JP2022552762A - ヘテロ環化合物およびこれを含む有機発光素子 - Google Patents
ヘテロ環化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP2022552762A JP2022552762A JP2021574980A JP2021574980A JP2022552762A JP 2022552762 A JP2022552762 A JP 2022552762A JP 2021574980 A JP2021574980 A JP 2021574980A JP 2021574980 A JP2021574980 A JP 2021574980A JP 2022552762 A JP2022552762 A JP 2022552762A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 37
- 239000000126 substance Substances 0.000 claims abstract description 41
- 239000010410 layer Substances 0.000 claims description 142
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 33
- 238000002347 injection Methods 0.000 claims description 32
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
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- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- TXUHJKCHFTYRJD-UHFFFAOYSA-N BrC1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1.BrC1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound BrC1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1.BrC1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 TXUHJKCHFTYRJD-UHFFFAOYSA-N 0.000 description 2
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000000304 alkynyl group Chemical group 0.000 description 2
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- 239000010405 anode material Substances 0.000 description 2
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- 230000000052 comparative effect Effects 0.000 description 2
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 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
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
本明細書は、ヘテロ環化合物およびこれを含む有機発光素子に関する。
有機発光素子は、2つの電極の間に有機薄膜を配置させた構造を有している。このような構造の有機発光素子に電圧が印加されると、2つの電極から注入された電子と正孔が有機薄膜で結合して対をなした後、消滅しながら光を発する。前記有機薄膜は、必要に応じて単層または多層から構成される。
有機薄膜の材料は、必要に応じて発光機能を有することができる。例えば、有機薄膜材料としては、それ自体が単独で発光層を構成できる化合物が使用されてもよく、またはホスト-ドーパント系発光層のホストまたはドーパントの役割を果たす化合物が使用されてもよい。その他にも、有機薄膜の材料として、正孔注入、正孔輸送、電子ブロック、正孔ブロック、電子輸送、電子注入などの役割を果たす化合物が使用されてもよい。
有機発光素子の性能、寿命または効率を向上させるために、有機薄膜の材料の開発が求められ続けている。
前記化学式1において、
R1およびR2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;または置換もしくは非置換のC2~C60のヘテロアリール基であるか、互いに隣接する基は、互いに結合して置換もしくは非置換のC6~C60の芳香族炭化水素環、または置換もしくは非置換のC2~C60のヘテロ環を形成し、
L1は、直接結合;置換もしくは非置換のC6~C60のアリーレン基;または置換もしくは非置換のC2~C60のヘテロアリーレン基であり、
X1~X3は、互いに同一または異なり、それぞれ独立して、N;またはCRaであり、少なくとも1つは、Nであり、
前記Ra、Ar2およびAr4は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-SiRR’R”;-P(=O)RR’;および置換もしくは非置換のC1~C60のアルキル基、置換もしくは非置換のC6~C60のアリール基、または置換もしくは非置換のC2~C60のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換のC6~C60の芳香族炭化水素環、または置換もしくは非置換のC2~C60のヘテロ環を形成し、
R3~R11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;-CN;置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-SiRR’R”;-P(=O)RR’;および置換もしくは非置換のC1~C60のアルキル基、置換もしくは非置換のC6~C60のアリール基、または置換もしくは非置換のC2~C60のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換のC6~C60の芳香族炭化水素環、または置換もしくは非置換のC2~C60のヘテロ環を形成し、
前記R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C40のアルキル基;または置換もしくは非置換のC6~C40のアリール基であり、
mは、1~6の整数であり、mが2以上の場合、括弧内の置換基は、互いに同一または異なる。
すなわち、前記化学式1で表される化合物は、フルオレン基を有する骨格に優れた電子輸送特性を有するアジン系の置換基を特定の位置に有するもので、電子求引(electron withdrawing)特性を強化してバンドギャップ(band gap)およびT1値の調節により、有機発光素子に含まれる場合、優れた効率および駆動を示すことを特徴とする。
また、バンドギャップ(band gap)およびT1値の調節により電子伝達能力および正孔ブロック能力を向上させることができ、分子の安定性も高くなるため、素子の駆動電圧を低下させ、光効率を向上させ、化合物の熱的安定性によって素子の寿命特性を向上させることができる特徴を有する。
本明細書において、「化学式または化合物構造に置換基が表されていない場合」は、炭素原子に水素原子が結合したことを意味する。ただし、重水素(2H、Deuterium)は水素の同位元素であるので、一部の水素原子は、重水素であってもよい。
すなわち、一例において、
で表されるフェニル基において重水素の含有量20%というのは、フェニル基が有し得る置換基の総数は5(式中のT1)個であり、そのうち重水素の個数が1(式中のT2)である場合、20%で表される。すなわち、フェニル基において重水素の含有量20%というのは、下記構造式で表されてもよい。
前記化学式2~4において、
X1~X3、R3~R11、L1、Ar2、Ar4およびmの定義は、前記化学式1における定義と同じである。
前記R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C40のアルキル基;または置換もしくは非置換のC6~C40のアリール基であってもよい。
前記構造式において、
は、前記化学式1の置換基と連結される位置を意味し、
R12は、置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-CN;または-P(=O)RR’であり、
前記RおよびR’は、前記化学式1における定義と同じである。
さらに他の実施態様において、R12は、-CNまたは-P(=O)RR’で置換もしくは非置換のフェニル基;ジベンゾフラン基;カルバゾール基;-CNで置換もしくは非置換のナフチル基;メチル基で置換もしくは非置換のピリジン基;または-CNであってもよい。
前記Ar3およびAr5は、前記化学式1のRaの定義と同じである。
前記Ar5は、前記化学式1のRaの定義と同じである。
前記Ar3は、前記化学式1のRaの定義と同じである。
前記Ar1およびAr5は、前記化学式1のRaの定義と同じである。
は、下記化学式1-1~1-5のいずれか1つで表されてもよい。
前記化学式1-1~1-5において、
は、前記化学式1のL1と連結される位置を意味し、
Ar11~Ar15は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-SiRR’R”;-P(=O)RR’;および置換もしくは非置換のC1~C60のアルキル基、置換もしくは非置換のC6~C60のアリール基、または置換もしくは非置換のC2~C60のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択され、
前記R、R’およびR”の定義は、前記化学式1における定義と同じである。
は、下記化学式1-6または1-7で表されてもよい。
前記化学式1-6および1-7において、
は、前記化学式1のL1と連結される位置を意味し、
R21は、水素;置換もしくは非置換のC6~C60のアリール基;または置換もしくは非置換のC2~C60のヘテロアリール基である。
で表され、前記Ar14は、置換もしくは非置換のC6~C60のアリール基であり、
前記L2は、直接結合;置換もしくは非置換のC6~C60のアリーレン基;または置換もしくは非置換のC2~C60のヘテロアリーレン基であり、
前記Z2は、置換もしくは非置換のC6~C60のアリール基;または置換もしくは非置換のC2~C60のヘテロアリール基であり、
aおよびbは、互いに同一または異なり、それぞれ1~6の整数であり、aおよびbが2以上の場合、括弧内の置換基は、互いに同一または異なる。
6-ブロモ-11,11-ジメチル-11H-ベンゾ[a]フルオレン(6-Bromo-11,11-dimethyl-11H-benzo[a]fluorine)(A)(10g、0.03mol、1eq)、ビス(ピナコラト)ジボロン(bis(pinacolato)diboron)(11.8g、0.046mol、1.5eq)、KOAc(9.1g、0.09mol、3eq)、Pd(dppf)Cl2(2.2g、0.003mol、0.1eq)に、1,4-ジオキサン(1,4-Dioxane)(100ml)を入れて、100℃で6h撹拌した。水を入れて反応を終結させた後、メチレンクロライド(MC)と水を用いて抽出した。その後、MgSO4で水分を除去した。シリカゲル(Silicagel)カラムで分離して、化合物5-2 9gを78%の収率で得た。
2-(4-ブロモフェニル)-4,6-ジフェニル-1,3,5-トリアジン(2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine)(B)(10g、0.025mol、1eq)、化合物5-2(10g、0.027mol、1.05eq)、K3PO4(11g、0.05mol、2eq)、Pd(PPh3)4(1.5g、0.001mol、0.05eq)に、1,4-ジオキサン(1,4-Dioxane)(100ml)を入れて、100℃で6h撹拌した。水を入れて反応を終結させた後、メチレンクロライド(MC)と水を用いて抽出した。その後、無水MgSO4で水分を除去した。シリカゲル(Silicagel)カラムで分離して、化合物5 7gを49%の収率で得た。
<実験例1>
1)有機発光素子の作製
OLED用ガラス(サムスン・コーニング社製)から得られた透明電極インジウムチンオキシド(ITO)薄膜を、トリクロロエチレン、アセトン、エタノール、蒸留水を順次に用いて各5分間超音波洗浄を実施した後、イソプロパノールに入れて保管した後に使用した。次に、真空蒸着装置の基板フォルダにITO基板を設け、真空蒸着装置内のセルに、下記の4,4’,4”-トリス(N,N-(2-ナフチル)-フェニルアミノ)トリフェニルアミン(4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine:2-TNATA)を入れた。
1)有機発光素子の作製
OLED用ガラス(サムスン・コーニング社製)から得られた透明電極インジウムチンオキシド(ITO)薄膜を、トリクロロエチレン、アセトン、エタノール、蒸留水を順次に用いて各5分間超音波洗浄を実施した後、イソプロパノールに入れて保管した後に使用した。次に、真空蒸着装置の基板フォルダにITO基板を設け、真空蒸着装置内のセルに、下記の4,4’,4”-トリス(N,N-(2-ナフチル)-フェニルアミノ)トリフェニルアミン(4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine:2-TNATA)を入れた。
次に、チャンバ内の真空度が10-6torrに到達するまで排気させた後、セルに電流を印加して2-TNATAを蒸発させて、ITO基板上に600Åの厚さの正孔注入層を蒸着した。真空蒸着装置内の他のセルに、下記のN,N’-ビス(α-ナフチル)-N,N’-ジフェニル-4,4’-ジアミン(N,N’-bis(α-naphthyl)-N,N’-diphenyl-4,4’-diamine:NPB)を入れて、セルに電流を印加して蒸発させて、正孔注入層上に300Åの厚さの正孔輸送層を蒸着した。
200:陽極
300:有機物層
301:正孔注入層
302:正孔輸送層
303:発光層
304:正孔阻止層
305:電子輸送層
306:電子注入層
400:陰極
Claims (14)
- 下記化学式1で表されるヘテロ環化合物:
前記化学式1において、
R1およびR2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;または置換もしくは非置換のC2~C60のヘテロアリール基であるか、互いに隣接する基は、互いに結合して置換もしくは非置換のC6~C60の芳香族炭化水素環、または置換もしくは非置換のC2~C60のヘテロ環を形成し、
L1は、直接結合;置換もしくは非置換のC6~C60のアリーレン基;または置換もしくは非置換のC2~C60のヘテロアリーレン基であり、
X1~X3は、互いに同一または異なり、それぞれ独立して、N;またはCRaであり、少なくとも1つは、Nであり、
前記Ra、Ar2およびAr4は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-SiRR’R”;-P(=O)RR’;および置換もしくは非置換のC1~C60のアルキル基、置換もしくは非置換のC6~C60のアリール基、または置換もしくは非置換のC2~C60のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換のC6~C60の芳香族炭化水素環、または置換もしくは非置換のC2~C60のヘテロ環を形成し、
R3~R11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;-CN;置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-SiRR’R”;-P(=O)RR’;および置換もしくは非置換のC1~C60のアルキル基、置換もしくは非置換のC6~C60のアリール基、または置換もしくは非置換のC2~C60のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換のC6~C60の芳香族炭化水素環、または置換もしくは非置換のC2~C60のヘテロ環を形成し、
前記R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C40のアルキル基;または置換もしくは非置換のC6~C40のアリール基であり、
mは、1~6の整数であり、mが2以上の場合、括弧内の置換基は、互いに同一または異なる。 - 前記化学式1の
は、下記化学式1-1~1-5のいずれか1つで表される、請求項1に記載のヘテロ環化合物:
前記化学式1-1~1-5において、
は、前記化学式1のL1と連結される位置を意味し、
Ar11~Ar15は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のC1~C60のアルキル基;置換もしくは非置換のC6~C60のアリール基;置換もしくは非置換のC2~C60のヘテロアリール基;-SiRR’R”;-P(=O)RR’;および置換もしくは非置換のC1~C60のアルキル基、置換もしくは非置換のC6~C60のアリール基、または置換もしくは非置換のC2~C60のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択され、
前記R、R’およびR”の定義は、前記化学式1における定義と同じである。 - 第1電極と、前記第1電極に対向して備えられた第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た1層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの1層以上は、請求項1~7のいずれか1項に記載のヘテロ環化合物を含む有機発光素子。
- 前記有機物層は、電子輸送層を含み、前記電子輸送層は、前記ヘテロ環化合物を含む、請求項8に記載の有機発光素子。
- 前記有機物層は、電子注入層または正孔輸送層を含み、前記電子注入層または正孔輸送層は、前記ヘテロ環化合物を含む、請求項8に記載の有機発光素子。
- 前記有機物層は、電子阻止層または正孔阻止層を含み、前記電子阻止層または正孔阻止層は、前記ヘテロ環化合物を含む、請求項8に記載の有機発光素子。
- 前記有機発光素子は、発光層、正孔注入層、正孔輸送層、電子注入層、電子輸送層、電子阻止層、および正孔阻止層からなる群より選択される1層または2層以上をさらに含む、請求項8に記載の有機発光素子。
- 前記有機発光素子は、第1電極と、前記第1電極上に備えられ、第1発光層を含む第1スタックと、前記第1スタック上に備えられる電荷生成層と、前記電荷生成層上に備えられ、第2発光層を含む第2スタックと、前記第2スタック上に備えられる第2電極とを含む、請求項8に記載の有機発光素子。
- 前記電荷生成層は、前記ヘテロ環化合物を含む、請求項13に記載の有機発光素子。
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