WO2013073896A1 - Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent utilisant lesdits composés - Google Patents

Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent utilisant lesdits composés Download PDF

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WO2013073896A1
WO2013073896A1 PCT/KR2012/009751 KR2012009751W WO2013073896A1 WO 2013073896 A1 WO2013073896 A1 WO 2013073896A1 KR 2012009751 W KR2012009751 W KR 2012009751W WO 2013073896 A1 WO2013073896 A1 WO 2013073896A1
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group
substituted
unsubstituted
alkyl
organic electroluminescent
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Seok-Keun Yoon
Su-Hyun Lee
Kyoung-Jin Park
Seung-Ae Kim
Hyuck-Joo Kwon
Kyung-Joo Lee
Bong-Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201280067085.4A priority Critical patent/CN104039921A/zh
Publication of WO2013073896A1 publication Critical patent/WO2013073896A1/fr

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Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent device using the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices 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 for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • the most important factor determining luminous efficiency in an organic EL device is the light-emitting material.
  • fluorescent materials have been widely used as a light-emitting material.
  • phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, development of phosphorescent light-emitting materials are widely being researched.
  • 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
  • Korean Patent Appln. Laying-Open No. 2010-0056490 discloses organic electroluminescent triphenylene compounds substituted with carbazole, dibenzofuran, dibenzothiophene, etc. However, not disclosed is a compound which is formed by bonding a heteroaryl group to a triphenylene group wherein the heteroaryl group is carbazole fused with a ring such as benzothiophene, indole, indene, benzofuran or silole, etc.
  • the objective of the present invention is to provide an organic electroluminescent compound imparting high luminous efficiency and a long operating lifespan to a device, and having suitable color coordinate; and an organic electroluminescent device having high efficiency and a long lifespan, using said compound as a light-emitting material.
  • L 1 represents a single bond, a substituted or unsubstituted 3- to 30- membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
  • Y 1 and Y 2 each independently represent -O-, -S-, -CR 11 R 12 -, -SiR 13 R 14 - or -NR 15 -, provided that Y 1 and Y 2 do not simultaneously exist;
  • Ar 1 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30- membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted 5- to 7- membered heterocycloalkyl group;
  • R 1 to R 6 , and R 11 to R 15 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30- membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7- membered heterocycloalkyl group, -NR 21 R 22 , -SiR 23 R 24 R 25 , -SR 26 , -OR 27 , a cyano group, a nitro group, or a hydroxyl group;
  • R 21 to R 27 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30- membered heteroaryl group;
  • a, b and c each independently represent an integer of 1 to 4, d and e each independently represent an integer of 1 to 3, and f represents 1 or 2; where a to f are integers of 2 or more, each of R 1 to R 6 is the same or different; and
  • the organic electroluminescent compounds according to the present invention have high luminous efficiency and good lifespan characteristics, and thus could provide an organic electroluminescent device having long operating lifespan.
  • the present invention makes it possible to manufacture a device free from crystallization since the organic electroluminescent compounds used in the present invention are highly efficient in transporting electrons. Further, the compounds have good layer formability and improve the current characteristics of the device. Therefore, it is possible to produce an organic electroluminescent device having lowered driving voltages and enhanced power efficiency.
  • the present invention relates to an organic electroluminescent compound represented by formula 1, above, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
  • 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.
  • Substituents of the substituted groups in L 1 , Ar 1 , R 1 to R 6 , R 11 to R 15 and R 21 to R 27 groups of formula 1, each independently are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group substituted or unsubstituted with a halogen; a (C6-C30)aryl group; a 3- to 30- membered heteroaryl group substituted or unsubstituted with a (C1-C30)alkyl or a (C6-C30)aryl; a (C3-C30)cycloalkyl group; a 5- to 7- membered heterocycloalkyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1
  • L 1 represents a single bond, a substituted or unsubstituted 3- to 30- membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group, preferably a single bond, a substituted or unsubstituted 3- to 20- membered heteroarylene group, or a substituted or unsubstituted (C6-C20)arylene group, more preferably a single bond; a 5- to 12- membered heteroarylene group unsubstituted or substituted with a (C6-C10)aryl group; or a (C6-C18)arylene group unsubstituted or substituted with a (C1-C6)alkyl group or a 5- to 12- membered heteroaryl group.
  • Y 1 and Y 2 each independently represent -O-, -S-, -CR 11 R 12 -, -SiR 13 R 14 - or -NR 15 -, provided that Y 1 and Y 2 do not simultaneously exist.
  • Ar 1 represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30- membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, or a substituted or unsubstituted 5- to 7- membered heterocycloalkyl group, preferably a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 3- to 20- membered heteroaryl group, more preferably a (C6-C18)aryl group unsubstituted or substituted with a (C1-C6)alkyl group or a 5- to 12- membered heteroaryl group; or a 5- to 12- membered heteroaryl group unsubstituted or substitute
  • R 1 to R 6 , and R 11 to R 15 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30- membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7- membered heterocycloalkyl group, -NR 21 R 22 , -SiR 23 R 24 R 25 , -SR 26 , -OR 27 , a cyano group, a nitro group, or a hydroxyl group, preferably hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsub
  • R 21 to R 27 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30- membered heteroaryl group, preferably a substituted or unsubstituted (C6-C20)aryl group, more preferably an unsubstituted (C6-C10)aryl group.
  • L 1 represents a single bond, a substituted or unsubstituted 3- to 20- membered heteroarylene group, or a substituted or unsubstituted (C6-C20)arylene group;
  • Y 1 and Y 2 each independently represent -O-, -S-, -CR 11 R 12 -, -SiR 13 R 14 - or -NR 15 -, provided that Y 1 and Y 2 do not simultaneously exist;
  • Ar 1 represents a substituted or unsubstituted (C6-C20)aryl group, or a substituted or unsubstituted 3- to 20- membered heteroaryl group;
  • R 1 to R 6 , and R 11 to R 15 each independently represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl group, a substituted or unsubstituted (C6-C20)aryl group, a substituted or unsubstituted 3- to 20-
  • L 1 represents a single bond; a 5- to 12- membered heteroarylene group unsubstituted or substituted with a (C6-C10)aryl group; or a (C6-C18)arylene group unsubstituted or substituted with a (C1-C6)alkyl group or a 5- to 12- membered heteroaryl group; Y 1 and Y 2 each independently represent -O-, -S-, -CR 11 R 12 -, -SiR 13 R 14 - or -NR 15 -, provided that Y 1 and Y 2 do not simultaneously exist; Ar 1 represents a (C6-C18)aryl group unsubstituted or substituted with a (C1-C6)alkyl group or a 5- to 12- membered heteroaryl group; or a 5- to 12- membered heteroaryl group unsubstituted or substituted with a (C6-C10)aryl group; R 1 to
  • L 1 represents a single bond, a 3- to 30- membered heteroarylene group, or a (C6-C30)arylene group
  • Y 1 and Y 2 each independently represent -O-, -S-, -CR 11 R 12 -, -SiR 13 R 14 - or -NR 15 -, provided that Y 1 and Y 2 do not simultaneously exist
  • Ar 1 represents a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30- membered heteroaryl group
  • R 1 to R 6 and R 11 to R 15 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30- membered heteroaryl group, -NR 21 R 22 or -SiR 23 R 24 R 25
  • R 21 to R 25 each independently represent a (C1-C30)alkyl group, or a (
  • L 1 represents a single bond, a phenylene, a biphenylene, a terphenylene, an indenylene, a fluorenylene, a triphenylenylene, a pyrenylene, a perylenylene, a fluoranthenylene, a 2,3-dihydro-1H-indenylene, a thiophenylene, a pyrrolylene, a pyrazolylene, a thiazolylene, an oxazolylene, an oxadiazolylene, a triazinylene, a tetrazinylene, a triazolylene, a furazanylene, a pyridylene, a pyrimidylene, a benzofuranylene, a benzothiophenylene, an indolylene, a benzoimidazolylene, a benzothiazolylene, a benzoisothiazolylene,
  • the representative organic electroluminescent compounds of the present invention include the following compounds, but not limited thereto:
  • organic electroluminescent compounds of the present invention can be prepared according to the following reaction schemes.
  • L 1 , Ar 1 , Y 1 , Y 2 , R 1 to R 6 , a, b, c, d, e and f are as defined in formula 1 above, and Hal represents a halogen.
  • the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • the above material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
  • Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes.
  • Said organic layer may comprise at least one organic electroluminescent compound of formula 1 according to the present invention, or an organic electroluminescent material comprising the compound.
  • the organic layer comprises a light-emitting layer, and 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 organic electroluminescent compound according to the present invention can be comprised of in the light-emitting layer. Where used in the light-emitting layer, the organic electroluminescent compound according to the present invention can be comprised as a host material.
  • the light-emitting layer can further comprise at least one dopant and, if needed, another compound as a second host material in addition to the organic electroluminescent compound according to the present invention, wherein the ratio of the organic electroluminescent compound according to the present invention (a first host material) to the second host material can be in the range of 1:99 to 99:1.
  • the second host material can be from any of the known phosphorescent dopants.
  • the phosphorescent dopant selected from the group consisting of the compounds of formula 2 to 6 below is preferable in view of luminous efficiency.
  • X represents O or S
  • R 31 to R 34 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted of unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, or R 35 R 36 R 37 Si-; R 35 to R 37 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group; M represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; Y 3
  • preferable examples of the second host material are as follows:
  • the dopant used in the manufacture of the organic electroluminescent device is preferably one or more phosphorescent dopants.
  • the phosphorescent dopant material applied to the electroluminescent device according to the present invention is not limited, but preferably may be selected from complex compounds of iridium, osmium, copper and platinum; more preferably 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 may be selected from compounds represented by the following formulas 7 to 9.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group
  • R 101 to R 109 , and R 111 to R 123 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl group, a cyano group, or a substituted or unsubstituted (C1-C30)alkoxy group
  • R 120 to R 123 are linked to an adjacent substituent to form a fused ring, e.g.
  • R 124 to R 127 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C6-C30)aryl group; where R 124 to R 127 are aryl groups, adjacent substituents may be linked to each other to form a fused ring, e.g.
  • R 201 to R 211 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a substituted or unsubstituted (C3-C30)cycloalkyl group; o and p each independently represent an integer of 1 to 3; where o or p is an integer of 2 or more, each of R 100 is the same or different; and n is an integer of 1 to 3.
  • the phosphorescent dopant materials include the following:
  • the organic layer of the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may 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 organic electroluminescent compound according to the present invention. Also, if needed, a yellow or orange light-emitting layer can be comprised in the device.
  • At least one layer (hereinafter,“a surface layer”) of the organic electroluminescent device preferably selected from a chalcogenide layer, a metal halide layer and a metal oxide layer; may be placed on an inner surface(s) of one or both electrode(s).
  • 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 placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • 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 an 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; 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, dipping, 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.
  • reaction mixture was extracted with ethylacetate (200 mL), the organic layer was dried with anhydrous MgSO 4 and then filtered. The solvent was removed under reduced pressure, and the remaining product was recrystallized to obtain compound 1-4 (8.5 g, 70 %).
  • reaction mixture was extracted with ethylacetate (100 mL), the organic layer was dried with anhydrous MgSO 4 and then filtered. The solvent was removed under reduced pressure, and the remaining product was recrystallized to obtain compound 1-7 (5.2 g, 74 %).
  • N-bromosuccineimide N-bromosuccineimide
  • DMF dimethylformamide
  • An OLED device was produced using the compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-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 60 nm on the ITO substrate.
  • N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl 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 20 nm on the hole injection layer.
  • compound C-28 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-phenyl-11,12-dihydroindolo[2,3-a] carbazole was introduced into another cell as another host material, and compound D-25 was introduced as a dopant.
  • the two host materials were evaporated at the same rate, 50 wt% respectively, based on the total amount of the host materials, and the dopant was evaporated at different rates and 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 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole was 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%, respectively to form an electron transport layer having a thickness of 30nm on the light-emitting layer. Then, 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 150 nm was 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 produced OLED device showed a green emission having a luminance of 610 cd/m 2 and a current density of 1.22 mA/cm 2 at a driving voltage of 4.2 V.
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound C-47 in place of compound C-28 .
  • the produced OLED device showed a green emission having a luminance of 1,830 cd/m 2 and a current density of 3.71 mA/cm 2 at a driving voltage of 4.96 V.
  • Comparative Example 1 Production of an OLED device using conventional
  • An OLED device was produced in the same manner as in Device Example 1, except that 4,4'-N,N'-dicarbazole-biphenyl was used as a host material and compound D-1 was used as a dopant to deposit a light-emitting layer; and a hole blocking layer having a thickness of 10 nm was deposited between the light-emitting layer and the electron transport layer by using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate.
  • the produced OLED device showed a green emission having a luminance of 1,000 cd/m 2 and a current density of 2.86 mA/cm 2 at a driving voltage of 4.9 V.
  • organic electroluminescent devices using the compounds according to the present invention as a light-emitting host material have superior luminous efficiency and power efficiency over devices using conventional materials.

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Abstract

La présente invention concerne un nouveau composé organique électroluminescent et un dispositif organique électroluminescent contenant ledit composé. En utilisant les composés organiques électroluminescents selon la présente invention, il est possible de fabriquer un dispositif OLED ayant une longue durée de vie de fonctionnement et une efficacité lumineuse élevée. De plus, les composés peuvent améliorer l'efficacité énergétique du dispositif pour réduire la consommation d'énergie globale.
PCT/KR2012/009751 2011-11-16 2012-11-16 Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent utilisant lesdits composés WO2013073896A1 (fr)

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