WO2014030921A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique contenant ceux-ci - Google Patents

Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique contenant ceux-ci 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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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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    • 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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    • H05B33/00—Electroluminescent light sources
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    • 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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    • H10K85/633—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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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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

La présente invention concerne un nouveau composé électroluminescent organique et un dispositif électroluminescent organique contenant celui-ci. Le composé électroluminescent organique de l'invention permet de fabriquer un dispositif OLED présentant des tensions d'attaque réduites et un rendement énergétique accru.
PCT/KR2013/007491 2012-08-21 2013-08-21 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique contenant ceux-ci WO2014030921A1 (fr)

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KR10-2012-0091229 2012-08-21

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