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WO2016013875A1 - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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Publication number
WO2016013875A1
WO2016013875A1 PCT/KR2015/007636 KR2015007636W WO2016013875A1 WO 2016013875 A1 WO2016013875 A1 WO 2016013875A1 KR 2015007636 W KR2015007636 W KR 2015007636W WO 2016013875 A1 WO2016013875 A1 WO 2016013875A1
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Prior art keywords
substituted
unsubstituted
arylsilyl
alkyl
aryl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2015/007636
Other languages
French (fr)
Inventor
Kyoung-Jin Park
Tae-Jin Lee
Jae-Hoon Shim
Yoo-Jin DOH
Hee-Choon Ahn
Young-Kwang Kim
Doo-Hyeon Moon
Jeong-Eun YANG
Su-Hyun Lee
Chi-Sik Kim
Ji-Song JUN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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 KR1020150102378A external-priority patent/KR102502306B1/en
Application filed by Rohm and Haas Electronic Materials Korea Ltd, Rohm and Haas Electronic Materials LLC filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to JP2017503533A priority Critical patent/JP6688781B2/en
Priority to EP15825119.9A priority patent/EP3172780A4/en
Priority to US15/327,663 priority patent/US20170207396A1/en
Priority to CN201580038391.9A priority patent/CN106537633B/en
Publication of WO2016013875A1 publication Critical patent/WO2016013875A1/en
Anticipated expiration legal-status Critical
Priority to US17/532,265 priority patent/US20220102644A1/en
Ceased legal-status Critical Current

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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • 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

Definitions

  • the present invention relates to an organic electroluminescent device.
  • 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 organic EL device converts electric energy into light when electricity is applied to an organic light-emitting material(s).
  • the organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • materials for forming the organic layer can be classified as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer.
  • Excitons having high energy are formed by recombinations between the holes and the electrons. The energy of excitons puts the light-emitting organic compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
  • the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
  • the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
  • the light-emitting layer formed by the light-emitting material needs to be uniform and stable.
  • the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein.
  • the light-emitting materials can be classified as a host material and a dopant material. Recently, the development of an organic EL device providing high efficiency and long lifespan is an urgent issue.
  • the host material acts as a solvent in a solid state and transfers energy, and thus needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability; high electro-chemical stability to achieve long lifespan; easiness of forming amorphous thin film; good adhesion to materials of adjacent layers; and non-migration to other layers.
  • the light-emitting material may be used as a mixture of a host and a dopant.
  • devices showing good electroluminescent characteristics have a structure comprising a light-emitting layer in which a dopant is doped into a host.
  • efficiency and lifespan of the device are highly affected by the host material, and thus selection of the host material is important.
  • the object of the present invention is to provide an organic electroluminescent device showing high efficiency and long lifespan.
  • 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 and one or more hole transport 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 the following formula 1; a second host compound is represented by the following formula 2; and at least one of the one or more hole transport layers comprises the compound represented by the following formula 3:
  • a 1 and A 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl, provided that a nitrogen-containing heteroaryl is excluded from the substituent of A 1 and A 2 ;
  • L 1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene
  • X 1 to X 16 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
  • 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
  • a 3 represents a substituted or unsubstituted (C6-C30)aryl
  • L 2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • l and m each independently, represent an integer of 0 or 1, l+m is 1 or 2;
  • 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 (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 unsubsti
  • r 1 to r 4 each independently, represent an integer of 1 to 4.
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having high efficiency and long lifespan is provided.
  • the organic electroluminescent device of the present invention can be used for the manufacture of a display system or a lighting system.
  • the details of the organic electroluminescent device of the present invention are as follows.
  • the compound of formula 1 may be represented by any one of the following formulae 4, 5, 6, and 7.
  • a 1 , A 2 , L 1 and X 1 to X 16 are as defined in formula 1 above.
  • a 1 and A 2 each independently, represent a substituted or unsubstituted (C6-C30)aryl.
  • a 1 and A 2 each independently, may represent preferably, a substituted or unsubstituted (C6-C18)aryl; and more preferably, a (C6-C18)aryl unsubstituted or substituted with a cyano, a halogen, a (C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl.
  • a 1 and A 2 may be selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted, a
  • the substituents of the substituted phenyl, etc. may be a cyano, a halogen, a (C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl.
  • a 1 and A 2 may be the same or different.
  • X 1 to X 16 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
  • X 1 to X 16 each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted 5- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C12)arylsilyl.
  • X 1 to X 16 may represent hydrogen; a cyano; a (C1-C10)alkyl; a (C6-C20)aryl unsubstituted or substituted with a cyano, a (C1-C10)alkyl, or a tri(C6-C12)arylsilyl; a 5- to 20-membered heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C15)aryl or a tri(C6-C12)arylsilyl; or a tri(C6-C12)arylsilyl unsubstituted or substituted with a (C1-C10)alkyl.
  • X 1 to X 16 each independently, may represent hydrogen; a cyano; a (C1-C6)alkyl; phenyl, biphenyl, terphenyl, or naphthyl, unsubstituted or substituted with a cyano, a (C1-C6)alkyl or triphenylsilyl; dibenzothiophene or dibenzofuran, unsubstituted or substituted with a (C1-C6)alkyl, phenyl, biphenyl, naphthyl, or triphenylsilyl; or triphenylsilyl unsubstituted or substituted with a (C1-C6)alkyl.
  • L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene.
  • L 1 may represent a single bond, or a substituted or unsubstituted (C6-C15)arylene.
  • L 1 may represent one selected from the following formulae 8 to 20.
  • Xi to Xp 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
  • Xi to Xp each independently, may represent preferably, hydrogen, a halogen, a cyano, a (C1-C10)alkyl, a (C3-C20)cycloalkyl, a (C6-C12)aryl, a (C1-C6)alkyldi(C6-C12)arylsilyl, or a tri(C6-C12)arylsilyl; and more preferably, hydrogen, a cyano, a (C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
  • Ma represents a substituted or unsubstituted nitrogen-containing 5- to 11-membered heteroaryl.
  • Ma may represent preferably, a substituted or unsubstituted nitrogen-containing 6- to 10-membered heteroaryl; and more preferably, a nitrogen-containing 6- to 10-membered heteroaryl substituted with an unsubstituted (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, or a 6- to 15-membered heteroaryl.
  • Ma may represent a substituted or unsubstituted monocyclic ring-type heteroaryl selected from the group consisting of 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, and a substituted or unsubstituted pyridazinyl, or a substituted or unsubstituted fused ring-type heteroaryl selected from the group consist
  • 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 pyrrolyl, etc., of Ma may be a (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, a cyano, a (C1-C6)alkyl, a tri(C6-C12)arylsilyl, or a 6- to 15-membered heteroaryl; and specifically, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, anthracenyl, dibenzothiophenyl, or dibenzofuranyl, unsubstituted or substituted with a cyano, a (C
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; and preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene.
  • La may represent a single bond, or any one of formulae 8 to 20.
  • 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
  • Xa to Xh each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted 10- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C10)arylsilyl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C6-C20) , mono- or polycyclic, aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
  • Xa to Xh each independently, may represent hydrogen, a cyano, a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsily, or a 10- to 20-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl, or may be linked to an adjacent substituent(s) to form 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.
  • a 3 represents a substituted or unsubstituted (C6-C30)aryl; preferably, a substituted or unsubstituted (C6-C18)aryl; and more preferably, a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C6-C12)aryl, a 5- to 15-membered heteroaryl, or a tri(C6-C12)arylsilyl.
  • a 3 may be selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, and a substituted or unsubstituted triphenylenyl.
  • the substituent of the substituted phenyl etc. may be a cyano, a (C6-C12)aryl, a 5- to 15-membered heteroaryl, or a tri(C6-C12)arylsilyl.
  • L 2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; and preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene.
  • 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 (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 unsubsti
  • R 1 to R 4 each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted 10- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C10)arylsilyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C6-C21), mono- or polycyclic, aromatic ring which may form a spiro structure, and the carbon atom(s) of the ring may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
  • R 1 to R 4 each independently, may represent hydrogen, a cyano, a (C6-C18)aryl unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted 10- to 20-membered heteroaryl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted benzindene, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted spiro[cyclopentane-indene], a substituted or unsubstituted spiro[cyclohexane-indene], or a substituted or unsubstituted spiro[cyclo
  • (C1-C30)alkyl indicates a linear or branched alkyl chain having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms consistuting the chain, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30) alkenyl indicates a linear or branched alkenyl chain having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms consistuting the chain and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl indicates a linear or branched alkynyl chain having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms consistuting the chain and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 ring backbone carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • “3- to 7-membered heterocycloalkyl” indicates a cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran,
  • “(C6-C30)aryl(ene)” indicates a monocyclic or fused ring-based radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phen
  • “3- to 30-membered heteroaryl” 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; 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, tetrazolyl, furazanyl, pyridy
  • the “nitrogen-containing 5- to 30-membered heteroaryl” indicates a heteroaryl group having 5 to 30, preferably 5 to 20, and more preferably 5 to 15 ring backbone atoms including at least one, preferably 1 to 4, nitrogen as the hetero atom; 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 pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl
  • 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.
  • triarylsilyl of X 1 to X 16 in formula 1 is preferably triphenylsilyl.
  • the first host compound represented by formula 1 includes the following, but is not limited thereto.
  • the second host compound represented by formula 2 includes the following, but is not limited thereto:
  • the hole transport compound represented by formula 3 includes the following, but is not limited thereto:
  • the organic electroluminescent device of the present invention comprises 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 and one or more hole transport 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; a second host compound is represented by formula 2; and at least one of the one or more hole transport layers comprises the compound represented by formula 3.
  • the light-emitting layer indicates a layer from which light is emitted. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound in a light-emitting layer.
  • the weight ratio in the light-emitting layer between the first host material and the second host material may be in the range of 1:99 to 99:1.
  • the organic layer may comprise at least one layer selected from a hole injection layer, an electron transport layer, an electron injection layer, an electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the dopant to be comprised in the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material for the organic electroluminescent device of the present invention 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 phosphorescent dopant 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 deuterium or a halogen(s), a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, or a substituted or unsubstituted (C3-C30)cycloalkyl; 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; adjacent substituents of R 120 to R 123 may
  • 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 deuterium or 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;
  • r and s each independently, represent an integer of 1 to 3; when r or s is an integer of 2 or more, each of R 100 may be the same or different; and
  • e represents an integer of 1 to 3.
  • the phosphorescent dopant material includes the following:
  • the organic layer may further comprise 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • 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 hole injection layer In addition to the hole transport layer, a hole injection layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer.
  • the hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds.
  • the electron blocking layer may be composed of two or more layers.
  • An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode.
  • the electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer.
  • Each of the layers may comprise two or more compounds.
  • the hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
  • 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.
  • each layer of the organic electroluminescent device of the present invention dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.
  • wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods.
  • 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.
  • the organic electroluminescent device of the present invention can be used for the manufacture of a display system or a lighting system.
  • OLED organic electroluminescent device
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for 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.
  • 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 the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate HI-1, 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 the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole injection layer having a thickness of 3 nm on the first hole injection layer.
  • N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (compound H3-3) 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.
  • a compound for a second hole transport layer shown in Table 1 below was then 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 30 nm on the first hole transport layer.
  • compounds H1-34 and H2-31 were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • D-25 was introduced into another cell as a dopant.
  • the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • HTL-A as a compound for a second hole transport layer
  • OLEDs were produced in the same manner as in Device Examples 1-1 to 1-4, except that compound HTL-A shown below was used as a compound for a second hole transport layer.
  • a driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and time taken to be reduced from 100% to 97% of the luminance at 15,000 nit and a constant current (T97 lifespan) of OLEDs were measured.
  • the organic electroluminescent device of the present invention has better lifespan characteristics than conventional devices by comprising a specific hole transport compound and a plurality of hosts.

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Abstract

The present invention relates to an organic electroluminescent device. The organic electroluminescent device of the present invention shows high luminous efficiency and good lifespan by comprising a specific combination of the plural kinds of host compounds and a specific hole transport compound.

Description

ORGANIC ELECTROLUMINESCENT DEVICE
The present invention relates to an organic electroluminescent device.
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 organic EL device converts electric energy into light when electricity is applied to an organic light-emitting material(s). Generally, the organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Depending on its function, materials for forming the organic layer can be classified as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc. When a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer. Excitons having high energy are formed by recombinations between the holes and the electrons. The energy of excitons puts the light-emitting organic compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
The most important factor determining luminous efficiency in the organic EL device is light-emitting materials. The light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility. Furthermore, the light-emitting layer formed by the light-emitting material needs to be uniform and stable. Depending on colors visualized by light-emission, the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and a yellow- or orange-emitting material can be additionally included therein. Depending on its function, the light-emitting materials can be classified as a host material and a dopant material. Recently, the development of an organic EL device providing high efficiency and long lifespan is an urgent issue. Particularly, considering EL characteristic requirements for a middle or large-sized panel of OLED, materials showing better characteristics than conventional ones must be urgently developed. The host material acts as a solvent in a solid state and transfers energy, and thus needs to have high purity and a molecular weight appropriate for vacuum deposition. Furthermore, the host material needs to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability; high electro-chemical stability to achieve long lifespan; easiness of forming amorphous thin film; good adhesion to materials of adjacent layers; and non-migration to other layers.
In order to enhance color purity, luminous efficiency and stability, the light-emitting material may be used as a mixture of a host and a dopant. Generally, devices showing good electroluminescent characteristics have a structure comprising a light-emitting layer in which a dopant is doped into a host. In the dopant/host material system, efficiency and lifespan of the device are highly affected by the host material, and thus selection of the host material is important.
Many prior art references such as WO 2013/168688 A1, WO 2009/060757 A1, and Japanese Patent Application Laying-Open No. 2013-183036 A disclose an organic electroluminescent device employing a biscarbazole derivative as a host material. However, they fail to specifically disclose an organic electroluminescent device employing, as a plurality of host materials, a biscarbazole derivative in which the nitrogen atoms of the carbazoles are linked to aryls, respectively, and a carbazole derivative in which the nitrogen atom of the carbazole is linked to a nitrogen-containing heteroaryl, and as a hole transport material, a biscarbazole derivative in which the nitrogen atoms of the carbazoles are linked to aryls, respectively.
The object of the present invention is to provide an organic electroluminescent device showing high efficiency and long lifespan.
The present inventors found that the above object can be achieved by 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 and one or more hole transport 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 the following formula 1; a second host compound is represented by the following formula 2; and at least one of the one or more hole transport layers comprises the compound represented by the following formula 3:
Figure PCTKR2015007636-appb-I000001
wherein
A1 and A2, each independently, represent a substituted or unsubstituted (C6-C30)aryl, provided that a nitrogen-containing heteroaryl is excluded from the substituent of A1 and A2;
L1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;
X1 to X16, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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;
Figure PCTKR2015007636-appb-I000002
wherein
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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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;
Figure PCTKR2015007636-appb-I000003
wherein
A3 represents a substituted or unsubstituted (C6-C30)aryl;
L2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
l and m each independently, represent an integer of 0 or 1, l+m is 1 or 2;
R1 to R4, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring which may form a spiro structure, and the carbon atom(s) of the ring may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
r1 to r4, each independently, represent an integer of 1 to 4; and
the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
According to the present invention, an organic electroluminescent device having high efficiency and long lifespan is provided. In addition, the organic electroluminescent device of the present invention can be used for the manufacture of a display system or a lighting system.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The details of the organic electroluminescent device of the present invention are as follows.
According to one embodiment of the organic electroluminescent device of the present invention, the compound of formula 1 may be represented by any one of the following formulae 4, 5, 6, and 7.
Figure PCTKR2015007636-appb-I000004
wherein A1, A2, L1 and X1 to X16 are as defined in formula 1 above.
In formula 1, A1 and A2, each independently, represent a substituted or unsubstituted (C6-C30)aryl. A1 and A2, each independently, may represent preferably, a substituted or unsubstituted (C6-C18)aryl; and more preferably, a (C6-C18)aryl unsubstituted or substituted with a cyano, a halogen, a (C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl. Specifically, A1 and A2, each independently, may be selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted naphthylphenyl, and a substituted or unsubstituted fluoranthenyl. Herein, the substituents of the substituted phenyl, etc., may be a cyano, a halogen, a (C1-C6)alkyl, a (C6-C12)aryl, or a tri(C6-C12)arylsilyl. In addition, A1 and A2 may be the same or different.
In formula 1, X1 to X16, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino, 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. Preferably, X1 to X16, each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted 5- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C12)arylsilyl. More preferably, X1 to X16, each independently, may represent hydrogen; a cyano; a (C1-C10)alkyl; a (C6-C20)aryl unsubstituted or substituted with a cyano, a (C1-C10)alkyl, or a tri(C6-C12)arylsilyl; a 5- to 20-membered heteroaryl unsubstituted or substituted with a (C1-C10)alkyl, a (C6-C15)aryl or a tri(C6-C12)arylsilyl; or a tri(C6-C12)arylsilyl unsubstituted or substituted with a (C1-C10)alkyl. Specifically, X1 to X16, each independently, may represent hydrogen; a cyano; a (C1-C6)alkyl; phenyl, biphenyl, terphenyl, or naphthyl, unsubstituted or substituted with a cyano, a (C1-C6)alkyl or triphenylsilyl; dibenzothiophene or dibenzofuran, unsubstituted or substituted with a (C1-C6)alkyl, phenyl, biphenyl, naphthyl, or triphenylsilyl; or triphenylsilyl unsubstituted or substituted with a (C1-C6)alkyl.
In formula 1, L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene. Preferably, L1 may represent a single bond, or a substituted or unsubstituted (C6-C15)arylene.
L1 may represent one selected from the following formulae 8 to 20.
Figure PCTKR2015007636-appb-I000005
Figure PCTKR2015007636-appb-I000006
Figure PCTKR2015007636-appb-I000007
Figure PCTKR2015007636-appb-I000008
wherein
Xi to Xp, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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; and
Figure PCTKR2015007636-appb-I000009
represents a bonding site to a mother nucleus.
Xi to Xp, each independently, may represent preferably, hydrogen, a halogen, a cyano, a (C1-C10)alkyl, a (C3-C20)cycloalkyl, a (C6-C12)aryl, a (C1-C6)alkyldi(C6-C12)arylsilyl, or a tri(C6-C12)arylsilyl; and more preferably, hydrogen, a cyano, a (C1-C6)alkyl, or a tri(C6-C12)arylsilyl.
In formula 2, Ma represents a substituted or unsubstituted nitrogen-containing 5- to 11-membered heteroaryl. Ma may represent preferably, a substituted or unsubstituted nitrogen-containing 6- to 10-membered heteroaryl; and more preferably, a nitrogen-containing 6- to 10-membered heteroaryl substituted with an unsubstituted (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, or a 6- to 15-membered heteroaryl.
Specifically, Ma may represent a substituted or unsubstituted monocyclic ring-type heteroaryl selected from the group consisting of 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, and a substituted or unsubstituted pyridazinyl, or a substituted or unsubstituted fused ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, and a substituted or unsubstituted quinoxalinyl. Preferably, 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 pyrrolyl, etc., of Ma may be a (C6-C18)aryl, a (C6-C12)aryl substituted with a cyano, a (C6-C12)aryl substituted with a (C1-C6)alkyl, a (C6-C12)aryl substituted with a tri(C6-C12)arylsilyl, a cyano, a (C1-C6)alkyl, a tri(C6-C12)arylsilyl, or a 6- to 15-membered heteroaryl; and specifically, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, anthracenyl, dibenzothiophenyl, or dibenzofuranyl, unsubstituted or substituted with a cyano, a (C1-C6)alkyl, or triphenylsilyl.
In formula 2, La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; and preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene.
Specifically, La may represent a single bond, or any one of formulae 8 to 20.
In formula 2, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino, 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. Preferably, Xa to Xh, each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted 10- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C10)arylsilyl, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C6-C20) , mono- or polycyclic, aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur. More preferably, Xa to Xh, each independently, may represent hydrogen, a cyano, a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsily, or a 10- to 20-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl, or may be linked to an adjacent substituent(s) to form 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.
In formula 3, A3 represents a substituted or unsubstituted (C6-C30)aryl; preferably, a substituted or unsubstituted (C6-C18)aryl; and more preferably, a (C6-C18)aryl unsubstituted or substituted with a cyano, a (C6-C12)aryl, a 5- to 15-membered heteroaryl, or a tri(C6-C12)arylsilyl. Specifically, A3 may be selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, and a substituted or unsubstituted triphenylenyl. Herein, the substituent of the substituted phenyl etc., may be a cyano, a (C6-C12)aryl, a 5- to 15-membered heteroaryl, or a tri(C6-C12)arylsilyl.
In formula 3, L2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; and preferably, a single bond, or a substituted or unsubstituted (C6-C12)arylene.
In formula 3, R1 to R4, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring which may form a spiro structure, and the carbon atom(s) of the ring may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur. Preferably, R1 to R4, each independently, may represent hydrogen, a cyano, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted 10- to 20-membered heteroaryl, or a substituted or unsubstituted tri(C6-C10)arylsilyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C6-C21), mono- or polycyclic, aromatic ring which may form a spiro structure, and the carbon atom(s) of the ring may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur. More preferably, R1 to R4, each independently, may represent hydrogen, a cyano, a (C6-C18)aryl unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted 10- to 20-membered heteroaryl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted benzindene, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted spiro[cyclopentane-indene], a substituted or unsubstituted spiro[cyclohexane-indene], or a substituted or unsubstituted spiro[fluorene-indene].
Herein, “(C1-C30)alkyl” indicates a linear or branched alkyl chain having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms consistuting the chain, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C2-C30) alkenyl” indicates a linear or branched alkenyl chain having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms consistuting the chain and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. “(C2-C30)alkynyl” indicates a linear or branched alkynyl chain having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms consistuting the chain and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. “(C3-C30)cycloalkyl” indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 ring backbone carbon atoms and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” indicates a cycloalkyl having 3 to 7, preferably 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, Furthermore, “(C6-C30)aryl(ene)” indicates a monocyclic or fused ring-based radical derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring backbone carbon atoms, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “3- to 30-membered heteroaryl” 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; 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, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. The “nitrogen-containing 5- to 30-membered heteroaryl” indicates a heteroaryl group having 5 to 30, preferably 5 to 20, and more preferably 5 to 15 ring backbone atoms including at least one, preferably 1 to 4, nitrogen as the hetero atom; 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 pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzoimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc. Furthermore, “halogen” includes F, Cl, Br, and I.
Herein, “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. In the present invention, the substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted mono- or di- arylamino, the substituted nitrogen-containing heteroaryl, and the substituted mono- or polycyclic, alicyclic or aromatic ring of A1, A2, L1, X1 to X16, Ma, La, Xa to Xh, A3, L2, and R1 to R4 in formulae 1 to 3, 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 (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a 3- to 7-membered heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a cyano, a 3- to 30-membered heteroaryl, or a tri(C6-C30)arylsilyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl, and preferably a halogen; a cyano; a (C1-C6)alkyl; a 5- to 15-membered heteroaryl; a (C6-C18)aryl unsubstituted or substituted with a cyano or a tri(C6-C12)arylsilyl; a tri(C6-C12)arylsilyl; and a (C1-C6)alkyl(C6-C12)aryl.
In formula 1, triarylsilyl of X1 to X16 in formula 1 is preferably triphenylsilyl.
The first host compound represented by formula 1 includes the following, but is not limited thereto.
Figure PCTKR2015007636-appb-I000010
Figure PCTKR2015007636-appb-I000011
Figure PCTKR2015007636-appb-I000012
Figure PCTKR2015007636-appb-I000013
Figure PCTKR2015007636-appb-I000014
Figure PCTKR2015007636-appb-I000015
Figure PCTKR2015007636-appb-I000016
Figure PCTKR2015007636-appb-I000017
Figure PCTKR2015007636-appb-I000018
Figure PCTKR2015007636-appb-I000019
Figure PCTKR2015007636-appb-I000020
Figure PCTKR2015007636-appb-I000021
Figure PCTKR2015007636-appb-I000022
Figure PCTKR2015007636-appb-I000023
Figure PCTKR2015007636-appb-I000024
Figure PCTKR2015007636-appb-I000025
Figure PCTKR2015007636-appb-I000026
Figure PCTKR2015007636-appb-I000027
Figure PCTKR2015007636-appb-I000028
Figure PCTKR2015007636-appb-I000029
Figure PCTKR2015007636-appb-I000030
Figure PCTKR2015007636-appb-I000031
Figure PCTKR2015007636-appb-I000032
Figure PCTKR2015007636-appb-I000033
Figure PCTKR2015007636-appb-I000034
Figure PCTKR2015007636-appb-I000035
Figure PCTKR2015007636-appb-I000036
Figure PCTKR2015007636-appb-I000037
Figure PCTKR2015007636-appb-I000038
Figure PCTKR2015007636-appb-I000039
Figure PCTKR2015007636-appb-I000040
Figure PCTKR2015007636-appb-I000041
Figure PCTKR2015007636-appb-I000042
Figure PCTKR2015007636-appb-I000043
Figure PCTKR2015007636-appb-I000044
Figure PCTKR2015007636-appb-I000045
Figure PCTKR2015007636-appb-I000046
Figure PCTKR2015007636-appb-I000047
Figure PCTKR2015007636-appb-I000048
Figure PCTKR2015007636-appb-I000049
Figure PCTKR2015007636-appb-I000050
Figure PCTKR2015007636-appb-I000051
Figure PCTKR2015007636-appb-I000052
Figure PCTKR2015007636-appb-I000053
Figure PCTKR2015007636-appb-I000054
Figure PCTKR2015007636-appb-I000055
Figure PCTKR2015007636-appb-I000056
Figure PCTKR2015007636-appb-I000057
Figure PCTKR2015007636-appb-I000058
Figure PCTKR2015007636-appb-I000059
Figure PCTKR2015007636-appb-I000060
Figure PCTKR2015007636-appb-I000061
Figure PCTKR2015007636-appb-I000062
The second host compound represented by formula 2 includes the following, but is not limited thereto:
Figure PCTKR2015007636-appb-I000063
Figure PCTKR2015007636-appb-I000064
Figure PCTKR2015007636-appb-I000065
Figure PCTKR2015007636-appb-I000066
Figure PCTKR2015007636-appb-I000067
Figure PCTKR2015007636-appb-I000068
Figure PCTKR2015007636-appb-I000069
Figure PCTKR2015007636-appb-I000070
Figure PCTKR2015007636-appb-I000071
Figure PCTKR2015007636-appb-I000072
Figure PCTKR2015007636-appb-I000073
Figure PCTKR2015007636-appb-I000074
Figure PCTKR2015007636-appb-I000075
Figure PCTKR2015007636-appb-I000076
Figure PCTKR2015007636-appb-I000077
Figure PCTKR2015007636-appb-I000078
Figure PCTKR2015007636-appb-I000079
Figure PCTKR2015007636-appb-I000080
Figure PCTKR2015007636-appb-I000081
Figure PCTKR2015007636-appb-I000082
Figure PCTKR2015007636-appb-I000083
Figure PCTKR2015007636-appb-I000084
Figure PCTKR2015007636-appb-I000085
Figure PCTKR2015007636-appb-I000086
Figure PCTKR2015007636-appb-I000087
Figure PCTKR2015007636-appb-I000088
Figure PCTKR2015007636-appb-I000089
Figure PCTKR2015007636-appb-I000090
Figure PCTKR2015007636-appb-I000091
Figure PCTKR2015007636-appb-I000092
Figure PCTKR2015007636-appb-I000093
Figure PCTKR2015007636-appb-I000094
Figure PCTKR2015007636-appb-I000095
Figure PCTKR2015007636-appb-I000096
Figure PCTKR2015007636-appb-I000097
Figure PCTKR2015007636-appb-I000098
Figure PCTKR2015007636-appb-I000099
Figure PCTKR2015007636-appb-I000100
Figure PCTKR2015007636-appb-I000101
Figure PCTKR2015007636-appb-I000102
Figure PCTKR2015007636-appb-I000103
Figure PCTKR2015007636-appb-I000104
Figure PCTKR2015007636-appb-I000105
Figure PCTKR2015007636-appb-I000106
Figure PCTKR2015007636-appb-I000107
Figure PCTKR2015007636-appb-I000108
Figure PCTKR2015007636-appb-I000109
Figure PCTKR2015007636-appb-I000110
Figure PCTKR2015007636-appb-I000111
Figure PCTKR2015007636-appb-I000112
Figure PCTKR2015007636-appb-I000113
Figure PCTKR2015007636-appb-I000114
Figure PCTKR2015007636-appb-I000115
Figure PCTKR2015007636-appb-I000116
Figure PCTKR2015007636-appb-I000117
Figure PCTKR2015007636-appb-I000118
Figure PCTKR2015007636-appb-I000119
Figure PCTKR2015007636-appb-I000120
Figure PCTKR2015007636-appb-I000121
Figure PCTKR2015007636-appb-I000122
Figure PCTKR2015007636-appb-I000123
Figure PCTKR2015007636-appb-I000124
The hole transport compound represented by formula 3 includes the following, but is not limited thereto:
Figure PCTKR2015007636-appb-I000125
Figure PCTKR2015007636-appb-I000126
Figure PCTKR2015007636-appb-I000127
Figure PCTKR2015007636-appb-I000128
Figure PCTKR2015007636-appb-I000129
Figure PCTKR2015007636-appb-I000130
Figure PCTKR2015007636-appb-I000131
Figure PCTKR2015007636-appb-I000132
Figure PCTKR2015007636-appb-I000133
Figure PCTKR2015007636-appb-I000134
Figure PCTKR2015007636-appb-I000135
Figure PCTKR2015007636-appb-I000136
Figure PCTKR2015007636-appb-I000137
Figure PCTKR2015007636-appb-I000138
Figure PCTKR2015007636-appb-I000139
Figure PCTKR2015007636-appb-I000140
Figure PCTKR2015007636-appb-I000141
Figure PCTKR2015007636-appb-I000142
Figure PCTKR2015007636-appb-I000143
Figure PCTKR2015007636-appb-I000144
Figure PCTKR2015007636-appb-I000145
Figure PCTKR2015007636-appb-I000146
Figure PCTKR2015007636-appb-I000147
The organic electroluminescent device of the present invention comprises 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 and one or more hole transport 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; a second host compound is represented by formula 2; and at least one of the one or more hole transport layers comprises the compound represented by formula 3.
The light-emitting layer indicates a layer from which light is emitted. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound in a light-emitting layer. In the organic electroluminescent device of the present invention, the weight ratio in the light-emitting layer between the first host material and the second host material may be in the range of 1:99 to 99:1.
In addition to the light-emitting layer and the hole transport layer, the organic layer may comprise at least one layer selected from a hole injection layer, an electron transport layer, an electron injection layer, an electron buffering layer, an interlayer, a hole blocking layer, and an electron blocking layer.
The dopant to be comprised in the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant. The phosphorescent dopant material for the organic electroluminescent device of the present invention 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.
Preferably, the phosphorescent dopant may be selected from the group consisting of compounds represented by the following formulae 101 to 103.
Figure PCTKR2015007636-appb-I000148
Figure PCTKR2015007636-appb-I000149
Figure PCTKR2015007636-appb-I000150
wherein L is selected from the following structures:
Figure PCTKR2015007636-appb-I000151
R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
R101 to R109, and R111 to R123, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, or a substituted or unsubstituted (C3-C30)cycloalkyl; adjacent substituents of R106 to R109 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; adjacent substituents of R120 to R123 may be linked to each other to form a substituted or unsubstituted fused ring, e.g., quinoline unsubstituted or substituted with halogen, alkyl, or aryl;
R124 to R127, 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 R124 to R127 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;
R201 to R211, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and adjacent substituents of R208 to R211 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 and s, each independently, represent an integer of 1 to 3; when r or s is an integer of 2 or more, each of R100 may be the same or different; and
e represents an integer of 1 to 3.
Specifically, the phosphorescent dopant material includes the following:
Figure PCTKR2015007636-appb-I000152
Figure PCTKR2015007636-appb-I000153
Figure PCTKR2015007636-appb-I000154
Figure PCTKR2015007636-appb-I000155
Figure PCTKR2015007636-appb-I000156
Figure PCTKR2015007636-appb-I000157
Figure PCTKR2015007636-appb-I000158
Figure PCTKR2015007636-appb-I000159
Figure PCTKR2015007636-appb-I000161
Figure PCTKR2015007636-appb-I000162
Figure PCTKR2015007636-appb-I000163
Figure PCTKR2015007636-appb-I000164
Figure PCTKR2015007636-appb-I000165
Figure PCTKR2015007636-appb-I000166
Figure PCTKR2015007636-appb-I000167
Figure PCTKR2015007636-appb-I000168
Figure PCTKR2015007636-appb-I000169
Figure PCTKR2015007636-appb-I000170
Figure PCTKR2015007636-appb-I000171
Figure PCTKR2015007636-appb-I000172
Figure PCTKR2015007636-appb-I000173
Figure PCTKR2015007636-appb-I000174
Figure PCTKR2015007636-appb-I000175
Figure PCTKR2015007636-appb-I000176
Figure PCTKR2015007636-appb-I000177
Figure PCTKR2015007636-appb-I000178
In the organic electroluminescent device of the present invention, the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device of the present invention, 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 4th period, transition metals of the 5th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
In the organic electroluminescent device of the present invention, preferably, at least one layer (hereinafter, "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. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and 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. Preferably, the chalcogenide includes SiOX (1≤X≤2), AlOX (1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In addition to the hole transport layer, a hole injection layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer. The hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting a hole). Each of the layers may comprise two or more compounds. The electron blocking layer may be composed of two or more layers.
An electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode. The electron buffering layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
In the organic electroluminescent device of the present invention, 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. In this case, 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. Furthermore, 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. Preferably, 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 light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used. Where a layer is formed with the first host compound and the second host compound of the present invention, they may be co-evaporated or mixture-evaporated.
When using a wet film-forming method, 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.
In the organic electroluminescent device of the present invention, two or more host compounds for a light-emitting layer may be co-evaporated or mixture-evaporated. Herein, 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. Herein, 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.
The organic electroluminescent device of the present invention can be used for the manufacture of a display system or a lighting system.
Hereinafter, the preparation method of the device comprising the host compounds and the hole transport compound of the present invention, and its luminescent properties will be explained in detail with reference to the following examples.
[Device Examples 1-1 to 1-4] OLED produced by an evaporation of a hole
transport compound of the present invention, and a co-evaporation of a first host compound and a second host compound of the present invention
An organic electroluminescent device (OLED) was produced comprising the light-emitting material of the present invention as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for 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. N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine (compound HI-1) was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate HI-1, 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 the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole injection layer having a thickness of 3 nm on the first hole injection layer. N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (compound H3-3) 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. A compound for a second hole transport layer shown in Table 1 below was then 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 30 nm on the first hole transport layer. As a host material, compounds H1-34 and H2-31 were introduced into two cells of the vacuum vapor depositing apparatus, respectively. D-25 was introduced into another cell as a dopant. The two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 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 introduced into two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at the same rate of 4:6, thereby forming an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing lithium quinolate (compound EI-1) as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
Figure PCTKR2015007636-appb-I000179
[Comparative Example 1-1] OLED produced by an evaporation of compound
HTL-A as a compound for a second hole transport layer
OLEDs were produced in the same manner as in Device Examples 1-1 to 1-4, except that compound HTL-A shown below was used as a compound for a second hole transport layer.
Figure PCTKR2015007636-appb-I000180
A driving voltage at 1,000 nit, luminous efficiency, CIE color coordinate, and time taken to be reduced from 100% to 97% of the luminance at 15,000 nit and a constant current (T97 lifespan) of OLEDs were measured.
The characteristics of the organic electroluminescent devices produced in device examples 1-1 to 1-4 and comparative example 1-1 are shown in Table 1 below.
Figure PCTKR2015007636-appb-I000181
As confirmed in the Device Examples above, the organic electroluminescent device of the present invention has better lifespan characteristics than conventional devices by comprising a specific hole transport compound and a plurality of hosts.

Claims (11)

  1. 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 and one or more hole transport layers; at least one light-emitting layer comprises one or more dopant compounds and two or more host compounds; a first host compound of the host compounds is represented by the following formula 1; a second host compound is represented by the following formula 2; and at least one hole transport layer comprises the compound represented by the following formula 3:
    Figure PCTKR2015007636-appb-I000182
    wherein
    A1 and A2, each independently, represent a substituted or unsubstituted (C6-C30)aryl, provided that a nitrogen-containing heteroaryl is excluded from the substituent of A1 and A2;
    L1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;
    X1 to X16, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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;
    Figure PCTKR2015007636-appb-I000183
    wherein
    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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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;
    Figure PCTKR2015007636-appb-I000184
    wherein
    A3 represents a substituted or unsubstituted (C6-C30)aryl;
    L2 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
    l and m each independently, represent an integer of 0 or 1, l+m is 1 or 2;
    R1 to R4, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring which may form a spiro structure, and the carbon atom(s) of the ring may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
    r1 to r4, each independently, represent an integer of 1 to 4; and
    the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  2. The organic electroluminescent device according to claim 1, wherein in formula 1, A1 and A2, each independently, are selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted tetracenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted naphthylphenyl, and a substituted or unsubstituted fluoranthenyl.
  3. The organic electroluminescent device according to claim 1, wherein in formula 1, L1 represents a single bond, or one selected from the following formulae 8 to 20.
    Figure PCTKR2015007636-appb-I000185
    Figure PCTKR2015007636-appb-I000186
    Figure PCTKR2015007636-appb-I000187
    Figure PCTKR2015007636-appb-I000188
    wherein
    Xi to Xp, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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; and
    Figure PCTKR2015007636-appb-I000189
    represents a bonding site to the mother nucleus.
  4. The organic electroluminescent device according to claim 1, wherein in formula 2, Ma represents a substituted or unsubstituted monocyclic ring-type heteroaryl selected from the group consisting of 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, and a substituted or unsubstituted pyridazinyl, or a substituted or unsubstituted fused ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, and a substituted or unsubstituted quinoxalinyl.
  5. The organic electroluminescent device according to claim 1, wherein in formula 2, La represents a single bond, or one selected from the following formulae 8 to 20.
    Figure PCTKR2015007636-appb-I000190
    Figure PCTKR2015007636-appb-I000191
    Figure PCTKR2015007636-appb-I000192
    Figure PCTKR2015007636-appb-I000193
    wherein
    Xi to Xp, 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 unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; 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; and
    Figure PCTKR2015007636-appb-I000194
    represents a bonding site to the mother nucleus.
  6. The organic electroluminescent device according to claim 1, wherein in formula 2, Xa to Xh, each independently, represent hydrogen, a cyano, a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsilyl, or a 10- to 20-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl; or may be linked to an adjacent substituent(s) to form 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.
  7. The organic electroluminescent device according to claim 1, wherein in formula 3, A3 is selected from the group consisting of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, and a substituted or unsubstituted triphenylenyl.
  8. The organic electroluminescent device according to claim 1, wherein in formula 3, R1 to R4, each independently, represent hydrogen, a cyano, a (C6-C18)aryl unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted 10- to 20-membered heteroaryl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene, a substituted or unsubstituted indole, a substituted or unsubstituted indene, a substituted or unsubstituted benzindene, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted spiro[cyclopentane-indene], a substituted or unsubstituted spiro[cyclohexane-indene], or a substituted or unsubstituted spiro[fluorene-indene].
  9. The organic electroluminescent device according to claim 1, wherein the compound of formula 1 is selected from the group consisting of:
    Figure PCTKR2015007636-appb-I000195
    Figure PCTKR2015007636-appb-I000196
    Figure PCTKR2015007636-appb-I000197
    Figure PCTKR2015007636-appb-I000198
    Figure PCTKR2015007636-appb-I000199
    Figure PCTKR2015007636-appb-I000200
    Figure PCTKR2015007636-appb-I000201
    Figure PCTKR2015007636-appb-I000202
    Figure PCTKR2015007636-appb-I000203
    Figure PCTKR2015007636-appb-I000204
    Figure PCTKR2015007636-appb-I000205
    Figure PCTKR2015007636-appb-I000206
    Figure PCTKR2015007636-appb-I000207
    Figure PCTKR2015007636-appb-I000208
    Figure PCTKR2015007636-appb-I000209
    Figure PCTKR2015007636-appb-I000210
    Figure PCTKR2015007636-appb-I000211
    Figure PCTKR2015007636-appb-I000212
    Figure PCTKR2015007636-appb-I000213
    Figure PCTKR2015007636-appb-I000214
    Figure PCTKR2015007636-appb-I000215
    Figure PCTKR2015007636-appb-I000216
    Figure PCTKR2015007636-appb-I000217
    Figure PCTKR2015007636-appb-I000218
    Figure PCTKR2015007636-appb-I000219
    Figure PCTKR2015007636-appb-I000220
    Figure PCTKR2015007636-appb-I000221
    Figure PCTKR2015007636-appb-I000222
    Figure PCTKR2015007636-appb-I000223
    Figure PCTKR2015007636-appb-I000224
    Figure PCTKR2015007636-appb-I000225
    Figure PCTKR2015007636-appb-I000226
    Figure PCTKR2015007636-appb-I000227
    Figure PCTKR2015007636-appb-I000228
    Figure PCTKR2015007636-appb-I000229
    Figure PCTKR2015007636-appb-I000230
    Figure PCTKR2015007636-appb-I000231
    Figure PCTKR2015007636-appb-I000232
    Figure PCTKR2015007636-appb-I000233
    Figure PCTKR2015007636-appb-I000234
    Figure PCTKR2015007636-appb-I000235
    Figure PCTKR2015007636-appb-I000236
    Figure PCTKR2015007636-appb-I000237
    Figure PCTKR2015007636-appb-I000238
    Figure PCTKR2015007636-appb-I000239
    Figure PCTKR2015007636-appb-I000240
    Figure PCTKR2015007636-appb-I000241
    Figure PCTKR2015007636-appb-I000242
    Figure PCTKR2015007636-appb-I000243
    Figure PCTKR2015007636-appb-I000244
    Figure PCTKR2015007636-appb-I000245
    Figure PCTKR2015007636-appb-I000246
    Figure PCTKR2015007636-appb-I000247
  10. The organic electroluminescent device according to claim 1, wherein the compound of formula 2 is selected from the group consisting of:
    Figure PCTKR2015007636-appb-I000248
    Figure PCTKR2015007636-appb-I000249
    Figure PCTKR2015007636-appb-I000250
    Figure PCTKR2015007636-appb-I000251
    Figure PCTKR2015007636-appb-I000252
    Figure PCTKR2015007636-appb-I000253
    Figure PCTKR2015007636-appb-I000254
    Figure PCTKR2015007636-appb-I000255
    Figure PCTKR2015007636-appb-I000256
    Figure PCTKR2015007636-appb-I000257
    Figure PCTKR2015007636-appb-I000258
    Figure PCTKR2015007636-appb-I000259
    Figure PCTKR2015007636-appb-I000260
    Figure PCTKR2015007636-appb-I000261
    Figure PCTKR2015007636-appb-I000262
    Figure PCTKR2015007636-appb-I000263
    Figure PCTKR2015007636-appb-I000264
    Figure PCTKR2015007636-appb-I000265
    Figure PCTKR2015007636-appb-I000266
    Figure PCTKR2015007636-appb-I000267
    Figure PCTKR2015007636-appb-I000268
    Figure PCTKR2015007636-appb-I000269
    Figure PCTKR2015007636-appb-I000270
    Figure PCTKR2015007636-appb-I000271
    Figure PCTKR2015007636-appb-I000272
    Figure PCTKR2015007636-appb-I000273
    Figure PCTKR2015007636-appb-I000274
    Figure PCTKR2015007636-appb-I000275
    Figure PCTKR2015007636-appb-I000276
    Figure PCTKR2015007636-appb-I000277
    Figure PCTKR2015007636-appb-I000278
    Figure PCTKR2015007636-appb-I000279
    Figure PCTKR2015007636-appb-I000280
    Figure PCTKR2015007636-appb-I000281
    Figure PCTKR2015007636-appb-I000282
    Figure PCTKR2015007636-appb-I000283
    Figure PCTKR2015007636-appb-I000284
    Figure PCTKR2015007636-appb-I000285
    Figure PCTKR2015007636-appb-I000286
    Figure PCTKR2015007636-appb-I000287
    Figure PCTKR2015007636-appb-I000288
    Figure PCTKR2015007636-appb-I000289
    Figure PCTKR2015007636-appb-I000290
    Figure PCTKR2015007636-appb-I000291
    Figure PCTKR2015007636-appb-I000292
    Figure PCTKR2015007636-appb-I000293
    Figure PCTKR2015007636-appb-I000294
    Figure PCTKR2015007636-appb-I000295
    Figure PCTKR2015007636-appb-I000296
    Figure PCTKR2015007636-appb-I000297
    Figure PCTKR2015007636-appb-I000298
    Figure PCTKR2015007636-appb-I000299
    Figure PCTKR2015007636-appb-I000300
    Figure PCTKR2015007636-appb-I000301
    Figure PCTKR2015007636-appb-I000302
    Figure PCTKR2015007636-appb-I000303
    Figure PCTKR2015007636-appb-I000304
    Figure PCTKR2015007636-appb-I000305
    Figure PCTKR2015007636-appb-I000306
    Figure PCTKR2015007636-appb-I000307
    Figure PCTKR2015007636-appb-I000308
    Figure PCTKR2015007636-appb-I000309
  11. The organic electroluminescent device according to claim 1, wherein the compound of formula 3 is selected from the group consisting of:
    Figure PCTKR2015007636-appb-I000310
    Figure PCTKR2015007636-appb-I000311
    Figure PCTKR2015007636-appb-I000312
    Figure PCTKR2015007636-appb-I000313
    Figure PCTKR2015007636-appb-I000314
    Figure PCTKR2015007636-appb-I000315
    Figure PCTKR2015007636-appb-I000316
    Figure PCTKR2015007636-appb-I000317
    Figure PCTKR2015007636-appb-I000318
    Figure PCTKR2015007636-appb-I000319
    Figure PCTKR2015007636-appb-I000320
    Figure PCTKR2015007636-appb-I000321
    Figure PCTKR2015007636-appb-I000322
    Figure PCTKR2015007636-appb-I000323
    Figure PCTKR2015007636-appb-I000324
    Figure PCTKR2015007636-appb-I000325
    Figure PCTKR2015007636-appb-I000326
    Figure PCTKR2015007636-appb-I000327
    Figure PCTKR2015007636-appb-I000328
    Figure PCTKR2015007636-appb-I000329
    Figure PCTKR2015007636-appb-I000330
    Figure PCTKR2015007636-appb-I000331
    Figure PCTKR2015007636-appb-I000332
PCT/KR2015/007636 2014-07-22 2015-07-22 Organic electroluminescent device Ceased WO2016013875A1 (en)

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EP15825119.9A EP3172780A4 (en) 2014-07-22 2015-07-22 Organic electroluminescent device
US15/327,663 US20170207396A1 (en) 2014-07-22 2015-07-22 Organic electroluminescent device
CN201580038391.9A CN106537633B (en) 2014-07-22 2015-07-22 organic electroluminescent device
US17/532,265 US20220102644A1 (en) 2014-07-22 2021-11-22 Organic electroluminescent device

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