WO2015190789A1 - Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé - Google Patents

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

Info

Publication number
WO2015190789A1
WO2015190789A1 PCT/KR2015/005744 KR2015005744W WO2015190789A1 WO 2015190789 A1 WO2015190789 A1 WO 2015190789A1 KR 2015005744 W KR2015005744 W KR 2015005744W WO 2015190789 A1 WO2015190789 A1 WO 2015190789A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
aryl
alkyl
organic electroluminescent
Prior art date
Application number
PCT/KR2015/005744
Other languages
English (en)
Inventor
Su-Hyun Lee
Chi-Sik Kim
Ji-Song JUN
Kyoung-Jin Park
Yoo-Jin DOH
Original Assignee
Rohm And Haas Electronic Materials Korea Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020150080294A external-priority patent/KR20150141147A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to EP15806916.1A priority Critical patent/EP3152197A4/fr
Priority to JP2016569049A priority patent/JP6549159B2/ja
Priority to US15/314,515 priority patent/US20170200904A1/en
Priority to CN201580027750.0A priority patent/CN106458972B/zh
Publication of WO2015190789A1 publication Critical patent/WO2015190789A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to organic electroluminescent compounds and organic electroluminescent device comprising the same.
  • An electroluminescent 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.
  • the first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green, and blue materials, respectively.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • an organic EL device has a structure of a multilayer comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • the selection of a compound comprised in the hole transport layer is known as a method for improving the characteristics of a device such as hole transport efficiency to the light-emitting layer, luminous efficiency, lifespan, etc.
  • 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
  • Korean Patent Appln. Laying-Open No. 2010-0130197 discloses a compound wherein a nitrogen-containing heteroaryl group such as triazine is bonded to the nitrogen atom of a carbazole fused with indene as an organic electroluminescent compound.
  • a nitrogen-containing heteroaryl group such as triazine
  • indene an organic electroluminescent compound
  • the objective of the present invention is to provide i) an organic electroluminescent compound which can produce an organic electroluminescent device having excellent lifespan characteristic, and ii) an organic electroluminescent device comprising the compound.
  • X 1 and X 2 each independently represent CH or N;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
  • Ar 1 represents a substituted or unsubstituted (C6-C18)aryl
  • Ar 2 represents a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted 5- to 15-membered heteroaryl;
  • Ar 1 and Ar 2 are different from each other;
  • R 1 and R 2 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 (C6-C30)aryl(C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C1-C30)alkylsilyl, a substituted or unsubstituted (C6-C30)arylsilyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkylsilyl, a substituted
  • R 3 represents hydrogen, deuterium, a halogen, a cyano, 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 are linked to an adjacent substituent(s) to form a mono- or polycyclic (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • 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 are linked to each other to form a mono- or polycyclic (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • a and b each independently represent an integer of 1 to 4, where a or b is an integer of 2 or more, each of R 1 and each of R 2 may be the same or different;
  • c is an integer of 1 to 2, where c is 2, each of R 3 may be the same or different;
  • the heteroaryl(ene) contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • organic electroluminescent compound according to the present invention it is possible to manufacture an organic electroluminescent device having improved lifespan characteristics.
  • the present invention relates to an organic electroluminescent compound of formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
  • Tg glass transition temperature
  • various substituents can be introduced to the host compound.
  • substituents should be introduced in an appropriate level to obtain appropriate Tg, and a molecular weight should be controlled to maintain a low deposition temperature. Accordingly, the present invention solves the problem by bonding unsymmetrically two substituents to a nitrogen-containing heterocyclic ring which determines the LUMO (lowest unoccupied molecular orbital) energy level.
  • the compound of formula 1 may be represented by one of the following formulae 2 to 7:
  • X 1 , X 2 , L 1 , Ar 1 , Ar 2 , R 1 to R 3 , R 11 , R 12 , a, b, and c are as defined in formula 1.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.;
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably
  • 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.
  • X 1 and X 2 each independently represent CH or N.
  • 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 a substituted or unsubstituted (C6-C12)arylene, and more preferably represents a single bond, or an unsubstituted (C6-C12)arylene.
  • Ar 1 represents a substituted or unsubstituted (C6-C18)aryl, and preferably represents a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C1-C6)alkyl, a (C6-C12)aryl, or a 5- to 15-membered heteroaryl.
  • Ar 2 represents a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted 5- to 15-membered heteroaryl, and preferably represents a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C1-C6)alkyl, a (C6-C12)aryl, or a 5- to 15-membered heteroaryl; or a 5- to 15-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted carbazole, or a substituted or unsubstituted fluorene.
  • Ar 1 and Ar 2 are different from each other.
  • R 1 and R 2 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 (C6-C30)aryl(C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C1-C30)alkylsilyl, a substituted or unsubstituted (C6-C30)arylsilyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkylsilyl, a substituted
  • R 3 represents hydrogen, deuterium, a halogen, a cyano, 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 are linked to an adjacent substituent(s) to form a mono- or polycyclic (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur, and preferably represents hydrogen.
  • 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 are linked to each other to form a mono- or polycyclic (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur, preferably each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or are linked to each other to form a mono- or polycyclic (C3-C15) alicyclic or aromatic ring, and more preferably each independently represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C12)aryl;
  • X 1 and X 2 each independently represent CH or N;
  • L 1 represents a single bond, or a substituted or unsubstituted (C6-C12)arylene;
  • Ar 1 represents a substituted or unsubstituted (C6-C18)aryl;
  • Ar 2 represents a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted 5- to 15-membered heteroaryl;
  • Ar 1 and Ar 2 are different from each other;
  • R 1 and R 2 each independently represent hydrogen, a substituted or unsubstituted (C6-C12)aryl, or a substituted or unsubstituted 5- to 15-membered heteroaryl;
  • R 3 represents hydrogen; and
  • R 11 and R 12 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or are linked
  • X 1 and X 2 each independently represent CH or N;
  • L 1 represents a single bond, or an unsubstituted (C6-C12)arylene;
  • Ar 1 represents a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C1-C6)alkyl, a (C6-C12)aryl, or a 5- to 15-membered heteroaryl;
  • Ar 2 represents a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C1-C6)alkyl, a (C6-C12)aryl, or a 5- to 15-membered heteroaryl; or a 5- to 15-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl;
  • Ar 1 and Ar 2 are different from each other;
  • R 1 and R 2 each independently represent hydrogen, an unsubstituted (C
  • the specific compounds of the present invention include the following compounds, but are not limited thereto:
  • organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, they can be prepared according to the following reaction scheme.
  • X 1 , X 2 , L 1 , Ar 1 , Ar 2 , R 1 to R 3 , R 11 , R 12 , a, b, and c are as defined in formula 1, and Hal represents a halogen.
  • the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • the above material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
  • the organic electroluminescent device comprises 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 comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the compound of formula 1 according to the present invention can be comprised in the light-emitting layer.
  • the compound of formula 1 according to the present invention can be comprised as a phosphorescent host material.
  • the light-emitting layer can further comprise one or more dopants.
  • a compound other than the compound of formula 1 according to the present invention can be additionally 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 second host material can be any of the known phosphorescent hosts. Specifically, the phosphorescent host selected from the group consisting of the compounds of formulae 11 to 15 below is preferable in terms of luminous efficiency.
  • A 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 of unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or -SiR 25 R 26 R 27 ;
  • 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 heteroaryl;
  • Y 1 and Y 2 each independently represent -O-, -S-, -N(R 31 )-, or -C(R 32 )(R 33 )-, provided that Y 1 and Y 2 do not simultaneously exist;
  • R 31 to R 33 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, and R 32 and R 33 may be the same or different;
  • h and i each independently represent an integer of 1 to 3;
  • j, k, l, and m each independently represent an integer of 0 to 4.
  • each of (Cz-L 4 ), each of (Cz), each of R 21 , each of R 22 , each of R 23 , or each of R 24 may be the same or different.
  • preferable examples of the second host material are as follows:
  • TPS represents a triphenylsilyl group
  • the dopant comprised in the organic electroluminescent device according to the present invention is preferably at least one phosphorescent dopant.
  • the dopant materials applied to the organic electroluminescent device according to the present invention are not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper, and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper, and platinum, and even more preferably ortho-metallated iridium complex compounds.
  • the dopants comprised in the organic electroluminescent device of the present invention may be preferably selected from 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(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; adjacent substituents of R 106 to R 109 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl; and adjacent substituents of R 120 to R 123 may be linked to each other
  • 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 adjacent substituents of R 124 to R 127 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl, and adjacent substituents of R 208 to R 211 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., fluorene unsubstituted or substituted with alkyl, dibenzothiophene unsubstituted or substituted with alkyl, or dibenzofuran unsubstituted or substituted with alkyl;
  • f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each of R 100 may be the same or different; and
  • n an integer of 1 to 3.
  • the dopant compounds include the following:
  • compositions for preparing an organic electroluminescent device comprises the compound according to the present invention as a host material or a hole transport material.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise the composition for preparing the organic electroluminescent device according to the present invention.
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by 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 at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may further comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device according to the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound according to the present invention. Also, if necessary, a yellow or orange light-emitting layer can be comprised in the device.
  • a surface layer is preferably 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 (including 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.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably 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; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent 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.
  • An OLED device was produced using the organic electroluminescent compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec, Japan) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 4 ,N 4' -diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine (compound 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. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate.
  • 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (compound HI-2) was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 3 nm on the first hole injection layer.
  • compound HT-1 N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine
  • compound HT-1 was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 40 nm on the second hole injection layer. Thereafter, compound H-44 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 and were deposited in a doping amount of 15 wt% (the amount of dopant) based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)-1,3,5-triazine (compound ET-1) and lithium quinolate (compound EI-1) were then introduced into another two cells, evaporated at the rate of 4:6, and deposited 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 on the electron injection layer.
  • All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
  • the produced OLED device showed a green emission of which the time taken for the luminance at 15,000 nit to be reduced from 100% to 95% at a constant current was 13.7 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound H-58 for the host as the light-emitting material.
  • the produced OLED device showed a green emission of which the time taken for the luminance at 15,000 nit to be reduced from 100% to 95% at a constant current was 8.9 hours.
  • Comparative Example 1 Production of an OLED device using a
  • OLED device was produced in the same manner as in Device Example 1, except for using the compound below for the host as the light-emitting material.
  • the produced OLED device showed a green emission of which the time taken for the luminance at 15,000 nit to be reduced from 100% to 95% at a constant current was 6.6 hours.

Landscapes

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

Abstract

La présente invention porte sur un composé électroluminescent organique et sur un dispositif électroluminescent organique comprenant ce composé électroluminescent organique. Le fait d'utiliser le composé électroluminescent organique selon la présente invention permet de produire un dispositif électroluminescent organique ayant des caractéristiques améliorées de durée de vie.
PCT/KR2015/005744 2014-06-09 2015-06-09 Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé WO2015190789A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP15806916.1A EP3152197A4 (fr) 2014-06-09 2015-06-09 Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
JP2016569049A JP6549159B2 (ja) 2014-06-09 2015-06-09 有機電界発光化合物及びそれを含む有機電界発光デバイス
US15/314,515 US20170200904A1 (en) 2014-06-09 2015-06-09 An organic electroluminescent compound and an organic electroluminescent device comprising the same
CN201580027750.0A CN106458972B (zh) 2014-06-09 2015-06-09 有机电致发光化合物及包含其的有机电致发光器件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20140069488 2014-06-09
KR10-2014-0069488 2014-06-09
KR10-2015-0080294 2015-06-08
KR1020150080294A KR20150141147A (ko) 2014-06-09 2015-06-08 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2015190789A1 true WO2015190789A1 (fr) 2015-12-17

Family

ID=54833815

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2015/005744 WO2015190789A1 (fr) 2014-06-09 2015-06-09 Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé

Country Status (1)

Country Link
WO (1) WO2015190789A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020509584A (ja) * 2017-02-28 2020-03-26 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネッセンスデバイス

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010136109A1 (fr) * 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20110111692A (ko) * 2010-04-05 2011-10-12 에스에프씨 주식회사 스피로 화합물 및 이를 포함하는 유기전계발광소자
KR20120092908A (ko) * 2011-02-14 2012-08-22 에스에프씨 주식회사 피리딘 유도체 화합물 및 이를 포함하는 유기전계발광소자
WO2013012297A1 (fr) * 2011-07-21 2013-01-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2013122402A1 (fr) * 2012-02-17 2013-08-22 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2014038867A1 (fr) * 2012-09-07 2014-03-13 Rohm And Haas Electronic Materials Korea Ltd. Nouvelle combinaison d'un composé hôte et d'un composé dopant et un dispositif électroluminescent organique la comprenant
WO2014200244A1 (fr) * 2013-06-11 2014-12-18 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2015046916A1 (fr) * 2013-09-26 2015-04-02 Rohm And Haas Electronic Materials Korea Ltd. Combinaison d'un composé hôte et d'un composé dopant
WO2015053524A1 (fr) * 2013-10-10 2015-04-16 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2015084021A1 (fr) * 2013-12-04 2015-06-11 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
US20150171340A1 (en) * 2013-12-17 2015-06-18 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2015093551A1 (fr) * 2013-12-18 2015-06-25 出光興産株式会社 Composé, matériau d'élément organique électroluminescent, composition d'encre, élément organique électroluminescent, dispositif électronique, et procédé de production du composé

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010136109A1 (fr) * 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20110111692A (ko) * 2010-04-05 2011-10-12 에스에프씨 주식회사 스피로 화합물 및 이를 포함하는 유기전계발광소자
KR20120092908A (ko) * 2011-02-14 2012-08-22 에스에프씨 주식회사 피리딘 유도체 화합물 및 이를 포함하는 유기전계발광소자
WO2013012297A1 (fr) * 2011-07-21 2013-01-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2013122402A1 (fr) * 2012-02-17 2013-08-22 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant
WO2014038867A1 (fr) * 2012-09-07 2014-03-13 Rohm And Haas Electronic Materials Korea Ltd. Nouvelle combinaison d'un composé hôte et d'un composé dopant et un dispositif électroluminescent organique la comprenant
WO2014200244A1 (fr) * 2013-06-11 2014-12-18 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2015046916A1 (fr) * 2013-09-26 2015-04-02 Rohm And Haas Electronic Materials Korea Ltd. Combinaison d'un composé hôte et d'un composé dopant
WO2015053524A1 (fr) * 2013-10-10 2015-04-16 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2015084021A1 (fr) * 2013-12-04 2015-06-11 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
US20150171340A1 (en) * 2013-12-17 2015-06-18 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2015093551A1 (fr) * 2013-12-18 2015-06-25 出光興産株式会社 Composé, matériau d'élément organique électroluminescent, composition d'encre, élément organique électroluminescent, dispositif électronique, et procédé de production du composé

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3152197A4 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020509584A (ja) * 2017-02-28 2020-03-26 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネッセンスデバイス

Similar Documents

Publication Publication Date Title
WO2015084021A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
WO2015099485A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2015037965A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
EP2831197A1 (fr) Nouveaux composés à électroluminescence organique et dispositif à électroluminescence organique les contenant
WO2013165189A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
WO2015099486A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
WO2014030921A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique contenant ceux-ci
WO2015012618A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2013109045A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2015084114A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2014196805A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
EP3177628A1 (fr) Composés électroluminescents organiques et dispositifs électroluminescents organiques les comprenant
WO2014185751A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
EP2683712A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant lesdits composés
EP3583097A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2014129846A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique comprenant ces composés
WO2016036207A1 (fr) Matériau de transport de trous et dispositif électroluminescent organique comprenant celui-ci
EP3201200A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2016006925A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2014200244A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
EP3152197A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2016021989A1 (fr) Composés électroluminescents organiques et dispositifs électroluminescents organiques les comprenant
EP3166947A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2014104704A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2017095156A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15806916

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2016569049

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 15314515

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE

REEP Request for entry into the european phase

Ref document number: 2015806916

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2015806916

Country of ref document: EP