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Organic electroluminescent device

專利號
US11177444B2
公開日期
2021-11-16
申請人
LG CHEM, LTD.(KR Seoul)
發(fā)明人
Dongheon Kim; Kongkyeom Kim; Hyungjin Lee; Nansra Heo; Woochul Lee
IPC分類
C07C15/28; C07D471/10; C07D251/24; H01L51/00; H01L51/50; C07D307/91; C09K11/06
技術(shù)領(lǐng)域
group,or,aryl,heteroaryl,atoms,carbon,alkyl,layer,host,material
地域: Seoul

摘要

The present specification relates to an organic electroluminescent device comprising: a first electrode; a second electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer comprises a light emitting layer and an electron transfer layer, the light emitting layer comprises a first host material, a second host material and a dopant material, the first host material has a HOMO energy level of ?5.9 eV or lower, and the second host material has a HOMO energy level higher than a HOMO energy level of the first host material by 0.1 eV to 0.2 eV.

說明書

TECHNICAL FIELD

This application is a National Stage Application of International Application No. PCT/KR2017/011335 filed Oct. 13, 2017, and claims the benefit of Korean Patent Application No. 10-2016-0133789 filed Oct. 14, 2016, all of which are hereby incorporated by reference in their entirety for all purposes as if fully set forth herein.

The present specification relates to an organic electroluminescent device.

BACKGROUND ART

An organic light emission phenomenon generally refers to a phenomenon converting electrical energy to light energy using an organic material. An organic electroluminescent device using an organic light emission phenomenon normally has a structure including an anode, a cathode, and an organic material layer therebetween. Herein, the organic material layer is often formed in a multilayer structure formed with different materials in order to increase efficiency and stability of the organic electroluminescent device, and for example, may be formed with a hole injection layer, a hole transfer layer, a light emitting layer, an electron transfer layer, an electron injection layer and the like. When a voltage is applied between the two electrodes in such an organic electroluminescent device structure, holes and electrons are injected to the organic material layer from the anode and the cathode, respectively, and when the injected holes and electrons meet, excitons are formed, and light emits when these excitons fall back to the ground state.

Development of new materials for such an organic electroluminescent device has been continuously required.

DISCLOSURE Technical Problem

權(quán)利要求

1
The invention claimed is:1. An organic electroluminescent device comprising:a first electrode;a second electrode; andan organic material layer provided between the first electrode and the second electrode,wherein the organic material layer comprises a light emitting layer and an electron transfer layer,the light emitting layer comprises a first host material, a second host material and a dopant material,the first host material has a HOMO energy level of ?5.9 eV or lower,the second host material has a HOMO energy level higher than a HOMO energy level of the first host material by 0.1 eV to 0.2 eV, andwherein the dopant material is a pyrene-based dopant material.2. The organic electroluminescent device of claim 1, wherein the light emitting layer is a blue light emitting layer.3. The organic electroluminescent device of claim 1, wherein the electron transfer layer comprises a compound having a structure of an electron donor and an electron acceptor bonding to each other.4. The organic electroluminescent device of claim 1, wherein the electron transfer layer comprises a compound represented by the following Chemical Formula 1 or Chemical Formula 2:embedded imagein Chemical Formulae 1 and 2,X1 is C or Si;at least one of R1 to R5 is each independently represented by -(Li)z1-A1;at least one of Ar1 to Ar3 is each independently represented by -(L2)z2-A2;a1 to a3 are the same as or different from each other, and each independently an integer of 1 to 4, a1+a2+a3≤6, and when a1 to a3 are an integer of 2 or greater, substituents in the parentheses are the same as or different from each other;L1 and L2 are the same as or different from each other, and each independently a direct bond; or a divalent group comprising one or more types selected from the group consisting of a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group, z1 and z2 are an integer of 1 or 2, and when z1 and z2 are 2, substituents in the parentheses are the same as or different from each other;A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group comprising one or more Ns; andthe rest of R1 to R5 that are not -(Li)z1-A1 and the rest of Ar1 to Ar3 that are not -(La)z2-A2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; and a substituted or unsubstituted heteroaryl group, a, b, d and e are the same as or different from each other and each independently an integer of 1 to 4, c is an integer of 1 to 3, and when a to e are each 2 or greater, substituents in the parentheses are the same as or different from each other.5. The organic electroluminescent device of claim 1, wherein at least one of the first host material and the second host material is represented by a compound of the following Chemical Formula 3:embedded imagein Chemical Formula 3,R100 is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; or a substituted or unsubstituted heteroaryl group, x is an integer of 1 to 6, and when x is 2 or greater, R100s are the same as or different from each other;L11 to L14 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group, u, v, w and y are each an integer of 1 or 2, and when y is 2, L11s are the same as or different from each other, when v is 2, Lits are the same as or different from each other, when w is 2, L13s are the same as or different from each other, and when y is 2, L14s are the same as or different from each other;Ar11 and Ar13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; andAr12 and Ar14 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; or a substituted or unsubstituted heteroaryl group.6. The organic electroluminescent device of claim 4, wherein Ai is a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrrole group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted pyrazole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted isoxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted triazole group; a substituted or unsubstituted isothiazole group; a substituted or unsubstituted oxadiazole group; a substituted or unsubstituted thiadiazole group; a substituted or unsubstituted dithiazole group; a substituted or unsubstituted tetrazole group; a substituted or unsubstituted diazine group; a substituted or unsubstituted oxazine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted isoquinoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinol group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted acridine group; a substituted or unsubstituted phenanthridine group; a substituted or unsubstituted diazanaphthalene group; a substituted or unsubstituted indole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted benzocarbazole group; a substituted or unsubstituted phenazine group; or a substituted or unsubstituted phenoxazine group.7. The organic electroluminescent device of claim 4, wherein A2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted perylenyl group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted phenalenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted spirobenzoanthracenefluorenyl group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrrole group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridazine group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted pyrazole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted isoxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted triazole group; a substituted or unsubstituted isothiazole group; a substituted or unsubstituted oxadiazole group; a substituted or unsubstituted thiadiazole group; a substituted or unsubstituted dithiazole group; a substituted or unsubstituted tetrazole group; a substituted or unsubstituted diazine group; a substituted or unsubstituted oxazine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted isoquinoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinol group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted acridine group; a substituted or unsubstituted phenanthridine group; a substituted or unsubstituted diazanaphthalene group; a substituted or unsubstituted indole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted benzocarbazole group; a substituted or unsubstituted phenazine group; or a substituted or unsubstituted phenoxazine group.8. The organic electroluminescent device of claim 4, wherein Chemical Formula 1 is represented by the following Chemical Formula 4:embedded imagein Chemical Formula 4,X2 to X4 are the same as or different from each other, and each independently CR; or N, and at least one of X2 to X4 is N;Ar4 and Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;L3 is a direct bond; or a divalent group comprising one or more types selected from the group consisting of a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group, z3 is an integer of 1 or 2, and when z3 is 2, L3s are the same as or different from each other;R and R6 to R10 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; and a substituted or unsubstituted heteroaryl group, f, g and i are the same as or different from each other and each independently an integer of 1 to 4, h and j are the same as or different from each other and each independently an integer of 1 to 3, and when f to j are each 2 or greater, substituents in the parentheses are the same as or different from each other; andthe rest of the substituents have the same definitions as in Chemical Formula 1.9. The organic electroluminescent device of claim 4, wherein Chemical Formula 2 is represented by the following Chemical Formula 5 or Chemical Formula 6:embedded imagein Chemical Formulae 5 and 6,X5 to X8 and X11 to X13 are the same as or different from each other, and each independently CR′; or N, at least one of X5 to X7 is N, and at least one of X11 to X13 is N;Ar6 to Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;R′ and R11, R12, R21 and R22 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; and a substituted or unsubstituted heteroaryl group, k and t are the same as or different from each other and each independently an integer of 1 to 4, l is an integer of 1 to 8, z is an integer of 1 to 9, p and r are the same as or different from each other and each independently an integer of 1 or greater, q and s are the same as or different from each other and each independently an integer of 1 or greater, p+q+k≤6, t+r+s≤6, and when k, l, p, q, r, s, t and z are each 2 or greater, substituents in the parentheses are the same as or different from each other.10. The organic electroluminescent device of claim 5, wherein Ar11 and Ar13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.11. The organic electroluminescent device of claim 5, wherein Ar11 and Ar13 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.12. The organic electroluminescent device of claim 1, wherein the organic material layer further comprises a hole injection layer, a hole transfer layer or an electron blocking layer.13. The organic electroluminescent device of claim 1, wherein the organic material layer further comprises a hole blocking layer or an electron injection layer.
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