WO2016186321A1 - Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant - Google Patents

Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant Download PDF

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WO2016186321A1
WO2016186321A1 PCT/KR2016/003716 KR2016003716W WO2016186321A1 WO 2016186321 A1 WO2016186321 A1 WO 2016186321A1 KR 2016003716 W KR2016003716 W KR 2016003716W WO 2016186321 A1 WO2016186321 A1 WO 2016186321A1
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substituted
unsubstituted
compound
mmol
alkyl
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PCT/KR2016/003716
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English (en)
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Young-Mook Lim
Su-Hyun Lee
Hyun-Ju Kang
Chi-Sik Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020160002155A external-priority patent/KR20160136211A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to EP16796648.0A priority Critical patent/EP3298016B1/fr
Priority to US15/573,167 priority patent/US20180105740A1/en
Priority to JP2017556856A priority patent/JP2018517679A/ja
Priority to CN201680026289.1A priority patent/CN107531716B/zh
Publication of WO2016186321A1 publication Critical patent/WO2016186321A1/fr
Priority to US17/572,837 priority patent/US20220135875A1/en
Priority to US18/302,882 priority patent/US20230272275A1/en

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Definitions

  • the present invention relates to phosphorous host materials and organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Light-emitting materials are classified into fluorescent, phosphorous, and thermally activated delayed fluorescent (TADF) materials.
  • TADF thermally activated delayed fluorescent
  • electrons and holes injected from electrodes recombine at a light-emitting layer to form an exciton.
  • Light is emitted as the exciton transfers to a ground state.
  • Singlet state excitons and triplet state excitons are formed in a ratio of 1:3.
  • a luminescence from the singlet state to the ground state is called fluorescence and a luminescence from the triplet state to the ground state is called phosphorous.
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green, and blue materials, respectively.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • thermally activated delayed fluorescence in which cross between a force system from a triplet state to a singlet state is possible using thermal energy.
  • KR 1477613 B1 discloses a compound in which pyridine, pyrimidine, or triazine is bonded to a nitrogen atom of carbazole fused with indole, directly or via a linker of phenylene.
  • said reference does not specifically disclose a compound in which pyridine, pyrimidine, or triazine is bonded to a nitrogen atom of carbazole fused with indole, via a linker of pyridylene or pyrimidinylene.
  • KR 1317923 B1 discloses a compound in which pyridine is bonded to a nitrogen atom of carbazole fused with indole, via a linker of pyrimidinylene.
  • said reference does not disclose any example using the compound as a phosphorous host material.
  • the objective of the present invention is first, to provide a phosphorous host material capable of producing an organic electroluminescent device with excellent lifespan characteristics, and second, to provide an organic electroluminescent device comprising the phosphorous host material.
  • a phosphorous host material comprising a compound represented by the following formula 1:
  • Z represents NR 4 , CR 5 R 6 , O, or S;
  • X 1 to X 4 each independently represent N or C(R 7 ), one or more of which are N;
  • Y 1 to Y 3 each independently represent N or C(R 8 ), two or more of which are N;
  • R 1 to R 8 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • a and b each independently represent an integer of 1 to 4;
  • c 1 or 2;
  • each of R 1 , each of R 2 , or each of R 3 may be the same or different;
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having significantly improved operational lifespan can be produced.
  • the present invention relates to a phosphorous host material comprising a compound represented by formula 1, and an organic electroluminescent device comprising the material.
  • the compound represented by formula 1 can be represented by one of the following formulas 2 to 6:
  • R 1 to R 3 , X 1 to X 4 , Z, and a to c are as defined in formula 1.
  • formula 1 in formula 1 can be represented by one of the following formulas 7 to 12:
  • R 1 , R 2 , Z, a, and b are as defined in formula 1.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.;
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms
  • 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.
  • Z represents NR 4 , CR 5 R 6 , O, or S.
  • X 1 to X 4 each independently represent N or C(R 7 ), one or more of which are N.
  • Y 1 to Y 3 each independently represent N or C(R 8 ), two or more of which are N.
  • R 1 to R 8 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)aryl
  • Z represents NR 4 , CR 5 R 6 , O, or S;
  • X 1 to X 4 each independently represent N or C(R 7 ), one or more of which are N;
  • Y 1 to Y 3 each independently represent N or C(R 8 ), two or more of which are N;
  • R 1 to R 8 each independently represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C15)aryl; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono- or polycyclic, (C3-C12) aromatic ring.
  • Z represents NR 4 , CR 5 R 6 , O, or S;
  • X 1 to X 4 each independently represent N or C(R 7 ), one or more of which are N;
  • Y 1 to Y 3 each independently represent N or C(R 8 ), two or more of which are N;
  • R 1 and R 2 each independently represent hydrogen; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, monocyclic (C3-C12) aromatic ring;
  • R 3 to R 6 each independently represent an unsubstituted (C1-C6)alkyl, or a (C6-C15)aryl unsubstituted or substituted with a (C1-C6)alkyl;
  • R 7 and R 8 each independently represent hydrogen.
  • the compound represented by formula 1 includes the following compounds, but is not limited thereto:
  • the compound of formula 1 according to the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, it can be prepared according to the following reaction scheme.
  • R 1 to R 3 , Z, X 1 to X 4 , Y 1 to Y 3 , and a to c are as defined in formula 1, and X represents halogen.
  • the present invention provides a phosphorous host material comprising the compound of formula 1, and an organic electroluminescent device comprising the material.
  • the above material can be comprised of the compound of formula 1 alone, or can further include conventional materials generally used in phosphorous host materials.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic layer may comprise the phosphorous host material of the present invention.
  • the organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the phosphorous host material of the present invention can be comprised in the light-emitting layer.
  • the light-emitting layer can further comprise one or more dopants.
  • another compound can be comprised as a second host material besides the compound of formula 1 (first host material).
  • the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1.
  • the second host material can be any of the known phosphorescent hosts. Specifically, the compound selected from the group consisting of the compounds of formulas 11 to 16 below is preferable in terms of luminous efficiency.
  • A represents -O- or -S-;
  • R 21 to R 24 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted of unsubstituted (C6-C30)aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, or -SiR 25 R 26 R 27 , R 25 to R 27 each independently represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene;
  • M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
  • Y 3 to Y 5 each independently represent CR 34 or N;
  • R 34 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted of unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
  • B 1 and B 2 each independently represent hydrogen, a substituted of unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
  • B 3 represents a substituted of unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 5- to 30-membered heteroaryl;
  • L 5 represents a single bond, a substituted of unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 5- to 30-membered heteroarylene.
  • preferable examples of the second host material are as follows:
  • TPS represents a triphenylsilyl group
  • the dopant used in the present invention is preferably at least one phosphorescent dopant.
  • the dopant materials applied to the organic electroluminescent device according to the present invention are not limited, but may be preferably selected from metallated complex compounds of iridium, osmium, copper, and platinum, more preferably selected from ortho-metallated complex compounds of iridium, osmium, copper, and platinum, and even more preferably ortho-metallated iridium complex compounds.
  • the dopant comprised in the organic electroluminescent device of the present invention is preferably selected from the group consisting of the compounds of formulas 101 to 103 below.
  • 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 cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, 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; and adjacent substituents of R 120 to R 123 may be linked to
  • 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;
  • f and g each independently represent an integer of 1 to 3; where f or g is an integer of 2 or more, each of R 100 may be the same or different; and
  • n an integer of 1 to 3.
  • the phosphorescent dopant compounds include the following:
  • a plurality of host materials is provided.
  • the plurality of host materials may comprise a compound represented by formula 1 and a compound represented by one of formulas 11 to 16.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic layer may comprise the plurality of host materials.
  • composition for preparing an organic electroluminescent device comprises the phosphorous host material of the present invention.
  • the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise the composition for preparing the organic electroluminescent device according to the present invention.
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the phosphorous host material of the present invention, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may further comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device according to the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the phosphorous host material according to the present invention. Also, if necessary, a yellow or orange light-emitting layer can be comprised in the device.
  • a surface layer is preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer.
  • a chalcogenide (including oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant is preferably placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device was produced using the phosphorous host material according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung-Corning, Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (compound HI-1) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a first hole injection layer having a thickness of 5 nm on the ITO substrate.
  • N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine (compound HI-2) was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 95 nm on the first hole injection layer.
  • compound HT-1 N-([1,1'-biphenyl]-4-yl)-N-(4-(9-(dibenzo[b,d]furan-4-yl)-9H-fluoren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine
  • compound HT-1 was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 20 nm on the second hole injection layer. Thereafter, compound C-1 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-74 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 12 wt% (the amount of dopant) based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • 2,4,6-tris(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (compound ET-1) was then introduced into another cell, and deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • Comparative Example 1-1 Production of an OLED device comprising
  • An OLED device was produced in the same manner as in Device Example 1-1, except for using compound A-1 as a host of the light-emitting layer.
  • An OLED device was produced using the phosphorous host material according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec, Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Compound HI-3 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.
  • Compound HT-1 was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer. Thereafter, the first host compound and second host compound of the Device Examples as listed in Table 2 below were introduced into two cells of the vacuum vapor depositing apparatus as hosts, and compound D-74 was introduced into another cell as a dopant.
  • the two host materials were evaporated at the same rate of 1:1, and the dopant material was evaporated at a different rate and were deposited in a doping amount of 10 wt% (the amount of dopant) based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the hole transport layer.
  • Compound ET-2 and compound EI-1 were then introduced into another two cells, evaporated at the rate of 4:6, and deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • All the materials used for producing the OLED device were those purified by vacuum sublimation at 10 -6 torr.
  • Comparative Examples 1-2 to 1-4 Production of an OLED device comprising a conventional phosphorous host material
  • An OLED device was produced in the same manner as in Device Example 1-2, except for using the first and second host compounds of the Comparative Examples as listed in Table 2 below as hosts of the light-emitting layer.
  • the organic electroluminescent device of the present invention has longer lifespan than the conventional devices.
  • An OLED device was produced using the phosphorous host material according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec, Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Compound HI-3 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.
  • Compound HT-3 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 second hole transport layer having a thickness of 60 nm on the first hole transport layer. Thereafter, a host compound as listed in Table 3 below was introduced into one cell of the vacuum vapor depositing apparatus as a host, and a dopant compound as listed in Table 3 below was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 3 wt% (the amount of dopant) based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • Compound ET-2 and compound EI-1 were then introduced into another two cells, evaporated at the rate of 1:1, and deposited to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • an OLED device was produced.
  • a driving voltage and efficiency properties were measured at 1,000 nit of luminance, red light was emitted, and time taken to be reduced from 100% to 97% of the luminance at 5,000 nit and a constant current of OLEDs are shown in Table 3 below.
  • An OLED device was produced in the same manner as in Device Examples 2-1 to 2-6, except for using compound A-2 instead of compound C-1 as a host of the light-emitting layer.
  • a driving voltage and efficiency properties were measured at 1,000 nit of luminance, red light was emitted, and time taken to be reduced from 100% to 97% of the luminance at 5,000 nit and a constant current of OLEDs are shown in Table 3 below.
  • An OLED device was produced using the phosphorous host material according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Geomatec, Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and was then stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Compound HI-3 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.
  • Compound HT-1 was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer. Thereafter, compound B-10 and compound C-71 were introduced into two cells of the vacuum vapor depositing apparatus as hosts, and compound D-102 was introduced into another cell as a dopant.
  • the two host materials were evaporated at the same rate of 1:1, and the dopant material was evaporated at a different rate and were deposited in a doping amount of 10 wt% (the amount of dopant) based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • Compound ET-2 and compound EI-1 were then introduced into another two cells, evaporated at the rate of 4:6, and deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • All the materials used for producing the OLED device were those purified by vacuum sublimation at 10 -6 torr.
  • An OLED device was produced in the same manner as in Device Example 3-1, except for using compound A-3 instead of compound C-71 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Example 3-1, except for using compound C-46 instead of compound C-71 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Example 3-2, except for using compound A-4 instead of compound C-46 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Example 3-1, except for using compound C-84 instead of compound C-71 as a host of the light-emitting layer.
  • An OLED device was produced in the same manner as in Device Example 3-3, except for using compound A-5 instead of compound C-84 as a host of the light-emitting layer.
  • the organic electroluminescent device of the present invention has longer lifespan than conventional devices.

Abstract

L'invention concerne des matériaux hôtes phosphorés et un dispositif électroluminescent organique le comprenant Le fait d'utiliser le matériau hôte phosphoré de la présente invention permet de produire un dispositif électroluminescent organique présentant une durée de vie fonctionnelle améliorée.
PCT/KR2016/003716 2015-05-19 2016-04-08 Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant WO2016186321A1 (fr)

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EP16796648.0A EP3298016B1 (fr) 2015-05-19 2016-04-08 Matériau hôte phosphoré et dispositif électroluminescent organique le comprenant
US15/573,167 US20180105740A1 (en) 2015-05-19 2016-04-08 Phosphorous host material and organic electroluminescent device comprising the same
JP2017556856A JP2018517679A (ja) 2015-05-19 2016-04-08 リンホスト材料及びそれを含む有機電界発光素子
CN201680026289.1A CN107531716B (zh) 2015-05-19 2016-04-08 发磷光的主体材料和包含所述发磷光的主体材料的有机电致发光装置
US17/572,837 US20220135875A1 (en) 2015-05-19 2022-01-11 Phosphorous host material and organic electroluminescent device comprising the same
US18/302,882 US20230272275A1 (en) 2015-05-19 2023-04-19 Phosphorous host material and organic electroluminescent device comprising the same

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KR10-2016-0002155 2016-01-07
KR1020160002155A KR20160136211A (ko) 2015-05-19 2016-01-07 인광 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR1020160034173A KR102638345B1 (ko) 2015-05-19 2016-03-22 인광 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
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CN109326741A (zh) * 2017-08-01 2019-02-12 江苏三月光电科技有限公司 一种含有氮杂苯类化合物的有机发光器件
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