JP5154639B2 - ナフチルカルバゾール誘導体、klホスト材料、これを用いた有機電界発光素子、これを用いた表示装置及び照明装置 - Google Patents
ナフチルカルバゾール誘導体、klホスト材料、これを用いた有機電界発光素子、これを用いた表示装置及び照明装置 Download PDFInfo
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- JP5154639B2 JP5154639B2 JP2010500830A JP2010500830A JP5154639B2 JP 5154639 B2 JP5154639 B2 JP 5154639B2 JP 2010500830 A JP2010500830 A JP 2010500830A JP 2010500830 A JP2010500830 A JP 2010500830A JP 5154639 B2 JP5154639 B2 JP 5154639B2
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- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical class I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- SHNBXKOUKNSCSQ-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 SHNBXKOUKNSCSQ-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007122 ortho-metalation reaction Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical compound [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
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Description
R1及びR2はそれぞれ独立的に水素、炭素数6乃至24の芳香族炭化水素基、及び少なくとも一つの不飽和脂肪族モエティを有する炭素数6乃至30の芳香族炭化水素基からなる群から選択され;
Xは炭素、シリコン、酸素及び硫黄からなる群から選択され、
Xが炭素又はシリコンの場合、mは4で、nは1乃至4の整数であり、
Xが酸素又は硫黄の場合、mは2で、nは1又は2である。)
正極;負極;及び前記負極と正極間に少なくとも一つの発光層を含み、
前記発光層が前記KLホスト材料を含む有機電界発光素子を提供する。
R1及びR2はそれぞれ独立的に水素、炭素数6乃至24の芳香族炭化水素基、及び少なくとも一つの不飽和脂肪族モエティを有する炭素数6乃至30の芳香族炭化水素基からなる群から選択され;
Xは炭素、シリコン、酸素及び硫黄からなる群から選択され、
Xが炭素又はシリコンの場合、mは4で、nは1乃至4の整数であり、
Xが酸素又は硫黄の場合、mは2で、nは1又は2である。
9−(4’−ブロモナフチル)−カルバゾールの製造
化合物2のUV及びPLの強度を図7に示した。
3,6−ジフェニルカルバゾールの製造
化合物6のUV及びPL強度を図8に示した。
KLホスト材料に下記化学式(5)の物質(K−3)を使用したことを除けば、実施例7と同じ方法で有機電界発光素子を製造した(図29参照)。
ホスト材料としてCBP(4,4’−ビス(カルバゾール−9−イル)−2,2'−ビフェニル)を使用し、ドーパントとしてBtp2Ir(acac)(ビス(2−(2'−ベンゾ[4,5−α]チエニル)ピリジナト−N,C3')イリジウム(アセチルアセトネート)(以下、「BTP」と称する)を使用したことを除けば、実施例7と同じように有機電界発光素子を製造した(図30参照)。
(Photo Research PR−650)を用いて測定した。
Claims (17)
- 下記化学式(1)の構造を有する化合物:
R1及びR2はそれぞれ独立的に水素、炭素数6乃至24の芳香族炭化水素基、及び少なくとも一つの不飽和脂肪族モエティを有する炭素数6乃至30の芳香族炭化水素基からなる群から選択され;
Xは炭素およびシリコンからなる群から選択され、
Xが炭素又はシリコンの場合、mは4で、nは1乃至4の整数である。) - ドーパントとともに使用する場合にエネルギー遷移が蛍光と燐光の各々又はすべてに転移され、これによるドーパントの発光と同時に発光する、有機電界発光素子の発光層を形成するためのKLホスト材料であり、
前記ホスト材料は発光層を形成するために蛍光及び燐光ドーパントのうち少なくとも一つのドーパントと組み合わせられ、
ホスト材料のエネルギーはドーパントを発光させ、同時にホスト材料自体を発光させるために蛍光及び燐光ドーパントのうち少なくとも一つのドーパントに転移され、
前記ホスト材料は下記化学式(1)の化合物であることを特徴とするKLホスト材料:
R1及びR2はそれぞれ独立的に水素、炭素数6乃至24の芳香族炭化水素基、及び少なくとも一つの不飽和脂肪族モエティを有する炭素数6乃至30の芳香族炭化水素基からなる群から選択され;
Xは炭素およびシリコンからなる群から選択され;
Xが炭素又はシリコンの場合、mは4で、nは1乃至4の整数である。) - 正極(anode);負極(cathode);及び前記負極と正極間に少なくとも一つの発光層を含み、
前記発光層が請求項3のKLホスト材料を含むことを特徴とする有機電界発光素子。 - 前記発光層が燐光ドーパント及び蛍光ドーパントのうち少なくとも一つのドーパントをさらに含むことを特徴とする請求項4に記載の有機電界発光素子。
- 前記KLホスト材料の発光及びドーパントの発光が単一層で起きることを特徴とする請求項4に記載の有機電界発光素子。
- 前記発光層で蛍光と燐光が同時に発光することを特徴とする請求項5に記載の有機電界発光素子。
- 前記発光層がKLホスト材料と互いに異なる二つ以上のドーパントを含む2層以上の多層構造であることを特徴とする請求項4に記載の有機電界発光素子。
- 前記発光層の厚さが1〜60nmであることを特徴とする請求項7に記載の有機電界発光素子。
- 前記ドーパントが互いに異なる燐光ドーパントであることを特徴とする請求項7に記載の有機電界発光素子。
- 前記ドーパントが前記発光層総100質量部に対して0.5〜35質量部で含まれることを特徴とする請求項4に記載の有機電界発光素子。
- 前記KLホスト材料からの発光はKLホスト材料のエネルギー転移によって前記ドーパントの発光と混合されて混色発光することを特徴とする請求項4に記載の有機電界発光素子。
- 前記混色発光が白色発光であることを特徴とする請求項12に記載の有機電界発光素子。
- 前記KLホスト材料が青色発光することを特徴とする請求項4に記載の有機電界発光素子。
- 前記負極(cathode)と前記発光層間に正孔遮断層が具備されないことを特徴とする請求項4に記載の有機電界発光素子。
- 請求項4乃至14のいずれか一項の有機電界発光素子を含むことを特徴とする表示装置。
- 請求項4乃至14のいずれか一項の有機電界発光素子を具備することを特徴とする照明装置。
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020070031148A KR101369662B1 (ko) | 2007-03-29 | 2007-03-29 | 신규 화합물, kl 호스트 재료 및 이를 포함한유기전계발광소자 |
KR10-2007-0031148 | 2007-03-29 | ||
KR10-2007-0031821 | 2007-03-30 | ||
KR1020070031821A KR101442826B1 (ko) | 2007-03-30 | 2007-03-30 | Kl 호스트 재료를 사용한 새로운 유기전계발광소자 및이를 구비한 표시장치 |
KR10-2007-0140745 | 2007-12-28 | ||
KR1020070140745A KR20090072588A (ko) | 2007-12-28 | 2007-12-28 | 유기전기발광소자 및 이를 구비한 표시장치 및 조명장치 |
PCT/KR2008/001716 WO2008120899A1 (en) | 2007-03-29 | 2008-03-27 | Naphthyl carbazole derivatives, kl host material, the organic light emitting device employing the same, the display device and the illumination device employing the same |
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JP2010522745A JP2010522745A (ja) | 2010-07-08 |
JP5154639B2 true JP5154639B2 (ja) | 2013-02-27 |
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KR100991416B1 (ko) * | 2007-12-31 | 2010-11-03 | 다우어드밴스드디스플레이머티리얼 유한회사 | 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
KR100924145B1 (ko) * | 2008-06-10 | 2009-10-28 | 삼성모바일디스플레이주식회사 | 유기전계발광소자 및 이의 제조방법 |
WO2010052932A1 (ja) | 2008-11-07 | 2010-05-14 | 保土谷化学工業株式会社 | トリフェニルシリル基とトリアリールアミン構造を有する化合物および有機エレクトロルミネッセンス素子 |
KR20100118700A (ko) * | 2009-04-29 | 2010-11-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
US20140054564A1 (en) * | 2010-07-30 | 2014-02-27 | Rohm And Haas Electronic Materials Korea Ltd. | Electroluminescent device using electroluminescent compound as luminescent material |
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