KR100259398B1 - 신규베릴륨계착물,이의제조방법및이를이용한저전압구동을위한유기발광소자 - Google Patents
신규베릴륨계착물,이의제조방법및이를이용한저전압구동을위한유기발광소자 Download PDFInfo
- Publication number
- KR100259398B1 KR100259398B1 KR1019980004989A KR19980004989A KR100259398B1 KR 100259398 B1 KR100259398 B1 KR 100259398B1 KR 1019980004989 A KR1019980004989 A KR 1019980004989A KR 19980004989 A KR19980004989 A KR 19980004989A KR 100259398 B1 KR100259398 B1 KR 100259398B1
- Authority
- KR
- South Korea
- Prior art keywords
- light emitting
- formula
- layer
- compound
- emitting device
- Prior art date
Links
- 229910052790 beryllium Inorganic materials 0.000 title claims abstract description 14
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000000034 method Methods 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 31
- 238000002347 injection Methods 0.000 claims description 30
- 239000007924 injection Substances 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 239000011521 glass Substances 0.000 claims description 14
- 230000032258 transport Effects 0.000 claims description 14
- 239000010409 thin film Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 9
- -1 beryllium halide Chemical class 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001572 beryllium Chemical class 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- UYWJEYYMHCWFCQ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=C(C=CC=C1)C=1SC2=C(N1)C=CC=C2.OC2=C(C=CC=C2)C=2SC1=C(N2)C=CC=C1 UYWJEYYMHCWFCQ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910001627 beryllium chloride Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 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 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- SMWMPMNQFQRVTR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(C=2SC3=CC=CC=C3N=2)=C1 SMWMPMNQFQRVTR-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000012857 radioactive material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/006—Beryllium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/181—Metal complexes of the alkali metals and alkaline earth metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019980004989A KR100259398B1 (ko) | 1997-02-22 | 1998-02-18 | 신규베릴륨계착물,이의제조방법및이를이용한저전압구동을위한유기발광소자 |
| KR1019990062660A KR100258749B1 (en) | 1997-02-22 | 1999-12-27 | Process for the preparation of organic luminescentdevices using novel beryllium complex |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019970005406 | 1997-02-22 | ||
| KR19970005406 | 1997-02-22 | ||
| KR97-5406 | 1997-02-22 | ||
| KR1019980004989A KR100259398B1 (ko) | 1997-02-22 | 1998-02-18 | 신규베릴륨계착물,이의제조방법및이를이용한저전압구동을위한유기발광소자 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR19980071472A KR19980071472A (ko) | 1998-10-26 |
| KR100259398B1 true KR100259398B1 (ko) | 2000-06-15 |
Family
ID=19497678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980004989A KR100259398B1 (ko) | 1997-02-22 | 1998-02-18 | 신규베릴륨계착물,이의제조방법및이를이용한저전압구동을위한유기발광소자 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0897652A1 (fr) |
| JP (1) | JP2000515926A (fr) |
| KR (1) | KR100259398B1 (fr) |
| TW (1) | TW373211B (fr) |
| WO (1) | WO1998037736A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6558817B1 (en) * | 1998-09-09 | 2003-05-06 | Minolta Co., Ltd. | Organic electroluminescent element |
| KR100373203B1 (ko) * | 1999-03-31 | 2003-02-25 | 주식회사 엘지화학 | 새로운 큐마린계 착물 및 이를 이용한 유기 발광 소자 |
| KR100578424B1 (ko) | 2002-05-07 | 2006-05-11 | 주식회사 엘지화학 | 새로운 유기 발광용 화합물 및 이를 이용한 유기 발광 소자 |
| JP5669346B2 (ja) | 2007-07-24 | 2015-02-12 | グレイセル・ディスプレイ・インコーポレーテッドＧｒａｃｅｌ Ｄｉｓｐｌａｙ Ｉｎｃ． | 新規な赤色エレクトロルミネッセンス化合物およびそれを使用した有機エレクトロルミネッセンスデバイス |
| KR100970713B1 (ko) * | 2007-12-31 | 2010-07-16 | 다우어드밴스드디스플레이머티리얼 유한회사 | 유기발광화합물을 발광재료로서 채용하고 있는 전기 발광소자 |
| KR101294620B1 (ko) * | 2010-06-07 | 2013-08-07 | 롬엔드하스전자재료코리아유한회사 | 유기발광화합물을 발광재료로서 채용하고 있는 전기 발광 소자 |
| JP6115395B2 (ja) * | 2013-08-14 | 2017-04-19 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子用金属錯体、並びに表示装置及び照明装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5529853A (en) * | 1993-03-17 | 1996-06-25 | Sanyo Electric Co., Ltd. | Organic electroluminescent element |
| JPH07133483A (ja) * | 1993-11-09 | 1995-05-23 | Shinko Electric Ind Co Ltd | Ｅｌ素子用有機発光材料及びｅｌ素子 |
| US5486406A (en) * | 1994-11-07 | 1996-01-23 | Motorola | Green-emitting organometallic complexes for use in light emitting devices |
-
1997
- 1997-07-08 EP EP97930874A patent/EP0897652A1/fr not_active Withdrawn
- 1997-07-08 JP JP10536500A patent/JP2000515926A/ja not_active Ceased
- 1997-07-08 WO PCT/KR1997/000134 patent/WO1998037736A1/fr not_active Application Discontinuation
- 1997-07-30 TW TW086111076A patent/TW373211B/zh not_active IP Right Cessation
-
1998
- 1998-02-18 KR KR1019980004989A patent/KR100259398B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000515926A (ja) | 2000-11-28 |
| EP0897652A1 (fr) | 1999-02-24 |
| KR19980071472A (ko) | 1998-10-26 |
| TW373211B (en) | 1999-11-01 |
| WO1998037736A1 (fr) | 1998-08-27 |
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