WO2014196805A1 - Composé électroluminescent organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2014196805A1
WO2014196805A1 PCT/KR2014/004963 KR2014004963W WO2014196805A1 WO 2014196805 A1 WO2014196805 A1 WO 2014196805A1 KR 2014004963 W KR2014004963 W KR 2014004963W WO 2014196805 A1 WO2014196805 A1 WO 2014196805A1
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unsubstituted
substituted
independently
represent
aryl
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Soo-Jin Yang
Hee-Choon Ahn
Tae-Jin Lee
Chi-Sik Kim
Young-Jun Cho
Kyung-Joo Lee
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201480028845.XA priority Critical patent/CN105263937A/zh
Publication of WO2014196805A1 publication Critical patent/WO2014196805A1/fr

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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device 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 to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
  • fluorescent materials have been widely used as light-emitting material.
  • phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, 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-emitting materials, respectively.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • the organic EL device may be manufactured with a multi-layered structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., are comprised.
  • a compound for the hole transport layer is important to enhance characteristics of the device, such as efficiency for transporting holes to the light-emitting layer, luminous efficiency, and lifespan.
  • 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
  • WO 2013/011891 discloses compounds for the organic EL device, in which a carbazole is fused with a benzene ring and a five-membered ring to construct a backbone, and the nitrogen atom of carbazole moiety of the backbone is bonded, directly or via a linker such as aryl or heteroaryl, to heteroaryl.
  • this reference fails to specifically disclose a compound in which a carbazole is fused with a benzene ring and a five-membered ring to construct a backbone, and the nitrogen atom of carbazole moiety of the backbone is bonded, directly or via a linker such as aryl or heteroaryl, to the benzene ring which is bonded to diarylamine and another group such as aryl; and an organic EL device which uses the compound for preparing a hole transport layer.
  • the objective of the present disclosure is to provide an organic electroluminescent compound, which can provide an organic electroluminescent device having high current efficiency.
  • ring A represents
  • ring B represents
  • ring C represents
  • X 1 and X 2 each independently, represent CR 4 or N;
  • Y represents -O-, -S-, -C(R 5 )(R 6 )-, -Si(R 7 )(R 8 )-, or -N(R 9 )-;
  • L 1 to L 3 each independently, represent a single bond, a substituted or unsubstituted (C2-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • Ar 1 represents a substituted or unsubstituted(C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, or -NR 10 R 11 ;
  • Ar 2 and Ar 3 each independently, represent a substituted or unsubstituted(C1-C30)alkyl, 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 substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 12 R 13 , -SiR 14 R 15 R 16 , -SR 17 , -OR 18 , a cyano, a nitro, or a hydroxy; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic,
  • R 5 to R 9 , and R 12 to R 16 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • R 10 and R 11 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • l, m, and n each independently, represent an integer of 0 to 3; where l, m, or n is an integer of 2 or more, each of L 1 to L 3 may be the same or different;
  • a and c each independently, represent an integer of 1 to 4; where a or c is an integer of 2 or more, each of R 1 and R 3 may be the same or different;
  • b represents 1 or 2; where b is 2, each of R 2 may be the same or different; and
  • the compound represented by formula 1 has the asymmetric structure in which the benzene mother nucleus is linked to three different substituents. Due to the asymmetric structure, the compound has lower crystallinity than those of a symmetric structure, and thus is advantageous to form an amorphous thin film [Chem. Rev. 2007, 107, page 960, 4.1.2]. Furthermore, the heteroaryl group makes the compound be used for a hole transport material as well as a host material; and the nitrogen-containing pentacyclic fused group provides the compound with high glass transition temperature.
  • the organic electroluminescent compound can provide an organic electroluminescent device having high current efficiency.
  • the present disclosure provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
  • (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 30, preferably 1 to 10, and more preferably 1 to 6 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10, carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10, carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7, carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • formula 1 may be selected from the following formulae [1-1] to [1-6].
  • 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(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted heterocycloalkyl, and the substituted arylalkyl in L 1 to L 3 , Ar 1 to Ar 3 , and R 1 to R 16 each independently, are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl, a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6
  • X 1 and X 2 each independently, represent CR 4 .
  • Y represents -O-, -S-, -C(R 5 )(R 6 )-, -Si(R 7 )(R 8 )-, or -N(R 9 )-.
  • L 1 to L 3 each independently, represent a single bond, or an unsubstituted (C6-C20)arylene; and more preferably, a single bond, or an unsubstituted (C6-C15)arylene.
  • L 1 to L 3 each independently, may represent a single bond, phenylene, biphenylene, or naphthylene.
  • Ar 1 represents a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or -NR 10 R 11 .
  • the heteroaryl may contain at least one hetero atom selected from N, O, and S.
  • R 10 and R 11 each independently, represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and more preferably, represent a substituted or unsubstituted (C6-C18)aryl.
  • Ar 1 may represent a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted acenaphthenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoimidazolyl, a substituted or unsubstituted
  • Ar 2 and Ar 3 each independently, represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and more preferably, represent a substituted or unsubstituted (C6-C20)aryl.
  • Ar 2 and Ar 3 each independently, may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted phenylnaphthyl, or a substituted or unsubstituted naphthylphenyl.
  • R 1 to R 3 each independently, represent hydrogen, or are linked to an adjacent substituent(s) to form a (3- to 20-membered) monocyclic aromatic ring; and more preferably, represent hydrogen, or are linked to an adjacent substituent(s) to form a (3- to 15-membered) monocyclic aromatic ring.
  • R 4 represents hydrogen.
  • R 5 to R 9 , and R 12 to R 16 each independently, represent an unsubstituted (C1-C10)alkyl, or an unsubstituted (C6-C20)aryl; and more preferably, an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C15)aryl.
  • l, m, and n each independently, represent an integer of 0 to 3; and where l, m, or n represents an integer of 2 or more, each of L 1 to L 3 may be the same or different.
  • l, m, and n each independently, represent 0 or 1.
  • a and c each independently, represent an integer of 1 to 4; and where a or c is an integer of 2 or more, each of R 1 and R 3 may be the same or different.
  • each of R 2 may be the same or different.
  • the heteroaryl in the definitions of the groups of formula 1 is pyrrolyl, imidazolyl, triazinyl, tetrazinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, or phenanthridinyl.
  • organic electroluminescent compound of formula 1 of the present disclosure includes the following, but is not limited thereto:
  • the organic electroluminescent compound of the present disclosure can be prepared by a synthetic method known to one skilled in the art. For example, it can be prepared according to the following reaction scheme 1 or 2.
  • ring A to ring C, L 1 to L 3 , R 1 , Ar 1 to Ar 3 , a, l, m, and n are as defined in formula 1 above, and Hal represents a halogen.
  • aryl boronic acid and aryl halide are reacted with each other under a basic condition (e.g. by potassium carbonate or potassium phosphate) to form a carbon-carbon bond.
  • the reaction is carried out in a mixed solvent of toluene and ethanol; and is usually performed under reflux by using palladium complex such as tetrakistriphenylphosphine palladium and a combination of palladium acetate and S-Phos (e.g. 2-dicyclophosphino-2’,6’-dimethoxyphenyl) as a catalyst.
  • aryl amine and aryl halide are reacted with each other under a basic condition (e.g. by sodium t-butoxide) to form a carbon-nitrogen bond.
  • the reaction is carried out in an aromatic organic solvent such as toluene or xylene; and is usually performed under reflux by using palladium complex such as a combination of palladium acetate and S-Phos (e.g. 2-dicyclophosphino-2’,6’-dimethoxyphenyl) as a catalyst.
  • the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • the material may consist of the organic electroluminescent compound of formula 1. Otherwise, the material may further comprise a conventional compound(s) which has been comprised for an organic electroluminescent device, in addition to the compound of formula 1.
  • the organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
  • the organic layer may comprise at least one compound of formula 1.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from 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 of the present disclosure may be comprised in at least one of the light-emitting layer and the hole transport layer.
  • the compound of the present disclosure may be comprised as a hole transport material.
  • the compound of the present disclosure may be comprised as a host material.
  • the organic electroluminescent device comprising the compound of the present disclosure may further comprise at least one host compound other than the compound of the present disclosure. Furthermore, the organic electroluminescent device may further comprise at least one dopant.
  • the compound of the present disclosure is comprised as a host material (a first host material) in a light-emitting layer
  • another compound may be comprised as a second host material.
  • the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
  • the second host material may be from any of the known phosphorescent host materials. Specifically, the material selected from the group consisting of the compounds of formulae 2 to 4 below is preferable as the second host material in view of luminous efficiency.
  • R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or R 25 R 26 R 27 Si-;
  • R 25 to R 27 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membere
  • the second host material includes the following:
  • the dopant for the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the phosphorescent dopant may be preferably selected from the group consisting of compounds represented by the following formulae 5 to 7.
  • L is selected from the following:
  • R 100 represents hydrogen, or a substituted or unsubstituted (C1-C30)alkyl
  • R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, or a substituted or unsubstituted (C3-C30)cycloalkyl
  • R 120 to R 123 may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, e.g.
  • R 124 to R 127 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; where R 124 to R 127 are aryl, they may be linked to an adjacent substituent(s) to form a (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, e.g.
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, or a (C1-C30)alkyl unsubstituted or substituted with a halogen;
  • o and p each independently, represent an integer of 1 to 3; where o or p is an integer of 2 or more, each of R 100 may be the same or different; and
  • q represents an integer of 1 to 3.
  • the phosphorescent dopant material includes the following:
  • the present disclosure provides a composition for preparing an organic electroluminescent device.
  • the composition may comprise the compound of the present disclosure as a material for a hole transport layer.
  • the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
  • the organic layer may comprise a light-emitting layer, which may comprise the composition for the organic electroluminescent device of the present disclosure.
  • the organic electroluminescent device of the present disclosure may further comprise, in addition to the compound of 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, in addition to the compound of formula 1, 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • the organic layer may further comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device of the present disclosure 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 of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • 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 of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • 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.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant 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
  • 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 light-emitting 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, and 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.
  • OLED was produced using the compound of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Samsung Corning) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was then 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 -diphenylbenzene-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.
  • Compound C-1 was then introduced into another cell of said vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, 9-(4-([1,1':3',1''-terphenyl]-4-yl)pyrimidin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole 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, so that the dopant was 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.
  • 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% 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 then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • An OLED was produced. All the materials used for producing the OLED were those purified by vacuum sublimation at 10 -6 torr. The produced OLED showed green emission having a luminance of 1,300 cd/m 2 and a current density of 2.8 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except for using compound C-4 to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 5,100 cd/m 2 and a current density of 11.0 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except for using compound C-12 to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 1,500 cd/m 2 and a current density of 3.2 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except for using compound C-11 to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 7,600 cd/m 2 and a current density of 15.5 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except for using compound C-3 to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 4,700 cd/m 2 and a current density of 9.8 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except for using N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 10,730 cd/m 2 and a current density of 27.0 mA/cm 2 .
  • the organic electroluminescent compound of the present disclosure has better luminous characteristics than the conventional compound.
  • the organic electroluminescent device using the compound of the present disclosure shows excellent luminous characteristics, particularly current efficiency.

Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique le comprenant. Par utilisation du composé électroluminescent organique de la présente invention, un dispositif électroluminescent organique présentant une excellente efficacité de courant peut être proposé.
PCT/KR2014/004963 2013-06-03 2014-06-03 Composé électroluminescent organique et dispositif électroluminescent organique le comprenant WO2014196805A1 (fr)

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CN105712962A (zh) * 2015-09-17 2016-06-29 德山新勒克斯有限公司 有机电子元件化合物、利用此的有机电子元件及电子装置
EP3322693A4 (fr) * 2015-06-18 2019-01-16 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux
US10290813B2 (en) * 2014-10-28 2019-05-14 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device including the same
CN110945675A (zh) * 2017-07-26 2020-03-31 罗门哈斯电子材料韩国有限公司 多种主体材料和包含其的有机电致发光装置
JP2021091726A (ja) * 2015-12-17 2021-06-17 株式会社半導体エネルギー研究所 有機化合物
US11849633B2 (en) 2019-10-23 2023-12-19 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device

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KR101917858B1 (ko) * 2016-10-07 2018-11-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2019022512A1 (fr) * 2017-07-26 2019-01-31 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant
US20220081450A1 (en) * 2018-12-14 2022-03-17 Idemitsu Kosan Co.,Ltd. Organic electroluminescent element, compound, material for organic electroluminescent element, and electronic device
CN111072668A (zh) * 2019-10-31 2020-04-28 陕西莱特光电材料股份有限公司 含氮化合物、电子元件以及电子装置
CN113135928B (zh) * 2020-01-17 2024-02-13 江苏三月科技股份有限公司 一种有机化合物及包含其的有机电致发光器件
CN113416164B (zh) * 2020-04-28 2022-04-19 江苏三月科技股份有限公司 一种含咔唑的有机化合物及其应用
CN114539270B (zh) * 2021-12-09 2024-03-29 上海钥熠电子科技有限公司 含有咔唑衍生物的化合物及其在有机电致发光器件中的应用
KR20230154659A (ko) * 2022-05-02 2023-11-09 엘티소재주식회사 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자
CN115448870B (zh) * 2022-09-30 2023-12-26 长春海谱润斯科技股份有限公司 一种包含咔唑基团的芳胺化合物及其有机电致发光器件

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US10290813B2 (en) * 2014-10-28 2019-05-14 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device including the same
WO2016089080A1 (fr) * 2014-12-02 2016-06-09 주식회사 두산 Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
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CN105712962A (zh) * 2015-09-17 2016-06-29 德山新勒克斯有限公司 有机电子元件化合物、利用此的有机电子元件及电子装置
JP2021091726A (ja) * 2015-12-17 2021-06-17 株式会社半導体エネルギー研究所 有機化合物
CN110945675A (zh) * 2017-07-26 2020-03-31 罗门哈斯电子材料韩国有限公司 多种主体材料和包含其的有机电致发光装置
US11849633B2 (en) 2019-10-23 2023-12-19 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device

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