WO2015142036A1 - Matériau tampon de confinement d'électrons et dispositif électroluminescent organique comportant de matériau - Google Patents

Matériau tampon de confinement d'électrons et dispositif électroluminescent organique comportant de matériau Download PDF

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WO2015142036A1
WO2015142036A1 PCT/KR2015/002580 KR2015002580W WO2015142036A1 WO 2015142036 A1 WO2015142036 A1 WO 2015142036A1 KR 2015002580 W KR2015002580 W KR 2015002580W WO 2015142036 A1 WO2015142036 A1 WO 2015142036A1
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electron
unsubstituted
substituted
layer
organic electroluminescent
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PCT/KR2015/002580
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Sang-Hee Cho
Jeong-Hwan Jeon
Hong-Yoep NA
Ji-Song JUN
Jae-Hoon Shim
Kyung-Hoon Choi
Chi-Sik Kim
Young-Jun Cho
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020150036184A external-priority patent/KR20150108330A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to EP15764173.9A priority Critical patent/EP3119767B2/fr
Priority to US15/125,606 priority patent/US20170117485A1/en
Priority to JP2016555464A priority patent/JP2017510071A/ja
Priority to CN201580012636.0A priority patent/CN106068267B/zh
Publication of WO2015142036A1 publication Critical patent/WO2015142036A1/fr
Priority to US17/328,729 priority patent/US11751476B2/en

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Definitions

  • the present invention relates to an electron buffering material and an organic electroluminescent device comprising the same.
  • the blue fluorescent materials used at present also have several problems.
  • a current characteristic of the blue fluorescent luminescent device changes to cause a problem of a change in luminance, and a drop of an interfacial characteristic between a light-emitting layer and an electron injection layer causes a decrease in luminance.
  • an absolute value of a LUMO (lowest unoccupied molecular orbital) energy of the host (Ah) is higher than that of the dopant (Ad), and hole traps are magnified so that efficiency increases due to interfacial luminescence between the electron transport layer and the fluorescent light-emitting layer, but there is a problem in that the lifespan decreases.
  • LUMO lowest unoccupied molecular orbital
  • a blue fluorescent light-emitting device comprising an electron buffer layer is realized.
  • the reference only focuses on a coordinate shift by doping an amine-based dopant to an anthracene-based host, and a control of a light-emitting zone and color coordinate enhancement by the electron buffer layer, and an increase in luminous efficiency or improvement in lifespan by inserting an electron buffer layer are not disclosed.
  • Japanese patent no. 4947909 discloses a blue fluorescent light-emitting device comprising an electron buffer layer, electrons which are efficiently injected to the light-emitting layer compared to Alq3 by inserting the electron buffer layer, and that mobility is varied to lower the driving voltage and enhance lifespan by preventing degradation of the light-emitting interface.
  • the electron buffering materials are limited to Alq3 derivatives, the group of the materials is small, and thus analysis of effective luminous efficiency and lifespan improvement is limited.
  • the objective of the present invention is to provide an electron buffer layer which can produce an organic electroluminescent device having excellent luminous efficiency and lifespan characteristics, and an organic electroluminescent device comprising the same.
  • an electron buffering material comprising a compound comprising a nitrogen-containing heteroaryl.
  • an electron injection is controlled, and the interfacial characteristic between the light-emitting layer and the electron injection layer is improved, and so it is possible to manufacture an organic electroluminescent device having excellent luminous efficiency and lifespan characteristics.
  • Figure 1 illustrates a schematic sectional view of an organic electroluminescent device comprising the electron buffering material according to one embodiment of the present invention.
  • Figure 2 illustrates an energy gap relationship among the layers of the organic electroluminescent device according to one embodiment of the present invention.
  • Figure 3 illustrates a comparison of luminous efficiency between an organic electroluminescent device comprising an electron buffer layer and an organic electroluminescent device not comprising any electron buffer layer.
  • the present invention relates to an electron buffering material comprising a compound comprising a nitrogen-containing heteroaryl, and an organic electroluminescent device comprising a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode; and an electron transport zone and an electron buffer layer between the light-emitting layer and the second electrode, wherein the electron buffer layer comprises the compound comprising a nitrogen-containing heteroaryl.
  • the electron buffering material according to the present invention can be a mixture or composition additionally comprising a material commonly used when producing an organic electroluminescent device.
  • an electron buffer layer can be inserted between the light-emitting layer and the second electrode to focus on obtaining high efficiency due to electron injection controlled by the LUMO energy level of the electron buffer layer and long lifespan.
  • LUMO lowest unoccupied molecular orbital
  • HOMO highest occupied molecular orbital
  • LUMO energy level (A) and HOMO energy level are expressed in absolute values in the present invention.
  • the values of the LUMO energy level are compared based on absolute values.
  • the electron buffer layer and the electron transport zone are inserted between the light-emitting layer and the second electrode.
  • the electron buffer layer can be located between the light-emitting layer and the electron transport zone, or between the electron transport zone and the second electrode.
  • an electron transport zone means a zone in which electrons are transported from the second electrode to the light-emitting layer.
  • the electron transport zone can comprise an electron transport compound, a reductive dopant, or a combination thereof.
  • the electron transport compound can be at least one selected from a group comprising oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, anthracene-based compounds, aluminum complexes, and gallium complexes.
  • the reductive dopant can be at least one selected from a group consisting of alkali metals, alkali metal compounds, alkaline-earth metals, rare earth metals, halides thereof, oxides thereof, and complexes thereof.
  • the electron transport zone can comprise an electron transport layer, an electron injection layer, or both of them.
  • the electron transport layer and the electron injection layer can each be composed of two or more layers.
  • Figure 1 illustrates a schematic sectional view of an organic electroluminescent device comprising the electron buffering material according to one embodiment of the present invention.
  • injection and transport of electrons can be controlled due to the difference of affinities between the light-emitting layer and the electron transport zone in accordance with LUMO energy levels.
  • Figure 2 illustrates an energy gap relationship among the layers of the organic electroluminescent device according to one embodiment of the present invention.
  • a nitrogen-containing heteroaryl can be a triazine derivative, a pyrimidine derivative, a quinazoline derivative, a quinoxaline derivative, etc. Electron injection characteristics can be controlled by varying the nitrogen-containing heteroaryl.
  • An electron buffering material compound comprising a triazine derivative can obtain suitable efficiency and lifespan characteristic through a specific level of restraint of electron injection by taking advantage of an appropriate barrier against the light-emitting layer.
  • An electron buffering material compound comprising a pyrimidine derivative can contribute to efficiency increase of the device by minimizing the electron injection barrier from the light-emitting layer in accordance with low LUMO energy levels.
  • An electron buffering material compound comprising a quinazoline or quinoxaline shows a big improvement of lifespan rather than the efficiency of the device by excessive electron injection block in accordance with high LUMO energy levels.
  • the compound comprising a nitrogen-containing heteroaryl comprised in the electron buffering material can be selected from the compounds represented by the following formulae 1 to 3:
  • A represents
  • R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, or -SiR 6 R 7 R 8 ; or R 1 to R 5 each independently are linked to an adjacent substituent(s) to form a mono- or polycyclic, substituted or unsubstituted (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • R 6 to R 8 each independently represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene;
  • M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • Cz, L 1 , and M may be fused to an adjacent substituent(s) to form a ring;
  • X 1 to X 3 each independently represent -N(R 9 )- or -C(R 10 )(R 11 )-;
  • Y represents -O-, -S-, -C(R 12 )(R 13 )-, -Si(R 14 )(R 15 )-, or -N(R 16 )-;
  • R 9 to R 16 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, or a (5- to 7-membered)heterocycloalkyl fused with at least one substituted or unsubstituted aromatic ring, and R 9 to R 16 may be the same or different; and R 10 and R 11 may be linked to each other to form a mono- or polycyclic, substituted or unsubstituted (C3-C30) alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
  • a, b, and d each independently represent an integer of 1 to 3;
  • c, e, and g each independently represent an integer of 1 to 4.
  • f 1 or 2;
  • each of (Cz-L 1 ), each of (Cz), each of R 1 , each of R 2 , each of R 3 , each of R 4 , or each of R 5 may be the same or different.
  • the specific compounds of which the nitrogen-containing heteroaryl is triazine include the following compounds, but are not limited thereto:
  • the specific compounds of which the nitrogen-containing heteroaryl is pyrimidine include the following compounds, but are not limited thereto:
  • the specific compounds of which the nitrogen-containing heteroaryl is quinoline include the following compounds, but are not limited thereto:
  • the specific compounds of which the nitrogen-containing heteroaryl is quinoxaline include the following compounds, but are not limited thereto:
  • the thickness of the electron buffer layer (126) can be 1 nm or more, but is not limited specifically. In detail, the thickness of the electron buffer layer (126) can be from 2 to 100 nm.
  • the electron buffer layer (126) can be formed on the light-emitting layer (125) in various methods that are known such as vacuum evaporation method, wet film-forming method, laser transfer method, etc.
  • the light-emitting layer comprised in the organic electroluminescent device of the present invention can comprise a host and a dopant.
  • the host compound can be a phosphorescent host compound or a fluorescent host compound.
  • the dopant compound can be a phosphorescent dopant compound or a fluorescent dopant compound.
  • the host compound and the dopant compound can be a fluorescent host compound and a fluorescent dopant compound, respectively.
  • Anthracene derivatives aluminum complexes, rubrene derivatives, arylamine derivatives, etc., can be used as a host material, and preferably, anthracene derivatives.
  • Examples of the host materials of the present invention include the following compounds, but are not limited thereto:
  • Examples of the dopant materials of the present invention include the following compounds, but are not limited thereto:
  • the dopant can be doped in an amount of less than about 25 wt%, preferably less than about 17 wt%, based on the total amount of the dopant and host of the light-emitting layer.
  • the thickness of the light-emitting layer (125) can be from about 5 nm to 100 nm, preferably from about 10 nm to 60 nm.
  • Light emission occurs at the light-emitting layer, and the light-emitting layer can be a mono- or multi-layer.
  • each light-emitting layer can emit different colors of light.
  • a white light-emitting device can be produced by forming three light-emitting layers (125) that emit blue, red, and green, respectively.
  • the light-emitting layer (125) can be formed on the hole transport layer (123) in various methods that are known such as vacuum evaporation method, wet film-forming method, laser transfer method, etc.
  • the organic electroluminescent device of the present invention may additionally comprises a hole injection layer or a hole transport layer between the first electrode and the light-emitting layer.
  • the organic electroluminescent device (100) comprises a substrate (101), a first electrode (110) formed on the substrate (101), an organic layer (120) formed on the first electrode (110), and a second electrode (130) facing the first electrode (110) formed on the organic layer (120).
  • the organic layer (120) comprises a hole injection layer (122), a hole transport layer (123) formed on the hole injection layer (122), a light-emitting layer (125) formed on the hole transport layer (123), an electron buffer layer (126) formed on the light-emitting layer (125), and an electron transport zone (129) formed on the electron buffer layer (126).
  • the electron transport zone (129) comprises an electron transport layer (127) formed on the electron buffer layer (126), and an electron injection layer (128) formed on the electron transport layer (127).
  • the substrate (101) can be a glass substrate, a plastic substrate, or a metal substrate used in a general organic electroluminescent device.
  • the first electrode (110) can be an anode, and can be formed by a material which has high work function.
  • Materials for the first electrode (110) can be indium tin oxide (ITO), tin oxide (TO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), or a mixture thereof.
  • the first electrode (110) can be formed in various methods that are known such as evaporation method, sputtering method, etc.
  • phthalocyanine compounds such as copper phthalocyanine, MTDATA (4,4',4"-tris[(3-methylphenyl)phenylamino]triphenylamine), 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine), N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine), Pani/DBSA (polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS (poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani/CSA (polyaniline/camphorsulfonic acid
  • hole injection layer (122) can be formed by using the following compound of formula 11:
  • R is selected from a group consisting of a cyano (-CN), a nitro (-NO 2 ), phenylsulfonyl (-SO 2 (C 6 H 5 )), a (C2-C5)alkenyl substituted with cyano or nitro, and a phenyl substituted with cyano or nitro.
  • the compound of formula 11 has a characteristic of being crystallized. Accordingly, the hole injection layer (122) can obtain strength by using the compound.
  • the hole injection layer (122) can be a mono- or multi-layer. When the hole injection layer (122) is a multi-layer of two or more layers, the compound of formula 11 can be used in one of them.
  • the thickness of the hole injection layer (122) can be from about 1 nm to about 1,000 nm, preferably from about 5 nm to 100 nm.
  • the hole injection layer (122) can be formed on the first electrode (110) in various methods that are known such as vacuum evaporation method, wet film-forming method, laser transfer method, etc.
  • Examples of the hole injection material comprised in the hole injection layer include the following compounds, but are not limited thereto:
  • Materials used in the hole transport layer (123) can be known hole transport materials.
  • aromatic amine-based derivatives specifically biphenyl diamine-based derivatives such as TPD(N,N'-bis-(3-methylphenyl)-N,N'-diphenylbenzydine), N 4 ,N 4 ,N 4' ,N 4' -tetra([1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine can be used, but are not limited thereto.
  • Examples of the hole transport material comprised in the hole transport layer include the following compounds, but are not limited thereto:
  • the hole transport layer (123) can be a mono- or multi-layer.
  • the thickness of the hole transport layer (123) can be from about 1 nm to about 100 nm, preferably from about 5 nm to 80 nm.
  • the hole transport layer (123) can be formed on the hole injection layer (122) in various methods that are known such as vacuum evaporation method, wet film-forming method, laser transfer method, etc.
  • the lifespan of the device becomes longer due to stabilized hole transport layer even for organic electroluminescent devices comprising an electron buffer layer of which lifespan is relatively short, i.e. upon comparing using a material of which HOMO characteristics and anion stability are improved to using a material of which HOMO characteristics and anion stability are vulnerable for a hole transport material of the hole transport layer, lifespan characteristics can be prevented from being decreased by using a material of which HOMO characteristics and anion stability are improved, due to relatively low deviation of lifespan according to the material groups consisting of the electron buffer layer even for a device comprising an electron buffer layer of which lifespan is relatively short.
  • Materials used in the electron transport layer (127) can be known electron transport materials.
  • electron transport materials For example, oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, anthracene-based compounds, aluminum complexes, gallium complexes, etc., can be used, but are not limited thereto.
  • Examples of the electron transport material comprised in the electron transport layer include the following compounds, but are not limited thereto:
  • the electron transport layer (127) can be a mixed layer comprising an electron transport compound and a reductive dopant.
  • the electron transport compound When formed as a mixed layer, the electron transport compound reduces to an anion so that electrons can be easily injected and transported to a light-emitting medium.
  • the electron transport compound is not specifically limited, and the known electron transport material can be used.
  • the reductive dopant can be alkali metals, alkali metal compounds, alkaline-earth metals, rare earth metals, halides thereof, oxides thereof, and complexes thereof.
  • Specific examples of the reductive dopant include lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li 2 O, BaO, and BaF 2 , but are not limited thereto.
  • the thickness of the electron transport layer (127) can be from about 5 nm to about 100 nm, preferably from about 10 nm to about 60 nm.
  • the electron transport layer (127) can be formed on the electron buffer layer (126) in various methods that are known such as vacuum evaporation method, wet film-forming method, laser transfer method, etc.
  • Materials used in the electron injection layer (128) can be known electron injection materials.
  • lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li 2 O, BaO, BaF 2 , etc. can be used, but are not limited thereto.
  • the thickness of the electron injection layer (128) can be from about 0.1 to about 10 nm, and preferably from about 0.3 nm to about 9 nm.
  • the electron injection layer (128) can be formed on the electron transport layer (127) in various methods that are known such as vacuum evaporation method, wet film-forming method, laser transfer method, etc.
  • Lithium quinoline complex metal can be used as the electron injection material comprised in the electron injection layer. Specifically, it can be exemplified as the following compound, but is not limited thereto.
  • the second electrode (130) can be a cathode, and can be formed by a material which has low work function.
  • Materials for the second electrode (130) can be aluminum (Al), calcium (Ca), magnesium (Mg), silver (Ag), cesium (Cs), lithium (Li), or a combination thereof.
  • the second electrode (130) can be formed in various methods that are known such as evaporation method, sputtering method, etc.
  • the organic electroluminescent device of Figure 1 is only an embodiment to be explained clearly, and the present invention should not be limited to the embodiment but can be varied to another mode.
  • an optional component of the organic electroluminescent device of Figure 1 besides a light-emitting layer and an electron buffer layer can be omitted such as the hole injection layer.
  • an optional component can be further added. Examples of the further added optional component are impurity layers such as n-doping layer and p-doping layer.
  • the organic electroluminescent device can emit light from both sides by placing a light-emitting layer each in both sides in between the impurity layers. The light-emitting layers of both sides can emit different colors.
  • the first electrode can be a transparent electrode and the second electrode can be a reflective electrode so that the organic electroluminescent device can be a bottom emission type
  • the first electrode can be a reflective electrode and the second electrode can be a transparent electrode so that the organic electroluminescent device can be a top emission type
  • a cathode, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode can be sequentially stacked on a substrate to be an inverted organic electroluminescent device.
  • Figure 2 illustrates an energy gap relationship among the layers of the organic electroluminescent device according to one embodiment of the present invention.
  • a hole transport layer (123), a light-emitting layer (125), an electron buffer layer (126), and an electron transport zone (129) are sequentially stacked, and electrons are injected from the cathode to the light-emitting layer (125) through the electron transport zone (129) and the electron buffer layer (126).
  • the LUMO energy level of the electron buffer layer (126) is higher than that of the host compound and the dopant compound of the light-emitting layer (125), and that of the electron transport layer (127). Specifically, LUMO energy levels have the following equational relationship: electron buffer layer > electron transport zone > host compound. According to conventional techniques, the light-emitting area of the light-emitting layer (125) has been shifted to the hole transport layer (123) side due to hole trap and emitted light at the interface.
  • the electron buffer layer (126) has a LUMO energy level as described above to allow an electron trap to occur so that the light-emitting area of the light-emitting layer shifts to the electron transport zone (129) side, thus the lifespan and efficiency of the organic electroluminescent device can be improved.
  • the HOMO energy level of the electron buffer layer (126) is higher than that of the dopant compound of the light-emitting layer (125), but is lower than that of the host compound and the electron transport zone (129).
  • the LUMO energy levels of the present invention can be easily measured by known various methods. Generally, LUMO energy levels are measured by cyclic voltammetry or ultraviolet photoelectron spectroscopy (UPS). Therefore, a person skilled in the art can easily comprehend the electron buffer layer, host material, and electron transport zone that satisfy the equational relationship of the LUMO energy levels of the present invention, and practice the present invention. HOMO energy levels can be easily measured by the same method of measuring LUMO energy levels.
  • the LUMO energy level of the host (Ah) is higher than that of the dopant (Ad).
  • the LUMO energy level of the electron buffer layer (Ab) is higher than that of the host (Ah).
  • the LUMO energy level of the electron buffer layer and the LUMO energy level of the host (Ah) have the following equational relationship:
  • the LUMO energy level of the electron buffer layer (Ab) can be set to have the following equational relationship:
  • the LUMO energy level of the electron buffer layer (Ab) can be set to have the following equational relationship:
  • the LUMO energy level of the electron buffer layer (Ab) can be set to have the following equational relationship:
  • the electron buffer layer can be comprised in organic electroluminescent devices emitting every color including blue, red, and green. Preferably, it can be comprised in an organic electroluminescent device emitting blue light (i.e. the main peak wavelength is from 430 to 470 nm, preferably, in the 450’s nm).
  • Examples 1 to 3 Organic electroluminescent device comprising an electron buffering material comprising a triazine derivative
  • An OLED device of the present invention was produced.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung-Corning) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 4 ,N 4' -diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 40 nm on the ITO substrate.
  • 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole injection layer having a thickness of 5 nm on the hole injection layer.
  • N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 25 nm on the hole injection layer.
  • compound H-1 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-2 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 2 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 20 nm on the hole transport layer.
  • 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell and lithium quinolate was introduced into another cell.
  • the two materials were evaporated at the same rate and deposited in a doping amount of 50 wt% each to form an electron transport layer having a thickness of 27 nm on the light-emitting layer. Thereafter, an electron buffer layer having a thickness of 9 nm was inserted between the light-emitting layer and the electron transport layer. After depositing lithium quinolate 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. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use. The driving voltage based on a luminance of 1,000 nits, luminous efficiency, CIE color coordinate, and lifespan of 10 hours based on a luminance of 2,000 nits and constant-current were measured.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • Comparative Example 1 Organic electroluminescent device not comprising an electron buffering material
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for increasing the thickness of the electron transport layer to 36 nm instead of forming the electron transport layer of 27 nm and the electron buffer layer of 9 nm.
  • the LUMO energy levels of the electron buffer layer are in the mid-1.9’s eV or higher so that the electron injection barrier at the interface between the light-emitting layer and the electron buffer layer is minimized to show fast electron injection characteristics, while showing similar voltage characteristics compared to Comparative Example 1.
  • the LUMO energy levels of Examples 1 and 2 maintain 1.8’s eV and obtained appropriate electron injection characteristics to show high efficiency.
  • the lifespans of Examples 1 to 3 were similar to Comparative Example 1.
  • Examples 4 to 7 Organic electroluminescent device comprising an electron buffering material comprising a triazine derivative
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for using different electron buffering materials.
  • ETL-1 EIL-1(27 )/EIL-1(2)/Al(80)
  • the LUMO energy levels of the electron buffer layer are between the mid- and high 1.9’s eV and 2.0 eV so that the electron injection barrier of the interface between the light-emitting layer and the electron buffer layer affects much, and thus showed slow electron injection characteristics compared to Comparative Example 1.
  • higher voltage characteristics were shown compared to Comparative Example 1. Accordingly, the injected electrons are not relatively sufficient compared to holes, and the possibility of forming excitons is dropped to show lower efficiency compared to Comparative Example 1. However, longer lifespans were shown compared to Comparative Example 1.
  • Examples 8 to 12 Organic electroluminescent device comprising an electron buffering material comprising a triazine derivative
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for using different electron buffering materials.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • the LUMO energy levels of the electron buffer layer are formed at the mid-1.9’s eV, and a specific level of electron injection barrier is applied so that appropriate electron injection characteristics are shown which satisfy both efficiency and lifespan.
  • higher efficiency and longer lifespan were shown compared to Comparative Example 1.
  • excellent lifespan characteristics were shown, i.e. 1.5% or more compared to Comparative Example 1 while showing high efficiency.
  • Examples 13 to 15 Organic electroluminescent device comprising an electron buffering material comprising a pyrimidine derivative
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for using different electron buffering materials.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • the LUMO energy levels of the electron buffer layer are formed in the mid-1.7’s to 1.8’s eV, and the electron injection barrier of the interface between the light-emitting layer and the electron buffer layer decreased compared to triazine derivatives to produce an organic electroluminescent device having fast voltage characteristics and fairly improved efficiency.
  • lifespan was similar or worse compared to Comparative Example 1 and worse than triazine derivatives.
  • Examples 16 to 18 Organic electroluminescent device comprising an electron buffering material comprising a quinazoline or quinoxaline derivative
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for using different electron buffering materials.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • the LUMO energy levels of the electron buffer layer are maintained in the mid-1.9’s to 2.0’s eV.
  • the electron injection ability of the quinazoline and quinoxaline derivatives were dropped drastically compared to triazine or pyrimidine derivatives so that a device having slow voltage characteristics and decreased efficiency was produced.
  • higher lifespan characteristics were shown compared to Comparative Example 1. This is due to interfacial light emission between the electron transport layer and the light-emitting layer being mitigated as a result of the decline of electron injection ability caused by the electron buffer layer.
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for using different electron buffering materials.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • Examples 19 and 20 characteristics of the device were compared according to existence of phenyl between the carbazole derivative and the triazine derivative.
  • the electron injection was disrupted due to increase of the LUMO energy values of Example 19 compared to Example 20 by inserting a phenyl therebetween.
  • high driving voltage and low efficiency were shown, but the lifespan improved.
  • Examples 21 and 22 characteristics of the device were compared according to existence of phenyl between the carbazole derivative and the triazine derivative.
  • the electron injection was disrupted due to increase of the LUMO energy values of Example 21 compared to Example 22 by inserting a phenyl therebetween.
  • high driving voltage and low efficiency were shown, but the lifespan improved.
  • similar tendency was shown regardless of meta or para substitution position of phenyl.
  • higher LUMO energy level difference was shown in Example 22 in which substitution was made at the meta position.
  • An OLED device was produced in the same manner as in Examples 1 to 3, except for using different electron buffering materials.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • triazine and quinazoline derivatives determining the LUMO energy level were compared by identically maintaining the derivative of the HOMO orbital zone for checking the device characteristics according to the derivatives determining the LUMO energy level.
  • Example 24 of a triazine derivative the LUMO energy level increased in that the electron injection was highly disrupted in Example 23 of a quinazoline derivative, and thus showed improved lifespan in spite of high driving voltage and low efficiency.
  • Example 26 of a quinoxaline derivative In contrast to Example 25 of a triazine derivative, the LUMO energy level increased in that the electron injection was highly disrupted in Example 26 of a quinoxaline derivative, and thus showed improved lifespan in spite of high driving voltage and low efficiency.
  • quinazoline and quinoxaline derivatives showed higher x- and y-coordinates compared to triazine derivatives. This is due to the electron injection ability being dropped due to the electron buffer layer, and the HOMO energy level of the electron buffer layer being lower than that of the anthracene host while the light-emitting zone got further from the interface between the electron transport layer and the light-emitting layer so that the excitons were not bounded within the light-emitting layer, and the electron buffer layer contributed to light emission.
  • Example 27 an OLED device comprising an electron buffer layer was produced having the same constitution as in Example 22, except for varying the electron transport layer.
  • Comparative Example 6 and Examples 32 to 35 Organic electroluminescent device comprising a multi-layered hole transport layer and comprising or non-comprising an electron buffer layer
  • Comparative Example 6 an OLED device was produced in the same manner as in Comparative Example 1, except for inserting two separate hole transport layers of 20 nm and 5 nm, respectively, rather than one hole transport layer of 25 nm, and changing the thickness of HI-1 to 60 nm.
  • ETL-1 EIL-1(36)/EIL-1(2)/Al(80)
  • Examples 32 to 35 an OLED device comprising an electron buffer layer was produced having the same constitution as in Comparative Example 6, except for varying the electron buffer layer.
  • Comparative Example 7 and Examples 36 to 39 Organic electroluminescent device comprising a multi-layered hole transport layer and comprising or non-comprising an electron buffer layer
  • Comparative Example 7 an OLED device was produced in the same manner as in Comparative Example 6, except for changing hole transport layer 2 to another derivative.
  • ETL-1 EIL-1(36)/EIL-1(2)/Al(80)
  • an OLED device comprising an electron buffer layer was produced having the same constitution as in Example 32, except for changing the hole transport layer and the electron buffer layer.
  • ETL-1 EIL-1(27)/EIL-1(2)/Al(80)
  • Comparative Examples 8 to 11 and Examples 40 to 43 Organic electroluminescent device comprising various light-emitting materials and comprising or non-comprising an electron buffer layer
  • Comparative Examples 8 to 10 an OLED device was produced in the same manner as in Comparative Example 1, except for varying the host to another derivative.
  • ETL-1 EIL-1(36)/EIL-1(2)/Al(80)
  • Examples 40 to 42 an OLED device was produced in the same manner as in Comparative Example 8, except for shortening the thickness of the electron transport layer to 27 nm, and inserting an electron buffer layer of 9 nm between the light-emitting layer and the electron transport layer.
  • Comparative Example 11 an OLED device was produced in the same manner as in Comparative Example 1, except for changing the blue dopant to compound D-1.
  • ETL-1 EIL-1(36)/EIL-1(2)/Al(80)
  • Example 43 an OLED device was produced in the same manner as in Comparative Example 11, except for shortening the thickness of the electron transport layer to 27 nm, and inserting an electron buffer layer of 9 nm between the light-emitting layer and the electron transport layer.
  • Examples 40 to 42 hosts other than H-1 were used since C-1 material was used for the electron buffer layer which can improve lifespan compared to Comparative Examples 8 to 10. As a result, similar tendency was shown compared to a device not having any electron buffer layer even for other hosts.
  • organic electroluminescent device 101 substrate
  • first electrode 120 organic layer
  • hole injection layer 123 hole transport layer

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Abstract

La présente invention concerne un matériau tampon de confinement d'électrons et un dispositif électroluminescent organique comportant ce matériau dans une couche tampon de confinement d'électrons. On obtient ainsi un dispositif électroluminescent organique aux excellentes caractéristiques en termes rendement lumineux et de durée de vie grâce au matériau tampon de confinement d'électrons selon la présente invention.
PCT/KR2015/002580 2014-03-17 2015-03-17 Matériau tampon de confinement d'électrons et dispositif électroluminescent organique comportant de matériau WO2015142036A1 (fr)

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EP15764173.9A EP3119767B2 (fr) 2014-03-17 2015-03-17 Dispositif électroluminescent organique comportant matériau tampon de confinement d'electrons
US15/125,606 US20170117485A1 (en) 2014-03-17 2015-03-17 Electron buffering material and organic electroluminescent device comprising the same
JP2016555464A JP2017510071A (ja) 2014-03-17 2015-03-17 電子バッファリング材料及びそれを含む有機電界発光デバイス
CN201580012636.0A CN106068267B (zh) 2014-03-17 2015-03-17 电子缓冲材料和包含其的有机电致发光装置
US17/328,729 US11751476B2 (en) 2014-03-17 2021-05-24 Electron buffering material and organic electroluminescent device comprising the same

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