ORGANIC LIGHT EMITTING DEVICE

The present disclosure relates to an organic light emitting device. In particular, the present disclosure relates to an organic light emitting diode and an organic light emitting device each of which includes at least one emitting material layer comprising an anthracene-based host substituted with at least one deuterium and a boron-based dopant, at least one electron blocking layer comprising an aryl-substituted amine-based compound, and optionally at least one hole blocking layer comprising at least one of an azine-based compound and a benzimidazole-based compound. The organic light emitting diode and the organic light emitting device has improved luminous efficiency and enhanced luminous lifespan.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the priority benefit under 35 U.S.C. § 119(a) of Korean Patent Application No. 10-2020-0065125, filed in the Republic of Korea on May 29, 2020, and Korean Patent Application No. 10-2021-0063694, filed in the Republic of Korea on May 17, 2021, the entire contents of which are expressly incorporated herein by reference in its entirety into the present application.

BACKGROUND

Technical Field

The present disclosure relates to anorganic light emitting device, and more specifically, to an organic light emitting device having excellent luminous efficiency and luminous lifespan.

Discussion of the Related Art

An organic light emitting diode (OLED) among a flat display device used widely has come into the spotlight as a display device replacing rapidly a liquid crystal display device (LCD). The OLED can be formed as a thin organic film less than 2000 Å and can implement unidirectional or bidirectional images by electrode configurations. Also, the OLED can be formed even on a flexible transparent substrate such as a plastic substrate so that a flexible or a foldable display device can be realized with ease using the OLED. In addition, the OLED can be driven at a lower voltage and the OLED has excellent high color purity compared to the LCD.

Since fluorescent material uses only singlet exciton energy in the luminous process, the related art fluorescent material shows low luminous efficiency. On the contrary, phosphorescent material can show high luminous efficiency since it uses triplet exciton energy as well as singlet exciton energy in the luminous process. However, metal complex, representative phosphorescent material, has short luminous lifespan for commercial use. Particularly, blue luminous materials has not showed satisfactory luminous efficiency and luminous lifespan compared to other color luminous materials. Therefore, there is a need to develop a new compound or a device structure that can enhance luminous efficiency and luminous lifespan of the organic light emitting diode.

SUMMARY

Accordingly, embodiments of the present disclosure are directed to an organic light emitting device that substantially obviates one or more of the problems due to the limitations and disadvantages of the related art.

An aspect of the present disclosure is to provide an organiclight emitting device with improved luminous efficiency and luminous lifespan.

To achieve these and other aspects of the inventive concepts, as embodied and broadly described, an organic light emitting device comprises: a substrate; and an organic light emitting diode over the substrate, the organic light emitting diode including a first electrode, a second electrode facing the first electrode and an emissive layer disposed between the first electrode and the second electrode, wherein the emissive layer comprises at least one emitting material layer disposed between the first electrode and the second electrode and at least one electron blocking layer disposed between the first electrode and the at least one emitting material layer, wherein the at least one emitting material layer includes a first host of an anthracene-based compound and a first dopant of a boron-based compound, wherein an anthracene core of the first host is deuterated and the first dopant has the following structure of Formula 3, and wherein the at least one electron blocking layer includes an amine-based compound having the following structure of Formula 5:

wherein each of R11to R14, each of R21to R24, each of R31to R35and each of R41to R45is independently selected from the group consisting of protium, deuterium, C1-C10alkyl, C6-C30aryl, C6-C30aryl amino and C5-C30hetero aryl, R11to R14, R21to R24, R31to R35and R41to R45may be identical to or different from each other; and R51is selected from the group consisting of protium, deuterium, C1-C10alkyl and C3-C15cyclo-alkyl, wherein the C6-C30aryl is optionally substituted with C1-C10alkyl;

As an example, the anthracene-based compound may have the following Formula 1:

wherein each of R1and R2is independently C6-C30aryl or C5-C30hetero aryl; L1is C6-C30arylene; a is 0 or 1; and b is an integer of 1 to 8.

The emissive layer may further comprise an electron transport layer or at least one hole blocking layer comprising at least one of an azine-based compound and a benzimidazole-based compound.

The emissive layer may include a single emitting part or comprise multiple emitting parts to form a tandem structure.

The emissive layer may include a first emitting part disposed between the first and second electrodes, a second emitting part disposed between the first emitting part and the second electrode and a first charge generation layer disposed between the first emitting part and the second emitting part, wherein the first emitting part includes a first emitting material layer and a first electron blocking layer disposed between the first electrode and the first emitting material layer, wherein the second emitting part includes a second emitting material layer, wherein at least one of the first emitting material layer and the second emitting material layer may include the first host and the first dopant.

Such an organic light emitting diode having the tandem structure may emit blue light, or white light.

The substrate may define a red pixel, a green pixel and a blue pixel and the organic light emitting diode may be located correspondingly to the red pixel, the green pixel and the blue pixel, and the organic light emitting device may further comprise a color conversion layer disposed between the substrate and the organic light emitting diode or over the organic light emitting diode correspondingly to the red pixel and the green pixel.

The substrate may define a red pixel, a green pixel and a blue pixel and the organic light emitting diode may be located correspondingly to the red pixel, the green pixel and the blue pixel, and the organic light emitting device may further comprise a color filter layer disposed between the substrate and the organic light emitting diode or over the organic light emitting diode correspondingly to the red pixel, the green pixel and the blue pixel.

DETAILED DESCRIPTION

Reference will now be made in detail to aspects of the disclosure, examples of which are illustrated in the accompanying drawings.

The organic light emitting diode of the present disclosure can enhance its luminous efficiency and its luminous lifespan by applying particular organic compounds into at least one emitting part. The organic light emitting diode can be applied into an organic light emitting device such as an organic light emitting display device or an organic light emitting illumination device.

FIG. 1is a schematic circuit diagram illustrating an organic light emitting display device of the present disclosure. As illustrated inFIG. 1, a gate line GL, a data line DL and power line PL, each of which cross each other to define a pixel region P, in the organic light emitting display device. A switching thin film transistor Ts, a driving thin film transistor Td, a storage capacitor Cst and an organic light emitting diode D are formed within the pixel region P. The pixel region P may include a red (R) pixel region, a green (G) pixel region and a blue (B) pixel region.

The switching thin film transistor Ts is connected to the gate line GL and the data line DL, and the driving thin film transistor Td and the storage capacitor Cst are connected between the switching thin film transistor Ts and the power line PL. The organic light emitting diode D is connected to the driving thin film transistor Td. When the switching thin film transistor Ts is turned on by a gate signal applied into the gate line GL, a data signal applied into the data line DL is applied into a gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

The driving thin film transistor Td is turned on by the data signal applied into the gate electrode so that a current proportional to the data signal is supplied from the power line PL to the organic light emitting diode D through the driving thin film transistor Td. And then, the organic light emitting diode D emits light having a luminance proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charge with a voltage proportional to the data signal so that the voltage of the gate electrode in the driving thin film transistor Td is kept constant during one frame. Therefore, the organic light emitting display device can display a desired image.

FIG. 2is a schematic cross-sectional view illustrating an organic light emitting display device in accordance with an exemplary aspect of the present disclosure. As illustrated inFIG. 2, the organic light emitting display device100comprises a substrate102, a thin-film transistor Tr over the substrate102, and an organic light emitting diode D connected to the thin film transistor Tr. As an example, the substrate102defines a red pixel, a green pixel and a blue pixel and the organic light emitting diode D is located in each pixel. In other words, the organic light emitting diode D, each of which emits red, green or blue light, is located correspondingly in the red pixel, the green pixel and the blue pixel.

The substrate102may include, but is not limited to, glass, thin flexible material and/or polymer plastics. For example, the flexible material may be selected from the group, but is not limited to, polyimide (PI), polyethersulfone (PES), polyethylenenaphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC) and combination thereof. The substrate102, over which the thin film transistor Tr and the organic light emitting diode D are arranged, forms an array substrate.

A buffer layer106may be disposed over the substrate102, and the thin film transistor Tr is disposed over the buffer layer106. The buffer layer106may be omitted.

A semiconductor layer110is disposed over the buffer layer106. In one exemplary aspect, the semiconductor layer110may include, but is not limited to, oxide semiconductor materials. In this case, a light-shield pattern may be disposed under the semiconductor layer110, and the light-shield pattern can prevent light from being incident toward the semiconductor layer110, and thereby, preventing the semiconductor layer110from being deteriorated by the light. Alternatively, the semiconductor layer110may include polycrystalline silicon. In this case, opposite edges of the semiconductor layer110may be doped with impurities.

A gate insulating layer120including an insulating material is disposed on the semiconductor layer110. The gate insulating layer120may include, but is not limited to, an inorganic insulating material such as silicon oxide (SiOx) or silicon nitride (SiNx).

A gate electrode130made of a conductive material such as a metal is disposed over the gate insulating layer120so as to correspond to a center of the semiconductor layer110. While the gate insulating layer120is disposed over a whole area of the substrate102inFIG. 2, the gate insulating layer120may be patterned identically as the gate electrode130.

An interlayer insulating layer140including an insulating material is disposed on the gate electrode130with covering over an entire surface of the substrate102. The interlayer insulating layer140may include an inorganic insulating material such as silicon oxide (SiOx) or silicon nitride (SiNx), or an organic insulating material such as benzocyclobutene or photo-acryl.

The interlayer insulating layer140has first and second semiconductor layer contact holes142and144that expose both sides of the semiconductor layer110. The first and second semiconductor layer contact holes142and144are disposed over opposite sides of the gate electrode130with spacing apart from the gate electrode130. The first and second semiconductor layer contact holes142and144are formed within the gate insulating layer120inFIG. 2. Alternatively, the first and second semiconductor layer contact holes142and144are formed only within the interlayer insulating layer140when the gate insulating layer120is patterned identically as the gate electrode130.

A source electrode152and a drain electrode154, which are made of conductive material such as a metal, are disposed on the interlayer insulating layer140. The source electrode152and the drain electrode154are spaced apart from each other with respect to the gate electrode130, and contact both sides of the semiconductor layer110through the first and second semiconductor layer contact holes142and144, respectively.

The semiconductor layer110, the gate electrode130, the source electrode152and the drain electrode154constitute the thin film transistor Tr, which acts as a driving element. The thin film transistor Tr inFIG. 2has a coplanar structure in which the gate electrode130, the source electrode152and the drain electrode154are disposed over the semiconductor layer110. Alternatively, the thin film transistor Tr may have an inverted staggered structure in which a gate electrode is disposed under a semiconductor layer and a source and drain electrodes are disposed over the semiconductor layer. In this case, the semiconductor layer may include amorphous silicon.

Although not shown inFIG. 2, a gate line and a data line, which cross each other to define a pixel region, and a switching element, which is connected to the gate line and the data line, is may be further formed in the pixel region. The switching element is connected to the thin film transistor Tr, which is a driving element. In addition, a power line is spaced apart in parallel from the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly keep a voltage of the gate electrode for one frame.

A passivation layer160is disposed on the source and drain electrodes152and154with covering the thin film transistor Tr over the whole substrate102. The passivation layer160has a flat top surface and a drain contact hole162that exposes the drain electrode154of the thin film transistor Tr. While the drain contact hole162is disposed on the second semiconductor layer contact hole144, it may be spaced apart from the second semiconductor layer contact hole144.

The organic light emitting diode (OLED) D includes a first electrode210that is disposed on the passivation layer160and connected to the drain electrode154of the thin film transistor Tr. The organic light emitting diode D further includes an emissive layer230and a second electrode220each of which is disposed sequentially on the first electrode210.

The first electrode210is disposed in each pixel region. The first electrode210may be an anode and include conductive material having relatively high work function value. For example, the first electrode210may include, but is not limited to, a transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), SnO, ZnO, indium cerium oxide (ICO), aluminum doped zinc oxide (AZO), and the like.

In one exemplary aspect, when the organic light emitting display device100is a top-emission type, a reflective electrode or a reflective layer may be disposed under the first electrode210. For example, the reflective electrode or the reflective layer may include, but is not limited to, aluminum-palladium-copper (APC) alloy.

In addition, a bank layer164is disposed on the passivation layer160in order to cover edges of the first electrode210. The bank layer164exposes a center of the first electrode210. The bank layer164may be omitted.

An emissive layer230is disposed on the first electrode210. In one exemplary embodiment, the emissive layer230may have a mono-layered structure of an emitting material layer. Alternatively, the emissive layer230may have a multiple-layered structure of a hole injection layer, a hole transport layer, an electron blocking layer, an emitting material layer, a hole blocking layer, an electron transport layer and/or an electron injection layer, as illustrated inFIGS. 3 and 4. The emissive layer230may have a single emitting part or may have multiple emitting parts to form a tandem structure.

The emissive layer230may include at least one emitting material layer including an anthracene-based host and a boron-based dopant and at least one electron blocking layer including an aryl amine-based compound. Alternatively, the emissive layer230may further comprise at least one hole blocking layer including at least one of an azine-based compound and a benzimidazole-based compound. The emissive layer230enables the OLED D and the organic light emitting display device100to improve their luminous efficiency and luminous lifespan considerably.

The second electrode220is disposed over the substrate102above which the emissive layer230is disposed. The second electrode220may be disposed over a whole display area, and may include a conductive material with a relatively low work function value compared to the first electrode210, and may be a cathode. For example, the second electrode220may include, but is not limited to, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloy thereof or combination thereof such as aluminum-magnesium alloy (Al—Mg).

In addition, an encapsulation film170may be disposed over the second electrode220in order to prevent outer moisture from penetrating into the organic light emitting diodeD.

The encapsulation film170may have, but is not limited to, a laminated structure of a first inorganic insulating film172, an organic insulating film174and a second inorganic insulating film176. The encapsulation film170may be omitted.

A polarizing plate may be attached onto the encapsulation film to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate. Further, a cover window may be attached onto the encapsulation film170or the polarizing plate. In this case, the substrate102and the cover window have flexible properties so that a flexible display device can be constructed.

As described above, the emissive layer230in the organic light emitting diode D includes particular compound so that the organic light emitting diode D can enhance its luminous efficiency and its luminous lifespan.FIG. 3is a schematic cross-sectional view illustrating an organic light emitting diode having a single emitting part in accordance with an exemplary embodiment of the present disclosure.

As illustrated inFIG. 3, the organic light emitting diode (OLED) D1in accordance with the first embodiment of the present disclosure includes first and second electrodes210and220facing each other and an emissive layer230disposed between the first and second electrodes210and220. In an exemplary embodiment, the emissive layer230includes an emitting material layer (EML)340, which may be a first EML, disposed between the first and second electrodes210and220and an electron blocking layer (EBL)330, which may be a first EBL, as a first exciton blocking layer disposed between the first electrode210and the EML340. Alternatively, the emissive layer230may further include a hole blocking layer (HBL)350, which may be a first HBL, as a second exciton blocking layer disposed between the EML340and the second electrode220.

In addition, the emissive layer230may further include a hole injection layer (HIL)310disposed between the first electrode210and the EBL330and a hole transport layer (HTL)320disposed between the HIL310and the EBL330. In addition, the emissive layer230may further include an electron injection layer (EIL)360disposed between the HBL350and the second electrode220. In an alternative embodiment, the emissive layer230may further include an electron transport layer (ETL) disposed between the HBL350and the EIL360.

The first electrode210may be an anode that provides a hole into the EML340. The first electrode210may include a conductive material having a relatively high work function value, for example, a transparent conductive oxide (TCO). In an exemplary embodiment, the first electrode210may include, but is not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), SnO, ZnO, indium cerium oxide (ICO), aluminum doped zinc oxide (AZO), and the like.

The second electrode220may be a cathode that provides an electron into the EML340. The second electrode220may include a conductive material having a relatively low work function values, i.e., a highly reflective material such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloy thereof or combination thereof such as aluminum-magnesium alloy (Al—Mg). For example, each of the first and second electrodes210and220may be laminated with a thickness of, but is not limited to, about 30 nm to about 300 nm.

The EML340includes a host342, which may be a first host, of an anthracene-based compound and a dopant344, which may be a first dopant, of a boron-based compound so that the EML340emits blue light. In this case, a core of the host342is deuterated. For example, the anthracene-core may be partially or fully deuterated. Also, a part or all of the hydrogens in the boron-based compound may be deuterated. Namely, the anthracene core of the host342is deuterated and the dopant344may not be deuterated or may be partially or fully deuterated. As an example, the host342of the anthracene-based compound having the partially or fully deuterated anthracene core may have the following structure of Formula 1:

In Formula 1, each of R1and R2is independently C6-C30aryl or C5-C30hetero aryl; L1is C6-C30arylene; a is 0 or 1; and b is an integer of 1 to 8.

Namely, the anthracene moiety as a core of the host342is substituted by deuterium (D), and the substituent except the anthracene moiety is not deuterated. As an example, each of R1and R2may be independently selected from the group, but is not limited to, consisting of phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, phenanthrenyl, carbazolyl and carbolinyl, for example, phenyl or naphthyl (e.g. 1-naphtyl or 2-naphthyl). L1may be phenylene or naphthylene and b may be 8.

In one exemplary embodiment, the host342may be selected from anyone having the following structure of Formula 2:

The first dopant344of the boron-based compound emitting blue light may have the following structure of Formula 3:

In Formula 3, each of R11to R14,each of R21to R24,each of R31to R35and each of R41to R45is independently selected from the group consisting of protium, deuterium, C1-C10alkyl, C6-C30aryl, C6-C30aryl amino and C5-C30hetero aryl, R11to R14,R21to R24,R31to R35and R41to R45may be identical to or different from each other; and R51is selected from the group consisting of protium, deuterium, C1-C10alkyl and C3-C15cyclo-alky, wherein the C6-C30aryl is optionally substituted with C1-C10alkyl.

When the aryl or aryl amino, which may be each of R11to R14, each of R21to R24, each of R31to R35and each of R41to R45, is substituted, the substituent may be, but is not limited to, C1-C10alkyl such as tert-butyl.

In the boron-based compound as the dopant344, the benzene ring, which is linked to the boron atom and two nitrogen atoms, is substituted by at least one of deuterium (D), C1-C10alkyl, C6-C30aryl and C6-C30aryl amino such that the OLED D1including the dopant344has improved luminous properties.

For example, the arylamino, which may be each of R11to R14, each of R21to R24, each of R31to R35and each of R41to R45, may be diphenylamine or phenyl-naphthylamine, and the aryl, which may be each of R11to R14, each of R21to R24, each of R31to R35and each of R41to R45, may be phenyl or naphthyl which is unsubstitued or substituted with at least one, for example 1-2, alkyl group. The alkyl, which may be each of R11to R14, each of R21to R24, each of R31to R35and each of R41to R45, may be C1-C5alkyl such as methyl, ethyl, propyl, butyl (e.g. tert-butyl) and pentyl, and the heteroaryl, which may be each of R11to R14, each of R21to R24, each of R31to R35and each of R41to R45, may be one of pyridyl, quinolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl. In this instance, each of the arylamino, the aryl, the alkyl and the heteroaryl may be deuterated

In addition, R51may be selected from the group consisting of protium, deuterium, C1-C10alkyl (e.g. methyl, ethyl, propyl, butyl or pentyl) and adamantyl.

In one exemplary embodiment, each of one of R11to R14, one of R21to R24, one of R31to R35and one of R41to R45may be tert-butyl, respectively, and each of the rest of R11to R14, the rest of R21to R24, the rest of R31to R35and the rest of R41to R45may be protium or deuterium, and R51may be protium, deuterium or methyl.

In another exemplary embodiment, each of one of R11to R14, one of R21to R24, one of R31to R35and one of R41to R45may be tert-butyl, respectively, another one of R31to R35may be tert-butyl phenyl, and the rest of R11to R14, the rest of R21to R24, the rest of R31to R35and the rest of R41to R45may be protium or deuterium, and R51may be protium, deuterium or methyl.

As an example, the dopant344of the boron-based compound may be selected from anyone having the following structure of Formula 4:

In one exemplary embodiment, the dopant344of the boron-based compound may be doped with a ratio of about 1 to about 50% by weight, for example, about 1 to about 30% by weight in the EML340. The EML340may be laminated with a thickness of, but is not limited to, about 10 nm to about 200 nm, preferably about 20 nm to about 100 nm, and more preferably about 20 nm to about 50 nm.

The HIL310is disposed between the first electrode210and the HTL320and improves an interface property between the inorganic first electrode210and the organic HTL320. In one exemplary embodiment, the HIL310may include a hole injection material selected from, but is not limited to, the group consisting of 4,4′4″-Tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4′,4″-Tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4′,4″-Tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4′,4″-Tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), Copper phthalocyanine (CuPc), Tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N′-Diphenyl-N,N′-bis(1-naphthyl)-1,1′-biphenyl-4,4″-diamine (NPB; NPD), 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (Dipyrazino[2,3-f: 2′3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HAT-CN), 1,3 ,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiphene)polystyrene sulfonate (PEDOT/PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and/or the compound having the following structure of Formula 12:

In an alternative embodiment, the HIL310may include a hole transport material, which will be described, doped with the hole injection material. In this case, the hole injection material may be doped with a ratio of about 1 to about 50% by weight, for example, about 1 to about 30% by weight in the HIL310. The HIL310may be omitted in compliance of the OLED D1property.

The HTL320is disposed adjacently to the EBL330between the first electrode210and the EBL330. In one exemplary embodiment, the HTL320may include a hole transport material selected from, but is not limited to, N,N′-Diphenyl-N,N′-bis(3-methylphenyl-1,1′-biphenyl-4,4′-diamine (TPD), NPB (NPD), N,N′-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (DNTPD), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), Poly [N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)-benzidine] (Poly-TPD), Poly [(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), 1,1-bis(4-(N,N′-di(p-tolyl)amino)phenyl)cyclohexane (TAPC), 3,5-Di(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine, N-([1,1′-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N4,N4,N4′,N4′-tetrakis([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,4′-diamine and/or the compound having the following structure of Formula 11:

In an exemplary embodiment, each of the HIL310and the HTL320may be laminated with a thickness of, but is not limited to, about 5 nm to about 200 nm, for example, about 5 nm to about 100 nm.

The EBL330prevents electrons from transporting from the EML340to the first electrode210. The EBL330may include an amine-based compound having the following structure of Formula 5:

As an example, at least two of R61to R64may be polycyclic. In this case, the monocyclic aryl may be phenyl, the monocyclic arylene may be phenylene, the polycyclic aryl may be C10-C20fused aryl such as naphthyl, anthracenyl, phenanthrenyl or pyrenyl, and the polycyclic arylene may be C10-C20fused arylene such as naphthylene, anthracenylene, phenanthrenylene or pyrenylene.

For example, the EBL330may be selected from any aryl-amine based compound having the following structure of Formula 6:

Alternatively, the OLED D1may further include the HBL350which prevents holes from transporting from the EML340to the second electrode220. As an example, the HBL350may include an azine-based compound having the following structure of Formula 7 and/or a benzimidazole-based compound having the following structure of Formula 9:

In Formula 7, each of Y1to Y5is independently CR71or nitrogen (N) and one to three of Y1to Y5is N, wherein R71is C6-C30aryl. L3is C6-C30arylene; R72is C6-C30aryl or C5-C30hetero aryl, wherein the C6-C30aryl is optionally substituted with another C6-C30aryl or C5-C30hetero aryl or forms a spiro structure with a C10-C30fused aryl ring or a C10-C30fused hetero aryl ring, wherein the another C6-C30aryl is optionally further substituted with other C6-C30aryl or C5-C30hetero aryl or forms a spiro structure with a C10-C30fused aryl ring; R73is hydrogen or adjacent two of R73form a fused aromatic ring; f is 0 or 1; g is 1 or 2; and his an integer of 0 to 4.

In Formula 9, Ar is C10-C30arylene; R81is C6-C30arylor C5-C30hetero aryl, each of the C6-C30aryl and the C5-C30hetero aryl is optionally substituted with C1-C10alkyl; and each of R82and R83is independently hydrogen, C1-C10alkyl or C6-C30aryl.

In one exemplary embodiment, the aryl group constituting R72in Formula 7 may be unsubstituted or substituted further with another C6-C30aryl group or C5-C30hetero aryl group, or form a spiro structure with other fused aryl ring or fused hetero aryl ring. For example, the aryl or the hetero aryl group that may be substituted to R72may be a C10-C30fused aryl group or a C10-C30fused hetero aryl group. R73in Formula 7 may be fused to form a naphthyl group. In one exemplary embodiment, the HBL350may be selected from any azine-based compound having the following structure of Formula 8:

As an example, “Ar” in Formula 9 may be a naphthylene group or an anthracenylene group, R81in Formula 9 may be a phenyl group or a benzimidazole group, R82in Formula 9 may be a methyl group, an ethyl group or a phenyl group and R83in Formula 9 may be hydrogen, a methyl group or a phenyl group. In one exemplary embodiment, the benzimidazole compound that can be introduced into the HBL350may be selected from any benzimidazole-based compound having the following structure of Formula 10:

In an exemplary embodiment, each of the EBL335and the HBL350may be independently laminated with a thickness of, but is not limited to, about 5 nm to about 200 nm, for example, about 5 nm to about 100 nm.

The compound having the structure of Formulae 7 to 10 has good electron transport property as well as excellent hole blocking property. Accordingly, the HBL350including the compound having the structure of Formulae 7 to 10 may function as a hole blocking layer and an electron transport layer.

In an alternative embodiment, the OLED D1may further include an electron transport layer (ETL) disposed between the HBL350and the EIL360. In one exemplary embodiment, the ETL may include, but is not limited to, oxadiazole-based compounds, triazole-based compounds, phenanthroline-based compounds, benzoxazole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds, triazine-based compounds, and the like.

The EIL360is disposed between the HBL350and the second electrode220, and can improve physical properties of the second electrode320and therefore, can enhance the life span of the OLED D1. In one exemplary embodiment, the EIL360may include, but is not limited to, an alkali halide or alkaline earth halide such as LiF, CsF, NaF, BaF2and the like, and/or an organic metal compound such as lithium benzoate, sodium stearate, and the like.

In an alternative embodiment, the EIL360may be an organic layer doped with the alkali metal such as Li, Na, K and/or Cs and/or the alkaline earth metal such as Mg, Sr, Ba and/or Ra. An organic host used in the EIL360may be the electron transport material and the alkali metal or the alkaline earth metal may be doped with a ratio of, but is not limited to, about 1 to about 30% by weight. As an example, each of the ETL and the EIL360may be laminated with a thickness of, but is not limited to, about 10 nm to about 200 nm, for example, about 10 nm to 100 nm.

The OLED D1can improve its luminous efficiency and can enhance its luminous lifespan by applying the host342of the anthracene-based compound having the structure of Formulae 1 to 2 and the dopant344of the boron-based compound having the structure of Formulae 3 to 4 into the EML340, the aryl amine-based compound having the structure of Formulae 5 and 6 into the EBL330, and optionally the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10 into the HBL350.

In the exemplary first embodiment, the OLED D1may have single emitting part. An OLED in accordance with the present disclosure may have a tandem structure including multiple emitting parts.FIG. 4is a schematic cross-sectional view illustrating an organic light emitting diode having two emitting parts in accordance with another exemplary embodiment of the present disclosure.

As illustrated inFIG. 4, the OLED D2in accordance with the second embodiment of the present disclosure includes first and second electrodes210and220facing each other and an emissive layer230A disposed between the first and second electrodes210and220. The emissive layer230A includes a first emitting part400disposed between the first electrode210and the second electrode220, a second emitting part500disposed between the first emitting part400and the second electrode220and a charge generation layer (CGL)470disposed between the first and second emitting parts400and500.

The first electrode210may be an anode and include conductive material having a relatively large work function values, for example, transparent conductive oxide (TCO) such as ITO, IZO, SnO, ZnO, ICO, AZO, and the like. The second electrode220may be a cathode and include a conductive material having a relatively small work function values such as Al, Mg, Ca, Ag, alloy thereof or combination thereof.

The first emitting part400includes a first emitting material layer (EML1)440disposed between the first electrode210and the CGL470and may further include a first electron blocking layer (EBL1)430disposed between the first electrode210and the EML1440, and optionally a first hole blocking layer (HBL1)450disposed between the EML1440and CGL470. In addition, the first emitting part400may further include a hole injection layer (HIL)410disposed between the first electrode210and the EBL1430and a first hole transport layer (HTL1)420disposed between the HIL410and the EBL1430.

The second emitting part500includes a second emitting material layer (EML2)540disposed between the CGL470and the second electrode220and may further include a second electron blocking layer (EBL2)530disposed between the CGL470and the EML2540, and optionally a secondhole blocking layer (HBL2)550disposed between the EML2540and the second electrode220. In addition, the second emitting part500may further include a second hole transport layer (HTL2)520disposed between the CGL470and EBL2530and an electron injection layer (EIL)560disposed between the HBL2550and the second electrode220.

As an example, each of the EML1440and the EML2540may independently comprise a host442or542, which may be a first host, of the anthracene-based compound having the structure of Formulae 1 to 2 and a dopant444or544, which may be a first dopant, of the boron-based compound having the structure of Formulae 3 to 4. While the anthracene core of the host442or542of the anthracene-based compound is partially or fully deuterated, the dopant444or544of the boron-based compound may not be deuterated or a part or all of the hydrogen may be deuterated. In this case, the OLED D2emits blue light. The host442in the EML1440may be identical to or different from the host542in the EML2540, and the dopant444in the EML1440may be identical to or different from the dopant544in the EML2540.

The HIL410is disposed between the first electrode210and the HTL1420and improves an interface property between the inorganic first electrode210and the organic HTL1420. In one exemplary embodiment, the HIL410include a hole injection material selected from, but is not limited to, the group consisting of MTDATA, NATA, 1T-NATA, 2T-NATA, CuPc, TCTA, NPB(NPD), HAT-CN, TDAPB, PEDOT/PSS, F4TCNQ, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and/or the compound having the structure of Formula 12. In an alternative embodiment, the HIL410may include a hole transport material doped with the hole injection material. The HIL410may be omitted in compliance with the OLED D2properties.

Each of the HTL1420and the HTL2520may independently include a hole transport material selected from, but is not limited to, TPD, DNTPD, NBP(NPD), CBP, poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine, N-([1,1′-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N4,N4,N4′,N4′-tetrakis([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4,4′-diamine and/or the compound having the structure of Formula 11. Each of the HIL410, the HTL1420and the HTL2520may be laminated with a thickness of, but is not limited to, about 5 nm to about 200 nm, for example, about 5 nm to about 100 nm.

Each of the EBL1430and the EBL2530prevents electrons from transporting from the EML1440or EML2540to the first electrode210or the CGL470, respectively. As an example, each of the EBL1430and the EBL2530may independently include the aryl amine-based compound having the structure of Formulae 5 to 6.

Each of the HBL1450and the HBL2550prevents holes from transporting from the EML1440or EML2540to the CGL470or the second electrode220, respectively. As an example, each of the HBL1450and the HBL2550may independently include the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10. Each of the EBL1430, the EBL2530, the HBL1450and the HBL2550may be laminated with a thickness of, but is not limited to, about 5 nm to about 200 nm, for example, about 5 nm to about 100 nm.

As described above, the compound having the structure of Formulae 7 to 10 has excellent electron transport property as well as excellent hole blocking property. Therefore, each of the HBL1450and the HBL2550may function as a hole blocking layer and an electron transport layer.

In an alternative embodiment, the first emitting part400may further include a first electron transport layer (ETL1) disposed between the HBL1450and the CGL470and/or the second emitting part500may further include a second electron transport layer (ETL2) disposed between the HBL2550and the EIL560. Each of the ETL1and the ETL2may independently include, but is not limited to, oxadiazole-based compounds, triazole-based compounds, phenanthroline-based compounds, benzoxazole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds, triazine-based compounds, and the like.

The EIL560is disposed between the HBL2550and the second electrode220. In one exemplary embodiment, the EIL560may include, but is not limited to, an alkali halide or an alkaline earth halide such as LiF, CsF, NaF, BaF2and the like, and/or an organic metal compound such as lithium benzoate, sodium stearate, and the like. In an alternative embodiment, the EIL560may include an organic layer doped with an alkali metal such as Li, Na, K and/or Cs and/or an alkaline earth metal such as Mg, Sr, Ba and/or Ra. The organic host used in the EIL560may be the electron transport material and the alkali metal or the alkaline earth metal may be doped with a ratio of, but is not limited to, about 1 to about 30% by weight. As an example, each of the ETL1, the ETL2and the EIL560may be laminated with a thickness of, but is not limited to, about 10 nm to about 200 nm, for example, about 10 nm to 100 nm.

The CGL470is disposed between the first emitting part400and the second emitting part500. The CGL470includes an N-type CGL480disposed adjacently to the first emitting part400and a P-type CGL490disposed adjacently to the second emitting part500. The N-type CGL480injects electrons into the first emitting part400and the P-type CGL490injects holes into the second emitting part500.

As an example, the N-type CGL480may be an organic layer doped with an alkali metal such as Li, Na, K and/or Cs and/or an alkaline earth metal such as Mg, Sr, Ba and/or Ra. For example, an organic host used in the N-type CGL480may include, but is not limited to, an organic compound such as Bphen or MTDATA. The alkali metal and/or the alkaline earth metal may be doped by about 0.01 to about 30% by weight in the N-type CGL480.

The P-type CGL490may include, but is not limited to, an inorganic material selected from the group consisting of tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3), vanadium oxide (V2O5) and combination thereof, and/or an organic material selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, N,N,N′,N′-Tetranaphthalenyl-benzidine (TNB), TCTA, N,N′-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8) and combination thereof.

The OLED D2in accordance with the second embodiment of the present disclosure can improve its luminous efficiency and can enhance its luminous lifespan by applying the anthracene-based compound having the structure of Formulae 1 to 2 as the first host and the boron-based compound having the structure of Formulae 3 to 4 as the first dopant into the EML1440and the EML2540, the aryl amine-based compound having the structure of Formulae 5 and 6 into the EBL1430and the EBL2530, and optionally the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10 into the HBL1450and the HBL2550. In addition, the organic light emitting display device100(See,FIG. 2) can implement an image having high color purity by laminating double stack structure of two emitting parts400and500each of which emits blue color light.

In the second embodiment, the OLED D2has a tandem structure of two emitting parts. Alternatively, an OLED may include three emitting parts that further includes a second CGL and a third emitting part disposed on the second emitting parts500except the EIL560(See,FIG. 7).

In the above embodiment, the organic light emitting display device100and the OLEDs D1and D2implement blue (B) emission. Alternatively, an organic light emitting display device and an OLED can implement a full color display device including white (W) emission.FIG. 5is a schematic cross-sectional view illustrating an organic light emitting display device in accordance with another exemplary embodiment of the present disclosure.

As illustrated inFIG. 5, the organic light emitting display device600comprises a first substrate602that defines each of a red pixel RP, a green pixel GP and a blue pixel BP, a second substrate604facing the first substrate602, a thin film transistor Tr over the first substrate602, an organic light emitting diode D disposed between the first and second substrates602and604and emitting white (W) light and a color filter layer680disposed between the organic light emitting diode D and the second substrate604.

Each of the first and second substrates602and604may include, but is not limited to, glass, flexible material and/or polymer plastics. For example, each of the first and second substrates602and604may be made of PI, PES, PEN, PET, PC and combination thereof. The first substrate602, over which a thin film transistor Tr and an organic light emitting diode D are arranged, forms an array substrate.

A buffer layer606may be disposed over the first substrate602, and the thin film transistor Tr is disposed over the buffer layer606correspondingly to each of the red pixel RP, the green pixel GP and the blue pixel BP. The buffer layer606may be omitted.

A semiconductor layer610is disposed over the buffer layer606. The semiconductor layer610may be made of oxide semiconductor material or polycrystalline silicon.

A gate insulating layer620including an insulating material, for example, inorganic insulating material such as silicon oxide (SiOx) or silicon nitride (SiNx) is disposed on the semiconductor layer610.

A gate electrode630made of a conductive material such as a metal is disposed over the gate insulating layer620so as to correspond to a center of the semiconductor layer610. An interlayer insulting layer640including an insulating material, for example, inorganic insulating material such as silicon oxide (SiOx) or silicon nitride (SiNx), or an organic insulating material such as benzocyclobutene or photo-acryl, is disposed on the gate electrode630.

The interlayer insulating layer640has first and second semiconductor layer contact holes642and644that expose both sides of the semiconductor layer610. The first and second semiconductor layer contact holes642and644are disposed over opposite sides of the gate electrode630with spacing apart from the gate electrode630.

A source electrode652and a drain electrode654, which are made of a conductive material such as a metal, are disposed on the interlayer insulating layer640. The source electrode652and the drain electrode654are spaced apart from each other with respect to the gate electrode630, and contact both sides of the semiconductor layer610through the first and second semiconductor layer contact holes642and644, respectively.

The semiconductor layer610, the gate electrode630, the source electrode652and the drain electrode654constitute the thin film transistor Tr, which acts as a driving element.

Although not shown inFIG. 5, a gate line and a data line, which cross each other to define a pixel region, and a switching element, which is connected to the gate line and the data line, may be further formed in the pixel region. The switching element is connected to the thin film transistor Tr, which is a driving element. In addition, a power line is spaced apart in parallel from the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly keep a voltage of the gate electrode for one frame.

A passivation layer660is disposed on the source and drain electrodes652and654with covering the thin film transistor Tr over the whole first substrate602. The passivation layer660has a drain contact hole662that exposes the drain electrode654of the thin film transistor Tr.

The organic light emitting diode (OLED) D is located over the passivation layer660. The OLED D includes a first electrode710that is connected to the drain electrode654of the thin film transistor Tr, a second electrode720facing from the first electrode710and an emissive layer730disposed between the first and second electrodes710and720.

The first electrode710formed for each pixel region may be an anode and may include a conductive material having relatively high work function value. For example, the first electrode710may include, ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, and the like. Alternatively, a reflective electrode or a reflective layer may be disposed under the first electrode710. For example, the reflective electrode or the reflective layer may include, but is not limited to, APC alloy.

A bank layer664is disposed on the passivation layer660in order to cover edges of the first electrode710. The bank layer664exposes a center of the first electrode710corresponding to each of the red pixel RP, the green pixel GP and the blue pixel BP. The bank layer664may be omitted.

An emissive layer730including emitting parts are disposed on the first electrode710. As illustrated inFIGS. 6 and 7, the emissive layer730may include multiple emitting parts800,900,1000,1100and1200and multiple charge generation layers870,1070and1170. Each of the emitting parts800,900,1000,1100and1200includes an emitting material layer and may further include a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and/or an electron injection layer.

The second electrode720is disposed over the first substrate602above which the emissive layer730is disposed. The second electrode720may be disposed over a whole display area, and may include a conductive material with a relatively low work function value compared to the first electrode710, and may be a cathode. For example, the second electrode720may include, but is not limited to, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloy thereof or combination thereof such as aluminum-magnesium alloy (Al—Mg).

Since the light emitted from the emissive layer730is incident to the color filter layer680through the second electrode720in the organic light emitting display device600in accordance with the second embodiment of the present disclosure, the second electrode720has a thin thickness so that the light can be transmitted.

The color filter layer680is disposed over the OLED D and includes a red color filter682, a green color filter684and a blue color filter686each of which is disposed correspondingly to the red pixel RP, the green pixel GP and the blue pixel BP, respectively. Although not shown inFIG. 5, the color filter layer680may be attached to the OLED D through an adhesive layer. Alternatively, the color filter layer680may be disposed directly on the OLED D.

In addition, an encapsulation film may be disposed over the second electrode720in order to prevent outer moisture from penetrating into the OLED D. The encapsulation film may have, but is not limited to, a laminated structure of a first inorganic insulating film, an organic insulating film and a second inorganic insulating film (See,170inFIG. 2). In addition, a polarizing plate may be attached onto the second substrate604to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate.

InFIG. 5, the light emitted from the OLED D is transmitted through the second electrode720and the color filter layer680is disposed over the OLED D. Alternatively, the light emitted from the OLED D is transmitted through the first electrode710and the color filter layer680may be disposed between the OLED D and the first substrate602. In addition, a color conversion layer may be formed between the OLED D and the color filter layer680. The color conversion layer may include a red color conversion layer, a green color conversion layer and a blue color conversion layer each of which is disposed correspondingly to each pixel (RP, GP and BP), respectively, so as to covert the white (W) color light to each of a red, green and blue color lights, respectively.

As described above, the white (W) color light emitted from the OLED D is transmitted through the red color filter682, the green color filter684and the blue color filter686each of which is disposed correspondingly to the red pixel RP, the green pixel GP and the blue pixel BP, respectively, so that red, green and blue color lights are displayed in the red pixel RP, the green pixel GP and the blue pixel BP.

FIG. 6is a schematic cross-sectional view illustrating an organic light emitting diode having a tandem structure of two emitting parts. As illustrated inFIG. 6, the organic light emitting diode (OLED) D3in accordance with the exemplary embodiment includes first and second electrodes710and720and an emissive layer730disposed between the first and second electrodes710and720. The emissive layer730includes a first emitting part800disposed between the first and second electrodes710and720, a second emitting part900disposed between the first emitting part800and the second electrode720and a charge generation layer (CGL)870disposed between the first and second emitting parts800and900.

The first emitting part800includes a first emitting material layer (EML1)840disposed between the first electrode710and the CGL870and may further include a first electron blocking layer (EBL1)830disposed between the first electrode710and the EML1840, and optionally a first hole blocking layer (HBL1)850disposed between the EML1840and the CGL870. In addition, the first emitting part800may further include a hole injection layer (HIL)810disposed between the first electrode and the EBL1830and a first hole transport layer (HTL1)820disposed between the HIL810and the EBL1830.

The EML1840includes a first host842of an anthracene-based compound and a first dopant844of a boron-based compound. While the anthracene-core in the first host842of the anthracene-based compound is partially or fully deuterated, the first dopant844of the boron-based compound may not be deuterated or a part or all of the hydrogen may be deuterated. The EML1840emits blue light.

The EBL1830may include the aryl amine-based compound having the structure of Formulae 5 to 6. The HBL1850may include the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10.As described above, the compound having the structure of Formulae 7 to 10 has excellent electron transport property as well as excellent hole blocking property. Therefore, the HBL1850may function as a hole blocking layer and an electron transport layer.

In an alternative embodiment, the first emitting part800may further include a first electron transport layer (ETL1) disposed between the HBL1850and the CGL870.

The second emitting part900includes a second emitting material layer (EML2)940disposed between the CGL870and the second electrode720and may further include a second hole transport layer (HTL2)920disposed between the CGL870and the EML2940and a second electron transport layer (ETL2) disposed between the EML2940and the second electrode720. In addition, the secondemitting part900may further include a second electron blocking layer (EBL2)930disposed between the HTL2920and the EML2940, a second hole blocking layer (HBL2)950disposed between the EML2940and the ETL2and an electron injection layer (EIL)960disposed between the ETL2and the second electrode720.

In one exemplary embodiment, the EML2940may emit redgreen (RG) light. In this case, the EML2940may include a second host942, a second dopant944as green dopant and a third dopant946as red dopant. For example, each of the second dopant944and the third dopant946may be fluorescent material, phosphorescent material and/or delayed fluorescent material, respectively.

In an alternative embodiment, the EML2940may emit yellow green (YG) light. In this case, the EML2940may include a second host, a second dopant as the green dopant and a third dopant as yellow dopant.

The second host and the second dopant as the green dopant for emitting yellow green may be the same as the host and the green dopant for emitting the red green (RG) light, respectively. The third dopant as the yellow dopant may include, but is not limited to, 5,6,11,12-Tetraphenylnaphthalene (Rubrene), 2, 8-Di-tert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene (TBRb), Bis(2-phenylbenzothiazolato)(acetylacetonate)irdium(III) (Ir(BT)2(acac)), Bis(2-(9, 9-diethytl-fluoren-2-yl)-1-phenyl-1H-benzo[d]imdiazolato)(acetylacetonate)iridium(III) (Ir(fbi)2(acac)), Bis(2-phenylpyridine)(3-(pyridine-2-yl)-2H-chromen-2-onate)iridium(III) (fac-Ir(ppy)2Pc) and/orBis(2-(2,4-difluorophenyl)quinoline)(picolinate)iridium(III) (FPQIrpic).

When the EML2940emits red green (RG) or yellow green (YG) light, each of the second and third dopants may be doped with a ratio of about 1 to about 50% by weight, for example, about 1 to about 30% by weight in the EML2940.

The CGL870is disposed between the first and second emitting parts800and900. The CGL870may be a PN-junction charge generation layer which includes an N-CGL880and a P-CGL890. Namely, the CGL870includes the N-CGL880disposed adjacently to the first emitting part800and the P-CGL890disposed adjacently to the second emitting part900.

The OLED D3in accordance with the third embodiment of the present disclosure can improve its luminous efficiency and can enhance its luminous lifespan by applying the first host842of the anthracene-based compound having the structure of Formulae 1 to 2 and the first dopant844of the boron-based compound having the structure of Formulae 3 to 4 into the EML1840, the aryl amine-based compound having the structure of Formulae 5 and 6 into the EBL1830, optionally the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10 into the HBL1850, and applying red green or yellow green luminescent materials into the EML2940. Particularly, the OLED D3includes a double stack structure that laminates a first emitting part800emitting blue (B) light and a second emitting part900emitting red green (RG) or yellow green (YG) light so that the organic light emitting display device600(See,FIG. 5) can emit white light (W).

In an alternative embodiment, the EML1840disposed between the first electrode710and the CGL870may be red green or yellow green emitting material layer, and the EML2940disposed between the CGL870and the second electrode720may be blue emitting material layer including the first host of the anthracene-based compound and the first dopant of the boron-based compound.

Alternatively, an organic light emitting diode may have a triple-stack structure.FIG. 7is a schematic cross-sectional view illustrating an organic light emitting diode in accordance with still another exemplary aspect of the present disclosure. As illustrated inFIG. 7, the organic light emitting diode (OLED) D4includes first and second electrodes710and720facing each other and an emissive layer730A disposed between the first and second electrodes710and720. The emissive layer730A includes a first emitting part1000disposed between the first and second electrodes710and720, a second emitting part1100disposed between the first emitting part1000and the second electrode720, a third emitting part1200disposed between the second emitting part1100and the second electrode720, a first charge generation layer (CGL1)1070disposed between the first and second emitting parts1000and1100, and a second charge generation layer (CGL2)1170disposed between the second and third emitting parts1100and1200.

At least one of the first to third emitting parts1000,1100and1200may emit blue (B) light and at least another of the first to third emitting parts1000,1100and1200may emit red green (RG) or yellow green (YG) light. Hereinafter, the OLED D4, where the first and third emitting parts1000and1200emit blue (B) light and the second emitting part1100emits red green (RG) or yellow green (YG) light, will be explained.

The first electrode710may be an anode injecting holes and may include conductive material having a relatively large work function values, for example, transparent conductive oxide (TCO) such as ITO, IZO, SnO, ZnO, ICO, AZO, and the like. The second electrode720may be a cathode injecting electrons and may include conductive material having a relatively small work function values such as Al, Mg, Ca, Ag, alloy thereof or combination thereof.

The first emitting part1000includes a first emitting material layer (EML1)1040disposed between the first electrode710and the CGL11070, and may further a first electron blocking layer (EBL1)1030disposed between the first electrode710and the EML11040, and optionally a first hole blocking layer (HBL1)1050disposed between the EML11040and the CGL11070. In addition, the first emitting part1000may further include a hole injection layer (HIL)1010disposed between the first electrode710and the EBL11030, a first hole transport layer (HTL1)1020disposed between the HIL1010and the EBL11030, and optionally a first electron transport layer (ETL1) disposed between the HBL11050and the CGL11070.

The second emitting part1100includes a second emitting material layer (EML2)1140disposed between the CGL11070and the CGL21170and may furtherinclude a second hole transport layer (HTL2)1120disposed between the CGL11070and the EML21140and a second electron transport layer (ETL2) disposed between the EML21140and the CGL21170. In addition, the second emitting part1100may further include a second electron blocking layer (EBL2)1130disposed between the HTL21120and the EML21140and/or a second hole blocking layer (HBL2)1150disposed between the EML21140and the ETL2.

The third emitting part1200includes a third emitting material layer (EML3)1240disposed between the CGL21170and the second electrode720and may further include a third electron blocking layer (EBL3)1230disposed between the CGL21170and the EML31240, and optionally a third hole blocking layer (HBL3)1250disposed between the EML31240and the second electrode720. In addition, the third emitting part1200may further include a third hole transport layer (HTL3)1220disposed between the CGL21170and the EBL31230, an electron injection layer (EIL)1260disposed between the HBL31250and the second electrode720, and optionally a third electron transport layer (ETL3) disposed between the HBL31250and the EIL1260.

Each of the EML11040and the EML31240may include a first host1042or1242which is the anthracene-based compound having the structure of Formulae 1 to 2 and a first dopant1044or1244which is the boron-based compound having the structure of Formulae 3 to 4. While the anthracene-core in each of the first hosts1042and1242ofthe anthracene-based compound is partially or fully deuterated, each of the first dopants1044and1244of the boron-based compound may not be deuterated or a part or all of the hydrogen in the boron-based compound may be deuterated. The first host1042in the EML11040may be identical to or different from the first host1242in the EML31240and the first dopant1044in the EML11040may be identical to or different from the first dopant1244in the EML31240. Each of the EML11040and the EML31240emit blue (B) light.

Each of the EBL11030and the EBL31230may include the aryl amine-based compound having the structure of Formulae 5 to 6, respectively. Each of the HBL11050and the HBL31250may include the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10, respectively. As described above, the compound having the structure of Formulae 7 to 10 has excellent electron transport property as well as excellent hole blocking property. Therefore, each of the HBL11050and the HBL31250may function as a hole blocking layer and an electron transport layer.

In one exemplary embodiment, the EML21140may emit red green (RG) light. In this case, the EML21140may include a second host1142, a second dopant1144of green dopant and a third dopant1146of red dopant.

In an alternative embodiment, the EML21140may emit yellow green (YG) light. In this case, the EML21140may include a second host1142, a seconddopant1144as green dopant and a third dopant1146as yellow dopant. The second host1142, the second dopant1144and the third dopant1146in the EML21140which emits red green (RG) or yellow green (YG) color may be identical to the materials as described above.

When the EML21140emits red green (RG) or yellow green (YG) light, the seconddopant1144and the third dopant1146may be doped with a ratio of about 1 to about 50% by weight, for example about 1 to about 30% by weight in the EML21140.

The CGL11070is disposed between the first emitting part1000and the second emitting part1100, and the CGL21170is disposed between the second emitting part1100and the third emitting part1200. Each of the CGL11070and the CGL21170may be a PN-junction CGL which includes a first or second N-type CGL1080or1180and a first or second P-type CGL1090or1190. The CGL11070includes the first N-type CGL1080disposed adjacently to the first emitting part1000and the first P-type CGL1090disposed adjacently to the second emitting part1100. The CGL21170includes the second N-type CGL1180disposed adjacently to the second emitting part1100and the second P-type GCL1190disposed adjacently to the third emitting part1200. Each of the first and second N-type CGLs1080and1180injects electrons to each of the first and second emitting parts1000and1100, respectively, and each of the first and second P-type CGLs1090and1190injects holes to each of the second and third emitting parts1100and1200, respectively.

The OLED D4in accordance with the third embodiment of the present disclosure can improve its luminous efficiency and can enhance its luminous lifespan by applying each of the first hosts1042and1242of the anthracene-based compound having the structure of Formulae 1 to 2 and each of first dopants1044and1244of the boron-based compound having the structure of Formulae 3 to 4 into each of the EML11040and the EML31240, respectively, the aryl amine-based compound having the structure of Formulae 5 and 6 into each of the EBL11030and the EBL31230, respectively, optionally the azine-based compound having the structure of Formulae 7 to 8 and/or the benzimidazole-based compound having the structure of Formulae 9 to 10 into the HBL11050and the HBL31250,respectively, and applying red green or yellow green luminescent materials into the EML21140. Particularly, the OLED D4includes a triple stack structure laminating two emitting parts1000and1200each of which emits blue (B) light and one emitting part1100which emits red green (RG) or yellow green (YG) light so that the organic light emitting display device600(See,FIG. 5) can emit white light (W).

InFIG. 7, a tandem-structured OLED D4laminating three emitting parts are illustrated. Alternatively, an OLED may further include at least one additional emitting parts and at least one additional charge generation layer.

In addition, an organic light emitting device in accordance with the present disclosure may include a color conversion layer.FIG. 8is a schematic cross-sectional view illustrating an organic light emitting display device in still another exemplary embodiment of the present disclosure.

As illustrated inFIG. 8, the organic light emitting display device1300comprises a first substrate1302that defines each of a red pixel RP, a green pixel GP and a blue pixel BP, a second substrate1304facing the first substrate1302, a thin film transistor Tr over the first substrate1302, an organic light emitting diode (OLED)D disposed between the first and second substrates1302and1304and emitting blue (B) light and a color conversion layer1380disposed between the OLED D and the second substrate1304. Although not shown inFIG. 8, a color filter layer may be disposed between the second substrate1304and the respective color conversion layer1380.

The thin film transistor Tr is disposed over the first substrate1302correspondingly to each of the red pixel RP, the green pixel GP and the blue pixel BP. A passivation layer1360, which has a drain contact hole exposing one electrode, for example a drain electrode, constituting the thin film transistor Tr, is formed with covering the thin film transistor Tr over the whole first substrate1302.

The OLED D, which includes a first electrode1410, an emissive layer1430and the second electrode1420, is disposed over the passivation layer1360. The first electrode1410may be connected to the drain electrode of the thin film transistor Tr through the drain contact hole. In addition, a bank layer1364covering edges of the first electrode1410is formed at the boundary between the red pixel RP, the green pixel GP and the blue pixel BP. In this case, the OLED D may have a structure ofFIG. 3orFIG. 4and can emit blue (B) light. The OLED D is disposed in each of the red pixel RP, the green pixel GP and the blue pixel BP to provide blue (B) light.

The color conversion layer1380may include a first color conversion layer1382corresponding to the red pixel RP and a second color conversion layer1384corresponding to the green pixel GP. As an example, the color conversion layer1380may include an inorganic luminescent material such as quantum dot (QD).

The blue (B) light emitted from the OLED D in the red pixel RP is converted into red (R) color light by the first color conversion layer1382and the blue (B) light emitted from the OLED D in the green pixel GP is converted into green (G) color light by the second color conversion layer1384. Accordingly, the organic light emitting display device1300can implement a color image.

In addition, when the light emitted from the OLED D is displayed through the first substrate1302, the color conversion layer1380may be disposed between the OLED D and the first substrate1302.

SYNTHESIS EXAMPLE 1

Synthesis of Host 1

(1) Synthesis of Intermediate H-1

Anhydrous cupric bromide (45 g, 0.202 mol ) was added into CCl4solutiondissolvinganthracene-D10 (18.8 g, 0.10 mol ). The mixture was heated and stirred under a nitrogen atmosphere for 12 hrs. After completion of reaction, white CuBr(I) compound was filtered off, and the filtrate was purified through 35 nm Alumina column. Under vacuum condition, the solvent was removed from the reaction solution purified through the columnto obtain the mixture including the intermediate H-1 (9-bromoanthracene-D9). The mixture includes the intermediate H-1, the starting material (anthracene-D10) and dibromo-byproduct. The mixture without additional purification was used as the starting material in the reaction Formula 1-2.

(2) Synthesis of Intermediate H-2

The intermediate H-1 (2.66 g, 0.01 mol) and naphtalene-1-boronic acid (1.72 g, 0.01 mol) was added into a rounded-bottom flask, and then toluene (30 ml) was added into the flask to form a mixture solution. Under a nitrogen atmosphere, the mixture solution was stirred with addition of NahdCO3aqueous solutiondissolving Na2CO3(2.12 g) indistilled water (10 ml). Pd(PPh3)4(0.25 g, 0.025 mmol) as catalyst was further added and stirred. After completion of reaction, the reaction solution was added into methanol solution to precipitate a product, and the precipitated product was filtered. In the reduce-pressure filter, the precipitated product was washed sequentially using water, hydrogen chloride aqueous solution (10% concentration), water and methanol. The precipitated product was purified to give an intermediate H-2 of white powder (2.6 g).

(3) Synthesis of Intermediate H-3

After dissolving the intermediate H-2 (2.8 g, 8.75 mmol) into dichloromethane (50 ml), Br2(1.4 g, 8.75 mmol) was added into the solution and then the solution was stirred under the room temperature (RT). After completion of reaction, 2M of Na2S2O3aqueous solution (10 ml) was added into the reactant and stirred. The organic layer was separated and washed using Na2S2O3aqueous solution (10% concentration, 10 ml) and distilled water. The organic layer was separated again, and water in the organic layer was removed by using MgSO4. After the organic layer was concentrated, excessive methanol was added to obtain a product. The product was filtered to give the intermediate H-3 (3.3 g).

(4) Synthesis of Host 1

The intermediate H-3 (1.96 g, 0.05 mol ) and naphtalene-2-boronic acid (1.02 g, 0.06 mol ) were added and dissolved into toluene (30 ml). The mixture solution was stirred under a nitrogen atmosphere. Na2CO3aqueous solution (1ml)dissolvingNa2CO3(1.90 g) into distilled water (8 ml) was added into the mixture solution. Pd(PPh3)4(0.125 g, 0.0125 mmol) was further added. The mixture solution was heated and stirred under a nitrogen atmosphere. After completion of reaction, the organic layer was separated, and methanol was added into the organic layer to precipitate a white solid mixture. The white solid mixture was purified by silica-gel column chromatography using the eluent of chloroform and hexane (volume ratio=1:3) to give the Host1 (2.30 g).

SYNTHESIS EXAMPLE 2

Synthesis of Host 2

The intermediate H-3 (1.96 g, 0.05 mol ) and 4-(naphtalene-2-yl)phenylboronic acid (1.49 g, 0.06 mol ) were added and dissolved into toluene (30 ml). The mixture solution was stirred under a nitrogen atmosphere. Na2CO3aqueous solution (1ml) dissolvingNa2CO3(1.90 g) into distilled water (8 ml) was added into the mixture solution. Pd(PPh3)4(0.125 g, 0.0125 mmol) was further added. The mixture solution was heated and stirred under a nitrogen atmosphere. After completion of reaction, the organic layer was separated, and methanol was added into the organic layer to precipitate a white solid mixture. The white solid mixture was purified by silica-gel column chromatography using the eluent of chloroform and hexane (volume ratio=1:3) to give the Host2 (2.30 g).

SYNTHESIS EXAMPLE 3

Synthesis of Dopant 11-2

(1) Synthesis of Intermediate I-P

Under a nitrogen atmosphere, 2,3-dichlorobromobenzene-D (22.0 g), the compound (I-E) (26.6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 2.68 g), NaOtBu (16.8 g), tri-t-butylphosphoniumtetrafluoroborate (tBu3PHBF4, 2.70 g) and xylene (300 ml) were put into a flask, and then the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=1/1 (volume ratio)) to give the intermediate (I-P) (35.0 g).

(2) Synthesis of Intermediate I-Q

Under a nitrogen atmosphere, the intermediate (I-P) (15.0 g), the intermediate (1-E) (8.4 g), Pd-132 (dichlorobis[di-t-butyl(4-dimethylaminophenyl)phosphino]palladium, 0.21 g) as a palladium catalyst, NaOtBu (4.3 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene) to give the intermediate (I-Q) (14.6 g).

Under a nitrogen atmosphere, 1.56 M of t-butyllithium pentane solution (27.5 ml) was added dropwisely added into a flask containing the intermediate (I-Q) (14.6 g) and t-butylbenzene (120 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 70° C., and then the mixture was stirred for 0.5 hour. The residue was cooled to −50° C., boron tribromide (10.7 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., N, N-diisopropylethylamine (EtNiPr2, 5.5 g) was added thereto, and the mixture was stirred at room temperature until heat generation was settled. Subsequently, the temperature of the mixture was raised to 100° C., and stirred and heating for 1 hour. The reaction solution was cooled to room temperature, the cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was partitioned. The organic layer was concentrated, and then purified with a silica gel short pass column (eluent: toluene). The obtained crude product was reprecipitated from heptane. Thus, the compound Dopant11-2 was obtained (0.5 g).

SYNTHESIS EXAMPLE 4

Synthesis of Dopant 11-3

(1) Synthesis of Intermediate I-F

Under a nitrogen atmosphere, 2,3-dichlorobromobenzene (22.0 g), the compound (I-E) (26.6 g), Pd(dba)2(2.68 g), NaOtBu (16.8 g), tBu3PHBF4(2.70 g) and xylene (300 ml) were put into a flask, and then the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=1/1 (volume ratio)) to give the intermediate (I-F) (38.0 g).

(2) Synthesis of Intermediate I-G

Under a nitrogen atmosphere, the intermediate (I-F) (15.0 g), the intermediate (1-E) (8.4 g), Pd-132 (0.21 g) as a palladium catalyst, NaOtBu (4.3 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene) to give the intermediate (I-G) (15.0 g).

Under a nitrogen atmosphere, 1.56 M of t-butyllithium pentane solution (27.5 ml) was added dropwisely added into a flask containing the intermediate (I-G) (15.0 g) and t-butylbenzene (120 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 70° C., and then the mixture was stirred for 0.5 hour. The residue was cooled to −50° C., boron tribromide (10.7 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.5 g) was added thereto, and the mixture was stirred at room temperature until heat generation was settled. Subsequently, the temperature of the mixture was raised to 100° C., and stirred and heating for 1 hour. The reaction solution was cooled to room temperature, the cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was partitioned. The organic layer was concentrated, and then purified with a silica gel short pass column (eluent: toluene). The obtained crude product was reprecipitated from heptane. Thus, the compound Dopant11-3 was obtained (6.5 g).

SYNTHESIS EXAMPLE 5

Synthesis of Dopant 11-4

(1) Synthesis of Intermediate I-S

Under a nitrogen atmosphere, 2,3-dichlorobromobenzene-D (22.0 g), the compound (I-R) (26.6 g), Pd(dba)2(2.68 g), NaOtBu (16.8 g), tBu3PHBF4(2.70 g) and xylene (300 ml) were put into a flask, and then the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=1/1 (volume ratio)) to give the intermediate (I-S) (38.0 g).

(2) Synthesis of Intermediate I-T

Under a nitrogen atmosphere, the intermediate (I-S) (15.0 g), the intermediate (I-R) (8.4 g), Pd-132 (0.21 g) as a palladium catalyst, NaOtBu (4.3 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene) to give the intermediate (I-T) (15.0 g).

Under a nitrogen atmosphere, 1.56 M of t-butyllithium pentane solution (27.5 ml) was added dropwisely added into a flask containing the intermediate (I-T) (15.0 g) and t-butylbenzene (120 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 70° C., and then the mixture was stirred for 0.5 hour. The residue was cooled to −50° C., boron tribromide (10.7 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.5 g) was added thereto, and the mixture was stirred at room temperature until heat generation was settled. Subsequently, the temperature of the mixture was raised to 100° C., and stirred and heating for 1 hour. The reaction solution was cooled to room temperature, the cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was partitioned. The organic layer was concentrated, and then purified with a silica gel short pass column (eluent: toluene). The obtained crude product was reprecipitated from heptane. Thus, the compound Dopantl 1-4 was obtained (8.0 g).

SYNTHESIS EXAMPLE 6

Synthesis of Dopant 11-1

(1) Synthesis of Intermediate I-5

(2) Synthesis of Intermediate I-6

Under a nitrogen atmosphere, the intermediate (I-5) (15.0 g), bis(4-tert-butylphenyl)amine (8.4 g), Pd-132 (0.21 g) as a palladium catalyst, NaOtBu (4.3 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene) to give the intermediate (I-6) (15.0 g).

Under a nitrogen atmosphere, 1.56 M of t-butyllithium pentane solution (27.5 ml) was added dropwisely added into a flask containing the intermediate (I-6) (15.0 g) and t-butylbenzene (120 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 70° C., and then the mixture was stirred for 0.5 hour. The residue was cooled to −50° C., boron tribromide (10.7 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.5 g) was added thereto, and the mixture was stirred at room temperature until heat generation was settled. Subsequently, the temperature of the mixture was raised to 100° C., and stirred and heating for 1 hour. The reaction solution was cooled to room temperature, the cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was partitioned. The organic layer was concentrated, and then purified with a silica gel short pass column (eluent: toluene). The obtained crude product was reprecipitated from heptane. Thus, the compound Dopant11-1 was obtained (6.5 g).

SYNTHESIS EXAMPLE 7

Synthesis of Dopant 21-2

(1) Synthesis of Intermediate I-N

Under a nitrogen atmosphere, the intermediate (I-M) (22.5 g), 4-bromo-tert-butylbenzene-D4 (17.0 g), Pd-132 (0.57 g), NaOtBu (11.5 g)and xylene (150 ml) were put into a flask, and then the mixed solution was heated with stirring for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-N) (30.0 g).

(2) Synthesis of Intermediate I-O

Under a nitrogen atmosphere, the intermediate (I-C) (12.0 g), the intermediate (I-N) (10.7 g), Pd-132 (0.19 g), NaOtBu (3.9 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1.5 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-O) (18.0 g).

Under a nitrogen atmosphere, 1.62 M of t-butyllithium pentane solution (40.0 ml) was added dropwisely added into a flask containing the intermediate (I-0) (18.0 g) and t-butylbenzene (90 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 60° C., and then the mixture was stirred for 1 hour. The residue was cooled to −50° C., boron tribromide (16.5 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.7 g) was added thereto, andthe mixture was stirred at 100° C. for 1 hour. After the reaction, aqueous sodium acetate solution was added into the reaction solvent, the mixture was stirred, ethyl acetate was added into the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, and then the crude product was purified with a silica gel column chromatography (eluent: toluene/heptane=3/7 (volume ratio)) to give the Dopant 21-2 (0.6 g).

SYNTHESIS EXAMPLE 8

Synthesis of Dopant 21-3

(1) Synthesis of Intermediate I-B

Under a nitrogen atmosphere, the intermediate (I-A) (22.5 g), 4-bromo-tert-butylbenzene (17.0 g), Pd-132 (0.57 g), NaOtBu (11.5 g)and xylene (150 ml) were put into a flask, and then the mixed solution was heated with stirring for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-B) (31.0 g).

(2) Synthesis of Intermediate I-D

Under a nitrogen atmosphere, the intermediate (I-C) (12.0 g), the intermediate (I-B) (10.7 g), Pd-132 (0.19 g), NaOtBu (3.9 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-D) (19.9 g).

Under a nitrogen atmosphere, 1.62 M of t-butyllithium pentane solution (40.0 ml) was added dropwisely added into a flask containing the intermediate (I-D) (18.0 g) and t-butylbenzene (90 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 60° C., and then the mixture was stirred for 1 hour. The components having a boiling point lower than a boiling point of t-butylbenzene was distilled under reduced pressure. The residue was cooled to −50° C., boron tribromide (16.5 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.7 g) was added thereto, andthe mixture was stirred at 100° C. for 1 hour. After the reaction, aqueous sodium acetate solution was added into the reaction solvent, the mixture was stirred, ethyl acetate was added into the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, and then the crude product was purified with a silica gel column chromatography (eluent: toluene/heptane=3/7 (volume ratio)) to give the Dopant 21-3 (4.0 g).

SYNTHESIS EXAMPLE 9

Synthesis of Dopant 21-4

(1) Synthesis of Intermediate I-J

Under a nitrogen atmosphere, the intermediate (I-A) (22.5 g), 4-bromo-tert-butylbenzene-D4 (17.0 g), Pd-132 (0.57 g), NaOtBu (11.5 g)and xylene (150 ml) were put into a flask, and then the mixed solution was heated with stirring for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-J) (31.0 g).

(2) Synthesis of Intermediate I-L

Under a nitrogen atmosphere, the intermediate (I-K) (12.0 g), the intermediate (I-J) (10.7 g), Pd-132 (0.19 g), NaOtBu (3.9 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-L) (19.9 g).

Under a nitrogen atmosphere, 1.62 M of t-butyllithium pentane solution (40.0 ml) was added dropwisely added into a flask containing the intermediate (I-L) (18.0 g) and t-butylbenzene (90 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 60° C., and then the mixture was stirred for 1 hour. The components having a boiling point lower than a boiling point of t-butylbenzene was distilled under reduced pressure. The residue was cooled to −50° C., boron tribromide (16.5 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.7 g) was added thereto, andthe mixture was stirred at 100° C. for 1 hour. After the reaction, aqueous sodium acetate solution was added into the reaction solvent, the mixture was stirred, ethyl acetate was added into the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, and then the crude product was purified with a silica gel column chromatography (eluent: toluene/heptane=3/7 (volume ratio)) to give the Dopant 21-4 (4.0 g).

SYNTHESIS EXAMPLE 10

Synthesis of Dopant 21-1

(1) Synthesis of Intermediate I-2

Under a nitrogen atmosphere, the intermediate (I-1) (22.5 g), 4-bromo-tert-butylbenzene (17.0 g), Pd-132 (0.57 g), NaOtBu (11.5 g)and xylene (150 ml) were put into a flask, and then the mixed solution was heated with stirring for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-2) (31.0 g).

(2) Synthesis of Intermediate I-4

Under a nitrogen atmosphere, the intermediate (I-3) (12.0 g), the intermediate (I-2) (10.7 g), Pd-132 (0.19 g), NaOtBu (3.9 g), and xylene (60 ml) were put into a flask, and the mixed solution was heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution, followed by stirring. Thereafter, the organic layer was separated and washed with water twice. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene/heptane=2/8 (volume ratio)) to give the intermediate (I-4) (19.9 g).

Under a nitrogen atmosphere, 1.62 M of t-butyllithium pentane solution (40.0 ml) was added dropwisely added into a flask containing the intermediate (I-4) (18.0 g) and t-butylbenzene (90 ml) at 0° C. After the completion of the dropwise addition of t-butyllithium pentane solution, the temperature of the mixture was raised to 60° C., and then the mixture was stirred for 1 hour. The components having a boiling point lower than a boiling point of t-butylbenzene was distilled under reduced pressure. The residue was cooled to −50° C., boron tribromide (16.5 g) was added thereto, the temperature of the mixture was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0° C., EtNiPr2(5.7 g) was added thereto, andthe mixture was stirred at 100° C. for 1 hour. After the reaction, aqueous sodium acetate solution was added into the reaction solvent, the mixture was stirred, ethyl acetate was added into the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, and then the crude product was purified with a silica gel column chromatography (eluent: toluene/heptane=3/7 (volume ratio)) to give the Dopant 21-1 (4.0 g).

Fabrication of Organic Light Emitting Diode (OLED)

An organic light emitting diode was fabricated by applying Host 1 synthesized in the Synthesis Example 1 as a host and Dopant 21-2 synthesized in the Synthesis Example 7 as a dopant into an emitting material layer (EML), E5 in Formula 6 into an electron blocking layer (EBL) and 2-phneyl-9,10-bis(2,2′-bipyridin-5-yl)anthracene into a a hole blocking layer (HBL). A glass substrate (40 mm×40 mm×40 mm) onto which ITO was coated as a thin film was washed and ultrasonically cleaned by solvent such as isopropyl alcohol, acetone and distilled water for 5 minutes and dried at 100° C. oven. After cleaning the substrate, the substrate was treated with O2plasma under vacuum for 2 minutes and then transferred to a vacuum chamber for depositing emission layer. Subsequently, an emissive layer and a cathode were deposited by evaporation from a heating boat under about 10−7Torr as the following order:

And then, cappling layer (CPL) was deposited over the cathode and the device was encapsualted by glass. After deposition of emissve layer and the cathode, the OLED was transferred from the depostion chamber to a dry box for film formation, followed by encapsulation using UV-curable epoxy and moisture getter.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 1, except that H1 in Formula 8 (Example 2) or H31 in Formula 10 (Example 3) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 1-3, except that Host 1-1 in the following Formula 13 as the host in the EML and NPB (N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 1-3, except that Host 1-2 in the following Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 1-3, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 1-3, except that Host 1-3 in the following Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 1-3, except that Host 1-4 in the following Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

EXPERIMENTAL EXAMPLE 1

Measurement of Luminous Properties of OLEDs

Each of the OLEDs, having 9 mm2of emission area, fabricated in Examples 1 to 3 and Comparative Examples 1 to 15 was connected to an external power source and then luminous properties for all the OLEDs were evaluated using a constant current source (KEITHLEY) and a photometer PR650at room temperature. In particular, driving voltage (V), current efficiency (Cd/A) and color coordinates at a current density of 10 mA/cm2and time period (T95) at which the luminance was reduced to 95% from initialluminance at 3000 nit at 40° C. and at a current density of 22.5 mA/m2. The measurement results are indicated in the following Table 1.

As indicated in Table 1, the OLEDs fabricated in Comparative Examples 7-9 using the Host 1, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 1-3 using the Host 1-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 4-6 and 10-12 using the Host 1-2 or Host 1-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 13-15 using the Host 1-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 7-9 using the Host 1 in the EML showed improved current efficiency and luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 7-9 using NPB in the EBL, the OLEDs fabricated in Examples 1-3 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 85.7% and 196.5%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formul 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Dopant 21-2 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 4, except that H1 in Formula 8 (Example 5) or H31 in Formula 10 (Example 6) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 4-6, except that Host 1-1 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 4-6, except that Host 1-2 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 4-6, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 4-6, except that Host 1-3 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 4-6, except that Host 1-4 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used

EXPERIMENTAL EXAMPLE 2

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 4-6 and Comparative Examples 16-30 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 2.

As indicated in Table 2, the OLEDs fabricated in Comparative Examples 22-24 using the Host 1, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 16-18 using the Host 1-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 19-21 and 25-27 using the Host 1-2 or Host 1-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 28-30 using the Host 1-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 22-24 using the Host 1 in the EML showed equivalent or a little bit reduced current efficiency and luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 22-24 using NPB in the EBL, the OLEDs fabricated in Examples 4-6 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 116.7% and 256.3%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Dopant 21-3 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 7, except that H1 in Formula 8 (Example 8) or H31 in Formula 10 (Example 9) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 7-9, except that Host 1-1 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 7-9, except that Host 1-2 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 7-9, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 7-9, except that Host 1-3 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 7-9, except that Host 1-4 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used

EXPERIMENTAL EXAMPLE 3

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 7-9 and Comparative Examples 31-45 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 3.

As indicated in Table 3, the OLEDs fabricated in Comparative Examples 37-39 using the Host 1, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 31-33 using the Host 1-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 34-36 and 40-42 using the Host 1-2 or Host 1-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 43-45 using the Host 1-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 37-39 using the Host 1 in the EML showed a little bit improved current efficiency and a little bit reduced luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 37-39 using NPB in the EBL, the OLEDs fabricated in Examples 7-9 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 104.6% and 250%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Dopant 21-4 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 10, except that H1 in Formula 8 (Example 11) or H31 in Formula 10 (Example 12) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 10-12, except that Host 1-1 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 10-12, except that Host 1-2 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 10-12, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 10-12, except that Host 1-3 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 10-12, except that Host 1-4 in Formula 13 as the host in the EML and NPB as the material in the EBL, respectively, were used

EXPERIMENTAL EXAMPLE 4

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 10-12 and Comparative Examples 46-60 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 4.

As indicated in Table 4, the OLEDs fabricated in Comparative Examples 52-54 using the Host 1, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 46-48 using the Host 1-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 49-51 and 55-57 using the Host 1-2 or Host 1-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 58-60 using the Host 1-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 52-54 using the Host 1 in the EML showed equivalent or a little bit reduced current efficiency and luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 52-54 using NPB in the EBL, the OLEDs fabricated in Examples 10-12 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 107.4% and 256.7%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Host 2 was used as the host in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 13, except that H1 in Formula 8 (Example 14) or H31 in Formula 10 (Example 15) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 13-15, except that Host 2-1 in the following Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 13-15, except that Host 2-2 in the followingFormula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 13-15, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 13-15, except that Host 2-3 in the following Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 13-15, except that Host 2-4 in the following Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

EXPERIMENTAL EXAMPLE 5

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 13-15 and Comparative Examples 61-75 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 5.

As indicated in Table 5, the OLEDs fabricated in Comparative Examples 67-69 using the Host 2, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 61-63 using the Host 2-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 64-66 and 70-72 using the Host 2-2 or Host 2-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 73-75 using the Host 2-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 67-69 using the Host 2 in the EML showed equivalent or a little bit improved current efficiency and luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 67-69 using NPB in the EBL, the OLEDs fabricated in Examples 13-15 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 107.4% and 201.2%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 13, except that Dopant 21-2 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 16, except that H1 in Formula 8 (Example 17) or H31 in Formula 10 (Example 18) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 16-18, except that Host 2-1 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 16-18, except that Host 2-2 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 16-18, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 16-18, except that Host 2-3 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 16-18, except that Host 2-4 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used

EXPERIMENTAL EXAMPLE 6

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 16-18 and Comparative Examples 76-90 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 6.

As indicated in Table 6, the OLEDs fabricated in Comparative Examples 82-84 using the Host 2, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 76-78 using the Host 2-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 79-81 and 85-87 using the Host 2-2 or Host 2-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 88-90 using the Host 2-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 82-84 using the Host 2 in the EML showed equivalent or a little bit reduced current efficiency and luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 82-84 using NPB in the EBL, the OLEDs fabricated in Examples 16-18 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 103.7% and 250%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formulal0 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 13, except that Dopant 21-3 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 19, except that H1 in Formula 8 (Example 20) or H31 in Formula 10 (Example 21) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 19-21, except that Host 2-1 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 19-21, except that Host 2-2 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 19-21, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 19-21, except that Host 2-3 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 19-21, except that Host 2-4 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used

EXPERIMENTAL EXAMPLE 7

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 19-21 and Comparative Examples 91-105 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 7.

As indicated in Table 7, the OLEDs fabricated in Comparative Examples 97-99 using the Host 2, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 91-93 using the Host 2-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 94-96 and 100-102 using the Host 2-2 or Host 2-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 103-105 using the Host 2-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 97-99 using the Host 2 in the EML showed equivalent current efficiency and a little bit reduced luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 97-99 using NPB in the EBL, the OLEDs fabricated in Examples 19-21 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 106.1% and 229.1%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 13, except that Dopant 21-4 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 22, except that H1 in Formula 8 (Example 23) or H31 in Formula 10 (Example 24) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 22-24, except that Host 2-1 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 22-24, except that Host 2-2 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 22-24, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 22-24, except that Host 2-3 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 22-42, except that Host 2-4 in Formula 14 as the host in the EML and NPB as the material in the EBL, respectively, were used

EXPERIMENTAL EXAMPLE 8

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 22-24 and Comparative Examples 106-120 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 8.

As indicated in Table 8, the OLEDs fabricated in Comparative Examples 112-114 using the Host 2, the anthracene core of which is deuterated, in the EML showed significantly increased luminous lifespan, compared to the OLEDs in Comparative Examples 106-108 using the Host 2-1, which is not deuterated, in the EML or the OLEDs in Comparative Examples 109-111 and 115-117 using the Host 2-2 or Host 2-3, the substituent of anthracene is deuterated, in the EML. In addition, compared to the OLEDs fabricated in Comparative Examples 118-120 using the Host 2-4, both the anthracene core and the substituent are deuterated, in the EML, the OLEDs fabricated in Comparative Examples 112-114 using the Host 2 in the EML showed equivalent or a little bit reduced current efficiency and luminous lifespan. Such results indicate that sufficient luminous efficiency and increased lifespan can be implemented with less expensive deuterium.

In addition, compared to the OLEDs fabricated in Comparative Examples 112-114 using NPB in the EBL, the OLEDs fabricated in Examples 22-24 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 104.1% and 248.5%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Host 2 was used as the host in the EML and E9 in Formula 6 as the material in the EBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 25, except that H1 in Formula 8 (Example 26) or H31 in Formula 10 (Example 27) was used as the material in the HBL.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 25, except that Dopant 21-2 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 28, except that H1 in Formula 8 (Example 29) or H31 in Formula 10 (Example 30) was used as the material in the HBL.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 25, except that Dopant 21-3 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 31, except that H1 in Formula 8 (Example 32) or H31 in Formula 10 (Example 33) was used as the material in the HBL.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 25, except that Dopant 21-4 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 34, except that H1 in Formula 8 (Example 35) or H31 in Formula 10 (Example 36) was used as the material in the HBL.

EXPERIMENTAL EXAMPLE 9

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 25-36 and Comparative Examples 68-69, 83-84, 98-99 and 113-114 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 9.

As indicated in Table 9, compared to the OLEDs fabricated in Comparative Examples 68-69, 83-84, 98-99 and 113-114 using NPB in the EBL, the OLEDs fabricated in Examples 25-36 using E9 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 122.3% and 238.6%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Host 2 was used as the host in the EML and Dopant 11-1 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 37, except that H1 in Formula 8 (Example 38) or H31 in Formula 10 (Example 39) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 38-39, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 37, except that Dopant 11-2 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 40, except that H1 in Formula 8 (Example 41) or H31 in Formula 10 (Example 42) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 41-42, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 37, except that Dopant 11-3 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 43, except that H1 in Formula 8 (Example 44) or H31 in Formula 10 (Example 45) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 44-45, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 37, except that Dopant 11-4 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 46, except that H1 in Formula 8 (Example 47) or H31 in Formula 10 (Example 48) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 47-48, except that NPB as the material in the EBL, respectively, was used.

EXPERIMENTAL EXAMPLE 10

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 37-48 and Comparative Examples 121-128 were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 10.

As indicated in Table 10, compared to the OLEDs fabricated in Comparative Examples 121-128 using NPB in the EBL, the OLEDs fabricated in Examples 37-48 using E5 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 105.6% and 250.8%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 1, except that Host 2 was used as the host in the EML, Dopant 11-1 was used as the dopant in the EML and E9 was used as the material in the EBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 49, except that H1 in Formula 8 (Example 50) or H31 in Formula 10 (Example 51) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 50-51, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 49, except that Dopant 11-2 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 52, except that H1 in Formula 8 (Example 53) or H31 in Formula 10 (Example 54) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 53-54, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 49, except that Dopant 11-3 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 55, except that H1 in Formula 8 (Example 56) or H31 in Formula 10 (Example 57) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 56-57, except that NPB as the material in the EBL, respectively, was used.

Fabrication of OLED

An OLED was fabricated using the same procedure and the same material as in Example 49, except that Dopant 11-4 was used as the dopant in the EML.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in Example 58, except that H1 in Formula 8 (Example 59) or H31 in Formula 10 (Example 60) was used as the material in the HBL.

Fabrication of OLEDs

An OLED was fabricated using the same procedure and the same material as in each of Examples 59-60, except that NPB as the material in the EBL, respectively, was used.

EXPERIMENTAL EXAMPLE 11

Measurement of Luminous Properties of OLEDs

Luminous properties for each of the OLEDs fabricated in Examples 49-60 and Comparative Examples 129-136were measured using the same procedure as in Experimental Example 1. The measurement results are indicated in the following Table 11.

As indicated in Table 11, compared to the OLEDs fabricated in Comparative Examples 129-136using NPB in the EBL, the OLEDs fabricated in Examples 49-60 using E9 of Formula 6 in the EBL enhanced their current efficiency and luminous lifespan up to 122.8% and 237.0%, respectively. Particularly, when the OLED includes H1 of Formula 8 or H31 of Formula 10 in the HBL, its current efficiency and luminous lifespan were significantly enhanced.