WO2016048109A1 - Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant - Google Patents

Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant Download PDF

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WO2016048109A1
WO2016048109A1 PCT/KR2015/010261 KR2015010261W WO2016048109A1 WO 2016048109 A1 WO2016048109 A1 WO 2016048109A1 KR 2015010261 W KR2015010261 W KR 2015010261W WO 2016048109 A1 WO2016048109 A1 WO 2016048109A1
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substituted
unsubstituted
alkyl
organic electroluminescent
compound
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PCT/KR2015/010261
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English (en)
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Doo-Hyeon Moon
Jeong-Eun YANG
Hee-Ryong Kang
Young-Mook Lim
Ji-Song JUN
Hee-Choon Ahn
Jin-Ri HONG
Su-Hyun Lee
Bitnari Kim
Tae-Jin Lee
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020150135889A external-priority patent/KR102648475B1/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US15/509,590 priority Critical patent/US10886474B2/en
Priority to CN201580050211.9A priority patent/CN107074764A/zh
Priority to CN202410181294.6A priority patent/CN118026916A/zh
Priority to JP2017513089A priority patent/JP6707530B2/ja
Priority to EP15845068.4A priority patent/EP3197869A4/fr
Publication of WO2016048109A1 publication Critical patent/WO2016048109A1/fr

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Definitions

  • the present disclosure relates to an organic electroluminescent compound, and an organic electroluminescent material 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 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)
  • Korean Patent Application Laying-open No. 10-2010-0108924 and Korean Patent Application Laying-open No. 10-2014-0015259 disclose a compound having a dibenzocarbazole backbone. However, they fail to specifically disclose a compound having a structure in which a carbazole is connected to a dibenzocarbazole backbone.
  • the objective of the present disclosure is to provide an organic electroluminescent compound, which can provide an organic electroluminescent device showing long lifespan, low driving voltage, and excellence in luminous efficiency such as current efficiency and power efficiency, color purity, solubility, and thermal stability.
  • Another objective of the present disclosure is to provide an organic electroluminescent material and an organic electroluminescent device comprising the organic electroluminescent compound.
  • L represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • X represents -O-, -S-, -CR 11 R 12 -, or -NR 13 -;
  • R 11 and R 12 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 substituted or unsubstituted, (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • R 13 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
  • R 1 to R 4 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)
  • R 1 and R 4 each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (C3-C30), 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;
  • a represents an integer of 0 to 4; where a is 2 or more, each of R 1 may be the same or different;
  • b and c each independently, represent an integer of 0 to 6; where b or c is 2 or more, each of R 2 or R 3 may be the same or different;
  • d represents an integer of 0 to 3; where d is 2 or more, each of R 4 may be the same or different;
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • the organic electroluminescent compound of the present disclosure has good color purity, solubility, and thermal stability.
  • an organic electroluminescent device showing low driving voltage, excellent current and power efficiencies, and significantly improved lifespan can be provided.
  • the present disclosure provides the organic electroluminescent compound represented by formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the compound.
  • alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • aryl(ene) indicates a monocyclic or fused ring radical derived from an aromatic hydrocarbon, and includes a spiro compound in which two rings are connected through one atom.
  • the aryl includes 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)” indicates an aryl group having 3 to 30 ring backbone atoms including at least one, preferably 1 to 4, hetero atom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N; 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); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazoly
  • 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.
  • L may represent a single bond or a substituted or unsubstituted (C6-C20)arylene.
  • L may represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthracenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted tetracenylene, a substituted or unsubstituted chrysenylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted triphenylenylene, or a substituted or unsubstituted fluoranthenylene.
  • the substituent may be preferably, a (C1-C20)alkyl, a (C6-C20)aryl unsubstituted or substituted with a 6- to 20-membered heteroaryl, or a 6- to 20-membered heteroaryl unsubstituted or substituted with a (C6-C20)aryl; and more preferably, a (C1-C6)alkyl, phenyl, naphthyl, biphenyl, carbazolyl unsubstituted or substituted with phenyl, or phenyl substituted with carbazolyl unsubstituted or substituted with phenyl.
  • X represents -O-, -S-, -CR 11 R 12 -, or -NR 13 -.
  • X may represent specifically, -O-, -S-, or -NR 13 -, and more specifically -NR 13 -.
  • R 11 and R 12 each independently, may represent a substituted or unsubstituted (C1-C20)alkyl, or a substituted or unsubstituted (C6-C20)aryl, or may be linked to each other to form a substituted or unsubstituted (C3-C20), mono- or polycyclic aromatic ring.
  • R 11 and R 12 each independently, may represent a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl, or may be linked to each other to form spirobifluorenyl along with the ring containing X.
  • R 11 and R 12 may be unsubstituted groups.
  • R 13 may represent a substituted or unsubstituted (C6-C20)aryl.
  • R 13 may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted phenyl-naphthyl, a substituted or unsubstituted naphthyl-phenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted triphenyleny
  • R 1 and R 4 each independently, may represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted 5- to 20-membered heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C20), mono- or polycyclic aromatic ring.
  • R 1 and R 4 each independently, may represent hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.
  • R 1 and R 4 may be unsubstituted groups.
  • R 2 and R 3 each independently, may be selected from hydrogen and the following formulae 2-1 to 2-3.
  • L a , L b , and L c each independently, represent a single bond, or a substituted or unsubstituted (C6-C30)arylene;
  • Z represents -S-, -O-, -NR 23 -, or -CR 24 R 25 -;
  • R 20 , and R 23 to R 25 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • R 14 to R 19 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-
  • f represents an integer of 0 to 3; g, h, i, and k, each independently, represent an integer of 0 to 4; j represents an integer of 0 to 5; where f, g, h, i, j, or k is 2 or more, each of R 14 , R 15 , R 16 , R 17 , R 18 , or R 19 may be the same or different;
  • the heteroaryl contains at least one hetero atom selected from N, O, and S;
  • * represents a bonding site
  • L a to L c each independently, may represent a single bond, or a substituted or unsubstituted (C6-C18)arylene. More specifically, L a to L c , each independently, may represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.
  • Z may represent -NR 23 -.
  • R 20 and R 23 to R 25 each independently, may represent a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C18)aryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic aromatic ring. More specifically, R 20 and R 23 to R 25 , each independently, may represent a substituted or unsubstituted (C1-C6)alkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.
  • R 14 to R 19 may represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, or a substituted or unsubstituted (C6-C18)aryl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30) mono- or polycyclic aromatic ring, whose carbon atom(s) may be replaced with one to three hetero atom(s) selected from nitrogen, oxygen, and sulfur.
  • R 14 to R 19 each independently, may represent hydrogen, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl, or may be linked to an adjacent substituent(s) to form a benzene ring or a naphthalene ring.
  • L may represent a single bond, or a substituted or unsubstituted (C6-C20)arylene;
  • X may represent -O-, -S-, -CR 11 R 12 -, or -NR 13 -;
  • R 11 and R 12 each independently, may represent a substituted or unsubstituted (C1-C20)alkyl, or a substituted or unsubstituted (C6-C20)aryl, or may be linked to each other to form a substituted or unsubstituted (C3-C20), mono- or polycyclic aromatic ring;
  • R 13 may represent a substituted or unsubstituted (C6-C20)aryl;
  • R 1 and R 4 each independently, may represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstit
  • e may represent 1;
  • X may represent -O-, -S-, or -NR 13 -;
  • R 13 may represent a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted phenyl-naphthyl, a substituted or unsubstituted naphthyl-phenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted trip
  • 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 any of the following reaction scheme 1 or 2.
  • an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material are provided.
  • 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 material.
  • the organic electroluminescent material indicates a material which is used for an organic electroluminescence.
  • the organic electroluminescent material may be a material for an organic electroluminescent device, which is used for preparing an organic electroluminescent device.
  • the organic electroluminescent material may be preferably, a material to be used for a light-emitting layer of an organic electroluminescent device, more preferably, a host material to be combined with a dopant material in a light-emitting layer of an organic electroluminescent device, and even more preferably a phosphorescent host material.
  • the host material may further comprise a compound represented by the following formula 3.
  • the weight ratio between the compound of formula 1 and the compound of formula 3 may be in the range of 1:99 to 99:1, and specifically 30:70 to 70:30.
  • the organic electroluminescent material may be a hole transport material. More preferably, the organic electroluminescent material may be a material to be used for 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 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, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron buffering layer, and an electron blocking layer.
  • the organic electroluminescent compound of formula 1 of the present disclosure may be comprised in the light-emitting layer.
  • the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as a host material, preferably a phosphorescent host material, and more preferably a phosphorescent red light-emitting host material.
  • the light-emitting layer may further comprise at least one or more dopants, and, if necessary, a second host material other than the compound of formula 1 of the present disclosure.
  • the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1 and specifically 30:70 to 70:30.
  • the second host material may be from any of the known phosphorescent hosts.
  • the compound selected from the group consisting of compounds of formula 3 is preferably the second host material in view of luminous efficiency.
  • an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises one or more light-emitting layers; at least one of the one or more light-emitting layers comprises one or more dopant compounds and two or more host compounds; a first host compound of the host compounds is represented by formula 1; and a second host compound is represented by formula 3 is provided.
  • Ma represents a substituted or unsubstituted nitrogen-containing 5- to 11-membered heteroaryl
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • Xa to Xh each independently, represent hydrogen, deuterium, a halogen, a cyano, 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 (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or un
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • Ma may represent a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted ind
  • Ma may represent a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted quinoxalinyl.
  • the substituents for the substituted nitrogen-containing 5- to 11-membered heteroaryl of Ma may be a (C6-C18)aryl unsubstituted or substituted with a cyano, a halogen, a (C1-C10)alkyl, or a tri(C6-C12)arylsilyl.
  • La may represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.
  • Xa to Xh each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted 6- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C15)arylsilyl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted 6- 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.
  • the formed mono- or polycyclic aromatic ring may be a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted benzindole, a substituted or unsubstituted indene, a substituted or unsubstituted benzofuran, or a substituted or unsubstituted benzothiophene.
  • the second host material includes the following, but is not limited thereto:
  • the dopant to be comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material 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) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the dopant to be comprised in the organic electroluminescent device of the present disclosure may be 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, 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 an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsub
  • the dopant material includes the following, but is not limited thereto.
  • a mixture or composition for preparing an organic electroluminescent device comprises the compound of the present disclosure.
  • the mixture or composition may be used for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device.
  • the mixture or composition for preparing a light-emitting layer of an organic electroluminescent device may be a mixture or composition for preparing a phosphorescent or fluorescent light-emitting layer, and specifically a phosphorescent red light-emitting layer of an organic electroluminescent device.
  • the compound of the present disclosure is comprised in the mixture or composition for preparing a hole transport layer of an organic electroluminescent device, it may be comprised as a hole transport material.
  • the compound of the present disclosure may be comprised as a host material.
  • the mixture or composition may further comprise 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, and specifically 30:70 to 70:30.
  • 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, wherein the organic layer may comprise a light-emitting layer or a hole transport layer, and the light-emitting layer or the hole transport layer may comprise the mixture or composition for an organic electroluminescent device of the present disclosure.
  • the organic electroluminescent device of the present disclosure may further comprise, in addition to the organic electroluminescent 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 art, besides the compound of the present disclosure. If necessary, the organic electroluminescent device of the present disclosure may further comprise a yellow- or 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.
  • 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 ink jet printing, nozzle printing, slot coating, 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.
  • two or more host compounds for a light-emitting layer may be co-evaporated or mixture-evaporated.
  • a co-evaporation indicates a process for two or more materials to be deposited as a mixture, by introducing each of the two or more materials into respective crucible cells, and applying electric current to the cells for each of the materials to be evaporated.
  • a mixture-evaporation indicates a process for two or more materials to be deposited as a mixture, by mixing the two or more materials in one crucible cell before the deposition, and applying electric current to the cell for the mixture to be evaporated.
  • a display system or a lighting system using the organic electroluminescent device of the present disclosure can be produced.
  • organic electroluminescent compound of the present disclosure the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
  • OLED was produced using the organic electroluminescent compound of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • HI-1 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.
  • HI-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 second hole injection layer having a thickness of 5 nm on the first hole injection layer.
  • HT-1 was introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
  • HT-3 was introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying 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 first host compound ( H-1 ) and a second host compound ( H2-41 ) were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • a dopant compound ( D-71 ) was introduced into another cell.
  • the two host materials were evaporated at a 1:1 rate, while the dopant was evaporated at a different rate from the host materials, 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 40 nm on the second hole transport layer.
  • ET-1 and EI-1 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at a 1:1 rate 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 then deposited by another vacuum vapor deposition apparatus on the electron injection layer to produce an OLED.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 29.5 cd/A at a driving voltage of 3.5V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 114 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-55 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 30.6 cd/A at a driving voltage of 3.6 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 29 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-56 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 29.2 cd/A at a driving voltage of 3.5 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 12 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-25 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 29.7 cd/A at a driving voltage of 3.5 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 89 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-66 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 29.9 cd/A at a driving voltage of 3.5 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 167 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-34 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 26.9 cd/A at a driving voltage of 3.4 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 62 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-34 and compound H2-528 were used as a first host and a second host of the light-emitting material, respectively.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 30.0 cd/A at a driving voltage of 3.6 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 58 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-67 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 29.7 cd/A at a driving voltage of 3.5 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 95 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-35 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 28.6 cd/A at a driving voltage of 3.6 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 95 hours.
  • OLED was produced in the same manner as in Device Example 1, except that compound H-68 was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 28.9 cd/A at a driving voltage of 3.6 V.
  • the minimum time taken to be reduced to 97% of the luminance at 5,000 nit was 18 hours.
  • OLED was produced in the same manner as in Device Example 1, except that a thickness of the first hole injection layer was 90 nm; compound H-1 was used to form the second hole transport layer instead of HT-3; compound H2-41 was used as a single host for the light-emitting layer; dopant compound D-71 was deposited in a doping amount of 2 wt% based on the total amount of the host and dopant; and a thickness of the electron transport layer was 35 nm.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 27.2 cd/A at a driving voltage of 4.4 V.
  • OLED was produced in the same manner as in Device Example 11, except that compound H-55 was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 23.4 cd/A at a driving voltage of 3.8 V.
  • OLED was produced in the same manner as in Device Example 11, except that compound H-56 was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 23.3 cd/A at a driving voltage of 3.7 V.
  • OLED was produced in the same manner as in Device Example 11, except that compound H-34 was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 26.9 cd/A at a driving voltage of 4.2 V.
  • OLED was produced in the same manner as in Device Example 11, except that compound H-67 was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 27.1 cd/A at a driving voltage of 4.5 V.
  • OLED was produced in the same manner as in Device Example 11, except that compound H-35 was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 25.5 cd/A at a driving voltage of 3.6 V.
  • OLED was produced in the same manner as in Device Example 11, except that compound H-68 was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 26.9 cd/A at a driving voltage of 3.8 V.
  • OLED was produced in the same manner as in Device Example 1, except that compound 1 as shown below was used as a first host of the light-emitting material.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 0.6 cd/A at a driving voltage of 7.8 V. Due to the low efficiency, lifespan cannot be measured.
  • OLED was produced in the same manner as in Device Example 11, except that compound 1 as shown above was used to form the second hole transport layer.
  • the produced OLED showed a red emission having a luminance of 1,000 cd/m 2 , and a current efficiency of 10.2 cd/A at a driving voltage of 5.5 V.
  • the organic electroluminescent compounds of the present invention provide better luminous efficiency and longer lifespan than the conventional organic electroluminescent compounds.
  • the device employing the organic electroluminescent compound of the present invention exhibits excellent luminous efficiency, in particular, excellent current/power efficiencies.

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Abstract

La présente invention concerne un composé organique électroluminescent, et un matériau organique électroluminescent et un dispositif organique électroluminescent comprenant ledit composé. Le composé organique électroluminescent de la présente invention présente une pureté de couleur, solubilité et stabilité thermique excellentes. Grâce au fait qu'elle comprend le composé organique électroluminescent et le matériau organique électroluminescent de la présente invention, la présente invention permet d'obtenir un dispositif organique électroluminescent présentant une faible tension de commande, d'excellentes efficacités de courant et de puissance, et une durée de vie significativement améliorée.
PCT/KR2015/010261 2014-09-26 2015-09-25 Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant WO2016048109A1 (fr)

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US15/509,590 US10886474B2 (en) 2014-09-26 2015-09-25 Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same
CN201580050211.9A CN107074764A (zh) 2014-09-26 2015-09-25 有机电致发光化合物以及包含其的有机电致发光材料和有机电致发光装置
CN202410181294.6A CN118026916A (zh) 2014-09-26 2015-09-25 有机电致发光化合物以及包含其的有机电致发光材料和有机电致发光装置
JP2017513089A JP6707530B2 (ja) 2014-09-26 2015-09-25 有機電界発光化合物、ならびにこれを含む有機電界発光材料及び有機電界発光デバイス
EP15845068.4A EP3197869A4 (fr) 2014-09-26 2015-09-25 Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant

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