WO2011010843A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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WO2011010843A1
WO2011010843A1 PCT/KR2010/004697 KR2010004697W WO2011010843A1 WO 2011010843 A1 WO2011010843 A1 WO 2011010843A1 KR 2010004697 W KR2010004697 W KR 2010004697W WO 2011010843 A1 WO2011010843 A1 WO 2011010843A1
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substituent
alkyl
aryl
fused
organic electroluminescent
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PCT/KR2010/004697
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French (fr)
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Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Rohm And Haas Electronic Materials Korea Ltd.
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Publication of WO2011010843A1 publication Critical patent/WO2011010843A1/en

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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same.
  • the organic electroluminescent compound according to the present invention is represented by Chemical Formula 1:
  • the organic EL device commonly has a configuration of anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission material layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the electroluminescent materials may be divided into host materials and dopant materials.
  • an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property.
  • development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
  • development of materials which are much superior to existing electroluminescent materials is urgently needed.
  • TBSA dispiro-fluorene-anthracene
  • TSF ter-spirofluorene
  • BTP bitriphenylene
  • a green fluorescent material As a green fluorescent material, a system wherein a coumarine derivative, a quinacridone derivative, DPT or the like as a dopant is doped to Alq as a host in a concentration from several % to dozens of % has been developed and widely used.
  • 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 invention is to overcome the problems described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, device life and appropriate color coordinates, as compared to conventional host materials.
  • Another object of the invention is to provide an organic electroluminescent device of high efficiency and long life by employing the organic electroluminescent compound as electroluminescent material.
  • the present invention relates to organic electroluminescent compounds represented by Chemical Formula (1), and an organic electroluminescent device using the same.
  • the organic electroluminescent compounds according to the invention exhibit high luminous efficiency, and excellent color purity and life property of the material, so that OLED's with very excellent operation life can be manufactured therefrom.
  • B 1 through B 9 independently represent CR 12 or N;
  • A represents (C6-C30)arylene with or with substituent(s), (C2-C30)heteroarylene with or with substituent(s), 5- to 7-membered heterocycloalkylene with or with substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or with substituent(s), (C3-C30)cycloalkylene with or with substituent(s), cycloalkylene fused with one or more aromatic ring(s) with or with substituent(s), (C2-C30)alkenylene with or with substituent(s), (C2-C30)alkynylene with or with substituent(s), (C6-C30)ar(C1-C30)alkylene with or with substituent(s), (C1-C30)alkylenethio with or with substituent(s), (C1-C30)alkyleneoxy with or with substituent(s), (C6-C30)aryleneoxy with or with substitu
  • R 51 through R 58 and R 61 through R 63 are the same as R 1 through R 12 ;
  • R 21 through R 28 independently represent (C1-C30)alkyl with or with substituent(s), (C6-C30)aryl with or with substituent(s) or (C3-C30)heteroaryl with or with substituent(s),
  • R a , R b , R c and R d independently represent (C1-C30)alkyl with or with substituent(s) or (C6-C30)aryl with or with substituent(s),
  • the Y represents S or O
  • R e and R f represent (C1-C30)alkyl with or with substituent(s), (C1-C30)alkoxy with or with substituent(s), (C6-C30)aryl with or with substituent(s) or (C6-C30)aryloxy with or with substituent(s); and
  • n an integer 1 or 2.
  • 'alkyl' 'alkoxy' and other substituents containing 'alkyl' moiety include both linear and branched species.
  • 'cycloalkyl' includes both adamantyl with or without substituent(s) and (C7-C30)bicycloalkyl with or without substituent(s).
  • 'aryl' means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s).
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • heteroaryl may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated.
  • the heteroaryl includes more than one heteroaryls linked by single bond(s).
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, is
  • the '(C1-C30)alkyl' groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the '(C6-C30)aryl' groups include (C6-C20)aryl or (C6-C12)aryl.
  • the '(C3-C30)heteroaryl' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the '(C3-C30)cycloalkyl' roups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
  • the '(C2-C30)alkenyl or alkynyl' groups include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
  • the term 'substituted' means having one or more substituent(s) independently selected from deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), a 5- to 7-membered heterocycloalkyl, a 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsily
  • the R 1 through R 12 , R 21 through R 28 , R 51 through R 58 , and R 61 through R 63 are selected from hydrogen, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl such as 1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl,
  • heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc., or , but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
  • R 1 through R 12 may be exemplified as following structures but are not limited thereto.
  • R 41 through R 48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
  • R 1 through R 12 are exemplified by the following structures, but not limited thereto.
  • organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but is not limited thereto.
  • the organic electroluminescent compound according to the present invention may be prepared as shown in following Reaction Scheme 1.
  • A, B 1 through B 9 and R 1 through R 11 are the same as definition in the Chemical Formula 1.
  • an organic electroluminescent device which comprises 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 organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the organic electroluminescent compound is used as a host material of the electroluminescent layer.
  • the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more dopants besides one or more organic electroluminescent compounds of Chemical Formula 1.
  • the dopant applied to the organic electroluminescent device of the present invention is not specifically limited.
  • the dopant applied to the organic electroluminescent device of the present invention may be selected from following Chemical Formulas 2 and 3.
  • Ar 11 and Ar 12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar 11 and Ar 12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono
  • Ar 13 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1;
  • Ar 13 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2;
  • Ar 14 and Ar 15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
  • R 201 through R 203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
  • d represents an integer from 1 to 4.
  • e represents an integer 0 or 1;
  • R 301 through R 308 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s).
  • the meaning of the electroluminescent layer may be a single layer as a layer where the light is emitted or may be a multiple layer where two or more layers are laminated.
  • the electroluminescent host of the present invention when host-dopant are used in mixture, it is confirmed that the luminous efficiency are remarkably improved by the electroluminescent host of the present invention. It may be configured at doping concentration of 0.5 to 10wt%.
  • the electroluminescent host of the present invention has superior conductivity with respect to the hole and electron and excellent stability in material, thereby showing a characteristic of remarkably increasing its life span as well as improving the luminous efficiency.
  • the dopant compounds of Chemical Formulas 2 and 3 may be exemplified as the compounds described in Korean Patent Application No. 10-2009-0023442. More preferably, they are selected from following structures but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer (hereinafter referred to as 'surface layer' selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
  • the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
  • Compound 1-2 (20 g, 83 %) was obtained via column separation by using hexane and ethyl acetate as a developing solvent.
  • Organic electroluminescent compounds 1 to 63 were prepared in the same manner as Preparation Example 1. 1 H NMR and MS/FAB data of the prepared organic electroluminescent compounds are given in Table 1.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • N , N'- bis(a-naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows.
  • Compound 1 was placed in a cell of a vacuum vapor deposition apparatus as host, and Compound E was placed in another cell as a dopant.
  • the two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 2 to 5 wt%.
  • Each compound used in the OLED was purified by vacuum sublimation at 10 -6 torr.
  • An OLED was manufactured in the same manner as Example 1 except that dinaphthylanthracene (DNA) instead of the Compound according to the present invention was used as host at an electroluminescent layer.
  • DNA dinaphthylanthracene
  • An OLED was manufactured as in Example 1 except for using Compound 1 of the present invention as host in the electroluminescent layer and using following Compound A as dopant.
  • An OLED was manufactured in the same manner as Example 2 except that dinaphthylanthracene (DNA) instead of the Compound according to the present invention was used as host at an electroluminescent layer.
  • DNA dinaphthylanthracene
  • Luminous efficiency of the OLED devices including the organic electroluminescent compound according to the present invention manufactured in Examples 1 and 2 and Comparative Examples 1 and 2 and the conventional electroluminescent compound was measured at 1,000 cd/m 2 . The result is given in Table 2.

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Abstract

The present invention relates to organic electroluminescent compounds and an organic electroluminescent device using the same. The organic electroluminescent compound accordingly to the present invention is represented by Chemical Formula 1.

Description

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same. The organic electroluminescent compound according to the present invention is represented by Chemical Formula 1:
[Chemical Formula 1]
Figure PCTKR2010004697-appb-I000001
In general, the organic EL device commonly has a configuration of anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode. Organic electroluminescent devices emitting blue, green or red light may be created depending on how to form the emission material layer.
In functional aspect, the electroluminescent materials may be divided into host materials and dopant materials. In general, an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property. Recently, development of an organic EL device having high efficiency and long operation life is becoming an imminent task. Especially, considering the level of EL performance required for medium-to-large sized OLED panels, development of materials which are much superior to existing electroluminescent materials is urgently needed.
In the meanwhile, for conventional blue materials, a number of materials have been developed and commercialized since the development of diphenylvinyl-biphenyl (DPVBi) by Idemitsu-Kosan. In addition to the blue material system from Idemitsu-Kosan, dinaphthylanthracene (DNA), tetra(t-butyl)perylene system or the like have been known. However, extensive research and development should be performed with respect to these materials. The distryl compound system of Idemitsu-Kosan, which is known to have the highest efficiency up to now, has 6 lm/W of power efficiency and beneficial device lifetime of more than 30,000 hr. However, when it is applied to a full-colored display, the color, which is sky blue, is not proper to be applied. In case of blue electroluminescence, it becomes advantageous from the aspect of the luminous efficiency, if the electroluminescent wavelength is shifted a little toward longer wavelength. However, it is not easy to apply the material to a display of high quality because of unsatisfactory color purity in blue. Furthermore, the research and development of such materials are urgent because of the problems in color purity, efficiency and thermal stability.
In order to develop a host material with high efficiency and long life, compounds based on different backbones have been disclosed, such as dispiro-fluorene-anthracene (TBSA), ter-spirofluorene (TSF) and bitriphenylene (BTP). These compounds, however, did not result in color purity and luminous efficiency at a sufficient level.
In the meanwhile, as a green fluorescent material, a system wherein a coumarine derivative, a quinacridone derivative, DPT or the like as a dopant is doped to Alq as a host in a concentration from several % to dozens of % has been developed and widely used. However, 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. Thus, the materials have limitations to be employed for a high performance panel of larger screen.
Further, since the OLED devices manufactured therefrom cannot give satisfactory level of device life by any means, required is development of host material having far improved stability and performances.
The object of the invention is to overcome the problems described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, device life and appropriate color coordinates, as compared to conventional host materials. Another object of the invention is to provide an organic electroluminescent device of high efficiency and long life by employing the organic electroluminescent compound as electroluminescent material.
The present invention relates to organic electroluminescent compounds represented by Chemical Formula (1), and an organic electroluminescent device using the same. The organic electroluminescent compounds according to the invention exhibit high luminous efficiency, and excellent color purity and life property of the material, so that OLED's with very excellent operation life can be manufactured therefrom.
[Chemical Formula 1]
Figure PCTKR2010004697-appb-I000002
wherein
B1 through B9 independently represent CR12 or N;
A represents (C6-C30)arylene with or with substituent(s), (C2-C30)heteroarylene with or with substituent(s), 5- to 7-membered heterocycloalkylene with or with substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or with substituent(s), (C3-C30)cycloalkylene with or with substituent(s), cycloalkylene fused with one or more aromatic ring(s) with or with substituent(s), (C2-C30)alkenylene with or with substituent(s), (C2-C30)alkynylene with or with substituent(s), (C6-C30)ar(C1-C30)alkylene with or with substituent(s), (C1-C30)alkylenethio with or with substituent(s), (C1-C30)alkyleneoxy with or with substituent(s), (C6-C30)aryleneoxy with or with substituent(s), (C6-C30)arylenethio with or with substituent(s), -O- or -S-;
R1 through R12 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or with substituent(s), (C6-C30)aryl with or with substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or with substituent(s), (C3-C30)heteroaryl with or with substituent(s), 5- to 7-membered heterocycloalkyl with or with substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or with substituent(s), (C3-C30)cycloalkyl with or with substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or with substituent(s), cyano, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, (C6-C30)ar(C1-C30)alkyl with or with substituent(s), (C2-C30)alkenyl with or with substituent(s), (C2-C30)alkynyl with or with substituent(s), carboxyl, nitro,
Figure PCTKR2010004697-appb-I000003
,
Figure PCTKR2010004697-appb-I000004
or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
W represents -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
R51 through R58 and R61 through R63 are the same as R1 through R12;
the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
the R21 through R28 independently represent (C1-C30)alkyl with or with substituent(s), (C6-C30)aryl with or with substituent(s) or (C3-C30)heteroaryl with or with substituent(s),
the Ra, Rb, Rc and Rd independently represent (C1-C30)alkyl with or with substituent(s) or (C6-C30)aryl with or with substituent(s),
the Y represents S or O, and
the Re and Rf represent (C1-C30)alkyl with or with substituent(s), (C1-C30)alkoxy with or with substituent(s), (C6-C30)aryl with or with substituent(s) or (C6-C30)aryloxy with or with substituent(s); and
m represents an integer 1 or 2.
In the present invention, 'alkyl' 'alkoxy' and other substituents containing 'alkyl' moiety include both linear and branched species. In the present invention, 'cycloalkyl' includes both adamantyl with or without substituent(s) and (C7-C30)bicycloalkyl with or without substituent(s).
In the present invention, 'aryl' means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s). Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. In the present invention, 'heteroaryl' means an aryl group containing 1 to 4 heteroatom(s) selected from B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
The '(C1-C30)alkyl' groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the '(C6-C30)aryl' groups include (C6-C20)aryl or (C6-C12)aryl. The '(C3-C30)heteroaryl' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the '(C3-C30)cycloalkyl' roups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The '(C2-C30)alkenyl or alkynyl' groups include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
In the term 'substituted or unsubstituted (or with or without) substituent(s)' described herein, the term 'substituted' means having one or more substituent(s) independently selected from deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), a 5- to 7-membered heterocycloalkyl, a 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl; or that adjacent substituent(s) are linked together to form a ring; and the R31 through R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
The R1 through R12, R21 through R28, R51 through R58, and R61 through R63 are selected from hydrogen, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl such as 1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl fused with one or more aromatic ring such as benzopyrrolidino, benzopiperidino, dibenzomorpholino, dibenzoazepino, etc., amino substituted by aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc. or heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc.,,
Figure PCTKR2010004697-appb-I000005
or
Figure PCTKR2010004697-appb-I000006
, but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
More specifically, the R1 through R12 may be exemplified as following structures but are not limited thereto.
Figure PCTKR2010004697-appb-I000007
Figure PCTKR2010004697-appb-I000008
Figure PCTKR2010004697-appb-I000009
Figure PCTKR2010004697-appb-I000011
wherein
R71 through R141 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s), (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), cyano, amino, (C1-C30)alkylamino, (C6-C30)arylamino, NR41R42, BR43R44, PR45R46, P(=O)R47R48, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring; and
the R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
More specifically, the R1 through R12 are exemplified by the following structures, but not limited thereto.
Figure PCTKR2010004697-appb-I000012
Figure PCTKR2010004697-appb-I000013
The organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but is not limited thereto.
Figure PCTKR2010004697-appb-I000014
Figure PCTKR2010004697-appb-I000015
Figure PCTKR2010004697-appb-I000016
Figure PCTKR2010004697-appb-I000017
Figure PCTKR2010004697-appb-I000018
Figure PCTKR2010004697-appb-I000019
Figure PCTKR2010004697-appb-I000020
Figure PCTKR2010004697-appb-I000021
Figure PCTKR2010004697-appb-I000022
Figure PCTKR2010004697-appb-I000023
Figure PCTKR2010004697-appb-I000024
Figure PCTKR2010004697-appb-I000025
Figure PCTKR2010004697-appb-I000026
Figure PCTKR2010004697-appb-I000027
Figure PCTKR2010004697-appb-I000028
Figure PCTKR2010004697-appb-I000029
Figure PCTKR2010004697-appb-I000030
Figure PCTKR2010004697-appb-I000031
Figure PCTKR2010004697-appb-I000032
Figure PCTKR2010004697-appb-I000033
Figure PCTKR2010004697-appb-I000034
The organic electroluminescent compound according to the present invention may be prepared as shown in following Reaction Scheme 1.
[Reaction Scheme 1]
Figure PCTKR2010004697-appb-I000035
wherein
A, B1 through B9 and R1 through R11 are the same as definition in the Chemical Formula 1.
Provided is an organic electroluminescent device, which comprises 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 organic electroluminescent compound(s) represented by Chemical Formula 1. The organic electroluminescent compound is used as a host material of the electroluminescent layer.
In addition, the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more dopants besides one or more organic electroluminescent compounds of Chemical Formula 1. The dopant applied to the organic electroluminescent device of the present invention is not specifically limited.
Preferably, the dopant applied to the organic electroluminescent device of the present invention may be selected from following Chemical Formulas 2 and 3.
[Chemical Formula 2]
Figure PCTKR2010004697-appb-I000036
wherein
Ar11 and Ar12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar11 and Ar12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
Ar13 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1;
Figure PCTKR2010004697-appb-I000037
Ar13 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2;
Figure PCTKR2010004697-appb-I000038
Ar14 and Ar15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
R201 through R203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
d represents an integer from 1 to 4;
e represents an integer 0 or 1; and
[Chemical Formula 3]
Figure PCTKR2010004697-appb-I000039
wherein
R211 through R214 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, NR301R302, BR303R304, PR305R306, P(=O)R307R308, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring; and
the R301 through R308 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s).
The meaning of the electroluminescent layer may be a single layer as a layer where the light is emitted or may be a multiple layer where two or more layers are laminated. In the configuration of the present invention, when host-dopant are used in mixture, it is confirmed that the luminous efficiency are remarkably improved by the electroluminescent host of the present invention. It may be configured at doping concentration of 0.5 to 10wt%. Compared to other host materials, the electroluminescent host of the present invention has superior conductivity with respect to the hole and electron and excellent stability in material, thereby showing a characteristic of remarkably increasing its life span as well as improving the luminous efficiency.
The dopant compounds of Chemical Formulas 2 and 3 may be exemplified as the compounds described in Korean Patent Application No. 10-2009-0023442. More preferably, they are selected from following structures but are not limited thereto.
Figure PCTKR2010004697-appb-I000040
Figure PCTKR2010004697-appb-I000041
Figure PCTKR2010004697-appb-I000042
Figure PCTKR2010004697-appb-I000043
Figure PCTKR2010004697-appb-I000044
Figure PCTKR2010004697-appb-I000045
Figure PCTKR2010004697-appb-I000046
In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
Further, in the organic electroluminescent device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). The organic layer may include an electroluminescent layer and a charge generating layer.
Further, the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device. The compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as 'surface layer' selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
The chalcogenide may be, for example, SiOx (1 ≤ x ≤ 2), AlOx (1 ≤ x ≤ 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device according to the present invention, it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
The present invention is further described with respect to organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 1
Figure PCTKR2010004697-appb-I000047
Preparation of Compound 1-1
After a 2-neck round bottom flask was filled with methyl-2-bromobenzoate (40 g, 152.6 mmol), naphthalen-1-ylboronic acid (31.5 g, 183.2 mmol), and tetrakis(triphenlphosphine)palladium[Pd(PPh3)4] (8.8 g, 7.62 mmol), the mixture was stirred while adding toluene (1 L) thereto. After adding 2M Potassuim carbonate (228 mL, 458 mmol) and ethanol (228 mL) thereto, the mixture was stirred under reflux at 100 ℃ for 5 hours. When the reaction was completed, the mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. After an organic layer was dried over MgSO4 and a solvent was removed by a rotary type evaporator, Compound 1-1 (35 g, 87 %) was obtained via column separation by using hexane and ethyl acetate as a developing solvent.
Preparation of Compound 1-2
After an 1-neck round bottom flask was filled with Compound 1-1 (24 g, 91.49 mmol) and formed a vacuum atmosphere, the 1-neck round bottom flask was filled with argon. Tetrahydrofuran (1 L) was added thereto and the mixture was stirred at -75 ℃ for 10 minutes. After MeLi(1.6M in hexane) (257 mL, 0.41 mmol) was added thereto, the mixture was stirred at -75 ℃ for 10 minutes and then at room temperature for 3 hours. Upon completion of the reaction, the mixture was extracted with distilled water and ethyl acetate. After an organic layer was dried over MgSO4 and a solvent was removed by a rotary type evaporator, Compound 1-2 (20 g, 83 %) was obtained via column separation by using hexane and ethyl acetate as a developing solvent.
Preparation of Compound 1-3
After the 1-neck round bottom flask was filled with Compound 1-2 (20 g, 76.23 mmol) and AcOH (300 mL) was added thereto, the mixture was stirred at 0 for 10 minutes. H3PO4 (400 mL) was added thereto and stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was neutralized with NaOH and extracted with distilled water and ethyl acetate. After an organic layer was dried over MgSO4 and a solvent was removed by a rotary type evaporator, Compound 1-3 (13.5 g, 72 %) was obtained via column separation by using hexane and ethyl acetate as a developing solvent.
Preparation of Compound 1-4
After the 1-neck round bottom flask was filled with Compound 1-3 (13.5 g, 55.25 mmol) and formed a vacuum atmosphere, the 1-neck round bottom flask was filled with argon. Tetrahydrofuran (500 mL) was added thereto and the mixture was stirred at 0 for 10 minutes. NBS (19.6 g, 0.11 mmol) was added thereto and stirred at room temperature for one day. Upon completion of the reaction, the mixture was extracted with distilled water and ethyl acetate. After an organic layer was dried over MgSO4 and a solvent was removed by a rotary type evaporator, Compound 1-4 (13 g, 73 %) was obtained via column separation by using hexane and ethyl acetate as a developing solvent.
Preparation of Compound 1-5
After the 1-neck round bottom flask was filled with Compound 1-4 (13 g, 42.21 mmol) and formed a vacuum atmosphere, the 1-neck round bottom flask was filled with argon. Tetrahydrofuran (500 mL) was added thereto and the mixture was stirred at -78 for 10 minutes. N-BuLi (2.5M in hexane) (24.1 mL, 60.32 mmol) was added dropwise and stirred at -78 ℃ for 1 hour and a half. After trimethylborate (6.85 mL, 60.32 mmol) was added at -78 ℃, the mixture was stirred for 30 minutes and then at room temperature for 4 hours. Upon completion of the reaction, the mixture was extracted with distilled water and ethyl acetate. After an organic layer was dried over MgSO4 and a solvent was removed by a rotary type evaporator, Compound 1-5 (8 g, 69 %) was obtained via column separation by using hexane and ethyl acetate as a developing solvent.
Preparation of Compound 1
Compound 1-5 (5.0 g, 13.4 mmol), 9-(4-bromophenyl)-10-phenylanthracene (6.59 g, 16.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), 2M K2CO3 aqueous solution (20 mL), toluene (100 mL), and ethanol (50 mL) were added and stirred under reflux for 12 hours. After the mixture was washed with distilled water and extracted with ethyl acetate, drying with magnesium sulfate and distillation under reduced pressure followed by column separation gave Compound 1 (4.3 g, 7.5 mmol, 56.1 %).
Organic electroluminescent compounds 1 to 63 were prepared in the same manner as Preparation Example 1. 1H NMR and MS/FAB data of the prepared organic electroluminescent compounds are given in Table 1.
[Table 1]
Figure PCTKR2010004697-appb-I000048
Figure PCTKR2010004697-appb-I000049
Figure PCTKR2010004697-appb-I000050
Figure PCTKR2010004697-appb-I000051
[Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent material according to the present invention.
First, a transparent electrode ITO thin film (15 Ω/□) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
Then, an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N'-bis(a-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. Compound 1 was placed in a cell of a vacuum vapor deposition apparatus as host, and Compound E was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 2 to 5 wt%.
Figure PCTKR2010004697-appb-I000052
Subsequently, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer. Then, after vapor-depositing lithium quinolate (Liq) of a following structure with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
Each compound used in the OLED was purified by vacuum sublimation at 10-6torr.
[Comparative Example 1] Manufacture of OLED device using conventional electroluminescent material
An OLED was manufactured in the same manner as Example 1 except that dinaphthylanthracene (DNA) instead of the Compound according to the present invention was used as host at an electroluminescent layer.
[Example 2] Manufacture of OLED device using the organic electroluminescent compounds of the present invention
An OLED was manufactured as in Example 1 except for using Compound 1 of the present invention as host in the electroluminescent layer and using following Compound A as dopant.
Figure PCTKR2010004697-appb-I000053
[Comparative Example 2] Manufacture of OLED device using conventional electroluminescent material
An OLED was manufactured in the same manner as Example 2 except that dinaphthylanthracene (DNA) instead of the Compound according to the present invention was used as host at an electroluminescent layer.
Luminous efficiency of the OLED devices including the organic electroluminescent compound according to the present invention manufactured in Examples 1 and 2 and Comparative Examples 1 and 2 and the conventional electroluminescent compound was measured at 1,000 cd/m2. The result is given in Table 2.
[Table 2]
Figure PCTKR2010004697-appb-I000054
As shown in Table 2, when the materials according to the present invention are applied to the green-light emitting device, color purity is maintained at the same level as or higher level than that of Comparative Example 1 and low driving voltage and improved luminous efficiency are acquired.
In addition, when the materials according to the present invention are applied to blue-light emitting device, luminous efficiency is remarkably improved with comparison to that of Comparative Example 1.

Claims (10)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    [Chemical Formula 1]
    Figure PCTKR2010004697-appb-I000055
    wherein
    B1 through B9 independently represent CR12 or N;
    A represents (C6-C30)arylene with or with substituent(s), (C2-C30)heteroarylene with or with substituent(s), 5- to 7-membered heterocycloalkylene with or with substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or with substituent(s), (C3-C30)cycloalkylene with or with substituent(s), cycloalkylene fused with one or more aromatic ring(s) with or with substituent(s), (C2-C30)alkenylene with or with substituent(s), (C2-C30)alkynylene with or with substituent(s), (C6-C30)ar(C1-C30)alkylene with or with substituent(s), (C1-C30)alkylenethio with or with substituent(s), (C1-C30)alkyleneoxy with or with substituent(s), (C6-C30)aryleneoxy with or with substituent(s), (C6-C30)arylenethio with or with substituent(s), -O- or -S-;
    R1 through R12 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or with substituent(s), (C6-C30)aryl with or with substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or with substituent(s), (C3-C30)heteroaryl with or with substituent(s), 5- to 7-membered heterocycloalkyl with or with substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or with substituent(s), (C3-C30)cycloalkyl with or with substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or with substituent(s), cyano, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, (C6-C30)ar(C1-C30)alkyl with or with substituent(s), (C2-C30)alkenyl with or with substituent(s), (C2-C30)alkynyl with or with substituent(s), carboxyl, nitro,
    Figure PCTKR2010004697-appb-I000056
    ,
    Figure PCTKR2010004697-appb-I000057
    or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
    W represents -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
    R51 through R58 and R61 through R63 are the same as R1 through R12;
    the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
    the R21 through R28 independently represent (C1-C30)alkyl with or with substituent(s), (C6-C30)aryl with or with substituent(s) or (C3-C30)heteroaryl with or with substituent(s),
    the Ra, Rb, Rc and Rd independently represent (C1-C30)alkyl with or with substituent(s) or (C6-C30)aryl with or with substituent(s),
    the Y represents S or O, and
    the Re and Rf represent (C1-C30)alkyl with or with substituent(s), (C1-C30)alkoxy with or with substituent(s), (C6-C30)aryl with or with substituent(s) or (C6-C30)aryloxy with or with substituent(s); and
    m represents an integer 1 or 2.
  2. The organic electroluminescent compound according to claim 1, wherein the substituent of R1 through R12, R21 through R28, R51 through R58 and R61 through R63 is further substituted by one or more substituent(s) selected from a group consisting of deuterium, halogen, (C1-C30)alkyl with or with halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or with (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or is linked to an adjacent substituent to form a ring; and
    the R31 through R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
  3. The organic electroluminescent compound according to claim 1, wherein R1 through R12 are the selected from the following structures:
    Figure PCTKR2010004697-appb-I000058
    Figure PCTKR2010004697-appb-I000059
    Figure PCTKR2010004697-appb-I000060
    Figure PCTKR2010004697-appb-I000061
    Figure PCTKR2010004697-appb-I000062
    wherein
    R71 through R141 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s), (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), cyano, amino, (C1-C30)alkylamino, (C6-C30)arylamino, NR41R42, BR43R44, PR45R46, P(=O)R47R48, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring; and
    the R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
  4. The organic electroluminescent compound according to claim 1, wherein R1 through R12 are selected from the following structures:
    Figure PCTKR2010004697-appb-I000063
    Figure PCTKR2010004697-appb-I000064
  5. The organic electroluminescent compound according to claim 1, which is selected from the following structures:
    Figure PCTKR2010004697-appb-I000065
    Figure PCTKR2010004697-appb-I000066
    Figure PCTKR2010004697-appb-I000067
    Figure PCTKR2010004697-appb-I000068
    Figure PCTKR2010004697-appb-I000069
    Figure PCTKR2010004697-appb-I000070
    Figure PCTKR2010004697-appb-I000071
    Figure PCTKR2010004697-appb-I000072
    Figure PCTKR2010004697-appb-I000073
    Figure PCTKR2010004697-appb-I000074
    Figure PCTKR2010004697-appb-I000075
    Figure PCTKR2010004697-appb-I000076
    Figure PCTKR2010004697-appb-I000077
    Figure PCTKR2010004697-appb-I000078
    Figure PCTKR2010004697-appb-I000079
    Figure PCTKR2010004697-appb-I000080
    Figure PCTKR2010004697-appb-I000081
    Figure PCTKR2010004697-appb-I000082
    Figure PCTKR2010004697-appb-I000083
    Figure PCTKR2010004697-appb-I000084
    Figure PCTKR2010004697-appb-I000085
  6. An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 5.
  7. The organic electroluminescent device according to claim 6, which comprises 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 organic electroluminescent compound(s) according to any of claims 1 to 5 and one or more dopant(s) represented by Chemical Formulas 2 and 3:
    [Chemical Formula 2]
    Figure PCTKR2010004697-appb-I000086
    wherein
    Ar11 and Ar12 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or Ar11 and Ar12 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
    Ar13 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1;
    Figure PCTKR2010004697-appb-I000087
    Ar13 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2;
    Figure PCTKR2010004697-appb-I000088
    Ar14 and Ar15 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
    R201 through R203 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s);
    d represents an integer from 1 to 4;
    e represents an integer 0 or 1; and
    [Chemical Formula 3]
    Figure PCTKR2010004697-appb-I000089
    wherein
    R211 through R214 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, NR301R302, BR303R304, PR305R306, P(=O)R307R308, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C1-C30)alkyloxy with or without substituent(s), (C1-C30)alkylthio with or without substituent(s), (C6-C30)aryloxy with or without substituent(s), (C6-C30)arylthio with or without substituent(s), (C1-C30)alkoxycarbonyl with or without substituent(s), (C1-C30)alkylcarbonyl with or without substituent(s), (C6-C30)arylcarbonyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), (C6-C30)aryloxycarbonyl with or without substituent(s), (C1-C30)alkoxycarbonyloxy with or without substituent(s), (C1-C30)alkylcarbonyloxy with or without substituent(s), (C6-C30)arylcarbonyloxy with or without substituent(s), (C6-C30)aryloxycarbonyloxy with or without substituent(s), carboxyl, nitro or hydroxyl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring; and
    the R301 through R308 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s).
  8. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more amine compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, or one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  9. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  10. The organic electroluminescent device according to claim 7, which is a white light-emitting organic electroluminescent device wherein the organic layer comprises one or more organic compound layer(s) emitting red, green or blue light at the same time.
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