US20180351108A1 - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDF

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US20180351108A1
US20180351108A1 US15/779,606 US201615779606A US2018351108A1 US 20180351108 A1 US20180351108 A1 US 20180351108A1 US 201615779606 A US201615779606 A US 201615779606A US 2018351108 A1 US2018351108 A1 US 2018351108A1
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substituted
unsubstituted
organic electroluminescent
compound
aryl
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Doo-Hyeon Moon
Ji-Song Jun
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Rohm and Haas Electronic Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from PCT/KR2016/012459 external-priority patent/WO2017099360A1/en
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Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • an electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(111) complexes have been widely known as phosphorescent light-emitting 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)picolinato 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 electron buffer layer is equipped to improve a problem of light-emitting luminance reduction which may occur due to the change of current properties in the device when the device is exposed to a high temperature during a process of producing panels.
  • the properties of the compounds comprised in the electron buffer layer are important.
  • the compound used in the the electron buffer layer is desirable to perform a role of controlling an electron injection by the electron withdrawing characteristics and the electron affinity LUMO (lowest unoccupied molecular orbital) energy level, and thus may perform a role to improve the efficiency and the lifespan of the organic electroluminescent device.
  • Korean Patent Application Laid-Open No. 2014-0119642 discloses a compound comprising the following structure.
  • Korean Patent Application Laid-Open No. 2015-0077220 discloses a compound comprising the following structure, i.e. a fused azepine core structure.
  • the object of the present disclosure is to provide (1) an organic electroluminescent compound being effective to produce an organic electroluminescent device having low driving voltage and/or excellent power efficiency and/or significantly improved operative lifespan, and (2) an organic electroluminescent device comprising the organic electroluminescent compound.
  • the organic electroluminescent compound of the present disclosure may produce the organic electroluminescent device having high triplet energy and improved efficiency.
  • the present inventors found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
  • X represents O or S
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 11 R 12 ;
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2 and R 3 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
  • R 11 to R 14 each independently, represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • n 1 or 2; where if n represents 2, each Ar may be the same or different;
  • a and b each independently, represent an integer of 1 to 3; c represents an integer of 1 to 4; where if a to c, each independently, represent an integer of 2 or more, each of R 1 to R 3 may be the same or different; and
  • the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
  • the organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device having low driving voltage and/or excellent power efficiency and/or improved driving lifespan.
  • an organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layers constituting an organic electroluminescent device, if necessary.
  • an organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. If necessary, the organic electroluminescent material may be comprised in any layers constituting an organic electroluminescent device.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • X represents O or S.
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene; and more preferably, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene.
  • L may represent a single bond, a substituted or unsubstituted phenylene, an unsubstituted biphenylene, an unsubstituted naphthylene, an unsubstituted carbazolylene, an unsubstituted quinazolinylene, an unsubstituted pyridinylene, a substituted or unsubstituted triazinylene, an unsubstituted pyrimidinylene, or an unsubstituted quinoxalinylene, wherein the substituents of the substituted phenylene may be at least one selected from the group consisting of a carbazolyl substituted with a phenyl, a triazinyl substituted with a diphenyl, and a diphenylamino, and the substituents of the substituted triazinylene may be a phenyl.
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 11 R 12 ; preferably, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —NR 11 R 12 ; more preferably, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or —NR 11 R 12 .
  • Ar may represent a substituted or unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted terphenyl, an unsubstituted naphthylphenyl, an unsubstituted fluoranthenyl, an unsubstituted triphenylenyl, a substituted triazinyl, an unsubstituted dibenzofuranyl, an unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, a fluorenyl substituted with a dimethyl, an unsubstituted isoquinolyl, a quinazolinyl unsubstituted or substituted with a phenyl, an unsubstituted pyridopyrimidinyl, a substituted pyridyl, a substituted pyrimidinyl,
  • R 1 to R 3 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2 and R 3 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • R 1 to R 3 each independently, represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2 and R 3 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • R 1 to R 3 each independently, represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2 and R 3 , respectively, to form an unsubstituted, mono- or polycyclic, (C5-C18) aromatic ring.
  • R 1 to R 3 each independently, may represent hydrogen, a substituted or unsubstituted phenyl, an unsubstituted naphthylphenyl, an unsubstituted naphthyl, a triazinyl substituted with a diphenyl, a carbazolyl substituted with a phenyl, or —NR_R 14 ; or may be linked to adjacent R 1 , R 2 and R 3 , respectively, to form an unsubstituted benzene ring, wherein the substituents of the substituted phenyl may be a mono- or di- (C6-C30)arylamino, preferably, at least one selected from the group consisting of a phenylbiphenylamino, diphenylamino and dimethylfluorenylphenylamino.
  • R 11 to R 14 each independently, represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; and more preferably, a substituted or unsubstituted (C6-C18)aryl.
  • R 11 and R 12 each independently, may represent an unsubstituted phenyl, an unsubstituted naphthyl, an unsbustituted biphenyl, an unsubstituted naphthylphenyl, or a fluorenyl substituted with a dimethyl
  • R 13 and R 14 each independently, may represent an unsubstituted phenyl, or an unsubstituted biphenyl.
  • n 1 or 2; where if n represents 2, each Ar may be the same or different.
  • a and b each independently, represent an integer of 1 to 3; c represents an integer of 1 to 4; where if a to c, each independently, represent an integer of 2 or more, each of R 1 to R 3 may be the same or different.
  • a to c each independently, represent 1 or 2.
  • L represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene;
  • Ar represents a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —NR 11 R 12 ;
  • R 1 to R 3 each independently, represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2 and R 3 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) alicyclic or aromatic ring, or the combination thereof,
  • L represents a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene;
  • Ar represents a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or —NR 11 R 12 ;
  • R 1 to R 3 each independently, represent hydrogen, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or —NR 13 R 14 ; or are linked to adjacent R 1 , R 2 and R 3 , respectively, to form an unsubstituted, mono- or polycyclic, (C5-C18) aromatic ring;
  • R 11 to R 14 each independently, represent a substituted
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, 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.
  • (C 2 -C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, 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 meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, 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 ring backbone 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.
  • (3- to 7- membered) heterocycloalkyl is a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, including at least one heteroatom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure.
  • the above aryl(ene) may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc.
  • (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
  • the above heteroaryl(ene) may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); may comprise a spiro structure; and includes a monocyclic ring-type heteroaryl such as fury!, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzo
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent.
  • the substituents of the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkyl, and the substituted mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof, in L, Ar, R 1 to R 3 , and R 11 to R 14 , each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C 2 -C30)alkenyl; a (C 2 -C30)alkynyl; a (C1-C30)al
  • the organic electroluminescent compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • organic electroluminescent compound of the present disclosure may be produced by a synthetic method known to a person skilled in the art, for example, the following reaction schemes:
  • L, Ar, R 1 to R 3 , n, a, b and c are as defined in formula 1.
  • the present disclosure also discloses an organic electroluminescent material comprising the compound of formula 1, and an organic electroluminescent device comprising the material.
  • the organic electroluminescent material may consist of the organic electroluminescent compound of the present disclosure as a sole compound, or may further comprise conventional materials generally used in organic electroluminescent materials.
  • the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.
  • the organic layer may comprise 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 a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
  • the hole auxiliary layer or the light-emitting auxiliary layer may be placed between the hole transport layer and the light-emitting layer, which may control a transport rate of a hole.
  • the hole auxiliary layer or the light-emitting auxiliary layer may be effective to produce an organic electroluminescent device having excellent efficiencies and/or improved lifespan.
  • the organic electroluminescent compound represented by formula 1 may be comprised in the light-emitting layer.
  • the organic electroluminescent compound of formula 1 may be comprised as a host material.
  • the light-emitting layer may further comprise at least one dopant.
  • another compound besides the organic electroluminescent compound of formula 1 may be further comprised as a second host material.
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the doping concentration of a dopant compound to a host compound in the light-emitting layer is preferable to be less than 20 wt %.
  • the second host material can use any of the known phosphorescent hosts.
  • the second host material may comprise the compound selected from the group consisting of the compounds represented by the following formulas 11 to 16:
  • E represents O or S
  • 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 (5- to 30-membered)heteroaryl, or —SiR 25 R 26 R 27 ; in which 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 (C 6 -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
  • Y 3 to Y 5 each independently, represent CR 34 or N, in which R 34 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • B 1 and B 2 each independently, represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • B 3 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • L 5 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene.
  • the preferred examples of the second host material are as follows:
  • TPS represents a triphenylsilyl group.
  • the dopant comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably selected from the 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 dopant comprised in the organic electroluminescent device of the present disclosure may comprise the compound selected from the group consisting of the compounds represented by the following formulas 101 to 103.
  • La is selected from the following structures:
  • R 100 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • 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 substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy;
  • R 106 to R 109 may be linked to adjacent R 106 to R 109 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and R 120 to R
  • 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; and R 124 to R 127 may be linked to adjacent R 124 to R 127 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and R 208 to R 211 may be linked to adjacent R 208 to R 211 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
  • r and s each independently, represent an integer of 1 to 3; where if r or s is an integer of 2 or more, each R 100 may be the same or different; and
  • e represents an integer of 1 to 3.
  • the present disclosure provides an electron buffer material comprising the compound represented by formula 1.
  • the electron buffer material indicates a material to control flow properties of an electon.
  • the electron buffer material may trap an electron, block an electron, or lower an energy barrier between an electron transport zone and a light-emitting layer.
  • the electron buffer material may be an electron buffer material of an organic electroluminescent device.
  • the electron buffer material in an organic electroluminescent device may be used in the electron buffer layer, or may also be simultaneously used in other zones such as an electron transport zone or a light-emitting layer.
  • the electron buffer material may be a mixture or a composition further comprising conventional materials generally used in producing an organic electroluminescent device.
  • the organic electroluminescent device of the present disclosure may comprise the compound of formula 1, and further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds, simultaneously.
  • 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 one or more additional light-emitting layers 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, a red, or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise a yellow or an orange 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.
  • Such a surface layer provides operation 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 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device was produced by using the organic electroluminescent compound according to the present disclosure.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (Geomatec) was subjected to an ultrasonic washing with acetone, isopropanol, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HIL-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 ⁇ 6 torr.
  • compound HIL-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HTL-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound HTL-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound C-39 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-71 was introduced into another cell as a dopant.
  • the two materials were evaporated at a different rate, and 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 40 nm on the second hole transport layer.
  • Compound ETL-1 and compound Liq were then introduced into another two cells, and evaporated at a rate of 1:1 to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus.
  • an OLED device was produced.
  • the produced OLED device showed a power efficiency of 26.9 Im/W at a driving voltage of 3.5 V, and a red emission having a luminance of 1,000 nits.
  • the early luminance is 100% at a constant current of 5,000 nits, the luminance after 16.7 hours was 95.7% (lifespan property).
  • An OLED device was produced in the same manner as in Device Example 1, except for using the following compound A as a host.
  • the produced OLED device showed a power efficiency of 17.9 Im/W at a driving voltage of 4.5 V, and a red emission having a luminance of 1,000 nits.
  • the early luminance is 100% at a constant current of 5,000 nits, the luminance after 16.7 hours was 19.9% (lifespan property).
  • An OLED device was produced by using the organic electroluminescent compound according to the present disclosure.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HIL-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 ⁇ 6 torr.
  • compound HIL-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HTL-1 was then introduced into the cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • Compound HTL-3 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound C-39 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-13 was introduced into another cell as a dopant.
  • the two materials were evaporated at a different rate, and 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 40 nm on the second hole transport layer.
  • Compound ETL-1 and compound Liq were then introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus.
  • an OLED device was produced.
  • Each of the materials used for producing the OLED device was purified by vacuum sublimation at 10 ⁇ 6 torr.
  • OLED devices were produced in the same manner as in Device Example 2-1, except for using compound C-36 and compound C-31, respectively, as a host.
  • An OLED device was produced in the same manner as in Device Example 2-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-13 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ETL-1 and compound Liq were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm.
  • the driving voltage, the power efficiency, and the CIE color coordinate at the luminance of 1,000 nits of the OLED devices produced in Device Examples 2-1 to 2-3 and Comparative Example 2 are provided in Table 1 below.
  • the OLED device using the compound of the present disclosure as a host not only has excellent luminance property, but also induces the increase in power efficiency by lowering the driving voltage to improve the power consumption, compared to the OLED device using the conventional luminescent material.
  • An OLED device was produced in the same manner as in Device Example 1, except that a thickness of the second hole transport layer lowered to 30 nm, and a light-emitting layer and an electron transport layer were deposited as follows: Compound C-39 (a first host) and compound B-8 (a second host) were introduced into two cells of the vacuum vapor deposition apparatus, respectively, as a host. Compound D-87 was introduced into another cell as a dopant.
  • the two host compounds were evaporated at different rate of 1:2, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 10 wt % based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Thereafter, compound ETL-1 and compound Liq were then introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • OLED devices were produced in the same manner as in Device Example 3-1, except for using compound C-36 and compound C-31, respectively, as a first host compound.
  • OLED devices were produced in the same manner as in Device Example 3-1, except for using only compound C-39, compound C-36, and compound C-31, respectively, as a host in the light-emitting layer instead of the first and second host compounds.
  • the driving voltage, current and the color of the light emission at the luminance of 1,000 cd/m 2 of the OLED devices produced in Device Examples 3-1 to 3-6 are provided in Table 2 below.
  • the OLED device comprising the compound of the present disclosure as any one of the plurality of host compounds as well as comprising the compound of the present disclosure as a sole host have the excellent luminance property.
  • An OLED device was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HIL-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 ⁇ 7 torr.
  • ITO transparent electrode indium tin oxide
  • compound HIL-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • Compound HTL-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 20 nm on the second hole injection layer.
  • Compound HTL-4 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: Compound BH-1 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound BD-1 was introduced into another cell as a dopant.
  • the two materials were evaporated at a different rate, and the dopant was deposited in a doping amount of 2 wt % based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer.
  • Compound C-36 as an electron buffer material was deposited as an electron buffer layer having a thickness of 5 nm on the light-emitting layer.
  • Compound ETL-2 was introduced into one cell and compound Liq was introduced into another cell, and evaporated at the same rate and deposited in a doping amount of 50 wt % to form an electron transport layer having a thickness of 25 nm on the electron buffer layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus.
  • an OLED device was produced.
  • Each of the materials used for producing the OLED device was purified by vacuum sublimation at 10 ⁇ 6 torr.
  • OLED devices were produced in the same manner as in Device Example 4-1, except for using compound C-39, compound C-31, and compound C-94, respectively, as an electron buffer material.
  • the driving voltage, luminous efficiency and the color of the light emission at the luminance of 1,000 nits of the OLED devices produced in Device Examples 4-1 to 4-4 are provided in Table 3 below.
  • the OLED device comprising the compound of the present disclosure as an electron buffer material has low driving voltage and excellent luminous efficiency.

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KR101641404B1 (ko) * 2013-12-17 2016-07-20 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101612164B1 (ko) 2013-12-27 2016-04-12 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20150082046A (ko) 2014-01-07 2015-07-15 삼성전자주식회사 버튼을 포함하는 전자 장치
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US10461258B2 (en) * 2015-12-24 2019-10-29 Idemitsu Kosan Co., Ltd. Compound

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KR20170067643A (ko) 2017-06-16
CN108290900A (zh) 2018-07-17
EP3386987A4 (en) 2019-07-31
TW201739749A (zh) 2017-11-16
US20210257555A1 (en) 2021-08-19
EP3386987B1 (en) 2020-04-15
JP2019501522A (ja) 2019-01-17
EP3386987A1 (en) 2018-10-17
TWI722046B (zh) 2021-03-21
JP6846424B2 (ja) 2021-03-24
KR102666615B1 (ko) 2024-05-20

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