C=Cc4c1c2c3[o]4 Chemical compound C(C1C(c2ccc3)(c4ccccc4)c(cc4)ccc4N(c(cc4)ccc4-c4c(cccc5)c5ccc4)c4ccc(c(cccc5)c5[o]5)c5c4)C=Cc4c1c2c3[o]4 PDZQAFZWDFKKFL-UHFFFAOYSA-N 0.000 description 1
- BRIWFSSSNCGXEA-UHFFFAOYSA-N C(Cc1ccc2)C=Cc1c2N(c(cc1)ccc1C(C=CC1)=CC1C1(c2c3c4c1cccc4[o]c3ccc2)c1ccccc1)c1cccc2c1cccc2 Chemical compound C(Cc1ccc2)C=Cc1c2N(c(cc1)ccc1C(C=CC1)=CC1C1(c2c3c4c1cccc4[o]c3ccc2)c1ccccc1)c1cccc2c1cccc2 BRIWFSSSNCGXEA-UHFFFAOYSA-N 0.000 description 1
- FPZZCYVJXUQSQN-UHFFFAOYSA-N C1C=C(c(cccc2)c2S2)C2=CC1N(c1ccccc1)c1ccc(C2(c3cccc4c3C3C2=CC=CC3O4)c2ccccc2)cc1 Chemical compound C1C=C(c(cccc2)c2S2)C2=CC1N(c1ccccc1)c1ccc(C2(c3cccc4c3C3C2=CC=CC3O4)c2ccccc2)cc1 FPZZCYVJXUQSQN-UHFFFAOYSA-N 0.000 description 1
- QYXCGESFULJCMV-QHOOKQDJSA-N C=C/C(/N(c(cc1)ccc1-c1ccccc1)c1ccc(c(CCC=C2)c2[o]2)c2c1)=C\C=C\C1(c2cccc3c2c2c1cccc2[o]3)c1ccccc1 Chemical compound C=C/C(/N(c(cc1)ccc1-c1ccccc1)c1ccc(c(CCC=C2)c2[o]2)c2c1)=C\C=C\C1(c2cccc3c2c2c1cccc2[o]3)c1ccccc1 QYXCGESFULJCMV-QHOOKQDJSA-N 0.000 description 1
- SHFANZPAOFQRFU-UHFFFAOYSA-N CC1(C)c2cc(N(c3ccc(C4(c5c6c7c4cccc7[o]c6ccc5)c4ccccc4)cc3)c3cccc4c3cccc4)ccc2-c2c1cccc2 Chemical compound CC1(C)c2cc(N(c3ccc(C4(c5c6c7c4cccc7[o]c6ccc5)c4ccccc4)cc3)c3cccc4c3cccc4)ccc2-c2c1cccc2 SHFANZPAOFQRFU-UHFFFAOYSA-N 0.000 description 1
- ZFQOZPXBCVHIRC-UHFFFAOYSA-N CC1(C)c2cccc(Cc3cccc(Br)c3)c2-c2c(Cc3ccccc3)cccc12 Chemical compound CC1(C)c2cccc(Cc3cccc(Br)c3)c2-c2c(Cc3ccccc3)cccc12 ZFQOZPXBCVHIRC-UHFFFAOYSA-N 0.000 description 1
- XNUMUNIJQMSNNN-UHFFFAOYSA-N O=C(c1ccccc1)c1cccc(Br)c1 Chemical compound O=C(c1ccccc1)c1cccc(Br)c1 XNUMUNIJQMSNNN-UHFFFAOYSA-N 0.000 description 1
- SZOFSHPSDMYXKP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1Nc1ccc(c(cccc2)c2[o]2)c2c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1Nc1ccc(c(cccc2)c2[o]2)c2c1 SZOFSHPSDMYXKP-UHFFFAOYSA-N 0.000 description 1
- AKUGXTUATOWIEL-UHFFFAOYSA-N c1ccc(C(c2ccc3)(c4cccc5c4c2c3[o]5)c(cc2)ccc2N(c2ccccc2)c2ccc(c3ccccc3[s]3)c3c2)cc1 Chemical compound c1ccc(C(c2ccc3)(c4cccc5c4c2c3[o]5)c(cc2)ccc2N(c2ccccc2)c2ccc(c3ccccc3[s]3)c3c2)cc1 AKUGXTUATOWIEL-UHFFFAOYSA-N 0.000 description 1
- WOZBRYMINSJFIK-UHFFFAOYSA-N c1ccc(C(c2ccc3)(c4cccc5c4c2c3cc5)c2cccc(N(c(cc3)ccc3-c3ccccc3)c3ccc(c4ccccc4[o]4)c4c3)c2)cc1 Chemical compound c1ccc(C(c2ccc3)(c4cccc5c4c2c3cc5)c2cccc(N(c(cc3)ccc3-c3ccccc3)c3ccc(c4ccccc4[o]4)c4c3)c2)cc1 WOZBRYMINSJFIK-UHFFFAOYSA-N 0.000 description 1
- PNYCLVDGRQKDOF-UHFFFAOYSA-N c1ccc(C2(c3cccc4c3c3c2cccc3[o]4)c(cc2)ccc2N(c(cc2)ccc2-c2ccccc2)c(cc2)cc3c2c(cccc2)c2[s]3)cc1 Chemical compound c1ccc(C2(c3cccc4c3c3c2cccc3[o]4)c(cc2)ccc2N(c(cc2)ccc2-c2ccccc2)c(cc2)cc3c2c(cccc2)c2[s]3)cc1 PNYCLVDGRQKDOF-UHFFFAOYSA-N 0.000 description 1
- QTKKZMFPMWSEFI-UHFFFAOYSA-N c1ccc(C2(c3cccc4c3c3c2cccc3[o]4)c(cc2)ccc2N(c2ccc(c(cccc3)c3[s]3)c3c2)c2cccc3c2cccc3)cc1 Chemical compound c1ccc(C2(c3cccc4c3c3c2cccc3[o]4)c(cc2)ccc2N(c2ccc(c(cccc3)c3[s]3)c3c2)c2cccc3c2cccc3)cc1 QTKKZMFPMWSEFI-UHFFFAOYSA-N 0.000 description 1
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Description
前記化学式6において、AはO、S、又はCR2R3であり、R2及びR3は各々独立的に水素原子、重水素原子、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30以下のアリール基、又は置換若しくは無置換の炭素数5以上30以下のヘテロアリール基である。
前記化学式8において、AはO、S、又はCR2R3であり、R2及びR3は各々独立的に水素原子、重水素原子、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30以下のアリール基、又は置換若しくは無置換の炭素数5以上30以下のヘテロアリール基である。
ITOで150nm厚さの陽極204を形成し、2−TNATAで60nm厚さの正孔注入層を形成し、30nm厚さの正孔輸送層を形成し、ADNにTBPを3%ドープした25nm厚さの発光層を形成し、Alq3で25nm厚さの電子輸送層を形成し、LiFで1nm厚さの電子注入層を形成し、Alで100nm厚さの陰極を形成した。
AN アノード
HTR 正孔輸送領域
EML 発光層
BFL バッファ層
ETR 電子輸送領域
CAT カソード
Claims (11)
- 以下の化学式1で表されるアミン化合物。
前記化学式1において、
Xは以下の化学式2で表わされる官能基から選択され、
YはC、Si又はGeであり、
Z1〜Z6はCR又はNであり、
Ar 1 は置換若しくは無置換のフェニル基であり、
Ar 2 〜Ar3は各々独立的に水素原子、重水素原子、ハロゲン原子、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、置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基、炭素数1以上20以下のアルキル基又は炭素数3以上20以下のシリル基であり、
L 1 は置換若しくは無置換の炭素数6以上30以下のアリーレン基、又は置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリーレン基であり、
L 2 〜L3は各々独立的に単結合、置換若しくは無置換の炭素数6以上30以下のアリーレン基、又は置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリーレン基であり、
R及びR’は各々独立的に、水素原子、重水素原子、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、置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基、又は炭素数1以上20以下のアルキル基であり、
前記化学式1におけるアミン部位の窒素原子は、L 1 のメタ位に結合される。 - 前記L1は、
置換若しくは無置換のフェニレン基、又は置換若しくは無置換のビフェニレン基である請求項1乃至請求項3のいずれか一項に記載のアミン化合物。 - 前記Ar2は、
置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換のジベンゾフラニル基、置換若しくは無置換のジベンゾチオフェニル基及び置換若しくは無置換のフルオレニル基の中から選択される請求項1に記載のアミン化合物。 - 前記Ar3は、
置換若しくは無置換のフェニル基、置換若しくは無置換のビフェニル基又は置換若しくは無置換のナフチル基である請求項1に記載のアミン化合物。 - アノードと、
前記アノード上に設けられる正孔輸送領域と、
前記正孔輸送領域上に設けられる発光層と、
前記発光層上に設けられる電子輸送領域と、
前記電子輸送領域上に設けられるカソードと、を含み、
前記正孔輸送領域は、
以下の化学式1で表されるアミン化合物を含む有機電界発光素子。
前記化学式1において、
Xは以下の化学式2で表わされる官能基から選択され、
YはC、Si又はGeであり、
Z1〜Z6はCR又はNであり、
Ar 1 は置換若しくは無置換のフェニル基であり、
Ar 2 〜Ar3は各々独立的に水素原子、重水素原子、ハロゲン原子、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、置換若しくは無置換の環形成炭素数5
以上30以下のヘテロアリール基、炭素数1以上20以下のアルキル基又は炭素数3以上20以下のシリル基であり、
L 1 は置換若しくは無置換の炭素数6以上30以下のアリーレン基、又は置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリーレン基であり、
L 2 〜L3は各々独立的に単結合、置換若しくは無置換の炭素数6以上30以下のアリーレン基、又は置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリーレン基であり、
R及びR’は各々独立的に、水素原子、重水素原子、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、置換若しくは無置換の環形成炭素数5以上30以下のヘテロアリール基、又は炭素数1以上20以下のアルキル基であり、
前記化学式1におけるアミン部位の窒素原子は、L 1 のメタ位に結合される。
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