WO2015084021A1 - Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant - Google Patents

Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant Download PDF

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WO2015084021A1
WO2015084021A1 PCT/KR2014/011698 KR2014011698W WO2015084021A1 WO 2015084021 A1 WO2015084021 A1 WO 2015084021A1 KR 2014011698 W KR2014011698 W KR 2014011698W WO 2015084021 A1 WO2015084021 A1 WO 2015084021A1
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group
substituted
unsubstituted
alkyl
aryl
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Kyung-Joo Lee
Chi-Sik Kim
Seon-Woo Lee
Su-Hyun Lee
Jeong-Eun YANG
Young-Kwang Kim
Hyo-Jung Lee
Young-Jun Cho
Kyoung-Jin Park
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201480063398.1A priority Critical patent/CN105745200B/zh
Priority to JP2016532083A priority patent/JP6599860B2/ja
Publication of WO2015084021A1 publication Critical patent/WO2015084021A1/fr

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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device with the advantage of providing 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 (see Appl. Phys. Lett. 51, 913, 1987).
  • the organic EL device generally comprises an anode, a cathode, and an organic layer formed between the two electrodes and emits light when holes injected from an anode and electrons injected from a cathode form the excited state by their recombination and then the excited state is returned to the ground state.
  • the organic layer of the organic EL device may be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a light-emitting layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • HBL hole blocking layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the most important factor determining luminescent efficiency in the organic EL device is the light-emitting material.
  • the light-emitting material is required to have the following features: high quantum efficiency, high movement degree of an electron and a hole, formability of a uniform light-emitting material layer, and stability.
  • a mixed system of a dopant/host material can be used as the light-emitting material to improve color purity, luminescent efficiency, and stability. If the dopant/host material system is used, the selection of host materials is important since host materials greatly influence the efficiency and performance of a light-emitting device. In conventional technique, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known phosphorescent host material.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • the present invention can minimize crystallization by heat during and after vapor deposition at high temperature by increasing thermal stability of the materials.
  • glass transition temperature should be increased in order to increase thermal stability.
  • Tg glass transition temperature
  • many substituents should be bonded.
  • the temperature of vapor deposition excessively increases and the materials degrade and get damaged during vapor deposition when many substituents are bonded.
  • a suitable Tg should be maintained by introduction of the suitable number of substituents and low vapor deposition temperature should be retained despite high molecular weight.
  • the present invention solves the above problems by introducing a carbazole group into the 9-position of a fluorene structure.
  • the materials of the present invention have high molecular weight, they have lower vapor deposition temperature than the carbazole derivatives having similar molecular weight.
  • the materials of the present invention have a high Tg.
  • This feature results from the substitution of a carbazole group at the 9-position of a fluorene structure thereby increasing steric hindrance of the fluorene structure.
  • the higher steric hindrance the lesser interaction between molecules and the lower vapor deposition temperature.
  • Korean Patent Nos. 10-0957288, 10-0948700, and 10-0955993 disclose the compounds wherein a nitrogen-containing heterocyclic group is bonded to a carbazole group, the compounds wherein a nitrogen-containing heterocyclic group is bonded to an arylcarbazole or carbazolylalkylene group, and specific structures of indolocarbazole derivatives, respectively, as host materials in a light-emitting layer.
  • the organic EL devices comprising the compounds recited in the above publications still do not satisfy power efficiency, luminescent efficiency, lifespan, etc.
  • the present inventors have tried to find organic electroluminescent compounds which can provide the organic EL device with properties superior to the compounds recited in the above publications and have found materials having high Tg and low temperature of vapor deposition via the introduction of a carbazole group at the 9-position of a fluorene structure, and thus can provide the organic EL device with high luminescent efficiency and excellent properties.
  • the object of the present invention is to provide organic electroluminescent compounds having high luminescent efficiency and to provide an organic EL device comprising the organic electroluminescent compounds and having long driving lifespan, and improved power efficiency and current efficiency.
  • a 1 represents a substituted or unsubstituted 5- to 30-membered heteroaryl group
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-membered heteroarylene group;
  • R 1 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkylamino group, a substituted or unsubstituted (C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group;
  • R 2 represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C1-C30)alkylsilyl group, a substituted or unsubstituted (C6-C30)arylsilyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkylsilyl group, a substituted or unsubstituted (C1-C30)alkylamino group, a substituted or un
  • R 2 forms a benzocarbazole by fusion to a carbazole ring
  • R 3 represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C1-C30)alkylsilyl group, a substituted or unsubstituted (C6-C30)arylsilyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkylsilyl group, a substituted or unsubstituted (C1-C30)alkylamino group, a substituted or un
  • X represents O, S, CR 11 R 12 , NR 13 , or SiR 13 R 14 ;
  • R 4 , R 5 and R 6 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C1-C30)alkylsilyl group, a substituted or unsubstituted (C6-C30)arylsilyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkylsilyl group, a substituted or unsubstituted (C1-C30)alkylamin
  • R 11 to R 14 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; or are linked to an adjacent substituent(s) to form a mono- or polycyclic (C3-C30) alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • a, c, d and e each independently represent an integer of 1 to 4; where a, c, d or e is an integer of 2 or more, each R 2 , R 4 , R 5 or R 6 is the same or different;
  • b represents an integer of 1 to 3; where b is an integer of 2 or more, each R 3 is the same or different;
  • n an integer of 0 or 1;
  • n an integer of 1 or 2;
  • the organic electroluminescent compounds according to the present invention have high luminescent efficiency compared with conventional material, and thus the organic EL device comprising the compounds as a light-emitting host material has long driving lifespan and improved power efficiency thereby reducing consumption power.
  • the present invention relates to an organic electroluminescent compound represented by formula 1, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic EL device comprising the material.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • 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 compound of formula 1 is represented by the following formula 3, 4, or 5:
  • a 1 , L 1 , R 1 to R 5 , a, b, c, d, m and n are as defined in formula 1.
  • a 1 represents pyridine, pyrimidine, triazine, pyrazine, quinoline, quinazoline, quinoxaline, or naphthyridine
  • L 1 represents a single bond or a (C6-C20)arylene group
  • R 1 represents a (C1-C20)alkyl group, a (C6-C20)aryl group, or a 5- to 20-membered heteroaryl group
  • R 2 represents hydrogen, deuterium, a (C6-C20)aryl group, a 5- to 20-membered heteroaryl group, a (C6-C20)arylamino group, or formula 2, or forms a benzocarbazole by fusion to a carbazole ring
  • R 3 , R 4 , R 5 and R 6 each independently represent hydrogen or a (C1-C20)alkyl group
  • R 11 to R 14 each independently represent a (C1-C20)alkyl group, a (C
  • the compound of formula 1 can be selected from the group consisting of the following compounds:
  • organic electroluminescent compounds according to the present invention can be prepared by known methods to one skilled in the art, and can be prepared, for example, according to the following reaction scheme 1:
  • a 1 , L 1 , R 1 to R 5 , a, b, c, d, m and n are as defined in formula 1 and Hal represents a halogen.
  • the present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • the material can be comprised of the organic electroluminescent compound of the present invention alone, or can further include conventional materials generally included in organic electroluminescent materials.
  • the organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises at least one organic electroluminescent compound of formula 1.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
  • the organic electroluminescent compound of formula 1 of the present invention can be included as a host material in the light-emitting layer.
  • the light-emitting layer may further include at least one dopant and, if necessary, may comprise other compounds, in addition to the organic electroluminescent compound of formula 1 of the present invention, as a second host material.
  • the present invention further provides materials for preparing an organic EL device.
  • the materials comprise the first and second host materials.
  • the first host material includes the organic electroluminescent compound of the present invention.
  • the first host material and the second host material may be in the range of 1:99 to 99:1 in a weight ratio.
  • the second host material can be any of the known phosphorescent hosts and preferably is selected from the group consisting of the compounds of the following formulae 6 to 10 in view of luminescent efficiency:
  • X represents O or S
  • R 21 to R 24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group, or R 25 R 26 R 27 Si-; or are linked to an adjacent substituent(s) to form a mono- or polycyclic (C5-C30) alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • 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- or 30-membered heteroarylene group;
  • M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- or 30-membered heteroaryl group;
  • Y 1 and Y 2 each independently represent -O-, -S-, -N(R 31 )- or -C(R 32 )(R 33 )-; and Y 1 and Y 2 are not simultaneously present;
  • R 31 to R 33 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- or 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic (C5-C30) alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and R 32 and R 33 may be 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.
  • each (Cz-L 4 ), each (Cz), each R 21 , each R 22 , each R 23 or each R 24 is the same or different.
  • the second host material includes the following:
  • TPS represents triphenylsilyl
  • the dopants are preferably one or more phosphorescent dopants.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not specifically limited, but preferably may be selected from complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the dopant used in the organic electroluminescent device of the present invention may be selected from the group consisting of the compounds represented by the following formulae 11 to 13:
  • 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
  • R 120 to R 123 are linked to an adjacent substituent(s) to form a fused ring, for example, 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
  • the dopant material includes the following:
  • the organic layer of the organic electroluminescent device of the present invention comprises the organic electroluminescent compounds of formula 1 and may further include 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 organic electroluminescent compounds 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 d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • the organic electroluminescent device of 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, besides the organic electroluminescent compound of the present invention; and may further include a yellow or orange light-emitting layer, if necessary.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide (including oxides) layer of silicon or aluminum is placed on an anode surface of a light-emitting medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
  • the surface layer provides operating stability for the organic electroluminescent device.
  • 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 a light-emitting 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 a light-emitting 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
  • a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
  • An organic light-emitting diode (OLED) device using the organic electroluminescent compound of the present invention was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an OLED device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • ITO indium tin oxide
  • N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalene-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of the vacuum vapor depositing apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of the vacuum vapor depositing apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • Compound H-34 was introduced as a host into one cell of the vacuum vapor depositing apparatus, and compound D-1 as a dopant was introduced into another cell.
  • the two materials were evaporated at different rates and the dopant was deposited in a doping amount of 15 wt%, based on the total weight 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(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidiazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rates and 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 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 green emission having a current density of 3.32 mA/cm 2 and a luminance of 1310 cd/m 2 at 2.5 V.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound H-57 was used as a host in a light-emitting material.
  • the produced OLED device showed green emission having a current density of 7.26 mA/cm 2 and a luminance of 2840 cd/m 2 at 2.6 V.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound H-90 was used as a host in a light-emitting material.
  • the produced OLED device showed green emission having a current density of 9.40 mA/cm 2 and a luminance of 3910 cd/m 2 at 2.7 V.
  • An OLED device was produced in the same manner as in Device Example 1, except that compound H-15 was used as a host in a light-emitting material.
  • the produced OLED device showed green emission having a current density of 2.45 mA/cm 2 and a luminance of 890 cd/m 2 at 2.6 V.
  • Comparative Example 1 Production of an OLED device by using
  • An OLED device was produced in the same manner as in Device Example 1, except that Compound 1 was used as a host and compound D-86 was used as a dopant in a light-emitting material.
  • the produced OLED device showed green emission having a current density of 5.20 mA/cm 2 and a luminance of 1020 cd/m 2 at 4.3 V.
  • the organic electroluminescent compound of the present invention provides more excellent luminescent property than conventional light-emitting materials. Furthermore, the organic electroluminescent device using the organic electroluminescent compound of the present invention as a light-emitting host material provides good luminescent property and reduces the driving voltage, thereby enhancing power efficiency and improving consumption power.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un nouveau composé organique électroluminescent et un dispositif organique électroluminescent le comprenant. Le composé organique électroluminescent selon la présente invention peut être utilisé dans une couche électroluminescente et présente une excellente efficacité luminescente ; et un dispositif organique électroluminescent comprenant les composés organiques électroluminescents selon la présente invention présente une longue durée de vie, et un rendement en courant et un rendement énergétique améliorés.
PCT/KR2014/011698 2013-12-04 2014-12-02 Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant WO2015084021A1 (fr)

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CN201480063398.1A CN105745200B (zh) 2013-12-04 2014-12-02 新颖有机电致发光化合物和包含所述化合物的有机电致发光装置
JP2016532083A JP6599860B2 (ja) 2013-12-04 2014-12-02 新規な有機電界発光化合物及びそれを含む有機電界発光デバイス

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KR1020130149733A KR102184893B1 (ko) 2013-12-04 2013-12-04 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

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WO2015142040A1 (fr) 2014-03-17 2015-09-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
JP2015189694A (ja) * 2014-03-27 2015-11-02 旭有機材工業株式会社 フルオレン誘導体及びその製造方法、化合物、組成物並びに硬化物
WO2015167199A1 (fr) * 2014-04-29 2015-11-05 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif organique électroluminescent le comportant
WO2015190789A1 (fr) * 2014-06-09 2015-12-17 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2017014546A1 (fr) * 2015-07-20 2017-01-26 Rohm And Haas Electronic Materials Korea Ltd. Matériau luminescent pour fluorescence retardée et dispositif électroluminescent organique comprenant ce dernier
CN106938992A (zh) * 2016-01-05 2017-07-11 三星显示有限公司 稠环化合物及包含所述稠环化合物的有机发光装置
EP3119751A4 (fr) * 2014-03-17 2017-12-27 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
WO2018095389A1 (fr) * 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Composé cyclique hétérocyclique fusionné contenant de l'azote et son application
CN109942552A (zh) * 2017-11-09 2019-06-28 诺瓦尔德股份有限公司 包含三嗪基、芴基和杂芴基的化合物
US10818846B2 (en) 2014-04-29 2020-10-27 Rohm And Haas Electronic Materials Korea Ltd. Electron transport material and organic electroluminescent device comprising the same
US10954254B2 (en) 2017-02-23 2021-03-23 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11276827B2 (en) 2016-01-05 2022-03-15 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US11723270B2 (en) 2017-07-21 2023-08-08 Samsung Sdi Co., Ltd. Organic optoelectronic diode and display device
US11800796B2 (en) 2015-07-20 2023-10-24 Rohm And Haas Electronic Materials Korea Ltd. Luminescent material for delayed fluorescence and organic electroluminescent device comprising the same
CN117777108A (zh) * 2024-02-27 2024-03-29 德州学院 一种含有咔唑并芴类的化合物、使用该化合物的有机发光器件及其制备方法

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106496097B (zh) * 2016-08-31 2019-02-01 河南省科学院化学研究所有限公司 一种3-溴-9-（9-苯基芴-9-基）咔唑的合成方法
CN106397303B (zh) * 2016-08-31 2019-04-12 河南省科学院化学研究所有限公司 一种9-(3-溴苯基)-3-(9-苯基-9h-芴基)-9h-咔唑的合成方法
CN107880028B (zh) * 2016-09-30 2021-03-02 中节能万润股份有限公司 一种以氮杂苯为核心的化合物及有机电致发光器件
CN107880031B (zh) * 2016-09-30 2021-03-02 中节能万润股份有限公司 以氮杂苯为核心的化合物及其在有机电致发光器件上的应用
CN108148048B (zh) * 2016-12-06 2021-03-30 中节能万润股份有限公司 以氮杂苯为核心的化合物及其在有机电致发光器件上的应用
CN108203428A (zh) * 2016-12-19 2018-06-26 江苏三月光电科技有限公司 一种以咔唑为核心的化合物及其应用
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CN108424420B (zh) * 2017-09-30 2021-01-12 北京绿人科技有限责任公司 含有硅原子的三嗪化合物及其应用和一种有机电致发光器件
EP3483153A1 (fr) * 2017-11-09 2019-05-15 Novaled GmbH Composés comprenant du groups triazine, fluorene et aryle et leur application en dispositifs électroniques organiques
KR102098920B1 (ko) * 2018-03-08 2020-04-10 대주전자재료 주식회사 붕소원자를 포함하는 유기 화합물 및 이를 이용한 유기 전기발광소자
CN110272427B (zh) * 2018-03-14 2022-03-29 江苏三月科技股份有限公司 一种以芴为核心的化合物、其制备方法及其在有机电致发光器件上的应用
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8377572B2 (en) * 2007-09-21 2013-02-19 Cheil Industries, Inc. Polymer and organic photoelectric device including the same
CN102977006A (zh) * 2012-12-21 2013-03-20 南京邮电大学 吡啶芴类有机电致磷光主体发光材料及其制备方法
US8586200B2 (en) * 2007-09-14 2013-11-19 Cheil Industries, Inc. Organic compound, and organic photoelectric device including the same
WO2013183851A1 (fr) * 2012-06-04 2013-12-12 (주)피엔에이치테크 Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique le comprenant
KR20140130297A (ko) * 2013-04-30 2014-11-10 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1486550B1 (fr) 2002-03-15 2014-05-21 Idemitsu Kosan Co., Ltd. Materiau destine a des dispositifs electroluminescents et dispositifs electroluminescents organiques realises a l'aide de ce materiau
JP4316387B2 (ja) 2002-03-22 2009-08-19 出光興産株式会社 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
EP2080762B1 (fr) 2006-11-09 2016-09-14 Nippon Steel & Sumikin Chemical Co., Ltd. Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique
WO2010131930A2 (fr) * 2009-05-15 2010-11-18 제일모직 주식회사 Composé pour dispositif photoélectrique organique et dispositif photoélectrique organique comprenant ce composé
KR20130136359A (ko) * 2012-06-04 2013-12-12 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8586200B2 (en) * 2007-09-14 2013-11-19 Cheil Industries, Inc. Organic compound, and organic photoelectric device including the same
US8377572B2 (en) * 2007-09-21 2013-02-19 Cheil Industries, Inc. Polymer and organic photoelectric device including the same
WO2013183851A1 (fr) * 2012-06-04 2013-12-12 (주)피엔에이치테크 Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique le comprenant
CN102977006A (zh) * 2012-12-21 2013-03-20 南京邮电大学 吡啶芴类有机电致磷光主体发光材料及其制备方法
KR20140130297A (ko) * 2013-04-30 2014-11-10 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ZHAO J.-F. ET AL.: "One-pot synthesis of 2-bromo-4,5-diazafluoren-9-one via a tandem oxidation-bromination-rearrangement of phenanthroline and its hammer-shaped donor- acceptor organic semiconductors", TETRAHEDRON, vol. 67, 2011, pages 1977 - 1982 *
ZHAO X.-H. ET AL.: "A bulky pyridinylfluorene-fuctionalizing approach to synthesize diarylfluorene-based bipolar host materials for efficient red, green, blue and white electrophosphorescent devices", JOURNAL OF MATERIALS CHEMISTRY C., vol. 1, 2013, pages 3482 - 3490, XP055234374, DOI: doi:10.1039/c3tc00875d *

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EP3415508A1 (fr) * 2014-03-17 2018-12-19 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
WO2015142040A1 (fr) 2014-03-17 2015-09-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
EP3119751A4 (fr) * 2014-03-17 2017-12-27 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
JP2015189694A (ja) * 2014-03-27 2015-11-02 旭有機材工業株式会社 フルオレン誘導体及びその製造方法、化合物、組成物並びに硬化物
WO2015167199A1 (fr) * 2014-04-29 2015-11-05 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif organique électroluminescent le comportant
US10818846B2 (en) 2014-04-29 2020-10-27 Rohm And Haas Electronic Materials Korea Ltd. Electron transport material and organic electroluminescent device comprising the same
WO2015190789A1 (fr) * 2014-06-09 2015-12-17 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2017014546A1 (fr) * 2015-07-20 2017-01-26 Rohm And Haas Electronic Materials Korea Ltd. Matériau luminescent pour fluorescence retardée et dispositif électroluminescent organique comprenant ce dernier
US11800796B2 (en) 2015-07-20 2023-10-24 Rohm And Haas Electronic Materials Korea Ltd. Luminescent material for delayed fluorescence and organic electroluminescent device comprising the same
CN106938992A (zh) * 2016-01-05 2017-07-11 三星显示有限公司 稠环化合物及包含所述稠环化合物的有机发光装置
US11276827B2 (en) 2016-01-05 2022-03-15 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
CN106938992B (zh) * 2016-01-05 2023-04-14 三星显示有限公司 稠环化合物及包含所述稠环化合物的有机发光装置
WO2018095389A1 (fr) * 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Composé cyclique hétérocyclique fusionné contenant de l'azote et son application
US11447496B2 (en) 2016-11-23 2022-09-20 Guangzhou Chinaray Optoelectronic Materials Ltd. Nitrogen-containing fused heterocyclic ring compound and application thereof
US10954254B2 (en) 2017-02-23 2021-03-23 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11723270B2 (en) 2017-07-21 2023-08-08 Samsung Sdi Co., Ltd. Organic optoelectronic diode and display device
CN109942552A (zh) * 2017-11-09 2019-06-28 诺瓦尔德股份有限公司 包含三嗪基、芴基和杂芴基的化合物
CN117777108A (zh) * 2024-02-27 2024-03-29 德州学院 一种含有咔唑并芴类的化合物、使用该化合物的有机发光器件及其制备方法
CN117777108B (zh) * 2024-02-27 2024-05-10 德州学院 一种含有咔唑并芴类的化合物、使用该化合物的有机发光器件及其制备方法

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