WO2015012618A1 - Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé - Google Patents

Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé Download PDF

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WO2015012618A1
WO2015012618A1 PCT/KR2014/006754 KR2014006754W WO2015012618A1 WO 2015012618 A1 WO2015012618 A1 WO 2015012618A1 KR 2014006754 W KR2014006754 W KR 2014006754W WO 2015012618 A1 WO2015012618 A1 WO 2015012618A1
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substituted
unsubstituted
aryl
alkyl
membered
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PCT/KR2014/006754
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Soo-Jin Yang
Doo-Hyeon Moon
Ji-Song JUN
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 CN201480038815.7A priority Critical patent/CN105358654B/zh
Publication of WO2015012618A1 publication Critical patent/WO2015012618A1/fr

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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 have been widely being researched.
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)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 2012/034627 discloses compounds for an organic EL device, in which only one substituent selected from a diarylamine, a heteroarylamine, and a nitrogen-containing heteroaryl group is bonded, directly or via a linker such as aryl, to a benzene ring of spirofluorene.
  • this reference fails to specifically disclose a compound in which two substituents are bonded to a linker or a benzene ring of spirofluorene, and an organic electroluminescent device employing the same for a hole transport layer.
  • the objective of the present disclosure is to provide an organic electroluminescent compound showing excellence in current efficiency and thermal stability due to high glass transition temperature.
  • the organic electroluminescent compound represented by formula 1, of the present disclosure includes a spirofluorene structure as a mother nucleus, which provides high glass transition temperature and excellent thermal stability.
  • Ar 1 to Ar 4 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, 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;
  • Ar 5 to Ar 8 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (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;
  • n and n each independently, represent an integer of 0 to 2; where m or n is 2, each of -N(Ar 1 )(Ar 2 ) or each of -N(Ar 3 )(Ar 4 ) may be the same or different;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; where m is 0, L 1 represents hydrogen, deuterium, 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 (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; where n is 0, L 2 represents hydrogen, deuterium, 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 (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • o 1 or 2; where o is 2, each of Ar 5 may be the same or different;
  • p, q, and r each independently, represent an integer of 1 to 4; where p, q, or r is an integer of 2 or more, each of Ar 6 , each of Ar 7 , or each of Ar 8 may be the same or different;
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, 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 R 1 and R 2 may be linked to each other to
  • the compound of formula 1 may be preferably represented by the following formula 2 or 3.
  • Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C30)aryl
  • L 1 , L 2 , Ar 5 to Ar 8 , and o to r are as defined in formula 1.
  • the compound of formula 1 may be preferably represented by the following formula 4.
  • Ar 1 and Ar 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl
  • L 1 ' represents a substituted or unsubstituted (C6-C30)arylene
  • Ar 5 to Ar 8 , and o to r are as defined in formula 1.
  • the organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device showing excellence in current efficienty and thermal stability due to its high glass transition temperature (Tg).
  • 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.
  • 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.
  • substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene) and the substituted heteroaryl(ene) in Ar 1 to Ar 8 , R 1 to R 3 , L 1 , and L 2 , 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
  • Ar 1 to Ar 4 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, 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; preferably, represent a substituted or unsubstituted (C6-C20)aryl; and more preferably, represent a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C15)aryl, or a di(C1-C6)alkyl(C6-C15)aryl.
  • Ar 1 to Ar 4 each independently, may be phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, phenanthrenyl, triphenylenyl, or fluoranthenyl.
  • Ar 1 and Ar 2 may be the same as Ar 3 or Ar 4 , wherein Ar 3 and Ar 4 may be the same or different.
  • Ar 5 to Ar 8 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (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; preferably represent hydrogen, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3- to 20-membered), mono- or polycyclic aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; and more preferably represent hydrogen, or may be linked to an adjacent substituent(
  • Ar 5 may be hydrogen; and one of Ar 6 to Ar 8 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably represents a single bond, or an unsubstituted (C6-C20)arylene; more preferably represents a single bond, or an unsubstituted (C6-C15)arylene; and specifically represents phenylene, biphenylene, or naphthylene.
  • L 1 represents hydrogen, deuterium, 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 (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and specifically represents hydrogen.
  • L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably represents a single bond, or an unsubstituted (C6-C20)arylene; more preferably represents a single bond, or an unsubstituted (C6-C15)arylene; and specifically represents phenylene, biphenylene, or naphthylene.
  • L 2 represents hydrogen, deuterium, 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 (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; and specifically represents hydrogen.
  • Ar 1 to Ar 4 each independently, represent a substituted or unsubstituted (C6-C20)aryl
  • Ar 5 to Ar 8 each independently, represet hydrogen, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3- to 20-membered), mono- or polycyclic aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur
  • m is 1 or 2
  • L 1 represents a single bond or an unsubstituted (C6-C20)arylene
  • where m represents hydrogen
  • n is 1 or 2
  • L 2 represents a single bond or an unsubstituted (C6-C20)arylene
  • n 0, L 2 represents hydrogen
  • Ar 1 to Ar 4 each independently, represent a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C15)aryl, or a di(C1-C6)alkyl(C6-C15)aryl;
  • Ar 5 to Ar 8 each independently, represent hydrogen, or may be linked to an adjacent substituent(s) to form a (3- to 15-membered), mono- or polycyclic aromatic ring unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C15)aryl, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • m is 1 or 2
  • L 1 represents a single bond or an unsubstituted (C6-C15)arylene; where m is 0, L 1 represents hydrogen; where n is 1 or 2, L 2 represents a single bond
  • organic electroluminescent compound of formula 1 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.
  • Ar 1 to Ar 8 , L 1 , L 2 , m, n, and o to r are as defined in formula 1 above, and Hal represents a halogen.
  • 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 (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 the present disclosure. 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 the present disclosure.
  • 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 an electron blocking layer.
  • the organic electroluminescent compound of the present disclosure may be comprised in at least one of the light-emitting layer and the hole transport layer.
  • the organic electroluminescent compound of the present disclosure may be comprised as a hole transport material.
  • the organic electroluminescent compound of the present disclosure may be comprised as a host material.
  • the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure may further comprise at least one compound other than the organic electroluminescent compound of the present disclosure, as a host material. Furthermore, the organic electroluminescent device may further comprise at least one dopant.
  • organic electroluminescent 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 compound selected from the group consisting of the compounds of formulae 11 to 13 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-membered
  • 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 101 to 103.
  • L is selected from the following structures:
  • 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;
  • c and d each independently, represent an integer of 1 to 3; where c or d is an integer of 2 or more, each of R 100 may be the same or different; and e represents an integer of 1 to 3.
  • the phosphorescent dopant material includes the following:
  • a mixture or composition for preparing an organic electroluminescent device comprises the compound of the present disclosure, as a host material or a hole transport material.
  • the mixture or composition may be a mixture or composition for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device.
  • 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 mixture or 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 (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone and isopropanol, 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-2 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-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-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 1,100 cd/m 2 and a current density of 2.4 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except that compound C-29 was used to form a hole transport layer having a thickness of 20 nm; and after introducing 7-(4-([1,1'-biphenyl]-4-yl)quinazolin-2-yl)-7H-benzo[c]carbazole as a host material and compound D-87 as a dopant into the two cells of the vacuum vapor depositing apparatus, respectively, the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 3 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.
  • the produced OLED showed red emission having a luminance of 1,880 cd/m 2 and a current density of 13.2 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except that compound C-8 was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 1,400 cd/m 2 and a current density of 2.9 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except that compound C-49 was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 2,100 cd/m 2 and a current density of 4.4 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 2, except that compound C-40 was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed red emission having a luminance of 2,500 cd/m 2 and a current density of 18.0 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except that N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 8,000 cd/m 2 and a current density of 20.9 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 2, except that N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed red emission having a luminance of 6,000 cd/m 2 and a current density of 80.0 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 1, except that compound-1 was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed green emission having a luminance of 9,000 cd/m 2 and a current density of 21.5 mA/cm 2 .
  • OLED was produced in the same manner as in Device Example 2, except that compound-1 was used to form a hole transport layer having a thickness of 20 nm.
  • the produced OLED showed red emission having a luminance of 7,000 cd/m 2 and a current density of 62.5 mA/cm 2 .
  • the organic electroluminescent compound of the present disclosure has high glass transition temperature, and provides higher current efficiency than conventional compounds.
  • the organic electroluminescent device shows excellent luminous efficiency, especially current efficienty by using the organic electroluminescent compound of the present disclosure.

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Abstract

La présente invention porte sur un nouveau composé électroluminescent organique et sur un dispositif électroluminescent organique le comprenant. Le composé électroluminescent organique selon l'invention possède une température de transition vitreuse élevée, et présente par conséquent une bonne stabilité thermique. L'utilisation du composé électroluminescent organique selon l'invention permet de fournir un dispositif électroluminescent organique présentant un excellent rendement électrique.
PCT/KR2014/006754 2013-07-25 2014-07-24 Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé WO2015012618A1 (fr)

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