WO2014030921A1 - Novel organic electroluminescence compounds and organic electroluminescence device containing the same - Google Patents

Novel organic electroluminescence compounds and organic electroluminescence device containing the same Download PDF

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WO2014030921A1
WO2014030921A1 PCT/KR2013/007491 KR2013007491W WO2014030921A1 WO 2014030921 A1 WO2014030921 A1 WO 2014030921A1 KR 2013007491 W KR2013007491 W KR 2013007491W WO 2014030921 A1 WO2014030921 A1 WO 2014030921A1
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substituted
unsubstituted
aryl
alkyl
membered
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PCT/KR2013/007491
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French (fr)
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Hee-Choon Ahn
Soo-Jin Yang
Jeong-Eun YANG
Tae-Jin Lee
Seung-Ae Kim
Kyung-Joo Lee
Hyuck-Joo Kwon
Bong-Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Publication of WO2014030921A1 publication Critical patent/WO2014030921A1/en

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • H10K2101/90—Multiple hosts in the emissive layer

Definitions

  • the present invention relates to novel organic electroluminescence compounds and organic electroluminescence device containing the same.
  • An organic light emitting diode is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • the most important factor determining luminous efficiency in an OLED is the light-emitting material.
  • fluorescent materials have been widely used as a light-emitting material.
  • phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, development of phosphorescent light-emitting materials are widely being researched.
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
  • a luminescent material can be used in combination with a host material as a light emitting material to improve color purity, luminous efficiency, and stability. Since host materials greatly influence the efficiency and performance of the EL device when using a host material/dopant system as a light emitting material, their selection is important.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • CuPc copper phthalocyanine
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
  • MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
  • an OLED using these materials is problematic in quantum efficiency and operational lifespan. It is because, when an OLED is driven under high current, thermal stress occurs between an anode and the hole injection layer. Thermal stress significantly reduces the operational lifespan of the device. Further, since the organic material used in the hole injection layer has very high hole mobility, the hole-electron charge balance may be broken and quantum yield (cd/A) may decrease.
  • Korean Patent Appln. Laying-Open No. KR 2011/102055 A discloses amine compounds comprising carbazole and triazine groups, as compounds for an OLED.
  • organic EL devices comprising the compounds disclosed in the above references are still not satisfactory in terms of power efficiency, luminous efficiency, quantum efficiency, lifespan, etc.
  • the objective of the present invention is to provide an organic electroluminescent compound which has higher luminous efficiency and a longer operational lifespan than the conventional materials; and an organic electroluminescent device having high efficiency and a long lifespan, using said compounds.
  • L 1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
  • L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
  • R 1 to R 4 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, -NR 11 R 12
  • R 11 to R 20 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; or are linked to an
  • a, b and c each independently represent an integer of 1 to 4; where a, b or c is an integer of 2 or more, each of R 1 , each of R 2 , or each of R 3 may be same or different; and
  • d represents an integer of 1 to 3; where d is an integer of 2 or more, each of R 4 may be same or different.
  • the compound according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operational lifespan.
  • using the compound according to the present invention it is possible to manufacture an electroluminescent device of lowered driving voltages and advanced power efficiency.
  • the compound represented by the above formula 1 has an amine compound structure comprising carbazole and dibenzothiophene backbones, and will be described in detail.
  • L 1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, preferably represents a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene, more preferably represents an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene, and even more preferably represents phenylene, naphthylene, biphenylene, terphenylene, dimethylfluorenylene, pyridylene, or isoquinolylene.
  • L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, preferably each independently represent a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene, more preferably each independently represent a single bond; an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene, and even more preferably each independently represent a single bond, phenylene, biphenylene, naphthylene, dimethylfluorenylene, pyridylene, or pyrimidinylene.
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl, preferably represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl, more preferably represents a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, a di(C6-C20)arylamino, a (C6-C20)aryl(5- to 21-membered)heteroarylamino, or a 5- to 21-membered heteroaryl; or a 5- to 21-membered heteroaryl unsubstituted or substituted with a (C6-C30)ary
  • R 1 to R 4 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, -
  • L 1 represents a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene
  • L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene
  • Ar 1 represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl
  • R 1 to R 4 each independently represent hydrogen, a halogen, a substituted or unsubstituted (C1-C15)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl.
  • L 1 represents an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene;
  • L 2 and L 3 each independently represent a single bond; an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene;
  • Ar 1 represents a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, a di(C6-C20)arylamino, a (C6-C20)aryl(5- to 21-
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
  • the substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted alkoxy, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in the above formula 1 preferably each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkeny
  • the representative organic electroluminescent compounds of the present invention include the following compounds, but are not limited thereto:
  • the compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, they can be prepared according to the following reaction scheme 1.
  • L 1 , L 2 , L 3 , Ar 1 , R 1 to R 4 , a, b, c, and d are as defined in formula 1 above, and Hal represents a halogen.
  • an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • Said organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes.
  • Said organic layer may comprise at least one compound of formula 1 according to the present invention.
  • the organic layer comprises a light-emitting layer, and at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and a electron blocking layer.
  • the compound represented by formula 1 can be comprised in at least one of the light-emitting layer and the hole transport layer. Where used in the hole transport layer, the compound represented by formula 1 can be comprised as a hole transport material. Where used in the light-emitting layer, the compound represented by formula 1 can be comprised as a host material; preferably, the light-emitting layer can further comprise at least one dopant; and if needed, a compound other than the compound represented by formula 1 can be comprised additionally as a second host material.
  • the second host material can be from any of the known phosphorescent dopants.
  • the phosphorescent dopant selected from the group consisting of the compounds of formula 2 to 4 below is preferable in view of luminous efficiency.
  • R 21 to R 24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted of unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or R 25 R 26 R 27 Si-;
  • R 25 to R 27 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-membered heteroarylene group;
  • M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroary
  • preferable examples of the second host material are as follows:
  • the dopant is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material applied to the electroluminescent device according to the present invention is not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper and platinum, and even more preferably ortho-metallated iridium complex compounds.
  • the phosphorescent dopants may be preferably selected from compounds represented by the following formulae 5 to 7.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
  • R 101 to R 109 , and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group; adjacent substituents of R 120 to R 123 may be linked to each other to form a fused ring, e.g. quinoline;
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; where R 124 to R 127 are aryl groups, adjacent substituents may be linked to each other to form a fused ring, e.g. fluorene;
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group or a substituted or unsubstituted (C6-C30)aryl group;
  • f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each of R 100 may be the same or different; and
  • n is an integer of 0 to 3.
  • the phosphorescent dopant materials include the following:
  • composition used for producing an organic electroluminescent device.
  • the composition comprises first host material, and if needed, second host material, and the compound according to the present invention may be comprised in the first host material.
  • the ratio of the first host material to the second host material may be in the range of 1:99 to 99:1.
  • the second host material may be selected from the phosphorescent host represented by formula 8 to 14 below.
  • X’ represents -O- or -S-
  • R 24 , R 25 , and R 30 each independently represent a substituted of unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
  • R 26 to R 29 , and R 31 to R 34 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted of unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or R 35 R 36 R 37 Si-;
  • R 35 to R 37 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-membered heteroarylene group;
  • M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
  • Y 1 to Y 5 each independently represent -O-, -S-, -N(R 41 )- or -C(R 42 )(R 43 )-, provided that Y 4 and Y 5 do not simultaneously exist;
  • R 41 to R 43 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, and R 42 and R 43 may be same or different;
  • p and q each independently represent an integer of 1 to 3;
  • h, i, j, k, l, m, r, and s each independently represent an integer of 1 to 4.
  • each of R 26 , each of R 27 , each of R 28 , each of R 29 , each of R 31 , each of R 32 , each of (Cz-L 4 ), each of (Cz), each of R 33 , or each of R 34 may be same or different.
  • the second host materials include the following:
  • a material used for an organic electroluminescent device comprises the organic electroluminescent compound according to the present invention as ahost material or a hole transport material.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes.
  • Said organic layer comprises a light emitting layer.
  • Said light emitting layer comprises the organic electroluminescent composition according to the present invention and the phosphorescent dopant material.
  • Said organic electroluminescent composition may be used as a host material.
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may further comprise at least one additional light-emitting layer and a charge generating layer.
  • the organic electroluminescent device according to the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound according to the present invention. Also, if needed, a yellow or orange light-emitting layer can be comprised in the device.
  • a surface layer may be placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide(includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device was produced using the light emitting material according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • organic electroluminescent compound C-3 according to the present invention was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • 5-(4-([1,1’:4’,1”-terphenyl]-3-yl)pyrimidin-2-yl)-5H-benzo[4,5]thieno[3,2-c]carbazole was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-1 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate and were deposited in a doping amount of 50 wt% each to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
  • the produced OLED device showed a green emission having a luminance of 6520 cd/m 2 and a current density of 14.9 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound C-104 as a hole transport layer.
  • the produced OLED device showed a green emission having a luminance of 3855 cd/m 2 and a current density of 8.6 mA/cm 2 .
  • Comparative Example 1 Production of an OLED device using conventional light emitting material
  • An OLED device was produced in the same manner as in Device Example 1, except for evaporating N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl as a hole transport material to form a hole transport layer having a thickness of 20 nm; using 4,4'-N,N'-dicarbazole-biphenyl as a host material, compound D-15 as a dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and depositing aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate to form a hole blocking layer having a thickness of 10 nm.
  • the produced OLED device showed a green emission having a luminance of 2250 cd/m 2 and a current density of 6.6 mA/cm 2 .
  • the organic electroluminescent compounds of the present invention have superior luminous characteristics over conventional materials, and so the devices using the organic electroluminescent compounds according to the present invention have superior luminous characteristics.

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device containing the same. Using the organic electroluminescent compound according to the present invention, it is possible to manufacture an OLED device of lowered driving voltages and advanced power efficiency.

Description

NOVEL ORGANIC ELECTROLUMINESCENCE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE CONTAINING THE SAME
The present invention relates to novel organic electroluminescence compounds and organic electroluminescence device containing the same.
An organic light emitting diode (OLED) is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor determining luminous efficiency in an OLED is the light-emitting material. Until now, fluorescent materials have been widely used as a light-emitting material. However, in view of electroluminescent mechanisms, since phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, development of phosphorescent light-emitting materials are widely being researched. Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
A luminescent material (dopant) can be used in combination with a host material as a light emitting material to improve color purity, luminous efficiency, and stability. Since host materials greatly influence the efficiency and performance of the EL device when using a host material/dopant system as a light emitting material, their selection is important.
At present, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances. Recently, Pioneer (Japan) et al. developed a high performance OLED using bathocuproine (BCP) and aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) etc. as host materials, which were known as hole blocking layer materials.
Though these phosphorous host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of an OLED is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although an OLED comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Further, the operational lifespan of an OLED is short and luminous efficiency is still required to be improved.
Meanwhile, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), etc. were used as a hole injection and transport material.
However, an OLED using these materials is problematic in quantum efficiency and operational lifespan. It is because, when an OLED is driven under high current, thermal stress occurs between an anode and the hole injection layer. Thermal stress significantly reduces the operational lifespan of the device. Further, since the organic material used in the hole injection layer has very high hole mobility, the hole-electron charge balance may be broken and quantum yield (cd/A) may decrease.
International Patent Publication No. WO 2011/040607 discloses amine compounds comprising two carbazole backbones of which the bonding positions are different (one is bonded via a nitrogen atom of carbazole, and the other is bonded via a carbon atom of carbazole), as compounds for an OLED.
In addition, Korean Patent Appln. Laying-Open No. KR 2011/102055 A discloses amine compounds comprising carbazole and triazine groups, as compounds for an OLED.
However, organic EL devices comprising the compounds disclosed in the above references are still not satisfactory in terms of power efficiency, luminous efficiency, quantum efficiency, lifespan, etc.
The objective of the present invention is to provide an organic electroluminescent compound which has higher luminous efficiency and a longer operational lifespan than the conventional materials; and an organic electroluminescent device having high efficiency and a long lifespan, using said compounds.
The present inventors found that the above objective can be achieved by a compound represented by the following formula 1:
Figure PCTKR2013007491-appb-I000001
wherein
L1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
R1 to R4 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, -NR11R12, -SiR13R14R15, -SR16, -OR17, -COR18 or -B(OR19)(OR20); or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur;
R11 to R20 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur;
a, b and c each independently represent an integer of 1 to 4; where a, b or c is an integer of 2 or more, each of R1, each of R2, or each of R3 may be same or different; and
d represents an integer of 1 to 3; where d is an integer of 2 or more, each of R4 may be same or different.
The compound according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operational lifespan. In addition, using the compound according to the present invention, it is possible to manufacture an electroluminescent device of lowered driving voltages and advanced power efficiency.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The compound represented by the above formula 1 has an amine compound structure comprising carbazole and dibenzothiophene backbones, and will be described in detail.
In formula 1 above, L1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, preferably represents a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene, more preferably represents an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene, and even more preferably represents phenylene, naphthylene, biphenylene, terphenylene, dimethylfluorenylene, pyridylene, or isoquinolylene.
In formula 1 above, L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene, preferably each independently represent a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene, more preferably each independently represent a single bond; an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene, and even more preferably each independently represent a single bond, phenylene, biphenylene, naphthylene, dimethylfluorenylene, pyridylene, or pyrimidinylene.
In formula 1 above, Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl, preferably represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl, more preferably represents a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, a di(C6-C20)arylamino, a (C6-C20)aryl(5- to 21-membered)heteroarylamino, or a 5- to 21-membered heteroaryl; or a 5- to 21-membered heteroaryl unsubstituted or substituted with a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, or a di(C6-C20)arylamino, and even more preferably each independently represent phenyl, naphthyl, biphenyl, terphenyl, naphthylphenyl, phenyl substituted with a dimethylfluorenyl, phenyl substituted with a pyridyl, phenyl substituted with a diphenylamino, phenyl substituted with a phenylpyridylamino, naphthyl substituted with a diphenylamino, dimethylfluorenyl, pyridyl, pyridyl substituted with a phenyl, pyridyl substituted with a naphthyl, pyridyl substituted with a dimethylfluorenyl, or pyridyl substituted with a diphenylamino.
In formula 1 above, R1 to R4 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, -NR11R12, -SiR13R14R15, -SR16, -OR17, -COR18 or -B(OR19)(OR20); or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur, preferably each independently represent hydrogen, a halogen, a substituted or unsubstituted (C1-C15)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl, more preferably each independently represent hydrogen; a halogen; an unsubstituted (C1-C6)alkyl; a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroaryl, and even more preferably each independently represent hydrogen, fluorine, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenyl substituted with a tert-butyl, or dibenzofuranyl.
According to one embodiment of the present invention, in formula 1, above, L1 represents a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene; L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl; and R1 to R4 each independently represent hydrogen, a halogen, a substituted or unsubstituted (C1-C15)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl.
According to another embodiment of the present invention, in formula 1, above, L1 represents an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene; L2 and L3 each independently represent a single bond; an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene; Ar1 represents a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, a di(C6-C20)arylamino, a (C6-C20)aryl(5- to 21-membered)heteroarylamino, or a 5- to 21-membered heteroaryl; or a 5- to 21-membered heteroaryl unsubstituted or substituted with a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, or a di(C6-C20)arylamino; and R1 to R4 each independently represent hydrogen; a halogen; an unsubstituted (C1-C6)alkyl; a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroaryl.
Herein, “alkyl” includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; “alkenyl” includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; “alkynyl” includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; “cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from B, N, O, S, P(=O), Si and P, preferably O, S and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; “aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.; “5- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 5 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. Further, “halogen” includes F, Cl, Br and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
The substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted alkoxy, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in the above formula 1 preferably each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkenyl, a 3- to 7-membered heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a 5- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 5- to 30-membered heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono or di(C1-C30)alkylamino, a mono or di(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C6-C30)aryl(5- to 30-membered)heteroarylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl, more preferably each independently are at least one selected from the group consisting of a (C1-C6)alkyl, a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, a 5- to 21-membered heteroaryl, a di(C6-C20)arylamino, and a (C6-C20)aryl(5- to 21-membered)heteroarylamino, and even more preferably each independently are at least one selected from the group consisting of methyl, tert-butyl, phenyl, naphthyl, dimethylfluorenyl, pyridyl, diphenylamino, and phenylpyridylamino.
The representative organic electroluminescent compounds of the present invention include the following compounds, but are not limited thereto:
Figure PCTKR2013007491-appb-I000002
Figure PCTKR2013007491-appb-I000003
Figure PCTKR2013007491-appb-I000004
Figure PCTKR2013007491-appb-I000005
Figure PCTKR2013007491-appb-I000006
Figure PCTKR2013007491-appb-I000007
Figure PCTKR2013007491-appb-I000008
Figure PCTKR2013007491-appb-I000009
Figure PCTKR2013007491-appb-I000010
Figure PCTKR2013007491-appb-I000011
Figure PCTKR2013007491-appb-I000012
Figure PCTKR2013007491-appb-I000013
Figure PCTKR2013007491-appb-I000014
Figure PCTKR2013007491-appb-I000015
Figure PCTKR2013007491-appb-I000016
Figure PCTKR2013007491-appb-I000017
Figure PCTKR2013007491-appb-I000018
Figure PCTKR2013007491-appb-I000019
Figure PCTKR2013007491-appb-I000020
Figure PCTKR2013007491-appb-I000021
Figure PCTKR2013007491-appb-I000022
The compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, they can be prepared according to the following reaction scheme 1.
[Reaction Scheme 1]
Figure PCTKR2013007491-appb-I000023
wherein L1, L2, L3, Ar1, R1 to R4, a, b, c, and d are as defined in formula 1 above, and Hal represents a halogen.
In another embodiment of the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
Said organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes. Said organic layer may comprise at least one compound of formula 1 according to the present invention.
One of the first and second electrodes is an anode, and the other is a cathode. The organic layer comprises a light-emitting layer, and at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and a electron blocking layer.
The compound represented by formula 1 can be comprised in at least one of the light-emitting layer and the hole transport layer. Where used in the hole transport layer, the compound represented by formula 1 can be comprised as a hole transport material. Where used in the light-emitting layer, the compound represented by formula 1 can be comprised as a host material; preferably, the light-emitting layer can further comprise at least one dopant; and if needed, a compound other than the compound represented by formula 1 can be comprised additionally as a second host material.
The second host material can be from any of the known phosphorescent dopants. Specifically, the phosphorescent dopant selected from the group consisting of the compounds of formula 2 to 4 below is preferable in view of luminous efficiency.
Figure PCTKR2013007491-appb-I000024
Figure PCTKR2013007491-appb-I000025
Figure PCTKR2013007491-appb-I000026
wherein Cz represents the following structure;
Figure PCTKR2013007491-appb-I000027
R21 to R24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted of unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or R25R26R27Si-; R25 to R27 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; L4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-membered heteroarylene group; M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; Y1 and Y2 represent -O-, -S-, -N(R31)- or -C(R32)(R33)-, provided that Y1 and Y2 do not simultaneously exist; R31 to R33 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, and R32 and R33 are the same or different; h and i each independently represent an integer of 1 to 3; j, k, l and m each independently represent an integer of 0 to 4; and where h, i, j, k, l or m is an integer of 2 or more, each of (Cz-L4), each of (Cz), each of R21, each of R22, each of R23 or each of R24 is the same or different.
Specifically, preferable examples of the second host material are as follows:
Figure PCTKR2013007491-appb-I000028
Figure PCTKR2013007491-appb-I000029
Figure PCTKR2013007491-appb-I000030
Figure PCTKR2013007491-appb-I000031
Figure PCTKR2013007491-appb-I000032
Figure PCTKR2013007491-appb-I000033
Figure PCTKR2013007491-appb-I000034
Figure PCTKR2013007491-appb-I000035
Figure PCTKR2013007491-appb-I000036
Figure PCTKR2013007491-appb-I000037
Figure PCTKR2013007491-appb-I000038
Figure PCTKR2013007491-appb-I000039
Figure PCTKR2013007491-appb-I000040
The dopant is preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the electroluminescent device according to the present invention is not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper and platinum, and even more preferably ortho-metallated iridium complex compounds.
The phosphorescent dopants may be preferably selected from compounds represented by the following formulae 5 to 7.
Figure PCTKR2013007491-appb-I000041
Figure PCTKR2013007491-appb-I000042
Figure PCTKR2013007491-appb-I000043
wherein L is selected from the following structures:
Figure PCTKR2013007491-appb-I000044
R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group;
R101 to R109, and R111 to R123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group; adjacent substituents of R120 to R123 may be linked to each other to form a fused ring, e.g. quinoline;
R124 to R127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; where R124 to R127 are aryl groups, adjacent substituents may be linked to each other to form a fused ring, e.g. fluorene;
R201 to R211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group or a substituted or unsubstituted (C6-C30)aryl group;
f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each of R100 may be the same or different; and
n is an integer of 0 to 3.
Specifically, the phosphorescent dopant materials include the following:
Figure PCTKR2013007491-appb-I000045
Figure PCTKR2013007491-appb-I000046
Figure PCTKR2013007491-appb-I000047
Figure PCTKR2013007491-appb-I000048
Figure PCTKR2013007491-appb-I000049
Figure PCTKR2013007491-appb-I000050
Figure PCTKR2013007491-appb-I000051
Figure PCTKR2013007491-appb-I000052
Figure PCTKR2013007491-appb-I000053
Figure PCTKR2013007491-appb-I000054
Figure PCTKR2013007491-appb-I000055
Figure PCTKR2013007491-appb-I000056
In another embodiment of the present invention provides a composition used for producing an organic electroluminescent device. The composition comprises first host material, and if needed, second host material, and the compound according to the present invention may be comprised in the first host material.
The ratio of the first host material to the second host material may be in the range of 1:99 to 99:1.
The second host material may be selected from the phosphorescent host represented by formula 8 to 14 below.
Figure PCTKR2013007491-appb-I000057
Figure PCTKR2013007491-appb-I000058
Figure PCTKR2013007491-appb-I000059
Figure PCTKR2013007491-appb-I000060
Figure PCTKR2013007491-appb-I000061
Figure PCTKR2013007491-appb-I000062
Figure PCTKR2013007491-appb-I000063
wherein Cz represents the following structure;
Figure PCTKR2013007491-appb-I000064
X’ represents -O- or -S-;
R24, R25, and R30 each independently represent a substituted of unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
R26 to R29, and R31 to R34 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted of unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or R35R36R37Si-;
R35 to R37 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group;
L4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-membered heteroarylene group;
M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
Y1 to Y5 each independently represent -O-, -S-, -N(R41)- or -C(R42)(R43)-, provided that Y4 and Y5 do not simultaneously exist;
R41 to R43 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, and R42 and R43 may be same or different;
p and q each independently represent an integer of 1 to 3;
h, i, j, k, l, m, r, and s each independently represent an integer of 1 to 4; and
where h, i, j, k, l, m, p, q, r, or s is an integer of 2 or more, each of R26, each of R27, each of R28, each of R29, each of R31, each of R32, each of (Cz-L4), each of (Cz), each of R33, or each of R34 may be same or different.
Specifically, the second host materials include the following:
Figure PCTKR2013007491-appb-I000065
Figure PCTKR2013007491-appb-I000066
Figure PCTKR2013007491-appb-I000067
Figure PCTKR2013007491-appb-I000068
Figure PCTKR2013007491-appb-I000069
Figure PCTKR2013007491-appb-I000070
Figure PCTKR2013007491-appb-I000071
Figure PCTKR2013007491-appb-I000072
Figure PCTKR2013007491-appb-I000073
Figure PCTKR2013007491-appb-I000074
Figure PCTKR2013007491-appb-I000075
Figure PCTKR2013007491-appb-I000076
Figure PCTKR2013007491-appb-I000077
Figure PCTKR2013007491-appb-I000078
Figure PCTKR2013007491-appb-I000079
Figure PCTKR2013007491-appb-I000080
Figure PCTKR2013007491-appb-I000081
In another embodiment of the present invention, a material used for an organic electroluminescent device is provided. The material comprises the organic electroluminescent compound according to the present invention as ahost material or a hole transport material.
In addition, the organic electroluminescent device according to the present invention comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes. Said organic layer comprises a light emitting layer. Said light emitting layer comprises the organic electroluminescent composition according to the present invention and the phosphorescent dopant material. Said organic electroluminescent composition may be used as a host material.
The organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal. The organic layer may further comprise at least one additional light-emitting layer and a charge generating layer.
In addition, the organic electroluminescent device according to the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound according to the present invention. Also, if needed, a yellow or orange light-emitting layer can be comprised in the device.
According to the present invention, at least one layer (hereinafter, “a surface layer”) may be placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer. Specifically, a chalcogenide(includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, said chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and said metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
In order to form each layer of the organic electroluminescent device according to the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, flow coating methods can be used.
When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
Hereinafter, the compound, the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
Example 1: Preparation of compound C-3
Figure PCTKR2013007491-appb-I000082
Preparation of compound 1-1
After adding xylene 400 mL to a mixture of 2-bromodibenzothiophene 20 g (76 mmol), aniline 14 g (152 mmol), Pd(OAc)2 0.5 g (2.3 mmol), P(t-Bu)3 3 mL (50 wt% xylene solution, 7.6 mmol), and Cs2CO3 50 g (152 mmol), the mixture was stirred at 160°C for 12 hours. The reaction mixture was extracted with ethylacetate (EA)/H2O, and dried with MgSO4. Then, the solvent was removed with a rotary evaporator, and the remaining product was purified with a column to obtain compound 1-1, 12 g (56 %).
Preparation of compound C-3
After adding xylene 150 mL to a mixture of compound 1-1, 8.5 g (31 mmol), 9-(4-bromophenyl)-9H-carbazole 10 g (31 mmol), Pd(OAc)2 0.57 g (0.62 mmol), P(t-Bu)3 1 mL (3.1 mmol), and NaOtBu 4.5 g (47 mmol), the mixture was stirred at 160°C for 12 hours. After completing the reaction, the mixture was washed with distilled water, extracted with EA, and the organic layer was dried with MgSO4. Then, the solvent was removed with a rotary evaporator, and the remaining product was purified with a column to obtain compound C-3, 9.2 g (57 %).
MS/EIMS found 517.5; calculated 516.17
Example 2: Preparation of compound C-104
Figure PCTKR2013007491-appb-I000083
Preparation of compound 2-1
After mixing 4-bromo-iodobenzene 20 g (71 mmol), dibenzo[b,d]thiophen-4-yl boronic acid 17.7 g (77 mol), Pd(PPh3)4 3.3 g (2.8 mmol), Na2CO3 18.8 g (177 mmol), toluene 360 mL, ethanol 90 mL, and water 90 mL, the mixture was stirred at 120°C for 2.5 hours. The reaction mixture was extracted with ethylacetate (EA)/H2O, dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain compound 2-1, 19 g (79 %).
Preparation of compound 2-2
After mixing compound 2-1, 18.5 g (54 mmol), aniline 5.9 mL (65 mmol), Pd(OAc)2 0.69 g (2.7 mmol), P(t-Bu)3 2.6 mL (5.4 mmol), NaOtBu 10.4 g (108 mmol), and toluene 260 mL, the mixture was stirred at 120°C for 5 hours. The reaction mixture was extracted with ethylacetate (EA)/H2O, dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain compound 2-2, 15 g (79 %).
Figure PCTKR2013007491-appb-I000084
Preparation of compound 2-3
After mixing compound 2-2, 15.3 g (44 mmol), 4,4’-dibromobiphenyl 27 g (87 mmol), Pd2(dba)3 1.2 g (1.3 mmol), P(o-tol)3 1.06 g (3.5 mmol), NaOtBu 8.4 g (87 mmol), and toluene 450 mL, the mixture was stirred at 120°C for 1.5 hours. The reaction mixture was extracted with ethylacetate (EA)/H2O, dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain a yellow solid product, compound 2-3, 13.4 g (53 %).
Preparation of compound C-104
After mixing compound 2-3, 13.4 g (23 mmol), carbazole 3.5 g (21 mmol), CuI 2 g (10 mmol), K3PO4 13.4 g (63 mmol), ethylenediamine 2.8 mL (42 mmol), and toluene 120 mL, the mixture was stirred at 120°C for 8 hours. The reaction mixture was extracted with ethylacetate (EA)/H2O, dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain a white solid product, compound C-104, 5.0 g (35 %).
MS/EIMS found 668.8; calculated 668.23
Example 3: Preparation of compound C-16
Figure PCTKR2013007491-appb-I000085
Preparation of compound 3-1
After mixing 4-bromoaniline 30 g (0.174 mol), phenyl boronic acid 28 g (0.227 mol), Pd(PPh3)4 6 g (0.005 mol), K2CO3 60 g (0.435 mol), toluene 350 mL, ethanol 150 mL, and water 150 mL, the mixture was stirred at 120°C for 12 hours. After completing the reaction, the mixture was extracted with ethylacetate (EA), the organic layer was dried with MgSO4, filtered, and the solvent was removed under reduced pressure. Then, the remaining product was purified with a column to obtain compound 3-1, 20 g (68 %).
Preparation of compound 3-2
After mixing compound 3-1, 12 g (59 mmol), 2-bromo-dibenzo[b,d]thiophene 17 g (65 mmol), Pd(OAc)2 0.5 g (2.03 mmol), P(t-Bu)3 1.43 mL (7.09 mmol), NaOt-Bu 14 g (118 mmol), and xylene 350 mL, the mixture was stirred at 150°C for 24 hours. The reaction mixture was extracted with ethylacetate (EA), the organic layer was dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain compound 3-2, 6 g (40 %).
Figure PCTKR2013007491-appb-I000086
Preparation of compound 3-3
After mixing carbazole 20 g (119 mmol), 4-bromo-4’-iodo-1,1’-biphenyl 70 g (239 mmol), CuI 11.4 g (60 mmol), K3PO4 76 g (358 mmol), and toluene 600 mL, the mixture was stirred at 80°C for 10 minutes. Then, ethylenediamine (EDA) 16 mL (239 mmol) was added to the mixture, and stirred at 140°C for 12 hours. The reaction mixture was extracted with ethylacetate (EA), the organic layer was dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain compound 3-3, 40 g (84 %).
Preparation of compound C-16
After mixing compound 3-2, 6 g (17 mmol), compound 3-3, 7.5 g (19 mmol), Pd(OAc)2 0.11 g (0.51 mmol), P(t-Bu)3 0.4 mL (1.7 mmol), NaOt-Bu 5 g (51 mmol), and xylene 120 mL, the mixture was stirred at 150°C for 4 hours. The reaction mixture was extracted with ethylacetate (EA), the organic layer was dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain a white solid product, compound C-16, 3 g (26 %).
MS/EIMS found 669; calculated 668.85
Example 4: Preparation of compound C-25
Figure PCTKR2013007491-appb-I000087
Preparation of compound 4-1
After mixing compound 3-1, 6 g (36 mmol), 4-bromo-dibenzo[b,d]thiophene 10 g (38 mmol), Pd(OAc)2 0.2 g (1.0 mmol), P(t-Bu)3 0.87 mL (3.7 mmol), NaOt-Bu 7 g (72 mmol), and xylene 180 mL, the mixture was stirred at 150°C for 24 hours. The reaction mixture was extracted with ethylacetate (EA), the organic layer was dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain compound 4-1, 6 g (48 %).
Preparation of compound C-25
After mixing compound 4-1, 5.3 g (15 mmol), compound 3-3, 5.5 g (14 mmol), Pd(OAc)2 0.11 g (0.45 mmol), P(t-Bu)3 0.36 mL (1.5 mmol), NaOt-Bu 4.3 g (45 mmol), and xylene 100 mL, the mixture was stirred at 150°C for 4 hours. The reaction mixture was extracted with ethylacetate (EA), the organic layer was dried with MgSO4, and distilled under reduced pressure. Then, the remaining product was purified with a column to obtain a white solid product, compound C-25, 4 g (40 %).
MS/EIMS found 668; calculated 668.85
Device Example 1: Production of an OLED device using the organic
electroluminescent compound according to the present invention
An OLED device was produced using the light emitting material according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzen-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, organic electroluminescent compound C-3 according to the present invention was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, 5-(4-([1,1’:4’,1”-terphenyl]-3-yl)pyrimidin-2-yl)-5H-benzo[4,5]thieno[3,2-c]carbazole was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-1 was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate and were deposited in a doping amount of 50 wt% each to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed a green emission having a luminance of 6520 cd/m2 and a current density of 14.9 mA/cm2.
Device Example 2: Production of an OLED device using the organic
electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound C-104 as a hole transport layer.
The produced OLED device showed a green emission having a luminance of 3855 cd/m2 and a current density of 8.6 mA/cm2.
Comparative Example 1: Production of an OLED device using conventional light emitting material
An OLED device was produced in the same manner as in Device Example 1, except for evaporating N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl as a hole transport material to form a hole transport layer having a thickness of 20 nm; using 4,4'-N,N'-dicarbazole-biphenyl as a host material, compound D-15 as a dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer; and depositing aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate to form a hole blocking layer having a thickness of 10 nm.
The produced OLED device showed a green emission having a luminance of 2250 cd/m2 and a current density of 6.6 mA/cm2.
It is verified that the organic electroluminescent compounds of the present invention have superior luminous characteristics over conventional materials, and so the devices using the organic electroluminescent compounds according to the present invention have superior luminous characteristics.

Claims (6)

  1. A compound represented by the following formula 1:
    Figure PCTKR2013007491-appb-I000088
    wherein
    L1 represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
    L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
    Ar1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
    R1 to R4 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, -NR11R12, -SiR13R14R15, -SR16, -OR17, -COR18 or -B(OR19)(OR20); or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur;
    R11 to R20 each independently represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur;
    a, b and c each independently represent an integer of 1 to 4; where a, b or c is an integer of 2 or more, each of R1, each of R2, or each of R3 may be same or different; and
    d represents an integer of 1 to 3; where d is an integer of 2 or more, each of R4 may be same or different.
  2. The compound according to claim 1, wherein the substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted alkoxy, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in L1, L2, L3, Ar1, R1 to R4, and R11 to R20 each independently are at least one selected from the group consisting of deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a (C1-C30)alkyl, a halo(C1-C30)alkyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a (C1-C30)alkoxy, a (C1-C30)alkylthio, a (C3-C30)cycloalkyl, a (C3-C30)cycloalkenyl, a 3- to 7-membered heterocycloalkyl, a (C6-C30)aryloxy, a (C6-C30)arylthio, a 5- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 5- to 30-membered heteroaryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, an amino, a mono or di(C1-C30)alkylamino, a mono or di(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, a (C6-C30)aryl(5- to 30-membered)heteroarylamino, a (C1-C30)alkylcarbonyl, a (C1-C30)alkoxycarbonyl, a (C6-C30)arylcarbonyl, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, and a (C1-C30)alkyl(C6-C30)aryl.
  3. The compound according to claim 1, wherein L1 represents a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene;
    L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted 5- to 21-membered heteroarylene;
    Ar1 represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl; and
    R1 to R4 each independently represent hydrogen, a halogen, a substituted or unsubstituted (C1-C15)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 21-membered heteroaryl.
  4. The compound according to claim 1, wherein L1 represents an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene;
    L2 and L3 each independently represent a single bond; an unsubstituted (C6-C20)arylene; a (C6-C20)arylene substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroarylene;
    Ar1 represents a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, a di(C6-C20)arylamino, a (C6-C20)aryl(5- to 21-membered)heteroarylamino, or a 5- to 21-membered heteroaryl; or a 5- to 21-membered heteroaryl unsubstituted or substituted with a (C6-C20)aryl, a (C1-C6)alkyl(C6-C20)aryl, or a di(C6-C20)arylamino; and
    R1 to R4 each independently represent hydrogen; a halogen; an unsubstituted (C1-C6)alkyl; a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-membered heteroaryl.
  5. The compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2013007491-appb-I000089
    Figure PCTKR2013007491-appb-I000090
    Figure PCTKR2013007491-appb-I000091
    Figure PCTKR2013007491-appb-I000092
    Figure PCTKR2013007491-appb-I000093
    Figure PCTKR2013007491-appb-I000094
    Figure PCTKR2013007491-appb-I000095
    Figure PCTKR2013007491-appb-I000096
    Figure PCTKR2013007491-appb-I000097
    Figure PCTKR2013007491-appb-I000098
    Figure PCTKR2013007491-appb-I000099
    Figure PCTKR2013007491-appb-I000100
    Figure PCTKR2013007491-appb-I000101
    Figure PCTKR2013007491-appb-I000102
    Figure PCTKR2013007491-appb-I000103
    Figure PCTKR2013007491-appb-I000104
    Figure PCTKR2013007491-appb-I000105
    Figure PCTKR2013007491-appb-I000106
    Figure PCTKR2013007491-appb-I000107
    Figure PCTKR2013007491-appb-I000108
    Figure PCTKR2013007491-appb-I000109
  6. An organic electroluminescent device comprising the compound according to claim 1.
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