Patent Application
20250223491
The present disclosure relates to a novel organic compound and an organic electroluminescent device using same. More specifically, the present disclosure relates to a compound with excellent electron transport capability and an organic electroluminescent device that includes the compound in one or more organic layers, thereby exhibiting an improvement in characteristics such as luminous efficiency, driving voltage, and lifespan.
In an organic electroluminescent device (hereinafter referred to as “organic EL device”), when a voltage is applied to two electrodes, holes and electrons are injected from the anode and cathode, respectively, into an organic layer where the injected holes and electrons meet to form an exciton. The exciton falls to the ground state, emitting light. In this regard, the materials used for the organic layer can be classified according to their functions into emission materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials.
The light-emitting layer materials of organic EL devices can be categorized into blue, green, and red emitting materials based on the emission color. Additionally, yellow and orange emitting materials are used to achieve better natural color implementation. To increase color purity and luminous efficiency through energy transfer, host/dopant systems may be employed as an emitting material. Dopant materials can be divided into fluorescent dopants, which use organic substances, and phosphorescent dopants, which use metal complex compounds bearing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency up to four times compared to fluorescence, drawing attention to both phosphorescent dopants and host materials.
To date, NPB, BCP, and Alq3 are widely known for use in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers. Anthracene derivatives have been reported as fluorescent dopant/host materials for emitting materials. Among luminous materials, phosphorescent materials, which have significant advantages in efficiency improvement, include Ir-bearing metal complex compounds such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, used as blue, green, and red dopant materials. Currently, CBP shows excellent characteristics as a phosphorescent host material.
However, existing materials, while advantageous in terms of luminous properties, have low glass transition temperatures and poor thermal stability, leading to unsatisfactory lifespan levels in organic EL devices.
The present disclosure aims to provide a novel organic compound with excellent electron injection and transport capabilities, electrochemical stability, and thermal stability, which can be used as an organic layer material in organic EL devices, specifically as an electron transport layer material or an N-type charge generation layer material.
Additionally, the present disclosure is to provide an organic EL device that includes the aforementioned novel organic compound and exhibits low driving voltage, high luminous efficiency, and improved lifespan.
To achieve the goals, the present disclosure provides an organic compound represented by the following Chemical Formula 1:
Also, the present disclosure provides an organic EL device including: an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes the organic compound described above. In this regard, the organic layer including the compound may be an electron transport layer.
Furthermore, the present disclosure provides an organic EL device including: an anode and a cathode spaced apart from each other; a plurality of lighting units interposed between the anode and the cathode; and an N-type charge generation layer and a P-type charge generation layer interposed between adjacent light units, wherein each light unit includes a hole transport layer, a light-emitting layer, and an electron transport layer, and the N-type charge generation includes the compound described above.
With excellent electron transport ability, luminescent ability, electrochemical stability, and thermal stability, the compound of the present disclosure can be used as a material for an organic layer in organic EL devices. Particularly, when used as material for at least one of an electron transport layer, an electron transport auxiliary layer, and an N-type charge generation layer, the compound of the present disclosure allows for the fabrication of organic EL with superior luminous performance, low driving voltage, high efficiency, and long lifespan compared to conventional materials, and makes it possible to manufacture full-color display panels with improved performance and lifespan.
Below, a detailed description will be given of the present disclosure.
The compound according to the present disclosure has the basic structure in which a phenanthridine moiety has a pyridine moiety bonded to the carbon at position 5 thereof, with various substituents (particularly, EWG), such as aryl, heteroaryl, etc., linked to the pyridine moiety, as illustrated in Chemical Formula 1. With excellent electron injection and transport capabilities, electrochemical stability, and thermal stability, the novel compound of Chemical Formula 1 according to the present disclosure can be used as a material for an electron transport layer, an electron transport auxiliary layer, or an N-type charge generation layer in organic EL devices, whereby an improvement can be brought about in luminous efficiency, lifespan, driving voltage, and progressive driving voltage characteristics in the organic EL devices. The carbon/nitrogen position numbers in the phenanthridine moiety can be represented as follows.
Specifically, the compound represented by Chemical Formula 1 has a pyridine moiety bonded to the carbon at position 5 of the phenanthridine moiety. In this case, the binding position of the pyridine moiety to the phenanthridine moiety is the ortho position of the nitrogen (N). The compound of the present disclosure with such a structure can bind to metals. Consequently, the compound of the present disclosure can form a gap state by binding with metals such as alkali metals and alkaline earth metals, which are dopants in the N-type charge generation layer. When used as an N-type charge generation layer material, the compound of the present disclosure improves properties of the electron transfer from an N-type charge generation layer to an electron transport layer. Additionally, when used as an N-type charge generation layer material, the compound of the present disclosure binds with alkali metals or alkaline earth metals in the N-type charge generation layer, preventing the alkali metal or alkaline earth metal from diffusing into the p-type charge generation layer. Therefore, using the compound of the present disclosure as an N-type charge generation layer material can improve the performance and lifespan of organic EL devices.
As mentioned in the foregoing, the compound represented by Chemical Formula 1 in the present disclosure exhibits excellent electron injection and transport capabilities. Therefore, the compound of the present disclosure may be used as a material for an organic layer material in organic EL devices, preferably as a material for an electron transport layer material. Furthermore, the compound of the present disclosure may be used as a material for an N-type charge generation layer material in tandem-structured organic EL devices. Applying the compound represented by Chemical Formula 1 as an electron transport layer material or an n-type charge generation layer material in organic EL devices can improve characteristics such as driving voltage, luminous efficiency, and lifespan, as well as prevent the increase of progressive driving voltage. Moreover, the compound can maximize the performance of full-color organic light-emitting panels to which the organic EL devices are applied.
In the compound represented by Chemical Formula 1, n may be an integer of 0 to 3 and particularly an integer of 0 to 2.
Here, when n is 0, L1 is meant to be a direct bond (single bond). When n is an integer of 1 to 3, Li is a divalent linker and may be selected from the group consisting of an arylene of C6-C30 and a heteroarylene of 5 to 30 nuclear atoms, and specifically from the group consisting of an arylene of C6-C18 and a heteroarylene of 5 to 18 nuclear atoms. Here, the plurality of Li may be same or different.
The arylene and heteroarylene groups for Li may each be unsubstituted or substituted with a substituent selected from the group consisting of a deuterium atom, a halogen, a cyano, a nitro, an alkenyl of C2-C40, an alkynyl of C2-C40, a cycloalkyl of C3-C40, a heterocycloalkyl of 3 to 40 nuclear atoms, an alkyl of C1-C40, an aryl of C6-C60, a heteroaryl of 5 to 60 nuclear atoms, an alkyloxy of C1-C40, an aryloxy of C6-C60, an alkylsilyl of C1-C40, an arylsilyl of C6-C60, an alkylboron of C1-C40, an arylboron of C6-C60, an arylphosphine of C6-C60, an arylphosphine oxide of C6-C60, and an arylamine of C6-C60, and specifically from the group consisting of a deuterium atom, a halogen, a cyano, a nitro, an alkyl of C1-C40, an alkenyl of C2-C40, an alkynyl of C2-C40, a cycloalkyl of C3-C40, a heterocycloalkyl of 3 to 40 nuclear atoms, an aryl of C6-C60, and a heteroaryl of 5 to 60 nuclear atoms. In this regard, if present, two or more substituents may be same or different.
According to an embodiment,
may be a linker represented by the following Chemical Formulas L1 to L5:
According to an embodiment, Li may be a direct bond or any one of the following linkers L-1 to L-51:
Depending on the bonding position of Li, the compound represented by Chemical Formula 1 may be compounds represented by the following Chemical Formulas 2 to 5, but with no limitations thereto:
In the compound represented by Chemical Formula 1, Ari may be selected from the group consisting of a hydrogen atom, a deuterium atom (D), a halogen, a cyano, a nitro, an amino, an alkyl of C1-C40, an alkenyl of C2-C40, an alkynyl of C2-C40, a cycloalkyl of C3-C40, a heterocycloalkyl of 3 to 40 nuclear atoms, an aryl of C6-C60, a heteroaryl of 5 to 60 nuclear atoms, an alkyloxy of C1-C40, an aryloxy of C6-C60, an alkylsilyl of C1-C40, an arylsilyl of C6-C60, an alkylboron of C1-C40, an arylboron of C6-C60, an arylphosphine of C6-C60, an arylphosphine oxide of C6-C60, an arylamine of C6-C60, and an aryl of C6-C60 substituted with an alkenyl of C2-C40, or may bond to an adjacent group (e.g., Ar1-L1) to form a fused ring. Specifically, Ar may be selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen, a cyano, a nitro, an alkyl of C1-C40, an alkenyl of C2-C40, an alkynyl of C2-C40, a cycloalkyl of C3-C40, a heterocycloalkyl of 3 to 40 nuclear atoms, an aryl of C6-C60, a heteroaryl of 5 to 60 nuclear atoms, and an aryl of C6-C60 substituted with an alkenyl of C2-C40, or may bond to an adjacent group (e.g., Ar1-L1) to form a fused ring. More specifically, Ar1 may be selected from the group consisting of a deuterium atom, a cyano, an alkyl of C1-C20, a cycloalkyl of C3-C20, a heterocyclic alkyl of 3 to 20 nuclear atoms, an aryl of C6-C30, a heteroaryl of 5 to 30 nuclear atoms, and an aryl of C6-C30 substituted with an alkenyl of C2-C20, or may bond to an adjacent group (e.g., Ar1-L1) to form a fused ring. Here, the fused ring may be at least one selected from the group consisting of a fused aliphatic ring of C3-C60 (specifically, fused aliphatic ring of C3-C30), a fused aromatic ring of C6-C60 (specifically, fused aromatic ring of C6-C30), a 5- to 60-membered, fused heteroaromatic ring containing one or more heteroatoms (e.g., N, O, S, Se, etc.) (specifically, 5- to 30-membered fused heteroaromatic ring containing one or more heteroatoms), a spiro ring of C3-C60, and a combination thereof.
According to an embodiment, Ar1 may be a substituent represented by any one selected from the group consisting of the following Chemical Formulas S1 to S12, but is not limited thereto. Particularly, when Ar is an electron withdrawing group (EWG) having high electronic affinity (electron absorptivity) such as the following 51, S2, etc., the compound of the present disclosure may be used as an electron transport layer material because the LUMO level may be adjusted similarly to other electron transport layer materials. Also, when the compound of the present disclosure, in which Ar is an EWG, is used as the N-type charge generation layer material, a reduction can be made a difference in LUMO level from adjacent electron transport layer, thus greatly improving the performance of the organic EL device:
Specifically, the substituent represented by Chemical Formula S1 may be a substituent represented by any one of the following Chemical Formulas Si-A to S1-D, but with no limitations thereto:
In addition, the compound represented by Chemical Formula S2 may be a substituent represented by the following Chemical formula S2-A:
In another embodiment, the Ar may be a substituent selected from the group consisting of the following substituents S2-1 to S2-68, but with no limitations thereto:
Depending on L1 and Ar1 defined above, the compound represented by Chemical Formula 1 may be a compound represented by any one of Chemical Formula 5 to 17, but with no limitations thereto:
Concrete examples of the compound represented by Chemical Formula 1 according to the present disclosure include, but are not limited to, the following Compounds A-1 to C-126:
As used herein, the term “alkyl” refers to a monovalent substituent derived from a saturated, linear or branched hydrocarbon of 1 to 40 carbon atoms. Examples of such alkyl may include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl or the like.
As used herein, the term “alkenyl” refers to a monovalent substituent derived from an unsaturated, linear or branched hydrocarbon of 2 to 40 carbon atoms with at least one carbon-carbon double bond therein. Examples of such alkenyl may include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl or the like.
As used herein, the term “alkynyl” refers to a monovalent substituent derived from an unsaturated, linear or branched hydrocarbon of 2 to 40 carbon atoms, with at least one carbon-carbon triple bond therein. Examples of such alkynyl may include, but are not limited to, ethynyl, 2-propynyl or the like.
As used herein, the term “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon of 3 to 40 carbon atoms. Examples of such cycloalkyl may include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine or the like.
As used herein, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon of 3 to 40 nuclear atoms, of which one or more carbons on the ring, preferably 1 to 3 carbons, are substituted with a heteroatom, such as N, O, Se, or S. Examples of the heterocycloalkyl may include morpholine, piperazine, and the like, but are not limited thereto.
As used herein, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon of 6 to 60 carbon atoms having a single ring or a combination of two or more rings. In addition, the two or more rings may be simply attached (pendant) or fused. Examples of such aryl may include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl or the like.
The term “heteroaryl”, as used herein, refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon of 5 to 60 nuclear atoms. In this regard, the substituent bears one or more and preferably one to three heteroatoms such as N, O, S, or Se as ring members. In addition, two or more rings may be simply attached (pendant) or fused to each other and may be in a form fused to an aryl group. Examples of such heteroaryl may include, but are not limited to, a 6-membered monocyclic ring such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; and a polycyclic ring such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole and carbazolyl; 2-furanyl; N-imidazolyl; 2-isoxazolyl; 2-pyridinyl; 2-pyrimidinyl or the like.
As used herein, the term “alkyloxy” refers to a monovalent substituent represented by R′O—, where R′ is an alkyl of 1 to 40 carbon atoms. Such alkyloxy may include a linear, branched or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy or the like.
The term “aryloxy”, as used herein, refers to a monovalent substituent represented by RO—, where R is an aryl of 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy or the like.
The term “alkylsilyl”, as used herein, refers to a silyl substituted with an alkyl of 1 to 40 carbon atoms and is intended to encompass di- and tri-alkylsilyl as well as mono-alkylsilyl. In addition, “arylsilyl” refers to a silyl substituted with an aryl of 5 to 60 carbon atoms and is intended to encompass a poly-arylsilyl such as di- and tri-arylsilyl as well as mono-arylsilyl.
As used herein, the term “alkylboron group” refers to a boron substituted with an alkyl of 1 to 40 carbon atoms, and the term “arylboron group” refers to a boron substituted with aryl of 6 to 60 carbon atoms.
As used herein, the term “alkylphosphinyl” refers to a phosphine substituted with an alkyl of 1 to 40 carbon atoms and is intended to encompass a di-alkylphosphinyl group as well as a mono-alkylphosphinyl group. As used herein, “arylphosphinyl group” refers to a phosphine substituted with a mono- or diaryl of 6 to 60 carbon atoms, and is intended to encompass a di-arylphosphinyl as well as a mono-arylphosphinyl.
As used herein, the term “arylamine” refers to an amine substituted with an aryl of 6 to 60 carbon atoms and is intended to encompass mono- and diarylamine.
The term “heteroarylamine”, as used herein, refers to an amine substituted with a heteroaryl of 5 to 60 nuclear atoms and is indented to encompass mono- and diheteroarylamine.
The term “(aryl) (heteroaryl)amine”, as used herein, refers to an amine substituted with an aryl of 6 to 60 carbon atom and a heteroaryl of 5 to 60 nuclear atoms.
As used herein, the term “fused ring” refers to a fused aliphatic ring of 3 to 40 carbon atoms, a fused aromatic ring of 6 to 60 carbon atoms, a fused heteroaliphatic ring of 3 to 60 nuclear atoms, a fused heteroaromatic ring of 5 to 60 nuclear atoms, or a combination thereof.
The present disclosure provides an organic electroluminescence device (hereinafter referred to as “organic EL device”) comprising the compound represented by Chemical Formula 1.
Hereinafter, the organic EL devices according to the first to third embodiments of the present disclosure will be explained in detail with reference to
As shown in
The one or more organic layers (300) may include any one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport auxiliary layer (360), an electron transport layer (340), and an electron injection layer (350), wherein at least one organic layer (300) contains the compound represented by Chemical Formula 1. Specifically, the organic layer containing the compound represented by Chemical Formula 1 may be an electron transport layer (340). That is, the compound represented by Chemical Formula 1 is included as an electron transport layer material in the organic EL device. In such an organic EL device, electrons are easily injected from the cathode or electron injection layer into the electron transport layer due to the compound of Chemical Formula 1 and can also quickly move from the electron transport layer to the light-emitting layer, resulting in a high binding force of holes and electrons in the light-emitting layer. Therefore, the organic EL device of the present disclosure exhibits excellent luminous efficiency, power efficiency, and brightness. Moreover, the compound of Chemical Formula 1 has excellent thermal and electrochemical stability, thereby improving the performance of the organic EL device.
The compound of Chemical Formula 1 can be used alone or in combination with an electron transport layer material known in the art.
The electron transport layer materials that can be mixed with the compound of Chemical Formula 1 include commonly known electron transport materials in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3, tris(8-quinolinolato)aluminum), gallium complexes (e.g., Gaq′2OPiv, Gaq′2OAc, 2(Gaq′2)), and others. These may be used alone or in combination.
In the present disclosure, when mixing the compound of Chemical Formula 1 with electron transport layer materials, the mixing ratio is not particularly limited and can be appropriately adjusted within the known range in the art.
The structure of the organic EL device of the present disclosure is not particularly limited, but for example, the anode (100), one or more organic layers (300), and the cathode (200) may be sequentially laminated on a substrate (see
In an embodiment, as shown in
The organic EL device of the present disclosure may be manufactured by forming the organic layer and electrode using known materials and methods in the art, except that at least one of the organic layers (e.g., the electron transport layer (340)) includes the compound represented by Chemical Formula 1.
The organic layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
The substrate usable in the present disclosure is not particularly limited and may include, for example, silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.
Examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.
Examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, lead, and alloys thereof; and multilayer structures such as LiF/Al or LiO2/Al, but are not limited thereto.
Furthermore, the hole injection layer, hole transport layer, light-emitting layer, and electron injection layer are not particularly limited and may employ conventional materials known in the art.
Hereinafter, the organic EL device according to the fourth embodiment of the present disclosure will be described with reference to
As shown in
This tandem-type organic EL device has at least two lighting units, and the number of lighting units may be increased by interposing the charge generation layer between adjacent lighting units.
By way of example, a plurality of lighting units may include a first lighting unit (400), a second lighting unit (500), . . . , and an m-th lighting unit (m=an integer of 3 or more, specifically 3-4). In this regard, a charge generation layer (600) including an N-type charge generation layer (610) and a P-type charge generation layer (620) is disposed between adjacent lighting units, and the N-type charge generation layer (610) includes the compound represented by Chemical Formula 1.
Specifically, the organic EL device according to the present disclosure includes: an anode (100) and a cathode (200) facing each other; a first lighting unit (400) disposed on the anode (100); a second lighting unit (500) disposed on the first lighting unit (400); and a charge generation layer (600) interposed between the first and second lighting units (400, 500) and including an N-type charge generation layer (610) and a P-type charge generation layer (620). In this regard, the N-type charge generation layer (610) contains the compound represented by Chemical Formula 1.
Each lighting unit (400, 500) includes a hole transport layer (410, 510), a light-emitting layer (420, 520), and an electron transport layer (430, 530). Specifically, the first lighting unit (400) includes a first hole transport layer (410), a first light-emitting layer (420), and a first electron transport layer (430), and the second lighting unit (500) includes a hole transport layer (510), a light-emitting layer (520), and an electron transport layer (530). Optionally, the first lighting unit (400) may additionally include a hole injection layer (440).
The hole transport layer (410, 510), light-emitting layer (420, 520), electron transport layer (430, 530), and hole injection layer (440) are not particularly limited and may employ conventional materials known in the art.
The charge generation layer (600) is disposed between the adjacent lighting units (400, 500), adjusting the charge between the lighting units (400, 500) to achieve charge balance.
The charge generation layer (600) includes: an N-type charge generation layer (610) located adjacent to the first lighting unit (400) and supplying electrons to the first lighting unit (400); and a P-type charge generation layer (620) located adjacent to the second lighting unit (500) and supplying holes to the second lighting unit (500).
The N-type charge generation layer (610) includes the compound represented by Chemical Formula 1. The compound of Chemical Formula 1 has excellent electron mobility and superior electron injection and transport capabilities. Therefore, when applied as an N-type charge generation layer material in an organic EL device, the compound of Chemical Formula 1 can prevent the increase in progressive driving voltage and the degradation of lifespan.
According to an embodiment, the N-type charge generation layer (610) includes a host with electron transport properties, wherein the host is the compound represented by Chemical Formula 1.
The N-type charge generation layer (610) may further include an N-type dopant.
So long as it is generally used in N-type charge generation layers, any N-type dopant is usable in the present disclosure without particular limitations thereto. For example, alkali metals such as Li, Na, K, Rb, Cs, and Fr; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, and Ra; lanthanide metals such as La (lanthanum), Ce (cerium), Pr (preseodyminum), Nd (neodymium), Pm (promethium), Sm (samarium), europium (europium), Gd (gadolinium), Tb (terbium), Dy (dysprosium), Ho (holmium), Er (erbium), Tm (thulium), Yb (ytterbium), and Lu (lutetium); and compounds of one or more of these metals may be used. Additionally, the N-type dopant may be an organic N-type dopant with electron donor properties that can donate at least a part of its electron charge to the organic host (e.g., the compound of Chemical Formula 1) to form a charge-transfer complex with the organic host, such as bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) and tetrathiafulvalene (TTF).
The thickness of the N-type charge generation layer (610) is not particularly limited and may be in the range of about 5 to 30 nm, for example.
The p-type charge generation layer (620) may be made of a metal or a p-type doped organic material. Examples of the metal include Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti, which may be used alone or as alloys of two or more. Additionally, the materials for the p-type dopant and host used in the p-type doped organic material are not particularly limited as long as they are commonly used materials. For example, the p-type dopant may be F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), iodine, FeCl3, FeF3, and SbCl5, which may be used alone or in combination of two or more. Non-limiting examples of the host include NPB (N,N′-bis(naphthalen-1-yl)-N,N′-bis (phenyl)-benzidine), TPD (N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)-benzidine), and TNB (N,N,N′,N′-tetranaphthalenyl-benzidine), which may be used alone or in combination of two or more.
The description of the substrate (not shown), anode (100), cathode (200), hole injection layer, hole transport layer, light-emitting layer, and electron injection layer is the same as described in the sections of the first to third embodiments above and thus is omitted here.
A better understanding of the present disclosure may be obtained through the following examples which are set forth to illustrate, but are not to be construed to limit, the present disclosure.
6-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenanthridine (7 g, 18.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.3 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (7.6 g, 54.9 mmol) in a mixture of toluene (50 ml), EtOH (10 ml) and H2O (10 ml) were heated for 12 hour under reflux. After completion of the reaction, the reaction mixture was subjected to extraction with methylene chloride. The organic layer thus obtained was added with MgSO4 and filtered. The solvent was removed from the filtered organic layer, followed by column chromatography to afford the title compound (7.8 g, yield 87).
[LCMS]: 488
The same procedure as in Synthesis Example 1 with the exception of using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.6 g, yield 83%)
[LCMS]: 564
The same procedure as in Synthesis Example 1 with the exception of using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.7 g, yield 86%)
[LCMS]: 487
The same procedure as in Synthesis Example 1 with the exception of using 4-(4-bromophenyl)-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.6 g, yield 83%)
[LCMS]: 563
The same procedure as in Synthesis Example 1 with the exception of using 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 82%).
[LCMS]: 564
The same procedure as in Synthesis Example with the exception of using 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.6 g, yield 83%).
[LCMS]: 563
The same procedure as in Synthesis Example 1 with the exception of using 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 82%).
[LCMS]: 564
The same procedure as in Synthesis Example 1 with the exception of using 2chloro-4phenyl-6(4-(pyridin-3-yl)phenyl)-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3.5-triazine was carried out to afford the title compound (8.3 g, yield 80%)
[LCMS]: 565
The same procedure as in Synthesis Example 1 with the exception of using 2-(5-bromopyridin-2-yl)-4.6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.0 g, yield 77%).
[LCMS]:565
The same procedure as in Synthesis Example 1 with the exception of using 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.0 g, yield 77%)
[LCMS]: 565
The same procedure as in Synthesis Example 1 with the exception of using 4-(4-bromopyridin-2-yl)-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.9 g, yield 76%).
[LCMS]: 564
The same procedure as in Synthesis Example 1 with the exception of using 4-([1,1′-biphenyl]-4-yl)-6-(5-bromopyridin-2-yl)-2-phenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.0 g, yield 76%).
[LCMS]: 640
The same procedure as in Synthesis Example 1 with the exception of using 4-chloro-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.6 g, yield 80%).
[LCMS]: 517
The same procedure as in Synthesis Example 1 with the exception of using 4-(3-bromophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.6 g, yield 79%).
[LCMS]: 593
The same procedure as in Synthesis Example 1 with the exception of using 4-chloro-2-phenylbenzofuro[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.5 g, yield 82%)
[LCMS]: 501
The same procedure as in Synthesis Example 1 with the exception of using 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.8 g, yield 82%).
[LCMS]: 517
The same procedure as in Synthesis Example 1 with the exception of using 2-(4-bromophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.6 g, yield 79%).
[LCMS]: 593
The same procedure as in Synthesis Example 1 with the exception of using 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.6 g, yield 79%)
[LCMS]: 526
The same procedure as in Synthesis Example 1 with the exception of using 2-chloro-3,5,6-triphenylpyrazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.0 g, yield 77%)
[LCMS]: 563
The same procedure as in Synthesis Example 1 with the exception of using 2-(3-bromophenyl)-3,5,6-triphenylpyrazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.2 g, yield 78%)
[LCMS]: 639
The same procedure as in Synthesis Example 1 with the exception of using 2-chloro-4-phenylquinazoline instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.7 g, yield 79%)
[LCMS]: 461
The same procedure as in Synthesis Example 1 with the exception of using 4′-chloro-3,2′:6′,3″-terpyridine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.0 g, yield 78%)
[LCMS]: 488
The same procedure as in Synthesis Example 1 with the exception of using 4-bromodibenzo[b,d]furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.3 g, yield 81%)
[LCMS]: 423
A-81
The same procedure as in Synthesis Example 1 with the exception of using 3-bromodibenzo[b,d]furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.3 g, yield 81%)
[LCMS]: 423
The same procedure as in Synthesis Example 1 with the exception of using 9-bromonaphtho[2,1-b]benzofuran instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.7 g, yield 77%)
[LCMS]: 473
The same procedure as in Synthesis Example 1 with the exception of using 8-bromobenzo[b]naphtho[1,2-d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.9 g, yield 77%)
[LCMS]: 489
The same procedure as in Synthesis Example 1 with the exception of using 3-bromodibenzo[b,d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.4 g, yield 80%)
[LCMS]: 439
The same procedure as in Synthesis Example 1 with the exception of using 2-(4-bromophenyl)naphthalene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.7 g, yield 80%)
[LCMS]: 459
The same procedure as in Synthesis Example 1 with the exception of using 1-bromo-4-phenylnaphthalene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.6 g, yield 78%).
[LCMS]: 459
The same procedure as in Synthesis Example 1 with the exception of using 9-bromo-10-phenylanthracene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.9 g, yield 74%).
[LCMS]: 509
The same procedure as in Synthesis Example 1 with the exception of using 2-bromo-9,10-di(naphthalen-2-yl)anthracene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.3 g, yield 74%)
[LCMS]: 685
The same procedure as in Synthesis Example 1 with the exception of using 5′-bromo-1,1′:3′,1″-terphenyl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.8 g, yield 76%).
[LCMS]: 485
The same procedure as in Synthesis Example 1 with the exception of using 9-bromophenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.0 g, yield 76%).
[LCMS]: 433
The same procedure as in Synthesis Example 1 with the exception of using 9-(3-bromophenyl)phenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.0 g, yield 75%)
[LCMS]: 509
The same procedure as in Synthesis Example 1 with the exception of using 2-bromophenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.0 g, yield 76%).
[LCMS]: 433
The same procedure as in Synthesis Example 1 with the exception of using 2-bromotriphenylene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.3 g, yield 71%).
[LCMS]: 483
The same procedure as in Synthesis Example 1 with the exception of using 2-bromopyrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.1 g, yield 73%).
[LCMS]: 457
The same procedure as in Synthesis Example 1 with the exception of using 1-bromopyrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.1 g, yield 73%).
[LCMS]: 457
The same procedure as in Synthesis Example 1 with the exception of using 4-bromo-2,9-dimethyl-1,10-phenanthroline instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.1 g, yield 72%)
[LCMS]: 463
6-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenanthridine (7 g, 18.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.3 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (7.6 g, 54.9 mmol) in a mixture of toluene (50 ml), EtOH (10 ml), and H2O (10 ml) were heated for 12 hour under reflux. After completion of the reaction, the reaction mixture was subjected to extraction with methylene chloride. The organic layer thus obtained was added with MgSO4 and filtered. The solvent was removed from the filtered organic layer, followed by column chromatography to afford the title compound (7.7 g, yield 86%).
[LCMS]: 488
The same procedure as in Synthesis Example 40 with the exception of using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 82%)
[LCMS]: 564
The same procedure as in Synthesis Example 40 with the exception of using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.6 g, yield 85%).
[LCMS]: 487
The same procedure as in Synthesis Example 40 with the exception of using 4-(4-bromophenyl)-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 82%)
[LCMS]: 563
The same procedure as in Synthesis Example 40 with the exception of using 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.4 g, yield 81%).
[LCMS]: 564
The same procedure as in Synthesis Example 40 with the exception of using 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 82%).
[LCMS]: 563
The same procedure as in Synthesis Example 40 with the exception of using 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.4 g, yield 81%).
[LCMS]: 564
The same procedure as in Synthesis Example 40 with the exception of using 2-chloro-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.2 g, yield 79%).
[LCMS]: 565
The same procedure as in Synthesis Example 40 with the exception of using 2-(5-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.9 g, yield 76%)
[LCMS]: 565
The same procedure as in Synthesis Example 40 with the exception of using 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.9 g, yield 76%)
[LCMS]:565
The same procedure as in Synthesis Example 40 with the exception of using 4-(4-bromopyridin-2-yl)-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.8 g, yield 75%).
[LCMS]: 564
The same procedure as in Synthesis Example 40 with the exception of using 4-([1,1′-biphenyl]-4-yl)-6-(5-bromopyridin-2-yl)-2-phenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.9 g, yield 75%).
[LCMS]: 640
The same procedure as in Synthesis Example 40 with the exception of using 4-chloro-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.5 g, yield 79%).
[LCMS]: 517
The same procedure as in Synthesis Example 40 with the exception of using 4-(3-bromophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 78%).
[LCMS]: 593
The same procedure as in Synthesis Example 40 with the exception of using 4-chloro-2-phenylbenzofuro[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.4 g, yield 81%)
[LCMS]: 501
The same procedure as in Synthesis Example 40 with the exception of using 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.7 g, yield 81%).
[LCMS]: 517
The same procedure as in Synthesis Example 40 with the exception of using 2-(4-bromophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.5 g, yield 78 %).
[LCMS]: 593
The same procedure as in Synthesis Example 40 with the excdeption of using 2-bromo-6,8diphenyl-[1,2,4]triazolo [1,5-a]pyridine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.5 g, yield 78%).
[LCMS]:526
The same procedure as in Synthesis Example 40 with the exception of using 2-chloro-3,5,6-triphenylpyrazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.9 g, yield 76%).
[LCMS]: 563
The same procedure as in Synthesis Example 40 with the exception of using 2-(3-bromophenyl)-3,5, 6-triphenylpyrazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.1 g, yield 77%)
[LCMS]: 639
The same procedure as in Synthesis Example 40 with the exception of using 2-chloro-4-phenylquinazoline instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.6 g, yield 78%).
[LCMS]: 461
The same procedure as in Synthesis Example 40 with the exception of using 4-bromodibenzo[b,d]furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.2 g, yield 80%)
[LCMS]: 423
The same procedure as in Synthesis Example 40 with the exception of using 3-bromodibenzo[b,d]furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.2 g, yield 80%).
[LCMS]: 423
The same procedure as in Synthesis Example 40 with the exception of using 9-bromonaphtho[2,1-b]benzofuran instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.6 g, yield 76%).
[LCMS]: 473
The same procedure as in Synthesis Example 40 with the exception of using 8-bromobenzo[b]naphtho[1,2-d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.8 g, yield 76%)
[LCMS]: 489
The same procedure as in Synthesis Example 40 with the exception of using 3-bromodibenzo[b,d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.3 g, yield 79%)
[LCMS]: 439
The same procedure as in Synthesis Example 40 with the exception of using 2-(4-bromophenyl)naphthalene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.6 g, yield 79%).
[LCMS]: 459
The same procedure as in Synthesis Example 40 with the exception of using 1-bromo-4-phenylnaphthalene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.5 g, yield 77%)
[LCMS]: 459
The same procedure as in Synthesis Example 40 with the exception of using 9-bromo-10-phenylanthracene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.8 g, yield 73%)
[LCMS]: 509
The same procedure as in Synthesis Example 40 with the exception of using 2-bromo-9,10-di(naphthalen-2-yl)anthracene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.2 g, yield 73%)
[LCMS]: 685
The same procedure as in Synthesis Example 40 with the exception of using 5′-bromo-1,1′:3′,1″-terphenyl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.7 g, yield 75%)
[LCMS]: 485
The same procedure as in Synthesis Example 40 with the exception of using 9-bromophenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (5.9 g, yield 75%).
[LCMS]: 433
The same procedure as in Synthesis Example 40 with the exception of using 9-(3-bromophenyl)phenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.9 g, yield 74%).
[LCMS]: 509
The same procedure as in Synthesis Example 40 with the exception of using 2-bromophenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (5.9 g, yield 75%).
[LCMS]: 433
The same procedure as in Synthesis Example 40 with the exception of using 2-bromotriphenylene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.2 g, yield 70%).
[LCMS]: 483
The same procedure as in Synthesis Example 40 with the exception of using 2-bromopyrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.0 g, yield 72%).
[LCMS]: 457
The same procedure as in Synthesis Example 40 with the exception of using 1-bromopyrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.0 g, yield 72%).
[LCMS]: 457
The same procedure as in Synthesis Example 40 with the exception of using 4-bromo-2,9-dimethyl-1,10-phenanthroline instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.0 g, yield 71%)
[LCMS]: 463
6-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenanthridine (7 g, 18.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.3 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (7.6 g, 54.9 mmol) in a mixture of toluene (50 ml), EtOH (10 ml), and H2O (10 ml) were heated for 12 hour under reflux. After completion of the reaction, the reaction mixture was subjected to extraction with methylene chloride. The organic layer thus obtained was added with MgSO4 and filtered. The solvent was removed from the filtered organic layer, followed by column chromatography to afford the title compound (7.5 g, yield 84%).
[LCMS]: 488
The same procedure as in Synthesis Example 79 with the exception of using 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.7 g, yield 84%)
[LCMS]: 564
The same procedure as in Synthesis Example 79 with the exception of using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.5 g, yield 84%)
[LCMS]: 487
The same procedure as in Synthesis Example 79 with the exception of using 4-(4-bromophenyl)-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.7 g, yield 84%).
[LCMS]: 563
The same procedure as in Synthesis Example 79 with the exception of using 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.3 g, yield 80%).
[LCMS]: 564
The same procedure as in Synthesis Example 79 with the exception of using 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.7 g, yield 84%).
[LCMS]: 563
The same procedure as in Synthesis Example 79 with the exception of using 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.3 g, yield 80%).
[LCMS]: 564
The same procedure as in Synthesis Example 79 with the exception of using 2-chloro-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.3 g, yield 80%).
[LCMS]: 565
The same procedure as in Synthesis Example 79 with the exception of using 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.1 g, yield 78%)
[LCMS]: 565
The same procedure as in Synthesis Example 79 with the exception of using 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.1 g, yield 78 %).
[LCMS]: 565
The same procedure as in Synthesis Example 79 with the exception of using 4-(4-bromopyridin-2-yl)-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.0 g, yield 77%).
[LCMS]: 564
The same procedure as in Synthesis Example 79 with the exception of using 4-([1,1′-biphenyl]-4-yl)-6-(5-bromopyridin-2-yl)-2-phenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.8 g, yield 75%).
[LCMS]: 640
The same procedure as in Synthesis Example 79 with the exception of using 4-chloro-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.4 g, yield 78%).
[LCMS]: 517
The same procedure as in Synthesis Example 79 with the exception of using 4-(3-bromophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.7 g, yield 80%).
[LCMS]: 593
The same procedure as in Synthesis Example 79 with the exception of using 4-chloro-2-phenylbenzofuro[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.3 g, yield 80%)
[LCMS]: 501
The same procedure as in Synthesis Example 79 with the exception of using 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.8 g, yield 82%).
[LCMS]: 517
The same procedure as in Synthesis Example 79 with the exception of using 2-(4-bromophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.6 g, yield 79).
[LCMS]: 593
The same procedure as in Synthesis Example 79 with the exception of using 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.7 g, yield 80%)
[LCMS]: 526
The same procedure as in Synthesis Example 79 with the exception of using 2-chloro-3,5,6-triphenylpyrazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (8.0 g, yield 77%)
[LCMS]: 563
The same procedure as in Synthesis Example 79 with the exception of using 2-(3-bromophenyl)-3,5,6-triphenylpyrazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.0 g, yield 77%)
[LCMS]: 639
The same procedure as in Synthesis Example 79 with the exception of using 2-chloro-4-phenylquinazoline instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.5 g, yield 77%)
[LCMS]: 461
The same procedure as in Synthesis Example 79 with the exception of using 4′-chloro-3,2′:6′,3″-terpyridine instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was carried out to afford the title compound (7.0 g, yield 78%).
[LCMS]: 488
The same procedure as in Synthesis Example 79 with the exception of using 4-bromodibenzo[b,d]furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.4 g, yield 82%)
[LCMS]: 423
The same procedure as in Synthesis Example 79 with the exception of using 3-bromodibenzo[b,d]furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.3 g, yield 81%)
[LCMS]: 423
The same procedure as in Synthesis Example 79 with the exception of using 9-bromonaphtho[2,1-b]benzofuran instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.5 g, yield 75%)
[LCMS]: 473
The same procedure as in Synthesis Example 79 with the exception of using 8-bromobenzo[b]naphtho[1,2-d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.7 g, yield 75%)
[LCMS]: 489
The same procedure as in Synthesis Example 79 with the exception of using 3-bromodibenzo[b,d]thiophene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.4 g, yield 80%)
[LCMS]: 439
The same procedure as in Synthesis Example 79 with the exception of using 2-(4-bromophenyl)naphthalene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.8 g, yield 81%)
[LCMS]: 459
The same procedure as in Synthesis Example 79 with the exception of using 1-bromo-4-phenylnaphthalene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.7 g, yield 79%)
[LCMS]: 459
The same procedure as in Synthesis Example 79 with the exception of using 9-bromo-10-phenylanthracene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.9 g, yield 74 %).
[LCMS]: 509
The same procedure as in Synthesis Example 79 with the exception of using 2-bromo-9,10-di(naphthalen-2-yl)anthracene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (9.3 g, yield 74%)
[LCMS]: 685
The same procedure as in Synthesis Example 79 with the exception of using 5′-bromo-1,1′:3′,1″-terphenyl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.6 g, yield 74%).
[LCMS]: 485
The same procedure as in Synthesis Example 79 with the exception of using 9-bromophenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.1 g, yield 77%).
[LCMS]: 433
The same procedure as in Synthesis Example 79 with the exception of using 9-(3-bromophenyl)phenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (7.1 g, yield 76%).
[LCMS]: 509
The same procedure as in Synthesis Example 79 with the exception of using 2-bromophenanthrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.0 g, yield 76%).
[LCMS]: 433
The same procedure as in Synthesis Example 79 with the exception of using 2-bromotriphenylene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.4 g, yield 72%).
[LCMS]: 483
The same procedure as in Synthesis Example 79 with the exception of using 2-bromopyrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.1 g, yield 73%).
[LCMS]: 457
The same procedure as in Synthesis Example 79 with the exception of using 1-bromopyrene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.2 g, yield 74%).
[LCMS]: 457
The same procedure as in Synthesis Example 79 with the exception of using 4-bromo-2,9-dimethyl-1,10-phenanthroline instead of 2-chloro-4,6-diphenyl-1,3,5-triazine was carried out to afford the title compound (6.1 g, yield 72%)
[LCMS]: 463
After Compound A-1 synthesized in the Synthesis Example was isolated to a high purity through sublimation, a blue organic EL device was fabricated using same as follows.
First, a glass substrate coated with 1,200 A-thick indium tin oxide (ITO) thin film was cleansed by ultrasonication in distilled water. Following washing with distilled water, the substrate was washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. under ultrasonication. Thereafter, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned for 5 minutes using UV, and then moved to a vacuum evaporator.
On the transparent ITO electrode prepared above, Compounds 1 and 2 were co-deposited at a weight ratio of 98:2 to form a 100 Å-thick hole injection on which Compound 1 was then deposited at a thickness of 1,400 Å to form a hole transport layer. A hole transport auxiliary layer 50 Å thick was formed by deposition of Compound 3 on the hole transport layer, followed by co-depositing Compounds 4 and 5 at a weight ratio of 98:2 to form a light-emitting layer 200 Å thick. An electron transport auxiliary layer was formed by depositing Compound 6 at a thickness of 50 Å on the light-emitting layer, followed by co-depositing Compounds A-1 and 7 at a weight ratio of 1:1 to form an electron transport layer 300 Å thick. Deposition of LiF on the electron transport layer formed a 10 Å-thick electron injection layer which was then coated with Al to form a 1,000 Å-thick cathode, leading to the fabrication of an organic EL device.
Structures of Compounds 1 to 7 used for the fabrication are as follows.
Blue organic EL devices were fabricated in the same manner as in Example 1 with the exception of using the compounds listed in the following Table 1, instead of Compound A-1, as electron transport layer materials, respectively.
Blue organic EL devices were fabricated in the same manner as in Example 1 with the exception of using Compounds A to L, instead of Compound A-1, as electron transport layer materials, respectively.
The blue organic EL devices fabricated in Examples 1 to 117 and Comparative Examples 1 to 12 were measured for current density, driving voltage at 10 mA/cm2, current efficiency, and emission wavelength, and the results are summarized in Table 1, below.
As understood from the data of Table 1, the blue organic EL devices of Examples 1 to 117 in which the compounds according to the present disclosure were used in the electron transport layer was superior in terms of driving voltage, emission peak, current efficiency, and lifespan, compared to the organic EL devices of Comparative Examples 1 to 4 characterized in that the phenanthroline was connected directly or via a linker; of Comparative Examples 5 to 11 characterized in that the phenanthridine is not bonded with pyridine; of Comparative Example 12 characterized in that three pyridines were linked to the phenanthridine.
After Compound A-1 synthesized in the Synthesis Example was isolated to a high purity through sublimation, a blue organic EL device wase fabricated using same as follows.
First, a glass substrate coated with 1,500 Å-thick indium tin oxide (ITO) thin film was cleansed by ultrasonication in distilled water. Following washing with distilled water, the substrate was washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. under ultrasonication. Thereafter, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned for 5 minutes using UV, and then moved to a vacuum evaporator.
On the transparent ITO electrode prepared above, Compounds 1 and 2 were co-deposited at a weight ratio of 98:2 to form a 100 Å-thick hole injection on which Compound 1 was then deposited at a thickness of 200 Å to form a hole transport layer. A hole transport auxiliary layer 50 Å thick was formed by deposition of Compound 3 on the hole transport layer, followed by co-depositing Compounds 4 and 5 at a weight ratio of 98:2 to form a light-emitting layer 200 Å thick. Compound 7 was deposited at a thickness of 150 Å on the light-emitting layer to form an electron transport zone on which a charge generation layer was formed by depositing Compound A-1 of the Example at a thickness of 80 Å. Co-deposition of Compounds 1 and 2 at a weight ratio of 98:2 on the charge generation layer formed a 100 Å-thick hole injection layer. A 350 Å-thick hole transport layer was formed by depositing Compound 1 on the hole injection layer. On the hole transport layer was deposited Compound 3 at a thickness of 50 Å to form a hole transport auxiliary layer, followed by co-depositing Compounds 4 and 5 at a weight ratio of 98:2 to form a 200 Å-thick light-emitting layer. On the light-emitting layer, deposition was made of Compound 6 to form a 50 Å-thick electron transport auxiliary layer and then Compounds 7 and 8 at a weight ratio of 1:1 to form 300 Å-thick electron transport zone. Deposition of LiF on the electron transport layer formed a 10 Å-thick electron injection layer which was then coated with Al to form a 1,000 Å-thick cathode, leading to the fabrication of an organic EL device.
Structures of Compounds 1 to 7 used for the fabrication are as given in Example 1 and the structure of Compound 8 is as follows.
Organic EL devices were fabricated in the same manner as in Example 118 with the exception of using Compounds listed in Table 2, instead of Compound A-1, as charge generation layer materials, respectively.
Organic EL devices were fabricated in the same manner as in Example 118 with the exception of using Compounds A to L, instead of Compound A-1, as charge generation layer materials, respectively. The Compounds A to L are as described in Comparative Examples 1 to 12.
The organic EL devices fabricated in Examples 118 to 234 and Comparative Examples 13 to 24 were measured for current density, driving voltage at 10 mA/cm2, current efficiency, and emission wavelength, and the results are summarized in Table 2, below.
As understood from the data of Table 2, the organic EL devices of Examples 118 to 234 in which the compounds according to the present disclosure were used in the electron transport layer were superior in terms of driving voltage, current efficiency, and lifespan, compared to the organic EL devices of Comparative Examples 13 to 16 characterized in that the phenanthroline was connected directly or via a linker; of Comparative Examples 17 to 23 characterized in that the phenanthridine is not bonded with pyridine; of Comparative Example 24 characterized in that three pyridines were linked to the phenanthridine.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0036267 | Mar 2022 | KR | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/KR2023/003875 | 3/23/2023 | WO |
