EP2217677A1 - Composés organiques électroluminescents et dispositif d'affichage les contenant - Google Patents

Composés organiques électroluminescents et dispositif d'affichage les contenant

Info

Publication number
EP2217677A1
EP2217677A1 EP07851144A EP07851144A EP2217677A1 EP 2217677 A1 EP2217677 A1 EP 2217677A1 EP 07851144 A EP07851144 A EP 07851144A EP 07851144 A EP07851144 A EP 07851144A EP 2217677 A1 EP2217677 A1 EP 2217677A1
Authority
EP
European Patent Office
Prior art keywords
group
chemical formula
aromatic ring
compound
organic electroluminescent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07851144A
Other languages
German (de)
English (en)
Inventor
Hyo-Nim Shin
Il Won Choi
Hyuck Joo Kwon
Young-Jun Cho
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gracel Display Inc
Original Assignee
Gracel Display Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gracel Display Inc filed Critical Gracel Display Inc
Publication of EP2217677A1 publication Critical patent/EP2217677A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems

Definitions

  • the present invention relates to novel organic electroluminescent compound represented and a display device comprising the same.
  • a green fluorescent material As a green fluorescent material, a system wherein a coumarine derivative (Compound d, C545T) , a quinacridone derivative (Compound e) , DPT (Compound f) or the like is doped to AIq (a host) , as a dopant, in a concentration from several % to not more than 20 % has been developed and widely used.
  • AIq a host
  • the conventional electroluminescent materials suffer from significant problem in view of lifetime with noticeable reduction of initial efficiency, though they show good performance in view of initial luminous efficiency at the level of practical use.
  • the materials have limitations to be employed for a high performance panel of larger screen.
  • the object of the present invention is to overcome the problems as described above, and to provide electroluminescent compounds having noticeably improved properties of the host which serves as a solvent or an energy carrier in the electroluminescent material, as compared to those of the conventional materials.
  • the object of the present invention is to provide a blue or green electroluminescent material with improved luminous efficiency and lifetime of the device, and an organic electroluminescent device comprising the same.
  • the present invention relates to organic electroluminescent compounds represented by Chemical Formula 1:
  • Rl to R3 independently represent phenyl group or C10-C20 fused multi-cyclic aromatic ring, and the phenyl group or C10-C20 fused multi-cyclic aromatic ring of Rl to R3 may be further substituted by Cl ⁇ C20 alkyl group, Cl ⁇ C20 alkoxy group, halogen, C5-C7 cycloalkyl group, phenyl group or a fused multi-cyclic aromatic group: and a display device using the same .
  • the electroluminescent materials mentioned in the present invention include, in a broad sense, any material employed as the organic substance in an organic electroluminescent device comprised of a first electrode, a second electrode and an organic substance interposed between the first and the second electrode; while they imply, in a narrow sense, what is applied to an electroluminescent host which serves as an electroluminescent medium in an electroluminescent layer.
  • Rl through R3 are independently selected from the group consisting of phenyl, naphtyl, anthryl, fluorenyl, phenanthryl, fluorancenyl, pyrenyl, perylenyl or naphthacenyl; and phenyl, naphthyl, anthryl, fluorenyl, phenanthryl, flurorancenyl, pyrenyl, perylenyl and naphthacenyl are optionally substituted by C1-C20 alkyl groups, C1-C20 alkoxy groups, halogen atoms, C5-C7 cycloalkyl groups, phenyl group, or a fused multicyclic aromatic group.
  • the organic electroluminescent compounds represented by Chemical Formula 1 according to the present invention can be represented by the following formulas, but these formulas cannot limit the scope of the present invention:
  • the present invention also provides an organic electroluminescent device comprised of a first electrode; a second electrode; and one or more organic layer (s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more compound (s) represented by Chemical Formula 1: [Chemical Formula 1]
  • Rl to R3 independently represent phenyl group or C10-C20 fused multi-cyclic aromatic ring, and the phenyl group or C10-C20 fused multi-cyclic aromatic ring of Rl to R3 may be further substituted by C1-C20 alkyl group, C1-C20 alkoxy group, halogen, C5-C7 cycloalkyl group, phenyl group or a fused multi-cyclic aromatic group.
  • the organic electroluminescent (EL) device is characterized in that the organic layer comprises EL region which comprises one or more EL dopant with one or more compound (s) represented by Chemical Formula (1) as an EL host.
  • the EL dopants applied to the organic EL device of the present invention are not particularly restricted, but exemplified by the compounds represented by one of Chemical Formulas 2 to 4: [Chemical Formula 2]
  • ArI and Ar2 are independently indenofluorene, fluorene or spiro- fluorene, represented by following chemical formulas:
  • RIl to Rl ⁇ are independently selected from the group consisting of C1-C20 alkyl, and phenyl or naphthyl with or without C1 ⁇ C5 alkyl substituent (s) ;
  • Ar3 to Ar ⁇ are independently selected from C5-C20 aromatic or multi-cyclic aromatic ring; provided that ArI and Ar2 are identical, Ar3 and Ar5 are identical, and Ar4 and Ar ⁇ are identical
  • a and B independently represent a chemical bond, or R17 and R18 independently represent an aromatic ring or a multi-cyclic aromatic ring wherein two or more aromatic rings have been fused;
  • R19 to R22 independently represent a linear or branched C1-C20 alkyl group with or without halogen substituent (s) ;
  • R23 to R26 independently represent hydrogen or an aromatic group;
  • Ar7 to ArIO independently represent an aromatic ring or a multi-cyclic aromatic ring wherein two or more aromatic rings have been fused.
  • the compounds of Chemical Formula 3 or Chemical Formula 4 may be specifically exemplified by compounds represented by one of the following formulas:
  • R19 to R22 represent methyl group or ethyl group.
  • the green EL compounds can be exemplified by the compounds represented by one of Chemical Formulas 5 to 7 : [Chemical Formula 5]
  • R27 and R28 independently represent a multicyclic aromatic ring wherein two more aromatic rings have been fused; R29 to R32 independently represent an aromatic ring; and each aromatic ring of R27 to R32 may be further substituted by C1-C20 alkyl group (s).
  • the compounds of Chemical Formula 6 and Chemical Formula 7 can be specifically exemplified by compounds
  • FIG. 1 shows luminous efficiency - current density property of Comparative Example 1
  • Fig. 2 shows current density - voltage property of a blue OLED according to Example 9;
  • Fig. 3 shows luminous efficiency - current density property of the blue OLED according to Example 9
  • Fig. 4 shows luminous efficiency - luminance property of a green OLED, to which conventional electroluminescent material was applied, according to Comparative Example 2;
  • Fig. 5 shows luminous efficiency - current density property of a green OLED according to Example 22
  • Fig. 6 shows luminous efficiency - current density property of green OLEDs according to Example 22, Comparative Example 3 and Comparative Example 4;
  • Fig. 7 is a curve to compare color purity of green OLEDs according to Example 22 and Comparative Example 2.
  • the solid obtained was washed sequentially with methanol (300 mL) , ethyl acetate (100 mL) and tetrahydrofuran (50 mL) , to provide the target compound (101) (10.0 g, 68%) as pale ivory solid.
  • An OLED device was made by using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ /D) obtained from glass for OLED was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopronanol before use.
  • an ITO substrate was equipped in a substrate folder of vacuum vapor-deposit device, and 4, 4' , 4"-tris (N, N- (2- naphthyl) -phenylamino) triphenylamine (2-TNATA) represented by following chemical formula was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 10-6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA to vapor-deposit a hole injection layer having 60 nrn of thickness on the ITO substrate.
  • N N, N' -bis ( ⁇ -naphthyl) -N, N' -diphenyl-4 , 4' -diamine (NPB) represented by following chemical formula, and electric current was applied to the cell to evaporate NPB to vapor- deposit a hole transport layer having 20 nm of thickness on the hole injection layer.
  • an electroluminescent layer was vapor-
  • an electroluminescent layer was vapor- deposited by doping of perylene in a concentration from 2 to 5 mol% with a thickness of 35 nm, on the hole transport layer.
  • a hole injection layer and a hole transport layer were formed as in Example 1, and an EL layer was vapor-deposited thereon as follows.
  • a compound according to the present invention for example, Compound 121
  • Coumarin 545T C545T
  • an EL layer was vapor-deposited by doping of Coumarine 545T (C545T) in a concentration from 2 to 5 mol% with a thickness of 35 nm, on the hole transport layer.
  • Example 2 According to the same procedure as in Example 1, an electron transport layer and an electron injection layer were vapor-deposited, and Al cathode was vapor-deposited with a thickness of 150 ran by using another vapor-deposition device, to manufacture an OLED.
  • a hole injection layer and a hole transport layer were formed as in Example 1.
  • Example 1 In one cell of the vacuum vapor- deposit device, charged was dinaphthylanthracene (DNA) as a blue EL material, and in another cell charged was perylene as another blue EL material.
  • An electroluminescent layer was vapor-deposited with a thickness of 35 nm, on the hole transport layer by using the vapor-deposit rate of 100:1.
  • Example 2 According to the same procedure as in Example 1, an electron transport layer and an electron injection layer were vapor-deposited, and Al cathode was vapor-deposited in a thickness of 150 nm by using another vapor-deposition device, to manufacture an OLED.
  • Example 2 Manufacture of OLED device by using conventional EL material A hole injection layer and a hole transport layer were formed as in Example 1. To another cell in the vapor- deposition device, charged was tris(8- hydroxyquinoline) aluminum (III) (AIq) as an EL host material, and to still another cell, charged was Coumarin 545T (C545T) . By evaporating the two substances in a different rate, an EL layer was vapor-deposited by doping with a thickness of 30 nm, on the hole transport layer. The doping concentration was preferably from 2 to 5 mol% on the basis of AIq.
  • Example 2 According to the same procedure as in Example 1, an electron transport layer and an electron injection layer were vapor-deposited, and Al cathode was vapor-deposited in a thickness of 150 nm by using another vapor-deposition device, to manufacture an OLED.
  • a hole injection layer and a hole transport layer were formed as in Example 1.
  • To another cell in the vapor- deposition device charged was dinaphthylanthracene (DNA) as a blue EL material, and to still another cell, charged was Coumarin 545T (C545T) .
  • DDL dinaphthylanthracene
  • C545T Coumarin 545T
  • an EL layer was vapor-deposited by doping, with a thickness of 30 nm, on the hole transport layer.
  • the doping concentration was preferably from 2 to 5 mol% on the basis of AIq.
  • a hole injection layer and a hole transport layer were formed as in Example 1.
  • Compound (A) disclosed by US Patent Publication No. 20060046097A1 having the structure shown below as a blue EL material, and to still another cell, charged was Coumarin 545T (C545T) .
  • C545T Coumarin 545T
  • an EL layer was vapor- deposited by doping, with a thickness of 30 nm, on the hole transport layer.
  • the doping concentration was preferably from 2 to 5 mol% on the basis of AIq.
  • Example 2 According to the same procedure as in Example 1, an electron transport layer and an electron injection layer were vapor-deposited, and Al cathode was vapor-deposited in a thickness of 150 nm by using another vapor-deposition device, to manufacture an OLED.
  • Example 1 Blue EL property of the OLED devices manufactured Blue luminous efficiencies of OLEDs manufactured from Examples 1 to 13 and Comparative Example 1, comprising an organic EL compound according to the present invention and a conventional electroluminescent compound, respectively, were measured at 500 cd/m2 and 2,000 cd/m2, individually, of which the results are shown in Table 3.
  • Table 3 shows the results of applying the material according to the present invention to a blue EL device.
  • the luminous efficiency of the EL material according to the invention was 5.26-6.30 cd/A at low luminance, and 4.80-5.88 cd/A at high luminance, while that of the EL material of Comparative Example 1 was 4.45 cd/A and 3.6 cd/A at low luminance and high luminance, respectively.
  • the EL device employing the organic EL compound according to the present invention showed higher luminous efficiency by 1.5 cd/A or more, as compared to that of Comparative Example. In particular, improvement in luminous efficiency by 2 cd/A or more was confirmed at high luminance for each compound.
  • Fig. 1 shows luminous efficiency - current density property of Comparative Example 1 employing DNA:perylene as a conventional EL material
  • Fig. 2 and Fig. 3 show current density - voltage property and luminous efficiency - current density property of Example 9 employing Compound (121) according to the present invention as an EL material.
  • the results shown in the figures confirmed noticeable improvement in performances
  • Table 4 shows the results of properties from the green EL device to which the material according to the present invention was applied. Alike the blue EL devices according to Experimental Example 1, excellent properties were confirmed at low luminance and high luminance, as compared to conventional EL material.
  • the EL material of the present invention having improved luminous efficiency while maintaining the color purity as such can be referred to as an epoch-making invention which surpasses one stage beyond the conventional materials.
  • Fig. 4 shows luminous efficiency - luminance property of Comparative Example 2 employing Alq:C545T as a conventional green EL material
  • Fig. 5 shows luminous efficiency - current density property of the green EL device of Example 22 employing Compound (121) according to the present invention as an EL material
  • Fig. 6 shows luminous efficiency - current density property of the green EL devices of Comparative Example 3 and 4 employing conventional EL material, and Example 22 employing Compound (121) according to the present invention as an EL material.
  • the EL material according to the present invention can be applied to both a blue OLED and a green OLED, and showed excellent results in view of performances. Those results show prominent characteristics of excellent EL material.
  • the invention of the material having those characteristics leads simplification of the structure of an OLED panel, to result in subsidiary result of reducing the production cost of an OLED. Due to the excellent features, innovative results may occur in development in the field of OLED' s.
  • Fig. 7 shows the comparison of color purity of a green EL device according to Example 22 employing Compound (121) of the present invention as an EL material with that of a green EL device according to Comparative Example 2.
  • the EL material of the invention showed good EL color property, as showing no significant difference as compared to a conventional pure green EL material.
  • a typical green EL peak at 520 nm was confirmed. This exhibits the fact that the organic EL compound having blue EL property according to the present invention has very good electric property to induce the feature of an EL dopant up to a maximum level.
  • the electroluminescent compound according to the invention has good luminous efficiency and excellent lifetime of the material, so that an OLED device having very good operation lifetime can be prepared.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé organique électroluminescent et un dispositif d'affichage l'employant. Le composé organique électroluminescent selon la présente invention présente une bonne efficacité lumineuse et une excellente durée de vie du matériau, et permet de préparer un dispositif DELO dont la durée de vie en fonctionnement est excellente.
EP07851144A 2007-11-23 2007-11-23 Composés organiques électroluminescents et dispositif d'affichage les contenant Withdrawn EP2217677A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/KR2007/005942 WO2009066814A1 (fr) 2007-11-23 2007-11-23 Composés organiques électroluminescents et dispositif d'affichage les contenant

Publications (1)

Publication Number Publication Date
EP2217677A1 true EP2217677A1 (fr) 2010-08-18

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EP07851144A Withdrawn EP2217677A1 (fr) 2007-11-23 2007-11-23 Composés organiques électroluminescents et dispositif d'affichage les contenant

Country Status (4)

Country Link
EP (1) EP2217677A1 (fr)
JP (1) JP2011504493A (fr)
CN (1) CN101874096A (fr)
WO (1) WO2009066814A1 (fr)

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Publication number Priority date Publication date Assignee Title
JP5723127B2 (ja) * 2009-09-28 2015-05-27 双葉電子工業株式会社 有機ｅｌ素子用化合物及び有機ｅｌ素子
CN102795983B (zh) * 2011-05-25 2016-01-20 海洋王照明科技股份有限公司 蒽醌衍生物材料及其制备方法和应用
CN109678645A (zh) * 2018-12-28 2019-04-26 陕西师范大学 一种基于双蒽的有机蓝色荧光材料及其制备方法和应用

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JP2004231563A (ja) * 2003-01-30 2004-08-19 Idemitsu Kosan Co Ltd ビアントリル誘導体、それを含む発光性塗膜形成用材料及び有機エレクトロルミネッセンス素子
KR100864364B1 (ko) * 2005-12-13 2008-10-17 주식회사 엘지화학 신규한 이미다조퀴나졸린 유도체, 이의 제조방법 및 이를이용한 유기전기소자
KR100872692B1 (ko) * 2006-03-06 2008-12-10 주식회사 엘지화학 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자
DE102006013802A1 (de) * 2006-03-24 2007-09-27 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
JP5088097B2 (ja) * 2006-11-02 2012-12-05 三菱化学株式会社 有機電界蛍光発光素子用材料、有機電界蛍光発光素子用組成物、有機電界蛍光発光素子、有機ｅｌディスプレイ及びカラーディスプレイ表示装置
KR100858816B1 (ko) * 2007-03-14 2008-09-17 삼성에스디아이 주식회사 안트라센 유도체 화합물을 포함하는 유기막을 구비하는유기 발광 소자

Non-Patent Citations (1)

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Title
See references of WO2009066814A1 *

Also Published As

Publication number Publication date
JP2011504493A (ja) 2011-02-10
WO2009066814A1 (fr) 2009-05-28
CN101874096A (zh) 2010-10-27

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